JP4613411B2 - Light emitting element - Google Patents
Light emitting element Download PDFInfo
- Publication number
- JP4613411B2 JP4613411B2 JP2000320568A JP2000320568A JP4613411B2 JP 4613411 B2 JP4613411 B2 JP 4613411B2 JP 2000320568 A JP2000320568 A JP 2000320568A JP 2000320568 A JP2000320568 A JP 2000320568A JP 4613411 B2 JP4613411 B2 JP 4613411B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- light
- derivatives
- pyromethene
- light emitting
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
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- 239000011737 fluorine Substances 0.000 claims description 4
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- 239000000539 dimer Substances 0.000 claims description 3
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- 238000000034 method Methods 0.000 description 13
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000000999 acridine dye Substances 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005606 carbostyryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical class C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- LBAIJNRSTQHDMR-UHFFFAOYSA-N magnesium phthalocyanine Chemical compound [Mg].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 LBAIJNRSTQHDMR-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- RSTDIKJOEIERRN-UHFFFAOYSA-N pyreno[4,5-c][1,2,5]thiadiazole Chemical class C1=CC=C2C3=NSN=C3C3=CC=CC4=CC=C1C2=C43 RSTDIKJOEIERRN-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000004322 quinolinols Chemical class 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
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [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
- 239000001022 rhodamine dye Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、電気エネルギーを光に変換できる素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機、光信号発生器などの分野に利用可能な発光素子に関するものである。
【０００２】
【従来の技術】
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機蛍光体内で再結合する際に発光するという有機積層薄膜発光素子の研究が近年活発に行われている。この素子は、薄型、低駆動電圧下での高輝度発光、蛍光材料を選ぶことによる多色発光が特徴であり注目を集めている。
【０００３】
この研究はコダック社のＣ．Ｗ．Ｔａｎｇらが有機積層薄膜素子が高輝度に発光することを示して以来（Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１（１２）２１，ｐ．９１３，１９８７）、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機積層薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に正孔輸送性のジアミン化合物、発光層である８−ヒドロキシキノリンアルミニウム、そして陰極としてＭｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電圧で１０００ｃｄ／ｍ2の緑色発光が可能であった。現在の有機積層薄膜発光素子は、上記の素子構成要素の他に電子輸送層を設けているものなど構成を変えているものもあるが、基本的にはコダック社の構成を踏襲している。
【０００４】
発光層のホスト材料としては、トリス（８−キノリノラト）アルミニウムを始めとする金属キレート化オキシノイド化合物、ジアリールブタジエン誘導体、スチルベン誘導体、ベンズオキサゾール誘導体、ベンゾチアゾール誘導体（特開昭６３−２６４６９２号公報）などがあげられる。
【０００５】
一方、ゲスト材料としてのドーパント材料には、レーザー染料として有用であることが知られている、７−ジメチルアミノ−４−メチルクマリンを始めとする蛍光性クマリン染料、ジシアノメチレンピラン染料、ジシアノメチレンチオピラン染料、ポリメチン染料、シアニン染料、オキソベンズアンスラセン染料、キサンテン染料、ローダミン染料、フルオレセイン染料、ピリリウム染料、カルボスチリル染料、ペリレン染料、アクリジン染料、ビス（スチリル）ベンゼン染料、ピレン染料、オキサジン染料、フェニレンオキサイド染料、ペリレン、テトラセン、ペンタセン、キナクリドン化合物、キナゾリン化合物、ピロロピリジン化合物、フロピリジン化合物、１，２，５−チアジアゾロピレン誘導体、ペリノン誘導体（特開平５−２７９６６２号公報）、ピロロピロール化合物（特開平５−３２０６６３号公報）、スクアリリウム化合物、ビオラントロン化合物、フェナジン誘導体、アクリドン化合物、ジアザフラビン誘導体などが知られている。
【０００６】
また発光材料、特にドーパント材料として、高輝度発光を示す化合物のピロメテン化合物が知られている（特開平９−１１８８８０号公報）。
【０００７】
【発明が解決しようとする課題】
しかし、従来技術に用いられる発光材料（ホスト材料、ドーパント材料）には、発光効率が低く消費電力が高いものや、化合物の耐久性が低く素子寿命の短いものが多かった。また、フルカラーディスプレイに必要な三原色の内、緑色発光においては高性能の発光材料が見い出されているが、青色や赤色、特に赤色においては十分な特性、とりわけ耐久性に優れた発光材料は得られていない。また、これまでのピロメテン化合物においても高輝度、高色純度には優れているものの、分子量が小さく熱的安定性に乏しいものが多かった。
【０００８】
本発明は、かかる従来技術の問題を解決し、発光効率が高く、耐久性にも優れた発光素子を提供することを目的とするものである。
【０００９】
すなわち本発明は、陽極と陰極の間に発光物質が存在し、電気エネルギーにより発光する素子であって、該素子が一般式（２）で表されるピロメテン化合物の金属錯体の２量体を発光層のドーパントとして含有することを特徴とする発光素子である。
【００１０】
【化２】
（ここで、Ｒ８〜Ｒ１４の少なくとも一つは他のピロメテン骨格との直接あるいは置換基を介しての連結に用いられる。それ以外はそれぞれ同じでも異なっていてもよく、水素、アルキル基、アリール基、複素環基、Ｒ ８ とＲ ９ の部位で縮合したナフタレン環、Ｒ １２ とＲ １３ の部位で縮合したナフタレン環の中から選ばれる。Ｒ１５およびＲ１６はフッ素である。連結に用いられる置換基はアルキル基、アラルキル基、アリール基、複素環基より選ばれる。）
【００１２】
【発明の実施の形態】
本発明において陽極は、光を取り出すために透明であれば酸化錫、酸化インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロール、ポリアニリンなどの導電性ポリマなど特に限定されるものでないが、ＩＴＯガラスやネサガラスを用いることが特に望ましい。透明電極の抵抗は素子の発光に十分な電流が供給できればよいので限定されないが、素子の消費電力の観点からは低抵抗であることが望ましい。例えば３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。また、ガラス基板はソーダライムガラス、無アルカリガラスなどが用いられ、また厚みも機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用できる。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法、化学反応法など特に制限を受けるものではない。
【００１３】
陰極は、電子を本有機物層に効率良く注入できる物質であれば特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、カルシウム、マグネシウムなどがあげられるが、電子注入効率をあげて素子特性を向上させるためにはリチウム、ナトリウム、カリウム、カルシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかし、これらの低仕事関数金属は、一般に大気中で不安定であることが多く、例えば、有機層に微量のリチウムやマグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を使用する方法が好ましい例として挙げることができるが、フッ化リチウムのような無機塩の使用も可能であることから特にこれらに限定されるものではない。更に電極保護のために白金、金、銀、銅、鉄、錫、アルミニウム、インジウムなどの金属、またはこれら金属を用いた合金、そしてシリカ、チタニア、窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子などを積層することが好ましい例として挙げられる。これらの電極の作製法も抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティング、コーティングなど導通を取ることができれば特に制限されない。
【００１４】
発光物質とは、１）正孔輸送層／発光層、２）正孔輸送層／発光層／電子輸送層、３）発光層／電子輸送層、４）正孔輸送層／発光層／正孔阻止層、５）正孔輸送層／発光層／正孔阻止層／電子輸送層、６）発光層／正孔阻止層／電子輸送層そして、７）以上の組合わせ物質を一層に混合した形態のいずれであってもよい。即ち、素子構成としては、上記１）〜６）の多層積層構造の他に７）のように発光材料単独または発光材料と正孔輸送材料や電子輸送材料を含む層を一層設けるだけでもよい。さらに、本発明における発光物質は自ら発光するもの、その発光を助けるもののいずれにも該当し、発光に関与している化合物、層などを指すものである。
【００１５】
正孔輸送層は正孔輸送性物質単独または二種類以上の物質を積層、混合するか正孔輸送性物質と高分子結着剤の混合物により形成され、正孔輸送性物質としてはＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミン、Ｎ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−４，４’−ジフェニル−１，１’−ジアミンなどのトリフェニルアミン類、ビス（Ｎ−アリルカルバゾール）またはビス（Ｎ−アルキルカルバゾール）類、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、オキサジアゾール誘導体やフタロシアニン誘導体、ポルフィリン誘導体に代表される複素環化合物、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリビニルカルバゾール、ポリシランなどが好ましいが、素子作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されるものではない。
【００１６】
発光材料はホスト材料のみでも、ホスト材料とドーパント材料の組み合わせでも、いずれであってもよい。また、ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれであってもよい。ドーパント材料は積層されていても、分散されていても、いずれであってもよい。
【００１７】
本発明における発光材料はピロメテン化合物もしくはその金属錯体の、いずれかの骨格を少なくとも１つ有する多量体（以後ピロメテン多量体と呼ぶ）を含有する。ピロメテン化合物は発光材料、特にドーパント材料として、高輝度発光を示すことは知られている。しかし、単量体のピロメテン化合物には、分子量が小さく熱的安定性に乏しいものが多い。一方でピロメテン化合物の分子量を大きくするために置換基を導入する方法は、材料の発光特性や素子の膜質、電荷輸送能等に悪影響を及ぼすことが多い。そこで本発明のピロメテン多量体を用いることによって、材料の発光特性等に悪影響を及ぼすことなく、分子量を増大することが可能となり、熱的安定性が高く、かつ、高輝度発光を示す材料を得ることができた。
【００１８】
本発明のピロメテン多量体はホスト材料として用いてもよいが、蛍光量子収率が高いことや、発光スペクトルの半値幅が小さいことから、ドーパント材料として好適に用いられる。ピロメテン多量体としては、下記一般式（１）の化合物もしくはその金属錯体の、多量体があげられる。
【００１９】
【化３】
ここで、Ｒ1〜Ｒ7の少なくとも一つは他のピロメテン骨格との直接あるいは置換基を介しての連結に用いられる。それ以外はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される芳香族、脂肪族、あるいは複素環の縮合環の中から選ばれる。
