CN114031736B - Modified phenolic resin for photoresist, preparation method thereof and photoresist composition - Google Patents
Modified phenolic resin for photoresist, preparation method thereof and photoresist composition Download PDFInfo
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- CN114031736B CN114031736B CN202111556168.7A CN202111556168A CN114031736B CN 114031736 B CN114031736 B CN 114031736B CN 202111556168 A CN202111556168 A CN 202111556168A CN 114031736 B CN114031736 B CN 114031736B
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- phenolic resin
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- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 44
- 239000005011 phenolic resin Substances 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 6
- 239000012065 filter cake Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 239000012046 mixed solvent Substances 0.000 claims description 19
- -1 cresol compound Chemical class 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 5
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 229940116333 ethyl lactate Drugs 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- QLNYTCSELYEEPV-UHFFFAOYSA-N 2,2-dimethylpropyl acetate Chemical compound CC(=O)OCC(C)(C)C QLNYTCSELYEEPV-UHFFFAOYSA-N 0.000 claims description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 4
- LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 claims description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 4
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003504 photosensitizing agent Substances 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- LLBBBYLDTDJMNU-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(O)C=C1O LLBBBYLDTDJMNU-UHFFFAOYSA-N 0.000 claims description 2
- KLNMQYHQWUWCPG-UHFFFAOYSA-N 2-anthracen-9-ylethanol Chemical compound C1=CC=C2C(CCO)=C(C=CC=C3)C3=CC2=C1 KLNMQYHQWUWCPG-UHFFFAOYSA-N 0.000 claims description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- UOSROERWQJTVNU-UHFFFAOYSA-N 9,10-bis(chloromethyl)anthracene Chemical compound C1=CC=C2C(CCl)=C(C=CC=C3)C3=C(CCl)C2=C1 UOSROERWQJTVNU-UHFFFAOYSA-N 0.000 claims description 2
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 claims description 2
- AUKRYONWZHRJRE-UHFFFAOYSA-N 9-anthrol Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=CC2=C1 AUKRYONWZHRJRE-UHFFFAOYSA-N 0.000 claims description 2
- YPNZWHZIYLWEDR-UHFFFAOYSA-N 9-naphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=C(C=CC=C3)C3=CC2=C1 YPNZWHZIYLWEDR-UHFFFAOYSA-N 0.000 claims description 2
- LUBXLGUQZVKOFP-UHFFFAOYSA-N 9-phenylanthracene Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 LUBXLGUQZVKOFP-UHFFFAOYSA-N 0.000 claims description 2
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 2
- XCHARIIIZLLEBL-UHFFFAOYSA-N Medicagenic acid 3-O-beta-D-glucoside Chemical compound C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C(O)=O)C)(C)C1=CCC2C3(C)CC(O)C4OC1OC(CO)C(O)C(O)C1O XCHARIIIZLLEBL-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- GSHJWFSWKUADLL-UHFFFAOYSA-N [8-(hydroxymethyl)anthracen-1-yl]methanol Chemical compound C1=CC(CO)=C2C=C3C(CO)=CC=CC3=CC2=C1 GSHJWFSWKUADLL-UHFFFAOYSA-N 0.000 claims description 2
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 238000012643 polycondensation polymerization Methods 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 238000004377 microelectronic Methods 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 8
- 239000004380 Cholic acid Substances 0.000 description 8
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 8
- 229960002471 cholic acid Drugs 0.000 description 8
- 235000019416 cholic acid Nutrition 0.000 description 8
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000001259 photo etching Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- AKILHCICTAEFLU-UHFFFAOYSA-N 2-hydroxy-1-(4-hydroxyphenyl)propan-1-one Chemical compound CC(O)C(=O)C1=CC=C(O)C=C1 AKILHCICTAEFLU-UHFFFAOYSA-N 0.000 description 1
- UJWRVYWLRMVCIR-UHFFFAOYSA-N 4-benzylbenzene-1,2,3-triol Chemical compound OC1=C(O)C(O)=CC=C1CC1=CC=CC=C1 UJWRVYWLRMVCIR-UHFFFAOYSA-N 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/32—Chemically modified polycondensates by organic acids or derivatives thereof, e.g. fatty oils
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Materials For Photolithography (AREA)
Abstract
The application belongs to the technical field of photoresist microelectronics chemistry, and discloses a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition, wherein the modified phenolic resin comprises a polymer structure shown in a formula I, n and m are molar ratio, n is more than or equal to 0.09 and less than or equal to 0.91,0.09 and m is less than or equal to 0.91, and n+m=1; the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following. The application improves the solubility of the phenolic resin, and simultaneously introduces the compound shown in the formula III into the side chain structure of the phenolic resin, thereby further improving the heat resistance of the phenolic resin. The photoresist composition prepared from the modified phenolic resin has excellent sensitivity and resolution.
