CN113943391A - Polymer resin and synthesis method thereof, photoresist containing polymer resin, preparation method of photoresist and use method of photoresist - Google Patents
Polymer resin and synthesis method thereof, photoresist containing polymer resin, preparation method of photoresist and use method of photoresist Download PDFInfo
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- CN113943391A CN113943391A CN202111204960.6A CN202111204960A CN113943391A CN 113943391 A CN113943391 A CN 113943391A CN 202111204960 A CN202111204960 A CN 202111204960A CN 113943391 A CN113943391 A CN 113943391A
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- resin monomer
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- 239000002952 polymeric resin Substances 0.000 title claims abstract description 66
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 66
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000001308 synthesis method Methods 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 100
- 239000011347 resin Substances 0.000 claims abstract description 100
- 239000000178 monomer Substances 0.000 claims abstract description 91
- -1 alicyclic hydrocarbon Chemical class 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical group CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001976 hemiacetal group Chemical group 0.000 claims abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 11
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 claims description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 2
- QLNYTCSELYEEPV-UHFFFAOYSA-N 2,2-dimethylpropyl acetate Chemical compound CC(=O)OCC(C)(C)C QLNYTCSELYEEPV-UHFFFAOYSA-N 0.000 claims description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 2
- BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 claims description 2
- PPPFYBPQAPISCT-UHFFFAOYSA-N 2-hydroxypropyl acetate Chemical compound CC(O)COC(C)=O PPPFYBPQAPISCT-UHFFFAOYSA-N 0.000 claims description 2
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001259 photo etching Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 11
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical group CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 11
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical group CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 10
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical group C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 description 10
- 229940026455 cedrol Drugs 0.000 description 10
- PCROEXHGMUJCDB-UHFFFAOYSA-N cedrol Natural products CC1CCC2C(C)(C)C3CC(C)(O)CC12C3 PCROEXHGMUJCDB-UHFFFAOYSA-N 0.000 description 10
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 230000004913 activation Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- LBHPSYROQDMVBS-UHFFFAOYSA-N (1-methylcyclohexyl) 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC1(C)CCCCC1 LBHPSYROQDMVBS-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical group C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FMEBJQQRPGHVOR-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)CCCC1 FMEBJQQRPGHVOR-UHFFFAOYSA-N 0.000 description 1
- VBZBISQOWJYWCC-UHFFFAOYSA-N 2-(2-carboxypropan-2-yldiazenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)N=NC(C)(C)C(O)=O VBZBISQOWJYWCC-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Abstract
The invention provides a polymer resin and a synthetic method thereof, a photoresist containing the polymer resin, a preparation method and a use method of the photoresist. The polymer resin is formed by polymerizing 50-70% of a first resin monomer, 10-30% of a second resin monomer, 10-30% of a third resin monomer and 1-10% of a fourth resin monomer in percentage by mole, wherein the first resin monomer, the second resin monomer, the third resin monomer and the fourth resin monomer respectively have the following structural general formulas:
wherein R isa1、Rb1、Rc1And Rd1Each independently selected from C1-C4 alkyl or hydrogen atom, Rb2Selected from hydrogen atoms, tert-butyl ether structures or hemiacetal structures, Rc2Is C1-C4 alkyl, Rd2Is alicyclic hydrocarbon acid-sensitive group. The application also provides a synthetic method of the polymer resin, a photoresist containing the polymer resin, a preparation method of the photoresist and a use method of the photoresist. The polymer resin synthesized by the method is used for chemically amplifying the photoresist, so that the process window can be effectively improved, and the focusing depth can be improved.
Description
Technical Field
The invention relates to the technical field of chemically amplified photoresist, in particular to polymer resin and a synthetic method thereof, photoresist containing the polymer resin, a preparation method and a use method of the photoresist.
Background
The photolithography technique includes forming a resist film made of a photoresist on top of a base material, selectively exposing the resist film to light or an electron beam through a photomask having a predetermined pattern, and then developing the resist film to form a pattern having a predetermined shape in the photoresist film. A photoresist composition in which an exposed portion becomes soluble in a developing solution is called a positive photoresist, and a photoresist composition in which an exposed portion becomes insoluble in a developing solution is called a negative photoresist.