【００２１】
連結に用いられる置換基は、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロアルカン、ハロアルケン、ハロアルキン、カルボニル基、エステル基、カルバモイル基、アミノ基、シリル基、シロキサニル基、スピロ基の中から選ばれる。
【００２２】
これらの置換基の内、アルキル基とは例えばメチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルキル基とは例えばシクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アラルキル基とは例えばベンジル基、フェニルエチル基などの脂肪族炭化水素を介した芳香族炭化水素基を示し、脂肪族炭化水素と芳香族炭化水素はいずれも無置換でも置換されていてもかまわない。また、アルケニル基とは例えばビニル基、アリル基、ブタジエニル基などの二重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルケニル基とは例えばシクロペンテニル基、シクロペンタジエニル基、シクロヘキセン基などの二重結合を含む不飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルキニル基とは例えばアセチレニル基などの三重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルコキシ基とは例えばメトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもかまわない。また、アルキルチオ基とはアルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリールエーテル基とは例えばフェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもかまわない。また、アリールチオエーテル基とはアリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリール基とは例えばフェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、複素環基とは例えばフラニル基、チオフェニル基、オキサゾリル基、ピリジル基、キノリニル基、カルバゾリル基などの炭素以外の原子を有する環状構造基を示し、これは無置換でも置換されていてもかまわない。
ハロゲンとはフッ素、塩素、臭素、ヨウ素を示す。ハロアルカン、ハロアルケン、ハロアルキンとは例えばトリフルオロメチル基などの、前述のアルキル基、アルケニル基、アルキニル基の一部あるいは全部が、前述のハロゲンで置換されたものを示し、残りの部分は無置換でも置換されていてもかまわない。アルデヒド基、カルボニル基、エステル基、カルバモイル基、アミノ基には脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環などで置換されたものも含み、さらに脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環は無置換でも置換されていてもかまわない。シリル基とは例えばトリメチルシリル基などのケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。シロキサニル基とは例えばトリメチルシロキサニル基などのエーテル結合を介したケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。隣接置換基との間に形成される縮合環および脂肪族環とは、Ｒ1とＲ2、Ｒ2とＲ3、Ｒ4とＲ5、Ｒ5とＲ6の部位で共役または非共役の縮合環を形成するものである。そしてこれら縮合環は環内構造に窒素、酸素、硫黄原子を含んでいてもよいし、さらに別の環と縮合してもよい。
【００２３】
また、金属に配位する時には、ピロメテン化合物単独でも混合配位子でも特に限定はされない。混合配位子の場合の第２の配位子としては、アルコキシ、フェノキシ、ハロゲン、アルキル、アリルその他縮合環炭化水素、複素環化合物、または酸素原子を介して結合された芳香環または複素環化合物などを導入することが可能である。
【００２４】
本発明のリガンドに配位できる金属は、特に限定されるものではないが、通常用いられる元素の一例として、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金などを挙げることができる。
【００２５】
さらに優れた色純度・輝度特性を得るために、ピロメテン多量体としては下記一般式（２）で表される化合物もしくはその金属錯体の、多量体が望ましい。
【００２６】
【化４】
ここで、Ｒ8〜Ｒ14の少なくとも一つは他のピロメテン骨格との直接あるいは置換基を介しての連結に用いられる。それ以外はそれぞれ同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される芳香族、脂肪族、あるいは複素環の縮合環の中から選ばれる。Ｒ15およびＲ16は同じでも異なっていてもよく、ハロゲン、水素、アルキル、アリール、複素環基から選ばれる。これらの置換基については上記一般式（１）の説明と同様である。
【００２８】
さらに材料の入手しやすさや、合成の容易さを考えると上記一般式（２）のＲ15およびＲ16はフッ素であることが望ましい。また、合成の収率や真空加熱等の蒸着による薄膜形成工程を考えると、ピロメテン多量体は２〜４量体であるのが好ましく、２量体であることがさらに好ましい。上記のピロメテン多量体の構造として、具体的に以下のようなものが挙げられる。
【００２９】
【化５】
【化６】
【化７】
【化８】
【化９】
ドーピング量は、多すぎると濃度消光現象が起きるため、ホスト物質に対して１０重量％以下で用いることが好ましく、更に好ましくは２重量％以下である。ドーピング方法としては、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着しても良い。また、ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれであってもよい。ドーパント材料は積層されていても、分散されていても、いずれであってもよい。さらに、ピロメテン多量体は、極めて微量でも発光することから微量のピロメテン多量体をホスト材料にサンドイッチ状に挟んで使用することも可能である。この場合、一層でも二層以上ホスト材料と積層しても良い。 発光材料に添加するドーパント材料は、前記ピロメテン多量体一種のみに限る必要はなく、複数のピロメテン多量体を混合して用いたり、既知のドーパント材料の一種類以上をピロメテン多量体と混合して用いてもよい。具体的には従来から知られている、ビス（ジイソプロピルフェニル）ペリレンテトラカルボン酸イミドなどのナフタルイミド誘導体、ペリノン誘導体、アセチルアセトンやベンゾイルアセトンとフェナントロリンなどを配位子とするＥｕ錯体などの希土類錯体、４−（ジシアノメチレン）−２−メチル−６−（ｐ−ジメチルアミノスチリル）−４Ｈ−ピランやその類縁体、マグネシウムフタロシアニン、アルミニウムクロロフタロシアニンなどの金属フタロシアニン誘導体、ローダミン化合物、デアザフラビン誘導体、オキサジン化合物などを共存させることができるが特にこれらに限定されるものではない。
【００３５】
ホスト材料としては特に限定されるものではないが、以前から発光体として知られていたアントラセンやピレンなどの縮合環誘導体、トリス（８−キノリノラト）アルミニウムを始めとする金属キレート化オキシノイド化合物、ビススチリルアントラセン誘導体やジスチリルベンゼン誘導体などのビススチリル誘導体、テトラフェニルブタジエン誘導体、クマリン誘導体、オキサジアゾール誘導体、ピロロピリジン誘導体、ペリノン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、チアジアゾロピリジン誘導体、ピロロピロール誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、そして、ポリチオフェン誘導体などが使用できる。
【００３６】
電子輸送性材料とは、電界を与えられた電極間において陰極からの電子を効率良く輸送することが必要で、電子注入効率が高く、注入された電子を効率良く輸送することが望ましい。そのためには電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。このような条件を満たす物質として、８−ヒドロキシキノリンアルミニウムに代表されるキノリノール誘導体金属錯体、トロポロン金属錯体、フラボノール金属錯体、ペリレン誘導体、ペリノン誘導体、ナフタレン、クマリン誘導体、オキサジアゾール誘導体、アルダジン誘導体、ビススチリル誘導体、ピラジン誘導体、フェナントロリン誘導体などがあるが特に限定されるものではない。これらの電子輸送材料は単独でも用いられるが、異なる電子輸送材料と積層または混合して使用しても構わない。
【００３７】
正孔阻止層とは、電界を与えられた電極間において陽極からの正孔が陰極からの電子と再結合することなく移動するのを防止するための層であり、各層を構成する材料の種類によっては、この層を挿入することにより正孔と電子の再結合確率が増加し、発光効率の向上が望める場合がある。したがって、正孔阻止性材料としては正孔輸送性材料よりも最高占有分子軌道レベルがエネルギー的に低く、隣接する層を構成する材料とエキサイプレックスを生成しにくいことが望まれる。
具体的にはフェナントロリン誘導体やトリアゾール誘導体などが挙げられるが、素子作製に必要な薄膜を形成し、陽極からの正孔の移動を効率よく阻止できる化合物であれば特に限定されるものではない。
【００３８】
以上の正孔輸送層、発光層、電子輸送層、正孔阻止層は単独または二種類以上の材料を積層、混合するか、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ（Ｎ−ビニルカルバゾール）、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルフォン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリサルフォン、ポリアミド、エチルセルロース、酢酸ビニル、ＡＢＳ樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
【００３９】
発光を司る物質の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法など特に限定されるものではないが、通常は、抵抗加熱蒸着、電子ビーム蒸着が特性面で好ましい。層の厚みは、発光を司る物質の抵抗値にもよるので限定することはできないが、１〜１０００ｎｍの間から選ばれる。
【００４０】
電気エネルギーとは主に直流電流を指すが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力、寿命を考慮するとできるだけ低いエネルギーで最大の輝度が得られるようにするべきである。
【００４１】
本発明におけるマトリクスとは、表示のための画素が格子状に配置されたものをいい、画素の集合で文字や画像を表示する。画素の形状、サイズは用途によって決まる。例えばパソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられるし、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法としては、線順次駆動方法やアクティブマトリックスのどちらでもよい。線順次駆動の方が構造が簡単であるという利点があるが、動作特性を考慮した場合、アクティブマトリックスの方が優れる場合があるので、これも用途によって使い分けることが必要である。
【００４２】
本発明におけるセグメントタイプとは、予め決められた情報を表示するようにパターンを形成し、決められた領域を発光させることになる。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示、自動車のパネル表示などがあげられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。
【００４３】
【実施例】
以下、実施例および比較例をあげて本発明を説明するが、本発明はこれらの例によって限定されるものではない。
【００４４】
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、エッチングを行った。得られた基板をアセトン、”セミコクリン５６”で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０-5Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フェニルアミノ）ビフェニルを５０ｎｍ蒸着した。次にホスト材料としてトリス（８−キノリノラト）アルミニウム錯体、ドーパンド材料として下記に示すＥＭ１を用いて、ドーパント濃度が１ｗｔ％になるように１５ｎｍの厚さに共蒸着し、ホスト材料を３５ｎｍの厚さに積層した。次にリチウムを０．５ｎｍ、銀を１５０ｎｍ蒸着して陰極とし、５×５ｍｍ角の素子を作製した。ここで言う膜厚は水晶発振式膜厚モニター表示値である。この発光素子は最高輝度１５０００ｃｄ／Ａの緑色発光を示した。この発光素子は５ｍＡの定電流駆動を行ったところ、１０００時間たっても輝度半減には至らなかった。
【００４５】
【化１０】
実施例２
ドーパント材料に下記に示すＥＭ２を用いた以外は実施例１と全く同様にして作製した。この発光素子は最高輝度１８０００ｃｄ／Ａの緑色発光を示した。この発光素子は５ｍＡの定電流駆動を行ったところ、１０００時間たっても輝度半減には至らなかった。
【００４７】
【化１１】
比較例１
ドーパント材料に下記に示すＥＭ３を用いた以外は実施例１と全く同様にして作製した。この発光素子は最高輝度１００００ｃｄ／Ａの緑色発光を示した。この発光素子は５ｍＡの定電流駆動を行ったところ、３００時間で輝度が半減した。
【００４９】
【化１２】
【発明の効果】
以上のように、ピロメテン多量体を発光材料として用いることにより、高輝度かつ耐久性に優れた発光素子を得ることができた。[0001]
BACKGROUND OF THE INVENTION
The present invention is an element that can convert electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. It relates to an element.
