CN102566273B - Positive photosensitive resin composition and method for forming pattern - Google Patents
Positive photosensitive resin composition and method for forming pattern Download PDFInfo
- Publication number
- CN102566273B CN102566273B CN201110346718.2A CN201110346718A CN102566273B CN 102566273 B CN102566273 B CN 102566273B CN 201110346718 A CN201110346718 A CN 201110346718A CN 102566273 B CN102566273 B CN 102566273B
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- Prior art keywords
- methyl
- benzaldehyde
- compound
- resin composition
- hydroxy
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 19
- -1 o-naphthoquinone diazide sulfonic acid ester Chemical class 0.000 claims abstract description 160
- 229920003986 novolac Polymers 0.000 claims abstract description 46
- 239000003822 epoxy resin Substances 0.000 claims abstract description 19
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 239000000758 substrate Substances 0.000 claims description 37
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229930192627 Naphthoquinone Natural products 0.000 claims description 17
- 150000002791 naphthoquinones Chemical group 0.000 claims description 17
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical group OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 7
- WNCNWLVQSHZVKV-UHFFFAOYSA-N 2,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C=C1O WNCNWLVQSHZVKV-UHFFFAOYSA-N 0.000 claims description 6
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
- CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- XVHIUKSUZLPFCP-UHFFFAOYSA-N 2-(hydroxymethyl)benzaldehyde Chemical compound OCC1=CC=CC=C1C=O XVHIUKSUZLPFCP-UHFFFAOYSA-N 0.000 claims description 3
- CDNQOMJEQKBLBN-UHFFFAOYSA-N 3-(hydroxymethyl)benzaldehyde Chemical compound OCC1=CC=CC(C=O)=C1 CDNQOMJEQKBLBN-UHFFFAOYSA-N 0.000 claims description 3
- ZFHUHPNDGVGXMS-UHFFFAOYSA-N 4-(hydroxymethyl)benzaldehyde Chemical group OCC1=CC=C(C=O)C=C1 ZFHUHPNDGVGXMS-UHFFFAOYSA-N 0.000 claims description 3
- 230000007261 regionalization Effects 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 230000018109 developmental process Effects 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 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 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 229940035423 ethyl ether Drugs 0.000 description 5
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 229910052581 Si3N4 Inorganic materials 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910021417 amorphous silicon Inorganic materials 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 150000003739 xylenols Chemical class 0.000 description 4
- 150000000181 1,2-naphthoquinones Chemical class 0.000 description 3
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-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
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- 239000000975 dye Substances 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
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- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
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- VZIRCHXYMBFNFD-HNQUOIGGSA-N 3-(2-Furanyl)-2-propenal Chemical compound O=C\C=C\C1=CC=CO1 VZIRCHXYMBFNFD-HNQUOIGGSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 235000011054 acetic acid Nutrition 0.000 description 2
- KVXNKFYSHAUJIA-UHFFFAOYSA-N acetic acid;ethoxyethane Chemical compound CC(O)=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-N 0.000 description 2
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- 239000002671 adjuvant Substances 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
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- QQQCWVDPMPFUGF-ZDUSSCGKSA-N alpinetin Chemical compound C1([C@H]2OC=3C=C(O)C=C(C=3C(=O)C2)OC)=CC=CC=C1 QQQCWVDPMPFUGF-ZDUSSCGKSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 229940109262 curcumin Drugs 0.000 description 2
- 239000004148 curcumin Substances 0.000 description 2
- 235000012754 curcumin Nutrition 0.000 description 2
- 238000007766 curtain coating Methods 0.000 description 2
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- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- IPSOQTFPIWIGJT-UHFFFAOYSA-N acetic acid;1-propoxypropane Chemical compound CC(O)=O.CCCOCCC IPSOQTFPIWIGJT-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron 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
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 229940024423 isopropyl isobutyrate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical class CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-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
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-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
- 150000003233 pyrroles Chemical class 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- XYRAEZLPSATLHH-UHFFFAOYSA-N trisodium methoxy(trioxido)silane Chemical compound [Na+].[Na+].[Na+].CO[Si]([O-])([O-])[O-] XYRAEZLPSATLHH-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Abstract
The present invention relates to a positive photosensitive resin composition and a method for forming a pattern using the same. In particular, a positive photosensitive resin composition having excellent crack resistance and a method for forming a pattern using the same are provided. The resin composition comprises a novolac resin , an epoxy resin (B) containing glycidyl groups, an o-naphthoquinone diazide sulfonic acid ester (C) and a solvent (D), wherein the novolac resin comprises a hydroxyl-type novolac resin (A-1), and the hydroxyl-type novolac resin (A-1) is obtained by condensing a hydroxybenzaldehyde compound and an aromatic hydroxyl compound.
Description
Technical field
The present invention relates to a kind of positive-type photosensitive resin composition and use this constituent to form the method for pattern.Particularly provide a kind of and use in the LCD assembly of semiconductor aggregation loop assembly and membrane transistor (hereinafter to be referred as TFT) is manufactured, the positive-type photosensitive resin composition that resistance to Fractured is good and use this constituent to form the method for pattern.
Background technology
On substrate, form as on the dielectric film or conductive metal film of the fine circuit designs such as LCD assembly loop or the long-pending body loop of semiconductor, be coated with equably light resistance composition, and under the light shield of designated shape, carry out exposure imaging, can make the pattern of required form.Then, will form the photoresistance film of pattern after light shield is removed metal film or dielectric film, then remove residual photoresistance film, can on substrate, form fine loop.Solvable or insoluble according to light resistance composition in exposed portion or photoresistance membrane portions, light resistance composition can be divided into eurymeric photoresistance and minus photoresistance two classes.
Japanese Patent Publication 2-51499 patent documentation discloses a kind of positive-type photosensitive resin composition, this constituent comprise a potpourri by m-cresol, p-Cresol and xylenols and aldehydes condensation and novolac resin and quinone two triazo-compounds, in application, there is the advantages such as high sensitivity and high residual film ratio, but, according to demand in recent years, its pattern forming has the problem of poor heat resistance and cannot reach standard.
Therefore, compared to aforementioned photosensitive resin composition, TOHKEMY 2007-304592 patent documentation discloses and uses novolac resin as represented in following structural as photosensitive resin composition, can on substrate, form the good pattern of thermotolerance, but its pattern forming but has the not good problem of resistance to Fractured;
(in formula, R represent H ,-OH or-CH
3, the integer that n is 3～20).
Summary of the invention
Fundamental purpose of the present invention is to provide a kind of positive-type photosensitive resin composition, particularly provide a kind of and use in the LCD assembly of semiconductor aggregation loop assembly and membrane transistor (hereinafter to be referred as TFT) is manufactured, the positive-type photosensitive resin composition that resistance to Fractured is good.
Another object of the present invention is to provide a kind of method of using aforementioned positive-type photosensitive resin composition to form pattern.
