Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12459966-B2
Application number	US-202217570868-A
Country	US
Kind code	B2
Filing date	Jan 7, 2022
Priority date	Feb 2, 2021
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

Abstract

Compound of Formula I,is provided. In Formula I, rings A, B, C, and D are 5- or 6-membered rings; each of X1-X5, X21-X22, and Z1-Z3 is C or N; each of L1, L2, and L3 is selected from a direct bond or a divalent linker; each of a and b is 0 or 1; Y is O, S, Se, or NRY; W is O, S, NRW, C═RW, or CRWRW′; up to 1 of Z1 to Z3 is N; each R, R′, RA, RB, RC, RD, RY, RW, and RW′ is hydrogen or a substituent. Formulations, OLEDs, and consumer products containing the same are also disclosed.

First claim

What is claimed is:

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:

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Tsai Jui-Yi
• Dyatkin Alexey Borisovich
• Shih Wei-Chun
• Layek Suman
• Chen Hsiao-Fan
• Boudreault Pierre-Luc T

Classifications

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title