IP Library › Granted Patent US 12,239,012
Granted Patent B2
US 12,239,012 · App. 18/322,617 · Granted Feb 25, 2025

Organic electroluminescent materials and devices

Inventors: Hsiao-Fan Chen (Lawrence Township, NJ); Jason Brooks (Philadelphia, PA); Douglas Williams (Mullica Hill, NJ); Charles J. Stanton, III (Wilmington, DE); Eugene S. Gutman (Philadelphia, PA); Wei Bao (Hockessin, DE)
Assignee: UNIVERSAL DISPLAY CORPORATION
H10K85/346C07F15/0086C09K11/02C09K11/06C09K2211/1022C09K2211/1029C09K2211/104C09K2211/1044C09K2211/185H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 12,239,012
App. No.
18/322,617
Granted
Feb 25, 2025
Kind
B2
Abstract

A compound is disclosed that is selected from the group consisting of a structure having and a structure having

Claims (201)

1. A compound selected from the group consisting of:

a structure having

and a structure having

wherein rings A and B are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;

wherein M is Pt or Pd;

wherein T 1 and T 2 are C;

wherein X 1 -X 5 , Z 1 , and Z 2 are each independently selected from the group consisting of carbon and nitrogen;

wherein each R A , R B , R C , and R D represents mono to a maximum possible number of substitutions, or no substitution;

wherein Y 1 is selected from the group consisting of CRR′, SiRR′, GeR″R″′, BR, O, and S;

wherein Y 2 and Y 3 are each selected from the group consisting of CRR′, SiRR′, BR, NR, O, and S;

wherein if one of Y 2 and Y 3 is O, S, or NR, the other is not O, S, or NR;

wherein n 1 and n 2 are each independently 0 or 1;

wherein when n 1 or n 2 is 1, L 1 or L 2 is present

wherein when n 1 or n 2 is 0, L 1 or L 2 is not present;

wherein n 1 +n 2 is at least 1;

wherein if present, L 1 and L 2 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C—O, S—O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;

wherein R 1 , R 2 , R, R′, R A , R B , R C , and R D are each independently a 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;

wherein R″ and R″′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heterocycloalkyl, arylalkyl, amino, aryl, heteroaryl, ether, and combinations thereof;

wherein any two substituents may be joined or fused together to form a ring;

when Y 1 is CRR′, BR, O, or S, R 1 comprises aryl;

when Y 1 is BR, at least one of the following is true:

i) R in BR is a 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, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

ii) R 1 is an aryl group comprising three or more phenyl rings that are joined to form a chain; or

iii) n 2 in Formula I is 1 and L 2 is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;

when Y 1 is SiRR′, at least one of the following is true:

i) R and R′ in SiRR′ are each independently a 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, wherein if aryl or heteroaryl are present, the aryl or heteroaryl are joined to form a fused ring; or

ii) R 1 is an aryl group comprising three or more phenyl rings that are joined to form a chain;

if Y 2 is CRR′ wherein at least one of R and R′ is hydrogen or deuterium, then at least one of the following is true:

i) the other of R and R′ of Y 2 is a substituent selected from the group consisting of 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; or

ii) Y 3 is CRR′ wherein at least one of R and R′ is hydrogen or a substituent selected from the group consisting of deuterium, halogen, 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.

2. The compound of claim 1 , wherein R 1 , R 2 , R, R′, R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein Y 1 is CRR′, Y 2 and Y 3 each have the formula CRR′, and Y 2 and Y 3 can be the same or different.

4. The compound of claim 3 , wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

5. The compound of claim 1 , wherein X 1 to X 5 are each C.

6. The compound of claim 1 , wherein at least one of X 1 to X 5 is N.

7. The compound of claim 1 , wherein L 1 is present and is selected from the group consisting of NR and O.

8. The compound of claim 1 , wherein L 2 is present and is a direct bond.

9. The compound of claim 1 , wherein one of Z 1 and Z 2 is N, and the other of Z 1 and Z 2 is C.

10. The compound of claim 1 , wherein one of Z 1 and Z 2 is a neutral carbene carbon, and the other one of Z 1 and Z 2 is an anionic carbon.

11. The compound of claim 1 , wherein Y 1 is selected from the group consisting of:

12. The compound of claim 1 , wherein Y 2 to Y 3 in Formula II is selected from the group consisting of:

wherein each of the dashed lines indicates a direct bond to T 1 or T 2 .

