CN104007617A - Positive photosensitive resin composition and pattern forming method thereof - Google Patents
Positive photosensitive resin composition and pattern forming method thereof Download PDFInfo
- Publication number
- CN104007617A CN104007617A CN201410055536.3A CN201410055536A CN104007617A CN 104007617 A CN104007617 A CN 104007617A CN 201410055536 A CN201410055536 A CN 201410055536A CN 104007617 A CN104007617 A CN 104007617A
- Authority
- CN
- China
- Prior art keywords
- novolac resin
- compound
- photosensitive organic
- hydroxy
- organic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000011342 resin composition Substances 0.000 title abstract 4
- -1 hydroxyl compound Chemical class 0.000 claims abstract description 97
- 229920003986 novolac Polymers 0.000 claims abstract description 79
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims abstract 7
- 150000002894 organic compounds Chemical class 0.000 claims description 55
- 150000007942 carboxylates Chemical class 0.000 claims description 29
- 229930192627 Naphthoquinone Natural products 0.000 claims description 25
- 150000002791 naphthoquinones Chemical group 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 17
- 239000004973 liquid crystal related substance Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 11
- 238000012545 processing Methods 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- 230000007261 regionalization Effects 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 6
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 230000018109 developmental process Effects 0.000 claims description 3
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000010408 film Substances 0.000 description 21
- 150000003739 xylenols Chemical class 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910021417 amorphous silicon Inorganic materials 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012752 auxiliary agent Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
- 238000002360 preparation method Methods 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003513 alkali Substances 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
- 239000002585 base Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940079877 pyrogallol Drugs 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
- 150000000181 1,2-naphthoquinones Chemical class 0.000 description 3
- 150000000343 2,5-xylenols Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 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
- 238000010586 diagram Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZRDYULMDEGRWRC-UHFFFAOYSA-N (4-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O ZRDYULMDEGRWRC-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 description 2
- 150000000341 2,3-xylenols Chemical class 0.000 description 2
- WNCNWLVQSHZVKV-UHFFFAOYSA-N 2,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C=C1O WNCNWLVQSHZVKV-UHFFFAOYSA-N 0.000 description 2
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- XVHIUKSUZLPFCP-UHFFFAOYSA-N 2-(hydroxymethyl)benzaldehyde Chemical compound OCC1=CC=CC=C1C=O XVHIUKSUZLPFCP-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 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
- LPYUENQFPVNPHY-UHFFFAOYSA-N 3-methoxycatechol Chemical compound COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-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
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XNWPXDGRBWJIES-UHFFFAOYSA-N Maclurin Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=C(O)C(O)=C1 XNWPXDGRBWJIES-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000013459 approach Methods 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
- 239000003990 capacitor Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 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
- 238000007766 curtain coating Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 208000013469 light sensitivity Diseases 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002883 o-cresols Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 239000012749 thinning agent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical class CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-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
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 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
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 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
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010189 synthetic method 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 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
- 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
- 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
Landscapes
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
The invention relates to a positive photosensitive resin composition and a method for forming patterns. The positive photosensitive resin composition comprises a novolac resin , an ester (B) of an o-naphthoquinone diazide sulfonic acid, a hydroxyl compound (C) and a solvent (D). The novolac resin comprises a hydroxyl novolac resin (A-1) and a xylenol novolac resin (A-2), wherein the hydroxyl novolac resin (A-1) is obtained by condensing a hydroxybenzaldehyde compound and an aromatic hydroxyl compound, and the xylenol novolac resin (A-2) is obtained by condensing an aldehyde compound and a xylenol compound. The positive photosensitive resin composition can form a pattern with high film thickness and good cross-sectional shape after post-baking.
Description
Technical field
The invention relates to a kind of positive type photosensitive organic compound and pattern formation method thereof, and relate to especially one for SIC (semiconductor integrated circuit) element, the liquid crystal display cells of thin film transistor (TFT) (hereinafter to be referred as TFT) or the processing procedure of contact panel, can be in rear roasting rear high thickness and the good pattern of section configuration of obtaining.
Background technology
Along with the microminiaturization of various electronic products in life, various intelligent mobile phones, slim TV and dynamical microprocessor improve day by day for high-resolution requirement, cause lithographic process to need more and more accurate, to form meticulousr live width.
For above-mentioned object, a day disclosure special permission 2003-98669 discloses a kind of positive type photosensitive organic compound, and said composition comprises novolac resin, light acid propellant and organic solvent.This novolac resin is in the phenols that the contains metacresols more than 50 percentage by weights (phenols beyond metacresol; such as pseudocuminol, xylenol and orthoresol) and the existence of the organic solvent such as aldehydes and acid catalyst under react; and use part or all hydroxyl of alkoxyalkyl protection novolac resin, can promote sensitivity and the resolution of positive type photosensitive organic compound.Secondly, a day disclosure special permission 2001-183838 discloses a kind of positive type photosensitive organic compound, and said composition comprises novolac resin, light acid propellant and by acid catalyzed bridging agent.This patent, in the time of synthetic novolac resin, is carried out polycondensation reaction under the existence of use alkali soluble resin and cresols compound and/or xylenol compound and acid catalyst, also can promote sensitivity and the resolution of positive type photosensitive organic compound.
But in aforesaid known technology, its photosensitive polymer combination cannot form the pattern of a high thickness after rear baking.Secondly, the pattern that formed is thus not good because of section configuration, causes the yield of successive process to reduce.Therefore, positive type photosensitive organic compound, how at rear roasting rear high thickness and the good pattern of section configuration of forming, has become an important topic in the art.
