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US 2026/0138995 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsTYLER FLEETHAM, NICHOLAS J. THOMPSON, CHUN LIN, JERALD FELDMAN, PETER WOLOHAN, BIN MA
Life of this patent
Estimating the term…
Abstract
Provided are new compositions of matter for host materials in OLEDs by incorporating deuterated moieties in the organic molecules. Also provided are formulations comprising these deuterated compounds. Further provided are OLEDs and related consumer products that utilize these deuterated compounds.
Claims20
A compound selected from the group consisting of Formula (9), Formula (13), and Formula (14) shown below:
- wherein:
- RX, RY, RZ, RAA, RAL, RAM, RAN, RAO, RAP, RAQ, RAR, and RAS each independently represents mono to the maximum allowable substitution, or no substitution;
- X69 to X83, X114 to X121 are each independently C or N;
- at least one of X114 to X116 is N;
- any two adjacent substituents of RX, RY, RZ, RAA, RAL, RAM, and RAN can join or fuse into a ring;
- wherein the compound is at least 20% deuterated;
- when the compound is Formula (9), each RX, RY, RZ, RAA, and R5 is independently hydrogen or a substituent selected from the group consisting of deuterium, carbazole, phenyl, pyridine, pyrazine, pyrimidine, pyridazine, triazine, and combinations thereof;
- at least one RX is D and at least one RY is D;
- at least one of the following two conditions is true:
- (1) R5 comprises a moiety selected from the group consisting of carbazole, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and the compound is at least 80% deuterated;
- or
- (2) R5 comprises phenyl, and each ortho and para position of each phenyl of Formula (9) is H or D;
- when the compound is Formula (13), each RAL, RAM, RAN, and RAO is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one RAL is D, at least one RAM is D, and at least one RAN is D;
- when the compound is Formula (14), at least one of the following two conditions is true:
- (a) each RAP, RAQ, RAR, or RAS is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
- at least one RAP, RAQ, RAR, or RAS is unique;
- and the compound only comprises one Si;
- and compound is more than 80% deuterated;
- or
- (b) each RAP, RAQ, RAR, and RAS is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one RAP is deuterium, at least one RAQ is deuterium, at least one RAR is deuterium, and at least one RAS is deuterium;
- any two adjacent RAP to RAS can be joined or fused to form a ring;
- and at least one RAP, RAQ, RAR, or RAS comprises a group selected from the group consisting of triazine, pyrimidine, pyridine, pyrazine, boryl, silane, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, tetraphenylene, and combinations thereof, with the proviso that each RAP to RAS does not comprises a 6-membered ring containing exactly one B and exactly one N.
21 more elements
An organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises a compound selected from the group consisting of Formula (9), Formula (13), and Formula (14) shown below:
- wherein:
- RX, RY, RZ, RAA, RAL, RAM, RAN, RAO, RAP, RAQ, RAR, and RAS each independently represents mono to the maximum allowable substitution, or no substitution;
- X69 to X83, X114 to X121 are each independently C or N;
- at least one of X114 to X116 is N;
- any two adjacent substituents of RX, RY, RZ, RAA, RAL, RAM, and RAN can join or fuse into a ring;
- wherein the compound is at least 20% deuterated;
- when the compound is Formula (9), each RX, RY, RZ, RAA, and R5 is independently hydrogen or a substituent selected from the group consisting of deuterium, carbazole, phenyl, pyridine, pyrazine, pyrimidine, pyridazine, triazine, and combinations thereof;
- at least one RX is D and at least one RY is D;
- at least one of the following two conditions is true:
- (1) R5 comprises a moiety selected from the group consisting of carbazole, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and the compound is at least 80% deuterated;
- or
- (2) R5 comprises phenyl, and each ortho and para position of each phenyl of Formula (9) is H or D;
- when the compound is Formula (13), each RAL, RAM, RAN, and RAO is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one RAL is D, at least one RAM is D, and at least one RAN is D;
- when the compound is Formula (14), at least one of the following two conditions is true:
- (a) each RAP, RAQ, RAR, or RAS is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
- at least one RAP, RAQ, RAR, or RAS is unique;
- and the compound only comprises one Si;
- and compound is more than 80% deuterated;
- or
- (b) each RAP, RAQ, RAR, and RAS is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one RAP is deuterium, at least one RAQ is deuterium, at least one RAR is deuterium, and at least one RAS is deuterium;
- any two adjacent RAP to RAS can be joined or fused to form a ring;
- and at least one RAP, RAQ, RAR, or RAS comprises a group selected from the group consisting of triazine, pyrimidine, pyridine, pyrazine, boryl, silane, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, tetraphenylene, and combinations thereof, with the proviso that each RAP to RAS does not comprises a 6-membered ring containing exactly one B and exactly one N.
26 more elements
A consumer product comprising an organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises the compound selected from the group consisting of Formula (9), Formula (13), and Formula (14) shown below:
- wherein:
- RX, RY, RZ, RAA, RAL, RAM, RAN, RAO, RAP, RAQ, RAR, and RAS each independently represents mono to the maximum allowable substitution, or no substitution;
- X69 to X83, X114 to X121 are each independently C or N;
- at least one of X114 to X116 is N;
- any two adjacent substituents of RX, RY, RZ, RAA, RAL, RAM, and RAN can join or fuse into a ring;
- wherein the compound is at least 20% deuterated;
- when the compound is Formula (9), each RX, RY, RZ, RAA, and R5 is independently hydrogen or a substituent selected from the group consisting of deuterium, carbazole, phenyl, pyridine, pyrazine, pyrimidine, pyridazine, triazine, and combinations thereof;
- at least one RX is D and at least one RY is D;
- at least one of the following two conditions is true:
- (1) R5 comprises a moiety selected from the group consisting of carbazole, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and the compound is at least 80% deuterated;
- or
- (2) R5 comprises phenyl, and each ortho and para position of each phenyl of Formula (9) is H or D;
- when the compound is Formula (13), each RAL, RAM, RAN, and RAO is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one RAL is D, at least one RAM is D, and at least one RAN is D;
- when the compound is Formula (14), at least one of the following two conditions is true:
- (a) each RAP, RAQ, RAR, or RAS is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
- at least one RAP, RAQ, RAR, or RAS is unique;
- and the compound only comprises one Si;
- and compound is more than 80% deuterated;
- or
- (b) each RAP, RAQ, RAR, and RAS is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one RAP is deuterium, at least one RAQ is deuterium, at least one RAR is deuterium, and at least one RAS is deuterium;
- any two adjacent RAP to RAS can be joined or fused to form a ring;
- and at least one RAP, RAQ, RAR, or RAS comprises a group selected from the group consisting of triazine, pyrimidine, pyridine, pyrazine, boryl, silane, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, tetraphenylene, and combinations thereof, with the proviso that each RM to RAS does not comprises a 6-membered ring containing exactly one B and exactly one N.
26 more elements
Dependencies are inferred from the claim text.