13. The compound of claim 1 , wherein the partial structure of:

in Formula I and Formula II is selected from the group consisting of:

wherein X is selected from the group consisting of O, S, NR′, BR′, CR′R″, and SiR′R″.

14. The compound of claim 1 , wherein the compound is the compound has a structure of

where the ligand

is L A , and the ligand

is L B ;

where L A is selected from the group consisting of the following structures:

L A

Structure of L A

R A1 -R A10

L A 1-(i)(j)(k)(l)(m)(n), wherein i is an integer from 1 to 77, and j, k, l, m, and n are each an integer from 1 to 86, wherein L A 1- (1)(1)(1)(1)(1)(1) to L A 1- (77)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m and R A6 = R A n,.

L A 2-(i)(j)(k)(l)(m)(n), wherein i is an integer from 1 to 77, and j, k, l, m, and n are each an integer from 1 to 86, wherein L A 2- (1)(1)(1)(1)(1)(1) to L A 2- (77)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m and R A6 = R A n,

L A 3-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o and p are each an integer from 1 to 86, wherein L A 3- (1)(1)(1)(1)(1)(1)(1)(1) to L A 3- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 4-(i)(j)(k)(l)(m)(n)(o) (p)(q)(r), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, p, q and r are each an integer from 1 to 86, wherein L A 4- (1)(1)(1)(1)(1)(1)(1)(1)(1)(1) to L A 4- (77)(86)(86)(86) (86)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o, R A8 = R A p, R A9 = R A q and R A10 = R A r,

L A 5-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o and p are each an integer from 1 to 86, wherein L A 5- (1)(1)(1)(1)(1)(1)(1)(1) to L A 5- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 6-(i)(j)(k)(l)(m)(n)(o) (p)(q)(r), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, p, q and r are each an integer from 1 to 86, wherein L A 6- (1)(1)(1)(1)(1)(1)(1)(1)(1)(1) to L A 6- (77)(86)(86)(86) (86)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o, R A8 = R A p, R A9 = R A q and R A10 = R A r,

L A 7-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o and p are each an integer from 1 to 86, wherein L A 7- (1)(1)(1)(1)(1)(1)(1)(1) to L A 7- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 8-(i)(j)(k)(l)(m)(n)(o) (p)(q)(r), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, p, q and r are each an integer from 1 to 86, wherein L A 8- (1)(1)(1)(1)(1)(1)(1)(1)(1)(1) to L A 8- (77)(86)(86)(86) (86)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o, R A8 = R A p, R A9 = R A q and R A10 = R A r,

L A 9-(i)(j)(k)(l)(m)(n)(o), wherein i is an integer from 1 to 77, and j, k, l, m, n, and o are each an integer from 1 to 86, wherein L A 9- (1)(1)(1)(1)(1)(1)(1) to L A 9- (77)(86)(86)(86) (86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n and R A 7 = R A o,

L A 10-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, and p are each an integer from 1 to 86, wherein L A 10- (1)(1)(1)(1)(1)(1)(1)(1) to L A 10- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 11-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, and p are each an integer from 1 to 86, wherein L A 11- (1)(1)(1)(1)(1)(1)(1)(1) to L A 11- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 12-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, and p are each an integer from 1 to 86, wherein L A 12- (1)(1)(1)(1)(1)(1)(1)(1) to L A 12- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 13-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, and p are each an integer from 1 to 86, wherein L A 13- (1)(1)(1)(1)(1)(1)(1)(1) to L A 13- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 14-(i)(j)(k)(l)(m)(n)(o)(p), wherein i is an integer from 1 to 77, and j, k, l, m, n, o, and p are each an integer from 1 to 86, wherein L A 14- (1)(1)(1)(1)(1)(1)(1)(1) to L A 14- (77)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m, R A6 = R A n, R A 7 = R A o and R A8 = R A p,

L A 15-(i)(j)(k)(l)(m)(n), wherein i is an integer from 1 to 77, and j, k, l, m, and n are each an integer from 1 to 86, wherein L A 15- (1)(1)(1)(1)(1)(1) to L A 15- (77)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m and R A6 = R A n,

L A 16-(i)(j)(k)(l)(m)(n), wherein i is an integer from 1 to 77, and j, k, l, m, and n are each an integer from 1 to 86, wherein L A 16- (1)(1)(1)(1)(1)(1) to L A 16- (77)(86)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l, R A5 = R A m and R A6 = R A n,

L A 17-(i)(j)(k)(l)(m), wherein i is an integer from 1 to 77, and j, k, l, and m are each an integer from 1 to 86, wherein L A 17- (1)(1)(1)(1)(1) to L A 17- (77)(86)(86)(86)(86), having the structure

wherein R A1 = R A i, R A2 = R A j, R A3 = R A k, R A4 = R A l and R A6 = R A m,

L A 18-(m)(n)(p)(q)(r), wherein p is an integer from 1 to 86, and m, n, q, and r are each an integer from 1 to 77, wherein L A 18- (1)(1)(1)(1)(1) to L A 18- (86)(86)(77)(86)(86), having the structure

wherein R A5 = R A m, R A6 = R A n, R A8 = R A p, R A9 , R A q, and R A10 = R A r,

wherein R A 1 to R A 86 have the following structures:

and

wherein L B is selected from the group consisting of the following structures:

L B

Structure of L B

R B1 - R B17

L B 1-(i)(j)(k)(o)(p)(q), wherein i is an integer from 1 to 74, and j, k, o, p, and q are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 1- (1)(1)(1)(1)(1)(1) to L B 1- (77)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, and R B10 = R A q,

L B 2-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r and s are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 2-(1)(1)(1)(1) (1)(1)(1)(1) to L B 2-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 3-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r and s are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 3-(1)(1)(1)(1) (1)(1)(1)(1) to L B 3-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

Wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 4-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u), wherein j, k, o, p, q, r, s, t, and u are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 4-(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 4-(77)(86) (86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, R B13 = R A t, and R B14 = R A u,

L B 5-(i)(j)(k)(o)(p)(q), wherein i, j, k, o, p, and q are each an integer from 1 to 86, wherein L B 5- (1)(1)(1)(1)(1)(1) to L B 5-(86)(86)(86) (86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p and R B11 = R A q, wherein i, j, k, o, p and q are integers from 1 to 86

L B 6-(i)(j)(k)(o)(p)(q) (r)(s), wherein p, q, r and s are each an integer from 1 to 86, and i, j, k, and o are each an integer from 1 to 77, wherein L B 6- (1)(1)(1)(1)(1)(1)(1) (1) to L B 6-(77)(77) (77)(77)(86)(86)(86) (86), having the structure

wherein R B2 = R A i, R B3 = R A j, R B4 = R A k, R B5 = R A o, R B6 = R A p, R B7 = R A q, R B8 = R A r, and R B9 = R A s,

L B 7-(i)(j)(k)(o)(p)(q), wherein j, k, o, p, and q are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 7- (1)(1)(1)(1)(1)(1) to L B 7-(77)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, and R B11 = R A q, wherein j, k, o, p and q are integers from 1 to 86 and i is an integer from 1 to 77.

L B 8-(i)(j)(k)(o)(p)(q) (r)(s), wherein q, r, and s are each an integer from 1 to 86, and i, j, k, o, and p are each an integer from 1 to 77, wherein L B 8-(1)(1) (1)(1)(1)(1)(1)(1) to L B 8-(77)(77)(77)(77) (77)(86)(86)(86), having the structure

wherein R B1 = R A i, R B2 = R A j, R B3 = R A k, R B4 = R A o, R B5 = R A p, R B6 = R A q, R B7 = R A r, and R B8 = R A s,

L B 9-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u), wherein i, j, k, o, p, q, r, s, t and u are each an integer from 1 to 86, wherein L B 9-(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 9-(86)(86) (86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t and R B15 = R A u,

L B 10-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u)(v)(w), wherein i, j, k, o, p, q, r, s, t, u, v, and w are each an integer from 1 to 86, wherein L B 10-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 10-(86)(86)(86) (86)(86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t, R B15 = R A u, R B16 = R A v and R B17 = R A w,

L B 11-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u)(v)(w), wherein i, j, k, o, p, q, r, s, t, u, v, and w are each an integer from 1 to 86, wherein L B 11-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 11-(86)(86)(86) (86)(86)(86)(86)(86) (86)(86)(86)(86), having the structure

Wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t, R B15 = R A u, R B16 = R A v and R B17 = R A w,

L B 12-(i)(j)(k)(o)(p)(q) (r)(s)(t), wherein i, j, k, o, p, q, r, s, and t are each an integer from 1 to 86, wherein L B 12-(1)(1)(1)(1) (1)(1)(1)(1)(1) to L B 12-(86)(86) (86)(86)(86)(86) (86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, and R B14 = R A t,

L B 13-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u), wherein i, j, k, o, p, q, r, s, t, and u are each an integer from 1 to 86, wherein L B 13- (1)(1)(1)(1)(1)(1) (1)(1)(1)(1) to L B 13- (86)(86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t, and R B15 = R A u,

L B 14-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u)(v)(w), wherein i, j, k, o, p, q, r, s, t, u, v, and w are each an integer from 1 to 86, wherein L B 14-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 14-(86)(86)(86) (86)(86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t, R B15 = R A u, R B16 = R A v and R B17 = R A w,

L B 15-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u)(v)(w), wherein i, j, k, o, p, q, r, s, t, u, v, and w are each an integer from 1 to 86, wherein L B 15-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 15-(86)(86)(86) (86)(86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t, R B15 = R A u, R B16 = R A v and R B17 = R A w,

L B 16-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u), wherein i, j, k, o, p, q, r, s, t and u are each an integer from 1 to 86, wherein L B 16-(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 16-(86)(86) (86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, R B13 = R A s, R B14 = R A t, and R B15 = R A u,

L B 17-(i)(j)(k)(o)(p)(q) (r)(s)(t), wherein j, k, o, p, q, r, s, and t are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 17- (1)(1)(1)(1) (1)(1)(1)(1)(1) to L B 17-(77)(86) (86)(86)(86)(86) (86)(86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, and R B13 = R A t,

L B 18-(i)(j)(k)(o)(p)(q) (r)(s)(t), wherein j, k, o, p, q, r, s, and t are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 18- (1)(1)(1)(1) (1)(1)(1)(1)(1) to L B 18-(77)(86) (86)(86)(86)(86) (86)(86)(86), having the structure

Wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, and R B13 = R A t,

L B 19-(i)(j)(k)(o)(p)(q) (r)(s)(t), wherein j, k, o, p, q, r, s, and t are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 19- (1)(1)(1)(1) (1)(1)(1)(1)(1) to L B 19-(77)(86) (86)(86)(86)(86) (86)(86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, and R B13 = R A t,

L B 20-(i)(j)(k)(o)(p)(q) (r)(s)(t), wherein j, k, o, p, q, r, s, and t are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 20- (1)(1)(1)(1) (1)(1)(1)(1)(1) to L B 20-(77)(86) (86)(86)(86)(86) (86)(86)(86), having the structure

Wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, and R B13 = R A t,

L B 21-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r, and s, are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 21- (1)(1)(1)(1) (1)(1)(1)(1) to L B 21-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 22-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r, and s, are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 22- (1)(1)(1)(1) (1)(1)(1)(1) to L B 22-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 23-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r, and s, are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 23- (1)(1)(1)(1) (1)(1)(1)(1) to L B 23-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 24-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r, and s, are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 24- (1)(1)(1)(1) (1)(1)(1)(1) to L B 24-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 25-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r, and s, are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 25- (1)(1)(1)(1) (1)(1)(1)(1) to L B 25-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 26-(i)(j)(k)(o)(p)(q) (r)(s), wherein j, k, o, p, q, r, and s, are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 26- (1)(1)(1)(1) (1)(1)(1)(1) to L B 26-(77)(86) (86)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, and R B12 = R A s,

L B 27-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u)(v)(w), wherein j, k, o, p, q, r, s, t, u, v, and w are each an integer from 1 to 86, and i is an integer from 1 to 77 wherein L B 27-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1)(1)(1) to L B 27- (77)(86)(86)(86)(86)(86) (86)(86)(86)(86)(86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, R B13 = R A t, R B14 = R A u, and R B15 = R B v,

L B 28-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u)(v), wherein j, k, o, p, q, r, s, t, u, and v are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 28-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1)(1) to L B 28- (77)(86)(86)(86)(86)(86) (86)(86)(86)(86)(86), having the structure

Wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, R B10 = R A q, R B11 = R A r, R B12 = R A s, R B13 = R A t, R B14 = R A u, and R B15 = R B v,

L B 29-(i)(j)(k)(o)(p)(q) (r)(s)(t)(u), wherein p, q, r, s, t, and u are each an integer from 1 to 86, and i, j, k, and o are each an integer from 1 to 77, wherein L B 29-(1)(1)(1)(1)(1)(1) (1)(1)(1)(1) to L B 29- (77)(86)(86)(86)(86)(86) (86)(86)(86)(86), having the structure

wherein R B2 = R A i, R B3 = R A j, R B4 = R A k, R B5 = R A o, R B6 = R A p, R B7 = R A q, R B8 = R A r, R B9 = R A s, R B10 = R A t, and R B11 = R A u,

L B 30-(i)(j)(k)(o)(p)(q), wherein i, k, o, p, and q are each an integer from 1 to 86, and i is an integer from 1 to 77, wherein L B 30-(1)(1)(1)(1)(1)(1) to L B 30-(77)(86)(86)(86) (86)(86), having the structure

wherein R B1 = R A i, R B6 = R A j, R B7 = R A k, R B8 = R A o, R B9 = R A p, and R B11 = R A q,

L B 31-(i)(j)(k)(o)(p)(q) (r)(s), wherein i, j, k, o, p, q, r, and s are each an integer from 1 to 86, wherein L B 31-(1)(1)(1)(1)(1)(1) (1)(1) to L B 31-(86)(86) (86)(86)(86)(86)(86)(86), having the structure

wherein R B6 = R A i, R B7 = R A j, R B8 = R A k, R B9 = R A o, R B10 = R A p, R B11 = R A q, R B12 = R A r, and R B13 = R A s,

15. 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, comprising the compound of claim 1 ; and

wherein the consumer product is one of a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tied together, a theater or stadium screen, a light therapy device, and a sign.

16. A formulation comprising a compound according to claim 1 .

17. A compound selected from the group consisting of:

18. 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 selected from the group consisting of:

a structure having

and

a structure having

wherein, rings A and B are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;

wherein M is Pt or Pd;

wherein T 1 and T 2 are C;

wherein X 1 -X 5 , Z 1 , and Z 2 are each independently selected from the group consisting of carbon and nitrogen;

wherein R A , R B , R C , and R D each represents mono to a maximum possible number of substitutions, or no substitution;

wherein Y 1 is selected from the group consisting of CRR′, SiRR′, GeR″R″′, BR, O, and S;

wherein Y 2 and Y 3 are each selected from the group consisting of CRR′, SiRR′, BR, NR, O, and S;

wherein if one of Y 2 and Y 3 is O, S, or NR, the other is not O, S, or NR;

wherein n 1 and n 2 are each independently 0 or 1;

wherein when n 1 or n 2 is 1, L 1 or L 2 is present

wherein when n 1 or n 2 is 0, L 1 or L 2 is not present;

wherein n 1 +n 2 is at least 1;

wherein if present, L 1 and L 2 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;

wherein R 1 , R 2 , R, R′, R A , R B , R C , and R D are each independently a 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;

wherein R″ and R″′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heterocycloalkyl, arylalkyl, amino, aryl, heteroaryl, ether, and combinations thereof;

wherein any two substituents may be joined or fused together to form a ring;

when Y 1 is CRR′, BR, O, or S, R 1 comprises aryl;

when Y 1 is BR, at least one of the following is true:

i) R in BR is a 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, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

ii) R 1 is an aryl group comprising three or more phenyl rings that are joined to form a chain; or

iii) n 2 in Formula I is 1 and L 2 is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;

when Y 1 is SiRR′, at least one of the following is true:

i) R and R′ in SiRR′ are each independently a 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, wherein if aryl or heteroaryl are present, the aryl or heteroaryl are joined to form a fused ring; or

ii) R 1 is an aryl group comprising three or more phenyl rings that are joined to form a chain;

if Y 2 is CRR′ wherein at least one of R and R′ is hydrogen or deuterium, then at least one of the following is true:

i) the other of R and R′ of Y 2 is a substituent selected from the group consisting of 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; or

ii) Y 3 is CRR′ wherein at least one of R and R′ is hydrogen or a substituent selected from the group consisting of halogen, 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.

19. The OLED of claim 18 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

20. The OLED of claim 19 , wherein the host is selected from the group consisting of:

and combinations thereof.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded May 24, 2023
From: CHEN, HSIAO-FAN; BROOKS, JASON
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 063738/0054 →
NUNC PRO TUNC ASSIGNMENT Recorded May 24, 2023
From: WILLIAMS, DOUGLAS; STANTON, CHARLES J., III; GUTMAN, EUGENE S.; BAO, WEI
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 063738/0065 →
Continuity (4)
Continuation 16884545 · May 27, 2020
Continuation In Part 16217467 · Dec 12, 2018
Provisional Application 62615729 · Jan 10, 2018
Related Publication 20240049590A1 · Feb 8, 2024
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