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US 10,707,423 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsLichang Zeng, Suman Layek, Walter Yeager, Kwang-Ohk Cheon, Chuanjun Xia
Life of this patent
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Abstract
The present invention relates to novel organic compounds containing oligocarbazoles. The compounds are useful for organic light-emitting diodes. The compounds are also useful for charge-transport and charge-blocking layers, and as hosts in the light-emissive layer for organic light emitting devices (OLEDs).
Claims19
A compound having formula I:
- wherein G1 has formula II:
- wherein G2 has formula III:
- wherein L is selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
- wherein G3 is selected from the group consisting of benzene, furan, thiophene, biphenyl, terphenyl, triphenylene, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, eindenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenocarbazole, benzofluorenothiophene, and benzothienodibenzothiophene;
- wherein R2, R4, R6, and R8 each independently represent mono, di, tri, or no substitution;
- wherein R1, R3, R5, and R7 each independently represent mono, di, tri, tetra, or no substitution;
- wherein R1, R2, R5, R6, R7, R8, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
- wherein R3, R4, and RA are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, triphenyl, and combinations thereof;
- wherein L is optionally further substituted by one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
- wherein G3 is optionally further substituted by one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, aryloxy, arylthio, arylseleno, heteroarylalkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
- wherein a is 0 or 1, and b is 0, 1, 2 or 3;
- wherein m is an integer from 1 to 10;
- wherein n is an integer from 0 to 9;
- wherein m is larger than n;
- and
- further wherein at least one of the following is true:
- (1) a=1 and L is selected from the group consisting of terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
- (2) b=1 and L is selected from the group consisting of phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof,
- (3) at least one of R1, R2, R3, R4, R5, R6 and, when present, R7, or R8 is at least monosubstituted with a substituent independently selected from the group consisting of deuterium, halide, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof,
- (4) L is selected from the group consisting of naphthalene and dibenzothiophene, and L is further substituted,
- (5) at least one G3 is further substituted,
- (6) RA, RB, or both are selected from the group consisting of deuterium, halide, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof,
- (7) a is 1 and b is 1,
- (8) a is 1, b is 0, and n is an integer from 1 to 9, and
- (9) b is 1, a is 0, and G3 is selected from the group consisting of furan, thiophene, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenocarbazole, benzofluorenothiophene, and benzothienodibenzothiophene.
22 more elements
A device comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound having formula I:
- wherein G1 has formula II:
- wherein G2 has formula III:
- wherein L is selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
- wherein G3 is selected from the group consisting of benzene, furan, thiophene, biphenyl, terphenyl, triphenylene, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenocarbazole, benzofluorenothiophene, and benzothienodibenzothiophene;
- wherein R2, R4, R6, and R8 each independently represent mono, di, tri, or no substitution;
- wherein R1, R3, R5, and R7 each independently represent mono, di, tri, tetra, or no substitution;
- wherein R1, R2, R5, R6, R7, R8, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
- wherein R3, R4, and RA are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, triphenyl, and combinations thereof;
- wherein L is optionally further substituted by one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
- wherein G3 is optionally further substituted by one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, aryloxy, arylthio, arylseleno, heteroarylalkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
- wherein a is 0 or 1, and b is 0, 1, 2 or 3;
- wherein m is an integer from 1 to 10;
- wherein n is an integer from 0 to 9;
- wherein m is larger than n;
- and
- further wherein at least one of the following is true:
- (1) a=1 and L is selected from the group consisting of terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
- (2) b=1 and L is selected from the group consisting of phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof,
- (3) at least one of R1, R2, R3, R4, R5, R6, and, when present, R7, or R8 is at least monosubstituted with a substituent independently selected from the group consisting of deuterium, halide, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof,
- (4) L is selected from the group consisting of naphthalene and dibenzothiophene, and L is further substituted,
- (5) at least one G3 is further substituted,
- (6) RA, RB, or both are selected from the group consisting of deuterium, halide, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof,
- (7) a is 1 and b is 1,
- (8) a is 1, b is 0, and n is an integer from 1 to 9, and
- (9) b is 1, a is 0, and G3 is selected from the group consisting of furan, thiophene, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenocarbazole, benzofluorenothiophene, and benzothienodibenzothiophene.
26 more elements
A formulation comprising a compound having formula I:
- wherein G1 has formula II:
- wherein G2 has formula III:
- wherein L is selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
- wherein G3 is selected from the group consisting of benzene, furan, thiophene, biphenyl, terphenyl, triphenylene, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenocarbazole, benzofluorenothiophene, and benzothienodibenzothiophene;
- wherein R2, R4, R6, and R8 each independently represent mono, di, tri, or no substitution;
- wherein R1, R3, R5, and R7 each independently represent mono, di, tri, tetra, or no substitution;
- wherein R1, R2, R5, R6, R7, R8, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof;
- wherein R3, R4, and RA are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, triphenyl, and combinations thereof;
- wherein L is optionally further substituted by one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryloxy, arylthio, arylseleno, nitrile, isonitrile, and combinations thereof;
- wherein G3 is optionally further substituted by one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, aryloxy, arylthio, arylseleno, heteroarylalkyl, heteroaryloxy, heteroarylthio, nitrile, isonitrile, and combinations thereof;
- wherein a is 0 or 1, and b is 0, 1, 2 or 3;
- wherein m is an integer from 1 to 10;
- wherein n is an integer from 0 to 9;
- wherein m is larger than n;
- and
- further wherein at least one of the following is true:
- (1) a=1 and L is selected from the group consisting of terphenyl, triphenylene, naphthalene, phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;
- (2) b=1 and L is selected from the group consisting of phenanthrene, chrysene, fluorene, xanthene, furan, thiophene, selenophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof,
- (3) at least one of R1, R2, R3, R4, R5, R6, and, when present, R7, or R8 is at least monosubstituted with a substituent independently selected from the group consisting of deuterium, halide, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof,
- (4) L is selected from the group consisting of naphthalene and dibenzothiophene, and L is further substituted,
- (5) at least one G3 is further substituted,
- (6) RA, RB, or both are selected from the group consisting of deuterium, halide, silyl, carbonyl, alkyloxyl, nitrile, isonitrile, benzene, biphenyl, terphenyl, triphenyl, and combinations thereof,
- (7) a is 1 and b is 1,
- (8) a is 1, b is 0, and n is an integer from 1 to 9, and
- (9) b is 1, a is 0, and G3 is selected from the group consisting of furan, thiophene, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, xanthene, chrysene, benzofuran, benzothiophene, dibenzoselenophene, indenocarbazole, benzothienocarbazole, benzofurocarbazole, benzoselenocarbazole, benzofluorenothiophene, and benzothienodibenzothiophene.
22 more elements
Dependencies are inferred from the claim text.