JP5742811B2 - 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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- JP5742811B2 JP5742811B2 JP2012222413A JP2012222413A JP5742811B2 JP 5742811 B2 JP5742811 B2 JP 5742811B2 JP 2012222413 A JP2012222413 A JP 2012222413A JP 2012222413 A JP2012222413 A JP 2012222413A JP 5742811 B2 JP5742811 B2 JP 5742811B2
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H05B33/00—Electroluminescent light sources
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- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Description
具体的に本発明によれば、下記構成1において、一般式(A)中、X、Yは、各々Sを表し、L3は、m−フェニレン基を表し、A1、A2、L1、L2、L3はピレンである場合を除く有機エレクトロルミネッセンス素子が提供される。
該発光層の少なくとも1層が下記一般式(A)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。
2.前記L3が、アリーレン基、ヘテロアリーレン基、2価の複素環基またはアルキレン基を表すことを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
11.前記窒素原子を含む置換基がジアリールアミノ基であることを特徴とする前記8に記載の有機エレクトロルミネッセンス素子。
16.前記一般式(B)で表されるリン光発光性の金属錯体のm2が0であることを特徴とする前記1〜15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。
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
本発明の有機EL素子においては、青色発光層の発光極大波長は430nm〜480nmにあるものが好ましく、緑色発光層は発光極大波長が510nm〜550nm、赤色発光層は発光極大波長が600nm〜640nmの範囲にある単色発光層であることが好ましく、これらを用いた表示装置であることが好ましい。また、これらの少なくとも3層の発光層を積層して白色発光層としたものであってもよい。更に、発光層間には非発光性の中間層を有していてもよい。本発明の有機EL素子としては白色発光層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。
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ホスト化合物について説明する。
一般式(A)で表される化合物について説明する。
本発明に係る発光ドーパントについて説明する。
本発明に係るリン光発光性ドーパントについて説明する。
一般式(B)で表される化合物について説明する。
蛍光ドーパントとしては、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が挙げられる。
注入層は必要に応じて設け、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。
阻止層は、上記の如く有機化合物薄膜の基本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。
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。
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。電子輸送層は単層または複数層設けることができる。
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。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。
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するものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。
本発明の有機EL素子に用いることのできる支持基板(以下、基体、基板、基材、支持体等とも言う)としては、ガラス、プラスチック等の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。
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、支持基板とを接着剤で接着する方法を挙げることができる。
有機層を挟み支持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。
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したり、あるいは所謂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素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極からなる有機EL素子の作製法を説明する。
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らに限定されない。
《有機EL素子1−1の作製》
陽極として100mm×100mm×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支持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。
有機EL素子1−1の作製において、発光層のホスト化合物であるCBPを表1に示す化合物に置き換え、例示化合物1−1を表1に示す化合物に置き換えた以外は同様にして、有機EL素子1−2〜1−15を作製した。
作製した有機EL素子1−1〜1−15の評価を行い、その結果を表1に示す。
得られた有機EL素子1−1〜1−16を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材としてエポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図3、図4に示すような照明装置を形成して評価した。
作製した有機EL素子について、23℃、乾燥窒素ガス雰囲気下で2.5mA/cm2定電流を印加した時の外部取り出し量子効率(%)を測定した。なお測定には分光放射輝度計CS−1000(コニカミノルタ製)を用いた。
2.5mA/cm2の一定電流で駆動したときに、輝度が発光開始直後の輝度(初期輝度)の半分に低下するのに要した時間を測定し、これを半減寿命時間(τ0.5)として寿命の指標とした。なお測定には分光放射輝度計CS−1000(コニカミノルタ製)を用いた。尚、表1の寿命は、有機EL素子1−1の寿命を100とした時の相対値で表した。得られた結果を表1に示す。
《有機EL素子2−1の作製》
陽極として100mm×100mm×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支持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。
有機EL素子2−1の作製において、発光層のホスト化合物として用いているCBPを表2に示す化合物に置き換え、発光層のドーパント化合物として用いているIr−1を表2に示す化合物に置き換えた以外は同様にして有機EL素子2−2〜2−15を各々作製した。
実施例1と同様にして、作製した有機EL素子2−1〜2−28の評価を行い、その結果を表2に示す。
《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の有機EL素子1−9を青色発光素子として用いた。
実施例2の有機EL素子2−4を緑色発光素子として用いた。
実施例1の有機EL素子1−1において、ホスト化合物をCBP、ドーパントをIr−14に変更した以外は同様にして、赤色発光素子を作製し、これを赤色発光素子として用いた。
《白色発光素子及び白色照明装置の作製》
実施例1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と同様に正孔注入/輸送層としてα−NPDを40nmの厚さで成膜し、さらに例示化合物1の入った前記加熱ボートと例示化合物1−75の入ったボート及びIr−4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1と発光ドーパントである例示化合物1−75及びIr−4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。
3 画素
5 走査線
6 データ線
A 表示部
B 制御部
101 有機EL素子
107 透明電極付きガラス基板
106 有機EL層
105 陰極
102 ガラスカバー
108 窒素ガス
109 捕水剤
Claims (15)
- 支持基板上に少なくとも陽極、陰極を有し、該陽極と該陰極間に少なくとも1層の発光層を有する有機エレクトロルミネッセンス素子において、