In view of this, need badly and propose a kind ofly in the rear pattern that forms high thickness after roasting, the good positive type photosensitive organic compound material with gathering around figuratum section configuration, to overcome the variety of problems of known technology.
Summary of the invention
The object of the invention is to propose a kind of variety of problems that substantially overcomes prior art, can after rear baking, form the positive type photosensitive organic compound material of the good pattern of high thickness and section configuration, and the formation method of pattern.
Therefore, an aspect of the present invention is to provide a kind of positive type photosensitive organic compound, its carboxylate (B) that comprises novolac resin (A), adjacent naphthoquinones two nitrine sulphonic acids, hydroxyl compound (C) and solvent (D).Above-mentioned novolac resin (A) comprises oh type novolac resin (A-1) and xylenol type novolac resin (A-2), wherein oh type novolac resin (A-1) is by hydroxy benzaldehyde compound and aromatic hydroxy compound condensation and obtain, and xylenol type novolac resin (A-2) is by aldehyde compound and xylenol compounds polycondensation and obtain.
Another aspect of the present invention is to provide a kind of pattern formation method, and it is sequentially to bestow coating processing, pre-baked processing, exposure-processed, development treatment and rear roasting processing by the positive type photosensitive organic compound to above-mentioned, uses and on substrate, forms pattern.Above-mentioned positive type photosensitive organic compound can be in rear roasting rear high thickness and the good pattern of section configuration of forming.
Another aspect of the present invention is to provide a kind of thin-film transistor array base-plate (thin-film transistor; TFT), it comprises above-mentioned pattern.
An aspect more of the present invention is to provide a kind of liquid crystal display (liquid crystal display; LCD) element, it comprises above-mentioned thin-film transistor array base-plate.
About structure and the pattern formation method of positive type photosensitive organic compound of the present invention, thin-film transistor array base-plate and liquid crystal display cells, be hereby described below.
Positive type photosensitive organic compound
Positive type photosensitive organic compound of the present invention, its carboxylate (B) that comprises novolac resin (A), adjacent naphthoquinones two nitrine sulphonic acids, hydroxyl compound (C) and solvent (D), below sequentially set forth.
Novolac resin (A)
The novolac resin (A) of positive type photosensitive organic compound of the present invention comprises oh type novolac resin (A-1) and xylenol type novolac resin (A-2).
Above-mentioned oh type novolac resin (A-1) is by hydroxy benzaldehyde compound and aromatic hydroxy compound, under acidic catalyst exists, obtains through condensation reaction.
The concrete example of aforesaid hydroxy benzaldehyde compound is: the hydroxy benzaldehyde compound of o-hydroxy benzaldehyde, m-hydroxy benzaldehyde, p-hydroxybenzaldehyde etc.; 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 compound of 5-tri hydroxybenzaldehyde etc.; The hydroxy alkyl benzaldehyde compound of o-methylol benzaldehyde, m-methylol benzaldehyde, p-methylol benzaldehyde etc.This hydroxy benzaldehyde compound is can be separately a kind of to be used or mixes multiple use.Wherein, above-mentioned hydroxy benzaldehyde compound is 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, o-methylol benzaldehyde are for better.
Secondly, the concrete example of the aromatic hydroxy compound of aforementioned and above-mentioned 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) class of 5-xylenols, DMP etc.; M-ethyl-phenol, p-ethyl-phenol, o-ethyl-phenol, 2,3,5-pseudocuminol, 2, alkylphenol (alkyl phenol) class of 3,5-triethyl phenol, 4-TBP, 3-tert-butyl phenol, 2-TBP, 2-tert-butyl-4-methyl-Phenol, the 2-tert-butyl group-5-methylphenol, the 6-tert-butyl group-3-methylphenol etc.; P-metoxyphenol, m-metoxyphenol, p-thanatol, m-thanatol, alkoxy phenol (alkoxy phenol) class to propoxyl group phenol, m-propoxyl group phenol etc.; Isopropenyl phenol (isopropenyl phenol) class of o-isopropenyl phenol, p-isopropenyl phenol, 2-methyl-4-isopropenyl phenol, 2-ethyl-4-isopropenyl phenol etc.; Aryl phenol (aryl phenol) class of phenylphenol (phenylphenol); 4,4'-dihydroxybiphenyl, bisphenol-A, m-benzenediol (resorcinol), p-benzenediol (hydroquinone), 1, polyhydroxy benzenes (polyhydroxyphenol) class of 2,3-benzenetriol (pyrogallol) etc. etc.Aforementioned aromatic hydroxy compound is can be separately a kind of to be used or mixes multiple use.Wherein, above-mentioned aromatic hydroxy compound is with o-cresols, m-cresol, p-Cresol, 2,5-xylenols, 3, and 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.
As for xylenol type novolac resin (A-2), be generally by aldehyde compound and xylenol (xylenol) compounds, under existing, aforesaid acidic catalyst obtains through polycondensation reaction.
The concrete example of aforesaid aldehyde compound 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 is can be separately a kind of to be used or mixes multiple use.Wherein, aldehyde compound is for better with formaldehyde, benzaldehyde.
The concrete example of aforesaid xylenol compounds is: 2,3-xylenols, 2,5-xylenols, 3,5-xylenols, DMP.