For meeting aforementioned object, the present invention relates to a kind of positive-type photosensitive resin composition, comprise novolac resin (A), containing the epoxy resin (B) of epoxypropane base (oxetanyl), repeatedly nitrogen sulphonic acids carboxylate (C) and solvent (D) of adjacent naphthoquinones two, wherein, this novolac resin (A) comprises oh type novolac resin (A-1), this oh type novolac resin (A-1) is by hydroxy benzaldehyde compound and aromatic hydroxy compound condensation and obtain, and based on novolac resin (A) 100 weight portions, the use amount of this oh type novolac resin (A-1) is 30～100 weight portions.
Positive-type photosensitive resin composition as previously mentioned, wherein, this hydroxy benzaldehyde compound is to be selected from the group that hydroxy benzaldehyde compound, 4-dihydroxy benzaldehyde compound, tri hydroxybenzaldehyde compound and hydroxy alkyl benzaldehyde compound form.
Positive-type photosensitive resin composition as previously mentioned, wherein, this hydroxy benzaldehyde compound is to be selected from the group that o-hydroxy benzaldehyde, m-hydroxy benzaldehyde and p-hydroxybenzaldehyde form.
Positive-type photosensitive resin composition as previously mentioned, wherein, this 4-dihydroxy benzaldehyde compound is to be selected from 2,3-4-dihydroxy benzaldehyde, 2,4-4-dihydroxy benzaldehyde, 2,5-4-dihydroxy benzaldehyde, 3, the group that 4-4-dihydroxy benzaldehyde and 3,5-4-dihydroxy benzaldehyde form.
Positive-type photosensitive resin composition as previously mentioned, wherein, this tri hydroxybenzaldehyde compound is to be selected from 2,3,4-tri hydroxybenzaldehyde, 2,4,5-tri hydroxybenzaldehyde, 2,4,6-tri hydroxybenzaldehyde, 3,4, the group that 5-tri hydroxybenzaldehyde forms.
Positive-type photosensitive resin composition as previously mentioned, wherein, this hydroxy alkyl benzaldehyde compound is to be selected from the group that comprises that o-methylol benzaldehyde, m-methylol benzaldehyde and p-methylol benzaldehyde form.
Positive-type photosensitive resin composition as previously mentioned, wherein, based on novolac resin (A) 100 weight portions, the use amount that contains the epoxy resin (B) of epoxypropane base is 5～40 weight portions, the adjacent naphthoquinones two repeatedly use amount of nitrogen sulphonic acids carboxylate (C) is 1～100 weight portion, and the use amount of solvent (D) is 500～2000 weight portions.
A kind of pattern formation method of the present invention, is that foregoing positive-type photosensitive resin composition is coated to substrate, more sequentially bestows pre-baked, exposure, development and rear roasting processing, forms pattern accordingly in this substrate.
A kind of electric crystal array film substrate of the present invention, comprises foregoing pattern.
A kind of LCD assembly of the present invention, comprises described electric crystal array film substrate.
In the present invention, with (methyl) acrylic acid, represent acrylic acid and/or methacrylic acid, similarly, with (methyl) acrylate, represent acrylate and/or methacrylate; With (methyl) acryloyl group, represent acryloyl group and/or methacryl; With (methyl) acryloyl-oxy basis representation acryloxy and/or methacryloxy.
Below one by one the each composition of the present invention is described in detail.
< positive-type photosensitive resin composition >
[novolac resin (A)]
Positive-type photosensitive resin composition novolac resin of the present invention (A) comprises oh type novolac resin (A-1), and optionally further comprises other novolac resins (A-2).
This oh type novolac resin (A-1) is by hydroxy benzaldehyde compound and aromatic hydroxy compound, under acidic catalyst exists, through condensation reaction, obtains.
Wherein, the concrete example of hydroxy benzaldehyde compound is: the hydroxy benzaldehyde compounds such as o-hydroxy benzaldehyde, m-hydroxy benzaldehyde, p-hydroxybenzaldehyde; 2,3-4-dihydroxy benzaldehyde, 2,4-4-dihydroxy benzaldehyde, 2,5-4-dihydroxy benzaldehyde, 3,4-4-dihydroxy benzaldehyde, 3, the 4-dihydroxy benzaldehyde compound of 5-4-dihydroxy benzaldehyde etc.; 2,3,4-tri hydroxybenzaldehyde, 2,4,5-tri hydroxybenzaldehyde, 2,4,6-tri hydroxybenzaldehyde, 3,4, the tri hydroxybenzaldehyde compounds such as 5-tri hydroxybenzaldehyde; The hydroxy alkyl benzaldehyde compounds such as o-methylol benzaldehyde, m-methylol benzaldehyde, p-methylol benzaldehyde.This hydroxy benzaldehyde compound can be used alone or mixing plural kinds of use.Wherein, with o-hydroxy benzaldehyde, m-hydroxy benzaldehyde, p-hydroxybenzaldehyde, 2,3-4-dihydroxy benzaldehyde, 2,4-4-dihydroxy benzaldehyde, 3,4-4-dihydroxy benzaldehyde, 2,3,4-tri hydroxybenzaldehyde is for better.
The concrete example of the aromatic hydroxy compound of the present invention and this hydroxy benzaldehyde compound condensation reaction is: phenol (phenol); Cresols (cresol) class of m-cresol (m-cresol), p-Cresol (p-cresol), o-cresols (o-cresol) etc.; 2,3-xylenols, 2,5-xylenols, 3, xylenol (xylenol) classes such as 5-xylenols, DMP; M-ethyl-phenol, p-ethyl-phenol, o-ethyl-phenol, 2,3,5-pseudocuminol, 2, alkylphenol (alkyl phenol) class of 3,5-triethyl phenol, 4-tributyl phenol, 3-tributyl phenol, 2-tributyl phenol, 2-the tributyl-4-methylphenol, 2-the tributyl-5-methylphenol, 6-the tributyl-3-methylphenol etc.; P-metoxyphenol, m-metoxyphenol, p-thanatol, m-thanatol, to alkoxy phenol (alkoxy phenol) classes such as propoxyl group phenol, m-propoxyl group phenol; Isopropenyl phenol (isopropenyl phenol) classes such as o-isopropenyl phenol, p-isopropenyl phenol, 2-methyl-4-isopropenyl phenol, 2-ethyl-4-isopropenyl phenol; Aryl phenol (aryl phenol) classes such as phenylphenol (phenyl phenol); 4,4'-dihydroxybiphenyl, bisphenol-A, m-benzenediol (resorcinol), p-benzenediol (hydroquinone), 1, polyhydroxy benzenes (polyhydroxyphenol) classes such as 2,3-benzenetriol (pyrogallol) etc.Aforementioned aromatic hydroxy compound can be used alone or mixing plural kinds of use.Wherein, with o-cresols, m-cresol, p-Cresol, 2,5-xylenols, 3,5-xylenols, 2,3,5-TEP etc. are for better.
The concrete example of aforementioned acidic catalyst is as hydrochloric acid, sulfuric acid, formic acid, acetic acid, oxalic acid, p-toluenesulfonic acid etc.
