JP2013037349A - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- JP2013037349A JP2013037349A JP2012146485A JP2012146485A JP2013037349A JP 2013037349 A JP2013037349 A JP 2013037349A JP 2012146485 A JP2012146485 A JP 2012146485A JP 2012146485 A JP2012146485 A JP 2012146485A JP 2013037349 A JP2013037349 A JP 2013037349A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- meth
- formula
- acrylate
- 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.)
- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000011347 resin Substances 0.000 claims abstract description 84
- 229920005989 resin Polymers 0.000 claims abstract description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 45
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 44
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 150000004292 cyclic ethers Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 2
- -1 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride Chemical class 0.000 description 116
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 93
- 239000002904 solvent Substances 0.000 description 43
- 239000010408 film Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000011248 coating agent Substances 0.000 description 22
- 238000000576 coating method Methods 0.000 description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 239000000758 substrate Substances 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000002834 transmittance Methods 0.000 description 12
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 7
- 0 C=CC(O*C(C1)C2C(CC3OC33)C3C1C2)=O Chemical compound C=CC(O*C(C1)C2C(CC3OC33)C3C1C2)=O 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 7
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- 150000007514 bases Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000003759 ester based solvent Substances 0.000 description 6
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 4
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000003566 oxetanyl group Chemical group 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000007261 regionalization Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GBOJZXLCJZDBKO-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 GBOJZXLCJZDBKO-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- SEEVRZDUPHZSOX-UHFFFAOYSA-N [1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=NOC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000004823 1,2-dimethylpropylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 2
- 125000004842 1,3-dimethylbutylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 2
- 125000004824 1,3-dimethylpropylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])([*:2])C([H])([H])[H] 0.000 description 2
- ZMSKAQFWYOSTQX-UHFFFAOYSA-N 1-(3-sulfanylpropanoyloxy)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OC(CCC)OC(=O)CCS ZMSKAQFWYOSTQX-UHFFFAOYSA-N 0.000 description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 2
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 125000004818 1-methylbutylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 125000004809 1-methylpropylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000004819 2-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 2
- 125000004820 3-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- WERQPPCVTFSKSO-UHFFFAOYSA-N 3a,7a-dimethyl-4,5-dihydro-2-benzofuran-1,3-dione Chemical compound C1CC=CC2(C)C(=O)OC(=O)C21C WERQPPCVTFSKSO-UHFFFAOYSA-N 0.000 description 2
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DOWVFPAIJRADGF-UHFFFAOYSA-N 4-ethenyl-2-benzofuran-1,3-dione Chemical compound C=CC1=CC=CC2=C1C(=O)OC2=O DOWVFPAIJRADGF-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- 125000004821 4-methylbutylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- OHMDZMAJDUVGHO-UHFFFAOYSA-N 5-ethenyl-2-benzofuran-1,3-dione Chemical compound C=CC1=CC=C2C(=O)OC(=O)C2=C1 OHMDZMAJDUVGHO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WNIHNYUROPJCLW-UHFFFAOYSA-N ethyl 2-ethoxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OCC WNIHNYUROPJCLW-UHFFFAOYSA-N 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 description 1
- WHRLOJCOIKOQGL-UHFFFAOYSA-N ethyl 2-methoxypropanoate Chemical compound CCOC(=O)C(C)OC WHRLOJCOIKOQGL-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- YDMWUMUNUXUYKT-UHFFFAOYSA-N ethyl [(1-oxo-1-phenylpropan-2-ylidene)amino] carbonate Chemical compound CCOC(=O)ON=C(C)C(=O)C1=CC=CC=C1 YDMWUMUNUXUYKT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ALPIESLRVWNLAX-UHFFFAOYSA-N hexane-1,1-dithiol Chemical compound CCCCCC(S)S ALPIESLRVWNLAX-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 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
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PBHPFFDRTUWVIT-UHFFFAOYSA-N oxetan-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CCO1 PBHPFFDRTUWVIT-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- WLVPQQDEYVVXJF-UHFFFAOYSA-N phenyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1=CC=CC=C1 WLVPQQDEYVVXJF-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QGOKIEUFWNCGFO-UHFFFAOYSA-N propanoic acid;pyrrole-2,5-dione Chemical compound CCC(O)=O.O=C1NC(=O)C=C1 QGOKIEUFWNCGFO-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229960004599 sodium borate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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Abstract
Description
本発明は感光性樹脂組成物に関する。 The present invention relates to a photosensitive resin composition.
近年の液晶表示パネル等では、フォトスペーサやオーバーコートを形成するために、感光性樹脂組成物が用いられる。このような感光性樹脂組成物としては、重合開始剤としてN−アセトキシ−1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]エタン−1−イミンを含む組成物が知られている(特許文献1)。 In recent liquid crystal display panels and the like, a photosensitive resin composition is used to form photo spacers and overcoats. Such a photosensitive resin composition contains N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine as a polymerization initiator. A composition is known (Patent Document 1).
しかしながら、従来から提案されている感光性樹脂組成物では、得られるパターンの幅の露光量依存性(露光マージン)は、必ずしも十分に満足できない場合があった。 However, in the conventionally proposed photosensitive resin compositions, the exposure amount dependency (exposure margin) of the width of the obtained pattern may not always be sufficiently satisfied.
本発明は、以下の発明を含む。
[1]樹脂、重合性化合物及び重合開始剤を含み、
樹脂が、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種に由来する構造単位を有する重合体であり、
重合開始剤が式(1)で表される化合物を含む重合開始剤である感光性樹脂組成物。
[式(1)中、Ra1及びRa2は、それぞれ独立に、Ra11、ORa11、CORa11、SRa11、CONRa12Ra13又はCNを表し、
Ra11、Ra12及びRa13は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基を表し、
Ra11、Ra12またはRa13で表わされる基の水素原子は、ORa21、CORa21、SRa21、NRa22Ra23、CONRa22Ra23、−NRa22−ORa23、−N(CORa22)−OCORa23、−C(=N−ORa21)−Ra22、−C(=N−OCORa21)−Ra22、CN、ハロゲン原子、又はCOOR21で置換されていてもよく、
Ra21、Ra22及びRa23は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基を表し、
Ra21、Ra22またはRa23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよく、
Ra11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa24−、−NRa24CO−、−NRa24COO−、−OCONRa24−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、
Ra24は、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアリールアルキル基又は炭素数2〜20の複素環基を表し、
Ra11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、Ra12とRa13及びRa22とRa23はそれぞれ一緒になって環を形成していてもよく、
Ra3及びRa4は、それぞれ独立に、Ra11、ORa11、SRa11、CORa11、CONRa12Ra13、NRa12CORa11、OCORa11、COORa11、SCORa11、OCSRa11、COSRa11、CSORa11、CN又はハロゲン原子を表し、
s及びtは、それぞれ独立に、0〜4の整数を表し、
Lは、酸素原子、硫黄原子、セレン原子、CRa31Ra32、CO、NRa33又はPRa34を表し、
Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基又は炭素数7〜30のアラルキル基を表し、
Ra31、Ra32、Ra33またはRa34で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよく、
Ra5は、ヒドロキシ基、カルボキシ基又は式(2)
(式(2)中、L1は、−O−、−S−、−NRa22−、−NRa22CO−、−SO2−、−CS−、−OCO−又は−COO−を表し、
L2は、炭素数1〜20のアルキル基からv個の水素原子を除いた基、炭素数6〜30のアリール基からv個の水素原子を除いた基、炭素数7〜30のアラルキル基からv個の水素原子を除いた基又は炭素数2〜20の複素環基からv個の水素原子を除いた基を表し、
L2で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa22−、−NRa22COO−、−OCONRa22−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、該アルキレン部分は分枝鎖状であってもよく、環状であってもよく、
Ra6は、ORa41、SRa41、CONRa42Ra43、NRa42CORa43、OCORa41、COORa41、SCORa41、OCSRa41、COSRa41、CSORa41、CN又はハロゲン原子を表し、
Ra41、Ra42及びRa43は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基又は炭素数7〜30のアラルキル基を表し、Ra41、Ra42及びRa43で表される基がアルキル部分を有する場合、該アルキル部分は分枝鎖状であってもよく、環状であってもよく、Ra42とRa43は、一緒になって環を形成していてもよく、
vは1〜3の整数を表す。)
で表される基を表す。]
The present invention includes the following inventions.
[1] including a resin, a polymerizable compound, and a polymerization initiator,
The resin is a polymer having a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride,
The photosensitive resin composition which is a polymerization initiator in which a polymerization initiator contains the compound represented by Formula (1).
[In the formula (1), R a1 and R a2 each independently represent R a11 , OR a11 , COR a11 , SR a11 , CONR a12 R a13 or CN;
R a11 , R a12 and R a13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or an alkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group,
The hydrogen atom of the group represented by R a11 , R a12 or R a13 is OR a21 , COR a21 , SR a21 , NR a22 R a23 , CONR a22 R a23 , —NR a22 —OR a23 , —N (COR a22 ) — OCOR a23 , —C (═N—OR a21 ) —R a22 , —C (═N—OCOR a21 ) —R a22 , CN, halogen atom, or COOR 21 may be substituted,
R a21 , R a22 and R a23 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or an alkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group,
The hydrogen atom of the group represented by R a21 , R a22 or R a23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group,
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 has an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR a24 -, - NR a24 CO -, - NR a24 COO -, - OCONR a24 -, - SCO -, - COS -, - OCS- or -CSO- by which it may be interrupted 1 to 5 times,
R a24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 has an alkyl moiety, the alkyl moiety may be branched or cyclic. And R a12 and R a13 and R a22 and R a23 may be combined to form a ring,
R a3 and R a4 are each independently, R a11, OR a11, SR a11, COR a11, CONR a12 R a13, NR a12 COR a11, OCOR a11, COOR a11, SCOR a11, OCSR a11, COSR a11, CSOR a11 , CN or a halogen atom,
s and t each independently represent an integer of 0 to 4,
L represents an oxygen atom, a sulfur atom, a selenium atom, CR a31 R a32 , CO, NR a33 or PR a34 ,
R a31 , R a32 , R a33 and R a34 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms,
When the group represented by R a31 , R a32 , R a33 or R a34 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R a31 , R a32 , R a33 and R a34 may each independently form a ring together with one of the adjacent benzene rings,
R a5 is a hydroxy group, a carboxy group or a formula (2)
(In the formula (2), L 1 represents —O—, —S—, —NR a22 —, —NR a22 CO— , —SO 2 —, —CS—, —OCO— or —COO—,
L 2 is a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. A group in which v hydrogen atoms are removed from or a group in which v hydrogen atoms are removed from a heterocyclic group having 2 to 20 carbon atoms,
When the group represented by L 2 has an alkylene moiety, the alkylene moiety is —O—, —S—, —COO— , —OCO— , —NR a22 —, —NR a22 COO— , —OCONR a22 —. , -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times, and the alkylene moiety may be branched or cyclic,
R a6 represents OR a41 , SR a41 , CONR a42 R a43 , NR a42 COR a43 , OCOR a41 , COOR a41 , SCOR a41 , OCSR a41 , COSR a41 , CSOR a41 , CN or a halogen atom,
R a41 , R a42 and R a43 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms, and R a41 , R When the group represented by a42 and R a43 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R a42 and R a43 together form a ring. May be formed,
v represents an integer of 1 to 3. )
Represents a group represented by ]
[2]樹脂が、さらに、炭素数2〜4の環状エーテル構造とエチレン性不飽和結合とを有する単量体に由来する構造単位を有する共重合体である[1]記載の感光性樹脂組成物。
[3][1]又は[2]記載の感光性樹脂組成物により形成されるパターン。
[4][3]記載のパターンを含む表示装置。
[2] The photosensitive resin composition according to [1], wherein the resin is a copolymer further having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond. object.
[3] A pattern formed from the photosensitive resin composition according to [1] or [2].
[4] A display device including the pattern according to [3].
本発明によれば、パターン形成時の露光マージンが広い感光性樹脂組成物を提供することが可能となる。 ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide the photosensitive resin composition with a wide exposure margin at the time of pattern formation.
以下、本発明を詳細に説明する。なお、本明細書において、各成分として例示する化合物は、特に断りのない限り、単独で又は組合せて使用することができる。 Hereinafter, the present invention will be described in detail. In addition, in this specification, the compound illustrated as each component can be used individually or in combination unless there is particular notice.
本発明の感光性樹脂組成物は、樹脂(A)、重合性化合物(B)及び重合開始剤(C)を含み、樹脂(A)が、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種に由来する構造単位を有する重合体であり、重合開始剤(C)が式(1)で表される化合物を含む重合開始剤である。さらに溶剤(D)を含むことが好ましい。 The photosensitive resin composition of the present invention includes a resin (A), a polymerizable compound (B), and a polymerization initiator (C), and the resin (A) is composed of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride. It is a polymer having a structural unit derived from at least one selected from the group, and the polymerization initiator (C) is a polymerization initiator containing a compound represented by the formula (1). Furthermore, it is preferable that a solvent (D) is included.
本発明の感光性樹脂組成物は、樹脂(A)を含み、樹脂(A)は、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種に由来する構造単位を有する重合体である。該構造単位は、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種が有する不飽和結合で重合することにより生成する構造単位である。
樹脂(A)としては、例えば、以下の樹脂[K1]〜[K6]等が挙げられる。
[K1]不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種(a)(以下「(a)」という場合がある)と、炭素数2〜4の環状エーテル構造とエチレン性不飽和結合とを有する単量体(b)(以下「(b)」という場合がある)との共重合体。
[K2](a)と(b)と、(a)と共重合可能な単量体(c)(ただし、(a)及び(b)とは異なる。)(以下「(c)」という場合がある)との共重合体
[K3](a)と(c)との共重合体
[K4](a)と(c)との共重合体に(b)を反応させて得られる樹脂。
[K5](b)と(c)との共重合体に(a)を反応させて得られる樹脂。
[K6](b)と(c)との共重合体に(a)を反応させ、さらにカルボン酸無水物を反応させて得られる樹脂。
The photosensitive resin composition of the present invention contains a resin (A), and the resin (A) has a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride. It is a polymer. This structural unit is a structural unit produced | generated by superposing | polymerizing with the unsaturated bond which at least 1 sort (s) chosen from the group which consists of unsaturated carboxylic acid and unsaturated carboxylic anhydride.
Examples of the resin (A) include the following resins [K1] to [K6].
[K1] at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (a) (hereinafter sometimes referred to as “(a)”), a cyclic ether structure having 2 to 4 carbon atoms, A copolymer with a monomer (b) having an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”).
[K2] (a), (b), and monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as “(c)”) [K3] Copolymer of (a) and (c) [K4] A resin obtained by reacting (b) with a copolymer of (a) and (c).
[K5] A resin obtained by reacting (a) with a copolymer of (b) and (c).
[K6] A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting with a carboxylic acid anhydride.
(a)としては、具体的には、例えば、アクリル酸、メタクリル酸、クロトン酸、o−、m−、p−ビニル安息香酸等の不飽和モノカルボン酸類;
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3−ビニルフタル酸、4−ビニルフタル酸、3,4,5,6−テトラヒドロフタル酸、1,2,3,6−テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸、1、4−シクロヘキセンジカルボン酸等の不飽和ジカルボン酸類;
メチル−5−ノルボルネン−2,3−ジカルボン酸、5−カルボキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−エチルビシクロ[2.2.1]ヘプト−2−エン等のカルボキシ基を含有するビシクロ不飽和化合物類;
無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3−ビニルフタル酸無水物、4−ビニルフタル酸無水物、3,4,5,6−テトラヒドロフタル酸無水物、1,2,3,6−テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン無水物(ハイミック酸無水物)等の不飽和ジカルボン酸類無水物;
Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo Bicyclounsaturated compounds containing a carboxy group such as [2.2.1] hept-2-ene, 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride (hymic acid anhydride);
こはく酸モノ〔2−(メタ)アクリロイルオキシエチル〕、フタル酸モノ〔2−(メタ)アクリロイルオキシエチル〕等の2価以上の多価カルボン酸の不飽和モノ〔(メタ)アクリロイルオキシアルキル〕エステル類;
α−(ヒドロキシメチル)アクリル酸のような、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和アクリレート類等が挙げられる。
これらのうち、共重合反応性の点やアルカリ水溶液への溶解性の点から、アクリル酸、メタクリル酸、無水マレイン酸等が好ましい。
Unsaturated mono [(meth) acryloyloxyalkyl] esters of polyvalent carboxylic acids such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl] Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility in an aqueous alkali solution.
(b)は、例えば、炭素数2〜4の環状エーテル構造(例えば、オキシラン環、オキセタン環及びテトラヒドロフラン環からなる群から選ばれる少なくとも1種)とエチレン性不飽和結合とを有する重合性化合物をいう。(b)は、炭素数2〜4の環状エーテル構造と(メタ)アクリロイルオキシ基とを有する単量体が好ましい。
尚、本明細書において、「(メタ)アクリル酸」とは、アクリル酸及びメタクリル酸よりなる群から選ばれる少なくとも1種を表す。「(メタ)アクリロイル」及び「(メタ)アクリレート」等の表記も、同様の意味を有する。
(B) is, for example, a polymerizable compound having a C2-C4 cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say. (B) is preferably a monomer having a C2-C4 cyclic ether structure and a (meth) acryloyloxy group.
In the present specification, “(meth) acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
(b)としては、例えば、オキシラニル基とエチレン性不飽和結合とを有する単量体(b1)(以下「(b1)」という場合がある)、オキセタニル基とエチレン性不飽和結合とを有する単量体(b2)(以下「(b2)」という場合がある)、テトラヒドロフリル基とエチレン性不飽和結合とを有する単量体(b3)(以下「(b3)」という場合がある)等が挙げられる。 Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond. Monomer (b2) (hereinafter sometimes referred to as “(b2)”), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”), etc. Can be mentioned.
(b1)は、例えば、直鎖状又は分枝鎖状の不飽和脂肪族炭化水素をエポキシ化した構造を有する単量体(b1−1)(以下「(b1−1)」という場合がある)、不飽和脂環式炭化水素をエポキシ化した構造を有する単量体(b1−2)(以下「(b1−2)」という場合がある)が挙げられる。 (B1) may be, for example, a monomer (b1-1) having a structure obtained by epoxidizing a linear or branched unsaturated aliphatic hydrocarbon (hereinafter referred to as “(b1-1)”) ), A monomer (b1-2) having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter sometimes referred to as “(b1-2)”).
