JP3981079B2 - 赤橙色または赤色発光を有するエレクトロルミネセンスイリジウム化合物及びかかる化合物で製造されたデバイス - Google Patents
赤橙色または赤色発光を有するエレクトロルミネセンスイリジウム化合物及びかかる化合物で製造されたデバイス Download PDFInfo
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- FSEXLNMNADBYJU-UHFFFAOYSA-N alpha-Phenylquinoline Natural products C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000001659 ion-beam spectroscopy Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- AIWZOHBYSFSQGV-LNKPDPKZSA-M sodium;(z)-4-oxopent-2-en-2-olate Chemical compound [Na+].C\C([O-])=C\C(C)=O AIWZOHBYSFSQGV-LNKPDPKZSA-M 0.000 description 1
- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052717 sulfur 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
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Description
IrL3 (I)
IrL2Z (II)
から選択される式を有する金属錯体を目的とし、
式中、
Zが、β−ジエノレート、アミノカルボキシレート、イミノカルボキシレート、サリチレート、ヒドロキシキノレート、及びジアリールホスフィノアルコキシドから選択され、
Lが、図1の式III、式IV、式V、式VI、及び式VII、ならびに図2の式VIII、式IX及び式Xから選択され、
式IIIにおいて、
R3〜R6が同一または異なっており、R3〜R6の少なくとも1つが、D、F、CnF2n+1、OCnF2n+1、及びOCF2Yから選択され、
式III〜VIIのいずれかにおいて、出現するごとに、
R1が、出現するごとに、同一または異なっており、D、CnH2n+1、OR11、SR11、N(R11)2、F、Cn(H+F)2n+1、OCn(H+F)2n+1、及びOCF2Yから選択されるか、または隣接する一対のR1が結合して5または6員環を形成することができ、
YがH、Cl、またはBrであり、
AがSまたはNR11であり、
式III〜Xのいずれかにおいて、出現するごとに、
R11が、出現するごとに、同一または異なっており、HまたはCnH2n+1であり、
nが1〜12の整数であり、
αが0、1または2であり、
式IV〜Xのいずれかにおいて、出現するごとに、
δが0または1〜4の整数であり、
式VIIにおいて、
E1〜E4が同一または異なっており、NまたはCR12であるが、ただし、少なくとも1つのEがNであり、
R12が、出現するごとに、同一または異なっており、H、D、SR11、N(R11)2、F、Cn(H+F)2n+1、OCn(H+F)2n+1、及びOCF2Yから選択され、または隣接した一対のR12が結合して5または6員環を形成するが、ただし、R12の少なくとも1つが、D、F、Cn(H+F)2n+1、OCn(H+F)2n+1、及びOCF2Yから選択され、
式VIII〜Xのいずれかにおいて、出現するごとに、
R2及びR7〜R10が、出現するごとに、同一または異なっており、H、D、CnH2n+1、OR11、SR11、及びN(R11)2から選択され、または隣接した一対のR基が結合して5または6員環を形成することができる。
1,3−ジフェニル−1,3−プロパンジオネート[DI]
2,2,6,6−テトラメチル−3,5−ヘプタンジオネート[TMH]
4,4,4−トリフルオロ−1−(2−チエニル)−1,3−ブタンジオネート[TTFA]
7,7−ジメチル−1,1,1,2,2,3,3−ヘプタフルオロ−4,6−オクタンジオネート[FOD]
