CN116643458A - Diamine compound, photosensitive polyimide resin composition, and preparation method and application thereof - Google Patents
Diamine compound, photosensitive polyimide resin composition, and preparation method and application thereof Download PDFInfo
- Publication number
- CN116643458A CN116643458A CN202310544455.9A CN202310544455A CN116643458A CN 116643458 A CN116643458 A CN 116643458A CN 202310544455 A CN202310544455 A CN 202310544455A CN 116643458 A CN116643458 A CN 116643458A
- Authority
- CN
- China
- Prior art keywords
- polyimide resin
- fluorine
- photosensitive polyimide
- general formula
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920001721 polyimide Polymers 0.000 title claims abstract description 249
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 247
- -1 Diamine compound Chemical class 0.000 title claims abstract description 171
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 5
- 229920001400 block copolymer Polymers 0.000 claims abstract description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 85
- 229910052731 fluorine Inorganic materials 0.000 claims description 85
- 239000011737 fluorine Substances 0.000 claims description 85
- 239000011347 resin Substances 0.000 claims description 62
- 229920005989 resin Polymers 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 238000002156 mixing Methods 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 12
- 239000002168 alkylating agent Substances 0.000 claims description 11
- 229940100198 alkylating agent Drugs 0.000 claims description 11
- 125000004427 diamine group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000012265 solid product Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 9
- 239000002184 metal Substances 0.000 abstract description 9
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 7
- 230000036211 photosensitivity Effects 0.000 abstract description 7
- 239000011368 organic material Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 145
- 230000015572 biosynthetic process Effects 0.000 description 116
- 238000003786 synthesis reaction Methods 0.000 description 116
- 239000000243 solution Substances 0.000 description 50
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 21
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 14
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000011161 development Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229940116333 ethyl lactate Drugs 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- GWGZFNRFNIXCGH-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)benzenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F GWGZFNRFNIXCGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 5
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 229940018563 3-aminophenol Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000013007 heat curing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- 238000012661 block copolymerization Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 229920005575 poly(amic acid) Polymers 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FTIZOZRCHJUWGR-UHFFFAOYSA-N 1-bromo-3-nitropropane Chemical group [O-][N+](=O)CCCBr FTIZOZRCHJUWGR-UHFFFAOYSA-N 0.000 description 2
- AWYIAICEJMLNSZ-UHFFFAOYSA-N 1-bromo-5-nitropentane Chemical group [O-][N+](=O)CCCCCBr AWYIAICEJMLNSZ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 2
- UHIDYCYNRPVZCK-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C)(C)C1=CC=C(O)C(N)=C1 UHIDYCYNRPVZCK-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- JDIAMHNYAPDMRB-UHFFFAOYSA-N 3-nitro-5-(trifluoromethyl)phenol Chemical group OC1=CC([N+]([O-])=O)=CC(C(F)(F)F)=C1 JDIAMHNYAPDMRB-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical group OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 2
- 239000005050 vinyl trichlorosilane Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- KXOXLYRTAZLDIS-MXWKQRLJSA-N (2R)-1-[(2S)-1-[(2R)-1-ethoxypropan-2-yl]oxypropan-2-yl]oxypropan-2-ol Chemical compound CCOC[C@@H](C)OC[C@H](C)OC[C@@H](C)O KXOXLYRTAZLDIS-MXWKQRLJSA-N 0.000 description 1
- OWSKJORLRSWYGK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) propanoate Chemical compound CCC(=O)OCCC(C)(C)OC OWSKJORLRSWYGK-UHFFFAOYSA-N 0.000 description 1
- KZDFOVZPOBSHDH-UHFFFAOYSA-N 1,1-diethoxy-2-methylpropane Chemical compound CCOC(C(C)C)OCC KZDFOVZPOBSHDH-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- VFFRLRQQWXGEBX-UHFFFAOYSA-N 1-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C=CC2=C1 VFFRLRQQWXGEBX-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ZRGKNKLDYARVPU-UHFFFAOYSA-N 1-ethoxypropan-2-ol;ethyl acetate Chemical compound CCOC(C)=O.CCOCC(C)O ZRGKNKLDYARVPU-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- CUEZEJLYFSYIAI-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethanol;ethyl acetate Chemical compound CCOC(C)=O.CCOCCOCCO CUEZEJLYFSYIAI-UHFFFAOYSA-N 0.000 description 1
- MTVLEKBQSDTQGO-UHFFFAOYSA-N 2-(2-ethoxypropoxy)propan-1-ol Chemical compound CCOC(C)COC(C)CO MTVLEKBQSDTQGO-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CXOWHCCVISNMIX-UHFFFAOYSA-N 2-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(N)=CC=C21 CXOWHCCVISNMIX-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GEVQWEYVCFTARO-UHFFFAOYSA-N 2-ethoxyethanol;ethyl acetate Chemical compound CCOCCO.CCOC(C)=O GEVQWEYVCFTARO-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- XRAAFZNZEZFTCV-UHFFFAOYSA-N 3-[[3-aminopropyl(diphenyl)silyl]oxy-diphenylsilyl]propan-1-amine Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(CCCN)O[Si](CCCN)(C=1C=CC=CC=1)C1=CC=CC=C1 XRAAFZNZEZFTCV-UHFFFAOYSA-N 0.000 description 1
- GIMFLOOKFCUUOQ-UHFFFAOYSA-N 3-amino-4-hydroxy-1,2-dihydropyrimidin-6-one Chemical compound NN1CN=C(O)C=C1O GIMFLOOKFCUUOQ-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- QMIJLOSXZVDDAT-UHFFFAOYSA-N 3-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=CC(N)=CC(O)=C21 QMIJLOSXZVDDAT-UHFFFAOYSA-N 0.000 description 1
- ZHVPTERSBUMMHK-UHFFFAOYSA-N 3-aminonaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(N)=CC2=C1 ZHVPTERSBUMMHK-UHFFFAOYSA-N 0.000 description 1
- YIPRQTYMJYGRER-UHFFFAOYSA-N 3-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=CC(N)=CC(C(O)=O)=C21 YIPRQTYMJYGRER-UHFFFAOYSA-N 0.000 description 1
- YOABZRCMJMKPFF-UHFFFAOYSA-N 3-triethoxysilylaniline Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC(N)=C1 YOABZRCMJMKPFF-UHFFFAOYSA-N 0.000 description 1
- YMTRNELCZAZKRB-UHFFFAOYSA-N 3-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=CC(N)=C1 YMTRNELCZAZKRB-UHFFFAOYSA-N 0.000 description 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ABJQKDJOYSQVFX-UHFFFAOYSA-N 4-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=C1 ABJQKDJOYSQVFX-UHFFFAOYSA-N 0.000 description 1
- HZVWUBNSJFILOV-UHFFFAOYSA-N 4-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=CC(O)=CC2=C1 HZVWUBNSJFILOV-UHFFFAOYSA-N 0.000 description 1
- TVTRDGVFIXILMY-UHFFFAOYSA-N 4-triethoxysilylaniline Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(N)C=C1 TVTRDGVFIXILMY-UHFFFAOYSA-N 0.000 description 1
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- FSBRKZMSECKELY-UHFFFAOYSA-N 5-aminonaphthalen-2-ol Chemical compound OC1=CC=C2C(N)=CC=CC2=C1 FSBRKZMSECKELY-UHFFFAOYSA-N 0.000 description 1
- FPKNJPIDCMAIDW-UHFFFAOYSA-N 5-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1C(O)=O FPKNJPIDCMAIDW-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- SERBLGFKBWPCJD-UHFFFAOYSA-N 6-aminonaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(N)=CC=C21 SERBLGFKBWPCJD-UHFFFAOYSA-N 0.000 description 1
- CKSZZOAKPXZMAT-UHFFFAOYSA-N 6-aminonaphthalene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(N)=CC=C21 CKSZZOAKPXZMAT-UHFFFAOYSA-N 0.000 description 1
- RYXAGNHPWGDUPR-UHFFFAOYSA-N 8-amino-1h-quinolin-2-one Chemical compound C1=C(O)N=C2C(N)=CC=CC2=C1 RYXAGNHPWGDUPR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- SWTCCCJQNPGXLQ-UHFFFAOYSA-N acetaldehyde di-n-butyl acetal Natural products CCCCOC(C)OCCCC SWTCCCJQNPGXLQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- IZRVEUZYBVGCFC-UHFFFAOYSA-N ethyl 2-hydroxyisovalerate Chemical compound CCOC(=O)C(O)C(C)C IZRVEUZYBVGCFC-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- AELWIPRGNLGYSD-UHFFFAOYSA-N ethyl acetate;1-methoxypropan-2-ol Chemical compound CCOC(C)=O.COCC(C)O AELWIPRGNLGYSD-UHFFFAOYSA-N 0.000 description 1
- IOTFKOAAMYQOBJ-UHFFFAOYSA-N ethyl acetate;2-methoxyethanol Chemical compound COCCO.CCOC(C)=O IOTFKOAAMYQOBJ-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- KPBVNLIIIPFLJH-UHFFFAOYSA-N n-(3-triethoxysilylphenyl)acetamide Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC(NC(C)=O)=C1 KPBVNLIIIPFLJH-UHFFFAOYSA-N 0.000 description 1
- ISSUVKPOXOWYKC-UHFFFAOYSA-N n-(3-trimethoxysilylphenyl)acetamide Chemical compound CO[Si](OC)(OC)C1=CC=CC(NC(C)=O)=C1 ISSUVKPOXOWYKC-UHFFFAOYSA-N 0.000 description 1
- QGDSATWEXGAHMP-UHFFFAOYSA-N n-(4-triethoxysilylphenyl)acetamide Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(NC(C)=O)C=C1 QGDSATWEXGAHMP-UHFFFAOYSA-N 0.000 description 1
- UGNSEBFFKOWYAL-UHFFFAOYSA-N n-(4-trimethoxysilylphenyl)acetamide Chemical compound CO[Si](OC)(OC)C1=CC=C(NC(C)=O)C=C1 UGNSEBFFKOWYAL-UHFFFAOYSA-N 0.000 description 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention belongs to the technical field of organic materials, and particularly relates to a diamine compound, a photosensitive polyimide resin composition, a preparation method and application thereof. The photosensitive polyimide resin composition provided by the invention comprises the following components: 100 parts of photosensitive polyimide resin, 1-50 parts of phenolic hydroxyl compound, 1-50 parts of photosensitizer, 0.001-10 parts of other auxiliary agents and 300-2000 parts of organic solvent; the photosensitive polyimide resin is a bagThe block copolymer comprises a molecular chain segment shown in a general formula (1) and a molecular chain segment shown in a general formula (2), wherein the mass ratio of the molecular chain segment shown in the general formula (1) to the molecular chain segment shown in the general formula (2) is (10:90) - (90:10). The photosensitive polyimide resin film prepared from the composition has high residual film rate and photosensitivity, and simultaneously has high metal adhesion and lower elastic modulus.
