JP2023507315A - エチレン/α-オレフィン共重合体を含む封止材フィルム用組成物およびそれを含む封止材フィルム - Google Patents
エチレン/α-オレフィン共重合体を含む封止材フィルム用組成物およびそれを含む封止材フィルム Download PDFInfo
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- 239000004711 α-olefin Substances 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 239000005977 Ethylene Substances 0.000 title claims abstract description 65
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims abstract description 58
- 239000003566 sealing material Substances 0.000 title claims abstract description 44
- 238000009826 distribution Methods 0.000 claims description 44
- 229920001577 copolymer Polymers 0.000 claims description 31
- 239000008393 encapsulating agent Substances 0.000 claims description 28
- 238000004132 cross linking Methods 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 18
- 239000000155 melt Substances 0.000 claims description 17
- 239000000565 sealant Substances 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 13
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 6
- 239000006096 absorbing agent Substances 0.000 claims description 6
- 239000012760 heat stabilizer Substances 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000004611 light stabiliser Substances 0.000 claims description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 4
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 229940106006 1-eicosene Drugs 0.000 claims description 2
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 claims description 2
- 229940069096 dodecene Drugs 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims 1
- 229940095068 tetradecene Drugs 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 139
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 80
- 239000010408 film Substances 0.000 description 65
- -1 cross-linking aid Substances 0.000 description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 47
- 229910052739 hydrogen Inorganic materials 0.000 description 45
- 239000001257 hydrogen Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 35
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- 239000000126 substance Substances 0.000 description 32
- 125000000217 alkyl group Chemical group 0.000 description 29
- 150000003623 transition metal compounds Chemical class 0.000 description 24
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- 125000000753 cycloalkyl group Chemical group 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 17
