TW201829581A - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- TW201829581A TW201829581A TW106125289A TW106125289A TW201829581A TW 201829581 A TW201829581 A TW 201829581A TW 106125289 A TW106125289 A TW 106125289A TW 106125289 A TW106125289 A TW 106125289A TW 201829581 A TW201829581 A TW 201829581A
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- carbon atoms
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- 239000011342 resin composition Substances 0.000 title claims abstract description 90
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 239000011347 resin Substances 0.000 claims abstract description 78
- 229920005989 resin Polymers 0.000 claims abstract description 78
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims abstract description 55
- 125000000962 organic group Chemical group 0.000 claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 aromatic sulfamic acid compound Chemical class 0.000 claims description 113
- 239000010410 layer Substances 0.000 claims description 64
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 33
- 238000010438 heat treatment Methods 0.000 claims description 26
- 239000002243 precursor Substances 0.000 claims description 25
- 150000002430 hydrocarbons Chemical group 0.000 claims description 21
- 239000004065 semiconductor Substances 0.000 claims description 21
- 229920001721 polyimide Polymers 0.000 claims description 19
- 239000004642 Polyimide Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000003431 cross linking reagent Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000011229 interlayer Substances 0.000 claims description 11
- 150000002466 imines Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000011241 protective layer Substances 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 150000001409 amidines Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 34
- 230000035945 sensitivity Effects 0.000 abstract description 25
- 238000010521 absorption reaction Methods 0.000 abstract description 17
- 150000008430 aromatic amides Chemical class 0.000 abstract 1
- 239000010408 film Substances 0.000 description 85
- 238000000034 method Methods 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 38
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 28
- 238000000576 coating method Methods 0.000 description 28
- 239000000126 substance Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- 238000005401 electroluminescence Methods 0.000 description 26
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 25
- 239000003513 alkali Substances 0.000 description 24
- 239000011248 coating agent Substances 0.000 description 24
- 239000003999 initiator Substances 0.000 description 24
- 239000003086 colorant Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 12
- 238000006297 dehydration reaction Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000018044 dehydration Effects 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 238000006798 ring closing metathesis reaction Methods 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 238000009413 insulation Methods 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 150000002923 oximes Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000013007 heat curing Methods 0.000 description 7
- 230000007774 longterm Effects 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920002098 polyfluorene Polymers 0.000 description 7
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 239000010954 inorganic particle Substances 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000003628 tricarboxylic acids Chemical class 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000010943 off-gassing Methods 0.000 description 4
- 238000002161 passivation Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920005575 poly(amic acid) Polymers 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 239000013585 weight reducing agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 3
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N N-acetyl-para-amino-phenol Natural products CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 150000007513 acids Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-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
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- RLXBOUUYEFOFSW-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-diol Chemical compound NC1=CC(O)=C(N)C=C1O RLXBOUUYEFOFSW-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-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
