Granted Patent B2

US 12,459,966 · App. 17/570,868 · Granted Nov 4, 2025

Inventors: Tyler Fleetham (Newtown, PA); Jui-Yi Tsai (Newtown, PA); Alexey Borisovich Dyatkin (Ambler, PA); Wei-Chun Shih (Lawrenceville, NJ); Suman Layek (Pennington, NJ); Hsiao-Fan Chen (Lawrence Township, NJ); Pierre-Luc T. Boudreault (Pennington, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

C07F15/0086H10K85/346H10K85/622H10K85/624H10K85/626H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K50/12H10K2101/10H10K2101/30H10K2101/40

Abstract

Claims (87)

1. A compound of Formula I:

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

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 21 , X 22 , Z 1 , Z 2 , and Z 3 is independently C or N;

each of L 1 , L 2 , and L 3 is independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═R, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, aryl, heteroaryl, alkyl, and cycloalkyl;

each of a and b is independently 0 or 1;

at least one of a and b is 1;

L 2 is not present if a=0;

L 3 is not present if b=0;

Y is selected from the group consisting of O, S, Se, and NR Y ;

W is selected from the group consisting of O, S, NR W , C═R W , and CR W R W′ ;

at most one of Z 1 , Z 2 , and Z 3 is N;

each of R A , R B , R C , and R D independently represents mono to the maximum allowable substitution, or no substitution;

each R, R′, R A , R B , R C , R D , R Y , R W , and R W′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

any two of R, R′, R A , R B , R C , R D , R Y , R W , and R W′ can be joined or fused to form a ring.

2. The compound of claim 1 , wherein each R, R′, R A , R B , R C , R D , R Y , R W , and R W′ is 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 each of rings A, B, C, and D is independently selected from the group consisting of pyridine, benzene, pyrrole, and imidazole.

4. The compound of claim 1 , wherein L 1 is a direct bond.

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

6. The compound of claim 1 , wherein b is 1 and L 3 is a direct bond.

7. The compound of claim 1 , wherein W is O.

8. The compound of claim 1 , wherein W is NR W or C═R W , wherein R W is joined or fused with R D to form a ring, or Y is NR Y and R W is joined or fused with R to form a ring, or both.

9. The compound of claim 1 , wherein Y is O.

10. The compound of claim 1 , wherein Y is NR Y , wherein R Y comprises aryl, which can be substituted.

11. The compound of claim 10 , wherein R is phenyl, which is ortho substituted by a substituent selected from the group consisting of aryl, alkyl, cycloalkyl, and combinations thereof.

12. The compound of claim 1 , wherein Z 2 or Z 3 is N.

13. The compound of claim 1 , wherein each of X 1 , X 2 , X 3 , X 4 , and X 5 is C.

14. The compound of claim 1 , wherein the compound has a structure selected from the group consisting of:

wherein:

X 6 to X 22 are each independently C or N

R E has the same definition as R A -R D ; and

each of Y E and Y W is independently selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′.

15. The compound of claim 1 , wherein the compound has a structure selected from the group consisting of:

wherein:

each of l, m, n, and o is independently an integer from 1 to 331;

each of p, q, and r is independently an integer from 1 to 337,

R A1 l is Rl,

R A2 m is Rm,

R A3 n is Rn,

R A4 o is Ro,

for p=1 to 331, Y A1 p is N-Rp,

for q=1 to 331, Y A2 q is N-Rq,

for r=1 to 331, Y A1 r is N-Rr,

each of Y A1 332, Y A2 332, and Y A3 332 is O,

each of Y A1 333, Y A2 333, and Y A3 333 is S,

each of Y A1 334, Y A2 334, and Y A3 334 is CMe 2 ,

each of Y A1 335, Y A2 335, and Y A3 335 is SiMe 2 ,

each of Y A1 336, Y A2 336, and Y A3 336 is CPh 2 ,

each of Y A1 337, Y A2 337, and Y A3 337 is SiPh 2 , and

wherein R1 to R331 are defined as follows:

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

17. 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, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 21 , X 22 , Z 1 , Z 2 , and Z 3 is independently C or N;

each of L 1 , L 2 , and L 3 is independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═R, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, aryl, heteroaryl, alkyl, and cycloalkyl;

each of a and b is independently 0 or 1;

at least one of a and b is 1;

L 2 is not present if a=0;

L 3 is not present if b=0;

Y is selected from the group consisting of O, S, Se, and NR Y ;

W is selected from the group consisting of O, S, NR W , C═R W , and CR W R W′ ;

at most one of Z 1 , Z 2 , and Z 3 is N;

each of R A , R B , R C , and R D independently represents mono to the maximum allowable substitution, or no substitution;

each R, R′, R A , R B , R C , R D , R Y , R W , and R W′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

any two of R, R′, R A , R B , R C , R D , R Y , R W , and R W′ can be joined or fused to form a ring.

18. The OLED of claim 17 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety 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).

19. The OLED of claim 18 , wherein the host is selected from the group consisting of:

and combinations thereof.

20. 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 of Formula I:

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

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 21 , X 22 , Z 1 , Z 2 , and Z 3 is independently C or N;

each of L 1 , L 2 , and L 3 is independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═R, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, aryl, heteroaryl, alkyl, and cycloalkyl;

each of a and b is independently 0 or 1;

at least one of a and b is 1;

L 2 is not present if a=0;

L 3 is not present if b=0;

Y is selected from the group consisting of O, S, Se, and NR Y ;

W is selected from the group consisting of O, S, NR W , C═R W , and CR W R W′ ;

at most one of Z 1 , Z 2 , and Z 3 is N;

each of R A , R B , R C , and R D independently represents mono to the maximum allowable substitution, or no substitution;

each R, R′, R A , R B , R C , R D , R Y , R W , and R W′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

any two of R, R′, R A , R B , R C , R D , R Y , R W , and R W′ can be joined or fused to form a ring.

Assignments (1)

Continuity (2)

References Cited (180)