JP4631259B2 - 有機エレクトロルミネッセンス素子及び表示装置 - Google Patents
有機エレクトロルミネッセンス素子及び表示装置 Download PDFInfo
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- JP4631259B2 JP4631259B2 JP2003324217A JP2003324217A JP4631259B2 JP 4631259 B2 JP4631259 B2 JP 4631259B2 JP 2003324217 A JP2003324217 A JP 2003324217A JP 2003324217 A JP2003324217 A JP 2003324217A JP 4631259 B2 JP4631259 B2 JP 4631259B2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CUIWZLHUNCCYBL-UHFFFAOYSA-N decacyclene Chemical compound C12=C([C]34)C=CC=C4C=CC=C3C2=C2C(=C34)C=C[CH]C4=CC=CC3=C2C2=C1C1=CC=CC3=CC=CC2=C31 CUIWZLHUNCCYBL-UHFFFAOYSA-N 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound 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 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
Images
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Description
下記一般式(3)で表される化合物を含有することを特徴とする有機エレクトロルミネッセンス素子。
一般式(3)において、R21、R23、R24、R26のうち少なくとも二つはアリール基であることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
(請求項3)
請求項1又は2に記載の化合物が、発光層に使用されることを特徴とする請求項1又は2に記載の有機エレクトロルミネッセンス素子。
(請求項4)
請求項1又は2に記載の化合物が、正孔ブロック層に使用されることを特徴とする請求項1又は2に記載の有機エレクトロルミネッセンス素子。
(請求項5)
りん光性化合物を含有することを特徴とする請求項1〜4のいずれか1項に記載の有機エレクトロルミネッセンス素子。
(請求項6)
りん光性化合物が、オスミウム、イリジウム、または、白金錯体系化合物であることを特徴とする請求項5に記載の有機エレクトロルミネッセンス素子。
(請求項7)
請求項1〜6のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする表示装置。
オルトトリジン5.0gと2,5ヘキサンジオン5.0gを酢酸50mlに溶解し3時間加熱攪拌した。反応終了後、反応液に、酢酸エチル、水を加えて有機層を抽出した。硫酸マグネシウムで乾燥後、溶媒を減圧留去してからカラムクロマトグラフィーで精製した後、アセトニトリルで再結晶し、化合物(1−2)を6.9g得た(収率80%)。
合成例1において、2,5ヘキサンジオンを1,2ジベンゾイルエタンに変更した以外は、合成例1にのっとって化合物(1−8)を合成した。
シクロヘキサノン20gとアニリン38gを濃塩酸中で40時間加熱還流した。反応液を中和後、反応液に、酢酸エチル、水を加えて有機層を抽出した。硫酸マグネシウムで乾燥後、溶媒を減圧留去してからカラムクロマトグラフィーで精製しアミン化合物を31g得た。該アミン化合物と1,2ジベンゾイルエタンを合成例2にのっとって合成し化合物(8−1)を得た。
(i)陽極/発光層/陰極
(ii)陽極/正孔輸送層/発光層/陰極
(iii)陽極/発光層/電子輸送層/陰極
(iv)陽極/正孔輸送層/発光層/電子輸送層/陰極
(v)陽極/陽極バッファー層/正孔輸送層/発光層/電子輸送層/陰極バッファー層/陰極
(vi)陽極/陽極バッファー層/正孔輸送層/発光層/正孔ブロック層/電子輸送層/陰極バッファー層/陰極
などの構造がある。
陽極としてガラス上にITOを150nm製膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をi−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定した。
以下のようにして得られた有機EL素子の評価を行った。
実施例1で作製した有機EL素子を温度23度、乾燥窒素ガス雰囲気下で2.5、10、100mA/cm2の一定電流で駆動した時の発光効率(lm/W)を測定した。各有機EL素子について、発光効率を有機EL素子OLED1−1の2.5mA/cm2の一定電流で駆動した時の発光効率を100とした時の相対値を%表示で表した。本測定は分光放射輝度計CS−1000(ミノルタ製)を用いて測定した。
結果を表1に示す。
実施例1のOLED1−1で作製した有機EL素子の正孔ブロック層の材料をBCから表2に記載の化合物に変更した以外は実施例1と全く同様にして有機EL素子OLED2−1、3、8、〜10を作製した。
実施例1で作製したそれぞれ赤色、緑色、青色発光有機EL素子を同一基板上に並置し、図1に示すアクティブマトリクス方式フルカラー表示装置を作製した。
3 画素
5 走査線
6 データ線
Claims (7)
- 一般式(3)において、R21、R23、R24、R26のうち少なくとも二つはアリール基であることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
- 請求項1又は2に記載の化合物が、発光層に使用されることを特徴とする請求項1又は2に記載の有機エレクトロルミネッセンス素子。
- 請求項1又は2に記載の化合物が、正孔ブロック層に使用されることを特徴とする請求項1又は2に記載の有機エレクトロルミネッセンス素子。
- りん光性化合物を含有することを特徴とする請求項1〜4のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- りん光性化合物が、オスミウム、イリジウム、または、白金錯体系化合物であることを特徴とする請求項5に記載の有機エレクトロルミネッセンス素子。
- 請求項1〜6のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする表示装置。
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WO2005030901A1 (ja) * | 2003-09-29 | 2005-04-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子 |
CN100505965C (zh) | 2004-11-25 | 2009-06-24 | 新日铁化学株式会社 | 有机电致发光元件 |
US20090198069A1 (en) * | 2005-03-25 | 2009-08-06 | Nagasaki University, National University Corporati | Metal complex, light-emitting device and display |
KR101402633B1 (ko) * | 2005-04-28 | 2014-06-03 | 시바 홀딩 인크 | 전기발광 장치 |
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JP4904734B2 (ja) * | 2005-07-20 | 2012-03-28 | 三菱化学株式会社 | 新規ピラゾール誘導体及びこれを含有する有機el素子 |
JPWO2007111263A1 (ja) | 2006-03-27 | 2009-08-13 | 出光興産株式会社 | 含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US7998995B2 (en) | 2006-12-08 | 2011-08-16 | Exelixis Patent Company Llc | LXR and FXR modulators |
KR101030020B1 (ko) * | 2008-09-02 | 2011-04-20 | 제일모직주식회사 | 피롤계 화합물 및 이를 포함하는 유기광전소자 |
TWI469968B (zh) * | 2009-03-31 | 2015-01-21 | Semiconductor Energy Lab | 雜環化合物及使用該雜環化合物之發光元件、發光裝置、照明裝置和電子設備 |
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JP6028668B2 (ja) * | 2013-04-17 | 2016-11-16 | コニカミノルタ株式会社 | 透明電極、電子デバイス及び有機エレクトロルミネッセンス素子 |
CN104230829B (zh) * | 2014-09-26 | 2016-04-20 | 天津师范大学 | 联苯双三唑化合物及其制备方法与应用 |
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JP2002203683A (ja) * | 2000-10-30 | 2002-07-19 | Toyota Central Res & Dev Lab Inc | 有機電界発光素子 |
JP2002305084A (ja) * | 2000-12-25 | 2002-10-18 | Fuji Photo Film Co Ltd | 新規インドール誘導体およびそれを利用した発光素子 |
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