Granted Patent B2

US 12,428,599 · App. 17/653,477 · Granted Sep 30, 2025

Inventors: Tyler Fleetham (Yardley, PA); Joseph A. Macor (Morrisville, PA); Neil Palmer (Frenchtown, NJ); Elena Sheina (Langhorne, PA); Mahesh Paudyal (Middletown, DE); Muazzam Idris (Wilmington, DE)

Assignee: Universal Display Corporation

C09K11/06C07F5/027C07F7/0812C07F7/0816H10K85/322H10K85/40H10K85/658C09K2211/1018H10K50/11H10K2101/10H10K2101/30

Abstract

Claims (191)

1. A compound of Formula I:

wherein

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

X 1 -X 9 are each independently C or N;

Y 1 is selected from the group consisting of a direct bond, O, S, Se, NR, SiRR′, CRR′, and P(O)R;

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

each R, R′, R A , R B , R C , and R D 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, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and

any two groups of R, R′, R A , R B , R C , and R D may be joined or fused to form a ring;

with the proviso that the following conditions are true:

R D is not joined with R A or R B are to form a ring;

when rings A and B are both 6-membered rings, no two R A or R B are joined to form a boracycle;

R C and R D are not joined to form a 5-membered ring;

when rings A and B are both benzene rings the compound of Formula 1 comprises a chemical structure selected from the group consisting of Formulas II, III, IV, V, VI, VII, VIII, and aza variants thereof,

when rings A, B, and D are all benzene rings R D is not Formula V;

Z 1 , Z 2 , and Z 3 are each independently C or N;

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

Ar 1 , Ar 2 , and Ar 3 are each a substituted or unsubstituted aryl or heteroaryl ring, with the proviso that none of Ar 1 , Ar 2 , and Ar 3 are joined to form a ring;

Y 2 , Y 3 , Y 4 , and Y 5 are each independently selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, and GeRR′.

2. The compound of claim 1 , wherein each R, R′, R A , R B , R C , and R D 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 the compound has the structure of Formula IX:

wherein

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

X 1 -X 14 are each independently C or N;

Y 1 is selected from the group consisting of a direct bond, O, S, Se, NR, SiRR′, CRR′, and P(O)R;

when X 10 -X 14 are all C, R D comprises a boryl group and Y 1 is not a direct bond;

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

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

any two adjacent groups of R, R′, R A , R B , R C , and R D may be joined or fused to form a ring.

4. The compound of claim 1 , wherein ring A is a 6-membered carbocyclic ring or wherein ring B is a 6-membered carbocyclic ring.

5. The compound of claim 1 , wherein at least one of ring A and ring B is a 5-membered ring.

6. The compound of claim 1 , wherein ring D is a 6-membered ring.

7. The compound of claim 1 , wherein all of X 1 -X 9 are C.

8. The compound of claim 1 , wherein all of X 10 -X 14 are C.

9. The compound of claim 1 , wherein at least one of X 1 -X 4 is N.

10. The compound of claim 1 , wherein ring D is selected from the group consisting of benzene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, and imidazole.

11. The compound of claim 1 , wherein two R C are joined to form a ring or wherein two R D are joined to form a ring.

12. The compound of claim 1 , wherein Y 1 is O or wherein Y 1 is NR.

13. The compound of claim 1 , wherein at least one of R A , R B , R C , and R D is joined to its respective ring by a single bond and comprises pyrimidine, triazine, quinazoline, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, anthracene, triphenylene, pyridine, pyrazine, fluorene, dibenzofuran, dibenzothiophene, carbazole, quinoline, isoquinoline, triarylboryl, boraanthracene or quinoxaline, which may be further substituted.

14. The compound of claim 1 , wherein R A and R B are joined or fused to form a ring, or R C and R D are joined or fused to form a ring.

15. The compound of claim 1 , wherein ring A and ring B are each independently selected from the group consisting of benzene, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, and pyrrole.

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

wherein X 10 -X 41 are each C or N,

Y 2 and Y 3 are each independently selected from the group consisting of O, S, Se, NR, SiRR′, CRR′, and P(O)R,

R, R′, R A , R B , R C , R D , R E , R F and R G are independently selected from the group consisting of

17. The compound of claim 1 , wherein the compound is selected from the group consisting of those as shown in the following table:

Compound

Structure of compound

for Compound-1-(Rj)(Rk)(Rl), Compound-1- (R1)(R1)(R1) to Compound-1-(R90)(R96)(R96) having the structure

for Compound-2-(Rj)(Rk)(Rl)(Rm), Compound-2- (R1)(R1)(R1)(R1) to Compound-2- (R90)(R96)(R96)(R96) having the structure

for Compound-3-(Rj)(Rk)(Rl), Compound-3- (R1)(R1)(R1) to Compound-3-(R90)(R96)(R96) having the structure

for Compound-4-(Rk)(Rl)(R/m), Compound-4- (R1)(R1)(R1) to Compound-4-(R96)(R96)(R96) having the stracture

for Compound-5-(Rj)(Rk)(Rl)(Rm)(Rn). Compound- 5-(R1)(R1)(R1)(R1)(R1) to Compound-5- (R90)(R96)(R96)(R96)(R96) having the structure

for Compound-6-(Rj)(Rk)(Rl)(Rm), Compound-6- (R1)(R1)(R1)(R1) to Compound-6- (R90)(R96)(R96)(R96) having the structure

for Compound-7-(Ri)(Rj)(Rk), Compound-7- (R1)(R1)(R1) to Compound-7-(R60)(R90)(R96) having the structure