- 238000000034 method Methods 0.000 description 16
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- 150000002367 halogens Chemical class 0.000 description 15
- 239000000178 monomer Substances 0.000 description 14
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- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000003426 co-catalyst Substances 0.000 description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
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- 229910000077 silane Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000010292 electrical insulation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JZJDQBZDSBCARL-UHFFFAOYSA-N CC1=C(CC2=C1C1=C(S2)C=CC=C1)C Chemical compound CC1=C(CC2=C1C1=C(S2)C=CC=C1)C JZJDQBZDSBCARL-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 3
- 239000005341 toughened glass Substances 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-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
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- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
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- RURFJXKOXIWFJX-UHFFFAOYSA-N (2,3,4,6-tetrafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C=C(F)C(F)=C1F RURFJXKOXIWFJX-UHFFFAOYSA-N 0.000 description 1
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- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
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- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- ZDKPIHMFWCOHRD-UHFFFAOYSA-N 1-[[4-[4-bis(2,4-ditert-butylphenoxy)phosphorylphenyl]phenyl]-(2,4-ditert-butylphenoxy)phosphoryl]oxy-2,4-ditert-butylbenzene Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C ZDKPIHMFWCOHRD-UHFFFAOYSA-N 0.000 description 1
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZMPKTELQGVLZTD-UHFFFAOYSA-N tripropylborane Chemical compound CCCB(CCC)CCC ZMPKTELQGVLZTD-UHFFFAOYSA-N 0.000 description 1
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 238000010507 β-hydride elimination reaction Methods 0.000 description 1
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Abstract
Description
(b)分子量分布が1.8~2.3;
(c)メルトインデックス(Melt Index、 MI、 190℃、2.16kg荷重条件)が1~100dg/分;および
(d)クロス分別クロマトグラフィー(Cross-Fractionation Chromatography、CFC)により結晶化温度を測定時に示される結晶化ピークの半値幅(Full Width at Half Maximum、FWHM)が15以上。
本発明の封止材フィルム用組成物は、下記(a)~(d)の条件を満たすエチレン/α-オレフィン共重合体を含むことを特徴とする。
(b)分子量分布が1.8~2.3;
