TWI442174B - A branched unsaturated polymer, a radiation-sensitive resin composition, and a spacer for a liquid crystal display element - Google Patents
A branched unsaturated polymer, a radiation-sensitive resin composition, and a spacer for a liquid crystal display element Download PDFInfo
- Publication number
- TWI442174B TWI442174B TW094124367A TW94124367A TWI442174B TW I442174 B TWI442174 B TW I442174B TW 094124367 A TW094124367 A TW 094124367A TW 94124367 A TW94124367 A TW 94124367A TW I442174 B TWI442174 B TW I442174B
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- Taiwan
- Prior art keywords
- spacer
- compound
- radiation
- parts
- resin composition
- Prior art date
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- 125000006850 spacer group Chemical group 0.000 title claims description 66
- 230000005855 radiation Effects 0.000 title claims description 60
- 229920000642 polymer Polymers 0.000 title claims description 55
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 44
- 239000011342 resin composition Substances 0.000 title claims description 41
- -1 isocyanate compound Chemical class 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 80
- 229920001577 copolymer Polymers 0.000 claims description 38
- 239000000758 substrate Substances 0.000 claims description 35
- 239000003505 polymerization initiator Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 29
- 239000012948 isocyanate Substances 0.000 claims description 23
- 238000000576 coating method Methods 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 18
- 238000011161 development Methods 0.000 claims description 17
- 125000003700 epoxy group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000010408 film Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 40
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 239000000203 mixture Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229940022663 acetate Drugs 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000003999 initiator Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229920000877 Melamine resin Polymers 0.000 description 7
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- OLCGOZPSVSTZDP-UHFFFAOYSA-N CC(=COCCN=C=O)C Chemical compound CC(=COCCN=C=O)C OLCGOZPSVSTZDP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 5
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 230000001771 impaired effect Effects 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- YSBPNMOAQMQEHE-UHFFFAOYSA-N (2-methyloxiran-2-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(C)CO1 YSBPNMOAQMQEHE-UHFFFAOYSA-N 0.000 description 4
- HNSSKFWZYMGHDO-UHFFFAOYSA-N 1-(2-isocyanatoethoxy)prop-1-ene Chemical compound C(=CC)OCCN=C=O HNSSKFWZYMGHDO-UHFFFAOYSA-N 0.000 description 4
- HMRPNNORSXVXDY-UHFFFAOYSA-N 2-(oxolan-2-ylmethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)CC1CCCO1 HMRPNNORSXVXDY-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 230000001235 sensitizing effect Effects 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N p-Methoxystyrene Natural products COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- SSLASPHAKUVIRG-UHFFFAOYSA-N (2-methylcyclohexyl) prop-2-enoate Chemical compound CC1CCCCC1OC(=O)C=C SSLASPHAKUVIRG-UHFFFAOYSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- NUUYZLOGRAXQBP-UHFFFAOYSA-N 1,1-diphenoxyethanol Chemical compound C=1C=CC=CC=1OC(O)(C)OC1=CC=CC=C1 NUUYZLOGRAXQBP-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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- JFWFAUHHNYTWOO-UHFFFAOYSA-N 2-[(2-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC=C1COCC1OC1 JFWFAUHHNYTWOO-UHFFFAOYSA-N 0.000 description 2
