JP4894284B2 - Capture agent sheet for organic electronic device and organic electronic device - Google Patents
Capture agent sheet for organic electronic device and organic electronic device Download PDFInfo
- Publication number
- JP4894284B2 JP4894284B2 JP2006033659A JP2006033659A JP4894284B2 JP 4894284 B2 JP4894284 B2 JP 4894284B2 JP 2006033659 A JP2006033659 A JP 2006033659A JP 2006033659 A JP2006033659 A JP 2006033659A JP 4894284 B2 JP4894284 B2 JP 4894284B2
- Authority
- JP
- Japan
- Prior art keywords
- organic electronic
- sheet
- scavenger
- electronic device
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000002516 radical scavenger Substances 0.000 claims description 66
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Chemical group 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 239000013589 supplement Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 39
- 229910052760 oxygen Inorganic materials 0.000 description 39
- 239000001301 oxygen Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000011368 organic material Substances 0.000 description 15
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 230000002000 scavenging effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 3
- -1 phenylethynyl group Chemical group 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- USJZIJNMRRNDPO-UHFFFAOYSA-N tris-decylalumane Chemical compound CCCCCCCCCC[Al](CCCCCCCCCC)CCCCCCCCCC USJZIJNMRRNDPO-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 2
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MSZVPIUTCYUSLM-UHFFFAOYSA-N bis(2-methylpropyl)-phenylalumane Chemical compound CC(C)C[Al](CC(C)C)C1=CC=CC=C1 MSZVPIUTCYUSLM-UHFFFAOYSA-N 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- YSTSZKYCLOUEDE-UHFFFAOYSA-N dimethyl(phenyl)alumane Chemical compound C[Al](C)C1=CC=CC=C1 YSTSZKYCLOUEDE-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- GNPSMYTXIPVJDU-UHFFFAOYSA-N dioctylalumane Chemical compound C(CCCCCCC)[AlH]CCCCCCCC GNPSMYTXIPVJDU-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 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 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FBGKRDKNTJRUQJ-UHFFFAOYSA-N methyl(diphenyl)alumane Chemical compound C=1C=CC=CC=1[Al](C)C1=CC=CC=C1 FBGKRDKNTJRUQJ-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 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
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
- HELJHQMKIXWTNN-UHFFFAOYSA-N tricyclopropylalumane Chemical compound C1CC1[Al](C1CC1)C1CC1 HELJHQMKIXWTNN-UHFFFAOYSA-N 0.000 description 1
- XBEXIHMRFRFRAM-UHFFFAOYSA-N tridodecylalumane Chemical compound CCCCCCCCCCCC[Al](CCCCCCCCCCCC)CCCCCCCCCCCC XBEXIHMRFRFRAM-UHFFFAOYSA-N 0.000 description 1
- VYDLWQPLCBCJGV-UHFFFAOYSA-N tridodecylborane Chemical compound CCCCCCCCCCCCB(CCCCCCCCCCCC)CCCCCCCCCCCC VYDLWQPLCBCJGV-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- OGJDNTCMTVTFAS-UHFFFAOYSA-N trioctylborane Chemical compound CCCCCCCCB(CCCCCCCC)CCCCCCCC OGJDNTCMTVTFAS-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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- FHAOCGKAMRAFMM-UHFFFAOYSA-N tris(2-ethylhexyl)alumane Chemical compound CCCCC(CC)C[Al](CC(CC)CCCC)CC(CC)CCCC FHAOCGKAMRAFMM-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
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/846—Passivation; Containers; Encapsulations comprising getter material or desiccants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Description
本発明は、酸素や水分に対して優れた捕捉能力を有する有機電子デバイス用捕捉剤シート、前記有機電子デバイス用捕捉剤シートの製造方法、及び、前記有機電子デバイス用捕捉剤シートを用いた有機電子デバイスに関する。 The present invention relates to a scavenger sheet for organic electronic devices having excellent scavenging ability for oxygen and moisture, a method for producing the scavenger sheet for organic electronic devices, and an organic material using the scavenger sheet for organic electronic devices. It relates to electronic devices.
従来から、有機ＥＬ（Eletroluminescence）、有機ＴＦＴ（Thin Film Transistor）、有機太陽電池等の有機化合物を用いた電子デバイスである有機電子デバイスが開発されている。
これらの有機電子デバイスは、水や酸素の痕跡量の存在によってその性能が鋭敏にしかも著しく悪影響を受ける有機化合物を使用しているため、痕跡量程度の微量の酸素及び／又は水が存在する場合でも、これらの影響を受けて性能が劣化する。
2. Description of the Related Art Conventionally, organic electronic devices that are electronic devices using organic compounds such as organic EL (Eletroluminescence), organic TFT (Thin Film Transistor), and organic solar cells have been developed.
Since these organic electronic devices use organic compounds whose performance is sensitive and significantly adversely affected by the presence of trace amounts of water and oxygen, trace amounts of oxygen and / or water are present. However, performance deteriorates under these influences.
これらの有機電子デバイスは、その主要な機能を発揮するために必要な部分に有機材料を用いており、前記有機材料に電子的な働きを行わせることによって前記機能を発揮するように構成された電子素子である。例えば、有機電子デバイスは、有機材料に電子及び正孔の注入、取り出しを繰り返すことによって種々の機能を発現する電子デバイスとして構成されている。すなわち、その有機材料を繰り返して酸化還元反応を行わせることをデバイス作動機構としている。 These organic electronic devices use an organic material in a part necessary for exhibiting the main functions, and are configured to exhibit the functions by causing the organic materials to perform electronic functions. It is an electronic element. For example, an organic electronic device is configured as an electronic device that exhibits various functions by repeatedly injecting and extracting electrons and holes from an organic material. That is, the device operating mechanism is to repeatedly perform the oxidation-reduction reaction of the organic material.
