JP5652235B2 - 有機エレクトロルミネッセンス素子、表示装置及び照明装置 - Google Patents
有機エレクトロルミネッセンス素子、表示装置及び照明装置 Download PDFInfo
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- JP5652235B2 JP5652235B2 JP2011026838A JP2011026838A JP5652235B2 JP 5652235 B2 JP5652235 B2 JP 5652235B2 JP 2011026838 A JP2011026838 A JP 2011026838A JP 2011026838 A JP2011026838 A JP 2011026838A JP 5652235 B2 JP5652235 B2 JP 5652235B2
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- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- FXFWLXFJBVILBE-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)borane Chemical group CC1=CC(C)=CC(C)=C1B(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C FXFWLXFJBVILBE-UHFFFAOYSA-N 0.000 description 1
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
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- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Description
本発明の有機EL素子について説明する。
下記の合成フローに従って、例示化合物1を合成した。
300ml三頭フラスコに、カルバゾール10g、硝酸100mlを加え、90℃まで加温し2時間撹拌した。
300ml三頭フラスコに、3,6−ジニトロカルバゾール9g、硫酸50mlを加え溶解させた。この溶液に、臭素3.3mlを滴下した後、90℃まで加温し2時間撹拌した。反応液を冷却後、氷水に反応液を注いだ。析出した結晶を濾過し、この析出物をシリカゲルクロマト(展開液 ヘキサン:酢酸エチル=10:1)により精製し、目的物を5.2g得た。
1,8−ジブロモ−3,6−ジニトロカルバゾール 5gをTHF100mlに溶解し、Pd/C 0.5gを加えた後、水素添加反応を室温で5時間行った。
100ml三頭フラスコに、1,8−ジブロモ−3,6−ジアミノカルバゾール1.5g、水12ml、EtOH10ml、HCl2ml加え、撹拌した。この溶液を10℃まで冷却して、亜硝酸ナトリウム7gを水10mlに溶かした溶液を滴下し、30分10℃で撹拌した。その後、H3PO2を10ml加え、更に10℃で4時間撹拌した。
三頭100mlフラスコに、1,8−ジブロモカルバゾール1g、フェニルボロン酸1.5g、pd(dba)20.1g、dppf0.1g、炭酸カリウム1.8gを加え、更にジメトキシエタン30ml、水10ml加えた。窒素気流化にて、6時間加熱還流行った。
三頭100mlフラスコに、1,8−ジフェニルカルバゾール0.6g、1,3−ジヨードベンゼン0.15g、銅粉0.12g、炭酸カリウム0.7gを加え、ジメチルアセトアミド30ml加えた。窒素気流化にて、内温135℃にて6時間加熱行った。
次いで、本発明の有機EL素子の構成層について説明する。本発明において、有機EL素子の層構成の好ましい具体例を以下に示すが、本発明はこれらに限定されない。
(ii)陽極/正孔輸送層/発光層/電子輸送層/陰極
(iii)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極
(iv)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(v)陽極/陽極バッファー層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vi)陽極//正孔輸送層/陽極バッファー層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vii)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
発光層は、ユニットを形成して発光層ユニットにすることもある。更に、発光層間には非発光性の中間層を有していてもよく、中間層は電荷発生層を含んでいてもよい。本発明の有機EL素子としては白色発光であることが好ましく、これらを用いた照明装置であることが好ましい。
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層、正孔阻止層も電子輸送層に含まれる。電子輸送層は単層もしくは複数層を設けることができる。
本発明に係る発光層は、電極または電子輸送層、正孔輸送層から注入されてくる電子及び正孔が再結合して発光する層であり、発光する部分は発光層の層内であっても発光層と隣接層との界面であってもよい。
本発明に用いられる発光ホストとしては、一般式(1)で示される部分構造を有する化合物であることが好ましい。
(発光ドーパント)
発光ドーパントについて説明する。
リン光ドーパントについて説明する。
