Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12349589-B2
Application number	US-202117528552-A
Country	US
Kind code	B2
Filing date	Nov 17, 2021
Priority date	Jan 28, 2020
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

A compound comprising a ligand LA comprising a moiety L having a structure of Formula Iis provided. In Formula I, LA coordinated to a metal M; A1 is selected from B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; where rings A, B, and C are 5- or 6-membered rings; Y1, Y2, and Y3 are selected from direct bonds, the metal M, and a variety of linkers; a+b+c=2 or 3; and one of a number of specific conditions is met. OLED devices, consumer products, and formulations including the compound are also provided.

First claim

What is claimed is:

1. A compound comprising a ligand L A ,
wherein L A comprises a moiety L having a structure of Formula I:

wherein:
L A coordinated to a metal M;
A 1 is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″;
each rings A, B, and C is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Y 1 , Y 2 , and Y 3 are each independently a moiety selected from the group consisting of direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO 2 , CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, metal M and combinations thereof;
wherein X is selected from the group consisting of O, S, Se, NR′, and CR″R′″;
a, b, and c are each independently 0 for not present or 1 for present;
a+b+c=2 or 3;
R A , R B , and R C each independently represent mono to the maximum allowable substitution, or no substitution;
each R, R′, R″, R′″, R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M can be coordinated to other ligands;
the ligand L A can be joined with other ligands to form a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two substituents of R, R′, R″, R′″, R A , R B , and R C can be joined or fused to form a ring;
if the compound comprises a ring that includes metal M and A1, then one or more of the following is true: (i) A 1 is not B, (ii) at least one of Y 1 , Y 2 , or Y 3 is present and is not metal M, O, or S, (iii) one of Y 1 , Y 2 , or Y 3 comprises metal M and one of the remaining two of Y 1 , Y 2 , or Y 3 is not present, or (iv) at least one of ring A, ring B, or Ring C is pyrazole or imidazole coordinated to metal M by a N atom; and
at least one of the following conditions is true:
1) At least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring;
2) At least one of Y 1 , Y 2 , or Y 3 is present as C═R;
3) A 1 is B and at least one of Y 1 , Y 2 , and Y 3 is present as a direct bond;
4) A 1 is B, a=b=1, and Y 1 is different from Y 2 ;
5) A 1 is N and at least one of Y 1 , Y 2 , and Y 3 is present as BR;
6) A 1 is B, a=b=1, and Y 1 is not O;
7) The compound comprises a metal-carbene bond; or
8) At least one pair of adjacent R A , R B , or R C join together to form a fused moiety comprising one or more rings fused to and extending from Ring A, Ring B, or Ring C, respectively, wherein the fused moiety coordinates directly to the metal M, and at most only one of rings A, B, or C is coordinated to the metal M.

2. The compound of claim 1 , wherein each R, R′, R″, R′″, R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of the metal M, 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 most only one of rings A, B, and C is coordinated to the metal M.

4. The compound of claim 3 , wherein none of rings A, B, and C are coordinated to the metal M.

5. The compound of claim 1 , wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.

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

wherein
each of X 1 , X 2 , X 3 , X 4 , X 3 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , and X 19 is independently C or N;
R D and R E each independently represent mono to the maximum allowable substitution, or no substitution;
each R D and R E is independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
each of Y 4 , Y 5 , and Y 6 is independently selected from the group consisting of C═R, NR, O, S, Se, BR, CRR′, SiRR′, GeRR′, and SnRR′; and
any two substituents of R, R′, R″, R′″, R A , R B , R C , R D and R E can be joined or fused to form a ring.

7. The compound of claim 1 , wherein the compound has a structure of

wherein:
Z 1 , Z 2 , Z 3 , and Z 4 are independently selected from C or N;
M 1 is Pd or Pt;
each one of rings A 1 , A 2 , A 3 , and A 4 is independently monocyclic or multicyclic ring structures comprising at least one 5-membered or 6-membered carbocyclic or heterocyclic ring;
K 1 to K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least one of K 3 and K 4 is a direct bond;
L 1 to L 4 are each independently selected from the group consisting of a single bond, absent a bond, O, S, C═R′, CR′R″, SiR′R″, BR′, BR′R″, and NR′, wherein at least two of L 1 to L 4 are present;
R 1 ′, R 2 ′, R 3 ′ and R 4 ′ each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R 1 ′, R 2 ′, R 3 ′ R 4 ′, R′, and R″ 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two of R 1 ′, R 2 ′, R 3 ′ R 4 ′, R′, and R″ can be joined or fused together to form a ring; and
at least one of R 1 ′, R 2 ′, R 3 ′, R 4 ′, L 1 , L 2 , L 3 , L 4 , ring A 1 , ring A 2 , ring A 3 , ring A 4 , or a combination thereof comprises a structure of Formula I.

8. The compound of claim 7 , wherein each one of rings A 1 , A 2 , A 3 , and A 4 is independently a monocyclic or a multicyclic aromatic ring structure.

9. The compound of claim 7 , wherein each one of rings A 1 , A 2 , A 3 , and A 4 is independently selected from the group consisting of phenyl, pyridine, pyrazine, pyrimidine, pyridazine, imidazole, imidazole derived carbene, pyrazole, furane, thiophene, pyrrole, and benzo-fused variants thereof.

10. The compound of claim 7 , wherein at least one of L 1 , L 2 , L 3 , and L 4 is O, NR′, or CR′R″.

11. The compound of claim 7 , wherein two of Z 1 , Z 2 , Z 3 , and Z 4 are C, and the remaining two of Z 1 , Z 2 , Z 3 , and Z 4 are N.

12. The compound of claim 7 , wherein two of Z 1 , Z 2 , Z 3 , and Z 4 are C, one of Z 1 , Z 2 , Z 3 , and Z 4 is carbene C, and the remaining one of Z 1 , Z 2 , Z 3 , and Z 4 is N.

13. The compound of claim 7 , wherein K 1 , K 2 , K 3 , and K 4 are all direct bonds.

14. The comp

Assignees

• Universal Display Corp

Inventors

• Macinnis Morgan C
• Chen Hsiao-Fan
• Fleetham Tyler
• Wolohan Peter
• Feldman Jerald
• Tsai Jui-Yi
• Boudreault Pierre-Luc T
• Dyatkin Alexey Borisovich
• Ji Zhiqiang
• Ryno Sean Michael
• Hamze Rasha
• Lin Chun
• Sheina Elena

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/342

  comprising iridium · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title