(c)メルトインデックス(Melt Index、 MI、 190℃、2.16kg荷重条件)が1~100dg/分;および
(d)クロス分別クロマトグラフィー(Cross-Fractionation Chromatography、CFC)により結晶化温度を測定時に示される結晶化ピークの半値幅(Full Width at Half Maximum、FWHM)が15以上。
本発明の封止材フィルム用組成物の製造方法は、下記化学式1および化学式2で表される遷移金属化合物を含む触媒組成物の存在下で、エチレンおよびα-オレフィン系単量体を重合することで、エチレン/α-オレフィン共重合体を製造するステップと、前記エチレン/α-オレフィン共重合体と、架橋剤、架橋助剤、およびシランカップリング剤を混合するステップと、を含むことを特徴とする。
R1は、水素;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数2~20のアルケニル;炭素数1~20のアルコキシ;炭素数6~20のアリール;炭素数7~20のアリールアルコキシ;炭素数7~20のアルキルアリール;または炭素数7~20のアリールアルキルであり、
R2およびR3は、それぞれ独立して、水素;ハロゲン;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数2~20のアルケニル;炭素数7~20のアリールアルキル;炭素数1~20のアルキルアミド;または炭素数6~20のアリールアミドであり、
R4およびR5は、それぞれ独立して、水素;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数6~20のアリール;または炭素数2~20のアルケニルであり、
R6~R9は、それぞれ独立して、水素;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数6~20のアリール;または炭素数2~20のアルケニルであり、
前記R6~R9のうち互いに隣接する2つ以上は、互いに連結されて環を形成してもよく、
Q1は、Si、C、N、P、またはSであり、
M1は、Ti、Hf、またはZrであり、
X1およびX2は、それぞれ独立して、水素;ハロゲン;炭素数1~20のアルキル;炭素数2~20のアルケニル;炭素数6~20のアリール;炭素数7~20のアルキルアリール;炭素数7~20のアリールアルキル;炭素数1~20のアルキルアミノ;または炭素数6~20のアリールアミノであり、
R10は、水素;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数2~20のアルケニル;炭素数1~20のアルコキシ;炭素数6~20のアリール;炭素数7~20のアリールアルコキシ;炭素数7~20のアルキルアリール;または炭素数7~20のアリールアルキルであり、
R11a~R11eは、それぞれ独立して、水素;ハロゲン;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数2~20のアルケニル;炭素数1~20のアルコキシ;または炭素数6~20のアリールであり、
R12は、水素;ハロゲン;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数2~20のアルケニル;炭素数6~20のアリール;炭素数7~20のアルキルアリール;炭素数7~20のアリールアルキル;炭素数1~20のアルキルアミド;または炭素数6~20のアリールアミドであり、
R13およびR14は、それぞれ独立して、水素;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数6~20のアリール;または炭素数2~20のアルケニルであり、
R15~R18は、それぞれ独立して、水素;炭素数1~20のアルキル;炭素数3~20のシクロアルキル;炭素数6~20のアリール;または炭素数2~20のアルケニルであり、
前記R15~R18のうち互いに隣接する2つ以上は、互いに連結されて環を形成してもよく、
Q2は、Si、C、N、P、またはSであり、
M2は、Ti、Hf、またはZrであり、
X3およびX4は、それぞれ独立して、水素;ハロゲン;炭素数1~20のアルキル;炭素数2~20のアルケニル;炭素数6~20のアリール;炭素数7~20のアルキルアリール;炭素数7~20のアリールアルキル;炭素数1~20のアルキルアミノ;または炭素数6~20のアリールアミノである。
-[Al(R19)-O]a-
R19は、それぞれ独立して、ハロゲンラジカル;炭素数1~20のヒドロカルビルラジカル;またはハロゲンで置換された炭素数1~20のヒドロカルビルラジカルであり、
aは2以上の整数であり、
[化学式4]
D(R19)3
前記化学式4中、
Dは、アルミニウムまたはホウ素であり、
R19は、それぞれ独立して、ハロゲンラジカル;炭素数1~20のヒドロカルビルラジカル;またはハロゲンで置換された炭素数1~20のヒドロカルビルラジカルであり、
[化学式5]
[L-H]+[Z(A)4]-または[L]+[Z(A)4]-
前記化学式5中、
Hは水素原子であり、
Zは13族元素であり、
Aは、それぞれ独立して、1以上の水素原子が置換基で置換されてもよい炭素数6~20のアリール;または炭素数1~20のアルキルであり、
前記置換基は、ハロゲン;炭素数1~20のヒドロカルビル;炭素数1~20のアルコキシ;または炭素数6~20のアリールオキシであり、
