US 2023/0144846 A1Published application

Organic electroluminescent materials and devices

AssigneeUniversal Display Corporation

InventorsJerald FELDMAN, Pierre-Luc T. BOUDREAULT, Nicholas J. THOMPSON, Tyler FLEETHAM

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Abstract

A compound of Formula I is provided. In Formula I, ring A is a heterocyclic ring; ring B is a 5- or 6-membered ring, and rings C and D are 6-membered rings; one of Z1, Z2, and Z3 is N and the remainder are C; at least one of K1, K2, and K3 is O or S; one of L1 and L2 is absent and the other one is a direct bond or a linker; when m=0, L1 is not present and X1 is NRA′; each R, R′, R″, RA′, RA, RB, RC, and RD is independently hydrogen or a substituent selected from the general substituents defined herein; and any two substituents may be joined or fused together to form a ring. Formulations, OLEDs, and consumer products incorporating such compounds are also provided.

Claims20

Dependent claims

A compound comprising a structure of Formula I,

wherein:
ring A is a 5-membered or 6-membered heterocyclic ring;
ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
each of ring C and ring D is independently a 6-membered carbocyclic or heterocyclic ring;
Z1, Z2, and Z3 are each independently C or N;
one of Z1, Z2, and Z3 is N and the remainder are C;
each of K1, K2, and K3 is independently selected from the group consisting of a direct bond, O, and S;
at least one of K1, K2, and K3 is not a direct bond;
ring A bonds to M through a metal-carbene bond;
RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
when present, L1 and L2 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
X is selected from the group consisting of O, S, Se, NR′, and CR″;
m is 0 or 1, n is 0 or 1, and m+n=1;
when m=0, L1 is not present and X1 is NRA′;
when m=1, X1 is N, n=0, and L2 is not present;
each R, R′, R″, RA′, RA, RB, RC, and RD is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
any two substituents may be joined or fused together to form a ring;
with the proviso that the compound is not
and with the proviso that the compound does not comprise a structure of formula 1,
wherein Z1 is C or Si and X1 is C or N.

17 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 comprising a structure of Formula I,
wherein:
ring A is a 5-membered or 6-membered heterocyclic ring;
ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
each of ring C and ring D is independently a 6-membered carbocyclic or heterocyclic ring;
Z1, Z2, and Z3 are each independently C or N;
one of Z1, Z2, and Z3 is N and the remainder are C;
each of K1, K2, and K3 is independently selected from the group consisting of a direct bond, O, and S;
at least one of K1, K2, and K3 is not a direct bond;
ring A bonds to M through a metal-carbene bond;
RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
when present, L1 and L2 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
X is selected from the group consisting of O, S, Se, NR′, and CR″;
m is 0 or 1, n is 0 or 1, and m+n=1;
when m=0, L1 is not present and X1 is NRA′;
when m=1, X1 is N, n=0, and L2 is not present;
each R, R′, R″, RA′, RA, RB, RC, and RD is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
any two substituents may be joined or fused together to form a ring;
with the proviso that the compound is not
and with the proviso that the compound does not comprise a structure of formula 1,
wherein Z1 is C or Si and X1 is C or N.

21 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 a compound comprising a structure of Formula I,
wherein:
ring A is a 5-membered or 6-membered heterocyclic ring;
ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
each of ring C and ring D is independently a 6-membered carbocyclic or heterocyclic ring;
Z1, Z2, and Z3 are each independently C or N;
one of Z1, Z2, and Z3 is N and the remainder are C;
each of K1, K2, and K3 is independently selected from the group consisting of a direct bond, O, and S;
at least one of K1, K2, and K3 is not a direct bond;
ring A bonds to M through a metal-carbene bond;
RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
when present, L1 and L2 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
X is selected from the group consisting of O, S, Se, NR′, and CR″;
m is 0 or 1, n is 0 or 1, and m+n=1;
when m=0, L1 is not present and X1 is NRA′;
when m=1, X1 is N, n=0, and L2 is not present;
each R, R′, R″, RA′, RA, RB, RC, and RD is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
any two substituents may be joined or fused together to form a ring;
with the proviso that the compound is not
and with the proviso that the compound does not comprise a structure of formula 1,
wherein Z1 is C or Si and X1 is C or N.

21 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/953,357Filed 27 Sep 2022
Priority: 14 Oct 2021
Published: 11 May 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification21 codes

C07F 15/0006
Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table: compounds of the platinum group
C07F 15/0086
Compounds of the platinum group: platinum compounds
H10K 50/11
OLEDs or polymer light-emitting diodes [PLED]: characterised by the electroluminescent [EL] layers
H10K 85/322
Metal complexes comprising a group IIIA element, e.g. Tris gallium [Gaq3]: comprising boron