[0002]
[Prior art]
In recent years, research on an organic laminated thin film light emitting device in which light is emitted when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between both electrodes has been actively conducted. This element is attracting attention because it is thin, has high luminance emission under a low driving voltage, and multicolor emission by selecting a fluorescent material.
[0003]
This study was conducted by Kodak's C.I. W. Since Tang et al. Have shown that organic laminated thin-film elements emit light with high brightness (Appl. Phys. Lett. 51 (12) 21, p. 913, 1987), many research institutions have studied. A typical structure of an organic laminated thin film light emitting device presented by a research group of Kodak Company is a hole transporting diamine compound on an ITO glass substrate, 8-hydroxyquinoline aluminum as a light emitting layer, and Mg: Ag as a cathode. It is provided sequentially, and is 1000 cd / m with a driving voltage of about 10V.2Green light emission was possible. Some organic multilayer thin film light emitting elements have different configurations such as those provided with an electron transport layer in addition to the above-described element constituent elements, but basically follow the configuration of Kodak Company.
[0004]
As the host material of the light emitting layer, metal chelated oxinoid compounds such as tris (8-quinolinolato) aluminum, diarylbutadiene derivatives, stilbene derivatives, benzoxazole derivatives, benzothiazole derivatives (Japanese Patent Laid-Open No. 63-264692), etc. Can be given.
[0005]
On the other hand, dopant materials as guest materials are known to be useful as laser dyes, such as fluorescent coumarin dyes such as 7-dimethylamino-4-methylcoumarin, dicyanomethylenepyran dyes, dicyanomethylenethiols. Pyran dye, polymethine dye, cyanine dye, oxobenzanthracene dye, xanthene dye, rhodamine dye, fluorescein dye, pyrylium dye, carbostyryl dye, perylene dye, acridine dye, bis (styryl) benzene dye, pyrene dye, oxazine dye, Phenylene oxide dyes, perylene, tetracene, pentacene, quinacridone compounds, quinazoline compounds, pyrrolopyridine compounds, furopyridine compounds, 1,2,5-thiadiazolopyrene derivatives, perinone derivatives (JP-A-5-27) 662 JP) pyrrolo pyrrole compound (JP-A-5-320663), squarylium compound, violanthrone compound, phenazine derivatives, acridone compounds, such Jiazafurabin derivatives are known.
[0006]
Further, as a light-emitting material, particularly a dopant material, a pyromethene compound, which is a compound exhibiting high-luminance light emission, is known (Japanese Patent Laid-Open No. 9-118880).
[0007]
[Problems to be solved by the invention]
However, many of the light emitting materials (host materials and dopant materials) used in the prior art have low light emission efficiency and high power consumption, and low compound durability and short device lifetime. Among the three primary colors required for full-color displays, high-performance light-emitting materials have been found for green light emission, but in blue and red, especially red, light-emitting materials with sufficient characteristics, especially excellent durability, are obtained. Not. In addition, although the conventional pyromethene compounds are excellent in high luminance and high color purity, many have low molecular weight and poor thermal stability.
[0008]
An object of the present invention is to solve such problems of the prior art and to provide a light emitting element having high luminous efficiency and excellent durability.
[0009]
That is, the present invention is an element in which a luminescent substance exists between an anode and a cathode and emits light by electric energy, and the element is a pyromethene compound represented by the general formula (2).ThingA light-emitting element containing a dimer of a metal complex as a dopant of a light-emitting layer.
[0010]
[Chemical formula 2]
(Where R8~ R14At least one of is used for linking with another pyromethene skeleton directly or via a substituent. Other than that, they may be the same or different, and hydrogen, alkyl group, aryl group, heterocyclic group,R 8 And R 9 Naphthalene ring condensed at the site of R 12 And R 13 Naphthalene ring condensed at the siteChosen from. R15And R16Is fluorine. The substituent used for connection is selected from an alkyl group, an aralkyl group, an aryl group, and a heterocyclic group. )
[0012]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, if the anode is transparent for extracting light, a conductive metal oxide such as tin oxide, indium oxide and indium tin oxide (ITO), or a metal such as gold, silver and chromium, copper iodide, sulfide Inorganic conductive materials such as copper and conductive polymers such as polythiophene, polypyrrole, and polyaniline are not particularly limited, but it is particularly desirable to use ITO glass or Nesa glass. The resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the element can be supplied. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode. However, since it is now possible to supply a substrate of about 10 Ω / □, it is particularly desirable to use a low resistance product. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm. Further, soda lime glass, non-alkali glass or the like is used for the glass substrate, and the thickness of the glass substrate only needs to be sufficient to maintain the mechanical strength, so 0.5 mm or more is sufficient. As for the glass material, it is better to use alkali-free glass because it is better to have less ions eluted from the glass.2Since soda lime glass with a barrier coating such as is commercially available, it can be used. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, or a chemical reaction method.
