JP6312368B2 - 有機化合物、発光素子、発光装置、電子機器及び照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器及び照明装置 Download PDFInfo
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- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- RIYPENPUNLHEBK-UHFFFAOYSA-N phenanthro[9,10-b]pyridine Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 RIYPENPUNLHEBK-UHFFFAOYSA-N 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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Description
本実施の形態では、一対の電極間にEL層を有し、該EL層は少なくとも正孔輸送層と発光層を有する構成について、図1を用いて説明する。
合成スキーム(A−1)に示すように、ハロゲン化フルオレン化合物(a1)と、カルバゾール化合物(a2)とをカップリングさせることで、一般式(G1)で表されるフルオレン化合物が得られる。
本実施の形態では、本発明の一態様である有機化合物と、三重項励起エネルギーを発光に変える発光性材料と、電子輸送性材料と、を発光層に用いた発光素子について、図2(A)及び図2(B)を用いて説明する。
本実施の形態では、本発明の一態様として、電荷発生層を挟んで発光層を複数有する構造の発光素子(以下、タンデム型発光素子という)について説明する。
本実施の形態では、本発明の一態様である発光装置について説明する。
本実施の形態では、本発明の一態様である発光素子を有する発光装置について説明する。
本実施の形態では、上記実施の形態に示す本発明の一態様の発光装置をその一部に含む電子機器について説明する。電子機器としては、ビデオカメラ、デジタルカメラ等のカメラ、ゴーグル型ディスプレイ、ナビゲーションシステム、音響再生装置(カーオーディオ、オーディオコンポ等)、コンピュータ、ゲーム機器、携帯情報端末(モバイルコンピュータ、携帯電話、スマートフォン、携帯型ゲーム機、電子書籍、またはタブレット型端末等)、記録媒体を備えた画像再生装置(具体的には、Digital Versatile Disc(DVD)等の記録媒体を再生し、その画像を表示しうる表示装置を備えた装置)などが挙げられる。これらの電子機器の具体例について、図6、及び図7を用いて説明する。
まず、下記構造式(100)で示すCzFLP(略称)の合成法の一例について説明する。
次に、下記構造式(101)で示すmCzFLP(略称)の合成法の一例について説明する。
次に、下記構造式(110)で示すCzFLP−II(略称)の合成法の一例について説明する。
まず、基板1100上に、珪素若しくは酸化珪素を含有した酸化インジウム−酸化スズ化合物(ITO−SiO2、以下ITSOと略記する。)をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、用いたターゲットの組成は、In2O3:SnO2:SiO2=85:10:5[重量%]とした。また、第1の電極1101の膜厚は、110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極1101は、発光素子の陽極として機能する電極である。
発光素子2は、発光素子1と正孔輸送層1112の構成が異なり、それ以外の構成は同じである。異なる構成のみ以下記載する。
比較発光素子3は、発光素子1と正孔輸送層1112の構成が異なり、それ以外の構成は同じである。異なる構成のみ以下記載する。
まず、基板1100上に、珪素若しくは酸化珪素を含有した酸化インジウム−酸化スズ化合物(ITO−SiO2、以下ITSOと略記する。)をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、用いたターゲットの組成は、In2O3:SnO2:SiO2=85:10:5[重量%]とした。また、第1の電極1101の膜厚は、110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極1101は、発光素子の陽極として機能する電極である。
発光素子5は、発光素子4と正孔輸送層1112の構成が異なり、それ以外の構成は同じである。異なる構成のみ以下記載する。
まず、基板1100上に、珪素若しくは酸化珪素を含有した酸化インジウム−酸化スズ化合物(ITO−SiO2、以下ITSOと略記する。)をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、用いたターゲットの組成は、In2O3:SnO2:SiO2=85:10:5[重量%]とした。また、第1の電極1101の膜厚は、110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極1101は、発光素子の陽極として機能する電極である。
比較発光素子7は、発光素子6と正孔輸送層1112、及び第1の発光層1113aの構成が異なり、それ以外の構成は同じである。異なる構成のみ以下記載する。
101 第1の電極
102 EL層
103 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
116 電荷発生層
201 第1の電極
203 第2の電極
210 EL層
211 正孔輸送層
212 発光層
213 第1の有機化合物
214 第2の有機化合物
215 第3の有機化合物
301 第1の電極
303 第2の電極
311 第1の発光層
312 第2の発光層
313 電荷発生層
450R 第1の発光素子
450G 第2の発光素子
450B 第3の発光素子
451 反射電極
452 半透過・半反射電極
453a 第1の透明導電層
453b 第2の透明導電層
454B 第1の発光層
454G 第2の発光層
454R 第3の発光層
455 EL層
501 素子基板
502 画素部
503 駆動回路部
504 駆動回路部
505 シール材
506 封止基板
507 引き回し配線
508 FPC
509 nチャネル型TFT
510 pチャネル型TFT
511 スイッチング用TFT
512 電流制御用TFT
513 第1の電極
514 絶縁物
515 EL層
516 第2の電極
517 発光素子
518 空間
611 筐体
612 支持台
613 表示部
614 スピーカー部
615 ビデオ入力端子
621 本体
622 筐体
623 表示部
624 キーボード
625 外部接続ポート
626 ポインティングデバイス
631 本体
632 筐体
633 表示部
634 音声入力部
635 音声出力部
636 操作キー
637 外部接続ポート
638 アンテナ
641 本体
642 表示部
643 筐体
644 外部接続ポート
645 リモコン受信部
646 受像部
647 バッテリー
648 音声入力部
649 操作キー
650 接眼部
701 筐体
702 液晶パネル
703 バックライト
704 筐体
705 ドライバIC
706 端子
801 筐体
802 光源
901 照明装置
902 テレビ装置
1100 基板
1101 第1の電極
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1113a 第1の発光層
1113b 第2の発光層
1114 電子輸送層
1114a 第1の電子輸送層
1114b 第2の電子輸送層
1115 電子注入層
5000 携帯型端末
5001 筐体
5003 表示部
5005 電源ボタン
5007 前面カメラ
5009 背面カメラ
5011 外部接続端子
5013 外部接続端子
5015 アイコン
6000 携帯型端末
6001 第1の筐体
6003 第2の筐体
6005 ヒンジ部
6007 第1の表示部
6009 第2の表示部
6011 電源ボタン
6013 カメラ
6015 カメラ
6017 テキストアイコン
6019 アイコン
6021 キーボード
Claims (12)
- 一対の電極間に、少なくとも正孔輸送層と発光層を有し、
前記正孔輸送層及び前記発光層のいずれか一方または両方に、
一般式(G0)で表される有機化合物を有する発光素子。
(式中、Ar1及びAr2は、それぞれ独立にフェニル基、ビフェニル基、または3〜6個のベンゼン環がメタ位で連結した基のいずれか一を表し、前記Ar1は置換基を有し、前記置換基はN−カルバゾリル基を含み、前記N−カルバゾリル基は置換基(但し、N−カルバゾリル基であることは除く)を有していてもよく、前記Ar2は無置換である。前記N−カルバゾリル基とはカルバゾリル基のN位で置換されている基である。) - 請求項1に記載の発光素子を用いた発光装置。
- 請求項2に記載の発光装置を用いた電子機器。
- 請求項2に記載の発光装置を用いた照明装置。
- 一般式(G0)で表される有機化合物。
(式中、Ar1及びAr2は、それぞれ独立にフェニル基、ビフェニル基、または3〜6個のベンゼン環がメタ位で連結した基のいずれか一を表し、前記Ar1は置換基を有し、前記置換基はN−カルバゾリル基を含み、前記N−カルバゾリル基は置換基(但し、N−カルバゾリル基であることは除く)を有していてもよく、前記Ar2は無置換である。前記N−カルバゾリル基とはカルバゾリル基のN位で置換されている基である。) - 請求項5において、前記Ar 1 はフェニル基である有機化合物。
- 一般式(G1)で表される骨格を含む有機化合物。
(式中、Ar2及びAr3は、それぞれ独立にフェニル基、ビフェニル基、または3〜6個のベンゼン環がメタ位で連結した基のいずれか一を表し、前記Ar2は無置換である。また、R1〜R8は、それぞれ独立に水素、または炭素数1〜12のアルキル基、置換または無置換のフェニル基、置換または無置換のビフェニル基のいずれか一を表す。) - 請求項7において、
前記Ar2がフェニル基またはビフェニル基であり、
前記Ar3がフェニレン基またはビフェニルジイル基である
ことを特徴とする有機化合物。 - 請求項8において、
前記Ar3がメタフェニレン基またはビフェニル−3,3’−ジイル基である
ことを特徴とする有機化合物。 - 構造式(G2−1)で表される有機化合物。
- 構造式(G2−2)で表される有機化合物。
- 構造式(G3)で表される有機化合物。
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