IP Library › Granted Patent US 12,509,415
Granted Patent B2
US 12,509,415 · App. 17/560,931 · Granted Dec 30, 2025

Compounds, liquid compositions including compounds, and electroluminescent devices

Inventors: Fumiaki Kato (Yokohama, JP); Tomoyuki Kikuchi (Yokohama, JP); Hiroko Endo (Yokohama, JP); Keigo Furuta (Yokohama, JP); Keisuke Korai (Yokoham, JP); Mitsunori Ito (Yokohama, JP); Naotoshi Suganuma (Yokohama, JP); Takao Motoyama (Hwaseong-si, JP); Dae Young Chung (Suwon-si, KR); Eun Joo Jang (Suwon-si, KR); Ha Il Kwon (Suwon-si, KR); Hyo Sook Jang (Suwon-si, KR); Soonmin Cha (Suwon-si, KR); Tae Ho Kim (Seongnam-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C07C211/54C07C211/61C07D209/82H10K71/135H10K71/15H10K85/631H10K85/6572H10K50/11H10K50/15
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Quick Facts
Patent No.
US 12,509,415
App. No.
17/560,931
Granted
Dec 30, 2025
Kind
B2
Abstract

Provided is a compound represented by Chemical Formula 1 capable of manufacturing an EL device by inkjet printing. In Chemical Formula 1, n is an integer of greater than or equal to 3 and less than or equal to 10, X is a group represented by Chemical Formula 2 and a plurality of X's may be the same or different from each other, and Y is a group represented by Chemical Formula 3 and a plurality of Y's may be the same or different from each other.

Claims (108)

1 . A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

n is an integer of greater than or equal to 3 and less than or equal to 10,

X is a group represented by Chemical Formula 2 and a plurality of X's are the same or different from each other, and

Y is a group represented by Chemical Formula 3 and a plurality of Y's are the same or different from each other,

wherein, in Chemical Formula 2,

R 1 , R 2 , and R 3 are each independently a hydrogen atom, a single bond, or an alkyl group having 1 to 10 carbon atoms and are the same or different and are optionally linked to each other to form a ring,

a and b are each independently an integer of greater than or equal to 2 and less than or equal to 10, and

c is greater than or equal to 1 and less than or equal to 6;

wherein, in Chemical Formula 3,

R 4 , R 5 , and R 6 are each independently a hydrogen atom, a single bond, or an alkyl group having 1 to 8 carbon atoms and are the same or different and are optionally linked to each other to form a ring,

d is greater than or equal to 1 and less than or equal to 5, and

e and f are each independently greater than or equal to 1 and less than or equal to 6.

2 . The compound of claim 1 , wherein the compound has a molecular weight of greater than or equal to about 3000 g/mole and less than or equal to about 10000 g/mole.

3 . A composition comprising

the compound of claim 1 , and

a low molecular weight compound having a molecular weight of less than about 2000 g/mole,

wherein a content of the low molecular weight compound is less than or equal to about 30 wt %.

4 . A composition comprising

the compound of claim 1 , and

a polymer compound having a molecular weight of greater than or equal to about 10000 g/mole,

wherein a content of the polymer compound is less than or equal to about 60 wt %.

5 . A composition comprising

the compound of claim 1 ,

a low molecular weight compound having a molecular weight of less than about 2000 g/mole, and

a polymer compound having a molecular weight of greater than or equal to about 10000 g/mole,

wherein a content of the low molecular weight compound is less than or equal to about 30 wt %, and

a content of the polymer compound is less than or equal to about 60 wt %.

6 . A liquid composition comprising

the compound of claim 1 , and

a solvent.

7 . A liquid composition comprising

the composition of claim 3 , and

a solvent.

8 . A liquid composition comprising

the composition of claim 4 , and

a solvent.

9 . A liquid composition comprising

the composition of claim 5 , and

a solvent.

10 . An electroluminescent device material, comprising

the compound of claim 1 , and

a solvent.

11 . An electroluminescent device material, comprising

the composition of claim 3 , and

a solvent.

12 . An electroluminescent device material, comprising

the composition of claim 4 , and

a solvent.

13 . An electroluminescent device material, comprising

the composition of claim 5 , and

a solvent.

