JP2012097056A - フェナンスレン化合物及びこれを用いた有機発光素子 - Google Patents
フェナンスレン化合物及びこれを用いた有機発光素子 Download PDFInfo
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- JP2012097056A JP2012097056A JP2010248352A JP2010248352A JP2012097056A JP 2012097056 A JP2012097056 A JP 2012097056A JP 2010248352 A JP2010248352 A JP 2010248352A JP 2010248352 A JP2010248352 A JP 2010248352A JP 2012097056 A JP2012097056 A JP 2012097056A
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- Prior art keywords
- compound
- light emitting
- phenanthrene
- organic light
- group
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- -1 Phenanthrene compound Chemical class 0.000 title claims abstract description 52
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052741 iridium Inorganic materials 0.000 claims description 3
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- 150000001875 compounds Chemical class 0.000 description 119
- 239000010410 layer Substances 0.000 description 99
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- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 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
- 150000004986 phenylenediamines Chemical class 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
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003281 rhenium Chemical class 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
- 150000003303 ruthenium Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 230000002123 temporal effect Effects 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
- 150000003518 tetracenes Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000001269 time-of-flight mass spectrometry 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 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
- 238000007740 vapor deposition Methods 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
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Abstract
Description
工程(a):3−ブロモ−3’−クロロビフェニルと、アリール基(Ar−)の基礎となるボロン酸誘導体とのPd触媒によるカップリング反応を行う工程
工程(b):工程(a)で得られた化合物と、フェナンスレンユニットの基礎となるビスピナコールボロン酸エステル誘導体とのPd触媒によるカップリング反応を行う工程
尚、上記合成スキームにおいて、本発明の要旨の範囲内でAr及びRをそれぞれ適宜選択することができ、所望のフェナンスレン化合物を合成することができる。
(i)(基板/)陽極/発光層/陰極
(ii)(基板/)陽極/ホール輸送層/電子輸送層/陰極
(iii)(基板/)陽極/ホール輸送層/発光層/電子輸送層/陰極
(iv)(基板/)陽極/ホール注入層/ホール輸送層/発光層/電子輸送層/陰極
(v)(基板/)陽極/ホール輸送層/発光層/ホール・エキシトンブロッキング層/電子輸送層/陰極
4−クロロ−2,2’−ジホルミルビフェニル:5.33g(21.8mmol)
酢酸:250mL
mBP−Bpin2(ボロン酸エステル):1.50g(3.69mmol)
2−クロロフェナンスレン:1.65g(7.76mmol)
酢酸パラジウム:83mg(0.37mmol)
XPhos(2−ジシクロヘキシルホスフィノ−2’,4’,6’−トリイソプロピルビフェニル):528mg(1.11mmol)
リン酸カリウム:2.35g(11.1mmol)
トルエン:80mL
水:2mL
実測値:m/z=506.34、計算値:C40H26=506.20
[1H−NMR(400MHz、CDCl3)]
δ 8.79(d,2H),8.73(d,2H),8.19(d,2H),8.08(s,2H),8.01(dd,2H),7.92(d,2H),7.90−7.60(m,14H).
例示化合物A04のトルエン希薄溶液を調製した後、この希薄溶液について、アルゴン雰囲気下、77K、励起波長350nmの条件下で燐光スペクトルの測定を行った。得られた燐光スペクトルの第一発光ピークのピーク波長からT1エネルギーを求めた。その結果、T1エネルギーは波長換算値で466nmであった。
ガラス基板上に、加熱蒸着により、例示化合物A04を成膜して測定用の薄膜を形成した。このとき測定用の薄膜の膜厚を20nmとした。次に、紫外可視分光光度計(日本分光株式会社製V−560)を用いて、上記測定用の薄膜について吸光スペクトルを測定した。得られた吸光スペクトルの吸収端よりエネルギーギャップを求めた。その結果、吸光スペクトルの吸収端は347nmであり、例示化合物A04のエネルギーギャップは3.57eVであった。
上記のエネルギーギャップの測定に用いた測定用の薄膜を用いて、光電子分光装置AC−3(理研計器株式会社製)によりイオン化ポテンシャルを測定した。測定の結果、例示化合物A04のイオン化ポテンシャルは6.43eVであった。
LUMO準位は、イオン化ポテンシャル値とエネルギーギャップ値の差から見積ることができる。ここで例示化合物A04では、LUMO準位は−2.86eVであった。
2−クロロフェナンスレン:3.00g(14.1mmol)
ビス(ピナコラト)ジボロン:4.30g(16.9mmol)
ビス(ジベンジリデンアセトン)パラジウム(0):406mg(0.71mmol)
トリシクロヘキシルホスフィン:593mg(2.12mmol)
酢酸カリウム:2.77g(28.2mmol)
1,4−ジオキサン:100mL
3−ブロモ−3’−クロロビフェニル:3.00g(11.2mmol)
4−ジベンゾチオフェンボロン酸:2.63g(11.6mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):352mg(0.31mmol)
トルエン:60mL
エタノール:30mL
10重量%炭酸ナトリウム水溶液:30mL
PT−Bpin:583mg(1.92mmol)
4−(3’−クロロビフェニル−3−イル)ジベンゾチオフェン:646mg(1.74mmol)
酢酸パラジウム:24mg(0.11mmol)
SPhos(2―ジシクロヘキシルホスフィノ―2’,6’−ジメトキシビフェニル):130mg(0.32mmol)
リン酸カリウム:1.11g(5.23mmol)
トルエン:25mL
水:0.6mL
実測値:m/z=512.30、計算値:C38H24S=512.16
[1H−NMR(400MHz、CDCl3)]
δ 8.77(d,1H),8.72(d,1H),8.30−8.15(m,3H),8.09(d,2H),7.98(dd,1H),7.91(d,1H),7.88−7.55(m,13H),7.48(m,2H).