蛍光ドーパント(蛍光性化合物ともいう)としては、クマリン系色素、ピラン系色素、シアニン系色素、クロコニウム系色素、スクアリウム系色素、オキソベンツアントラセン系色素、フルオレセイン系色素、ローダミン系色素、ピリリウム系色素、ペリレン系色素、スチルベン系色素、ポリチオフェン系色素、または希土類錯体系蛍光体等や、レーザー色素に代表される蛍光量子収率が高い化合物が挙げられる。
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層または複数層設けることができる。
阻止層は、上記の如く有機化合物薄膜の基本的な構成層の他に、必要に応じて設けられるものである。例えば、特開平11−204258号公報、同11−204359号公報、及び「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の237頁等に記載されている正孔阻止(ホールブロック)層がある。
注入層は必要に応じて設けられ、電子注入層と正孔注入層があり、上記の如く陽極と発光層または正孔輸送層との間、及び陰極と発光層または電子輸送層との間に存在させてもよい。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としては、Au等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。
一方、陰極としては仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質として用いられる。
本発明の有機EL素子に用いることのできる基板としては、ガラス、プラスチック等、種類には特に限定はなく、また透明であっても不透明であってもよい。基板側から光を取り出す場合には、基板は透明であることが好ましい。
有機EL素子の製造方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層(電子注入層)/陰極から構成される有機EL素子の製造方法について説明する。
本発明に用いられる封止手段としては、例えば、封止部材と電極、基板とを接着剤で接着する方法を挙げることができる。
有機層を挟み基板と対向する側の前記封止膜、あるいは前記封止用フィルムの外側に、素子の機械的強度を高めるために保護膜、あるいは保護板を設けてもよい。特に封止が前記封止膜により行われている場合には、その機械的強度は必ずしも高くないため、このような保護膜、保護板を設けることが好ましい。これに使用することができる材料としては、前記封止に用いたのと同様なガラス板、ポリマー板・フィルム、金属板・フィルム等を用いることができるが、軽量且つ薄膜化ということからポリマーフィルムを用いることが好ましい。
有機EL素子は空気よりも屈折率の高い(屈折率が1.7〜2.1程度)層の内部で発光し、発光層で発生した光のうち15%から20%程度の光しか取り出せないことが一般的に言われている。これは、臨界角以上の角度θで界面(透明基板と空気との界面)に入射する光は、全反射を起こし素子外部に取り出すことができないことや、透明電極ないし発光層と透明基板との間で光が全反射を起こし、光が透明電極ないし発光層を導波し、結果として光が素子側面方向に逃げるためである。
本発明の有機EL素子は、基板の光取り出し側に、例えば、マイクロレンズアレイ状の構造を設けるように加工すること、あるいは集光シートと組み合わせることにより、特定方向、例えば、素子発光面に対し正面方向に集光することにより、特定方向上の輝度を高めることができる。
本発明の有機EL素子は、表示デバイス、ディスプレイ、各種発光光源として用いることができる。発光光源として、例えば、照明装置(家庭用照明、車内照明)、時計や液晶用バックライト、看板広告、信号機、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられるがこれに限定するものではないが、特に液晶表示装置のバックライト、照明用光源としての用途に有効に用いることができる。
本発明の表示装置について説明する。本発明の表示装置は、本発明の有機EL素子を具備したものである。
本発明の照明装置について説明する。本発明の照明装置は、本発明の有機EL素子を有する。
本発明の有機EL素子を具備した、本発明の照明装置の一態様について説明する。
《有機EL素子の作製》
〔有機EL素子1−1の作製〕
100mm×100mm、厚さ1.1mmのガラス基板上に、陽極としてITO(インジウムチンオキシド)を100nm成膜した基板(NHテクノグラス社製NA45)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基板をイソ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。
上記有機EL素子1−1の作製において、発光層の形成に用いる発光ホストを比較1から表1に記載のように、比較2及び本発明に係る例示化合物にそれぞれ変更した以外は同様にして、有機EL素子1−2〜1−20を作製した。
上記作製した有機EL素子1−1〜1−20について、下記の各評価を行った。
各有機EL素子を、室温(約23℃〜25℃)で、2.5mA/cm2の定電流条件下で発光させ、発光開始直後の発光輝度(L)[cd/m2]を測定することにより、外部取り出し量子効率(η)を算出した。なお、発光輝度の測定は、CS−1000(コニカミノルタセンシング製)を用いた。
有機EL素子を、室温(約23℃〜25℃)で、2.5mA/cm2の定電流条件下による連続発光を行い、初期輝度の1/2の輝度になるのに要する時間(半減期τ1/2)を測定し、これを発光寿命の尺度とした。なお、発光寿命は有機EL素子1−1を100とする相対値で表した。
有機EL素子について、2.5mA/cm2の定電流条件下で発光させた時の駆動電圧と発光輝度50%になった時の駆動電圧を測定し、ΔV=(初期電圧−輝度50%時電圧)を測定し、比較試料との相対値で示した。表1では有機EL素子1−1のΔVを100とする相対値で表した。この値が低い方が駆動時の電圧上昇が少なく好ましい。