Based on novolac resin (A) 100 weight portions, the use amount of oh type novolac resin (A-1) is generally 30～100 weight portions, is preferably 40～100 weight portions, is more preferred from 50～100 weight portions.If oh type novolac resin (A-1) use amount is during lower than 30 weight portion, the pattern that photosensitive resin composition forms easily has crack to produce and the low problem of residual film ratio.
Other novolac resins (A-2), are generally by aldehydes such as aforementioned aromatic hydroxy compound and non-hydroxyl benzaldehydes, under aforementioned acidic catalyst exists, through condensation reaction, obtain.
Wherein, the concrete example of the aldehydes such as non-hydroxyl benzaldehyde is: formaldehyde, paraformaldehyde (paraformaldehyde), trioxymethylene (trioxane), acetaldehyde, propionic aldehyde, butyraldehyde, trimethyl-acetaldehyde, acryl aldehyde (acrolein), crotonaldehyde (crotonaldehyde), hexamethylene aldehyde (cyclo hexanealdehyde), furtural (furfural), furylacrolein (furylacrolein), benzaldehyde, terephthalaldehyde (terephthal aldehyde), phenylacetaldehyde, α-hydrocinnamicaldehyde, beta-phenyl propionic aldehyde, o-tolyl aldehyde, m-tolyl aldehyde, p-tolualdehyde, o-chlorobenzaldehyde, m-chlorobenzaldehyde, p-chlorobenzaldehyde, cinnamic acid etc.Aforementioned aldehydes can be used alone or mixing plural kinds of use.Wherein, with formaldehyde for better.
Aforementioned oh type novolac resin (A-1) and other novolac resins (A-2), all can be used the novolac resin of single kind, also can mix two or more variety classes novolac resin.
[containing the epoxy resin (B) of epoxypropane base]
In normal Photosensitive resin of the present invention, containing the epoxy resin (B) of epoxypropane base, be by unsaturated carboxylic acid monomer (b1), containing epoxypropane based compound (b2) and other unsaturated monomers (b3) institute's copolymerization, obtain.Wherein:
The concrete example of unsaturated carboxylic acid monomer (b1) is: the unsaturated monocarboxylic acid classes such as acrylic acid, methacrylic acid, butenoic acid, α-chloroacrylic acid, ethylacrylic acid and cinnamic acid; Unsaturated dicarboxylic acid (acid anhydride) classes such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride; Unsaturated polyvalent carboxylic acid (acid anhydride) class more than 3 valencys etc.Wherein, with acrylic acid, methacrylic acid for better.This unsaturated carboxylic acid monomer (b1) can be used alone or mixing plural kinds of use.
Concrete example containing epoxypropane based compound (b2) is: 3-(methyl) acryloyl-oxy methyl epoxypropane (3-[(meth) acryloyloxy-methyl] oxetane), 3-(methyl) acryloyl-oxy methyl-3-ethyl epoxypropane, 3-(methyl) acryloyl-oxy methyl-2-methyl epoxypropane, 3-(methyl) acryloyl-oxy Methyl-2-trifluoromethyl epoxypropane, 3-(methyl) acryloyl-oxy methyl-2-pentafluoroethyl group epoxypropane, 3-(methyl) acryloyl-oxy methyl-2-benzyl ring Ethylene Oxide, 3-(methyl) acryloyl-oxy methyl-2,2-difluoro epoxypropane, 3-(methyl) acryloyl-oxy methyl-2,2,4-trifluoro-epoxy propane, 3-(methyl) acryloyl-oxy methyl-2,2,4,4-ptfe ring Ethylene Oxide, 3-(methyl) acrylyl oxy-ethyl epoxypropane, 3-(methyl) acrylyl oxy-ethyl-3-ethyl epoxypropane, 2-ethyl-3-(methyl) acrylyl oxy-ethyl epoxypropane, 3-(methyl) acrylyl oxy-ethyl-2-trifluoromethyl epoxypropane, 3-(methyl) acrylyl oxy-ethyl-2-pentafluoroethyl group epoxypropane, 3-(methyl) acrylyl oxy-ethyl-2-benzyl ring Ethylene Oxide, the fluoro-3-of 2,2-bis-(methyl) acrylyl oxy-ethyl epoxypropane, 3-(methyl) acrylyl oxy-ethyl-2,2,4-trifluoro-epoxy propane, 3-(methyl) acrylyl oxy-ethyl-2,2,4,4-ptfe ring Ethylene Oxide, 2-(methyl) acryloyl-oxy methyl epoxypropane, 2-methyl-2-(methyl) acryloyl-oxy methyl epoxypropane, 3-methyl-2-(methyl) acryloyl-oxy methyl epoxypropane, 4-methyl-2-(methyl) acryloyl-oxy methyl epoxypropane, 2-(methyl) acryloyl-oxy Methyl-2-trifluoromethyl epoxypropane, 2-(methyl) acryloyl-oxy methyl-3-trifluoromethyl epoxypropane, 2-(methyl) acryloyl-oxy methyl-4-trifluoromethyl epoxypropane, 2-(methyl) acryloyl-oxy methyl-2-pentafluoroethyl group epoxypropane, 2-(methyl) acryloyl-oxy methyl-3-pentafluoroethyl group epoxypropane, 2-(methyl) acryloyl-oxy methyl-4-pentafluoroethyl group epoxypropane, 2-(methyl) acryloyl-oxy methyl-2-benzyl ring Ethylene Oxide, 2-(methyl) acryloyl-oxy methyl-3-benzyl ring Ethylene Oxide, 2-(methyl) acryloyl-oxy methyl 4-phenyl epoxypropane, the fluoro-2-of 2,3-bis-(methyl) acryloyl-oxy methyl epoxypropane, the fluoro-2-of 2,4-bis-(methyl) acryloyl-oxy methyl epoxypropane, the fluoro-2-of 3,3-bis-(methyl) acryloyl-oxy methyl epoxypropane, the fluoro-2-of 2,4-bis-(methyl) acryloyl-oxy methyl epoxypropane, the fluoro-2-of 3,4-bis-(methyl) acryloyl-oxy methyl epoxypropane, the fluoro-2-of 4,4-bis-(methyl) acryloyl-oxy methyl epoxypropane, 2-(methyl) acryloyl-oxy methyl-3,3,4-trifluoro-epoxy propane, 2-(methyl) acryloyl-oxy methyl-3,4,4-trifluoro-epoxy propane, 2-(methyl) acryloyl-oxy methyl-3,3,4,4-ptfe ring Ethylene Oxide, 2-(methyl) acrylyl oxy-ethyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-2-methyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-4-methyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-2-trifluoromethyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-3-trifluoromethyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-4-trifluoromethyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-2-pentafluoroethyl group epoxypropane, 2-(methyl) acrylyl oxy-ethyl-3-pentafluoroethyl group epoxypropane, 2-(methyl) acrylyl oxy-ethyl-4-pentafluoroethyl group epoxypropane, 2-(methyl) acrylyl oxy-ethyl-2-benzyl ring Ethylene Oxide, 2-(methyl) acrylyl oxy-ethyl-3-benzyl ring Ethylene Oxide, 2-(methyl) acrylyl oxy-ethyl-4-benzyl ring Ethylene Oxide, the fluoro-2-of 2,3-bis-(methyl) acrylyl oxy-ethyl epoxypropane, the fluoro-2-of 2,4-bis-(methyl) acrylyl oxy-ethyl epoxypropane, the fluoro-2-of 3,3-bis-(methyl) acrylyl oxy-ethyl epoxypropane, the fluoro-2-of 3,4-bis-(methyl) acrylyl oxy-ethyl epoxypropane, the fluoro-2-of 4,4-bis-(methyl) acrylyl oxy-ethyl epoxypropane, 2-(methyl) acrylyl oxy-ethyl-3,3,4-trifluoro-epoxy propane, 2-(methyl) acrylyl oxy-ethyl-3,4,4-trifluoro-epoxy propane, 2-(methyl) acrylyl oxy-ethyl-3,3,4,4-ptfe ring Ethylene Oxide, (methyl) acrylic acid ring butyl ester etc.Containing epoxypropane based compound (b2), can be used alone or mixing plural kinds of use.
