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US 10,593,892 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsPeter Wolohan, Bin Ma, George Fitzgerald, Daniel W. Silverstein
Life of this patent
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Abstract
This invention relates to the development of heterocyclic materials with high triplet excitation energy, which can be used as host materials in electroluminescent devices such as a PHOLED. The materials improve the performance of such devices by enhancing the lifetime and efficiency of the device when the newly developed heterocyclic materials are utilized as a host.
Claims18
A compound having a formula selected from the group consisting of Formula I and Formula II:
- 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 R5 and R6 optionally join to form a phenyl ring or substituted phenyl ring
- wherein at least one of R1 to R6 comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene;
- wherein at least one of R1 to R6 comprises at least one chemical group selected from the group consisting of aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene,
- wherein each occurrence of X1 and X2 is independently selected from the group consisting of NR, SiRR′, GeRR′, O, S, and Se;
- and
- wherein each occurrence of R and R′ is 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;
- and adjacent substituents of R and R′ are optionally fused or joined to form a ring.
5 more elements
A compound of Formula III or Formula IV
- wherein X1 is selected from the group consisting of NR, SiRR′, and GeRR′
- X2 is O;
- R, R′, R1, R2, R3, R4, R7, R8, R9, and R10 are 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;
- and adjacent substituents of R and R′ optionally join to form a ring;
- and
- at least one of R1, R2, R3, R4, R7, R8, R9, and R10 comprises a chemical group selected from the group consisting of silyl, non-fused five-membered heteroaromatic ring, and tetraphenylene.
3 more elements
An organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a formula selected from the group consisting of Formula I and Formula II:
- 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 R5 and R6 optionally join to form a phenyl ring or substituted phenyl ring
- wherein at least one of R1 to R6 comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene;
- wherein at least one of R1 to R6 comprises at least one chemical group selected from the group consisting of aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene,
- wherein each occurrence of X1 and X2 is independently selected from the group consisting of NR, SiRR′, GeRR′, O, S, and Se;
- wherein each occurrence of R and R′ is 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;
- and adjacent substituents of R and R′ are optionally fused or joined to form a ring.
7 more elements
Dependencies are inferred from the claim text.