The novolac resin (A) of positive type photosensitive organic compound of the present invention is in not affecting under the prerequisite of overall physical property, can further comprise other novolac resin (A-3), be generally by aldehyde compound and aromatic hydroxy compound, under aforesaid acidic catalyst exists, obtain through polycondensation reaction.And this aldehyde compound and aromatic hydroxy compound are as above-mentioned cited, do not repeat separately at this, but the structure of this other novolac resin (A-3) all needs to be different from above-mentioned oh type novolac resin (A-1) and xylenol type novolac resin (A-2).
Aforesaid oh type novolac resin (A-1), xylenol type novolac resin (A-2) and other novolac resin (A-3), all can use the novolac resin of single kind, also can mix two or more different types of novolac resin.Based on novolac resin (A) 100 weight portions, the use amount of this oh type novolac resin (A-1) is 50 weight portion to 95 weight portions, the use amount of xylenol type novolac resin (A-2) is 5 weight portion to 50 weight portions, and the use amount of other novolac resin (A-3) is that 0 weight portion is to 45 weight portions.Because oh type novolac resin (A-1) has better developability, xylenol type novolac resin (A-2) has better residual film ratio, if positive type photosensitive organic compound does not use oh type novolac resin (A-1) or xylenol type novolac resin (A-2), the positive type photosensitive organic compound of gained in rear roasting after, have the not good problem with thickness deficiency of section configuration.But when using the oh type novolac resin (A-1) and xylenol type novolac resin (A-2) of above-mentioned scope, the positive type photosensitive organic compound of gained has the good advantage of section configuration after rear baking, also can avoid in rear when roasting the figure shortcomings such as causing thickness deficiency that flows because being heated.
Be separately 100 percentage by weights based on this oh type novolac resin (A-1) with the total use amount of this xylenol type novolac resin (A-2), the use amount of this oh type novolac resin (A-1) is 50 percentage by weight to 95 percentage by weights, and the use amount of this xylenol type novolac resin (A-2) is 5 percentage by weight to 50 percentage by weights.When the use amount of this oh type novolac resin (A-1) is 50 percentage by weight to 95 percentage by weights, and when the use amount of this xylenol type novolac resin (A-2) is 5 percentage by weight to 50 percentage by weight, the positive type photosensitive organic compound of gained has the good advantage of section configuration after rear baking.
The carboxylate (B) of adjacent naphthoquinones two nitrine sulphonic acids
The carboxylate (B) of adjacent naphthoquinones two nitrine sulphonic acids of the present invention can be selected known frequent user, is not particularly limited.In preferred embodiment of the present invention, the carboxylate (B) of aforementioned adjacent naphthoquinones two nitrine sulphonic acids can include but not limited to the adjacent naphthoquinones two nitrine sulfonic acid of adjacent naphthoquinones two nitrine-4-sulfonic acid, adjacent naphthoquinones two nitrine-5-sulfonic acid, adjacent naphthoquinones two nitrine-6-sulfonic acid etc. and the carboxylate of hydroxyl compound, and the right carboxylate with above-mentioned adjacent naphthoquinones two nitrine sulfonic acid and multi-hydroxy compound is for better.
The carboxylate (B) of above-mentioned adjacent naphthoquinones two nitrine sulphonic acids is esterification or part esterification completely, and the skeleton of the hydroxyaryl class that comprises (one) hydroxy benzophenone ketone and/or (two) formula (I) and/or (hydroxy phenyl) hydro carbons of (three) formula (II), is hereby described below.
(1) concrete example of hydroxy benzophenone ketone 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 or 2,3,3', 4,4', 5'-hexahydroxy benzophenone.
(2) concrete example of hydroxy aryl compound is for having the structure shown in formula (I):
In formula (I), R
1to R
3for hydrogen atom or rudimentary alkyl (alkyl); R
4to R
9for hydrogen atom, halogen atom, rudimentary alkyl, rudimentary alkoxy (alkoxy), rudimentary fat thiazolinyl (alkenyl) and naphthenic base (cycloalkyl); R
10and R
11represent hydrogen atom, halogen atom and rudimentary alkyl; X and y are 1 to 3 integer; Z is 0 to 3 integer; And n is 0 or 1.
In preferred embodiment of the present invention, the hydroxy aryl compound with the structure shown in formula (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) phenylmethane, two (4-hydroxy phenyl) diphenylphosphino ethane, two (4-hydroxyl-3-tert-butyl-phenyl) diphenylphosphino ethane, 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-aminomethyl phenyl)-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 or 1-[1-(3-methyl-4-hydroxy phenyl) isopropyl]-4-[1, two (3-methyl-4-hydroxy phenyl) ethyls of 1-] benzene.
(3) concrete example of (hydroxy phenyl) hydrocarbon compound is as shown in the formula the structure shown in (II):
In formula (II), R
12and R
13for hydrogen atom or low alkyl group; And x' and
y' be 1 to 3 integer.
In preferred embodiment of the present invention, (hydroxy phenyl) hydro carbons with the structural formula shown in formula (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 or two (2,4-dihydroxy phenyl) methane.
In addition, the carboxylate (B) of above-mentioned adjacent naphthoquinones two nitrine sulphonic acids also can comprise the skeleton of (four) other aromatic hydroxyl, its concrete example is phenol, p-metoxyphenol, xylenol, p-dihydroxy-benzene, bisphenol-A, naphthols (naphthol), catechol (pyrocatechol), 1, 2, 3-benzenetriol methyl ether (pyrogallolmonomethyl ether), 1, 2, 3-benzenetriol-1, 3-dimethyl ether (pyrogallol-1, 3-dimethyl ether), 3, 4, 3 of 5-trihydroxybenzoic acid (gallic acid) or part esterification or part etherificate, 4, 5-trihydroxybenzoic acid.