The concrete example of other unsaturated monomers (b3) is: (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-butyl acrylate, (methyl) acrylic acid secondary butyl ester, three grades of butyl esters of (methyl) acrylic acid, (methyl) isopropyl acrylate, (methyl) cyclohexyl acrylate, (methyl) acrylic acid-2-methyl cyclohexyl, (methyl) acrylic acid two encircles pentyl ester, (methyl) acrylic acid two cyclopentyloxy ethyl esters, (methyl) isobornyl acrylate, diethyl maleate (diethyl maleate), DEF (diethyl fumarate), diethyl itaconate (diethyl itaconate), (methyl) 2-Hydroxy ethyl acrylate, (methyl) 2-hydroxypropyl acrylate, styrene, α-methyl styrene, m-methyl styrene, p-methylstyrene, p-methoxystyrene etc.Wherein, with styrene, three grades of butyl esters of methacrylic acid, methacrylic acid two, encircle pentyl ester, acrylic acid two cyclopentyloxy ethyl esters, p-methoxystyrene better.Other unsaturated monomers (b3) can be used alone or mixing plural kinds of use.
Epoxy resin (B) containing epoxypropane base of the present invention, the solvent using when synthetic is generally ethylene glycol list propyl ether, diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, acetic acid methoxyl ethyl ester, ethoxyethyl acetate(EA), diethylene glycol monomethyl ether, TC, diethylene glycol single-butyl ether, propylene glycol monomethyl ether acetate, propylene glycol list ethylether acetate, propylene glycol list propyl ether acetate, MEK and acetone compared with dust head.Wherein, with diethylene glycol dimethyl ether, propylene glycol monomethyl ether acetate for better.Aforementioned solvents can be used alone or mixing plural kinds of use.
Epoxy resin (B) containing epoxypropane base of the present invention, the initiator using when synthetic, be generally free radical shape polymerization initiator, its concrete example is as 2,2 '-azobis isobutyronitrile (2,2 '-azobisiso-butyronitrile), 2,2 '-azo two (2,4-methyl pentane nitrile) [2,2 '-azobis (2,4-dimethylvaleronitrile)], 2, azo (azo) compounds such as 2 '-azo two (4-methoxyl-2,4-methyl pentane nitriles); The per-compound such as dibenzoyl peroxide (benzoylperoxide).
Based on novolac resin (A) 100 weight portions, the use amount that contains the epoxy resin (B) of epoxypropane base is generally 5～40 weight portions, is preferably 7～35 weight portions, is more preferred from 10～30 weight portions.Owing to can forming structure more closely in rear when roasting with oh type novolac resin (A-1) containing the epoxy resin (B) of epoxypropane base, therefore be difficult for producing crack or wrinkling.When the use amount containing the epoxy resin (B) of epoxypropane base is during between 5～40 weight portion, can on substrate, form the good pattern of resistance to Fractured.
[repeatedly nitrogen sulphonic acids carboxylate (C) of adjacent naphthoquinones two]
The photonasty material of positive-type photosensitive resin composition of the present invention adopts repeatedly nitrogen sulphonic acids carboxylate (C) of adjacent naphthoquinones two, this carboxylate (C) has no particular limits, can select frequent user, wherein, be preferably the repeatedly carboxylate of nitrogen sulfonic acid and hydroxyl compound of adjacent naphthoquinones two, better person is the repeatedly carboxylate of nitrogen sulfonic acid and multi-hydroxy compound of adjacent naphthoquinones two, and esterification or the partly esterification completely of aforementioned carboxylate; This neighbour's naphthoquinones two repeatedly concrete example of nitrogen sulfonic acid is: adjacent naphthoquinones two is repeatedly repeatedly nitrogen-6-sulfonic acid etc. of nitrogen-5-sulfonic acid, adjacent naphthoquinones two of nitrogen-4-sulfonic acid, adjacent naphthoquinones two repeatedly.The kind of aforementioned hydroxyl compound is listed as follows:
(1) hydroxy benzophenone ketone compounds, its concrete example is: 2,3,4-trihydroxybenzophenone, 2,4,4'-trihydroxybenzophenone, 2,4,6-trihydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, 2,2', 4,4'-tetrahydroxybenzophenone, 2,3', 4,4', 6-pentahydroxybenzophenone, 2,2', 3,4,4'-pentahydroxybenzophenone, 2,2', 3,4,5'-pentahydroxybenzophenone, 2,3', 4,5,5'-pentahydroxybenzophenone, 2,3,3', 4,4', 5'-hexahydroxy benzophenone etc.
(2) the represented hydroxy aryl compound of general expression (I)
In formula, R
1～R
3for hydrogen atom or low alkyl group, R
4～R
9for hydrogen atom, halogen atom, low alkyl group, lower alkoxy (alkoxy), rudimentary fat thiazolinyl (alkenyl) or naphthenic base (cycloalkyl), R
10and R
11for hydrogen atom, halogen atom or low alkyl group, the integer that x, y and z are 1～3, n is 0 or 1.The concrete example of the represented hydroxy aryl compound of general expression (I) is: three (4-hydroxy phenyl) methane, two (4-hydroxyl-3,5-3,5-dimethylphenyl)-4-hydroxy phenyl methane, two (4-hydroxyl-3,5-3,5-dimethylphenyl)-3-hydroxy phenyl methane, two (4-hydroxyl-3,5-3,5-dimethylphenyl)-2-hydroxy phenyl methane, two (4-hydroxyl-2,5-3,5-dimethylphenyl)-4-hydroxy phenyl methane, two (4-hydroxyl-2,5-3,5-dimethylphenyl)-3-hydroxy phenyl methane, two (4-hydroxyl-2,5-3,5-dimethylphenyl)-2-hydroxy phenyl methane, two (4-hydroxyl-3,5-3,5-dimethylphenyls)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyl-2,5-3,5-dimethylphenyls)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyl-3,5-3,5-dimethylphenyls)-2,4-dihydroxy benzenes methylmethane, two (4-hydroxyl-2,5-3,5-dimethylphenyls)-2,4-dihydroxy benzenes methylmethane, two (4-hydroxy phenyl)-3-methoxyl-4-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxy phenyl)-3-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxy phenyl)-2-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxy phenyl)-4-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxyl-6-methyl aryl)-2-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxyl-6-aminomethyl phenyl)-3-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxyl-6-aminomethyl phenyl)-4-hydroxy phenyl methane, two (3-cyclohexyl-4-hydroxyl-6-aminomethyl phenyls)-3,4-dihydroxy benzenes methylmethane, two (3-cyclohexyl-6-hydroxy phenyl)-3-hydroxy phenyl methane, two (3-cyclohexyl-6-hydroxy phenyl)-4-hydroxy phenyl methane, two (3-cyclohexyl-6-hydroxy phenyl)-2-hydroxy phenyl methane, two (3-cyclohexyl-6-hydroxy-4-methyl phenyl)-2-hydroxy phenyl methane, two (3-cyclohexyl-6-hydroxy-4-methyl phenyl)-4-hydroxy phenyl methane, two (3-cyclohexyl-6-hydroxy-4-methyl phenyl)-3,4-dihydroxy benzenes methylmethane, 1-[1-(4-hydroxy phenyl) isopropyl]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] benzene, 1-[1-(3-methyl-4-hydroxy phenyl) isopropyl]-4-[1, two (3-methyl-4-hydroxy phenyl) ethyls of 1-] benzene etc.