[0013]
The cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer, but is generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium, calcium. Magnesium and the like can be mentioned, but lithium, sodium, potassium, calcium, magnesium or alloys containing these low work function metals are effective for improving the device characteristics by increasing the electron injection efficiency. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the vacuum vapor deposition thickness gauge display) to be stable. Although a method using a high electrode can be mentioned as a preferred example, it is not particularly limited to these because an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum, indium, or alloys using these metals, and inorganic substances such as silica, titania, silicon nitride, polyvinyl alcohol, vinyl chloride, Preferred examples include laminating hydrocarbon polymers. The method for producing these electrodes is not particularly limited as long as conduction can be achieved such as resistance heating, electron beam, sputtering, ion plating, and coating.
[0014]
The light-emitting substance is 1) hole transport layer / light-emitting layer, 2) hole transport layer / light-emitting layer / electron transport layer, 3) light-emitting layer / electron transport layer, 4) hole transport layer / light-emitting layer / hole Blocking layer, 5) Hole transport layer / light emitting layer / hole blocking layer / electron transport layer, 6) Light emitting layer / hole blocking layer / electron transport layer, and 7) Form in which one or more of the above combination materials are mixed Any of these may be used. That is, as the element structure, in addition to the multilayer laminated structure of 1) to 6) above, only a single layer including a light emitting material alone or a layer containing a light emitting material and a hole transport material or an electron transport material may be provided. Furthermore, the luminescent substance in the present invention corresponds to both a substance that emits light by itself and a substance that assists the light emission, and refers to a compound, a layer, or the like that is involved in light emission.
[0015]
The hole transport layer is formed by laminating and mixing a hole transport material alone or two or more kinds of materials, or a mixture of a hole transport material and a polymer binder. '-Diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl-N, N'-diphenyl-4,4'- Triphenylamines such as diphenyl-1,1′-diamine, bis (N-allylcarbazole) or bis (N-alkylcarbazole) s, pyrazoline derivatives, stilbene compounds, hydrazone compounds, oxadiazole derivatives and phthalocyanine derivatives , Heterocyclic compounds typified by porphyrin derivatives, in the case of polymer systems, polycarbonates or styrene derivatives having the above monomers in the side chain, polyvinylcarbazo Le, is preferred such as polysilane, forming a thin film required for device fabrication, and can inject holes from the anode, and is not particularly limited as long as it is a further compound capable of transporting holes.
[0016]
The light emitting material may be either a host material alone or a combination of a host material and a dopant material. Further, the dopant material may be included in the entire host material, or may be included partially. The dopant material may be either laminated or dispersed.
[0017]
The light-emitting material in the present invention contains a multimer having at least one skeleton of a pyromethene compound or a metal complex thereof (hereinafter referred to as a pyromethene multimer). It is known that a pyromethene compound exhibits high luminance light emission as a light emitting material, particularly as a dopant material. However, many monomeric pyromethene compounds have low molecular weight and poor thermal stability. On the other hand, a method of introducing a substituent in order to increase the molecular weight of the pyromethene compound often adversely affects the light emission characteristics of the material, the film quality of the device, the charge transporting ability, and the like. Therefore, by using the pyromethene multimer of the present invention, it is possible to increase the molecular weight without adversely affecting the light emission characteristics of the material, and to obtain a material having high thermal stability and high luminance emission. I was able to.
[0018]
Although the pyromethene multimer of the present invention may be used as a host material, it is preferably used as a dopant material because it has a high fluorescence quantum yield and a small half-value width of an emission spectrum. Examples of the pyromethene multimer include a multimer of a compound of the following general formula (1) or a metal complex thereof.
[0019]
[Chemical 3]
Where R1~ R7At least one of is used for linking with another pyromethene skeleton directly or via a substituent. Other than that, they may be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl Thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, adjacent substitution It is selected from aromatic, aliphatic, or heterocyclic condensed rings formed with the group.
[0021]
Substituents used for linking are alkyl groups, cycloalkyl groups, aralkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, mercapto groups, alkoxy groups, alkylthio groups, aryl ether groups, aryl thioether groups, aryl groups, heterocyclic rings. Selected from the group, haloalkane, haloalkene, haloalkyne, carbonyl group, ester group, carbamoyl group, amino group, silyl group, siloxanyl group, and spiro group.
[0022]
Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. The aralkyl group is an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. It doesn't matter. The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group or a butadienyl group, which may be unsubstituted or substituted. The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. . The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The alkoxy group refers to an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom. The aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom. The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group, which may be unsubstituted or substituted. The heterocyclic group is a cyclic structural group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, or a carbazolyl group, which may be unsubstituted or substituted. Absent.
Halogen is fluorine, chlorine, bromine or iodine. Haloalkane, haloalkene, haloalkyne means, for example, a part or all of the above-mentioned alkyl group, alkenyl group, alkynyl group such as trifluoromethyl group substituted with the above-mentioned halogen, and the remaining part may be unsubstituted It may be replaced. Aldehyde groups, carbonyl groups, ester groups, carbamoyl groups, amino groups include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic rings, etc. The cyclic hydrocarbon, aromatic hydrocarbon and heterocyclic ring may be unsubstituted or substituted. A silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. A fused ring and an aliphatic ring formed between adjacent substituents are R1And R2, R2And RThree, RFourAnd RFive, RFiveAnd R6A conjugated or non-conjugated condensed ring is formed at the site. These condensed rings may contain a nitrogen, oxygen or sulfur atom in the ring structure, or may be condensed with another ring.