該発光層の少なくとも1層が下記一般式(A)で表される化合物(下記化合物B−2およびB−8を除く。)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。
- 支持基板上に少なくとも陽極、陰極を有し、該陽極と該陰極間に少なくとも1層の発光層を有する有機エレクトロルミネッセンス素子において、
該発光層の少なくとも1層が下記一般式(A)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。
- 支持基板上に少なくとも陽極、陰極を有し、該陽極と該陰極間に少なくとも1層の発光層を有する有機エレクトロルミネッセンス素子において、
該発光層の少なくとも1層が下記一般式(A)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。
- 前記n1が1または2であることを特徴とする請求項1〜3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。
- 前記n2が1または2であ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。
- 前記nが1または2であることを特徴とする請求項1〜5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。
- 前記A1、A2の少なくとも一方がジアリールアミノ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。
- 前記発光層にリン光発光性の金属錯体を含有することを特徴とする請求項1〜7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。
- 前記リン光発光性の金属錯体がIr錯体であることを特徴とする請求項8に記載の有機エレクトロルミネッセンス素子。
- 前記リン光発光性の金属錯体が下記一般式(B)で表されることを特徴とする請求項8または9に記載の有機エレクトロルミネッセンス素子。
- 前記一般式(B)で表されるリン光発光性の金属錯体のm2が0であることを特徴とする請求項10に記載の有機エレクトロルミネッセンス素子。
- 前記一般式(B)で表されるリン光発光性の金属錯体のB1〜B5で形成される含窒素複素環がイミダゾール環であることを特徴とする請求項10または11に記載の有機エレクトロルミネッセンス素子。
- 白色に発光することを特徴とする請求項1〜12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1〜13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1〜13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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JP4947955B2 (ja) | 2005-11-04 | 2012-06-06 | 三洋電機株式会社 | ジベンゾチオフェン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
JPWO2007055186A1 (ja) * | 2005-11-09 | 2009-04-30 | コニカミノルタホールディングス株式会社 | 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 |
TWI420963B (zh) * | 2005-12-15 | 2013-12-21 | Idemitsu Kosan Co | Organic electroluminescent element materials and organic electroluminescent devices using the same |
US7651791B2 (en) * | 2005-12-15 | 2010-01-26 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
EP2463930B1 (en) | 2006-01-05 | 2017-04-12 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
EP1998387B1 (en) * | 2006-03-17 | 2015-04-22 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
US20070224446A1 (en) | 2006-03-24 | 2007-09-27 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
JP5619418B2 (ja) * | 2007-07-10 | 2014-11-05 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
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2007
- 2007-12-10 EP EP11196141.3A patent/EP2437326A3/en not_active Withdrawn
- 2007-12-10 EP EP07859762.2A patent/EP2101365B1/en active Active
- 2007-12-10 WO PCT/JP2007/073777 patent/WO2008072596A1/ja active Application Filing
- 2007-12-10 US US12/443,410 patent/US8541112B2/en active Active
- 2007-12-10 JP JP2008549306A patent/JP5493357B2/ja active Active
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2011
- 2011-09-16 US US13/234,601 patent/US9048434B2/en active Active
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2012
- 2012-10-04 JP JP2012222413A patent/JP5742811B2/ja active Active
- 2012-10-04 JP JP2012222406A patent/JP5626303B2/ja active Active
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2013
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- 2013-08-15 US US13/967,959 patent/US9293715B2/en not_active Expired - Fee Related
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2014
- 2014-11-04 JP JP2014224106A patent/JP5930002B2/ja active Active
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Also Published As
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US20130328031A1 (en) | 2013-12-12 |
US9293715B2 (en) | 2016-03-22 |
US10109800B2 (en) | 2018-10-23 |
JPWO2008072596A1 (ja) | 2010-03-25 |
US9048434B2 (en) | 2015-06-02 |
EP2101365A1 (en) | 2009-09-16 |
JP2013021365A (ja) | 2013-01-31 |
JP2015043460A (ja) | 2015-03-05 |
US20170054092A1 (en) | 2017-02-23 |
JP5493357B2 (ja) | 2014-05-14 |
EP2437326A2 (en) | 2012-04-04 |
US20150162550A1 (en) | 2015-06-11 |
US9627630B2 (en) | 2017-04-18 |
EP2437326A3 (en) | 2013-11-13 |
US20130328032A1 (en) | 2013-12-12 |
JP5626303B2 (ja) | 2014-11-19 |
JP5930002B2 (ja) | 2016-06-08 |
US20120007498A1 (en) | 2012-01-12 |
EP2101365B1 (en) | 2018-07-04 |
WO2008072596A1 (ja) | 2008-06-19 |
US20100084966A1 (en) | 2010-04-08 |
US8541112B2 (en) | 2013-09-24 |
JP2013048261A (ja) | 2013-03-07 |
EP2101365A4 (en) | 2011-06-08 |
US9590188B2 (en) | 2017-03-07 |
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