JP2013038395A - 複合材料、発光素子、発光装置、電子機器、照明装置、及び有機化合物 - Google Patents
複合材料、発光素子、発光装置、電子機器、照明装置、及び有機化合物 Download PDFInfo
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- JP2013038395A JP2013038395A JP2012149361A JP2012149361A JP2013038395A JP 2013038395 A JP2013038395 A JP 2013038395A JP 2012149361 A JP2012149361 A JP 2012149361A JP 2012149361 A JP2012149361 A JP 2012149361A JP 2013038395 A JP2013038395 A JP 2013038395A
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- 239000002131 composite material Substances 0.000 title claims abstract description 202
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 198
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 57
- 150000002484 inorganic compounds Chemical class 0.000 claims abstract description 38
- 229910010272 inorganic material Inorganic materials 0.000 claims abstract description 37
- 239000000463 material Substances 0.000 claims description 124
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- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 49
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- 125000001424 substituent group Chemical group 0.000 claims description 6
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- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- 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
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 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
- 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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Abstract
【解決手段】有機化合物と、該有機化合物に対して電子受容性を示す無機化合物とを含み、該有機化合物が有する環はベンゼン環のみであり、該有機化合物が有する該ベンゼン環の数は、4以上25以下である複合材料を提供する。
【選択図】図9
Description
本実施の形態では、本発明の一態様の複合材料について説明する。
本実施の形態では、本発明の一態様の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、本発明の一態様の、発光素子を有する発光装置について図3を用いて説明する。なお、図3(A)は、発光装置を示す上面図、図3(B)は図3(A)をA−B及びC−Dで切断した断面図である。
本実施の形態では、本発明を適用した一態様である発光装置を用いて完成させた様々な電子機器および照明器具の一例について、図6、図7を用いて説明する。
まず、ガラス基板を真空蒸着装置内の基板ホルダーに固定する。そして、mBP3Pと酸化モリブデン(VI)とをそれぞれ別の抵抗加熱式の蒸発源に入れ、10−4Pa程度まで減圧した状態で、共蒸着法によりmBP3Pと酸化モリブデンとを含む膜を形成した。この時、mBP3Pと酸化モリブデンの比率が質量比で4:2、4:1、4:0.5(=mBP3P:酸化モリブデン)となるようにそれぞれ共蒸着した。なお、膜厚は50nmとした。
まず、ガラス基板を真空蒸着装置内の基板ホルダーに固定する。そして、p−セキシフェニル(略称:6P)と酸化モリブデン(VI)とをそれぞれ別の抵抗加熱式の蒸発源に入れ、10−4Pa程度まで減圧した状態で、共蒸着法により6Pと酸化モリブデンとを含む膜を形成した。この時、6Pと酸化モリブデンの比率が質量比で4:2、4:1、4:0.5(=6P:酸化モリブデン)となるようにそれぞれ共蒸着した。なお、膜厚は50nmとした。
まず、ガラス基板を真空蒸着装置内の基板ホルダーに固定する。そして、1,4−ビス(トリフェニルシリル)ベンゼン(略称:SiPSi)と酸化モリブデン(VI)とをそれぞれ別の抵抗加熱式の蒸発源に入れ、10−4Pa程度まで減圧した状態で、共蒸着法によりSiPSiと酸化モリブデンとを含む膜を形成した。この時、SiPSiと酸化モリブデンの比率が質量比で4:2、4:1、4:0.5(=SiPSi:酸化モリブデン)となるようにそれぞれ共蒸着した。なお、膜厚は50nmとした。
まず、ガラス基板1100上に、酸化珪素を含むインジウム錫酸化物(ITSO)膜をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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。
まず、ガラス基板1100上に、ITSO膜をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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。
発光素子3の正孔輸送層1112は、mBP3Pを20nmの膜厚となるように成膜することで形成した。正孔輸送層1112以外は、発光素子2と同様に作製した。
まず、ガラス基板1100上に、ITSO膜をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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。
発光素子5の正孔注入層1111は、4,4’−ビス(トリフェニルシリル)ビフェニル(略称:SiBiSi)と酸化モリブデン(VI)を共蒸着することで形成した。その膜厚は、50nmとし、SiBiSiと酸化モリブデンの比率は、質量比で4:2(=SiBiSi:酸化モリブデン)となるように調節した。正孔注入層1111以外は、発光素子4と同様に作製した。
mBP22PSiの合成スキームを以下に示す。
1H NMR(CDCl3,300MHz):δ(ppm)=7.30−7.59(m,38H),7.74−7.79(m,8H),7.95(d,J=1.5Hz,4H),7.97(d,J=1.5Hz,2H)。
まず、ガラス基板1100上に、ITSO膜をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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。
発光素子7は、正孔輸送層1112以外は、実施例7の発光素子6と同様の材料、方法及び条件を適用して作製した。
発光素子8は、第1の発光層1113a以外は、上記発光素子7と同様の材料、方法及び条件を適用して作製した。
発光素子9は、電子輸送層1114以外は、上記発光素子8と同様の材料、方法及び条件を適用して作製した。
まず、ガラス基板1100上に、ITSO膜をスパッタリング法にて成膜し、陽極として機能する第1の電極1101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。
上記実施例で用いたトリス[3−メチル−1−(2−メチルフェニル)−5−フェニル−1H−1,2,4−トリアゾラト]イリジウム(III)(略称:[Ir(Mptz1−mp)3]を合成する例を示す。
まず、アセトイミド酸エチル塩酸塩15.5g、トルエン150mL、トリエチルアミン(Et3N)31.9gを500mL三ツ口フラスコに入れ、室温で10分間撹拌した。この混合物にベンゾイルクロリド17.7gとトルエン30mLの混合溶液を50mL滴下ロートより滴下し、室温で24時間撹拌した。所定時間経過後、反応混合物を吸引濾過し、固体をトルエンで洗浄した。得られた濾液を、濃縮してN−(1−エトキシエチリデン)ベンズアミドを得た(赤色油状物、収率82%)。ステップ1の合成スキームを以下に示す。
次に、o−トリルヒドラジン塩酸塩8.68g、四塩化炭素100mL、トリエチルアミン(Et3N)35mLを300mLナスフラスコに入れ、室温で1時間撹拌した。所定時間経過後、この混合物に上記ステップ1で得られたN−(1−エトキシエチリデン)ベンズアミド8.72gを加えて室温で24時間撹拌した。所定時間経過後、反応混合物に水を加え、水層から有機物をクロロホルムで抽出した。抽出溶液及び有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムを加えて乾燥させた。得られた混合物を自然濾過し、濾液を濃縮して油状物を得た。得られた油状物をシリカゲルカラムクロマトグラフィーにより精製した。展開溶媒にはジクロロメタンを用いた。得られたフラクションを濃縮して、3−メチル−1−(2−メチルフェニル)−5−フェニル−1H−1,2,4−トリアゾール(略称:HMptz1−mp)を得た(橙色油状物、収率84%)。ステップ2の合成スキームを以下に示す。
次に、上記ステップ2で得られた配位子HMptz1−mp2.71g、トリス(アセチルアセトナト)イリジウム(III)1.06gを、三方コックを付けた反応容器に入れた。この反応容器をアルゴン置換し、250℃にて48時間加熱し、反応させた。この反応混合物をジクロロメタンに溶解し、シリカゲルカラムクロマトグラフィーにより精製した。展開溶媒には、まず、ジクロロメタン用い、次いでジクロロメタン:酢酸エチル=10:1(体積比)の混合溶媒を用いた。得られたフラクションを濃縮して固体を得た。この固体を酢酸エチルで洗浄し、次いで、ジクロロメタンと酢酸エチルの混合溶媒にて再結晶し、有機金属錯体[Ir(Mptz1−mp)3]を得た(黄色粉末、収率35%)。ステップ3の合成スキームを以下に示す。
1H NMR.δ(CDCl3):1.94−2.21(m,18H),6.47−6.76(m,12H),7.29−7.52(m,12H)。
101 第1の電極
102 EL層
108 第2の電極
401 ソース側駆動回路
402 画素部
403 ゲート側駆動回路
404 封止基板
405 シール材
407 空間
408 引き回し配線
409 FPC(フレキシブルプリントサーキット)
410 素子基板
411 スイッチング用TFT
412 電流制御用TFT
413 第1の電極
414 絶縁物
416 EL層
417 第2の電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
501 基板
502 第1の電極
503 第2の電極
504 EL層
505 絶縁層
506 隔壁層
701 正孔注入層
702 正孔輸送層
703 発光層
704 電子輸送層
705 電子注入層
706 電子注入バッファー層
707 電子リレー層
708 複合材料層
800 第1のEL層
801 第2のEL層
802 EL層
803 電荷発生層
811 照明装置
812 照明装置
813 卓上照明器具
900 発光装置
901 第1の基板
902 第2の基板
903 第1の端子
904 第2の端子
908 発光素子
909 絶縁層
910 補助配線
911 乾燥剤
912 シール材
913a 光取り出し構造
913b 光取り出し構造
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
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
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7312 マイクロフォン
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
7501 照明部
7502 傘
7503 可変アーム
7504 支柱
7505 台
7506 電源
Claims (20)
- 有機化合物と、前記有機化合物に対して電子受容性を示す無機化合物とを含み、
前記有機化合物が有する環はベンゼン環のみであり、
前記有機化合物が有する前記ベンゼン環の数は、4以上25以下である複合材料。 - 分子量が350以上2000以下である有機化合物と、前記有機化合物に対して電子受容性を示す無機化合物とを含み、
前記有機化合物が有する環はベンゼン環のみである複合材料。 - 有機化合物と、遷移金属酸化物とを含み、
前記有機化合物が有する環はベンゼン環のみであり、
前記有機化合物が有する前記ベンゼン環の数は、4以上25以下である複合材料。 - 分子量が350以上2000以下である有機化合物と、遷移金属酸化物とを含み、
前記有機化合物が有する環はベンゼン環のみである複合材料。 - 請求項3又は請求項4において、
前記遷移金属酸化物は、チタン酸化物、バナジウム酸化物、タンタル酸化物、モリブデン酸化物、タングステン酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、銀酸化物から選ばれる一種又は複数種である複合材料。 - 請求項1乃至請求項5のいずれか一項において、
前記有機化合物が、炭素数1〜6のアルキル基を置換基として有する複合材料。 - 請求項1乃至請求項6のいずれか一項において、
前記有機化合物が、珪素で架橋されたベンゼン環を有する複合材料。 - 請求項1乃至請求項7のいずれか一項において、
前記有機化合物が、トリアルキルシリル基を置換基として有する複合材料。 - 請求項1乃至請求項8のいずれか一項において、
前記有機化合物の最高被占有軌道準位は、光電子分光法での測定値が−5.7eV以下である複合材料。 - 一対の電極間に発光物質を含む層を有し、
前記発光物質を含む層は、請求項1乃至請求項9のいずれか一項に記載の複合材料を含む層を有する発光素子。 - 請求項10において、
前記複合材料を含む層が、前記一対の電極のうち陽極として機能する電極と接する発光素子。 - 請求項10又は請求項11において、
前記発光物質を含む層は、第1の層を、前記複合材料を含む層の陰極側に接して有し、
前記第1の層に含まれる有機化合物が有する環はベンゼン環のみであり、
前記第1の層に含まれる有機化合物が有する前記ベンゼン環の数は、4以上25以下である発光素子。 - 請求項12において、
前記発光物質を含む層は、発光層を、前記第1の層の陰極側に接して有し、
前記発光層において、第1の有機化合物が第2の有機化合物中に分散されており、
前記第2の有機化合物が有する環はベンゼン環のみであり、
前記第2の有機化合物が有する前記ベンゼン環の数は、4以上25以下である発光素子。 - 請求項10において、
前記複合材料を含む層が、前記一対の電極のうち陰極として機能する電極と接する発光素子。 - 一対の電極間に第1の発光物質を含む層乃至第nの発光物質を含む層(nは2以上の自然数)を有し、
第kの発光物質を含む層(kは、1以上n未満の自然数)と第(k+1)の発光物質を含む層との間に、請求項1乃至請求項9のいずれか一項に記載の複合材料を含む層を有する発光素子。 - 請求項15において、
第1の層を、前記複合材料を含む層の陰極側に接して有し、
前記第1の層に含まれる有機化合物が有する環はベンゼン環のみであり、
前記第1の層に含まれる有機化合物が有する前記ベンゼン環の数は、4以上25以下である発光素子。 - 請求項10乃至請求項16のいずれか一項に記載の発光素子を有する発光装置。
- 請求項17に記載の発光装置を表示部に有する電子機器。
- 請求項17に記載の発光装置を発光部に有する照明装置。
- 構造式(112)で表される有機化合物。
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JP6194089B2 (ja) | 2017-09-06 |
TWI550057B (zh) | 2016-09-21 |
JP6034603B2 (ja) | 2016-11-30 |
US20130009138A1 (en) | 2013-01-10 |
US9419239B2 (en) | 2016-08-16 |
JP2017034278A (ja) | 2017-02-09 |
TW201305316A (zh) | 2013-02-01 |
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