Granted Patent B2

US 12,509,628 · App. 18/062,668 · Granted Dec 30, 2025

Inventors: Jui-Yi Tsai (Newtown, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Jerald Feldman (Cherry Hill, NJ); Bert Alleyne (Newtown, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

C09K11/06H10K50/11H10K85/346C09K2211/185

Abstract

Claims (91)

1 . A compound of Formula I,

wherein:

M is Pd or Pt;

each of X 1 to X 14 is independently C or N;

one of Z 1 and Z 2 is C and the other is N;

Y is selected from the group consisting of O, S, Se, N*R, CRR′, SiRR′, and GeRR′;

K 1 is selected from the group consisting of a direct bond, O, and S;

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 , 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, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;

at least one of R, R′, R A , R B , R C , or R D is a substituent R*;

one of the following two statements is true:

(i) R* comprises a 5-membered or 6-membered heterocyclic ring;

(ii) R* comprises Formula Ia,

wherein each of R Y and R Z independently represents mono to the maximum allowable substitution, or no substitution;

R 1 , R 2 , R 3 , R 4 , R Y and R Z is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;

wherein at least one of R 1 , R 2 , R 3 , and R 4 is not hydrogen; and

any two substituents may be joined or fused to form a ring.

2 . The compound of claim 1 , wherein R* comprises a structure selected from the group consisting of

wherein:

L is selected from the group consisting of a direct bond, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, partially or fully deuterated variants thereof, and combinations thereof;

R 1 is selected from the group consisting of alkyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, partially or fully deuterated variants thereof, and combinations thereof;

Z is selected from the group consisting of N, NR Z , O, S, Se, CR Z R Z′ , and SiR Z R Z′ ;

Z is N if L is bonded to Z;

if R* is Formula III and Z is N, then L is not a direct bond;

each of X 15 to X 37 is independently C or N;

at least one of X 32 to X 37 is N;

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

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

any two of R Z , R Z′ , R E , R F , R G , R H , and R I may be joined or fused to form a ring.

3 . The compound of claim 2 , wherein R* has a structure of Formula II, wherein each of X 15 to X 23 is C; and/or each of X 24 to X 31 is C.

4 . The compound of claim 2 , wherein R* has a structure of Formula II, wherein at least one of X 19 to X 23 is N; and/or at least one of X 24 to X 27 is N.

5 . The compound of claim 2 , wherein R* has a structure of Formula II, wherein L is bonded to X 32 .

6 . The compound of claim 2 , wherein R* has a structure of Formula III, wherein Z is NR Z .

7 . The compound of claim 1 , wherein each R, R′, R A , R B , R C , and R D is independently 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, boryl, and combinations thereof.

8 . The compound of claim 1 , wherein at least one R D is a substituent R*.

9 . The compound of claim 1 , wherein each of X 1 to X 14 is C.

10 . The compound of claim 1 , wherein at least one of X 1 to X 14 is N.

11 . The compound of claim 1 , wherein K 1 is O.

12 . The compound of claim 1 , wherein Z 1 is C and Z 2 is N.

13 . The compound of claim 1 , wherein Y is N*R.

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

wherein:

R 1 is selected from the group consisting of alkyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, partially or fully deuterated variants thereof, and combinations thereof;

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

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

any two of R Z , R E , R F , R G , and R H may be joined or fused to form a ring.

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

16 . The compound of claim 1 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;

each of X 1 to X 14 is independently C or N;

one of Z 1 and Z 2 is C and the other is N;

Y is selected from the group consisting of O, S, Se, N*R, CRR′, SiRR′, and GeRR′;

K 1 is selected from the group consisting of a direct bond, O, and S;

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 , 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, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;

at least one of R, R′, R A , R B , R C , or R D is a substituent R*;

one of the following two statements is true:

(i) R* comprises a 5-membered or 6-membered heterocyclic ring;

(ii) R* comprises Formula Ia,

wherein each of R Y and R Z independently represents mono to the maximum allowable substitution, or no substitution;

R 1 , R 2 , R 3 , R 4 , R Y and R Z is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;

wherein at least one of R 1 , R 2 , R 3 , and R 4 is not hydrogen; and

any two substituents may be joined or fused 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, dibenzothiphene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, boryl, silyl, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 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 (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;

each of X 1 to X 14 is independently C or N;

one of Z 1 and Z 2 is C and the other is N;

Y is selected from the group consisting of O, S, Se, N*R, CRR′, SiRR′, and GeRR′;

K 1 is selected from the group consisting of a direct bond, O, and S;

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 , 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, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;

at least one of R, R′, R A , R B , R C , or R D is a substituent R*;

one of the following two statements is true:

(i) R* comprises a 5-membered or 6-membered heterocyclic ring;

(ii) R* comprises Formula Ia,

wherein each of R Y and R Z independently represents mono to the maximum allowable substitution, or no substitution;

R 1 , R 2 , R 3 , R 4 , R Y and R Z is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;

wherein at least one of R 1 , R 2 , R 3 , and R 4 is not hydrogen; and

any two substituents may be joined or fused to form a ring.

Assignments (1)

Continuity (4)

References Cited (181)