14 . An electroluminescent device, comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode,

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

15 . The electroluminescent device of claim 14 , wherein the organic layer comprising the compound is a hole transport layer or a hole injection layer.

16 . The electroluminescent device of claim 14 , wherein the organic layer comprises a light emitting layer comprising semiconductor nanoparticles or an organometallic complex.

17 . An electroluminescent device, comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode,

wherein at least one layer of the organic layer comprises the composition of claim 3 .

18 . The electroluminescent device of claim 17 , wherein the organic layer comprising the composition is a hole transport layer or a hole injection layer.

19 . The electroluminescent device of claim 17 , wherein the organic layer comprises a light emitting layer comprising semiconductor nanoparticles or an organometallic complex.

20 . An electroluminescent device, comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode,

wherein at least one layer of the organic layer comprises the composition of claim 4 .

21 . The electroluminescent device of claim 20 , wherein the organic layer comprising the composition is a hole transport layer or a hole injection layer.

22 . The electroluminescent device of claim 20 , wherein the organic layer comprises a light emitting layer comprising semiconductor nanoparticles or an organometallic complex.

23 . An electroluminescent device, comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode,

wherein at least one layer of the organic layer comprises the composition of claim 5 .

24 . The electroluminescent device of claim 23 , wherein the organic layer comprising the composition is a hole transport layer or a hole injection layer.

25 . The electroluminescent device of claim 23 , wherein the organic layer comprises a light emitting layer comprising semiconductor nanoparticles or an organometallic complex.

26 . A method of manufacturing an electroluminescent device comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode, comprising

applying the liquid composition according to claim 6 by inkjet printing, and

drying the liquid composition to remove a solvent to form a hole transport layer.

27 . The method of claim 26 , which comprises

applying an ink for a light emitting layer comprising semiconductor nanoparticles and a solvent for a light emitting layer on the surface of the hole transport layer by a wet method, and

drying the ink for the light emitting layer to remove the solvent to form the light emitting layer.

28 . A method of manufacturing an electroluminescent device comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode, comprising

applying the liquid composition according to claim 7 by inkjet printing, and

drying the liquid composition to remove a solvent to form a hole transport layer.

29 . The method of claim 28 , which comprises

applying an ink for a light emitting layer comprising semiconductor nanoparticles and a solvent for a light emitting layer on the surface of the hole transport layer by a wet method, and

drying the ink for the light emitting layer to remove the solvent to form the light emitting layer.

30 . A method of manufacturing an electroluminescent device comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode, comprising

applying the liquid composition according to claim 8 by inkjet printing, and

drying the liquid composition to remove a solvent to form a hole transport layer.

31 . The method of claim 30 , which comprises

applying an ink for a light emitting layer comprising semiconductor nanoparticles and a solvent for a light emitting layer on the surface of the hole transport layer by a wet method, and

drying the ink for the light emitting layer to remove the solvent to form the light emitting layer.

32 . A method of manufacturing an electroluminescent device comprising

a first electrode and a second electrode, and

at least one organic layer between the first electrode and the second electrode, comprising

applying the liquid composition according to claim 9 by inkjet printing, and

drying the liquid composition to remove a solvent to form a hole transport layer.

33 . The method of claim 32 , which comprises

applying an ink for a light emitting layer comprising semiconductor nanoparticles and a solvent for a light emitting layer on the surface of the hole transport layer by a wet method, and

drying the ink for the light emitting layer to remove the solvent to form the light emitting layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2021
From: KATO, FUMIAKI; KIKUCHI, TOMOYUKI; ENDO, HIROKO; FURUTA, KEIGO; KORAI, KEISUKE; ITO, MITSUNORI; SUGANUMA, NAOTOSHI; MOTOYAMA, TAKAO; CHUNG, DAE YOUNG; JANG, EUN JOO; KWON, HA IL; JANG, HYO SOOK; CHA, SOONMIN; KIM, TAE HO
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 058498/0436 →
Priority Claims (1)
JP 2020-215216 · Dec 24, 2020 · national
Continuity (1)
Related Publication 20220213022A1 · Jul 7, 2022
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