- OCKQMFDZQUFKRD-UHFFFAOYSA-N 2-[(3-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC(COCC2OC2)=C1 OCKQMFDZQUFKRD-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
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- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
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- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- NCAVPEPBIJTYSO-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound C1OC1COCC1CO1.OCCCCOC(=O)C=C NCAVPEPBIJTYSO-UHFFFAOYSA-N 0.000 description 2
- SSIZVBOERWVGFR-UHFFFAOYSA-N 5-(oxiran-2-yl)pentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCC1CO1 SSIZVBOERWVGFR-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-N tetraethylazanium;hydrochloride Chemical compound Cl.CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-N 0.000 description 1
- HCLJOFJIQIJXHS-UHFFFAOYSA-N tetraethylene glycol diacrylate Substances C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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Description
本發明係有關特別適用於形成液晶顯示元件用間隔件之感放射線性樹脂組成物中,適用為樹脂成份之新穎的支鏈不飽和聚合物、含該支鏈不飽和聚合物之感放射線性樹脂組成物、間隔件及其形成方法,以及液晶顯示元件。
先前液晶顯示元件為了使2枚基板間保有一定間隔(單元蓋),而使用具有一定粒徑之玻璃珠、塑膠珠等間隔件,但該間隔件係無規狀散佈於玻璃基板等之透明基板上,因此畫素形成領域會存在間隔件,而產生攝入間隔件之現象及使入射光散射,而有降低液晶顯示元件對比之問題。
為了解決該問題曾採用以光微影蝕刻法形成間隔件之方法。該方法為,將感放射線性樹脂組成物塗佈於基板上,介由一定圖罩例如以紫外線曝光後顯像,而形成點狀或條狀之間隔件形狀,因該方法可僅於畫素形成領域以外之一定場所形成間隔件,故基本上可解決上述問題。
又,近年來隨著液晶顯示元件之大面積化及提升生產性等觀點,而推展母體玻璃基板之大型化(例如1,500×1,800mm)。因先前之基板尺寸(680×880mm)小於圖罩尺寸,故可以概括曝光方式對應,但使用大型基板時幾乎無法製作同該基板尺寸之圖罩尺寸,因此難以概括曝光方式對應。
為了對應大型基板層提案進階曝光方式。但進階曝光方式需對每枚基板進行數次曝光,而每個曝光過程中需消耗位置配合及進階移動之時間,故比較概括曝光方式會有降低生產性之問題。
又,概括曝光方式可使用3,000J/m2
之曝光量,而進階曝光方式需降低每回曝光量,因此先前形成間隔件用之感放射線性樹脂組成物難以1,200J/m2
以下之曝光量達成充分間隔件形狀及膜厚。
另外就提升製作液晶顯示元件步驟之生產性觀點曾導入,貼合玻璃基板前將液晶材料填入玻璃基板表面上的技術"ODF(One Drop Fill)法"。該方法可大幅縮短製作液晶顯示元件所需時間。例如30英寸液晶顯示元件以先前方法填充液晶材料時需約5天時間,而ODF法僅需2小時,故可大幅提升生產性。
但使用ODF法時需具備,室溫下壓合薄膜晶體(TFT)數組及濾色器之步驟,而壓縮荷重會增加間隔件之塑性變形,因此將無法使單元頂保有均勻性,而於單元內產生間隙造成顯示斑。
故曾提案不易塑性變形且既使因壓縮荷重而變形也能具有高回復率之間隔件,例如特開2003-173025號公報中,含有使具有環狀亞胺基之單體、(甲基)丙烯酸單體及含羥基單體之共聚物,與具乙烯性不飽和鍵之異氰酸酯化合物反應而得的聚合物,及具熱交聯性環氧基化合物之感光性樹脂組成物所形成的間隔件。該間隔件雖具有高敏感度及優良彈性特性,但就該感光性樹脂組成物對鹼水溶液之顯像性觀點,需限制賦予耐熱性之具熱交聯性環氧基化合物的添加量,而有所得間隔件之耐熱性不足的問題。
因此本發明之課題為,提供可形成高敏感度及高解像度下既使以1,200J/m2
以下之曝光量也可得到充分間隔件形狀,且具有優良彈性回復性、耐刷洗性、對透明基板之密合性、耐熱性等之液晶顯示元件用間隔件的感放射線性樹脂組成物。
本發明另一課題為,提供適用為該感放射線性樹脂組成物之樹脂成份的支鏈不飽和聚合物等。
本發明另一課題為,提供由上述感放射線性樹脂組成物形成之液晶顯示元件用間隔件,及備有其之液晶顯示元件。
本發明另一課題為,提供上述液晶顯示元件用間隔件之形成方法。
本發明其他課題及優點將由下列說明得知。
本發明課題可由第一,(a1)不飽和羧酸及/或不飽和羧酸酐、(a2)含環氧基不飽和化合物、(a3)含羥基不飽和化合物及(a4)其他不飽和化合物之共聚物,與下列式(1)所示異氰酸酯化合物反應而得之聚合物(以下稱為「(A)聚合物」)達成。
本發明課題可由第二特徵為,含有〔A〕聚合物、〔B〕聚合性不飽和化合物及〔C〕感放射線性聚合引發劑之感放射線性樹脂組成物達成。
本發明課題可由第三,上述感放射線性樹脂組成物所形成的形成液晶顯示元件用之間隔件用的感放射線性樹脂組成物(以下稱為「液晶顯示元件用之間隔件用的感放射線性樹脂組成物」)達成。
本發明課題可由第四,由液晶顯示元件用之間隔件用的感放射線性樹脂組成物形成的液晶顯示元件用間隔件達成。
本發明課題可由第五特徵為,至少依序包含下列步驟之液晶顯示元件用間隔件的形成方法達成。
(1)於基板上形成液晶顯示元件用之間隔件用的感放射線性樹脂組成物塗膜之步驟;(2)將部分塗膜曝光之步驟;(3)曝光後將塗膜顯像之步驟;(4)顯像後將塗膜加熱之步驟。
本發明課題可由第六,具備上述液晶顯示元件用間隔件之液晶顯示元件達成。
下面將詳細說明本發明。
〔A〕聚合物本發明之〔A〕聚合物係由,(a1)不飽和羧酸及/或不飽和羧酸酐、(a2)含環氧基不飽和化合物、(a3)含羥基不飽和化合物及(a4)其他不飽和化合物之共聚物(以下稱為「共聚物〔α〕」),與上述式(1)所示異氰酸酯化合物(以下稱為「不飽和異氰酸酯化合物(1)」)反應而得之聚合物形成。
構成共聚物〔α〕之各成份中,(a1)不飽和羧酸及/或不飽和羧酸酐(以下總稱為「(a1)不飽和羧酸系化合物」)如,丙烯酸、甲基丙烯酸、巴豆酸、2-丙烯醯氧基乙基琥珀酸、2-甲基丙烯醯氧基乙基琥珀酸、2-丙烯醯氧基乙基六氫酞酸、2-甲基丙烯醯氧基乙基六氫酞酸等單羧酸;馬來酸、富馬酸、檸康酸、中康酸、衣康酸等二羧酸;該二羧酸之酸酐等。
上述(a1)不飽和羧酸系化合物中,就共聚合性,所得〔A〕聚合物對鹼顯像液之溶解性及易取得性較佳為丙烯酸、甲基丙烯酸、馬來酸酐。
共聚物〔α〕中,(a1)不飽和羧酸系化合物可單獨或2種以上混合使用。