(3) represented (hydroxy phenyl) hydrocarbon compound of general expression (II)
In formula, R
12and R
13for hydrogen atom or low alkyl group, the integer that x' and y' are 1～3.The concrete example of represented (hydroxy phenyl) hydro carbons of general expression (II) is: 2-(2,3,4-trihydroxy phenyl)-2-(2', 3', 4'-trihydroxy phenyl) propane, 2-(2,4-dihydroxy phenyl)-2-(2', 4'-dihydroxy phenyl) propane, 2-(4-hydroxy phenyl)-2-(4'-hydroxy phenyl) propane, two (2,3,4-trihydroxy phenyl) methane, two (2,4-dihydroxy phenyl) methane etc.
(4) other aromatic hydroxy compounds, concrete example is: phenol, p-metoxyphenol, xylenol, p-dihydroxy-benzene, bisphenol-A, naphthols (naphthol), catechol (pyrocatechol), 1,2,3-benzenetriol methyl ether (pyrogallol monomethyl ether), 1,2,3-benzenetriol-1,3-dimethyl ether (pyrogallol-1,3-dimethyl ether), 3,4, the Gallic Acid of 5-trihydroxybenzoic acid (gallic acid), part esterification or part etherificate etc.
Aforementioned hydroxyl compound is with 2,3,4-trihydroxybenzophenone, 2,3,4, and 4'-tetra-hydroxyl oxygen base benzophenone are for better.Aforementioned hydroxyl compound is can be separately a kind of to be used or mixes several uses.
Repeatedly nitrogen sulphonic acids carboxylate (C) of the adjacent naphthoquinones two of photonasty material in resin combination of the present invention, can use and contain the repeatedly compound of nitrogen base of quinone two, for example: adjacent naphthoquinones two repeatedly nitrogen-4 (or 5) sulfonic acid halogen and the hydroxyl compound shown in aforementioned (one)～(four) through the complete esterification of condensation reaction or partly esterification and obtaining, aforementioned condensation reaction is conventionally at dioxane (dioxane), N-pyrrolidone (N-pyrrolidone), in the organic solvents such as acetamide (acetamide), carry out, simultaneously, condensation reaction is at triethanolamine (triethanolamine), the alkaline condensing agent such as alkali carbonate or alkali metal hydrogencarbonate carries out more favourable under existing.
Now, based on 100 % by mole of hydroxyl total amounts in hydroxyl compound, be preferably more than 50 % by mole, be more preferred from 60 % by mole of above and adjacent naphthoquinones two repeatedly the condensation of nitrogen-4 (or 5)-sulfonic acid halogen form carboxylate, that is, esterification degree more than 50% for better, preferably more than 60%.
Based on novolac resin (A) 100 weight portions, the use amount that in the present invention, adjacent naphthoquinones two changes nitrogen sulphonic acids carboxylate (C) is generally 1～100 weight portion, be preferably 10～50 weight portions, be more preferred from 20～40 weight portions, when adjacent naphthoquinones two is when repeatedly the use amount of nitrogen sulphonic acids carboxylate (C) is between 1～100 weight portion, can improve the sensitivity of resin combination.
[solvent (D)]
The organic solvent that solvent used in the present invention (D) need be selected easily and other organic principles dissolve mutually.
Solvent used in the present invention (D) concrete example is: ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, TC, diethylene glycol list n-propyl ether, diethylene glycol list n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol list ethylether, propylene glycol monomethyl ether, propylene glycol list ethylether, DPGME, dihydroxypropane single-ethyl ether, dipropylene glycol list n-propyl ether, dipropylene glycol list n-butyl ether, tripropylene glycol monomethyl ether, they (gathering) alkylene glycol mono alkane ethers such as tripropylene glycol list ethylether, they (gathering) alkylene glycol mono alkane ether acetate classes such as ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol list ethylether acetate, other ethers of diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran etc., the ketone of MEK, cyclohexanone, 2-HEPTANONE, 3-heptanone etc., the lactic acid alkane ester classes such as 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate, 3-methoxy methyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, ethoxy ethyl acetate, hydroxacetic acid ethyl ester, 2-hydroxy-3-methyl methyl butyrate, 3-methyl-3-methoxyl butylacetic acid ester, 3-methyl-3-methoxyl butyl propionic ester, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-Amyl acetate, isoamyl acetate, n-butyl propionate, ethyl butyrate, propyl butyrate, isopropyl isobutyrate, the positive butyl ester of butyric acid, methyl pyruvate, ethyl pyruvate, pyruvic acid n-propyl, methyl acetoacetate, ethyl acetoacetate, other ester classes of 2-oxygen base ethyl butyrate etc., toluene, dimethylbenzene etc. aromatic hydrocarbon based, the carboxylic acid amines such as 1-METHYLPYRROLIDONE, DMF, DMA.Wherein, with propylene glycol monomethyl ether acetate and ethyl lactate for better.Aforementioned solvents can be used alone or mixing plural kinds of use.
Based on novolac resin (A) 100 weight portions, the use amount of solvent in photosensitive resin composition of the present invention (D) is generally 500～2, and 000 weight portion is preferably 600～1,800 weight portions, is more preferred from 700～1,500 weight portions.
[adjuvant (E)]
Positive-type photosensitive resin composition of the present invention, can further add aromatic hydroxy compound, uses sensitivity or the viscosity of adjusting constituent.The concrete example that is suitable for aromatic hydroxy compound of the present invention is as commercially available products (Japanese Honshu chemical industry system) such as TPPA-1000P, TPPA-100-2C, TPPA-1100-3C, TPPA-1100-4C, TPPA-1200-24X, TPPA-1200-26X, TPPA-1300-235T, TPPA-1600-3M6C, TPPA-MF, wherein, with TPPA-600-3M6C, TPPA-MF, for better, aforementioned aromatic hydroxy compound can a kind ofly separately be used or mix plural number kind and use.Based on novolac resin (A) 100 weight portions, the use amount of aromatic hydroxy compound is generally 0～20 weight portion, is preferably 0.5～18 weight portion, is more preferred from 1.0～15 weight portions.
Positive-type photosensitive resin composition of the present invention, can optionally further add adherence auxiliary agent, the agent that has an even surface, thinning agent and compatible good dyestuff.
Adherence auxiliary agent of the present invention comprises melamine (melamine) compound, silane system (silane) compound, its role is to increase the adherence between positive-type photosensitive resin composition and attaching substrates.Wherein, the concrete example of melamine is as commercially available products such as: Cymel-300, Cymel-303 (Mitsui Chemicals system), MW-30MH, MW-30, MS-11, MS-001, MX-750, MX-706 (three and chemistry system).And the concrete example of silane based compound is as vinyltrimethoxy silane, vinyltriethoxysilane, 3-(methyl) acryloxy propyl trimethoxy silicane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, APTES, 3-glycidoxypropyltrime,hoxysilane, 3-glycidoxy propyl group methyl dimethoxysilane, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-metacryloxy propyl trimethoxy silicane, 3-mercapto propyl trimethoxy silicane, two-1, 2-(trimethoxy is silica-based) ethane etc.Based on novolac resin (A) 100 weight portions, the use amount of melamine compound adherence auxiliary agent is generally 0～20 weight portion, is preferably 0.5～18 weight portion, is more preferred from 1.0～15 weight portions; The use amount of silane based compound adherence auxiliary agent is generally 0～2 weight portion, is preferably 0.001～1 weight portion, is more preferred from 0.005～0.8 weight portion.
It is that interfacial agent, silicon are interfacial agent that the agent that has an even surface of the present invention comprises fluorine.Wherein, fluorine is that the concrete example of interfacial agent is as Flourate FC-430, FC-431 (3M system), the commercially available products such as F-top EF122A, 122B, 122C, 126, BL20 (Tochem product system).And silicon is that the concrete example of interfacial agent is as commercially available products such as SF8427, SH29PA (Toray Dow Corning Silicone system).Based on novolac resin (A) 100 weight portions, the use amount of aforementioned interfacial agent is generally 0～1.2 weight portion, is preferably 0.025～1.0 weight portion, is more preferred from 0.050～0.8 weight portion.
Be suitable for thinning agent of the present invention as commercially available products such as RE801, RE802 (Ink of kingdom system).
The concrete example that is suitable for the compatible good dyestuff of the present invention as: curcumin (curcumin), cumarin (coumarin) are, azo (azo) dyestuff etc., in addition, the present invention also can add other adjuvant according to need again, for example: plasticizer, stabilization agent etc.
< positive-type photosensitive resin composition forms the method > of pattern
The present invention uses aforementioned positive-type photosensitive resin composition to form the method for pattern, by coating processes such as rotary coating, curtain coating coating or print roll coatings, this photosensitive resin composition is coated on substrate, and in pre-baked (prebake) mode, removal of solvents is formed to pre-baked film after coating.Wherein, pre-baked condition according to each composition kind, coordinate ratio and different, be generally temperature between 70～110 ℃, carry out 1～15 minute.
After pre-baked, this film is exposed in specifying under light shield, then at the temperature of 23 ± 2 ℃, impregnated in developer solution, last 15 seconds～5 minutes, by this part of not wanting is removed and form specific pattern.The light that exposure is used, take ultraviolet rays such as g line, h line, i lines as good, and ultraviolet lamp can be (surpassing) high-pressure mercury-vapor lamp and metal halid lamp.
The concrete example of developer solution used herein is as NaOH, potassium hydroxide, sodium carbonate, sodium bicarbonate, sal tartari, saleratus, sodium silicate, sodium methyl silicate, ammoniacal liquor, ethamine, diethylamine, dimethylethanolamine, tetramethylphosphonihydroxide hydroxide amine, tetraethylammonium hydroxide, choline, pyrroles, piperidines and 1,8-diazabicylo-(5,4,0)-alkali compounds such as 7-hendecene.
Preferably, the concentration of developer solution, between 0.001 % by weight～10 % by weight, is more preferably between 0.005 % by weight～5 % by weight, is more preferably again between 0.01 % by weight～1 % by weight.
While using the developer solution that aforementioned alkali compounds forms, conventionally after developing, with water, clean, then with pressurized air or air-dry this film of compressed nitrogen.Then, using the heating arrangements such as hot plate or baking oven to carry out rear roasting (postbake) to this film processes.Rear roasting temperature is generally 100～250 ℃, and wherein, using the heat time of hot plate is 1 minute～60 minutes, and using the heat time of baking oven is 5 minutes～90 minutes.After above treatment step, can form pattern in substrate.
< electric crystal array film substrate >
The manufacture method of electric crystal array film substrate of the present invention (abbreviation tft array substrate) is to form according to the method for aforementioned formation pattern.That is, positive-type photosensitive resin composition of the present invention is coated on the glass substrate of films such as containing aluminium, chromium, silicon nitride or amorphous silicon or plastic base with coating methods such as the coating of rotary coating, curtain coating or print roll coatings and formed an eurymeric photoresist layer, then through pre-baked, exposure, develop and after roasting process form photoresist pattern after, carry out etching and photoresistance and peel off; Repeat above-mentioned steps and can make an electric crystal array film substrate containing most membrane transistors or electrode.
At this, with reference to figure pair of L, CD is illustrated with tft array substrate.
Figure mono-is the cross-sectional schematic that illustrates LCD tft array substrate.(1) first, aluminium film on glass substrate 101 etc. locates to arrange gate 102a and storage capacitors Cs electrode 102b; (2) secondly, in upper capping oxidation silicon fiml (SiOx) 103 of gate 102a or silicon nitride film (SiNx) 104 etc., form dielectric film, and on this dielectric film; (3) form the noncrystalline silicon layer (a-Si) 105 as semiconductor active layer; (4) then, in order to reduce junction impedance, be provided with the noncrystalline silicon layer 106 of doping nitrogen impurity; (5) then, use the metals such as aluminium to form collector 107a and source electrode 107b, this collector 107a is connected on data signals line (not shown), and this source electrode 107b is connected on pixel electrode (or sub-pixel electrode) 109; (6) last, for protection is as noncrystalline silicon layer (a-Si) 105, collector 107a or the source electrode 107b etc. of semiconductor active layer, silicon nitride film etc. is set as diaphragm 108.
< LCD assembly >
LCD assembly of the present invention, has comprised foregoing tft array substrate, and this tft array substrate is according to pattern formation method of the present invention and constitutor.In addition, also can contain according to need other portion's material.
