JP6925802B2 - 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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- JP6925802B2 JP6925802B2 JP2016253831A JP2016253831A JP6925802B2 JP 6925802 B2 JP6925802 B2 JP 6925802B2 JP 2016253831 A JP2016253831 A JP 2016253831A JP 2016253831 A JP2016253831 A JP 2016253831A JP 6925802 B2 JP6925802 B2 JP 6925802B2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 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
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 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
- 150000003457 sulfones Chemical class 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
- 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
- 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
- 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
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical group 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
- 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
一般式(G0−53)で表されるベンゾイミダゾ[1,2−a]ベンゾイミダゾール誘導体の構造を以下に示す。
次に、下記合成スキーム(c)に示すように上記一般式(G0−53)で表されるベンゾイミダゾ[1,2−a]ベンゾイミダゾール誘導体と、ハロゲンを含む白金の金属化合物(テトラクロロ白金酸カリウム等)とを酢酸、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。これにより、一般式(G53)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1では、実施の形態において構造式(100)で表される本発明の有機金属錯体、{3−[6−(1H−ピラゾール−1−イル−κN2)−1,2−フェニレン−κC1]オキシ[7−メチル−5−(2−ピリジニル−κN)−5H−ベンゾイミダゾ[1,2−a]ベンゾイミダゾール−3,4−ジイル−κC4]}白金(II)(略称:[Pt(ppzObibipy)])の合成例を具体的に例示する。[Pt(ppzObibipy)]の構造式を以下に示す。
まず、2−アミノピリジン8.8g(91mmol)、t−ブトキシドカリウム20g(180mmol)を、三口フラスコに入れフラスコ内を窒素置換した。この混合物にテトラヒドロフラン(略称:THF)250mLを加え、0℃で1時間攪拌した。その後、THF150mLと4−ブロモ−2−フルオロニトロベンゼン21g(91mmol)の混合液を滴下して加え、0℃で50分間攪拌した。この反応物に酢酸エチルと水を加えてろ過し、ろ液を酢酸エチルで抽出した。抽出液を飽和食塩水で洗浄し、硫酸マグネシウムを加えてろ過した。得られたろ液を濃縮し、セライト(和光純薬工業株式会社、カタログ番号:531−16855;以下同じ)、アルミナ、セライトの順に充填したろ過補助剤を通してろ過した。ろ液の溶媒を留去し、得られた残渣をヘキサンで超音波洗浄することにより目的物16g(収率:61%、橙色固体)を得た。ステップ1の合成スキームを下記式(a−1)に示す。
次に、上記ステップ1で合成したN−(5−ブロモ−2−ニトロフェニル)−ピリジン−2−アミン14g(47mmol)、水8.4g(470mmol)、エタノール480mL、塩化スズ(II)45g(230mmol)を、還流管を付けた三口フラスコに入れ、窒素気流下にて80℃で2時間加熱した。この反応物を室温まで冷やし、2M水酸化ナトリウム水溶液にゆっくり入れ、1時間攪拌した。得られた反応物をろ過し、ろ液をクロロホルムで抽出した。抽出液を水、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、得られた残渣をヘキサンで超音波洗浄することにより目的物10g(収率:84%、薄赤紫色固体)を得た。ステップ2の合成スキームを下記式(b−1)に示す。
次に、上記ステップ2で合成した5−ブロモ−N−(2−ピリジニル)−1,2−フェニレンジアミン11g(41mmol)を、還流管を付けた三口フラスコに入れ、THF45mL、1,1’−カルボニルジイミダゾール8.6g(53mmol)を加え、80℃で2時間加熱し、室温にて18時間攪拌した。得られた混合物に水を加え、酢酸エチルで抽出した。抽出液を水、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にて再結晶し、目的物8.8g(収率:75%、黒紫色固体)を得た。ステップ3の合成スキームを下記式(c−1)に示す。
次に、上記ステップ3で合成した6−ブロモ−1−(2−ピリジニル)−2−ベンゾイミダゾリノン8.8g(30mmol)、3−フルオロ−2−ニトロトルエン5.2g(33mmol)、炭酸カリウム8.4g(61mmol)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(略称:DMSO)120mLを加え、100℃で23時間加熱した。得られた反応物をろ過し、ろ液を酢酸エチルで抽出した。抽出液を水、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:トルエン=1:5を展開溶媒としたシリカカラムクロマトグラフィーにて精製し、さらにそれをヘキサンにて洗浄することにより目的物12g(収率:91%、黄色固体)を得た。ステップ4の合成スキームを下記式(d−1)に示す。
次に、上記ステップ4で合成した5−ブロモ−1−(3−メチル−2−ニトロフェニル)−3−(2−ピリジニル)−2−ベンゾイミダゾリノン12g(28mmol)、水6.2g、エタノール280mL、塩化スズ(II)26g(140mmol)を、還流管を付けた三口フラスコに入れ、窒素気流下にて80℃で5時間加熱した。得られた反応物を氷で冷やした2M水酸化ナトリウム水溶液に入れ、1時間攪拌させた。この混合液をクロロホルムで抽出し、抽出液を水、飽和食塩水にて洗浄した。さらにこれに硫酸マグネシウムを加え、ろ過し、ろ液を濃縮した。得られた残渣をヘキサンにて洗浄することにより目的物9.1g(収率:83%、黄色固体)を得た。ステップ5の合成スキームを下記式(eー1)に示す。
上記ステップ5で合成した5−ブロモ−1−(3−メチル−2−アミノフェニル)−3−(2−ピリジニル)−2−ベンゾイミダゾリノン10g(25mmol)を三口フラスコに入れ、容器を0℃に冷やした。ここで、塩化ホスホリル15mL(160mmol)を滴下し、100℃で5時間加熱した。得られた反応物にトルエンを加え、氷水へ攪拌しながらゆっくり入れた。ここに3M水酸化ナトリウム水溶液を加え、1時間攪拌した。得られた混合物をろ過し、ろ物は水、酢酸エチルにて洗浄し、ろ液は酢酸エチルで抽出後、飽和食塩水にて洗浄し、硫酸マグネシウムで乾燥した後、濃縮した。洗浄したろ物と、濃縮で得られた残渣を合わせて、エタノールで超音波洗浄することにより、目的物5.7g(収率:72%、薄茶色固体)を得た。ステップ6の合成スキームを下記式(f−1)に示す。
次に2−ブロモフェノール1.5g(8.8mmol)、ピラゾール0.50g(7.3mmol)、炭酸カリウム1.6g(15mmol)、ヨウ化銅0.28g(1.5mmol)、trans−N,N’−ジメチルシクロヘキサン−1,2−ジアミン210mgを還流管を付けた三口フラスコに入れた。フラスコ内を窒素置換し、トルエン37mLを加え、110℃で13時間加熱した。得られた反応物を酢酸エチルに溶解し、セライトを通した後の溶液を濃縮した。得られた残渣を、酢酸エチル:ヘキサン=1:2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0.70g(収率:60%、黄色固体)を得た。ステップ7の合成スキームを下記式(g−1)に示す。
次に、上記ステップ7で合成した3−(1H−ピラゾール−1−イル)フェノール0.69g(4.3mmol)、上記ステップ6で合成した3−ブロモ−7−メチル−5−(2−ピリジニル)−5H−ベンゾイミダゾ[1,2−a]ベンゾイミダゾール1.8g(4.7mmol)、ヨウ化銅0.25g(1.3mmol)、ピコリン酸0.80mg(6.5mmol)、リン酸カリウム1.6g(15mmol)、DMSO22mL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た。窒素気流下にて150℃で27時間加熱した。得られた反応物をろ過し、ろ物を水、エタノールにて洗浄し固体を得た。得られた固体を、酢酸エチル:ヘキサン=1:20を展開溶媒としたシリカ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0.37g(収率19%、黄白色固体)を得た。ステップ8の合成スキームを下記式(h−1)に示す。
次に、上記ステップ8で合成したH2ppzObibipy0.37g(0.80mmol)、テトラクロロ白金(II)酸カリウム0.37g(0.88mmol)、氷酢酸15mLを、還流管を付けた三口フラスコに入れ、窒素気流下にて130℃で30時間加熱した。得られた反応物をろ過し、ろ物を熱クロロホルムに溶解し、セライト、中性シリカゲル、セライトの順に充填したろ過補助剤を通し、ろ過した。ろ液を濃縮し、得られた固体をクロロホルムにて再結晶することにより本発明の有機金属錯体[Pt(ppzObibipy)]を黄白色固体として得た(収率31%)。ステップ9の合成スキームを下記式(i−1)に示す。
次に、[Pt(ppzObibipy)]のジクロロメタン溶液の紫外可視吸収スペクトル(以下、単に「吸収スペクトル」という)及び発光スペクトルを測定した。吸収スペクトルの測定には、紫外可視分光光度計((株)日本分光製 V550型)を用い、ジクロロメタン溶液を石英セルに入れ、室温で測定を行った。また、発光スペクトルの測定には、絶対PL量子収率測定装置((株)浜松ホトニクス製 C11347−01)を用い、グローブボックス((株)ブライト製 LABstarM13(1250/780)にて、窒素雰囲気下でジクロロメタン脱酸素溶液を石英セルに入れ、密栓し、室温で測定を行った。得られた吸収スペクトル及び発光スペクトルの測定結果を図15に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。また、図15において2本の実線が示されているが、細い実線は吸収スペクトルを示し、太い実線は発光スペクトルを示している。図15に示す吸収スペクトルは、ジクロロメタン溶液を石英セルに入れて測定した吸収スペクトルから、ジクロロメタンのみを石英セルに入れて測定した吸収スペクトルを差し引いた結果を示している。
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110nm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
503 EL層
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
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 (6)
- 請求項1または請求項2に記載の有機金属錯体を有する発光素子。
- 請求項3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4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4に記載の発光装置と、
筐体と、
を有する照明装置。
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KR102456659B1 (ko) | 2014-12-26 | 2022-10-18 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치 |
JP6775303B2 (ja) | 2015-02-27 | 2020-10-28 | 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 |
JP6697299B2 (ja) | 2015-04-01 | 2020-05-20 | 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 |
JP6764671B2 (ja) | 2015-04-14 | 2020-10-07 | 株式会社半導体エネルギー研究所 | 複素環化合物、発光素子、発光装置、電子機器、および照明装置 |
KR102623039B1 (ko) | 2015-05-15 | 2024-01-08 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 기기 및 조명 장치 |
KR20160140393A (ko) | 2015-05-29 | 2016-12-07 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 표시 장치, 전자 기기 및 조명 장치 |
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US20170183368A1 (en) | 2017-06-29 |
JP2021183620A (ja) | 2021-12-02 |
CN106916189B (zh) | 2021-09-07 |
JP7167270B2 (ja) | 2022-11-08 |
JP2023015131A (ja) | 2023-01-31 |
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