[0023]
Further, when coordinated to a metal, there is no particular limitation on the pyromethene compound alone or a mixed ligand. As the second ligand in the case of a mixed ligand, alkoxy, phenoxy, halogen, alkyl, allyl and other condensed ring hydrocarbons, heterocyclic compounds, or aromatic rings or heterocyclic compounds bonded through an oxygen atom Etc. can be introduced.
[0024]
The metal that can be coordinated to the ligand of the present invention is not particularly limited. Examples of commonly used elements include boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum. be able to.
[0025]
In order to obtain more excellent color purity and luminance characteristics, the pyromethene multimer is preferably a multimer of a compound represented by the following general formula (2) or a metal complex thereof.
[0026]
[Formula 4]
Where R8~ R14At least one of is used for linking with another pyromethene skeleton directly or via a substituent. Other than that, they may be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl Thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, adjacent substitution It is selected from aromatic, aliphatic, or heterocyclic condensed rings formed with the group. R15And R16May be the same or different and are selected from halogen, hydrogen, alkyl, aryl, and heterocyclic groups. These substituents are the same as described in the general formula (1).
[0028]
Furthermore, considering the availability of materials and the ease of synthesis, R in the above general formula (2)15And R16Is preferably fluorine. Moreover, when considering the thin film formation process by vapor deposition such as synthesis yield and vacuum heating, the pyromethene multimer is preferably a 2 to tetramer, and more preferably a dimer. Specific examples of the structure of the above pyromethene multimer include the following.
[0029]
[Chemical formula 5]
[Chemical 6]
[Chemical 7]
[Chemical 8]
[Chemical 9]
If the doping amount is too large, a concentration quenching phenomenon occurs, so that it is preferably used in an amount of 10% by weight or less, more preferably 2% by weight or less based on the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited. Further, the dopant material may be included in the entire host material, or may be included partially. The dopant material may be either laminated or dispersed. Further, since the pyromethene multimer emits light even in a very small amount, it can be used by sandwiching a small amount of the pyromethene multimer between the host materials. In this case, one or more layers may be laminated with the host material. The dopant material added to the light emitting material need not be limited to only one type of pyromethene multimer, and a plurality of pyromethene multimers may be used in combination, or one or more types of known dopant materials may be used in combination with pyromethene multimers. May be. Specifically, conventionally known rare earth complexes such as naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, oxazine compounds, etc. However, the present invention is not particularly limited thereto.
[0035]
Although it does not specifically limit as a host material, Metal chelating oxinoid compounds, such as fused ring derivatives, such as anthracene and pyrene, tris (8- quinolinolato) aluminum which were known as a light emitter for a long time, bisstyryl Bisstyryl derivatives such as anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, pyrrolopyrrole derivatives In the polymer system, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polythiophene derivatives, and the like can be used.
[0036]
The electron transporting material is required to efficiently transport electrons from the cathode between electrodes to which an electric field is applied. It is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is required that the material has a high electron affinity, a high electron mobility, excellent stability, and a substance that does not easily generate trapping impurities during manufacturing and use. As substances satisfying such conditions, quinolinol derivative metal complexes represented by 8-hydroxyquinoline aluminum, tropolone metal complexes, flavonol metal complexes, perylene derivatives, perinone derivatives, naphthalene, coumarin derivatives, oxadiazole derivatives, aldazine derivatives, Although there are bisstyryl derivatives, pyrazine derivatives, phenanthroline derivatives, etc., there is no particular limitation. These electron transport materials are used alone, but may be laminated or mixed with different electron transport materials.
[0037]
The hole blocking layer is a layer for preventing the holes from the anode from moving between the electrodes to which an electric field is applied without recombining with the electrons from the cathode, and the kind of material constituting each layer. Depending on the case, insertion of this layer may increase the probability of recombination of holes and electrons, and may improve the light emission efficiency. Therefore, it is desirable that the hole-occluding material has a lower maximum occupied molecular orbital level than the hole-transporting material in terms of energy, and it is difficult to generate an exciplex with the material constituting the adjacent layer.
Specific examples include a phenanthroline derivative and a triazole derivative. However, the compound is not particularly limited as long as it is a compound that forms a thin film necessary for device fabrication and can efficiently block the movement of holes from the anode.
[0038]
The above hole transport layer, light-emitting layer, electron transport layer, and hole blocking layer may be a single material or a laminate of two or more materials, mixed, or a polymer binder such as polyvinyl chloride, polycarbonate, polystyrene, poly (N -Vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polysulfone, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane resin, etc. It can also be used by being dispersed in a soluble resin, a curable resin such as a phenol resin, a xylene resin, a petroleum resin, a urea resin, a melamine resin, an unsaturated polyester resin, an alkyd resin, an epoxy resin, or a silicone resin.
[0039]
The formation method of the substance responsible for light emission is not particularly limited, such as resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, coating method, etc., but resistance heating evaporation and electron beam evaporation are usually preferable in terms of characteristics. . The thickness of the layer is not limited because it depends on the resistance value of the substance responsible for light emission, but is selected from 1 to 1000 nm.
[0040]
Electrical energy mainly refers to direct current, but pulsed current or alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance should be obtained with the lowest possible energy in consideration of the power consumption and lifetime of the element.
