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US 12,598,908 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsHsiao-Fan Chen, Jerald Feldman
Life of this patent
Estimating the term…
Abstract
A compound having a structure of Formula I, is provided. In Formula I, two of Z1, Z2, Z3, and Z4 are C and the other two are N; each of X1 to X16 is independently C or N; each of L1 and L2 is independently a direct bond or a linker; one of L1 and L2 is present; M is Pd or Pt; each RA, RB, RC, and RD is independently hydrogen or a substitutent selected from the General Substituent; and any two of RA, RB, RC, and RD can be joined or fused together to form a ring. Formulations, OLEDs, and consumer products including the compound of Formula I are also disclosed.
Claims20
A compound having a structure of Formula I:
- wherein:
- rings A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- either Z1 and Z4 are both C and Z2 and Z3 are both N, or Z1 and Z4 are both N and Z2 and Z3 are both C;
- each of X1-X16 is independently C or N;
- each of L1 and L2 is 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″;
- a and b are each independently 0 or 1;
- when a is 0, L1 is absent and X1 is not bonded to X8, and when b is 0, L2 is absent and X7 is not bonded to X14;
- a+b=1;
- when Z1 and Z4 are both C, a=0;
- when Z1 and Z4 are both N, b=0 or L2 is a direct bond;
- when a=1, X1 and X8 are both C;
- when b=1, X7 and X14 are both C;
- M is Pd or Pt;
- RA, RB, RC, and RD each independently represents mono to the maximum allowable substitution, or no substitution;
- each R, R′, R″, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two of R, R′, R″, RA, RB, RC, and RD can be joined or fused together to form a ring, except that at least one of the following is true (1) no RA is joined or fused to an RC to form a ring, or (2) no RB is joined or fused to an RD to form a ring;
- wherein at least one of the following is true:
- (i) at least one of ring A or ring B is a 5-membered ring or a heterocyclic ring;
- (ii) b=1 and L2 is a direct bond;
- (iii) at least one RA bonded to ring A or at least one RB bonded to ring B is not H;
- (iv) two RC are joined or fused to form a ring;
- (v) two RD are joined or fused to form a ring;
- or
- (vi) a is 0;
- and
- with the proviso that the compound is not
24 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 having a structure of Formula I:
- wherein:
- rings A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- either Z1 and Z4 are both C and Z2 and Z3 are both N, or Z1 and Z4 are both N and Z2 and Z3 are both C;
- each of X1-X16 is independently C or N;
- each of L1 and L2 is 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″;
- a and b are each independently 0 or 1;
- when a is 0, L′ is absent and X1 is not bonded to X8, and when b is 0, L2 is absent and X7 is not bonded to X14;
- a+b=1;
- when Z1 and Z4 are both C, a=0;
- when Z1 and Z4 are both N, b=0 or L2 is a direct bond;
- when a=1, X1 and X8 are both C;
- when b=1, X7 and X14 are both C;
- M is Pd or Pt;
- RA, RB, RC, and RD each independently represents mono to the maximum allowable substitution, or no substitution;
- each R, R′, R″, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two of R, R′, R″, RA, RB, RC, and RD can be joined or fused together to form a ring, except that at least one of the following is true (1) no RA is joined or fused to an RC to form a ring, or (2) no RB is joined or fused to an RD to form a ring;
- wherein at least one of the following is true:
- (i) at least one of ring A or ring B is a 5-membered ring or a heterocyclic ring;
- (ii) b=1 and L2 is a direct bond;
- (iii) at least one RA bonded to ring A or at least one RB bonded to ring B is not H;
- (iv) two RC are joined or fused to form a ring;
- (v) two RD are joined or fused to form a ring;
- or
- (vii) a is 0;
- and
- with the proviso that the compound is not
29 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 having a structure of Formula I:
- wherein:
- rings A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- either Z1 and Z4 are both C and Z2 and Z3 are both N, or Z1 and Z4 are both N and Z2 and Z3 are both C;
- each of X1-X16 is independently C or N;
- each of L1 and L2 is 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″;
- a and b are each independently 0 or 1;
- when a is 0, L1 is absent and X1 is not bonded to X8, and when b is 0, L2 is absent and X7 is not bonded to X14;
- a+b=1;
- when Z1 and Z4 are both C, a=0;
- when Z1 and Z4 are both N, b=0 or L2 is a direct bond;
- when a=1, X1 and X8 are both C;
- when b=1, X7 and X14 are both C;
- M is Pd or Pt;
- RA, RB, RC, and RD each independently represents mono to the maximum allowable substitution, or no substitution;
- each R, R′, R″, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two of R, R′, R″, RA, RB, RC, and RD can be joined or fused together to form a ring, except that at least one of the following is true (1) no RA is joined or fused to an RC to form a ring, or (2) no RB is joined or fused to an RD to form a ring:
- wherein at least one of the following is true:
- (i) at least one of ring A or ring B is a 5-membered ring or a heterocyclic ring;
- (ii) b=1 and L2 is a direct bond;
- (iii) at least one RA bonded to ring A or at least one RB bonded to ring B is not H;
- (iv) two RC are joined or fused to form a ring;
- (v) two RD are joined or fused to form a ring;
- or
- (vi) a is 0;
- and
- with the proviso that the compound is not
29 more elements
Dependencies are inferred from the claim text.