(b1−1)としては、グリシジル(メタ)アクリレート、β−メチルグリシジル(メタ)アクリレート、β−エチルグリシジル(メタ)アクリレート、グリシジルビニルエーテル、o−ビニルベンジルグリシジルエーテル、m−ビニルベンジルグリシジルエーテル、p−ビニルベンジルグリシジルエーテル、α−メチル−o−ビニルベンジルグリシジルエーテル、α−メチル−m−ビニルベンジルグリシジルエーテル、α−メチル−p−ビニルベンジルグリシジルエーテル、2,3−ビス(グリシジルオキシメチル)スチレン、2,4−ビス(グリシジルオキシメチル)スチレン、2,5−ビス(グリシジルオキシメチル)スチレン、2,6−ビス(グリシジルオキシメチル)スチレン、2,3,4−トリス(グリシジルオキシメチル)スチレン、2,3,5−トリス(グリシジルオキシメチル)スチレン、2,3,6−トリス(グリシジルオキシメチル)スチレン、3,4,5−トリス(グリシジルオキシメチル)スチレン、2,4,6−トリス(グリシジルオキシメチル)スチレン等が挙げられる。 As (b1-1), glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p -Vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene 2,3,5-tris (glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2,4,6- Examples include tris (glycidyloxymethyl) styrene.
(b1−2)としては、ビニルシクロヘキセンモノオキサイド、1,2−エポキシ−4−ビニルシクロヘキサン(例えば、セロキサイド2000;ダイセル化学工業(株)製)、3,4−エポキシシクロヘキシルメチル(メタ)アクリレート(例えば、サイクロマーA400;ダイセル化学工業(株)製)、3,4−エポキシシクロヘキシルメチル(メタ)アクリレート(例えば、サイクロマーM100;ダイセル化学工業(株)製)、式(I)で表される化合物及び式(II)で表される化合物等が挙げられる。 Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate ( For example, Cyclomer A400 (manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Chemical Industries, Ltd.), represented by formula (I) Examples thereof include compounds and compounds represented by formula (II).
[式(I)及び式(II)中、Ra及びRbは、互いに独立に、水素原子、又は炭素数1〜4のアルキル基を表し、該アルキル基に含まれる水素原子は、ヒドロキシ基で置換されていてもよい。
Xa及びXbは、互いに独立に、単結合、−Rc−、*−Rc−O−、*−Rc−S−、*−Rc−NH−を表す。
Rcは、炭素数1〜6のアルカンジイル基を表す。
*は、Oとの結合手を表す。]
[In Formula (I) and Formula (II), R a and R b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group May be substituted.
X a and X b are each independently a single bond, -R c -, * - R c -O -, * - R c -S -, * - represents the R c -NH-.
R c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]
炭素数1〜4のアルキル基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基等が挙げられる。
水素原子がヒドロキシで置換されたアルキル基としては、ヒドロキシメチル基、1−ヒドロキシエチル基、2−ヒドロキシエチル基、1−ヒドロキシプロピル基、2−ヒドロキシプロピル基、3−ヒドロキシプロピル基、1−ヒドロキシ−1−メチルエチル基、2−ヒドロキシ−1−メチルエチル基、1−ヒドロキシブチル基、2−ヒドロキシブチル基、3−ヒドロキシブチル基、4−ヒドロキシブチル基等が挙げられる。
R1及びR2としては、好ましくは水素原子、メチル基、ヒドロキシメチル基、1−ヒドロキシエチル基、2−ヒドロキシエチル基が挙げられ、より好ましくは水素原子、メチル基が挙げられる。
Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
Examples of the alkyl group in which a hydrogen atom is substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy Examples include a -1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
R 1 and R 2 are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.
アルカンジイル基としては、メチレン基、エチレン基、プロパン−1,2−ジイル基、プロパン−1,3−ジイル基、ブタン−1,4−ジイル基、ペンタン−1,5−ジイル基、ヘキサン−1,6−ジイル基等が挙げられる。
X1及びX2としては、好ましくは単結合、メチレン基、エチレン基、*−CH2−O−(*はOとの結合手を表す)基、*−CH2CH2−O−基が挙げられ、より好ましくは単結合、*−CH2CH2−O−基が挙げられる。
Examples of alkanediyl groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- Examples include 1,6-diyl group.
X 1 and X 2 are preferably a single bond, a methylene group, an ethylene group, * —CH 2 —O— (* represents a bond to O), or * —CH 2 CH 2 —O— group. More preferably, a single bond and a * —CH 2 CH 2 —O— group are mentioned.
式(I)で表される化合物としては、式(I−1)〜式(I−15)で表される化合物等が挙げられる。好ましくは式(I−1)、式(I−3)、式(I−5)、式(I−7)、式(I−9)、式(I−11)〜式(I−15)が挙げられる。より好ましくは式(I−1)、式(I−7)、式(I−9)、式(I−15)が挙げられる。 Examples of the compound represented by the formula (I) include compounds represented by the formula (I-1) to the formula (I-15). Preferably Formula (I-1), Formula (I-3), Formula (I-5), Formula (I-7), Formula (I-9), Formula (I-11) to Formula (I-15) Is mentioned. More preferably, Formula (I-1), Formula (I-7), Formula (I-9), and Formula (I-15) are mentioned.
式(II)で表される化合物としては、式(II−1)〜式(II−15)で表される化合物等が挙げられる。好ましくは式(II−1)、式(II−3)、式(II−5)、式(II−7)、式(II−9)、式(II−11)〜式(II−15)が挙げられる。より好ましくは式(II−1)、式(II−7)、式(II−9)、式(II−15)が挙げられる。 Examples of the compound represented by the formula (II) include compounds represented by the formula (II-1) to the formula (II-15). Preferably Formula (II-1), Formula (II-3), Formula (II-5), Formula (II-7), Formula (II-9), Formula (II-11) to Formula (II-15) Is mentioned. More preferably, Formula (II-1), Formula (II-7), Formula (II-9), and Formula (II-15) are mentioned.
式(I)で表される化合物及び式(II)で表される化合物は、それぞれ単独で用いることができる。また、それらは、任意の比率で混合することができる。混合する場合、その混合比率はモル比で、好ましくは式(I):式(II)で、5:95〜95:5、より好ましくは10:90〜90:10、さらに好ましくは20:80〜80:20である。 The compound represented by the formula (I) and the compound represented by the formula (II) can be used alone. They can also be mixed in any ratio. When mixing, the mixing ratio is a molar ratio, preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, and still more preferably 20:80 in the formula (I): formula (II). ~ 80: 20.
オキセタニル基とエチレン性不飽和結合とを有する単量体(b2)としては、オキセタニル基と(メタ)アクリロイルオキシ基とを有する単量体がより好ましい。(b2)としては、3−メチル−3−メタクリルロイルオキシメチルオキセタン、3−メチル−3−アクリロイルオキシメチルオキセタン、3−エチル−3−メタクリロイルオキシメチルオキセタン、3−エチル−3−アクリロイルオキシメチルオキセタン、3−メチル−3−メタクリロイルオキシエチルオキセタン、3−メチル−3−アクリロイルオキシエチルオキセタン、3−エチル−3−メタクリロイルオキシエチルオキセタン、3−エチル−3−アクリロイルオキシエチルオキセタン等が挙げられる。 As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable. (B2) includes 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, and the like.
テトラヒドロフリル基とエチレン性不飽和結合とを有する単量体(b3)としては、テトラヒドロフリル基と(メタ)アクリロイルオキシ基とを有する単量体がより好ましい。(b3)としては、具体的には、テトラヒドロフルフリルアクリレート(例えば、ビスコートV#150、大阪有機化学工業(株)製)、テトラヒドロフルフリルメタクリレート等が挙げられる。 As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
(b)としては、得られるカラーフィルタの耐熱性、耐薬品性等の信頼性をより高くすることができる点で、(b1)であることが好ましい。さらに、着色硬化性樹脂組成物の保存安定性が優れるという点で、(b1−2)がより好ましい。 (B) is preferably (b1) in that the color filter obtained can have higher reliability such as heat resistance and chemical resistance. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.
(c)としては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−ブチル(メタ)アクリレート、sec−ブチル(メタ)アクリレート、tert−ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ドデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、シクロペンチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−メチルシクロヘキシル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン−8−イル(メタ)アクリレート(当該技術分野では、慣用名として「ジシクロペンタニル(メタ)アクリレート」といわれている。また、「トリシクロデシル(メタ)アクリレート」という場合がある。)、トリシクロ[5.2.1.02,6]デセン−8−イル(メタ)アクリレート(当該技術分野では、慣用名として「ジシクロペンテニル(メタ)アクリレート」といわれている。)、ジシクロペンタニルオキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、アダマンチル(メタ)アクリレート、アリル(メタ)アクリレート、プロパルギル(メタ)アクリレート、フェニル(メタ)アクリレート、ナフチル(メタ)アクリレート、ベンジル(メタ)アクリレート等の(メタ)アクリル酸エステル類;
2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート等のヒドロキシ基含有(メタ)アクリル酸エステル類;
マレイン酸ジエチル、フマル酸ジエチル、イタコン酸ジエチル等のジカルボン酸ジエステル;
Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decan-8-yl (meth) acrylate (in this technical field, it is called “dicyclopentanyl (meth) acrylate” as a common name. In the case of “tricyclodecyl (meth) acrylate”) There is a bird) Black (in the art, it is said that "dicyclopentenyl (meth) acrylate" as trivial name.) [5.2.1.0 2,6] decene-8-yl (meth) acrylate, dicyclopenta Nyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate, etc. (Meth) acrylic acid esters of
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate;
ビシクロ[2.2.1]ヘプト−2−エン、5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシメチルビシクロ[2.2.1]ヘプト−2−エン、5−(2’−ヒドロキシエチル)ビシクロ[2.2.1]ヘプト−2−エン、5−メトキシビシクロ[2.2.1]ヘプト−2−エン、5−エトキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジヒドロキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジ(ヒドロキシメチル)ビシクロ[2.2.1]ヘプト−2−エン、5,6−ジ(2’−ヒドロキシエチル)ビシクロ[2.2.1]ヘプト−2−エン、5,6−ジメトキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジエトキシビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシ−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシ−5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−ヒドロキシメチル−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−tert−ブトキシカルボニルビシクロ[2.2.1]ヘプト−2−エン、5−シクロヘキシルオキシカルボニルビシクロ[2.2.1]ヘプト−2−エン、5−フェノキシカルボニルビシクロ[2.2.1]ヘプト−2−エン、5,6−ビス(tert−ブトキシカルボニル)ビシクロ[2.2.1]ヘプト−2−エン、5,6−ビス(シクロヘキシルオキシカルボニル)ビシクロ[2.2.1]ヘプト−2−エン等のビシクロ不飽和化合物類; Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2′-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2 .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] hept-2-ene, 5,6-di (2′-hydroxyethyl) bicyclo [2.2. 1] hept-2-ene, 5,6-dimethoxybicyclo [2. .1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene, 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene Bicyclo unsaturated compounds;
N−フェニルマレイミド、N−シクロヘキシルマレイミド、N−ベンジルマレイミド、N−スクシンイミジル−3−マレイミドベンゾエート、N−スクシンイミジル−4−マレイミドブチレート、N−スクシンイミジル−6−マレイミドカプロエート、N−スクシンイミジル−3−マレイミドプロピオネート、N−(9−アクリジニル)マレイミド等のジカルボニルイミド誘導体類; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;
スチレン、α−メチルスチレン、m−メチルスチレン、p−メチルスチレン、ビニルトルエン、p−メトキシスチレン、アクリロニトリル、メタクリロニトリル、塩化ビニル、塩化ビニリデン、アクリルアミド、メタクリルアミド、酢酸ビニル、1,3−ブタジエン、イソプレン、2,3−ジメチル−1,3−ブタジエン等が挙げられる。
これらのうち、共重合反応性及び耐熱性の点から、スチレン、N−フェニルマレイミド、N−シクロヘキシルマレイミド、N−ベンジルマレイミド、ビシクロ[2.2.1]ヘプト−2−エン等が好ましい。
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , Isoprene, 2,3-dimethyl-1,3-butadiene and the like.
Of these, styrene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are preferable from the viewpoint of copolymerization reactivity and heat resistance.
樹脂[K1]において、それぞれに由来する構造単位の比率は、樹脂[K1]を構成する全構造単位中、以下の範囲にあることが好ましい。
(a)に由来する構造単位;5〜60モル%、より好ましくは10〜50モル%。
(b)に由来する構造単位;40〜95モル%、より好ましくは50〜90モル%。
樹脂[K1]の構造単位の比率が、上記の範囲にあると、感光性樹脂組成物の保存安定性、感光性樹脂組成物からパターンを形成する際の現像性、並びに、得られるパターンの耐溶剤性、耐熱性及び機械強度に優れる傾向がある。
樹脂[K1]としては、(b)が(b1)である樹脂が好ましく、(b)が(b1−2)である樹脂がより好ましい。
In the resin [K1], the ratio of the structural units derived from each is preferably in the following range among all the structural units constituting the resin [K1].
Structural unit derived from (a); 5-60 mol%, more preferably 10-50 mol%.
Structural unit derived from (b); 40 to 95 mol%, more preferably 50 to 90 mol%.
When the ratio of the structural unit of the resin [K1] is in the above range, the storage stability of the photosensitive resin composition, the developability when forming a pattern from the photosensitive resin composition, and the resistance of the resulting pattern are improved. It tends to be excellent in solvent resistance, heat resistance and mechanical strength.
As the resin [K1], a resin in which (b) is (b1) is preferable, and a resin in which (b) is (b1-2) is more preferable.
樹脂[K1]は、例えば、文献「高分子合成の実験法」(大津隆行著 発行所(株)化学同人 第1版第1刷 1972年3月1日発行)に記載された方法及び当該文献に記載された引用文献を参考にして製造することができる。 The resin [K1] is, for example, a method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., First Edition, First Edition, issued March 1, 1972) and the document Can be produced with reference to the cited references described in 1.
具体的には、(a)及び(b)の所定量、重合開始剤及び溶剤等を反応容器中に入れて、例えば、脱酸素雰囲気下で、攪拌しながら、加熱及び保温する方法が挙げられる。なお、ここで用いられる重合開始剤及び溶剤等は、特に限定されず、当該分野で通常使用されているもののいずれをも使用することができ、例えば、重合開始剤としては、アゾ化合物(2,2′−アゾビスイソブチロニトリル、2,2′−アゾビス(2,4−ジメチルバレロニトリル)等)や有機過酸化物(ベンゾイルペルオキシド等)が挙げられ、溶剤としては、各モノマーを溶解するものであればよく、感光性樹脂組成物の溶剤として後述する溶剤(D)等を用いることができる。 Specifically, a method in which a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel and heated and kept warm while stirring in a deoxygenated atmosphere, for example. . The polymerization initiator and the solvent used here are not particularly limited, and any of those usually used in the field can be used. For example, as the polymerization initiator, an azo compound (2, 2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent dissolves each monomer. Any solvent may be used, and a solvent (D) described later can be used as a solvent for the photosensitive resin composition.
なお、得られた共重合体は、反応後の溶液をそのまま使用してもよいし、濃縮あるいは希釈した溶液を使用してもよいし、再沈殿等の方法で固体(粉体)として取り出したものを使用してもよい。特に、この重合の際に溶剤として、後述する溶剤(D)を使用することにより、反応後の溶液をそのまま使用することができ、製造工程を簡略化することができる。 In addition, the obtained copolymer may use the solution after reaction as it is, a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used. In particular, by using a solvent (D) described later as a solvent in the polymerization, the solution after the reaction can be used as it is, and the manufacturing process can be simplified.
樹脂[K2]において、それぞれに由来する構造単位の比率は、樹脂[K2]を構成する全構造単位中、以下の範囲にあることが好ましい。
(a)に由来する構造単位;4〜45モル%、より好ましくは10〜30モル%。
(b)に由来する構造単位;2〜95モル%、より好ましくは5〜80モル%。
(c)に由来する構造単位;1〜65モル%、より好ましくは5〜60モル%。
樹脂[K2]の構造単位の比率が、上記の範囲にあると、保存安定性、現像性、得られるパターンの耐溶剤性、耐熱性及び機械強度に優れる傾向がある。
樹脂[K2]としては、(b)が(b1)である樹脂が好ましく、(b)が(b1−2)である樹脂がより好ましい。
In the resin [K2], the ratio of the structural units derived from each is preferably within the following range among all the structural units constituting the resin [K2].
Structural unit derived from (a); 4-45 mol%, more preferably 10-30 mol%.
Structural unit derived from (b); 2-95 mol%, more preferably 5-80 mol%.
Structural unit derived from (c); 1 to 65 mol%, more preferably 5 to 60 mol%.
When the ratio of the structural unit of the resin [K2] is in the above range, the storage stability, developability, solvent resistance of the resulting pattern, heat resistance, and mechanical strength tend to be excellent.
As the resin [K2], a resin in which (b) is (b1) is preferable, and a resin in which (b) is (b1-2) is more preferable.
樹脂[K2]は、例えば、樹脂[K1]の製造方法として記載した方法と同様に製造することができる。
具体的には、(a)、(b)及び(c)の所定量、重合開始剤及び溶剤を反応容器中に仕込んで、脱酸素雰囲気下で、攪拌、加熱、保温する方法が挙げられる。得られた共重合体は、反応後の溶液をそのまま使用してもよいし、濃縮あるいは希釈した溶液を使用してもよいし、再沈殿等の方法で固体(粉体)として取り出したものを使用してもよい。
Resin [K2] can be produced, for example, in the same manner as the method described as the production method of resin [K1].
Specifically, a predetermined amount of (a), (b) and (c), a polymerization initiator, and a solvent are charged into a reaction vessel, and the mixture is stirred, heated and kept warm in a deoxygenated atmosphere. As the obtained copolymer, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation. May be used.
樹脂[K3]において、それぞれに由来する構造単位の比率は、樹脂[K3]を構成する全構造単位中、以下の範囲にあることが好ましい。
(a)2〜55モル%、より好ましくは10〜50モル%
(c)45〜98モル%、より好ましくは50〜90モル%
樹脂[K3]は、例えば、樹脂[K1]と同様の方法により製造することができる。
In the resin [K3], the ratio of the structural unit derived from each is preferably in the following range among all the structural units constituting the resin [K3].
