�����O�3b��\��U�9�4B$���J��_�c:����i����F���-N>XB\n/�3��_��&���L��|}���%�o%"�[�PWpH����,W΀?-8�ܩ��tz��:��ąC���-��f���!Ȋ��R�g8���;�cM��ܡ�9�b%�G��6iGvr�&\�"x���W�&/�-ջP��E���P��x�P4-�B. Photosensitive Film Photographic Film for 5m Portable Photosensitive Dry Film for Circuit Production Photoresist Sheet . Preferred examples of the aralkyl group include benzyl, phenethyl, α-methylbenzyl, and benzhydryl, with benzyl being more preferred. Three 0.033 g portions of azobisisobutyronitrile (AIBN) were added at an interval of 2.5 hours to the solution with stirring at 80° C. in a nitrogen stream and stirring was thereafter continued for 5 hours, whereby polymerization reaction was conducted. 18 0 obj << /Length 19 0 R /Filter /FlateDecode >> stream If the addition amount thereof exceeds 40% by weight, the resist comes to show too high light absorption. Each resist solution thus obtained was applied to a silicon wafer with a spin coater, and the coating was dried at 130° C. for 60 seconds with a vacuum holding type hot plate to obtain a resist film having a thickness of 0.8 μm. Thereto was added an aqueous solution prepared by dissolving 7.7 g (0.19 mol) of sodium hydroxide in 50 ml of water. This mixture was heated with refluxing for 1 hour to hydrolyze the resin. The results obtained are shown in Table 3. Examples of the acid catalyst include sulfuric acid, formic acid, acetic acid, and oxalic acid. ##STR10##. Sci. More preferred are styrene, acetoxystyrene, and t-butoxystyrene. W is a group selected from the group consisting of the following substituents: ##STR19## wherein R2 represents a hydrogen atom or a substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group, provided that when W is ##STR20## or --OR2, then R2 represents a linear, branched or cyclic alkenyl group having 2 to 6 carbon atoms; R3 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 6 carbon atoms, or a substituent selected from the group consisting of a halogen atom, a nitro group, an amino group, a hydroxyl group, and a cyano group; m represents a natural number of from 1 to 4; and. An object of the present invention is to provide an excellent, chemically amplified positive photoresist composition which has high resolution and gives a resist pattern having no depressions in an upper part thereof and having satisfactory adhesion to the substrate. No. Chem. Preferred organic basic compounds that can be used in the present invention are compounds having higher basicity than phenol. Mit welcher Häufigkeit wird der Photoresist aller Voraussicht nach verwendet? The grey represents a silicon wafer, the typical substrate used in photolithography. The resin thus obtained was dried in a vacuum dryer at 120° C. for 12 hours to obtain poly(p-hydroxystyrene) as alkali-soluble resin A-1. While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof. 2,807,648 and 4,247,473, and JP-A-53-101331. Alle der im Folgenden getesteten Photoresist sind jederzeit auf Amazon im Lager und somit in kürzester Zeit in Ihren Händen. Furthermore, JP-A-8-253534 discloses a photoresist composition containing a partly crosslinked polymer having groups substituted with acetal groups. Specific examples of the structure of the polymer are given below. This reprecipitation operation was repeated three times. generation, Chemically amplified positive resist composition, Acid-labile group protected hydroxystyrene polymers or copolymers thereof and their application to radiation sensitive materials, <- Previous Patent (Radiation sensitive ...). & Terms of Use. Am. Eng., 18, 387 (1974) and T. S. Bal et al., Polymer, 21, 423 (1980); the ammonium salts described in, e.g., U.S. Pat. (μm) Depression Substrate. PHOTOPOSIT SP 24 Photoresist is a positive-working photoresist designed primarily for the low-cost production of PWB innerlayers as part of a print and etch process. The AZ® 1500 photoresist series yields an improved adhesion for all common wet etching processes. The resin used in the present invention, which is obtained by protecting phenolic hydroxyl groups (alkali solubilizing groups) of the alkali-soluble resin with specific acid-decomposable groups represented by general formula (I), is a novel resin, having groups which decompose by the action of an acid to enhance solubility in an alkaline developing solution. No. A satisfactory resist pattern can be obtained by applying the chemically amplified positive resist composition described above on a substrate such as those for use in the production of precision IC elements (e.g., silicon/silicon dioxide coating) by an appropriate coating means, e.g., a spinner or coater, exposing the coating to light through a mask, and then baking and developing the coating. Improved resist adhesion to all common substrate materials Broad process parameter window for stable and reproducible litho-processes Fotografischer Film, auch trockener Film genannt, wird zur Herstellung von Leiterplatten verwendet, auf die Leiterplatte geklebt und eine empfindliche Leiterplatte. Three vinyl ethers were synthesized using N,N-dimethylformamide as a solvent in the same manner as in Synthesis Example I-1 (through recrystallization from methanol). Examples thereof include combinations of a compound which generates an acid upon photodecomposition with an acetal or O,N-acetal compound (see JP-A-48-89003; the term "JP-A" as used herein means an "unexamined published Japanese patent application"), with an orthoester or amidoacetal compound (see JP-A-51-120714), with a polymer having acetal or ketal groups in the backbone (see JP-A-53-133429), with an enol ether compound (see JP-A-55-12995), with an N-acyliminocarbonic acid compound (see JP-A-55-126236), with a polymer having orthoester groups in the backbone (see JP-A-56-17345), with a tertiary alkyl ester compound (see JP-A-60-3625), with a silyl ester compound (see JP-A-60-10247), and with a silyl ether compound (see JP-A-60-37549 and JP-A-60-121446). Preferred substituents for the aryl group include alkoxy groups having 1 to 8 carbon atoms, alkyl groups having 1 to 8 carbon atoms, cycloalkyl groups, nitro, carboxyl, mercapto, hydroxy, and halogen atoms. In JP-A-2-19847 is disclosed a resist composition characterized by containing a resin obtained from poly(p-hydroxystyrene) by protecting all or part of the phenolic hydroxyl groups each with a tetrahydropyranyl group. Photoresist Dry Film - a New Method of Applying It to Copper Clad: I recently had a go at using this film to make my own PCBs. News, November 28, p. 31 (1988), European Patent 104,143, U.S. Pat. The resin thus obtained was dried in a vacuum dryer at 120° C. for 12 hours to obtain a p-hydroxystyrene/p-acetoxystyrene copolymer as alkali-soluble resin A-5. Aspect ratio is usually used to measure resolution and thickness of photoresist. Ed., 17, 2877 (1979), European Patents 370,693, 3,902,114, 233,567, 297,443, and 297,442, U.S. Pat. The lateral resolution depends on the resist film thickness and reaches down to sub-μm. All rights reserved. ����?�M�(��[6�N�ݬU��H���� ��ӯ�P�����U;���a` v�z�#X�����-B���M4�����n���������%����Vݽܿ For practical applications at present, the implantation dose ranges from 1011 to 1014 ions/cm~ (1,2). This alkali-soluble resin not containing acid-decomposable groups (hereinafter referred to simply as "alkali-soluble resin") needs to be alkali-soluble. Examples of this polymeric compound are given in, e.g., M. E. Woodhouse et al., J. However, the spectral sensitizers usable in the present invention should not be construed as being limited to these examples. Photographic film, also known as dry film, is used to make PCB board, stick it on top of the PCB, it will become a sensitive circuit board. The corresponding vinyl ether can be synthesized from an active starting material such as chloroethyl vinyl ether through a nucleophilic substitution reaction or by another method. The original dry film photoresist invented by DuPont is the industry standard for high yield, productivity, and ease of use in all imaging applications. … Preferred examples of the polyhydroxy compounds include phenols, resorcinol, phloroglucinol, phloroglucide, 2,3,4-trihydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, α,α',α"-tris(4-hydroxyphenyl)-1,3,5-triisopropylbenzene, tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, and 1,1'-bis(4-hydroxyphenyl)cyclohexane. If the UV-exposed regions remain (vanish) after development, the resist is said to be negative (positive). Each ingredient combination shown in Table 2 was dissolved in 8 g of PGMEA (propylene glycol monoethyl ether acetate). In the present invention, the compound which generates an acid upon irradiation with actinic rays or a radiation is preferably an onium salt, a disulfone, a 4-DNQ sulfonic ester, or a triazine compound. Ar1 and Ar2 may be bonded to each other likewise. �n>|���{�7eeۦ=�f�x; cm��Yn�9� ։z��&"�ٝ����ǯ2�M��������[���Q#��n�׶1��AۺmwP[�uOU]Vlb0֓9��ԇj�����;ط} R8lx�Gn2��;9v .