JP2007502877A - トリフェニルホスフィン単位を含むオリゴマーおよびポリマー - Google Patents
トリフェニルホスフィン単位を含むオリゴマーおよびポリマー Download PDFInfo
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- JP2007502877A JP2007502877A JP2006523599A JP2006523599A JP2007502877A JP 2007502877 A JP2007502877 A JP 2007502877A JP 2006523599 A JP2006523599 A JP 2006523599A JP 2006523599 A JP2006523599 A JP 2006523599A JP 2007502877 A JP2007502877 A JP 2007502877A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 89
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 20
- 239000011574 phosphorus Substances 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003017 phosphorus Chemical class 0.000 claims abstract description 8
- 150000002829 nitrogen Chemical class 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 239000000178 monomer Substances 0.000 claims description 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000005259 triarylamine group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 230000005669 field effect Effects 0.000 claims description 6
- 239000012212 insulator Substances 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000005620 boronic acid group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 230000003606 oligomerizing effect Effects 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims description 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 29
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 25
- 239000010410 layer Substances 0.000 description 14
- -1 poly (p-phenylene vinylene) Polymers 0.000 description 14
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000001194 electroluminescence spectrum Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 238000005424 photoluminescence Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- QENIALCDPFDFHX-UHFFFAOYSA-N 1,4-dibromo-2,5-dimethylbenzene Chemical group CC1=CC(Br)=C(C)C=C1Br QENIALCDPFDFHX-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- ZHYUWWWSSFWEMN-UHFFFAOYSA-N 1-bromo-4-[(4-bromo-2,5-dimethylphenyl)-phenylphosphoryl]-2,5-dimethylbenzene Chemical compound C1=C(Br)C(C)=CC(P(=O)(C=2C=CC=CC=2)C=2C(=CC(Br)=C(C)C=2)C)=C1C ZHYUWWWSSFWEMN-UHFFFAOYSA-N 0.000 description 1
- NSSQDDFIIFKZGJ-UHFFFAOYSA-N 2,8-dibromo-6,6,12,12-tetraoctylindeno[2,1-a]fluorene Chemical compound CCCCCCCCC1(CCCCCCCC)C=C2C3=CC=C(Br)C=C3C(CCCCCCCC)(CCCCCCCC)C2=C2C1=C1C=C(Br)C=CC1=C2 NSSQDDFIIFKZGJ-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- SNNVSEONCOCCRZ-UHFFFAOYSA-N C1CC=CCCC=C1[Ni]C1=CCCC=CCC1 Chemical compound C1CC=CCCC=C1[Ni]C1=CCCC=CCC1 SNNVSEONCOCCRZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
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- DNSGBRIAZLZWQB-UHFFFAOYSA-N bis(4-bromo-2,5-dimethylphenyl)-phenylphosphane Chemical compound C1=C(Br)C(C)=CC(P(C=2C=CC=CC=2)C=2C(=CC(Br)=C(C)C=2)C)=C1C DNSGBRIAZLZWQB-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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Abstract