(A) 2 to 55 mol%, more preferably 10 to 50 mol%
(C) 45-98 mol%, more preferably 50-90 mol%
Resin [K3] can be manufactured by the same method as resin [K1], for example.
樹脂[K4]は、(a)と(c)との共重合体を得て、(b)が有する炭素数2〜4の環状エーテルを(a)が有するカルボン酸及び/又はカルボン酸無水物に付加させることにより製造することができる。
まず(a)と(c)との共重合体を、[K1]の製造方法として記載した方法と同様に製造する。この場合、それぞれに由来する構造単位の比率は、(a)と(c)との共重合体を構成する全構造単位中、以下の範囲にあることが好ましい。
(a)5〜50モル%、より好ましくは10〜45モル%
(c)50〜95モル%、より好ましくは55〜90モル%
Resin [K4] obtains a copolymer of (a) and (c), and (a) has a carboxylic acid and / or carboxylic acid anhydride having (a) a cyclic ether having 2 to 4 carbon atoms that (b) has It can manufacture by adding to.
First, a copolymer of (a) and (c) is produced in the same manner as the method described as the production method of [K1]. In this case, the ratio of the structural units derived from each is preferably in the following range among all the structural units constituting the copolymer of (a) and (c).
(A) 5 to 50 mol%, more preferably 10 to 45 mol%
(C) 50 to 95 mol%, more preferably 55 to 90 mol%
次に、前記共重合体中の(a)に由来するカルボン酸及び/又はカルボン酸無水物の一部に、(b)が有する炭素数2〜4の環状エーテルを反応させる。
(a)と(c)との共重合体の製造に引き続き、フラスコ内雰囲気を窒素から空気に置換し、(b)、カルボン酸又はカルボン酸無水物と環状エーテルとの反応触媒(例えばトリス(ジメチルアミノメチル)フェノール等)及び重合禁止剤(例えばハイドロキノン等)等をフラスコ内に入れて、例えば、60〜130℃で、1〜10時間反応することにより、樹脂[K4]を得ることができる。
(b)の使用量は、(a)100モルに対して、5〜80モルが好ましく、より好ましくは10〜75モルである。この範囲とすることにより、保存安定性、現像性、耐溶剤性、耐熱性、機械強度及び感度のバランスが良好になる傾向がある。環状エーテルの反応性が高く、未反応の(b)が残存しにくいことから、樹脂[K4]に用いる(b)としては(b1)が好ましく、さらに(b1−1)が好ましい。
前記反応触媒の使用量は、(a)、(b)及び(c)の合計量に対して0.001〜5質量%が好ましい。前記重合禁止剤の使用量は、(a)、(b)及び(c)の合計量に対して0.001〜5質量%が好ましい。
仕込方法、反応温度及び時間等の反応条件は、製造設備や重合による発熱量等を考慮して適宜調整することができる。なお、重合条件と同様に、製造設備や重合による発熱量等を考慮し、仕込方法や反応温度を適宜調整することができる。
Next, the C2-C4 cyclic ether which (b) has is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer.
Subsequent to the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether (for example, tris ( (Dimethylaminomethyl) phenol and the like) and a polymerization inhibitor (for example, hydroquinone and the like) are placed in a flask and reacted at, for example, 60 to 130 ° C. for 1 to 10 hours to obtain a resin [K4]. .
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By setting it as this range, there exists a tendency for the balance of storage stability, developability, solvent resistance, heat resistance, mechanical strength, and sensitivity to become favorable. Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K4], and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 mass% with respect to the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5% by mass with respect to the total amount of (a), (b) and (c).
The reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization. In addition, like the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.
樹脂[K5]は、第一段階として、上述した樹脂[K1]の製造方法と同様にして、(b)と(c)との共重合体を得る。上記と同様に、得られた共重合体は、反応後の溶液をそのまま使用してもよいし、濃縮あるいは希釈した溶液を使用してもよいし、再沈殿等の方法で固体(粉体)として取り出したものを使用してもよい。
(b)及び(c)に由来する構造単位の比率は、前記の共重合体を構成する全構造単位の合計モル数に対して、以下の範囲にあることが好ましい。
(b)に由来する構造単位;5〜95モル%、より好ましくは10〜90モル%。
(c)に由来する構造単位;5〜95モル%、より好ましくは10〜90モル%。
Resin [K5] obtains a copolymer of (b) and (c) as a first step in the same manner as in the method for producing resin [K1] described above. Similarly to the above, the obtained copolymer may be used as it is after the reaction, or may be a concentrated or diluted solution, or may be solid (powder) by a method such as reprecipitation. You may use what was taken out as.
The ratio of the structural units derived from (b) and (c) is preferably in the following range with respect to the total number of moles of all structural units constituting the copolymer.
Structural unit derived from (b); 5-95 mol%, more preferably 10-90 mol%.
Structural unit derived from (c); 5-95 mol%, more preferably 10-90 mol%.
さらに、樹脂[K4]の製造方法と同様の条件で、(b)と(c)との共重合体が有する(b)に由来する環状エーテルに、(a)が有するカルボン酸又はカルボン酸無水物を反応させることにより、樹脂[K5]を得ることができる。
前記の共重合体に反応させる(a)の使用量は、(b)100モルに対して、5〜80モルが好ましい。環状エーテルの反応性が高く、未反応の(b)が残存しにくいことから、樹脂[K5]に用いる(b)としては(b1)が好ましく、さらに(b1−1)が好ましい。
Further, under the same conditions as in the method for producing the resin [K4], the cyclic ether derived from (b) of the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic acid anhydride of (a). Resin [K5] can be obtained by reacting the product.
As for the usage-amount of (a) made to react with the said copolymer, 5-80 mol is preferable with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K5], and (b1-1) is more preferable.
樹脂[K6]は、樹脂[K5]に、さらにカルボン酸無水物を反応させた樹脂である。環状エーテルとカルボン酸又はカルボン酸無水物との反応により発生するヒドロキシ基に、カルボン酸無水物を反応させる。
カルボン酸無水物としては、無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3−ビニルフタル酸無水物、4−ビニルフタル酸無水物、3,4,5,6−テトラヒドロフタル酸無水物、1,2,3,6−テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン無水物(ハイミック酸無水物)等が挙げられる。カルボン酸無水物の使用量は、(a)の使用量1モルに対して、0.5〜1モルが好ましい。
Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. Carboxylic anhydride is reacted with a hydroxy group generated by reaction of cyclic ether with carboxylic acid or carboxylic anhydride.
Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride (highmic acid anhydride) and the like. It is done. As for the usage-amount of carboxylic acid anhydride, 0.5-1 mol is preferable with respect to 1 mol of usage-amount of (a).
樹脂(A)としては、具体的に、3,4−エポキシシクロヘキシルメチル(メタ)アクリレート/(メタ)アクリル酸共重合体、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレート/(メタ)アクリル酸共重合体等の樹脂[K1];グリシジル(メタ)アクリレート/ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体、グリシジル(メタ)アクリレート/スチレン/(メタ)アクリル酸共重合体、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレート/(メタ)アクリル酸/N−シクロヘキシルマレイミド共重合体、3−メチル−3−(メタ)アクリルロイルオキシメチルオキセタン/(メタ)アクリル酸/スチレン共重合体等の樹脂[K2];ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体、スチレン/(メタ)アクリル酸共重合体等の樹脂[K3];ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体にグリシジル(メタ)アクリレートを付加させた樹脂、トリシクロデシル(メタ)アクリレート/スチレン/(メタ)アクリル酸共重合体にグリシジル(メタ)アクリレートを付加させた樹脂、トリシクロデシル(メタ)アクリレート/ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体にグリシジル(メタ)アクリレートを付加させた樹脂等の樹脂[K4];トリシクロデシル(メタ)アクリレート/グリシジル(メタ)アクリレートの共重合体に(メタ)アクリル酸を反応させた樹脂、トリシクロデシル(メタ)アクリレート/スチレン/グリシジル(メタ)アクリレートの共重合体に(メタ)アクリル酸を反応させた樹脂等の樹脂[K5];トリシクロデシル(メタ)アクリレート/グリシジル(メタ)アクリレートの共重合体に(メタ)アクリル酸を反応させた樹脂にさらにテトラヒドロフタル酸無水物を反応させた樹脂等の樹脂[K6]等が挙げられる。
これらの樹脂は、単独で用いても2種以上を併用してもよい。
Specific examples of the resin (A) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2.6. ] Resin such as decyl acrylate / (meth) acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meta ) Acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3- ( Resin [K2] such as (meth) acryloyloxymethyloxetane / (meth) acrylic acid / styrene copolymer; benzyl (meth) acrylate / Glycidyl (meth) acrylate was added to resin [K3]; benzyl (meth) acrylate / (meth) acrylic acid copolymer such as (meth) acrylic acid copolymer and styrene / (meth) acrylic acid copolymer Resin, tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer added with glycidyl (meth) acrylate, tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic Resin such as resin obtained by adding glycidyl (meth) acrylate to acid copolymer [K4]; resin obtained by reacting (meth) acrylic acid with tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer , Tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate Resin such as a resin obtained by reacting (meth) acrylic acid with the polymer [K5]; a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid and tetrahydro Examples thereof include a resin [K6] such as a resin reacted with phthalic anhydride.
These resins may be used alone or in combination of two or more.
中でも、樹脂(A)としては、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種に由来する構造単位と、炭素数2〜4の環状エーテル構造とエチレン性不飽和結合とを有する単量体に由来する構造単位とを有する共重合体である、樹脂[K1]及び樹脂[K2]が好ましく、炭素数2〜4の環状エーテル構造とエチレン性不飽和結合とを有する単量体に由来する構造単位が、それぞれ、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレートに由来する構造単位である樹脂[K1]及び樹脂[K2]がより好ましい。 Among them, as the resin (A), a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, a cyclic ether structure having 2 to 4 carbon atoms, and ethylenic unsaturated Resin [K1] and resin [K2], which are copolymers having a structural unit derived from a monomer having a bond, are preferable, and a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond The resin [K1] and the resin [K2] are structural units derived from 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate, respectively. Is more preferable.
樹脂(A)のポリスチレン換算の重量平均分子量は、好ましくは3,000〜100,000であり、より好ましくは5,000〜50,000である。樹脂(A)の重量平均分子量が上記の範囲にあると、感光性樹脂組成物は塗布性に優れる傾向があり、またパターンを形成する際の現像時に未硬化塗膜の画素部分の膜減りが生じにくく、さらに現像時に未硬化塗膜の非画素部分の現像液への溶解性に優れる傾向がある。
樹脂(A)の分子量分布[重量平均分子量(Mw)/数平均分子量(Mn)]は、好ましくは1.1〜6であり、より好ましくは1.2〜4である。
樹脂(A)の酸価は、好ましくは20〜150mg−KOH/gであり、好ましくは40〜135mg−KOH/g、より好ましくは50〜135mg−KOH/gである。ここで酸価は樹脂1gを中和するに必要な水酸化カリウムの量(mg)として測定される値であり、例えば水酸化カリウム水溶液を用いて滴定することにより求めることができる。
The weight average molecular weight in terms of polystyrene of the resin (A) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000. When the weight average molecular weight of the resin (A) is in the above range, the photosensitive resin composition tends to be excellent in coating property, and the film portion of the pixel portion of the uncured coating film is reduced during development when forming a pattern. In addition, it tends to be less likely to occur, and further tends to be excellent in solubility in a non-pixel portion of an uncured coating film during development.
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (A) is preferably 1.1 to 6, and more preferably 1.2 to 4.
The acid value of the resin (A) is preferably 20 to 150 mg-KOH / g, preferably 40 to 135 mg-KOH / g, more preferably 50 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin, and can be determined by titration using, for example, an aqueous potassium hydroxide solution.
樹脂(A)の含有量は、樹脂(A)及び重合性化合物(B)の合計量に対して、好ましくは5〜95質量%、より好ましくは20〜80質量%であり、さらに好ましくは40〜60質量%である。樹脂(A)の含有量が、上記の範囲にあると、現像性、密着性、耐溶剤性及び機械特性に優れる傾向がある。 The content of the resin (A) is preferably 5 to 95% by mass, more preferably 20 to 80% by mass, and still more preferably 40% with respect to the total amount of the resin (A) and the polymerizable compound (B). -60 mass%. When content of resin (A) exists in said range, there exists a tendency which is excellent in developability, adhesiveness, solvent resistance, and a mechanical characteristic.
本発明の感光性樹脂組成物は、重合性化合物(B)を含む。
重合性化合物(B)は、重合開始剤(C)から発生した活性ラジカルによって重合しうる化合物であって、例えば、重合性のエチレン性不飽和二重結合を有する化合物等であり、好ましくは(メタ)アクリル酸エステル化合物が挙げられる。
The photosensitive resin composition of the present invention contains a polymerizable compound (B).
The polymerizable compound (B) is a compound that can be polymerized by active radicals generated from the polymerization initiator (C), and is, for example, a compound having a polymerizable ethylenically unsaturated double bond, preferably ( A meth) acrylic acid ester compound is mentioned.
エチレン性不飽和二重結合を1つ有する重合性化合物(B)としては、前記(a)、(b)及び(c)として挙げた化合物が挙げられ、中でも、(メタ)アクリル酸エステル類が好ましい。 Examples of the polymerizable compound (B) having one ethylenically unsaturated double bond include the compounds mentioned as the above (a), (b) and (c). Among them, (meth) acrylic acid esters include preferable.
エチレン性不飽和二重結合を2つ有する重合性化合物(B)としては、1,3−ブタンジオールジ(メタ)アクリレート、1,3−ブタンジオール(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジアクリレート、ビスフェノールAのビス(アクリロイロキシエチル)エーテル、エトキシ化ビスフェノールAジ(メタ)アクリレート、プロポキシ化ネオペンチルグリコールジ(メタ)アクリレート、エトキシ化ネオペンチルグリコールジ(メタ)アクリレート、3−メチルペンタンジオールジ(メタ)アクリレート等が挙げられる。 Examples of the polymerizable compound (B) having two ethylenically unsaturated double bonds include 1,3-butanediol di (meth) acrylate, 1,3-butanediol (meth) acrylate, and 1,6-hexanediol diene. (Meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di Acrylate, bis (acryloyloxyethyl) ether of bisphenol A, ethoxylated bisphenol A di (meth) acrylate, propoxylated neopentyl glycol di (meth) acrylate, ethoxylated neopentyl glycol di Meth) acrylate, 3-methyl-pentanediol di (meth) acrylate.
エチレン性不飽和二重結合を3つ以上有する重合性化合物(B)としては、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリス(2−ヒドロキシエチル)イソシアヌレートトリ(メタ)アクリレート、エトキシ化トリメチロールプロパントリ(メタ)アクリレート、プロポキシ化トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、トリペンタエリスリトールテトラ(メタ)アクリレート、トリペンタエリスリトールペンタ(メタ)アクリレート、トリペンタエリスリトールヘキサ(メタ)アクリレート、トリペンタエリスリトールヘプタ(メタ)アクリレート、トリペンタエリスリトールオクタ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレートと酸無水物との反応物、ジペンタエリスリトールペンタ(メタ)アクリレートと酸無水物との反応物、トリペンタエリスリトールヘプタ(メタ)アクリレートと酸無水物カプロラクトン変性トリメチロールプロパントリ(メタ)アクリレート、カプロラクトン変性ペンタエリスリトールトリ(メタ)アクリレート、カプロラクトン変性トリス(2−ヒドロキシエチル)イソシアヌレートトリ(メタ)アクリレート、カプロラクトン変性ペンタエリスリトールテトラ(メタ)アクリレート、カプロラクトン変性ジペンタエリスリトールペンタ(メタ)アクリレート、カプロラクトン変性ジペンタエリスリトールヘキサ(メタ)アクリレート、カプロラクトン変性トリペンタエリスリトールテトラ(メタ)アクリレート、カプロラクトン変性トリペンタエリスリトールペンタ(メタ)アクリレート、カプロラクトン変性トリペンタエリスリトールヘキサ(メタ)アクリレート、カプロラクトン変性トリペンタエリスリトールヘプタ(メタ)アクリレート、カプロラクトン変性トリペンタエリスリトールオクタ(メタ)アクリレート、カプロラクトン変性ペンタエリスリトールトリ(メタ)アクリレートと酸無水物との反応物、カプロラクトン変性ジペンタエリスリトールペンタ(メタ)アクリレートと酸無水物との反応物、カプロラクトン変性トリペンタエリスリトールヘプタ(メタ)アクリレートと酸無水物等が挙げられる。中でも、3官能以上のモノマーが好ましく、ジペンタエリスリトールヘキサ(メタ)アクリレートがより好ましい。 Examples of the polymerizable compound (B) having three or more ethylenically unsaturated double bonds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meta) ) Acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate , Tripentaerythritol tetra (meth) acrylate, tripentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripenta Lithritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, reaction product of pentaerythritol tri (meth) acrylate and acid anhydride, reaction product of dipentaerythritol penta (meth) acrylate and acid anhydride, Tripentaerythritol hepta (meth) acrylate and acid anhydride caprolactone modified trimethylolpropane tri (meth) acrylate, caprolactone modified pentaerythritol tri (meth) acrylate, caprolactone modified tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, Caprolactone-modified pentaerythritol tetra (meth) acrylate, caprolactone-modified dipentaerythritol penta (meth) acrylate, caprolactone-modified dipe Taerythritol hexa (meth) acrylate, caprolactone-modified tripentaerythritol tetra (meth) acrylate, caprolactone-modified tripentaerythritol penta (meth) acrylate, caprolactone-modified tripentaerythritol hexa (meth) acrylate, caprolactone-modified tripentaerythritol hepta (meth) Acrylate, caprolactone-modified tripentaerythritol octa (meth) acrylate, reaction product of caprolactone-modified pentaerythritol tri (meth) acrylate and acid anhydride, reaction product of caprolactone-modified dipentaerythritol penta (meth) acrylate and acid anhydride, Examples include caprolactone-modified tripentaerythritol hepta (meth) acrylate and acid anhydrides. Among these, a tri- or higher functional monomer is preferable, and dipentaerythritol hexa (meth) acrylate is more preferable.