The concrete example of the basic comprising form of foregoing liquid crystal display module as: (1) by the driven units such as TFT and pixel electrode (conductive layer) through arranging the tft array substrate of the present invention (driving substrate) being formed, and between the colored filter substrate forming by colored filter and to electrode (conductive layer), get involved interval body and subtend configuration, finally in gap part, enclose liquid crystal material and form.Or, (2) the one-piece type tft array substrate of colored filter of colored filter will directly be formed on tft array substrate of the present invention, and configured getting involved interval body and subtend configuration between the subtend substrate of electrode (conductive layer), finally in gap part, enclosed liquid crystal material and formation etc.
The concrete example of aforementioned conductive layer is as ITO film; The metal films such as aluminium, zinc, copper, iron, nickel, chromium, molybdenum; The metal oxide film of silicon dioxide etc. etc.Wherein, with the rete of the tool transparency for better, again take ITO film as best.
The base materials such as aforementioned tft array substrate of the present invention, colored filter substrate and subtend substrate, its concrete example as: the known glass such as soda-lime glass, low-expansion glass, alkali-free glass, quartz glass, in addition, also can adopt the substrate consisting of plastic foil etc.
Accompanying drawing explanation
Fig. 1 is the cross-sectional schematic that illustrates LCD tft array substrate.
Symbol description
101 glass substrates; 102a gate; 102b Cs electrode; 103 silicon oxide films (SiOx);
104 silicon nitride films (SiNx); 105 noncrystalline silicon layers (a-Si);
The noncrystalline silicon layer of 106 doping nitrogen impurities; 107a collector; 107b source electrode;
108 diaphragms; 109 pixel electrodes.
Embodiment
The present invention will be described further with regard to following examples, but will be appreciated that, described embodiment is the use for illustrating only, and should not be interpreted as restriction of the invention process.
[synthesis example 1]
On four cervical vertebra bottles of 1000 milliliters of volumes, nitrogen inlet, stirrer, well heater, condenser pipe and thermometer are set, after importing nitrogen, add m-cresol 64.89g (0.6 mole), p-Cresol 43.26g (0.4 mole), 3,4-4-dihydroxy benzaldehyde 55.25g (0.4 mole) and oxalic acid 1.80g (0.02 mole).Slowly stir and make reaction solution be warming up to 100 ℃, and polymerization 5 hours at this temperature.Then, reaction solution is warming up to 180 ℃, with the pressure of 10mmHg, carries out drying under reduced pressure, will after solvent devolatilization, can obtain oh type novolac resin (A-1-1).
[synthesis example 2]
To be same as the step of aforementioned synthesis example 1, prepare oh type novolac resin (A-1-2), difference is in replacing 3,4-4-dihydroxy benzaldehyde with o-hydroxy benzaldehyde 48.85g (0.4 mole).
[synthesis example 3]
To be same as the step of aforementioned synthesis example 1, prepare oh type novolac resin (A-1-3), difference is in replacing 3,4-4-dihydroxy benzaldehyde with 2,3,4-tri hydroxybenzaldehyde 61.65g (0.4 mole).
[synthesis example 4]
To be same as the step of aforementioned synthesis example 1, prepare novolac resin (A-2-1), difference is in the formaldehyde 32.43g with 37 % by weight (0.4 mole) and replaces 3,4-4-dihydroxy benzaldehyde.
[synthesis example 5]
To be same as the step of aforementioned synthesis example 1, prepare novolac resin (A-2-2), difference is in replacing 3,4-4-dihydroxy benzaldehyde with benzaldehyde 42.45g (0.4 mole).
[synthesis example 6]
On four cervical vertebra bottles of 1000 milliliters of volumes, nitrogen inlet, stirrer, well heater, condenser pipe and thermometer are set, import after nitrogen add propylene glycol monomethyl ether acetate 200g, 3-(methyl) acryloyl-oxy methyl-2-benzyl ring Ethylene Oxide 30g, methacrylic acid 25g, methacrylic acid two encircles pentyl ester 35g and styrene 10g.Slowly stir and make reaction solution be warming up to 80 ℃, then by 2,2 '-azobis isobutyronitrile 2g is dissolved in propylene glycol monomethyl ether acetate 20g, and is added in four cervical vertebra bottles at one hour interval with the amount of five equal portions.The temperature of reaction of polymerization process maintains 80 ℃, polymerization time 4 hours.Complete after polymerization, by solvent devolatilization, can be containing the epoxy resin (B-1) of epoxypropane base.
[synthesis example 7]
To be same as the step preparation of aforementioned synthesis example 6 containing the epoxy resin (B-2) of epoxypropane base, difference is in changing feed composition, with 3-(methyl) acryloyl-oxy methyl-3-ethyl epoxypropane 30g, replaces 3-(methyl) acryloyl-oxy methyl-2-benzyl ring Ethylene Oxide.
[synthesis example 8]
To be same as the step preparation of aforementioned synthesis example 6 containing the epoxy resin (B-3) of epoxypropane base, difference is in changing feed composition, with 2-(methyl) acryloyl-oxy methyl-4-trifluoromethyl epoxypropane 30g, replaces 3-(methyl) acryloyl-oxy methyl-2-benzyl ring Ethylene Oxide.
[synthesis example 9]
On four cervical vertebra bottles of 1000 milliliters of volumes, nitrogen inlet, stirrer, well heater, condenser pipe and thermometer are set, after importing nitrogen, add diethylene glycol dimethyl ether 200g, methacrylic acid 30g, glytidyl methacrylate (glycidyl methacrylate) 25g, styrene 20g and three grades of butyl ester 25g of methacrylic acid.Slowly stir and make reaction solution be warming up to 85 ℃, then by 2,2 '-azobis isobutyronitrile 2g is dissolved in diethylene glycol dimethyl ether, and is added in four cervical vertebra bottles at one hour interval with five aliquot.The temperature of reaction of polymerization process maintains 85 ℃, polymerization time 6 hours.Complete after polymerization, by solvent devolatilization, can obtain epoxy resin (B '-1).
[synthesis example 10]
To be same as the step of aforementioned synthesis example 9, prepare epoxy resin (B '-2), difference is in changing feed composition, with o-vinyl benzene methyl epoxy propyl ether 25g substituent methyl Glycidyl Acrylate.
The embodiment of < photosensitive resin composition and comparative example >
Embodiment 1
By 2 of the epoxy resin (B-1) containing epoxypropane base of the oh type novolac resin (A-1-1) of 100 weight portions, 15 weight portions and 25 weight portions, 3,4-trihydroxybenzophenone and 1,2-naphthoquinones two potpourri that repeatedly carboxylate (C-1) (average esterification degree 85%) of nitrogen-5-sulfonic acid forms, add in the solvent (D-1) of the propylene glycol monomethyl ether acetate of 750 weight portions, with swing-out stirrer, stir this potpourri is dissolved in solvent, carry out polyreaction 3 hours, can make positive-type photosensitive resin composition of the present invention.Below each test item of note detects, and acquired results is as shown in table 1.
Embodiment 2～8
Be same as the method for operating of embodiment 1, different places are: the kind of feed change and use amount thereof, its formula and testing result are as shown in table 1.
Comparative example 1～6
Be same as the method for operating of embodiment 1, different places are: the kind of feed change and use amount thereof, its formula and testing result are as shown in table 1.