Description
本発明は、半導体オリゴマーおよびポリマー、その合成並びに光学デバイスにおける使用に関する。
1つのクラスの光電デバイスは、有機材料を、発光(有機発光デバイスあるいは「OLED」)のために、または光電池か光検出器(「光起電」デバイス)の活性部分として用いるものである。これらのデバイスの基本構造は、半導体有機層が、この有機層を介して、負電荷キャリアー(電子)を注入するか受容するためのカソードと、正電荷キャリアー(正孔)を注入するか受容するためのアノードとの間にはさまれたものである。
本発明者等は、従来技術のトリアリールアミンに替えてトリアリールホスフィンを用いることは、材料の正孔輸送性における有意な改善およびより深い青色発光をもたらすことを驚くべきことに見出した。
a.各LGは同一であるか異なり、反応性ホウ素基を含み、および第2のモノマーは、ハロゲンおよび式―OSO2−Zの基から独立に選択される2つの反応基を含み、または
b.各LGは、独立に、ハロゲンまたは式−O−SO2−Zの基を含み、および第2のモノマーは2つの反応性ホウ素基(同一であるか異なる)を含む。
本発明を、ポリマーとポリマー化に関して以下に記載するが、しかしながら、この記載は、対応するオリゴマーおよびオリゴマー化にも同様に当てはまることが認識されるであろう。
本発明によるポリマーは、式(I)の繰り返し単位を含まない比較ポリマーと比べて、有意により大きいHOMO−LUMOバンドギャップ(Eg)を有する(以下の表1を参照されたい)。更に、本発明によるポリマーは、光ルミネセンス(PL)およびエレクトロルミネセンス(EL)の双方について、より青い1931 PaL CIE座標を有する(以下の表2を参照されたい)。
ポリマー1
6,6,12,12,−テトラ(n−オクチル)トランス−インデノフルオレン−2,8−ジイル(T8IF)とモノマー1から誘導された繰り返し単位のコポリマー(85%T8IF:15%ホスフィンの比)(ポリマー1)を、モノマー1(15mol%)、6,6,12,12−テトラ(n−オクチル)インデノフルオレン−2,8−ジボロン酸のエチレングリコールエステル(T8IF−B、50mol%)および2,8−ジブロモ−6,6,12,12−テトラ(n−オクチル)インデノフルオレン(T8−IF−Br、35mol%)を用いるWO 00/53656に述べられる方法に従ってスズキ重合により生成した。
ポリマー2を、モノマー1の代わりにモノマー2を用いたことを除いては、上記のポリマー1についての手法に従って生成した。
エレクトロルミネセンスデバイス1および2を、ポリマー1およびポリマー2をそれぞれ用いて作製した。デバイスを、インジウムスズ酸化物のアノードを有するガラス基板、およびこの上に(a)H. C. Starck as Baytron Pから入手可能なポリ(エチレンジオキシチオフェン)/ポリ(スチレンスルホネート)の層をスピンコーティングにより堆積し、(b)キシレン溶液から本発明のポリマーの層をスピンコーティングにより堆積し、(c)カルシウムの第1の層およびアルミニウムの第2のキャップ層を含むカソードを真空蒸着により堆積することにより形成した。デバイスを、Saes Getters SpAから入手可能な気密容器を用いて密閉した。
Claims (23)
- 各Ar1、Ar2およびAr3が、任意に置換されたフェニル基である請求項1に記載のオリゴマーまたはポリマー。
- 少なくとも1つのAr3が、任意に置換された、分枝の、環状のまたは直鎖のC1−20アルキル若しくはC1−20アルコキシ;C1−20フルオロアルキル、フッ素、任意に置換されたジアリールアミンおよび任意に置換されたジアリールホスフィンから成る群から選択される置換基により置換される請求項1または2に記載のオリゴマーまたはポリマー。
- Eが、窒素、置換されていないリンまたは酸化リンから成る群から選択される請求項1〜3のいずれか一項に記載のオリゴマーまたはポリマー。
- 前記第2の繰り返し単位が、前記第1の繰り返し単位とは異なる請求項1〜4のいずれか一項に記載のオリゴマーまたはポリマー。
- 3つ以上の異なる繰り返し単位を含む請求項1〜5のいずれか一項に記載のオリゴマーまたはポリマー。
- 前記第2の繰り返し単位および任意の他の繰り返し単位が、任意に置換されたフェニル、フルオレン、スピロビフルオレン、インデノフルオレン、ヘテロアリール、ジヒドロフェナントレンおよび/またはトリアリールアミンから選択される請求項5または6に記載のオリゴマーまたはポリマー。
- 各LGが、同一であるか異なり、独立に、水素;ボロン酸基、ボロン酸エステル基およびボラン基から選択される反応性ホウ素基;式−OSO2−Zの基(式中、Zは、任意に置換されたアルキルおよびアリールから成る群から選択される)から選択される請求項8に記載の方法。
- 各LGが、独立に、ハロゲンまたは式−OSO2−Zの基であり、前記式(II)のモノマーが、ニッケル錯体触媒の存在下でオリゴマー化またはポリマー化される請求項9に記載の方法。
- 前記式(II)のモノマーを、パラジウム錯体触媒および塩基の存在下で、第2の芳香族モノマーとオリゴマー化またはポリマー化し、および
a.各LGは同一であるか異なり、反応性ホウ素基を含み、および前記第2のモノマーは、ハロゲンおよび式−OSO2−Zの基から独立に選択される2つの反応性基を含み、または
b.各LGは、独立に、ハロゲンまたは式−O−SO2−Zの基を含み、および前記第2のモノマーは、同一であるか異なる2つの反応性ホウ素基を含む
請求項9に記載の方法。 - 1つのLGが、反応性ホウ素基であり、他のLGが、ハロゲンまたは式−OSO2−Zの基であり、前記式(II)のモノマーを、パラジウム錯体触媒および塩基の存在下でオリゴマー化またはポリマー化する請求項9に記載の方法。
- LGが、式−B(OR1)2を有する請求項13に記載のモノマー。
- 少なくとも1つのR1が、直鎖の、分枝のまたは環状のC1−20アルキルを示す請求項13または14に記載のモノマー。
- 前記式(IV)の残基の少なくとも1つの炭素原子が、置換されている請求項16に記載のモノマー。
- 請求項1〜7のいずれか一項に記載のオリゴマーまたはポリマーを含む光学デバイス。
- 前記オリゴマーまたはポリマーが、正孔注入のための第1の電極と、電子注入のための第2の電極との間の層中に位置する請求項18に記載の光学デバイス。
- 前記デバイスが、エレクトロルミネセンスデバイスである請求項19に記載の光学デバイス。
- 請求項1〜7のいずれか一項に記載のオリゴマーまたはポリマーを含むスイッチングデバイス。
