IP Library Granted Patent US 12673934
Granted Patent B2
US 12673934 · App. 17/815,835 · Granted Jul 7, 2026

Compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the compound

Inventors: Michelle Groarke (Binningen, CH); Hiroaki Toyoshima (Chiyoda-ku, JP); Masatoshi Saito (Sodegaura, JP); Natalia Chebotareva (Hagenthal le bas, FR)
Assignee: IDEMITSU KOSAN CO., LTD.
C07D401/14C07D403/10H10K50/16H10K85/615H10K85/654H10K85/6572
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Quick Facts
Patent No.
US 12673934
App. No.
17/815,835
Granted
Jul 7, 2026
Kind
B2
Abstract

Specific compounds represented by formula (I), a material for an organic electroluminescence device comprising said specific compound, an organic electroluminescence device comprising said specific compound, an electronic equipment comprising said organic electroluminescence device and the use of said compounds in an organic electroluminescence device.

Claims (61)

1 . A compound of formula (I):

wherein

—L 1 -(L 2 ) m - is:

L 3 is a group of a formula

wherein

X 10 is N or CR 10 ,

X 11 is N or CR 11 ,

X 12 is N or CR 12 ,

X 13 is N or CR 13 ,

X 14 is N or CR 14 ;

wherein at least one of X 10 , X 11 , X 12 , X 13 and X 14 is N; and one of X 10 , X 11 , X 12 , X 13 and X 14 ;

R a and R b are each independently an unsubstituted aromatic hydrocarbon group comprising 6 to 30 ring atoms,

n is 0 or 1,

X 1 is N,

HetAr has formula (II) or (III):

or, if n is 1, HetAr has formula (II), (III), or (IV):

X 4 is N or CR 4 ,

X 5 is N or CR 5 ,

X 6 is N or CR 6 ,

X 7 is N or CR 7 ,

X 8 is N or CR 8 ,

wherein at least one of X 4 , X 5 , X 6 , X 7 , and X 8 is N,

X 16 is N or CR 16 ,

X 17 is N or CR 17 ,

X 18 is N or CR 18 ,

X 19 is N or CR 19 ,

X 20 is N or CR 20 ,

wherein at least one of X 16 , X 17 , X 18 , X 19 , and X 20 is N,

o and p are each independently 0, 1, 2, 3, or 4,

q is 0, 1, 2, or 3 and

R 1 , R 4 , R 3 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are each independently hydrogen, an unsubstituted or substituted aromatic hydrocarbon group comprising 6 to 30 ring atoms or an unsubstituted or substituted heteroaromatic group comprising 3 to 30 ring atoms, an unsubstituted or substituted alkyl group comprising 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group comprising 3 to 18 ring carbon atoms or CN, or

two adjacent groups R 9 , two adjacent groups R 15 , or two adjacent groups R 21 and/or two adjacent groups selected from R 4 , R 5 , R 6 , R 7 , R 8 , R 16 , R 17 , R 18 , R 19 , and R 20 form together a substituted or unsubstituted carbocyclic or heterocyclic ring, ring;

R c and R d are each independently an unsubstituted or substituted aromatic hydrocarbon group comprising 6 to 30 ring atoms or an unsubstituted or substituted heteroaromatic group comprising 3 to 30 ring atoms, an unsubstituted or substituted alkyl group comprising 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group comprising 3 to 18 ring carbon atoms, and

a dotted line is a bonding site.

2 . The compound according to of claim 1 , wherein -(L 3 ) n -HetAr has formula (IIa), (IIb), (IIc), (IIIa), (IIIb), (IIIc), (IVa), (IVb), or (IVc):

wherein one of one of R 1 , R 12 , R 13 and R 14 in formula (IIIa), one of one of R 10 , R 12 , R 13 , and R 14 in formula (IIIb) and one of one of R 10 , R 1 , R 13 , and R 14 in formula (IIIc) is a bonding site.

3 . The compound of claim 1 , wherein o, p, and q are 0.

4 . The compound of claim 1 , wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are hydrogen.

5 . The compound of claim 1 , wherein R a and R b are each independently an unsubstituted aromatic hydrocarbon group comprising 6 to 18 ring atoms.

6 . The compound of claim 1 , wherein R c and R d are each independently an unsubstituted or substituted aromatic hydrocarbon group comprising 6 to 18 ring atoms.

7 . The compound of claim 1 , wherein n is 0.

8 . A material for an organic electroluminescence device, comprising:

the compound of claim 1 .

9 . An organic electroluminescence device, comprising:

a cathode;

an anode; and

an organic thin film layer comprising an emitting layer disposed between the cathode and the anode,

wherein at least one layer of the organic thin film layer comprises the compound of claim 1 .

10 . The device of claim 9 , wherein the organic thin film layer further comprises an electron-transporting zone provided between the emitting layer and the cathode.

11 . The device of claim 10 , wherein the electron-transporting zone comprises an electron-transporting layer provided between the emitting layer and the cathode.

12 . The device of claim 10 , wherein the electron-transporting zone further comprises a metal, a metal complex, and/or a metal compound.

13 . Electronic An electronic equipment, comprising:

the organic electroluminescence device of claim 9 .

14 . Use of a-A method of making an organic electroluminescence device, the method comprising:

combining the compound of claim 1 and the organic electroluminescence device.

15 . The compound of claim 1 , wherein -L 1 -(L 2 ) m - is:

16 . The compound of claim 1 , wherein -L 1 -(L 2 ) m - is:

17 . The compound of claim 1 , wherein -L 1 -(L 2 ) m - is:

18 . The compound of claim 1 , wherein -L 1 -(L 2 ) m - is:

19 . The compound of claim 1 , wherein -L 1 -(L 2 ) m - is:

20 . The compound of claim 1 , wherein -L 1 -(L 2 ) m - is: