JP2017524040A - 光電素子のフレキシブル基板用ポリイミドフィルム用組成物 - Google Patents
光電素子のフレキシブル基板用ポリイミドフィルム用組成物 Download PDFInfo
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- JP2017524040A JP2017524040A JP2016551162A JP2016551162A JP2017524040A JP 2017524040 A JP2017524040 A JP 2017524040A JP 2016551162 A JP2016551162 A JP 2016551162A JP 2016551162 A JP2016551162 A JP 2016551162A JP 2017524040 A JP2017524040 A JP 2017524040A
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- Prior art keywords
- polyimide precursor
- group
- polyimide
- solvent
- precursor composition
- Prior art date
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 139
- 239000000758 substrate Substances 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 230000009975 flexible effect Effects 0.000 title claims abstract description 25
- 239000004642 Polyimide Substances 0.000 claims abstract description 81
- 239000002243 precursor Substances 0.000 claims abstract description 77
- 239000000126 substance Substances 0.000 claims abstract description 51
- 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 claims abstract description 29
- 238000010438 heat treatment Methods 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000004985 diamines Chemical class 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000011521 glass Substances 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical group 0.000 claims description 4
- 238000002834 transmittance Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 29
- 239000010408 film Substances 0.000 description 24
- -1 siloxane repeating unit Chemical group 0.000 description 24
- 125000000962 organic group Chemical group 0.000 description 23
- 239000000243 solution Substances 0.000 description 15
- 229920005575 poly(amic acid) Polymers 0.000 description 14
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 11
- 239000009719 polyimide resin Substances 0.000 description 11
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 8
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- BCJIMAHNJOIWKQ-UHFFFAOYSA-N 4-[(1,3-dioxo-2-benzofuran-4-yl)oxy]-2-benzofuran-1,3-dione Chemical compound O=C1OC(=O)C2=C1C=CC=C2OC1=CC=CC2=C1C(=O)OC2=O BCJIMAHNJOIWKQ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 2
- PXQNJDUJSVCPCD-UHFFFAOYSA-N C(C)N(C=O)CC.C(C)N(C=O)CC Chemical compound C(C)N(C=O)CC.C(C)N(C=O)CC PXQNJDUJSVCPCD-UHFFFAOYSA-N 0.000 description 2
- WKOCXPIOHONZAM-UHFFFAOYSA-N N,N-diethylacetamide Chemical compound C(C)(=O)N(CC)CC.C(C)(=O)N(CC)CC WKOCXPIOHONZAM-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 description 1