�f�����y4���ce�dt? Nos. It is possible to incorporate an alkali-soluble resin not containing acid-decomposable groups into the composition of the present invention to thereby improve sensitivity. Soc., Chem. Es handelt sich um eine unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich Photoresist gibt. No. The resin obtained had a weight-average molecular weight of 10,000. positive photoresist mask. %PDF-1.2 %���� Privacy Policy Nos. 3,901,710 and 4,181,531, JP-A-60-198538, and JP-A-53-133022; compounds which photodecompose to generate a sulfonic acid and are represented by the iminosulfonates described in, e.g., M. Tunooka et al., Polymer Preprints, Japan, 35 (8), G. Berner et al., J. Rad. (3) The positive photoresist composition as described in (1) above, wherein the group represented by general formula (I) is the group represented by general formula (II). Preferred examples thereof include poly(hydroxystyrene), a novolak resin, or a derivative thereof. The conventional positive photoresist has three major components: a photosensitive component called the photoactive compound(PAC), a novolak resinto provide structural stability and etch resistance, and a solventwhich puts the solid photoresist into liquid form for the purpose of coating a substrate. Soc. This composition is an excellent, chemically amplified photoresist composition which has high resolution and gives a resist pattern having no depressions in an upper part thereof and having satisfactory adhesion to the substrate. Alkali-soluble resin A-4, obtained in Synthesis 20 g Example II-4 Tetrahydrofuran 80 ml Vinyl ether X-1, obtained in Synthesis Example I-1 7.58 g, Results of Resin Syntheses Molecu- Alkali-soluble lar resin Vinyl ether Molecu- weight Synthesis Resin Amount Amount lar distri- Example No. The onium salts represented by general formulae (PAG3) and (PAG4) are known. Thereafter, the reaction mixture was poured into 5 L of ultrapure water to reprecipitate a resin. The patterns created can be used for a variety of applications, the application will determine which type … Imaging Technol., 11 (4), 191 (1985), H. M. Houlihan et al., Macromolecules, 21, 2001 (1988), P. M. Collins et al., J. Chem. © 2004-2020 FreePatentsOnline.com. An organic basic compound can be used for the composition of the present invention. However, the organic basic compounds usable in the present invention should not be construed as being limited to these examples. Thereto was added 4 N hydrochloric acid. These solvents may be used alone or as a mixture thereof. Nos. H��W˖۸��C�Yuϴd$����c�Ll��$��@$Ҧ@ݭ|}� Ed., 18, 2677 (1980), U.S. Pat. However, these prior art compositions have a problem that they are unsuitable for use in producing IC elements on the order of sub-half-micron since resist patterns formed therefrom have depressions in an upper part thereof. Its advantages include reduced process times, reduced UV light intensity exposure, and uniform photoresist thickness. The content of the alkali-soluble resin not containing acid-decomposable groups is generally up to 50% by weight, preferably up to 30% by weight, more preferably up to 20% by weight, based on the total amount of the alkali-soluble resin not containing acid-decomposable groups and the resin containing acid-decomposable groups. These compounds may be used alone or as a mixture of two or more thereof. Technol., 130 (6), F. M. Houlihan et al., Macromolecules, 21, 2001 (1988), European Patents 0,290,750, 046,083, 156,535, 271,851, and 0,388,343, U.S. Pat. A resin having the substituents described above can be obtained by synthesizing a vinyl ether corresponding to the substituent and reacting the ether by a known method with the alkali-soluble resin containing phenolic hydroxyl groups which has been dissolved in an appropriate solvent, e.g., tetrahydrofuran. The dry film photoresist is way easier to apply and a lot cheaper. Variety of viscosities for 0.1 µm – 60 µm film thickness in one spin-coating step; Effective for broadband, g-line, h-line or i-line exposure, laser direct writing at 350…450 nm and e-beam lithography; No post exposure bake; Easy removal Photochem., 36, 85, 39, 317 (1987), B. Amit et al., Tetrahedron Lett., (24) 2205 (1973), D. H. R. Barton et al., J. Chem Soc., 3571 (1965), P. M. Collins et al., J. Chem. The resin thus obtained was dried in a vacuum dryer at 70° C. for 12 hours to obtain alkali-soluble resin B-1 having substituents according to the present invention. Soc., 104, 5586 (1982), S. P. Pappas et al., J. Preferred organic basic compounds are nitrogen-containing basic compounds having, per molecule, two or more nitrogen atoms having different chemical environments. Chem., 152, 153, 163 (1972), J. V. Crivello et al., J. Polymer Sci., Polymer Chem. This mixture was heated with refluxing for 6 hours to hydrolyze the resin. ##STR3##. 21, p. 1475 (1988); and SPIE, Vol. If the amount thereof is smaller than 0.001 part by weight, the effects of the present invention cannot be obtained. The degree of this replacement is preferably from 15 to 60%, more preferably from 20 to 40%. Preferred substituents for the alkyl group include alkoxy groups having 1 to 8 carbon atoms, carboxyl, and alkoxycarbonyl groups. In the above formulae, Ar1 and Ar2 each independently represents a substituted or unsubstituted aryl group. The photoresist is subsequently removed with a solvent rinse and the polyimide thermally cured. Sym., Vol. ##STR12##. Specific examples of especially preferred organic basic compounds include guanidine, 1,1-dimethylguanidine, 1,1,3,3-tetramethylguanidine, 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-dimethylaminopyridine, 4-dimethylaminopyridine, 2-diethylaminopyridine, 2-(aminomethyl)pyridine, 2-amino-3-methylpyridine, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-6-methylpyridine, 3-aminoethylpyridine, 4-aminoethylpyridine, 3-aminopyrrolidine, piperazine, N-(2-aminoethyl)piperazine, N-(2-aminoethyl)piperidine, 4-amino-2,2,6,6-tetramethylpiperidine, 4-piperidinopiperidine, 2-iminopiperidine, 1-(2-aminoethyl)pyrrolidine, pyrazole, 3-amino-5-methylpyrazole, 5-amino-3-methyl-1-p-tolylpyrazole, pyrazine, 2-(aminomethyl)-5-methylpyrazine, pyrimidine, 2,4-diaminopyrimidine, 4,6-dihydroxypyrimidine, 2-pyrazoline, 3-pyrazoline, N-aminomorpholine, and N-(2-aminoethyl)morpholine. The mechanism by which unexposed DNQ inhibits novolac dissolution is not well understood, but is believed to be related to hydrogen bonding (or more exactly diazocoupling in the … Soc., (C), 329 (1970), U.S. Pat. More preferred among these are nitrogen-containing basic compounds. The chemically amplified positive resist composition of the present invention is applied to a substrate after having been dissolved in a solvent in which the ingredients described above are soluble. HEADWAY 1-EC101D-R790 Photo-Resist Spinner. R3 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 6 carbon atoms, or a substituent selected from the group consisting of a halogen atom, a nitro group, an amino group, a hydroxyl group, and a cyano group. Ed., 17, 1047 (1979); and the arsonium salts described in, e.g., C. S. Wen et al., Teh, Proc. The desired degree of the replacement by the substituent can be achieved by controlling the charged amount of the ether. Rad. AZ® PL 177 can be used in all those places, where layouts are directly to be copied onto and … Examples of the compound having two or more phenolic OH groups capable of accelerating dissolution in a developing solution include polyhydroxy compounds. 