[0041]
The matrix in the present invention refers to a matrix in which pixels for display are arranged in a lattice pattern, and displays characters and images by a set of pixels. The shape and size of the pixel are determined by the application. For example, a rectangular pixel with a side of 300 μm or less is normally used for displaying images and characters on a personal computer, monitor, television, etc. In a large display such as a display panel, a pixel with a side of mm order is used. . In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
[0042]
The segment type in the present invention means that a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation status display of an audio device or an electromagnetic cooker, the panel display of an automobile, etc. The matrix display and the segment display may coexist in the same panel.
[0043]
【Example】
EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated, this invention is not limited by these examples.
[0044]
Example 1
A glass substrate on which an ITO transparent conductive film was deposited to a thickness of 150 nm (Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporated product) was cut into 30 × 40 mm and etched. The obtained substrate was ultrasonically washed with acetone and “Semicocrine 56” for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was treated with UV-ozone for 1 hour immediately before producing the device, and placed in a vacuum vapor deposition apparatus. The degree of vacuum in the apparatus was 5 × 10.-FiveIt exhausted until it became Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 50 nm. Next, using a tris (8-quinolinolato) aluminum complex as a host material and EM1 shown below as a dopant material, it was co-evaporated to a thickness of 15 nm so that the dopant concentration would be 1 wt%. Laminated. Next, lithium was deposited at a thickness of 0.5 nm and silver was deposited at a thickness of 150 nm to form a cathode having a 5 × 5 mm square. The film thickness mentioned here is a display value of a crystal oscillation type film thickness monitor. This light-emitting element emitted green light with a maximum luminance of 15000 cd / A. When this light emitting element was driven at a constant current of 5 mA, the luminance was not reduced to half even after 1000 hours.
[0045]
Embedded image
Example 2
It was produced in the same manner as in Example 1 except that EM2 shown below was used as the dopant material. This light-emitting element emitted green light with a maximum luminance of 18000 cd / A. When this light emitting element was driven at a constant current of 5 mA, the luminance was not reduced to half even after 1000 hours.
[0047]
Embedded image
Comparative Example 1
It was produced in the same manner as in Example 1 except that EM3 shown below was used as the dopant material. This light-emitting element emitted green light with a maximum luminance of 10,000 cd / A. When the light emitting element was driven at a constant current of 5 mA, the luminance was reduced by half in 300 hours.
[0049]
Embedded image
【The invention's effect】
As described above, by using a pyromethene multimer as a light emitting material, a light emitting device having high luminance and excellent durability could be obtained.
Claims (2)
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| JP2000320568A JP4613411B2 (en) | 2000-10-20 | 2000-10-20 | Light emitting element |
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| JP2000320568A JP4613411B2 (en) | 2000-10-20 | 2000-10-20 | Light emitting element |
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| ES2454551T3 (en) | 2004-12-28 | 2014-04-10 | Gemin X Pharmaceuticals Canada Inc. | Dipyrrolic compounds, compositions, and methods for the treatment of cancer or viral diseases |
| TWI512400B (en) * | 2009-09-29 | 2015-12-11 | Fujifilm Corp | Colored curable composition, color resist, color filter and method for producing the same, and solid-state image sensor, image display device with the color filter |
| JP5694714B2 (en) * | 2009-10-23 | 2015-04-01 | 富士フイルム株式会社 | Dye multimer, colored curable composition, color filter and method for producing the same |
| JP5324513B2 (en) * | 2010-03-31 | 2013-10-23 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
| JP5566919B2 (en) * | 2010-08-20 | 2014-08-06 | 富士フイルム株式会社 | Colored curable composition, color filter and method for producing the same, solid-state imaging device, liquid crystal display device, and organic EL display device |
| CN107039591A (en) * | 2011-08-02 | 2017-08-11 | 南加利福尼亚大学 | The compound of symmetry breakdown Intramolecular electron transfer and the organic photovoltaic devices comprising it can be undergone in polarized media |
| WO2016072119A1 (en) * | 2014-11-07 | 2016-05-12 | ソニー株式会社 | Solid-state imaging device, and electronic device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09118880A (en) * | 1995-08-22 | 1997-05-06 | Toray Ind Inc | Light emission element |
| JPH09289081A (en) * | 1996-04-23 | 1997-11-04 | Mitsubishi Chem Corp | Organic electroluminous element |
| JPH10338695A (en) * | 1997-05-30 | 1998-12-22 | Avl Medical Instr | Indacene derivative |
| JPH1197180A (en) * | 1997-09-24 | 1999-04-09 | Mitsui Chem Inc | Organic electroluminescence element |
-
2000
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09118880A (en) * | 1995-08-22 | 1997-05-06 | Toray Ind Inc | Light emission element |
| JPH09289081A (en) * | 1996-04-23 | 1997-11-04 | Mitsubishi Chem Corp | Organic electroluminous element |
| JPH10338695A (en) * | 1997-05-30 | 1998-12-22 | Avl Medical Instr | Indacene derivative |
| JPH115796A (en) * | 1997-05-30 | 1999-01-12 | Avl Medical Instr | Indacene derivative |
| JPH1197180A (en) * | 1997-09-24 | 1999-04-09 | Mitsui Chem Inc | Organic electroluminescence element |
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