IP Library › Granted Patent US 12,466,844
Granted Patent B2
US 12,466,844 · App. 17/246,885 · Granted Nov 11, 2025

Organic electroluminescent materials and devices

Inventors: Hsiao-Fan Chen (Lawrence Township, NJ); Tyler Fleetham (Newtown, PA); Rasha Hamze (Philadelphia, PA); Scott Beers (Flemington, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
C07F5/02H10K85/322H10K85/40H10K85/622H10K85/631H10K85/654H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12,466,844
App. No.
17/246,885
Granted
Nov 11, 2025
Kind
B2
Abstract

Provided are organoboron compounds. Also provided are formulations comprising these organoboron compounds. Further provided are OLEDs and related consumer products that utilize these organoboron compounds.

Claims (115)

1 . A compound of

wherein:

moiety A is a monocyclic or multicyclic fused ring system comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;

X 1 -X 13 are each independently C or N;

Y is N or CR;

R is a 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;

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

each of R A , R B , R C , and R D is independently a 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, with at least one of R A , R B , R C , and R D being a ring or ring structure G;

any two adjacent R, R A , R B , R C , or R D can be joined or fused together to form a ring,

one R B and one R C can be joined or fused together to form a ring and

wherein at least one of the following is true:

i) moiety A comprises three fused rings, wherein one of the three fused rings is a 6-membered ring that is fused to the ring containing Y and a 5-membered ring fuses to said 6-membered ring;

ii) at least one of R B and R C is a substituted or unsubstituted group selected from the group consisting of phenyl, triphenylsilyl, naphthalene, fluorene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-naphthalene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene and at least one of R A and R D is 1,3-diisopropyl benzene;

iii) moiety A and moiety D are each a monocyclic ring system comprising a 6-membered ring, any two adjacent R, R B , or R C , can be joined or fused together to form a ring, and at least one of R A and R D is a pendant heteroaryl group; or

iv) at least one R A and at least one R D is carbazole or one of R A or R D is carbazole and the other of R A and R D is 1,3-diisopropyl benzene.

2 . The compound of claim 1 , wherein each of 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 moiety A is monocyclic.

4 . The compound of claim 1 , wherein moiety A contains two fused rings, or three fused rings.

5 . The compound of claim 1 , wherein the ring or ring structure G is a substituted or unsubstituted 5-membered or 6-membered carbocyclic or heterocyclic ring.

6 . The compound of claim 1 , wherein the ring or ring structure G is a substituted or unsubstituted aromatic ring, or a multicyclic fused ring moiety.

7 . The compound of claim 1 , wherein X 1 -X 13 are each C.

8 . The compound of claim 1 , wherein at least one of X 1 -X 13 is N.

9 . The compound of claim 1 , wherein Y is N.

10 . The compound of claim 1 , wherein one or more of R A , R B , R C , and R D are independently a substituted or unsubstituted group selected from the group consisting of phenyl, triphenylsilyl, naphthalene, fluorene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-naphthalene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

11 . The compound of claim 1 , wherein the compound of Formula I is selected from the group consisting of:

wherein ring A 1 , ring A 2 , and ring A 3 are each independently 5-membered or 6-membered aromatic rings; and X 14 -X 17 are each independently C or N.

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

Compound name

Structure

Compound I-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 47 to 64, 107 to 124, and 167 to 184, wherein Compound I- [(A1)(A47)] to Compound I- [(A365)(A184)] having the structure

Compound II-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound II-[(A1)(A16)] to Compound II-[(A365)(A365)] having the structure

Compound III-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound III-[(A1)(A16)] to Compound III-[(A365)(A365)] having the structure

Compound IV-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound IV-[(A1)(A16)] to Compound IV-[(A365)(A365)] having the structure

Compound V-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 47 to 64, 107 to 124, and 167 to 184, wherein Compound V-[(A1)(A47 to Compound V-[(A365)(A184)] having the structure

Compound VI-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound VI-[(A1)(A1)] to Compound VI-[(A365)(A365)] having the structure

Compound VII-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound VII-[(A1)(A16)] to Compound VII-[(A365)(A365)] having the structure

Compound VIII-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound VIII-[(A1)(A16)] to Compound VIII-[(A365)(A365)] having the structure

Compound IX-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound IX-[(A1)(A16)] to Compound IX- [(A365)(A365)] having the structure

Compound X-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound X-[(A1)(A16)] to Compound X-[(A365)(A365)] having the structure

Compound XI-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XI-[(A1)(A16)] to Compound XI-[(A365)(A365)] having the structure

Compound XII-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XII-[(A1)(A16)] to Compound XII-[(A365)(A365)] having the structure

Compound XIII-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XIII-[(A1)(A16)] to Compound XIII-[(A365)(A365)] having the structure

Compound XIV-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XIV-[(A1)(A16)] to Compound XIV-[(A365)(A365)] having the structure

Compound XV-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XV-[(A1)(A16)] to Compound XV-[(A365)(A365)] having the structure

Compound XVI-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XVI-[(A1)(A16)] to Compound XVI-[(A365)(A365)] having the structure