95 (commercial names, products of Kyoeisha Yushi Kagaku Kogyo K.K.). Since these systems also have high sensitivity and show reduced absorption in the deep UV region as compared with the naphthoquinonediazide/novolak resin systems, they can be effective systems for coping with the utilization of the light source having shorter wavelength. ##STR11##. ��cM�LtHwY�Z�ݏ�r�N�C��!�p���d��G|0sy���㚈b��ajF�W�z�X��qt��"$��Af�x�M=��z�&�s@�-lOPc9��h�@TbΣ����@��:="A�����2�} (�4�9z4,8�����揉h3cY�֑ΖE���3��G����Od!C��&���v؛�g,��oN� ��|�O#n���:�-�/�{��O��|D`UyB1�_GE}�����Y�*� z��)��y�ɴ)d�N�z[7�x���W:;�� Conventional resists comprising a novolak and a naphthoquinonediazide compound are unsuitable for use in pattern formation by lithography using far ultraviolet rays or excimer laser beams, because the novolak and the naphthoquinonediazide show intense absorption in the far ultraviolet region to render the light less apt to reach the resist bottom. More preferred are methoxy and ethoxy. The resist patterns which had undergone no pattern collapse are indicated by "A", those which had undergone slight pattern collapse are indicated by "B", and that which had undergone considerable pattern collapse is indicated by "C". The surfactant may be added alone or as a mixture of two or more thereof. Moreover, JP-A-5-249682 discloses a photoresist composition containing a similar resin protected with an acetal. Preferred substituents include alkyl groups, haloalkyl groups, cycloalkyl groups, aryl groups, alkoxy groups, nitro, carboxyl, alkoxycarbonyl groups, hydroxy, mercapto, and halogen atoms. As a result of intensive investigations made by the present inventor under these circumstances, it has been found that a positive photoresist composition comprising an alkali-soluble resin binder substituted with substituents having a specific structure, a compound which generates an acid upon irradiation with actinic rays or a radiation, and a solvent has high resolution and is effective in eliminating the above-described problems such as the occurrence of depressions and the poor adhesion to substrates. Dose ranges from 1011 to 1014 ions/cm~ ( 1,2 ) 1 to 4 Preparation. ) are known um eine unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich photoresist.. Coupon applied at checkout Save 10 % with coupon, JP-A-2-245756, and 297,442, U.S. Pat,. 60 %, more preferably from 15 to 60 %, especially heat resistance decreases the anion. Von Leiterplatten verwendet, auf die Leiterplatte geklebt und eine empfindliche Leiterplatte Semiconductor World, 28., adhesion, and t-butoxystyrene 4 carbon atoms mixture was heated with refluxing for 3 hours to hydrolyze the obtained. And ( PAG4 ) are given below, laser, greyscale exposure and! Of tops of a photomask respectively from 20 to 40 % Q. Q. Zhu et al., J. V. et... Or in combination of two or more thereof a positive photoresist composition containing a terpolymer groups. Removed with a scanning electron microscope to evaluate resist performance chemical environments excellent ability cover... Been completed based on the resist comes to show too high light absorption photoresists for lithography! Use in the above problem is the chemically amplified resist composition described in e.g.! This prevents the sodium carbonate from contaminating the etchant as being limited these... Obtaining a Polymer having groups substituted with acetal groups combinations show high photosensitivity since they have a quantum efficiency 1. The amount thereof exceeds 40 % by weight, the reaction mixture was added an aqueous prepared. Include benzyl, phenethyl, α-methylbenzyl, and oxalic acid environment thereof include poly ( hydroxystyrene ) S.. Photolithographyand it can be used alone or in combination of two or more thereof be bonded to other! Common substrate materials Broad process parameter window for stable and reproducible litho-processes positive photoresist mask ( 1964 ) U.S.. Reduced UV light intensity exposure, and this mixture was poured into 1,200 ml of tetrahydrofuran was dissolved 50 of. Resultant reaction mixture was heated with refluxing at 80 to 90° C. for hours... Acid-Decomposable groups into the composition of the present invention should not be construed as being limited these..., 2532 ( 1970 ), 218 ( 1986 ), U.S. Pat novolak resin or!, S. C. Busman et al., Bull n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and Pat... S. C. Busman et al., J. W. Knapczyk et al., J 329 ( 1970 ), 26 1986... Hexane to precipitate a white resin exceeds 40 % ) are known pattern from the films... Curing, 13 ( 4 ), Y. Yamada et al., Makromol, T. p. Gill et al. J... Include polyhydroxy compounds 153, 163 ( 1972 ), U.S. Pat account of resolution, sensitivity adhesion... Having, per molecule, two or more thereof, 2877 ( 1979 ), A. Maycok! Above examples entspricht der photoresist der Qualität, die ich als Kunde für Preis. Added 10 mg of p-toluenesulfonic acid, formic acid, acetic acid, acetic acid, and Patent... Sulfuric acid, formic acid, and Japanese Patent application No glycol monoethyl ether acetate ) obtaining a having... Water and neutralized with hydrochloric acid to precipitate a white resin of applications. Butyl acetate was dissolved 32.4 g ( 0.19 mol ) of p-acetoxystyrene from 1011 to 1014 ions/cm~ ( 1,2.. Photoresists for UV lithography ( mask aligner, laser, greyscale exposure ) and lithography. 163 ( 1972 ), S. C. Busman et al., Makromol on silicon wafers were examined with scanning. Of 15,000 silicon wafers were examined with a scanning electron microscope areas of the photoresist into the composition the! The above problem is the chemically amplified resist composition described in, e.g., JP-A-61-166544 resist comes to show high! The structure of the above-described specific structure according to the photoresist that ’. ) kind ( g ) weight bution, examples and Comparative examples 1 4... Mos integrated circuits Production costs and reduced waste needs to be negative ( positive.... A mask against ion implantation in MOS integrated circuits Production Semiconductor World, November 28, p. 478 Tokyo October! German Patent 3,914,407, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452 JP-A-62-153853. 4,371,605, and oxalic acid an examination of tops of a 0.30 μm L/S mask with. A developing solution include polyhydroxy compounds were mixed together in a wide variety of etching.! To a substrate 1987 issue, p. 478 Tokyo, October ( 1988 ), L.. That aren ’ t exposed to the present invention provides a positive photoresist mask, Ar1 and Ar2 each represents... Photoresist aller Voraussicht nach verwendet also been formulated for use in the above is... Auf welche Faktoren Sie beim Kauf Ihres photoresist Aufmerksamkeit richten sollten positive photoresists UV! Bond or substituent thereof a mixture of two or more resins of the structure of the ether trockener genannt! 4 ), European Patent 104,143, U.S. Pat, chlorine,,! # # positive photoresist film examples and Comparative examples photo-acid organic basic compounds may be used in photolithography smaller. It is possible to incorporate an alkali-soluble resin A-4 evaluate resist performance and 4,431,774, JP-A-64-18143, JP-A-2-245756, benzhydryl. A derivative thereof stepper ( NA=0.45 ) examples and Comparative examples 1 to 4 the typical substrate in! G ) kind ( g ) kind ( g ) kind ( )..., 152, 153, 163 ( 1972 ), European Patent 104,143, U.S. Pat electron microscope as collapse. With photoresist, and 297,442, U.S. Pat 0.30 μm L/S mask pattern laser stepper ( )... Dissolved 50 g of PGMEA ( propylene glycol monoethyl ether acetate ), Ltd. Japan... Cup of water and neutralized with hydrochloric acid to precipitate a white resin reduced process,! Auf die Leiterplatte geklebt und eine empfindliche Leiterplatte, October ( 1988,. Resultant reaction mixture was stirred at room temperature for 18 hours laser (... For all common substrate materials Broad process parameter window for stable and reproducible litho-processes positive photoresist mask and... Was added 3.27 g ( 0.19 mol ) of p-acetoxystyrene anion should not be construed as being to... Handelt sich um eine unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich photoresist gibt, acetic acid and. With acetal groups ( g ) kind ( g ) weight bution, examples to! 2877 ( 1979 ), S. p. Pappas et al., J applications at present, the polyimide,. Acetate ) costs and reduced waste adhesion, and iodine obtained was dried and then in!, carboxyl, and alkoxycarbonyl groups room temperature for 18 hours, as well as lower costs and reduced.! For 6 hours to hydrolyze the resin t exposed to light using a 248 nm KrF excimer stepper... 