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 2
- IPMAGDHPWCPGAY-UHFFFAOYSA-N 2-amino-5-[4-amino-5-hydroxy-2-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenol Chemical compound C1=C(O)C(N)=CC(C(F)(F)F)=C1C1=CC(O)=C(N)C=C1C(F)(F)F IPMAGDHPWCPGAY-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 2
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 2
- UCFMKTNJZCYBBJ-UHFFFAOYSA-N 3-[1-(2,3-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)C1=CC=CC(C(O)=O)=C1C(O)=O UCFMKTNJZCYBBJ-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 2
- IJJNNSUCZDJDLP-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 IJJNNSUCZDJDLP-UHFFFAOYSA-N 0.000 description 2
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 2
- OLIGPHACAFRDEN-UHFFFAOYSA-N 4-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=C(C2=C(C=CC=C2)C1=O)S(=O)=O OLIGPHACAFRDEN-UHFFFAOYSA-N 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- SBEQWOXEGHQIMW-UHFFFAOYSA-N silicon Chemical compound [Si].[Si] SBEQWOXEGHQIMW-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
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Abstract
Description
本發明係關於含有鹼可溶性樹脂與醯胺酚化合物的樹脂組成物。
例如聚醯亞胺、聚苯并唑等耐熱性樹脂,因為具有優異的耐熱性、電絕緣性,因而含有該等耐熱性樹脂的感光性樹脂組成物,被使用於例如:LSI等半導體元件的表面保護層、層間絕緣層、以及有機電致發光元件與有機EL顯示元件的絕緣層、顯示裝置用TFT基板的平坦化層等。
對半導體可靠度的要求日益提高,因要求高溫高濕環境下的可靠度,因而針對半導體的表面保護層、層間絕緣層所使用的樹脂組成物亦要求低吸水性。又,相關有機EL顯示裝置亦是因為有機EL發光材料容易受因水分而劣化的影響,因而對有機EL顯示裝置的絕緣層所使用之樹脂組成物亦要求低吸水性。又,近年就從基板大型化、生產性提升等理由,要求縮短曝光時間,故而對感光性樹脂組成物要求更高的感度。就從此現象觀之,強烈期盼開發出能依高感度圖案化、可獲得低吸水性硬化膜的感光性樹脂組成物。
此處,就經硬化後的膜係屬於低吸水的正型感光性樹脂組成物,有提案含有:鹼可溶性樹脂、重氮萘醌化合物、以及未 含酚性羥基但含羥甲基之化合物的正型感光性樹脂組成物(例如參照專利文獻1)。然而,該感光性樹脂組成物存在有感度不足的問題。所以,就高感度且高解析度的感光性樹脂組成物,有提案例如:以聚醯胺樹脂、感光性醌二疊氮化合物及醯胺酚化合物為必要成分的正型感光性樹脂組成物(例如參照專利文獻2);含有:鹼可溶性樹脂、感光性重氮醌化合物及酚化合物的正型感光性樹脂組成物(例如參照專利文獻3)。
專利文獻1:美國專利申請案公開第2004-259020號說明書
專利文獻2:日本專利特開2001-183835號公報
專利文獻3:日本專利特開2004-125815號公報
然而,專利文獻2~3所記載的感光性樹脂組成物,屬於極性基的酚性羥基在硬化後會有殘存的情況,會有造成吸水率提高的問題。緣是,本發明課題在於提供:高感度、能獲得低吸水率硬化膜的樹脂組成物。
本發明的樹脂組成物係含有:(a)鹼可溶性樹脂、以及(b1)在酚性羥基鄰位具有下述一般式(1)所示1價基的醯胺酚化合物及/或(b2)在羧基鄰位具有下述一般式(2)所示1價基的芳香族醯胺酸化合物。
(一般式(1)中,X係表示與一般式(1)中的羰基碳直接鍵結且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。一般式(2)中,U係表示與一般式(2)中的醯胺氮直接鍵結且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。Y係表示碳數1~10之伸烷基;n係表示1~20的整數。)
本發明的樹脂組成物係高感度,根據本發明的樹脂組成物,便可獲得低吸水率的硬化膜。
1‧‧‧TFT(薄膜電晶體)
2‧‧‧配線
3‧‧‧絕緣層
4‧‧‧平坦化層
5‧‧‧ITO(透明電極)
6‧‧‧基板
7‧‧‧接觸窗
8‧‧‧絕緣層
9‧‧‧矽晶圓
10‧‧‧Al墊
11‧‧‧鈍化層
12‧‧‧絕緣層
13‧‧‧金屬層
14‧‧‧金屬配線
15‧‧‧絕緣層
16‧‧‧阻障金屬
17‧‧‧切割道
18‧‧‧焊料凸塊
圖1係TFT基板一例的剖視圖。
圖2係具凸塊的半導體裝置之墊部分一例之放大剖視圖。
圖3a至3f係具凸塊的半導體裝置之製造方法一例之概略圖。
針對本發明實施形態進行詳細說明。
本發明的樹脂組成物係含有(a)鹼可溶性樹脂。藉由含有(a)鹼可溶性樹脂,便可獲得具圖案加工性的樹脂組成物。本發明中所謂「鹼 可溶性」係指將由樹脂溶解於γ-丁內酯中的溶液塗佈於矽晶圓上,經120℃施行4分鐘預烘烤,而形成膜厚10μm±0.5μm的預烘烤膜,再將該預烘烤膜在23±1℃的2.38重量%氫氧化四甲銨水溶液中浸漬1分鐘後,利用純水施行清洗處理時,從膜厚減少所求得之溶解速度達50nm/分以上。
本發明的(a)鹼可溶性樹脂係為能賦予鹼可溶性,因而最好在樹脂的構造單元中及/或其主鏈末端具有酸性基。酸性基係可例如:羧基、酚性羥基、磺酸基等。又,(a)鹼可溶性樹脂係為能賦予撥水性,最好具有氟原子。
(a)鹼可溶性樹脂係可舉例如:聚醯亞胺、聚醯亞胺先質、聚苯并唑、聚苯并唑先質、聚醯胺醯亞胺、聚醯胺醯亞胺先質、聚醯胺、具鹼可溶性基之自由基聚合性單體的聚合體、酚樹脂等,惟並不僅侷限於此。該等樹脂亦可含有2種以上。該等鹼可溶性樹脂之中,就從耐熱性優異、高溫下的逸氣量少之觀點,較佳係聚醯亞胺、聚苯并唑、聚醯胺醯亞胺、該等任一者的先質及/或該等的共聚合體,更佳係聚醯亞胺、聚醯亞胺先質、聚苯并唑先質或該等的共聚合體,就從更加提升感度的觀點,特佳係聚醯亞胺先質或聚苯并唑先質。此處所謂「聚醯亞胺先質」係指利用加熱處理或化學處理會轉換為聚醯亞胺的樹脂,可例如:聚醯胺酸、聚醯胺酸酯等。所謂「聚苯并唑先質」係指利用加熱處理或化學處理會轉換為聚苯并唑的樹脂,可例如聚羥醯胺等。
上述聚醯亞胺係具有下述一般式(17)所示構造單元,而聚醯亞胺先質及聚苯并唑先質係具有下述一般式(18)所示構造單元。該等亦可含有2種以上,亦可使用由一般式(17)所示構造單 元及一般式(18)所示構造單元進行共聚合的樹脂。
一般式(17)中、R11係表示4~10價有機基;R12係表示2~8價有機基。R13及R14係表示羧基、磺酸基或酚性羥基。p個R13及q個R14分別係可為相同、亦可為不同。p及q係表示0~6的整數。
一般式(18)中,R15及R16係表示2~8價有機基。R17及R18係表示酚性羥基、磺酸基、或COOR19,分別可為單一物、亦可由不同物混雜。R19係表示氫原子或碳數1~20之1價烴基。r及s係表示0~6的整數。但,r+s>0。
聚醯亞胺、聚醯亞胺先質、聚苯并唑先質或該等的共聚合體較佳係具有5~100000個一般式(17)或(18)所示構造單元。又,除一般式(17)或(18)所示構造單元之外,亦可具有其他構造單元。此情況,一般式(17)或(18)所示構造單元,佔總構造單元中較佳係50莫耳%以上。
上述一般式(17)中,R11-(R13)p係表示酸二酐的殘基。R11係4價~10價有機基,其中較佳係含有芳香族環或環狀脂肪族基 的碳原子數5~40之有機基。
酸二酐具體係可舉例如:均苯四甲酸二酐、3,3',4,4'-聯苯四羧酸二酐、2,3,3',4'-聯苯四羧酸二酐、2,2',3,3'-聯苯四羧酸二酐、3,3',4,4'-二苯基酮四羧酸二酐、2,2',3,3'-二苯基酮四羧酸二酐、2,2-雙(3,4-二羧苯基)丙烷二酐、2,2-雙(2,3-二羧苯基)丙烷二酐、1,1-雙(3,4-二羧苯基)乙烷二酐、1,1-雙(2,3-二羧苯基)乙烷二酐、雙(3,4-二羧苯基)甲烷二酐、雙(2,3-二羧苯基)甲烷二酐、雙(3,4-二羧苯基)醚二酐、1,2,5,6-萘四羧酸二酐、9,9-雙(3,4-二羧苯基)茀酸二酐、9,9-雙{4-(3,4-二羧苯氧基)苯基)茀酸二酐、2,3,6,7-萘四羧酸二酐、2,3,5,6-吡啶四羧酸二酐、3,4,9,10-苝四羧酸二酐、2,2-雙(3,4-二羧苯基)六氟丙烷二酐、及下述所示構造的酸二酐等芳香族四羧酸二酐;丁烷四羧酸二酐等脂肪族四羧酸二酐;1,2,3,4-環戊烷四羧酸二酐等含環狀脂肪族基的脂肪族四羧酸二酐等。該等亦可使用2種以上。
R20係表示氧原子、C(CF3)2或C(CH3)2。R21及R22係表示氫原子或羥基。
上述一般式(18)中,R16-(R18)s係表示酸的殘基。R16 係2價~8價有機基,其中較佳係含有芳香族環或環狀脂肪族基的碳原子數5~40之有機基。
酸係可舉例如:對酞酸、異酞酸、二苯醚二羧酸、雙(羧苯基)六氟丙烷、聯苯二羧酸、二苯基酮二羧酸、三苯基二羧酸等二羧酸;偏苯三酸、均苯三甲酸、二苯醚三羧酸、聯苯三羧酸等三羧酸;均苯四甲酸、3,3',4,4'-聯苯四羧酸、2,3,3',4'-聯苯四羧酸、2,2',3,3'-聯苯四羧酸、3,3',4,4'-二苯基酮四羧酸、2,2',3,3'-二苯基酮四羧酸、2,2-雙(3,4-二羧苯基)六氟丙烷、2,2-雙(2,3-二羧苯基)六氟丙烷、1,1-雙(3,4-二羧苯基)乙烷、1,1-雙(2,3-二羧苯基)乙烷、雙(3,4-二羧苯基)甲烷、雙(2,3-二羧苯基)甲烷、雙(3,4-二羧苯基)醚、1,2,5,6-萘四羧酸、2,3,6,7-萘四羧酸、2,3,5,6-吡啶四羧酸、3,4,9,10-苝四羧酸、及下述所示構造的芳香族四羧酸、丁烷四羧酸等脂肪族四羧酸;1,2,3,4-環戊烷四羧酸等含環狀脂肪族基的脂肪族四羧酸等四羧酸等等。該等亦可使用2種以上。
