IP Library Granted Patent US 12679826
Granted Patent B2
US 12679826 · App. 17/922,706 · Granted Jul 14, 2026

Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic apparatus

Inventors: Masatoshi Saito (Sodegaura, JP); Kei Yoshida (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
C07D403/10H10K59/00H10K85/654H10K85/6572H10K50/166
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Quick Facts
Patent No.
US 12679826
App. No.
17/922,706
Granted
Jul 14, 2026
Kind
B2
Abstract

A compound represented by the following formula (1), wherein L 1 is a single bond or an arylene group, and Ar 1 and Ar 2 are an unsubstituted aryl group.

Claims (62)

1 . A compound represented by the following formula (1):

wherein in the formula (1),

Ar 1 and Ar 2 are independently an unsubstituted aryl group having 6 to 50 ring carbon atoms;

R 1 and R 2 form an unsubstituted, saturated or unsaturated hydrocarbon ring having 6 to 50 ring carbon atoms by bonding with each other, or do not form the ring;

R 3 and R 4 , and R 1 and R 2 which do not form the ring are independently a hydrogen atom, or a substituent R a ;

one or more sets of the adjacent two or more of R 11 to R 18 form an unsubstituted, saturated or unsaturated hydrocarbon ring having 6 to 50 ring carbon atoms, or an unsubstituted, saturated or unsaturated heterocyclic ring having 5 to 50 ring atoms, by bonding with each other, or do not form the rings;

R 11 to R 18 which do not form the rings are independently a hydrogen atom, or a substituent R a ;

L 1 is a divalent group represented by any one of the following formulas (a1) to (a9):

wherein in the formulas (a1) to (a9), *1 is bonded with a benzene ring on a carbazolyl group side, and *2 is bonded with a benzene ring on a triazine ring side,

wherein the substituent R a is selected from the group consisting of:

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R 901 )(R 902 )(R 903 ),

—O-(R 904 ),

—S-(R 905 ),

—N(R 906 )(R 907 ), and

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (wherein, R 901 to R 907 are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; when two or more of each of R 901 to R 907 are present, the two or more of each of R 901 to R 907 may be the same as or different from each other).

2 . The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by any one of the following formulas (2-1) to (2-8):

wherein in the formulas (2-1) to (2-8), Ar 1 , Ar 2 , R 1 to R 4 , and R 11 to R 18 are the same as defined in the formula (1).

3 . The compound according to claim 1 , wherein L 1 in the formula (1) is a group represented by the formula (a1).

4 . The compound according to claim 1 , wherein Ar 1 and Ar 2 in the formula (1) are independently

an unsubstituted phenyl group,

an unsubstituted biphenyl group,

an unsubstituted terphenyl group,

an unsubstituted naphthyl group, or

an unsubstituted phenanthryl group.

5 . The compound according to claim 1 , wherein Ar 1 and Ar 2 in the formula (1) are independently a group represented by any one of the following formulas (b1) to (b4):

wherein in the formulas (b1) to (b4), *3 represents a binding site with a triazine ring.

6 . The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by any one of the following formulas (4-1) to (4-6):

wherein in the formulas (4-1) to (4-6), R 1 to R 4 , and R 11 to R 18 are the same as defined in the formula (1).

7 . The compound according to claim 1 , wherein R 1 and R 2 in the formula (1) are a hydrogen atom.

8 . The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (5):

wherein in the formula (5), L 1 , Ar 1 , Ar 2 , R 3 , R 4 , and R 11 to R 18 are the same as defined in the formula (1).

9 . The compound according to claim 1 , wherein R 3 and R 4 in the formula (1) are a hydrogen atom.

10 . The compound according to claim 1 , wherein R 11 to R 18 in the formula (1) are a hydrogen atom.

11 . The compound according to claim 1 , wherein the substituent R a is selected from the group consisting of

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, and

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

12 . The compound according to claim 1 , wherein the compound represented by the formula (1) comprises at least one deuterium atom.

13 . The compound according to claim 1 , which is a material for an organic electroluminescence device.

14 . An electron-transporting material for an organic electroluminescence device, comprising the compound according to claim 1 .

15 . An organic electroluminescence device comprising

a cathode;

an anode; and

one or two or more organic layers arranged between the cathode and the anode,

wherein at least one layer of the organic layers comprises the compound according to claim 1 .

16 . An electronic apparatus comprising the organic electroluminescence device according to claim 15 .

17 . An organic electroluminescence device comprising an anode, an emitting layer, an electron-transporting region, and a cathode in this order,

wherein the electron-transporting region comprises the compound according to claim 1 .

18 . The organic electroluminescence device according to claim 17 , wherein the electron-transporting region comprises a first electron-transporting layer, and a second electron-transporting layer,

the organic electroluminescence device comprises the emitting layer, the first electron-transporting layer, and the second electron-transporting layer in this order, and

at least one layer of the first electron-transporting layer and the second electron-transporting layer comprises the compound.

19 . The organic electroluminescence device according to claim 17 , wherein a hole-transporting region is provided between the anode and the emitting layer.