Organic electroluminescent materials and devices
Novel phosphorescent tetradentate platinum (II) compounds comprising a twisted aryl group are provided. Also provided are novel phosphorescent tetradentate platinum (II) compounds comprising an imidazo[1,2-f]phenanthridine moiety. The compounds may be used in organic light emitting devices to provide improved device efficiency, line shape and lifetime.
1. A compound having the formula:
wherein A and B are independently selected from the group consisting of a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein A-B connects to Pt through one covalent bond and one coordination bond;
wherein A and B can be substituted and the substituents can be to form polycyclic rings;
wherein X and Y are independently selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R and R′ are 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 R 3 may represent mono, di, or tri substitutions;
wherein R 1 may represent a mono substitution:
wherein R 1 , R 2 , and R 3 are 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 two adjacent substituents of R 1 , R 2 , and R 3 are optionally joined to form a fused ring;
wherein at least one of R 1 and R 2 is:
wherein R′ 1 and R′ 2 are independently selected from the group consisting of alkyl and aryl hydrogen, and deuterium, wherein at least one of R′ 1 and R′ 2 is not hydrogen or deuterium; and
wherein C is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted.
2. The compound of claim 1 , wherein at least one of R′ 1 and R′ 2 is an alkyl and the other of R′ 1 and R′ 2 is hydrogen or deuterium.
3. The compound of claim 1 , wherein each of R′ 1 and R′ 2 is an alkyl.
4. The compound of claim 1 , wherein each of R′ 1 and R′ 2 is an aryl.
5. The compound of claim 1 , wherein C is benzene.
6. The compound of claim 1 , wherein A-B is selected from the group consisting of:
wherein R a and R b may represent mono, di, tri or tetra substitutions;
wherein R c may represent mono, di, or tri substitutions;
wherein R a , R b , and R c are 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; and
wherein two adjacent substituents of R a , R b , and R c are optionally joined to form a fused ring.
7. The compound of claim 1 , wherein the compound is selected from the group consisting of:
8. A first device comprising an organic light emitting device, the organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of the Formula IV,
wherein A and B are independently selected from the group consisting of a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein A-B connects to Pt through one covalent bond and one coordination bond;
wherein A and B can be substituted and the substituents can be combined to form polycyclic rings;
wherein X and Y are independently selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R and R′ are 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 R 3 may represent mono, di, or tri substitutions;
wherein R 1 may represent a mono substitution:
wherein R 1 , R 2 , and R 3 are 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 two adjacent substituents of R 1 , R 2 , and R 3 are optionally joined to form a fused ring;
wherein at least one of R 1 and R 2 is:
wherein R′ 1 and R′ 2 are independently selected from the group consisting of alkyl, aryl, hydrogen, and deuterium, wherein at least one of R′ 1 and R′ 2 is not hydrogen or deuterium; and
wherein C is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted.
9. The first device of claim 8 , wherein the first device is a consumer product.
10. A compound having the formula:
wherein ring A is a 6-membered carbocyclic or heterocyclic ring and ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein L 1 and L 2 are independently selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein Z 1 and Z 2 are independently a nitrogen atom or a carbon atom;
wherein R 1 and R 5 may represent a mono or di substitutions;
wherein R 2 , R 3 , and R 4 may represent a mono, di, tri, or tetra substitutions;
wherein R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are 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; and
wherein two adjacent substituents R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are optionally joined to form a fused ring.
11. The compound of claim 10 , wherein the compound has the formula:
12. The compound of claim 10 , wherein the compound has the formula:
wherein R 6 may represent mono, di, tri, or tetra substitutions; and
wherein R 6 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.
13. The compound of claim 10 , wherein the compound has the formula:
wherein R 6 may represent mono, di, tri, or tetra substitutions; and
wherein R 6 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.
14. The compound of claim 10 , wherein the compound has the formula:
wherein R 6 may represent mono, di, tri, or tetra substitutions; and
wherein R 6 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.
15. The compound of claim 10 , wherein the compound has the formula:
16. The compound of claim 10 , wherein the compound has the formula:
17. The compound of claim 10 , wherein the compound is selected from the group consisting of:
18. A first device comprising an organic light emitting device, the organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:
wherein ring A is a 6-membered carbocyclic or heterocyclic ring and ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein L 1 and L 2 are independently selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein Z 1 and Z 2 are independently a nitrogen atom or a carbon atom;
wherein R 1 and R 5 may represent a mono or di substitutions;
wherein R 2 , R 3 , and R 4 may represent a mono, di, tri, or tetra substitutions;
wherein R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are 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; and
wherein two adjacent substituents R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are optionally joined to form a fused ring.
19. The first device of claim 18 , wherein the compound is selected from the group consisting of:
20. The first device of claim 18 , wherein the first device is a consumer product.