1,1,1,3,5,5,5−ヘプタフルオロ−2,4−ペンタンジオネート[F7acac]
1,1,1,5,5,5−ヘキサフルオロ−2,4−ペンタンジオネート[F6acac]
1−フェニル−3−メチル−4−i−ブチリル−ピラゾリノネート[FMBP]
8−ヒドロキシキノリネート[8hq]
2−メチル−8−ヒドロキシキノリネート[Me−8hq]
10−ヒドロキシベンゾキノリネート[10−hbq]
などがある。
親ヒドロキシキノリン化合物は概して市販されている。
R14が、出現するごとに、同一または異なっていてもよく、Cn(H+F)2n+1及びC6(H+F)5から選択され、
R15が、出現するごとに、同一または異なっていてもよく、H及びCn(H+F)2n+1から選択され、
λが2または3である。
1,1−ビス(トリフルオロメチル)−2−(ジフェニルホスフィノ)−エトキシド[tfmdpeO]
親ホスフィノアルカノール化合物は概して市販されている。
本発明はまた、2つの電気的接触層の間に配置された少なくとも1つの光活性層を含む電子デバイスに関するものであり、そこにおいて、前記デバイスの少なくとも1つの光活性層が、本発明の錯体を含有する。図6に示すように、代表的なデバイス100が、アノード層110及びカソード層150、及びアノード110とカソード150との間の層120,130、及び任意に140を有する。層120、130、及び140が一括して、活性層と称される。正孔注入/輸送層120がアノードに隣接している。電子輸送材料を含む任意の層140がカソードに隣接している。正孔注入/輸送層120とカソード(または任意の電子輸送層)との間に光活性層130がある。層120、130、及び140が個々に、及び一括して活性層と称される。
この実施例は、配位子親化合物(HL)、2−(2−チエニル)−5−(トリフルオロメチル)ピリジンの調製について説明する。
この実施例は、中間ジクロロ架橋ダイマー、[IrCl{2−(2−チエニル)−5−(トリフルオロメチル)ピリジン}2]2の調製について説明する。
この実施例は、トリス環金属イリジウム錯体、[Ir{2−(2−チエニル)−5−(トリフルオロメチル)ピリジン}3]、表1の化合物1−aの調製について説明する。
この実施例は、配位子親化合物、1−(4−t−ブチルフェニル)−イソキノリンの調製について説明する。
この実施例は、ジクロロ架橋ダイマー、IrCl{1−(4−t−Bu−フェニル)−イソキノリン}2]2の調製について説明する。
この実施例は、ビス環金属イリジウム錯体、[Ir(acac){1−(4−t−Bu−フェニル)−イソキノリン}2]、表1の化合物1−jの調製について説明する。
この実施例は、配位子親化合物、1−(ペルジューテロフェニル)−イソキノリンの調製について説明する。
この実施例は、ジクロロ架橋ダイマー、[IrCl{1−(ペルジューテロフェニル)−イソキノリン}2]2の調製について説明する。
この実施例は、ビス環金属イリジウム錯体、Ir(acac){1−(ペルジューテロフェニル)−イソキノリン}2、表1の化合物1−mの調製について説明する。
この実施例は、本発明のイリジウム錯体を使用するOLEDの形成について説明する。
この実施例は、ポリ(フルオレン)ポリマー母材中のドーパントとして本発明の赤色発光材料を使用するOLEDの形成について説明する。得られたブレンドは、OLED中の活性赤色発光層として用いられる。イリジウム錯体、[Ir(acac){1−(4−t−Bu−フェニル)−イソキノリン}2]、表1の1−j化合物を、実施例6に記載したように調製する。ポリフルオレンポリマーは、(非特許文献4)に記載されているように調製され、そこにおいて、モノマー単位のジハロ、好ましくはジブロモ誘導体が、ビス(1,5−シクロオクタジエン)ニッケル(0)などのゼロ価ニッケル化合物の化学量論量と反応させられる。
本発明は以下の実施の態様を含むものである。
1.式I及び式II:
IrL 3 (I)
IrL 2 Z (II)
から選択される式を有する少なくとも1つの化合物を含む活性層であって、
式中、
Zが、β−ジエノレート、アミノカルボキシレート、イミノカルボキシレート、サリチレート、ヒドロキシキノレート、及びジアリールホスフィノアルコキシドから選択され、
Lが、図1の式III、式IV、式V、式VI、及び式VII、ならびに図2の式VIII、式IX及び式Xから選択され、
式IIIにおいて、
R 3 〜R 6 が同一または異なっており、R 3 〜R 6 の少なくとも1つが、D、F、C n F 2n+1 、OC n F 2n+1 、及びOCF 2 Yから選択され、
式III〜VIIのいずれかにおいて、出現するごとに、
R 1 が、出現するごとに、同一または異なっており、D、C n H 2n+1 、OR 11 、SR 11 、N(R 11 ) 2 、F、C n (H+F) 2n+1 、OC n (H+F) 2n+1 、及びOCF 2 Yから選択されるか、または隣接する一対のR 1 が結合して5または6員環を形成することができ、
YがH、Cl、またはBrであり、
AがSまたはNR 11 であり、
式III〜Xのいずれかにおいて、出現するごとに、
R 11 が、出現するごとに、同一または異なっており、HまたはC n H 2n+1 であり、
nが1〜12の整数であり、
αが0、1または2であり、
式IV〜Xのいずれかにおいて、出現するごとに、
δが0または1〜4の整数であり、
式VIIにおいて、
E 1 〜E 4 が同一または異なっており、NまたはCR 12 であるが、ただし、少なくとも1つのEがNであり、
R 12 が、出現するごとに、同一または異なっており、H、D、SR 11 、N(R 11 ) 2 、F、C n (H+F) 2n+1 、OC n (H+F) 2n+1 、及びOCF 2 Yから選択され、または隣接した一対のR 12 が結合して5または6員環を形成するが、ただし、R 12 の少なくとも1つが、D、F、C n (H+F) 2n+1 、OC n (H+F) 2n+1 、及びOCF 2 Yから選択され、
式VIII〜Xのいずれかにおいて、出現するごとに、
R 2 及びR 7 〜R 10 が、出現するごとに、同一または異なっており、H、D、C n H 2n+1 、OR 11 、SR 11 、及びN(R 11 ) 2 から選択され、または隣接した一対のR基が結合して5または6員環を形成することができるが、
ただし、活性層が、前記少なくとも1つの化合物、20重量%未満を含有する場合、希釈剤が存在していることを特徴とする活性層。
2.570〜700nmの範囲の発光最大を有する発光材料を含むことを特徴とする、前記1に記載の活性層を含む有機電子デバイス。
3.R 5 がCF 3 であり、及び/またはR 8 がOCH 3 及びOHから選択され、及び/またはR 9 がt−ブチルであることを特徴とする、前記1に記載の活性層、または前記2に記載のデバイス。
4.N,N’−ジフェニル−N,N’−ビス(3−メチルフェニル)−[1,1’−ビフェニル]−4,4’−ジアミン、1,1−ビス[(ジ−4−トリルアミノ)フェニル]シクロヘキサン、N,N’−ビス(4−メチルフェニル)−N,N’−ビス(4−エチルフェニル)−[1,1’−(3,3’−ジメチル)ビフェニル]−4,4’−ジアミン、テトラキス−(3−メチルフェニル)−N,N,N’,N’−2,5−フェニレンジアミン、α−フェニル−4−N,N−ジフェニルアミノスチレン、p−(ジエチルアミノ)ベンズアルデヒドジフェニルヒドラゾン、トリフェニルアミン、ビス[4−(N,N−ジエチルアミノ)−2−メチルフェニル](4−メチルフェニル)メタン、1−フェニル−3−[p−(ジエチルアミノ)スチリル]−5−[p−(ジエチルアミノ)フェニル]ピラゾリン、1,2−トランス−ビス(9H−カルバゾル−9−イル)シクロブタン、N,N,N’,N’−テトラキス(4−メチルフェニル)−(1,1’−ビフェニル)−4,4’−ジアミン、ポルフィリン化合物、及びそれらの組合せから選択される正孔輸送層を更に含むことを特徴とする、前記2または3に記載のデバイス。
5.トリス(8−ヒドロキシキノラト)アルミニウム、2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン、4,7−ジフェニル−1,10−フェナントロリン、2−(4−ビフェニリル)−5−(4−t−ブチルフェニル)−1,3,4−オキサジアゾール、3−(4−ビフェニリル)−4−フェニル−5−(4−t−ブチルフェニル)−1,2,4−トリアゾール、及びそれらの組合せから選択される電子輸送層を更に含むことを特徴とする、前記2〜4のいずれかに記載のデバイス。
6.表1に示した錯体1−a〜1−mから選択される化合物。
7.式I及び式IIから選択される式を有する前記少なくとも1つの化合物が、表1に示した錯体1−a〜1−mから選択されることを特徴とする、前記1または3に記載の活性層、あるいは前記2〜5のいずれかに記載のデバイス。
8.前記希釈剤が、ポリ(N−ビニルカルバゾール)、ポリシラン、4,4’−N,N’−ジカルバゾールビフェニル、及び第三級芳香族アミンから選択されることを特徴とする、前記1、3及び7のいずれかに記載の活性層、あるいは前記2〜5、及び7のいずれかに記載のデバイス。
9.前記希釈剤が、ポリアリーレンビニレン、ポリフルオレン、ポリオキサジアゾール、ポリアニリン、ポリチオフェン、ポリピリジン、ポリフェニレン、それらのコポリマー、及びそれらの組合せから選択される共役ポリマーであることを特徴とする、前記1、3及び7〜8のいずれかに記載の活性層、あるいは前記2〜5、及び7〜8のいずれかに記載の有機電子デバイス。
10.前記希釈剤が、ポリアリーレンビニレン、ポリフルオレン、ポリオキサジアゾール、ポリアニリン、ポリチオフェン、ポリピリジン、ポリフェニレン、それらのコポリマー、及びそれらの組合せから選択される共役ポリマーであることを特徴とする、前記1、3及び7〜9のいずれかに記載の活性層、あるいは前記2〜5及び7〜9のいずれか一項に記載の有機電子デバイス。
Claims (3)
- 式I及び式II:
IrL3 (I)
IrL2Z (II)
から選択される式を有する少なくとも1つの化合物を含む活性層であって、
式中、
Zが、β−ジエノレート、アミノカルボキシレート、イミノカルボキシレート、サリチレート、ヒドロキシキノレート、及びジアリールホスフィノアルコキシドから選択され、
Lが、下記の式IIIであり、
R3〜R6が同一または異なっており、R3〜R6の少なくとも1つが、D、F、CnF2n+1、OCnF2n+1、及びOCF2Yから選択され、ただし、AがSの時、F、およびC n F 2n+1 を除く、
式IIIにおいて、
R1が、出現するごとに、同一または異なっており、D、CnH2n+1、OR11、SR11、N(R11)2、F、Cn(H+F)2n+1、OCn(H+F)2n+1、及びOCF2Yから選択されるか、または隣接する一対のR1が結合して5または6員環を形成することができ、
YがH、Cl、またはBrであり、
AがSまたはNR11であり、
式IIIにおいて、
R11が、出現するごとに、同一または異なっており、HまたはCnH2n+1であり、
nが1〜12の整数であり、
αが0、1または2であり、
ただし、活性層が、前記少なくとも1つの化合物が20重量%未満を含有する場合、希釈剤が存在していることを特徴とする活性層。 - 前記活性層が、570〜700nmの範囲の発光最大を有する発光材料を含むことを特徴とする、請求項1に記載の活性層を含む有機電子デバイス。
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KR20110032008A (ko) | 2011-03-29 |
JP2005508437A (ja) | 2005-03-31 |
KR20110112454A (ko) | 2011-10-12 |
ATE515550T1 (de) | 2011-07-15 |
EP1442094A2 (en) | 2004-08-04 |
JP2007270155A (ja) | 2007-10-18 |
EP2325279A3 (en) | 2012-05-30 |
KR20050043757A (ko) | 2005-05-11 |
KR101106874B1 (ko) | 2012-01-25 |
CN1705730A (zh) | 2005-12-07 |
KR20100066592A (ko) | 2010-06-17 |
EP2034000B1 (en) | 2015-05-06 |
CA2466143A1 (en) | 2003-05-15 |
EP2034000A3 (en) | 2011-01-12 |
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