The carboxylate (B) of aforementioned adjacent naphthoquinones two nitrine sulphonic acids is preferably the skeleton that comprises hydroxyaryl class or hydroxy phenyl hydro carbons, its concrete example is 1-[1-(4-hydroxy phenyl) isopropyl]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] benzene and 1, the carboxylate, 4 of 2-naphthoquinones two nitrine-5-sulfonic acid, 4'-ethylenebis (2-methylphenol) and 1, the carboxylate, 2 of 2-naphthoquinones two nitrine-5-sulfonic acid, 3,4, the carboxylate of 4'-tetrahydroxybenzophenone and 1,2-naphthoquinones, two nitrine-5-sulfonic acid.The carboxylate (B) of aforementioned adjacent naphthoquinones two nitrine sulphonic acids is can be separately a kind of to be used or mixes multiple use.
According to the carboxylate (B) of the adjacent naphthoquinones two nitrine sulphonic acids in positive type photosensitive organic compound of the present invention, can use the compound that contains quinone diazido, for example: adjacent naphthoquinones two nitrine-4 (or 5)-sulfonic acid halogen and above-mentioned (one)～(fours') hydroxyl compound is through condensation reaction, completely esterification or part esterification and compound.Aforementioned condensation reaction is carried out conventionally in the organic solvents such as dioxane (dioxane), N-pyrrolidone (N-pyrrolidone), acetamide (acetamide), is preferably under the alkaline condensing agents such as triethanolamine (triethanolamine), alkali carbonate or alkali metal hydrogencarbonate exist and carries out.
In preferred embodiment of the present invention, 100 % by mole of the hydroxyl total amounts based in hydroxyl compound; Be more preferred from more than 50 % by mole; You Jia is that 60 % by mole of above hydroxyl and adjacent naphthoquinones two nitrine-4 (or 5) sulfonic acid halogen condensations form carboxylate, that is esterification degree is more than 50%; Be more preferred from more than 60%.
In concrete example of the present invention, use amount based on novolac resin (A) is 100 weight portions, the use amount of the carboxylate (B) of adjacent naphthoquinones two nitrine sulphonic acids of the present invention is generally 5 weight portion to 50 weight portions, so with 10 weight portion to 45 weight portions for better, again with 15 weight portion to 40 weight portions for better.In the time of skeleton that the carboxylate (B) of adjacent naphthoquinones two nitrine sulphonic acids comprises above-mentioned hydroxyaryl class or hydroxy phenyl hydro carbons, the positive type photosensitive organic compound of gained has the good advantage of section configuration in rear after roasting.
Hydroxyl compound (C)
Hydroxyl compound of the present invention (C) can use the kind that (one)～(fours') that use with the carboxylate (B) of aforementioned adjacent naphthoquinones two nitrine sulphonic acids hydroxyl compound is identical, and better with (one)～(threes') hydroxyl compound.
Aforementioned hydroxyl compound (C) again with the hydroxy aryl compound of (two) for better, its concrete example is three (4-hydroxy phenyl) methane, 1-[1-(4-hydroxy phenyl) isopropyl]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] benzene, two (4-hydroxyl-3,5-3,5-dimethylphenyl) phenylmethane, 2,4,6-trihydroxybenzophenone, 1,2,3-benzenetriol methyl ether (pyrogallol monomethyl ether) etc.Aforementioned hydroxyl compound (C) is can be separately a kind of to be used or mixes multiple use.
Be 100 weight portions based on novolac resin (A), the use amount of aforesaid hydroxyl compound (C) is 1 weight portion to 30 weight portion, so with 5 to 30 weight portions for better, again with 10 to 25 weight portions for better.When positive type photosensitive organic compound does not use hydroxyl compound (C), the positive type photosensitive organic compound of gained has the not good problem of section configuration after rear baking.In the time that hydroxyl compound (C) uses above-mentioned scope, the positive type photosensitive organic compound of gained has the good advantage of section configuration after rear baking.
Solvent (D)
The solvent (D) that positive type photosensitive organic compound of the present invention uses refers to easily and other organic principle dissolving but organic solvent of not reacting to each other with mentioned component mutually.
In concrete example of the present invention, this solvent (D) is (gathering) alkylene glycol mono alkane ethers of glycol monoethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol list positive propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, Triethylene glycol ethyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, dipropylene glycol monomethyl ether, DPE, dipropylene glycol list positive propyl ether, dipropylene glycol mono-n-butyl ether, Tripropylene glycol monomethyl Ether, tripropylene glycol list ether etc., (gathering) alkylene glycol mono alkane ether acetate class of glycol methyl ether acetate, ethylene glycol ether acetate, 1-Methoxy-2-propyl acetate, propylene-glycol ethyl ether acetate etc., other ethers of diethylene glycol dimethyl ether, diethylene glycol MEE, 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 (ethyl lactate), 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 class of 2-oxygen base ethyl butyrate etc., toluene, dimethylbenzene etc. aromatic hydrocarbon based, the carboxylic acid amine of 1-METHYLPYRROLIDONE, DMF, DMA etc.Above-mentioned solvent (D) can one uses separately or mixes multiple use.Preferably, this solvent (D) is dihydroxypropane single-ether, 1-Methoxy-2-propyl acetate or ethyl lactate.