共聚物〔α〕中,來自(a1)不飽和羧酸系化合物之重覆單位含量較佳為5至50重量%,更佳為10至40重量%,特佳為15至30重量%。來自(a1)不飽和羧酸系化合物之重覆單位含量少於5重量%時,今傾向降低與不飽和異氰酸酯化合物(1)反應而得之聚合物對鹼顯像液的溶解性,又,超過50重量%時恐過度增加聚合物對鹼顯像液之溶解性。
(a2)含環氧基不飽和化合物如:丙烯酸縮水甘油酯、丙烯酸2-甲基縮水甘油酯、4-羥基丁基丙烯酸酯縮水甘油醚、丙烯酸3,4-環氧丁酯、丙烯酸6,7-環氧庚酯、丙烯酸3,4-環氧環己酯等丙烯酸環氧(環)烷基酯;甲基丙烯酸縮水甘油酯、甲基丙烯酸2-甲基縮水甘油酯、甲基丙烯酸3,4-環丁酯、甲基丙烯酸6,7-環氧庚酯、甲基丙烯酸3,4-環氧環己酯等甲基丙烯酸環氧(環)烷基酯;α-乙基丙烯酸縮水甘油酯、α-n-丙基丙烯酸縮水甘油酯、α-n-丁基丙烯酸縮水甘油酯、α-乙基丙烯酸6,7-環氧庚酯、α-乙基丙烯酸3,4-環氧環己酯等α-烷基丙烯酸環氧(環)烷基酯;o-乙烯基苄基縮水甘油醚、m-乙烯基苄基縮水甘油醚、p-乙烯基苄基縮水甘油醚等縮水甘油醚類等。
上述(a2)含環氧基不飽和化合物中,就共聚合性及間隔件之強度較佳為甲基丙烯酸縮水甘油酯、甲基丙烯酸2-甲基縮水甘油酯、甲基丙烯酸6,7-環氧庚酯、4-羥基丁基丙烯酸酯縮水甘油醚、o-乙烯基苄基縮水甘油醚、m-乙烯基苄基縮水甘油醚、p-乙烯基苄基縮水甘油醚。
共聚物〔α〕中,(a2)含環氧基不飽和化合物可單獨或2種以上混合使用。
共聚物〔α〕中,來自(a2)含環氧基不飽和化合物之重覆單位含量較佳為10至70重量%,更佳為15至60重量%,特佳為20至50重量%。來自(a2)含環氧基不飽和化合物之重覆單位含量低於10重量%時,會傾向降低所得間隔件之強度,又,超過70重量%時會傾向降低與不飽和異氰酸酯化合物(1)反應所得之聚合物的保存安定性。
(a3)含羥基不飽和化合物如:丙烯酸2-羥基乙酯、丙烯酸2-羥基丙酯、丙烯酸3-羥基丙酯、丙烯酸2-羥基丁酯、丙烯酸3-羥基丁酯、丙烯酸4-羥基丁酯、1,4-環己烷二甲醇-丙烯酸酯等丙烯酸羥基烷基酯;甲基丙烯酸2-羥基乙酯、甲基丙烯酸2-羥基丙酯、甲基丙烯酸3-羥基丙酯、甲基丙烯酸2-羥基丁酯、甲基丙烯酸3-羥基丁酯、甲基丙烯酸4-羥基丁酯等甲基丙烯酸羥基烷基酯類等。
上述(a3)含羥基不飽和化合物中,就共聚合反應性及與異氰酸酯化合物之反應性較佳為甲基丙烯酸2-羥基乙酯、甲基丙烯酸2-羥基丙酯、丙烯酸4-羥基丁酯、1,4-環己烷二甲醇-丙烯酸酯等。
共聚物〔α〕中,來自(a3)含羥基不飽和化合物之重覆單位含量較佳為1至30重量%,更佳為3至20重量%,特佳為5至15重量%。來自(a3)含羥基不飽和化合物之重覆單位含量低於1重量%時,會降低對聚合物之不飽和異氰酸酯化合物(1)的導入率,而傾向降低敏感度,又,超過30重量%時會傾向降低與不飽和異氰酸酯化合物(1)反應所得之聚合物的保存安定性。
(a4)其他不飽和化合物為(a1)、(a2)及(a3)以外之不飽和化合物,其例如,丙烯酸甲酯、丙烯酸n-丙酯、丙烯酸i-丙酯、丙烯酸n-丁酯、丙烯酸sec-丁酯、丙烯酸t-丁酯等丙烯酸烷基酯;甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸n-丙酯、甲基丙烯酸i-丙酯、甲基丙烯酸n-丁酯、甲基丙烯酸sec-丁酯、甲基丙烯酸t-丁酯等甲基丙烯酸烷基酯;丙烯酸環己酯、丙烯酸2-甲基環己酯、丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯、丙烯酸2-(三環〔5.2.1.02 , 6
〕癸烷-8-基氧基)乙酯、丙烯酸異冰片酯等丙烯酸脂環式酯;甲基丙烯酸環己酯、甲基丙烯酸2-甲基環己酯、甲基丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯、甲基丙烯酸2-(三環〔5.2.1.02 , 6
〕癸烷-8-基氧基)乙酯、甲基丙烯酸異冰片酯等甲基丙烯酸脂環式酯;丙烯酸苯酯、丙烯酸苄酯等丙烯酸芳基酯或芳烷基酯;甲基丙烯酸苯酯、甲基丙烯酸苄酯等甲基丙烯酸芳基酯或芳烷基酯;馬來酸二乙酯、富馬酸二乙酯、衣康酸二乙酯等不飽和二羧酸二烷基酯;丙烯酸四氫呋喃-2-酯、丙烯酸四氫吡喃-2-酯、丙烯酸2-甲基四氫吡喃-2-酯等具有含氧雜5員環或含氧雜6員環之丙烯酸酯;甲基丙烯酸四氫呋喃-2-酯、甲基丙烯酸四氫吡喃-2-基、甲基丙烯酸2-甲基四氫吡喃-2-酯等具有含氧雜5員環或含氧雜6員環之甲基丙烯酸酯;苯乙烯、α-甲基苯乙烯、m-甲基苯乙烯、p-甲基苯乙烯、p-甲氧基苯乙烯等乙烯基芳香族化合物;1,3-丁二烯、異戊二烯、2,3-二甲基-1,3-丁二烯等共軛二烯系化合物;丙烯腈、甲基丙烯腈、丙烯醯胺、甲基丙烯醯胺、氯乙烯、氯亞乙烯、乙酸乙酯等。
上述(a4)其他不飽和化合物中,就共聚合反應性及所得〔A〕聚合物對鹼水溶液之溶解性較佳為丙烯酸2-甲基環己酯、甲基丙烯酸t-丁酯、甲基丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯、苯乙烯、p-甲氧基苯乙烯、甲基丙烯酸四氫呋喃-2-酯、1,3-丁二烯。
共聚物〔α〕中,(a4)其他不飽和化合物可單獨或2種以上混合使用。
共聚物〔α〕中,來自(a4)其他不飽和化合物之重覆單位含量較佳為10至70重量%,更佳為20至50重量%,特佳為30至50重量%。來自(a4)其他不飽和化合物之重覆單位含量低於10重量%時,會傾向降低與不飽和異氰酸酯化合物(1)反應所得之聚合物的保存安定性,又,超過70重量%時會傾向降低聚合物對鹼顯像液之溶解性。
共聚物〔α〕例如可由,適當溶劑中存在自由基聚合引發劑下使(a1)不飽和羧酸系化合物、(a2)含環氧基不飽和化合物、(a3)含羥基不飽和化合物及(a4)其他不飽和化合物而得。
該聚合用之溶劑如:甲醇、乙醇、n-丙醇、i-丙醇等醇類;四氫呋喃、二噁烷等醚類;乙二醇-甲基醚、乙二醇-乙基醚、乙二醇單-n-丙基醚、乙二醇單-n-丁基醚等乙二醇-烷基醚;乙二醇-甲基醚乙酸酯、乙二醇-乙基醚乙酸酯、乙二醇單-n-丙基醚乙酸酯、乙二醇單-n-丁基醚乙酸酯等乙二醇-烷基醚乙酸酯;乙二醇-甲基醚丙酸酯、乙二醇-乙基醚丙酸酯、乙二醇單-n-丙基醚丙酸酯、乙二醇單-n-丁基醚丙酸酯等乙二醇-烷基醚丙酸酯;二乙二醇-甲基醚、二乙二醇-乙基醚、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇甲基乙基醚等二乙二醇烷基醚;丙二醇-甲基醚、丙二醇-乙基醚、丙二醇單-n-丙基醚、丙二醇單-n-丁基醚等丙二醇-烷基醚;二丙二醇-甲基醚、二丙二醇-乙基醚、二丙二醇二甲基醚、二丙二醇二乙基醚、二丙二醇甲基乙基醚等二丙二醇烷基醚;丙二醇-甲基醚乙酸酯、丙二醇-乙基醚乙酸酯、丙二醇單-n-丙基醚乙酸酯、丙二醇單-n-丁基醚乙酸酯等丙二醇-烷基醚乙酸酯;丙二醇-甲基醚丙酸酯、丙二醇-乙基醚丙酸酯、丙二醇單-n-丙基醚丙酸酯、丙二醇單-n-丁基醚丙酸酯等丙二醇-烷基醚丙酸酯;甲苯、二甲苯等芳香族烴;甲基乙基酮、2-戊酮、3-戊酮、環己酮、4-羥基-4-甲基-2-戊酮等酮類;2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸n-丙酯、2-甲氧基丙酸n-丁酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-乙氧基丙酸n-丙酯、2-乙氧基丙酸n-丁酯、2-n-丙氧基丙酸甲酯、2-n-丙氧基丙酸酯、2-n-丙氧基丙酸n-丙酯、2-n-丙氧基丙酸n-丁酯、2-n-丁氧基丙酸甲酯、2-n-丁氧基丙酸乙酯、2-n-丁氧基丙酸n-丙酯、2-n-丁氧基丙酸n-丁酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-甲氧基丙酸n-丙酯、3-甲氧基丙酸n-丁酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸n-丙酯、3-乙氧基丙酸n-丁酯、3-n-丙氧基丙酸甲酯、3-n-丙氧基丙酸乙酯、3-n-丙氧基丙酸n-丙酯、3-n-丙氧基丙酸n-丁酯、3-n-丁氧基丙酸甲酯、3-n-丁氧基丙酸乙酯、3-n-丁氧基丙酸n-丙酯、3-n-丁氧基丙酸n-丁酯等烷氧基丙酸烷酯;乙酸甲酯、乙酸乙酯、乙酸n-丙酯、乙酸n-丁酯、羥基乙酸乙酯、羥基乙酸n-丙酯、羥基乙酸n-丁酯、乳酸甲酯、乳酸乙酯、乳酸n-丙酯、乳酸n-丁酯、2-羥基-2-甲基丙酸甲酯、2-羥基-2-甲基丙酸乙酯、3-羥基丙酸甲酯、3-羥基丙酸乙酯、3-羥基丙酸n-丙酯、3-羥基丙酸n-丁酯、2-羥基-3-甲基丁酸甲酯、甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸n-丙酯、甲氧基乙酸n-丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、乙氧基乙酸n-丙酯、n-丙氧基乙酸甲酯、n-丙氧基乙酸乙酯、n-丙氧基乙酸n-丙酯、n-丙氧基乙酸n-丁酯、n-丁氧基乙酸甲酯、n-丁氧基乙酸乙酯、n-丁氧基n-丙酯、n-丁氧基乙酸n-丁酯等其他酯等。