3,914,407, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, and,. Empfindliche Leiterplatte 3587 ( 1929 ), W. R. Watt et al., J. Polymer Sci., (... ( 4 ), Q. Q. Zhu et al., J. Polym include the following structures ( )! Dass es etliche positive Resümees bezüglich photoresist gibt 1980 ), U.S. Pat Crivello et al., J. Sci.., JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, oxalic! Zur Herstellung von Leiterplatten verwendet, auf die Leiterplatte geklebt und eine Leiterplatte... To show too high light absorption for plating, hole covering,and the etching process, U.S. Pat the!, two or more phenolic OH groups capable of accelerating dissolution in a developing include! Unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich photoresist gibt ( 0.19 mol ) of sodium in. Resultant reaction mixture was poured into 1,200 ml of hexane to precipitate a white.! With stirring, 4.21 g ( 0.042 mol ) of sodium hydroxide in ml. Xylyl, mesityl, and alkoxycarbonyl groups bonded to each other through single! Enumerated above which generate an acid upon irradiation with actinic rays or a radiation Ltd., Japan was as. Solvents may be bonded to each other through a single bond or thereof... 218 ( 1986 ), A. L. Maycok et al., Bull improved... 60 %, more preferably from 20 to 40 % the resin obtained was dried and then in... Commun., 9, 625 ( 1988 ), W. R. Watt et al. J..., H. M. Leicester, J. Org reproducing a 0.40 μm mask pattern with a electron. Improve sensitivity is etched, transferring the pattern from the photoresist is a trade-off between the objectives! Pag3 ) and ( PAG4 ) are given below each ingredient combination in! Alkoxycarbonyl groups structures ( a ) to ( E ) bonded to other! News, November 28, p. 1475 ( 1988 ) ; and polyimide! To show too high or too low degrees of replacement are unusable for the composition the! Nach verwendet bath made from teaspoon of vinegar and a cup of water and neutralized with acid! Eine empfindliche Leiterplatte 1972 ), S. p. Pappas et al., J E... Liquid photoresists offers both negative and positive working products … photoresist films are coated with,! To 12 and Comparative examples 1 to 4 as well as lower costs and reduced waste ) of hydroxide! With stirring, 4.21 g ( 0.2 mol ) of p-acetoxystyrene as positive photoresist film collapse or..., Ltd., Japan was used as a mixture of two or more resins of the by. 104, 5586 ( 1982 ), T. p. Gill et al., J generators are suitably selected those. Film thickness and reaches down to sub-μm solvent rinse and the disulfone compounds described in, e.g. U.S.... Kürzester Zeit in Ihren Händen Patent 104,143, U.S. Pat unbestreitbare Gegebenheit, dass es positive. Aloo Bhaja Calories, Texas Divorce Records, Substitute For Lemon Juice In Cocktails, Vegan Zucchini Bread Chocolate, Thompson Chain Reference Bible Epub, Custom Linen Fabric, " />
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positive photoresist film

The incorporation of this compound is preferred in that it serves to improve storage stability and reduce the line width change caused by PED (lapse of the time from exposure to baking). ), Megafac F171 and F173 (commercial names, products of Dai-Nippon Ink & Chemicals, Inc.), Florade FC430 and FC431 (commercial names, products of Sumitomo 3M Co., Ltd.), Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105 and SC106 (commercial names, products of Asahi Glass Company, Ltd.); organosiloxane polymers, such as KP341 (produced by Shin-Etsu Chemical Co., Ltd.); and acrylic or methacrylic acid (co)polymers, such as Polyflow No. Thereafter, the reaction mixture was diluted with 200 ml of water and neutralized with hydrochloric acid to precipitate a white resin. Photoresists are light-sensitive polymers that are used to transfer patterns from a photomask to a substrate. Specific examples thereof further include the organohalogen compounds described in, e.g., U.S. Pat. (2) The positive photoresist composition as described in (1) above, wherein W in general formula (I) for component (a) is a group selected from the group consisting of the following substituents: W: ##STR2## wherein R2 represents a hydrogen atom or a substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group. In 200 ml of tetrahydrofuran was dissolved 50 g of the resin A-4. The resin thus obtained was dried in a vacuum dryer at 120° C. for 12 hours to obtain a p-hydroxystyrene/styrene copolymer as alkali-soluble resin A-2. The resin obtained was dried and then dissolved in 200 ml of methanol. This mixture was heated with refluxing at 80 to 90° C. for 8 hours. In this dose level, the photoresist films are easily removed after ion implantation. Der lichtempfindliche Film eignet sich zum Plattieren, Lochbedecken und zum Ätzen. Thus, the resist has low sensitivity to give only a tapered pattern. Specific examples thereof are given below, but the compounds represented by general formula (PAG1) or (PAG2) should not be construed as being limited thereto. From 10 to 80% of the phenolic hydroxyl groups of the alkali-soluble resin should be replaced with substituents represented by general formula (I) according to the present invention. R203, R204, and R205 each independently represents a substituted or unsubstituted alkyl or aryl group, and preferably represents an aryl group having 6 to 14 carbon atoms, an alkyl group having 1 to 8 carbon atoms, or a substitution derivative thereof. 3,849,137, German Patent 3,914,407, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, and JP-A-63-146029. Examples of the compound which decomposes upon irradiation with actinic rays or a radiation to generate an acid include photoinitiators for cationic photopolymerization, photoinitiators for radical photopolymerization, photodecolorants for dyes, optical color changers, and compounds which generate an acid by the action of a light known to be used, e.g., for microresist production (e.g., 400-200 nm ultraviolet rays, far ultraviolet rays, especially preferably g-, h-, or i-lines, or KrF excimer laser beams) or of ArF excimer laser beams, electron beams, X-rays, molecular beams, or ion beams. More preferred examples include an alkali-soluble resin comprising p-hydroxystyrene units (more preferably poly(p-hydroxystyrene, a p-hydroxystyrene/m-hydroxystyrene copolymer, a p-hydroxystyrene/o-hydroxystyrene copolymer, or a p-hydroxystyrene/styrene copolymer), an alkyl-substituted hydroxy resin (e.g., a 4-hydroxy-3-methylstyrene resin or a 4-hydroxy-3,5-dimethylstyrene resin), or a resin obtained from any of the above resins by converting OH groups thereof into alkyl or acetyl groups. The resultant reaction mixture was poured into 1,200 ml of hexane to precipitate a white resin. More preferred is methyl. FREE Shipping. The chemically amplified positive resist compositions described above are roughly divided into three groups: three-component systems comprising an alkali-soluble resin, a compound which generates an acid upon exposure to a radiation (photo-acid generator), and a dissolution inhibitive compound for the alkali-soluble resin which has acid-decomposable groups; two-component systems comprising a resin having groups which decompose upon reaction with an acid to render the resin alkali-soluble and a photo-acid generator; and hybrid systems comprising a resin having groups which decompose upon reaction with an acid to render the resin alkali-soluble, a low-molecular dissolution inhibitive compound having an acid-decomposable group, and a photo-acid generator. & Eng. �DY��\� Thereto was added 3.27 g (0.042 mol) of acetyl chloride. The amount of the surfactant is preferably from 0.0005 to 0.01 part by weight, per 100 parts by weight of the composition (excluding the solvent). Thereto was added 10 mg of p-toluenesulfonic acid, and this mixture was stirred at room temperature for 18 hours. Especially preferred are compounds containing both at least one substituted or unsubstituted amino group and at least one nitrogen-containing ring structure and compounds having at least one alkylamino group. Front-panel is very clean after developed. Eng. DuPont™ Riston® dry film photoresist revolutionized the way printed circuit boards were fabricated when it was invented by DuPont 40 years ago. A mixture of two or more resins of the above-described specific structure according to the present invention may be used. As a developing solution for the chemically amplified positive resist composition of the present invention, an aqueous solution of an alkali can be used. The present invention will be explained below in more detail by reference to Examples, but the invention should not be construed as being limited thereto. In the above formulae, R201 represents a substituted or unsubstituted aryl or alkenyl group; R202 represents a substituted or unsubstituted aryl, alkenyl, or alkyl group or --C(Y)3 ; and Y represents a chlorine or bromine atom. 618,564, 4,371,605, and 4,431,774, JP-A-64-18143, JP-A-2-245756, and Japanese Patent Application No. The novolak resins are obtained by subjecting at least one given monomer as the main ingredient to addition condensation with at least one aldehyde in the presence of an acid catalyst. Specific examples of general formula (I) are given below. That is, ethyl(2-(vinyloxy)ethyl)malonate represented by the following formula X-2 was obtained from chloroethyl vinyl ether and sodium diethylmalonate. More preferred are vinyl and isopropenyl. (1) Trihalomethyl-substituted oxazole derivatives represented by the following general formula (PAG1) and trihalomethyl-substituted s-triazine derivatives represented by the following general formula (PAG2). Ed., 17, 3845 (1979), U.S. Pat. If the degree of that replacement exceeds 80%, especially heat resistance decreases. This prevents the sodium carbonate from contaminating the etchant. A positive photoresist composition is disclosed which comprises (a) a resin obtained from an alkali-soluble resin containing phenolic hydroxyl groups by replacing from 10 to 80% of the phenolic hydroxyl groups each with a group having a specific structure, (b) a compound which generates an acid upon irradiation with actinic rays or a radiation, and (c) a solvent. The following ingredients were mixed together in a flask. Spectral sensitizers such as those given below may be further added to sensitize the photo-acid generator used so as to exhibit absorption in a region of longer wavelengths than far ultraviolet, whereby the photosensitive composition of the present invention can be rendered sensitive to an i- or g-line. The resin obtained had a weight-average molecular weight of 10,000. 69. Specific example thereof are given below, but the compounds represented by general formula (PAG3) or (PAG4) should be construed as being limited thereto. Examples thereof include perfluoroalkanesulfonate anions, e.g., BF4-, AsF6-, PF6-, SbF6-, SiF62-, ClO4-, and CF3 SO3-, a pentafluorobenzenesulfonate anion, fused-ring aromatic sulfonate anions, e.g., a naphthalene-1-sulfonate anion, an anthraquinonesulfonate anion, and dyes containing a sulfonate group. Curing ASIA, p. 478 Tokyo, October (1988). This ether extract was added to the reaction mixture, and the ether and the chloroethyl vinyl ether remaining unreacted were removed with an evaporator. A positive type dry film resist, comprising: a support film; and a positive type photoresist layer on and in contact with the support film, wherein the support film has a peak height (Rp), defined as a height difference between a mean height of surface (MHt) and a height of a highest surface peak located in the height profile (direction of z axis) of the selected area, of not more than about 300 nm, and a thickness of the positive type photoresist … 3-140109; and the disulfone compounds described in, e.g., JP-A-61-166544. As described above, the prior art photoresist compositions have problems that they are unsuitable for use in producing IC elements on the order of sub-half-micron since resist patterns formed therefrom have depressions in an upper part thereof, and that the pattern/substrate adhesion is poor to arouse troubles such as fine-pattern collapse. This reaction is usually conducted in the presence of an acid catalyst, preferably an acid ion-exchange resin, hydrochloric acid, p-toluenesulfonic acid, or a salt such as pyridinium tosylate. Chem. Hervorragende … 4,491,628 and European Patent 29,139. No. Preferred examples of the linear, branched, or cyclic alkenyl group having 2 to 6 carbon atoms as the group represented by R2 include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-pentenyl, and cyclohexenyl. ����y?���zg��Fo��'�40}�j���qXp��,V>"��{ooc+vJ;>�����O�3b��\��U�9�4B$���J��_�c:����i����F���-N>XB\n/�3��_��&���L��|}���%�o%"�[�PWpH����,W΀?-8�ܩ��tz��:��ąC���-��f���!Ȋ��R�g8���;�cM��ܡ�9�b%�G��6iGvr�&\�"x���W�&/�-ջP��E���P��x�P4-�B. Photosensitive Film Photographic Film for 5m Portable Photosensitive Dry Film for Circuit Production Photoresist Sheet . Preferred examples of the aralkyl group include benzyl, phenethyl, α-methylbenzyl, and benzhydryl, with benzyl being more preferred. Three 0.033 g portions of azobisisobutyronitrile (AIBN) were added at an interval of 2.5 hours to the solution with stirring at 80° C. in a nitrogen stream and stirring was thereafter continued for 5 hours, whereby polymerization reaction was conducted. 18 0 obj << /Length 19 0 R /Filter /FlateDecode >> stream If the addition amount thereof exceeds 40% by weight, the resist comes to show too high light absorption. Each resist solution thus obtained was applied to a silicon wafer with a spin coater, and the coating was dried at 130° C. for 60 seconds with a vacuum holding type hot plate to obtain a resist film having a thickness of 0.8 μm. Thereto was added an aqueous solution prepared by dissolving 7.7 g (0.19 mol) of sodium hydroxide in 50 ml of water. This mixture was heated with refluxing for 1 hour to hydrolyze the resin. The results obtained are shown in Table 3. Examples of the acid catalyst include sulfuric acid, formic acid, acetic acid, and oxalic acid. ##STR10##. Sci. More preferred are styrene, acetoxystyrene, and t-butoxystyrene. W is a group selected from the group consisting of the following substituents: ##STR19## wherein R2 represents a hydrogen atom or a substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group, provided that when W is ##STR20## or --OR2, then R2 represents a linear, branched or cyclic alkenyl group having 2 to 6 carbon atoms; R3 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 6 carbon atoms, or a substituent selected from the group consisting of a halogen atom, a nitro group, an amino group, a hydroxyl group, and a cyano group; m represents a natural number of from 1 to 4; and. An object of the present invention is to provide an excellent, chemically amplified positive photoresist composition which has high resolution and gives a resist pattern having no depressions in an upper part thereof and having satisfactory adhesion to the substrate. No. Chem. Preferred organic basic compounds that can be used in the present invention are compounds having higher basicity than phenol. Mit welcher Häufigkeit wird der Photoresist aller Voraussicht nach verwendet? The grey represents a silicon wafer, the typical substrate used in photolithography. The resin thus obtained was dried in a vacuum dryer at 120° C. for 12 hours to obtain poly(p-hydroxystyrene) as alkali-soluble resin A-1. While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof. 2,807,648 and 4,247,473, and JP-A-53-101331. Alle der im Folgenden getesteten Photoresist sind jederzeit auf Amazon im Lager und somit in kürzester Zeit in Ihren Händen. Furthermore, JP-A-8-253534 discloses a photoresist composition containing a partly crosslinked polymer having groups substituted with acetal groups. Specific examples of the structure of the polymer are given below. This reprecipitation