JP6661234B2 - 有機金属錯体、発光素子、発光装置、電子機器及び照明装置 - Google Patents
有機金属錯体、発光素子、発光装置、電子機器及び照明装置 Download PDFInfo
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- JP6661234B2 JP6661234B2 JP2016091106A JP2016091106A JP6661234B2 JP 6661234 B2 JP6661234 B2 JP 6661234B2 JP 2016091106 A JP2016091106 A JP 2016091106A JP 2016091106 A JP2016091106 A JP 2016091106A JP 6661234 B2 JP6661234 B2 JP 6661234B2
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- 239000005060 rubber Substances 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000004575 stone Substances 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
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 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
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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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
- C07F15/0086—Platinum compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/121—Active-matrix OLED [AMOLED] displays characterised by the geometry or disposition of pixel elements
- H10K59/1213—Active-matrix OLED [AMOLED] displays characterised by the geometry or disposition of pixel elements the pixel elements being TFTs
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
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- H10K59/123—Connection of the pixel electrodes to the thin film transistors [TFT]
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- Inorganic Chemistry (AREA)
- Geometry (AREA)
- Physics & Mathematics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
まず、下記一般式(G0)で表されるフェノチアジン誘導体又はフェノキサジン誘導体の合成法の一例について説明する。なお、一般式(G0)中、R1乃至R13はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。Aは五員複素芳香環骨格を表し、当該骨格中に2又は3の窒素原子を含む。また、Qは硫黄又は酸素を表す。
まず、下記合成スキームに示すように、一般式(G0)で表されるフェノチアジン誘導体又はフェノキサジン誘導体と、テトラクロロ白金酸カリウムおよび酢酸、または酢酸を含む溶媒を用いて、不活性ガス雰囲気にて加熱することにより、一般式(G1)で表される本発明の一態様である有機金属錯体が得られる。
続いて、本発明の一態様である発光素子の例について図1(A)を用いて以下、詳細に説明する。
マイクロキャビティ構造を有する発光素子は、上記一対の電極を、反射電極と半透過・半反射電極とから構成することにより得られる。反射電極と半透過・半反射電極は上述の第1の電極と第2の電極に相当する。反射電極と半透過・半反射電極との間には少なくともEL層を有し、EL層は少なくとも発光領域となる発光層を有している。
本発明の一態様の発光装置について図2を用いて説明する。なお、図2(A)は、発光装置を示す上面図、図2(B)は図2(A)をA−BおよびC−Dで切断した断面図である。この発光装置は、発光素子の発光を制御するものとして、点線で示された駆動回路部(ソース線駆動回路)601、画素部602、駆動回路部(ゲート線駆動回路)603を含んでいる。また、604は封止基板、605はシール材であり、シール材605で囲まれた内側は、空間607になっている。
本発明の一態様である照明装置を図6を参照しながら説明する。図6(B)は照明装置の上面図、図6(A)は図6(B)におけるe−f断面図である。
本発明の一態様である電子機器の例について説明する。電子機器として、例えば、テレビジョン装置(テレビ、またはテレビジョン受信機ともいう)、コンピュータ用などのモニタ、デジタルカメラ、デジタルビデオカメラ、デジタルフォトフレーム、携帯電話機(携帯電話、携帯電話装置ともいう)、携帯型ゲーム機、携帯情報端末、音響再生装置、パチンコ機などの大型ゲーム機などが挙げられる。これらの電子機器の具体例を以下に示す。
本合成例では、実施形態において構造式(100)で表した本発明の一態様の有機金属錯体である{2−[6−(3,5−ジメチル−ピラゾール−1−イル−κN2)−1,2−フェニレン−κC1]オキシ[10−(2−ピリジニル−κN)−フェノチアジン−2,1−ジイル−κC1]}白金(II)(略称:[Pt(pptOppz)])の合成例を具体的に例示する。以下に[Pt(pptOppz)]の構造式を示す。
まず、2−メトキシフェノチアジン3.1g、2−ヨードピリジン3.1g、ナトリウム−t−ブトキシド2.0gを、還流管を付けた三口フラスコ内に入れ、フラスコ内を窒素置換した。この混合物に、トルエン97mL、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(製品名:SPhos)0.56g、トリス(ジベンジリデンアセトン)ジパラジウム(0)(略称:Pd2(dba)3)0.62gを加え、130℃で14時間加熱攪拌した。得られた混合物に水を加え、酢酸エチルにて有機層を抽出した。抽出液を飽和食塩水にて洗浄した後、硫酸マグネシウムを加え、ろ過した。ろ液の溶媒を留去し、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することにより目的物の茶色油状物を2.2g、収率52%で得た。ステップ1の合成スキームを下記式(1−1)に示す。
次に、2−メトキシ−10−(ピリジン−2−イル)−フェノチアジン7.1g、ピリジン塩酸塩13gを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換し、170℃で7時間加熱撹拌した。さらにピリジン塩酸塩2gを加え、170℃で6時間加熱撹拌した。フラスコ内の温度を90℃に下げ、そこで酢酸エチルと水を加え、30分間攪拌した。得られた混合溶液の有機層を酢酸エチルで抽出した。抽出液を飽和食塩水にて洗浄し、硫酸マグネシウムを加え、ろ過した。ろ液の溶媒を留去し、得られた残渣に酢酸エチル:ヘキサン=1:2の溶液を加え、ろ過した。このろ物を酢酸エチルに溶解しセライト(和光純薬工業株式会社、カタログ番号:531−16855)を充填させたろ過補助剤に通した。ろ液の溶媒を留去し、トルエンにて再結晶することにより目的物の緑灰色固体を3.0g、収率:45%で得た。ステップ2の合成スキームを下記式(1−2)に示す。
次に、1,3−ジヨードベンゼン5.0g、3,5−ジメチルピラゾール1.6g、酸化銅(I)220mg、ピリジン−2−アルドキシム370mg、炭酸セシウム12gを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換し、アセトニトリル300mLを加え、37時間還流させた。得られた混合物をジクロロメタンに溶かし、セライトを充填したろ過補助剤に通した。ろ液の溶媒を留去し、酢酸エチル:ヘキサン=1:5を展開溶媒としたシリカゲルカラムクロマトグラフィーにて精製することで目的物の褐色油状物を3.0g、収率:40%で得た。ステップ3の合成スキームを下記式(1−3)に示す。
次に、2−ヒドロキシ−10−(ピリジン−2−イル)−フェノチアジン1.0g、1−(3−ヨードフェニル)−3,5−ジメチルピラゾール1.3g、ピコリン酸1.1g、リン酸カリウム3.6gを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換し、ジメチルスルホキシド100mL、ヨウ化銅0.33gを加え、150℃にて14時間加熱した。さらにピコリン酸1.1g、リン酸カリウム3.6g、ヨウ化銅0.33gを加え、150℃にて15時間加熱した。得られた混合物に水を加え、酢酸エチルにて有機層を抽出した。抽出液を飽和食塩水にて洗浄し、硫酸マグネシウムを加え、ろ過した。ろ液の溶媒を留去し、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することにより目的物の黄色固体を1.3g、収率:82%で得た。ステップ4の合成スキームを下記式(1−4)に示す。
次に、HpptOppz1.3g、テトラクロロ白金(II)酸カリウム1.3g、氷酢酸40mLをフラスコに入れ、フラスコ内を窒素置換し、56時間還流させた。得られた混合物に水を加え20分間撹拌し、ろ過した。このろ物を、ジクロロメタン:ヘキサン=7:5を展開溶媒とした中性シリカゲルカラムクロマトグラフィーにて精製した。得られた目的物のフラクションから溶媒を留去し、クロロホルム、ジクロロメタン、メタノール、ヘキサンの混合溶媒にて再結晶したところ黄白色固体を0.42g、収率:21%で得た。ステップ5の合成スキームを下記式(1−5)に示す。
まず、ガラス基板上に、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て成膜し、第1の電極101を形成した。なお、その膜厚は70nmとし、電極面積は2mm×2mmとした。
102 第2の電極
103 EL層
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
117 P型層
118 電子リレー層
119 電子注入バッファ層
400 基板
401 第1の電極
403 EL層
404 第2の電極
405 シール材
406 シール材
407 封止基板
412 パッド
420 ICチップ
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース線駆動回路)
602 画素部
603 駆動回路部(ゲート線駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用FET
612 電流制御用FET
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
623 nチャネル型FET
624 pチャネル型FET
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 第1の層間絶縁膜
1021 第2の層間絶縁膜
1022 電極
1024W 発光素子の第1の電極
1024R 発光素子の第1の電極
1024G 発光素子の第1の電極
1024B 発光素子の第1の電極
1025 隔壁
1028 EL層
1029 発光素子の第2の電極
1031 封止基板
1032 シール材
1033 透明な基材
1034R 赤色の着色層
1034G 緑色の着色層
1034B 青色の着色層
1035 黒色層(ブラックマトリックス)
1037 第3の層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
2001 筐体
2002 光源
3001 照明装置
5000 表示領域
5001 表示領域
5002 表示領域
5003 表示領域
5004 表示領域
5005 表示領域
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
7210 第2の表示部
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
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9038 操作スイッチ
9310 携帯情報端末
9311 表示パネル
9312 表示領域
9313 ヒンジ
9315 筐体
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 操作キー
9638 コンバータ
9639 ボタン
Claims (10)
- 下記式(G1)で表される有機金属錯体。
(但し、式(G1)において、R1乃至R13はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。Aは五員複素芳香環骨格を表し、当該骨格中に2又は3の窒素原子を含む。また、Qは硫黄原子又は酸素原子を表す。) - 下記式(G2)で表される有機金属錯体。
(但し、式(G2)において、R1乃至R13はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。また、X1、Y1及びZ1 のうち2又は3が炭素原子であり、当該炭素原子は置換基を有していても有していなくても良く、X 1 、Y 1 及びZ 1 のうち2が炭素原子であるとき、X 1 、Y 1 及びZ 1 のうち1が窒素原子である。また、Qは硫黄原子又は酸素原子を表す。) - 下記式(G3)で表される有機金属錯体。
(但し、式(G3)において、R1乃至R13及びR20はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。また、X 2 及びZ 2 の一方が炭素原子を表し、他方が炭素原子または窒素原子を表す。当該炭素原子は置換基を有していても有していなくても良い。また、Qは硫黄原子又は酸素原子を表す。) - 下記式(G4)で表される有機金属錯体。
(但し、式(G4)において、R1乃至R13及びR21はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。また、Y 3 及びZ 3 の一方が炭素原子を表し、他方が炭素原子または窒素原子を表す。当該炭素原子は置換基を有していてもいなくても良い。また、Qは硫黄原子又は酸素原子を表す。) - 下記式(G5)で表される有機金属錯体。
(但し、式(G5)において、R1乃至R13及びR22はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。また、X 4 及びY 4 の一方が炭素原子を表し、他方が炭素原子または窒素原子を表す。当該炭素原子は置換基を有していてもいなくても良い。また、Qは硫黄原子又は酸素原子を表す。) - 下記式(G6)で表される有機金属錯体。
(但し、式(G6)において、R1乃至R13及びR30乃至R32はそれぞれ独立に、水素、置換又は無置換の炭素数1乃至6のアルキル基、置換又は無置換のフェニル基のいずれかを表す。また、Qは硫黄原子又は酸素原子を表す。) - 請求項1乃至請求項6のいずれか一項に記載の有機金属錯体を用いた発光素子。
- 請求項7に記載の発光素子と、トランジスタ、または、基板と、を有する発光装置。
- 請求項8に記載の発光装置と、センサ、操作ボタン、スピーカ、または、マイクと、を有する電子機器。
- 請求項8に記載の発光装置と、筐体と、を有する照明装置。
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JP6847589B2 (ja) | 2015-05-20 | 2021-03-24 | 株式会社半導体エネルギー研究所 | 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 |
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US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
JP4154138B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
JP2003342284A (ja) | 2002-05-30 | 2003-12-03 | Canon Inc | 金属配位化合物、発光素子及び表示装置 |
JP4628108B2 (ja) | 2003-02-14 | 2011-02-09 | 株式会社半導体エネルギー研究所 | 有機金属錯体、及び電界発光素子を有する電子機器 |
TWI541247B (zh) | 2011-02-18 | 2016-07-11 | 美國亞利桑那州立大學董事會 | 具有幾何失真電荷轉移態之四配位鉑及鈀錯合物及彼等於發光裝置中之應用 |
US9238668B2 (en) | 2011-05-26 | 2016-01-19 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US9493698B2 (en) * | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102349659B1 (ko) | 2013-06-10 | 2022-01-11 | 아리조나 보드 오브 리젠츠 온 비하프 오브 아리조나 스테이트 유니버시티 | 개질된 방출 스펙트럼을 갖는 인광성 네자리 금속 착물 |
WO2015027060A1 (en) | 2013-08-21 | 2015-02-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
JP6804823B2 (ja) | 2013-10-14 | 2020-12-23 | アリゾナ・ボード・オブ・リージェンツ・オン・ビハーフ・オブ・アリゾナ・ステイト・ユニバーシティーArizona Board of Regents on behalf of Arizona State University | 白金錯体およびデバイス |
US9941479B2 (en) * | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
US10115912B2 (en) * | 2015-04-28 | 2018-10-30 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
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US10115912B2 (en) | 2018-10-30 |
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