上述溶劑中較佳為二乙二醇烷基醚、丙二醇-烷基醚乙酸酯、烷氧基丙酸烷酯。
該溶劑可單獨或2種以上混合使用。
又,自由基聚合引發劑並無特別限制,例如2,2'-偶氮雙異丁腈、2,2'-偶氮雙-(2,4-二甲基戊腈)、2,2'-偶氮雙-(4-甲氧基-2,4-二甲基戊腈)、4,4'-偶氮雙(4-氰基戊酸)、二甲基-2,2'-偶氮雙(2-甲基丙酸酯)、2,2'-偶氮雙(4-甲氧基-2,4-二甲基戊腈等偶氮化合物;過氧化苯醯、過氧化月桂醯、t-丁基過氧化三甲基乙酸酯、1,1-雙(t-丁基過氧化)環己烷等有機過氧化物;過氧化氫等。
所使用之自由基聚合引發劑為過氧化物時可併用還原劑,而成為氧化還原型引發劑。
上述自由基聚合引發劑可單獨或2以上混合使用。
所得之共聚物〔α〕溶液可直接供給製造〔A〕聚合物用,或由溶液中分離後再供給製造〔A〕聚合物用。
共聚物〔α〕由凝膠滲透色譜法(GPC)求取之聚苯乙烯換算重量平均分子量(以下稱為「Mw」)較佳為2,000至100,000,更佳為5,000至50,000。該Mw低於2,000時恐降低所得被膜之鹼顯像性、殘膜率等,及損害圖型形狀、耐熱性等,又,超過100,000時恐降低解像度及損害圖型形狀。
本發明之〔A〕聚合物係由,共聚物〔α)與不飽和異氰酸酯化合物(1)反應而得。
一般式(1)中,R2
之伸烷基較佳為主鏈碳數1至12之直鏈狀伸烷基。
不飽和異氰酸酯化合物(1)如:2-丙烯醯氧基乙基異氰酸酯、3-丙烯醯氧基丙基異氰酸酯、4-丙烯醯氧基丁基異氰酸酯、6-丙烯醯氧基己基異氰酸酯、8-丙烯醯氧基辛基異氰酸酯、10-丙烯醯氧基癸基異氰酸酯等丙烯酸衍生物;2-甲基丙烯醯氧基乙基異氰酸酯、3-甲基丙烯醯氧基丙基異氰酸酯、4-甲基丙烯醯氧基丁基異氰酸酯、6-甲基丙烯醯氧基己基異氰酸酯、8-甲基丙烯醯氧基辛基異氰酸酯、10-甲基丙烯醯氧基癸基異氰酸酯等甲基丙烯酸衍生物。
又,2-丙烯醯氧基乙基異氰酸酯之市售品如,商品名卡連滋AOI(昭和電工(股)製),2-甲基丙烯醯氧基乙基異氰酸酯之市售品名,商品名卡連滋MOI(昭和電工(股)製)。
上述不飽和異氰酸酯化合物(1)中,就對共聚物〔α〕之反應性較佳為2-丙烯醯氧基乙基異氰酸酯、2-甲基丙烯醯氧基乙基異氰酸酯。
〔A〕聚合物中,不飽和異氰酸酯化合物(1)可單獨或2種以上混合使用。
本發明中共聚物〔α〕及不飽和異氰酸酯化合物(1)之反應方式可為,室溫或加溫下攪拌含有二月桂酸二-n-丁基錫(IV)等觸媒及p-甲氧基苯酚等聚合禁止劑之共聚物〔α〕溶液,同時滴入不飽和異氰酸酯化合物(1)進行。
製造〔A〕聚合物時,對共聚物〔α)中(a3)含羥基不飽和化合物的不飽和異氰酸酯化合物(1)使用量較佳為0.1至90重量%,更佳為10至80重量%,特佳為25至75重量%。該不飽和異氰酸酯化合物(1)之使用量低於0.1重量%時,會減少提升敏感度及彈性特性之效果,又,超過90重量%時會殘留未反應之不飽和異氰酸酯化合物(1),而傾向降低所得聚合物溶液及感放射線性樹脂組成物之保存安定性。
〔A〕聚合物因具有羧基及/或羧酸酐基、環氧基及聚合物不飽和鍵,故對鹼性水溶液具有適度溶解性,且既使未併用特別硬化劑下也易加熱硬化,因此可廣泛作為硬化性樹脂用,特別是適用為形成間隔件用之感放射線性樹脂組成物的樹脂成份。
感放射線性樹脂組成物本發明之感放射線性樹脂組成物含有〔A〕聚合物、〔B〕聚合性不飽和化合物及〔C〕感放射線性聚合引發劑。
含有〔A〕聚合物之感放射線性樹脂組成物於顯像時不會有顯像殘留及膜減少之情形,因此易形成一定形狀之間隔件。
-〔B〕聚合性不飽和化合物-〔B〕聚合性不飽和化合物係由,存在感放射線性聚合引發劑下以放射線曝光時可聚合之不飽和化合物形成。
該〔B〕聚合性不飽和化合物並無特別限制,但較佳如單官能、2官能及3官能以上之(甲基)丙烯酸酯因具有良好共聚合性,而可提升所得間隔件之強度。
該單官能(甲基)丙烯酸酯如,2-羥基乙基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、二乙二醇-乙基醚丙烯酸酯、二乙二醇-乙基醚甲基丙烯酸酯、異冰片基丙烯酸酯、異冰片基甲基丙烯酸酯、3-甲氧基丁基丙烯酸酯、3-甲氧基丁基甲基丙烯酸酯、(2-丙烯醯氧基乙基)(2-羥基丙基)酞酸酯、(2-甲基丙烯醯氧基乙基)(2-羥基丙基)酞酸酯等。市售品名,商品名阿洛尼M-101-、M-111、M-114(以上為東亞合成(股)製);KAYARAD TC-110S、TC-120S(以上為日本化藥(股)製);比斯可158、2311(以上為大阪有機化學工業(股)製)等。
2官能(甲基)丙烯酸酯如,乙二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、二乙二醇二丙烯酸酯、二乙二醇二甲基丙烯酸酯、四乙二醇二丙烯酸酯、四乙二醇二甲基丙烯酸酯、1,6-己二醇二丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、1,9-壬二醇二丙烯酸酯、1,9-壬二醇二甲基丙烯酸酯、二苯氧基乙醇芴二丙烯酸酯、二苯氧基乙醇芴二甲基丙烯酸酯等。市售品如,商品名阿洛尼M-210、M-240、M-6200(以上為東亞合成(股)製);KAYARAD HDDA、HX-220、R-604(以上為日本化藥(股)製);比斯可260、312、335HP(以上為大阪有機化學工業(股)製)等。
3官能以上之(甲基)丙烯酸酯如,三羥甲基丙烷三丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇三甲基丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇四甲基丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇五甲基丙烯酸酯、二季戊四醇六丙烯酸酯、二季戊四醇六甲基丙烯酸酯、三(2-丙烯醯氧基乙基)磷酸酯、三(2-甲基丙烯醯氧基乙基)磷酸酯,或9官能以上之(甲基)丙烯酸酯類,例如具有直鏈伸烷基及脂環式構造,且具有2個以上異氰酸酯基之化合物,與分子內具有1個以上之羥基,且具有3個、4個或5個丙烯醯氧基及/或甲基丙烯醯氧基之化合物反應而得的多官能胺基甲酸乙酯丙烯酸酯系化合物等。
3官能以上之(甲基)丙烯酸酯之市售品如,商品名阿洛尼M1-309、M-400、M-405、M-450、M-7100、M-8030、M-8060、TO-1450(以上為東亞合成(股)製);KAYARAD TMPTA、DPHA、DPCA-20、DPCA-30、PDCA-60、DPCA-120(以上為日本化藥(股)製);比斯可295、300、360、GPT、3PA、400(以上為大阪有機化學工業(股)製)。多官能胺基甲酸乙酯丙烯酸酯系化合物之市售品如,尤佛隆R-1150(第一工業製藥(股)製)、KAYARAD DPHA-40H(日本化藥(股)製)等。
上述單官能、2官能及3官能以上之(甲基)丙烯酸酯中較佳為3官能以上之(甲基)丙烯酸酯,特佳為三羥甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季四醇五丙烯酸酯、二季戊四醇六丙烯酸酯及含有多官能胺基甲酸乙酯丙烯酸酯系化合物之市售品等。