Description
Technical Field
The invention belongs to the technical field of organic materials, and particularly relates to a diamine compound, a photosensitive polyimide resin composition, a preparation method and application thereof.
Background
In recent years, development of a film for a planarization layer and a film for an insulating layer, which are prepared from a positive photosensitive polyimide resin composition developed using an alkaline aqueous solution, has been actively carried out in the field of organic Electroluminescence (EL) display technology.
In general, the composition of the positive photosensitive polyimide resin composition developed using an alkaline aqueous solution includes: resins of polyamic acid/polyimide having an ester group protection, ester compounds of naphthoquinone diazide, phenolic hydroxyl compounds, thermally crosslinked compounds, and the like. The arrangement and combination of these compounds often cannot take into account the performance index problem of the polyimide resin film, and thus the obtained polyimide resin film can only show excellent performance in one aspect or some aspects, for example, the ester compound of the added diazinonaphthoquinone can improve the dissolution rate of the exposed part of the photosensitive resin film, but if the content is too high, the development process is hindered, and the sensitivity is greatly reduced, so that researchers add various phenolic hydroxyl compounds capable of promoting the dissolution of the film into the polyimide resin composition, and although the sensitivity of the photosensitive polyimide resin film prepared by the method is obviously improved, the residual film rate, resolution and other characteristics of the film are reduced; on the other hand, the added thermal crosslinking compound can crosslink among polyimide resin molecules, so that the thermodynamic property of the film is greatly improved, but the crosslinking compound is easy to decompose at high temperature, so that a small part of small molecules remain, and the small molecules slowly volatilize in the application process of the EL display device, thereby adversely affecting the service life of the EL display device.
Patent CN 114200775a discloses a positive type polyimide resin composition, which is prepared by blending a non-fluorine-containing polyimide resin and a fluorine-containing polyimide resin, and the obtained film has high residual film rate and resolution, but the mechanical blending cannot guarantee the uniformity problem of mass production of the obtained polyimide resin composition, and the reproducibility problem of obtaining an excellent polyimide resin film; patent CN 111936552a proposes a photosensitive resin composition in which a soft aliphatic long-chain group and an aromatic group having heat resistance are introduced into a resin, and a photosensitive polyimide resin film obtained has high elongation and high heat resistance, but the polyimide resin molecular segments thus synthesized are mostly randomly copolymerized, and a photosensitive polyimide resin film having optimal performance cannot be obtained.
Therefore, how to provide a positive type photosensitive polyimide resin composition which can satisfy high sensitivity and high residual film rate and has high thermal resistance and transmittance at the same time is a great problem which is urgently needed to be solved by the person skilled in the art.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a photosensitive polyimide resin composition, and a preparation method and application thereof, wherein the photosensitive polyimide resin in the composition contains a fluorine-free molecular segment and a fluorine-containing molecular segment, so that the polarity difference is provided, and the photosensitive polyimide resin film prepared from the composition has high residual film rate and photosensitivity, and meanwhile, the photosensitive polyimide resin in the composition has a block structure, so that the prepared photosensitive polyimide resin film has high metal adhesion and lower elastic modulus; the second object of the present invention is to provide a diamine compound which can provide a diamine compound having a novel structure for a photosensitive polyimide resin film with high elongation and high permeability by optimally designing the molecular structure of the diamine compound used for synthesizing the photosensitive polyimide resin.
The invention provides a photosensitive polyimide resin composition, which comprises the following components in parts by weight:
the photosensitive polyimide resin (A) is a block copolymer comprising a molecular chain segment shown in a general formula (1) and a molecular chain segment shown in a general formula (2), and the mass ratio of the molecular chain segment shown in the general formula (1) to the molecular chain segment shown in the general formula (2) is (10:90) - (90:10). In the present invention, in view of the fact that too many molecular segments of the general formula (2) may cause a decrease in the adhesiveness between the photosensitive polyimide resin film and the base substrate, and that warpage of the film is likely to occur, too low a polarity between the molecules of the photosensitive polyimide resin is insufficient, and it is not possible to ensure that the obtained photosensitive polyimide resin film has a high residual film rate, it is more preferable that the mass ratio of the molecular segments of the general formula (1) to the molecular segments of the general formula (2) is (40:60) to (80:20).
In the present invention, the molecular segment represented by the general formula (1) and the molecular segment represented by the general formula (2) are specifically as follows:
wherein R is 1 Is a fluorine-free tetracarboxylic dianhydride residue; r is R 2 Is a fluorine-free diamine residue; r is R 3 Is a fluorine-containing tetracarboxylic dianhydride residue; r is R 4 Is a fluorine-containing diamine residue; r is R 5 And R is 6 Independently a hydrogen atom or an alkyl group; n and n 1 Independently an integer from 10 to 100000; e. f is independently an integer from 1 to 2; g is an integer from 1 to 6; p and q are independently integers from 0 to 4, and p+q > 0;
In the general formula (2), the fluorine-containing diamine residue (R 4 ) removing-NH for the fluorine-containing diamine compound of the structure represented by the general formula (3) and/or the general formula (4) 2 and-CF 3 A post residue;
wherein R is 7 And R is 8 Is methylene; t is an integer from 1 to 6.
Preferably, the fluorine-containing diamine compound(s) (formula (3) and/or formula (4)) are specifically one or more of the following compounds:
in the present invention, the fluorine-containing diamine compound (formula (3) and/or formula (4)) is more preferably:
preferably, in the general formula (2)Specifically, the structure is represented by the following general formula (5):
wherein R is 10 And R is 11 Independently a 3-or 4-valent organic group having 2 to 30 carbon atoms; r is R 9 A 3-to 6-valent organic group having 3 to 40 carbon atoms; r is R 12 And R is 13 Independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; n is n 2 Represents an integer of 100 to 5000; u and v are independently integers of 0 or 1, and u+v > 0; j is an integer of 1 or 2; k is an integer of 1 to 6.
Preferably, in the general formula (2), the fluorine-containing tetracarboxylic dianhydride residue (R 3 ) The corresponding fluorine-containing tetracarboxylic dianhydride is specifically one or more of the following compounds:
in the present invention, the fluorine-containing tetracarboxylic dianhydride residue (R 3 ) The corresponding fluorine-containing tetracarboxylic dianhydride is more preferably one or two of the following compounds:
in the general formula (1), the fluorine-free diamine residue (R 2 ) Removal of-NH for fluorine-free diamines 2 The residue preferably contains a diphenyl ether structure, and a high metal adhesion and high heat resistance cured film can be obtained by introducing the diphenyl ether structure; the fluorine-free diamine is specifically one or more of the following compounds:
in the present invention, the fluorine-free diamine is more preferably one or both of the following compounds from the viewpoint of increasing the mechanical properties of the photosensitive polyimide resin film:
preferably, in the general formula (1), the fluorine-free tetracarboxylic dianhydride residue (R 1 ) The corresponding fluorine-free tetracarboxylic dianhydride is specifically one or more of the following compounds:
in the present invention, the fluorine-free tetracarboxylic dianhydride residue (R 1 ) The corresponding fluorine-free tetracarboxylic dianhydride is more preferably one or two of the following compounds:
in the present invention, R of the general formula (2) 3 And R is 4 To which an F atom-containing group is attached. The F atom has strong electronegativity, can increase the hydrophobicity of the photosensitive polyimide resin film, inhibit the film damage during development, and is beneficial to improving the film residue rate; in addition, F atoms have a large steric hindrance, and the permeability of the polyimide resin film can be increased. The addition ratio is preferably 1 to 50% by weight, more preferably 10 to 40% by weight, and particularly 10%, 15%, 20%, 25%, 30%, 35% or 40% by weight, based on 100 parts by weight of the photosensitive polyimide resin (a).
