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US 12,593,378 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsLichang Zeng, Ting-Chih Wang, Alexey Borisovich Dyatkin, Chuanjun Xia
Life of this patent
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Abstract
A mixture of carbazole and triazine derivatives that can be thermally evaporated from one crucible to fabricate thin films for electroluminescent devices is disclosed.
Claims20
A composition of material comprising a mixture of a first compound and a second compound,
- wherein the first compound has a formula:
- wherein G1 is selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and fluorene;
- wherein L1, L2 and L3 are each independently selected from the group consisting of direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
- wherein G4 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, fluorene, and combinations thereof;
- wherein G2, G3, and G5 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 G2, G3, G4, and G5 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 0 to 7,
- wherein n is an integer from 0 to 4;
- wherein, when m or n is larger than 1, each G4 or G5 can be same or different;
- wherein, if n is 0 and m is equal to or greater than 1, then each G4 is selected from the group consisting of phenyl, and biphenyl;
- wherein when n is equal to or greater than 1, L1 is not a direct bond;
- wherein when m and n are both 0, L1 is biphenyl;
- wherein when G4 is present and is fluorene, L1 is not a direct bond;
- wherein the second compound has a structure of Formula II:
- wherein R1, and R4 each independently represent mono, di, tri, or tetra substitution, or no substitution;
- wherein R2, and R3 each independently represent mono, di, or tri substitution, or no substitution;
- wherein R1 to R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any two adjacent substituents are optionally joined or fused into a ring;
- and
- wherein at least one of the following is true:
- (i) at least one of R5 or R6 is a fused ring system selected from dibenzofuran, dibenzothiophene, dibenzoselenophene, or fluorene, and the fused ring system is substituted by an aryl or heteroaryl other than unsubstituted benzene, or (ii) the first compound is partially or fully deuterated.
18 more elements
A 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 mixture of a first compound and a second compound, wherein the first compound has a formula:
- wherein G1 is selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and fluorene;
- wherein L1, L2 and L3 are each independently selected from the group consisting of direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof;
- wherein G4 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, fluorene, and combinations thereof;
- wherein G2, G3, and G5 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 G2, G3, G4, and G5 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 0 to 7,
- wherein n is an integer from 0 to 4;
- wherein, when m or n is larger than 1, each G4 or G5 can be same or different;
- wherein, if n is 0 and m is equal to or greater than 1, then each G4 is selected from the group consisting of phenyl, and biphenyl;
- wherein when n is equal to or greater than 1, L1 is not a direct bond;
- wherein when m and n are both 0, L1 is biphenyl;
- wherein when G4 is present and is fluorene, L1 is not a direct bond;
- wherein the second compound has a structure of Formula II:
- wherein R1, and R4 each independently represent mono, di, tri, or tetra substitution, or no substitution;
- wherein R2, and R3 each independently represent mono, di, or tri substitution, or no substitution;
- wherein R1 to R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any two adjacent substituents are optionally joined or fused into a ring;
- and
- wherein at least one of the following is true:
- (i) at least one of R5 or R6 is a fused ring system selected from dibenzofuran, dibenzothiophene, dibenzoselenophene, or fluorene, and the fused ring system is substituted by an aryl or heteroaryl other than unsubstituted benzene, or (ii) is partially or fully deuterated.
21 more elements
Dependencies are inferred from the claim text.