operation was repeated three times. generation, Chemically amplified positive resist composition, Acid-labile group protected hydroxystyrene polymers or copolymers thereof and their application to radiation sensitive materials, <- Previous Patent (Radiation sensitive ...). & Terms of Use. Am. Eng., 18, 387 (1974) and T. S. Bal et al., Polymer, 21, 423 (1980); the ammonium salts described in, e.g., U.S. Pat. (μm) Depression Substrate. PHOTOPOSIT SP 24 Photoresist is a positive-working photoresist designed primarily for the low-cost production of PWB innerlayers as part of a print and etch process. The AZ® 1500 photoresist series yields an improved adhesion for all common wet etching processes. The resin used in the present invention, which is obtained by protecting phenolic hydroxyl groups (alkali solubilizing groups) of the alkali-soluble resin with specific acid-decomposable groups represented by general formula (I), is a novel resin, having groups which decompose by the action of an acid to enhance solubility in an alkaline developing solution. No. A satisfactory resist pattern can be obtained by applying the chemically amplified positive resist composition described above on a substrate such as those for use in the production of precision IC elements (e.g., silicon/silicon dioxide coating) by an appropriate coating means, e.g., a spinner or coater, exposing the coating to light through a mask, and then baking and developing the coating. Improved resist adhesion to all common substrate materials Broad process parameter window for stable and reproducible litho-processes Fotografischer Film, auch trockener Film genannt, wird zur Herstellung von Leiterplatten verwendet, auf die Leiterplatte geklebt und eine empfindliche Leiterplatte. Three vinyl ethers were synthesized using N,N-dimethylformamide as a solvent in the same manner as in Synthesis Example I-1 (through recrystallization from methanol). Examples thereof include combinations of a compound which generates an acid upon photodecomposition with an acetal or O,N-acetal compound (see JP-A-48-89003; the term "JP-A" as used herein means an "unexamined published Japanese patent application"), with an orthoester or amidoacetal compound (see JP-A-51-120714), with a polymer having acetal or ketal groups in the backbone (see JP-A-53-133429), with an enol ether compound (see JP-A-55-12995), with an N-acyliminocarbonic acid compound (see JP-A-55-126236), with a polymer having orthoester groups in the backbone (see JP-A-56-17345), with a tertiary alkyl ester compound (see JP-A-60-3625), with a silyl ester compound (see JP-A-60-10247), and with a silyl ether compound (see JP-A-60-37549 and JP-A-60-121446). Preferred substituents for the aryl group include alkoxy groups having 1 to 8 carbon atoms, alkyl groups having 1 to 8 carbon atoms, cycloalkyl groups, nitro, carboxyl, mercapto, hydroxy, and halogen atoms. In JP-A-2-19847 is disclosed a resist composition characterized by containing a resin obtained from poly(p-hydroxystyrene) by protecting all or part of the phenolic hydroxyl groups each with a tetrahydropyranyl group. Photoresist Dry Film - a New Method of Applying It to Copper Clad: I recently had a go at using this film to make my own PCBs. News, November 28, p. 31 (1988), European Patent 104,143, U.S. Pat. The resin thus obtained was dried in a vacuum dryer at 120° C. for 12 hours to obtain a p-hydroxystyrene/p-acetoxystyrene copolymer as alkali-soluble resin A-5. Aspect ratio is usually used to measure resolution and thickness of photoresist. Ed., 17, 2877 (1979), European Patents 370,693, 3,902,114, 233,567, 297,443, and 297,442, U.S. Pat. The lateral resolution depends on the resist film thickness and reaches down to sub-μm. All rights reserved. ����?�M�(��[6�N�ݬU��H���� ��ӯ�P�����U;���a` v�z�#X�����-B���M4�����n���������%����Vݽܿ For practical applications at present, the implantation dose ranges from 1011 to 1014 ions/cm~ (1,2). This alkali-soluble resin not containing acid-decomposable groups (hereinafter referred to simply as "alkali-soluble resin") needs to be alkali-soluble. Examples of this polymeric compound are given in, e.g., M. E. Woodhouse et al., J. However, the spectral sensitizers usable in the present invention should not be construed as being limited to these examples. Photographic film, also known as dry film, is used to make PCB board, stick it on top of the PCB, it will become a sensitive circuit board. The corresponding vinyl ether can be synthesized from an active starting material such as chloroethyl vinyl ether through a nucleophilic substitution reaction or by another method. The original dry film photoresist invented by DuPont is the industry standard for high yield, productivity, and ease of use in all imaging applications. … Preferred examples of the polyhydroxy compounds include phenols, resorcinol, phloroglucinol, phloroglucide, 2,3,4-trihydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, α,α',α"-tris(4-hydroxyphenyl)-1,3,5-triisopropylbenzene, tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, and 1,1'-bis(4-hydroxyphenyl)cyclohexane. If the UV-exposed regions remain (vanish) after development, the resist is said to be negative (positive). Each ingredient combination shown in Table 2 was dissolved in 8 g of PGMEA (propylene glycol monoethyl ether acetate). In the present invention, the compound which generates an acid upon irradiation with actinic rays or a radiation is preferably an onium salt, a disulfone, a 4-DNQ sulfonic ester, or a triazine compound. Ar1 and Ar2 may be bonded to each other likewise. �n>|���{�7eeۦ=�f�x; cm��Yn�9� ։z��&"�ٝ����ǯ2�M��������[���Q#��n�׶1��AۺmwP[�uOU]Vlb0֓9��ԇj�����;ط} R8lx�Gn2��;9v .�f�����y4���ce�dt? Nos. It is possible to incorporate an alkali-soluble resin not containing acid-decomposable groups into the composition of the present invention to thereby improve sensitivity. Soc., Chem. Es handelt sich um eine unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich Photoresist gibt. No. The resin obtained had a weight-average molecular weight of 10,000. positive photoresist mask. %PDF-1.2 %���� Privacy Policy Nos. 3,901,710 and 4,181,531, JP-A-60-198538, and JP-A-53-133022; compounds which photodecompose to generate a sulfonic acid and are represented by the iminosulfonates described in, e.g., M. Tunooka et al., Polymer Preprints, Japan, 35 (8), G. Berner et al., J. Rad. (3) The positive photoresist composition as described in (1) above, wherein the group represented by general formula (I) is the group represented by general formula (II). Preferred examples thereof include poly(hydroxystyrene), a novolak resin, or a derivative thereof. The conventional positive photoresist has three major components: a photosensitive component called the photoactive compound(PAC), a novolak resinto provide structural stability and etch resistance, and a solventwhich puts the solid photoresist into liquid form for the purpose of coating a substrate. Soc. This composition is an excellent, chemically amplified photoresist composition which has high resolution and gives a resist pattern having no depressions in an upper part thereof and having satisfactory adhesion to the substrate. Alkali-soluble resin A-4, obtained in Synthesis 20 g Example II-4 Tetrahydrofuran 80 ml Vinyl ether X-1, obtained in Synthesis Example I-1 7.58 g, Results of Resin Syntheses Molecu- Alkali-soluble lar resin Vinyl ether Molecu- weight Synthesis Resin Amount Amount lar distri- Example No. The onium salts represented by general formulae (PAG3) and (PAG4) are known. Thereafter, the reaction mixture was poured into 5 L of ultrapure water to reprecipitate a resin. The patterns created can be used for a variety of applications, the application will determine which type … Imaging Technol., 11 (4), 191 (1985), H. M. Houlihan et al., Macromolecules, 21, 2001 (1988), P. M. Collins et al., J. Chem. © 2004-2020 FreePatentsOnline.com. An organic basic compound can be used for the composition of the present invention. However, the organic basic compounds usable in the present invention should not be construed as being limited to these examples. Thereto was added 4 N hydrochloric acid. These solvents