Organic electroluminescent materials and devices
A composition of materials including a first compound having a structure according to Formula I
1. A composition of materials comprising a first compound, wherein the first compound has a formula:
wherein G 1 is selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and fluorene;
wherein L 1 is selected from the group consisting of phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein L 2 and L 3 are each independently selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein G 4 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, and combinations thereof;
wherein G 2 , G 3 , and G 5 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof;
wherein G 2 , G 3 , G 4 , and G 5 are each optionally further substituted with one or more unfused substituents selected from the group consisting of deuterium, alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, halogen, nitro, nitrile, silyl, phenyl, biphenyl, terphenyl, pyridine, and combinations thereof;
wherein m is an integer from 1 to 7,
wherein n is an integer from 1 to 4; and
wherein, when m or n is larger than 1, each G 4 or G 5 can be same or different.
2. The composition of claim 1 , wherein G 4 has the structure selected from the group consisting of:
3. The composition of claim 1 , wherein G 1 has the structure selected from the group consisting of:
wherein X is selected from a group consisting of O, S and Se;
wherein R B1 and R B2 are independently selected from a group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxyl, aryl, heteraryl, halogen, and combinations thereof; and
wherein R B1 and R B2 are optionally joined to form a ring.
4. The composition of claim 1 , wherein L 1 is selected from the group consisting of:
5. The composition of claim 1 , wherein G 2 , G 3 and G 5 are independently selected from the group consisting of:
wherein R B1 and R B2 are independently selected from a group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxyl, aryl, heteraryl, halogen, and combinations thereof; and
wherein R B1 and R B2 are optionally joined to form a ring.
6. The composition of claim 1 , wherein at least one of G 2 , G 3 , G 4 and G 5 is substituted with at least one fluorine atom.
7. The composition of claim 1 , wherein the first compound has the formula:
wherein X is selected from a group consisting of O, S and Se.
8. The composition of claim 1 , wherein the first compound is selected from the group consisting of:
Compound A10 through A12, each represented
by the formula
wherein in Compound A10: X = O,
in Compound A11: X = S,
in Compound A12: X = Se
Compound A13 through A15, each represented
by the formula
wherein in Compound A13: X = O,
in Compound A14: X = S,
in Compound A15: X = Se
Compound A16 through A18, each represented
by the formula
wherein in Compound A16: X = O,
in Compound A17: X = S,
in Compound A18: X = Se
Compound A19 through A21, each represented
by the formula
wherein in Compound A19: X = O,
in Compound A20: X = S,
in Compound A21: X = Se
Compound A22 through A24, each represented
by the formula
wherein in Compound A22: X = O,
in Compound A23: X = S,
in Compound A24: X = Se
Compound A25 through A27, each represented
by the formula
wherein in Compound A25: X = O,
in Compound A26: X = S,
in Compound A27: X = Se
Compound A40 through A42, each represented
by the formula
wherein in Compound A40: X = O,
in Compound A41: X = S,
in Compound A42: X = Se
Compound A43 through A45, each represented
by the formula
wherein in Compound A43: X = O,
in Compound A44: X = S,
in Compound A45: X = Se
Compound A46 through A48, each represented
by the formula
wherein in Compound A46: X = O,
in Compound A47: X = S,
in Compound A48: X = Se
Compound A58 through A60, each represented
by the formula
wherein in Compound A58: X = O,
in Compound A59: X = S,
in Compound A60: X = Se
Compound A61 through A63, each represented
by the formula
wherein in Compound A61: X = O,
in Compound A62: X = S,
in Compound A63: X = Se
Compound A64 through A66, each represented
by the formula
wherein in Compound A64: X = O,
in Compound A65: X = S,
in Compound A66: X = Se
Compound A91 through A93, each represented
by the formula
wherein in Compound A91: X = O,
in Compound A92: X = S,
in Compound A93: X = Se
Compound A94 through A96, each represented
by the formula
wherein in Compound A94: X = O,
in Compound A95: X = S,
in Compound A96: X = Se
Compound A97 through A99, each represented
by the formula
wherein in Compound A97: X = O,
in Compound A98: X = S,
in Compound A99: X = Se
Compound A100 through A102, each represented
by the formula
wherein in Compound A100: X = O,
in Compound A101: X = S,
in Compound A102: X = Se
Compound A103 through A105, each represented
by the formula
wherein in Compound A103: X = O,
in Compound A104: X = S,
in Compound A105: X = Se
and
Compound A106 through A108, each represented
by the formula
wherein in Compound A106: X = O,
in Compound A107: X = S,
in Compound A108: X = Se
9. The composition of claim 1 , wherein the composition comprises a second compound;
wherein the second compound has the formula II:
wherein Ar 1 is selected from the group consisting of triphenylene, and aza-triphenylene;
wherein Ar 2 is selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, naphthalene, pyridine, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, and combinations thereof;
wherein Ar 3 is selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, pyridine, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, carbazole, aza-carbazole, and combinations thereof; and
wherein Ar 1 , Ar 2 and Ar 3 are each, independently, optionally further substituted with one or more substitutions selected from the group consisting of deuterium, halogen, alkyl, aryl, heteroaryl, and combinations thereof.
