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US 11,696,492 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsHsiao-Fan Chen, Daniel W. Silverstein, Peter Wolohan, Tyler Fleetham, Jason Brooks, Charles J. Stanton, III, Olexandr Tretyak, Raghupathi Neelarapu, Katarina Rohlfing, Douglas Williams
Life of this patent
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Abstract
A novel compound having a benzimidazole based structure is disclosed that is selected from one of the following structures: The compound is useful in improving photophysical performance of OLEDs.
Claims20
A compound selected from the group consisting of:
- wherein,
- A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
- ring B may or may not be present;
- M is selected from the group consisting of Pt, Pd, Cu, and Au;
- Z1, Z2, Z3, Z4, Z5, Z6, Z6′, Z7 and Z7′ are each independently selected from the group consisting of C and N;
- wherein one of Z6′ and Z7′ is a neutral carbene carbon, and the other one of Z6′ and Z7′ is an anionic carbon;
- m1, m2 and m3 are each independently an integer of 0 or 1;
- when m2 is 0, each m1 and m3 is 1:
- when m2 is 1, each m1 and m3 can be 0 or 1;
- when m1 is 0, L1 is not present;
- when m2 is 0, L2 is not present;
- when m3 is 0, L3 is not present;
- L1, L2, and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
- each RA, RB, RC, RD, and RE represents mono- to maximum possible number of substitutions, or no substitution;
- each RA, RB, RC, RD, RE, R and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof,
- R1 is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and
- any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L2 is present and is a direct bond, then at least one pair of RD, one pair of RE, or one RD and one RE are joined together to form a fused ring.
14 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 selected from the group consisting of:
- wherein,
- A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
- ring B may or may not be present;
- M is selected from the group consisting of Pt, Pd, Cu, and Au;
- Z1, Z2, Z3, Z4, Z5, Z6, Z6′, Z7 and Z7′ are each independently selected from the group consisting of C and N;
- wherein one of Z6′ and Z7′ is a neutral carbene carbon, and the other one of Z6′ and Z7′ is an anionic carbon;
- m1, m2 and m3 are each independently an integer of 0 or 1;
- when m2 is 0, each m1 and m3 is 1;
- when m2 is 1, each m1 and m3 can be 0 or 1;
- when m1 is 0, L1 is not present;
- when m2 is 0, L2 is not present;
- when m3 is 0, L3 is not present;
- L1, L2, and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
- each RA, RB, RC, RD, and RE represents mono- to maximum possible number of substitutions, or no substitution;
- each RA, RB, RC, RD, RE, R and R′ is a hydrogen or a substituent independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
- R1 is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L2 is present and is a direct bond, then at least one pair of RD, one pair of RE, or one RD and one RE are joined together to form a fused ring.
19 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 selected from the group consisting of:
- wherein,
- A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
- ring B may or may not be present;
- M is selected from the group consisting of Pt, Pd, Cu, and Au;
- Z1, Z2, Z3, Z4, Z5, Z6, Z6′, Z7 and Z7′ are each independently selected from the group consisting of C and N;
- wherein one of Z6′ and Z7′ is a neutral carbene carbon, and the other one of Z6′ and Z7′ is an anionic carbon;
- m1, m2 and m3 are each independently an integer of 0 or 1;
- when m2 is 0, each m1 and m3 is 1;
- when m2 is 1, each m1 and m3 can be 0 or 1;
- when m1 is 0, L1 is not present;
- when m2 is 0, L2 is not present;
- when m3 is 0, L3 is not present;
- L1, L2, and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
- each RA, RB, RC, RD, and RE represents mono- to maximum possible number of substitutions, or no substitution;
- each RA, RB, RC, RD, RE, R and R′ is a hydrogen or a substituent independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
- R1 is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L2 is present and is a direct bond, then at least one pair of RD, one pair of RE, or one RD and one RE are joined together to form a fused ring.
19 more elements
Dependencies are inferred from the claim text.