MePT−Bpin:440mg(1.38mmol)
4−(3’−クロロビフェニル−3−イル)ジベンゾチオフェン:394mg(1.06mmol)
酢酸パラジウム:14mg(0.062mmol)
SPhos(2―ジシクロヘキシルホスフィノ―2’,6’−ジメトキシビフェニル):78mg(0.19mmol)
リン酸カリウム:675mg(3.18mmol)
トルエン:18mL
水:0.4mL
実測値:m/z=526.37、計算値:C39H26S=526.18
下記に示す比較化合物H01乃至H05について、実施例1と同様の方法でT1エネルギー及びLUMO準位の評価を行った。結果を表3に示す。実施例1乃至3の結果と合わせて、結果を表3に示す。
基板上に、陽極/ホール輸送層/発光層/ホールブロッキング層/電子輸送層/陰極がこの順に設けられている有機発光素子を、以下に示す方法で作製した。尚、本実施例で使用した化合物の一部を下記に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて例示化合物A09を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて例示化合物B08を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて化合物H02を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて化合物H03を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
実施例4において、発光層のホストとして、例示化合物A04に代えて化合物H05を使用した他は、実施例4と同様の方法で素子を作製した。また得られた素子について実施例4と同様に評価を行った。結果を表5に示す。
Claims (9)
- 前記R1乃至R21がいずれも水素原子であることを特徴とする、請求項1に記載のフェナンスレン化合物。
- 陽極と陰極と、
前記陽極と前記陰極との間に挟持される有機化合物層と、から構成される有機発光素子において、
前記有機化合物層に請求項1又は2に記載のフェナンスレン化合物が含まれることを特徴とする、有機発光素子。 - 前記フェナンスレン化合物が発光層に含まれることを特徴とする、請求項3に記載の有機発光素子。
- 前記発光層がホストとゲストとからなり、前記ホストが前記フェナンスレン化合物であることを特徴とする、請求項4に記載の有機発光素子。
- 前記ゲストが燐光発光材料であることを特徴とする、請求項5に記載の有機発光素子。
- 前記燐光発光材料がイリジウム錯体であることを特徴とする、請求項6に記載の有機発光素子。
- 請求項3乃至7のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続するスイッチング素子とを有することを特徴とする、表示装置。
- 画像を表示するための表示部と、画像情報を入力するための入力部と、を有し、
前記表示部が複数の画素を有し、
前記複数の画素が、請求項3乃至7のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続するスイッチング素子と、を有することを特徴とする、画像入力装置。
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PCT/JP2011/075016 WO2012060307A1 (en) | 2010-11-05 | 2011-10-25 | Phenanthrene compound and organic light emitting device using the same |
CN2011800521037A CN103347841A (zh) | 2010-11-05 | 2011-10-25 | 菲化合物和使用该菲化合物的有机发光器件 |
KR1020137013613A KR101523153B1 (ko) | 2010-11-05 | 2011-10-25 | 페난트렌 화합물 및 이를 사용한 유기 발광 디바이스 |
US13/880,250 US8729541B2 (en) | 2010-11-05 | 2011-10-25 | Phenanthrene compound and organic light emitting device using the same |
EP11837957.7A EP2635545A1 (en) | 2010-11-05 | 2011-10-25 | Phenanthrene compound and organic light emitting device using the same |
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JP2009215333A (ja) * | 2008-03-07 | 2009-09-24 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料ならびに有機エレクトロルミネッセンス素子 |
JP2009221442A (ja) * | 2008-03-19 | 2009-10-01 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料ならびに有機エレクトロルミネッセンス素子 |
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US8154195B2 (en) * | 2007-07-07 | 2012-04-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
TW200909560A (en) * | 2007-07-07 | 2009-03-01 | Idemitsu Kosan Co | Organic electroluminescence device and material for organic electroluminescence devcie |
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WO2006130598A2 (en) * | 2005-05-31 | 2006-12-07 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
JP2009051764A (ja) * | 2007-08-27 | 2009-03-12 | Hodogaya Chem Co Ltd | 置換されたフェナントレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
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JP2009215333A (ja) * | 2008-03-07 | 2009-09-24 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料ならびに有機エレクトロルミネッセンス素子 |
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US8729541B2 (en) | 2014-05-20 |
KR101523153B1 (ko) | 2015-05-26 |
EP2635545A1 (en) | 2013-09-11 |
KR20140058395A (ko) | 2014-05-14 |
JP5653179B2 (ja) | 2015-01-14 |
WO2012060307A1 (en) | 2012-05-10 |
CN103347841A (zh) | 2013-10-09 |
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