In concrete example of the present invention, the use amount based on novolac resin (A) is 100 weight portions, and the use amount of above-mentioned solvent (D) is generally 100 to 500 weight portions; Be preferably 100 to 450 weight portions; Be more preferred from 100 to 400 weight portions.
Adjuvant (E)
Positive type photosensitive organic compound alternative of the present invention comprises adjuvant (E), can include but not limited to: adherence auxiliary agent, the agent that has an even surface, thinning agent and sensitizer etc.
Above-mentioned adherence auxiliary agent can include but not limited to melamine (melamine) compound and silane system (silane) compound, to increase the adherence between positive type photosensitive organic compound and attaching substrates.The concrete example of aforementioned melamine is as: commercially available Cymel-300, Cymel-303 (CYTEC manufacture), MW-30MH, MW-30, MS-11, MS-001, MX-750 or MX-706 (three and chemistry system) commercially available product.The concrete example of aforementioned silane (silane) based compound is as vinyltrimethoxy silane, vinyltriethoxysilane, 3-(methyl) acryloxy propyl trimethoxy silicane, vinyl three (2-methoxy ethoxy) silane, N-(2-amido ethyl)-3-aminocarbonyl propyl methyl dimethoxysilane, N-(2-amido ethyl)-3-aminocarbonyl propyl trimethoxy silane, 3-aminocarbonyl propyl triethoxysilane, 3-glycidoxypropyltrime,hoxysilane, 3-glycidoxy dimethyl methyl TMOS, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-mercaptopropyl trimethoxysilane or two-1, 2-(trimethoxy is silica-based) ethane.
In concrete example of the present invention, use amount based on novolac resin (A) is 100 weight portions, the use amount of the adherence auxiliary agent of aforementioned melamine compound is generally 0 weight portion to 20 weight portion, so with 0.5 weight portion to 18 weight portion for better, again with 1.0 weight portion to 15 weight portions for better; The use amount of the adherence auxiliary agent of aforementioned silane based compound is generally 0 weight portion to 2 weight portion, so with 0.001 weight portion to 1 weight portion for better, again with 0.005 weight portion to 0.8 weight portion for better.
The above-mentioned agent that has an even surface can include but not limited to that fluorine is that surfactant or silicon are surfactant.Aforementioned fluorine is that the concrete example of surfactant is as commercially available Flourate FC-430, FC-431 (3M system) or Ftop EF122A, 122B, 122C, 126, BL20 (Tochem product system).Aforementioned silicon is that the concrete example of surfactant is as commercially available SF8427 or SH29PA (Toray Dow Corning Silicone system).
In concrete example of the present invention, use amount based on novolac resin (A) is 100 weight portions, the use amount of aforementioned surfactants is generally 0 weight portion to 1.2 weight portion, so with 0.025 weight portion to 1.0 weight portion for better, again with 0.050 weight portion to 0.8 weight portion for better.
The concrete example of above-mentioned thinning agent is as commercially available RE801 or RE802 (Ink of kingdom system) etc.
The concrete example of above-mentioned sensitizer as: TPPA-1000P, TPPA-100-2C, TPPA-1100-3C, TPPA-1100-4C, TPPA-1200-24X, TPPA-1200-26X, TPPA-1300-235T, TPPA-1600-3M6C or TPPA-MF commercially available product (island, Japanese Honshu chemical industry system), be wherein preferably TPPA-600-3M6C or TPPA-MF.Aforesaid sensitizer is can be separately a kind of to be used or mixes multiple use.
Above-mentioned adjuvant (E) is can be separately a kind of or mix multiple use.In concrete example of the present invention, use amount based on novolac resin (A) is 100 weight portions, the use amount of aforementioned sensitizer is generally 0 weight portion to 20 weight portion, so with 0.5 weight portion to 18 weight portion for better, again with 1.0 weight portion to 15 weight portions for better.In addition, the present invention also can add other adjuvant according to need again, for example: plasticizer, stabilizing agent etc.
The preparation method of positive type photosensitive organic compound
The preparation of positive type photosensitive organic compound of the present invention, generally by the carboxylate (B) of above-mentioned novolac resin (A), adjacent naphthoquinones two nitrine sulphonic acids, hydroxyl compound (C) and solvent (D), in known stirrer, stir, make it be uniformly mixed into solution state, and can optionally add various adjuvants (E), can make positive type photosensitive organic compound.
Pattern formation method
The positive light sensitivity composition of above-mentioned gained can be via sequentially bestowing after pre-baked (prebake) step, step of exposure, development step and rear roasting (postbake) treatment step, and form pattern in substrate.
Profess it, the present invention uses aforementioned positive type photosensitive organic compound to form the method for pattern, by coating processes such as rotary coating, curtain coating coating or print roll coatings, aforementioned positive type photosensitive organic compound is coated on substrate, and after coating, remove solvent with pre-bake mode, and form a pre-baked film.Wherein, pre-baked condition, according to the kind of each composition, coordinate ratio and different, is generally temperature between 70 to 110 DEG C, carries out 1 to 15 minute.
After pre-baked, this film is exposed under the mask of specifying, then at the temperature of 23 ± 2 DEG C, impregnated in developer solution, last 15 seconds to 5 minutes, by this part of not wanting is removed and form specific pattern.The light that uses of exposure, taking the ultraviolet ray of g line, h line, i line etc. 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 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 or 1,8-diazabicylo-[5, the alkali compounds of 4,0]-7-hendecene.