前記[L-H]+は、トリメチルアンモニウム;トリエチルアンモニウム;トリプロピルアンモニウム;トリブチルアンモニウム;ジエチルアンモニウム;トリメチルホスホニウム;またはトリフェニルホスホニウムであり、
前記[L]+は、N,N-ジエチルアニリニウム;またはトリフェニルカルボニウムである。
また、本発明の封止材フィルム用組成物は、封止材フィルムに含まれて用いられることができる。
以下、実施例により本発明をさらに詳細に説明する。しかし、下記実施例は、本発明を例示するためのものであって、これらにのみ本発明の範囲が限定されるのではない。
合成例1
(1)リガンド化合物の製造
<N-tert-ブチル-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-ジメチルシランアミンの合成>
100mLのシュレンクフラスコに、クロロ(1,2-ジメチル-6,7-ジヒドロ-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)ジメチルシランの化合物4.65g(15.88mmol)を定量して添加した後、これにTHF80mlを投入した。常温でtBuNH2(4eq、6.68ml)を投入した後、常温で3日間反応させた。反応後、THFを除去した後、ヘキサンで濾過した。溶媒乾燥後、黄色液体を4.50g(86%)の収率で得た。
1H-NMR (in CDCl3, 500 MHz): 7.99 (d, 1H), 7.83 (d, 1H), 7.35 (dd, 1H), 7.24 (dd, 1H), 3.49 (s, 1H), 2.37 (s, 3H), 2.17 (s, 3H), 1.27 (s, 9H), 0.19 (s, 3H), -0.17 (s, 3H).
1H-NMR (in CDCl3, 500 MHz): 7.99 (d, 1H), 7.68 (d, 1H), 7.40 (dd, 1H), 7.30 (dd, 1H), 3.22 (s, 1H), 2.67 (s, 3H), 2.05 (s, 3H), 1.54 (s, 9H), 0.58 (s, 3H), 0.57 (s, 3H), 0.40 (s, 3H), -0.45 (s, 3H).
(1)リガンド化合物の製造
<N-tert-ブチル-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(2-エチルフェニル)(メチル)シランアミンの合成>
(i)クロロ-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(2-エチルフェニル)(メチル)シランの製造
100mLのシュレンクフラスコに、1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン2g(1eq、9.99mmol)とTHF50mLを入れ、n-BuLi 4mL(1eq、9.99mmol、2.5M in ヘキサン)を-30℃で滴下した後、常温で一晩撹拌した。撹拌したLi-complex THF溶液を、ジクロロ(2-エチルフェニル)(メチル)シラン2.19mL(1.0eq、9.99mmol)とTHF50mLが入ったシュレンクフラスコに-78℃でカニューレーションした後、常温で一晩撹拌した。撹拌後、真空乾燥した後、ヘキサン60mLで抽出し、さらに真空乾燥した後、ヘキサンで洗浄してアイボリー色の固体3.83g(99%、dr=1:1)を得た。
100mLの丸底フラスコに、クロロ-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(2-エチルフェニル)(メチル)シラン3.87g(10.1mmol)を定量して添加した後、これにヘキサン40mLを投入した。常温でt-BuNH2(10eq、10.5mL)を投入した後、常温で2日間反応させた。反応後、ヘキサンを除去した後、ヘキサンで濾過した。溶媒乾燥後、黄色固体3.58g(84.4%、dr=1:0.8)を得た。
1H-NMR(CDCl3, 500 MHz): δ 7.98(t, 2H), 7.71(d, 1H), 7.55(d, 1H), 7.52(d, 1H), 7.48(d, 1H), 7.30(t, 1H), 7.26-7.22(m, 3H), 7.19(dd, 2H), 7.12-7.06(m, 3H), 7.00(t, 1H), 3.08-2.84(m, 4H) 3.05-2.84(m, 2H), 2.28(s, 3H), 2.20(s, 3H), 2.08(s, 3H), 1.62(s, 3H), 1.26-1.22(m, 6H), 1.06(s, 9H), 0.99(s, 9H), 0.05(s, 3H), -0.02(s, 3H)
1H NMR(CDCl3, 500 MHz): δ 7.90(d, 1H), 7.85(d, 1H), 7.74(d, 1H), 7.71(d, 1H), 7.40(d, 1H), 7.37(d, 1H), 7.27(d, 1H), 7.23(t, 2H), 7.17(t, 2H), 7.13(t, 2H), 7.06(t, 1H), 7.01(t, 1H), 6.86(t, 1H), 2.97-2.91(m, 2H), 2.90-2.82(m, 2H), 2.33(s, 3H), 2.22(s, 3H), 1.96(s, 3H), 1.68(s, 9H), 1.66(s, 9H), 1.38(s, 3H), 1.32(t, 3H), 1.24(t, 3H), 1.07(s, 3H), 0.88(s, 3H), 0.85(s, 3H), 0.72(s, 3H), 0.19(s, 3H), 0.01(s, 3H)