Description
Technical Field
The application relates to the technical field of photoresist microelectronics chemistry, in particular to a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition.
Background
Photoresist is a core consumable material for integrated circuit fabrication and is also a critical factor affecting integrated circuit performance, yield and reliability. Photoresists can be classified into positive photoresists and negative photoresists according to the chemical reaction mechanism and development principle of the photoresist. The exposed areas of the positive photoresist undergo a photolytic reaction that degrades the photoresist into a substance that is soluble in the developer. The exposed areas of the negative photoresist undergo a crosslinking reaction and are insoluble in the developer, and the unexposed areas are soluble in the developer.
The G/I line photoresist uses linear phenolic resin as main resin and diazonaphthoquinone as sensitizer, and the pattern of mask is transferred and copied onto the wafer through exposure, development and other photoetching process. The linear phenolic resin has strong dry corrosion resistance and wet corrosion resistance, but the linear phenolic resin has lower glass transition temperature and insufficient heat resistance, and the heat resistance temperature of the photoresist required in most microelectronic processing technologies at the day before is 200 ℃ or higher. However, the heat resistance of the general phenolic novolac resin is insufficient, the migration of the catalyst is increased in the photoetching process, the circuit device with higher resolution cannot be met, and the conventional phenolic novolac resin can deform the photoetching pattern at a temperature higher than 140 ℃ to influence the resolution of the photoresist. In the fabrication of integrated circuits, the resolution of the photoresist directly affects the precision performance of the lithographic device. Under the condition of ensuring the quality of the pattern, improving the photoetching efficiency and resolution of the photoresist is an important point of the development of the current photoresist product formula.
Disclosure of Invention
In order to solve the technical problems, the application provides a modified phenolic resin for photoresist, a preparation method thereof and a photoresist composition.
The technical scheme of the application is as follows:
a modified phenolic resin for photoresist comprising a polymer structure of formula I:
wherein n and m are molar ratios, n is more than or equal to 0.09 and less than or equal to 0.91,0.09 and m is more than or equal to 0.91, and n+m=1;
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
Preferably, 0.1.ltoreq.n.ltoreq.0.8, more preferably 0.2.ltoreq.n.ltoreq.0.5.
A preparation method of modified phenolic resin for photoresist comprises the following steps:
(1) Under the protective atmosphere and anhydrous condition, adding the phenolic resin of the formula II, the compound of the formula III and the catalyst into an organic solvent, and uniformly stirring to react;
(2) After the reaction is finished, precipitating in water or normal hexane or water ethanol mixed solvent, filtering, drying a filter cake, dissolving the filter cake in an organic solvent, and precipitating, filtering and drying the filter cake again in water or normal hexane or water ethanol mixed solvent to obtain the modified phenolic resin for photoresist;
the phenolic resin of the formula II and the compound of the formula III have the following structures:
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
Preferably, the catalyst in step (1) is one or more of 4-Dimethylaminopyridine (DMAP), 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC), dicyclohexylcarbodiimide (DCC), N' -Carbonyldiimidazole (CDI).
Preferably, the molar ratio of the compound of formula III to phenolic resin in step (1) is from 0.2 to 0.4; the reaction temperature is 20-40 ℃ and the reaction time is 10-24 hours.
Preferably, the phenolic resin formula II is a polymer formed by condensation polymerization of cresol compounds and aldehyde compounds, wherein the cresol compounds comprise one or more of m-cresol, p-cresol, o-cresol, xylenol and tricresyl; the aldehyde compound comprises one or more of formaldehyde, acetaldehyde and propionaldehyde; the molecular weight of the phenolic resin is 1000-20000g/mol, preferably 2000-10000g/mol, more preferably 3000-8000g/mol.
Preferably, the organic solvent used in steps (1) and (2) is one or more of N, N-Dimethylformamide (DMF), N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, butyl acetate, and neopentyl acetate.
The photoresist composition comprises, by mass, 10-50 parts of the modified phenolic resin, 0.5-10 parts of a photosensitizer, 0.1-10 parts of an auxiliary agent and 60-90 parts of an organic solvent.
