JP5751985B2 - 縮合多環化合物およびそれを有する有機発光素子 - Google Patents
縮合多環化合物およびそれを有する有機発光素子 Download PDFInfo
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- JP5751985B2 JP5751985B2 JP2011181581A JP2011181581A JP5751985B2 JP 5751985 B2 JP5751985 B2 JP 5751985B2 JP 2011181581 A JP2011181581 A JP 2011181581A JP 2011181581 A JP2011181581 A JP 2011181581A JP 5751985 B2 JP5751985 B2 JP 5751985B2
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- light emitting
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- organic
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 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
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 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
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003057 platinum Chemical class 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
- 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 150000003839 salts Chemical class 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
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 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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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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Description
A−1
本発明に係る縮合多環化合物の基本骨格は平面性が高い基本骨格である。平面性の高い化合物に置換基としてアルキル基やアリール基、複素環基を設けることで、溶媒に対する溶解性や真空蒸着時の昇華性が向上する。
特許文献1に記載の化合物(ここでは化合物1と呼ぶ)及び本発明に係る縮合多環化合物である例示化合物B−1の希薄溶液中における蛍光発光特性を測定した。
以下に本発明に係る縮合多環化合物をA群乃至C群として例示する。
A群に示す例示化合物は、式[1]におけるR1乃至R22のいずれかに置換基を設けた化合物である。これらは、置換基の位置や種類を様々に変化させることで物性値の細かい調節が可能である。
本発明に係る縮合多環化合物の合成ルートを、例示化合物B−1の場合を一例として説明する。以下に合成スキームを記す。
次に本実施形態に係る有機発光素子を説明する。
本実施形態に係る有機発光素子は、表示装置や照明装置に用いることができる。他にも電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライトなどに用いることができる。
[中間体1−3の合成]
5−ブロモアセナフテンキノン:2.6g(10mmol)
1,3−ジフェニル−2−プロパノン:2.1g(10mmol)
エタノール:50ml
この反応溶液に、0.31gの水酸化カリウムを30mlのエタノールに溶解させた溶液を60℃で撹拌しながら滴下した。滴下終了後、還流下でさらに1時間加熱した。
中間体1:4.1g(9.5mmol)
アントラニル酸:1.6g(11mmol)
亜硝酸イソアミル:1.3g(11mmol)
トルエン:100ml
この反応溶液を、窒素下、撹拌しながら95℃で3時間加熱した。反応終了後、溶媒を減圧留去して、生じた固体をシリカゲルカラム(クロロホルム:ヘプタン=1:3)によって精製し、中間体2を3.9g得た(収率84%)。
中間体2:2.0g(4.1mmol)
ビス(ピナコラト)ジボロン:1.3g(5.0mmol)
[1,1’−ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリド ジクロロメタン付加物:0.33g(0.41mmol)
酢酸カリウム:1.3g(13mmol)
1,4−ジオキサン(脱水):20ml
この反応溶液を、窒素下、撹拌しながら5時間加熱還流させた。反応終了後、析出した塩をろ過によって除いた。
特許文献2に記載の合成法に従って、中間体2を合成した。具体的には、下記のスキームに従って合成を行った。
中間体3:1.2g(2.3mmol)
中間体7:1.0g(2.1mmol)
テトラキス(トリフェニルホスフィン)パラジウム(0):0.24g(0.21mmol)
トルエン:10ml
エタノール:2ml
2M炭酸ナトリウム水溶液:3ml
この反応溶液を、窒素下、撹拌しながら5時間加熱還流した。反応終了後、有機層を分離して硫酸マグネシウムで乾燥し、ろ過を行った。得られたろ液の溶媒を減圧留去して、生じた固体をシリカゲルカラム(クロロホルム:ヘプタン=1:3)によって精製し、中間体8を1.5g得た(収率88%)。
中間体8:0.50g(0.62mmol)
三フッ化ホウ素ジエチルエーテル錯体:0.44g(3.1mmol)
ジクロロメタン(脱水):50ml
トリフルオロ酢酸:10ml
この反応溶液に、0.28gの2,3−ジクロロ−5,6−ジシアノ−1,4−ベンゾキノン(DDQ)を少量ずつ室温下で加えた。添加終了後、窒素下、室温で1時間撹拌したのち、TLCにより中間体8の消失を確認した。
得られた固体をメタノールで洗浄したのち、トルエン/ヘプタンで再結晶して、例示化合物B−1を0.40g得た(収率80%)。
MALDI−TOF MS(マトリックス支援イオン化−飛行時間型質量分析)によりこの化合物のM+である802.3を確認した。
