IP Library Granted Patent US 10,454,043
Granted Patent B2
US 10,454,043 · App. 15/522,927 · Granted Oct 22, 2019

Heterocyclic compound and organic light-emitting element using same

Inventors: Mi-Jin Kim (Ulsan, KR); Kee-Yong Kim (Suwon, KR); Yang-Soo Ha (Osan, KR); Jin-Seok Choi (Suwon, KR); Dae-Hyuk Choi (Yongin, KR); Sung-Jin Eum (Yongin, KR); Joo-Dong Lee (Seongnam, KR)
Assignee: HEESUNG MATERIAL LTD.
H01L51/0072C07D471/04C07D471/14C07D519/00C07F9/6561C09K11/06H01L51/0052H01L51/0054H01L51/0058H01L51/0061H01L51/0067H01L51/0073H01L51/0074H01L51/50H01L51/5072
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Quick Facts
Patent No.
US 10,454,043
App. No.
15/522,927
Granted
Oct 22, 2019
Kind
B2
Abstract

The present specification relates to a novel hetero-cyclic compound and an organic light emitting device using the same.

Claims (36)

1. A hetero-cyclic compound represented by the following Chemical Formula 4 or 5:

in Chemical Formula 4 and 5,

R 2 to R 9 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; —SiR 10 R 11 R 12 ; —P(═O)R 13 R 14 ;

a substituted or unsubstituted C 6 to C 60 aryl; a substituted or unsubstituted C 2 to C 60 heteroaryl; and an amine which is unsubstituted or substituted with one or more substituents selected from a substituted or unsubstituted C 1 to C 60 alkyl, a substituted or unsubstituted C 6 to C 60 aryl, and a substituted or unsubstituted C 2 to C 60 heteroaryl,

R 10 to R 14 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C 1 to C 60 alkyl; a substituted or unsubstituted C 6 to C 60 aryl; or a substituted or unsubstituted C 2 to C 60 heteroaryl, and

E is selected from the group consisting of hydrogen; deuterium; —SiR 20 R 21 R 22 ; —P(═O)R 23 R 24 ; a substituted phenyl group; a substituted or unsubstituted C 10 to C 60 polycyclic aryl; a substituted or unsubstituted C 2 to C 60 heteroaryl; and an amine which is unsubstituted or substituted with a substituted or unsubstituted C 6 to C 60 aryl, or a substituted or unsubstituted C 2 to C 60 heteroaryl,

wherein when E is substituted, a substituent is selected from the group consisting of C 1 to C 60 alkyl group; C 6 to C 60 aryl group unsubstituted or substituted with C 1 to C 60 alkyl group; C 2 to C 60 heteroaryl group unsubstituted or substituted with a substituent selected from the group consisting of C 1 to C 60 alkyl group, C 2 to C 60 hetereoaryl group, and C 6 to C 60 aryl group unsubstituted or substituted with C 1 to C 60 alkyl group; amine group; —SiR 20 R 21 R 22 ; and —P(═O)R 23 R 24 ,

wherein when E is hydrogen, R 3 is selected from the group consisting of a substituted or unsubstituted C 6 to C 60 aryl, and a substituted or unsubstituted C 2 to C 60 heteroaryl,

r is an integer of 1 to 5,

when r is 2 or more, E's are the same as or different from each other,

R 20 to R 24 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C 1 to C 60 alkyl; a substituted or unsubstituted C 6 to C 60 aryl; or a substituted or unsubstituted C 2 to C 60 heteroaryl.