Compound XVII-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XVII-[(A1)(A16)] to Compound XVII-[(A365)(A365)] having the structure

Compound XVIII-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XVIII-[(A1)(A1)] to Compound XVIII-[(A365)(A365)] having the structure

Compound XIX-[(Ai)(Aj)], wherein i is an integer from 1 to 365 and j is an integer from 16, 47 to 64, 76, 107 to 124, 136, 167 to 184, 196, 256, 316 and 365, wherein Compound XIX-[(A1)(A16)] to Compound XIX-[(A365)(A365)] having the structure

wherein A1 to A365 have the following structures:

Ai, Aj

Structure of Ai and Aj

R

A1 has the structure

A2 has the structure

A3 has the structure

A4 has the structure

A5 to A64 have the structure

wherein R = Rm, wherein m = i − 4 or m = j − 4, and

A65 to A124 have the structure

wherein R = Rm, wherein m = i − 64 or m = j − 64, and

A125 to A184 have the structure

wherein R = Rm, wherein m = i − 124 or m = j − 124, and

A185 to A244 have the structure

wherein R = Rm, wherein m = i − 184 or m = j − 184, and

A245 to A304 have the structure

wherein R = Rm, wherein m = i − 244 or m = j − 244, and

A305 to A364 have the structure

wherein R = Rm, wherein m = i − 304 or m = j − 304, and

A365 has the structure

wherein R1 to R60 have the following structures:

13 . A compound selected from the group consisting of:

14 . 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

wherein:

moiety A is a monocyclic or multicyclic fused ring system comprising5-membered and/or 6-membered carbocyclic or heterocyclic rings;

X 1 -X 13 are each independently C or N;

Y is N or CR;

R is a 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;

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

each of R A , R B , R C , and R D is independently a 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, with at least one of R A , R B , R C , and R D being a ring or ring structure G; and

any two adjacent R, R A , R B , R C , or R D can be joined or fused together to form a ring,

one R B and one R C can be joined or fused together to form a ring and

wherein at least one of the following is true:

i) moiety A comprises three fused rings, wherein one of the three fused rings is a 6-membered ring that is fused to the ring containing Y and a 5-membered ring fuses to said 6-membered ring;

ii) at least one of R B and R C is a substituted or unsubstituted group selected from the group consisting of phenyl, triphenylsilyl, naphthalene, fluorene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-naphthalene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene and at least one of R A and R D is 1,3-diisopropyl benzene;

iii) moiety A and moiety D are each a monocyclic ring system comprising a 6-membered ring, any two adjacent R, R B , or R C , can be joined or fused together to form a ring, and at least one of R A and R D is a pendant heteroaryl group; or

iv) at least one R A and at least one R D is carbazole or one of R A or R D is carbazole and the other of R A and R D is 1,3-diisopropyl benzene.

15 . The OLED of claim 14 , wherein the compound is a fluorescent emitter.

16 . The OLED of claim 14 , wherein the first organic layer further comprises a phosphorescent sensitizer, and the compound is a fluorescent acceptor.

17 . The OLED of claim 14 , wherein one or more organic layers, disposed between the anode and cathode, comprise a host, wherein the host comprises at least one chemical moiety selected from the group consisting of naphthalene, fluorene, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho [3,2,1-de]anthracene, aza-naphthalene, aza-fluorene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho [3,2,1-de]anthracene).

18 . The OLED of claim 17 , wherein the host is selected from the group consisting of:

and combinations thereof.

19 . 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

wherein:

moiety A is a monocyclic or multicyclic fused ring system comprising5-membered and/or 6-membered carbocyclic or heterocyclic rings;

X 1 -X 13 are each independently C or N;

Y is N or CR;

R is a 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;

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

each of R A , R B , R C , and R D is independently a 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, with at least one of R A , R B , R C , and R D being a ring or ring structure G; and

any two adjacent R, R A , R B , R C , or R D can be joined or fused together to form a ring,

one R B and one R C can be joined or fused together to form a ring and

wherein at least one of the following is true:

i) moiety A comprises three fused rings, wherein one of the three fused rings is a 6-membered ring that is fused to the ring containing Y and a 5-membered ring fuses to said 6-membered ring;

ii) at least one of R B and R C is a substituted or unsubstituted group selected from the group consisting of phenyl, triphenylsilyl, naphthalene, fluorene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-naphthalene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene and at least one of R A and R D is 1,3-diisopropyl benzene;

iii) moiety A and moiety D are each a monocyclic ring system comprising a 6-membered ring, any two adjacent R, R B , or R C , can be joined or fused together to form a ring, and at least one of R A and R D is a pendant heteroaryl group; or

iv) at least one R A and at least one R D is carbazole or one of R A or R D is carbazole and the other of R A and R D is 1,3-diisopropyl benzene.

20 . A formulation comprising a compound according to claim 1 .

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded May 3, 2021
From: CHEN, HSIAO-FAN; FLEETHAM, TYLER; HAMZE, RASHA; BEERS, SCOTT
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 056112/0578 →
Continuity (2)
Provisional Application 63024001 · May 13, 2020
Related Publication 20210363163A1 · Nov 25, 2021
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