JP2017508845A - Oled用途向けの白金(ii)エミッター - Google Patents
Oled用途向けの白金(ii)エミッター Download PDFInfo
- Publication number
- JP2017508845A JP2017508845A JP2016554890A JP2016554890A JP2017508845A JP 2017508845 A JP2017508845 A JP 2017508845A JP 2016554890 A JP2016554890 A JP 2016554890A JP 2016554890 A JP2016554890 A JP 2016554890A JP 2017508845 A JP2017508845 A JP 2017508845A
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- JP
- Japan
- Prior art keywords
- carbon atoms
- emitter
- light emitting
- oled
- emitting device
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 14
- 238000010791 quenching Methods 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 28
- -1 Cyano, carboxyl Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000005504 styryl group Chemical group 0.000 claims description 11
- 125000004442 acylamino group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 238000011978 dissolution method Methods 0.000 claims description 2
- 238000007738 vacuum evaporation Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 28
- 238000000034 method Methods 0.000 abstract description 8
- 238000002207 thermal evaporation Methods 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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- 239000003446 ligand Substances 0.000 description 19
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- 230000015572 biosynthetic process Effects 0.000 description 14
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- 238000003786 synthesis reaction Methods 0.000 description 14
- 229910052697 platinum Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 0 CC(C)(C)c1cc(*)cc(C(C)(C)C)c1 Chemical compound CC(C)(C)c1cc(*)cc(C(C)(C)C)c1 0.000 description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 10
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- 229960000583 acetic acid Drugs 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- 229910004298 SiO 2 Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
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- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
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- 239000011630 iodine Chemical group 0.000 description 4
- 229910052740 iodine Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- ZHBOFZNNPZNWGB-UHFFFAOYSA-N 9,10-bis(phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 ZHBOFZNNPZNWGB-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006619 Stille reaction Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- 125000004404 heteroalkyl group Chemical group 0.000 description 2
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
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- AUXWRXDUGJBOSV-UHFFFAOYSA-N CC(C1CC1)C1=CCCC1 Chemical compound CC(C1CC1)C1=CCCC1 AUXWRXDUGJBOSV-UHFFFAOYSA-N 0.000 description 1
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- 238000003747 Grignard reaction Methods 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- FXCWJOMEAGKNSP-UHFFFAOYSA-K [Cl-].[Cl-].[Cl-].Cl.[K+].[Pt+2] Chemical group [Cl-].[Cl-].[Cl-].Cl.[K+].[Pt+2] FXCWJOMEAGKNSP-UHFFFAOYSA-K 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- GOPDFXUMARJJEA-UHFFFAOYSA-N amino(nitro)azanide Chemical compound N[N-][N+]([O-])=O GOPDFXUMARJJEA-UHFFFAOYSA-N 0.000 description 1
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- YVVVSJAMVJMZRF-UHFFFAOYSA-N c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 Chemical compound c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 YVVVSJAMVJMZRF-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明において、我々は、発光量子変換効率が高く、自己消光定数の小さい、新しい配位子核を有する白金(II)エミッターを設計している。それらは、工業において使用する準備ができている。
またB、および、
本明細書に開示されている内容を理解しやすくするため、本明細書で使用される幾つもの用語、略号または他の省略表現を以下に定義しておく。定義されていない用語、略号または省略表現はいずれも、本出願の提出の際に当業者が使用している通常の意味を持つと理解される。
一つの実施形態では、白金(II)エミッターは、以下の構造Iの化学構造を有する。
さらにB、および、
一つの実施形態では、構造Iの化学構造を有する白金(II)エミッターは、以下の構造IIの化学構造を有する四座配位子から製造できる。
またB、および
エミッターを工業において使用するためには、満たすべき多くの基準があり、本発明のエミッターが満たしている基準を以下に示す。
このことは、B基、と、
マグネシウム(3.3g、137mmol、1.2当量)と40mLの無水ジエチルエーテルとの溶液に、窒素雰囲気下において、滴下漏斗で原料511(41.5mL、137mmol、1.2当量)をゆっくり加えた。環流させながら3時間撹拌した後、中間体3101が形成され、それを更なる精製を行わずに使用した。
構造を図2に示すが、それは、エミッターが平面構造ではないことを示している。単結晶のX線回折データを、300mmのイメージングプレート検出器(image plate detector)を有するMAR PSD回折計またはBruker X8 Proteum回折計で集めた。回折像を作成し、回折強度はDENZOプログラムを用いて積分し、結晶構造はSHELXS−97プログラムを用いた直接法で解明した。
エミッター1002の紫外可視吸収・発光スペクトルを図3に示す。
OLEDはすべて、ITO/MoO3(5nm)/HTL(50nm)/TCTA:エミッター1002(10nm)/ETL(50nm)/LiF(1.2nm)/Al(150nm)という簡単な構造のものを製造した。TAPC(ジ−[4−(N,N−ジトリル−アミノ)−フェニル]シクロヘキサン)を正孔輸送層(HTL)として使用し、TmPyPB(1,3,5−tri(m−ピリド−3−イル−フェニル))またはTm3PyBPZ(2,4,6−トリス(3−(3−(ピリジン−3−イル)フェニル)フェニル)−1,3,5−トリアジン)を電子伝達層(ETL)として使用した。
エミッター1002のOLEDの効率が高く、効率ロールオフが低いことを説明するため、理論計算およびフェトム秒時間分解蛍光測定を実施した。エミッター1002の三重項励起状態の形状に基づいたM062X/6−311G*(lanl2dz)レベルでのTDDFT計算では、発光波長が512nmである。これは、実験データ(517nm)と一致する。予想されるように、エミッター1002の場合、T1状態とS0状態との間の形状の相違は非常に小さい。これは、T1からS0への非放射減衰率定数(knr)が非常にゆっくりであることを意味する。エミッター1002の調光器の最適化形状を図9に示す。計算した形状パラメータは、X線結晶構造解析データとよく一致している。Pt−Pt間の距離は4.616Åであり、Pt−Pt間の相互作用は生じていない。
HOMOおよびLUMOは主にO^N^C^N配位子に局在化している(図10を参照)。発光は主にHOMO−1→LUMO+1からのものであり(81.4%)、これは主として配位子の置換基のπ−π*遷移に起因する。
Claims (18)
- 構造I:
また、B、および
の化学構造を有する有機発光ダイオード(OLED)エミッター。 - 前記R1〜R13が独立して、水素、ハロゲン、ヒドロキシル、1〜10個の炭素原子を含む非置換アルキル、1〜20個の炭素原子を含む置換アルキル、4〜20個の炭素原子を含むシクロアルキル、6〜20個の炭素原子を含む非置換アリール、6〜20個の炭素原子を含む置換アリール、1〜20個の炭素原子を含むアシル、1〜20個の炭素原子を含むアルコキシ、1〜20個の炭素原子を含むアシルオキシ、アミノ、ニトロ、1〜20個の炭素原子を含むアシルアミノ、1〜20個の炭素原子を含むアラルキル、シアノ、1〜20個の炭素原子を含むカルボキシル、チオール、スチリル、1〜20個の炭素原子を含むアミノカルボニル、1〜20個の炭素原子を含むカルバモイル、1〜20個の炭素原子を含むアリールオキシカルボニル、1〜20個の炭素原子を含むフェノキシカルボニル、または1〜20個の炭素原子を含むアルコキシカルボニル基である、請求項1に記載のOLEDエミッター。
- R14〜R21が独立して、水素、ハロゲン、ヒドロキシル、1〜10個の炭素原子を含む非置換アルキル、1〜20個の炭素原子を含む置換アルキル、4〜20個の炭素原子を含むシクロアルキル、6〜20個の炭素原子を含む非置換アリール、6〜20個の炭素原子を含む置換アリール、1〜20個の炭素原子を含むアシル、1〜20個の炭素原子を含むアルコキシ、1〜20個の炭素原子を含むアシルオキシ、アミノ、ニトロ、1〜20個の炭素原子を含むアシルアミノ、1〜20個の炭素原子を含むアラルキル、シアノ、1〜20個の炭素原子を含むカルボキシル、チオール、スチリル、1〜20個の炭素原子を含むアミノカルボニル、1〜20個の炭素原子を含むカルバモイル、1〜20個の炭素原子を含むアリールオキシカルボニル、1〜20個の炭素原子を含むフェノキシカルボニル、または1〜20個の炭素原子を含むアルコキシカルボニル基である、請求項5に記載のOLEDエミッター。
- 希薄溶液において発光λmaxが520nm未満である緑色発光を示す、請求項1に記載のOLEDエミッター。
- 6μs未満という短い発光寿命を有する、請求項1に記載のOLEDエミッター。
- 自己消光定数が10−7dm3mol−1s−1のオーダー以下である、請求項1に記載のOLEDエミッター。
- 発光材料として請求項1に記載の少なくとも一種のOLEDエミッターを含む、発光デバイス。
- 前記デバイスが有機発光ダイオード(OLED)である、請求項11に記載の発光デバイス。
- 前記デバイスが真空蒸着によって作製される、請求項11に記載の発光デバイス。
- 前記デバイスが溶解法によって作製される、請求項11に記載の発光デバイス。
- 前記デバイスが一つの放射層を含む、請求項11に記載の発光デバイス。
- 前記デバイスが複数の放射層を含む、請求項11に記載の発光デバイス。
- 1000cd/m−2での効率ロールオフが10%未満である、請求項11に記載の発光デバイス。
- 発光色が変わらない(CIExの変化が0.03未満であり、かつ/またはCIEyの変化が0.02未満である)状態で、前記エミッターのドーピング濃度が2〜30重量%である、請求項11に記載の発光デバイス。
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JP2010050451A (ja) * | 2002-05-01 | 2010-03-04 | Univ Of Hong Kong | 電界発光材料 |
WO2005042444A2 (ja) * | 2003-11-04 | 2005-05-12 | Takasago Perfumery Co Ltd | 白金錯体及び発光素子 |
US20070103060A1 (en) * | 2003-11-04 | 2007-05-10 | Takasago International Corporation | Platinum complex and light emitting device |
JP2006093542A (ja) * | 2004-09-27 | 2006-04-06 | Fuji Photo Film Co Ltd | 発光素子 |
US20060073359A1 (en) * | 2004-09-27 | 2006-04-06 | Fuji Photo Film Co., Ltd. | Light-emitting device |
US20130274473A1 (en) * | 2012-04-12 | 2013-10-17 | The University Of Hong Kong | Platinum(ii) complexes for oled applications |
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JP2023503662A (ja) * | 2019-12-11 | 2023-01-31 | 広東阿格蕾雅光電材料有限公司 | 四座配位白金(ii)錯体の製造及び使用 |
JP7385754B2 (ja) | 2019-12-11 | 2023-11-22 | 広東阿格蕾雅光電材料有限公司 | 四座配位白金(ii)錯体の製造及び使用 |
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CN111793094A (zh) | 2020-10-20 |
EP3126471A1 (en) | 2017-02-08 |
WO2015149677A1 (en) | 2015-10-08 |
JP6431085B2 (ja) | 2018-11-28 |
US10038153B2 (en) | 2018-07-31 |
KR101904629B1 (ko) | 2018-10-04 |
EP3126471B1 (en) | 2019-01-02 |
JP6916769B2 (ja) | 2021-08-11 |
US20150287937A1 (en) | 2015-10-08 |
CN106795428B (zh) | 2020-09-25 |
CN106795428A (zh) | 2017-05-31 |
EP3126471A4 (en) | 2017-11-15 |
US10998510B2 (en) | 2021-05-04 |
JP2019021925A (ja) | 2019-02-07 |
US20180323384A1 (en) | 2018-11-08 |
CN111793094B (zh) | 2023-08-08 |
KR20160131004A (ko) | 2016-11-15 |
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