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US 2023/0145950 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsHsiao-Fan CHEN, Jerald FELDMAN, Tyler FLEETHAM, Morgan C. MACINNIS
Life of this patent
Estimating the term…
Abstract
A compound of Formula I, is provided. In Formula I, rings A, B, and D are independently 5- or 6-membered rings; Z1-Z3 and X1-X5 are independently C or N; each of K1 and K2 are a direct bond, O, and S; Y1 is BR, NR1, O, S, Se, or CRR′; represents a single bond or no bond; when present, L1, L2, L3, and L4 are each independently a direct bond or a linker; each substituent is hydrogen or a general substituent and can be joined together to form a ring. Formulations, OLEDs, and consumer products containing the same are also provided.
Claims20
A compound of Formula I,
- wherein:
- rings A, B, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- Z1, Z2, and Z3 are each independently C or N;
- each of X1, X2, X3, X4, and X5 is independently C or N;
- K1 and K2 are each independently selected from the group consisting of a direct bond, O, and S;
- a is 0 or 1, b is 0 or 1;
- Y1 is selected from the group consisting of BR, NR1, O, S, Se, and CRR′, represents a single bond or no bond;
- when represents a single bond, a+b is 1, and a+b is 2 when represents no bond;
- when represents a single bond, L1 is selected from the group consisting of BR, BRR′, NR2, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;
- L2, L3, and L4 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;
- each one of RA′, RB′, RC′, and RD′, independently represents mono to the maximum allowable substitution, or no substitution;
- each R1, R2, R, R′, R″, RA′, RB′, RC′, RD′, and, when represents no bond, L1, 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, selenyl, and combinations thereof;
- any two adjacent R1, R2, R, R′, R″, RA′, RB′, RC′, and RD′ may be joined or fused together to form a ring, with the provisos that:
- (i) RA and RB do not form a ring and, if present, R1 and RC do not form a ring, and
- (ii) if K2 is a direct bond and L1 is NR2, then K1 is selected from O and S, and R2 is not joined with any other group to form a 5-membered ring.
12 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 of Formula I,
- wherein:
- rings A, B, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- Z1, Z2, and Z3 are each independently C or N;
- each of X1, X2, X3, X4, and X5 is independently C or N;
- K1 and K2 are each independently selected from the group consisting of a direct bond, O, and S;
- a is 0 or 1, b is 0 or 1;
- Y1 is selected from the group consisting of BR, NR1, O, S, Se, and CRR′,
- represents a single bond or no bond;
- when represents a single bond, a+b is 1, and a+b is 2 when represents no bond;
- when represents a single bond, L1 is selected from the group consisting of BR, BRR′, NR2, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;
- L2, L3, and L4 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;
- each one of RA′, RB′, RC′, and RD′, independently represents mono to the maximum allowable substitution, or no substitution;
- each R1, R2, R, R′, R″, RA′, RB′, RC′, RD′, and, when represents no bond, L1, 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, selenyl, and combinations thereof;
- any two adjacent R1, R2, R, R′, R″, RA′, RB′, RC′, and RD′ may be joined or fused together to form a ring, with the provisos that:
- (i) RA and RB do not form a ring and, if present, R1 and RC do not form a ring, and
- (ii) if K2 is a direct bond and L1 is NR2, then K1 is selected from O and S, and R2 is not joined with any other group to form a 5-membered ring.
17 more elements
A consumer product comprising an organic light-emitting device comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound of Formula I,
- wherein:
- rings A, B, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- Z1, Z2, and Z3 are each independently C or N;
- each of X1, X2, X3, X4, and X5 is independently C or N;
- K1 and K2 are each independently selected from the group consisting of a direct bond, O, and S;
- a is 0 or 1, b is 0 or 1;
- Y1 is selected from the group consisting of BR, NR1, O, S, Se, and CRR′,
- represents a single bond or no bond;
- when represents a single bond, a+b is 1, and a+b is 2 when represents no bond;
- when represents a single bond, L1 is selected from the group consisting of BR, BRR′, NR2, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;
- L2, L3, and L4 are each independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof;
- each one of RA′, RB′, RC′, and RD′, independently represents mono to the maximum allowable substitution, or no substitution;
- each R1, R2, R, R′, R″, RA′, RB′, RC′, RD′, and, when represents no bond, L1, 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, selenyl, and combinations thereof;
- any two adjacent R1, R2, R, R′, R″, RA′, RB′, RC′, and RD′ may be joined or fused together to form a ring, with the provisos that:
- (i) RA and RB do not form a ring and, if present, R1 and RC do not form a ring, and
- (ii) if K2 is a direct bond and L1 is NR2, then K1 is selected from O and S, and R2 is not joined with any other group to form a 5-membered ring.
17 more elements
Dependencies are inferred from the claim text.