有機材料及びその酸化体又は還元体は、本質的な酸素及び／又は水との化学的反応性が無機材料に対して高く、これが有機材料を劣化させ本来の電子デバイスとしての機能を損ね、性能が劣化する原因となる。
また、有機電子デバイスを配置するには通常密封容器が用いられ、これには極力、酸素及び／又は水分を痕跡量以下に保つことが必要である。従って、有機電子デバイスの作製は、超高真空下及び／又は不活性雰囲気下で製造操作を行っている。
Organic materials and their oxidants or reductants have a high chemical reactivity with inorganic materials, which is essential for oxygen and / or water, which degrades organic materials and impairs their original functions as electronic devices. Cause deterioration.
In addition, a sealed container is usually used to arrange the organic electronic device, and it is necessary to keep oxygen and / or moisture below a trace amount as much as possible. Therefore, an organic electronic device is manufactured by performing a manufacturing operation under an ultrahigh vacuum and / or an inert atmosphere.
さらに有機電子デバイスの構成として、材料由来のアウトガス及び／又は密封容器の封止部分から侵入する劣化因子を捕捉する捕捉剤を電子デバイス内に配することによって、これらの影響を出来るだけ小さくするように配慮している（例えば、特許文献１参照）。
しかしながら、現在までに知られているこれらの捕捉剤は、系内の酸素及び／又は水を除去する能力が十分なものは少ない。また同一の物質によって、水及び酸素を共に捕捉しうる捕捉材は極めて少ない。
Furthermore, as a constitution of the organic electronic device, by arranging a capture agent that captures outgas derived from the material and / or a deterioration factor entering from the sealed portion of the sealed container in the electronic device, these effects are made as small as possible. (For example, refer to Patent Document 1).
However, few of these scavengers known to date have sufficient capacity to remove oxygen and / or water in the system. In addition, there are very few trapping materials that can trap both water and oxygen by the same substance.
例えば、有機ＥＬディスプレイは自発光型電子デバイスであり、発光層にむけてエレクトロンとホールを注入し、発光層を励起して、その励起状態から基底状態に遷移する時に発光するメカニズムである。したがって、微量の酸素や水があると、励起エネルギーをクエンチしたり、また、発光分子が水や酸素の攻撃を受けてダークスッポトを形成するため、有機ＥＬデバイスの寿命に対して非常に悪影響を与える。このため、有機ＥＬデバイスには系内に捕捉剤を設置して微量の水分や酸素を吸収させてこれらの影響を排除するようにしている。 For example, an organic EL display is a self-luminous electronic device having a mechanism that emits light when electrons and holes are injected into a light emitting layer to excite the light emitting layer and transition from the excited state to the ground state. Therefore, if there is a small amount of oxygen or water, the excitation energy is quenched, or the light emitting molecules are attacked by water or oxygen to form dark spots, which has a very adverse effect on the lifetime of the organic EL device. give. For this reason, in organic EL devices, a trapping agent is installed in the system to absorb a small amount of moisture and oxygen to eliminate these effects.
しかしながら、現在までに知られている捕捉剤は系内の水分を除去しうる捕捉剤が大部分で、系内の酸素を除去しうる捕捉剤には適当なものがなく、そのため水分と酸素をともに除去できる捕捉剤が求められている。
特許文献２には、水及び酸素に非常に高い反応性を持つアルカリ（土類）金属類を捕捉剤として用いる発明が開示されているが、アルカリ（土類）金属はその取り扱いが著しく危険を伴う煩雑なものであり、デバイス内に配する場合もその方法が限定されている。
However, most of the scavengers known to date are scavengers that can remove moisture in the system, and there are no suitable scavengers that can remove oxygen in the system, so moisture and oxygen can be removed. There is a need for a scavenger that can be removed together.
Patent Document 2 discloses an invention in which alkali (earth) metals having very high reactivity with water and oxygen are used as a scavenger, but handling of alkali (earth) metals is extremely dangerous. This is a complicated process, and the method is also limited when it is arranged in the device.
また、アルカリ（土類）金属の水及び／又は酸素の捕捉機構を考察すると、特に水との反応によって水素を発生することになり、水素の高い蒸気圧は有機電子デバイスの封止を破壊する高い可能性がある。
さらに、これらを配したデバイスが廃棄処分や事故などで破壊され、通常の大気雰囲気中の高濃度な水及び／又は酸素に晒された場合、自然発火の可能性があり危険なものである。それ故、一般的な捕捉材として使用するには適当ではない。
Also, considering the water and / or oxygen trapping mechanism of alkali (earth) metal, hydrogen will be generated especially by reaction with water, and the high vapor pressure of hydrogen will destroy the sealing of organic electronic devices. There is a high possibility.
Furthermore, when a device provided with these is destroyed by disposal or accident and exposed to high-concentration water and / or oxygen in a normal atmospheric atmosphere, there is a possibility of spontaneous ignition and danger. Therefore, it is not suitable for use as a general capturing material.
一方、特許文献３に記載された発明では、有機ＥＬ層を構成する材料を捕捉剤として用いることを特徴としている。しかし、水及び／又は酸素との反応速度は電子ないし正孔を授受している、すなわち励起状態にある有機材料の方が著しく速い。そのため捕捉剤として提案されている有機材料が本質的にその機能を高く保持しているか疑問であり、さらに透明性に関してもヘテロ元素（酸素、窒素、硫黄など）を含む有機材料が劣化した場合に着色してしまうことは一般的に知られており、捕捉剤層が薄いとしても問題となる可能性がある。
このように、従来の捕捉剤は、酸素及び水素の双方を捕捉できるものはあまりなく、あったとしても取扱が危険なものである。
On the other hand, the invention described in Patent Document 3 is characterized in that a material constituting the organic EL layer is used as a scavenger. However, the reaction rate with water and / or oxygen is remarkably faster in an organic material that is transferring electrons or holes, that is, in an excited state. For this reason, it is doubtful whether the organic material proposed as a scavenger inherently retains its function high, and in terms of transparency, when organic materials containing hetero elements (oxygen, nitrogen, sulfur, etc.) deteriorate Coloring is generally known and can be problematic even if the scavenger layer is thin.
Thus, there are not many conventional scavengers capable of scavenging both oxygen and hydrogen, and if any, they are dangerous to handle.
本発明は、取り扱いが容易で、水及び酸素に対して強い捕捉能力を有する有機電子デバイス用捕捉剤シートを提供することを課題としている。
また、本発明は、取り扱いが容易で、水及び酸素に対して強い捕捉能力を有する有機電子デバイス用捕捉剤シートの製造方法を提供することを課題としている。
また、本発明は、取り扱いが容易で、水や酸素の影響が小さく長寿命な有機電子デバイスを提供することを課題としている。
An object of the present invention is to provide a scavenger sheet for organic electronic devices that is easy to handle and has a strong scavenging ability for water and oxygen.
Moreover, this invention makes it a subject to provide the manufacturing method of the capture | acquisition agent sheet | seat for organic electronic devices which is easy to handle and has a strong capture capability with respect to water and oxygen.
Another object of the present invention is to provide an organic electronic device that is easy to handle, has little influence of water and oxygen, and has a long lifetime.
本発明によれば、下記化学式で示される捕捉剤をシート状部材に被着して成ることを特徴とする有機電子デバイス用捕捉剤シートが提供される。
Ｒ１Ｒ２Ｒ３Ｍ
但し、Ｒ１、Ｒ２及びＲ３は、各々、水素原子、ハロゲン原子、アルキル基、アルケニル基、アルキニル基、環式アルキル基及、アリール基、アルコキシ基及びカルボキシル基からなる群より選ばれた１種のものであって、互いに同じでも異なっていてもよいが、補足剤として１つ以上のＣ−Ｍ結合を有するように選ばれたものである。Ｍはアルミニウム又はボロンである。
According to the present invention, there is provided a scavenger sheet for organic electronic devices, characterized in that a scavenger represented by the following chemical formula is applied to a sheet-like member.
R 1 R 2 R 3 M
Provided that R 1 , R 2 and R 3 are each selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyclic alkyl group, an aryl group, an alkoxy group and a carboxyl group. One, which may be the same or different from each other, but has been selected as a supplement with one or more CM bonds. M is aluminum or boron.
ここで、前掲の捕捉剤と他の捕捉剤とを混合した捕捉剤を、前記シート状部材に被着して成るように構成してもよい。
また、前記他の捕捉剤が、前掲の捕捉剤とは反応しない有機溶媒に溶解するものであるようにしてもよい。
Here, you may comprise so that the capture | acquisition agent which mixed the capture | acquisition agent mentioned above and other capture | acquisition agents may adhere to the said sheet-like member.
The other scavenger may be dissolved in an organic solvent that does not react with the scavenger described above.
また、本発明によれば、前記いずれか一に記載の捕捉剤とバインダーを混合して前記シート状部剤に塗布することを特徴とする有機電子デバイス用捕捉剤シートの製造方法が提供される。
また、本発明によれば、前記いずれか一に記載の有機電子デバイス用捕捉剤シートを所定の位置に被着させて成ることを特徴とする有機電子デバイスが提供される。
In addition, according to the present invention, there is provided a method for producing a capturing agent sheet for organic electronic devices, wherein the capturing agent according to any one of the above and a binder are mixed and applied to the sheet-shaped member. .
According to the present invention, there is provided an organic electronic device comprising the organic electronic device scavenger sheet according to any one of the above, which is deposited at a predetermined position.
本発明の有機電子デバイス用捕捉剤シートは、取り扱いが容易で、水分捕捉能及び酸素捕捉能ともに優れた捕捉剤を使用している。したがって、有機電子デバイスに使用することにより、有機電子デバイスに悪影響を与える水分や酸素を除去することが可能になる。よって、有機電子デバイスの長寿命化を図ることが可能になる。
また、本発明によれば、簡単な方法によって有機電子デバイス用捕捉剤シートを製造することが可能になる。
また、本発明の有機電子デバイスによれば、水や酸素による寿命低下を抑制することができるため、取り扱いが容易で、長寿命化が可能になるという効果を奏する。
The scavenger sheet for organic electronic devices of the present invention is easy to handle and uses a scavenger excellent in both moisture scavenging ability and oxygen scavenging ability. Therefore, by using it in an organic electronic device, it becomes possible to remove moisture and oxygen that adversely affect the organic electronic device. Therefore, it is possible to extend the life of the organic electronic device.
Moreover, according to this invention, it becomes possible to manufacture the capture | acquisition agent sheet | seat for organic electronic devices by a simple method.
In addition, according to the organic electronic device of the present invention, it is possible to suppress a decrease in life due to water or oxygen, and therefore, there is an effect that the handling is easy and the life can be extended.
前記問題点を解決するために種々検討した結果、捕捉剤として優れた性能を持つ下記化学式（１）で表される化合物を見出した。前記、捕捉剤をバインダー（粘着剤）と混合してシート状部材に塗布し捕捉剤シートを作製し、有機電子デバイス中の所望の位置に前記捕捉剤シートを貼付し、前記有機電子デバイス中の水分や酸素を吸収・吸着して捕捉する。
従来の捕捉剤が水分のみの吸収能力しかなかったが、本発明の実施の形態に係る捕捉剤は水分以外の酸素の吸収に対しても優れた能力を有する特徴がある。そのため、従来、有機電子デバイス用に検討されてきた種々の捕捉剤より優れており、又、安全に使用できる。
尚、有機電子デバイスは、その主要な機能を発揮するために必要な部分に有機材料を用いており、前記有機材料に電子的な働きを行わせることによって機能を発揮するように構成された電子素子である。
As a result of various studies to solve the above problems, a compound represented by the following chemical formula (1) having excellent performance as a scavenger was found. The scavenger is mixed with a binder (adhesive) and applied to a sheet-like member to produce a scavenger sheet, and the scavenger sheet is pasted at a desired position in the organic electronic device. Absorbs and adsorbs moisture and oxygen.
