IP Library Granted Patent US 11,814,401
Granted Patent B2
US 11,814,401 · App. 17/135,414 · Granted Nov 14, 2023

Luminescent material and electroluminescent display device using the same

Inventors: HeeJun Park (Paju-si, KR); Jaemin Moon (Paju-si, KR); Kusun Choung (Paju-si, KR); Hee Ryong Kang (Hwaseong-si, KR); Hyun Kim (Hwaseong-si, KR); Ga Won Lee (Hwaseong-si, KR); Seung Hyun Yoon (Hwaseong-si, KR); Kyoung-Jin Park (Hwaseong-si, KR)
Assignees: LG DISPLAY CO., LTD; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
C07F15/0033H10K85/342H10K50/15
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Quick Facts
Patent No.
US 11,814,401
App. No.
17/135,414
Granted
Nov 14, 2023
Kind
B2
Abstract

A new luminescent material and an electroluminescent display device using the same are disclosed, in which the luminescent material includes a compound expressed by the following chemical formula 1 and may be used as a dopant of a light emitting layer of a green, yellow-green or red color:

Claims (61)

1. A luminescent material comprising a compound expressed by the following chemical formula 1:

in the chemical formula 1,

X a is selected from oxygen or sulfur;

X b and X c are independently selected from nitrogen or carbon;

R 1 and R 2 are independently selected from the group consisting of hydrogen, heavy hydrogen, —F, —Cl, —Br, —I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, alkyl group of substituted or unsubstituted C 1 -C 20 , alkenyl group of substituted or unsubstituted C 2 -C 20 , alkynyl group of substituted or unsubstituted C 2 -C 20 , heteroalkyl group of substituted or unsubstituted C 1 -C 20 , aralkyl group of substituted or unsubstituted C 7 -C 20 , aryl group of substituted or unsubstituted C 6 -C 30 , heteroaryl group of substituted or unsubstituted C 3 -C 30 , and heteroaralkyl group of substituted or unsubstituted C 3 -C 20 ;

m is selected from integers of 1 to 4;

two or more R 1 are equal to or different from one another if m is 2 or more;

two R 1 , which are combined with adjacent carbons, are optionally combined with each other to form a ring;

n is selected from integers of 1 to 8;

two or more R 2 are equal to or different from one another if n is 2 or more;

two R 2 , which are combined with adjacent carbons, are optionally combined with each other to form a ring;

two R 2 , which are combined with a same carbon, are optionally combined with each other to form a ring;

X-Y is an auxiliary ligand; and

A and B indicate values of ligands combined with iridium, wherein A is an integer of 1 to 3, B is an integer of 0 to 2, and a sum of A and B is 3.

2. The luminescent material of claim 1 , wherein the chemical formula 1 is a compound expressed by the following chemical formula 2:

in the chemical formula 2,

X a , X b , X c , R 1 , R 2 , m, and n are as defined in the chemical formula 1,

R 3 and R 4 are respectively equal to R 1 ,

o and p are equal to m,

C is equal to A of the chemical formula 1, and D is equal to B of the chemical formula 1.

3. The luminescent material of claim 1 , wherein the chemical formula 1 is a compound expressed by the following chemical formula 3:

in the chemical formula 3,

X a , X b , X c , R 1 , R 2 , m, and n are as defined in the chemical formula 1,

R 5 , R 6 , and R 7 are respectively equal to R 1 ,

E is equal to A of the chemical formula 1, and F is equal to B of the chemical formula 1.

4. The luminescent material of claim 2 , wherein the chemical formula 2 is a compound selected from a group including the following compounds 1 to 60 and 111 to 119:

5. The luminescent material of claim 3 , wherein the chemical formula 3 is a compound selected from a group including the following compounds 61 to 110:

6. The luminescent material of claim 1 , wherein the luminescent material emits light of a green, a yellow-green or red color.

7. An electroluminescent display device comprising:

a substrate;

a first electrode provided on the substrate;

a light emitting layer provided on the first electrode; and

a second electrode provided on the light emitting layer,

wherein the light emitting layer includes a luminescent material comprising a compound expressed by the following chemical formula 1:

in the chemical formula 1,

X a is selected from oxygen or sulfur;

X b and X c are independently selected from nitrogen or carbon;

R 1 and R 2 are independently selected from the group consisting of hydrogen, heavy hydrogen, —F, —Cl, —Br, —I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, alkyl group of substituted or unsubstituted C 1 -C 20 , alkenyl group of substituted or unsubstituted C 2 -C 20 , alkynyl group of substituted or unsubstituted C 2 -C 20 , heteroalkyl group of substituted or unsubstituted C 1 -C 20 , aralkyl group of substituted or unsubstituted C 7 -C 20 , aryl group of substituted or unsubstituted C 6 -C 30 , heteroaryl group of substituted or unsubstituted C 3 -C 30 , and heteroaralkyl group of substituted or unsubstituted C 3 -C 20 ;

m is selected from integers of 1 to 4;

two or more R 1 are equal to or different from one another if m is 2 or more;

two R 1 , which are combined with adjacent carbons, are optionally combined with each other to form a ring;

n is selected from integers of 1 to 8;

two or more R 2 are equal to or different from one another if n is 2 or more;

two R 2 , which are combined with adjacent carbons, are optionally combined with each other to form a ring;

two R 2 , which are combined with a same carbon, are optionally combined with each other to form a ring;

X-Y is an auxiliary ligand; and

A and B indicate values of ligands combined with iridium, wherein A is an integer of 1 to 3, B is an integer of 0 to 2, and a sum of A and B is 3.

8. The electroluminescent display device of claim 7 , wherein the chemical formula 1 is a compound expressed by the following chemical formula 2:

in the chemical formula 2,

X a , X b , X c , R 1 , R 2 , m, and n are as defined in the chemical formula 1,

R 3 and R 4 are respectively equal to R 1 ,

o and p are equal to m,

C is equal to A of the chemical formula 1, and D is equal to B of the chemical formula 1.

9. The electroluminescent display device of claim 7 , wherein the chemical formula 1 is a compound expressed by the following chemical formula 3:

in the chemical formula 3,

X a , X b , X c , R 1 , R 2 , m, and n are as defined in the chemical formula 1,

R 5 , R 6 , and R 7 are respectively equal to R 1 ,

E is equal to A of the chemical formula 1, and F is equal to B of the chemical formula 1.

10. The electroluminescent display device of claim 7 , wherein the light emitting layer includes a dopant and a host, the dopant comprising the luminescent material.

11. The electroluminescent display device of claim 7 , wherein the light emitting layer includes a first stack emitting light of a first color, a second stack emitting light of a second color, and a charge generating layer provided between the first stack and the second stack, and one of the first stack or the second stack includes the luminescent material.

12. The electroluminescent display device of claim 11 , wherein one stack including the luminescent material is provided to emit light of a green, a yellow-green or red color.

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2020
From: PARK, HEEJUN; MOON, JAEMIN; CHOUNG, KUSUN; KANG, HEE RYONG; KIM, HYUN; LEE, GA WON; YOON, SEUNG HYUN; PARK, KYOUNG-JIN
To: LG DISPLAY CO., LTD.; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 054859/0078 →
Priority Claims (1)
KR 10-2019-0179888 · Dec 31, 2019 · national
Continuity (1)
Related Publication 20210198298A1 · Jul 1, 2021