JP6490685B2 - 電気光学素子およびその使用 - Google Patents
電気光学素子およびその使用 Download PDFInfo
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- JP6490685B2 JP6490685B2 JP2016530368A JP2016530368A JP6490685B2 JP 6490685 B2 JP6490685 B2 JP 6490685B2 JP 2016530368 A JP2016530368 A JP 2016530368A JP 2016530368 A JP2016530368 A JP 2016530368A JP 6490685 B2 JP6490685 B2 JP 6490685B2
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- 229920000642 polymer Polymers 0.000 claims description 77
- -1 phenylene vinylene Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 20
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 13
- 125000005259 triarylamine group Chemical group 0.000 claims description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 11
- 239000011368 organic material Substances 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 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 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229920001940 conductive polymer Polymers 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 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 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002322 conducting polymer Substances 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 239000010410 layer Substances 0.000 description 79
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- 229920000547 conjugated polymer Polymers 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
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- 238000005259 measurement Methods 0.000 description 7
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- 150000001412 amines Chemical class 0.000 description 6
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 5
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Natural products C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
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- 125000005504 styryl group Chemical group 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 4
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 4
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- 238000007740 vapor deposition Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical class C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
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- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 229910052749 magnesium Inorganic materials 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
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- 238000003077 quantum chemistry computational method Methods 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical group 0.000 description 2
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- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000005267 main chain polymer Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- ABCGFHPGHXSVKI-UHFFFAOYSA-O meso-tetrakis(n-methyl-4-pyridyl)porphine(4+) Chemical compound C1=C[N+](C)=CC=C1C(C1=CC=C(N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(=N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(N1)=C1C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 ABCGFHPGHXSVKI-UHFFFAOYSA-O 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- AODWRBPUCXIRKB-UHFFFAOYSA-N naphthalene perylene Chemical group C1=CC=CC2=CC=CC=C21.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 AODWRBPUCXIRKB-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 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 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000005266 side chain polymer Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 150000004882 thiopyrans Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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Description
−モノクロもしくはマルチカラーディスプレイ要素用の、白色もしくは着色バックライト(例えば、電卓、携帯電話およびその他の携帯用途に)、
−大面積ディスプレイ(例えば、交通標識もしくはポスターとして)、
−異なる色や形の様々な照明要素、
−携帯用の、モノクロもしくはフルカラーパッシブマトリックスディスプレイ(例えば、携帯電話、PDAおよびカムコーダー用)、
−様々な異なる用途のための、フルカラー、大面積かつ高解像度のアクティブマトリックスディスプレイ(例えば、携帯電話、PDA、ラップトップ型パソコンおよびテレビ用)。
a)アノード、
b)カソード、
c)アノードとカソードとの間に配置され、少なくとも1つの半導電性有機材料を含んでなる、少なくとも1つの発光層、および
d)前記少なくとも1つの発光層と前記アノードの間に位置し、正孔伝導構造単位を有するポリマーを含んでなる、少なくとも1つの中間層
を具備してなる電気光学素子であって、
前記正孔伝導構造単位を有するポリマーが、さらに電子伝導特性を有する構造単位を有することを特徴とする、電気光学素子を提供するものである。
Rは、水素原子、C6〜C60−アリール基、ピリジル基、キノリル基、C1〜20−アルキル基またはC1〜20−アルコキシ基であり、ここでこれらの基は1以上のラジカルR2によって置換されていなくても置換されていてもよく;
mは、0〜4の整数であり;
R1は、C6〜C60−アリール基、ピリジル基、キノリル基、C1〜20−アルキル基またはC1〜20−アルコキシ基であり、ここでこれらの基は1以上のラジカルR2によって置換されていなくても置換されていてもよく;
R2は、水素原子、C6〜60−アリール基、ピリジル基、キノリル基、C1〜20−アルキル基またはC1〜20−アルコキシ基であり;
Lは、C6〜60−アリーレン基、ピリジニレン基、キノリニレン基、またフルオレニレン基であり、ここでこれらの基は1以上のラジカルR2によって置換されていなくても置換されていてもよく;
Ar1は、C6〜60−アリール基、ピリジニル基またはキノリニル基であり、ここでこれらの基は1以上のラジカルR2によって置換されていなくても置換されていてもよい。
Ar1は、同一であるか異なり、異なる繰り返し単位においては独立に、単結合または置換されていてもよい、単環式もしくは多環式のアリール基であり、
Ar2は、同一であるか異なり、異なる繰り返し単位においては独立に、置換されていてもよい、単環式もしくは多環式のアリール基であり、
Ar3は、同一であるか異なり、異なる繰り返し単位においては独立に、置換されていてもよい、単環式もしくは多環式のアリール基であり、かつ
mは、1、2または3である。
rは、0、1、2、3または4であり、かつ
sは、0、1、2、3、4または5である。
T1およびT2は、それぞれ独立に、チオフェン、セレノフェン、チエノ[2,3b]チオフェン、チエノ[3,2b]チオフェン、ジチエノチオフェン、ピロール、アニリンから選択され、それらの全ては任意にR9に置換され、
R9は、出現毎に独立に、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、SCN、C(=O)NR0R00、−C(=O)X、−C(=O)R0、−NH2、−NR0R00、SH、SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、所望により置換されたシリル、または1〜40個の炭素原子を有する、カルビルもしくはヒドロカルビルから選択され、置換されてもよく、1以上のヘテロ原子を含んでもよく、
Ar4およびAr5は、独立に、単環式もしくは多環式の、アリールもしくはヘテロアリール(これらは、置換されていてもよく、また、隣接するチオフェンもしくはセレノフェン基の一方あるいは両方に2,3‐位で縮合していてもよい)、
cとeは、独立に、0、1、2、3または4であり、ここで、1<c+e≦6を満たし、かつ
dとfは、独立に、0、1、2、3または4である。
A、BおよびB’は、独立におり、複数存在する場合に互いに独立に、二価の基、好ましくは、−CR11R12−、−NR11−、−PR11−、−O−、−S−、−SO−、−SO2−、−CO−、−CS−、−CSe−、−P(=O)R11−、−P(=S)R11−および−SiR11R12−から選択され、
R11およびR12は、独立に、同一または異なる基であり、H、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、−SCN、-C(=O)NR0R00、−C(=O)X、-C(=O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、置換されていてもよいシリル、または1〜40個の炭素原子を有し、置換されていてもよく、1以上のヘテロ原子を含んでいてもよい、カルビルもしくはヒドロカルビルから選択され、かつR11およびR12基は、それらが結合するフルオレン部分とスピロ基を形成してもよく、
Xは、ハロゲンであり、
R0とR00は、独立に、Hまたは1個以上のヘテロ原子を含んでいてもよく、置換されていてもよい、カルビルもしくはヒドロカルビル基であり、
gの各々は、独立に、0または1であり、同じ副単位中のそれぞれ対応するhは、0および1以外であり、
mは、1以上の整数であり、
Ar1とAr2は、独立に、単環式もしくは多環式の、アリールもしくはヘテロアリールであり、これらは置換されていてもよく、インデノフルオレン基の7,8‐位もしくは8,9‐位で縮合していてもよく、かつ
aとbは、独立に、0または1である。
R11およびR12は、式(23)で定義されるものであり、
rは、0、1、2、3または4であり、
Rは、R11の定義のうちの1つを有する。
Lは、H、ハロゲン、または1〜12個の炭素原子を有する、任意にフッ素化された、直鎖もしくは分岐の、アルキルもしくはアルコキシ基であり、好ましくは、H、F、メチル、i‐プロピル、t‐ブチル、n‐ペントキシまたはトリフルオロメチルであり、そして
L’は、1〜12個のC原子を有する、フッ素化されていてもよい、直鎖もしくは分岐の、アルキルもしくはアルコキシ基であり、好ましくは、n‐オクチルまたはn‐オクチルオキシである。
本発明によるポリマーを調整するために、まず電子輸送化合物をモノマーに転換することが必要であった。
本発明によるポリマーP1〜P4および比較ポリマーC1は、以下のモノマー(パーセンテージ=mol%)を使用し、WO03/048225A2に従って、スズキカップリングにより合成される。前述のモノマーを有する発光ポリマーの合成は、WO05/040302およびWO03/020790に開示される。
PLEDの製造
ポリマー有機発光ダイオード(PLED)の製造については既に、文献(例えば、WO2004/037887A2に)に多数記載されている。実例を通して本発明を説明するために、PLEDはスピンコートにより、P1〜P4および比較ポリマーC1で製造される。典型的な素子は、以下に示される構造を有する。
上記で特定した方法において、部品は製造され、20nmのP1およびP3、ならびに20nmのC1で特徴づけられる。使用される発光ポリマーは、メルク製の青色発光ポリマーである。結果は、表1に示される。
青色素子間のさらなる比較は、メルク製のポリマーSPB−078で行われる。ここで使用される中間層は、ポリマーP2およびP4ならびに比較ポリマーC1である。結果は表2に示される。ここで特に注意すべきは、本発明によるポリマーの使用の結果、素子の理想的により良い電気的安定性である。これは、寿命測定の間の電圧の明らかな小ささに現れている。
白色ポリマーとともに用いることでも、素子寿命、作動電圧および電圧の抑制された上昇における改善を達成することができる。中間層ポリマーP1およびC1は、ここでメルク製の白色ポリマーSPW−110と共に使用される。
メルク製のさらなる白色ポリマーSPW−138は、同様に詳述される方法で、素子を製造することに用いられる。
Claims (16)
- a)アノード、
b)カソード、
c)アノードとカソードとの間に配置され、少なくとも1つの半導電性有機材料を含んでなる、少なくとも1つの発光層、および
d)前記少なくとも1つの発光層と前記アノードの間に位置し、正孔伝導構造単位を有するポリマーを含んでなる、少なくとも1つの中間層
を具備してなる電気光学素子であって、
前記正孔伝導構造単位を有するポリマーが、さらに電子伝導特性を有する構造単位を有し、かつ
前記電子伝導特性を有する構造単位のLUMOが、発光層中の前記半導電性有機材料のLUMOより低いものであることを特徴とする、電気光学素子。 - 前記電子伝導特性を有する構造単位のLUMOが、−2.3eVよりも低いものであることを特徴とする、請求項1に記載の電気光学素子。
- 前記電子伝導特性を有する構造単位が、以下の式(I)〜(IV)の構造単位の群から選択されるものであることを特徴とする、請求項1または2に記載の電気光学素子。
R1〜R4は、それぞれ独立に、水素原子、環内に6〜50個の炭素原子を有する、置換もしくは非置換の芳香族環ヒドロカルビル基、5〜50個の環原子を有する、置換もしくは非置換の芳香族ヘテロ環基、1〜50個の炭素原子を有する、置換もしくは非置換のアルキル基、環内に3〜50個の炭素原子を有する、置換もしくは非置換のシクロアルキル基、1〜50個の炭素原子を有する、置換もしくは非置換のアルコキシ基、環内に6〜50個の炭素原子を有する、置換もしくは非置換のアラルキル基、環内に5〜50個の炭素原子を有する、置換もしくは非置換のアリールオキシ基、環内に5〜50個の炭素原子を有する、置換もしくは非置換のアリールチオ基、1〜50個の炭素原子を有する、置換もしくは非置換のアルコキシカルボニル基、1〜50個の炭素原子を有する、置換もしくは非置換のシリル基、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基、またはヒドロキシ基であり、かつ
1以上の、R1およびR2、R3およびR 4 のペアが、環系を形成していてもよい) - 正孔伝導ポリマー中の前記電子伝導特性を有する構造単位の割合が、0.01〜30mol%の範囲にあることを特徴とする、請求項1〜3のいずれか一項に記載の電気光学素子。
- 正孔伝導ポリマーが、トリアリールアミン由来の、正孔伝導特性を有する構造単位を有することを特徴とする、請求項1〜4のいずれか一項に記載の電気光学素子。
- 正孔伝導ポリマーが、フルオレン、スピロビフルオレン、インデノフルオレン、フェナントレン、ジヒドロフェナントレン、ジベンゾチオフェン、ジベンゾフランおよびそれらの誘導体から得られる繰り返し構造単位を有することを特徴とする、請求項1〜6のいずれか一項に記載の電気光学素子。
- 前記発光層の前記半導電性有機材料が、半導電性ポリマーであることを特徴とする、請求項1〜7のいずれか一項に記載の電気光学素子。
- 前記半導電性コポリマーが、フルオレン、スピロビフルオレン、インデノフルオレン、フェナントレン、ジヒドロフェナントレン、フェニレン、ジベンゾチオフェン、ジベンゾフラン、フェニレンビニレン、およびそれらの誘導体から得られる繰り返し構造単位を有し、これらの繰り返し単位は置換されていてもよい、ものであることを特徴とする、請求項8に記載の電気光学素子。
- 前記半導電性コポリマーが、トリアリールアミンから得られる繰り返し単位を有することを特徴とする、請求項8または9に記載の電気光学素子。
- さらに、前記アノードと正孔伝導ポリマーで構成される中間層の間に配置される正孔注入層を具備してなることを特徴とする、
請求項1〜10のいずれか一項に記載の電気光学素子。 - 基板上、特に透明基板上、に配置されることを特徴とする、請求項1〜11のいずれか一項に記載の電気光学素子。
- 前記電気化学素子が、アノード、正孔注入層、中間層、1以上の発光層、正孔ブロック層、電子輸送層およびカソードのみからなり、透明基板上に配置されてもよい、ことを特徴とする請求項1〜12のいずれか一項に記載の電気光学素子。
- 前記電気光学素子が、有機発光ダイオード(OLED)または有機発光電子化学電池(OLEC)であることを特徴とする、請求項1〜13のいずれか一項に記載の電気光学素子。
- 請求項1〜14のいずれか一項に記載の電気光学素子の、一般照明、バックライトおよびディスプレイ装置での使用。
- 治療および/または美容処置用途での使用のための、請求項1〜14のいずれか一項に記載の電気光学素子。
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