Although the conventional scavenger had only the ability to absorb moisture, the scavenger according to the embodiment of the present invention has a characteristic of having an excellent ability to absorb oxygen other than moisture. Therefore, it is superior to various scavengers that have been conventionally studied for organic electronic devices, and can be used safely.
In addition, the organic electronic device uses an organic material in a part necessary for exhibiting its main function, and an electronic device configured to exhibit a function by causing the organic material to perform an electronic function. It is an element.
以下に本発明の実施の形態についてさらに詳細に説明する。本発明の実施の形態に係る有機電子デバイス用補足剤シートに用いる捕捉剤は、下記式（１）で表される化合物である。
Ｒ１Ｒ２Ｒ３Ｍ ・・・（１）
但し、Ｒ１、Ｒ２及びＲ３は、各々、水素原子、ハロゲン原子、アルキル基、アルケニル基、アルキニル基、環式アルキル基及、アリール基、アルコキシ基及びカルボキシル基からなる群より選ばれた１種のものであって、互いに同じでも異なっていてもよいが、補足剤として１つ以上のＣ−Ｍ結合を有するように選ばれたものである。Ｍはアルミニウム又はボロンである。
Hereinafter, embodiments of the present invention will be described in more detail. The scavenger used for the supplementary sheet for organic electronic devices according to the embodiment of the present invention is a compound represented by the following formula (1).
R 1 R 2 R 3 M (1)
Provided that R 1 , R 2 and R 3 are each selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyclic alkyl group, an aryl group, an alkoxy group and a carboxyl group. One, which may be the same or different from each other, but has been selected as a supplement with one or more CM bonds. M is aluminum or boron.
Ｒ１、Ｒ２、Ｒ３の基は、炭素数が１〜２０好ましくは２〜１８であり、同一でも異なっていてもよい。これらの化合物は水分、酸素などがこのＣ−Ｍ結合と反応することにより、有機電子デバイス用捕捉剤としての有用な役割を果たす。
例えば、水との反応は、
Ｃ−Ｍ ＋ Ｈ２Ｏ → Ｃ−Ｈ ＋ Ｍ（ＯＨ）
酸素も同様にＣ−Ｍ結合で、次のように反応する。
２Ｃ−Ｍ ＋ Ｏ２ → ２Ｃ−Ｏ−Ｍ
The groups R 1 , R 2 and R 3 have 1 to 20 carbon atoms, preferably 2 to 18 carbon atoms, and may be the same or different. These compounds play a useful role as a scavenger for organic electronic devices by reacting moisture, oxygen, and the like with the CM bond.
For example, the reaction with water
C-M + H 2 O → C-H + M (OH)
Oxygen also reacts as follows with a CM bond.
2C-M + O 2 → 2C-OM
Ｒ１、Ｒ２及びＲ３の具体例としては、水素原子、ハロゲン原子、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、ヘキサデシル基、オクタデシル基、の如き炭素数１〜１８のアルキル基、プロペニル基、ブテニル基、オクテニル基、ドデセニル基、オクタデセニル基の如き不飽和基を有するアルケニル基、プロピニル基、フェニルエチニル基の如きアルキニル基、シクロプロピル基、シクロヘキシル基の如き脂環式アルキル基、フェニル基、ベンジル基の如きアリール基、エトキシ基、プロポキシ基、ブトキシ基などのアルコキシ基、などを好適に挙げることができる。
これらアルキル基、アルケニル基、アルキニル基、アルコキシ基は直鎖状でもよく環状でもよく、また分岐していてもよい。
Specific examples of R 1 , R 2 and R 3 include hydrogen atom, halogen atom, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, C1-C18 alkyl group such as undecyl group, dodecyl group, hexadecyl group, octadecyl group, propenyl group, butenyl group, octenyl group, dodecenyl group, alkenyl group having an unsaturated group such as octadecenyl group, propynyl group, Preferable examples include alkynyl groups such as phenylethynyl group, alicyclic alkyl groups such as cyclopropyl group and cyclohexyl group, aryl groups such as phenyl group and benzyl group, alkoxy groups such as ethoxy group, propoxy group and butoxy group. be able to.
These alkyl group, alkenyl group, alkynyl group and alkoxy group may be linear, cyclic or branched.
前記式（１）で示される化合物の具体例としては、トリエチルアルミニウム、トリ−ｎ−プロピルアルミニウム、トリイソプロピルアルミニウム、トリシクロプロピルアルミニウム、トリ−ｎ−ブチルアルミニウム、トリイソブチルアルミニウム、トリ‐ｔ−ブチルアルミニウム、トリ−２−メチルブチルアルミニウム、トリ−ｎ−ヘキシルアルミニウム、トリシクロヘキシルアルミニウム、トリ（２−エチルヘキシル）アルミニウム、トリ−ｎ−オクチルアルミニウム、トリ−ｎ−デシルアルミニウム、トリフェニルアルミニウム、トリベンジルアルミニウム、ジメチルフェニルアルミニウム、ジブチルフェニルアルミニウム、ジイソブチルフェニルアルミニウム、メチルジフェニルアルミニウム、エトキシヂエチルアルミニウム、エトキシジ−ｎ−オクチルアルミニウム、トリエチルボラン、トリブチルボラン、トリ−ｎ−オクチルボラン、トリ−ｎ−ドデシルボラン、トリフェニルボランなどを挙げることができる。これらの化合物は、単独でも、あるいは２種類以上の化合物を混合して使用することもできる。 Specific examples of the compound represented by the formula (1) include triethylaluminum, tri-n-propylaluminum, triisopropylaluminum, tricyclopropylaluminum, tri-n-butylaluminum, triisobutylaluminum, tri-t-butyl. Aluminum, tri-2-methylbutylaluminum, tri-n-hexylaluminum, tricyclohexylaluminum, tri (2-ethylhexyl) aluminum, tri-n-octylaluminum, tri-n-decylaluminum, triphenylaluminum, tribenzylaluminum , Dimethylphenylaluminum, dibutylphenylaluminum, diisobutylphenylaluminum, methyldiphenylaluminum, ethoxydiethylaluminum, ethoxy Can be mentioned di -n- octyl aluminum, triethyl borane, tributyl borane, tri -n- octyl borane, tri -n- dodecyl borane, and the like triphenyl borane. These compounds can be used alone or in admixture of two or more kinds.