With advances in lithography, rapid advances in the field of miniaturization have resulted, which generally involve shortening the wavelength of the exposure light wave. For example, ultraviolet radiation typified by g-line and i-line radiation, to KrF excimer laser (248nm), ArF excimer laser (193 nm). In addition, the use of even shorter wavelengths, e.g. F, has also been investigated2Excimer laser (157nm), extreme ultraviolet radiation (EUV), electron beam, X-ray, and the like. These photolithography techniques, in order to realize patterns of very fine dimensions, require photoresist materials with high resolution. Chemically amplified photoresist is the predominant of these types of photoresist materials.
After comparing the conventional phenolic resin (Novolak) positive photoresist, KrF photoresist of p-hydroxystyrene resin (PHS resin) has revolutionized photoresist materials based on the concept of chemical amplification (or chemical amplification), greatly promoting the high-speed development of ICs. Because of its lower UV absorption (248nm), higher heat resistance and good adhesion, it has become the first choice for KrF application resin.
With the increasing requirements of advanced manufacturing processes and process nodes, the defects of conventional PHS-based ESCAP type resins, high activation energy resins, are further manifested, and in particular, the depth of focus DOF window needs to be further improved.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, it is an object of the present invention to provide a polymer resin, a photoresist containing the polymer resin, a method for preparing the photoresist and a method for using the photoresist, which can improve the process window and improve the depth of focus DOF.
In order to achieve the above object, a first aspect of the present invention provides a polymer resin, which is formed by polymerizing 50 to 70% of a first resin monomer, 10 to 30% of a second resin monomer, 10 to 30% of a third resin monomer, and 1 to 10% of a fourth resin monomer, in terms of total mole percentage, wherein the first resin monomer, the second resin monomer, the third resin monomer, and the fourth resin monomer have structural general formulas:
Further, at least one of the following technical characteristics is also included:
a1) the first resin monomer accounts for 60-65% of the total mole percentage;
a2) the second resin monomer accounts for 15-20% of the total mole percentage;
a3) the third resin monomer accounts for 18-20% of the total mole percentage;
a4) the fourth resin monomer accounts for 2-6% of the total mole percentage.
Further, the molar ratio of the third resin monomer to the fourth resin monomer is 3:1 to 9: 1.
Further, at least one of the following technical characteristics is also included:
b1) the first resin monomer is selected from one of the following structures:
b2) the second resin monomer is selected from one of the following structures:
b3) the third resin monomer is selected from one of the following structures:
b4) the fourth resin monomer is selected from one of the following structures:
further, at least one of the following technical characteristics is also included:
c1) the weight average molecular weight of the polymer resin is 6000-15000, preferably 11000-13000, more preferably 11700-12400;
c2) the molecular weight distribution index PDI of the polymer resin is 1.1-1.9.
In a second aspect of the present invention, a method for synthesizing a polymer resin is provided, which includes the following steps of adding a first resin monomer, a second resin monomer, a third resin monomer, a fourth resin monomer and a solvent into a reaction vessel under the protection of an inert gas, then adding an initiator for reaction, stirring for reaction for the first time, and cooling to room temperature; and then adding alkali, stirring for reaction for the second time, adding water for precipitation, filtering to obtain a filter cake, and drying the filter cake to obtain the polymer resin.
Preferably, one of the following technical features is also included: the first stirring reaction is to stir for 6-24 hours at the temperature of 60-70 ℃; the base is triethylamine; and the second stirring reaction is to stir for 6-16 hours at the temperature of 60-70 ℃.
The solvent comprises one or more of methanol, tetrahydrofuran or Propylene Glycol Methyl Ether Acetate (PGMEA);
the initiator comprises one or two of 2,2' -azobis- (2-methyl propionate) or azobisisobutyronitrile.
In a third aspect of the present invention, a photoresist is provided, which comprises the following components: 4-10 parts by mass of the polymer resin, 3-8 wt% of a photoacid generator relative to the polymer resin, 10-40 mol% of a nitrogen-containing compound relative to the photoacid generator, 0.5-2 wt% of a dye relative to the photoacid generator, and a solvent: make up to 100 parts by mass.