重合性化合物(B)の含有量は、樹脂(A)及び重合性化合物(B)の合計量に対して、好ましくは5〜95質量%、より好ましくは20〜80質量%である。重合性化合物(B)の含有量が、前記の範囲にあると、感度や、硬化されたパターンの強度や平滑性、信頼性、機械強度が良好になる傾向がある。 The content of the polymerizable compound (B) is preferably 5 to 95% by mass and more preferably 20 to 80% by mass with respect to the total amount of the resin (A) and the polymerizable compound (B). When the content of the polymerizable compound (B) is in the above range, the sensitivity, the strength and smoothness of the cured pattern, the reliability, and the mechanical strength tend to be good.
本発明の感光性樹脂組成物は、重合開始剤(C)を含み、重合開始剤(C)は式(1)で表される化合物(以下「化合物(1)」という場合がある)を含む。 The photosensitive resin composition of the present invention contains a polymerization initiator (C), and the polymerization initiator (C) contains a compound represented by the formula (1) (hereinafter sometimes referred to as “compound (1)”). .
式(1)中、Ra1及びRa2は、それぞれ独立に、Ra11、ORa11、CORa11、SRa11、CONRa12Ra13又はCNを表し、
Ra11、Ra12及びRa13は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基を表し、
Ra11、Ra12及びRa13で表わされる基の水素原子は、ORa21、CORa21、SRa21、NRa22Ra23、CONRa22Ra23、−NRa22−ORa23、−N(CORa22)−OCORa23、−C(=N−ORa21)−Ra22、−C(=N−OCORa21)−Ra22、CN、ハロゲン原子、又はCOOR21で置換されていてもよく、
Ra21、Ra22及びRa23は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基を表し、
Ra21、Ra22及びRa23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよく、
Ra11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa24−、−NRa24CO−、−NRa24COO−、−OCONRa24−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、
Ra24は、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアリールアルキル基又は炭素数2〜20の複素環基を表し、
Ra11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、Ra12とRa13及びRa22とRa23はそれぞれ一緒になって環を形成していてもよい。本明細書において、「Ra12とRa13及びRa22とRa23はそれぞれ一緒になって環を形成している」とは、「Ra12とRa13及びRa22とRa23はそれぞれ一緒になって接続する窒素原子、炭素原子または酸素原子とともに環を形成している」ことを意味する。
Ra3及びRa4は、それぞれ独立に、Ra11、ORa11、SRa11、CORa11、CONRa12Ra13、NRa12CORa11、OCORa11、COORa11、SCORa11、OCSRa11、COSRa11、CSORa11、CN又はハロゲン原子を表し、
s及びtは、それぞれ独立に、0〜4の整数を表し、
Lは、酸素原子、硫黄原子、セレン原子、CRa31Ra32、CO、NRa33又はPRa34を表し、
Ra31、Ra32、Ra33またはRa34は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基又は炭素数7〜30のアラルキル基を表し、
Ra31、Ra32、Ra33及びRa34で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよい。本明細書において「Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成している」とは、「Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって接続する窒素原子またはりん原子とともに環を形成している」ことを意味する。
Ra5は、ヒドロキシ基、カルボキシ基又は式(2)
(式(2)中、L1は、−O−、−S−、−NRa22−、−NRa22CO−、−SO2−、−CS−、−OCO−又は−COO−を表し、
L2は、炭素数1〜20のアルキル基からv個の水素原子を除いた基、炭素数6〜30のアリール基からv個の水素原子を除いた基、炭素数7〜30のアラルキル基からv個の水素原子を除いた基又は炭素数2〜20の複素環基からv個の水素原子を除いた基を表し、
L2で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa22−、−NRa22COO−、−OCONRa22−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、該アルキレン部分は分枝鎖状であってもよく、環状であってもよく、
Ra6は、ORa41、SRa41、CONRa42Ra43、NRa42CORa43、OCORa41、COORa41、SCORa41、OCSRa41、COSRa41、CSORa41、CN又はハロゲン原子を表し、
Ra41、Ra42またはRa43は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基又は炭素数7〜30のアラルキル基を表し、Ra41、Ra42及びRa43で表される基がアルキル部分を有する場合、該アルキル部分は分枝鎖状であってもよく、環状であってもよく、Ra42とRa43は、一緒になって環を形成していてもよい。本明細書において「Ra42とRa43は、一緒になって環を形成している」とは、「Ra42とRa43は、一緒になってそれぞれが接続する窒素原子または炭素原子とともに環を形成している」ことを意味する。
vは1〜3の整数を表す。)
で表される基を表す。
In formula (1), R a1 and R a2 each independently represent R a11 , OR a11 , COR a11 , SR a11 , CONR a12 R a13 or CN,
R a11 , R a12 and R a13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or an alkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group,
The hydrogen atoms of the groups represented by R a11 , R a12 and R a13 are OR a21 , COR a21 , SR a21 , NR a22 R a23 , CONR a22 R a23 , —NR a22 —OR a23 , —N (COR a22 ) — OCOR a23 , —C (═N—OR a21 ) —R a22 , —C (═N—OCOR a21 ) —R a22 , CN, halogen atom, or COOR 21 may be substituted,
R a21 , R a22 and R a23 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or an alkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group,
The hydrogen atom of the group represented by R a21 , R a22 and R a23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group,
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 has an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR a24 -, - NR a24 CO -, - NR a24 COO -, - OCONR a24 -, - SCO -, - COS -, - OCS- or -CSO- by which it may be interrupted 1 to 5 times,
R a24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 has an alkyl moiety, the alkyl moiety may be branched or cyclic. In addition, R a12 and R a13 and R a22 and R a23 may be combined to form a ring. In the present specification, “R a12 and R a13 and R a22 and R a23 are combined to form a ring” means “R a12 and R a13 and R a22 and R a23 are each combined. A nitrogen atom, a carbon atom or an oxygen atom connected to each other.
R a3 and R a4 are each independently, R a11, OR a11, SR a11, COR a11, CONR a12 R a13, NR a12 COR a11, OCOR a11, COOR a11, SCOR a11, OCSR a11, COSR a11, CSOR a11 , CN or a halogen atom,
s and t each independently represent an integer of 0 to 4,
L represents an oxygen atom, a sulfur atom, a selenium atom, CR a31 R a32 , CO, NR a33 or PR a34 ,
R a31 , R a32 , R a33 or R a34 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms,
When the group represented by R a31 , R a32 , R a33 and R a34 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R a31 , R a32 , R a33 and R a34 may independently form a ring together with one of the adjacent benzene rings. In the present specification, “R a31 , R a32 , R a33 and R a34 each independently form a ring together with one of the adjacent benzene rings” means “R a31 , R a32. , R a33 and R a34 each independently form a ring with a nitrogen atom or a phosphorus atom connected together with one of the adjacent benzene rings.
R a5 is a hydroxy group, a carboxy group or a formula (2)
(In the formula (2), L 1 represents —O—, —S—, —NR a22 —, —NR a22 CO— , —SO 2 —, —CS—, —OCO— or —COO—,
L 2 is a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. A group in which v hydrogen atoms are removed from or a group in which v hydrogen atoms are removed from a heterocyclic group having 2 to 20 carbon atoms,
When the group represented by L 2 has an alkylene moiety, the alkylene moiety is —O—, —S—, —COO— , —OCO— , —NR a22 —, —NR a22 COO— , —OCONR a22 —. , -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times, and the alkylene moiety may be branched or cyclic,
R a6 represents OR a41 , SR a41 , CONR a42 R a43 , NR a42 COR a43 , OCOR a41 , COOR a41 , SCOR a41 , OCSR a41 , COSR a41 , CSOR a41 , CN or a halogen atom,
R a41 , R a42 or R a43 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms, and R a41 , R When the group represented by a42 and R a43 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R a42 and R a43 together form a ring. It may be formed. In the present specification, “R a42 and R a43 together form a ring” means “R a42 and R a43 together form a ring together with the nitrogen atom or carbon atom to which each is connected. It means “forming”.
v represents an integer of 1 to 3. )
Represents a group represented by
式(1)中のRa11、Ra12、Ra13、Ra21、Ra22、Ra23、Ra24、Ra31、Ra32、Ra33及びRa34、並びに式(2)中のRa22、Ra41、Ra42、及びRa43を表す炭素数1〜20のアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、s−ブチル基、t−ブチル基、ペンチル基、イソペンチル基、t−ペンチル基、ヘキシル基、ヘプチル基、オクチル基、イソオクチル基、2−エチルヘキシル基、t−オクチル基、ノニル基、イソノニル基、デシル基、イソデシル基、ウンデシル基、ドデシル基、テトラデシル基、ヘキサデシル基、オクタデシル基、イコシル基、シクロペンチル基、シクロヘキシル基、シクロヘキシルメチル基等が挙げられる。 R a11 , R a12 , R a13 , R a21 , R a22 , R a23 , R a24 , R a31 , R a32 , R a33 and R a34 in formula (1), and R a22 , R in formula (2) Examples of the alkyl group having 1 to 20 carbon atoms representing a41 , Ra42 and Ra43 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an s-butyl group, and a t-butyl group. , Pentyl, isopentyl, t-pentyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl Group, tetradecyl group, hexadecyl group, octadecyl group, icosyl group, cyclopentyl group, cyclohexyl group, cyclohexylmethyl group and the like.
式(1)中のRa11、Ra12、Ra13、Ra21、Ra22、Ra23、Ra24、Ra31、Ra32、Ra33及びRa34、並びに式(2)中のRa22、Ra41、Ra42、及びRa43を表す炭素数6〜30のアリール基としては、例えば、フェニル基、トリル基、キシリル基、エチルフェニル基、ナフチル基、アントリル基、フェナントリル基、上記アルキル基で1つ以上置換されたフェニル基、ビフェニリル基、ナフチル基、アントリル基等が挙げられる。 R a11 , R a12 , R a13 , R a21 , R a22 , R a23 , R a24 , R a31 , R a32 , R a33 and R a34 in formula (1), and R a22 , R in formula (2) Examples of the aryl group having 6 to 30 carbon atoms representing a41 , Ra42 , and Ra43 include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and the above alkyl group. One or more substituted phenyl group, biphenylyl group, naphthyl group, anthryl group and the like can be mentioned.
式(1)中のRa11、Ra12、Ra13、Ra21、Ra22、Ra23、Ra24、Ra31、Ra32、Ra33及びRa34、並びに式(2)中のRa22、Ra41、Ra42、及びRa43を表す炭素数7〜30のアラルキル基としては、例えば、ベンジル基、α−メチルベンジル基、α、α−ジメチルベンジル基、フェニルエチル基等が挙げられる。 R a11 , R a12 , R a13 , R a21 , R a22 , R a23 , R a24 , R a31 , R a32 , R a33 and R a34 in formula (1), and R a22 , R in formula (2) Examples of the C 7-30 aralkyl group representing a 41 , R a42 , and R a43 include benzyl group, α-methylbenzyl group, α, α-dimethylbenzyl group, phenylethyl group, and the like.
式(1)中のRa11、Ra12、Ra13、Ra21、Ra22、Ra23及びRa24を表す炭素数2〜20の複素環基としては、例えば、ピリジル基、ピリミジル基、フリル基、チエニル基、テトラヒドロフリル基、ジオキソラニル基、ベンゾオキサゾール−2−イル基、テトラヒドロピラニル基、ピロリジル基、イミダゾリジル基、ピラゾリジル基、チアゾリジル基、イソチアゾリジル基、オキサゾリジル基、イソオキサゾリジル基、ピペリジル基、ピペラジル基、モルホリニル基等が挙げられ、好ましくは5〜7員複素環である。 Examples of the heterocyclic group having 2 to 20 carbon atoms representing R a11 , R a12 , R a13 , R a21 , R a22 , R a23 and R a24 in the formula (1) include a pyridyl group, a pyrimidyl group, and a furyl group. , Thienyl group, tetrahydrofuryl group, dioxolanyl group, benzoxazol-2-yl group, tetrahydropyranyl group, pyrrolidyl group, imidazolidyl group, pyrazolidyl group, thiazolidyl group, isothiazolidyl group, isoxazolidyl group, isoxazolidyl group, piperidyl group , A piperazyl group, a morpholinyl group, and the like, preferably a 5- to 7-membered heterocyclic ring.
式(1)中のRa12とRa13、Ra22とRa23、及び式(2)中のRa42とRa43とが一緒になって形成し得る環、並びにRa31、Ra32、Ra33及びRa34が隣接するベンゼン環と一緒になって形成し得る環としては、例えば、シクロペンタン環、シクロヘキサン環、シクロペンテン環、ベンゼン環、ピペリジン環、モルホリン環、ラクトン環、ラクタム環等が挙げられ、好ましくは5〜7員環である。 R a12 and R a13 , R a22 and R a23 in formula (1), and R a42 and R a43 in formula (2) can be formed together, and R a31 , R a32 , R a33 Examples of the ring that R a34 can form together with the adjacent benzene ring include a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a benzene ring, a piperidine ring, a morpholine ring, a lactone ring, and a lactam ring. , Preferably a 5- to 7-membered ring.
式(2)中のL2は、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基からv個の水素原子を除いた基を表す。 L 2 in the formula (2) is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms. Represents a group excluding a hydrogen atom.
炭素数1〜20のアルキル基からv個の水素原子を除いた基としては、例えば、vが1の場合、メチレン基、エチレン基、プロピレン基、メチルエチレン基、ブチレン基、1−メチルプロピレン基、2−メチルプロピレン基、1,2−ジメチルプロピレン基、1,3−ジメチルプロピレン基、1−メチルブチレン基、2−メチルブチレン基、3−メチルブチレン基、4−メチルブチレン基、2,4−ジメチルブチレン基、1,3−ジメチルブチレン基、ペンチレン基、へキシレン基、ヘプチレン基、オクチレン基、ノニレン基、デシレン基、ドデシレン基、トリデシレン基、テトラデシレン基、ペンタデシレン基、エタン−1,1−ジイル基、プロパン−2,2−ジイル基等のアルキレン基が挙げられる。 Examples of the group in which v hydrogen atoms are removed from an alkyl group having 1 to 20 carbon atoms include, for example, when v is 1, a methylene group, an ethylene group, a propylene group, a methylethylene group, a butylene group, and a 1-methylpropylene group. 2-methylpropylene group, 1,2-dimethylpropylene group, 1,3-dimethylpropylene group, 1-methylbutylene group, 2-methylbutylene group, 3-methylbutylene group, 4-methylbutylene group, 2,4 -Dimethylbutylene group, 1,3-dimethylbutylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, dodecylene group, tridecylene group, tetradecylene group, pentadecylene group, ethane-1,1- Examples thereof include alkylene groups such as a diyl group and a propane-2,2-diyl group.
炭素数6〜30のアリール基からv個の水素原子を除いた基としては、例えば、vが1の場合、1,2−フェニレン基、1,3−フェニレン基、1,4−フェニレン基、2,6−ナフチレン基、1,4−ナフチレン基、2,5−ジメチル−1,4−フェニレン基、ジフェニルメタン−4,4’−ジイル基、2,2−ジフェニルプロパン−4,4’−ジイル基、ジフェニルスルフィド−4,4’−ジイル基、ジフェニルスルホン−4,4’−ジイル基等のアリーレン基が挙げられる。 Examples of the group in which v hydrogen atoms are removed from an aryl group having 6 to 30 carbon atoms include, when v is 1, 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 2,6-naphthylene group, 1,4-naphthylene group, 2,5-dimethyl-1,4-phenylene group, diphenylmethane-4,4′-diyl group, 2,2-diphenylpropane-4,4′-diyl Groups, arylene groups such as diphenylsulfide-4,4′-diyl group, diphenylsulfone-4,4′-diyl group, and the like.
炭素数7〜30のアラルキル基からv個の水素原子を除いた基としては、例えば、vが1の場合、式(a)で表される基及び式(b)で表される基等が挙げられる。
[式(a)及び(b)中、L3及びL5は、炭素数1〜10のアルキレン基を表し、L4及びL6は、単結合又は炭素数1〜10のアルキレン基を表す。]
炭素数1〜10のアルキレン基としては、例えば、メチレン基、エチレン基、プロピレン基、メチルエチレン基、ブチレン基、1−メチルプロピレン基、2−メチルプロピレン基、1,2−ジメチルプロピレン基、1,3−ジメチルプロピレン基、1−メチルブチレン基、2−メチルブチレン基、3−メチルブチレン基、4−メチルブチレン基、2,4−ジメチルブチレン基、1,3−ジメチルブチレン基、ペンチレン基、へキシレン基、ヘプチレン基、オクチレン基、ノニレン基、デシレン基等が挙げられる。
Examples of the group in which v hydrogen atoms are removed from an aralkyl group having 7 to 30 carbon atoms include, for example, when v is 1, a group represented by the formula (a) and a group represented by the formula (b). Can be mentioned.
[In Formulas (a) and (b), L 3 and L 5 represent an alkylene group having 1 to 10 carbon atoms, and L 4 and L 6 represent a single bond or an alkylene group having 1 to 10 carbon atoms. ]
Examples of the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, propylene group, methylethylene group, butylene group, 1-methylpropylene group, 2-methylpropylene group, 1,2-dimethylpropylene group, 1 , 3-dimethylpropylene group, 1-methylbutylene group, 2-methylbutylene group, 3-methylbutylene group, 4-methylbutylene group, 2,4-dimethylbutylene group, 1,3-dimethylbutylene group, pentylene group, Examples include a hexylene group, a heptylene group, an octylene group, a nonylene group, and a decylene group.
炭素数2〜20の複素環基からv個の水素原子を除いた基としては、例えば、vが1の場合、2,5−ピリジンジイル基、2,6−ピリジンジイル基、2,5−ピリミジンジイル基、2,5−チオフェンジイル基、3,4−テトラヒドロフランジイル基、2,5−テトラヒドロフランジイル基、2,5−フランジイル基、3,4−チアゾールジイル基、2,5−ベンゾフランジイル基、2,5−ベンゾチオフェンジイル基、N−メチルインドール−2,5−ジイル基、2,5−ベンゾチアゾールジイル基、2,5−ベンゾオキサゾールジイル基等の2価の複素環基が挙げられる。 Examples of the group in which v hydrogen atoms are removed from a heterocyclic group having 2 to 20 carbon atoms include, for example, when v is 1, 2,5-pyridinediyl group, 2,6-pyridinediyl group, 2,5- Pyrimidinediyl group, 2,5-thiophenediyl group, 3,4-tetrahydrofurandiyl group, 2,5-tetrahydrofurandiyl group, 2,5-furandiyl group, 3,4-thiazoldiyl group, 2,5-benzofurandyl And divalent heterocyclic groups such as 2,5-benzothiophenediyl group, N-methylindole-2,5-diyl group, 2,5-benzothiazolediyl group, 2,5-benzoxazolediyl group It is done.
