Granted Patent B2

US 12,495,715 · App. 17/844,508 · Granted Dec 9, 2025

Inventors: Bin Ma (Plainsboro, NJ); Wei-Chun Shih (Lawrenceville, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Jui-Yi Tsai (Newtown, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Jerald Feldman (Cherry Hill, NJ); Chun Lin (Yardley, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/342C07F15/0033C09K11/06C09K2211/1048C09K2211/185H10K50/11H10K2101/10

Abstract

Claims (111)

1 . A compound of formula Ir(L A ) m (L B ) n ;

wherein m and n are each independently 1 or 2;

wherein m+n=3;

wherein L A has a structure of Formula I

wherein L B has a structure of Formula II

wherein ring D is a 5-membered or 6-membered heterocyclic ring;

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

wherein X for each occurrence is independently C or N;

wherein X 1 —X 12 are each independently C or N;

wherein Y is selected from the group consisting of a BR, BRR′, NR, PR, O, S, Se, C═O, C═S, C═Se, C—NR, C═CRR′, S═O, SO 2 , CR, CRR′, SiRR′, and GeRR′;

Z is C or N, with a proviso that in Formula I, Y is not CRR′, if one of X 1 —X 4 is N;

L is a direct bond or NR;

wherein each R, R′, R″, R F , R A , R B , R C , R D , and R E is a 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, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein L A and L B are not identical;

wherein any two substituents can be joined or fused to form a ring;

wherein if ring D is an imidazole or pyrazole ring, then at least two R A or two R D substituents are joined to form a ring;

wherein if ring D is a pyridine ring, then at least one of the following two conditions is true:

(i) two R D substituents are joined to form a ring;

(ii) no R D substituent that is para to L is silyl or germyl, and at least one R D substituent comprises two or more carbon atoms;

wherein none of X 1 —X 8 is directly attached to CN if R F is

and X 2 is not directly attached to an F; and

wherein Formula II does not include

2 . The compound of claim 1 , wherein at least one R B , R C , or R E is selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, halogen, nitrile, silyl, germyl, and combinations thereof.

3 . The compound of claim 1 , wherein Y is O, S, or Se.

4 . The compound of claim 1 , wherein R F comprises a substituted 6-membered aromatic ring, an arylalkyl group, or a silyl group.

5 . The compound of claim 1 , wherein R B comprises a silyl group, or an alkyl fluoride group; and/or

wherein R C is alkyl; and/or wherein two R A substituents are joined to form a ring.

6 . The compound of claim 1 , wherein ring D is a 5-membered heterocyclic ring; or a 6-membered heterocyclic ring, or wherein ring D is an imidazole or pyrazole ring and two R A substituents are joined to form a ring and two R D substituents are joined to form a ring.

7 . The compound of claim 1 , wherein R D comprises a fused 6-membered ring, a polycyclic fused ring structure, an arylalkyl group, an alkyl group, a silyl group, or an alkyl fluoride group.

8 . The compound of claim 1 , wherein R E comprises an alkyl group, a silyl group, or an aryl group.

9 . The compound of claim 1 , wherein L is a direct bond.

10 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:

wherein R AA represents mono to the maximum number of substitutions, or no substitution;

wherein X 13 —X 16 are each independently C or N; and

wherein each R A is independently a 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, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

11 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:

wherein R CC , and R F1 each independently represents mono to the maximum number of substitutions, or no substitution; and

wherein each of R F1 and R CC is independently a 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, ary, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

12 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of

13 . The compound of claim 1 , wherein the ligand L B is selected from the group consisting of:

wherein:

T is selected from the group consisting of B, Al, Ga, and In;

each of Y 1 to Y 13 is independently selected from the group consisting of C and N;

Y′ is selected from the group consisting of BR e , BR e R f , NR e , PR e , P(O)R e , O, S, Se, C═O, C═S, C═Se, C═NR e , C═CR e R f , S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;

R e and R f can be fused or joined to form a ring;

each R a , R b , R e , and R d independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;

each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; the general substituents defined herein; and

any two R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R f can be fused or joined to form a ring or form a multidentate ligand.

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

wherein:

R a ′, R b ′, and R c ′ each independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;

each of R a1 , R b1 , R c1 , R N , R a ′, R b ′, and R c ′ is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

any two R a ′, R b ′, and R c ′ can be fused or joined to form a ring or form a multidentate ligand.

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

wherein R1 to R80 have the structures defined below:

wherein each Q1 to Q70 has the structure defined below:

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 Ir(L A ) m (L B ) n ;

wherein m and n are each independently 1 or 2;

wherein m+n=3;

wherein L A has a structure of Formula I

wherein L B has a structure of Formula II

wherein ring D is a 5-membered or 6-membered heterocyclic ring;

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

wherein X for each occurrence is independently C or N;

wherein X 1 —X 12 are each independently C or N;

wherein Y is selected from the group consisting of a BR, BRR′, NR, PR, O, S, Se, C═O, C═S, C═Se, C—NR, C═CRR′, S═O, SO 2 , CR, CRR′, SiRR′, and GeRR′;

Z is C or N, with a proviso that in Formula I, Y is not CRR′, if one of X 1 —X 4 is N;

L is a direct bond or NR;

wherein each R, R′, R″, R F , R A , R B , R C , R D , and R E is a 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, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein L A and L B are not identical;

wherein any two substituents can be joined or fused to form a ring;

wherein if ring D is an imidazole or pyrazole ring, then at least two R A or two R D substituents are joined to form a ring;

wherein if ring D is a pyridine ring, then at least one of the following two conditions is true:

(i) two R D substituents are joined to form a ring;

(ii) no R D substituent that is para to L is silyl or germyl, and at least one R D substituent comprises two or more carbon atoms;

wherein none of X 1 —X 8 is directly attached to CN if R F is

and X 2 is not directly attached to an F; and

wherein Formula II does not include

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, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 -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 Ir(L A ) m (L B ) n ;

wherein m and n are each independently 1 or 2;

wherein m+n=3;

wherein L A has a structure of Formula I

wherein L B has a structure of Formula II

wherein ring D is a 5-membered or 6-membered heterocyclic ring;

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

wherein X for each occurrence is independently C or N;

wherein X 1 —X 12 are each independently C or N;

wherein Y is selected from the group consisting of a BR, BRR′, NR, PR, O, S, Se, C═O, C═S, C═Se, C—NR, C═CRR′, S═O, SO 2 , CR, CRR′, SiRR′, and GeRR′;

Z is C or N, with a proviso that in Formula I, Y is not CRR′, if one of X 1 —X 4 is N;

L is a direct bond or NR;

wherein each R, R′, R″, R F , R A , R B , R C , R D , and R E is a 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, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein L A and L B are not identical;

wherein any two substituents can be joined or fused to form a ring;

wherein if ring D is an imidazole or pyrazole ring, then at least two R A or two R D substituents are joined to form a ring;

wherein if ring D is a pyridine ring, then at least one of the following two conditions is true:

(i) two R D substituents are joined to form a ring;

(ii) no R D substituent that is para to L is silyl or germyl, and at least one R D substituent comprises two or more carbon atoms;

wherein none of X 1 —X 8 is directly attached to CN if R F is

and X 2 is not directly attached to an F; and

wherein Formula II does not include

Assignments (1)

Continuity (2)

References Cited (192)