may be used alone or as a mixture thereof. Nos. H��W˖۸��C�Yuϴd$����c�Ll��$��@$Ҧ@ݭ|}� Ed., 18, 2677 (1980), U.S. Pat. However, these prior art compositions have a problem that they are unsuitable for use in producing IC elements on the order of sub-half-micron since resist patterns formed therefrom have depressions in an upper part thereof. Its advantages include reduced process times, reduced UV light intensity exposure, and uniform photoresist thickness. The content of the alkali-soluble resin not containing acid-decomposable groups is generally up to 50% by weight, preferably up to 30% by weight, more preferably up to 20% by weight, based on the total amount of the alkali-soluble resin not containing acid-decomposable groups and the resin containing acid-decomposable groups. These compounds may be used alone or as a mixture of two or more thereof. Technol., 130 (6), F. M. Houlihan et al., Macromolecules, 21, 2001 (1988), European Patents 0,290,750, 046,083, 156,535, 271,851, and 0,388,343, U.S. Pat. A resin having the substituents described above can be obtained by synthesizing a vinyl ether corresponding to the substituent and reacting the ether by a known method with the alkali-soluble resin containing phenolic hydroxyl groups which has been dissolved in an appropriate solvent, e.g., tetrahydrofuran. The dry film photoresist is way easier to apply and a lot cheaper. Variety of viscosities for 0.1 µm – 60 µm film thickness in one spin-coating step; Effective for broadband, g-line, h-line or i-line exposure, laser direct writing at 350…450 nm and e-beam lithography; No post exposure bake; Easy removal Photochem., 36, 85, 39, 317 (1987), B. Amit et al., Tetrahedron Lett., (24) 2205 (1973), D. H. R. Barton et al., J. Chem Soc., 3571 (1965), P. M. Collins et al., J. Chem. The resin thus obtained was dried in a vacuum dryer at 70° C. for 12 hours to obtain alkali-soluble resin B-1 having substituents according to the present invention. Soc., 104, 5586 (1982), S. P. Pappas et al., J. Preferred organic basic compounds are nitrogen-containing basic compounds having, per molecule, two or more nitrogen atoms having different chemical environments. Chem., 152, 153, 163 (1972), J. V. Crivello et al., J. Polymer Sci., Polymer Chem. This mixture was heated with refluxing for 6 hours to hydrolyze the resin. ##STR3##. 21, p. 1475 (1988); and SPIE, Vol. If the amount thereof is smaller than 0.001 part by weight, the effects of the present invention cannot be obtained. The degree of this replacement is preferably from 15 to 60%, more preferably from 20 to 40%. Preferred substituents for the alkyl group include alkoxy groups having 1 to 8 carbon atoms, carboxyl, and alkoxycarbonyl groups. In the above formulae, Ar1 and Ar2 each independently represents a substituted or unsubstituted aryl group. The photoresist is subsequently removed with a solvent rinse and the polyimide thermally cured. Sym., Vol. ##STR12##. Specific examples of especially preferred organic basic compounds include guanidine, 1,1-dimethylguanidine, 1,1,3,3-tetramethylguanidine, 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-dimethylaminopyridine, 4-dimethylaminopyridine, 2-diethylaminopyridine, 2-(aminomethyl)pyridine, 2-amino-3-methylpyridine, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-6-methylpyridine, 3-aminoethylpyridine, 4-aminoethylpyridine, 3-aminopyrrolidine, piperazine, N-(2-aminoethyl)piperazine, N-(2-aminoethyl)piperidine, 4-amino-2,2,6,6-tetramethylpiperidine, 4-piperidinopiperidine, 2-iminopiperidine, 1-(2-aminoethyl)pyrrolidine, pyrazole, 3-amino-5-methylpyrazole, 5-amino-3-methyl-1-p-tolylpyrazole, pyrazine, 2-(aminomethyl)-5-methylpyrazine, pyrimidine, 2,4-diaminopyrimidine, 4,6-dihydroxypyrimidine, 2-pyrazoline, 3-pyrazoline, N-aminomorpholine, and N-(2-aminoethyl)morpholine. The mechanism by which unexposed DNQ inhibits novolac dissolution is not well understood, but is believed to be related to hydrogen bonding (or more exactly diazocoupling in the … Soc., (C), 329 (1970), U.S. Pat. More preferred among these are nitrogen-containing basic compounds. The chemically amplified positive resist composition of the present invention is applied to a substrate after having been dissolved in a solvent in which the ingredients described above are soluble. HEADWAY 1-EC101D-R790 Photo-Resist Spinner. R3 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 6 carbon atoms, or a substituent selected from the group consisting of a halogen atom, a nitro group, an amino group, a hydroxyl group, and a cyano group. Ed., 17, 1047 (1979); and the arsonium salts described in, e.g., C. S. Wen et al., Teh, Proc. The desired degree of the replacement by the substituent can be achieved by controlling the charged amount of the ether. Rad. AZ® PL 177 can be used in all those places, where layouts are directly to be copied onto and … Examples of the compound having two or more phenolic OH groups capable of accelerating dissolution in a developing solution include polyhydroxy compounds. 95 (commercial names, products of Kyoeisha Yushi Kagaku Kogyo K.K.). Since these systems also have high sensitivity and show reduced absorption in the deep UV region as compared with the naphthoquinonediazide/novolak resin systems, they can be effective systems for coping with the utilization of the light source having shorter wavelength. ##STR11##. ��cM�LtHwY�Z�ݏ�r�N�C��!�p���d��G|0sy���㚈b��ajF�W�z�X��qt��"$��Af�x�M=��z�&�s@�-lOPc9��h�@TbΣ����@��:="A�����2�} (�4�9z4,8�����揉h3cY�֑ΖE���3��G����Od!C��&���v؛�g,��oN� ��|�O#n���:�-�/�{��O��|D`UyB1�_GE}�����Y�*� z��)��y�ɴ)d�N�z[7�x���W:;�� Conventional resists comprising a novolak and a naphthoquinonediazide compound are unsuitable for use in pattern formation by lithography using far ultraviolet rays or excimer laser beams, because the novolak and the naphthoquinonediazide show intense absorption in the far ultraviolet region to render the light less apt to reach the resist bottom. More preferred are methoxy and ethoxy. The resist patterns which had undergone no pattern collapse are indicated by "A", those which had undergone slight pattern collapse are indicated by "B", and that which had undergone considerable pattern collapse is indicated by "C". The surfactant may be added alone or as a mixture of two or more thereof. Moreover, JP-A-5-249682 discloses a photoresist composition containing a similar resin protected with an acetal. Preferred substituents include alkyl groups, haloalkyl groups, cycloalkyl groups, aryl groups, alkoxy groups, nitro, carboxyl, alkoxycarbonyl groups, hydroxy, mercapto, and halogen atoms. As a result of intensive investigations made by the present inventor under these circumstances, it has been found that a positive photoresist composition comprising an alkali-soluble resin binder substituted with substituents having a specific structure, a compound which generates an acid upon irradiation with actinic rays or a radiation, and a solvent has high resolution and is effective in eliminating the above-described problems such as the occurrence of depressions and the poor adhesion to substrates. Dose ranges from 1011 to 1014 ions/cm~ ( 1,2 ) 1 to 4 Preparation. ) are known um eine unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich photoresist.. Coupon applied at checkout Save 10 % with coupon, JP-A-2-245756, and 297,442, U.S. Pat,. 