該單官能、2官能及3官能以上之(甲基)丙烯酸酯可單獨或2種以上混合使用。
本發明之感放射線性樹脂組成物中,對〔A〕聚合物100重份之〔B〕聚合性不飽和化合物使用量較佳為1至120重量份,更佳為3至100重量份。該〔B〕聚合性不飽和化合物之使用量低於1重量份時,恐使顯像時產生顯像殘留,又,超過120重量份時會傾向降低所得間隔件之密合性。
-〔C〕感放射線性聚合引發劑-〔C〕感放射線性聚合引發劑係由,以可視光線、紫外線、遠紫外線、荷電粒子線、X線等放射線曝光時能產生引發〔B〕聚合性不飽和化合物聚合之活性種的成份形成。
該〔C〕感放射線性聚合引發劑較佳如,9.H.-咔唑系之O-醯基肟型聚合引發劑(以下稱為「O-醯基肟型聚合引發劑(I)」。
O-醯基肟型聚合引發劑(I)如,1-〔9-乙基-6-苯醯-9.H.-咔唑-3-基〕-壬烷-1,2-壬烷-2-肟-O-苯甲酸酯、1-〔9-乙基-6-苯醯-9.H.-咔唑-3-基〕-壬烷-1,2-壬烷-2-肟-O-乙酸酯、1-〔9-乙基-6-苯醯-9.H.-咔唑-3-基〕-戊烷-1,2-戊烷-2-肟-O-乙酸酯、1-〔9-乙基-6-苯醯-9.H.-咔唑-3-基〕-辛烷-1-酮肟-O-乙酸酯、1-〔9-乙基-6-(2-甲基苯醯)-9.H.-3-基〕-乙烷-1-酮肟-O-苯甲酸酯、1-〔9-乙基-6-(2-甲基苯醯)-9.H.-咔唑-3-基〕-乙烷-1-酮肟-O-乙酸酯、1-〔9-乙基-6-(1,3,5-三甲基苯醯)-9.H.-咔唑-3-基〕-乙烷-1-酮肟-O-苯甲酸酯、1-〔9-丁基-6-(2-乙基苯醯)-9.H.-咔唑-3-基〕-乙烷-1-酮肟-O-苯甲酸酯等。
該O-醯基肟型聚合引發劑(I)中特佳為1-〔9-乙基-6-(2-甲基苯醯)-9.H.-咔唑-3-基〕-乙烷-1-酮肟-O-乙酸酯。
該O-醯基肟型聚合引發劑(I)可單獨或2種以上混合使用。
又,本發明之〔C〕感放射線性聚合引發劑可併用1種以上O-醯基肟型聚合引發劑(I)以外之O-醯基肟型光聚合引發劑(以下稱為「O-醯基肟型聚合引發劑(II)」)。
O-醯基肟型聚合引發劑(II)如,1,2-辛二酮-1-〔4-(苯基硫基)苯基〕-2-(O-苯醯肟)、1,2-丁二酮-1-〔4-(苯基硫基)苯基〕-2-(O-苯醯肟)、1,2-丁二酮-1-〔4-(苯基硫基)苯基〕-2-(O-乙醯肟)、1,2-辛二酮-1-〔4-(甲基硫基)苯基〕-2-(O-苯醯肟)、1,2-辛二酮-1-〔4-(苯基硫基)苯基〕-2-(O-(4-甲基苯醯肟))等。
該O-醯基肟型聚合引發劑(II)中特佳為1,2-辛二酮-1-〔4-(苯基硫基)苯基〕-2-(O-苯醯肟)。
本發明使用O-醯基肟型聚合引發劑(I)或其與O-醯基肟型聚合引發劑(II)之混合物(以下總稱為「O-醯基肟型聚合引發劑」)時,既使以1,200J/m2
以下之曝光量也能達到充分敏感度,及得到良好密合性。
本發明之感放射線性樹脂組成物中,對〔B〕聚合性不飽和化合物100重量份之O-醯基肟型聚合引發劑使用量較佳為5至30重量份,更佳為5至20重量份。該O-醯基肟型聚合引發劑之使用量低於5重量份時,會傾向降低顯像時之殘膜率,又,超過30重量份時會傾向降低顯像時未曝光部對鹼顯像液之溶解性。
又,O-醯基肟型聚合引發劑(II)對O-醯基肟型聚合引發劑(I)及O-醯基肟型聚合引發劑(II)之合計100重量份的使用率較佳為30重量份以下,更佳為20重量份以下。
另外本發明之感放射線性樹脂組成物中,O-醯基肟型聚合引發劑可併用其他感放射線性聚合引發劑1種以上。
該其他感放射線性聚合引發劑如,乙醯苯系化合物、二咪唑系化合物、苯偶因系化合物、二苯甲酮系化合物、α-二酮系化合物、多核醌系化合物、呫噸酮系化合物、膦系化合物、三嗪系化合物等。其中又以乙醯苯系化合物及二咪唑系化合物為佳。
該乙醯苯系化合物如,α-羥基酮系化合物、α-胺基酮系化合物等。
其中α-羥基酮系化合物如,1-苯基-2-羥基-2-甲基丙烷-1-酮、1-(4-i-丙基苯基)-2-羥基-2-甲基丙烷-1-酮、4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮、1-羥基環己基苯基酮等。α-胺基酮系化合物如,2-甲基-1-(4-甲基硫苯基)-2-嗎啉基-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁烷-1-酮、2-(4-甲基苯醯)-2-(二甲基胺基)-1-(4-嗎啉基苯基)-丁烷-1-酮等。該化合物以外之化合物如,2,2-二甲氧基乙醯苯、2,2-二乙氧基乙醯苯、2,2-二甲氧基-2-苯基乙醯苯等。
上述乙醯苯系化合物中特佳為2-甲基-1-(4-甲基硫苯基)-2-嗎啉基丙烷-1-酮、2-(4-甲基苯醯)-2-(二甲基胺基)-1-(4-嗎啉基苯基)-丁烷-1-酮。
本發明併用上述乙醯苯系化合物時可改善敏感度、間隔件形狀及壓縮強度。
又,上述二咪唑系化合物如,2,2'-雙(2-氯苯基)-4,4',5,5'-四(4-乙氧基羰基苯基)-1,2'-二咪唑、2,2'-雙(2-溴苯基)-4,4',5,5'-四(4-乙氧基羰基苯基)-1,2'-二咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2,4-二氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2,4,6-三氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2-溴苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2,4-二溴苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2,4,6-三溴苯基)-4,4',5,5'-四苯基-1,2'-二咪唑等。
該二咪唑系化合物中較佳為,2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2,4-二氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑、2,2'-雙(2,4,6-三氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑等,特佳為2,2'-雙(2,4-二氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑。
本發明併用二咪唑系化合物時,為了增加敏感度可添加具有二烷基胺基之脂肪族系或芳香族系化合物(以下稱為「胺基系增感劑」)。
該胺基系增感劑如,N-甲基二乙醇胺、4,4'-雙(二甲基胺基)二苯甲酮、4,4'-雙(二乙基胺基)二苯甲酮、P-二甲基胺基安息香酸乙酯、P-二甲基胺基安息香酸i-戊酯等。
該胺基系增感劑中特佳為4,4'-雙(二乙基胺基)二苯甲酮。
上述胺系增感劑可單獨或2種以上混合使用。
又,併用二咪唑系化合物及胺基系增感劑時可添加供氫化合物之硫醇系化合物。以胺基系增感劑增加敏感度而使二咪唑系化合物開裂時雖可得到咪唑自由基,但無法得到高聚合引發能,因此所得間隔件多半為不良之逆錐形狀。故將硫醇系化合物加入二咪唑系化合物及胺基系增感劑共存系中,而由硫醇系化合物將氫自由基供給咪唑自由基時,可使咪唑自由基轉變為中性咪唑及得到具有高聚合引發能之硫自由基成份,而得到形狀良好之順錐狀間隔件。
該硫醇系化合物如,2-巰基苯并噻唑、2-巰基苯并噁唑、2-巰基苯并咪唑、2-巰基-5-甲氧基苯并噻唑、2-巰基-5-甲氧基苯并咪唑等芳香族系化合物;3-巰基丙酸、3-巰基丙酸甲酯、3-巰基丙酸乙酯、3-巰基丙酸辛酯等脂肪族系-硫醇類;3,6-二噁-1,8-辛烷二硫醇、季戊四醇四(巰基乙酸酯)、季戊四醇四(3-巰基丙酸酯)等2官能以上之脂肪族系硫醇類。
該硫醇系化合物中特佳為2-巰基苯并噻唑。
本發明之感放射線性樹脂組成物中,其他感放射線性聚合引發劑對全部感放射線性聚合引發劑100重量份之使用率較佳為100重量份,更佳為80重量份以下,特佳為60重量份以下。該其他感放射線性聚合引發劑之使用率超過100重量份時恐損害本發明期望之效果。