水分、酸素などとの反応で発生する生成物の蒸気圧を考えると、炭素数が６以上の基で好ましくはトリ−ｎ−ヘキシルアルミニウム、トリ−ｎ−オクチルアルミニウム、トリ−ｎ−ドデシルアルミニウム、などである。
本発明の実施の形態に用いられる捕捉剤は、前記式（１）で示した捕捉剤に他の捕捉剤（水分は捕捉するが酸素は捕捉しない捕捉剤である乾燥剤を含む。）を混合することもできる。前記他の捕捉剤としては、化学的に水分子と反応するもの、物理的に水分子を吸着するもの、その他いずれのものでもよい。
Considering the vapor pressure of the product generated by the reaction with moisture, oxygen, etc., preferably a group having 6 or more carbon atoms, preferably tri-n-hexyl aluminum, tri-n-octyl aluminum, tri-n-dodecyl aluminum, Etc.
The scavenger used in the embodiment of the present invention is a mixture of the scavenger represented by the formula (1) with another scavenger (including a desiccant that captures moisture but does not trap oxygen). You can also The other scavenger may be any one that chemically reacts with water molecules, one that physically adsorbs water molecules, or any other one.
化学的に水分子と反応するものとしては、金属酸化物、硫酸塩、金属ハロゲン化物、有機金属化合物などが挙げられる。金属酸化物としては、酸化カルシウム、酸化バリウム、酸化マグネシウムなどが挙げられる。硫酸塩としては、硫酸リチウム、硫酸ナトリウム、硫酸カルシウム、硫酸マグネシウムなどが挙げられる。金属ハロゲン化物としては、塩化カルシウム、塩化マグネシウム、塩化ストロンチュウムなどが挙げられる。有機金属化合物としては、トリアシルシクロボロキシン、アルミニュウムオキサイドオクチレートなどが挙げられる。
物理的に吸着するものとしては、ゼオライト、シリカゲル、活性アルミナなどが挙げられる。
Examples of those that chemically react with water molecules include metal oxides, sulfates, metal halides, and organometallic compounds. Examples of the metal oxide include calcium oxide, barium oxide, and magnesium oxide. Examples of the sulfate include lithium sulfate, sodium sulfate, calcium sulfate, and magnesium sulfate. Examples of the metal halide include calcium chloride, magnesium chloride, strontium chloride and the like. Examples of the organometallic compound include triacylcycloboroxine and aluminum oxide octylate.
Examples of the material that physically adsorbs include zeolite, silica gel, activated alumina, and the like.
前記式（１）で表される捕捉剤と混合するその他の捕捉剤は、前記式（１）の捕捉剤をトルエン、キシレン、パラフィン、流動パラフィン、デカリン、ジグライムなどの非水溶媒である芳香族有機溶媒、脂肪族溶媒、エーテル系溶媒などに溶解した溶液中に均一に溶解、分散でき、少なくとも沈殿しないものが好ましい。特に好ましいのはボロンオキサイドオクチレート、アルミニウムオキサイドオクチレートなどである。 The other scavenger mixed with the scavenger represented by the formula (1) is an aromatic that is a non-aqueous solvent such as toluene, xylene, paraffin, liquid paraffin, decalin, diglyme, etc. Those that can be uniformly dissolved and dispersed in a solution dissolved in an organic solvent, an aliphatic solvent, an ether solvent, etc., and at least do not precipitate are preferable. Particularly preferred are boron oxide octylate, aluminum oxide octylate and the like.
本発明の実施の形態に用いられる捕捉剤のバインダーの種類としては、無機系の材料でも良く、有機系の材料でも良い。
無機系バインダーとしては、アルコキシシランのポリマーが挙げられる。アルコキシシランとしてはテトラメトキシシラン、メチルトリメトキシシラン、エチルトリメトキシシラン、ジメトキジメチルシラン、ジメトキシジエチルシラン、テトラエトキシシラン、メチルトリエトキシシラン、エチルトリエトキシシラン、ジエトキシジメチルシラン、ジエトキシジエチルシラン、ジメトキシメチルフェニルシランなどが挙げられる。また、塗膜強度を向上させるために、少量のアルコキシジルコニウムを添加することもできる。
The kind of binder of the scavenger used in the embodiment of the present invention may be an inorganic material or an organic material.
Examples of the inorganic binder include alkoxysilane polymers. Alkoxysilanes include tetramethoxysilane, methyltrimethoxysilane, ethyltrimethoxysilane, dimethoxydimethylsilane, dimethoxydiethylsilane, tetraethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, diethoxydimethylsilane, diethoxydiethylsilane And dimethoxymethylphenylsilane. A small amount of alkoxyzirconium can also be added to improve the coating strength.