- NQZOFDAHZVLQJO-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 NQZOFDAHZVLQJO-UHFFFAOYSA-N 0.000 description 1
- JERFEOKUSPGKGV-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(SC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 JERFEOKUSPGKGV-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- YSMXOEWEUZTWAK-UHFFFAOYSA-N 3-[4-[[4-(3-aminophenoxy)phenyl]methyl]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(CC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 YSMXOEWEUZTWAK-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YARZEPAVWOMMHZ-UHFFFAOYSA-N 4-(3,4-dicarboxy-4-phenylcyclohexa-1,5-dien-1-yl)phthalic acid Chemical compound OC(=O)C1C=C(C=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=CC1(C(O)=O)C1=CC=CC=C1 YARZEPAVWOMMHZ-UHFFFAOYSA-N 0.000 description 1
- QNLCDRXVEPWSBQ-UHFFFAOYSA-N 4-(4,5-dicarboxy-5-phenylcyclohexa-1,3-dien-1-yl)phthalic acid Chemical compound OC(=O)C1=CC=C(C=2C=C(C(C(O)=O)=CC=2)C(O)=O)CC1(C(O)=O)C1=CC=CC=C1 QNLCDRXVEPWSBQ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- TZKDBUSJDGKXOE-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfinylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 TZKDBUSJDGKXOE-UHFFFAOYSA-N 0.000 description 1
- PJCCVNKHRXIAHZ-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)phenyl]methyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1CC(C=C1)=CC=C1OC1=CC=C(N)C=C1 PJCCVNKHRXIAHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- ZKGNPQKYVKXMGJ-UHFFFAOYSA-N N,N-dimethylacetamide Chemical compound CN(C)C(C)=O.CN(C)C(C)=O ZKGNPQKYVKXMGJ-UHFFFAOYSA-N 0.000 description 1
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- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- HKWWRLBGQRLBRM-UHFFFAOYSA-N [4-[4-(4-aminophenoxy)benzoyl]phenyl]-[4-(4-aminophenoxy)phenyl]methanone Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(=O)C=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HKWWRLBGQRLBRM-UHFFFAOYSA-N 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
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Abstract
Description
R3及びR4は、それぞれ独立して炭素数1〜5のアルキル基であり、
R5及びR6は、それぞれ独立して炭素数4〜10のアリール基であり、
R7及びR8のうち少なくとも一つは、炭素数2〜10のアルケニル基であり、
m1、m2及びm3は、それぞれ独立して1以上の整数である。
R3及びR4は、それぞれ独立して炭素数1〜5のアルキル基であり、
R5及びR6は、それぞれ独立して炭素数4〜10のアリール基であり、
R7及びR8のうち少なくとも一つは、炭素数2〜10のアルケニル基であり、
m1、m2及びm3は、それぞれ独立して1以上の整数である。
X1は、酸二無水物から誘導された芳香族、脂環族または脂肪族基を含む4価有機基であり、
