Granted Patent B2

US 12,624,055 · App. 17/651,816 · Granted May 12, 2026

Inventors: Peter Wolohan (Princeton Junction, NJ); Tyler Fleetham (Yardley, PA); Hsiao-Fan Chen (Lawrence Township, NJ)

Assignee: Universal Display Corporation

C07F5/027C07F5/02C07F7/0816H10K85/623H10K85/626H10K85/654H10K85/6572H10K85/658H10K50/11H10K2101/10

Abstract

Claims (69)

1 . A compound having a structure of Formula I:

wherein

rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

L 1 , L 2 , L 3 , L 4 , L′, and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P (O)R, and GeRR′;

a, b, c, d, e and f are each 0 for not present or 1 for present;

a+b+c and d+e+f are each greater than or equal to 2;

with the proviso that the following two conditions are true:

1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and

2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR;

R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and

any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring.

2 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are all aryl.

3 . The compound of claim 1 , wherein at least one of rings A, B, C, D, E, and F is heteroaryl.

4 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are all 6-membered rings.

5 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are each benzene rings.

6 . The compound of claim 1 , wherein at least one of rings A, B, C, D, E, and F is a 5-membered ring.

7 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are all single rings.

8 . The compound of claim 1 , wherein at least one of rings A, B, C, D, E, and F is a fused ring.

9 . The compound of claim 1 , wherein rings A, B, C, D, E, and F are each independently selected from the group consisting of benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

10 . The compound of claim 1 , wherein L1, L2, L3, L4, L5, and L6 are each independently optionally present or being selected from the group consisting of O, S, NR, CRR′, and SiRR′, wherein R and R′ are each independently 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.

11 . The compound of claim 1 , wherein each of R1, R2, R3, R4, R5, and R6 are joined to its respective ring by a single bond and comprises hydrogen, deuterium, alkyl, heteroalkyl, pyrimidine, triazine, quinazoline, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, anthracene, triphenylene, pyridine, pyrazine, fluorene, dibenzofuran, dibenzothiophene, carbazole, quinoline, isoquinoline, triarylboryl, boraanthracene or quinoxaline, which may be further substituted.

12 . The compound of claim 1 , wherein each of R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of

13 . The compound of claim 1 , wherein one, two, or three of R1, R2, and R3 are not hydrogen, and the remainder of R1, R2, and R3 are hydrogen.

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

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

where R1, R2, R3, R4, R5 and R6 are independently comprising a structure selected from the group consisting of

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 having a structure of Formula I:

wherein

rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P (O)R, and GeRR′;

a, b, c, d, e and f are each 0 for not present or 1 for present;

a+b+c and d+e+fare each greater than or equal to 2;

with the proviso that the following two conditions are true:

1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and

2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR;

R 1 , R 2 , R 3 , R 4 , R 5 , and Re are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and

any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring.

18 . The OLED of claim 17 , wherein the compound is a host, and the organic layer is an emissive layer that comprises a phosphorescent emitter.

19 . The OLED of claim 17 , wherein the phosphorescent emitter is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate 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 carbon and nitrogen;

Y′ is selected from the group consisting of BR e , NR e , PRE, O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , P(O)R e , 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 c , and R d 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 d1 , R a , R b , R c , R d , R e R f , R a ′, R c ′, R B , and R N is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and

any two adjacent substituents of 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.

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 having a structure of Formula I:

wherein

rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SIRR′, P (O)R, and GeRR′;

a, b, c, d, e and f are each 0 for not present or 1 for present;

a+b+c and d+e+fare each greater than or equal to 2;

with the proviso that the following two conditions are true:

1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and

2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L2, L3, L5 and L6 are not all NR;

R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and

any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring.

Assignments (1)

Continuity (2)

References Cited (400)