アルコキシシランのポリマーはアルコキシシランに水を０．１ｍｏｌ％以上添加し、さらに触媒として酸あるいはアルカリをごく微量添加させ反応を起こさせる。触媒を添加せずに加熱することにより重合反応を起こさせることも可能である。反応溶液を高温で濃縮乾燥することにより重合体を得ることができるが、溶媒に再溶解して保存することが好ましい。 In the alkoxysilane polymer, 0.1 mol% or more of water is added to the alkoxysilane, and a very small amount of acid or alkali is added as a catalyst to cause the reaction. It is also possible to cause the polymerization reaction by heating without adding a catalyst. The polymer can be obtained by concentrating and drying the reaction solution at a high temperature, but it is preferable to redissolve it in a solvent and store it.
有機系バインダーとしては、前記式（１）の捕捉剤と反応しない重合体を用いることができる。重合体としては、樹脂及び弾性体である。
樹脂としては、例えばアクリル樹脂、スチレン樹脂等である。アクリル樹脂はアクリル基を有するモノマーを重合して得られる樹脂であり、またアクリル基を有するモノマーあるいはオリゴマーを塗布成膜後に熱、光などの手段で反応させて得られる樹脂である。スチレン系樹脂はスチレン基を有する樹脂であり、またスチレン基の一部を混入させた樹脂である。
As the organic binder, a polymer that does not react with the scavenger of the formula (1) can be used. Examples of the polymer include a resin and an elastic body.
Examples of the resin include acrylic resin and styrene resin. The acrylic resin is a resin obtained by polymerizing a monomer having an acrylic group, and is a resin obtained by reacting a monomer or oligomer having an acrylic group with a means such as heat or light after coating film formation. The styrene resin is a resin having a styrene group, and is a resin in which a part of the styrene group is mixed.
弾性体としては各種のゴムであり、例えばポリイソプレンゴム、ポリブタジエンゴム、スチレンーブタジエンゴム、ポリイソブチレンゴム、エチレンープロピレンゴム、アクリロニトリルブタジジエンゴムなどである。
また有機バインダーとして液状ポリマー、石油樹脂を用いることが出来る。液状ポリマーとしては、液状ポリブテン、液状ポリブタジエンなどがあげられる。石油樹脂としては、日石ネオポリマーなどが上げられる。
Examples of the elastic body include various rubbers such as polyisoprene rubber, polybutadiene rubber, styrene-butadiene rubber, polyisobutylene rubber, ethylene-propylene rubber, and acrylonitrile butadiene rubber.
Liquid polymers and petroleum resins can be used as the organic binder. Examples of the liquid polymer include liquid polybutene and liquid polybutadiene. Examples of petroleum resins include Nisseki Neopolymer.
また有機系バインダーと無機系バインダーを混合してもよく、あらかじめ反応させたハイブリットタイプの樹脂でも良い。ハイブリットタイプの樹脂としてはカネカゼムラック等アクリルシリコン系が挙げられる。
これらの透明樹脂を有機溶媒に溶解することにより塗膜形成用溶液を作製できる。樹脂溶液の濃度は１０ｗｔ％以上、好ましくは２０〜８０ｗｔ％用いる。
Further, an organic binder and an inorganic binder may be mixed, or a hybrid type resin that has been reacted in advance may be used. Examples of the hybrid type resin include acrylic silicones such as Kanekazemulac.
A solution for forming a coating film can be prepared by dissolving these transparent resins in an organic solvent. The concentration of the resin solution is 10 wt% or more, preferably 20 to 80 wt%.
捕捉剤シートの作製はバインダー溶液に式（１）の捕捉剤を含む捕捉剤をバインダーの固形分に対し１０ｗｔ％以上、好ましくは２０〜８０ｗｔ％添加し十分に攪拌する。均一になった溶液をシート状部材に塗布してシートを作製した後、使用した溶媒を減圧下で除去して、目的とする捕捉剤シートを得る。捕捉剤シートには必要に応じて表面保護フィルムをラップし、使用時に表面保護フィルムをはがして使用することにより、捕捉剤の性能を落とすことなく保持できる。なお、これらの一連の作業は不活性雰囲気下で行なうことが望ましい。 For producing the scavenger sheet, a scavenger containing the scavenger of formula (1) is added to the binder solution in an amount of 10 wt% or more, preferably 20 to 80 wt% with respect to the solid content of the binder, and sufficiently stirred. After the uniform solution is applied to a sheet-like member to produce a sheet, the solvent used is removed under reduced pressure to obtain a target scavenger sheet. If necessary, a surface protective film is wrapped on the capture agent sheet, and the surface protective film is peeled off at the time of use, so that the performance of the capture agent can be maintained without deteriorating. In addition, it is desirable to perform these series of operations in an inert atmosphere.
以上のように、本発明の実施の形態に係る捕捉剤シートは、水分捕捉能及び酸素捕捉能ともに極めて優れた捕捉剤を使用している。また、前述したアルカリ（土類）金属のような危険性はないため、取り扱いが容易である。したがって、有機電子デバイスに容易に使用することが可能になり又、有機電子デバイスに悪影響を与える水分や酸素を低減することが可能になる。 As described above, the scavenger sheet according to the embodiment of the present invention uses a scavenger that is extremely excellent in both moisture scavenging ability and oxygen scavenging ability. Moreover, since there is no danger like the alkali (earth) metal mentioned above, handling is easy. Therefore, the organic electronic device can be easily used, and moisture and oxygen that adversely affect the organic electronic device can be reduced.