Y1は、下記化学式4で表されるジアミンから誘導される2価有機基を含む2価有機基であり、
pは、繰り返し単位を表す1以上の整数である。
前記R1からR8及びm1からm3は、化学式2で説明した通りである。
X2は、酸二無水物から誘導された芳香族、脂環族または脂肪族基を含む4価有機基であり、
Y2は、ジアミンから誘導された芳香族、脂環族または脂肪族基を含む2価有機基であり、
qは、繰り返し単位を表す1以上の整数である。
Aは、単一結合、−O−、−NH−、−CO−、−S−、−SO2−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)n1−、−O(CH2)n2O−、または−OCO(CH2)n3OCO−であり、n1、n2及びn3は、それぞれ1〜10の整数であり、
R11、R12、R13、R14、R15及びR16は、それぞれ独立して水素原子、ハロゲン原子、またはヒドロキシ基から選択される。
前記R31〜R35は、それぞれ独立して炭素数1〜10のアルキル基(例えば、メチル基、エチル基、プロピル基、イソプロピル基、t−ブチル基、ペンチル基、ヘキシル基など)、または炭素数1〜10のフルオロアルキル基(例えば、フルオロメチル基、パーフルオロエチル基、トリフルオロメチル基など)であり、
前記a1は0または2の整数、b1は0〜4の整数、c1は0〜8の整数、d1及びe1はそれぞれ独立して0〜3の整数であり、
前記A1は、単一結合、−O−、−CR46R47−、−C(=O)−、−C(=O)NH−、−S−、−SO2−、フェニレン基及びこれらの組み合わせからなる群から選択される。この際、前記R46及びR47は、それぞれ独立して水素原子、炭素数1〜10のアルキル基(例えば、メチル基、エチル基、プロピル基、イソプロピル基、t−ブチル基、ペンチル基、ヘキシル基など)、及び炭素数1〜10のフルオロアルキル基(例えば、フルオロメチル基、フルオロエチル基、トリフルオロメチル基など)からなる群から選択される。
まず、ACD/Labs社製のACD/Percepta platformのACD/LogP module(ここで、ACD/LogP moduleは、分子の2D構造を用いて、QSPR(Quantitative Structure−Property Relationship)方法論に基づいたアルゴリズム法)を使用して計算された25℃での分配係数(LogP値)は、次の通りである。
DMAc:N,N−ジメチルアセトアミド(N,N−Dimethylacetamide)
DEAc:N,N−ジエチルアセトアミド(N,N−Diethylacetamide)
DEF:N,N−ジエチルホルムアミド(N,N−Diethyl formamide)
DMF:N,N−ジメチルホルムアミド(N,N−Dimethyl formamide)
NMP:N−メチルピロリドン(N−methylpyrrolidone)
NEP:N−エチルピロリドン(N−ethylpyrrolidene)
化学式2の前駆体
2,2′−ビス(トリフルオロメチル)−ベンジジン(2,2´−bis(trifluoromethyl)benzidine;TFMB)0.061molと、アミノ変性オルガノポリシロキサン(Amino modified organopolysiloxane)(P_PDMS_V、分子量;1070Mw、信越化学社から入手)0.0068molとをDEF:トルエン(Toluene)(vol/vol 7:3)150gに溶かし、BPDA 0.068molと溶媒(DEF)100gとを添加して、15℃で2時間撹拌した後、25℃で10時間撹拌した。この際、反応は、無水条件で行われた。結果として得られた反応溶液にDEFを添加し、反応溶液の粘度が5,000cPとなるように、固形分25重量%で調節した後、24時間均一に混合して、ポリイミド前駆体溶液を製造した。
化学式3の前駆体(P_PDMS_V)の含量が30重量%となるようにしたことを除いては、実施例1と同様な方法により前駆体組成物を製造した。
化学式3の前駆体(P_PDMS_V)の含量が50重量%となるようにしたことを除いては、実施例1と同様な方法により前駆体組成物を製造した。
BPDAの代わりにオキシジフタル酸無水物(Oxydiphthalic anhydride;ODPA)を使用し、化学式3の前駆体(P_PDMS_V)の含量が30重量%となるようにしたことを除いては、実施例1と同様な方法により前駆体組成物を製造した。
化学式5の前駆体(BPDA−TFMB)
3,3′,4,4′−ビフェニルテトラカルボン酸二無水物(3,3´,4、4´−Biphenyltetracaboxylic dianhydride)20gを窒素雰囲気の下でジエチルホルムアミド(diethylformamide,DEF)150gに20分間にかけて溶解させた。結果として得られたBPDA/DEF溶液に、ジアミン系化合物として2,2′−ビス(トリフルオロメチル)−ベンジジン(2,2´−bis(trifluoromethyl)benzidine;TFMB)32.6gをDEF 110gに溶解させて製造したTFMB/DEF溶液を添加し、25℃で2時間反応させた後、40℃に昇温させて24時間反応させた。結果として得られた反応溶液にDEFを添加し、反応溶液の粘度が5,000cPとなるように、固形分10重量%で調節した後、24時間均一に混合して、ポリイミド前駆体溶液を製造した。
BPDAの代わりにオキシジフタル酸無水物(Oxydiphthalic anhydride;ODPA)を使用したことを除いては、比較例1と同様な方法により前駆体組成物を製造した。