The sensitizer is prepared by reacting diazonaphthoquinone with a compound with a plurality of phenolic hydroxyl groups; wherein, the mol ratio of the polyphenol hydroxyl compound to the diazonaphthoquinone is 1:1-1:4, preferably 1:2-1:3.
the diazonaphthoquinone comprises 2-diazonaphthoquinone-1-naphthoquinone-4-sulfonyl chloride and 2-diazonaphthoquinone-1-naphthoquinone-5-sulfonyl chloride; the polyphenol hydroxyl compound comprises 2,3, 4-trihydroxy diphenyl methane, 2,3, 4' -tetrahydroxy diphenyl methane, 2,3, 4-trihydroxy diphenyl ketone, 2',4,4' -tetrahydroxybenzophenone, 2,3, 4' -tetrahydroxybenzophenone, 2',3, 4-tetrahydroxybenzophenone, 2,3', 4' -tetrahydroxybenzophenone. Preferred are 2,3, 4-trihydroxybenzophenone and 2,3, 4' -tetrahydroxybenzophenone.
Preferably, the sensitizer comprises one or more of the following compounds G1, G2, G3 and G4, wherein the compound G1 is prepared from 2,3, 4' -tetrahydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride in a molar ratio of 1:2, and the compound G2 is prepared by 2,3, 4' -tetrahydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:4, and the compound G3 is prepared from 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:2, and the compound G4 is prepared by 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:3, reacting to obtain the product.
The auxiliary agent comprises one or more of epoxy compounds, esters compounds, ethers compounds, polyhydroxy compounds, anthracene compounds and polymers thereof.
Preferably, the auxiliary is one or more of butyl lactate, 4- (1-isopropylidene) bis (2, 6-bisphenol), 2',4' -tetrahydroxybenzophenone, 2,3,4 '-tetrahydroxybenzophenone, 2',4 '-dihydroxypropiophenone, 2,4' -dihydroxydiphenylmethane, dibutyl phthalate, 9-anthracenol, 1, 8-bis (hydroxymethyl) anthracene, 9- (2-hydroxyethyl) anthracene, 9, 10-bis (chloromethyl) anthracene, 2-anthranilic acid, 9, 10-diphenyl anthracene, 9-phenyl anthracene, 9- (1-naphthyl) anthracene.
Preferably, the organic solvent comprises one or more of anisole, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, ethyl acetate, butyl acetate, neopentyl acetate, xylene and toluene. Preferred are one or more of propylene glycol methyl ether acetate, propylene glycol monomethyl ether and ethyl lactate.
In addition, the components of the photoresist composition may further include a leveling agent, etc., and the type and amount of the leveling agent are not particularly limited in the present application, and the leveling agent can reduce the surface tension of the photoresist composition, promote the uniform distribution of the photoresist layer prepared from the photoresist composition, and prevent spots or scars, etc.
The preparation method of the photoresist composition is not particularly limited, and may include the steps of: sequentially adding phenolic resin, a photosensitizer, a plasticizer, an additive and an organic solvent into a light-proof glassware according to the formula proportion, and vibrating for 12-96 hours in a light-proof manner to fully dissolve the materials; then filtering the photoresist solution with a filter of 0.5 μm or less; the filtrate was collected in a light-shielding glass to obtain a photoresist composition.
The resolution test method is not particularly limited: using a gumming machine to carry out gumming on a 2-inch wafer, adjusting the rotating speed of spin coating according to the thickness of the photoresist layer, and baking and hardening after the spin coating is finished to form the photoresist layer with a certain thickness; at 365nm radiation, the reticle is provided with a linewidth of 3-0.1 μm, the ratio of linewidth to grating pitch being 1:1-1:5, exposing; then, development was performed with 2.38wt% aqueous tetramethylammonium hydroxide; the minimum line width that can be clearly observed after development.
The baking hardening temperature is 50-150deg.C, the time is 0.5-5min, the preferable temperature is 90-100deg.C, and the time is 30-60s.
The development time is 10 to 180s, preferably 30 to 60s.
The photoresist composition of the present application can be applied to G-line photoresist or I-line photoresist.
The phenolic resin is the core material in the G/I line photoresist, and the application designs and synthesizes a modified phenolic resin. Compared with the prior art, the application has the following advantages:
(1) The application improves the solubility of the phenolic resin, and simultaneously introduces the compound shown in the formula III into the side chain structure of the phenolic resin, thereby further improving the heat resistance of the phenolic resin.
(2) The photoresist composition prepared from the modified phenolic resin has excellent sensitivity and resolution.