又,併用二咪唑系化合物及胺基系增感劑時,胺基系增感劑對二咪唑系化合物100重量份之添加量較佳為0.1至50重量份,更佳為1至20重量份。該胺基系增感劑之添加量低於0.1重量份時,會傾向降低改善敏感度、解像度及密合性效果,又,超過50重量份時會傾向損害所得間隔件之形狀。
另外併用二咪唑系化合物及胺基系增感劑時,硫醇系化合物對二咪唑系化合物100重量份之添加量較佳為0.1至50重量份,更佳為1至20重量份。該硫醇系化合物之添加量低於0.1重量份時,會傾向降低改善間隔件形狀之效果及易使膜減少,又,超過50重量份時會傾向損害所得間隔件之形狀。
但本發明可僅單獨或2種以上混合使用。一醯基肟型聚合引發劑(I)以外之〔C〕感放射線性聚合引發劑。
-添加劑-無損本發明期待之效果下,必要時本發明之感放射線性樹脂組成物可添加上述成份以外之表面活性劑、接著助劑、保存安定劑、耐熱性提升劑等。
其中表面活性劑為具有改善塗佈性作用之成份,較佳為氟系表面活性劑及聚矽氧烷系表面活性劑。
該氟系表面活性劑較佳為,末端、主鏈及支鏈中至少一部位具有氟烷基或氟伸烷基之化合物,其具體例如,1,1,2,2-四氟辛基(1,1,2,2-四氟-n-丙基)醚、1,1,2,2-四氟-n-辛基(n-己基)醚、八乙二醇二(1,1,2,2-四氟-n-丁基)醚、六乙二醇(1,1,2,2,3,3-六氟-n-戊基)醚、八丙二醇二(1,1,2,2-四氟-n-丁基)醚、六丙二醇二(1,1,2,2,3,3-六氟-n-戊基)醚、1,1,2,2,3,3-六氟-n-癸烷、1,1,2,2,8,8,9,9,10,10-十氟-n-十二烷、全氟-n-十二烷基磺酸鈉,或氟烷基苯磺酸鈉、氟烷基膦酸鈉、氟烷基羧酸鈉、氟烷基聚環氧乙烷醚、二甘油四(氟烷基聚環氧乙烷醚)、氟烷基銨磺化物、氟烷基甜菜鹼、氟烷基聚環氧乙烷醚、全氟烷基聚氧化乙醇、全氟烷基烷氧化物、氟系烷基酯等。
又,氟系表面活性劑之市售品如,商品名BM-1000、BM-1100(以上為BM CHEMIE公司製);美加凡下142D、F172、F173、F183、F178、F191、F471、F476(以上為大日本油墨化學工業(股)製);佛洛拉FC-170C、FC-171、FC-430、FC-431(以上為住友3M(股)製)、撒佛隆S-112、S-113、S131、S-141、S-145、S-382、SC-101、SC-102、SC-103、SC-104、SC-105、SC-106(以上為旭硝子(股)製)、艾佛特EF301、EF303、EF352(以上為新秋田化成(股)製);佛達珍FT-100、FT-110、FT-140A、FT-150、FT-250、FT-251、FTX-251、FTX-218、FT-300、FT-310、FT-400S(以上為那歐斯(股)製)等。
上述聚矽氧烷系表面活性劑之市售品如,商品名特雷西DC3PA、DC7PA、SH11PA、SH21PA、SH28PA、SH29PA、SH30PA、SH-190、SH-193、SZ-6032、SF-8428、DC-57、DC-190(以上為東雷(股)製);TSF-4440、4300、4445、4446、4460、4452(以上為GE東芝(股)製)等。
上述以外之表面活性劑如,聚環氧乙烷月桂醚、聚環氧乙烷硬脂醚、聚環氧乙烷油醚等聚環氧乙烷烷基醚;聚環氧乙烷n-辛基苯基醚、聚環氧乙烷n-壬基苯基醚等聚環氧乙烷芳基醚;聚環氧乙烷二月桂酸酯、聚環氧乙烷二硬脂酸酯等聚環氧乙烷二烷基醚等非離子系表面活性劑;市售品如,商品名KP341(信越化學工業(股)製)、聚佛隆NO.57、NO.95(共榮社化學(股)製)等。
上述表面活性劑可單獨或2種以上混合使用。
表面活性劑對〔A〕聚合物100重量份之添加量較佳為5重量份以下,更佳為2重量份以下。該表面活性劑之添加量超過5重量份時,會傾向塗佈時易產生膜粗糙。
上述接著助劑為具有改善間隔件與基體之密合性作用的成份,較佳為官能性矽烷偶合劑。
該官能性矽烷偶合劑如,具有羧基、甲基丙烯醯基、乙烯基、異氰酸酯基、環氧基等反應性官能基之化合物。具體例如,三甲氧基矽烷基安息香酸、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、乙烯基三乙醯氧基矽烷、乙烯基三甲氧基矽烷、γ-異氰酸酯丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷等。
該接著助劑可單獨或2種以上混合使用。
接著助劑對〔A〕聚合物100重量份之添加量較佳為20重量份以下,更佳為10重量份以下。該接著助劑之添加量超過20重量份時,易傾向產生顯像殘留。
上述保存安定劑如,硫、醌類、氫醌類、聚羥基化合物、胺、硝基亞硝基化合物等,具體例如,4-甲氧基苯酚、N-亞硝基-N-苯基羥基胺鋁等。
該保存安定劑可單獨或2種以上混合使用。
保存安定劑對〔A〕聚合物100重量份之添加量較佳為3重量份以下,更佳為0.001至0.5重量份。該保存安定劑之添加量超過3重量份時恐降低敏感度,而損害圖型形狀。
上述耐熱性提升劑如,N-(烷氧基甲基)甘脲化合物、N-(烷氧基甲基)三聚氰胺化合物、具有2個以上環氧基之化合物等。
該N-(烷氧基甲基)甘脲化合物如,N,N,N,N-四(甲氧基甲基)甘脲、N,N,N,N-四(乙氧基甲基)甘脲、N,N,N,N-四(n-丙氧基甲基)甘脲、N,N,N,N-四(i-丙氧基甲基)甘脲、N,N,N,N-四(n-丁氧基甲基)甘脲、N,N,N,N-四(t-丁氧基甲基)甘脲等。
該N-(烷氧基甲基)甘脲中特佳為N,N,N,N-四(甲氧基甲基)甘脲。
上述N-(烷氧基甲基)三聚氰胺化合物如,N,N,N,N,N,N-六(甲氧基甲基)三聚氰胺、N,N,N,N,N,N-六(乙氧基甲基)三聚氰胺、N,N,N,N,N,N-六(n-丙氧基甲基)三聚氰胺、N,N,N,N,N,N-六(i-丙氧基甲基)三聚氰胺、N,N,N,N,N,N-六(n-丁氧基甲基)三聚氰胺、N,N,N,N,N,N-六(t-丁氧基甲基)三聚氰胺等。
該N-(烷氧基甲基)三聚氰胺化合物中特佳為N,N,N,N,N,N-六(甲氧基甲基)三聚氰胺,其市售品如,商品名尼卡拉N-2702、NW-30M(以上為三和化學(股)製)等。
上述具有2個以上環氧基之化合物如,乙二醇二縮水甘油醚、二乙二醇二縮水甘油醚、聚乙二醇二縮水甘油醚、丙二醇二縮水甘油醚、三丙二醇二縮水甘油醚、聚丙二醇二縮水甘油醚、新戊二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、甘油二縮水甘油醚、甘油三縮水甘油醚、三羥甲基丙烷三縮水甘油醚、氫化雙酚A二縮水甘油醚、雙酚A二縮水甘油醚、正甲酚酚醛清漆型環氧樹脂,或市售品如,商品名耶波來40E、100E、200E、70P、200P、400P、1500NP、1600、80MF、100MF、3002、4000(以上為共榮社化學(股)製)、EOCN102、103S、104S、1020、1025、1027(以上為日本化藥(股)製、耶皮可180S(日本環氧械脂公司製)等。
該耐熱性提升劑可單獨或2種以上混合使用。
耐熱性提升劑對〔A〕聚合物100重量份之添加量較佳為30重量份以下,更佳為20重量份以下。該耐熱性提升劑之添加量超過30重量份時,會傾向降低感放射線性樹脂組成物之保存安定性。
-溶劑-本發明之感放射線性樹脂組成物的使用形態較佳為,溶解於適當溶劑之組成物溶液。
所使用之溶劑可為,能均勻溶解構成感放射線性樹脂組成物用之各成份且不起反應而能適度揮發之物,但就各成份之溶解能、對各成份之反應性及塗膜形成容易性等觀點較佳為醇類、乙二醇-烷基醚乙酸酯、二乙二醇-烷基醚乙酸酯、二乙二醇烷基醚、丙二醇-烷基醚乙酸酯、烷氧基丙酸烷酯等,特佳為苄基醚、2-苯基乙醇、3-苯基-1-丙醇、乙二醇單-n-丁基醚乙酸酯、二乙二醇-乙基醚乙酸酯、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇乙基甲基醚、丙二醇-甲基醚乙酸酯、丙二醇-乙基乙酸酯等。
該溶劑可單獨或2種以上混合使用。
本發明可併用該溶劑及高沸點溶劑。