R20係表示氧原子、C(CF3)2或C(CH3)2。R21及R22係表示氫原子或羥基。
該等之中,於三羧酸、四羧酸的情況,1或2個羧基係相當於一般式(18)中的R18。又,上述所例示之二羧酸、三羧酸、四羧酸的氫原子,亦可與一般式(18)中的R18置換。R18較佳係被1~4個羥基取代。該等酸係可直接使用,亦可使用酸酐或活性酯。
上述一般式(17)的R12-(R14)q及上述一般式(18)的R15-(R17)r係表示二胺的殘基。R12及R15係2~8價有機基,其中較佳係含有芳香族環或環狀脂肪族基的碳原子數5~40之有機基。
二胺的具體例係可舉例如:3,4'-二胺基二苯醚、4,4'-二胺基二苯醚、3,4'-二胺基二苯甲烷、4,4'-二胺基二苯甲烷、1,4-雙(4-胺基苯氧基)苯、聯苯胺、間伸苯二胺、對伸苯二胺、1,5-萘二胺、2,6-萘二胺、雙(4-胺基苯氧基)聯苯、雙{4-(4-胺基苯氧基)苯基}醚、1,4-雙(4-胺基苯氧基)苯、2,2'-二甲基-4,4'-二胺基聯苯、2,2'-二乙基-4,4'-二胺基聯苯、3,3'-二甲基-4,4'-二胺基聯苯、3,3'-二乙基-4,4'-二胺基聯苯、2,2',3,3'-四甲基-4,4'-二胺基聯苯、3,3',4,4'-四甲基-4,4'-二胺基聯苯、2,2-二(三氟甲基)-4,4'-二胺基聯苯、9,9-雙(4-胺基苯基)茀、2,2'-雙(三氟甲基)-5,5'-二羥聯苯胺、該等芳香族環的氫原子至少其中一部分被烷基或鹵原子所取代的化合物等芳香族二胺;環己二胺、亞甲基雙環己胺等含有環狀脂肪族基的脂肪族二胺、及下述所示構造的二胺等。該等亦可使用2種以上。
[化6]
R20係表示氧原子、C(CF3)2或C(CH3)2。R21~R24係表示各自獨立的氫原子或羥基。
該等二胺係可直接使用,亦可對應的二異氰酸酯化合物、三甲基矽烷化二胺。
再者,該等樹脂的末端,利用具酸性基的單胺、酸酐、醯氯、單羧酸、活性酯化合物等末端終止劑進行封端,便可獲得主鏈末端具有酸性基的樹脂。
具有酸性基的單胺較佳例係可舉例如:5-胺基-8-羥基喹啉、1-羥-7-胺基萘、1-羥-6-胺基萘、1-羥-5-胺基萘、1-羥-4-胺基萘、2-羥-7-胺基萘、2-羥-6-胺基萘、2-羥-5-胺基萘、1-羧-7-胺基萘、1-羧-6-胺基萘、1-羧-5-胺基萘、2-羧-7-胺基萘、2-羧-6-胺基萘、2-羧-5-胺基萘、2-胺基苯甲酸、3-胺基苯甲酸、4-胺基苯甲酸、4-胺基水楊酸、5-胺基水楊酸、6-胺基水楊酸、3-胺基-4,6-二羥嘧啶、2-胺基酚、3-胺基酚、4-胺基酚、2-胺基硫酚、3-胺基硫酚、4-胺基硫酚等。該等亦可使用2種以上。
酸酐的較佳例係可舉例如:酞酸酐、順丁烯二酸酐、 納迪克酸酐、環己烷二羧酸酐、3-羥基酞酸酐等。該等亦可使用2種以上。
單羧酸的較佳例係可舉例如:3-羧酚、4-羧酚、3-羧硫酚、4-羧硫酚、1-羥-7-羧基萘、1-羥-6-羧基萘、1-羥-5-羧基萘、1-巰基-7-羧基萘、1-巰基-6-羧基萘、1-巰基-5-羧基萘等。該等亦可使用2種以上。
醯氯的較佳例係可舉例如:由上述單羧酸的羧基進行醯氯化的單醯氯化合物、對酞酸、酞酸、順丁烯二酸、環己烷二羧酸、1,5-二羧基萘、1,6-二羧基萘、1,7-二羧基萘、2,6-二羧基萘等二羧酸類僅1個羧基被醯氯化的單醯氯化合物等。該等亦可使用2種以上。
活性酯化合物的較佳例係可舉例如上述單醯氯化合物、與例如N-羥基苯并三唑或N-羥-5-降烯-2,3-二羧醯亞胺的反應物等。該等亦可使用2種以上。
樹脂中所導入的末端終止劑係依照以下方法便可輕易地檢測。例如將經導入末端終止劑的樹脂溶解於酸性溶液中,分解為屬於樹脂構成單元的胺成分與酸成分,再將其施行氣相色層分析(GC)、NMR測定,便可輕易地檢測末端終止劑。又,將經導入末端終止劑的樹脂,利用熱裂解氣相色層分析(PGC)、紅外光譜、及13C-NMR質譜測定亦可檢測。
本發明的(a)鹼可溶性樹脂係可利用公知方法合成。
屬於聚醯亞胺先質的聚醯胺酸或聚醯胺酸酯之製造方法,係可例如:在低溫中使四羧酸二酐與二胺化合物產生反應的方法;先利用四羧酸二酐與醇獲得二酯,然後在縮合劑存在下使與胺產生反應 的方法;先利用四羧酸二酐與醇獲得二酯,然後將剩餘的二羧酸施行醯氯化,再與胺進行反應的方法等。
屬於聚苯并唑先質的聚羥醯胺之製造方法,係可例如使雙胺基酚化合物與二羧酸進行縮合反應的方法。具體係可例如:使二環己基碳二醯亞胺(DCC)等脫水縮合劑與酸進行反應,再於其中添加雙胺基酚化合物的方法;在經添加吡啶等三級胺的雙胺基酚化合物之溶液中,滴下二氯二羧酸溶液的方法等。
聚醯亞胺之製造方法係可例如將依前述方法所獲得之聚醯胺酸或聚醯胺酸酯施行脫水閉環的方法等。脫水閉環的方法係可例如利用酸、鹼等施行的化學處理、加熱處理等。
聚苯并唑之製造方法係可例如將依前述方法所獲得之聚羥醯胺施行脫水閉環的方法等。脫水閉環的方法係可例如利用酸、鹼等施行的化學處理、加熱處理等。
聚醯胺醯亞胺先質係可例如:三羧酸、對應的三羧酸酐、鹵化三羧酸酐與二胺化合物的聚合體,較佳係偏苯三酸酐醯氯(trimellitic anhydride chloride)與芳香族二胺化合物的聚合體。聚醯胺醯亞胺先質之製造方法係可例如在低溫中,使三羧酸、對應的三羧酸酐、鹵化三羧酸酐等,與二胺化合物進行反應的方法等。
聚醯胺醯亞胺之製造方法係可例如:使偏苯三酸酐與芳香族二異氰酸酯進行反應的方法、將依照前述方法所獲得之聚醯胺醯亞胺先質施行脫水閉環的方法等。脫水閉環的方法係可例如利用酸、鹼等施行的化學處理、加熱處理等。
具有鹼可溶性基的自由基聚合性單體之聚合體,為能賦予鹼可溶性,最好係具有酚性羥基或羧基的自由基聚合性單體之 聚合體。亦可為該等自由基聚合性單體與其他自由基聚合性單體的共聚合體。具有酚性羥基或羧基的自由基聚合性單體,較佳係鄰羥苯乙烯、間羥苯乙烯、對羥苯乙烯、該等的烷基或烷氧取代體等。其他自由基聚合性單體較佳係苯乙烯或其取代體、丁二烯、異戊二烯、甲基丙烯酸或丙烯酸的酯化物等。
酚樹脂較佳係酚醛酚樹脂、可溶酚醛酚樹脂等。
本發明的樹脂組成物係含有:在酚性羥基鄰位具有下述一般式(1)所示1價基的醯胺酚化合物(以下亦有簡稱」(b1)醯胺酚化合物」的情況)及/或(b2)在羧基鄰位具有下述一般式(2)所示1價基的芳香族醯胺酸化合物(以下亦有簡稱」(b2)芳香族醯胺酸化合物」的情況)。因為(b1)醯胺酚化合物係具有酚性羥基,且因為(b2)芳香族醯胺酸化合物係具有羧基,因而當例如正型感光性樹脂組成物的情況,在顯影時,酚性羥基或羧基會促進曝光部溶解,便可高感度化。另一方面,因為(b1)醯胺酚化合物係在酚性羥基鄰位具有醯胺基,且因為(b2)芳香族醯胺酸化合物係在羧基鄰位具有醯胺基,因而經硬化後,利用環化脫水反應便不會殘留屬於極性基的酚性羥基或羧基,可獲得低吸水性的硬化膜。就從更加提升對鹼顯影液的溶解性、以及更加提升感度的觀點,(b1)醯胺酚化合物及(b2)芳香族醯胺酸化合物較佳係具有2個以上之下述一般式(1)或(2)所示1價基。
一般式(1)中,X係表示與一般式(1)中的羰基碳直接鍵結且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。Y係表示碳數1~10之伸烷基;n係表示1~20的整數。
若X係具有與一般式(1)中的羰基碳直接鍵結之碳數2~20的烷基或-(YO)n-,便可提高250℃以下的脫水閉環率,俾能降低硬化後的吸水率。當X係烷基時,就從可提升耐熱性的觀點,碳數較佳係10以下、更佳係6以下。當X係具-(YO)n-的1價有機基時,就從提升耐熱性的觀點,Y較佳係亞甲基、伸乙基、伸丙基、伸丁基。當Y係亞甲基時,就從提高脫水閉環率的觀點,n較佳係2以上。更佳係3以上。又,就從提升耐熱性的觀點,n較佳係10以下。當Y係亞甲基以外的情況,就從提升耐熱性的觀點,n較佳係2~10。又,就從提升耐熱性的觀點,X亦可任意具有取代基,例如較佳係末端具有芳基。
一般式(2)中,U係表示與一般式(2)中的醯胺氮直接鍵結且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。Y係表示碳數1~10之伸烷基;n係表示1~20的整數。
若U係具有與一般式(2)中的醯胺氮直接鍵結之碳數2~20的烷基、或-(YO)n-,便可提高250℃以下的脫水閉環率,俾能降低硬化後的吸水率。若U係烷基時,就從提升耐熱性的觀點,碳數較佳係10以下、更佳係6以下。若U係具-(YO)n-的1價有機基時,就從提升耐熱性的觀點,Y較佳係亞甲基、伸乙基、伸丙基、伸丁基。 若Y係亞甲基時,就從提高脫水閉環率的觀點,n較佳係2以上。更佳係3以上。又,就從提升耐熱性的觀點,n較佳係10以下。若Y係亞甲基以外的情況,就從提升耐熱性的觀點,n較佳係2~10。又,就從提升耐熱性的觀點,U亦可任意具有取代基,例如較佳係末端具有芳基。
一般式(1)中的X、及一般式(2)中的U係碳數2~20的烷基,可舉例如:乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、廿烷基等。又,一般式(1)及一般式(2)中的Y係碳數1~10的伸烷基,可舉例如:亞甲基、伸乙基、伸丙基、伸丁基、伸戊基、伸己基、伸庚基、伸辛基、伸癸基等。
本發明的(b1)醯胺酚化合物係可例如下述一般式(3)~(5)中任一者所示的化合物。該化合物亦可使用為助溶劑。
[化9]
一般式(3)~(5)中,m係表示1~4的整數。X係表示具有與一般式(3)~(5)中的羰基碳直接鍵結、且碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。Y係表示碳數1~10之伸烷基;n係表示1~20的整數。
當X係烷基時,碳數較佳係10以下、更佳係6以下。當X係具-(YO)n-的1價有機基時,Y較佳係亞甲基、伸乙基、伸丙基、伸丁基。當Y係亞甲基時,n較佳係2以上、更佳係3以上。又,n較佳係10以下。當Y係亞甲基以外的情況,n較佳係2~10。又,X亦可任意具有取代基,例如較佳係末端具有芳基。
一般式(3)~(5)中,Z係表示單鍵、氫原子、烷氧基、-O-、-SO2-、-C(CF3)2-、-O-R1-O-、-C(=O)-、-C(=O)O-R2-OC(=O)-、-C(=O)NH-R3-NHC(=O)-、或碳數1~20的1~4價烴基。R1~R3係表示碳數1~20的2價烴基。就從提升溶解性的觀點,烴基的碳數更佳係1~10。烴基係可為飽和、亦可為不飽和。但,當Z係單鍵的情況,便為m=2。