In the present invention, the molecular segment of the general formula (1) preferably has a weight average molecular weight of 10000 to 100000, more preferably 20000 to 60000, and most preferably 30000 to 40000; the molecular weight distribution of the molecular segment represented by the general formula (1) is preferably 1.5 to 2, more preferably 1.6 to 1.75; the molecular chain segment represented by the general formula (2) preferably has a weight average molecular weight of 8000 to 80000, more preferably 10000 to 50000, and most preferably 25000 to 30000; the molecular weight distribution of the molecular segment represented by the general formula (2) is preferably 1.5 to 2, more preferably 1.6 to 1.75.
In the present invention, in order to improve the adhesiveness between the photosensitive polyimide resin film and the base substrate, a small amount of disiloxane compound is preferably copolymerized in the main chain of the photosensitive polyimide resin (a) in addition to not reducing the heat resistance of the photosensitive polyimide resin film; the disiloxane compounds include, but are not limited to, one or more of 1, 3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA), 1, 3-bis (4-anilino) tetramethyldisiloxane, 1, 3-bis (3-aminopropyl) tetraphenyldisiloxane, and 1, 3-bis (4-aminopropyl) tetramethyldisiloxane; the addition ratio of the disiloxane compound is preferably 1 to 15% by weight, more preferably 1 to 10% by weight, and particularly may be 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10% by weight, relative to 100% by weight of the photosensitive polyimide resin (a).
In the present invention, in order to control the molecular weight of the resin polymer, it is preferable to perform a capping treatment at the ends of the both end structural units of the photosensitive polyimide resin (a) through a capping group, whereby the molecular weight of the resin polymer can be controlled, the stability of the molecular chain of the resin polymer can be improved, and the preservation safety of the photosensitive polyimide resin composition can be increased; the blocking agent used is preferably a monoamine compound including, but not limited to, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 2-aminophenol, 3-aminophenol, 4-aminophenol, 3-amino-4, 6-dihydroxypyrimidine, 1-hydroxy-2-aminonaphthalene, 1-hydroxy-3-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-amino-2-hydroxynaphthalene, 2-hydroxy-3-aminonaphthalene, 2-hydroxy-4-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 1-carboxy-2-aminonaphthalene, 1-carboxy-3-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-amino-2-carboxy-naphthalene, 2-carboxy-3-amino-2-carboxy-4-amino-2-hydroxy-6-aminonaphthalene, 2-hydroxy-8-aminoquinoline, and one or more of these; the addition ratio of the blocking agent is preferably 0.5 to 20% by weight, more preferably 1 to 10% by weight, and particularly may be 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10% by weight, relative to 100% by weight of the photosensitive polyimide resin (a).
In the invention, the photosensitive polyimide resin (A) is formed by alkylation of corresponding polyamic acid, and the polyamic acid is extremely easy to be controlled in alkaline aqueous solution, difficult to be controlled, poor in stability and difficult to be stored; the proportion of carboxyl in the polymer is reduced, and an alkylating agent is added to alkylate the carboxyl into ester groups, so that the dissolution rate of the resin polymer to an alkaline aqueous solution can be adjusted, and the introduction of the ester groups in the polyamide acid can also reduce the proportion of polyimide structures in the polyimide resin film, so that the water absorption rate of the resin film is reduced, and the content of the ester groups is not excessively large, so that the dissolution of the alkaline aqueous solution is not facilitated; alkylating agents useful in the present invention include, but are not limited to, N-dimethylformamide dimethyl acetal, N-dimethylformamide diethyl acetal (DMFDEA, hereinafter DEA), N-dimethylformamide dipropylacetal, N-dimethylformamide dibutyl acetal, N, one or more of N-dimethylacetamide dimethyl acetal, N-dimethylacetamide diethyl acetal, N-dimethylformamide dibenzyl acetal, 1-dimethoxy-2-methylpropane and 1, 1-diethoxy-2-methylpropane; in order to achieve the best effect of the photosensitive polyimide resin film on the dissolution rate of the alkaline aqueous solution, the alkylating agent is preferably used in an amount of 0.5 to 3.5 times, more preferably 1.5 to 2.5 times, and particularly 1.5 times, 1.6 times, 1.7 times, 1.8 times, 1.9 times, 2 times, 2.1 times, 2.2 times, 2.3 times, 2.4 times or 2.5 times the total molar amount of the polymerized monomer-fluorine-free tetracarboxylic dianhydride and the fluorine-containing tetracarboxylic dianhydride.
In the present invention, the preparation solvent of the photosensitive polyimide resin (a) is preferably a high boiling polar aprotic organic solvent, including but not limited to one or more of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, N-dimethylisobutyramide, γ -butyrolactone, γ -valerolactone and α -methyl- γ -butyrolactone, more preferably N-methylpyrrolidone.
The photosensitive polyimide resin composition contains the phenolic hydroxyl compound (B), and the photosensitive polyimide resin composition prepared by adding the phenolic hydroxyl compound is almost insoluble in alkaline developing solution, the exposure part is very soluble in the alkaline developing solution, and the dissolution rate difference between the exposure area and the non-exposure area is obvious, so that the development process is accurately controlled, and the photosensitivity is improved; in the invention, the phenolic hydroxyl group-containing compound (B) is specifically one or more of the following compounds:
for the phenolic hydroxyl compound (B) used in the present invention, a weight average molecular weight of 100 to 800 is preferable; the proportion of the phenolic hydroxyl compound (B) to be added is preferably 1 to 50% by weight, more preferably 3 to 40% by weight, and specifically 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39% or 40% by weight based on 100% by weight of the photosensitive polyimide resin (a).
The photosensitive polyimide resin composition of the present invention contains a photosensitizer (C), and as the photosensitizer used in the present invention, an ester compound formed by bonding a phenolic hydroxyl compound and a sulfonic acid of a diazinoquinone is generally selected, wherein the diazidonaphthoquinone-4-sulfonyl ester compound and the diazidonaphthoquinone-5-sulfonyl ester compound are preferably used; from the viewpoint of improving sensitivity, a compound comprising a diazidonaphthoquinone-4-sulfonyl ester is preferable; from the viewpoints of compound stability and long-term reliability of the cured film, a compound containing a diazidonaphthoquinone-5-sulfonyl ester is preferable; the phenolic hydroxyl compound used may be the same as or different from the compound of component B; in the invention, the photosensitizer (C) is specifically one or more of the following compounds:
wherein Q is independently selected fromOr H, the curved segment indicates the connection location.
For the photosensitizer (C) used in the present invention, the weight average molecular weight is preferably 100 to 2000, more preferably 500 to 1000; the proportion of the photosensitizer (C) to be added is preferably 1 to 50% by weight, more preferably 1 to 40% by weight, and specifically may be 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39% or 40% by weight with respect to 100% by weight of the photosensitive polyimide resin (a).
In the present invention, in order to improve wettability of the photosensitive polyimide resin film with the base substrate, the other auxiliary agent (D) added to the photosensitive polyimide resin composition of the present invention preferably includes a surfactant including, but not limited to, one or more of ethanol, isopropanol, isobutanol, acetone, cyclohexanone, methyl isobutyl ketone, tetrahydrofuran, 1, 4-dioxane, ethyl lactate, and propylene glycol methyl ether acetate; the surfactant is preferably added in an amount of 0.001 to 2% by weight, more preferably 0.01 to 1.5% by weight, and particularly may be 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 1.1%, 1.2%, 1.3%, 1.4% or 1.5% by weight based on 100 parts by weight of the photosensitive polyimide resin (a).
In the present invention, in order to improve the adhesion of the photosensitive polyimide resin film to the base substrate, the other auxiliary agent (D) added to the photosensitive polyimide resin composition of the present invention preferably includes a silane coupling agent including, but not limited to, an aminosilane compound and/or a vinylsilane compound; the aminosilane compounds include, but are not limited to, one or more of 3- (trimethoxysilyl) aniline, 3- (triethoxysilyl) aniline, N- (3- (trimethoxysilyl) phenyl) acetamide, N- (3- (triethoxysilyl) phenyl) acetamide, 4- (trimethoxysilyl) aniline, 4- (triethoxysilyl) aniline, N- (4- (trimethoxysilyl) phenyl) acetamide, and N- (4- (triethoxysilyl) phenyl) acetamide; the vinyl silane compounds include, but are not limited to, one or more of vinyl trimethoxysilane, vinyl triethoxysilane, vinyl trichlorosilane, and vinyl tris (beta-methoxyethoxy) silane; the silane coupling agent is preferably added in an amount of 0.1 to 10% by weight, more preferably 0.1 to 5% by weight, and particularly may be 0.1%, 0.3%, 0.5%, 0.7%, 1%, 1.3%, 1.5%, 1.7%, 2%, 2.3%, 2.5%, 2.7%, 3%, 3.2%, 3.5%, 3.7%, 4%, 4.2%, 4.5%, 4.7% or 5% by weight to 100% by weight of the photosensitive polyimide resin (a).
In the present invention, in order to improve the coatability of the photosensitive polyimide resin film to the base substrate, the photosensitive polyimide resin composition of the present invention contains an organic solvent (E), the organic solvent (E) includes, but is not limited to, gamma-butyrolactone, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol n-propyl ether, diethylene glycol n-butyl ether, triethylene glycol methyl ether, triethylene glycol ethyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol ethyl ether, tetrahydrofuran, dioxane, methyl ethyl ketone, acetone, diisobutyl ketone, cyclohexanone, and the like 2-heptanone, 3-heptanone, diacetone alcohol, ethylene glycol methyl ether ethyl acetate, ethylene glycol ethyl ether ethyl acetate, diethylene glycol methyl ether ethyl acetate, diethylene glycol ethyl ether ethyl acetate, propylene glycol methyl ether ethyl acetate, propylene glycol ethyl ether ethyl acetate, ethyl lactate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 2-hydroxy-3-methylbutyrate, methyl 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate and xylene, preferably gamma-butyrolactone; the organic solvent (E) is preferably added in a proportion of 300 to 2000% by weight, more preferably 500 to 1500% by weight, and particularly 500%, 550%, 600%, 650%, 700%, 750%, 800%, 850%, 900%, 950%, 1000%, 1050%, 1100%, 1150%, 1200%, 1250%, 1300%, 1350%, 1400%, 1450% or 1500% by weight to 100% by weight of the photosensitive polyimide resin (a).