[test item]
The < > of resistance to Fractured
Mode by positive-type photosensitive resin composition with rotary coating, is coated on the Silicon Wafer of one 6 inch, then at 110 ℃ of temperature, within pre-baked 160 seconds, forms the pre-baked film of one 1.2 μ m.Then,, in specifying under light shield, take ultraviolet light, (exposure machine model is as AG500-4N; M & R Nano Technology system) 6mJ/cm
2light quantity irradiate after, then film be impregnated in to the developer solution (2.38% Tetramethylammonium hydroxide) 60 seconds of 23 ℃, the film of exposed portion is removed, then with pure water, clean, after the temperature of 160 ℃, bake 5 minutes again, make positive-type photosensitive resin composition form pattern.
A part for pattern is flooded after 30 minutes, by the state of observation by light microscope patterned surfaces in N-methylpyrrole pyridine ketone (NMP).Zero represents that pattern does not change, and ╳ represents that pattern has crack to produce.
< residual film ratio >
In the test item < > of resistance to Fractured, the pre-baked film of gained is taken up an official post and is got a measuring point and record a thickness (δ).Then film be impregnated in to the developer solution (2.38% Tetramethylammonium hydroxide) of 23 ℃ after 1 minute, at identical measuring point, record another thickness (δ
d).Finally by following formula, calculate and can obtain residual film ratio.Residual film ratio (%)=[(δ
d)/(δ)] × 100.Zero: residual film ratio >=90%; △: 90% > residual film ratio >=80%; ╳: residual film ratio < 80%.
As described above, it is only preferred embodiment of the present invention, can not limit practical range of the present invention with this, i.e. all simple equivalences of doing according to the present patent application the scope of the claims and description of the invention content change and modify, and all should still belong in patent covering scope of the present invention.
Wherein, C-1 is 2,3,4-trihydroxybenzophenone and the repeatedly carboxylate of nitrogen-5-sulfonic acid of 1,2-naphthoquinones two;
C-2 is 2,3,4,4'-Tetrahydroxybenzophenone and the repeatedly carboxylate of nitrogen-5-sulfonic acid of 1,2-naphthoquinones two;
D-1 is propylene glycol monomethyl ether acetate (PGMEA, propylene glycol monomethyl ether acetate);
D-2 is propylene glycol list ethylether (PGEE, propylene glycol monoethyl ether);
D-3 is ethyl lactate (EL, ethyl lactate); E-1 is 3-glycidoxypropyltrime,hoxysilane (trade name KBM-403, SHIN-ETSU HANTOTAI's chemistry system);
E-2 is interfacial agent, trade name SH29PA, Toray Dow Corning Silicone system.
Claims (10)
1. a positive-type photosensitive resin composition, is characterized in that, comprises following component:
Novolac resin (A);
Containing the epoxy resin (B) of epoxypropane base;
Repeatedly nitrogen sulphonic acids carboxylate (C) of adjacent naphthoquinones two; And
Solvent (D);
Wherein, this novolac resin (A) comprises oh type novolac resin (A-1), this oh type novolac resin (A-1) is by hydroxy benzaldehyde compound and aromatic hydroxy compound condensation and obtain, and based on novolac resin (A) 100 weight portions, the use amount of this oh type novolac resin (A-1) is 30～100 weight portions, should be by unsaturated carboxylic acid monomer (b1) containing the epoxy resin (B) of epoxypropane base, contain epoxypropane based compound (b2) and other unsaturated monomers (b3) institute's copolymerization and obtain.
2. positive-type photosensitive resin composition according to claim 1, it is characterized in that, this hydroxy benzaldehyde compound is to be selected from the group that hydroxy benzaldehyde compound, 4-dihydroxy benzaldehyde compound, tri hydroxybenzaldehyde compound and hydroxy alkyl benzaldehyde compound form.
3. positive-type photosensitive resin composition as claimed in claim 2, is characterized in that, this hydroxy benzaldehyde compound is to be selected from the group that o-hydroxy benzaldehyde, m-hydroxy benzaldehyde and p-hydroxybenzaldehyde form.
4. positive-type photosensitive resin composition as claimed in claim 2, is characterized in that, this 4-dihydroxy benzaldehyde compound is to be selected from 2,3-4-dihydroxy benzaldehyde, 2,4-4-dihydroxy benzaldehyde, 2,5-4-dihydroxy benzaldehyde, 3, the group that 4-4-dihydroxy benzaldehyde and 3,5-4-dihydroxy benzaldehyde form.
5. positive-type photosensitive resin composition as claimed in claim 2, is characterized in that, this tri hydroxybenzaldehyde compound is to be selected from 2,3,4-tri hydroxybenzaldehyde, 2,4,5-tri hydroxybenzaldehyde, 2,4,6-tri hydroxybenzaldehyde, 3,4, the group that 5-tri hydroxybenzaldehyde forms.
6. positive-type photosensitive resin composition as claimed in claim 2, is characterized in that, this hydroxy alkyl benzaldehyde compound is to be selected from the group that o-methylol benzaldehyde, m-methylol benzaldehyde and p-methylol benzaldehyde form.
7. positive-type photosensitive resin composition as claimed in claim 1, it is characterized in that, based on novolac resin (A) 100 weight portions, the use amount that contains the epoxy resin (B) of epoxypropane base is 5～40 weight portions, the adjacent naphthoquinones two repeatedly use amount of nitrogen sulphonic acids carboxylate (C) is 1～100 weight portion, and the use amount of solvent (D) is 500～2000 weight portions.
8. a pattern formation method, is characterized in that, the positive-type photosensitive resin composition described in arbitrary claim in claim 1～7 is coated to substrate, more sequentially bestows pre-baked, exposure, development and rear roasting processing, forms pattern accordingly in this substrate.
9. an electric crystal array film substrate, comprises pattern claimed in claim 8.
10. a LCD assembly, comprises electric crystal array film substrate claimed in claim 9.
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| TW099139862 | 2010-11-18 | ||
| TW99139862A TWI443463B (en) | 2010-11-18 | 2010-11-18 | A positive-type photosensitive resin composition and a method for forming a pattern of the composition |
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| CN1207058A (en) * | 1995-11-30 | 1999-02-03 | 阿迈隆国际公司 | Heat ablative coating composition |
| CA2228654A1 (en) * | 1997-02-18 | 1998-08-18 | James J. Briguglio | Positive-tone photoimageable crosslinkable coating |
| CN1224858A (en) * | 1998-01-30 | 1999-08-04 | 莫顿国际股份有限公司 | Positive-tone photoimageable crosslinkable coating |
| CN1500119A (en) * | 2001-02-26 | 2004-05-26 | 音思万有限公司 | Positive photodefinable compsn. of polycarboxylic acid, phenolic and thermocurable resins |
| KR101324646B1 (en) * | 2006-05-08 | 2013-11-01 | 주식회사 동진쎄미켐 | Photoresist composition |
| KR20090021001A (en) * | 2007-08-24 | 2009-02-27 | 삼성전자주식회사 | Making method of display device and composition of sealant therefor |
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| CN102566273A (en) | 2012-07-11 |
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