US 12,598,905 B2Granted

Organic electroluminescent materials and devices

AssigneeUniversal Display Corporation

InventorsZhiqiang Ji, Alexey Borisovich Dyatkin, Jui-Yi Tsai

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Abstract

A compound comprising a first ligand LA of Formula I is provided. In Formula I, A is a 5- or 6-membered aryl or heteroaryl ring; each of Z1-Z11 is either C or N; each of Y1-Y4 is selected from a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′; at least one of Y1 and Y2 is not a direct bond; at least one of Y3 and Y4 is not a direct bond; each RA, RB, RC, R, and R′ is independently hydrogen or a variety of substituents; any two adjacent substitutions in RA, RB and RC can be joined or fused into a ring; ligand LA is coordinated to a metal M; LA is optionally linked with other ligands; and M is optionally coordinated to other ligands. Organic light emitting devices and consumer products containing the compounds are also disclosed.

Claims20

Dependent claims

A metal-containing compound having a structure of M(LA)x(LB)y(LC)z, wherein x is 1 or 2;

y is 1 or 2;
z is 0, 1, or 2;
and x+y+z is the oxidation state of the metal M;
wherein the compound is a heteroleptic compound;
wherein a first ligand LA has a structure of Formula I,
wherein A is a 6-membered heteroaryl ring;
wherein LB and LC are each independently selected from the group consisting of:
wherein Ra, Rb, Rc, Rd, RA, RB, and RC each represent mono to a maximum possible number of substitutions, or no substitution;
wherein X1-X13 and Z1-Z3 are each independently selected from the group consisting of C and N;
wherein Z4-Z11 are each C;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein Y1, Y2, Y3, and Y4 are each independently selected from the group consisting of a direct bond, BR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein at least one of Y1 and Y2 is not a direct bond;
wherein at least one of Y3 and Y4 is not a direct bond;
wherein Ra, Rb, Rc, Rd, RA, RB, RC, R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RA is selected from the group consisting of cycloalkyl, aryl, partially or fully deuterated variants thereof, partially or fully deuterated alkyl, and combinations thereof;
wherein any two adjacent substitutions in Ra, Rb, Rc, Rd, RA, RB and RC are optionally joined or fused into a ring;
wherein, when X is CRR′, SiRR′, or GeRR′, R and R′ are optionally fused or joined to form a ring;
wherein any of LA, LB, or LC is optionally linked with other ligands to form a tetradentate or hexadentate ligand.

16 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 having a structure of M(LA)xLB)y(LC)z, wherein x is 1 or 2;
y is 1 or 2;
z is 0, 1, or 2;
and x+y+z is the oxidation state of the metal M;
wherein the compound is a heteroleptic compound;
wherein a first ligand LA has a structure of Formula I,
wherein A is a 6-membered heteroaryl ring;
wherein LB and LC are each independently selected from the group consisting of
wherein Ra, Rb, Rc, Rd, RA, RB, and RC each represent mono to a maximum possible number of substitutions, or no substitution;
wherein X1-X13 and Z1-Z3 are each independently selected from the group consisting of C and N;
wherein Z4-Z11 are each C;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein Y1, Y2, Y3, and Y4 are each independently selected from the group consisting of a direct bond, BR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein at least one of Y1 and Y2 is not a direct bond;
wherein at least one of Y3 and Y4 is not a direct bond;
wherein Ra, Rb, Rc, Rd, RA, RB, RC, R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RA is selected from the group consisting of cycloalkyl, aryl, partially or fully deuterated variants thereof, partially or fully deuterated alkyl, and combinations thereof;
wherein any two adjacent substitutions in Ra, Rb, Rc, Rd, RA, RB and RC are optionally joined or fused into a ring;
wherein, when X is CRR′, SiRR′, or GeRR′, R and R′ are optionally fused or joined to form a ring;
wherein any of LA, LB, or LC is optionally linked with other ligands to form a tetradentate or hexadentate ligand.

20 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 having a structure of M(LA)xLB)y(LC)z, wherein x is 1 or 2;
y is 1 or 2;
z is 0, 1, or 2;
and x+y+z is the oxidation state of the metal M;
wherein the compound is a heteroleptic compound;
wherein a first ligand LA has a structure of Formula I,
wherein A is a 6-membered heteroaryl ring;
wherein LB and LC are each independently selected from the group consisting of:
wherein Ra, Rb, Rc, RA, RB, and RC each represent mono to a maximum possible number of substitutions, or no substitution;
wherein X1-X13 and Z1-Z3 are each independently selected from the group consisting of C and N;
wherein Z4-Z11 are each C;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein Y1, Y2, Y3, and Y4 are each independently selected from the group consisting of a direct bond, BR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein at least one of Y1 and Y2 is not a direct bond;
wherein at least one of Y3 and Y4 is not a direct bond;
wherein Ra, Rb, Rc, Rd, RA, RB, RC, R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one RA is selected from the group consisting of cycloalkyl, aryl, partially or fully deuterated variants thereof, partially or fully deuterated alkyl, and combinations thereof;
wherein any two adjacent substitutions in Ra, Rb, Rc, Rd, RA, RB and Rc are optionally joined or fused into a ring;
wherein, when X is CRR′, SiRR′, or GeRR′, R and R′ are optionally fused or joined to form a ring;
wherein any of LA, LB, or LC is optionally linked with other ligands to form a tetradentate or hexadentate ligand.

20 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/009,455Filed 15 Jun 2018 · us provisional application
Priority: 23 Jun 2017
Published: US 2018/0375035 A127 Dec 2018
Granted: 7 Apr 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

H10K 85/342
Transition metal complexes, e.g. Rupolypyridine complexes: comprising iridium
C07F 15/0033
Compounds of the platinum group: iridium compounds
C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
H10K 85/346
Transition metal complexes, e.g. Rupolypyridine complexes: comprising platinum