Organic electroluminescent materials and devices
A compound having a Pt tetradentate structure selected from the group consisting of is provided. In the structures of Formula 1 and Formula 2, rings C and D each independently represent 5- or 6-membered carbocyclic or heterocyclic ring; L 1 , L 2 , and L 3 are each independently a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , SiRR′, GeRR′, alkyl, cycloalkyl, or a combination thereof; the sum of n1 and n2 is 1 or 2; X is selected from NR E , O, S, and Se; X 3 and X 4 each independently carbon or nitrogen; and one of Q 1 , Q 3 , and Q 4 is oxygen, and the remaining two of Q 1 , Q 3 , and Q 4 each represents a direct bond. Formulations and devices, such as an OLEDs, that include the compound of Formulas 1 and 2 are also described.
1. A compound having a Pt tetradentate structure, having the formula selected from the group consisting of:
wherein rings C and D each independently represents aryl or heteroaryl;
wherein R A , R B1 , R C , and R D each independently represents mono, di, tri, tetra-substitution, or no substitution;
wherein R B2 represents mono, di-substitution, or no substitution;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
wherein n1 and n2 are each independently an integer of 1 or 0; the sum of n1 and n2 is at least 1; when n1 is 0, L 1 is not present; and when n2 is 0, L 2 is not present;
wherein X is selected from the group consisting of NR E , O, S, and Se;
wherein R A , R B1 , R B2 , R C , R D , R E , 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 any adjacent R A , R B , R C , R D , R E , R, and R′ are optionally joined to form a ring;
wherein X 3 and X 4 each independently selected from the group consisting of carbon and nitrogen; and
wherein one of Q 1 , Q 3 , and Q 4 is oxygen, and the remaining two of Q 1 , Q 3 , and Q 4 each represents a direct bond.
2. The compound of claim 1 , wherein Q 1 is oxygen, and Q 3 and Q 4 each represents a direct bond.
3. The compound of claim 1 , wherein n1 is 1, and n2 is 0.
4. The compound of claim 1 , wherein n1 is 0, and n2 is 1.
5. The compound of claim 1 , wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, NR, O, SiRR′, alkyl, cycloalkyl, and combinations thereof.
6. The compound of claim 1 , wherein L 1 , L 2 , and L 3 each independently represents a direct bond.
7. The compound of claim 1 , wherein at least one of L 1 , L 2 , and L 3 is SiRR′ or GeRR′, and R and R′ are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.
8. The compound of claim 1 , wherein the compound has at least one Pt-carbene bond.
9. The compound of claim 1 , wherein the rings of C and D are each independently selected from the group consisting of phenyl, pyridine, benzimidazole, and imidazole.
10. The compound of claim 1 , wherein X is NR E .
11. The compound of claim 1 , wherein the compound is selected from the group consisting of
wherein Y is selected from the group consisting of CR 1 R 2 , SiR 1 R 2 , NR 1 , O, S, and Se;
wherein R 1 , and R 2 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 each X is selected from the group consisting of NR E , O, S, and Se; and
wherein any adjacent R 1 , and R 2 are optionally joined to form a ring.
12. The compound of claim 1 , wherein the compound is selected from the group consisting of
wherein Y is selected from the group consisting of CR 1 R 2 , SiR 1 R 2 , NR 1 , O, S, and Se;
wherein R 1 , and R 2 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; and
wherein any adjacent R 1 , and R 2 are optionally joined to form a ring.
13. The compound of claim 1 , wherein the compound is selected from the group consisting of:
14. A first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a Pt tetradentate structure, having the formula selected from the group consisting of:
wherein rings C and D each independently represents aryl or heteroaryl;
wherein R A , R B1 , R C , and R D each independently represent mono, di, tri, tetra-substitution, or no substitution;
wherein R B2 represents mono, di-substitution, or no substitution;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
wherein n1 and n2 are each independently an integer of 1 or 0; the sum of n1 and n2 is at least 1; when n1 is 0, L 1 is not present; and when n2 is 0, L 2 is not present;
wherein X is selected from the group consisting of NR E , O, S, and Se;
wherein R A , R B1 , R B2 , R C , R D , R E , 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 any adjacent R A , R B , R C , R D , R E , R, and R′ are optionally joined to form a ring;
wherein X 3 and X 4 each independently selected from the group consisting of carbon and nitrogen; and
wherein one of Q 1 , Q 3 , and Q 4 is oxygen, the remaining two of Q 1 , Q 3 , and Q 4 each represents a direct bond.
15. The first organic light emitting device of claim 14 , wherein the first organic light emitting device is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.
16. The first organic light emitting device of claim 14 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
17. The first organic light emitting device of claim 14 , wherein the organic layer further comprises a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , and C n H 2n -Ar 1 ;
wherein n is from 1 to 10; and
wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
18. The first organic light emitting device of claim 14 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
19. The first organic light emitting device of claim 14 , wherein the organic layer further comprises a host and the host is selected from the group consisting of:
and combinations thereof.
20. A formulation comprising a compound having a Pt tetradentate structure, having the formula selected from the group consisting of:
wherein rings C, and D each independently represent aryl or heteroaryl;
wherein R A , R B1 , R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein R B2 represents mono, or di-substitution, or no substitution;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
wherein n1 and n2 are each independently an integer of 1 or 0; the sum of n1 and n2 is at least 1; when n1 is 0, L 1 is not present; and when n2 is 0, L 2 is not present;
wherein X is selected from the group consisting of NR E , O, S, and Se;
wherein R A , R B1 , R B2 , R C , R D , R E , 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 any adjacent R A , R B ,R C , R D , R E , R, and R′ are optionally joined to form a ring;
wherein X 3 and X 4 each independently selected from the group consisting of carbon and nitrogen; and
wherein one of Q 1 , Q 3 and Q 4 is oxygen, the remaining two of Q 1 , Q 3 and Q 4 each represent a direct bond.