Polymer resin: the acetyl groups of the first resin monomer drop off during the alcoholysis reaction to form hydroxyl groups, and in the using process of the photoresist, in the range, the proper alkali solubility level, etching resistance and transparency can be obtained, and other structural units can be utilized to realize good balance. The second resin monomer is mainly used for adjusting the etching resistance and the transparency in the using process of the photoresist. The third resin monomer and the fourth resin monomer are mainly structural units derived from acrylate, and the ester structural units have the following functions: the polarity can be changed by deprotection under acidic condition, and the resin contrast can be obviously improved and the alkali solubility level of the resin can be improved by introducing proper structural units. Meanwhile, the resin compound may exhibit good photosensitivity.
Photoacid generators: which upon exposure to light generates a protonic acid (H +) that facilitates deprotection of functional units in the polymer resin having polarity changes by deprotection under acidic conditions. Structurally mainly comprises an onium salt part with a cation structure and RnSO with an anion structure3Moiety (wherein: Rn representsn C-atom structural linear or nonlinear F-containing compounds) and common nonionic photoacid.
Nitrogen-containing compounds: it is generally a basic compound, including aliphatic (or aromatic) tertiary amine compounds, and the like, and such compounds are mainly used for controlling acid diffusion and improving resolution. Any one or a mixture of many groups that have been proposed for use in photoresists for KrF excimer lasers and ArF excimer lasers can be used.
Dye: for increasing the sensitivity.
Solvent: for dissolving polymer resins, photoacid generators, nitrogen-containing compounds, and dyes.
Further, at least one of the following technical characteristics is also included: d1) the solvent is at least one selected from propylene glycol methyl ether acetate, propylene glycol methyl ether, ethyl lactate, anisole, propylene glycol monoacetate, propylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, butyl acetate, neopentyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, diacetone alcohol and gamma-butyrolactone;
d2) the photoacid generator is selected from at least one of the following structures,
d3) the dye is selected from at least one of the following structures:
d4) the nitrogen-containing compound is at least one selected from triethanolamine, tetrabutylammonium hydroxide, tris (3, 6-dioxaheptyl) amine, trioctylamine, triisopropanolamine, triethylene diamine, 2-ethyl-N, N-bis (2-ethylhexyl) -1-hexylamine, 2-phenylbenzimidazole and diphenylamine.
In a fourth aspect of the present invention, a method for preparing a photoresist is provided, which comprises the following steps: the polymer resin, the photoacid generator, the nitrogen-containing compound, the dye, and the solvent are mixed to obtain the photoresist.
In a fifth aspect of the present invention, a method for using a photoresist is provided, which comprises the following steps: coating the photoresist on a silicon wafer, and sequentially carrying out prebaking, exposure, postbaking and development to obtain a photoetching pattern; preferably, at least one of the following technical characteristics is also included:
e1) the pre-drying temperature is 110 ℃, and the pre-drying time is 90 s;
e2) the exposure energy is 20 to 25mj/m2；
e3) The post-drying temperature is 130 ℃, and the post-drying time is 90 s;
e4) the developing solution used for the development was 2.38% TMAH solution, and the time for the development was 30 seconds.
Compared with the prior art, the invention has the following beneficial effects: by introducing a new low activation energy monomer into the conventional ESCAP type resin, the process window can be effectively improved, the DOF (degree of freedom) of the focusing depth can be improved, and the focusing depth can be obviously improved by 50-100 nm.
Drawings
FIG. 1 is a process window of depth of focus at 140P270 for example 2-1 of the present invention;
FIG. 2 is a depth of focus process window at 140P270 for comparative example 2-1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings (if the drawings do not exist, the description is made for certain embodiments of the present invention, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. Unless defined otherwise, technical or scientific terms used herein shall have the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs. As used herein, the word "comprising" and similar words are intended to mean that the element or item listed before the word covers the element or item listed after the word and its equivalents, but does not exclude other elements or items.