式(1)中のRa3及びRa4、式(2)中のRa6を表すハロゲン原子、並びに式(1)中のRa11、Ra12、Ra13、Ra21、Ra22及びRa23が置換基として有してもよいハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。 R a3 and R a4 in formula (1), a halogen atom representing R a6 in formula (2), and R a11 , R a12 , R a13 , R a21 , R a22 and R a23 in formula (1) are Examples of the halogen atom that may be present as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
式(1)中のRa11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基か、あるいは式(2)中のL2で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa24−、−NRa24CO−、−NRa24COO−、−OCONRa24−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、この時中断する結合基は1種又は2種以上の基でもよく、連続して中断し得る基の場合は2つ以上連続して中断してもよい。
式(1)中のRa11、Ra12、Ra13、Ra21、Ra22、Ra23、Ra31、Ra32、Ra33またはRa34で表される基、あるいは式(2)中のRa41、Ra42またはRa43で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよい。
また、式(2)中のL2で表される基がアルキレン部分を有する場合、該アルキレン部分は、分枝鎖状であってもよく、環状であってもよい。
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 in formula (1) or the group represented by L 2 in formula (2) has an alkylene moiety , the alkylene moiety, -O -, - S -, - COO -, - OCO -, - NR a24 -, - NR a24 CO -, - NR a24 COO -, - OCONR a24 -, - SCO -, - COS It may be interrupted 1 to 5 times by-, -OCS- or -CSO-, and the linking group interrupted at this time may be one kind or two or more groups, and in the case of a group which can be interrupted successively, 2 Two or more may be interrupted continuously.
R a11 in equation (1), R a12, R a13, R a21, R a22, R a23, R a31, R a32, groups represented by R a33 or R a34, or in the formula (2), R a41 , R a42 or R a43 has an alkyl moiety, the alkyl moiety may be branched or cyclic.
Moreover, when the group represented by L 2 in Formula (2) has an alkylene moiety, the alkylene moiety may be branched or cyclic.
化合物(1)の中でも、式(3):
[式(3)中、L’は、硫黄原子又はNRa50を表し、Ra50は、直鎖状、分枝鎖状又は環状の炭素数1〜20のアルキル基を表し、Ra1、Ra2、Ra3、Ra4、Ra5、s及びtは、上記と同じ意味を表す。]
で表される化合物が好ましい。
Among the compounds (1), the formula (3):
[In the formula (3), L ′ represents a sulfur atom or NR a50 , R a50 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, R a1 , R a2 , R a3 , R a4 , R a5 , s and t have the same meaning as described above. ]
The compound represented by these is preferable.
さらに、式(4):
[式(4)中、Ra51及びRa52は、それぞれ独立に、炭素数1〜20のアルキル基を表し、Ra53は、ヒドロキシ基、カルボキシ基又は式(5)
(式(5)中、L11は、−O−又は*−OCO−を表し、*はL12との結合手を表し、L12は、炭素数1〜20のアルキレン基を表し、該アルキレン基は、1〜3個の−O−により中断されていてもよく、Ra54は、ORa55又はCOORa55を表し、Ra55は、水素原子又は炭素数1〜6のアルキル基を表す。)
で表される基を表す。]
で表される化合物がより好ましい。
化合物(1)がこれらの化合物であると、化合物の製造が容易であり、さらに該化合物を含む感光性樹脂組成物から高感度でパターンを製造することができる。
Furthermore, Formula (4):
[Equation (4), R a51 and R a52 each independently represent an alkyl group having 1 to 20 carbon atoms, R a53 is a hydroxy group, a carboxy group, or the formula (5)
(In the formula (5), L 11 represents -O- or * -OCO-, * represents a bond to L 12, L 12 represents an alkylene group having 1 to 20 carbon atoms, said alkylene The group may be interrupted by 1 to 3 —O—, R a54 represents OR a55 or COOR a55 , and R a55 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.)
Represents a group represented by ]
The compound represented by these is more preferable.
When the compound (1) is any of these compounds, it is easy to produce the compound, and a pattern can be produced with high sensitivity from the photosensitive resin composition containing the compound.
Ra51及びRa52を表すアルキル基の炭素数は、好ましくは1〜10であり、より好ましくは1〜4である。
Ra53は、好ましくは式(5)で表される基である。
L12を表すアルキレン基の炭素数は、好ましくは1〜10であり、より好ましくは1〜4である。
Ra54は、好ましくはヒドロキシ基又はカルボキシ基であり、より好ましくはヒドロキシ基である。
Carbon number of the alkyl group representing R a51 and R a52 is preferably 1 to 10, more preferably 1 to 4.
R a53 is preferably a group represented by Formula (5).
The number of carbon atoms of the alkylene group representing L 12 is preferably 1 to 10, more preferably 1 to 4.
R a54 is preferably a hydroxy group or a carboxy group, more preferably a hydroxy group.
化合物(1)としては、下記式で表される化合物が挙げられる。これらの化合物であると、パターン形成時の露光マージンが広くなる傾向がある。中でも、化合物No.2、化合物No.26、化合物No.44、化合物No.45及び化合物No.46が好ましい。 Examples of the compound (1) include compounds represented by the following formula. These compounds tend to increase the exposure margin during pattern formation. Among these, compound no. 2, Compound No. 26, Compound No. 44, compound no. 45 and compound no. 46 is preferred.
化合物(1)の製造方法は、特に限定されないが、例えば、特開2011−132215号公報に記載の方法で製造できる。 Although the manufacturing method of compound (1) is not specifically limited, For example, it can manufacture by the method of Unexamined-Japanese-Patent No. 2011-132215.
化合物(1)の含有量は、重合開始剤(C)の総量に対して、好ましくは30〜100質量%、より好ましくは50〜100質量%である。化合物(1)の含有量が前記の範囲内にあると、パターン製造時の露光マージンが広い傾向がある。 The content of the compound (1) is preferably 30 to 100% by mass, more preferably 50 to 100% by mass, based on the total amount of the polymerization initiator (C). When the content of the compound (1) is within the above range, the exposure margin during pattern production tends to be wide.
本発明の感光性樹脂組成物は、重合開始剤(C)として、化合物(1)とは異なる重合開始剤を含んでいてもよい。重合開始剤(C)としては、光又は熱の作用により重合を開始する化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。
重合開始剤(C)として、例えば、ビイミダゾール化合物、アルキルフェノン化合物、トリアジン化合物、アシルホスフィンオキサイド化合物、オキシム化合物が挙げられる。また、特開2008−181087号公報に記載された光及び/又は熱カチオン重合開始剤(例えば、オニウムカチオンとルイス酸由来のアニオンとから構成されているもの)を用いてもよい。中でも、ビイミダゾール化合物、アルキルフェノン化合物及びオキシム化合物からなる群から選ばれる少なくとも1種であることが好ましく、ビイミダゾール化合物、アルキルフェノン化合物及びオキシム化合物からなる群から選ばれる2種以上であることがより好ましい。これらの重合開始剤であると、特に、高感度になる傾向があり好ましい。
The photosensitive resin composition of this invention may contain the polymerization initiator different from a compound (1) as a polymerization initiator (C). The polymerization initiator (C) is not particularly limited as long as it is a compound that initiates polymerization by the action of light or heat, and a known polymerization initiator can be used.
Examples of the polymerization initiator (C) include biimidazole compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and oxime compounds. Moreover, you may use the light and / or thermal cationic polymerization initiator (For example, what is comprised from the onium cation and the anion derived from a Lewis acid) described in Unexamined-Japanese-Patent No. 2008-181087. Among these, at least one selected from the group consisting of a biimidazole compound, an alkylphenone compound, and an oxime compound is preferable, and two or more types selected from the group consisting of a biimidazole compound, an alkylphenone compound, and an oxime compound are preferable. More preferred. These polymerization initiators are particularly preferred because they tend to be highly sensitive.
前記ビイミダゾール化合物としては、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾール、2,2’−ビス(2,3−ジクロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾール(例えば、特開平6−75372号公報、特開平6−75373号公報等参照。)、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾール、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラ(アルコキシフェニル)ビイミダゾール、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラ(ジアルコキシフェニル)ビイミダゾール、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラ(トリアルコキシフェニル)ビイミダゾール(例えば、特公昭48−38403号公報、特開昭62−174204号公報等参照。)、4,4’5,5’−位のフェニル基がカルボアルコキシ基により置換されているイミダゾール化合物(例えば、特開平7−10913号公報等参照。)等が挙げられる。好ましくは2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾール、2,2’−ビス(2、3−ジクロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾール、2,2’−ビス(2、4−ジクロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾールが挙げられる。 Examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2 -Chlorophenyl) -4,4 ', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (trialkoxy) Nyl) biimidazole (for example, see JP-B-48-38403, JP-A-62-174204, etc.), and the phenyl group at the 4,4′5,5′-position is substituted with a carboalkoxy group. Examples thereof include imidazole compounds (for example, see JP-A-7-10913). Preferably, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) -4,4 ′, 5 Examples include 5'-tetraphenylbiimidazole and 2,2'-bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole.
前記のアルキルフェノン化合物は、α−ヒドロキシアルキルフェノン、α−アルコキシアルキルフェノン又はα−(N−置換アミノ)アルキルフェノンを部分構造として有する化合物であり、具体的には、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、ベンジルジメチルケタール、2−ヒドロキシ−1−〔4−(2−ヒドロキシエトキシ)フェニル〕−2−メチルプロパン−1−オン、2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]―フェニル}−2−メチル−プロパン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−(4−メチルチオフェニル)−2−モルホリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタン−1−オン、2−(2−メチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(3−メチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(4−メチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−エチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−プロピルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−ブチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2,3−ジメチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2、4−ジメチルベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−クロロベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−ブロモベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(3−クロロベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(4−クロロベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(3−ブロモベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(4−ブロモベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−メトキシベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(3−メトキシベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(4−メトキシベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−メチル−4−メトキシベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−メチル−4−ブロモベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−(2−ブロモ−4−メトキシベンジル)−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−ヒドロキシ−2−メチル−1−〔4−(1−メチルビニル)フェニル〕プロパン−1−オンのオリゴマー、2−(ジメチルアミノ)−2−[(4−メチルフェニル)メチル]−1−[4−(4−モルホリニル)フェニル]ブタン−1−オン等が挙げられる。 The alkylphenone compound is a compound having α-hydroxyalkylphenone, α-alkoxyalkylphenone or α- (N-substituted amino) alkylphenone as a partial structure, specifically, diethoxyacetophenone, 2-hydroxy -2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, 2-hydroxy-1 -{4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl} -2-methyl-propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4 -Methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethyl Ruamino-1- (4-morpholinophenyl) butan-1-one, 2- (2-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (3-methylbenzyl) -2 -Dimethylamino-1- (4-morpholinophenyl) butanone, 2- (4-methylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-ethylbenzyl) -2-dimethyl Amino-1- (4-morpholinophenyl) butanone, 2- (2-propylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-butylbenzyl) -2-dimethylamino- 1- (4-morpholinophenyl) butanone, 2- (2,3-dimethylbenzyl) -2-dimethylamino-1- (4-morpholinov Nyl) butanone, 2- (2,4-dimethylbenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-chlorobenzyl) -2-dimethylamino-1- (4-morpholino) Phenyl) butanone, 2- (2-bromobenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (3-chlorobenzyl) -2-dimethylamino-1- (4-morpholinophenyl) Butanone, 2- (4-chlorobenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (3-bromobenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (4-Bromobenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-methoxybenzyl) 2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (3-methoxybenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (4-methoxybenzyl) -2 -Dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-methyl-4-methoxybenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-methyl-4) -Bromobenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- (2-bromo-4-methoxybenzyl) -2-dimethylamino-1- (4-morpholinophenyl) butanone, 2- Hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one oligomer, 2- (dimethylamino) -2 - [(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one, and the like.
前記トリアジン化合物としては、2,4−ビス(トリクロロメチル)−6−(4−メトキシフェニル)−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−(4−メトキシナフチル)−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−ピペロニル−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−(4−メトキシスチリル)−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−〔2−(5−メチルフラン−2−イル)エテニル〕−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−〔2−(フラン−2−イル)エテニル〕−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−〔2−(4−ジエチルアミノ−2−メチルフェニル)エテニル〕−1,3,5−トリアジン、2,4−ビス(トリクロロメチル)−6−〔2−(3,4−ジメトキシフェニル)エテニル〕−1,3,5−トリアジン等が挙げられる。 Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl). ) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (Trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2- Methylphenyl) ete Le] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.
前記アシルホスフィンオキサイド化合物としては、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド等が挙げられる。 Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
前記オキシム化合物としては、N−ベンゾイルオキシ−1−(4−フェニルスルファニルフェニル)ブタン−1−オン−2−イミン、N−エトキシカルボニルオキシ−1−フェニルプロパン−1−オン−2−イミン、N−ベンゾイルオキシ−1−(4−フェニルスルファニルフェニル)オクタン−1−オン−2−イミン、N−アセトキシ−1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]エタン−1−イミン、N−アセトキシ−1−[9−エチル−6−{2−メチル−4−(3,3−ジメチル−2,4−ジオキサシクロペンタニルメチルオキシ)ベンゾイル}−9H−カルバゾール−3−イル]エタン−1−イミン等が挙げられる。イルガキュアOXE01、OXE02(以上、BASF社製)、N−1919(ADEKA社製)等の市販品を用いてもよい。 Examples of the oxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-ethoxycarbonyloxy-1-phenylpropan-1-one-2-imine, N -Benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] Ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H -Carbazol-3-yl] ethane-1-imine and the like. Commercial products such as Irgacure OXE01, OXE02 (manufactured by BASF) and N-1919 (ADEKA) may be used.
さらに重合開始剤(C)としては、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾイン化合物;ベンゾフェノン、o−ベンゾイル安息香酸メチル、4−フェニルベンゾフェノン、4−ベンゾイル−4’−メチルジフェニルサルファイド、3,3’,4,4’−テトラ(tert−ブチルパーオキシカルボニル)ベンゾフェノン、2,4,6−トリメチルベンゾフェノン等のベンゾフェノン化合物;9,10−フェナンスレンキノン、2−エチルアントラキノン、カンファーキノン等のキノン化合物;10−ブチル−2−クロロアクリドン、ベンジル、フェニルグリオキシル酸メチル、チタノセン化合物等が挙げられる。これらは、後述の重合開始助剤(C1)と組み合わせて用いることが好ましい。
また、連鎖移動を起こしうる基を有する光重合開始剤として、特表2002−544205号公報に記載されている光重合開始剤を使用してもよい。
Furthermore, as the polymerization initiator (C), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with a polymerization initiation assistant (C1) described later.
Moreover, you may use the photoinitiator described in the Japanese translations of PCT publication No. 2002-544205 gazette as a photoinitiator which has the group which can raise | generate chain transfer.
重合開始剤(C)の含有量は、樹脂(A)及び重合性化合物(B)の合計量に対して、好ましくは0.5〜30質量%、より好ましくは1〜20質量%であり、さらに好ましくは1〜10質量%である。重合開始剤(C)の含有量が前記の範囲にあると、高感度でパターンを得ることができ、さらに得られるパターンの可視光透過率が高い傾向がある。 The content of the polymerization initiator (C) is preferably 0.5 to 30% by mass, more preferably 1 to 20% by mass, based on the total amount of the resin (A) and the polymerizable compound (B). More preferably, it is 1-10 mass%. When the content of the polymerization initiator (C) is in the above range, a pattern can be obtained with high sensitivity, and the visible light transmittance of the obtained pattern tends to be high.
本発明の感光性樹脂組成物において、さらに、上述した重合開始剤(C)とともに、重合開始助剤(C1)を用いてもよい。重合開始助剤(C1)は、重合開始助剤(C1)は、重合開始剤(C)と組み合わせて用いられ、重合開始剤によって重合が開始された重合性化合物の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤(C1)としては、チオキサントン化合物、チアゾリン化合物、アルコキシアントラセン化合物、アミン化合物及びカルボン酸化合物等が挙げられる。これらと重合開始剤(C)とを組み合わせることで、高感度でパターンを得ることができる。 In the photosensitive resin composition of the present invention, a polymerization initiation assistant (C1) may be used together with the polymerization initiator (C) described above. The polymerization initiation assistant (C1) is used in combination with the polymerization initiator (C1), and is used to accelerate the polymerization of the polymerizable compound initiated by the polymerization initiator. Or a sensitizer. Examples of the polymerization initiation assistant (C1) include thioxanthone compounds, thiazoline compounds, alkoxyanthracene compounds, amine compounds, and carboxylic acid compounds. By combining these with the polymerization initiator (C), a pattern can be obtained with high sensitivity.
チオキサントン化合物としては、2−イソプロピルチオキサントン、4−イソプロピルチオキサントン、2,4−ジエチルチオキサントン、2,4−ジクロロチオキサントン、1−クロロ−4−プロポキシチオキサントン等が挙げられる。 Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.
チアゾリン化合物としては、式(III−1)〜式(III−3)で表される化合物、特開2008−65319号公報記載の化合物等が挙げられる。 Examples of the thiazoline compound include compounds represented by formulas (III-1) to (III-3), and compounds described in JP-A-2008-65319.
アルコキシアントラセン化合物としては、9,10−ジメトキシアントラセン、2−エチル−9,10−ジメトキシアントラセン、9,10−ジエトキシアントラセン、2−エチル−9,10−ジエトキシアントラセン、9,10−ジブトキシアントラセン、2−エチル−9,10−ジブトキシアントラセン、特開2009−139932号公報記載の化合物等が挙げられる。 Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Anthracene, 2-ethyl-9,10-dibutoxyanthracene, compounds described in JP-A-2009-139932, and the like can be mentioned.
アミン化合物としては、トリエタノールアミン、メチルジエタノールアミン、トリイソプロパノールアミン等の脂肪族アミン化合物、4−ジメチルアミノ安息香酸メチル、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸イソアミル、4−ジメチルアミノ安息香酸2−エチルヘキシル、安息香酸2−ジメチルアミノエチル、N,N−ジメチルパラトルイジン、4,4’−ビス(ジメチルアミノ)ベンゾフェノン(通称;ミヒラーズケトン)、4,4’−ビス(ジエチルアミノ)ベンゾフェノンのような芳香族アミン化合物が挙げられる。 Examples of amine compounds include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 4-dimethylamino. Of 2-ethylhexyl benzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (common name; Michler's ketone), 4,4′-bis (diethylamino) benzophenone Such aromatic amine compounds are mentioned.
カルボン酸化合物としては、フェニルスルファニル酢酸、メチルフェニルスルファニル酢酸、エチルフェニルスルファニル酢酸、メチルエチルフェニルスルファニル酢酸、ジメチルフェニルスルファニル酢酸、メトキシフェニルスルファニル酢酸、ジメトキシフェニルスルファニル酢酸、クロロフェニルスルファニル酢酸、ジクロロフェニルスルファニル酢酸、N−フェニルグリシン、フェノキシ酢酸、ナフチルチオ酢酸、N−ナフチルグリシン、ナフトキシ酢酸等の芳香族ヘテロ酢酸類が挙げられる。 Carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N -Aromatic heteroacetic acids such as phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.
重合開始助剤(C1)を含む場合、その含有量は、樹脂(A)及び重合性化合物(B)の合計量に対して、好ましくは0.1〜10質量%、より好ましくは1〜7質量%である。重合開始助剤(C1)の量が前記の範囲にあると、高感度でパターンを得ることができ、得られるパターンは形状が良好である。 When the polymerization initiation assistant (C1) is contained, the content thereof is preferably 0.1 to 10% by mass, more preferably 1 to 7 with respect to the total amount of the resin (A) and the polymerizable compound (B). % By mass. When the amount of the polymerization initiation assistant (C1) is in the above range, a pattern can be obtained with high sensitivity, and the resulting pattern has a good shape.
また、本発明の感光性樹脂組成物は、さらに多官能チオール化合物(T)を含有していてもよい。多官能チオール化合物(T)とは、分子内に2個以上の−SHを有する化合物をいう。特に、脂肪族炭化水素基に由来する炭素原子に結合する−SHを2個以上有する化合物を用いると、本発明の感光性樹脂組成物の感度が高くなる傾向にある。 Moreover, the photosensitive resin composition of this invention may contain the polyfunctional thiol compound (T) further. The polyfunctional thiol compound (T) refers to a compound having two or more —SH in the molecule. In particular, when a compound having two or more —SH bonded to a carbon atom derived from an aliphatic hydrocarbon group is used, the sensitivity of the photosensitive resin composition of the present invention tends to increase.
多官能チオール化合物(T)としては、具体的には、ヘキサンジチオール、デカンジチオール、1,4−ビス(メチルスルファニル)ベンゼン、ブタンジオールビス(3−スルファニルプロピオネート)、ブタンジオールビス(3−スルファニルアセテート)、エチレングリコールビス(3−スルファニルアセテート)、トリメチロールプロパントリス(3−スルファニルアセテート)、ブタンジオールビス(3−スルファニルプロピオネート)、トリメチロールプロパントリス(3−スルファニルプロピオネート)、トリメチロールプロパントリス(3−スルファニルアセテート)、ペンタエリスリトールテトラキス(3−スルファニルプロピオネート)、ペンタエリスリトールテトラキス(3−スルファニルアセテート)、トリスヒドロキシエチルトリス(3−スルファニルプロピオネート)、ペンタエリスリトールテトラキス(3−スルファニルブチレート)、1,4−ビス(3−スルファニルブチルオキシ)ブタン等が挙げられる。 Specific examples of the polyfunctional thiol compound (T) include hexanedithiol, decanedithiol, 1,4-bis (methylsulfanyl) benzene, butanediol bis (3-sulfanylpropionate), butanediol bis (3- Sulfanyl acetate), ethylene glycol bis (3-sulfanyl acetate), trimethylolpropane tris (3-sulfanyl acetate), butanediol bis (3-sulfanylpropionate), trimethylolpropane tris (3-sulfanylpropionate), Trimethylolpropane tris (3-sulfanyl acetate), pentaerythritol tetrakis (3-sulfanylpropionate), pentaerythritol tetrakis (3-sulfanyl acetate), trishydro Shiechirutorisu (3-sulfanyl propionate), pentaerythritol tetrakis (3-sulfanyl butyrate), 1,4-bis (3-sulfanyl-butyloxy) include butane and the like.
多官能チオール化合物(T)の含有量は、重合開始剤(C)に対して、好ましくは0.1〜10質量%、より好ましくは0.5〜7質量%である。多官能チオール化合物(T)の含有量が前記の範囲にあると、感光性樹脂組成物の感度が高くなり、また現像性が良好になる傾向があり好ましい。 The content of the polyfunctional thiol compound (T) is preferably 0.1 to 10% by mass, more preferably 0.5 to 7% by mass with respect to the polymerization initiator (C). When the content of the polyfunctional thiol compound (T) is in the above range, the sensitivity of the photosensitive resin composition is increased and the developability tends to be favorable, which is preferable.
本発明の感光性樹脂組成物は、溶剤(D)を含むことが好ましい。
本発明において使用し得る溶剤としては、例えば、エステル溶剤(−COO−を含む溶剤)、エステル溶剤以外のエーテル溶剤(−O−を含む溶剤)、エーテルエステル溶剤(−COO−と−O−とを含む溶剤)、エステル溶剤以外のケトン溶剤(−CO−を含む溶剤)、アルコール溶剤、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等の中から選択して用いることができる。
The photosensitive resin composition of the present invention preferably contains a solvent (D).
Examples of the solvent that can be used in the present invention include ester solvents (solvents containing —COO—), ether solvents other than ester solvents (solvents containing —O—), ether ester solvents (—COO— and —O— and Selected from the group consisting of ketone solvents other than ester solvents (solvents containing —CO—), alcohol solvents, aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.
エステル溶剤としては、乳酸メチル、乳酸エチル、乳酸ブチル、2−ヒドロキシイソブタン酸メチル、酢酸エチル、酢酸n−ブチル、酢酸イソブチル、ギ酸ペンチル、酢酸イソペンチル、プロピオン酸ブチル、酪酸イソプロピル、酪酸エチル、酪酸ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸プロピル、アセト酢酸メチル、アセト酢酸エチル、シクロヘキサノールアセテート、γ−ブチロラクトンなどが挙げられる。 As ester solvents, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.
エーテル溶剤としては、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、3−メトキシ−1−ブタノール、3−メトキシ−3−メチルブタノール、テトラヒドロフラン、テトラヒドロピラン、1,4−ジオキサン、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジプロピルエーテル、ジエチレングリコールジブチルエーテル、アニソール、フェネトール、メチルアニソールなどが挙げられる。 Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and the like methyl anisole.
エーテルエステル溶剤としては、メトキシ酢酸メチル、メトキシ酢酸エチル、メトキシ酢酸ブチル、エトキシ酢酸メチル、エトキシ酢酸エチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、2−メトキシプロピオン酸メチル、2−メトキシプロピオン酸エチル、2−メトキシプロピオン酸プロピル、2−エトキシプロピオン酸メチル、2−エトキシプロピオン酸エチル、2−メトキシ−2−メチルプロピオン酸メチル、2−エトキシ−2−メチルプロピオン酸エチル、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテートなどが挙げられる。 Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether Acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and the like diethylene glycol monobutyl ether acetate.
ケトン溶剤としては、4−ヒドロキシ−4−メチル−2−ペンタノン、アセトン、2−ブタノン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、4−メチル−2−ペンタノン、シクロペンタノン、シクロヘキサノン、イソホロンなどが挙げられる。 Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone. Etc.
アルコール溶剤としては、メタノール、エタノール、プロパノール、ブタノール、ヘキサノール、シクロヘキサノール、エチレングリコール、プロピレングリコール、グリセリンなどが挙げられる。 Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
芳香族炭化水素溶剤としては、ベンゼン、トルエン、キシレン、メシチレンなどが挙げられる。 Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
アミド溶剤としては、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロリドンなどが挙げられる。
これらの溶剤は、単独でも2種類以上を組み合わせて用いてもよい。
Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
These solvents may be used alone or in combination of two or more.
上記の溶剤のうち、塗布性、乾燥性の点から、1atmにおける沸点が120℃以上180℃以下である有機溶剤が好ましく、中でも、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、ジエチレングリコールメチルエチルエーテル、3−エトキシプロピオン酸エチル、3−メトキシブチルアセテート及び3−メトキシ−1−ブタノールからなる群から選ばれる少なくとも1種を含む溶剤が好ましく、3−メトキシブチルアセテートを含む溶剤がより好ましい。 Among the above-mentioned solvents, organic solvents having a boiling point of 120 ° C. or more and 180 ° C. or less at 1 atm are preferable from the viewpoint of coating properties and drying properties. Among them, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ethyl ether, A solvent containing at least one selected from the group consisting of ethyl 3-ethoxypropionate, 3-methoxybutyl acetate and 3-methoxy-1-butanol is preferred, and a solvent containing 3-methoxybutyl acetate is more preferred.
感光性樹脂組成物における溶剤(D)の含有量は、感光性樹脂組成物に対して、好ましくは60〜95質量%であり、より好ましくは70〜90質量%である。言い換えると、感光性樹脂組成物の固形分は、好ましくは5〜40質量%であり、より好ましくは10〜30質量%である。ここで、固形分とは、感光性樹脂組成物から溶剤(D)を除いた量のことをいう。溶剤(D)の含有量が前記の範囲にあると、感光性樹脂組成物を塗布した膜の平坦性が高い傾向がある。 The content of the solvent (D) in the photosensitive resin composition is preferably 60 to 95% by mass and more preferably 70 to 90% by mass with respect to the photosensitive resin composition. In other words, the solid content of the photosensitive resin composition is preferably 5 to 40% by mass, and more preferably 10 to 30% by mass. Here, solid content means the quantity remove | excluding the solvent (D) from the photosensitive resin composition. When the content of the solvent (D) is in the above range, the flatness of the film coated with the photosensitive resin composition tends to be high.
本発明の感光性樹脂組成物は界面活性剤(E)を含有することが好ましい。界面活性剤としては、例えば、シリコーン系界面活性剤、フッ素系界面活性剤、フッ素原子を有するシリコーン系界面活性剤等が挙げられる。 The photosensitive resin composition of the present invention preferably contains a surfactant (E). Examples of the surfactant include a silicone surfactant, a fluorine surfactant, a silicone surfactant having a fluorine atom, and the like.
シリコーン系界面活性剤としては、シロキサン結合を有する界面活性剤が挙げられる。
具体的には、トーレシリコーンDC3PA、同SH7PA、同DC11PA、同SH21PA、同SH28PA、同SH29PA、同SH30PA、ポリエーテル変性シリコーンオイルSH8400(商品名:東レ・ダウコーニング(株)製)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化学工業(株)製)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF−4446、TSF4452、TSF4460(モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製)等が挙げられる。
Examples of the silicone surfactant include surfactants having a siloxane bond.
Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH29PA, SH30PA, polyether-modified silicone oil SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322 , KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (Momentive Performance Materials Japan GK) Manufactured) and the like.
フッ素系界面活性剤としては、フルオロカーボン鎖を有する界面活性剤が挙げられる。
具体的には、フロリナート(登録商標)FC430、同FC431(住友スリーエム(株)製)、メガファック(登録商標)F142D、同F171、同F172、同F173、同F177、同F183、同R30(DIC(株)製)、エフトップ(登録商標)EF301、同EF303、同EF351、同EF352(三菱マテリアル電子化成(株)製)、サーフロン(登録商標)S381、同S382、同SC101、同SC105(旭硝子(株)製)、E5844((株)ダイキンファインケミカル研究所製)等が挙げられる。
Examples of the fluorosurfactant include surfactants having a fluorocarbon chain.
Specifically, Florinart (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), MegaFac (registered trademark) F142D, F171, F172, F173, F177, F183, R183 (DIC) ), Ftop (registered trademark) EF301, EF303, EF351, EF351, EF352 (manufactured by Mitsubishi Materials Denkasei), Surflon (registered trademark) S381, S382, SC101, SC105 (Asahi Glass) And E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).
フッ素原子を有するシリコーン系界面活性剤としては、シロキサン結合及びフルオロカーボン鎖を有する界面活性剤が挙げられる。具体的には、メガファック(登録商標)R08、同BL20、同F475、同F477、同F443(DIC(株)製)等が挙げられる。好ましくはメガファック(登録商標)F475が挙げられる。 Examples of the silicone-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation) and the like can be mentioned. Preferably, MegaFac (registered trademark) F475 is used.
界面活性剤(E)の含有量は、感光性樹脂組成物の総量に対して、0.001質量%以上0.2質量%以下であり、好ましくは0.002質量%以上0.1質量%以下、より好ましくは0.01質量%以上0.05質量%以下である。界面活性剤を前記の範囲で含有することにより、塗膜の平坦性を良好にすることができる。 Content of surfactant (E) is 0.001 mass% or more and 0.2 mass% or less with respect to the total amount of the photosensitive resin composition, Preferably it is 0.002 mass% or more and 0.1 mass%. Below, more preferably 0.01 mass% or more and 0.05 mass% or less. By containing the surfactant in the above range, the flatness of the coating film can be improved.
本発明の感光性樹脂組成物には、必要に応じて、充填剤、他の高分子化合物、密着促進剤、酸化防止剤、紫外線吸収剤、光安定剤、連鎖移動剤等の種々の添加剤を併用してもよい。 In the photosensitive resin composition of the present invention, various additives such as fillers, other polymer compounds, adhesion promoters, antioxidants, ultraviolet absorbers, light stabilizers, chain transfer agents, etc., are optionally added. May be used in combination.
本発明の感光性樹脂組成物は、顔料および染料などの着色剤を実質的に含有しない。すなわち、本発明の感光性樹脂組成物において、組成物全量に対する着色剤の含量は、例えば、好ましくは1質量%未満、より好ましくは0.5質量%未満である。 The photosensitive resin composition of the present invention does not substantially contain colorants such as pigments and dyes. That is, in the photosensitive resin composition of the present invention, the content of the colorant relative to the total amount of the composition is, for example, preferably less than 1% by mass, more preferably less than 0.5% by mass.
本発明の感光性樹脂組成物は、光路長が1cmの石英セルに充填し、分光光度計を使用して測定波長400〜700nmの条件下で透過率を測定した場合の平均透過率が、好ましくは70%以上であり、より好ましくは80%以上である。 The photosensitive resin composition of the present invention preferably has an average transmittance when filling a quartz cell having an optical path length of 1 cm and measuring the transmittance under a measurement wavelength of 400 to 700 nm using a spectrophotometer. Is 70% or more, more preferably 80% or more.
本発明の感光性樹脂組成物は、塗膜とした際に、塗膜の平均透過率が、好ましくは90%以上であり、さらに95%以上となることがより好ましい。この平均透過率は、加熱硬化(例えば、100〜250℃、5分〜3時間)後の厚みが3μmの塗膜に対して、分光光度計を使用して、測定波長400〜700nmの条件下で測定した場合の平均値である。これにより、可視光領域での透明性に優れた塗膜を提供することができる。
通常、着色剤を含有しない樹脂組成物から塗膜を作製した場合、測定波長400nm付近での透過率が低下して黄色や茶色に着色しやすい。しかしながら、本発明の感光性樹脂組成物は、可視光領域全域(400〜700nm)において高い透過率を示す塗膜を提供することができる。
When the photosensitive resin composition of the present invention is used as a coating film, the average transmittance of the coating film is preferably 90% or more, and more preferably 95% or more. This average transmittance is measured under the conditions of a measurement wavelength of 400 to 700 nm using a spectrophotometer for a coating film having a thickness of 3 μm after heat curing (for example, 100 to 250 ° C., 5 minutes to 3 hours). It is an average value when measured by. Thereby, the coating film excellent in transparency in the visible light region can be provided.
Usually, when a coating film is produced from a resin composition that does not contain a colorant, the transmittance near a measurement wavelength of 400 nm is lowered, and it tends to be colored yellow or brown. However, the photosensitive resin composition of the present invention can provide a coating film exhibiting high transmittance in the entire visible light region (400 to 700 nm).
本発明の感光性樹脂組成物は、基板上に塗布し、溶剤等揮発成分を除去(乾燥)して膜を形成し、フォトマスクを介して該膜を露光(フォトリソグラフ法)して、現像することにより製造することができる。前記のフォトリソグラフ法において、露光の際にフォトマスクを用いないこと、及び/又は現像しないことにより、パターンを有さない塗膜を形成できる。
作製するパターンの膜厚は、特に限定されず、用いる材料、用途等によって適宜調整することができ、例えば、0.1〜30μm、好ましくは1〜20μm、さらに好ましくは1〜6μmである。
The photosensitive resin composition of the present invention is applied onto a substrate, a volatile component such as a solvent is removed (dried) to form a film, the film is exposed through a photomask (photolithographic method), and developed. Can be manufactured. In the photolithography method, a coating film having no pattern can be formed by not using a photomask and / or not developing during exposure.
The film thickness of the pattern to be produced is not particularly limited, and can be appropriately adjusted depending on the material used, application, and the like, and is, for example, 0.1 to 30 μm, preferably 1 to 20 μm, and more preferably 1 to 6 μm.
基板としては、石英ガラス、ホウケイ酸ガラス、アルミナケイ酸塩ガラス、表面をシリカコートしたソーダライムガラスなどのガラス板や、ポリカーボネート、ポリメタクリル酸メチル、ポリエチレンテレフタレートなどの樹脂板、シリコン、前記基板上にアルミニウム、銀、銀/銅/パラジウム合金薄膜などを形成したものが用いられる。これらの基板上には、カラーフィルタ層、樹脂層、絶縁膜、導電膜、トランジスタ、回路等が形成されていてもよい。 As the substrate, quartz glass, borosilicate glass, alumina silicate glass, glass plate such as soda lime glass coated with silica on the surface, resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, on the substrate In addition, aluminum, silver, or a silver / copper / palladium alloy thin film is used. On these substrates, a color filter layer, a resin layer, an insulating film, a conductive film, a transistor, a circuit, and the like may be formed.
