IP Library › Granted Patent US 12,528,833

Granted Patent B2

US 12,528,833 · App. 17/497,028 · Granted Jan 20, 2026

Organic electroluminescent materials and devices

Inventors: Jui-Yi Tsai (Newtown, PA); Alexey Borisovich Dyatkin (Ambler, PA); Walter Yeager (Yardley, PA); Pierre-Luc T. Boudreault (Pennington, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

C07F15/0086 H10K85/346 H10K85/622 H10K85/624 H10K85/626 H10K85/633 H10K85/654 H10K85/6572 H10K85/6574 H10K85/6576 H10K50/11 H10K2101/10 H10K2101/30 H10K2101/40

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Quick Facts

Patent No.: US 12,528,833
App. No.: 17/497,028
Granted: Jan 20, 2026
Kind: B2

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Abstract

Provided are organometallic compounds having Formula I: Also provided are formulations including these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

Claims (126)

1 . A compound of Formula I:

wherein:

M is Pd or Pt;

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

R X is represented by the structure

Ring A, Ring B, Ring C, Ring D, and Ring E are each independently a single ring or a polycyclic fused ring system independently formed from one or more 5-membered or 6-membered carbocyclic or heterocyclic ring;

at least one of Ring A, Ring B, Ring C, Ring D, and Ring E comprises a polycyclic fused ring system comprising four or more 5-membered or 6-membered rings that are each independently heterocyclic or carbocyclic;

X 1 and X 2 , are each independently C or N;

Y 1 , Y 2 , and Y 3 are each independently selected from the group consisting of a direct bond, O, and S;

Z 1 is C or N;

Z 2 is N, X 3 is C, and the ring of Ring C containing X 3 and Z 2 is pyridine;

L 1 , L 2 , and L 3 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;

m1, m2 and m3 are each independently an integer of 0 or 1;

when m1 is 0, L 1 is absent, when m2 is 0, L 2 is absent, and when m3 is 0, L 3 is absent;

at least two of m1, m2 and m3 are 1;

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

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

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

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

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

3 . The compound of claim 1 , wherein the polycyclic fused ring system comprises at least four 5-membered or 6-membered rings that are each independently aryl or heteroaryl.

4 . The compound of claim 1 , wherein Ring A, Ring D, or Ring E is benzene.

5 . The compound of claim 1 , wherein Z 1 is N.

6 . The compound of claim 1 , wherein Z 1 is C.

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

8 . The compound of claim 1 , wherein X is NR X and R X is represented by the structure

wherein each of R E1 , R E2 , R E3 , R E4 , and R E5 is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

9 . The compound of claim 8 , wherein at least one of R E1 , R E3 , and R E5 is alkyl or substituted or unsubstituted aryl.

10 . The compound of claim 1 , wherein at least one of Y 1 , Y 2 , and Y 3 is O.

11 . The compound of claim 1 , wherein m1=1 and L 1 is 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.

12 . The compound of claim 1 , wherein m2=1 and L 2 is 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.

13 . The compound of claim 1 , wherein m3=1 and L 3 is 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.

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

wherein each of X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 13 , X 14 , X 15 is independently C or N;

X 10 , X 11 , and X 12 are each C;

wherein Y 4 is selected from the group consisting of O, S, and NR Y ;

wherein R Y is hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.

15 . The compound of claim 1 , wherein the compound has the formula A k a -(Rl)(Rm)(Rn)(Ro)(Rp)(Rq)(Rr)(Rs), wherein a is an integer from 1 to 36, wherein k is integer from 1 to 70; wherein each of l, m, n, o, p, q, r, and s is independently an integer from 1 to 331; and wherein each A k a -(Rl)(Rm)(Rn)(Ro)(Rp)(Rq)(Rr)(Rs) has the structure defined as follows:

Structure of

A k a -

(Rl)(Rm)(Rn)(Ro)(Rp)(Rq)(Rr)(Rs)

when a is 1, A 1 1 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 1 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 2, A 1 2 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 2 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 3, A 1 3 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 3 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 4, A 1 4 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 4 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 5, A 1 5 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 5 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 6, A 1 6 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 6 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 7, A 1 7 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 7 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 8, A 1 8 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 8 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 9, A 1 9 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 9 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 10, A 1 10 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 10 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 11, A 1 11 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 11 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 12, A 1 12 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 12 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 13, A 1 13 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 13 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 14, A 1 14 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 14 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 15, A 1 15 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 15 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 16, A 1 16 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 16 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 17, A 1 17 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 17 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 18, A 1 18 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 18 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 19, A 1 19 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 19 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 20, A 1 20 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 20 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 21, A 1 21 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 21 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 22, A 1 22 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 22 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 23, A 1 23 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 23 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 24, A 1 24 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 24 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 25, A 1 25 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 25 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 26, A 1 26 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 26 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 27, A 1 27 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 27 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 28, A 1 28 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 28 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 29, A 1 29 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 29 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 30, A 1 30 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 30 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 31, A 1 31 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 31 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 32, A 1 32 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 32 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 33, A 1 33 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 33 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 34, A 1 34 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 34 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

when a is 35, A 1 35 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 35 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331, have the structure

when a is 36, A 1 36 -(R1)(R1)(R1)(R1)(R1)(R1)(R1)(R1) to A 70 36 -(R331)(R331)(R331)(R331)(R331)(R331)(R331)(R331), have the structure

wherein X1 to X70 are defined as follows:

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:

M is Pd or Pt;

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

R X is represented by the structure

X 1 and X 2 , are each independently C or N;

Y 1 , Y 2 , and Y 3 are each independently selected from the group consisting of a direct bond, O, and S;

Z 1 is C or N;

Z 2 is N, X 3 is C, and the ring of Ring C containing X 3 and Z 2 is pyridine;

m1, m2 and m3 are each independently an integer of 0 or 1;

when m1 is 0, L 1 is absent, when m2 is 0, L 2 is absent, and when m3 is 0, L 3 is absent;

at least two of m1, m2 and m3 are 1;

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

wherein any two of R, R′, R A , R B , R C , R D , and R E can be joined or fused together 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 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:

M is Pd or Pt;

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

R X is represented by the structure

X 1 and X 2 , are each independently C or N;

Y 1 , Y 2 , and Y 3 are each independently selected from the group consisting of a direct bond, O, and S;

Z 1 is C or N;

Z 2 is N, X 3 is C, and the ring of Ring C containing X 3 and Z 2 is pyridine;

m1, m2 and m3 are each independently an integer of 0 or 1;

when m1 is 0, L 1 is absent, when m2 is 0, L 2 is absent, and when m3 is 0, L 3 is absent;

at least two of m1, m2 and m3 are 1;

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

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

Assignments (1)

NUNC PRO TUNC ASSIGNMENT Recorded Oct 8, 2021

From: TSAI, JUI-YI; DYATKIN, ALEXEY BORISOVICH; YEAGER, WALTER; BOUDREAULT, PIERRE-LUC T.

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 057739/0413 →

Continuity (2)

Provisional Application 63115110 · Nov 18, 2020

Related Publication 20220153769A1 · May 19, 2022

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