TFMBの代わりに2,2−ビス[4−(4−アミノフェノキシ)フェニル]ヘキサフルオロプロパン(2,2−bis[4−(4−aminophenoxy)phenyl]hexafluopropane;BAPP)を使用したことを除いては、比較例1と同様な方法により前駆体組成物を製造した。
製造したポリイミド前駆体溶液を約10ミクロンの厚さでガラス基板にスピンコーティングした。ポリイミド前駆体溶液が塗布されたガラス基板をオーブンに入れ、3℃/minの速度で加熱し、80℃、120℃、180℃、250℃で30分〜1時間を維持して硬化工程を行った。
ガラスストレスはBow値で表し、測定方法は次の通りである。10cm×10cmのガラスをストレス測定器(TENCOR社製のFLX2320)に設置し、レーザで中央をスキャンした後、両側1cmを除いた総8cmのセンター部分で、左右の両側4cm間の距離でガラスが反った程度(高さ)偏差を測定した。
前記製造例によって製造されたそれぞれのポリイミドフィルムに対して、最大延伸率、モデュラス、最大ストレス及び熱膨脹係数をそれぞれ測定した。
フィルム硬化条件:250℃ multi−step
○:フィルム変形がない、△:部分的にフィルム変形が発生、×:フィルム変形が発生
厚さ方向位相差Rthは、Axoscanを用いて測定した。フィルムを一定のサイズにカットして厚さを測定した後、Axoscanで位相差を測定して位相差値を補償するために、C−plate方向に補正しながら測定した厚さを入力した。
Claims (18)
- 化学式1の構造を含むジアミンまたは酸二無水物から来由されたポリイミド前駆体を含有する光電素子のフレキシブル基板用ポリイミド前駆体組成物:
R3及びR4は、それぞれ独立して炭素数1〜5のアルキル基であり、
R5及びR6は、それぞれ独立して炭素数4〜10のアリール基であり、
R7及びR8のうち少なくとも一つは、炭素数2〜10のアルケニル基であり、
m1、m2及びm3は、それぞれ独立して1以上の整数である。 - 前記化学式1の構造を含むジアミンまたは酸二無水物から来由されたポリイミド前駆体を、ポリイミド前駆体の総重量を基準として50重量%以下含有する、請求項1に記載のフレキシブル基板用ポリイミド前駆体組成物。
- 前記化学式1の構造を含むジアミンまたは酸二無水物から来由されたポリイミド前駆体は、分子量が600以上かつ7,000以下である、請求項1に記載のポリイミド前駆体組成物。
- 前記化学式1において、m1、m2及びm3は、それぞれ独立して1〜10の整数である、請求項1に記載のポリイミド前駆体組成物。
- 前記組成物は、分配係数が正数の値を表す溶媒にポリイミド前駆体が溶解されている、請求項1に記載のポリイミド前駆体組成物。
- 前記溶媒は、アミン系第1溶媒と、非アミン系第2溶媒とを含む、請求項5に記載のポリイミド前駆体組成物。
- 前記アミン系第1溶媒と非アミン系第2溶媒の体積比が50〜90:10〜50である、請求項6に記載のポリイミド前駆体組成物。
- 前記アミン系第1溶媒が、炭素数2以上のアルキル基に置換された3次アミンである、請求項6に記載のポリイミド前駆体組成物。
- 前記非アミン系第2溶媒は、トルエンまたはテトラヒドロフランである、請求項6に記載のポリイミド前駆体組成物。
- シリカ系粒子を更に含む、請求項1に記載のポリイミド前駆体組成物。
- 請求項1から10のうちいずれか一項に記載のポリイミド前駆体組成物をガラス基板上に塗布した後に硬化させて得た光電素子のフレキシブル基板用ポリイミドフィルム。
- モデュラスが4GPa以下、引張ストレスが150MPa以下、熱膨脹係数(CTE)が100〜250℃で30ppm以上かつ200ppm以下である、請求項11に記載の光電素子のフレキシブル基板用ポリイミドフィルム。
- 前記フィルムは、350nm〜760nm波長の光に対する平均透過度が80%以上である、請求項11に記載のポリイミドフィルム。
- 請求項1から10のうちいずれか一項に記載のポリイミド前駆体組成物をガラス基板上に塗布した後に硬化させて得た、ガラス基板上にポリイミドフィルムが形成された積層体。
- 前記積層体は、100〜350℃の熱処理工程後に基板が受けるストレスが60MPa以下である、請求項14に記載の積層体。
- 前記ポリイミドフィルムは、モデュラスが4GPa以下、引張ストレスが150MPa以下、熱膨脹係数(CTE)が100〜250℃で30ppm以上かつ200ppm以下である、請求項14に記載の積層体。
- 請求項11に記載のポリイミドフィルムをフレキシブル基板として含む光電素子。
- 請求項11に記載のポリイミドフィルムで製造されたフレキシブル基板を含むフレキシブルディスプレイ。
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KR101993652B1 (ko) | 2019-09-24 |
EP3266808B1 (en) | 2020-12-09 |
CN106133025A (zh) | 2016-11-16 |
JP6501312B2 (ja) | 2019-04-17 |
US10544266B2 (en) | 2020-01-28 |
CN106133025B (zh) | 2019-03-12 |
EP3266808A1 (en) | 2018-01-10 |
KR20160108252A (ko) | 2016-09-19 |
EP3266808A4 (en) | 2018-10-03 |
US20170096530A1 (en) | 2017-04-06 |
TW201638158A (zh) | 2016-11-01 |
TWI595025B (zh) | 2017-08-11 |
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