Synthesis of Polymer resin
Example 1-1 Synthesis of Polymer resin A-2
In the synthesis of the polymer resin A-2, a first resin monomer is acetoxystyrene, a second resin monomer is styrene, a third resin monomer is tert-butyl acrylate, and a fourth resin monomer is cedrol methacrylate, which account for 60%, 20%, 18% and 2% of the total mole percentage respectively. The reaction formula is as follows:
the preparation method comprises the following steps: in a 500ml dry four-neck flask equipped with a stirrer and a condenser and protected by nitrogen, acetoxystyrene (90.0g, 0.555mol), styrene (19.3g, 0.185mol), tert-butyl acrylate (21.3g, 0.166mol), cedrol methacrylate (5.4g, 0.0186mol) and solvent methanol (140g) are added, after the reaction system is decompressed and vacuumized, nitrogen is replaced for 3 times, the reaction solution is stirred and mixed, cooled to 0 ℃, initiator V601(17g) is then added, stirred for 10 minutes, and then the temperature of the reaction system is raised to 65 ℃ and reacted for 18 hours; the reaction system was cooled to room temperature until the polymerization was completed.
Changing a system device into a distillation device, adding methanol (150g) to dilute a system, dropwise adding triethylamine (15g) and water (5g), heating the system to 62-65 ℃, reacting for 8h (in the process, acetyl in acetoxystyrene is removed to form hydroxyl), slowly adding the mixed solution dropwise into 5L of deionized water for settling to obtain a solid compound, collecting the solid compound through No. 40 filter paper, dissolving the solid compound to about 20% by using tetrahydrofuran, settling the compound by using 5L of deionized water again, and repeating the operation twice. The solid compound was collected and dried in a vacuum oven at 45 ℃ for 48h to give solid polymer resin A-2(128.2g, mass yield 83.8%, molecular weight 11900).
Example 1-2 Synthesis of Polymer resin A-3
In the synthesis of the polymer resin A-3, a first resin monomer is acetoxystyrene, a second resin monomer is styrene, a third resin monomer is tert-butyl acrylate, and a fourth resin monomer is cedrol methacrylate, which respectively account for 60%, 20%, 16% and 4% of the total mole percentage. The reaction formula is as follows:
the difference compared to polymer resin A-2 is the different loadings of t-butyl acrylate and cedrol methacrylate. Tert-butyl acrylate (19.0g, 0.148mol), cedrol methacrylate (10.7g, 0.0368mol), and other experimental conditions were unchanged to give solid polymer resin A-3(129.7g, mass yield 83.1%, molecular weight 11900).
Examples 1-3 Synthesis of Polymer resin A-4
In the synthesis of the polymer resin A-4, a first resin monomer is acetoxystyrene, a second resin monomer is styrene, a third resin monomer is tert-butyl acrylate, and a fourth resin monomer is cedrol methacrylate, which respectively account for 65%, 18%, 15% and 2% of the total mole percentage. The reaction formula is as follows:
the difference compared to polymer resin A-2 is the different amounts of styrene, t-butyl acrylate and cedrol methacrylate charged. Styrene (16.0g, 0.154mol), t-butyl acrylate (16.4g, 0.128mol), cedrol methacrylate (5.0g, 0.0172mol), and other experimental conditions were unchanged to give solid polymer resin A-4(116.3g, mass yield 80.5%, molecular weight 11800).
Examples 1-4 Synthesis of Polymer resin A-5
In the synthesis of the polymer resin A-5, a first resin monomer is acetoxystyrene, a second resin monomer is styrene, a third resin monomer is tert-butyl acrylate, and a fourth resin monomer is 2-methyl-2-adamantanol methacrylate, wherein the total mole percentages of the first resin monomer, the second resin monomer and the fourth resin monomer are respectively 60%, 20%, 18% and 2%. The reaction formula is as follows:
the difference compared to polymer resin A-2 was that cedrol methacrylate (5.4g, 0.0186mol) was replaced with 2-methyl-2-adamantanol methacrylate (4.3g, 0.0184 mol). Other experimental conditions were not changed to obtain solid polymer resin A-5(126.5g, mass yield 83.3%, molecular weight 11900).
Examples 1-5 Synthesis of Polymer resin A-6
In the synthesis of the polymer resin A-6, a first resin monomer is acetoxystyrene, a second resin monomer is styrene monomer, a third resin monomer is tert-butyl acrylate, and a fourth resin monomer is 1-methyl cyclohexyl methacrylate, wherein the total mole percentages of the first resin monomer, the second resin monomer and the fourth resin monomer are respectively 60%, 20%, 15% and 5%. The reaction formula is as follows:
compared with the polymer resin A-2, the difference is that the charging amount of tert-butyl acrylate is different, and cedrol methacrylate is replaced by 1-methyl cyclohexyl methacrylate. Tert-butyl acrylate (17.8g, 0.0.139mol) and 1-methylcyclohexyl methacrylate (8.4g, 0.0461mol) were subjected to the same experimental conditions to obtain solid polymer resin A-6(125.3g, mass yield 82.2%, molecular weight 11700).