また、有機電子デバイスの適当な所定位置に両面テープや接着剤等によって被着して使用することにより、有機電子デバイスの長寿命化に非常に効果を発揮する。例えば捕捉剤シートを貼付したキャップガラスで有機電子デバイスを封止することにより、封止後のデバイス中の微量の水分や酸素を、シートに含まれる捕捉剤によって吸収、吸着し、有機物の劣化を防いで、有機電子デバイスの寿命を大幅に延長することができる。 In addition, it is very effective in extending the life of the organic electronic device by being attached to a predetermined position of the organic electronic device with a double-sided tape or an adhesive. For example, by sealing an organic electronic device with a cap glass with a capture agent sheet attached, a small amount of moisture or oxygen in the device after sealing is absorbed and adsorbed by the capture agent contained in the sheet, and the organic matter is deteriorated. This can significantly extend the lifetime of the organic electronic device.
また、本実施の形態に係る有機電子デバイス用捕捉剤シートは、シート状のため、有機電子デバイスの形状に応じて適当な形と大きさに裁断し、有機電子デバイス内の好適な位置に被着して配設することができる。したがって、有機電子デバイスの長寿命化を図ることが可能になるばかりでなく、有機電子デバイスの性能を阻害することなく使用できるという効果を奏する。 In addition, since the organic electronic device scavenger sheet according to the present embodiment is in the form of a sheet, it is cut into a suitable shape and size according to the shape of the organic electronic device and covered at a suitable position in the organic electronic device. It can be worn and arranged. Therefore, it is possible not only to extend the life of the organic electronic device but also to use it without impairing the performance of the organic electronic device.
尚、本実施の形態に係る有機電子デバイス用捕捉剤シートは、有機ＥＬ（Eletroluminescence）パネル、有機ＴＦＴ（Thin Film Transistor）、有機太陽電池、有機光電変換膜を用いたＣＭＯＳセンサ（有機ＣＭＯＳセンサ）等、有機材料を用いた各種の有機電子デバイスに適用可能である。 Note that the organic electronic device scavenger sheet according to the present embodiment includes an organic EL (Eletroluminescence) panel, an organic TFT (Thin Film Transistor), an organic solar cell, and a CMOS sensor using an organic photoelectric conversion film (organic CMOS sensor). The present invention can be applied to various organic electronic devices using organic materials.
次に、本発明の実施例について説明するが、これらに限定されるものではない。
［実施例１］
十分に乾燥した液状ポリマー（日石ポリブテン、ＬＶ−１００）の５０ｗｔ％トルエン溶液１００グラムにトリデシルアルミニウム１００グラムを均一に溶解した。片面に粘着剤を塗布したテープの裏面側に本溶液を塗布した後、減圧下で溶媒を除去して捕捉剤シートを作成した。捕捉剤層の厚さは０．７ｍｍ厚にコントロールした。
Next, although the Example of this invention is described, it is not limited to these.
[Example 1]
100 grams of tridecyl aluminum was uniformly dissolved in 100 grams of a 50 wt% toluene solution of a sufficiently dried liquid polymer (Nisseki Polybutene, LV-100). After this solution was applied to the back side of the tape coated with adhesive on one side, the solvent was removed under reduced pressure to prepare a scavenger sheet. The thickness of the scavenger layer was controlled to 0.7 mm.
前記捕捉剤シートを貼付したキャップガラスを用いて封止した有機ＥＬは、良好な発光輝度を示し、発光寿命も良好であった。
また、前記有機電子デバイス用捕捉剤シートの脱水性能を測定した。１００ｃｍ２に成形した捕捉剤シートを、湿度５．０％に調整した密閉容器（内容積６４０ｃｍ３）に入れ、容器内に静置した湿度センサーで容器内の湿度の経時変化を測定した。
The organic EL sealed with the cap glass on which the scavenger sheet was attached showed good emission luminance and good emission lifetime.
Further, the dehydrating performance of the organic electronic device scavenger sheet was measured. The scavenger sheet molded to 100 cm 2 was placed in a sealed container (internal volume 640 cm 3 ) adjusted to a humidity of 5.0%, and the change over time in the humidity of the container was measured with a humidity sensor placed in the container.
本実施例１に係る捕捉剤シートの水分捕捉能の測定結果を図１に示す。図１において、グラフＡは本実施例１の捕捉剤シートの特性を示すもので、比較対象として、同面積の既存のシート型捕捉剤（ダイニック株式会社製ＨＤ−ＳＯ５）の特性を併記している。
本実施例１の捕捉剤シートは、前記既存のシート型捕捉剤に比べて優れた吸湿能力を示した。
FIG. 1 shows the measurement results of the moisture capturing ability of the scavenger sheet according to Example 1. In FIG. 1, graph A shows the characteristics of the scavenger sheet of Example 1, and the characteristics of an existing sheet-type scavenger of the same area (HD-SO5 manufactured by Dynic Co., Ltd.) are also shown for comparison. Yes.
The scavenger sheet of Example 1 showed excellent moisture absorption ability compared to the existing sheet-type scavenger.
また、前記捕捉剤シートの酸素捕捉能を測定した。１００ｃｍ２に成形した捕捉剤シートを、酸素濃度１０．０％に調整した密閉容器（内容積６４０ｃｍ３）に入れ、容器内に静置した酸素濃度センサーで容器内の酸素濃度の経時変化を測定した。測定結果を図２に示す。図２において、グラフＡは本実施例１の捕捉剤シートの特性を示すもので、比較対象として、同面積の既存のシート型捕捉剤（ダイニック株式会社製ＨＤ−ＳＯ５）の特性を併記している。
本実施例１の捕捉剤シートは、前記既存のシート型捕捉剤には無い、優れた酸素捕捉能力を示した。
Further, the oxygen scavenging ability of the scavenger sheet was measured. The scavenger sheet molded to 100 cm 2 is placed in a sealed container (internal volume 640 cm 3 ) adjusted to 10.0% oxygen concentration, and the time-dependent change in oxygen concentration in the container is measured with an oxygen concentration sensor placed in the container. did. The measurement results are shown in FIG. In FIG. 2, graph A shows the characteristics of the scavenger sheet of Example 1, and the characteristics of an existing sheet-type scavenger of the same area (HD-SO5 manufactured by Dynic Co., Ltd.) are also shown for comparison. Yes.
