公开(公告)号：US11075346B2

公开(公告)日：2021-07-27

申请号：US16427388

申请日：2019-05-31

申请人： UDC IRELAND LIMITED

发明人： Christian Lennartz ,  Stefan Metz ,  Korinna Dormann ,  Gerhard Wagenblast ,  Ute Heinemeyer ,  Hannah Mangold ,  Minlu Zhang ,  Thomas-Wesley Holcombe

IPC分类号： H01L51/00 ,  H01L51/50 ,  C09K11/06 ,  C09K11/02

摘要： The present invention relates to organic light-emitting devices comprising (a) an anode, (i) a cathode, and (e) an emitting layer between the anode and cathode, comprising 2 to 40% by weight of a luminescent organometallic complex X having a difference of the singlet energy (ES1(X)) and the triplet energy (ET1(X)) of of ≤0.3 eV [Δ(ES1(X))−(ET1(X))≤0.3], 0.05 to 5.0% by weight of a fluorescent emitter Y and 55 to 97.95% by weight of a host compound(s), wherein the amount of the organometallic complex X, the fluorescent emitter Y and the host compound(s) adds up to a total of 100% by weight and the singlet energy of the luminescent organometallic complex X (ES1(X)) is greater than the singlet energy of the fluorescent emitter Y (ES1(Y)) [(ES1(X))>ES1(Y)]. By doping, for example, an emitting layer containing a luminescent organometallic complex having a small S1-T1 splitting, with a fluorescent emitter the emission decay time can significantly be shortened without sacrificing external quantum efficiency (EQE) because of very efficient energy transfer.

公开(公告)号：US20200044165A1

公开(公告)日：2020-02-06

申请号：US16427388

申请日：2019-05-31

申请人： UDC IRELAND LIMITED

发明人： Christian Lennartz ,  Stefan Metz ,  Korinna Dormann ,  Gerhard Wagenblast ,  Ute Heinemeyer ,  Hannah Mangold ,  Minlu Zhang ,  Thomas-Wesley Holcombe

IPC分类号： H01L51/00 ,  H01L51/50 ,  C09K11/06 ,  C09K11/02

摘要： The present invention relates to organic light-emitting devices comprising (a) an anode, (i) a cathode, and (e) an emitting layer between the anode and cathode, comprising 2 to 40% by weight of a luminescent organometallic complex X having a difference of the singlet energy (ES1(X)) and the triplet energy (ET1(X)) of of ≤0.3 eV [Δ(ES1(X))−(ET1(X))≤0.3], 0.05 to 5.0% by weight of a fluorescent emitter Y and 55 to 97.95% by weight of a host compound(s), wherein the amount of the organometallic complex X, the fluorescent emitter Y and the host compound(s) adds up to a total of 100% by weight and the singlet energy of the luminescent organometallic complex X (ES1(X)) is greater than the singlet energy of the fluorescent emitter Y (ES1(Y)) [(ES1(X))>ES1(Y)]. By doping, for example, an emitting layer containing a luminescent organometallic complex having a small S1-T1 splitting, with a fluorescent emitter the emission decay time can significantly be shortened without sacrificing external quantum efficiency (EQE) because of very efficient energy transfer.

公开(公告)号：US09862739B2

公开(公告)日：2018-01-09

申请号：US15300582

申请日：2015-03-26

申请人： UDC IRELAND LIMITED

发明人： Stefan Metz ,  Korinna Dormann ,  Glauco Battagliarin ,  Christian Eickhoff ,  Flavio Luiz Benedito ,  Soichi Watanabe ,  Gerhard Wagenblast ,  Thomas Geβner ,  Christian Lennartz ,  Peter Murer

IPC分类号： C07F15/00 ,  H01L51/50 ,  H01L51/00 ,  C09K11/06

CPC分类号： C07F15/0033 ,  C09B57/00 ,  C09B57/10 ,  C09B69/008 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1074 ,  C09K2211/1088 ,  C09K2211/185 ,  H01L51/0054 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0085 ,  H01L51/0094 ,  H01L51/5016 ,  Y02E10/549

摘要： Cyclometallated Ir complex comprising three N,N diaryl substituted carbene ligands, bearing substituents in the 2 position of the non-cyclometallated aryl ring; an organic electronic device, preferably an organic light-emitting diode (OLED), comprising at least one cyclometallated Ir complex as described above, a light-emitting layer comprising said cyclometallated Ir complex preferably as emitter material, preferably in combination with at least one host material, use of said cyclometallated Ir complex in an OLED and an apparatus selected from the group consisting of stationary visual display units, mobile visual display units, illumination units, units in items of clothing, units in handbags, units in accessories, units in furniture and units in wallpaper comprising said organic electronic device, preferably said OLED, or said light-emitting layer. The present invention further relates to a process for the preparation of said cyclometallated Ir complex.

公开(公告)号：US20170183367A1

公开(公告)日：2017-06-29

申请号：US15300582

申请日：2015-03-26

申请人： UDC IRELAND LIMITED

发明人： Stefan Metz ,  Korinna Dormann ,  Glauco Battagliarin ,  Christian Eickhoff ,  Flavio Luiz Benedito ,  Soichi Watanabe ,  Gerhard Wagenblast ,  Thomas Geßner ,  Christian Lennartz ,  Peter Murer

IPC分类号： C07F15/00 ,  C09K11/06 ,  H01L51/00

CPC分类号： C07F15/0033 ,  C09B57/00 ,  C09B57/10 ,  C09B69/008 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1074 ,  C09K2211/1088 ,  C09K2211/185 ,  H01L51/0054 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0085 ,  H01L51/0094 ,  H01L51/5016 ,  Y02E10/549

摘要： Cyclometallated Ir complex comprising three N,N diaryl substituted carbene ligands, bearing substituents in the 2 position of the non-cyclometallated aryl ring; an organic electronic device, preferably an organic light-emitting diode (OLED), comprising at least one cyclometallated Ir complex as described above, a light-emitting layer comprising said cyclometallated Ir complex preferably as emitter material, preferably in combination with at least one host material, use of said cyclometallated Ir complex in an OLED and an apparatus selected from the group consisting of stationary visual display units, mobile visual display units, illumination units, units in items of clothing, units in handbags, units in accessories, units in furniture and units in wallpaper comprising said organic electronic device, preferably said OLED, or said light-emitting layer. The present invention further relates to a process for the preparation of said cyclometallated Ir complex.

公开(公告)号：US11605790B2

公开(公告)日：2023-03-14

申请号：US16853032

申请日：2020-04-20

申请人： UDC Ireland Limited

发明人： Peter Murer ,  Korinna Dormann ,  Flavio Luiz Benedito ,  Glauco Battagliarin ,  Stefan Metz ,  Ute Heinemeyer ,  Christian Lennartz ,  Gerhard Wagenblast ,  Soichi Watanabe ,  Thomas Geßner

IPC分类号： C09K11/06 ,  C07F15/00 ,  C09B57/10 ,  C09B57/00 ,  H01L51/50 ,  H01L51/00

摘要： An organic electronic device, preferably an organic light-emitting diode (OLED), comprising at least one metal-carbene complex comprising one, two or three specific bidentate diazabenzimidazole carbene ligands; a light-emitting layer comprising said metal-carbene complex as emitter material, preferably in combination with at least one host material; the use of said metal-carbene complex in an OLED; an apparatus selected from the group consisting of stationary visual display units, mobile visual display units, illumination units, units in items of clothing, units in handbags, units in accessories, units in furniture and units in wallpaper comprising said organic electronic device, preferably said OLED, or said light-emitting layer; the metal-carbene complex comprising one, two or three specific bidentate diazabenzimidazole carbene ligands mentioned above and a process for the preparation of said metal-carbene complex.

公开(公告)号：US20190016740A1

公开(公告)日：2019-01-17

申请号：US16132798

申请日：2018-09-17

申请人： UDC IRELAND LIMITED

发明人： Stefan Metz ,  Korinna Dormann ,  Glauco Battagliarin ,  Christian Eickhoff ,  Flavio Luiz Benedito ,  Soichi Watanabe ,  Gerhard Wegenblast ,  Thomas Beßner ,  Christian Lennartz ,  Peter Murer

IPC分类号： C07F15/00 ,  C09B57/10 ,  C09B69/00 ,  C09K11/06 ,  H01L51/00 ,  C09B57/00 ,  H01L51/50

CPC分类号： C07F15/0033 ,  C09B57/00 ,  C09B57/10 ,  C09B69/008 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1074 ,  C09K2211/1088 ,  C09K2211/185 ,  H01L51/0054 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0085 ,  H01L51/0094 ,  H01L51/5016 ,  Y02E10/549

摘要： Cyclometallated Ir complex comprising three N,N diaryl substituted carbene ligands, bearing substituents in the 2 position of the non-cyclometallated aryl ring; an organic electronic device, preferably an organic light-emitting diode (OLED), comprising at least one cyclometallated Ir complex as described above, a light-emitting layer comprising said cyclometallated Ir complex preferably as emitter material, preferably in combination with at least one host material, use of said cyclometallated Ir complex in an OLED and an apparatus selected from the group consisting of stationary visual display units, mobile visual display units, illumination units, units in items of clothing, units in handbags, units in accessories, units in furniture and units in wallpaper comprising said organic electronic device, preferably said OLED, or said light-emitting layer. The present invention further relates to a process for the preparation of said cyclometallated Ir complex.

公开(公告)号：US20180351115A1

公开(公告)日：2018-12-06

申请号：US16054011

申请日：2018-08-03

申请人： UDC IRELAND LIMITED

发明人： Oliver Molt ,  Nicolle Langer ,  Evelyn Fuchs ,  Korinna Dormann ,  Christian Schildknecht ,  Soichi Watanabe ,  Gerhard Wagenblast ,  Christian Lennartz ,  Thomas Schaefer ,  Heinz Wolleb ,  Teresa Marina Figueira Duarte ,  Stefan Metz ,  Peter Murer

IPC分类号： H01L51/00 ,  C07D405/14 ,  C07F7/08 ,  C07F15/00 ,  C09K11/02 ,  C09K11/06 ,  C07D307/91 ,  H01L51/50

CPC分类号： H01L51/0085 ,  C07D307/91 ,  C07D405/14 ,  C07F7/0816 ,  C07F15/0033 ,  C07F15/0086 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1088 ,  C09K2211/185 ,  H01L51/0065 ,  H01L51/0067 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0077 ,  H01L51/0087 ,  H01L51/0094 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5036 ,  H01L51/5048 ,  H01L51/5052 ,  H01L51/5072 ,  H01L51/5096 ,  Y02E10/549

摘要： The present invention relates to metal-carbene complexes comprising a central atom selected from iridium and platinum, and diazabenzimidazolocarbene ligands, to organic light diodes which comprise such complexes, to light-emitting layers comprising at least one such metal-carbene complex, to a device selected from the group comprising illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED and to the use of such a metal-carbene complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge or exciton blocker.

公开(公告)号：US20180182980A1

公开(公告)日：2018-06-28

申请号：US15578763

申请日：2016-05-31

申请人： UDC IRELAND LIMITED

发明人： Christian Lennartz ,  Falk May ,  Hannah Stephanie Mangold ,  Minlu Zhang ,  Glauco Battagliarin ,  Ilona Stengel ,  Thomas Wesley Holcombe ,  Stefan Metz

IPC分类号： H01L51/00 ,  C09K11/06 ,  C09K11/02

CPC分类号： H01L51/0085 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1018 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1088 ,  C09K2211/185 ,  C09K2211/188 ,  H01L51/0055 ,  H01L51/0058 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0091 ,  H01L51/0094 ,  H01L51/5016 ,  H01L51/5028 ,  H01L2251/5376 ,  H01L2251/55 ,  Y02E10/549

摘要： The present invention relates to organic light-emitting devices comprising (a) an anode, (i) a cathode, and (e) an emitting layer between the anode and cathode, comprising 40.01 to 99.95% by weight of a luminescent organometallic complex X having a difference of the singlet energy (ES1(X)) and the triplet energy (ET1(X)) of smaller than 0.2 eV [Δ(ES1(X))−(ET1(X)) ES1(Y)]. By doping, for example, an emitting layer containing a luminescent organometallic complex having a small S1−T1 splitting, with a fluorescent emitter the emission decay time can significantly be shortened without sacrificing external quantum efficiency (EQE) because of very efficient energy transfer.

公开(公告)号：US20170331054A1

公开(公告)日：2017-11-16

申请号：US15610783

申请日：2017-06-01

申请人： UDC Ireland Limited

发明人： Peter Murer ,  Glauco Battagliarin ,  Korinna Dormann ,  Stefan Metz ,  Gerhard Wagenblast ,  Flavio Luiz Benedito ,  Soichi Watanabe ,  Christian Lennartz ,  Thomas Gessner

IPC分类号： H01L51/00 ,  C09K11/06 ,  C07F15/00 ,  H01L51/50

CPC分类号： H01L51/0085 ,  C07F5/025 ,  C07F15/0033 ,  C07F15/0086 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1088 ,  C09K2211/1092 ,  C09K2211/185 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5096 ,  H05B33/14 ,  Y02E10/549 ,  Y02P70/521

摘要： The present invention relates to metal-carbene complexes of the general formula to organic electronic devices, especially OLEDs (Organic Light-Emitting Diodes) which comprise such complexes, to an apparatus selected from the group consisting of illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED, to the use of such a metal-carbene complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge or exciton blocker

公开(公告)号：US09673408B2

公开(公告)日：2017-06-06

申请号：US14908606

申请日：2014-07-29

申请人： UDC Ireland Limited

发明人： Peter Murer ,  Glauco Battagliarin ,  Korinna Dormann ,  Stefan Metz ,  Gerhard Wagenblast ,  Flavio Luiz Benedito ,  Soichi Watanabe ,  Christian Lennartz ,  Thomas Geβner

IPC分类号： C01G55/00 ,  C07D487/04 ,  H01L51/00 ,  C07F15/00 ,  H05B33/14 ,  C09K11/06 ,  C07F5/02 ,  C09K11/02 ,  H01L51/50

CPC分类号： H01L51/0085 ,  C07F5/025 ,  C07F15/0033 ,  C07F15/0086 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1088 ,  C09K2211/1092 ,  C09K2211/185 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5096 ,  H05B33/14 ,  Y02E10/549 ,  Y02P70/521

摘要： The present invention relates to metal-carbene complexes of the general formula (I), where variable M is Ir or Pt and that are characterized by variable R being a group of formula (a). The complexes are used in organic electronic devices, especially OLEDs (Organic Light-Emitting Diodes), illuminating elements, stationary visual display units and in material layers as emitter, charge transport material and/or charge or exiton blocker.