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US 12,284,911 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsLichang Zeng, Vadim Adamovich, Chuanjun Xia, Michael Weaver
Life of this patent
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Abstract
A dual host system for OLEDs that contains hole-transporting indolocarbazole and electron-transporting indolocarbazole exhibiting superior performance in the OLEDs is disclosed.
Claims20
A composition comprising, a mixture of a first compound and a second compound;
- wherein the first compound has a structure of Formula I:
- wherein the second compound has a structure of Formula II:
- wherein L1, L2, L3 and L4 are each independently selected from the group consisting of direct bond, alkyl, alkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
- wherein G1 and G2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, benzene, biphenyl, terphenyl, naphthalene, triphenylene, pyrene, anthracene, phenanthrene, fluoranthene, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;
- wherein G3 is selected from the group consisting of pyridine, pyramidine, pyrazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, benzimidazole, aza-triphenylene, phenanthroline, aza-pyrene, aza-anthracene, aza-fluorene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-carbazole, and combinations thereof;
- wherein G4 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof;
- wherein G3 is optionally further substituted with substituent selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof;
- wherein R1, R2, R3, R4, R5 and R6 each independently represents mono to maximum allowable substitutions, or no substitution;
- wherein R1, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkyloxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- wherein, when any of R1, R2, R3, L1, or L2 comprises heteroaryl, the heteroaryl is independently selected from the group consisting of dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, thiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, indazole, indoxazine, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and aza-analogs thereof;
- and
- wherein any two adjacent substituents optionally join or fuse into a ring.
9 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a mixture of a first compound and a second compound;
- wherein the first compound has a structure of Formula I:
- wherein the second compound has a structure of Formula II:
- wherein L1, L2, L3 and L4 are each independently selected from the group consisting of direct bond, alkyl, alkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
- wherein G1 and G2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, benzene, biphenyl, terphenyl, naphthalene, triphenylene, pyrene, anthracene, phenanthrene, fluoranthene, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;
- wherein G3 is selected from the group consisting of pyridine, pyramidine, pyrazine, triazine, quinoline, isoquinoline, quinazoline, aza-triphenylene, phenanthroline, aza-pyrene, aza-anthracene, aza-fluorene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-carbazole, and combinations thereof;
- wherein G4 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof;
- wherein G3 is optionally further substituted with substituent selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof;
- wherein R1, R2, R3, R4, R5 and R6 each independently represents mono to maximum allowable substitutions, or no substitution;
- wherein R1, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkyloxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- wherein, when any of R1, R2, R3, L1, or L2 comprises heteroaryl, the heteroaryl is independently selected from the group consisting of dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, thiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, indazole, indoxazine, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and aza-analogs thereof;
- and
- wherein any two adjacent substituents optionally join or fuse into a ring.
13 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- an emissive layer comprising a first host and an emissive dopant;
- and
- an electron blocking layer (EBL),
- wherein the emissive layer and the electron blocking layer are disposed between the anode and the cathode, the EBL comprising an EBL compound having a structure of Formula I:
- wherein L1, L2 are each independently selected from the group consisting of direct bond, alkyl, alkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
- wherein G1 and G2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, benzene, biphenyl, terphenyl, naphthalene, triphenylene, pyrene, anthracene, phenanthrene, fluoranthene, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;
- wherein R1, R2, and R3 each independently represents mono to maximum allowable substitutions, or no substitution;
- wherein R1, R2, and R3 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkyloxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- wherein, when any of R1, R2, R3, L1, or L2 comprises heteroaryl, the heteroaryl is independently selected from the group consisting of dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, thiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, indazole, indoxazine, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and aza-analogs thereof;
- wherein any two adjacent substituents optionally join or fuse into a ring;
- and
- wherein the EBL compound and the first host are the same.
11 more elements
Dependencies are inferred from the claim text.