The scavenger sheet of Example 1 exhibited an excellent oxygen scavenging ability that was not found in the existing sheet-type scavenger.
［実施例２］
十分に乾燥した液状ポリマー（日石ポリブテン、ＬＶ−１００）の５０ｗｔ％トルエン溶液２００グラムにトリデシルアルミニウム１００グラムとトリアシルシクロトリボロキシン５０グラムを均一に溶解した。片面に粘着剤を塗布したテープの反対側に本溶液を塗布した後、減圧下で溶媒を除去して捕捉剤シートを作成した。捕捉剤層の厚さは０．７ｍｍ厚にコントロールした。本実施例２においても、前記実施例１と同様に、優れた水分捕捉能及び酸素捕捉能を示した。
[Example 2]
100 grams of tridecylaluminum and 50 grams of triacylcyclotriboroxine were uniformly dissolved in 200 grams of a 50 wt% toluene solution of a well-dried liquid polymer (Nisseki Polybutene, LV-100). After this solution was applied to the opposite side of the tape coated with adhesive on one side, the solvent was removed under reduced pressure to prepare a scavenger sheet. The thickness of the scavenger layer was controlled to 0.7 mm. In Example 2, as in Example 1, excellent moisture capturing ability and oxygen capturing ability were exhibited.
本発明の有機電子デバイス用捕捉剤シートは、捕捉剤として前記式（１）に示した捕捉剤が使用でき、又、有機ＥＬパネル、有機ＴＦＴ、有機太陽電池、有機ＣＭＯＳセンサ等の有機材料を用いた各種の有機電子デバイスに利用可能である。 The scavenger sheet for organic electronic devices of the present invention can use the scavenger shown in the above formula (1) as a scavenger, and organic materials such as organic EL panels, organic TFTs, organic solar cells, and organic CMOS sensors. It can be used for various organic electronic devices used.
Claims (5)
Ｒ１Ｒ２Ｒ３Ｍ
（Ｒ１、Ｒ２及びＲ３は、各々炭素数６以上の、アルキル基、アルケニル基、アルキニル基、環式アルキル基、アリール基及びアルコキシ基からなる群より選ばれた１種のものであって、互いに同じでも異なっていてもよいが、補足剤として１つ以上のＣ−Ｍ結合を有するように選ばれたものである。Ｍはアルミニウム又はボロンである。） A capture agent sheet for organic electronic devices, comprising a capture agent represented by the following formula attached to a sheet-like member.
R 1 R 2 R 3 M
(R 1 , R 2 and R 3 are each one kind selected from the group consisting of alkyl groups, alkenyl groups, alkynyl groups, cyclic alkyl groups, aryl groups and alkoxy groups each having 6 or more carbon atoms. And may be the same or different from each other, but are selected as supplements to have one or more CM bonds, where M is aluminum or boron.)
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| KR (1) | KR101312415B1 (en) |
| TW (1) | TWI458384B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2009060B1 (en) * | 2006-04-18 | 2013-03-13 | Komatsu Seiren Co., Ltd. | Hot-melt type member and organic el display panel |
| JP2009095824A (en) * | 2007-09-27 | 2009-05-07 | Toshiba Corp | Transparent desiccant and organic electroluminescence device |
| JP5348869B2 (en) * | 2007-10-17 | 2013-11-20 | 小松精練株式会社 | Hot melt type member for organic electronic device, barrier film sealing member, organic electronic device sealing panel using them |
| JP5594930B2 (en) * | 2007-10-17 | 2014-09-24 | 小松精練株式会社 | Hot-melt type member for organic thin film solar cell and organic thin film solar cell case sealing panel |
| JP5773160B2 (en) * | 2009-06-30 | 2015-09-02 | Jsr株式会社 | Moisture or oxygen scavenging composition, cured body, and electronic device |
| JP2012038660A (en) * | 2010-08-10 | 2012-02-23 | Futaba Corp | Water-capturing agent and organic electronic device using the same |
| CN113169277A (en) * | 2018-11-26 | 2021-07-23 | 住友化学株式会社 | Method for manufacturing organic photoelectric conversion element |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206075A (en) * | 1991-12-19 | 1993-04-27 | Exxon Chemical Patents Inc. | Sealable polyolefin films containing very low density ethylene copolymers |
| JP2002190384A (en) * | 2000-12-19 | 2002-07-05 | Ricoh Co Ltd | Electroluminescent element |
| JP2003317942A (en) * | 2002-04-26 | 2003-11-07 | Seiko Epson Corp | Electroluminescence device, its manufacturing method, and electronic device |
| TWI225501B (en) * | 2002-11-06 | 2004-12-21 | Delta Optoelectronics Inc | Packaging material used for a display device and method of forming thereof |
| JP4820536B2 (en) * | 2003-06-25 | 2011-11-24 | 彬雄 谷口 | Method for manufacturing organic electroluminescence device |
| US7193100B2 (en) * | 2003-12-31 | 2007-03-20 | Albemarle Corporation | Haloaluminoxane compositions, their preparation, and their use in catalysis |
| CN1657155A (en) * | 2004-02-17 | 2005-08-24 | 李秉哲 | Film type drier for closed electronic device and its manufacturing method |
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2006
- 2006-02-10 JP JP2006033659A patent/JP4894284B2/en not_active Expired - Fee Related
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2007
- 2007-01-31 KR KR1020070009774A patent/KR101312415B1/en active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20070081423A (en) | 2007-08-16 |
| JP2007214017A (en) | 2007-08-23 |
| TW200806071A (en) | 2008-01-16 |
| KR101312415B1 (en) | 2013-09-27 |
| TWI458384B (en) | 2014-10-21 |
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