Drawings
FIG. 1 is a cross-sectional view of example 2 after exposure with a resolution of 0.35 microns.
FIG. 2 is a cross-sectional view of example 3 after exposure with a resolution of 0.45 microns.
FIG. 3 is a DSC secondary temperature rise test curve of example 7 at a temperature rise rate of 10deg.C/min.
FIG. 4 is a DSC secondary temperature rise test curve of example 8 at a temperature rise rate of 10deg.C/min.
Detailed Description
The present application will be described in further detail with reference to specific examples, but embodiments of the present application are not limited thereto, and may be performed with reference to conventional techniques for process parameters that are not specifically noted.
Example 1
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) Cholic acid (formula III), 0.5 times equivalent DBU and 20mL anhydrous DMF solvent (0.1 times equivalent of the ratio of the equivalents of hydroxyl groups of the phenolic resin to the equivalents of hydroxyl groups of the phenolic resin, all mentioned below) were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried to a filter cake. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.42, m=0.58). DSC test results showed that the glass transition temperature (T g ) Increasing from 98 ℃ to 124 ℃.
Example 2
10g of phenolic resin was charged with nitrogen(formula II, R) 1 Is H, R 2 Is CH 3 ) 0.3 times equivalent of cholic acid (formula III), 0.3 times equivalent of DCC, 0.1 times equivalent of DMAP and 20mL of anhydrous DMF solvent are added into a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake is dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.25, m=0.75). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 118 ℃.
Example 3
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.8 times equivalent of cholic acid (formula III), 0.8 times equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.69, m=0.31). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 125 ℃.
Example 4
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.1 times equivalent of cholic acid (formula III), 0.2 times equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.09, m=0.91). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 106 ℃.
Example 5
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.4 times the equivalent of cholic acid (formula III), 0.4 times the equivalentTo a reaction flask, 0.1-fold equivalent of DMAP and 20mL of anhydrous DMF solvent were added, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.35, m=0.65). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 120 ℃.
Example 6
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 1.0 times equivalent of cholic acid (formula III), 1.0 times equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.89, m=0.11). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 125 ℃.
Example 7
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.55 times equivalent of cholic acid (formula III), 5.5 times equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.49, m=0.51). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 124 ℃.
Example 8
10g of a phenolic resin (formula II, R 1 Is H, R 2 Is CH 3 ) 0.9 times equivalent of cholic acid (formula III), 5.5 times equivalent of CDI and 20mL of anhydrous DMF solvent were added to a reaction flask, stirred at room temperature for 12 hours, and mixed in water/ethanol (6/4, v/v)Precipitating in solvent, filtering, and drying filter cake. The filter cake was dissolved in tetrahydrofuran, precipitated in a water/ethanol (6/4, v/v) mixed solvent, filtered, and dried, and the procedure was repeated twice to give a modified phenolic resin (formula I, n=0.78, m=0.22). DSC test results show that the phenolic resin T g Increasing from 98 ℃ to 125 ℃.
Example 9
The modified phenolic resins and phenolic resins of examples 1 to 8 were used as main resins of photoresists, the specific components of the photoresists were 100 parts of (modified) phenolic resin, 15 parts of photosensitizer G2,0.5 part of leveling agent FC-4430,0.5 parts of crosslinking agent 2,4' -dihydroxypropiophenone dissolved in 400 parts of Propylene Glycol Methyl Ether Acetate (PGMEA), and then filtered with 0.45 μm and 0.22 μm filters, respectively, to obtain photoresist compositions. The resolution of the resulting photoresist was tested as follows: taking a wafer with silicon dioxide coated on the surface, spin-coating the photoresist obtained by the method on the surface, coating the photoresist with the thickness of 1.5 mu m, heating at 100 ℃ for 1min, and baking for hardening to form a photoresist layer with a certain thickness; at 365nm radiation, the reticle is provided with a linewidth of 3-0.1 μm, the ratio of linewidth to grating pitch being 1:1-1:5, exposing; then, the corresponding patterns were obtained by developing with 2.38% aqueous tetramethylammonium hydroxide as a developer for 60 seconds, washing and fixing with deionized water, and resolution testing was performed on the micropatterns using a scanning electron microscope, and the results are shown in Table 1 in detail.
TABLE 1
Remarks: phenolic resin of formula II, R 1 Is H, R 2 Is CH 3 。
The above examples are preferred embodiments of the present application, but the embodiments of the present application are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present application should be made in the equivalent manner, and the embodiments are included in the protection scope of the present application.