The invention also provides a preparation method of the photosensitive polyimide resin composition, which comprises the following steps:
mixing the photosensitive polyimide resin, the phenolic hydroxyl compound, the photosensitizer, other auxiliary agents and the organic solvent according to a proportion to obtain the photosensitive polyimide resin composition.
In the preparation method provided by the invention, the photosensitive polyimide resin is preferably prepared according to the following steps:
a) Mixing and reacting the fluorine-free diamine compound and the fluorine-free tetracarboxylic dianhydride compound in a solvent to obtain a resin solution without fluorine molecular chain segments;
b) Mixing and reacting a fluorine-containing diamine compound and a fluorine-containing tetracarboxylic dianhydride compound in a solvent to obtain a resin solution containing fluorine molecular chain segments;
step a) and step b) are not sequential;
c) Mixing the resin solution without the fluorine molecular chain segments with the resin solution with the fluorine molecular chain segments for reaction, then adding an alkylating agent for continuous reaction, and adding water to separate out a solid product to obtain the photosensitive polyimide resin.
In the preparation step of the photosensitive polyimide resin provided by the invention, in the step a), the mixing reaction is preferably carried out under the protection of nitrogen; a certain amount of disiloxane compound is preferably added to the reaction system; the temperature of the mixing reaction is preferably 60-90 ℃; the time of the mixing reaction is preferably 2-6 hours; the end point of the mixing reaction is preferably determined by measuring the weight average molecular weight (Mw) of the resin solution using a gel permeation chromatograph, and the reaction is preferably stopped when the weight average molecular weight satisfies 6000 to 40000.
In the preparation step of the photosensitive polyimide resin provided by the invention, in the step b), the mixing reaction is preferably carried out under the protection of nitrogen; a certain amount of disiloxane compound is preferably added to the reaction system; the temperature of the mixing reaction is preferably 60-90 ℃; the time of the mixing reaction is preferably 2-6 hours; the end point of the mixing reaction is preferably determined by measuring the weight average molecular weight (Mw) of the resin solution using a gel permeation chromatograph, and the reaction is preferably stopped when the weight average molecular weight satisfies 6000 to 30000.
In the preparation step of the photosensitive polyimide resin provided by the invention, in the step c), the temperature of the mixing reaction is preferably 40-50 ℃; the time of the mixing reaction is preferably 2-4 hours; after the mixing reaction is finished, a blocking agent is preferably added into the reaction system; the reaction temperature after adding the end capping agent is preferably 40-50 ℃; the reaction time after adding the end capping reagent is preferably 2-4 hours; the alkylating agent is preferably added dropwise; the dripping time is preferably 10 to 30min, more preferably 20min; the temperature of the continuous reaction after the alkylating agent is added is preferably 40-50 ℃; the time for continuing the reaction after the alkylating agent is added is preferably 2-3 hours; the reaction system is preferably cooled to room temperature before the solid product is separated out by adding water; the solid product is preferably collected by means of reduced pressure filtration; the solid product collected is preferably washed with water and dried; the number of times of water washing is preferably 2-3 times; the drying mode is preferably vacuum drying; the drying temperature is preferably 60-100 ℃, more preferably 80 ℃; the drying time is preferably 48 to 72 hours.
In the preparation method provided by the invention, in order to remove mechanical impurities and metal ions in the photosensitive polyimide resin composition, the preparation method preferably further comprises the step of filtering the uniformly mixed photosensitive polyimide resin composition; wherein the filter pore size adopted by the filtration is preferably 0.01-5 μm, more preferably one or more of 0.5 μm, 0.2 μm, 0.1 μm, 0.05 μm and 0.01 μm pore size are used together; the filter material includes, but is not limited to, polyethylene (PE), polypropylene (PP), nylon (NY) or Polytetrafluoroethylene (PTFE), preferably polyethylene.
The invention also provides a photosensitive polyimide resin film which is prepared from the photosensitive polyimide resin composition.
The preparation process of the photosensitive polyimide resin film provided by the invention preferably comprises three stages, specifically: 1) preparing a pre-baked film, 2) exposing and developing, and 3) performing heat curing treatment; the further explanation is as follows:
1) Preparing a pre-baking film: coating the photosensitive polyimide resin composition on a base substrate, and then heating and drying to prepare a pre-baked film; wherein, the coating method is preferably a slit coating method, a spin coating method, a spraying method or a printing method; the base substrate includes, but is not limited to, a silicon wafer, ceramic, glass, quartz, or ITO (indium tin oxide); the drying temperature is preferably 50-150 ℃, more preferably 80-130 ℃; the drying time is preferably 1 min-60 min; the film thickness of the pre-baked film varies depending on the solid content and viscosity of the photosensitive polyimide resin composition slurry, and is preferably 0.1 to 15. Mu.m, more preferably 5 to 10. Mu.m; the film thickness is preferably measured using a film thickness meter.
2) Exposure and development: irradiating the pre-baked film with light rays, exposing the pre-baked film with the light rays through a mask plate with a specific pattern, and washing off the exposed part with a developing solution to obtain a pre-baked film of photosensitive polyimide resin with a required pattern; among them, light rays for exposure include, but are not limited to, ultraviolet rays, visible rays, electron beams, or X-rays, preferably i-rays (365 nm), h-rays (405 nm), or g-rays (436 nm) of a mercury lamp; the developing solution used for washing the exposure part is preferably an alkaline aqueous solution, the solute preferably comprises one or more of tetramethyl ammonium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, the mass concentration is preferably 2.375-2.385%, and the developing solution is environment-friendly and suitable for industrial application.
3) And (3) heat curing: performing heat curing treatment on the pre-baked film of the photosensitive polyimide resin with the specific pattern at a certain temperature for a period of time to obtain a cured film of the photosensitive polyimide resin; wherein, the heat curing treatment process is preferably as follows: the temperature is raised stepwise at a heating rate of 2.5 ℃/min, the highest curing temperature is preferably 200-300 ℃, and the curing time is preferably 30-90 min.
The invention also provides a novel diamine compound for preparing photosensitive polyimide resin, which has a chemical structure shown in a general formula (3) or a general formula (4):
wherein R is 7 And R is 8 Is methylene; t is an integer from 1 to 6.
Compared with the prior art, the technical scheme provided by the invention at least comprises the following beneficial effects:
1. the molecular chain segment combination mode in the polyimide resin (A) is block polymerization, and the photosensitive polyimide resin obtained by the combination mode has high metal adhesion and lower elastic modulus;
2. according to the invention, the fluorine-free polyimide resin chain segments and the fluorine-containing polyimide resin chain segments are combined, and the distribution that the fluorine content is gradually increased from the substrate to the film surface is formed due to the polarity difference of the two resin chain segments, so that the photosensitive polyimide resin film can maintain high residual film rate and sensitivity during development by utilizing the hydrophobicity of the fluorine-rich atom surface and the alkali solubility of carboxylic acid, and meanwhile, the permeability of the photosensitive polyimide resin film can be increased due to the existence of fluorine atoms.
3. The invention introduces a novel fluorine-containing diamine compound containing an aromatic structure and a carbon chain into the main chain of polyimide resin (A), and the photosensitive polyimide resin film prepared from the diamine compound has high heat resistance and excellent tensile property.
4. The photosensitive polyimide resin film prepared by the invention can be applied to passivation films, surface protection films and interlayer insulating films on semiconductor element circuits of semiconductor devices, and particularly can be applied to insulating layers and planarization layers between Thin Film Transistors (TFTs) in organic electroluminescent display devices.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only embodiments of the present invention, and that other drawings can be obtained according to the provided drawings without inventive effort for a person skilled in the art.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the fluorine-containing diamine compound (I-1) in Synthesis example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the fluorine-containing diamine compound (I-17) in Synthesis example 4 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the fluorine-free tetracarboxylic dianhydride compound (IV-11) of synthesis example 7 according to the invention.
Detailed Description
The following will clearly and fully describe the aspects of the synthesis examples, examples and comparative examples of the present invention, and it is apparent that the synthesis examples, examples and comparative examples described are only some of the present invention, but not all of the synthesis examples, examples and comparative examples.
The evaluation methods of the synthesis examples, examples and comparative examples are as follows:
( 1) Gel permeation chromatography was performed on the resin solution (standard: conversion of polystyrene )
Preparing 2ml of resin solution, adding N-methyl pyrrolidone solvent, preparing the concentration of the resin solution sample to 8mg/ml, standing for 1 hour, and waiting forThe resin solution was sufficiently dissolved, and then the prepared resin solution was filtered with a 0.45 μm filter membrane, and the weight average molecular weight (M) of the resin polymer in the resin solution was started to be measured w ) And molecular weight distribution (PDI). The gel permeation chromatograph used was of the type Waters-e2695, waters, inc., U.S.; the detector model is Waters-2414, waters, USA; the chromatographic column is TSKgel ALPHA-4000, tosoh Corp; the mobile phase is N-methyl pyrrolidone solvent.
