JP5279254B2 - 有機発光素子及び表示装置 - Google Patents
有機発光素子及び表示装置 Download PDFInfo
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- JP5279254B2 JP5279254B2 JP2007325914A JP2007325914A JP5279254B2 JP 5279254 B2 JP5279254 B2 JP 5279254B2 JP 2007325914 A JP2007325914 A JP 2007325914A JP 2007325914 A JP2007325914 A JP 2007325914A JP 5279254 B2 JP5279254 B2 JP 5279254B2
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- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006059 cover glass Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N germanium monoxide Inorganic materials [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N nickel(II) oxide Inorganic materials [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical compound [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/611—Charge transfer complexes
-
- 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
- H10K85/60—Organic compounds having low molecular weight
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
(式(4)において、R11乃至R13は、式(3)のR11乃至R13と同様である。)
インダン−1,3−ジオン:0.73g(5mmol)
マロノニトリル:0.66g(10mmol)
メタノール:15ml
図4に示される構造の有機発光素子を作製した。
実施例1において、塗料組成物の組成を以下のようにした他は、実施例1と同様の方法により有機発光素子を作製した。
例示化合物No.1−1:4質量部
クロロホルム:49900質量部
実施例1において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.1−9を使用した他は、実施例1と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例2において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.1−9を使用した他は、実施例2と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例1において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−1を使用した他は、実施例1と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例2において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−1を使用した他は、実施例2と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例1において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−11を使用した他は、実施例1と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例2において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−11を使用した他は、実施例2と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例1において、塗料組成物の組成を以下のようにした他は、実施例1と同様の方法により有機発光素子を作製した。
クロロホルム:49900質量部
得られた素子について実施例1と同様に評価した。結果を表1に示す。
実施例2において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに下記式(IV)に示されるベンゾキノン誘導体を使用した他は、実施例2と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に評価した。結果を表1に示す。
図6に示される構造の有機発光素子を作製した。
実施例9において、塗料組成物の組成を以下のようにした他は、実施例9と同様の方法により有機発光素子を作製した。
例示化合物No.1−1:4質量部
クロロホルム:99900質量部
実施例9において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.1−9を使用した他は、実施例9と同様の方法により有機発光素子を作製した。得られた素子について実施例9と同様に評価した。結果を表2に示す。
実施例10において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.1−9を使用した他は、実施例10と同様の方法により有機発光素子を作製した。得られた素子について実施例9と同様に評価した。結果を表2に示す。
実施例9において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−1を使用した他は、実施例9と同様の方法により有機発光素子を作製した。得られた素子について実施例9と同様に評価した。結果を表2に示す。
実施例10において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−1を使用した他は、実施例10と同様の方法により有機発光素子を作製した。得られた素子について実施例9と同様に評価した。結果を表2に示す。
実施例9において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−11を使用した他は、実施例9と同様の方法により有機発光素子を作製した。得られた素子について実施例9と同様に評価した。結果を表2に示す。
実施例10において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに例示化合物No.2−11を使用した他は、実施例10と同様の方法により有機発光素子を作製した。得られた素子について実施例9と同様に評価した。結果を表2に示す。
実施例9において、塗料組成物の組成を以下のようにした他は、実施例1と同様の方法により有機発光素子を作製した。
クロロホルム:99900質量部
実施例10において、塗料組成物を調製する際に、例示化合物No.1−1の代わりに式(IV)に示されるベンゾキノン誘導体を使用した他は、実施例10と同様の方法により有機発光素子を作製した。得られた素子について実施例10と同様に評価した。結果を表2に示す。
2 陽極
3 発光層
4 陰極
5 正孔輸送層
6 電子輸送層
7 正孔注入層
8 電子注入層
9 正孔/エキシトンブロッキング層
10,20,30,40,50,60,70,94 有機発光素子
80,100 表示装置
81 走査信号ドライバー
82 情報信号ドライバー
83 電流供給源
84,90 画素回路
91 第一の薄膜トランジスタ(TFT1)
92 コンデンサー(Cadd)
93 第二の薄膜トランジスタ(TFT2)
101 基板
102 防湿層
103 ゲート電極
104 ゲート絶縁膜
105 半導体膜
106 ドレイン電極
107 ソース電極
108 TFT素子
109 絶縁膜
110 コンタクトホール(スルーホール)
111 陽極
112 有機層
113 陰極
114 第一の保護層
115 第二の保護層
Claims (5)
- 陽極と陰極と、
該陽極と該陰極との間に挟持される有機化合物からなる層と、から構成され、
該有機化合物からなる層に下記一般式(1)又は(2)で示されるテトラシアノ化合物が少なくとも一種類含まれることを特徴とする、有機発光素子。
- 前記テトラシアノ化合物が正孔注入層及び正孔輸送層のいずれかに含まれることを特徴とする、請求項1又は2に記載の有機発光素子。
- 前記テトラシアノ化合物が電子注入層及び電子輸送層のいずれかに含まれることを特徴とする、請求項1又は2に記載の有機発光素子。
- 請求項1乃至4のいずれか一項に記載の有機発光素子を具備することを特徴とする、表示装置。
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JP5286752B2 (ja) * | 2007-11-21 | 2013-09-11 | 三菱化学株式会社 | 電子写真感光体、電子写真カートリッジ、画像形成装置、及び画像形成方法 |
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