10. The composition of claim 9 , wherein the second compound is selected from the group consisting of
wherein X is selected from the group consisting of O, S and Se;
wherein R 1 and R 4 each independently represents mono, di, or tri, substitution, or no substitution;
wherein R 2 , R 3 , R 5 , and R 6 each independently represents mono, di, tri, or tetra substitution, or no substitution; and
wherein R 1 to R 6 are each independently selected from the group consisting of hydrogen, deuterium, benzene, biphenyl, terphenyl, naphthalene, fluorene, triphenylene, phenanthrene, dibenzofuran, dibenzothiophene, carbazole and combinations thereof.
11. The composition of claim 9 , wherein the second compound is selected from the group consisting of
Compound E1 through E3, each represented
by the formula
wherein in Compound E1: X = O,
in Compound E2: X = S,
in Compound E3: X = Se
Compound E4 through E6, each represented
by the formula
wherein in Compound E4: X = O,
in Compound E5: X = S,
in Compound E6: X = Se
Compound E7 through E9, each represented
by the formula
wherein in Compound E7: X = O,
in Compound E8: X = S,
in Compound E9: X = Se
Compound E10 through E12, each represented
by the formula
wherein in Compound E10: X = O,
in Compound E11: X = S,
in Compound E12: X = Se
Compound E13 through E15, each represented
by the formula
wherein in Compound E13: X = O,
in Compound E14: X = S,
in Compound E15: X = Se
Compound E16 through E18, each represented
by the formula
wherein in Compound E16: X = O,
in Compound E17: X = S,
in Compound E18: X = Se
Compound E19 through E21, each represented
by the formula
wherein in Compound E19: X = O,
in Compound E20: X = S,
in Compound E21: X = Se
Compound E22 through E24, each represented
by the formula
wherein in Compound E22: X = O,
in Compound E23: X = S,
in Compound E24: X = Se
Compound E25 through E27, each represented
by the formula
wherein in Compound E25: X = O,
in Compound E26: X = S,
in Compound E27: X = Se
Compound E28
Compound E29
Compound E30
12. The composition of claim 1 , wherein the composition comprises a second compound; wherein the second compound is a phosphorescent emissive Ir complex having at least one substituent selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.
13. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising A composition of materials comprising a first compound, wherein the first compound has a formula:
wherein G 1 is selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and fluorene;
wherein L 1 is selected from the group consisting of phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein L 2 and L 3 are each independently selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
wherein G 4 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, and combinations thereof;
wherein G 2 , G 3 , and G 5 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof;
wherein G 2 , G 3 , G 4 , and G 5 are each optionally further substituted with one or more unfused substituents selected from the group consisting of deuterium, alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, halogen, nitro, nitrile, silyl, phenyl, biphenyl, terphenyl, pyridine, and combinations thereof;
wherein m is an integer from 1 to 7,
wherein n is an integer from 1 to 4; and
wherein, when m or n is larger than 1, each G 4 or G 5 can be same or different.
14. The first device of claim 13 , wherein the organic layer is an emissive layer and the composition is a host.
15. The first device of claim 13 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the phosphorescent emissive dopant 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 each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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 two adjacent substitutents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.
16. The first device of claim 15 , wherein at least one of R a , R b , R c , and R d is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.
17. The first device of claim 13 , wherein the organic layer is a blocking layer and the composition is a blocking material in the organic layer, or the organic layer is an electron transporting layer and the composition is an electron transporting material in the organic layer.
18. The first device of claim 13 , wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.