(2) Film thickness test
The thickness of the pre-baked film and the developed film of the photosensitive polyimide resin was measured using a film thickness meter (field emission scanning electron microscope, EX-30).
(3) Residual film rate test
The residual film rate is calculated according to the following formula: residual film ratio (%) =film thickness after development/film thickness of pre-baked film×100%.
(4) Sensitivity test
The pre-baked film of photosensitive polyimide resin was exposed using an exposure machine (SMA-150 GA-TR) i line (365 nm), after exposure, development was performed using a developing apparatus (AD-1200, mikasa) using an aqueous solution of tetramethylammonium hydroxide with a concentration of 2.38% as a developing solution, repeated twice, then washed with purified water, dried, and after the exposed portion was completely dissolved, the lowest exposure amount at the time of development to form a pattern was taken as sensitivity.
(5) Thermal decomposition temperature test (T) 1％ )
A10 mg sample of the photosensitive polyimide resin film was prepared, and the sample piece was heated to 150℃at a heating rate of 10℃per minute in the first stage, kept for 30 minutes, cooled to 50℃in the second stage, and heated from 50℃to 800℃at a heating rate of 10℃per minute in the third stage using a thermogravimetric analyzer (Germany, fast, TG209F 1) under a nitrogen flow. The temperature corresponding to the 1% weight loss was determined from the measured weight-temperature curve as the corresponding thermal decomposition temperature.
(6) Mechanical property test
A10 μm thick photosensitive polyimide resin film sample was prepared, a rectangular film with a size of 100mm by 10mm was produced, the film sample was stretched with a tensile tester (RTH-20-RACK 1310, japan) at a clamp pitch of 50mm, and a stress-strain curve was obtained by stretching, and mechanical properties of the film were obtained as an elastic modulus (GPa) and elongation at break (%).
(7) Light transmittance test
Ultraviolet absorbance (a) of the photosensitive resin film 1 μm thick after 250 ℃ treatment was measured using an ultraviolet-visible spectrophotometer (beijing-plague, TU-1810) at a wavelength of 400nm, and the light transmittance (T) of the resin film was calculated from lambert-beer law t=exp (-a) ×100.
(8) Cu metal adhesion evaluation
A substrate (copper-plated substrate) having a copper-plated film of a metal material layer formed by electroplating at a thickness of 2 μm was prepared by sputtering 100nm of titanium and copper on a silicon wafer, coating a photosensitive polyimide resin composition on the substrate by spin coating using a spin coater (Mikasa, japan), and heating at 120℃for 3 minutes using a heating plate (Suwang, EC-7050) to prepare a pre-baked film having a film thickness of 10. Mu.m. The pre-baked film is put into a high temperature clean furnace (CLH-21 CDV-S, japan), the temperature is raised to 250 ℃ from the room temperature in a staged way at the heating rate of 2.5 ℃/min, the heat treatment time of 250 ℃ is kept for 1h, and the temperature in the furnace is naturally cooled to below 50 ℃ to obtain the fully cured photosensitive polyimide resin film. After 10 rows and 10 columns of checkered cuts were cut at 2mm intervals on the cured film using a single blade knife, the cured film was placed in a high-temperature storage tester and stored at 150 ℃ for 500 hours, and the number of peeled lattices out of 100 lattices was counted by peeling off by Sellotape (registered trademark), thereby evaluating the adhesion between the metal material and the resin cured film. The number of peels was less than 5, evaluated as optimal, the number of peels was less than 10, evaluated as optimal, the number of peels was less than 20, evaluated as good, the number of peels was greater than 20, and evaluated as bad.
The following will describe the synthesis examples, examples and comparative examples with reference to the technical means, and the specific contents are as follows:
synthesis example 1
The synthesis of the fluorine-containing diamine compound (I-1) has the following chemical reaction formula:
2-trifluoromethyl-4-nitrophenol (0.05 mol) (CAS: 1548-61-4), bromonitromethane (0.11 mol) (CAS: 563-70-2) and CsOH.H were sequentially introduced into a 500ml three-port reaction flask under nitrogen protection 2 O (0.30 mol) (CAS: 35103-79-8) was dissolved in 150ml of DMSO solvent and reacted for 48 hours in an oil bath at 150℃and after completion of TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated, followed by purification by column chromatography to give intermediate 1 (11.44 g, yield 86%);
the intermediate 1 (0.03 mol), 5% Palladium on carbon (50% aqueous solution) (1.20 mmol) and 170ml ethylene glycol methyl ether were charged into a 500ml autoclave, and hydrogen was replaced and the autoclave was pressurized with hydrogen to bring the internal pressure of the autoclave to 10kgf/cm 2 Heating to 35 ℃, and stirring for 2h; after the reaction is finished, slowly releasing the pressure, and decompressing and filtering the reaction liquid to obtain a transparent solution; ethanol and petroleum ether were added to the solution, stirred for 12 hours to precipitate a solid, and the solid was filtered under reduced pressure to obtain a white solid, and the solid was dried in a vacuum oven at 50℃for 20 hours to obtain a fluorine-containing diamine compound (I-1) (5.07 g, yield 82%) whose nuclear magnetic resonance hydrogen spectrum is shown in FIG. 1.
Synthesis example 2
The synthesis of the fluorine-containing diamine compound (I-3) has the following chemical reaction formula:
synthesis example 1 was different in that bromonitromethane (0.11 mol) (CAS: 563-70-2) was replaced with 1-bromo-3-nitropropane (0.11 mol) (CAS: 16694-53-4), and other components and synthesis conditions were unchanged, to obtain a fluorine-containing diamine compound (I-3) (5.55 g, yield 79%).
Synthesis example 3
The synthesis of the fluorine-containing diamine compound (I-5) has the following chemical reaction formula:
synthesis example 1 was different from Synthesis example 1 in that bromonitromethane (0.11 mol) (CAS: 563-70-2) was replaced with 1-bromo-5-nitropentane (0.11 mol) (CAS: 82655-19-4), and other components and synthesis conditions were unchanged, to obtain a fluorine-containing diamine compound (I-5) (5.90 g, yield 75%).
Synthesis example 4
The synthesis of the fluorine-containing diamine compound (I-17) has the following chemical reaction formula:
the difference from synthesis example 3 was that 2-trifluoromethyl-4-nitrophenol (0.05 mol) (CAS: 1548-61-4) was replaced with 3-nitro-5- (trifluoromethyl) phenol (0.05 mol) (CAS: 349-57-5), and the other components and synthesis conditions were unchanged, to obtain a fluorine-containing diamine compound (I-17) (4.96 g, yield 63%) whose nuclear magnetic resonance hydrogen spectrum was shown in FIG. 2.
Synthesis example 5
The synthesis of the fluorine-free diamine compound (D-1) has the following chemical reaction formula:
The difference from synthesis example 3 was that 2-trifluoromethyl-4-nitrophenol (0.05 mol) (CAS: 1548-61-4) was replaced with p-nitrophenol (0.05 mol) (CAS: 100-02-7), and the other components and synthesis conditions were unchanged, to obtain a fluorine-free diamine compound (D-1) (4.78 g, yield 82%).
Synthesis example 6
The synthesis of the fluorine-containing tetracarboxylic dianhydride compound (II-4) has the chemical reaction formula as follows:
2, 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (BAHF) (0.05 mol) (CAS: 83558-87-6) and allyl glycidyl ether (0.3 mol) (CAS: 106-92-3) were added to a 1L three-port reaction flask at normal temperature, and dissolved in gamma-butyrolactone (GBL) (100 g), and the reaction system was cooled to-15 ℃; then, slowly dropwise adding trimellitic anhydride acyl chloride (0.11 mol) (CAS: 1204-28-0) dissolved in 50g of gamma-butyrolactone (GBL) into the mixture, ensuring that the temperature of the reaction liquid does not exceed 0 ℃ in the dropwise adding process, continuously reacting for 5 hours below 0 ℃ after the dropwise adding is finished, and naturally heating to room temperature; the obtained reaction solution was concentrated by a rotary evaporator, and then poured into 1L of toluene to precipitate, and after filtration, the solid was dried in a vacuum oven at 60℃for 24 hours to obtain 27.15g (yield: 76%) of a fluorine-containing tetracarboxylic dianhydride compound (II-4).
Synthesis example 7
The synthesis of the fluorine-free tetracarboxylic dianhydride compound (IV-11) has the following chemical reaction formula:
2, 2-bis (3-amino-4-hydroxyphenyl) propane (0.05 mol) (CAS: 1220-78-6) and allyl glycidyl ether (0.3 mol) (CAS: 106-92-3) were added into a 1L three-port reaction flask at normal temperature, and dissolved in 100g of gamma-butyrolactone (GBL), and the reaction system was cooled to-15 ℃; then, slowly dropwise adding trimellitic anhydride acyl chloride (0.11 mol) (CAS: 1204-28-0) dissolved in 50g of gamma-butyrolactone (GBL) into the mixture, ensuring that the temperature of the reaction liquid does not exceed 0 ℃ in the dropwise adding process, continuously reacting for 5 hours below 0 ℃ after the dropwise adding is finished, and naturally heating to room temperature; the obtained reaction solution was concentrated by a rotary evaporator, and then poured into 1L of toluene to precipitate, and after filtration, the solid was dried in a vacuum oven at 60℃for 24 hours to obtain 23.96g (yield 79%) of a fluorine-free tetracarboxylic dianhydride compound (IV-11) whose nuclear magnetic resonance hydrogen spectrum is shown in FIG. 1.
