Luminescent material and electroluminescent display device using the same

Patent metadata

Field	Value
Publication number	US-11814401-B2
Application number	US-202017135414-A
Country	US
Kind code	B2
Filing date	Dec 28, 2020
Priority date	Dec 31, 2019
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

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:

First claim

What is claimed is:

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 i

Assignees

• Lg Display Co Ltd
• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Park Heejun
• Moon Jaemin
• Choung Kusun
• Kang Hee Ryong
• Kim Hyun
• Lee Ga Won
• Yoon Seung Hyun
• Park Kyoung-Jin

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title