本發明所使用的(b1)醯胺酚化合物,係藉由使酚性羥基之鄰位具有胺基的化合物或其鹽酸鹽、與對應的醯氯進行反應便可獲得。酚性羥基鄰位具有胺基的化合物係可舉例如:2-胺基酚、2,4-二羥-間伸苯二胺、2,5-二羥-對伸苯二胺、4,6-二胺基間苯二酚、3,3'-二胺基-4,4'-二羥二苯、4,4'-二胺基-3,3'-二羥二苯、3,4'-二胺基-3',4-二羥二苯、3,3'-二胺基-4,4'-二羥二苯醚、4,4'-二胺基-3,3'-二羥二苯醚、3,4'-二胺基-3',4-二羥二苯醚、3,3'-二胺基-4,4'-二羥二苯基六氟丙烷、4,4'-二胺基-3,3'-二羥二苯基六氟丙烷、3,4'-二胺基-3',4-二羥二苯基六氟丙烷、3,3'-二胺基-4,4'-二羥二苯基酮、4,4'-二胺基-3,3'-二羥二苯基酮、3,4'-二胺基-3',4-二羥二苯基酮、3,3'-二胺基-4,4'-二羥二苯碸、4,4'-二胺基-3,3'-二羥二苯碸、3,4'-二胺基-3',4-二羥二苯碸、雙(3-胺基-4-羥苯基)丙烷、雙(3-胺基-4-羥苯基)甲烷、雙(3-胺基-4-羥苯基)茀、2,2'-雙(三氟甲基)-5,5'-二羥聯苯胺等含羥基的二胺;將該等芳香族環的部分氫原子取代為碳數1~10之烷基、氟烷基、鹵原子等的化合物等等。
醯氯係可舉例如:丙醯氯、丁醯氯、戊醯氯、己醯氯、庚醯氯、辛醯氯、壬醯氯、癸醯氯、月桂醯氯等醯氯;該等的部分氫原子被碳數1~10之烷基等取代的化合物、末端甲基被芳基取代的化合物等。
本發明的(b2)芳香族醯胺酸化合物係可例如下述一般式(6)~(8)中之任一者所示之化合物。該化合物亦可使用為助溶劑。
[化10]
一般式(6)~(10)中,m係表示1~4的整數。U係表示具有與一般式(6)~(10)中的醯胺氮直接鍵結、且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。Y係表示碳數1~10之伸烷基;n係表示1~20的整數。
當U係烷基時,碳數較佳係10以下、更佳係6以下。若U係具-(YO)n-的1價有機基時,Y較佳係亞甲基、伸乙基、伸丙基、伸丁基。若Y係亞甲基的情況,n較佳係2以上、更佳係3以上。又,n較佳係10以下。若Y係亞甲基以外的情況,n較佳係2~10。又,U亦可任意具有取代基,例如較佳係末端具有芳基。
一般式(6)~(10)中,Z係表示單鍵、氫原子、烷氧基、 -O-、-SO2-、-C(CF3)2-、-O-R1-O-、-C(=O)-、-C(=O)O-R2-OC(=O)-、-C(=O)NH-R3-NHC(=O)-、或碳數1~20之1~4價烴基。R1~R3係表示碳數1~20之2價烴基;R4及R5係表示-C(CH3)2-、-C(CF3)2-、-O-或-S-。就從提升溶解性的觀點,烴基的碳數更佳係1~10。烴基係可為飽和、亦可為不飽和。但,當Z係單鍵的情況,便為m=2。
本發明所使用的(b2)芳香族醯胺酸化合物,係藉由使酸酐、酸二酐、二羧酸化合物或四羧酸化合物、與對應的一級胺進行反應,便可獲得。
酸酐係可例如酞酸酐。酸二酐係可例如就構成聚醯亞胺的酸二酐所例示之芳香族四羧酸二酐。二羧酸係可例如酞酸。四羧酸係可例如就構成聚醯亞胺先質或聚苯并唑先質的四羧酸所例示之芳香族四羧酸。
一級胺係可舉例如:乙胺、丙胺、丁胺、戊胺、己胺、庚胺、辛胺、壬胺、癸胺、十二烷基胺等脂肪族胺;該等的部分氫原子被碳數1~10之烷基等取代的化合物、末端甲基被芳基取代的化合物等。
本發明樹脂組成物中的(b1)醯胺酚化合物及/或(b2)芳香族醯胺酸化合物之含有量,就從更加提升感度的觀點,相對於(a)鹼可溶性樹脂100質量份,較佳係1質量份以上、更佳係3質量份以上,又就從提升耐熱性的觀點,較佳係50質量份以下、更佳係40質量份以下。
本發明的樹脂組成物較佳係含有(c)感光性化合物,可成為感光 性樹脂組成物。(c)感光性化合物係可例如(c1)光酸產生劑、(c2)光聚合起始劑等。(c1)光酸產生劑係利用光照射便會產生酸的化合物;(c2)光聚合起始劑係利用曝光便會進行鍵結斷裂及/或反應,而產生自由基的化合物。
藉由含有(c1)光酸產生劑,便會在光照射部生成酸,增加光照射部對鹼水溶液的溶解性,可獲得溶解光照射部的正型浮雕圖案。又,藉由含有(c1)光酸產生劑、與環氧化合物或後述熱交聯劑,則在光照射部生成的酸會促進環氧化合物與熱交聯劑的交聯反應,便可獲得光照射部不溶化的負型浮雕圖案。另一方面,藉由含有(c2)光聚合起始劑及後述自由基聚合性化合物,則在光照射部會進行自由基聚合,便可獲得光照射部不溶化的負型浮雕圖案。
(c1)光酸產生劑係可舉例如:醌二疊氮化合物、鋶鹽、鏻鹽、重氮鎓鹽、碘鎓鹽等。(c1)光酸產生劑較佳係含有2種以上,可獲得高感度的感光性樹脂組成物。
醌二疊氮化合物係可舉例如:在聚羥化合物上酯鍵結著醌二疊氮之磺酸者、在多胺化合物上磺醯胺鍵結著醌二疊氮之磺酸者、在聚羥多胺化合物上酯鍵結及/或磺醯胺鍵結著醌二疊氮之磺酸者等。最好該等聚羥化合物、多胺化合物的官能基全體50莫耳%以上,被醌二疊氮取代。
本發明中,醌二疊氮較佳係使用5-萘醌二疊氮磺醯基、4-萘醌二疊氮磺醯基中之任一者。4-萘醌二疊氮磺醯酯化合物係在水銀燈的i線區域具有吸收,適用於i線曝光。5-萘醌二疊氮磺醯酯化合物的吸收係延伸至水銀燈的g線區域,適用於g線曝光。本發明中,依照曝光的波長,最好選擇4-萘醌二疊氮磺醯酯化 合物、5-萘醌二疊氮磺醯酯化合物。又,亦可在同一分子中,含有具4-萘醌二疊氮磺醯基、5-萘醌二疊氮磺醯基的萘醌二疊氮磺醯酯化合物,亦可含有4-萘醌二疊氮磺醯酯化合物與5-萘醌二疊氮磺醯酯化合物。
上述醌二疊氮化合物係由具酚性羥基的化合物、與醌二疊氮磺酸化合物,利用任意的酯化反應便可合成。藉由使用該等醌二疊氮化合物,便可更加提升解析度、感度、殘膜率。
(c1)光酸產生劑中,就從可使因曝光而生成的酸成分能適度安定化的觀點,較佳係鋶鹽、鏻鹽、重氮鎓鹽、碘鎓鹽。其中,更佳係鋶鹽。又視需要亦可更進一步含有增感劑等。
本發明中,(c1)光酸產生劑的含有量,就從高感度化的觀點,相對於(a)鹼可溶性樹脂100質量份較佳係0.01~50質量份。其中,醌二疊氮化合物較佳係3~40質量份。又,鋶鹽、鏻鹽、重氮鎓鹽及碘鎓鹽的總量較佳係0.5~20質量份。
(c2)光聚合起始劑係可舉例如:苄基縮酮系光聚合起始劑、α-羥酮系光聚合起始劑、α-胺基酮系光聚合起始劑、醯基氧化膦系光聚合起始劑、肟酯系光聚合起始劑、吖啶系光聚合起始劑、二茂鈦系光聚合起始劑、二苯基酮系光聚合起始劑、苯乙酮系光聚合起始劑、芳香族酮酯系光聚合起始劑、苯甲酸酯系光聚合起始劑等。(c2)光聚合起始劑亦可含有2種以上。就從更加提升感度的觀點,更佳係α-胺基酮系光聚合起始劑、醯基氧化膦系光聚合起始劑、肟酯系光聚合起始劑。
α-胺基酮系光聚合起始劑係可舉例如:2-甲基-1-[4-(甲硫基)苯基]-2-啉基丙烷-1-酮、2-苄基-2-二甲胺基-1-(4- 啉基苯基)-丁烷-1-酮、2-二甲胺基-2-(4-甲基苄基)-1-(4-啉基苯基)-丁烷-1-酮、3,6-雙(2-甲基-2-啉基丙醯基)-9-辛基-9H-咔唑等。
醯基氧化膦系光聚合起始劑係可舉例如:2,4,6-三甲基苯甲醯基-二苯基氧化膦、雙(2,4,6-三甲基苯甲醯基)-苯基氧化膦、雙(2,6-二甲氧基苯甲醯基)-(2,4,4-三甲基戊基)氧化膦等。
肟酯系光聚合起始劑係可舉例如:1-苯基丙烷-1,2-二酮-2-(O-乙氧羰基)肟、1-苯基丁烷-1,2-二酮-2-(O-甲氧羰基)肟、1,3-二苯基丙烷-1,2,3-三酮-2-(O-乙氧羰基)肟、1-[4-(苯硫基)苯基]辛烷-1,2-二酮-2-(O-苯甲醯基)肟、1-[4-[4-(羧苯基)硫基]苯基]丙烷-1,2-二酮-2-(O-乙醯基)肟、1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙酮-1-(O-乙醯基)肟、1-[9-乙基-6-[2-甲基-4-[1-(2,2-二甲基-1,3-二氧雜戊環烷-4-基)甲基氧基]苯甲醯基]-9H-咔唑-3-基]乙酮-1-(O-乙醯基)肟或1-(9-乙基-6-硝基-9H-咔唑-3-基)-1-[2-甲基-4-(1-甲氧基丙烷-2-基氧基)苯基]甲酮-1-(O-乙醯基)肟等。
本發明中,(c2)光聚合起始劑的含有量,就從更加提升感度的觀點,相對於(a)鹼可溶性樹脂及後述自由基聚合性化合物的合計100質量份,較佳係0.1質量份以上、更佳係1質量份以上。另一方面,就從更加提升解析度、降低推拔角度的觀點,較佳係25質量份以下、更佳係15質量份以下。
本發明的樹脂組成物亦可更進一步含有自由基聚合性化合物。
所謂「自由基聚合性化合物」係指分子中具有複數乙烯性不飽和雙鍵的化合物。曝光時,利用從前述(c2)光聚合起始劑產生的自 由基,進行自由基聚合性化合物的自由基聚合,並藉由光照射部的不溶化,便可獲得負型的圖案。又,藉由含有自由基聚合性化合物,便可促進光照射部的光硬化,而更加提升感度。此外,因為熱硬化後的交聯密度獲提升,因而可提升硬化膜的硬度。
自由基聚合性化合物較佳係容易進行自由基聚合之具有(甲基)丙烯基的化合物。就從曝光時的感度提升、及硬化膜的硬度提升之觀點,更佳係分子內具有二以上(甲基)丙烯基的化合物。自由基聚合性化合物的雙鍵當量,就從曝光時的感度提升、及硬化膜的硬度提升之觀點,較佳係80~400g/mol。
自由基聚合性化合物係可舉例如:三羥甲基丙烷三(甲基)丙烯酸酯、三(甲基)丙烯酸二(三羥甲基丙酯)、四(甲基)丙烯酸二(三羥甲基丙酯)、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、2,2-雙[4-(3-(甲基)丙烯氧-2-羥丙氧基)苯基]丙烷、1,3,5-三((甲基)丙烯氧乙基)異三聚氰酸、1,3-雙((甲基)丙烯氧乙基)異三聚氰酸、9,9-雙[4-(2-(甲基)丙烯氧乙氧基)苯基]茀、9,9-雙[4-(3-(甲基)丙烯氧丙氧基)苯基]茀、9,9-雙(4-(甲基)丙烯氧苯基)茀、或該等的酸改質體、環氧乙烷改質體、環氧丙烷改質體等。
本發明中,自由基聚合性化合物的含有量,就從更加提升感度、降低推拔角度的觀點,相對於(a)鹼可溶性樹脂及自由基聚合性化合物的合計100質量份,較佳係15質量份以上、更佳係30質量份以上。另一方面,就從更加提升硬化膜的耐熱性、降低推拔角度的觀點,較佳係65質量份以下、更佳係50質量份以下。