Synthesis example 8
Synthesis of photosensitizer naphthaquinone diazide compound (VI-3)
1, 1-tris (4-hydroxyphenyl) ethane (V-2) (0.05 mol) (CAS: 27955-94-8), 1, 2-naphthoquinone-2-diazide-5-sulfonyl chloride (0.125 mol) (CAS: 1001756-09-7) and 1, 4-dioxane (450 g) were added to a 1L reaction flask at room temperature, stirring was started, nitrogen was replaced, and stirring was performed until complete dissolution; to this was slowly added dropwise a mixture of triethylamine (0.135 mol) and 1, 4-dioxane (45 g), after the completion of the addition, the temperature was raised to 35℃and the reaction was carried out for 4 hours, after the completion of the addition, the filtrate was filtered under reduced pressure, 3L of water was added dropwise to the filtrate, and the precipitated solid was collected by filtration, and finally the precipitate was repeatedly washed 2 times with 10L of purified water and dried in a vacuum oven at 50℃for 24 hours to obtain a photosensitizer naphthoquinone diazide compound (VI-3) as shown in the following formula:
Synthesis example 9
Synthesis of polyimide resin (A-1)
150g N-methylpyrrolidone (NMP), 4' -diaminodiphenyl ether (III-1) (15 mmol) (CAS: 101-80-4) and 1, 3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) (2.5 mmol) (CAS: 2469-55-8) were sequentially added to a dry three-necked flask under nitrogen atmosphere, the temperature was raised to 60℃and the non-fluorocarboxylic dianhydride compound (IV-11) (30 mmol) and 20g NMP in Synthesis example 7 were added for 5 hours, and the weight average molecular weight (M) of the resin polymer in the resin solution was measured by gel permeation chromatograph w ) Stopping the reaction when the weight average molecular weight is 30000-40000, and preparing a resin solution 1 without fluorine molecular chain segments;
150g N-methylpyrrolidone (NMP), the fluorine-containing diamine compound (I-5) (20 mmol) in Synthesis example 3 and 1, 3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) (2.5 mmol) were sequentially added to a dry three-necked flask under the protection of nitrogen, the temperature was raised to 60℃and the fluorine-containing tetracarboxylic dianhydride compound (II-4) (20 mmol) in Synthesis example 6 and 20g of NMP were added for 3 hours, and the weight average molecular weight (M) of the resin polymer in the resin solution was measured by gel permeation chromatograph w ) Stopping the reaction when the weight average molecular weight reaches 20000-30000, and preparing a resin solution 2 containing fluorine molecular chain segments;
Mixing resin solution 1 (100% by weight) and resin solution 2 (100% by weight) in the same dry reaction bottle, reacting for 3h at 50 ℃, adding 3-aminophenol (10 mmol) (CAS: 591-27-5) and 10g NMP as end-capping agents, continuing to react for 2h, dropwise adding alkylating agent N, N-dimethylformamide diethyl acetal (DEA) (77.5 mmol) (CAS: 1188-33-6) and 10g NMP within 20 min after the reaction is completed, and continuing to stir for 3h; then, the reaction solution was cooled to room temperature, the solution was slowly added to 2L of purified water, a white solid was precipitated, the solid was collected by filtration under reduced pressure, washed 2 times with purified water, and then dried in a vacuum oven at 80℃for 48 hours to obtain 85.62g of a polyimide resin (A-1).
Synthesis example 10
Synthesis of polyimide resin (A-2)
The difference from synthesis example 9 was that the molar ratio of 4,4' -diaminodiphenyl ether (III-1) was adjusted to (19 mmol), the molar ratio of the fluorine-free tetracarboxylic dianhydride compound (IV-11) was adjusted to (26 mmol), the molar ratio of the fluorine-containing diamine compound (I-5) was adjusted to (16 mmol), and the molar ratio of the fluorine-containing tetracarboxylic dianhydride compound (II-4) was adjusted to (24 mmol), and other components and synthesis conditions were unchanged, to obtain 82.81g of a polyimide resin (A-2).
Synthesis example 11
Synthesis of polyimide resin (A-3)
The difference from synthesis example 9 was that the molar ratio of 4,4' -diaminodiphenyl ether (III-1) was adjusted to (23 mmol), the molar ratio of the fluorine-free tetracarboxylic dianhydride compound (IV-11) was adjusted to (22 mmol), the molar ratio of the fluorine-containing diamine compound (I-5) was adjusted to (12 mmol), and the molar ratio of the fluorine-containing tetracarboxylic dianhydride compound (II-4) was adjusted to (28 mmol), and other components and synthesis conditions were unchanged, to obtain 85.36g of a polyimide resin (A-3).
Synthesis example 12
Synthesis of polyimide resin (A-4)
The difference from synthesis example 9 was that the molar ratio of 4,4' -diaminodiphenyl ether (III-1) was adjusted to (27 mmol), the molar ratio of the fluorine-free tetracarboxylic dianhydride compound (IV-11) was adjusted to (18 mmol), the molar ratio of the fluorine-containing diamine compound (I-5) was adjusted to (8 mmol) and the molar ratio of the fluorine-containing tetracarboxylic dianhydride compound (II-4) was adjusted to (32 mmol), and the other components and synthesis conditions were unchanged, to obtain 81.45g of a polyimide resin (A-4).
Synthesis example 13
Synthesis of polyimide resin (A-5)
The difference from synthesis example 9 was that the molar ratio of 4,4' -diaminodiphenyl ether (III-1) was adjusted to (31 mmol), the molar ratio of the fluorine-free tetracarboxylic dianhydride compound (IV-11) was adjusted to (14 mmol), the molar ratio of the fluorine-containing diamine compound (I-5) was adjusted to (4 mmol), and the molar ratio of the fluorine-containing tetracarboxylic dianhydride compound (II-4) was adjusted to (36 mmol), and other components and synthesis conditions were unchanged, to obtain 89.02g of a polyimide resin (A-5).
Synthesis example 14
Synthesis of polyimide resin (A-6)
The difference from synthesis example 11 was that the mixing ratio of resin solution 1 (100% by weight) and resin solution 2 (100% by weight) was adjusted to be the mixing ratio of resin solution 1 (80% by weight) and resin solution 2 (20% by weight), and 78.87g of polyimide resin (A-6) was obtained without changing other components and synthesis conditions.
Synthesis example 15
Synthesis of polyimide resin (A-7)
The difference from synthesis example 11 was that the mixing ratio of resin solution 1 (100% by weight) and resin solution 2 (100% by weight) was adjusted to be the mixing ratio of resin solution 1 (60% by weight) and resin solution 2 (40% by weight), and 78.87g of polyimide resin (A-7) was obtained without changing other components and synthesis conditions.
Synthesis example 16
Synthesis of polyimide resin (A-8)
The difference from synthesis example 11 was that the mixing ratio of resin solution 1 (100% by weight) and resin solution 2 (100% by weight) was adjusted to be the mixing ratio of resin solution 1 (40% by weight) and resin solution 2 (60% by weight), and 78.87g of polyimide resin (A-8) was obtained without changing other components and synthesis conditions.
Synthesis example 17
Synthesis of polyimide resin (A-9)
The difference from synthesis example 15 was that 83.72g of a polyimide resin (A-9) was obtained by substituting the fluorine-containing diamine compound (I-5) (20 mmol) with the fluorine-containing diamine compound (I-1) (20 mmol) in the same amount, and the other components and synthesis conditions were unchanged.
Synthesis example 18
Synthesis of polyimide resin (A-10)
The difference from synthesis example 15 was that 82.19g of a polyimide resin (A-10) was obtained by substituting the fluorine-containing diamine compound (I-5) (20 mmol) with the fluorine-containing diamine compound (I-3) (20 mmol) in the same amount, and the other components and synthesis conditions were unchanged.
Synthesis example 19
Synthesis of polyimide resin (A-11)
The difference from synthesis example 15 was that 82.19g of a polyimide resin (A-11) was obtained by substituting the fluorine-containing diamine compound (I-5) (20 mmol) with the fluorine-containing diamine compound (I-17) (20 mmol) in the same amount, and the other components and synthesis conditions were unchanged.
Synthesis example 20
Synthesis of polyimide resin (A-12)
The difference from Synthesis example 9 was that the fluorine-containing diamine compound (I-5) (20 mmol) was replaced with the fluorine-free diamine compound (D-1) (20 mmol) in Synthesis example 5 in an amount of the same substances, the fluorine-containing tetracarboxylic dianhydride compound (II-4) (20 mmol) in Synthesis example 6 was replaced with the 3,3', 4' -biphenyltetracarboxylic dianhydride (IV-2) (20 mmol) (CAS: 2420-87-3) in an amount of the same substances, and other components and synthesis conditions were unchanged, to give 78.69g of a polyimide resin (A-12).
Synthesis example 21
Synthesis of polyimide resin (A-13)
The difference from synthesis example 9 was that no fluorine-containing diamine compound (I-5) (20 mmol) was added and other components and synthesis conditions were not changed, to obtain 75.42g of polyimide resin (A-13).
Synthesis example 22
Synthesis of polyimide resin (A-14)
300g N-methylpyrrolidone (NMP), 4' -diaminodiphenyl ether (III-1) (15 mmol) (CAS: 101-80-4), the fluorine-containing diamine compound (I-5) (20 mmol) in Synthesis example 3 and 1, 3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) (5 mmol) (CAS: 2469-55-8) were successively added to a dry three-necked flask under nitrogen atmosphere, the temperature was raised to 60 ℃, the fluorine-free tetracarboxylic dianhydride compound (IV-11) (30 mmol) in Synthesis example 7, the fluorine-containing tetracarboxylic dianhydride compound (II-4) (20 mmol) in Synthesis example 6 and 40g NMP were added, the reaction was continued for 3 hours, the 3-aminophenol (10 mmol) (CAS: 591-27-5) and 10g NMP as a capping reagent, and after the reaction was completed, the alkylating agent N, N-dimethylformamide Diethylacetal (DEA) (77.5 mmol) (CAS: 8-33-6) and 10g NMP were added dropwise over 20 minutes, and stirring was continued for 3 hours; then, the reaction solution was cooled to room temperature, the solution was slowly added to 2L of purified water, a white solid was precipitated, the solid was collected by filtration under reduced pressure, washed 2 times with purified water, and then dried in a vacuum oven at 80℃for 48 hours to give 73.26g of a polyimide resin (A-14).
Synthesis example 23 Synthesis of polyimide resin (A-15)
300g N-methylpyrrolidone (NMP), 4' -diaminodiphenyl ether (III-1) (15 mmol) (CAS: 101-80-4), the non-fluorinated diamine compound (D-1) (20 mmol) in Synthesis example 5 and 1, 3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) (5 mmol) (CAS: 2469-55-8) were sequentially added to a dry three-necked flask under nitrogen atmosphere, the temperature was raised to 60 ℃, the non-fluorinated tetracarboxylic dianhydride compound (IV-11) (30 mmol) in Synthesis example 7, 3', 4' -biphenyltetracarboxylic dianhydride (IV-2) (20 mmol) and 40g NMP were added, the reaction was continued for 3 hours, the capping agent 3-aminophenol (10 mmol) (CAS: 591-27-5) and 10g NMP were added, the alkylating agent N, N-dimethylformamide Diethylacetal (DEA) (77.5 mmol) (1188-33-6) and 10g were added dropwise after the completion of the reaction for 20 minutes, and stirring was continued for 3 hours; then, the reaction solution was cooled to room temperature, the solution was slowly added to 2L of purified water, a white solid was precipitated, the solid was collected by filtration under reduced pressure, washed 2 times with purified water, and then dried in a vacuum oven at 80℃for 48 hours to give 77.25g of a polyimide resin (A-15).
The components and amounts of the polyimide resins (A-1) to (A-15) are shown in Table 1 below.
Table 1: components and amounts of polyimide resins (A-1 to 15)
Example 1
Under the protection of nitrogen, 10g of polyimide resin (A-1), 1.38g of phenolic hydroxyl compound (V-4) (CAS: 110726-28-8) and 3.52g of photosensitizer diazinonaphthoquinone compound (VI-3) in Synthesis example 8 were respectively added to 120g of gamma-butyrolactone (GBL), stirred at 25 ℃ until completely dissolved, reacted for 6 hours, 0.13g of silane coupling agent compound vinyltrichlorosilane (CAS: 75-94-5) and 0.05g of Ethyl Lactate (EL) were added, stirring was continued for 2 hours until the reaction was completed, and the reaction solution was filtered through a filter having a pore diameter of 0.01 μm made of Polyethylene (PE) to obtain a photosensitive polyimide resin composition (S-1).
Coating the filtered photosensitive polyimide resin composition (S-1) on a 6-inch silicon wafer by a spin coating method, drying for 3min at 120 ℃, and measuring the film thickness of a pre-baked film by using a film thickness meter; next, the pre-baked film was exposed through a mask plate using an i-line (365 nm) of a mercury lamp, the exposed portion was dissolved using a tetramethylammonium hydroxide developer having a mass concentration of 2.38% to obtain a pre-baked film of a photosensitive polyimide resin having a specific pattern, after development, the pre-baked film of the photosensitive polyimide resin was put into a high temperature cleaning oven (CLH-21 CDV-S, japan), heated to 150 ℃ and 200 ℃ at a heating rate of 2.5 ℃/min for 10 minutes each, finally heated to 250 ℃, heat-treated for 1 hour at 250 ℃, and cooled to 50 ℃ or less to obtain a cured film (F-1) of the photosensitive polyimide resin.
Example 2
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-2) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-2) and a cured film (F-2) of the photosensitive polyimide resin.
Example 3
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-3) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-3) and a cured film (F-3) of the photosensitive polyimide resin.
Example 4
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-4) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-4) and a cured film (F-4) of the photosensitive polyimide resin.
Example 5
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-5) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-5) and a cured film (F-5) of the photosensitive polyimide resin.
Example 6
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-6) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-6) and a cured film (F-6) of the photosensitive polyimide resin.
Example 7
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-7) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-7) and a cured film (F-7) of the photosensitive polyimide resin.
Example 8
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-8) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-8) and a cured film (F-8) of the photosensitive polyimide resin.
Example 9
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-9) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-9) and a cured film (F-9) of the photosensitive polyimide resin.
Example 10
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-10) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-10) and a cured film (F-10) of the photosensitive polyimide resin.
Example 11
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-11) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-11) and a cured film (F-11) of the photosensitive polyimide resin.
Example 12
The difference from example 1 was that the polyimide resin (A-1) was replaced with an equal mass of the polyimide resin (A-7), and the mass of the photosensitizer, the naphthoquinone diazide compound (VI-3), was replaced with 4.52g from 3.52g, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-12) and a cured film (F-12) of the photosensitive polyimide resin.
Example 13
The difference from example 1 was that the polyimide resin (A-1) was replaced with an equal mass of the polyimide resin (A-7), and the mass of the photosensitizer, the naphthoquinone diazide compound (VI-3), was replaced with 5.52g from 3.52g, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-13) and a cured film (F-13) of the photosensitive polyimide resin.
Example 14
The difference from example 1 was that the polyimide resin (A-1) was replaced with the polyimide resin (A-7) of equal mass, the phenolic hydroxyl compound (V-4) (CAS: 110726-28-8) was replaced with 2.38g from 1.38g in mass, and other components and synthesis conditions were unchanged, to obtain the photosensitive polyimide resin composition (S-14) and the cured film (F-14) of the photosensitive polyimide resin.
Example 15
The difference from example 1 was that the polyimide resin (A-1) was replaced with the polyimide resin (A-7) of equal mass, the phenolic hydroxyl compound (V-4) (CAS: 110726-28-8) was replaced with 3.38g from 1.38g in mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-15) and a cured film (F-15) of the photosensitive polyimide resin.
Comparative example 1
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-12) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-16) and a cured film (F-16) of the photosensitive polyimide resin.
Comparative example 2
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-13) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-17) and a cured film (F-17) of the photosensitive polyimide resin.
Comparative example 3
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-14) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-18) and a cured film (F-18) of the photosensitive polyimide resin.
Comparative example 4
The difference from example 1 is that the polyimide resin (A-1) was replaced with a polyimide resin (A-15) of equal mass, and other components and synthesis conditions were unchanged, to obtain a photosensitive polyimide resin composition (S-19) and a cured film (F-19) of the photosensitive polyimide resin.
Weight average molecular weight (M) of resin Polymer in photosensitive polyimide resin solution w ) And molecular weight distribution (PDI) are shown in table 2 below.
Table 2: weight average molecular weight of resin Polymer (M w ) And molecular weight distribution (PDI)
The residual film ratio of the pre-baked film of the photosensitive polyimide resin, and the thermodynamic properties, optical properties and Cu metal adhesion of the cured films (F-1 to 19) of the photosensitive polyimide resin were tested and evaluated, and the results are shown in table 3 below.
Table 3: performance test data of photosensitive polyimide resin film
/>
As is clear from the comparison of examples 1 to 5, the molar ratio of the acid anhydride compound and the diamine compound of the fluorine-containing segment in the polyimide resin is changed while the parts by weight of the fluorine-containing molecular segment and the fluorine-containing molecular segment in the polyimide resin are not changed, and from the data, the content of fluorine element is increased along with the molar ratio of the acid anhydride compound and the diamine compound from low to high, and although the residual film rate of the photosensitive polyimide resin film is very high, the Cu metal adhesion of the film is gradually reduced due to the excessive fluorine content, the mechanical property is gradually reduced after the increase, and the photosensitive polyimide resin film shows more excellent thermodynamic property and photosensitive property when the molar ratio of the fluorine-containing acid anhydride compound to the fluorine-containing diamine compound is 7:3.
As is clear from the comparison between examples 6 to 8 and example 3, the molar ratio of the acid anhydride compound and the diamine compound in the polyimide resin was controlled to be unchanged, and the weight parts of the fluorine-free molecular segment and the fluorine-containing molecular segment in the polyimide resin were changed, so that the results showed that: with the decrease of the number of the fluorine-free molecular chain segments and the increase of the number of the fluorine-containing molecular chain segments, the residual film rate and the transmittance of the formed resin film are gradually increased, but the Cu metal adhesion of the resin film is obviously reduced, and when the weight ratio of the fluorine-free molecular chain segments to the fluorine-containing molecular chain segments is 60 percent to 40 percent, the photosensitive polyimide resin film has more excellent and balanced comprehensive performance.
From comparison of examples 9, 10 and example 7, it is found that the length of the novel long chain diamine compound segment is changed to control the length of the molecular chain in the polyimide resin, and we found that: the longer the molecular segment of the polyimide resin is, the lower the modulus of elasticity of the photosensitive polyimide resin film is, the higher the elongation at break is, and the heat resistance is slightly poor.