2. The hetero-cyclic compound of claim 1 , wherein Chemical Formula 5 is represented by any one of the following Chemical Formula 6:

in Chemical Formula 6,

E is selected from the group consisting of hydrogen; deuterium;

halogen; —SiR 20 R 21 R 22 ; —P(═O)R 23 R 24 ; a substituted or unsubstituted C 1 to C 60 alkyl; a substituted phenyl group; a substituted or unsubstituted C 10 to C 60 polycyclic aryl; a substituted or unsubstituted C 2 to C 60 heteroaryl; and an amine which is unsubstituted or substituted with a substituted or unsubstituted C 6 to C 60 aryl, or a substituted or unsubstituted C 2 to C 60 heteroaryl,

wherein when E is substituted, a substituent is selected from the group consisting of C 1 to C 60 alkyl group; C 6 to C 60 aryl group unsubstituted or substituted with C 1 to C 60 alkyl group; C 2 to C 60 heteroaryl group unsubstituted or substituted with a substituent selected from the group consisting of C 1 to C 60 alkyl group, C 2 to C 60 heteroaryl group, and C 6 to C 60 aryl group unsubstituted or substituted with C 1 to C 60 alkyl group; amine group; —SiR 20 R 21 R 22 ; and —P(═O)R 23 R 24 ,

r is an integer of 1 to 5,

when r is 2 or more, E's are the same as or different from each other,

R 20 to R 24 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C 1 to C 60 alkyl; a substituted or unsubstituted C 6 to C 60 aryl; or a substituted or unsubstituted C 2 to C 60 heteroaryl,

L is selected from the group consisting of a direct bond; a substituted or unsubstituted C 6 to C 60 arylene; and a substituted or unsubstituted C 2 to C 60 heteroarylene,

m is an integer of 1 to 3,

n is an integer of 1 to 3,

Z is selected from the group consisting of hydrogen; deuterium; —P(═O)R 15 R 16 ; —SiR 17 R 18 R 19 ; a substituted or unsubstituted C 1 to C 60 alkyl; a substituted or unsubstituted C 6 to C 60 aryl; a substituted or unsubstituted C 2 to C 60 heteroaryl; and an amine which is unsubstituted or substituted with one or more substituents selected from a substituted or unsubstituted C 1 to C 60 alkyl, a substituted or unsubstituted C 6 to C 60 aryl, and a substituted or unsubstituted C 2 to C 60 heteroaryl,

wherein when E is hydrogen, Z is selected from the group consisting of a substituted or unsubstituted C 6 to C 60 aryl, and a substituted or unsubstituted C 2 to C 60 heteroaryl,

when m is 2 or more, L's are the same as or different from each other,

when n is 2 or more, Z's are the same as or different from each other,

R 15 to R 19 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C 1 to C 60 alkyl; a substituted or unsubstituted C 6 to C 60 aryl; or a substituted or unsubstituted C 2 to C 60 heteroaryl, and

the definitions of R 2 and R 4 to R 9 are the same as those defined in Chemical Formula 5.

3. The hetero-cyclic compound of claim 1 , wherein the hetero-cyclic compound represented by Chemical Formula 4 or 5 is selected from the following compounds:

4. An organic light emitting device comprising:

a positive electrode;

a negative electrode; and

one or more organic material layers provided between the positive electrode and the negative electrode,

wherein one or more layers of the organic material layers comprise the hetero-cyclic compound of claim 1 .

5. The organic light emitting device of claim 4 , wherein the organic material layer comprising the hetero-cyclic compound is at least one layer selected from a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injection layer.

6. The organic light emitting device of claim 4 , wherein the organic material layer comprising the hetero-cyclic compound is an electron transporting layer.

Assignments (2)
CHANGE OF NAME Recorded Feb 13, 2020
From: HEESUNG MATERIAL LTD.
To: LT MATERIALS CO., LTD.
Reel/Frame 051926/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2017
From: KIM, MI-JIN; KIM, KEE-YONG; HA, YANG-SOO; CHOI, JIN-SEOK; CHOI, DAE-HYUK; EUM, SUNG-JIN; LEE, JOO-DONG
To: HEESUNG MATERIAL LTD.
Reel/Frame 042193/0725 →
Priority Claims (1)
KR 10-2014-0150750 · Oct 31, 2014 · national
Continuity (1)
Related Publication 20170324046A1 · Nov 9, 2017