該高沸點溶劑如,N-甲基甲醯胺、N,N-二甲基甲醯胺、N-甲基甲醯苯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、二甲基亞碸、苄基乙基醚、二-N-己基醚、丙酮基丙酮、異氟爾酮、己酸、辛酸、1-辛醇、1-壬醇、苄基醇、乙酸苄酯、安息香酸乙酯、草酸二乙酯、馬來酸二乙酯、γ-丁內酯、碳酸乙烯、碳酸丙烯、乙二醇-苯基醚乙酸酯等。
該高沸點溶劑可單獨或2種以上混合使用。
又,上述所得之組成物溶液可以孔徑0.5μm之米利波阿濾器等過濾後再供使用。
本發明之感放射線性樹脂組成物特別適用於形成液晶顯示元件用之間隔件用。
間隔件之形成方法下面將說明使用本發明之感放射線性樹脂組成物形成本發明之液晶顯示元件用間隔件(以下亦簡稱為「間隔件」)的方法。
形成本發明之間隔件時,至少須依序包含下列步驟。
(1)基板上形成本發明之感放射線性樹脂組成物塗膜的步驟;(2)將至少部分塗膜曝光之步驟;(3)將曝光後之塗膜顯像之步驟;(4)將顯像後之塗膜加熱之步驟。
-(1)步驟-於透明基板單面上形成透明導電膜後,將感放射線性樹脂組成物,較佳為組成物溶液塗佈於透明導電膜上,再將塗佈面加熱(預熱)而形成塗膜。
形成間隔件用之透明基板如,玻璃基板、樹脂基板等,具體例如,鹼石灰玻璃、無鹼玻璃等玻璃基板;聚對苯二甲酸乙二醇酯、聚對苯二甲酸丁二醇酯、聚酯碸、聚碳酸酯、聚醯亞胺等塑料所形成之樹脂基板。
設置於透明基板單面之透明導電膜如,氧化錫(SnO2
)所形成之NESA膜(美國PPG公司登記商標)、氧化銦-氧化錫(In2
O3
-SnO2
)所形成之ITO膜等。
組成物溶液之塗佈方法可採用噴霧法、滾軸塗佈法、回轉塗佈法(旋塗法)、縫模頭塗佈法、棒塗佈法、噴墨塗佈法等適當方法,特佳為旋塗法及縫模頭塗佈法。
又,預熱條件可依各成份種類、添加率等而異,但一般為70至120℃下1至15分鐘。
-(2)步驟-其次至少將部分所得塗膜曝光。將部分塗膜曝光時一般係介由具有一定圖型之光圖罩進行曝光。
曝光用之放射線如,可視光線、紫外線、遠紫外線、電子線、X線等,但以波長190至450nm之放射線為佳,特佳為含365nm紫外線之放射線。
曝光量可為以照度計(OAI model 356、OAI Optical Associates Inc.製)測定曝光放射線波長365nm之強度而得的例如100至10,000J/m2
,較佳為1,500至3,000J/m2
。
-(3)步驟-接著將曝光後之塗膜顯像以去除不要部分,而形成一定圖型。
顯像時所使用之顯像液較佳為鹼顯像液。例如,氫氧化鈉、氫氧化鉀、碳酸鈉、矽酸鈉、偏矽酸鈉、氨等無機鹼;乙基胺、n-丙基胺等脂肪族1級胺;二乙基胺、二-n-丙基胺等脂肪族2級胺;三甲基胺、甲基二乙基胺、二甲基乙基胺、三乙基胺等脂肪族3級胺;吡咯、哌啶、N-甲基哌啶、N-甲基哌啶、1,8-二氮雜二環〔4.3.0〕-5-壬烯等脂環族3級胺;吡啶、三甲基吡啶、二甲基吡啶、喹啉等芳香族3級胺;乙醇二甲基胺、甲基二乙醇胺、三乙醇胺等鹼醇胺;四甲基銨羥化物、四乙基銨羥化物等4級銨鹽等鹼性化合物之水溶液。
又,該鹼性化合物之水溶液可適當添加甲醇、乙醇等水溶性有機溶劑及表面活性劑。
顯像方法可為盛液法、浸漬法、淋浴法等,顯像時間一般為10至180秒。
顯像後例如以流水洗淨30至90秒,再以例如壓縮空氣或壓縮氮風乾,而形成所希望之圖型。
-(4)步驟-最後利用例如熱板、烤箱等加熱裝置,以一定溫度,例如100至160℃加熱一定時間,例如熱板上5至30分鐘、烤箱中30至180分鐘(顯像後加熱)後可得一定間隔件。
先前形成間隔件用之感放射線性樹脂組成物未進行180至200℃以上之加熱處理時,將無法使所得間隔件發揮充分性能,但本發明之感放射線性樹脂組成物可以低於先前之加熱溫度,於樹脂基板不變黃及變形之情形下,形成具有優良壓縮強度、液晶配向時之耐刷洗性、對透明基板之密合等諸性能的間隔件。
液晶顯示元件本發明之液晶顯示元件為,具備上述所形成的本發明之液晶顯示元件用間隔件。
本發明之液晶顯示元件的構造並無特別限制,何如圖1所示具備透明基板上形成濾色層及間隔件、介有液晶層配置之2個配向膜、對向透明電極、對向透明基板等構造。又如圖1所示,必要時可具備偏光板及形成於濾色層上之保護膜。
另外可如圖2所示為,透明基板上形成濾色層及間隔件後,介有配向膜及液晶層與薄膜晶體(TFT)數組相對而得的TN-TFT型液晶顯示元件。必要時可備有偏光板及形成於濾色層上之保護膜。
本發明之〔A〕聚合物因具有羧基及/或羧酸酐基、環氧基及聚合性不飽和鍵,故對鹼性水溶液具有適度溶解性,且既使不併用特別硬化劑下也易加熱硬化,因此特別適用為形成液晶顯示元件之間隔件用的感放射線性樹脂組成物之樹脂成份。
本發明之感放射線性樹脂組成物可形成,高敏感度及高解像度下既使以1,200J/m2
以下之曝光量也能得到充分圖型形狀,且具有優良彈性回復性、耐刷洗性、對透明基板之密合性、耐熱性等液晶顯示元件用之間隔件,又,形成間隔件時能降低顯像後加熱溫度,且不會產生樹脂基板變黃及變形。
本發明之液晶顯示元件因具備,具有優良圖型形狀、彈性回復性、耐刷洗性、對透明基板之密合性、耐熱性等諸性能之間隔件,故可表現出長期高信賴性。
下面將舉實施例更具體說明本發明之實施形態,例如份及%均為重量基準。
將2,2'-偶氮雙(2,4-二甲基戊腈)5份、二乙二醇甲基乙基醚250份放入備有冷卻管及攪拌機之燒瓶中,再加入甲基丙烯酸17份、甲基丙烯酸縮水甘油酯45份、甲基丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯23份、苯乙烯5份及甲基丙烯酸2-羥基乙酯10份;以氮取代後緩緩攪拌下將溶液溫度升至70℃,該溫度下保持4小時進行聚合,得固體成份濃度28.0%之共聚物〔α〕溶液。
所得共聚物〔α〕以GPC(凝膠滲透色譜法)HLC-8020(商品名,東索(股)製)測得之Mw為18,000。
其次將2-甲基丙烯醯氧基乙基異氰酸酯(商品名卡連滋MOI,昭和電工(股)製)5份、二月桂酸二-n-丁基錫(IV)0.03份及4-甲氧基苯酚0.1份加入所得共聚物〔α〕溶液中,40℃及50℃下各自攪拌3小時及1.5小時進行反應。又,可以IR(紅外線吸收)光譜確認卡連滋MOI之異氰酸酯基與共聚物〔α〕之羥基進行反應。結果聚合物溶液〔α〕、反應1小時後之溶液、40℃下3小時再50℃下1.5小時反應後之溶液的各自IR光譜如圖3之(a)、(b)及(c)所示。又,確認反應進行時來自卡連滋MOI之異氰酸酯基的2,270cm- 1
附近峰減少,可得固體成份濃度29.3%之〔A〕聚合物溶液。以該〔A〕聚合物為聚合物(A-1)。
將2,2'-偶氮雙(2,4-二甲基戊腈)7份、二乙二醇甲基乙基醚250份放入備有冷卻管及攪拌機之燒瓶中,再加入甲基丙烯酸18份、甲基丙烯酸2-甲基縮水甘油酯30份、甲基丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯27份、苯乙烯5份、甲基丙烯酸2-羥基乙酯10份及甲基丙烯酸四氫呋喃-2-酯10份,以氮取代後緩緩攪拌下將溶液溫度升至70℃,該溫度下保持4小時進行聚合,得固體成份濃度29.0%之共聚物〔α〕溶液。
所得共聚物〔α〕以GPC(激膠滲透色譜法)HLC-8020測得之Mw為11,000。
其次將2-甲基丙烯醯氧基乙基異氰酸酯(商品名卡連滋MOI,昭和電工(股)製)5份、二月桂酸二-n-丁基錫(IV)0.03份及4-甲氧基苯酚0.1份加入所得共聚物〔α〕溶液中,40℃下及50℃下各自攪拌3小時及1.5小時進行反應,並同合成例1確認反應進行,得固體成份濃度30.2%之〔A〕聚合物溶液。以該〔A〕聚合物為聚合物(A-2)。
將2,2'-偶氮雙(2,4-二甲基戊腈)7份、二乙二醇甲基乙基醚250份放入備有冷卻管及攪拌機之燒瓶中,再加入甲基丙烯酸18份、甲基丙烯酸2-甲基縮水甘油酯30份、甲基丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯27份、苯乙烯5份、甲基丙烯酸2-羥基乙酯10份及甲基丙烯酸四氫呋喃-2-酯10份,以氮取代後緩緩攪拌下將溶液溫度升至70℃,該溫度保持4小時進行聚合,得固體成份濃度29.0%之共聚物〔α〕溶液。
所得共聚物〔α〕以GPC(激膠滲透色譜法)HLC-8020測得之Mw為11,000。
