IP Library Granted Patent US 12,559,459
Granted Patent B2
US 12,559,459 · App. 15/550,590 · Granted Feb 24, 2026

Aromatic heterocyclic derivative, and organic electroluminescent element, illumination device, and display device using aromatic heterocyclic derivative

Inventors: Motoaki Sugino (Akishima, JP); Eisaku Katoh (Hachioji, JP)
Assignee: MERCK PATENT GMBH
C07D209/82C07D405/14C07D409/14
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Quick Facts
Patent No.
US 12,559,459
App. No.
15/550,590
Granted
Feb 24, 2026
Kind
B2
Abstract

The present invention addresses the problem of providing a novel aromatic heterocyclic derivative, providing an organic EL element that uses the derivative and has high luminous efficiency, long luminescence life, and few changes over time when used under high temperatures, and providing a display device and an illumination device that are equipped with the organic El element. This aromatic heterocyclic derivative is characterized by having a specific structure which includes a carbazole ring.

Claims (51)

1 . An organic electroluminescent element comprising a light emitting layer comprising an aromatic heterocyclic derivative having a structure represented by Formula (H2), wherein the aromatic heterocyclic derivative is contained in the light emitting layer as a host compound:

in Formula (H2),

Y 1 , Y 2 and Y 3 each independently represent:

CR′ or a nitrogen atom, and at least two of Y 1 , Y 2 and Y 3 represents a nitrogen atom;

R′, Ar 1 and Ar 2 each represent:

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 30 ring forming carbon atoms,

provided that not all of R′, Ar 1 and Ar 2 represent hydrogen atoms at the same time;

X represents an oxygen atom or a sulfur atom;

Ra and Rb each independently represent a substituent;

L 1 represents:

a single bond, a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring forming carbon atoms, or

a divalent linking group composed of a combination thereof;

L 2 represents:

a single bond,

a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring forming carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring forming atoms, or

a divalent linking group composed of a combination thereof;

R 1 and R 2 each independently represent:

a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a cyano group, a halogen atom, or

an unsubstituted or substituted aryl group having 6 to 30 ring forming carbon atoms, provided that the substituted aryl group has a substituent represented by Formulas (A-1) or (A-2);

R 3 represents:

a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

a substituted or unsubstituted aryl group having 6 to 30 ring forming carbon atoms, or

a substituted or unsubstituted heteroaryl group having 5 to 30 ring forming atoms;

n1 represents an integer of 0 to 3,

n2 represents an integer of 0 to 4,

na2 represents an integer of 0 to 2,

nb2 represents an integer of 0 to 4,

when n1 to n2, na2 and nb2 each represent an integer of 2 or more, a plurality of R 1 , R 2 , Ra, and Rb may be the same or different, and adjacent Ra and Rb may be bonded together to form a ring structure,

in Formulas (A-1) and (A-2),

A 1 to A 5 and A 11 to A 18 each independently represent CRc or a nitrogen atom, and

Rc represents a hydrogen atom, a substituent, or a bond,

one of A 1 to A 5 and one of A 11 to A 18 represent CRc, and Rc represents a bond which is directly bonded to an aryl group having 6 to 30 ring forming carbon atoms and represented by R 1 and R 2 ,

other Rc may be the same or different, and adjacent Rc may be bonded together to form a ring structure; and

X 11 represents an oxygen atom or a sulfur atom.

2 . The organic electroluminescent element of claim 1 ,

wherein L 1 represents a single bond, a phenylene group, a biphenylene group, or an alkylene group having 2 carbon or fewer.

3 . A display device provided with the organic electroluminescent element described in claim 2 .

4 . A lighting device provided with the organic electroluminescent element described in claim 2 .

5 . The organic electroluminescent element of claim 1 ,

wherein L 2 represents a single bond, a phenylene group, a heteroarylene group, or an alkylene group having 2 carbon or fewer.

6 . A display device provided with the organic electroluminescent element described in claim 5 .

7 . A lighting device provided with the organic electroluminescent element described in claim 5 .

8 . The organic electroluminescent element of claim 1 ,

wherein

the light emitting layer further contains another host compound having a different structure from the aforesaid aromatic heterocyclic derivative.

9 . A display device provided with the organic electroluminescent element described in claim 8 .

10 . A lighting device provided with the organic electroluminescent element described in claim 8 .

11 . A display device provided with the organic electroluminescent element described in claim 1 .

12 . A lighting device provided with the organic electroluminescent element described in claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 15, 2021
From: KONICA MINOLTA, INC.
To: MERCK PATENT GMBH
Reel/Frame 054929/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2017
From: SUGINO, MOTOAKI; KATOH, EISAKU
To: KONICA MINOLTA, INC.
Reel/Frame 043270/0067 →
Priority Claims (1)
JP 2015-026039 · Feb 13, 2015 · national
Continuity (1)
Related Publication 20180037546A1 · Feb 8, 2018
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