Preferably, the concentration of developer solution is 0.001 percentage by weight to 10 percentage by weight; Better is 0.005 percentage by weight to 5 percentage by weight; You Jia is 0.01 percentage by weight to 1 percentage by weight.
While using the developer solution that aforementioned alkali compounds forms, conventionally after developing, clean with water, then with pressurized air or the air-dry aforementioned film of compressed nitrogen.Then, use the heating arrangements such as hot plate or baking oven to carry out rear roasting processing to aforementioned film.Rear roasting temperature is generally 100 to 250 DEG C, and wherein, using the heat time of hot plate is 1 to 60 minute, and using the heat time of baking oven is 5 to 90 minutes.After above treatment step, can form pattern in substrate.
The thickness of above-mentioned pattern is 5 μ m to 25 μ m, is preferably 8 μ m to 25 μ m, is more preferred from 10 μ m to 25 μ m, and in the time that the thickness of pattern is 5 μ m to 25 μ m, this pattern can be beneficial to the meticulous laying of conductive layer, insulation course or diaphragm.
Thin-film transistor array base-plate
Thin-film transistor array base-plate of the present invention is obtained with aforesaid method.In brief, can utilize the coating methods such as rotary coating, curtain coating coating or print roll coating, positive type photosensitive organic compound of the present invention is coated on the glass substrate or plastic base of a film that contains aluminium, chromium, silicon nitride or amorphous silicon etc., 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, after above-mentioned steps, can make the thin-film transistor array base-plate containing multiple thin film transistor (TFT)s or electrode.
Refer to Fig. 1, it is the cut-away section schematic diagram that illustrates liquid crystal display according to an embodiment of the invention (LCD) element tft array substrate.First, aluminium film on glass substrate 101 etc. locates to arrange grid 102a and storage capacitors Cs electrode 102b.Secondly, in the upper capping oxidation silicon fiml (SiO of grid 102a
x) 103 or silicon nitride film (SiN
x) 104 grades and form dielectric film, and on this dielectric film, form the amorphous silicon layer (a-Si) 105 as semiconductor active layer.Then,, in order to reduce junction impedance, the amorphous silicon layer 106 of doping nitrogen impurity can be set on amorphous silicon layer 105.Afterwards, use the metals such as aluminium, form drain electrode 107a and source electrode 107b, it is upper that the 107a that wherein drains is connected in data signal line (figure does not illustrate), and source electrode 107b is connected on pixel electrode (or pixel electrode) 109.Then, for protection is as the amorphous silicon layer 105 of semiconductor active layer, drain electrode 107a or source electrode 107b etc., silicon nitride film etc. is set as diaphragm 108.
Liquid crystal display cells
Liquid crystal display cells of the present invention at least comprises above-mentioned tft array substrate, and can include according to need other parts.
The concrete example of the basic comprising form of above-mentioned liquid crystal display cells for (1) by the driving element of TFT etc. and pixel electrode (conductive layer) through arranging the tft array substrate (driving substrate) of the invention described above forming, and between the colored filter substrate forming by colored filter and to electrode (conductive layer), get involved interval body and subtend configuration, finally enclose liquid crystal material and form in gap part.Another kind of mode, (2) the one-piece type tft array substrate of colored filter of glory optical filter will directly be formed on the tft array substrate in the invention described above, and configure getting involved interval body and subtend configuration between the subtend substrate of electrode (conductive layer), finally enclose liquid crystal material and formation etc. in gap part, wherein the liquid crystal material of aforementioned use can be any liquid-crystal compounds or liquid-crystal composition, herein and be not particularly limited.
The concrete example of above-mentioned conductive layer is ITO film; The metal film of aluminium, zinc, copper, iron, nickel, chromium, molybdenum etc.; Or the metal oxide film of silicon dioxide etc.Preferably, it is the rete for the tool transparency; Be more preferred from ITO film.
The base material that tft array substrate of the present invention, colored filter substrate and subtend substrate etc. use, its concrete example is the known glass of soda-lime glass, low-expansion glass, alkali-free glass or quartz glass, in addition, also can adopt the substrate being made up of plastic foil etc.
The invention has the advantages that: the prepared pattern of positive type photosensitive organic compound of the present invention through after have high thickness and the good advantage of section configuration after roasting.
Below utilize several embodiments so that application of the present invention to be described, so it,, not in order to limit the present invention, has and conventionally knows the knowledgeable in the technology of the present invention field, without departing from the spirit and scope of the present invention, and when being used for a variety of modifications and variations.
Brief description of the drawings
For above and other objects of the present invention, feature, advantage and embodiment can be become apparent, appended the description of the drawings is as follows:
Fig. 1 illustrates the cut-away section schematic diagram of tft array substrate used for liquid crystal display element according to an embodiment of the invention;
Fig. 2 is the section configuration schematic diagram that illustrates the present invention and assess the diaphragm with pattern of embodiment 1 to 10 and comparative example 1 to 7 gained;
Wherein, symbol description:
101: glass substrate liquid crystal display cells 102a: grid
102b: storage capacitors Cs electrode 103: silicon oxide film
104: silicon nitride film 105: amorphous silicon layer
106: amorphous silicon layer 107a: drain electrode
107b: source electrode 08: diaphragm
109: pixel electrode 01: vertical configuration section
203: suitable taper section 205: contrary taper section
207: oblate shape section.
