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公开(公告)号:US11626563B2
公开(公告)日:2023-04-11
申请号:US16814529
申请日:2020-03-10
Applicant: UNIVERSAL DISPLAY CORPORATION
Inventor: Bin Ma , Vadim Adamovich , Edward Barron , Jui-Yi Tsai , Mingjuan Su , Lech Michalski , Chuanjun Xia , Michael S. Weaver , Walter Yeager , Bert Alleyne
Abstract: A compound having a formula (LA)mIr(LB)3−m having a structure selected from is disclosed. In the structures of formula (LA)mIr(LB)3-m, m is 1 or 2, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and, R6 is selected from C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof.
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公开(公告)号:US11108000B2
公开(公告)日:2021-08-31
申请号:US15970244
申请日:2018-05-03
Applicant: Universal Display Corporation
Inventor: Bin Ma , Walter Yeager , Edward Barron , Alan Deangelis , Chuanjun Xia , Vadim Adamovich , Scott Beers , Harvey R. Wendt , Suman Layek
Abstract: A compound having the formula Ir(LA)n(LB)3−n is disclosed wherein LA is an aza-DBF ligand and LB is an alkyl-substituted phenylpyridine ligand, wherein the compound has a structure according to Formula I: wherein A1, A2, A3, A4, A5, A6, A7, and A8 comprise carbon or nitrogen; wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is nitrogen; wherein ring B is bonded to ring A through a C—C bond; wherein the iridium is bonded to ring A through a Ir—C bond; wherein X is O, S, or Se; wherein R1 and R2 each independently represent mono-, di-, tri-, tetra-substitution, or no substitution; wherein R′ and R″ each independently represent mono-, di-substitution, or no substitution; wherein any adjacent substitutions in R′, R″, R1, R2, R3, R4, R5, and R6 are optionally linked together to form a ring; wherein R1, R2, R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein R3, R4, R5, and R6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof; wherein n is an integer from 1 to 3; and wherein total number of carbons in at least one of the pairs R3 and R4, and R5 and R6 is at least four.
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公开(公告)号:US11024807B2
公开(公告)日:2021-06-01
申请号:US16789860
申请日:2020-02-13
Applicant: Universal Display Corporation
Inventor: Lichang Zeng , Zhiqiang Ji , Edward Barron
Abstract: A compound capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature is provided. The compound includes at least one substituent R, where each of the at least one substituent R has the formula of: —G1-G2, where the dashed line denotes the bond through which R is attached in the first compound; G1 is a non-aromatic cyclic or polycyclic group; G2 is selected from aryl and heteroaryl; and G1 and G2 are independently, optionally further substituted with a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. Organic light emitting devices, consumer products, and formulations containing the compound are also provided.
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公开(公告)号:US10978648B2
公开(公告)日:2021-04-13
申请号:US15718931
申请日:2017-09-28
Applicant: Universal Display Corporation
Inventor: Chun Lin , Bin Ma , Chuanjun Xia , Lichang Zeng , Alan Deangelis , Edward Barron
Abstract: Novel heteroleptic iridium carbene complexes are provided. The complexes have lower-than expected sublimation temperatures, which is beneficial for the processing of these materials in solid state applications. Selective substitution of the ligands provides for phosphorescent compounds that are suitable for use in a variety of OLED devices. The carbene complexes can also be used as materials in a hole blocking layer and/or an electron transport layer to improve device performance.
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公开(公告)号:US10957866B2
公开(公告)日:2021-03-23
申请号:US15600016
申请日:2017-05-19
Applicant: Universal Display Corporation
Inventor: Lichang Zeng , Mingjuan Su , Edward Barron , Zhiqiang Ji , Chuanjun Xia
Abstract: New metal complexes containing a substituted fused aromatic moiety is disclosed. The substituents on the fused aromatic moiety fine-tune molecular energy levels and solid-state self-assembly, conducive to improved material performance in devices useful for phosphorescent organic light emitting devices.
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公开(公告)号:US20200220088A1
公开(公告)日:2020-07-09
申请号:US16814529
申请日:2020-03-10
Applicant: UNIVERSAL DISPLAY CORPORATION
Inventor: BIN Ma , Vadim Adamovich , Edward Barron , Jui-Yi Tsai , Mingjuan Su , Lech Michalski , Chuanjun Xia , Michael S. Weaver , Walter Yeager , Bert Alleyne
Abstract: A compound having a formula (LA)mIr(LB)3-m having a structure selected from is disclosed. In the structures of formula (LA)mIr(LB)3-m, m is 1 or 2, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and, R6 is selected from C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof.
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公开(公告)号:US10672996B2
公开(公告)日:2020-06-02
申请号:US15239961
申请日:2016-08-18
Applicant: Universal Display Corporation
Inventor: Bin Ma , Vadim Adamovich , Edward Barron , Jui-Yi Tsai , Mingjuan Su , Lech Michalski , Chuanjun Xia , Michael S. Weaver , Walter Yeager , Bert Alleyne
Abstract: The present invention relates to organometallic complexes for use as emitters where a molecule of the compound has an orientation factor greater than 0.67, and devices, such as organic light emitting diodes, including the same.
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公开(公告)号:US10411200B2
公开(公告)日:2019-09-10
申请号:US14796213
申请日:2015-07-10
Applicant: Universal Display Corporation
Inventor: Bin Ma , Walter Yeager , Edward Barron , Alan Deangelis , Chuanjun Xia , Vadim Adamovich , Scott Beers , Harvey Wendt , Suman Layek
Abstract: A compound having the formula Ir(LA)n(LB)3-n is disclosed wherein LA is an aza-DBF ligand and LB is an alkyl-substituted phenylpyridine ligand, wherein the compound has a structure according to Formula I: wherein A1, A2, A3, A4, A5, A6, A7, and A8 comprise carbon or nitrogen; wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is nitrogen; wherein ring B is bonded to ring A through a C—C bond; wherein the iridium is bonded to ring A through a Ir—C bond; wherein X is O, S, or Se; wherein R1 and R2 each independently represent mono-, di-, tri-, tetra-substitution, or no substitution; wherein R′ and R″ each independently represent mono-, di-substitution, or no substitution; wherein any adjacent substitutions in R′, R″, R1, R2, R3, R4, R5, and R6 are optionally linked together to form a ring; wherein R1, R2, R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein R3, R4, R5, and R6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof; wherein n is an integer from 1 to 3; and wherein total number of carbons in at least one of the pairs R3 and R4, and R5 and R6 is at least four.
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公开(公告)号:US20180287076A1
公开(公告)日:2018-10-04
申请号:US15918179
申请日:2018-03-12
Applicant: Universal Display Corporation
Inventor: Jui-Yi Tsai , Lichang Zeng , Zhiqiang Ji , Alexey Borisovich Dyatkin , Walter Yeager , Edward Barron
Abstract: A compound having the formula: Formula I is disclosed. The compound is useful as emitters in OLEDs.
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公开(公告)号:US09773985B2
公开(公告)日:2017-09-26
申请号:US13798839
申请日:2013-03-13
Applicant: Universal Display Corporation
Inventor: Lichang Zeng , Edward Barron , Bin Ma , Chuanjun Xia
CPC classification number: H01L51/0085 , C07F15/0033 , C09K11/06 , C09K2211/1029 , C09K2211/1044 , C09K2211/185 , H01L51/5016 , H01L2251/308
Abstract: A compound according to Formula I, as well as, devices and formulations containing the compound as described. The compound has the general formula wherein n=1 or 2; wherein X1-X2 is a bidentate ligand having the formula: wherein each of R1, R2, R3, R4 and R5 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein each of R3, R4 and R5 can also be selected from two adjacent substituents joined to form into a ring; wherein each of Z1, Z2, Z3, Z4, Z6, Z7, Z8 is independently selected from C, CH or N; wherein ring A is connected to ring B through N—C bond; and wherein Y1-Y2 is a different bidentate ligand other than X1-X2.
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