(1)リガンド化合物の製造
<N-tert-ブチル-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(メチル)(2-メチルフェニル)シランアミンの合成>
(i)クロロ-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(メチル)(2-メチルフェニル)シランの製造
250mLのシュレンクフラスコに、1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン2.0g(1.0eq、9.985mmol)とTHF50mLを入れ、n-BuLi 4.2mL(1.05eq、10.484mmol、2.5M in ヘキサン)を-30℃で滴下した後、常温で一晩撹拌した。撹拌したLi-complex THF溶液を、ジクロロ(O-トリルメチル)シラン2.46g(1.2eq、11.982mmol)とTHF30mLが入ったシュレンクフラスコに-78℃でカニューレーションした後、常温で一晩撹拌した。撹拌後、真空乾燥した後、ヘキサン100mLで抽出した。
抽出したクロロ-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(メチル)(2-メチルフェニル)シラン4.0g(1.0eq、10.0mmol)をヘキサン10mLで撹拌した後、t-BuNH2 4.2mL(4.0eq、40.0mmol)を常温で投入した後、常温で一晩撹拌した。撹拌後、真空乾燥した後、ヘキサン150mLで抽出した。溶媒乾燥後、べたつきのある液体4.26g(99%、dr=1:0.83)を得た。
1H-NMR(CDCl3, 500 MHz): δ 7.95(t, 2H), 7.70(d, 1H), 7.52(d, 1H), 7.47-7.44(m, 2H), 7.24-7.02(m, 9H), 6.97(t, 1H), 3.59(s, 1H), 3.58(s, 1H), 2.50(s, 3H), 2.44(s, 3H), 2.25(s, 3H), 2.16(s, 3H), 2.06(s, 3H), 1.56(s, 3H), 1.02(s, 9H), 0.95(s, 9H), -0.03(s, 3H), -0.11(s, 3H)
1H NMR(CDCl3, 500 MHz): δ 7.83(d, 1H), 7.80(d, 1H), 7.74(d, 1H), 7.71(d, 1H), 7.68(d, 1H), 7.37(d, 1H), 7.31-6.90(m, 9H), 6.84(t, 1H), 2.54(s, 3H), 2.47(s, 3H), 2.31(s, 3H), 2.20(s, 3H), 1.65(s, 9H), 1.63(s, 9H), 1.34(s, 3H), 1.00(s, 3H), 0.98(s, 3H), 0.81(s, 3H), 0.79(s, 3H), 0.68(s, 3H), 0.14(s, 3H), -0.03(s, 3H)
(1)リガンド化合物の製造
<N-tert-ブチル-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(メチル)(フェニル)シランアミンの合成>
(i)クロロ-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(メチル)(フェニル)シランの製造
250mLのシュレンクフラスコに、1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン10g(1.0eq、49.925mmol)とTHF100mLを入れ、n-BuLi 22mL(1.1eq、54.918mmol、2.5M in ヘキサン)を-30℃で滴下した後、常温で3時間撹拌した。撹拌したLi-complex THF溶液を、ジクロロ(メチル)(フェニル)シラン8.1mL(1.0eq、49.925mmol)とTHF70mLが入ったシュレンクフラスコに-78℃でカニューレーションした後、常温で一晩撹拌した。撹拌後、真空乾燥した後、ヘキサン100mLで抽出した。
抽出したクロロ-1-(1,2-ジメチル-3H-ベンゾ[b]シクロペンタ[d]チオフェン-3-イル)-1,1-(メチル)(フェニル)シランヘキサン溶液100mLにt-BuNH2 42mL(8eq、399.4mmol)を常温で投入した後、常温で一晩撹拌した。撹拌後、真空乾燥した後、ヘキサン150mLで抽出した。溶媒乾燥後、黄色固体13.36g(68%、dr=1:1)を得た。
1H NMR(CDCl3, 500 MHz): δ 7.93(t, 2H), 7.79(d,1H), 7.71(d,1H), 7.60(d, 2H), 7.48(d, 2H), 7.40~7.10(m, 10H, aromatic), 3.62(s, 1H), 3.60(s, 1H), 2.28(s, 6H), 2.09(s, 3H), 1.76(s, 3H), 1.12(s, 18H), 0.23(s, 3H), 0.13(s, 3H)
1H NMR(CDCl3, 500 MHz): δ 7.98(d, 1H), 7.94(d, 1H), 7.71(t, 6H), 7.50~7.30(10H), 2.66(s, 3H), 2.61(s, 3H), 2.15(s, 3H), 1.62(s, 9H), 1.56(s, 9H), 1.53(s, 3H), 0.93(s, 3H), 0.31(s, 3H), 0.58(s, 3H), 0.51(s, 3H), -0.26(s, 3H), -0.39(s, 3H)