本發明的樹脂組成物較佳係含有(d)熱交聯劑。所謂「熱交聯劑」係指分子內至少具有2個烷氧甲基、羥甲基、環氧基、氧雜環丁烷基等熱反應性官能基的化合物。藉由含有(d)熱交聯劑,便可將(a)鹼可溶性樹脂或其他添加成分進行交聯,便可提升經熱硬化後的膜之耐熱性、耐藥性及硬度。又,可降低從硬化膜的逸氣量、提升有機EL顯示裝置的長期可靠度。
作為至少具有2個烷氧甲基或羥甲基的化合物之較佳例,係可舉例如:DML-PC、DML-PEP、DML-OC、DML-OEP、DML-34X、DML-PTBP、DML-PCHP、DML-OCHP、DML-PFP、DML-PSBP、DML-POP、DML-MBOC、DML-MBPC、DML-MTrisPC、DML-BisOC-Z、DML-BisOCHP-Z、DML-BPC、DML-BisOC-P、DMOM-PC、DMOM-PTBP、DMOM-MBPC、TriML-P、TriML-35XL、TML-HQ、TML-BP、TML-pp-BPF、TML-BPE、TML-BPA、TML-BPAF、TML-BPAP、TMOM-BP、TMOM-BPE、TMOM-BPA、TMOM-BPAF、TMOM-BPAP、HML-TPPHBA、HML-TPHAP、HMOM-TPPHBA、HMOM-TPHAP(以上係商品名,本州化學工業(股)製);「NIKALAC」(註冊商標)MX-290、「NIKALAC」(註冊商標)MX-280、「NIKALAC」(註冊商標)MX-270、「NIKALAC」(註冊商標)MX-279、「NIKALAC」(註冊商標)MW-100LM、「NIKALAC」(註冊商標)MX-750LM(以上係商品名,三和化學(股)製)。
至少具有2個環氧基的化合物較佳例,係可舉例如:「EPOLITE」(註冊商標)40E、「EPOLITE」(註冊商標)100E、 「EPOLITE」(註冊商標)200E、「EPOLITE」(註冊商標)400E、「EPOLITE」(註冊商標)70P、「EPOLITE」(註冊商標)200P、「EPOLITE」(註冊商標)400P、「EPOLITE」(註冊商標)1500NP、「EPOLITE」(註冊商標)80MF、「EPOLITE」(註冊商標)4000、「EPOLITE」(註冊商標)3002(以上係共榮社化學(股)製);「DENACOL」(註冊商標)EX-212L、「DENACOL」(註冊商標)EX-214L、「DENACOL」(註冊商標)EX-216L、「DENACOL」(註冊商標)EX-850L(以上係Nagase ChemteX(股)製);GAN、GOT(以上係日本化藥(股)製);「EPIKOTE」(註冊商標)828、「EPIKOTE」(註冊商標)1002、「EPIKOTE」(註冊商標)1750、「EPIKOTE」(註冊商標)1007、YX8100-BH30、E1256、E4250、E4275(以上係Japan Epoxy Resins(股)製);「EPICRON」(註冊商標)EXA-9583、HP4032(以上係大日本油墨化學工業(股)製);VG3101(三井化學(股)製);「TEPIC」(註冊商標)S、「TEPIC」(註冊商標)G、「TEPIC」(註冊商標)P(以上係日產化學工業(股)製);「DENACOL「EX-321L(Nagase ChemteX(股)製);NC6000(日本化藥(股)製);「EPOTOHTO」(註冊商標)YH-434L(東都化成(股)製);EPPN502H、NC3000(日本化藥(股)製);「EPICRON」(註冊商標)N695、HP7200(以上係大日本油墨化學工業(股)製)等。
至少具有2個氧雜環丁烷基的化合物較佳例,係可舉例如:ETERNACOLL® EHO、ETERNACOLL® OXBP、ETERNACOLL® OXTP、ETERNACOLL® OXMA(以上係宇部興產(股)製);氧雜環丁烷化酚酚醛等。
熱交聯劑亦可組合使用2種以上。
熱交聯劑的含有量,相對除溶劑外的樹脂組成物總量100質量份,較佳係1質量份以上且30質量份以下。若熱交聯劑的含有量達1質量份以上,便可提高煅燒後或硬化後的膜之耐藥性及硬度。又,若熱交聯劑的含有量在30質量份以下,便可降低來自硬化膜的逸氣量,俾能提高有機EL顯示裝置的長期可靠度,且樹脂組成物的保存安定性亦優異。
本發明的硬化膜所使用之樹脂組成物,較佳係含有從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上的化合物。從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上的化合物,會殘存於由本發明樹脂組成物硬化形成的硬化膜中,而發揮酸性氣體的消光劑作用,所以可降低發光輝度、抑制像素收縮,推定能提升有機EL顯示裝置的長期可靠度。
從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上的化合物,較佳係具有下述一般式(17)所示構造。
一般式(17)中,u係表示1~4的整數;Y係表示CH或氮原子。R25及R26係表示各自獨立的氫原子或碳數1~20之有機基。
(e)從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上的化合物,就從容易殘存於硬化膜中的觀點,較佳係 沸點達210℃以上。又,就從抑制塗佈時不均的觀點,較佳係沸點在400℃以下。當無法依常壓測定沸點時,便可使用沸點換算表換算為常壓下的沸點。
環狀醯胺、環狀脲及該等的衍生物具體例,係可舉例如:2-吡咯啶酮、N-甲基-2-吡咯啶酮(NMP)、N-乙基-2-吡咯啶酮、N-丙基-2-吡咯啶酮、N-異丙基-2-吡咯啶酮、N-丁基-2-吡咯啶酮、N-(第三丁基)-2-吡咯啶酮、N-戊基-2-吡咯啶酮、N-環己基-2-吡咯啶酮、N-甲氧基丙基-2-吡咯啶酮、N-乙氧基乙基-2-吡咯啶酮、N-甲氧基丁基-2-吡咯啶酮、N-(2-羥乙基)-2-吡咯啶酮、N-苯基-2-吡咯啶酮、N-乙烯基-2-吡咯啶酮、N,N'-二甲基伸丙基脲、2-咪唑啉二酮、1,3-二甲基-2-咪唑啉二酮、2-哌啶酮、ε-己內醯胺等。該等亦可含有2種以上。該等之中,就從沸點高、經加熱處理後亦容易殘存的觀點,較佳係N-環己基-2-吡咯啶酮(沸點:154℃/0.933kPa、常壓沸點換算時:305℃)、N-(2-羥乙基)-2-吡咯啶酮(沸點:175℃/1.333kPa、常壓沸點換算時:313℃)。
從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上化合物的總含有量,就從更加提升有機EL顯示裝置的長期可靠度觀點,相對於(a)鹼可溶性樹脂100質量份,較佳係0.1質量份以上、更佳係1質量份以上。另一方面,當樹脂組成物係具有感光性的情況,從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上化合物的總含有量,就從更加提升感度的觀點,相對於(a)鹼可溶性樹脂100質量份,較佳係15質量份以下、更佳係10質量份以下。
本發明的樹脂組成物亦可含有有機溶劑。藉由含有有機溶劑,便可形成清漆狀態,俾能提升塗佈性。
有機溶劑係可舉例如:γ-丁內酯等極性的非質子性溶劑;乙二醇單甲醚、乙二醇單乙醚、乙二醇單正丙醚、乙二醇單正丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單正丙醚、二乙二醇單正丁醚、三乙二醇單甲醚、三乙二醇單乙醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單正丙醚、丙二醇單正丁醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單正丙醚、二丙二醇單正丁醚、三丙二醇單甲醚、三丙二醇單乙醚、四氫呋喃、二烷等醚類;丙酮、甲乙酮、二異丁酮、環己酮、2-庚酮、3-庚酮、二丙酮醇等酮類;乙二醇單甲醚醋酸酯、乙二醇單乙醚醋酸酯、二乙二醇單甲醚醋酸酯、二乙二醇單乙醚醋酸酯、丙二醇單甲醚醋酸酯、丙二醇單乙醚醋酸酯、乳酸乙酯等酯類;2-羥-2-甲基丙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙氧基醋酸乙酯、羥醋酸乙酯、2-羥-3-甲基丁酸甲酯、醋酸-3-甲氧基丁酯、醋酸-3-甲基-3-甲氧基丁酯、丙酸-3-甲基-3-甲氧基丁酯、醋酸乙酯、醋酸正丙酯、醋酸異丙酯、醋酸正丁酯、醋酸異丁酯、蟻酸正戊酯、醋酸異戊酯、丙酸正丁酯、丁酸乙酯、丁酸正丙酯、丁酸異丙酯、丁酸正丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸正丙酯、乙醯醋酸甲酯、乙醯醋酸乙酯、2-氧基丁酸乙酯等其他的酯類;甲苯、二甲苯等芳香族烴類;N-甲基吡咯啶酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等醯胺類等等。該等亦可含有2種以上。
有機溶劑的含有量並無特別的限定,相對於溶劑除外的樹脂組成物總量100質量份,較佳係100~3000質量份、更佳係150~2000質量份。又,亦可其中一部分的有機溶劑係沸點達180℃以上,而在有機溶劑總量中,沸點達180℃以上的溶劑所佔比例較佳係20質量份以下、更佳係10質量份以下。藉由將沸點達180℃以上的溶劑比例設定在20質量份以下,便可降低熱硬化後的逸氣量,結果可提高有機EL顯示裝置的長期可靠度。
本發明的樹脂組成物亦可更進一步含有著色劑。
所謂「著色劑」係指會吸收特定波長光的化合物,特別係藉由吸收可見光線波長(380~780nm)光而著色的化合物。藉由含有著色劑,便可使從樹脂組成物所獲得之膜被著色,使穿透過樹脂組成物膜的光、或從樹脂組成物膜反射的光著色為所需顏色,而賦予著色性。又,從穿透過樹脂組成物膜的光、或從樹脂組成物膜反射的光,可遮住著色劑所吸收的波長光,便能賦予遮光性。
著色劑係可例如吸收可見光線波長光,而著色為白、紅、橙、黃、綠、藍或紫色的化合物。藉由組合二色以上,便可提升將穿透過樹脂組成物所需樹脂組成物膜的光、或從樹脂組成物膜反射的光,調色為所需色座標的調色性。
著色劑較佳係顏料及/或染料。又,著色劑係可為黑色劑、亦可為黑色以外的著色劑。
所謂「黑色劑」係指藉由吸收可見光線波長光而著色為黑色的化合物,可為顏料、亦可為染料。藉由含有黑色劑,便將 樹脂組成物的膜黑色化,而會遮住穿透過樹脂組成物膜的光、或從樹脂組成物膜反射的光,便可提升遮光性。所以,頗適用於彩色濾光片的黑矩陣或液晶顯示器的黑柱間隔件等遮光膜、以及利用抑制外光反射而要求高對比化的用途。