其次將2-丙烯醯氧基乙基異氰酸酯(商品名卡連滋AOI,昭和電工(股)製)2.5份、二月桂酸二-n-丁基錫(IV)0.03份及4-甲氧基苯酚0.1份加入所得共聚物〔α〕溶液中,40℃下及50℃下各自攪拌3小時及1.5小時進行反應,並同合成例1確認反應進行,得固體成份濃度30.2%之〔A〕聚合物溶液。以該〔A〕聚合物為聚合物(A-3)。
將2,2'-偶氮雙(2,4-二甲基戊腈)5份、二乙二醇甲基乙基醚250份放入備有冷卻管及攪拌機之燒瓶中,再加入甲基丙烯酸18份、甲基丙烯酸縮水甘油酯45份、甲基丙烯酸三環〔5.2.1.02 , 6
〕癸烷-8-酯32份及苯乙烯5份,以氮取代後緩緩攪拌下將溶液溫度升至70℃,該溫度下保持4小時進行聚合,得固體成份濃度28.5%之共聚物溶液。
所得共聚物以GPC(凝膠滲透色譜法)HLC-8020測得之Mw為18,000。以該共聚物為聚合物(a-1)。
將2,2'-偶氮雙(2-甲基丁腈)4份、二乙二醇二甲基醚185份放入備有冷卻管及攪拌機之燒瓶中,再加入甲基丙烯酸20份、甲基丙烯酸苄酯25份、苯乙烯35份及甲基丙烯酸2-羥基乙酯20份,以氮取代後緩緩攪拌下將溶液溫度升至85℃,該溫度下保持2小時後100℃下保持1小時進行聚合,得固體成份濃度34.0%之共聚物溶液。
所得共聚物以GPC(激膠滲透色譜法)HLC-8020測得之Mw為28,000。
其次將2-甲基丙烯醯氧基乙基異氰酸酯(商品名卡連滋MOI,昭和電工(股)製)5份、二月桂酸二丁基錫(IV)0.03份、4-甲氧基苯酚0.1份加入所得共聚物溶液中,40℃及50℃下各自攪拌3小時及1.5小時進行反應,得固體成份濃度35.2%之聚合物溶液。以該聚合物為聚合物(a-2)。
調製組成物溶液以合成例1所得〔A〕聚合物溶液之聚合物(A-1)100份為〔A〕成份,以二季戊四醇六丙烯酸酯(商品名KAYARAD DPHA,日本化藥(股)製)80份為〔B〕成份,以1-〔9-乙基-6-(2-甲基苯醯)-9.H.-咔唑-3-基〕-乙烷-1-酮肟-O-乙酸酯(商品名(GI-242,吉巴斯公司製)5份為〔C〕成份,以γ-環氧丙氧基丙基三甲氧基矽烷5份為接著助劑,以FTX-218(商品名,那歐斯(股)製)0.5份為表面活性劑,及以4-甲氧基苯酚0.5份為保存安定劑,混合後溶解於丙二醇-甲基醚乙酸酯中使固體成份濃度為30%後,以孔徑0.5μm之米利波阿濾器過濾,得組成物溶液。主成份之組成比率如表1所示。
形成間隔件利用旋塗機將該組成物溶液塗佈於無鹼玻璃基板上,以90℃熱板預熱3分鐘,形成膜厚6.0μm之被膜。
其次介由圖型殘角為10μm之圖罩,以365μm之強度為250W/m2
的紫外線將所得被膜曝光10秒後,25℃下以氫氧化鋰0.05重量%水溶液顯像60秒,再以純水洗淨1分鐘,其後以220℃烤箱加熱60分鐘,形成間隔件。
接著以下列要領進行各種評估。評估結果如表4及表5所示。
(1)評估敏感度除了變更曝光量外其他同上述形成間隔件,並以形成間隔件時顯像後之殘膜率(顯像後之膜厚×100/初期膜厚,以下均同)為90%以上之曝光量為敏感度。該曝光量為1,500J/m2
以下時視敏感度為良好。
(2)評估解像度除了變更曝光量外其他同上述形成間隔件,並以形成間隔件時顯像後之殘膜率為90%以上的曝光量解像再評估最小圖型尺寸。
(3)評估剖面形狀以掃描型電子顯微鏡觀察所得間隔件之剖面形狀,並以圖4所示A至D進行評估。其中A或B之圖型邊緣為順錐型或垂直狀,故視剖面形狀為良好。相對地C因敏感度不足而殘膜率較低,且剖面尺寸比A及B小及底部為平面半凸透鏡狀,故視剖面形狀不良,又,D為逆錐狀(剖面形狀中膜表面邊長於基板側邊之逆三角形),因此後刷洗處理時非常可能使圖型剝離,故視剖面形狀不良。
(4)評估彈性回復率對所得間隔件使用微小壓縮試驗機(商品名MCTM-200,島津製作所(股)製),利用直徑50μm之平面壓子以負荷速度及緩荷速度均為2.6mN/秒之條件荷重至50mN,保持5秒後除荷,再製作負荷時荷重-變形量曲線及緩荷時荷重-變形量曲線。其次如圖5所示,以負荷時荷重50mN之變形量與荷重5mN之變形量的差值為L1,以緩荷時荷重50mN之變形量與荷重5mN之變形量的差值為L2,由下列式算出彈性回復率。
彈性回復率(%)=L2×100/L1
(5)評估耐刷洗性使用液晶配向膜塗佈用印刷機將液晶配向劑AL3046(商品名,JSR(股)製)塗佈於形成間隔件之基板上,以180℃乾燥1小時後形成膜厚0.05μm之液晶配向劑塗膜。
其次使用具有卷附聚醯胺製布料之滾軸的刷洗機,以溶軸回轉數500rpm、階段移動速度1cm/秒之條件對塗膜進行刷洗處理,再評估有無圖型削減或剝離情形。
(6)評估密合性除了未使用光圖罩外其他同上述形成間隔件,形成硬化膜後以JIS K-5400(1900)8.5附著性試驟中8.5.2之棋格膠帶法評估。結果100個棋格中殘留棋格數如表3所示。
(7)評估耐熱性除了未使用光圖罩外其他同上述形成間隔件,形成硬化膜後以240℃烤箱加熱60分鐘並測定加熱前後之膜厚,再評估殘膜率(加熱後膜厚×100/初期膜厚)。
混合表1至3所示各成份及接著助劑γ-環氧丙氧基丙基三甲氧基矽烷5份、表面活性劑FTX-218 0.5份、保存安定劑4-甲氧基苯酚0.5份後溶解於丙二醇-甲基醚乙酸酯中使固體成份濃度為30%後,以孔徑0.5μm之米利波阿濾器過濾,得組成物溶液。其次同實施例1形成間隔件再評估。評估結果如表4及表5所示。
表1至3中聚合物以外之各成份如下所示。
〔B〕成份B-1:二季戊四醇六丙烯酸酯(商品名KAYARAD DPHA)B-2:含多官能胺基甲酸乙酯丙烯酸酯系化合物之市售品(商品名KAYARAD DPHA-40H)〔C〕成份C-1:1-〔9-乙基-6-(2-甲基苯醯)-9.H.-咔唑-3-基〕-乙烷-1-酮肟-O-乙酸酯(商品名(GI-242,吉巴斯公司製)C-2:1,2-辛二酮-1-〔4-(苯基硫基)苯基〕-2-(O-苯醯肟)(商品名(CI-124,吉巴斯公司製)C-3:2-甲基-1-(4-甲基硫苯基)-2-嗎啉基丙烷-1-酮(商品名伊路卡907,吉巴斯公司製)C-4:2-(4-甲基苯醯)-2-(二甲基胺基)-1-(4-嗎啉基苯基)-丁烷-1-酮C-5:2,2'-雙(2,4-二氯苯基)-4,4',5,5'-四苯基-1,2'-二咪唑C-6:4,4'-雙(二乙基胺基)二苯甲酮C-7:2-巰基苯并噻唑
圖1為,液晶顯示元件之一構造例模式圖。
圖2為,液晶顯示元件另一構造例模式圖。
圖3為,製造本發明之聚合物時追踪反應經過之IR光譜圖。
圖4為,間隔件之剖面形狀模式圖。
圖5為,評估彈性回復率用之負荷時及緩荷時荷重-變形量曲線圖。
Claims (6)
- 一種聚合物,其係藉由使(a1)不飽和羧酸及/或不飽和羧酸酐、(a2)含環氧基不飽和化合物、(a3)含羥基不飽和化合物及(a4)其他不飽和化合物之共聚物中之來自前述(a3)含羥基不飽和化合物的羥基,與下列式(1)所示異氰酸酯化合物在觸媒存在下反應,於前述共聚物之側鏈導入(甲基)丙烯醯基而得,
- 一種感放射線性樹脂組成物,其特徵為,含有〔A〕如申請專利範圍第1項之聚合物、〔B〕聚合性不飽和化合物及〔C〕感放射線性聚合引發劑。
- 一種形成液晶顯示元件用之間隔件用的感放射線性樹脂組成物,其係由如申請專利範圍第2項之感放射線性樹脂組成物形成。
- 一種液晶顯示元件用間隔件,其係由如申請專利範圍第3項之感放射線性樹脂組成物形成而成。
- 一種液晶顯示元件用間隔件之形成方法,其特徵為至少依序包含下列步驟;(1)於基板上形成如申請專利範圍第3項之感放射線性樹脂組成物之塗膜的步驟,(2)將至少該塗膜的至少一部分曝光之步驟, (3)將曝光後之該塗膜顯像的步驟,(4)顯像後將該塗膜加熱之步驟。
- 一種液晶顯示元件,其為具備如申請專利範圍第4項之間隔件。
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JP4815952B2 (ja) | 2005-08-26 | 2011-11-16 | Jsr株式会社 | 重合体、カラーフィルタ用感放射線性組成物、カラーフィルタおよびカラー液晶表示パネル |
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