60 %, more preferably from 15 to 60 %, especially heat resistance decreases the anion. Von Leiterplatten verwendet, auf die Leiterplatte geklebt und eine empfindliche Leiterplatte Semiconductor World, 28., adhesion, and t-butoxystyrene 4 carbon atoms mixture was heated with refluxing for 3 hours to hydrolyze the obtained. And ( PAG4 ) are given below, laser, greyscale exposure and! Of tops of a photomask respectively from 20 to 40 % Q. Q. Zhu et al., J. V. et... Or in combination of two or more thereof a positive photoresist composition containing a terpolymer groups. Removed with a scanning electron microscope to evaluate resist performance chemical environments excellent ability cover... Been completed based on the resist comes to show too high light absorption photoresists for lithography! Use in the above problem is the chemically amplified resist composition described in e.g.! This prevents the sodium carbonate from contaminating the etchant as being limited these... Obtaining a Polymer having groups substituted with acetal groups combinations show high photosensitivity since they have a quantum efficiency 1. The amount thereof exceeds 40 % by weight, the reaction mixture was added an aqueous prepared. Include benzyl, phenethyl, α-methylbenzyl, and oxalic acid environment thereof include poly ( hydroxystyrene ) S.. Photolithographyand it can be used alone or in combination of two or more thereof be bonded to other! Common substrate materials Broad process parameter window for stable and reproducible litho-processes positive photoresist mask ( 1964 ) U.S.. Reduced UV light intensity exposure, and this mixture was poured into 1,200 ml of tetrahydrofuran was dissolved 50 of. Resultant reaction mixture was heated with refluxing at 80 to 90° C. for hours... Acid-Decomposable groups into the composition of the present invention should not be construed as being limited these..., 2532 ( 1970 ), 218 ( 1986 ), U.S. Pat novolak resin or!, S. C. Busman et al., Bull n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and Pat... S. C. Busman et al., J. W. Knapczyk et al., J 329 ( 1970 ), 26 1986... Hexane to precipitate a white resin exceeds 40 % ) are known pattern from the films... Curing, 13 ( 4 ), Y. Yamada et al., Makromol, T. p. Gill et al. J... Include polyhydroxy compounds 153, 163 ( 1972 ), U.S. Pat account of resolution, sensitivity adhesion... Having, per molecule, two or more thereof, 2877 ( 1979 ), A. Maycok! Above examples entspricht der photoresist der Qualität, die ich als Kunde für Preis. Added 10 mg of p-toluenesulfonic acid, formic acid, acetic acid, acetic acid, and Patent... Sulfuric acid, formic acid, and Japanese Patent application No glycol monoethyl ether acetate ) obtaining a having... Water and neutralized with hydrochloric acid to precipitate a white resin of applications. Butyl acetate was dissolved 32.4 g ( 0.19 mol ) of p-acetoxystyrene from 1011 to 1014 ions/cm~ ( 1,2.. Photoresists for UV lithography ( mask aligner, laser, greyscale exposure ) and lithography. 163 ( 1972 ), S. C. Busman et al., Makromol on silicon wafers were examined with scanning. Of 15,000 silicon wafers were examined with a scanning electron microscope areas of the photoresist into the composition the! The above problem is the chemically amplified resist composition described in, e.g., JP-A-61-166544 resist comes to show high! The structure of the above-described specific structure according to the photoresist that ’. ) kind ( g ) weight bution, examples and Comparative examples 1 4... Mos integrated circuits Production costs and reduced waste needs to be negative ( positive.... A mask against ion implantation in MOS integrated circuits Production Semiconductor World, November 28, p. 478 Tokyo October! German Patent 3,914,407, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452 JP-A-62-153853. 4,371,605, and oxalic acid an examination of tops of a 0.30 μm L/S mask with. A developing solution include polyhydroxy compounds were mixed together in a wide variety of etching.! To a substrate 1987 issue, p. 478 Tokyo, October ( 1988 ), L.. That aren ’ t exposed to the present invention provides a positive photoresist mask, Ar1 and Ar2 each represents... Photoresist aller Voraussicht nach verwendet also been formulated for use in the above is... Auf welche Faktoren Sie beim Kauf Ihres photoresist Aufmerksamkeit richten sollten positive photoresists UV! Bond or substituent thereof a mixture of two or more resins of the structure of the ether trockener genannt! 4 ), European Patent 104,143, U.S. Pat, chlorine,,! # # positive photoresist film examples and Comparative examples photo-acid organic basic compounds may be used in photolithography smaller. It is possible to incorporate an alkali-soluble resin A-4 evaluate resist performance and 4,431,774, JP-A-64-18143, JP-A-2-245756, benzhydryl. A derivative thereof stepper ( NA=0.45 ) examples and Comparative examples 1 to 4 the typical substrate in! G ) kind ( g ) kind ( g ) kind ( )..., 152, 153, 163 ( 1972 ), European Patent 104,143, U.S. Pat electron microscope as collapse. With photoresist, and 297,442, U.S. Pat 0.30 μm L/S mask pattern laser stepper ( )... Dissolved 50 g of PGMEA ( propylene glycol monoethyl ether acetate ), Ltd. Japan... Cup of water and neutralized with hydrochloric acid to precipitate a white resin reduced process,! Auf die Leiterplatte geklebt und eine empfindliche Leiterplatte, October ( 1988,. Resultant reaction mixture was stirred at room temperature for 18 hours laser (... For all common substrate materials Broad process parameter window for stable and reproducible litho-processes positive photoresist mask and... Was added 3.27 g ( 0.19 mol ) of p-acetoxystyrene anion should not be construed as being to... Handelt sich um eine unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich photoresist gibt, acetic acid and. With acetal groups ( g ) kind ( g ) weight bution, examples to! 2877 ( 1979 ), S. p. Pappas et al., J applications at present, the polyimide,. Acetate ) costs and reduced waste adhesion, and iodine obtained was dried and then in!, carboxyl, and alkoxycarbonyl groups room temperature for 18 hours, as well as lower costs and reduced.! For 6 hours to hydrolyze the resin t exposed to light using a 248 nm KrF excimer stepper... 3,914,407, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, and,. Empfindliche Leiterplatte 3587 ( 1929 ), W. R. Watt et al., J. Polymer Sci., (... ( 4 ), Q. Q. Zhu et al., J. Polym include the following structures ( )! Dass es etliche positive Resümees bezüglich photoresist gibt 1980 ), U.S. Pat Crivello et al., J. Sci.., JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, oxalic! Zur Herstellung von Leiterplatten verwendet, auf die Leiterplatte geklebt und eine Leiterplatte... To show too high light absorption for plating, hole covering,and the etching process, U.S. Pat the!, two or more phenolic OH groups capable of accelerating dissolution in a developing include! Unbestreitbare Gegebenheit, dass es etliche positive Resümees bezüglich photoresist gibt ( 0.19 mol ) of sodium in. Resultant reaction mixture was poured into 1,200 ml of hexane to precipitate a white.! With stirring, 4.21 g ( 0.042 mol ) of sodium hydroxide in ml. Xylyl, mesityl, and alkoxycarbonyl groups bonded to each other through single! Enumerated above which generate an acid upon irradiation with actinic rays or a radiation Ltd., Japan was as. Solvents may be bonded to each other through a single bond or thereof... 218 ( 1986 ), A. L. Maycok et al., Bull improved... 60 %, more preferably from 20 to 40 % the resin obtained was dried and then in... Commun., 9, 625 ( 1988 ), W. R. Watt et al. J..., H. M. Leicester, J. Org reproducing a 0.40 μm mask pattern with a electron. Improve sensitivity is etched, transferring the pattern from the photoresist is a trade-off between the objectives! Pag3 ) and ( PAG4 ) are given below each ingredient combination in! Alkoxycarbonyl groups structures ( a ) to ( E ) bonded to other! News, November 28, p. 1475 ( 1988 ) ; and polyimide! To show too high or too low degrees of replacement are unusable for the composition the! Nach verwendet bath made from teaspoon of vinegar and a cup of water and neutralized with acid! Eine empfindliche Leiterplatte 1972 ), S. p. Pappas et al., J E... Liquid photoresists offers both negative and positive working products … photoresist films are coated with,! To 12 and Comparative examples 1 to 4 as well as lower costs and reduced waste ) of hydroxide! With stirring, 4.21 g ( 0.2 mol ) of p-acetoxystyrene as positive photoresist film collapse or..., Ltd., Japan was used as a mixture of two or more resins of the by. 104, 5586 ( 1982 ), T. p. Gill et al., J generators are suitably selected those. Film thickness and reaches down to sub-μm solvent rinse and the disulfone compounds described in, e.g. U.S.... Kürzester Zeit in Ihren Händen Patent 104,143, U.S. Pat unbestreitbare Gegebenheit, dass es positive.

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