製造例1
1.5Lの連続工程反応器に、ヘキサン溶媒を5.0kg/h、1-ブテンを0.76kg/hで投入しながら130℃で予熱した。トリイソブチルアルミニウム化合物(Tibal;0.045mmol/分)、前記合成例1および2で得た遷移金属化合物を3:7のモル比で混合した混合物(0.120μmol/分)、ジメチルアニリニウムテトラキス(ペンタフルオロフェニル)ボレート助触媒(0.144μmol/分)を同時に反応器に投入した。次いで、前記反応器内にエチレン(0.87kg/h)および水素ガス(20cc/分)を投入し、89barの圧力で、連続工程で130.1℃に60分以上維持させて共重合反応を進行することで、共重合体を得た。その後、真空オーブンで12時間以上乾燥した後、物性を測定した。
重合条件を下記表1のように変更したことを除き、製造例1と同様にエチレン/α-オレフィン共重合体を製造した。
実験例1
前記製造例および比較製造例で製造したエチレン/α-オレフィン共重合体に対して、下記の方法により物性を測定して表2に示した
ASTM D-792に準じて測定した。
ASTM D-1238(条件E、190℃、2.16Kg荷重)に準じて測定した。
ASTM D-1238に準じてMI10(条件E、190℃、10Kg荷重)およびMI2.16(条件E、190℃、2.16Kg荷重)を測定し、MI10/MI2.16により計算した。
溶融温度(Tm)および結晶化温度(Tc)は、PerkinElmer社製の示差走査熱量計(Differential Scanning Calorimeter、DSC 6000)を利用して得ることができる。具体的に、DSCを用いて、窒素雰囲気下で共重合体の温度を200℃に上昇させて5分間維持した後、30℃に冷却し、さらに温度を上昇させながらDSC曲線を観察した。この際、昇温速度および冷却速度はそれぞれ10℃/分とした。
重量平均分子量(Mw)と数平均分子量(Mn)は、生成された共重合体に対して下記のゲル浸透クロマトグラフィー(Gel Permeation Chromatography、GPC)分析条件下で測定し、分子量分布はMw/Mnの比から計算した。
-カラム:Agilent Olexis
-溶媒:卜リクロロベンゼン
-流速:1.0ml/分
-試料濃度:1.0mg/ml
-注入量:200μl
-カラム温度:160℃
-検出器(Detector):Agilent High Temperature RI detector
-標準(Standard):ポリスチレン(Polystyrene)(三次関数で補正)
-データプロセッシング(Data processing):Cirrus
測定設備としては、PolymerChar社のCFCを使用した。先ず、o-ジクロロベンゼンを溶媒とし、共重合体の溶液をCFC分析機内のオーブンで130℃で60分間完全に溶解した後、135℃に調整されたTREFカラムに注いだ後、95℃に冷却し、ここで45分間安定化させた。次いで、TREFカラムの温度を0.5℃/分の速度で-20℃に降下させた後、-20℃で10分間維持させた。その後、溶離量(質量%)を赤外線分光光度計を用いて測定した。次いで、予め設定された温度までTREFカラムの温度を20℃/分の速度で上昇させ、予め設定された時間(すなわち、約27分)中に到達した温度で前記温度を維持させる操作を、TREFの温度が130℃に達するまで繰り返し、それぞれの温度範囲の間に溶離された分画の量(質量%)を測定した。また、各温度で溶離された分画をGPCカラムに送り、o-ジクロロベンゼンを溶媒として使用した点を除き、GPC測定原理と同様に分子量(Mw)を測定した。FWHM値は、CFCにより得た温度による溶出量グラフ(dW/dT vs T)をプログラム(Origin)上でガウス曲線(Gaussian curve)の形態でフィッティング(fitting)してから計算した。
実施例1
前記製造例1のサンプル500gに、t-ブチル1-(2-エチルヘキシル)モノパーオキシカーボネート(TBEC)1phr(parts per hundred rubber)、トリアリルイソシアヌレート(TAIC)0.5phr、メタクリルオキシプロピルトリメトキシシラン(MEMO)0.2phrを投入し、封止材フィルム用組成物を製造した。その後、40℃で1時間ソーキング(Soaking)してから15時間エージングした。
サンプルとして、それぞれ製造例2~4、比較製造例1~7の共重合体を使用したことを除き、前記実施例1と同様に封止材フィルムを製造した。
実験例2
2つの離型フィルム(厚さ:約100μm)の間に上記で製造された厚さ500μmの封止材フィルム(15cm×15cm)を入れ、真空ラミネータにて、工程温度150℃、工程時間19分30秒(5分真空/1分加圧/13分30秒圧力を続く)間ラミネートして架橋させた。
23℃±1の温度と50%±3の湿度条件下で、Agilent 4339B High-Resistance meter(アジレント・テクノロジー株式会社製)を用いて、1000Vの電圧を60秒間加えながら測定した。
550nmでの光透過率を、Shimadzu UV-3600分光光度計を用いて測定した。
-測定モード:transmittance
-波長インターバル:1nm
-測定速度:medium
実験例3