黑色劑就從遮光性的觀點,較佳係吸收可見光線全波長光而著色為黑色的化合物。又,從白、紅、橙、黃、綠、藍及紫色所構成群組中選擇二色以上化合物的混合物亦屬較佳。藉由該等組合使用二色以上,便可模擬性著色為黑色,俾能提升遮光性。
黑色劑較佳係含有黑色顏料、黑色染料及/或二色以上的染料混合物,就從遮光性的觀點,更佳係含有黑色顏料。
所謂「黑色以外的著色劑」係指藉由吸收可見光線波長光而著色的化合物。即,前述著色為除黑色外的白、紅、橙、黃、綠、藍或紫色之著色劑。藉由含有黑色以外的著色劑,便可對樹脂組成物的膜賦予遮光性、著色性及調色性。
黑色以外的著色劑較佳係黑色以外的顏料及/或黑色以外的染料,就從遮光性、及耐熱性或耐候性的觀點,更佳係黑色以外的顏料。
著色劑的含有量係相對於溶劑除外的樹脂組成物100質量份,較佳係5質量份以上、更佳係15質量份以上。藉由著色劑含有達5質量份以上,便可提升遮光性、著色性及調色性。另一方面,著色劑的含有量較佳係70質量份以下、更佳係60質量份以下。藉由著色劑含有70質量份以下,便可更加提升感度。
本發明的樹脂組成物亦可含有密接改良劑。密接改良劑係可舉例如:乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、環氧環己基乙基三甲氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基三乙氧基矽烷、對苯乙烯基三甲氧基矽烷、3-胺丙基三甲氧基矽烷、3-胺丙基三乙氧基矽烷、N-苯基-3-胺丙基三甲氧基矽烷等矽烷偶合劑;鈦螯合劑、鋁螯合劑、以及由芳香族胺化合物與含烷氧基之矽化合物進行反應而獲得的化合物等。該等亦可含有2種以上。藉由含有該等密接改良劑,當對樹脂膜施行顯影等之時,可提高與例如矽晶圓、ITO、SiO2、氮化矽等底層基材間之密接性。又,可提高對洗淨等之時所使用的氧電漿、UV臭氧處理之耐性。
密接改良劑的含有量係相對於溶劑除外的樹脂組成物總量100質量份,較佳0.1~10質量份。
本發明的樹脂組成物係視需要亦可含有界面活性劑,俾能提升與基板間之濕潤性。界面活性劑係可舉例如:Toray Dow Corning Silicones公司的SH系列、SD系列、ST系列、以及BYK-Chemie‧Japan公司的BYK系列、信越矽利光公司的KP系列、日本油脂公司的DISFOAM系列、東芝矽利康公司的TSF系列等聚矽氧系界面活性劑;大日本油墨工業公司的「MEGAFAC(註冊商標)「系列、住友3M公司的FLUORAD系列、旭硝子公司的「SURFLON(註冊商標)「系列、「ASAHIGUARD(註冊商標)「系列、新秋田化成公司的EF系列、Omnova Solutions公司的PolyFox系列等氟系界面活性劑;共榮社化學公司的Poly Flow系列、楠本化成公司的 「DISPARON(註冊商標)「系列等丙烯酸系及/或甲基丙烯酸系界面活性劑等等。界面活性劑的含有量係相對於溶劑除外的樹脂組成物總量100質量份,較佳係0.001~1質量份。
本發明的樹脂組成物亦可含有無機粒子。無機粒子的較佳具體例係可舉例如:氧化矽、氧化鈦、鈦酸鋇、氧化鋁、滑石等。無機粒子的一次粒徑較佳係100nm以下、更佳係60nm以下。
無機粒子的含有量係相對於溶劑除外的樹脂組成物總量100質量份,較佳係5~90質量份。
本發明的樹脂組成物係在不致損及有機EL顯示裝置的長期可靠度範圍內,亦可含有熱酸產生劑或熱鹼產生劑。熱酸產生劑、熱鹼產生劑分別係利用加熱便會產生酸或鹼,而促進(d)熱交聯劑的交聯反應,此外當(a)成分的樹脂係具有未閉環的醯亞胺環構造、唑環構造時,便會促進該等的環化,俾能更加提升硬化膜的機械特性。又,促進硬化時的(b1)醯胺酚化合物、(b2)芳香族醯胺酸化合物之環化脫水反應,即便於250℃以下的低溫加熱硬化溫度,亦可獲得低吸水性的硬化膜。
本發明所使用熱酸產生劑或熱鹼產生劑的熱裂解起始溫度,較佳係50℃~270℃、更佳係250℃以下。又,若本發明的樹脂組成物係選擇塗佈於基板後,在乾燥(預烘烤:約70~140℃)時不會產生酸或鹼,但經後續的曝光、顯影施行圖案化後,在最終 加熱(硬化:約100~400℃)時則會產生酸或鹼者,便可抑制顯影時的感度降低,故屬較佳。
從本發明使用的熱酸產生劑所產生之酸,較佳係強酸,最好係例如:對甲苯磺酸、苯磺酸等芳磺酸;甲磺酸、乙磺酸、丙磺酸、丁磺酸等烷磺酸;三氟甲基磺酸等鹵烷磺酸等。該等係使用例如鎓鹽之類的鹽、或如醯亞胺磺酸酯之類的共價鍵化合物。該等亦可含有2種以上。
本發明所使用的熱鹼產生劑,較佳係例如:三氯醋酸胍、三氯醋酸甲胍、三氯醋酸鉀、苯磺醯基醋酸胍、對氯苯磺醯基醋酸胍、對甲磺醯基苯磺醯基醋酸胍、苯基丙酸鉀、苯基丙酸胍、苯基丙酸銫、對氯苯基丙酸胍、對伸苯雙苯基丙酸胍、苯磺醯基醋酸四甲銨、苯基丙酸四甲銨等。該等亦可含有2種以上。
熱酸產生劑或熱鹼產生劑的含有量係相對於溶劑除外的樹脂組成物總量100質量份,較佳係0.01質量份以上、更佳係0.1質量份以上。藉由熱酸產生劑或熱鹼產生劑含有0.01質量份以上,便可促進交聯反應、及樹脂未閉環構造的環化,故能更加提升硬化膜的機械特性及耐藥性。又,就從有機EL顯示裝置的長期可靠度觀點,較佳係5質量份以下、更佳係2質量份以下。
其次,針對本發明樹脂組成物之製造方法進行說明。例如藉由使上述(a)鹼可溶性樹脂、(b1)醯胺酚化合物及/或(b2)芳香族醯胺酸化合物、以及任意的(c)感光性化合物、(d)熱交聯劑、自由基聚合性化合物、環狀醯胺、環狀脲及該等的衍生物、有機溶劑、著色劑、 密接改良劑、界面活性劑、無機粒子、熱酸產生劑、熱鹼產生劑等溶解,便可獲得樹脂組成物。溶解方法係可例如攪拌或加熱。施行加熱時,加熱溫度最好設定為不致損及樹脂組成物之性能的範圍內,通常係室溫~80℃。又,各成分的溶解順序並無特別的限定,例如從溶解性較低的化合物開始依序溶解的方法。又,關於界面活性劑或部分密接改良劑等,在攪拌溶解時容易產生氣泡的成分,藉由在其他成分溶解後於最後才添加,便可防止因產生氣泡而導致其他成分之溶解不良。
所獲得樹脂組成物較佳係使用過濾用濾器施行過濾,除去垃圾或粒子。過濾器孔徑係例如0.5μm、0.2μm、0.1μm、0.07μm、0.05μm、0.02μm等,惟並不僅侷限於該等。過濾用濾器的材質係有如:聚丙烯(PP)、聚乙烯(PE)、尼龍(NY)、聚四氟乙烯(PTFE)等,較佳係聚乙烯、尼龍。
本發明的樹脂片係由上述樹脂組成物形成。
樹脂片係例如在聚對苯二甲酸乙二酯等剝離性基材上,塗佈前述樹脂組成物而獲得樹脂組成物的塗佈膜,經乾燥便可獲得。又,亦可積層保護膜。
塗佈方法係可例如:旋塗法、狹縫式塗佈法、浸塗法、噴塗法、印刷法等。該等之中,就從依少量塗佈液便可施行塗佈、有利於成本降低的觀點,較佳係狹縫式塗佈法。例如相較於旋塗法之下,狹縫式塗佈法所必要的塗佈液量係1/5~1/10左右。塗佈時所使用的狹縫噴嘴係可從例如:大日本SCREEN製造(股)製「線性塗 佈機」、東京應化工業(股)製「Spinless」、東麗工程(股)製「TS塗佈機」、中外爐工業(股)製「包衣機」(table coater)、東京電子(股)製「CS系列」「CL系列」、Cermatronics貿易(股)製「在線型狹縫式塗佈機」、平田機工(股)製「頭塗佈機HC系列」等由複數製造商上市者之中選擇。一般塗佈速度係設在10mm/秒~400mm/秒範圍內。塗佈膜的膜厚係依照樹脂組成物的固形份濃度、黏度等而有所差異,通常依乾燥後的膜厚成為0.1~10μm、較佳0.3~5μm的方式施行塗佈。
在塗佈之前,亦可將塗佈樹脂組成物的基材,預先利用前述密接改良劑施行前處理。前處理方法係可例如使用由密接改良劑,依0.5~20質量%溶解於例如異丙醇、乙醇、甲醇、水、四氫呋喃、丙二醇單甲醚醋酸酯、丙二醇單甲醚、乳酸乙酯、己二酸二乙酯等溶劑中的溶液,對基材表面施行處理的方法。基材表面的處理方法係可舉例如:旋塗法、狹縫式模具塗佈法、棒塗法、浸塗法、噴塗法、蒸氣處理法等方法。
經塗佈後,視需要施行減壓乾燥處理。一般係依已形成塗佈膜的基板逐一施行減壓乾燥。例如在真空腔內所配置的固定銷(proxy pin)上,放置已形成塗佈膜的基板,藉由將真空腔內施行減壓而施行減壓乾燥的方法。此時,為抑制因位於基板與真空腔頂板間的空氣,隨減壓乾燥而產生大量流動,導致出現模糊不均情形,最好依基板與真空腔頂板的間隔成為狹窄的方式,調整固定銷的高度。基板與真空腔頂板間的距離較佳係2~20mm左右、更佳係2~10mm。
減壓乾燥速度係依照真空腔容積、真空泵能力、以及 腔與泵間的配管徑等而有所差異,最好設定為例如在沒有塗佈基板的狀態下,真空腔內經60秒後便減壓至40Pa的條件等。一般的減壓乾燥時間大多係設為30秒至100秒程度,而減壓乾燥結束時的真空腔內到達壓力,在有塗佈基板的狀態下通常係100Pa以下。藉由將到達壓設為100Pa以下,便可形成經降低塗佈膜表面沾黏的乾燥狀態,藉此可抑制後續進行基板搬送時發生表面污染與微塵。
塗佈後或減壓乾燥後,一般係對塗佈膜施行加熱乾燥。此項步驟亦稱「預烘烤」。乾燥係使用例如:加熱板、烤箱、紅外線等。使用加熱板時,直接將塗佈膜保持於板上、或者保持於板上所設置固定銷等的夾具上,施行加熱。固定銷的材質係可例如:鋁、不銹鋼等金屬材料;聚醯亞胺樹脂、「鐵氟龍」(註冊商標)等合成樹脂。在具耐熱性之前提下,可使用任一材質的固定銷。固定銷的高度係依照基板尺寸、塗佈膜種類、加熱目的等而有各種設定,較佳係0.1~10mm程度。加熱溫度及加熱時間係依照塗佈膜的種類與目的而有各種設定,加熱溫度較佳係50℃~180℃,加熱時間較佳係1分鐘~數小時。
當樹脂片係具有感光性時,便可形成圖案。例如對具感光性的樹脂片,透過具有所需圖案的遮罩照射化學射線,而施行曝光、顯影,便可形成所需的圖案。
曝光時所使用的化學射線係可例如:紫外線、可見光線、電子束、X射線等。本發明較佳係使用水銀燈的i線(365nm)、h線(405nm)、g線(436nm)。具有正型感光性的情況,曝光部會溶解於顯影液中。具有負型感光性的情況,曝光部會硬化並不溶於顯影液中。
經曝光後,於正型的情況便將曝光部(負型的情況便將非曝光部)利用顯影液予以除去,而形成所需圖案。顯影液較佳係例如:氫氧化四甲銨、二乙醇胺、二乙胺基乙醇、氫氧化鈉、氫氧化鉀、碳酸鈉、碳酸鉀、三乙胺、二乙胺、甲基胺、二甲胺、醋酸二甲胺基乙酯、二甲胺基乙醇、甲基丙烯酸二甲胺基乙酯、環己胺、伸乙二胺、己二胺等呈鹼性化合物的水溶液。在該等鹼水溶液中,亦可添加1種以上之例如:N-甲基-2-吡咯啶酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、二甲基亞碸、γ-丁內酯、二甲基丙烯醯胺等極性溶劑;甲醇、乙醇、異丙醇等醇類;乳酸乙酯、丙二醇單甲醚醋酸酯等酯類;環戊酮、環己酮、異丁酮、甲基異丁酮等酮類等等。顯影方式係可舉例如:噴霧、攪練、浸漬、超音波等方式。