- 第1の面および第2の面を有する絶縁体;前記絶縁体の前記第1の面上に位置するゲート電極;前記絶縁体の前記第2の面上に位置する請求項1〜7のいずれか一項に記載のオリゴマーまたはポリマー;および前記オリゴマーまたはポリマー上に位置するドレイン電極およびソース電極を含む電界効果トランジスタ。
- 請求項22に記載の電界効果トランジスタを含む集積回路。
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EP03018832.0 | 2003-08-19 | ||
EP03018832 | 2003-08-19 | ||
PCT/EP2004/009249 WO2005017065A1 (en) | 2003-08-19 | 2004-08-18 | Oligomer and polymer comprising triphenyl phosphine units |
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US (1) | US7893172B2 (ja) |
EP (1) | EP1660608B1 (ja) |
JP (1) | JP4885717B2 (ja) |
KR (1) | KR20060081698A (ja) |
CN (1) | CN1836024B (ja) |
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JPWO2005019374A1 (ja) * | 2003-08-21 | 2006-10-19 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
JP2007518842A (ja) * | 2003-12-13 | 2007-07-12 | メルク パテント ゲーエムベーハー | オリゴマーおよびポリマー |
JP2008536324A (ja) * | 2005-04-15 | 2008-09-04 | ケンブリッジ ディスプレイ テクノロジー リミテッド | パルス駆動されるディスプレー |
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JP2007224282A (ja) * | 2006-01-16 | 2007-09-06 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
JP2009536981A (ja) * | 2006-05-12 | 2009-10-22 | メルク パテント ゲーエムベーハー | インデノフルオレンポリマー系有機半導体材料 |
WO2009053088A1 (de) | 2007-10-24 | 2009-04-30 | Merck Patent Gmbh | Optoelektronische vorrichtung |
DE102008045662A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008045664A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008045663A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
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- 2004-08-18 US US10/568,659 patent/US7893172B2/en not_active Expired - Fee Related
- 2004-08-18 CN CN2004800235586A patent/CN1836024B/zh not_active Expired - Fee Related
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JP2005515264A (ja) * | 2001-07-10 | 2005-05-26 | ダウ グローバル テクノロジーズ インコーポレーテッド | 電場応答性ポリマー及びそれから製造されるデバイス |
WO2003035713A1 (en) * | 2001-10-25 | 2003-05-01 | Cambridge Display Technology Limited | Conjugated polymer preparation via suzuki-coupling in emulsion |
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JPWO2005019374A1 (ja) * | 2003-08-21 | 2006-10-19 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
JP5168785B2 (ja) * | 2003-08-21 | 2013-03-27 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
JP2007518842A (ja) * | 2003-12-13 | 2007-07-12 | メルク パテント ゲーエムベーハー | オリゴマーおよびポリマー |
JP2008536324A (ja) * | 2005-04-15 | 2008-09-04 | ケンブリッジ ディスプレイ テクノロジー リミテッド | パルス駆動されるディスプレー |
Also Published As
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KR20060081698A (ko) | 2006-07-13 |
EP1660608B1 (en) | 2015-07-08 |
WO2005017065A1 (en) | 2005-02-24 |
EP1660608A1 (en) | 2006-05-31 |
CN1836024A (zh) | 2006-09-20 |
US7893172B2 (en) | 2011-02-22 |
CN1836024B (zh) | 2011-03-16 |
JP4885717B2 (ja) | 2012-02-29 |
US20070031698A1 (en) | 2007-02-08 |
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