Back to results
US 12,600,739 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsWei-Chun Shih, Tyler Fleetham, Zhiqiang Ji, Pierre-Luc T. Boudreault
Life of this patent
Estimating the term…
Abstract
Provided are organometallic compounds of of Formula I: Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.
Claims21
A compound of Formula I:
- wherein:
- M is Pd or Pt;
- each of X1-X16 is independently C or N;
- each of Y1-Y4 is independently CR or N, with at least one of them being CR;
- each of RA, RB, RC, and RD represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
- each of R, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of RA, RB, RC, and RD comprising an electron-withdrawing group;
- any two adjacent R, RA, RB, RC, and RD can be joined or fused to form a ring;
- and
- wherein at least one of the following is true:
- i) the at least one of RA, RB, RC, and RD that comprises the electron-withdrawing group is selected from the group consisting of CHF2, CF2CF3, CF(CF3)2, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSO2CF3, OSeO2CF3, OCN, SCN, SeCN;
- ii) at least one of Y1-Y4 is N;
- or
- iii) each of Y1-Y4 is CR and each R is hydrogen, methyl, or unsubstituted phenyl.
10 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises a compound of Formula I:
- wherein:
- M is Pd or Pt;
- each of X1-X16 is independently C or N;
- each of Y1-Y4 is independently CR or N, with at least one of them being CR;
- each of RA, RB, RC, and RD represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
- each of R, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of RA, RB, RC, and RD comprising an electron-withdrawing group;
- any two adjacent R, RA, RB, RC, and RD can be joined or fused to form a ring;
- and
- wherein at least one of the following is true:
- i) the at least one of RA, RB, RC, and RD that comprises the electron-withdrawing group is selected from the group consisting of CHF2, CF2CF3, CF(CF3)2, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSO2CF3, OSeO2CF3, OCN, SCN, SeCN;
- ii) at least one of Y1-Y4 is N;
- or
- iii) each of Y1-Y4 is CR and each R is hydrogen, methyl, or unsubstituted phenyl.
15 more elements
A consumer product comprising an organic light-emitting device comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises a compound of Formula I:
- wherein:
- M is Pd or Pt;
- each of X1-X16 is independently C or N;
- each of Y1-Y4 is independently CR or N, with at least one of them being CR;
- each of RA, RB, RC, and RD represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
- each of R, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of RA, RB, RC, and RD comprising an electron-withdrawing group;
- any two adjacent R, RA, RB, RC, and RD can be joined or fused to form a ring;
- and
- wherein at least one of the following is true:
- i) the at least one of RA, RB, RC, and RD that comprises the electron-withdrawing group is selected from the group consisting of CHF2, CF2CF3, CF(CF3)2, COCH3, CHO, COCF3, COOMe, COOCF3, NO2, SF3, SiF3, PF4, SF5, OCF3, SCF3, SeCF3, SOCF3, SeOCF3, SO2F, SO2CF3, SeO2CF3, OSO2CF3, OSeO2CF3, OCN, SCN, SeCN;
- ii) at least one of Y1-Y4 is N;
- or
- iii) each of Y1-Y4 is CR and each R is hydrogen, methyl, or unsubstituted phenyl.
15 more elements
Dependencies are inferred from the claim text.