IP Library Granted Patent US 10,916,709
Granted Patent B2
US 10,916,709 · App. 15/539,223 · Granted Feb 9, 2021

Organic compound and organic electroluminescent element comprising same

Inventors: Min-Sik Eum (Seoul, KR); Hojun Son (Seoul, KR); Woo Jae Park (Seoul, KR); Tae Hyung Kim (Yongin-si, KR); Jiyi Kim (Yongin-si, KR); Youngmi Beak (Yongin-si, KR)
Assignee: DOOSAN SOLUS CO., LTD.
H01L51/0067C07D213/16C07D239/26C07D251/24C09K11/025C09K11/06H01L51/0052H01L51/0054H01L51/0055H01L51/0056H01L51/0059H01L51/0061H01L51/0072H01L51/0085H01L51/5004C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/185H01L51/508H01L51/5016H01L51/5072H01L51/5092H01L51/52H01L2251/552
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Quick Facts
Patent No.
US 10,916,709
App. No.
15/539,223
Granted
Feb 9, 2021
Kind
B2
Abstract

The present invention relates to a novel organic compound, and an organic electroluminescent element having improved characteristics, such as luminous efficiency, driving voltage, and lifespan, by containing the novel organic compound in one or more organic material layers.

Claims (38)

1. An organic electroluminescent element comprising, in the order,

an anode;

a hole injection layer;

a hole transport layer;

a light emitting layer;

an auxiliary electron transport layer;

an electron transport layer; and

cathode,

wherein the auxiliary electron transport layer comprises a compound of the following Formula 1:

wherein,

R a and R b are the same or different from each other and are each independently a C 1 -C 40 alkyl group or a C 6 -C 60 aryl group,

R 1 and R 2 are the same or different from each other and are each independently selected from the group consisting of a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, an amino group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 -C 40 alkyloxy group, a C 6 -C 60 aryloxy group, a C 1 -C 40 alkylsilyl group, a C 6 -C 60 arylsilyl group, a C 1 -C 40 alkylboron group, a C 6 -C 60 arylboron group, a C 1 -C 40 phosphine group, a C 1 -C 40 phosphine oxide group, and a C 6 -C 60 arylamine group, or in this case, adjacent ones of R 1 and R 2 are optionally respectively to each other to form a fused ring,

R 3 is a hydrogen,

L is selected from the group consisting of a single bond, a C 6 -C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms, with the proviso that where L is a C 6 -C 18 arylene group, the C 6 -C 18 arylene group is selected from the group consisting of phenylene, biphenylene, and terphenylene,

Z 1 to Z 5 are the same or different from each other and are each independently N or C(R 4 ), and provided that Z 1 to Z 5 include three N, and when C(R 4 ) is present in a plural number, they are optionally the same as or different from each other,

c and e are each an integer of 0 to 4,

d is an integer of 0 to 3,

m and n are each an integer of 1 to 3, and

R 4 is selected from the group consisting of a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, an amino group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 -C 40 alkyloxy group, a C 6 -C 60 aryloxy group, a C 1 -C 40 alkylsilyl group, a C 6 -C 60 arylsilyl group, a C 1 -C 40 alkylboron group, a C 6 -C 60 arylboron group, a C 1 -C 40 phosphine group, a C 1 -C 40 phosphine oxide group, and a C 6 -C 60 arylamine group, or bonded to an adjacent substituent to form a fused ring,

with the proviso that:

(i) the compound, in which Z 1 to Z 5 include three N, L is a single bond, R 3 is a hydrogen and n is 1, is excluded: and

(ii) the compound, in which Z 1 to Z 5 include three N, L is a single bond, R 3 is a hydrogen, and n is 2, is represented by Formula 8:

wherein Z 3 is N, and R a , R b , R 1 , R 2 , R 4 , c, and d are the same as defined above with regard to Formula 1, and

wherein the alkyl and aryl groups of R a and R b ; the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyloxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, phosphine, phosphine oxide, and arylamine groups of R 1 , R 2 and R 4 are optionally each independently unsubstituted or substituted with at least one selected from the group consisting of a deuterium, a halogen, a cyano group, a nitro group, an amino group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 -C 40 alkyloxy group, a C 6 -C 60 aryloxy group, a C 1 -C 40 alkylsilyl group, a C 6 -C 60 arylsilyl group, a C 1 -C 40 alkylboron group, a C 6 -C 60 arylboron group, a C 1 -C 40 phosphine group, a C 1 -C 40 phosphine oxide group, and a C 6 -C 60 arylamine group, and provided that when the substituent is present in a plural number, they are optionally the same or different from each other.

2. The organic electroluminescent element of claim 1 , wherein the compound is selected from the group consisting of the compounds of the following Formula 3 and 4:

wherein,

R a , R b , R 1 , R 2 , R 3 , c, d, e, Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are the same as defined in claim 1 ,

3. The organic electroluminescent element of claim 1 , wherein the structure represented by

wherein * is a site where to bond with L, in Formula 1 is the group of the following C-9:

wherein,

R 4 is the same as defined in claim 1 .

4. The organic electroluminescent element of claim 1 , wherein R a and R b are each independently a methyl or a phenyl.

5. The organic electroluminescent element of claim 1 , wherein L is selected from the group consisting of the structures represented by the following L-1 to L-7:

wherein * is a site where to bond.

6. The organic electroluminescent element of claim 1 , wherein the compound represented by Formula 1 is selected from the group consisting of the following Compounds 21, 23, 61, 62, 89, 91, 189, 191 to 197, 199 to 204, 217 to 219, 221 to 224, 226 to 228, 233 to 239, 243 to 250:

7. The organic electroluminescent element of claim 1 , which further comprises an auxiliary light emitting layer between the hole transport layer and the light emitting layer.

8. The organic electroluminescent element of claim 1 , wherein the light emitting layer comprises a host and a dopant, said host being the compound of the formula 1.

9. The organic electroluminescent element of claim 1 , which is blue organic electroluminescent element.

Assignments (3)
CHANGE OF NAME Recorded Dec 29, 2020
From: DOOSAN SOLUS CO., LTD.
To: SOLUS ADVANCED MATERIALS CO., LTD.
Reel/Frame 054867/0169 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2020
From: DOOSAN CORPORATION
To: DOOSAN SOLUS CO., LTD.
Reel/Frame 052128/0274 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2017
From: EUM, MIN-SIK; SON, HOJUN; PARK, WOO JAE; KIM, TAE HYUNG; KIM, JIYI; BEAK, YOUNGMI
To: DOOSAN CORPORATION
Reel/Frame 042796/0574 →
Priority Claims (4)
KR 10-2014-0188953 · Dec 24, 2014 · national
KR 10-2015-0171639 · Dec 3, 2015 · national
KR 10-2015-0171678 · Dec 3, 2015 · national
KR 10-2015-0178926 · Dec 15, 2015 · national
Continuity (1)
Related Publication 20180053900A1 · Feb 22, 2018