Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12598908-B2
Application number	US-202117410645-A
Country	US
Kind code	B2
Filing date	Aug 24, 2021
Priority date	Sep 30, 2020
Publication date	Apr 7, 2026
Grant date	Apr 7, 2026

Abstract

A compound having a structure of Formula I,

is provided. In Formula I, two of Z 1 , Z 2 , Z 3 , and Z 4 are C and the other two are N; each of X 1 to X 16 is independently C or N; each of L 1 and L 2 is independently a direct bond or a linker; one of L 1 and L 2 is present; M is Pd or Pt; each R A , R B , R C , and R D is independently hydrogen or a substitutent selected from the General Substituent; and any two of R A , R B , R C , and R D can be joined or fused together to form a ring. Formulations, OLEDs, and consumer products including the compound of Formula I are also disclosed.

First claim

What is claimed is:

1 . A compound having a structure of Formula I:

wherein:
rings A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
either Z 1 and Z 4 are both C and Z 2 and Z 3 are both N, or Z 1 and Z 4 are both N and Z 2 and Z 3 are both C;
each of X 1 -X 16 is independently C or N;
each of L 1 and L 2 is independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO 2 , CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
X is selected from the group consisting of O, S, Se, NR′, and CR″;
a and b are each independently 0 or 1;
when a is 0, L 1 is absent and X 1 is not bonded to X 8 , and when b is 0, L 2 is absent and X 7 is not bonded to X 14 ;
a+b=1;
when Z 1 and Z 4 are both C, a=0;
when Z 1 and Z 4 are both N, b=0 or L2 is a direct bond;
when a=1, X 1 and X 8 are both C;
when b=1, X 7 and X 14 are both C;
M is Pd or Pt;
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″, R A , R B , R C , and R D is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
any two of R, R′, R″, R A , R B , R C , and R D can be joined or fused together to form a ring, except that at least one of the following is true (1) no R A is joined or fused to an R C to form a ring, or (2) no R B is joined or fused to an R D to form a ring;
wherein at least one of the following is true:
(i) at least one of ring A or ring B is a 5-membered ring or a heterocyclic ring;
(ii) b=1 and L 2 is a direct bond;
(iii) at least one R A bonded to ring A or at least one R B bonded to ring B is not H;
(iv) two R C are joined or fused to form a ring;
(v) two R D are joined or fused to form a ring; or
(vi) a is 0; and
with the proviso that the compound is not

2 . The compound of claim 1 , wherein each R, 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 each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 1 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 is C.

4 . 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 , X 12 , X 13 , X 14 , X 15 , and X 16 is N.

5 . The compound of claim 1 , wherein at least one of X 4 , X 5 , and X 6 is N, and at least one of X 11 , X 12 , and X 13 is N.

6 . The compound of claim 1 , wherein a=1 and L 1 is selected from a direct bond, O, S, CRR′, SiRR′, and NR.

7 . The compound of claim 1 , wherein Mis Pt.

8 . The compound of claim 1 , wherein rings A and B are each independently a 5-membered or 6-membered aryl or heteroaryl ring.

9 . The compound of claim 1 , wherein ring A and ring B are the same.

10 . 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 Formula I:

wherein:
rings A and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
either Z 1 and Z 4 are both C and Z 2 and Z 3 are both N, or Z 1 and Z 4 are both N and Z 2 and Z 3 are both C;
each of X 1 -X 16 is independently C or N;
each of L 1 and L 2 is independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO 2 , CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
X is selected from the group consisting of O, S, Se, NR′, and CR″;
a and b are each independently 0 or 1;
when a is 0, L′ is absent and X 1 is not bonded to X 8 , and when b is 0, L2 is absent and X 7 is not bonded to X 14 ;
a+b=1;
when Z 1 and Z 4 are both C, a=0;
when Z 1 and Z 4 are both N, b=0 or L2 is a direct bond;
when a=1, X 1 and X 8 are both C;
when b=1, X 7 and X 14 are both C;
M is Pd or Pt;
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″, R A , R B , R C , and R D is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, 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, R′, R″, R A , R B , R C , and R D can be joined or fused together to form a ring, except that at least one of the following is true (1) no R A is joined or fused to an R C to form a ring, or (2) no R B is joined or fused to an R D to form a ring;
wherein at least one of the following is true:
(i) at least one of ring A or ring B is a 5-membered ring or a heterocyclic ring;
(ii) b=1 and L2 is a direct bond;
(iii) at least one R A bonded to ring A or at least one R B bonded to ring B is not H;
(iv) two R C are joined or fused to form a ring;
(v) two R D are joined or fused to form a ring; or
(vii) a is 0; and
with the proviso that the compound is not

11 . The OLED of claim 10 , 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).

12 . The OLED of claim 11 , wherein the host is selected from the group consisting of:

and combinations thereof.

13 . The OLED of claim 10 , wherein the organic layer further comprises

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Feldman Jerald

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/185

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title