Comparative example 1-1 Synthesis of Polymer resin A-1
In the synthesis of the polymer resin A-1, a first resin monomer is acetoxystyrene, a second resin monomer is styrene, and a third resin monomer is tert-butyl acrylate, wherein the total mole percentages of the first resin monomer, the second resin monomer and the third resin monomer are respectively 60%, 20% and 20%. The reaction formula is as follows:
the preparation method comprises the following steps: adding acetoxystyrene (90.0g, 0.555mol), styrene (19.3g, 0.185mol), tert-butyl acrylate (23.7g, 0.185mol) and solvent methanol (140g) into a 500ml dry four-neck flask equipped with a stirrer and a condenser and protected by nitrogen, vacuumizing the reaction system under reduced pressure, replacing the nitrogen for 3 times, stirring the reaction solution for mixing and dissolving, cooling to 0 ℃, adding an initiator V601(17g), stirring for 10 minutes, heating the reaction system to 65 ℃, and reacting for 18 hours; the reaction system was cooled to room temperature until the polymerization was completed.
Changing a system device into a distillation device, adding methanol (150g) to dilute a system, dropwise adding triethylamine (15g) and water (5g), heating the system to 62-65 ℃, reacting for 8h (in the process, acetyl in acetoxystyrene is removed to form hydroxyl), slowly adding the mixed solution dropwise into 5L of deionized water for settling to obtain a solid compound, collecting the solid compound through No. 40 filter paper, dissolving the solid compound to about 20% by using tetrahydrofuran, settling the compound by using 5L of deionized water again, and repeating the operation twice. The solid compound was collected and dried in a vacuum oven at 45 ℃ for 48h to give solid polymer resin A-1(122.4g, mass yield 81.6%, molecular weight 12400).
The detailed descriptions of examples 1-1 to 1-5 and comparative examples 1-1 above are collated into the following table, as shown in Table 1:
TABLE 1 statistical table of polymer resin charges
As shown in Table 1, in examples 1-1 to 1-5 and comparative example 1-1, the obtained polymer resins A-1 to A-6 had weight average molecular weights of 12400, 11900, 11800, 11900, and 11700, and molecular PDIs of 1.75, 1.73, 1.71, 1.80, 1.76, and 1.81, respectively.
Second, preparation of photoresist
1. Photoresist composition
(ii) Polymer resin
② photoacid generators
③ Nitrogen-containing compounds
C-1: tris (3,6 dioxaheptyl) amine
Solvent
S-1: propylene Glycol Methyl Ether Acetate (PGMEA)
S-2: propylene Glycol Methyl Ether (PGME)
S-3: ethyl Lactate (EL)
Dye (v)
D-1：
2. Preparation of photoresist
Adding polymer resin, a photoacid generator, a nitrogen-containing compound and a dye into a solvent, and mixing to obtain the photoresist.
EXAMPLE 2-1 Photoresist
10g of the polymer resin A-2, 0.4g of the photoacid generator B-1, 0.24g of the photoacid generator B-2, 0.13g of tris (3, 6-dioxaheptyl) amine and 0.07g of the dye D-1 were dissolved in a mixed solution of 44.59g of PGMEA, 22.30g of PGME and 22.29gEL, and mixed with stirring to obtain a resist.
Photoresists of examples 2-2 to 2-4 and comparative examples 2-1 to 2-4 were prepared according to the above-described methods, and specific values are shown in table 2 below.
TABLE 2 statistical table for photoresist feeding
3. Method for using photoresist
The positive photoresists obtained in the above examples 2-1 to 2-4 and comparative examples 2-1 to 2-4 were respectively subjected to spin coating on a Si substrate, coating with the photoresist 2400A, prebaking on a hot plate at 110 ℃ for 90s, then selectively exposing (135nm Line/Space) with a KrF exposure machine XT860M (annular0.8/0.75/0.375), then postbaking on a hot plate at 130 ℃ for 60s, developing the wafer with 2.38% TMAH developer after cooling to room temperature for 30s, and finally rinsing with deionized water for 30s to form the desired photolithographic pattern.
The evaluation of the lithography results of examples 2-1 to 2-4 and comparative examples 2-1 to 2-4 is shown in the following Table 3:
TABLE 3 depth of focus for examples and comparative examples at different reticle sizes
Wherein depth of focus (DOF) is in nm;
140P 270: represents MASK CD: 140nm, Pitch: 270 nm;
140P 280: represents MASK CD: 140nm, Pitch: 280 nm;
150P 340: represents MASK CD: 140nm, Pitch: 340 nm;
155P 380: represents MASK CD: 140nm, Pitch: 380 nm.
Depth of focus is an important parameter in measuring the exposure process window, which characterizes the quality of the imaging of the exposure system in relation to the position of the wafer surface. Within the depth of focus range, the quality of the exposure imaging can be guaranteed.
As is clear from tables 1, 2 and 3, comparative example 2-2 is a comparative example of examples 2-1 to 2-4, the low activation energy resin monomer introduced in examples 2-1, 2-2 and 2-4 is cedryl methacrylate, the focusing depths of examples 2-1, 2-2 and 2-4 are 250nm, 250nm and 250nm, the focusing depth of comparative example 2-2 is 150nm and the focusing depth is improved by 100nm under 140P270 conditions, respectively; under the condition of 140P280, 250nm, 300nm and 250nm, the focusing depth of the comparative example 2-2 is 150nm, and the focusing depth is improved by 100-150 nm; under the condition of 150P340, the focusing depth is 300nm, 300nm and 300nm, the focusing depth of the comparative example 2-2 is 200nm, and the focusing depth is improved by 100 nm; under the condition of 150P380, the focusing depth is 150nm, 200nm and 250nm, the focusing depth of comparative examples 2-2 is 150nm, and the focusing depth is improved by 0-100 nm.
The low activation energy resin monomer introduced in the examples 2-3 is 1-ethyl-cyclopentanol methacrylate, under the condition of 140P270, the focusing depth of the examples 2-3 is 300nm, the focusing depth of the comparative examples 2-2 is 150nm, and the focusing depth is improved by 150 nm; under the condition of 140P280, the focusing depth of the embodiment 2-3 is 250nm, the focusing depth of the comparative example 2-2 is 150nm, and the focusing depth is improved by 100 nm; under the condition of 150P340, the focusing depth of the embodiment 2-3 is 300nm, the focusing depth of the comparative example 2-2 is 200nm, and the focusing depth is improved by 100 nm; under the condition of 150P380, the focusing depth of the example 2-3 is 150nm, the focusing depth of the comparative example 2-2 is 150nm, and the focusing depth is improved by 0 nm.
In summary, as shown in comparative examples 2-1 to 2-4, the focus depth of the conventional ESCAP type resin ranges from 100-.
Although the embodiments of the present invention have been described in detail hereinabove, it is apparent to those skilled in the art that various modifications and variations can be made to these embodiments. However, it is to be understood that such modifications and variations are within the scope and spirit of the present invention as set forth in the following claims. Moreover, the invention as described herein is capable of other embodiments and of being practiced or of being carried out in various ways.
Claims (10)
1. A polymer resin is formed by respectively carrying out polymerization reaction on 50-70% of a first resin monomer, 10-30% of a second resin monomer, 10-30% of a third resin monomer and 1-10% of a fourth resin monomer in percentage by mole, wherein the structural general formulas of the first resin monomer, the second resin monomer, the third resin monomer and the fourth resin monomer are respectively as follows:
2. The polymer resin according to claim 1, further comprising at least one of the following technical features:
a1) the first resin monomer accounts for 60-65% of the total mole percentage;
a2) the second resin monomer accounts for 15-20% of the total mole percentage;
a3) the third resin monomer accounts for 18-20% of the total mole percentage;
a4) the fourth resin monomer accounts for 2-6% of the total mole percentage.
3. The polymer resin according to claim 2, wherein the molar ratio of the third resin monomer to the fourth resin monomer is 3:1 to 9: 1.
