Granted Patent B2

US 12,247,042 · App. 17/483,987 · Granted Mar 11, 2025

Inventors: Jui-Yi Tsai (Newtown, PA); Alexey Borisovich Dyatkin (Ambler, PA); Jerald Feldman (Cherry Hill, NJ); Walter Yeager (Yardley, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Hsiao-Fan Chen (Lawrence Township, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

C07F15/0086H10K85/346H10K85/40H10K85/622H10K85/624H10K85/626H10K85/633H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K2101/30H10K2101/40

Abstract

Claims (128)

1. A compound having a structure of the following Formula I

wherein:

M is Pd or Pt;

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 is independently C or N;

ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, S, and NR;

L 1 is a one atom or two atom linking group;

Y 1 is selected from the group consisting of O, S, BR, PR, Se and NR Y ;

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

each R, R Y , 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, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;

any two of R, R Y , R A , R B , R C , and R D can be joined or fused to form a ring; and when Y 1 comprises a substituent that is an aromatic ring, then at least one of the following is true:

i) L 1 is a two atom linking group; or

ii) said aromatic ring is substituted with at least one other ring.

2. The compound of claim 1 , each R, R Y , 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 at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 is N.

4. The compound of claim 1 , wherein each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 is C.

5. The compound of claim 1 , wherein one of K 1 and K 2 is a direct bond and the other of K 1 and K 2 is selected from the group consisting of O, S, and NR.

6. The compound of claim 1 , wherein K 1 is O and K 2 is a direct bond; or K 1 is a direct bond and K 2 is O.

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

8. The compound of claim 1 , wherein Y 1 is NR Y , and R Y is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereon, and combinations thereof.

9. The compound of claim 1 , wherein a one atom or two atom linking group L 1 is selected from the group consisting of —X—, —X—X′—, and —X L ═X L′ —; wherein X and X′ are each independently selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeRR″ and X L and X L′ are each independently selected from the group consisting of N and CR L ;

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

any two R′, R″, and R L can be joined or fused to form a ring.

10. The compound of claim 9 , wherein one of the following conditions is true:

L 1 is —X—;

X is S; X is O; and

X is NR′.

11. The compound of claim 9 , wherein one of the following conditions is true:

L 1 is —X—X′—;

at least one of X and X′ is NR′;

at least one of X and X′ is BR′;

at least one of X and X′ is CR′R″;

at least one of X and X′ is S; and

at least one of X and X′ is O.

12. The compound of claim 9 , wherein one of the following conditions is true:

L 1 is —X L =X L′ —;

at least one of X L and X L′ is N; and

at least one of X L and X L′ is CR L .

13. The compound of claim 1 , wherein M is Pt.

14. The compound of claim 1 , wherein the compound is selected from the group consisting of Compound Pt(L A x-(Ri)(Rj)(Rk)(Rl)(Ym))(L B y-(Rn)(Ro)(Rp)(Rq) a )(L Z ), wherein x is an integer from 1 to 3, y is an integer from 1 to 25, z is an integer from 1 to 25, wherein i, j, k, and l are each independently an integer from 1 to 24, m is an integer from 1 to 11, n, o, and p are each independently an integer from 1 to 24, and q is an integer from 1 to 11,

wherein, when x is 1 or 2, y is an integer from 1 to 19;

wherein, when x is 3, y is an integer from 20-25;

wherein a is 0 or 1 and Rq is not present when a is 0;

wherein L Z is a bridge structure between L A x-(Ri)(Rj)(Rk)(Rl)(Ym) and L B y-(Rn)(Ro)(Rp)(Rq) a ;

wherein each L A x-(Ri)(Rj)(Rk)(Rl)(Ym) has the structure defined below:

Structure of

Structure of

L A x-

L A x-(Ri)(Rj)(Rk)(Rl)(Ym)

(Ri)(Rj)(Rk)(Rl)(Ym)

when x is 1, L A 1- (R1)(R1)(R1)(R1)(Y1) to L A 1- (R24)(R24)(R24)(R24)(Y11), have the structure

when x is 2, L A 2- (R1)(R1)(R1)(R1)(Y1) to L A 2- (R24)(R24)(R24)(R24)(Y11), have the structure

when x is 3, L A 3- (R1)(R1)(R1)(R1)(Y1) to L A 3- (R24)(R24)(R24)(R24)(Y11), have the structure

wherein L B y-(Rn)(Ro)(Rp)(Rq) a has the following structures:

Structure of

L B y-(Rn)(Ro)(Rp)(Rq) a

when y is 1, a is 0, and L B 1-(R1)(R1)(R1) to L B 1- (R24)(R24)(R24), have the structure

when y is 2, a is 0, and L B 2-(R1)(R1)(R1) to L B 2- (R24)(R24)(R24), have the structure

when y is 3, a is 0, and L B 3-(R1)(R1)(R1) to L B 3- (R24)(R24)(R24), have the structure

when y is 4, a is 0, and L B 4-(R1)(R1)(R1) to L B 4- (R24)(R24)(R24), have the structure

when y is 5, L B 5- (R1)(R1)(R1)(Y1) to L B 5- (R24)(R24)(R24)(Y11), have the structure

when y is 6, L B 6- (R1)(R1)(R1)(Y1) to L B 6- (R24)(R24)(R24)(Y11), have the structure

when y is 7, L B 7- (R1)(R1)(R1)(Y1) to L B 7- (R24)(R24)(R24)(Y11), have the structure

when y is 8, a is 0, and L B 8-(R1)(R1)(R1) to L B 8- (R24)(R24)(R24), have the structure

when y is 9, L B 9- (R1)(R1)(R1)(Y1) to L B 9- (R24)(R24)(R24)(Y11), have the structure

when y is 10, a is 0, and L B 10-(R1)(R1)(R1) to L B 10- (R24)(R24)(R24), have the structure

when y is 11, a is 0, and L B 11-(R1)(R1)(R1) to L B 11- (R24)(R24)(R24), have the structure

when y is 12, a is 0, and L B 12-(R1)(R1)(R1) to L B 12- (R24)(R24)(R24), have the structure

when y is 13, L B 13- (R1)(R1)(R1)(Y1) to L B 13- (R24)(R24)(R24)(Y11), have the structure

when y is 14, L B 14- (R1)(R1)(R1)(Y1) to L B 14- (R24)(R24)(R24)(Y11), have the structure

when y is 15, L B 15- (R1)(R1)(R1)(Y1) to L B 15- (R24)(R24)(R24)(Y11), have the structure

when y is 16, a is 0, L B 16-(R1)(R1)(R1) to L B 16- (R24)(R24)(R24), have the structure

when y is 17, a is 0, L B 17-(R1)(R1)(R1) to L B 17- (R24)(R24)(R24), have the structure

when y is 18, a is 0, L B 18-(R1)(R1)(R1) to L B 18- (R24)(R24)(R24), have the structure

when y is 19, a is 0, L B 19-(R1)(R1)(R1) to L B 19- (R24)(R24)(R24), have the structure

when y is 20, a is 0, L B 20-(R1)(R1)(R1) to L B 20- (R24)(R24)(R24), have the structure

when y is 21, a is 0, L B 21-(R1)(R1)(R1) to L B 21- (R24)(R24)(R24), have the structure

when y is 22, L B 22- (R1)(R1)(R1)(Y1) to L B 22- (R24)(R24)(R24)(Y11), have the structure

when y is 23, a is 0, L B 23-(R1)(R1)(R1) to L B 23- (R24)(R24)(R24), have the structure

when y is 24, a is 0, L B 24-(R1)(R1)(R1) to L B 24- (R24)(R24)(R24), have the structure

when y is 25, L B 25- (R1)(R1)(R1)(Y1) to L B 25- (R24)(R24)(R24)(Y11), have the structure

wherein R1 to R24 have the following structures:

wherein Y1 to Y11 have the following structures:

and

wherein L 1 is selected from the group consisting of:

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

16. 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 the following Formula I

wherein:

M is Pd or Pt;

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 is independently C or N;

ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, S, and NR;

L 1 is an organic linker;

Y 1 is selected from the group consisting of O, S, BR, PR, Se and NR Y ;

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

each R, R Y , 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, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, 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 of R, R Y , R A , R B , R C , and R D can be joined or fused to form a ring; and

when Y 1 comprises a substituent that is an aromatic ring, then at least one of the following is true:

i) L 1 is a two atom linking group; or

ii) said aromatic ring is substituted with at least one other ring.

17. The OLED of claim 16 , wherein the organic layer further comprises a host, wherein the 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).

18. The OLED of claim 17 , wherein the host is selected from the group consisting of:

and combinations thereof.

19. 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 the following Formula I

wherein:

M is Pd or Pt;

each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 is independently C or N;

ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, S, and NR;

Ln is an organic linker;

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

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

each R, R Y , 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, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, 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 of R, R Y , R A , R B , R C , and R D can be joined or fused to form a ring; and

when Y 1 comprises a substituent that is an aromatic ring, then at least one of the following is true:

i) L 1 is a two atom linking group; or

ii) said aromatic ring is substituted with at least one other ring.

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

each X 9′ , X 12′ , X 14 , and X 15 is independently C or N;

each R E and R F independently represents mono to the maximum allowable substitution, or no substitution;

R E and R F 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, 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 of R E , R F and R A , R B , R C , and R D can be joined or fused to form a ring.

Assignments (1)

Continuity (2)

References Cited (194)