JP6341772B2 - 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 - Google Patents
有機金属錯体、発光素子、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP6341772B2 JP6341772B2 JP2014126049A JP2014126049A JP6341772B2 JP 6341772 B2 JP6341772 B2 JP 6341772B2 JP 2014126049 A JP2014126049 A JP 2014126049A JP 2014126049 A JP2014126049 A JP 2014126049A JP 6341772 B2 JP6341772 B2 JP 6341772B2
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- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- CMLCVSPDRZVSRT-UHFFFAOYSA-N n,9-diphenyl-n-(9,9'-spirobi[fluorene]-2-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 CMLCVSPDRZVSRT-UHFFFAOYSA-N 0.000 description 1
- SFSWXKUCNTZAPG-UHFFFAOYSA-N n,n-diphenyl-4-[3-[4-(n-phenylanilino)phenyl]quinoxalin-2-yl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C(=NC2=CC=CC=C2N=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 SFSWXKUCNTZAPG-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer 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
- 238000000967 suction filtration Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 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
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 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
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
本実施の形態では、本発明の一態様である有機金属イリジウム錯体について説明する。
まず、下記一般式(G0)で表されるピリミジン誘導体の合成方法の一例について説明する。
次に、一般式(G0)で表されるピリミジン誘導体を用いて形成される、一般式(G2)で示される本発明の一態様である有機金属イリジウム錯体の合成方法について説明する。
本実施の形態では、本発明の一態様として実施の形態1で示した有機金属イリジウム錯体を発光層に用いた発光素子について図1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、有機金属イリジウム錯体に加え、他の2種類以上の有機化合物を発光層に用いた発光素子について説明する。
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EL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有機金属イリジウム錯体を発光層に用いた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、本発明の一態様である発光素子を適用して作製された発光装置を用いて完成させた様々な電子機器の一例について、図5を用いて説明する。
本実施の形態では、本発明の一態様である有機金属イリジウム錯体を含む発光装置を適用した照明装置の一例について、図6を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機金属イリジウム錯体、ビス{2−[6−(2,6−ジメチルフェニル)−4−ピリミジニル−κN3]フェニル−κC}(2,4−ペンタンジオナト−κO,O’)イリジウム(III)(略称:[Ir(ppm−dmp)2(acac)])の合成方法について説明する。なお、[Ir(ppm−dmp)2(acac)]の構造を以下に示す。
まず、4,6−ジクロロピリミジン5.0g、フェニルボロン酸4.9g、炭酸ナトリウム7.1g、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド(略称:PdCl2(PPh3)2)0.34g、アセトニトリル20mL、水20mLを、還流管を付けた100mL丸底フラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を1時間照射することで加熱した。得られた混合物からジクロロメタンにて有機層を抽出し、有機層を水、飽和食塩水にて洗浄し、硫酸マグネシウムを加えて乾燥させた。この混合物を自然ろ過した。ろ液の溶媒を留去し、得られた残渣を、展開溶媒にジクロロメタンを用いたフラッシュカラムクロマトグラフィーにより精製することで、目的物1.6g(収率:23%,淡い黄色の固体)を得た。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。ステップ1の合成スキームを下記(a−1)に示す。
次に上記ステップ1で得た4−クロロ−6−フェニルピリミジン1.6g、2,6−ジメチルフェニルボロン酸1.5g、炭酸ナトリウム1.8g、PdCl2(PPh)259mg、N,N−ジメチルホルムアミド(略称:DMF)20mL、水20mLを100mL丸底フラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を2時間照射することで加熱した。得られた混合物からジクロロメタンにて有機層を抽出し、有機層を水、飽和食塩水にて洗浄し、硫酸マグネシウムを加えて乾燥させた。この混合物を自然ろ過した。ろ液の溶媒を留去し、得られた残渣を、展開溶媒に酢酸エチル:ヘキサン=1:5を用いたフラッシュカラムクロマトグラフィーにより精製し、目的物であるHppm−dmpを0.50g得た(収率:23%、淡い黄色の油状物)。ステップ2の合成スキームを下記(a−2)に示す。
上記ステップ2の合成方法で得たHppm−dmp1.0g、塩化イリジウム(III)水和物0.57g、2−エトキシエタノール20mL、水20mLを100mL丸底フラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を3時間照射することで加熱した。得られた混合物を、メタノールにて吸引ろ過し、目的物である[Ir(ppm−dmp)2Cl]2を1.1g得た(収率:74%、橙色の固体)。ステップ3の合成スキームを下記(a−3)に示す。
上記ステップ3で得た[Ir(ppm−dmp)2Cl]21.1g、炭酸ナトリウム0.77g、アセチルアセトン(略称:Hacac)0.23g、2−エトキシエタノール30mLを、還流管を付けた100mL丸底フラスコに入れ、フラスコ内をアルゴン置換して、マイクロ波(2.45GHz 120W)を2時間照射することで加熱した。得られた混合物を、メタノールにて吸引ろ過し、ろ液の溶媒を留去した。得られた残渣を、酢酸エチル:ヘキサン=1:5を展開溶媒としたフラッシュカラムクロマトグラフィーにて精製し、ヘキサンにて再結晶をすることにより、本発明の一態様である有機金属イリジウム錯体[Ir(ppm−dmp)2(acac)]を得た(収率:59%、橙色粉末固体)。得られた橙色粉末固体0.21gを、トレインサブリメーション法により昇華精製した。昇華精製条件は、圧力2.7Pa、アルゴンガスを流量5.0mL/minで流しながら、240℃で固体を加熱した。昇華精製後、目的物の橙色固体を収率48%で得た。ステップ4の合成スキームを下記(a−4)に示す。
まず、ガラス製の基板900上に酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法により成膜し、陽極として機能する第1の電極901を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
作製した発光素子1および比較発光素子2の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
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(E)
201 陽極
202 陰極
203 EL層
204 発光層
205 燐光性化合物
206 第1の有機化合物
207 第2の有機化合物
301 第1の電極
302(1) 第1のEL層
302(2) 第2のEL層
302(n−1) 第(n−1)のEL層
302(n) 第(n)のEL層
304 第2の電極
305 電荷発生層(I)
305(1) 第1の電荷発生層(I)
305(2) 第2の電荷発生層(I)
305(n−2) 第(n−2)の電荷発生層(I)
305(n−1) 第(n−1)の電荷発生層(I)
401 素子基板
402 画素部
403 駆動回路部(ソース線駆動回路)
404a、404b 駆動回路部(ゲート線駆動回路)
405 シール材
406 封止基板
407 配線
408 FPC(フレキシブルプリントサーキット)
409 nチャネル型TFT
410 pチャネル型TFT
411 スイッチング用TFT
412 電流制御用TFT
413 第1の電極(陽極)
414 絶縁物
415 EL層
416 第2の電極(陰極)
417 発光素子
418 空間
900 基板
901 第1の電極
902 EL層
903 第2の電極
911 正孔注入層
912 正孔輸送層
913 発光層
914 電子輸送層
915 電子注入層
7100 テレビジョン装置
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7302 筐体
7304 表示パネル
7305 アイコン
7306 アイコン
7311 操作ボタン
7312 操作ボタン
7313 接続端子
7321 バンド
7322 留め金
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
8001 照明装置
8002 照明装置
8003 照明装置
8004 照明装置
Claims (7)
- 式(G2)で表される有機金属錯体。
(但し、式(G2)中、R1およびR2は、それぞれ独立に、炭素数1〜6のアルキル基を表す。Lは、ベータジケトン構造を有するモノアニオン性の二座キレート配位子を表す。) - 式(G3)で表される有機金属錯体。
(但し、式(G3)中、R1およびR2は、それぞれ独立に、炭素数1〜6のアルキル基を表す。) - 式(100)で表される有機金属錯体。
- 請求項1乃至請求項3のいずれか一に記載の有機金属錯体を有する発光素子。
- 請求項4に記載の発光素子を有する発光装置。
- 請求項5に記載の発光装置を有する電子機器。
- 請求項5に記載の発光装置を有する照明装置。
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KR102353663B1 (ko) | 2016-05-20 | 2022-01-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
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