4. The polymer resin of claim 1, further comprising at least one of the following technical features,
b1) the first resin monomer is selected from one of the following structures:
b2) the second resin monomer is selected from one of the following structures:
b3) the third resin monomer is selected from one of the following structures:
b4) the fourth resin monomer is selected from one of the following structures:
5. the polymer resin according to claim 1, further comprising at least one of the following technical features:
c1) the weight average molecular weight of the polymer resin is 6000-15000; preferably, the weight average molecular weight of the polymer resin is 11000-13000;
c2) the molecular weight distribution index PDI of the polymer resin is 1.1-1.9.
6. A method for synthesizing polymer resin according to any one of claims 1 to 5, comprising the steps of adding the first resin monomer, the second resin monomer, the third resin monomer, the fourth resin monomer and a solvent into a reaction vessel under the protection of inert gas, then adding an initiator for reaction, stirring for reaction, and cooling to room temperature; then adding alkali, stirring for reaction, adding water for precipitation, filtering to obtain a filter cake, and drying the filter cake to obtain the polymer resin.
7. A photoresist, comprising the following components: 4 to 10 parts by mass of the polymer resin according to any one of claims 1 to 5, 3 to 8% by weight of a photoacid generator with respect to the polymer resin, 10 to 40 mol% of a nitrogen-containing compound with respect to the photoacid generator, 0.5 to 2% by weight of a dye with respect to the photoacid generator, a solvent: make up to 100 parts by mass.
8. The photoresist of claim 7, further comprising at least one of the following features:
d1) the solvent is at least one selected from propylene glycol methyl ether acetate, propylene glycol methyl ether, ethyl lactate, anisole, propylene glycol monoacetate, propylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, butyl acetate, neopentyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, diacetone alcohol and gamma-butyrolactone;
d2) the photoacid generator is selected from at least one of the following structures:
d3) the dye is selected from at least one of the following structures:
d4) the nitrogen-containing compound is at least one selected from triethanolamine, tetrabutylammonium hydroxide, tris (3, 6-dioxaheptyl) amine, trioctylamine, triisopropanolamine, triethylene diamine, 2-ethyl-N, N-bis (2-ethylhexyl) -1-hexylamine, 2-phenylbenzimidazole and diphenylamine.
9. A method for preparing the photoresist according to claim 7 or 8, comprising the steps of: mixing the polymer resin according to any one of claims 1 to 5, a photoacid generator, a nitrogen-containing compound, a dye, and a solvent to obtain the photoresist.
10. A method of using the photoresist of claim 7 or 8, comprising the steps of: coating the photoresist on a silicon wafer, and sequentially carrying out prebaking, exposure, postbaking and development to obtain a photoetching pattern; preferably, at least one of the following technical features is also included:
e1) the pre-drying temperature is 110 ℃, and the pre-drying time is 90 s;
e2) the exposure energy is 20 to 25mj/m2；
e3) The post-drying temperature is 130 ℃, and the post-drying time is 90 s;
e4) the developing solution used for the development was 2.38% TMAH solution, and the time for the development was 30 seconds.
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| CN101974121A (en) * | 2010-09-28 | 2011-02-16 | 昆山西迪光电材料有限公司 | Chemical amplified high-resolution silicon-containing I-ray ultraviolet photoresist and forming resin thereof |
| CN105237669A (en) * | 2015-09-11 | 2016-01-13 | 苏州瑞红电子化学品有限公司 | Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method |
| CN108132584A (en) * | 2017-12-22 | 2018-06-08 | 江苏汉拓光学材料有限公司 | A kind of photoetching compositions comprising poly(4-hydroxystyrene) Type of Collective object and acrylate copolymer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101974121A (en) * | 2010-09-28 | 2011-02-16 | 昆山西迪光电材料有限公司 | Chemical amplified high-resolution silicon-containing I-ray ultraviolet photoresist and forming resin thereof |
| CN105237669A (en) * | 2015-09-11 | 2016-01-13 | 苏州瑞红电子化学品有限公司 | Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method |
| CN108132584A (en) * | 2017-12-22 | 2018-06-08 | 江苏汉拓光学材料有限公司 | A kind of photoetching compositions comprising poly(4-hydroxystyrene) Type of Collective object and acrylate copolymer |
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