1H−NMR(CDCl3,500MHz) δ(ppm):8.60(1H,d),8.52(1H,d),8.27(1H,d),8.03(1H,d),7.99(1H,d),7.91(1H,d),7.88−7.82(2H,m),7.75−7.49(19H,m),7.48−7.42(2H,m),7.42−7.37(2H,m),6.69(1H,d),6.64(1H,d),6.57(1H,d)
また、例示化合物B−1の希薄トルエン溶液(1×10−6M)について、日立製F−4500を用いて励起波長500nmにおいて発光スペクトルの測定を行った。得られた発光スペクトルの最大ピーク波長は605nmであった。
[中間体9の合成]
MALDI−TOF MSによりこの化合物のM+である1026.5を確認した。
1H−NMR(CDCl3,500MHz) δ(ppm):8.66(1H,d),8.58(1H,d),8.36(1H,d),8.05(1H,d),8.01(1H,d),7.93(2H,t),7.88(1H,d),7.79−7.73(2H,m),7.71−7.61(5H,m),7.61−7.39(12H,m),6.68(1H,d),6.64(1H,d),6.56(1H,d),1.46(18H,s),1.43(18H,s)
例示化合物B−1と同様の方法で発光スペクトルを測定したところ、最大ピーク波長は607nmであった。
[中間体11の合成]
中間体13:0.30g(0.36mmol)
2,6−ジメチルフェニルボロン酸(東京化成工業製):0.11g(0.72mmol)
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:0.030g(0.072mmol)
酢酸パラジウム(II):0.0081g(0.036mmol)
トルエン:10ml
エタノール:1ml
2Mりん酸三カリウム水溶液:1ml
この反応溶液を、窒素下、撹拌しながら8時間加熱還流した。反応終了後、メタノール5mlと水5mlを加えて析出した固体をろ過した。
[有機発光素子の作製]
本実施例では、基板上に順次陽極/ホール輸送層/電子ブロッキング層/発光層/ホールブロッキング層/電子輸送層/陰極が設けられた構成の有機発光素子を以下に示す方法で作製した。
ホール輸送層(30nm):HTL−1
電子ブロッキング層(10nm):EBL−1
発光層(30nm) ホスト材料:H6(60wt%)、アシスト材料:H22(39.5wt%)、ゲスト材料:B−1(0.5wt%)
ホールブロッキング層(10nm):HBL−1
電子輸送層(30nm):ETL−1
金属電極層1(1nm):LiF
金属電極層2(100nm):Al
実施例4においてホスト材料、アシスト材料、ゲスト材料を代えた以外は、実施例4と同様の方法で素子を作製した。
本実施例では、基板上に順次陽極/ホール輸送層/電子ブロッキング層/第一発光層(赤色)/第二発光層(緑色)/第三発光層(青色)/ホールブロッキング層/電子輸送層/陰極が設けられた構成の有機発光素子を以下に示す方法で作製した。
ホール輸送層(30nm):HTL−1
電子ブロッキング層(10nm):EBL−1
第一発光層(5nm) ホスト材料:H6(80wt%)、アシスト材料:H22(19.5wt%)、ゲスト材料:B−1(0.5wt%)
第二発光層(7nm) ホスト材料:H12(98wt%)、ゲスト材料:GML−1(2wt%)
第三発光層(10nm) ホスト材料:H12(97wt%)、ゲスト材料:BML−1(3wt%)
ホールブロッキング層(10nm):HBL−2
電子輸送層(30nm):ETL−1
金属電極層1(1nm):LiF
金属電極層2(100nm):Al
得られた有機発光素子について、電流電圧特性をヒューレッドパッカード社製・微小電流計4140Bで測定し、発光輝度は、トプコン社製BM7―fastで測定した。
ITO電極を正極、Al電極を負極にして、4.6Vの印加電圧をかけたところ、発光効率が9.6cd/Aの白色発光が観測された。
5 緑色発光層
6 赤色発光層
17 TFT素子
20 陽極
21 有機化合物層
22 陰極
Claims (12)
- 下記一般式[1]で示されることを特徴とする縮合多環化合物。
式[1]においてR1乃至R22は水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基からそれぞれ独立に選ばれる。 - 前記一般式[1]において、R7、R9乃至R12、R14、R17、R19乃至R22が水素原子であることを特徴とする請求項1に記載の縮合多環化合物。
- 前記一般式[1]において、R5乃至R7、R9乃至R12、R14乃至R17、R19乃至R22が水素原子であることを特徴とする請求項1に記載の縮合多環化合物。
- 陽極及び陰極と、前記陽極及び前記陰極の間に配置されている有機化合物層とを有する有機発光素子であって、
前記有機化合物層は請求項1乃至3のいずれか一項に記載の縮合多環化合物を有することを特徴とする有機発光素子。 - 前記有機化合物層は発光層を有し、前記発光層が前記縮合多環化合物を有することを特徴とする請求項4に記載の有機発光素子。
- 前記有機化合物層は、発光部を有し、前記発光部は複数の発光層を有し、
前記複数の発光層のうちの少なくともひとつは前記縮合多環化合物を有し、
前記複数の発光層は、それぞれの発光層がそれぞれ異なる発光色を発する発光層であり、
前記異なる発光色の混色により白色を発することを特徴とする請求項4または5に記載の有機発光素子。 - 前記有機化合物層は複数の発光層を有し、前記複数の発光層の少なくともひとつは、前記縮合多環化合物を有し、かつ赤色を発する発光層であり、
前記赤色を発する発光層以外の発光層の発光色と前記赤色との混色より白色を発することを特徴とする請求項4または5に記載の有機発光素子。 - 複数の画素を有し、前記画素は請求項4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されてい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、前記表示部は複数の画素を有し、前記画素は請求項4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されてい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。
- 請求項4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されているインバータ回路とを有することを特徴とする照明装置。
- 露光光源を有する、電子写真方式の画像形成装置であって、
前記露光光源は、請求項4乃至7のいずれか一項に記載の有機発光素子を有することを特徴とする露光光源。 - 電子写真方式の画像形成装置に設けられる露光光源であって、
前記露光光源は、請求項4乃至7のいずれか一項に記載の有機発光素子を有することを特徴とする露光光源。
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