Granted Patent B2

US 12,262,628 · App. 18/437,316 · Granted Mar 25, 2025

Inventors: Hsiao-Fan Chen (Lawrence Township, NJ); Tyler Fleetham (Newtown, PA); Rasha Hamze (Philadelphia, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/322C07F5/027C09K11/02C09K11/06C09K2211/1007C09K2211/1018H10K50/121H10K2101/27

Abstract

Claims (137)

1. A compound of Formula I

wherein:

rings A and B are each independently a 5-membered or 6-membered heterocyclic ring;

rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

L is N or CR;

X is O, S, NR, BR, BRR′, CRR′, or SiRR′;

R A , R B , R C , and R D each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;

R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;

R and R′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;

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

with the proviso that if rings A and B are both a 5-membered heterocyclic ring, then:

one of the following conditions i) and ii) is true:

i) L is N; or

ii) L is CR and R is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein if R is aryl, the aryl is a substituted aryl;

and at least one of the following conditions iii) and iv) is true:

iii) in at least one of ring A and ring B, the atom adjacent to the nitrogen atom is a carbon substituted with hydrogen; or

iv) two R A or two R B are joined to form a ring.

2. The compound of claim 1 , wherein R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and

R and R′ are each 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 rings C and D are each benzene rings.

4. The compound of claim 1 , wherein rings C and D are each 6-membered heterocyclic rings.

5. The compound of claim 1 , wherein rings A and B are each pyridine rings.

6. The compound of claim 1 , wherein rings A and B are each 5-membered heterocyclic rings.

7. The compound of claim 1 , wherein X is O, S, NR, BR.

8. The compound of claim 1 , wherein X is BRR′, CRR′ or SiRR′, with R and R′ joined together to form a 6-membered heterocyclic ring.

9. The compound of claim 1 , wherein at least one pair of adjacent substituents selected from the group consisting of two adjacent R A substituents, two adjacent R B substituents, two adjacent R C substituents, and two adjacent R D substituents are joined together to form a fused 6-membered aromatic ring, which can be further fused.

10. The compound of claim 1 , wherein at least two pairs of adjacent substituents selected from the group consisting of two adjacent R A substituents, two adjacent R B substituents, two adjacent R C substituents, and two adjacent R D substituents are joined together to form a fused 6-membered aromatic ring, which can be further fused.

11. The compound of claim 1 , wherein L is N.

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

wherein:

X 1 -X 20 are each independently CR or N;

L 1 and L 2 are each independently N or CR;

R E , and R F are each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

13. The compound of claim 1 , wherein the compound is selected from the group consisting of the following compounds, wherein i, j are independently an integer from 1 to 725, and k is an integer from 1 to 61:

Compound name

Structure

Compound I-[(Ai)(Aj)][(Ai)(Aj)]Rk, wherein Compound I-[(A1)(A1)][(A1)(A1)]R1 to Compound I-[(A725)(A725)][(A725)(A725)]R61 having the structure

Compound II-[(Ai)(Aj)]Rk, wherein Compound II-[(A1)(A1)]R1 to Compound II-[(A725)(A725)]R61 having the structure

Compound III-[(Ai)(Aj)]Rk, wherein Compound III-[(A1)(A1)]R1 to Compound III-[(A725)(A725)]R61 having the structure

Compound IV-[(Ai)(Aj)]Rk, wherein Compound IV-[(A1)(A1)]R1 to Compound IV-[(A725)(A725)]R61 having the structure

Compound V-[(Ai)(Aj)]Rk, wherein Compound V-[(A1)(A1)]R1 to Compound V-[(A725)(A725)]R61 having the structure

Compound VI-[(Ai)(Aj)]Rk, wherein Compound VI-[(A1)(A1)]R1 to Compound VI-[(A725)(A725)]R61 having the structure

Compound VII-[(Ai)(Aj)]Rk, wherein Compound VII-[(A1)(A1)]R1 to Compound VII-[(A725)(A725)]R61 having the structure

Compound VIII-[(Ai)(Aj)]Rk, wherein i, j are independently an integer from 1 to 725, and k is an integer from 1 to 61, wherein Compound VIII-[(A1)(A1)]R1 to Compound VIII-[(A725)(A725)]R50 having the structure

Compound IX-[(Ai)(Aj)]Rk, wherein Compound IX-[(A1)(A1)]R1 to Compound IX-[(A725)(A725)]R50 having the structure

Compound X-[(Ai)(Aj)]Rk, wherein Compound X-[(A1)(A1)]R1 to Compound X-[(A725)(A725)]R50 having the structure

Compound XI-[(Ai)(Aj)]Rk, wherein Compound XI-[(A1)(A1)]R1 to Compound XI-[(A725)(A725)]R50 having the structure

Compound XII-[(Ai)(Aj)][(Ai)(Aj)]Rk, wherein Compound XII-[(A1)(A1)][(A1)(A1)]R1 to Compound XII-[(A725)(A725)][(A725)(A725)]R61 having the structure

Compound XIII-[(Ai)(Aj)][(Ai)(Aj)]Rk, wherein Compound XIII-[(A1)(A1)][(A1)(A1)]R1 to Compound XIII-[(A725)(A725)][(A725)(A725)]R61 having the structure

Compound XIV-[(Ai)(Aj)][(Ai)(Aj)]Rk, wherein Compound XIV-[(A1)(A1)][(A1)(A1)]R1 to Compound XIV-[(A725)(A725)][(A725)(A725)]R61 having the structure

Compound XV-[(Ai)(Aj)][(Ai)(Aj)]Rk, wherein Compound XV-[(A1)(A1)][(A1)(A1)]R1 to Compound XV-[(A725)(A725)][(A725)(A725)]R61 having the structure

wherein L A and L B each independently have the following structure:

wherein each Ai and Aj has the structure defined below, wherein k′ is an integer from 1 to 60:

Ai, Aj

Structure of Ai and Aj

R

wherein, for i = 1 or j = 1, A1 has the structure

wherein, for i = 2 to 61 or j = 2 to 61, A2 to A61 have the structure

wherein R = Rk', wherein for each i, k' = i − 1, and for each j, k' = j − 1, and

wherein, for i = 62 to 121 or j = 62 to 121, A62 to A121 have the structure

wherein R = Rk', wherein for each i, k' = i − 61, and for each j, k' = j − 61, and

wherein, for i = 122 to 181 or j = 122 to 181, A122 to A181 have the structure

wherein R = Rk', wherein for each i, k' = i − 121, and for each j, k' = j − 121, and

wherein, for i = 182 or j = 182, A182 has the structure

wherein, for i = 183 to 242 or j = 183 to 242, A183 to A242 have the structure

wherein R = Rk', wherein for each i, k' = i − 182, and for each j, k' = j − 182, and

wherein, for i = 243 or j = 243, A243 has the structure

wherein, for i = 244 to 303 or j = 244 to 303, A244 to A303 have the structure

wherein R = Rk', wherein for each i, k' = i − 243, and for each j, k' = j − 243, and

wherein, for i = 304 or j = 304, A304 has the structure

wherein, for i = 305 to 364 or j = 305 to 364, A305 to A364 have the structure

wherein R = Rk', wherein for each i, k' = i − 304, and for each j, k' = j − 304, and

wherein, for i = 365 or j = 365, A365 has the structure

wherein, for i = 366 ro 425 or j = 366 to 425, A366 to A425 have the structure

wherein R = Rk', wherein for each i, k' = i − 365, and for each j, k' = j − 365, and

wherein, for i = 426 to 475 or j = 426 to 475, A426 to A475 have the structure

wherein R = Rk', wherein for each i, k' = i − 425, and for each j, k' = j − 425, and

wherein, for i = 476 to 525 or j = 476 to 525, A476 to A525 have the structure

wherein R = Rk', wherein for each i, k' = i − 475, and for each j, k' = j − 475, and

wherein, for i = 526 to 575 or j = 526 to 575, A526 to A575 have the structure

wherein R = Rk', wherein for each i, k' = i − 525, and for each j, k' = j − 525, and

wherein, for i = 576 to 625 or j = 576 to 625, A576 to A625 have the structure

wherein R = Rk', wherein for each i, k' = i − 575, and for each j, k' = j − 575, and

wherein, for i = 626 to 675 or j = 626 to 675, A626 to A675 have the structure

wherein R = Rk', wherein for each i, k' = i − 625, and for each j, k' = j − 625, and

wherein, for i = 676 to 725 or j = 676 to 725, A676 to A725 have the structure

wherein R = Rk', wherein for each i, k' = i − 675, and for each j, k' = j − 575, and

wherein Rk and Rk′ have the following structures:

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

15. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a compound of Formula I

wherein:

rings A and B are each independently a 5-membered or 6-membered heterocyclic ring;

rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

L is N or CR;

X is O, S, NR, BR, BRR′, CRR′, or SiRR′;

R A , R B , R C , and R D each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;

R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;

R and R′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;

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

with the proviso that if rings A and B are both a 5-membered heterocyclic ring, then:

one of the following conditions i) and ii) is true:

i) L is N; or

ii) L is CR and R is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein if R is aryl, the aryl is a substituted aryl;

and at least one of the following conditions iii) and iv) is true:

iii) in at least one of ring A and ring B, the atom adjacent to the nitrogen atom is a carbon substituted with hydrogen; or

iv) two R A or two R B are joined to form a ring.

16. The OLED of claim 15 , wherein the compound is a fluorescent emitter.

17. The OLED of claim 15 , wherein the compound is a sensitizer and the OLED further comprises an acceptor; and wherein the acceptor is selected from the group consisting of fluorescent emitter, delayed fluorescence emitter, and combination thereof.

18. The OLED of claim 15 , wherein the first organic layer further comprises a phosphorescent sensitizer, or the OLED comprises a second organic layer disposed between the anode and the cathode, wherein the second organic layer comprises a phosphorescent sensitizer;

wherein the compound is a fluorescent acceptor; and

wherein the phosphorescent sensitizer 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:

each Y 1 to Y 13 are each independently selected from the group consisting of carbon and nitrogen; Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, 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 c , and R a independently represent from zero, mono, or up to a maximum allowed substitution to its associated ring; each R a , R b , R c , R d , R e and R f is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and two adjacent substituents of R a , R b , R c , and R a can be fused or joined to form a ring or form a multidentate ligand.

19. The OLED of claim 15 , wherein one or more organic layers, disposed between the anode and cathode, comprise a host, wherein the host comprises at least one chemical group selected from the group consisting of anthracene, naphthalene, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

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:

rings A and B are each independently a 5-membered or 6-membered heterocyclic ring;

rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

L is N or CR;

X is O, S, NR, BR, BRR′, CRR′, or SiRR′;

R A , R B , R C , and R D each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;

R A , R B , R C , and R D are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;

R and R′ are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof;

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

with the proviso that if rings A and B are both a 5-membered heterocyclic ring, then:

one of the following conditions i) and ii) is true:

i) L is N; or

ii) L is CR and R is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein if R is aryl, the aryl is a substituted aryl;

and at least one of the following conditions iii) and iv) is true:

iii) in at least one of ring A and ring B, the atom adjacent to the nitrogen atom is a carbon substituted with hydrogen; or

iv) two R A or two R B are joined to form a ring.

Assignments (1)

Continuity (3)

References Cited (176)