As is clear from the comparison between example 11 and example 7, the polyimide resin film formed by changing the position of the diamine group (from para to meta) in the novel long-chain diamine compound has reduced heat resistance and mechanical properties.
As is clear from comparison of examples 12, 13 and example 7, as the amount of the photosensitive agent naphthoquinone diazide compound increases, the residual film rate of the resin film increases, and the sensitivity of the corresponding resin film decreases.
As is clear from the comparison of examples 14, 15 and example 7, the film residue ratio of the resin film was significantly reduced with the increase in the amount of the phenolic hydroxyl compound, and the corresponding thermodynamic properties were also significantly reduced.
As is clear from comparison of comparative example 1 and example 7, the block polymerization mode of the polyimide resin molecule segment is controlled to be unchanged, the whole polyimide resin molecule does not contain fluorine element, the residual film rate and the transmittance of the resin film are greatly reduced, the photosensitivity is obviously reduced, and the existence of fluorine element plays an important role in the performance of the resin film.
As is clear from the comparison between comparative example 2 and example 7, the novel diamine compound of the present invention was not added, the block polymerization system of the polyimide resin molecular segment was not changed, the mechanical properties of the resin film were remarkably reduced, and the residual film rate and the photosensitivity were reduced.
As is clear from comparison of comparative example 3 and example 7, the polymerization mode of the polyimide resin molecular chain segment is changed from block copolymerization to random copolymerization, and the elastic modulus of the resin film is improved, but the Cu metal adhesion of the film is greatly reduced, which indicates that the polymerization mode of the polyimide resin molecular chain segment plays an important role in the performance of the resin film.
As can be seen from comparison of comparative example 4 and example 7, the polymerization mode of the polyimide resin molecular chain segment is changed from block copolymerization to random copolymerization, and the whole polyimide resin molecule does not contain fluorine element, the synthesis method is similar to the common method in the market, and the result shows that: the residual film rate, the transmittance and the photosensitivity of the synthetic resin film are all superior to those of resin films synthesized by the method in the market.
In summary, the novel diamine compound and the synthesized polyimide resin molecules are polymerized in a block copolymerization mode, so that the positive photosensitive polyimide resin film with high photosensitivity and high residual film rate and high thermal resistance and transmittance can be completely obtained.
With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.
Claims (10)
1. The photosensitive polyimide resin composition is characterized by comprising the following components in parts by weight:
The photosensitive polyimide resin is a block copolymer comprising a molecular chain segment shown in a general formula (1) and a molecular chain segment shown in a general formula (2), wherein the mass ratio of the molecular chain segment shown in the general formula (1) to the molecular chain segment shown in the general formula (2) is (10:90) - (90:10);
wherein R is 1 Is a fluorine-free tetracarboxylic dianhydride residue; r is R 2 Is a fluorine-free diamine residue; r is R 3 Is a fluorine-containing tetracarboxylic dianhydride residue; r is R 4 Is a fluorine-containing diamine residue; r is R 5 And R is 6 Independently a hydrogen atomA child or alkyl group; n and n 1 Independently an integer from 10 to 100000; e. f is independently an integer from 1 to 2; g is an integer from 1 to 6; p and q are independently integers from 0 to 4, and p+q > 0;
the fluorine-containing diamine residue is removed-NH by the fluorine-containing diamine compound with the structure shown in the general formula (3) and/or the general formula (4) 2 and-CF 3 A post residue;
wherein R is 7 And R is 8 Is methylene; t is an integer from 1 to 6.
2. The photosensitive polyimide resin composition according to claim 1, wherein the fluorine-containing diamine compound is specifically one or more of the following compounds:
3. the photosensitive polyimide resin composition according to claim 1, wherein the compound represented by the general formula (2)Specifically, the structure is represented by the following general formula (5):
wherein R is 10 And R is 11 Independently a 3-or 4-valent organic group having 2 to 30 carbon atoms; r is R 9 A 3-to 6-valent organic group having 3 to 40 carbon atoms; r is R 12 And R is 13 Independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; n is n 2 Represents an integer of 100 to 5000; u and v are independently integers of 0 or 1, and u+v > 0; j is an integer of 1 or 2; k is an integer of 1 to 6.
4. The photosensitive polyimide resin composition according to claim 1, wherein the fluorine-containing tetracarboxylic dianhydride corresponding to the fluorine-containing tetracarboxylic dianhydride residue is specifically one or more of the following compounds:
5. the photosensitive polyimide resin composition according to claim 1, wherein the fluorine-free diamine residue is fluorine-free diamine-removed-NH 2 The residue is one or more of the following compounds:
6. the photosensitive polyimide resin composition according to claim 1, wherein the fluorine-free tetracarboxylic dianhydride corresponding to the fluorine-free tetracarboxylic dianhydride residue is specifically one or more of the following compounds:
7. a method for producing the photosensitive polyimide resin composition according to any one of claims 1 to 6, comprising the steps of:
Mixing the photosensitive polyimide resin, the phenolic hydroxyl compound, the photosensitizer, other auxiliary agents and the organic solvent to obtain the photosensitive polyimide resin composition.
8. The method of claim 8, wherein the photosensitive polyimide resin is prepared by:
mixing and reacting the fluorine-free diamine compound and the fluorine-free tetracarboxylic dianhydride compound in a solvent to obtain a resin solution without fluorine molecular chain segments;
mixing and reacting a fluorine-containing diamine compound and a fluorine-containing tetracarboxylic dianhydride compound in a solvent to obtain a resin solution containing fluorine molecular chain segments;
mixing the resin solution without the fluorine molecular chain segments with the resin solution with the fluorine molecular chain segments for reaction, then adding an alkylating agent for continuous reaction, and adding water to separate out a solid product to obtain the photosensitive polyimide resin.
9. A photosensitive polyimide resin film, characterized by being produced from the photosensitive polyimide resin composition according to any one of claims 1 to 6.
10. A diamine compound having a chemical structure represented by the general formula (3) or the general formula (4):
wherein R is 7 And R is 8 Is methylene; t is an integer from 1 to 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310544455.9A CN116643458A (en) | 2023-05-15 | 2023-05-15 | Diamine compound, photosensitive polyimide resin composition, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310544455.9A CN116643458A (en) | 2023-05-15 | 2023-05-15 | Diamine compound, photosensitive polyimide resin composition, and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116643458A true CN116643458A (en) | 2023-08-25 |
Family
ID=87642761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310544455.9A Pending CN116643458A (en) | 2023-05-15 | 2023-05-15 | Diamine compound, photosensitive polyimide resin composition, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116643458A (en) |
-
2023
- 2023-05-15 CN CN202310544455.9A patent/CN116643458A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2133743B1 (en) | Photosensitive resin composition, process for producing patterned hardened film with use thereof and electronic part | |
| KR100944135B1 (en) | Positive photosensitive resin composition | |
| KR101588364B1 (en) | Method for producing polyhydroxyimide and positive photosensitive resin composition containing polyhydroxyimide obtained by the production method | |
| CN114315686B (en) | Alkynyl-containing diamine, preparation method thereof and application thereof in preparation of photosensitive resin composition | |
| CN115343914B (en) | Alkali-soluble resin, photosensitive resin composition, and photosensitive cured film | |
| CN111848954A (en) | Modified polyimide precursor resin, photosensitive resin composition and application thereof | |
| CN111171317A (en) | Modified polyimide precursor resin, photosensitive resin composition containing same and application | |
| Hsu et al. | A novel positive photosensitive polybenzoxazole precursor for microelectronic applications | |
| CN115246930B (en) | Novel polyimide resin, photosensitive polyimide resin composition, and preparation methods and applications thereof | |
| CN116789590B (en) | Diamine compound containing piperidine group, and preparation method and application thereof | |
| CN114836033B (en) | Resin precursor composition, resin film thereof, preparation method and application | |
| CN114621437B (en) | Compound for preparing photosensitive resin film, preparation method and application thereof | |
| Ho et al. | Synthesis and characteristics of organic soluble photoactive polyimides | |
| CN115010924B (en) | Photosensitive polyimide resin composition, polyimide resin film containing photosensitive polyimide resin composition and application of photosensitive polyimide resin composition | |
| CN116643458A (en) | Diamine compound, photosensitive polyimide resin composition, and preparation method and application thereof | |
| CN113467187B (en) | Resin composition, resin film, and display device | |
| CN114755891A (en) | Positive photosensitive resin composition and preparation method thereof | |
| CN114634429B (en) | Photosensitive diamine monomer and preparation method thereof, resin containing photosensitive diamine monomer and photosensitive resin composition | |
| CN114196015A (en) | Photosensitive polyimide resin precursor, preparation method thereof, photosensitive polyimide resin precursor composition and photosensitive polyimide film | |
| KR102260889B1 (en) | Soluble polyimides and positive photosensitive resin composition containing the same | |
| CN115268215A (en) | Photosensitive polyimide resin composition, photosensitive polyimide film containing same and application of photosensitive polyimide resin composition | |
| CN114200775B (en) | Positive polyimide resin composition | |
| CN114539524B (en) | Photosensitive resin precursor polymer, photosensitive resin composition slurry and application thereof | |
| CN116970276B (en) | Polyimide resin, photosensitive resin composition containing polyimide resin and photosensitive cured film | |
| CN114920934B (en) | Preparation method and application of photosensitive polyimide resin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |