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US 11,958,825 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorPeter Wolohan
Life of this patent
Estimating the term…
Abstract
The present invention includes novel compounds containing deuterated or partially deuterated xanthene and thioxanthene structures. These compounds may be useful as host materials with high triplet energies for phosphorescent electroluminescent devices.
Claims18
A compound of Formula I:
- wherein
- D is selected from the group consisting of CRd1Rd2, SiRd1Rd2 and GeRd1Rd2;
- wherein Rd1 and Rd2 are independently selected from the group consisting of deuterium, partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, partially or fully deuterated heteroalkyl, partially or fully deuterated aryl, partially or fully deuterated heteroaryl, and partially or fully deuterated silyl;
- or Rd1 and Rd2 together form a cycloalkyl or heteroalkyl ring, each of which is optionally substituted and/or includes a carbon-carbon double bond;
- E is selected from a direct bond, O, S, or Se;
- A1, A2, A3, A4, A5, A6, A7, and A8 are independently selected from CRA or N;
- wherein no more than two of A1, A2, A3, and A4, or no more than two of A5, A6, A7, and A8, are N, and no two N are adjacent to one another;
- wherein RA for each CRA is independently hydrogen, or is independently selected from the group consisting of deuterium, halide, alkyl, deuteroalkyl, cycloalkyl, deuterocycloalkyl, heteroalkyl, deuteroheteroalkyl, deuteroarylalkyl, alkoxy, aryloxy, silyl, deuterosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, pyridine, pyrimidine, pyrazine, tetraphenylene, azatetraphenylene, tetraphenylenecarbonitrile, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one RA comprises a group selected from the group consisting of
- wherein X1-to X30 are each independently selected from the group consisting of N and CR;
- wherein each respective aromatic ring has more than two N, and no two N are adjacent to one another;
- Y is selected from the group consisting of C and Si;
- Z1 and Z2 are each independently selected from the group consisting of NR, N, O, S, and Se;
- L1, L2, L3, and L4 are each independently selected from the group consisting of BR, O, SiR2, and CR2;
- and
- each R is independently hydrogen, or is selected from the group consisting of deuterium, halide, alkyl, deuteroalkyl, cycloalkyl, deuterocycloalkyl, heteroalkyl, deuteroheteroalkyl, deuteroarylalkyl, alkoxy, aryloxy, silyl, deuterosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, pyridine, pyrimidine, pyrazine, tetraphenylene, azatetraphenylene, tetraphenylenecarbonitrile, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
13 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound of
- wherein
- D is selected from the group consisting of CRd1Rd2, SiRd1Rd2 and GeRd1Rd2;
- wherein Rd1 and Rd2 are independently selected from the group consisting of deuterium, partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, partially or fully deuterated heteroalkyl, partially or fully deuterated aryl, partially or fully deuterated heteroaryl, and partially or fully deuterated silyl;
- or Rd1 and Rd2 together form a cycloalkyl or heteroalkyl ring, each of which is optionally substituted and/or includes a carbon-carbon double bond;
- E is selected from a direct bond, O, S, or Se;
- A1, A2, A3, A4, A5, A6, A7, and A8 are independently selected from CRA or N;
- wherein no more than two of A1, A2, A3, and A4, or no more than two of A5, A6, A7, and A8, are N, and no two N are adjacent to one another;
- wherein RA for each CRA is independently hydrogen, or is independently selected from the group consisting of deuterium, halide, alkyl, deuteroalkyl, cycloalkyl, deuterocycloalkyl, heteroalkyl, deuteroheteroalkyl, deuteroarylalkyl, alkoxy, aryloxy, silyl, deuterosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, pyridine, pyrimidine, pyrazine, tetraphenylene, azatetraphenylene, tetraphenylenecarbonitrile, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one RA comprises a group selected from the group consisting of:
- wherein X1-to X30 are each independently selected from the group consisting of N and CR;
- wherein each respective aromatic ring has more than two N, and no two N are adjacent to one another;
- Y is selected from the group consisting of C and Si;
- Z1 and Z2 are each independently selected from the group consisting of NR, N, O, S, and Se;
- L1, L2, L3, and L4 are each independently selected from the group consisting of BR, O, SiR2, and CR2;
- and
- each R is independently hydrogen, or is selected from the group consisting of deuterium, halide, alkyl, deuteroalkyl, cycloalkyl, deuterocycloalkyl, heteroalkyl, deuteroheteroalkyl, deuteroarylalkyl, alkoxy, aryloxy, silyl, deuterosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, pyridine, pyrimidine, pyrazine, tetraphenylene, azatetraphenylene, tetraphenylenecarbonitrile, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
17 more elements
A consumer product comprising an organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound of Formula I:
- wherein
- D is selected from the group consisting of CRd1Rd2, SiRd1Rd2 and GeRd1Rd2;
- wherein Rd1 and Rd2 are independently selected from the group consisting of deuterium, partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, partially or fully deuterated heteroalkyl, partially or fully deuterated aryl, partially or fully deuterated heteroaryl, and partially or fully deuterated silyl;
- or Rd1 and Rd2 together form a cycloalkyl or heteroalkyl ring, each of which is optionally substituted and/or includes a carbon-carbon double bond;
- E is selected from a direct bond, O, S, or Se;
- A1, A2, A3, A4, A5, A6, A7, and A8 are independently selected from CRA or N;
- wherein no more than two of A1, A2, A3, and A4, or no more than two of A5, A6, A7, and A8, are N, and no two N are adjacent to one another;
- wherein RA for each CRA is independently hydrogen, or is independently selected from the group consisting of deuterium, halide, alkyl, deuteroalkyl, cycloalkyl, deuterocycloalkyl, heteroalkyl, deuteroheteroalkyl, deuteroarylalkyl, alkoxy, aryloxy, silyl, deuterosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, pyridine, pyrimidine, pyrazine, tetraphenylene, azatetraphenylene, tetraphenylenecarbonitrile, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- wherein at least one RA comprises a group selected from the group consisting of:
- wherein X1-to X30 are each independently selected from the group consisting of N and CR;
- wherein each respective aromatic ring has more than two N, and no two N are adjacent to one another;
- Y is selected from the group consisting of C and Si;
- Z1 and Z2 are each independently selected from the group consisting of NR, N, O, S, and Se;
- L1, L2, L3, and L4 are each independently selected from the group consisting of BR, O, SiR2, and CR2;
- and
- each R is independently hydrogen, or is selected from the group consisting of deuterium, halide, alkyl, deuteroalkyl, cycloalkyl, deuterocycloalkyl, heteroalkyl, deuteroheteroalkyl, deuteroarylalkyl, alkoxy, aryloxy, silyl, deuterosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, pyridine, pyrimidine, pyrazine, tetraphenylene, azatetraphenylene, tetraphenylenecarbonitrile, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
17 more elements
Dependencies are inferred from the claim text.