塗布は、スピンコーター、スリット&スピンコーター、スリットコーター、インクジェット、ロールコーター、ディップコーター等の種々の塗布装置を用いて行うことができる。 The coating can be performed using various coating apparatuses such as a spin coater, a slit & spin coater, a slit coater, an ink jet, a roll coater, and a dip coater.
次いで、乾燥又はプリベークして、溶剤等の揮発成分を除去することが好ましい。これにより、平滑な膜を得ることができる。
この場合の膜の膜厚は、特に限定されず、用いる材料、用途等によって適宜調整することができ、例えば、1〜6μm程度が例示される。
Then, it is preferable to dry or pre-bake to remove volatile components such as a solvent. Thereby, a smooth film can be obtained.
The film thickness of the film in this case is not particularly limited, and can be adjusted as appropriate depending on the material used, application, and the like.
さらに、得られた膜に、目的のパターンを形成するためのフォトマスクを介して、光、例えば、水銀灯、発光ダイオードから発生する紫外線等を照射する。この際のフォトマスクの形状は特に限定されず、形状や大きさは、パターンの用途に応じて選択すればよい。
近年の露光機では、350nm未満の光を、この波長域をカットするフィルタを用いてカットしたり、436nm付近、408nm付近、365nm付近の光を、これらの波長域を取り出すバンドパスフィルタを用いて選択的に取り出して、露光面全体に均一に平行光線を照射したりすることができる。このときマスクと基板との正確な位置合わせを行うために、マスクアライナ、ステッパ等の装置を使用してもよい。
Further, the obtained film is irradiated with light, for example, ultraviolet rays generated from a mercury lamp or a light emitting diode through a photomask for forming a target pattern. The shape of the photomask at this time is not particularly limited, and the shape and size may be selected according to the application of the pattern.
In recent exposure machines, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm is used using a bandpass filter that extracts these wavelength ranges. It is possible to selectively take out and irradiate parallel light uniformly on the entire exposure surface. At this time, an apparatus such as a mask aligner or a stepper may be used to accurately align the mask and the substrate.
露光後の塗膜を現像液に接触させて所定部分、例えば、非露光部を溶解させ、現像することにより、目的とするパターン形状を得ることができる。
現像方法は、液盛り法、ディッピング法、スプレー法等のいずれでもよい。さらに現像時に基材を任意の角度に傾けてもよい。
A desired pattern shape can be obtained by bringing the exposed coating film into contact with a developer to dissolve a predetermined portion, for example, a non-exposed portion, and developing.
The developing method may be any of a liquid piling method, a dipping method, a spray method, and the like. Further, the substrate may be inclined at an arbitrary angle during development.
現像に使用する現像液は、塩基性化合物の水溶液が好ましい。
塩基性化合物は、無機及び有機の塩基性化合物のいずれでもよい。
無機の塩基性化合物の具体例としては、水酸化ナトリウム、水酸化カリウム、燐酸水素二ナトリウム、燐酸二水素ナトリウム、燐酸水素二アンモニウム、燐酸二水素アンモニウム、燐酸二水素カリウム、ケイ酸ナトリウム、ケイ酸カリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム、ホウ酸ナトリウム、ホウ酸カリウム、アンモニア等が挙げられる。
The developer used for development is preferably an aqueous solution of a basic compound.
The basic compound may be either an inorganic or organic basic compound.
Specific examples of inorganic basic compounds include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, silicic acid. Examples include potassium, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium borate, potassium borate, and ammonia.
有機の塩基性化合物としては、例えば、テトラメチルアンモニウムヒドロキシド、2−ヒドロキシエチルトリメチルアンモニウムヒドロキシド、モノメチルアミン、ジメチルアミン、トリメチルアミン、モノエチルアミン、ジエチルアミン、トリエチルアミン、モノイソプロピルアミン、ジイソプロピルアミン、エタノールアミン等が挙げられる。
これらの無機及び有機の塩基性化合物の水溶液中の濃度は、好ましくは0.01〜10質量%であり、より好ましくは0.03〜5質量%である。
Examples of organic basic compounds include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine, and ethanolamine. Is mentioned.
The concentration of these inorganic and organic basic compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.
前記の現像液は、界面活性剤を含んでいてもよい。
界面活性剤は、ノニオン系界面活性剤、アニオン系界面活性剤又はカチオン系界面活性剤のいずれでもよい。
ノニオン系界面活性剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアリールエーテル、ポリオキシエチレンアルキルアリールエーテル、その他のポリオキシエチレン誘導体、オキシエチレン/オキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンソルビトール脂肪酸エステル、グリセリン脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンアルキルアミン等が挙げられる。
The developer may contain a surfactant.
The surfactant may be any of a nonionic surfactant, an anionic surfactant, or a cationic surfactant.
Nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene / oxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene Examples include ethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene fatty acid ester, and polyoxyethylene alkylamine.
アニオン系界面活性剤としては、例えば、ラウリルアルコール硫酸エステルナトリウムやオレイルアルコール硫酸エステルナトリウムのような高級アルコール硫酸エステル塩類、ラウリル硫酸ナトリウムやラウリル硫酸アンモニウムのようなアルキル硫酸塩類、ドデシルベンゼンスルホン酸ナトリウムやドデシルナフタレンスルホン酸ナトリウムのようなアルキルアリールスルホン酸塩類等が挙げられる。 Examples of the anionic surfactant include higher alcohol sulfates such as sodium lauryl alcohol sulfate and sodium oleyl alcohol sulfate, alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate, sodium dodecylbenzenesulfonate, and dodecyl sodium sulfate. And alkylaryl sulfonates such as sodium naphthalene sulfonate.
カチオン系界面活性剤としては、例えば、ステアリルアミン塩酸塩やラウリルトリメチルアンモニウムクロライドのようなアミン塩又は第四級アンモニウム塩等が挙げられる。
アルカリ現像液中の界面活性剤の濃度は、好ましくは0.01〜10質量%の範囲、より好ましくは0.05〜8質量%、さらに好ましくは0.1〜5質量%である。
Examples of the cationic surfactant include amine salts or quaternary ammonium salts such as stearylamine hydrochloride and lauryltrimethylammonium chloride.
The concentration of the surfactant in the alkali developer is preferably in the range of 0.01 to 10% by mass, more preferably 0.05 to 8% by mass, and still more preferably 0.1 to 5% by mass.
現像後、水洗を行うことで、パターンを得ることができる。さらに必要に応じて、ポストベークを行ってもよい。ポストベークは、150〜240℃の温度範囲で、10〜180分間行うことが好ましい。 A pattern can be obtained by washing with water after development. Furthermore, you may post-bake as needed. Post bake is preferably performed at a temperature range of 150 to 240 ° C. for 10 to 180 minutes.
このようにして本発明の感光性樹脂組成物から得られるパターンは、例えば、カラーフィルタ基板及び/又はアレイ基板の一部を構成するフォトスペーサ、パターニング可能なオーバーコート、層間絶縁膜、液晶配向制御用突起、マイクロレンズ、膜厚調整のためのコート層等、タッチパネル用の部材として有用であり、上記のようにして得られるパターンを有さない塗膜は、カラーフィルタ基板及び/又はアレイ基板の一部を構成するオーバーコートとして有用である。前記のカラーフィルタ基板及びアレイ基板は、液晶表示装置、有機EL表示装置、電子ペーパー等に有用である。 In this way, the pattern obtained from the photosensitive resin composition of the present invention is, for example, a photo spacer constituting a part of a color filter substrate and / or an array substrate, a patternable overcoat, an interlayer insulating film, and a liquid crystal alignment control. A coating film that is useful as a member for a touch panel, such as a projection for projection, a microlens, and a coating layer for adjusting a film thickness, and having no pattern obtained as described above is used for a color filter substrate and / or an array substrate. It is useful as an overcoat that constitutes a part. The color filter substrate and the array substrate are useful for liquid crystal display devices, organic EL display devices, electronic paper, and the like.
以下、実施例によって本発明をより詳細に説明する。例中の「%」及び「部」は、特記ない限り、質量%及び質量部である。 Hereinafter, the present invention will be described in more detail with reference to examples. Unless otherwise specified, “%” and “parts” in the examples are% by mass and parts by mass.
合成例1
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を0.02L/分で流して窒素雰囲気とし、ジエチレングリコールエチルメチルエーテル100質量部を入れ、撹拌しながら70℃まで加熱した。次いで、メタクリル酸40質量部、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレート(式(I−1)で表される化合物及び式(II−1)で表される化合物の混合物、モル比=50:50)160質量部をジエチレングリコールエチルメチルエーテル120質量部に溶解して、溶液を調製した。得られた溶解液を、滴下ポンプを用いて4時間かけて、70℃に保温したフラスコ内に滴下した。
一方、重合開始剤2,2’−アゾビス(2,4−ジメチルバレロニトリル)30質量部をジエチレングリコールエチルメチルエーテル100質量部に溶解した溶液を、別の滴下ポンプを用いて、5時間かけてフラスコ内に滴下した。重合開始剤の溶液の滴下が終了した後、4時間、70℃に保持し、その後室温まで冷却して、固形分38.2質量%、酸価113mg−KOH/g(固形分換算)の共重合体(樹脂Aa)の溶液を得た。得られた樹脂Aaの重量平均分子量(Mw)は7.2×103、分子量分布(Mn/Mw)は1.83であった。樹脂Aaは、下記の構造単位を有する。
Synthesis example 1
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a reflux condenser, a dropping funnel and a stirrer to form a nitrogen atmosphere, and 100 parts by mass of diethylene glycol ethyl methyl ether was added and heated to 70 ° C. with stirring. Subsequently, 40 parts by mass of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate (a compound represented by the formula (I-1) and a formula (II-1) 160 parts by mass of a mixture of the compounds to be prepared (molar ratio = 50: 50) was dissolved in 120 parts by mass of diethylene glycol ethyl methyl ether to prepare a solution. The obtained solution was dropped into a flask kept at 70 ° C. for 4 hours using a dropping pump.
On the other hand, a solution obtained by dissolving 30 parts by mass of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 100 parts by mass of diethylene glycol ethyl methyl ether was added to a flask over another 5 hours using another dropping pump. It was dripped in. After completion of the dropwise addition of the polymerization initiator solution, the mixture was kept at 70 ° C. for 4 hours, and then cooled to room temperature, so that the solid content was 38.2% by mass and the acid value was 113 mg-KOH / g (in terms of solid content). A solution of the polymer (resin Aa) was obtained. The obtained resin Aa had a weight average molecular weight (Mw) of 7.2 × 10 3 and a molecular weight distribution (Mn / Mw) of 1.83. Resin Aa has the following structural units.
合成例2
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を0.02L/分で流して窒素雰囲気とし、3−メトキシ−1−ブタノール200部及び3−メトキシブチルアセテート105部を入れ、撹拌しながら70℃まで加熱した。次いで、メタクリル酸60部、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレート(式(I−1)で表される化合物及び式(II−1)で表される化合物の、モル比、50:50の混合物。)240部を、3−メトキシブチルアセテート140部に溶解して溶液を調製し、この溶解液を、滴下ロートを用いて4時間かけて、70℃に保温したフラスコ内に滴下した。
一方、重合開始剤2,2’−アゾビス(2,4−ジメチルバレロニトリル)30部を3−メトキシブチルアセテート225部に溶解した溶液を、別の滴下ロートを用いて4時間かけてフラスコ内に滴下した。重合開始剤の溶液の滴下が終了した後、4時間、70℃に保持し、その後室温まで冷却して、固形分32.6%、酸価110mg−KOH/g(固形分換算)の共重合体(樹脂Ab)の溶液を得た。得られた樹脂Abの重量平均分子量Mwは、1.34×104、分子量分布(Mn/Mw)は2.50であった。樹脂Abは、以下の構造単位を有する。
Synthesis example 2
In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, nitrogen was allowed to flow at 0.02 L / min to form a nitrogen atmosphere, and 200 parts of 3-methoxy-1-butanol and 105 parts of 3-methoxybutyl acetate were added and stirred. While heating to 70 ° C. Next, 60 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate (a compound represented by the formula (I-1) and a formula (II-1) (Mix ratio of compound: 50:50) 240 parts are dissolved in 140 parts of 3-methoxybutylacetate to prepare a solution, and this solution is added over 70 hours using a dropping funnel over 70 hours. The solution was dropped into a flask kept at a temperature of ° C.
On the other hand, a solution obtained by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts of 3-methoxybutyl acetate was placed in a flask using another dropping funnel over 4 hours. It was dripped. After completion of the dropwise addition of the polymerization initiator solution, the mixture was kept at 70 ° C. for 4 hours, and then cooled to room temperature. A solution of coalescence (resin Ab) was obtained. The obtained resin Ab had a weight average molecular weight Mw of 1.34 × 10 4 and a molecular weight distribution (Mn / Mw) of 2.50. Resin Ab has the following structural units.
合成例3
撹拌機、温度計、還流冷却器及び、滴下ロートを備えたフラスコ内に窒素を0.02L/分で流して窒素雰囲気とし、プロピレングリコールモノメチルエーテルアセテート257質量部を入れ、撹拌しながら70℃まで加熱した。次いで、アクリル酸8部、シクロヘキシルマレイミド70部、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレート(式(I−1)で表される化合物及び式(II−1)で表される化合物を、モル比で、50:50で混合。)32質量部を、プロピレングリコールモノメチルエーテルアセテート140質量部に溶解して溶液を調製し、該溶液を、滴下ロートを用いて4時間かけて、70℃に保温したフラスコ内に滴下した。
一方、重合開始剤2,2’−アゾビス(2,4−ジメチルバレロニトリル)15質量部をプロピレングリコールモノメチルエーテルアセテート225質量部に溶解した溶液を、別の滴下ロートを用いて4時間かけてフラスコ内に滴下した。重合開始剤の溶液の滴下が終了した後、4時間、70℃に保持し、その後室温まで冷却して、重量平均分子量Mw6.8×103、分子量分布Mw/Mn2.23、固形分26.7質量%、溶液酸価31mg−KOH/gの樹脂B1溶液を得た。上記の固形分と溶液酸価とから固形分酸価を計算すると、114mg−KOH/gである。
Synthesis example 3
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel to form a nitrogen atmosphere, and 257 parts by mass of propylene glycol monomethyl ether acetate was added and stirred to 70 ° C. Heated. Next, 8 parts of acrylic acid, 70 parts of cyclohexylmaleimide, 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate (compound represented by formula (I-1) and formula (II- The compound represented by 1) is mixed at a molar ratio of 50:50.) A solution is prepared by dissolving 32 parts by mass in 140 parts by mass of propylene glycol monomethyl ether acetate, and the solution is added using a dropping funnel. Then, the solution was dropped into a flask kept at 70 ° C. over 4 hours.
On the other hand, a solution obtained by dissolving 15 parts by mass of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts by mass of propylene glycol monomethyl ether acetate was added to a flask over another 4 hours using another dropping funnel. It was dripped in. After completion of the dropwise addition of the polymerization initiator solution, the temperature was maintained at 70 ° C. for 4 hours, and then cooled to room temperature, and the weight average molecular weight Mw 6.8 × 10 3 , molecular weight distribution Mw / Mn 2.23, solid content 26. A resin B1 solution having 7% by mass and a solution acid value of 31 mg-KOH / g was obtained. When the solid content acid value is calculated from the solid content and the solution acid value, it is 114 mg-KOH / g.
合成例4
撹拌機、温度計、還流冷却器及び、滴下ロートを備えたフラスコ内に窒素を0.02L/分で流して窒素雰囲気とし、プロピレングリコールモノメチルエーテルアセテート257質量部を入れ、撹拌しながら70℃まで加熱した。次いで、アクリル酸57質量部、ビニルトルエン83部、3,4−エポキシトリシクロ[5.2.1.02.6]デシルアクリレート(式(I−1)で表される化合物及び式(II−1)で表される化合物を、モル比で、50:50で混合。)238質量部を、プロピレングリコールモノメチルエーテルアセテート140質量部に溶解して溶液を調製し、該溶液を、滴下ロートを用いて4時間かけて、70℃に保温したフラスコ内に滴下した。一方、重合開始剤2,2’−アゾビス(2,4−ジメチルバレロニトリル)30質量部をプロピレングリコールモノメチルエーテルアセテート225質量部に溶解した溶液を、別の滴下ロートを用いて4時間かけてフラスコ内に滴下した。重合開始剤の溶液の滴下が終了した後、4時間、70℃に保持し、その後室温まで冷却して、重量平均分子量Mwは、1.04×104、分子量分布Mw/Mn1.98、固形分37.4質量%、固形分酸価112mg−KOH/gの樹脂B2溶液を得た。樹脂Adは、下記の構造単位を有する。
Synthesis example 4
Nitrogen was allowed to flow at 0.02 L / min in a flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel to form a nitrogen atmosphere, and 257 parts by mass of propylene glycol monomethyl ether acetate was added and stirred to 70 ° C. Heated. Subsequently, 57 parts by mass of acrylic acid, 83 parts of vinyl toluene, 3,4-epoxytricyclo [5.2.1.0 2.6 ] decyl acrylate (compound represented by formula (I-1) and formula (II) The compound represented by -1) is mixed at a molar ratio of 50:50.) A solution is prepared by dissolving 238 parts by mass in 140 parts by mass of propylene glycol monomethyl ether acetate, and the solution is added to the dropping funnel. It was dripped in the flask kept at 70 degreeC over 4 hours using it. On the other hand, a solution obtained by dissolving 30 parts by mass of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts by mass of propylene glycol monomethyl ether acetate was added to a flask using another dropping funnel over 4 hours. It was dripped in. After completion of dropping of the polymerization initiator solution, the solution was kept at 70 ° C. for 4 hours, and then cooled to room temperature. The weight average molecular weight Mw was 1.04 × 10 4 , molecular weight distribution Mw / Mn 1.98, solid A resin B2 solution having a content of 37.4% by mass and a solid content acid value of 112 mg-KOH / g was obtained. Resin Ad has the following structural units.
