JP2004221068A - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JP2004221068A JP2004221068A JP2003422956A JP2003422956A JP2004221068A JP 2004221068 A JP2004221068 A JP 2004221068A JP 2003422956 A JP2003422956 A JP 2003422956A JP 2003422956 A JP2003422956 A JP 2003422956A JP 2004221068 A JP2004221068 A JP 2004221068A
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- Prior art keywords
- atom
- ring
- bond
- light emitting
- general formula
- Prior art date
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- 239000010410 layer Substances 0.000 claims abstract description 97
- 239000000463 material Substances 0.000 claims abstract description 76
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- 239000012044 organic layer Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 78
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 38
- 125000004434 sulfur atom Chemical group 0.000 claims description 36
- 125000004437 phosphorous atom Chemical group 0.000 claims description 24
- 229910052698 phosphorus Inorganic materials 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 15
- 229910021645 metal ion Inorganic materials 0.000 claims description 15
- 239000003446 ligand Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- -1 n-octyl Chemical group 0.000 description 60
- 238000000034 method Methods 0.000 description 35
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- 230000000052 comparative effect Effects 0.000 description 17
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- 150000004696 coordination complex Chemical class 0.000 description 12
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- 125000003118 aryl group Chemical group 0.000 description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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- 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 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
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- 239000002356 single layer Substances 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical group C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical group C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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Abstract
【解決手段】 一対の電極間に、発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、発光層は、りん光発光材料と、特定の化合物とを各々少なくとも一つ含有する有機電界発光素子。
【選択図】 なし
Description
1.一対の電極間に、発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、発光層は、りん光発光材料と、下記一般式(I)で表される化合物とを各々少なくとも一つ含有する有機電界発光素子。
一般式(I):
2.発光層が、前記一般式(I)で表される化合物をホスト材料として含有する前記1に記載の有機電界発光素子。
3.発光層が、前記一般式(I)で表される化合物を主成分として含有し、りん光発光材料が実質的に発光する前記1又は2に記載の有機電界発光素子。
4.前記一般式(I)で表される化合物が、下記一般式(II)で表される前記1に記載の有機電界発光素子。
一般式(II):
5.前記一般式(I)で表される化合物が、下記一般式(III)で表される前記1に記載の有機電界発光素子。
一般式(III):
6.発光層が、りん光発光材料を少なくとも一種と、ホスト材料を少なくとも二種含有することを特徴とする1〜5に記載の有機電界発光素子。
発光材料(本発明ではりん光発光材料)を分散して層中に保持する機能、
陽極や正孔輸送層等から正孔を受け取る機能、陰極や電子輸送層等から電子を受け取る機能、
正孔及び/又は電子を輸送する機能、
正孔と電子の再結合の場を提供する機能、
再結合により生成した励起子のエネルギーを発光材料に移動させる機能、及び
正孔及び/又は電子を発光材料に輸送する機能、
のうち少なくとも一種の機能を有する材料を意味する。
また、本発明のホスト材料で再結合が行われる場合には、まずホスト材料の励起子が生成することから、ホスト材料の励起状態は分解や熱失活を引き起こさず、安定であることが好ましい。このことはすなわち、光に対しても安定なホスト材料が好ましいことをも意味するものである。
さらにEL素子では駆動時の発熱による膜の破壊や材料の分解が劣化の大きな要因であることから、ホスト材料もまた熱による分解がなく、高温まで安定なアモルファス膜を保持できる材料であることが好ましい。
アルキル基(好ましくは炭素数1〜20、より好ましくは炭素数1〜12、特に好ましくは炭素数1〜8であり、例えばメチル、エチル、iso−プロピル、tert−ブチル、n−オクチル、n−デシル、n−ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシル等が挙げられる。)、アルケニル基(好ましくは炭素数2〜20、より好ましくは炭素数2〜12、特に好ましくは炭素数2〜8であり、例えばビニル、アリル、2−ブテニル、3−ペンテニル等が挙げられる。)、アルキニル基(好ましくは炭素数2〜20、より好ましくは炭素数2〜12、特に好ましくは炭素数2〜8であり、例えばプロパルギル、3−ペンチニル等が挙げられる。)、アリール基(好ましくは炭素数6〜30、より好ましくは炭素数6〜20、特に好ましくは炭素数6〜12であり、例えばフェニル、p−メチルフェニル、ナフチル等が挙げられる。)、置換カルボニル基(好ましくは炭素数1〜20、より好ましくは炭素数1〜16、特に好ましくは炭素数1〜12であり、例えばアセチル、ベンゾイル、メトキシカルボニル、フェニルオキシカルボニル、ジメチルアミノカルボニル、フェニルアミノカルボニル、等が挙げられる。)、アミノ基(好ましくは炭素数0〜20、より好ましくは炭素数1〜16、特に好ましくは炭素数1〜12であり、例えばジメチルアミノ、メチルカルボニルアミノ、エチルスルフォニルアミノ、ジメチルアミノカルボニルアミノ基、フタルイミド基等が挙げられる。)。
本発明のEL素子において、発光層は、りん光発光材料、及び一般式(I)乃至(III)で表される化合物以外に、EL素子の発光性能を最適化するために適宜その他の成分(電荷注入及び/又は輸送能をもつ化合物など)を含有してもよいが、りん光発光材料及び一般式(I)乃至(III)で表される化合物のみから構成される形態が好ましい。
発光層は、りん光発光材料と一般式(I)〜(III)で表される金属錯体のみから構成されるのがより好ましい。
陽極は洗浄その他の処理により、素子の駆動電圧を下げ、発光効率を高めることも可能である。例えばITOの場合、UV−オゾン処理、プラズマ処理等が効果的である。
洗浄したITO基板を蒸着装置に入れ、TPD(N,N’−ジフェニル−N,N’−ジ(m−トリル)ベンジジン)を50nm蒸着し、この上にAlq及びIr(ppy)3を17:1の質量比で36nm蒸着し、さらにこの上に化合物aを36nm蒸着した。得られた有機薄膜上にパターニングしたマスク(発光面積が4mm×5mmとなる)を設置し、フッ化リチウムを3nm蒸着した後アルミニウムを60nm蒸着して比較例1の有機EL素子を作製した。
Alqに代えて下記化合物CBPを用いたこと以外は上記比較例1と同様にして、比較例2の有機EL素子を作製した。比較例1と同様にして、比較例2の有機EL素子を評価した結果、CIE色度が(x,y)=(0.276 , 0.630)、発光ピーク波長が516nmの緑色発光が得られ、最高輝度は27000cd/m2、外部量子効率は12.7%であった。
Alqに代えて下記化合物b(特開2002−305083号公報の段落番号[0034]に記載の化合物(H−4))を用いたこと以外は、上記比較例1と同様にして、比較例3の有機EL素子を作製した。比較例1と同様にして、比較例3の有機EL素子を評価した結果、CIE色度が(x,y)=(0.286 , 0.624)、発光ピーク波長が522nmの緑色発光が得られ、最高輝度は21000cd/m2、外部量子効率は11.4%であった。
Alqに代えて本発明の例示化合物H−2を用いたこと以外は上記比較例1と同様にして、実施例1の有機EL素子を作製した。比較例1と同様にして、実施例1の有機EL素子を評価した結果、CIE色度が(x,y)=(0.320 , 0.610)、発光ピーク波長が520nmの緑色発光が得られ、最高輝度は73000cd/m2、外部量子効率は17.4%であった。
上記実施例1及び比較例2の有機EL素子において、初期輝度を合わせた輝度半減時間を測定したところ、比較例2の有機EL素子が8時間であったのに対し、実施例1の有機EL素子は45時間であった。
Claims (5)
- 一対の電極間に、発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、発光層は、りん光発光材料と、下記一般式(I)で表される化合物とを各々少なくとも一つ含有する有機電界発光素子。
- 発光層が、前記一般式(I)で表される化合物をホスト材料として含有する請求項1に記載の有機電界発光素子。
- 発光層が、前記一般式(I)で表される化合物を主成分として含有し、りん光発光材料が実質的に発光する請求項1又は2に記載の有機電界発光素子。
- 前記一般式(I)で表される化合物が、下記一般式(II)で表される請求項1〜3のいずれかに記載の有機電界発光素子。
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WO2010058787A1 (ja) | 2008-11-21 | 2010-05-27 | 富士フイルム株式会社 | 有機電界発光素子 |
WO2010084690A1 (ja) | 2009-01-22 | 2010-07-29 | 富士フイルム株式会社 | 有機電界発光素子 |
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EP2031037A1 (en) | 2007-08-29 | 2009-03-04 | Fujifilm Corporation | Organic electroluminescence device |
EP2061086A2 (en) | 2007-11-15 | 2009-05-20 | FUJIFILM Corporation | Thin film field effect transistor and display using the same |
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WO2010058787A1 (ja) | 2008-11-21 | 2010-05-27 | 富士フイルム株式会社 | 有機電界発光素子 |
WO2010084690A1 (ja) | 2009-01-22 | 2010-07-29 | 富士フイルム株式会社 | 有機電界発光素子 |
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