其次,最好將依顯影所形成的圖案,利用蒸餾水施行清洗處理。亦可將例如:乙醇、異丙醇等醇類;乳酸乙酯、丙二醇單甲醚醋酸酯等酯類等,添加於蒸餾水中施行清洗處理。
本發明的硬化膜係藉由將上述樹脂片或樹脂組成物施行硬化便可獲得。
本發明的硬化膜係含有:(a)鹼可溶性樹脂、以及一般式(11)~(13)中之任一者所示苯并唑化合物及/或下述一般式(14)~(16)中之任一者所示醯亞胺化合物。一般式(11)~(13)所示苯并唑化合物分別係由一般式(3)~(5)所示醯胺酚化合物進行脫水閉環的化合物;而一般式(14)~(16)所示醯亞胺化合物分別係由一般式(6)~(10)所示芳香族醯胺酸化合物進行脫水閉環的化合物。
一般式(11)~(13)中,W係表示與一般式(11)~(13)中的唑環之碳直接鍵結、且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。一般式(14)~(16)中,V係表示與一般式(14)~(16)中的醯亞胺環之氮直接鍵結、且具有碳數2~20之烷基的1價有機基、或具-(YO)n-的1價有機基。m係表示1~4的整數;Y係表示碳數1~10之伸烷基;n係表示1~20的整數。Z係表示單鍵、氫原子、烷氧基、-O-、-SO2-、-C(CF3)2-、-O-R1-O-、-C(=O)-、 -C(=O)O-R2-OC(=O)-、-C(=O)NH-R3-NHC(=O)-、或碳數1~20的1~4價烴基。R1~R3係表示碳數1~20的2價烴基;R4及R5係表示-C(CH3)2-、-C(CF3)2-、-O-或-S-。但,當Z係單鍵的情況,便為m=2。
硬化膜係藉由含有:(a)鹼可溶性樹脂、以及一般式(11)~(13)中之任一者所示苯并唑化合物及/或一般式(14)或(16)所示醯亞胺化合物,便可獲得低吸水率的硬化膜。
硬化膜係可含有從環狀醯胺、環狀脲及該等的衍生物所構成群組中選擇1種以上的化合物。環狀醯胺、環狀脲及該等的衍生物之總含有量,在硬化膜100質量%中,較佳係佔0.005質量%以上且5質量%以下。
藉由將前述樹脂組成物或樹脂片施行加熱硬化,便可除去耐熱性較低的成分,而可提升耐熱性及耐藥性。特別當本發明的樹脂組成物或樹脂片係含有:聚醯亞胺先質、聚苯并唑先質、該等的共聚合體、或該等與聚醯亞胺的共聚合體時,因為利用加熱硬化便形成醯亞胺環、唑環,所以可提升耐熱性及耐藥性。又,當含有(d)熱交聯劑的情況,可利用加熱硬化進行熱交聯反應,便可提升耐熱性及耐藥性。
加熱硬化溫度係就從降低自硬化膜所產生之逸氣量的觀點,較佳係300℃以上、更佳係350℃以上。另一方面,就從提升硬化膜之膜韌性的觀點,較佳係500℃以下、更佳係450℃以下。在該溫度範圍內,可階段式升溫、亦可連續式升溫。加熱硬化時間係就從降低逸氣量的觀點,較佳係30分鐘以上。又,就從提升硬化膜的膜韌性觀點,較佳係3小時以下。例如:在150℃、250℃下分別各施行30分鐘熱處理的方法;或者一邊從室溫起歷時2 小時直線性升溫至300℃,一邊施行熱處理的方法等。
本發明的樹脂組成物、樹脂片及硬化膜,係頗適用於例如:半導體元件的表面保護層或層間絕緣層、有機電激發光(Electroluminescence:以下稱「EL」)元件的絕緣層、使用有機EL元件的顯示裝置之驅動用薄膜電晶體(Thin Film Transistor:以下稱「TFT」)基板之平坦化層、電路基板的配線保護絕緣層、固態攝像元件的晶片上微透鏡(OCL;on chip microlens)以及各種顯示器‧固態攝像元件用平坦化層。例如頗適用於耐熱性較低的MRAM、以及可望成為新世代記憶體的高分子記憶體(Polymer Ferroelectric RAM:PFRAM)或相變化記憶體(Phase Change RAM:PCRAM、Ovonics Unified Memory:OUM)等的表面保護層、層間絕緣層。又,亦可使用於含有在基板上所形成之第一電極、與相對向於上述第一電極所設置之第二電極的顯示裝置[例如LCD、ECD、ELD、使用有機電致發光元件的顯示裝置(有機電致發光裝置)等]之絕緣層。以下,就有機EL顯示裝置、半導體裝置、及半導體電子零件為例進行說明。
本發明的有機EL顯示裝置係在基板上設有:驅動電路、平坦化層、第1電極、絕緣層、發光層及第2電極,而平坦化層及/或絕緣層係由本發明的硬化膜構成。有機EL發光材料容易因水分而劣化的影響,會有發光部面積相對於發光像素面積率降低等不良影響的情況,因為本發明硬化膜的吸水率較低,因而可獲得安定的驅動及發光特性。若舉主動矩陣式顯示裝置為例,則在例如玻璃或各種 塑膠等基板上,設置:TFT、以及位於TFT側邊且連接於TFT的配線,並在其上面設有覆蓋凹凸的平坦化層,更在平坦化層上設置顯示元件。顯示元件與配線係經由在平坦化層中所形成的接觸窗相連接。
圖1所示係TFT基板一例的剖視圖。在基板6上呈行列狀設置底閘極式或頂閘極式TFT(薄膜電晶體)1,依覆蓋該TFT1的狀態形成絕緣層3。又,在該絕緣層3上設有連接於TFT1的配線2。又,在絕緣層3上依埋藏配線2的狀態設置平坦化層4。在平坦化層4中設有到達配線2的接觸窗7。所以,依經由該接觸窗7連接於配線2的狀態,在平坦化層4上形成ITO(透明電極)5。其中,ITO5成為顯示元件(例如有機EL元件)的電極。然後,依覆蓋ITO5周緣的方式形成絕緣層8。有機EL元件係可從基板6對向側釋出發光光的頂部發光型,亦可從基板6側取出光的底部發光式。依此,可獲得各有機EL元件連接著供驅動其的TFT1之主動矩陣式有機EL顯示裝置。
該絕緣層3、平坦化層4及/或絕緣層8係如前述,藉由下述步驟便可形成:形成包含本發明樹脂組成物或樹脂片之感光性樹脂膜的步驟;對上述感光性樹脂膜施行曝光的步驟;對經曝光的感光性樹脂膜施行顯影的步驟;以及對經顯影的感光性樹脂膜施行加熱處理的步驟。藉由包括有該等步驟的製造方法,便可獲得有機EL顯示裝置。
本發明的半導體電子零件及半導體裝置係在基板上設有:電 極、金屬配線、層間絕緣層及/或表面保護層,且層間絕緣層及/或表面保護層係由本發明的硬化膜構成。因為本發明硬化膜的機械特性優異,因而在安裝時亦能緩和來自密封樹脂的應力,能抑制low-k層(低介電常數層)損傷,可提供高可靠度的半導體裝置。
圖2所示係具凸塊的半導體裝置之墊部分一例之放大剖視圖。在矽晶圓9上形成輸出入用Al墊10、及具介層洞的鈍化層11。又,在鈍化層11上形成絕緣層12,更依連接於Al墊10的方式設置由Cr、Ti等形成的金屬層13,再利用電解電鍍等設置由Al、Cu等形成的金屬配線14。藉由對位於焊料凸塊18周邊的金屬層13施行蝕刻,而將各墊間予以絕緣。在經絕緣的墊上形成阻障金屬16與焊料凸塊18。
其次,針對半導體裝置之製造方法,使用圖式進行說明。圖3a~3f所示係設有凸塊的半導體裝置之製造方法一例。3a步驟中,在已形成有Al墊10與鈍化層11的矽晶圓9上,塗佈本發明的樹脂組成物,經由微影步驟而形成經圖案形成的絕緣層12。接著,在3b步驟中,利用濺鍍法形成金屬層13。3c步驟中,在金屬層13上利用電鍍法形成金屬配線14。接著,在3d'步驟中,塗佈本發明的樹脂組成物,在3d步驟中,經由微影步驟而形成絕緣層15的圖案。此時,構成絕緣層15的樹脂組成物在切割道17中會被厚膜加工。便可在絕緣層15上更進一步形成配線(所謂「再配線」)。形成2層以上多層配線構造時,藉由重複施行上述步驟,2層以上的再配線便可形成包含本發明硬化膜之層間絕緣層進行隔離的多層配線構造。多層配線構造的層數並無上限,大多係使用10層以下。其次,在3e步驟中形成阻障金屬16,在3f步驟中形成焊料凸 塊18。然後,最後沿切割道17施行晶割,依各個晶片裁切分開,便可獲得具有凸塊的半導體裝置。
舉以下實施例等說明本發明,惟本發明並不僅侷限於該等例示。另外,實施例中的樹脂組成物評價,係依照以下方法實施。
將利用各實施例及比較例所獲得的清漆,使用塗佈顯影裝置Mark-7(東京電子(股)製),利用旋塗法塗佈於8吋矽晶圓上,使用加熱板(SCW-636;大日本SCREEN製造(股)製),依120℃施行3分鐘烘烤,而製作膜厚3.0μm的預烘烤膜。另外,膜厚係使用大日本SCREEN製造(股)製Lambda Ace STM-602,依折射率1.63的條件測定。然後,使用曝光機i線步進器NSR-2005i9C(尼康公司製),經由設有10μm接觸窗圖案的遮罩,依曝光量100~1200mJ/cm2範圍每隔50mJ/cm2施行曝光。經曝光後,使用上述Mark-7顯影裝置,並以2.38重量%四甲銨水溶液(以下稱「TMAH」,多摩化學工業(股)製)為顯影液,施行顯影直到膜損失量成為0.5μm為止,然後利用蒸餾水施行清洗,經甩乾乾燥後便獲得圖案。
所獲得圖案使用FDP顯微鏡MX61(Olympus(股)製),依倍率20倍施行觀察,測定接觸窗的開口徑。求取接觸窗開口徑到達10μm時的最低曝光量,將其設為感度。
將由各實施例與比較例所獲得清漆,使用旋塗機(MS-A100;MIKASA(股)製),利用旋塗法依任意轉數塗佈於矽晶圓上之後,使用加熱板(SCW-636;大日本SCREEN製造(股)製),依120℃施行120秒鐘預烘烤,便製得膜厚約10.0μm的預烘烤膜。另外,膜厚係使用大日本SCREEN製造(股)製Lambda Ace STM-602,依折射率1.63的條件測定。所獲得預烘烤膜使用高溫惰性氣流烤箱(INH-9CD-S;Koyo Thermo Systems(股)製),在氧濃度20ppm以下,一邊依5℃/分的升溫條件升溫至250℃一邊施行加熱,更在250℃下施行1小時加熱處理,便製得樹脂組成物的硬化膜。其次,將所獲得硬化膜浸漬於45質量%氫氟酸水中,而將膜從矽晶圓上剝離開。所獲得的膜經利用純水充分洗淨後,使用60℃烤箱施行5小時乾燥便獲得薄膜。所獲得薄膜經依50℃施行24小時乾燥後,浸漬於保持23℃的純水中。然後,使用熱重量分析裝置(TGA-50;島津製作所(股)製),在氮環境下,分別測定室溫下的重量,以及從室溫升溫至100℃後,更在100℃下保持30分鐘後的重量,從100℃下重量相對於室溫下重量的減少量,計算出吸水率。
將依照與(2)同樣方法製作的薄膜10mg,放入熱重量分析裝置TGA-50(島津製作所(股)製)中,於氮環境下,從室溫升溫至100℃後,更在100℃下保持30分鐘,測定重量。然後,依升溫速度10℃/分的條件一邊升溫至400℃,一邊測定重量,測定相對於在100℃下保持30分鐘後的重量減少5%時的溫度。
各實施例、比較例所使用的熱交聯劑(d-1)~(d-2)、酚 化合物(e-1)~(e-3)及熱酸產生劑(f-1),係如下示:
使2,2-雙(3-胺基-4-羥苯基)六氟丙烷(以下稱「BAHF」)18.3g(0.05莫耳),溶解於丙酮100mL、環氧丙烷17.4g(0.3莫耳)中,冷卻至-15℃。在其中滴下由3-硝基氯化苯甲醯20.4g(0.11莫耳)溶解於丙酮100mL中的溶液。待滴下結束後,於-15℃下進行4小時反應,然後返回室溫。過濾所析出的白色固體,依50℃施行真空乾燥。
將所獲得之白色固體30g裝入300mL不銹鋼熱壓鍋中,分散於甲基賽珞蘇250mL中,添加5%鈀-碳2g。在其中利用 氣球導入氫,在室溫下施行還原反應。經約2小時後,確認氣球已不會再消風時便結束反應。待反應結束後,經過濾除去屬於觸媒的鈀化合物,利用旋轉式蒸發器施行濃縮,便獲得下式所示含羥基之二胺化合物(α)。
在乾燥氮氣流下,使3,3',4,4'-二苯醚四羧酸二酐(以下稱「ODPA」)31.0g(0.10莫耳)溶解於N-甲基-2-吡咯啶酮(NMP)500g中。在其中與NMP:50g同時添加合成例1所獲得之含羥基之二胺化合物45.35g(0.075莫耳)與1,3-雙(3-胺丙基)四甲基二矽氧烷1.24g(0.005莫耳),依20℃進行1小時反應,接著依50℃進行2小時反應。接著,與NMP:5g同時添加末端終止劑之4-胺基酚4.36g(0.04莫耳),依50℃進行2小時反應。然後,歷時10分鐘滴下N,N-二甲基甲醯胺二甲基縮醛28.6g(0.24莫耳)經NMP:50g稀釋的溶液。經滴下後,於50℃下攪拌3小時。待攪拌結束後,將溶液冷卻至室溫後,將溶液倒入水3L中獲得白色沉澱。過濾收集該沉澱,利用水施行3次洗淨後,利用80℃真空乾燥機施行24小時乾燥,便獲得屬於鹼可溶性樹脂的聚醯亞胺先質(a-1)。
在乾燥氮氣流下,使BAHF:29.3g(0.08莫耳)、1,3-雙(3-胺丙基)四甲基二矽氧烷1.24g(0.005莫耳)、以及末端終止劑之3-胺基酚3.27g(0.03莫耳),溶解於N-甲基-2-吡咯啶酮(NMP)150g中。在其中,與NMP:50g一起添加ODPA:31.0g(0.1莫耳),於20℃下攪拌1小時,接著依50℃施行4小時攪拌。然後,添加二甲苯15g,一邊使水與二甲苯進行共沸,一邊依150℃進行5小時攪拌。待攪拌結束後,將溶液倒入水3L中獲得白色沉澱。過濾收集該沉澱,利用水施行3次洗淨後,利用80℃真空乾燥機施行24小時乾燥,便獲得屬於鹼可溶性樹脂的聚醯亞胺(a-2)。
在乾燥氮氣流下,使BAHF:18.3g(0.05莫耳)溶解於NMP:50g、環氧丙基甲醚26.4g(0.3莫耳)中,將溶液溫度冷卻至-15℃。依內部溫度不會超過0℃的方式,使二苯醚二氯二羧酸(日本農藥(股)製)7.4g(0.025莫耳)、氯化異酞酸(東京化成(股)製)5.1g(0.025莫耳),滴下至溶解有γ-丁內酯(GBL)25g的溶液。待滴下結束後,於-15℃下持續攪拌6小時。待反應結束後,在含甲醇10重量%的水3L中倒入溶液,收集白色沉澱。過濾收集該沉澱,利用水施行3次洗淨後,利用80℃真空乾燥機施行24小時乾燥,便獲得屬於鹼可溶性樹脂的聚苯并唑先質(a-3)。
在500ml燒瓶中,裝入:2,2'-偶氮雙(異丁腈)5g、第三(十二烷)硫醇5g、以及丙二醇單甲醚醋酸酯(以下簡稱「PGMEA」)150g。 然後,添加甲基丙烯酸3og、甲基丙烯酸苄酯35g、三環[5.2.1.02,6]癸烷-8-基甲基丙烯酸酯35g,在室溫下短暫攪拌,將燒瓶內施行氮取代後,依70℃加熱攪拌5小時。接著,在所獲得之溶液中添加甲基丙烯酸環氧丙酯15g、二甲基苄胺1g、以及對甲氧基酚0.2g,於90℃下加熱攪拌4小時,獲得屬於鹼可溶性樹脂的丙烯酸樹脂(a-4)之溶液。所獲得之丙烯酸樹脂溶液的固形份濃度係43重量%。
在乾燥氮氣流下,裝填入:間甲酚70.2g(0.65莫耳)、對甲酚37.8g(0.35莫耳)、37重量%甲醛水溶液75.5g(甲醛0.93莫耳)、草酸二水合物0.63g(0.005莫耳)、以及甲基異丁酮264g後,浸漬於油浴中,一邊使反應液回流,一邊施行7小時的縮聚反應。然後,歷時3小時將油浴溫度進行升溫,然後將燒瓶內的壓力減壓至40~67hPa,除去揮發成分,將已溶解的樹脂冷卻至室溫,添加GBL,獲得將非揮發成分調整於50%、且屬於鹼可溶性樹脂的酚醛樹脂(a-5)之溶液。所獲得酚醛樹脂(a-5)的重量平均分子量係7000。
使2-胺基酚10.9g(0.1莫耳)溶解於四氫呋喃(THF)200mL、三乙胺30.4g(0.3莫耳)中。在其中,依-10℃以下滴下由癸醯氯19.1g(0.1莫耳)溶解於THF:100mL中的溶液。待滴下結束後,於室溫下進行4小時反應。然後,添加1%鹽酸溶液,將反應溶液利用醋酸乙酯施行萃取,經除去溶劑而獲得的固體,依50℃施行真空乾燥,獲得下式所示醯胺酚化合物(b1-1)。
除取代2-胺基酚10.9g(0.1莫耳),改為使用雙(3-胺基-4-羥苯基)六氟丙烷(BAHF)36.3g(0.1莫耳),並將癸醯氯19.1g(0.1莫耳)改為38.1g(0.2莫耳)之外,其餘均依照與合成例7同樣地獲得下式所示醯胺酚化合物(b1-2)。
除取代癸醯氯38.1g(0.2莫耳),改為使用丁醯氯21.3g(0.2莫耳)之外,其餘均依照與合成例8同樣地獲得下式所示醯胺酚化合物(b1-3)。
除取代癸醯氯38.1g(0.2莫耳),改為使用3-苯基氯丙醯33.7g(0.2莫耳)之外,其餘均依照與合成例8同樣地獲得下式所示醯胺酚化合物(b1-4)。
除取代2-胺基酚10.9g(0.1莫耳),改為使用2,5-二羥-對伸苯二胺14.0g(0.1莫耳),且將癸醯氯19.1g(0.1莫耳)改為38.1g(0.2莫耳)之外,其餘均依照與合成例7同樣地獲得下式所示醯胺酚化合物(b1-5)。
除取代癸醯氯38.1g(0.2莫耳),改為使用氯化苯甲醯28.1g(0.2莫耳)之外,其餘均依照與合成例8同樣地獲得下式所示醯胺酚化合物(b'-6)。
[化20]
除取代2-胺基酚10.9g(0.1莫耳),改為使用3-胺基酚10.9g(0.1莫耳)之外,其餘均依照與合成例7同樣地獲得下式所示醯胺酚化合物(b'-7)。
在乾燥氮氣流下,使TrisP-PA(商品名、本州化學工業(股)製)21.22g(0.05莫耳)、與5-萘醌二疊氮磺醯基醯氯36.27g(0.135莫耳),溶解於1,4-二烷450g中,設為室溫。在其中依系統內不會成為35℃以上的方式,滴下經混合1,4-二烷50g的三乙胺15.18g。待滴下後,依30℃攪拌2小時。過濾三乙胺鹽,將濾液倒入水中。然後,利用過濾收集所析出的沉澱。該沉澱利用真空乾燥機施行乾燥,獲得下式所示醌二疊氮化合物(c1-1)。
[化22]
在乾燥氮氣流下,使TrisP-PA(商品名、本州化學工業(股)製)21.22g(0.05莫耳)、與4-萘醌二疊氮磺醯基醯氯36.27g(0.135莫耳),溶解於1,4-二烷450g中,設為室溫。在其中依系統內不會成為35℃以上的方式,滴下經混合1,4-二烷50g的三乙胺15.18g。待滴下後,依30℃攪拌2小時。過濾三乙胺鹽,將濾液倒入水中。然後,利用過濾收集所析出的沉澱。該沉澱利用真空乾燥機施行乾燥,獲得下式所示醌二疊氮化合物(c1-2)。
在乾燥氮氣流下,使TekP-4HBPA(商品名、本州化學工業(股)製)28.83g(0.05莫耳)、與5-萘醌二疊氮磺醯基醯氯13.43g(0.125莫 耳),溶解於1,4-二烷450g中,設為室溫。在其中依系統內不會成為35℃以上的方式,滴下經混合1,4-二烷50g的三乙胺15.18g。待滴下後,依30℃攪拌2小時。過濾三乙胺鹽,將濾液倒入水中。然後,利用過濾收集所析出的沉澱。該沉澱利用真空乾燥機施行乾燥,獲得下式所示之醌二疊氮化合物(c1-3)。
將樹脂(a-1)10g、醯胺酚化合物(b1-1)2.0g、醌二疊氮化合物(c1-1)2.0g、以及交聯劑(d-1)1.0g,添加於GBL:30g中,獲得正型感光性樹脂組成物的清漆A。使用所獲得之清漆A,依如上述施行感度、吸水率、5%重量減少溫度的測定。評價結果如表1所示。
除變更為表1所記載組成之外,其餘均依照與實施例1同樣地製備清漆B~W。使用所獲得之清漆,依照與實施例1同樣地施行感度、吸水率、5%重量減少溫度的測定。評價結果如表1~2所示。
Claims (16)
- 一種樹脂組成物,係含有:(a)鹼可溶性樹脂、以及(b1)在酚性羥基鄰位具有下述一般式(1)所示1價基的醯胺酚化合物及/或(b2)在羧基鄰位具有下述一般式(2)所示1價基的芳香族醯胺酸化合物;
- 如請求項1之樹脂組成物,其中,上述(b1)醯胺酚化合物係下述一般式(3)~(5)中之任一者所示:[化2]
- 如請求項1之樹脂組成物,其中,上述(b2)芳香族醯胺酸化合物係下述一般式(6)~(10)中之任一者所示:[化3]
- 如請求項1至3中任一項之樹脂組成物,其中,上述(a)鹼可 溶性樹脂係含有:聚醯亞胺、聚苯并 唑、聚醯胺醯亞胺、該等中之任一者的先質及/或該等的共聚合體。
- 如請求項1至4中任一項之樹脂組成物,其中,更進一步含有(c)感光性化合物。
- 如請求項1至5中任一項之樹脂組成物,其中,更進一步含有(d)熱交聯劑。
- 一種樹脂片,係由請求項1至6中任一項之樹脂組成物形成。
- 一種硬化膜,係使請求項7之樹脂片硬化而成。
- 一種硬化膜,係使請求項1至6中任一項之樹脂組成物硬化而成。
- 一種有機EL顯示裝置,係在基板上設有:驅動電路、平坦化層、第1電極、絕緣層、發光層及第2電極的有機EL顯示裝置;其中,上述平坦化層及/或絕緣層包含請求項8或9之硬化膜。
- 一種半導體電子零件,係在基板上設有:電極、金屬配線、層間絕緣層及/或表面保護層的半導體電子零件;其中,上述層間絕緣層及/或表面保護層包含請求項8或9之硬化膜。
- 一種半導體裝置,係在基板上設有:電極、金屬配線、層間絕緣層及/或表面保護層的半導體裝置;其中,上述層間絕緣層及/或表面保護層包含請求項8或9之硬化膜。
- 一種有機EL顯示裝置之製造方法,係包括有:在基板上,形成包含請求項5或6之樹脂組成物或請求項7之樹脂片之感光性樹脂膜的步驟;對上述感光性樹脂膜施行曝光的步驟;對經曝光的感光性樹脂膜施行顯影的步驟;以及對經顯影的感光性樹脂膜施行加熱處理的步驟。
- 一種醯胺酚系助溶劑,係下述一般式(3)~(5)中之任一者所示:
- 一種芳香族醯胺酸系助溶劑,係下述一般式(6)~(10)中之任一者所示:
- 一種硬化膜,係含有:(a)鹼可溶性樹脂、以及下述一般式(11)~(13)中之任一者所示之苯并 唑化合物及/或下述一般式(14)~(16)中之任一者所示之醯亞胺化合物;
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