IP Library Granted Patent US 9,905,777
Granted Patent B2
US 9,905,777 · App. 14/420,539 · Granted Feb 27, 2018

Compound and organic electroluminescence device comprising same

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,905,777
App. No.
14/420,539
Granted
Feb 27, 2018
Kind
B2
Abstract

The present invention relates to a novel compound and an organic electroluminescence device including the same, and the compound according to the present invention may be used in an organic material layer, preferably a light-emitting layer of an organic electroluminescence device, thereby enhancing the light-emitting efficiency, driving voltage, lifespan, and the like of the organic electroluminescence device.

Claims (31)

1. A compound represented by the following Formula 1:

in Formula 1,

A 1 to A 4 are each independently CR 1 or N, and here, at least one or more thereof are N,

B 1 to B 4 are each independently CR 2 or N,

R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group, or adjacent group form a fused ring,

L is a single bond, or a C 6 to C 30 arylene group or a heteroarylene group having 5 to 30 nuclear atoms,

Cy is selected from the group consisting of compounds of the following Formulae 2a to 2f, and

in Formulae 2a to 2f,

X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N(Ar 1 ), C(Ar 2 )(Ar 3 ) and Si(Ar 4 )(Ar 5 ), and here, at least one of X 1 and X 2 is N(Ar 1 ),

a plurality of R 5 's is the same as or different from each other, and a plurality of R 6 's is the same as or different from each other, and

R 3 to R 6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group,

Ar 1 to Ar 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group,

the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group of R 1 to R 6 and Ar 1 to Ar 5 are each independently unsubstituted or substituted with one or more selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group and a C 6 to C 60 arylamine group, and

L is linked to any one of X 1 , X 2 , R 3 , R 4 , R 5 and R 6 of Formulae 2a to 2f.

2. The compound of claim 1 , wherein

of Formula 1 is selected from the group consisting of structures represented by the following S-1 to S-30:

in the structures represented by S-1 to S-30,

R 1 and R 2 are the same as those defined in claim 1 , and a plurality of R 1 's is the same as or different from each other, and a plurality of R 2 's is the same as or different from each other.

3. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 40 nuclear atoms and a C 6 to C 60 arylamine group.

4. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, or structures represented by the following A1 to A70:

5. The compound of claim 1 , wherein L of Formula 1 is a single bond or phenylene,

X 1 and X 2 are N(Ar 1 ), and here, Ar 1 is the same as or different from each other, and

Ar 1 is selected from the group consisting of hydrogen, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 40 nuclear atoms.

6. The compound of claim 1 , wherein L is linked to any one of X 1 and R 6 of Formulae 2a to 2f.

7. An organic electroluminescence device comprising:

an anode;

a cathode; and

an organic material layer having one or more layers interposed between the anode and the cathode,

wherein at least one of the organic material layer having one or more layers comprises the compound of claim 1 .

8. The organic electroluminescence device of claim 7 , wherein the organic material layer comprising the compound is selected from the group consisting of a hole injection layer, a hole transporting layer and a light-emitting layer.

9. The organic electroluminescence device of claim 7 , wherein the organic material layer comprising the compound is a light-emitting layer, and the compound is a phosphorescent host material of the light-emitting layer.

Assignments (4)
CHANGE OF NAME Recorded Jan 4, 2021
From: DOOSAN SOLUS CO., LTD.
To: SOLUS ADVANCED MATERIALS CO., LTD.
Reel/Frame 054887/0911 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2020
From: DOOSAN CORPORATION
To: DOOSAN SOLUS CO., LTD.
Reel/Frame 052970/0277 →
CHANGE OF ADDRESS Recorded Jun 18, 2020
From: DOOSAN CORPORATION
To: DOOSAN CORPORATION
Reel/Frame 052971/0480 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2015
From: KIM, TAE HYUNG; LEE, IN HYUK; KIM, HOE MOON; SHIN, JIN YONG; PARK, HO CHEOL; LEE, CHANG JUN; BEAK, YOUNG MI; LEE, EUN JUNG
To: DOOSAN CORPORATION
Reel/Frame 035554/0869 →