Embodiment
Prepare novolac resin (A)
It is below the oh type novolac resin (A-1) of preparing synthesis example A-1-1 to A-3-3 according to table 1.Synthesis example A-1-1
On four cervical vertebra bottles of 1000 milliliters of volumes, nitrogen inlet, stirrer, well heater, condenser pipe and thermometer are set, import and add 0.30 mole of 0.70 mole of m-cresol, p-Cresol, 3,0.020 mole of 0.5 mole of 4-4-dihydroxy benzaldehyde and oxalic acid after nitrogen.Slowly stir and make reaction solution be warming up to 100 DEG C, and at this temperature polycondensation 6 hours.Then, reaction solution is warming up to 180 DEG C, carries out drying under reduced pressure with the pressure of 10mmHg, will after solvent devolatilization, can obtain oh type novolac resin (A-1-1).
Synthesis example A-1-2 to A-3-3
With the synthetic method of the oh type novolac resin of synthesis example A-1-1, it is kind and the use amount that changes reactant in oh type novolac resin (A-1) that difference is in synthesis example A-1-2 to A-3-3, its formula is as shown in table 1, does not separately repeat herein.
Prepare positive type photosensitive organic compound
It is below the positive light sensitivity composition with table 3 Preparation Example 1 to 10 and comparative example 1 to 7 according to table 2.
Embodiment 1
Oh type novolac resin (A-1-1) by 70 weight portions by synthesis example A-1-1 gained, 30 weight portions are by the oh type novolac resin (A-2-1) of synthesis example A-2-1 gained, 1-[1-(4-hydroxy phenyl) isopropyl of 30 weight portions]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] benzene and 1, the carboxylate (B-1) (average esterification degree 85%) of 2-naphthoquinones two nitrine-5-sulfonic acid, three (4-hydroxy phenyl) methane (C-1) of 10 weight portions, add 1-Methoxy-2-propyl acetate (the propylene glycol monomethyl ether acetate of 300 weight portions, PGMEA) in solvent (D-1), stir said mixture is dissolved in solvent with swing-out stirrer, can make positive type photosensitive organic compound of the present invention.The positive type photosensitive organic compound of gained is assessed with following each evaluation method, and its result is as described in Table 2, and wherein the detection method of etching rear decoloring, resolution and residual film ratio repeats after holding.
Embodiment 2 to 10
With the preparation method of the positive type photosensitive organic compound of embodiment 1, it is kind and the use amounts that change positive type photosensitive organic compound Raw that difference is in embodiment 2 to 10, and its formula and testing result are as shown in table 2, separately do not repeat herein.
Comparative example 1 to 7
With the preparation method of the positive type photosensitive organic compound of embodiment 1, it is kind and the use amounts that change positive type photosensitive organic compound Raw that difference is in comparative example 1 to 7, and its formula and testing result are also as shown in table 3.
Evaluation method
1. roasting pattern thickness after measuring
By the positive type photosensitive organic compound of embodiment 1 to 10 and comparative example 1 to 7, on plain glass substrate, be coated with in rotary coating mode, in pre-baked 120 seconds at 100 DEG C, can obtain the pre-baked film of approximately 10 μ m.This pre-baked film, under the mask (Japanese Filcon system) of line and spacing (line and space), is utilized to 200mJ/cm
2ultraviolet light (exposure machine model AG500-4N; M & R Nano Technology system) irradiate after, then with 2.38%TMAH aqueous solution, at 23 DEG C, developed 3 minutes, the film of exposed part on substrate is removed, then clean and obtain pattern with pure water.After after 120 DEG C of temperature roasting 2 minutes, can obtain the diaphragm on plain glass substrate with pattern, and measure its thickness in blooming machine (grand bright science and technology, MFS-630-F).
2. the section configuration of roasting pattern after evaluating
By the diaphragm with pattern of above-described embodiment 1 to 10 and comparative example 1 to 7 gained, to take with SEM, and observe the section configuration of roasting pattern thereafter, its judgment standard is as following and coordinate as shown in the section configuration of Fig. 2:
◎: vertical configuration section 201
Zero: along taper section 203
╳: contrary taper section 205, oblate shape section 207
The positive type photosensitive organic compound of above-described embodiment and comparative example gained, thereafter roasting pattern thickness and afterwards the assessment result of the section configuration of roasting pattern if table 2 is with as shown in table 3.
Result from table 2 with table 3, in the time that positive type photosensitive organic compound uses oh type novolac resin (A-1) and the xylenol type novolac resin (A-2) of aforementioned proportion, prepared pattern through after have high thickness and the good advantage of section configuration after baking.Secondly, when positive type photosensitive organic compound uses the carboxylate (B) of the adjacent naphthoquinones two nitrine sulphonic acids of the skeleton of hydroxyl aryl or hydroxy phenyl hydro carbons simultaneously, and again and with hydroxy aryl compound during as hydroxyl compound (C), the pattern making thus has preferably advantage of section configuration, therefore really can reach object of the present invention.
What need supplement is, though the present invention is using specific compound, composition, reaction conditions, processing procedure, analytical approach or particular instrument as illustration, positive type photosensitive organic compound of the present invention and pattern formation method thereof are described, only in the technical field of the invention any have conventionally know that the knowledgeable is known, the present invention is not limited to this, without departing from the spirit and scope of the present invention, positive type photosensitive organic compound of the present invention and pattern formation method thereof also can use other compound, composition, reaction conditions, processing procedure, analytical approach or instrument to carry out.
Although the present invention discloses as above with embodiment; so it is not in order to limit the present invention; in the technical field of the invention any have conventionally know the knowledgeable; without departing from the spirit and scope of the present invention; when being used for a variety of modifications and variations, the scope that therefore protection scope of the present invention ought define depending on accompanying claims is as the criterion.
Table 3
B-1 1-[1-(4-hydroxy phenyl) isopropyl]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] carboxylate of benzene and 1,2-naphthoquinones, two nitrine-5-sulfonic acid
B-2 4,4 '-ethylenebis (2-methylphenol) and 1, the carboxylate of 2-naphthoquinones two nitrine-5-sulfonic acid
The carboxylate of B-3 2,3,4,4'-Tetrahydroxybenzophenone and 1,2-naphthoquinones, two nitrine-5-sulfonic acid
C-1 tri-(4-hydroxy phenyl) methane
C-2 1-[1-(4-hydroxy phenyl) isopropyl]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] benzene
Two (4-hydroxyl-3,5-the 3,5-dimethylphenyl)-4-phenylmethanes of C-3
C-4 2,4,6-trihydroxybenzophenone
C-5 Pyrogallol acid methyl ether (pyrogallol monomethyl ether)
D-1 1-Methoxy-2-propyl acetate (PGMEA, propylene glycol monomethyl ether acetate)
D-2 ethyl lactate (EL, ethyl lactate)
D-3 dihydroxypropane single-ether (PGEE, propylene glycol monoethyl ether)
E-1 surfactant: trade name SF8427; Toray Dow Corning Silicone system
E-2 adherence auxiliary agent: trade name Cyme1-303; CYTEC system.
Claims (9)
1. a positive type photosensitive organic compound, comprises:
Novolac resin (A), wherein said novolac resin (A) comprises oh type novolac resin (A-1) and xylenol type novolac resin (A-2), described oh type novolac resin (A-1) is by hydroxy benzaldehyde compound and aromatic hydroxy compound condensation and obtain, and described xylenol type novolac resin (A-2) is by aldehyde compound and xylenol compounds polycondensation and obtain;
The carboxylate (B) of adjacent naphthoquinones two nitrine sulphonic acids;
Hydroxyl compound (C); And
Solvent (D).
2. positive type photosensitive organic compound as claimed in claim 1, the skeleton that the carboxylate (B) of wherein said adjacent naphthoquinones two nitrine sulphonic acids comprises hydroxy benzophenone ketone and/or hydroxyaryl class and/or hydroxy phenyl hydro carbons.
3. positive type photosensitive organic compound as claimed in claim 1, wherein said hydroxyl compound (C) comprises hydroxy benzophenone ketone compounds and/or hydroxy aryl compound and/or hydroxy phenyl hydrocarbon compound.
4. positive type photosensitive organic compound as claimed in claim 1, be wherein 100 weight portions based on described novolac resin (A), the use amount of described oh type novolac resin (A-1) is 50 weight portion to 95 weight portions, the use amount of described xylenol type novolac resin (A-2) is 5 weight portion to 50 weight portions, the use amount of the carboxylate (B) of described adjacent naphthoquinones two nitrine sulphonic acids is 5 weight portion to 50 weight portions, the use amount of described hydroxyl compound (C) is 1 weight portion to 30 weight portion, and the use amount of described solvent (D) is 100 weight portion to 500 weight portions.
5. positive type photosensitive organic compound as claimed in claim 4, be wherein 100 percentage by weights based on described oh type novolac resin (A-1) with the total use amount of described xylenol type novolac resin (A-2), the use amount of described oh type novolac resin (A-1) is 50 percentage by weight to 95 percentage by weights, and the use amount of described xylenol type novolac resin (A-2) is 5 percentage by weight to 50 percentage by weights.
6. a pattern formation method, it is by the positive type photosensitive organic compound as described in claim 1 to 5 any one sequentially being bestowed to a coating processing, a pre-baked processing, an exposure-processed, a development treatment and a rear roasting processing, being used and form a pattern on a substrate.
7. pattern formation method as claimed in claim 6, the thickness of the pattern that wherein formed is between 5 μ m to 25 μ m.
8. a thin-film transistor array base-plate, it comprises pattern as claimed in claim 7.
9. a liquid crystal display cells, it comprises thin-film transistor array base-plate as claimed in claim 8.
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| CN104614942A (en) * | 2015-01-08 | 2015-05-13 | 苏州瑞红电子化学品有限公司 | Ultraviolet positive photoresist and high heat resistance film forming resin thereof |
| CN104965389A (en) * | 2015-01-08 | 2015-10-07 | 苏州瑞红电子化学品有限公司 | FPD/TP positive photoresist used for flexible substrate |
| CN105607418A (en) * | 2015-12-23 | 2016-05-25 | 苏州瑞红电子化学品有限公司 | High heat-resistant photoresist composition and application technology thereof |
| CN106200267A (en) * | 2015-05-25 | 2016-12-07 | 奇美实业股份有限公司 | Positive photosensitive resin composition, pattern forming method and application thereof |
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| CN113589649A (en) * | 2021-08-13 | 2021-11-02 | 北京北旭电子材料有限公司 | Resin composition, photoresist composition and patterning method |
| CN113589649B (en) * | 2021-08-13 | 2024-06-04 | 北京北旭电子材料有限公司 | Resin composition, photoresist composition and patterning method |
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| Publication number | Publication date |
|---|---|
| TWI465851B (en) | 2014-12-21 |
| JP2014164303A (en) | 2014-09-08 |
| TW201433884A (en) | 2014-09-01 |
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