Organic electroluminescent materials and devices

1. A compound having the Formula (I):

wherein one of the E 1 and E 2 is N, and one of the E 1 and E 2 is B;

wherein E 3 and E 4 is carbon;

wherein ring Y and ring Z are 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring fused to ring X;

wherein ring Y is selected from the group consisting of:

wherein E 5 is selected from the group consisting of NR, O, S, and Se; and

wherein R is selected from the group consisting of 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 2 and R 3 represent mono, di, tri, tetra substitutions or no substitution;

wherein R 2 and R 3 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 R 1 is selected from the group consisting of 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 two adjacent R 2 , and R 3 are optionally joined to form a ring, which may be further substituted.

2. The compound of claim 1 , wherein E 1 is B, and E 2 is N.

3. The compound of claim 1 , wherein E 1 is N, and E 2 is B.

4. The compound of claim 1 , wherein ring Y is

5. The compound of claim 1 , wherein ring Z is selected from the group consisting of:

wherein E 5 is selected from the group consisting of NR, O, S, and Se; and

wherein R is selected from the group consisting of 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.

6. The compound of claim 1 , wherein ring Z is

7. The compound of claim 1 , wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of phenyl, pyridine, triazine, pyrimidine, phenanthrene, naphthalene, anthracene, triphenylene, pyrene, chrysene, fluoranthene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene, each of which may be further substituted.

8. The compound of claim 1 , wherein the compound has the formula

9. The compound of claim 1 , wherein the compound is a compound having Formula (II):

wherein R 21 and R 22 are independently are aryl or heteroaryl, each of which may be further substituted;

R 23 and R 24 are independently aryl or heteroaryl, each of which may be further substituted; and

G is arylene, heteroarylene, or combinations thereof.

10. The compound of claim 9 , wherein G is phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

11. The compound of claim 10 , which is

12. The compound of claim 1 , wherein the compound is a compound having Formula (III):

wherein R 31 and R 32 independently are aryl or heteroaryl, which may be further substituted;

wherein G 1 , G 2 , and G 3 independently are arylene or heteroarylene.

13. The compound of claim 12 , wherein G 1 , G 2 , and G 3 independently are phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

14. The compound of claim 13 , which is:

15. The compound of claim 1 , wherein, the compound is a compound having Formula (IV):

wherein G 4 is arylene or heteroarylene.

16. The compound of claim 15 , wherein G 4 is phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

17. The compound of claim 16 , which is:

18. The compound of claim 1 , wherein the compound is a compound of Formula (V)

wherein R 51 is aryl or heteroaryl.

19. The compound of claim 18 , wherein R 51 is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

20. The compound of claim 18 , which is:

21. The compound of claim 1 , wherein the compound is a compound of Formula (VI)

wherein R 61 and R 62 independently are aryl or heteroaryl.

22. The compound of claim 21 , wherein:

R 61 is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof; and

R 62 is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

23. The compound of claim 22 , which is:

24. The compound of claim 1 , wherein the compound is a compound of Formula (VII)

wherein R 71 and R 72 independently are aryl or heteroaryl.

25. The compound of claim 24 , wherein:

R 71 is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof; and

R 72 is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

26. The compound of claim 25 , which is:

27. The compound of claim 1 , where the compound is a compound having Formula (VIII):

wherein G 5 is arylene or heteroarylene; and

R 81 and R 82 are independently aryl or heteroaryl, each of which is substituted with at least one acyclic or cyclic aliphatic substituent.

28. The compound of claim 27 , wherein G 5 is phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

29. The compound of claim 27 , which is:

30. A first device comprising a first organic light emitting device, which further comprises:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode comprising a compound having the Formula (I):

wherein one of the E 1 and E 2 is N, and one of the E 1 and E 2 is B;

wherein E 3 and E 4 is carbon;

wherein ring Y and ring Z are 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring fused to ring X;

wherein ring Y is selected from the group consisting of:

wherein E 5 is selected from the group consisting of NR, O, S, and Se; and

wherein R is selected from the group consisting of 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 2 and R 3 represent mono, di, tri, tetra substitutions or no substitution;

wherein R 2 and R 3 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 R 1 is selected from the group consisting of 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 two adjacent R 2 , and R 3 are optionally joined to form a ring, which may be further substituted.

31. The first device of claim 30 , wherein the first device is a consumer product.

32. The first device of claim 30 , wherein the first device is an organic light-emitting device.

33. The first device of claim 30 , wherein the first device comprises a lighting panel.

34. The first device of claim 30 , wherein the organic layer is an emissive layer and the compound of Formula (I) is an emissive dopant.

35. The first device of claim 34 , where the device is a delayed fluorescence device.

36. The first device of claim 30 , wherein the organic layer is an emissive layer and the compound of Formula (I) is a host.

37. The first device of claim 36 , wherein the emissive layer further comprises a fluorescent emissive dopant.

38. The first device of claim 36 , wherein the emissive layer further comprises an emissive dopant, which is a transition metal complex having at least one ligand or part of the ligand, if the ligand is more than bidentate, selected from the group consisting of:

wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution; and

wherein R a , R b , R c , and R d 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 , R c , and R d are optionally joined to form a fused ring or form a multidentate ligand.

39. The first device of claim 30 , wherein the organic layer is a hole injecting layer or a hole transporting layer.

40. The first device of claim 30 , wherein the organic layer is an electron injecting layer or an electron transporting layer.

41. The first device of claim 30 , wherein the organic layer is an exciton blocking layer or a charge blocking layer.