for Compound-8-(Ri)(Rj)(Rk), Compound-8- (R1)(R1)(R1) to Compound-8-(R60)(R90)(R96) having the structure

for Compound-9-(Ri)(Rj)(Rk), Compound-9- (R1)(R1)(R1) to Compound-9-(R60)(R90)(R96) having the structure

for Compound-10-(Ri)(Rj)(Rk), Compound-10- (R1)(R1)(R1) to Compound-10-(R60)(R90)(R96) having the structure

for Compound-11-(Rj)(Rk), Compound-11-(R1)(R1) to Compound-11-(R90)(R96) having the structure

for Compound-12-(Rj)(Rk)(Rl), Compound-12- (R1)(R1)(R1) to Compound-12-(R90)(R96)(R96) having the structure

for Compound-13-(Ri)(Rj)(Rk), Compound-13- (R1)(R1)(R1) to Compound- 13-(R60)(R90)(R96) having the structure

for Compound-14-(Ri)(Rj)(Rk), Compound-14- (R1)(R1)(R1) to Compound-14-(R60)(R90)(R96) having the structure

for Compound-15-(Ri)(Rj)(Rk)(Rl), Compound-15- (R1)(R1)(R1)(R1) to Compound-15- (R60)(R90)(R96)(R96) having the structure

for Compound-16-(Ri)(Rk)(Rl)(Rm), Compound-16- (R1)(R1)(R1)(R1) to Compound-16- (R60)(R96)(R96)(R96) having the structure

for Compound-17-(Ri)(Rk)(Rl)(Rm), Compound-17- (R1)(R1)(R1)(R1) to Compound-17- (R60)(R96)(R96)(R96) having the structure

for Compound-18-(Ri)(Rk)(Rl), Compound-18- (R1)(R1)(R1) to Compound-18-(R60)(R96)(R96) having the structure

for Compound-19-(Ri)(Rj)(Rk), Compound-19- (R1)(R1)(R1) to Compound-19-(R60)(R90)(R96) having the structure

for Compound-20-(Ri)(Rk), Compound-20-(R1)(R1) to Compound-20-(R60)(R96) having the structure

for Compound-21-(Ri)(Rj), Compound-21-(R1)(R1) to Compound-21-(R60)(R90) having the structure

for Compound-22-(Ri)(Rj), Compound-22-(R1)(R1) to Compound-22-(R60)(R90) having the structure

for Compound-23-(Ri)(Rj)(Rk), Compound-23- (R1)(R1)(R1) to Compound-23-(R60)(R90)(R96) having the structure

for Compound-24-(Ri)(Rj)(Rk), Compound-24- (R1)(R1)(R1) to Compound-24-(R60)(R90)(R96) having the structure

for Compound-25-(Ri)(Rj)(Rk)(Rl), Compound-25- (R1)(R1)(R1)(R1) to Compound-25- (R60)(R90)(R96)(R96) having the structure

for Compound-26-(Ri)(Rj)(Rk)(Rl), Compound-26- (R1)(R1)(R1)(R1) to Compound-26- (R60)(R90)(R96)(R96) having the structure

for Compound-27-(Ri)(Rk)(Rl)(R/m), Compound-27- (R1)(R1)(R1)(R1) to Compound-27- (R60)(R96)(R96)(R96) having the structure

for Compound-28-(Ri)(Rk)(Rl)(Rm), Compound-28- (R1)(R1)(R1)(R1) to Compound-28- (R60)(R96)(R96)(R96) having the structure

for Compound-29-(Ri)(Rk)(Rl)(Rm). Compound-29- (R1)(R1)(R1)(R1) to Compound-29- (R60)(R96)(R96)(R96) having the structure

for Compound-30-(Ri)(Rk)(Rl)(Rm). Compound-30- (R1)(R1)(R1)(R1) to Compound-30- (R60)(R96)(R96)(R96) having the structure

for Compound-31-(Ri)(Rk)(Rl)(Rm), Compound-31- (R1)(R1)(R1)(R1) to Compound-31- (R60)(R96)(R96)(R96) having the structure

for Compound-32-(Ri)(Rj)(Rk)(Rl)(Rm), Compound- 32-(R1)(R1)(R1)(R1)(R1) to Compound-32- (R60)(R90)(R96)(R96)(R96) having the structure

for Compound-33-(Ri)(Rj)(Rk), Compound-33- (R1)(R1)(R1) to Compound-33-(R60)(R90)(R96) having the structure

for Compound-34-(Ri)(Rj)(Rk), Compound-34- (R1)(R1)(R1) to Compound-34-(R60)(R90)(R96) having the structure

wherein i is an integer from 1 to 60, j is an integer from 1 to 90, and k, l, m, and n are each independently an integer from 1 to 96, and

R1 to R96 are defined as given in the following list:

Structure

R1

R2

R3

R4

R5

R6

R7

R8

R9

R10

R11

R12

R13

R14

R15

R16

R17

R18

R19

R20

R21

R22

R23

R24

R25

R26

R27

R28

R29

R30

R31

R32

R33

R34

R35

R36

R37

R38

R39

R40

R41

R42

R43

R44

R45

R46

R47

R48

R49

R50

R51

R52

R53

R54

R55

R56

R57

R58

R59

R60

R61

R62

R63

R64

R65

R66

R67

R68

R69

R70

R71

R72

R73

R74

R75

R76

R77

R78

R79

R80

R81

R82

R83

R84

R85

R86

R87

R88

R89

R90

R91

R92

R93

R94

R95

R96

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

19. 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 the compound according to claim 1 .

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 according to claim 1 .

Assignments (1)

Continuity (2)

References Cited (400)