Claims (12)
1. The application of the modified phenolic resin in preparing photoresist is characterized in that the modified phenolic resin comprises a polymer structure shown in a formula I:
wherein n and m are molar ratios, n is more than or equal to 0.09 and less than or equal to 0.69,0.31 and m is more than or equal to 0.91, and n+m=1;
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
2. The use according to claim 1, wherein 0.2.ltoreq.n.ltoreq.0.4.
3. The use according to claim 1 or 2, characterized in that the preparation method of the modified phenolic resin comprises the following steps:
(1) Under the protective atmosphere and anhydrous condition, adding the phenolic resin of the formula II, the compound of the formula III and the catalyst into the organic solvent A, and uniformly stirring to react;
(2) After the reaction is finished, precipitating in water or normal hexane or water ethanol mixed solvent, filtering, drying a filter cake, dissolving the filter cake in an organic solvent A, and precipitating, filtering and drying the filter cake again in water or normal hexane or water ethanol mixed solvent to obtain the modified phenolic resin for photoresist;
the phenolic resin of the formula II and the compound of the formula III have the following structures:
the R is 1 And R is 2 H, CH each independently of the other 3 、CH 2 CH 3 、CH 2 CH 2 CH 3 One or more of the following.
4. The use according to claim 3, wherein the catalyst in step (1) is one or more of 4-dimethylaminopyridine, 1, 8-diazabicyclo [5.4.0] undec-7-ene, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, dicyclohexylcarbodiimide, N' -carbonyldiimidazole.
5. The use according to claim 4, wherein the molar ratio of the compound of formula III to phenolic resin in step (1) is from 0.2 to 0.4; the reaction temperature is 20-40 ℃ and the reaction time is 10-24 hours.
6. The use according to claim 5, wherein the phenolic resin of formula II is a polymer obtained by condensation polymerization of a cresol compound and an aldehyde compound, the cresol compound comprising one or more of m-cresol, p-cresol, o-cresol, xylenol and tricresyl; the aldehyde compound comprises one or more of formaldehyde, acetaldehyde and propionaldehyde; the molecular weight of the phenolic resin is 1000-20000g/mol.
7. The use according to claim 6, wherein the phenolic resin has a molecular weight of 2000-10000g/mol.
8. The use according to claim 7, wherein the phenolic resin has a molecular weight of 3000-8000g/mol.
9. The method according to claim 6, wherein the organic solvent A used in the steps (1) and (2) is one or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, butyl acetate and neopentyl acetate.
10. A photoresist composition, which is characterized by comprising 10-50 parts of the modified phenolic resin according to any one of claims 1-9, 0.5-10 parts of a photosensitizer, 0.1-10 parts of an auxiliary agent and 60-90 parts of an organic solvent B in mass fraction.
11. The photoresist composition according to claim 10, wherein the sensitizer comprises one or more of the following compounds G1, G2, G3 and G4, wherein the compound G1 is composed of 2,3, 4' -tetrahydroxybenzophenone and 2-diazonaphthoquinone-1-4-sulfonyl chloride in a molar ratio of 1:2, and the compound G2 is prepared by 2,3, 4' -tetrahydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:4, and the compound G3 is prepared from 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:2, and the compound G4 is prepared by 2,3, 4-trihydroxybenzophenone and 2-diazonium-1 naphthoquinone-4-sulfonyl chloride according to a molar ratio of 1:3, reacting to obtain the product.
12. The photoresist composition according to claim 10 or 11, wherein the adjuvant is one or more of butyl lactate, 4- (1-isopropylidene) bis (2, 6-bisphenol), 2',4' -tetrahydroxybenzophenone, 2,3,4 '-tetrahydroxybenzophenone, 2',4 '-dihydroxypropiophenone, 2,4' -dihydroxydiphenylmethane, dibutyl phthalate, 9-anthracenol, 1, 8-bis (hydroxymethyl) anthracene, 9- (2-hydroxyethyl) anthracene, 9, 10-bis (chloromethyl) anthracene, 2-anthranilic acid, 9, 10-diphenylanthracene, 9-phenylanthracene, 9- (1-naphthyl) anthracene;
the organic solvent B comprises one or more of anisole, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, methyl isobutyl ketone, cyclopentanone, cyclohexanone, methyl ethyl ketone, diheptanone, ethyl lactate, ethyl acetate, butyl acetate, neopentyl acetate, xylene and toluene.
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