得られた樹脂Aa、Ab、Ac、Adの重量平均分子量(Mw)及び数平均分子量(Mn)の測定は、GPC法を用いて、以下の条件で行なった。
装置:K2479((株)島津製作所製)
カラム:SHIMADZU Shim−pack GPC−80M
カラム温度:40℃
溶媒:THF(テトラヒドロフラン)
流速:1.0mL/min
検出器:RI
校正用標準物質 ;TSK STANDARD POLYSTYRENE F−40、F−4、F−288、A−2500、A−500(東ソー(株)製)
上記で得られたポリスチレン換算の重量平均分子量及び数平均分子量の比(Mw/Mn)を分子量分布とした。
The weight average molecular weight (Mw) and number average molecular weight (Mn) of the obtained resins Aa, Ab, Ac, and Ad were measured using the GPC method under the following conditions.
Apparatus: K2479 (manufactured by Shimadzu Corporation)
Column: SHIMADZU Shim-pack GPC-80M
Column temperature: 40 ° C
Solvent: THF (tetrahydrofuran)
Flow rate: 1.0 mL / min
Detector: RI
Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The polystyrene-converted weight average molecular weight and number average molecular weight ratio (Mw / Mn) obtained above was defined as molecular weight distribution.
実施例及び比較例
表1に示す組成となるように、各成分を混合して、感光性樹脂組成物を得た。
Examples and Comparative Examples Each component was mixed so as to have the composition shown in Table 1 to obtain a photosensitive resin composition.
なお、表1中、
樹脂(Aa)〜(Ad)は、固形分換算の質量部を表す。
重合性化合物(B);ジペンタエリスリトールヘキサアクリレート(KAYARAD DPHA;日本化薬(株)製)
化合物(1);式(1A)で表される化合物:特開2011−132215号公報に記載される方法により製造した。
重合開始剤(Ca);N−アセトキシ−1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]エタン−1−イミン(IRGACURE OXE 02;BASFジャパン社製)
溶剤(Da);3-メトキシ−1−ブタノール
溶剤(Db);ジエチレングリコールエチルメチルエーテル
溶剤(Dc);プロピレングリコールモノメチルエーテルアセテート
溶剤(Dd);3−メトキシブチルアセテート
溶剤(De);3−エトキシエチルプロピオネート
界面活性剤(E);ポリエーテル変性シリコーンオイル(東レ・ダウコーニング(株)製;トーレシリコーンSH8400)
溶剤(D)は、感光性樹脂組成物の固形分量が表1の「固形分量〔%〕」となるように混合し、溶剤(D)中の溶剤成分(Da)〜(Dd)の値は、溶剤(D)中での質量比を表す。
界面活性剤(E)の含有量は、感光性樹脂組成物に対する質量比(%)を表す。
In Table 1,
Resin (Aa)-(Ad) represents the mass part of solid content conversion.
Polymerizable compound (B); dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
Compound (1): Compound represented by formula (1A): produced by the method described in JP2011-132215A.
Polymerization initiator (Ca); N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine (IRGACURE OXE 02; manufactured by BASF Japan)
Solvent (Da); 3-methoxy-1-butanol Solvent (Db); Diethylene glycol ethyl methyl ether Solvent (Dc); Propylene glycol monomethyl ether acetate Solvent (Dd); 3-methoxybutyl acetate solvent (De); 3-ethoxyethyl Propionate
Surfactant (E); polyether-modified silicone oil (manufactured by Toray Dow Corning Co., Ltd .; Tore Silicone SH8400)
The solvent (D) is mixed so that the solid content of the photosensitive resin composition becomes “solid content [%]” in Table 1, and the values of the solvent components (Da) to (Dd) in the solvent (D) are Represents a mass ratio in the solvent (D).
The content of the surfactant (E) represents a mass ratio (%) to the photosensitive resin composition.
<組成物の平均透過率>
得られた感光性樹脂組成物について、それぞれ、紫外可視近赤外分光光度計(V−650;日本分光(株)製)(石英セル、光路長;1cm)を用いて、400〜700nmにおける平均透過率(%)を測定した。結果を表2に示す。
<Average transmittance of composition>
About the obtained photosensitive resin composition, the average in 400-700 nm was respectively used for the ultraviolet visible near infrared spectrophotometer (V-650; JASCO Corporation make) (quartz cell, optical path length: 1 cm). The transmittance (%) was measured. The results are shown in Table 2.
<塗膜の形成>
2インチ角のガラス基板(イーグルXG;コーニング社製)を、中性洗剤、水およびアルコールで順次洗浄してから乾燥した。このガラス基板上に、上記で得られた感光性樹脂組成物を、ポストベーク後の膜厚が3.0μmになるようにスピンコートし、次にクリーンオーブン中、90℃で3分間プリベークした。その後、230℃で20分加熱して塗膜を得た。
<Formation of coating film>
A 2-inch square glass substrate (Eagle XG; manufactured by Corning) was sequentially washed with a neutral detergent, water and alcohol and then dried. The photosensitive resin composition obtained above was spin-coated on this glass substrate so that the film thickness after post-baking was 3.0 μm, and then pre-baked at 90 ° C. for 3 minutes in a clean oven. Then, it heated at 230 degreeC for 20 minutes, and obtained the coating film.
<塗膜の透過率>
得られた塗膜について、顕微分光測光装置(OSP−SP200;OLYMPUS社製)を用いて、400nmにおける透過率(%)及び400〜700nmにおける平均透過率(%)を測定した。400nmにおける透過率が高いほど、塗膜の着色が少ないことを示す。結果を表2に示す。
<Transparency of coating film>
About the obtained coating film, the transmittance | permeability (%) in 400 nm and the average transmittance (%) in 400-700 nm were measured using the microspectrophotometer (OSP-SP200; product made by OLYMPUS). It shows that there is so little coloring of a coating film that the transmittance | permeability in 400 nm is high. The results are shown in Table 2.
<パターン形成>
2インチ角のガラス基板(イーグルXG;コーニング社製)を、中性洗剤、水及びアルコールで順次洗浄してから乾燥した。このガラス基板上に、感光性樹脂組成物を、60mJ/cm2の露光量(365nm基準)で露光し、現像、水洗、ポストベーク後の膜厚が3.0μmになるようにスピンコートし、次にクリーンオーブン中、80℃で2分間プリベークした。冷却後、この感光性樹脂組成物を塗布した基板と石英ガラス製フォトマスクとの間隔を200μmとし、露光機(TME−150RSK;トプコン(株)製、光源;超高圧水銀灯)を用いて、大気雰囲気下、60mJ/cm2の露光量(365nm基準)で光照射した。なお、このときの感光性樹脂組成物への照射は、超高圧水銀灯からの放射光を、光学フィルタ(UV−33;旭テクノグラス(株)製)を通過させて、使用した。また、フォトマスクとして、パターン(1辺が13μmである正方形の透光部を有し、当該正方形の間隔が100μm)が同一平面上に形成されたフォトマスクを用いた。
光照射後、非イオン系界面活性剤0.12%と水酸化カリウム0.04%を含む水系現像液に前記塗膜を25℃で60秒間浸漬して現像し、水洗後、オーブン中、235℃で15分間ポストベークを行い、パターンを得た。
<Pattern formation>
A 2-inch square glass substrate (Eagle XG; manufactured by Corning) was sequentially washed with a neutral detergent, water and alcohol and then dried. On this glass substrate, the photosensitive resin composition is exposed at an exposure amount of 60 mJ / cm 2 (based on 365 nm), spin-coated so that the film thickness after development, water washing and post-baking is 3.0 μm, Next, it was pre-baked at 80 ° C. for 2 minutes in a clean oven. After cooling, the distance between the substrate coated with the photosensitive resin composition and the quartz glass photomask was set to 200 μm, and the exposure apparatus (TME-150RSK; manufactured by Topcon Corporation, light source: ultrahigh pressure mercury lamp) In the atmosphere, light was irradiated with an exposure amount of 60 mJ / cm 2 (based on 365 nm). In addition, the irradiation to the photosensitive resin composition at this time used the radiated light from an ultrahigh pressure mercury lamp through the optical filter (UV-33; Asahi Techno Glass Co., Ltd.). In addition, a photomask having a pattern (having a square light-transmitting portion with one side of 13 μm and an interval of the square of 100 μm) formed on the same plane was used as the photomask.
After the light irradiation, the coating film was immersed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide for 60 seconds at 25 ° C. A post bake was performed at 15 ° C. for 15 minutes to obtain a pattern.
<パターン幅の測定>
得られたパターンについて、三次元非接触表面形状計測システム(Micromap MM527N−PS−M100;(株)菱化システム社製)でパターンの幅を測定した。尚、基板面から、パターンの高さに対し5%の高さの部分で、パターンの幅を測定した。
結果を表2に示す。
<Measurement of pattern width>
About the obtained pattern, the width | variety of the pattern was measured with the three-dimensional non-contact surface shape measuring system (Micromap MM527N-PS-M100; Co., Ltd. Ryoka Systems Co., Ltd.). The width of the pattern was measured from the substrate surface at a portion having a height of 5% with respect to the height of the pattern.
The results are shown in Table 2.
<露光マージン評価>
露光量を80mJ/cm2に代える以外は上記と同じ方法でパターンを得た。露光量60mJ/cm2の条件で得たパターンの幅をW60、露光量80mJ/cm2の条件で得たパターンの幅をW80としたとき、下記式で表される値を露光量依存性とした。
(露光量依存性)=(W80−W60)/(80−60)
露光量依存性の値が小さい方が、露光量の振れに対して得られるパターンの幅の振れが小さく、露光マージンは広いことを意味する。
<Evaluation of exposure margin>
A pattern was obtained by the same method as above except that the exposure dose was changed to 80 mJ / cm 2 . Exposure 60 mJ / cm 2 conditions obtained in the pattern of the width W 60 of, when the width of the pattern obtained under the conditions of exposure 80 mJ / cm 2 was W 80, exposure latitude the value represented by the following formula It was sex.
(Exposure dose dependency) = (W 80 -W 60 ) / (80-60)
A smaller value of the exposure dose dependency means that the fluctuation of the pattern width obtained with respect to the fluctuation of the exposure dose is smaller, and the exposure margin is wider.
表2に示すとおり、化合物(1)を含む感光性樹脂組成物は、露光量依存性の値が小さいことから、露光マージンが広いことが確認された。
このような感光性樹脂組成物により形成したパターンを利用して表示装置を製造することにより、歩留まりを向上させることが可能となる。
As shown in Table 2, it was confirmed that the photosensitive resin composition containing the compound (1) has a wide exposure margin because the value of exposure dose dependency is small.
By manufacturing a display device using a pattern formed from such a photosensitive resin composition, the yield can be improved.
本発明によれば、パターン形成時の露光マージンが広い感光性樹脂組成物を提供することが可能となる。本発明の感光性樹脂組成物から得られるパターンは、液晶表示装置、有機EL表示装置、電子ペーパーなどの部材として好適に使用し得る。 ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide the photosensitive resin composition with a wide exposure margin at the time of pattern formation. The pattern obtained from the photosensitive resin composition of the present invention can be suitably used as a member for liquid crystal display devices, organic EL display devices, electronic paper, and the like.
Claims (4)
樹脂が、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種に由来する構造単位を有する重合体であり、
重合開始剤が式(1)で表される化合物を含む重合開始剤である感光性樹脂組成物。
[式(1)中、Ra1及びRa2は、それぞれ独立に、Ra11、ORa11、CORa11、SRa11、CONRa12Ra13又はCNを表し、
Ra11、Ra12及びRa13は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基を表し、
Ra11、Ra12またはRa13で表わされる基の水素原子は、ORa21、CORa21、SRa21、NRa22Ra23、CONRa22Ra23、−NRa22−ORa23、−N(CORa22)−OCORa23、−C(=N−ORa21)−Ra22、−C(=N−OCORa21)−Ra22、CN、ハロゲン原子、又はCOOR21で置換されていてもよく、
Ra21、Ra22及びRa23は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアラルキル基又は炭素数2〜20の複素環基を表し、
Ra21、Ra22またはRa23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよく、
Ra11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa24−、−NRa24CO−、−NRa24COO−、−OCONRa24−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、
Ra24は、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基、炭素数7〜30のアリールアルキル基又は炭素数2〜20の複素環基を表し、
Ra11、Ra12、Ra13、Ra21、Ra22またはRa23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、Ra12とRa13及びRa22とRa23はそれぞれ一緒になって環を形成していてもよく、
Ra3及びRa4は、それぞれ独立に、Ra11、ORa11、SRa11、CORa11、CONRa12Ra13、NRa12CORa11、OCORa11、COORa11、SCORa11、OCSRa11、COSRa11、CSORa11、CN又はハロゲン原子を表し、
s及びtは、それぞれ独立に、0〜4の整数を表し、
Lは、酸素原子、硫黄原子、セレン原子、CRa31Ra32、CO、NRa33又はPRa34を表し、
Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基又は炭素数7〜30のアラルキル基を表し、
Ra31、Ra32、Ra33またはRa34で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、Ra31、Ra32、Ra33及びRa34は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよく、
Ra5は、ヒドロキシ基、カルボキシ基又は式(2)
(式(2)中、L1は、−O−、−S−、−NRa22−、−NRa22CO−、−SO2−、−CS−、−OCO−又は−COO−を表し、
L2は、炭素数1〜20のアルキル基からv個の水素原子を除いた基、炭素数6〜30のアリール基からv個の水素原子を除いた基、炭素数7〜30のアラルキル基からv個の水素原子を除いた基又は炭素数2〜20の複素環基からv個の水素原子を除いた基を表し、
L2で表される基がアルキレン部分を有する場合、該アルキレン部分は、−O−、−S−、−COO−、−OCO−、−NRa22−、−NRa22COO−、−OCONRa22−、−SCO−、−COS−、−OCS−又は−CSO−により1〜5回中断されていてもよく、該アルキレン部分は分枝鎖状であってもよく、環状であってもよく、
Ra6は、ORa41、SRa41、CONRa42Ra43、NRa42CORa43、OCORa41、COORa41、SCORa41、OCSRa41、COSRa41、CSORa41、CN又はハロゲン原子を表し、
Ra41、Ra42及びRa43は、それぞれ独立に、水素原子、炭素数1〜20のアルキル基、炭素数6〜30のアリール基又は炭素数7〜30のアラルキル基を表し、Ra41、Ra42及びRa43で表される基がアルキル部分を有する場合、該アルキル部分は分枝鎖状であってもよく、環状であってもよく、Ra42とRa43は、一緒になって環を形成していてもよく、
vは1〜3の整数を表す。)
で表される基を表す。] A resin, a polymerizable compound and a polymerization initiator,
The resin is a polymer having a structural unit derived from at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride,
The photosensitive resin composition which is a polymerization initiator in which a polymerization initiator contains the compound represented by Formula (1).
[In the formula (1), R a1 and R a2 each independently represent R a11 , OR a11 , COR a11 , SR a11 , CONR a12 R a13 or CN;
R a11 , R a12 and R a13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or an alkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group,
The hydrogen atom of the group represented by R a11 , R a12 or R a13 is OR a21 , COR a21 , SR a21 , NR a22 R a23 , CONR a22 R a23 , —NR a22 —OR a23 , —N (COR a22 ) — OCOR a23 , —C (═N—OR a21 ) —R a22 , —C (═N—OCOR a21 ) —R a22 , CN, halogen atom, or COOR 21 may be substituted,
R a21 , R a22 and R a23 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or an alkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group,
The hydrogen atom of the group represented by R a21 , R a22 or R a23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group,
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 has an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR a24 -, - NR a24 CO -, - NR a24 COO -, - OCONR a24 -, - SCO -, - COS -, - OCS- or -CSO- by which it may be interrupted 1 to 5 times,
R a24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,
When the group represented by R a11 , R a12 , R a13 , R a21 , R a22 or R a23 has an alkyl moiety, the alkyl moiety may be branched or cyclic. And R a12 and R a13 and R a22 and R a23 may be combined to form a ring,
R a3 and R a4 are each independently, R a11, OR a11, SR a11, COR a11, CONR a12 R a13, NR a12 COR a11, OCOR a11, COOR a11, SCOR a11, OCSR a11, COSR a11, CSOR a11 , CN or a halogen atom,
s and t each independently represent an integer of 0 to 4,
L represents an oxygen atom, a sulfur atom, a selenium atom, CR a31 R a32 , CO, NR a33 or PR a34 ,
R a31 , R a32 , R a33 and R a34 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms,
When the group represented by R a31 , R a32 , R a33 or R a34 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R a31 , R a32 , R a33 and R a34 may each independently form a ring together with one of the adjacent benzene rings,
R a5 is a hydroxy group, a carboxy group or a formula (2)
(In the formula (2), L 1 represents —O—, —S—, —NR a22 —, —NR a22 CO— , —SO 2 —, —CS—, —OCO— or —COO—,
L 2 is a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. A group in which v hydrogen atoms are removed from or a group in which v hydrogen atoms are removed from a heterocyclic group having 2 to 20 carbon atoms,
When the group represented by L 2 has an alkylene moiety, the alkylene moiety is —O—, —S—, —COO— , —OCO— , —NR a22 —, —NR a22 COO— , —OCONR a22 —. , -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times, and the alkylene moiety may be branched or cyclic,
R a6 represents OR a41 , SR a41 , CONR a42 R a43 , NR a42 COR a43 , OCOR a41 , COOR a41 , SCOR a41 , OCSR a41 , COSR a41 , CSOR a41 , CN or a halogen atom,
R a41 , R a42 and R a43 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms, and R a41 , R When the group represented by a42 and R a43 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R a42 and R a43 together form a ring. May be formed,
v represents an integer of 1 to 3. )
Represents a group represented by ]
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JP2013164471A (en) * | 2012-02-09 | 2013-08-22 | Jsr Corp | Curable resin composition, cured film for display device, formation method of cured film for display device, and display device |
JP2015014783A (en) * | 2013-06-04 | 2015-01-22 | 日立化成株式会社 | Method for manufacturing transparent substrate with cured film, photosensitive resin composition, photosensitive element, and electronic component |
JPWO2015125469A1 (en) * | 2014-02-19 | 2017-03-30 | 日立化成デュポンマイクロシステムズ株式会社 | Resin composition, cured film and pattern cured film formed thereby, and method for producing the same |
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TW201308008A (en) | 2013-02-16 |
KR20130006334A (en) | 2013-01-16 |
JP6060539B2 (en) | 2017-01-18 |
CN102866584A (en) | 2013-01-09 |
KR101867103B1 (en) | 2018-06-12 |
CN102866584B (en) | 2019-05-28 |
TWI546622B (en) | 2016-08-21 |
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