《有機EL素子の作製》
〔有機EL素子2−1の作製〕
陽極として100mm×100mm、厚さ1.1mmのガラス基板上に、ITO(インジウムチンオキシド)を、厚さ100nmで製膜した基板(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基板をイソ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。
上記有機EL素子2−1の作製において、発光層の形成に用いる発光ホストを、比較1から表2に記載のように、比較2及び本発明に係る例示化合物にそれぞれ変更した以外は同様にして、有機EL素子2−2〜2−20を作製した。
上記作製した有機EL素子2−1〜2−20について、実施例1に記載の方法と同様にして、発光効率の評価(外部取り出し量子効率の測定)、発光寿命の測定、駆動時の電圧上昇の測定を行い、得られた結果を表2に示す。なお、上記各評価においては、有機EL素子2−1の各特性値を100とした相対値で表した。
《フルカラー表示装置の作製》
(青色発光素子の作製)
実施例1で作製した有機EL素子1−11を、青色発光素子として用いた。
実施例1に記載の有機EL素子1−1の作製において、発光ドーパントとして、D−26に代えて、D−1を用いた以外は同様にして、緑色発光素子を作製した。
実施例1に記載の有機EL素子1−1の作製において、発光ドーパントとして、D−26に代えて、D−10を用いた以外は同様にして、赤色発光素子を作製した。
《白色発光素子及び白色照明装置の作製》
実施例1に記載の透明電極基板の電極を、20mm×20mmにパターニングし、その上に実施例1と同様にして正孔輸送層としてα−NPDを25nmの厚さで成膜し、更に、発光ホストである例示化合物16の入った加熱ボートと、D−26の入ったボート及びD−10の入ったボートをそれぞれ独立に通電して、発光ホストである例示化合物16と発光ドーパントとしてD−26、及びD−10の蒸着速度が100:5:0.6になるように調節し、膜厚30nmの厚さになるように蒸着し、発光層を設けた。
《白色の有機EL素子の作製》
陽極として100mm×100mm、厚さ1.1mmのガラス基板上に、ITO(インジウムチンオキシド)を100nm成膜した基板(NHテクノグラス社製NA45)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基板をイソ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。
3 画素
5 走査線
6 データ線
7 発光した光
A 表示部
B 制御部
101 有機EL素子
102 ガラスカバー
105 陰極
106 有機EL層
107 透明電極付きガラス基板
108 窒素ガス
109 捕水剤
Claims (6)
- 下記一般式(2)または一般式(3)で表される部分構造を有す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。
- 前記有機エレクトロルミネッセンス素子の発光形式がりん光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。
- 発光色が青色であることを特徴とする請求項1または2に記載の有機エレクトロルミネッセンス素子。
- 発光色が白色であることを特徴とする請求項1または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から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を備えたことを特徴とする表示装置。
- 請求項1から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を備えたことを特徴とする照明装置。
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US10418564B2 (en) * | 2014-04-11 | 2019-09-17 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US9732069B2 (en) | 2014-05-21 | 2017-08-15 | Samsung Electronics Co., Ltd. | Carbazole compound and organic light emitting device including the same |
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US8221905B2 (en) * | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
EP2460866B1 (en) * | 2008-05-13 | 2019-12-11 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and lighting device |
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US8895966B2 (en) * | 2010-03-31 | 2014-11-25 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence element, and organic electroluminescence element using same |
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