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US 12,522,625 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsZhiqiang Ji, Alexey Borisovich Dyatkin, Jui-Yi Tsai, Pierre-Luc T. Boudreault
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Abstract
Cyclometalated iridium complexes having triphenylene or aza triphenylene and bulky alkyl substitution that can be used as emitters in OLEDs to improve the external quantum efficiency (EQE) and lifetime of OLEDs are disclosed.
Claims20
A compound of (LA)3-nIr(LB)n of Formula I
- wherein n=0, 1, or 2;
- wherein Z1 to Z16 are each independently C or N;
- wherein any of Z13 to Z16 is C when it forms a bond with Ir, or when it forms a bond with the ring having R1;
- wherein any chelate ring comprising Ir is a 5-membered ring;
- wherein R1 to R6 each independently represents mono to the maximum allowable substitution, or no substitution;
- wherein each R1 to R6 is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
- wherein any two substituents may be joined or fused together to form a ring;
- and
- wherein at least one of R1 and R2 is an alkyl or cycloalkyl group comprising five or more C atoms;
- wherein at least one of the following is true:
- i) at least one R1 or R2 is fully or partially deuterated;
- or
- ii) n=2;
- and
- wherein one of the following is true:
- A) the ring having R1 bonds to Z14 and one of the following is true:
- I) Z7 is N;
- or
- II) Z5 and Z8 are N;
- B) the ring having R1 bonds to Z15 and one of the following is true:
- 1) Z10 is N;
- or
- 2) Z9 and Z12 are N;
- or
- C) Z5 to Z16 are each C and if at least one of R1 and R2 is cycloalkyl comprising five or more C atoms, said cycloalkyl is not adamantyl and at least one of the following is true for said cycloalkyl:
- a) said cycloalkyl is partially deuterated;
- or
- b) said cycloalkyl has the structure selected from the group of
- or
- D) Z5 to Z16 are each C and at least one R1 or R2 comprises an alkyl group that is fully or partially deuterated and said alkyl group comprises a cycloalkyl substituent group that is nondeuterated.
27 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 compound of (LA)3-nIr(LB)n of Formula I
- wherein n=0, 1, or 2;
- wherein Z1 to Z16 are each independently C or N;
- wherein any of Z13 to Z16 is C when it forms a bond with Ir, or when it forms a bond with the ring having R1;
- wherein any chelate ring comprising Ir is a 5-membered ring;
- wherein R1 to R6 each independently represents mono to the maximum allowable substitution, or no substitution;
- wherein each R1 to R6 is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
- wherein any two substituents may be joined or fused together to form a ring;
- and
- wherein at least one of R1 and R2 is an alkyl or cycloalkyl group comprising five or more C atoms;
- wherein at least one of the following is true:
- i) at least one R1 or R2 is fully or partially deuterated;
- or
- ii) n=2;
- and
- wherein one of the following is true:
- A) the ring having R1 bonds to Z14 and one of the following is true:
- I) Z7 is N;
- or
- II) Z5 and Z8 are N;
- B) the ring having R1 bonds to Z15 and one of the following is true:
- 1) Z10 is N;
- or
- 2) Z9 and Z12 are N;
- or
- C) Z5 to Z16 are each C and if at least one of R1 and R2 is cycloalkyl comprising five or more C atoms, said cycloalkyl is not adamantyl and at least one of the following is true for said cycloalkyl:
- a) said cycloalkyl is partially deuterated;
- or
- b) said cycloalkyl has the structure selected from the group of
- or
- D) Z5 to Z16 are each C and at least one R1 or R2 comprises an alkyl group that is fully or partially deuterated and said alkyl group comprises a cycloalkyl substituent group that is nondeuterated.
31 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, comprising a compound of (LA)3-nIr(LB)n of Formula I
- wherein n=0, 1, or 2;
- wherein Z1 to Z16 are each independently C or N;
- wherein any of Z13 to Z16 is C when it forms a bond with Ir, or when it forms a bond with the ring having R1;
- wherein any chelate ring comprising Ir is a 5-membered ring;
- wherein R1 to R6 each independently represents mono to the maximum allowable substitution, or no substitution;
- wherein each R1 to R6 is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
- wherein any two substituents may be joined or fused together to form a ring;
- and
- wherein at least one of R1 and R2 is an alkyl or cycloalkyl group comprising five or more C atoms;
- wherein at least one of the following is true:
- i) at least one R1 or R2 is fully or partially deuterated;
- or
- ii) n=2;
- and
- wherein one of the following is true:
- A) the ring having R1 bonds to Z14 and one of the following is true:
- I Z7 is N;
- or
- II) Z5 and Z8 are N;
- B) the ring having R1 bonds to Z15 and one of the following is true:
- 1) Z10 is N;
- or
- 2) Z9 and Z12 are N;
- or
- C) Z5 to Z16 are each C and if at least one of R1 and R2 is cycloalkyl comprising five or more C atoms, said cycloalkyl is not adamantyl and at least one of the following is true for said cycloalkyl:
- a) said cycloalkyl is partially deuterated;
- or
- b) said cycloalkyl has the structure selected from the group of
- or
- D) Z5 to Z16 are each C and at least one R1 or R2 comprises an alkyl group that is fully or partially deuterated and said alkyl group comprises a cycloalkyl substituent group that is nondeuterated.
31 more elements
Dependencies are inferred from the claim text.