前記実施例2または比較例3の封止材フィルム(厚さ500μm)、フッ素系バックシート、低鉄強化ガラス、および結晶質シリコン太陽電池を用いて太陽電池モジュールを製造した。配列されたモジュールの内部を、真空ラミネータ(Vacuum Laminator)を用いて150℃の条件で20分間減圧しながら、太陽電池モジュールを製造した。
上記で製造した太陽電池モジュールを対象として初期出力を測定し、85℃、85%RH、-1,000V下で288時間経過した後の、初期出力に対する損失率(%)を計算した。
Claims (12)
- 下記(a)~(d)の条件を満たすエチレン/α-オレフィン共重合体を含む封止材フィルム用組成物:
(a)密度が0.85~0.89g/cc;
(b)分子量分布が1.8~2.3;
(c)メルトインデックス(Melt Index、 MI、 190℃、2.16kg荷重条件)が1~100dg/分;および
(d)クロス分別クロマトグラフィー(Cross-Fractionation Chromatography、CFC)により結晶化温度を測定時に示される結晶化ピークの半値幅(Full Width at Half Maximum、FWHM)が15以上。 - 前記メルトインデックスが2~20dg/分である、請求項1に記載の封止材フィルム用組成物。
- 前記結晶化ピークの半値幅が16~50である、請求項1又は2に記載の封止材フィルム用組成物。
- 前記エチレン/α-オレフィン共重合体の溶融温度が70℃以下である、請求項1~3のいずれか一項に記載の封止材フィルム用組成物。
- 前記エチレン/α-オレフィン共重合体の重量平均分子量(Mw)が40,000~150,000g/molである、請求項1~4のいずれか一項に記載の封止材フィルム用組成物。
- 前記エチレン/α-オレフィン共重合体は、メルトインデックス(MI2.16、190℃、2.16kg荷重条件)に対するメルトインデックス(MI10、190℃、10kg荷重条件)値である溶融流動指数(MFRR、Melt Flow Rate Ratio、 MI10/MI2.16)が8.0以下である、請求項1~5のいずれか一項に記載の封止材フィルム用組成物。
- 前記エチレン/α-オレフィン共重合体の結晶化温度が70℃以下である、請求項1~6のいずれか一項に記載の封止材フィルム用組成物。
- 前記α-オレフィンは、プロピレン、1-ブテン、1-ペンテン、4-メチル-1-ペンテン、1-ヘキセン、1-ヘプテン、1-オクテン、1-デセン、1-ウンデセン、1-ドデセン、1-テトラデセン、1-ヘキサデセン、および1-エイコセンから構成される群から選択される1種以上を含む、請求項1~7のいずれか一項に記載の封止材フィルム用組成物。
- 前記α-オレフィンは、共重合体に対して0超過99モル%以下で含まれる、請求項1~8のいずれか一項に記載の封止材フィルム用組成物。
- 不飽和シラン化合物、アミノシラン化合物、架橋剤、架橋助剤、光安定剤、UV吸収剤、および熱安定剤からなる群から選択される1種以上をさらに含む、請求項1~9のいずれか一項に記載の封止材フィルム用組成物。
- 請求項1から10の何れか一項に記載の封止材フィルム用組成物を含む封止材フィルム。
- 請求項11に記載の封止材フィルムを含む太陽電池モジュール。
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KR101924198B1 (ko) | 2015-12-23 | 2018-11-30 | 주식회사 엘지화학 | 필름 가공성 및 투명도가 우수한 저밀도 폴리에틸렌 공중합체 |
KR102083001B1 (ko) | 2016-09-23 | 2020-02-28 | 주식회사 엘지화학 | 올레핀계 공중합체 및 이의 제조 방법 |
KR101797890B1 (ko) * | 2017-01-20 | 2017-11-14 | 한화케미칼 주식회사 | 혼성 촉매 조성물, 이의 제조방법, 및 이를 이용하여 제조된 폴리올레핀 |
US11339235B2 (en) | 2017-12-22 | 2022-05-24 | Lg Chem, Ltd. | Olefin-based polymer |
KR102342780B1 (ko) | 2018-02-08 | 2021-12-23 | 주식회사 엘지화학 | 혼성 담지 메탈로센 촉매의 제조방법 |
KR102421535B1 (ko) | 2018-05-04 | 2022-07-20 | 주식회사 엘지화학 | 에틸렌/알파-올레핀 공중합체, 이의 제조방법 |
WO2019212303A1 (ko) | 2018-05-04 | 2019-11-07 | 주식회사 엘지화학 | 에틸렌/알파-올레핀 공중합체 및 이의 제조방법 |
KR102622329B1 (ko) * | 2018-05-04 | 2024-01-09 | 주식회사 엘지화학 | 에틸렌/알파-올레핀 공중합체, 이의 제조방법 및 이를 포함하는 광학필름용 수지 조성물 |
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2020
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- 2020-12-08 JP JP2022535672A patent/JP7418900B2/ja active Active
- 2020-12-08 US US17/779,337 patent/US11884801B2/en active Active
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