IP Library › Granted Patent US 10,700,285
Granted Patent B2
US 10,700,285 · App. 15/120,330 · Granted Jun 30, 2020

Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Inventors: Soung Yun Mun (Cheonan-si, KR); Sun-Hee Lee (Cheonan-si, KR); Jung Cheol Park (Suwon-si, KR); DaeSung Kim (Yongin-si, KR); Bum Sung Lee (Cheonan-si, KR); Seok hyun Kim (Seongnam-si, KR)
Assignee: DUK SAN NEOLUX CO., LTD.
H01L51/0061C07D209/86C07D401/10C07D403/04C07D403/10C07D403/12C07D405/04C07D405/12C07D409/04C07D409/12C09K11/06H01L51/0072H01L51/0074H01L51/006H01L51/0058H01L51/50H01L51/5016H01L51/5056H01L51/5096Y02E10/549
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Quick Facts
Patent No.
US 10,700,285
App. No.
15/120,330
Granted
Jun 30, 2020
Kind
B2
Abstract

Provided are a compound of Formula 1 and an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode and comprising the compound, the element showing improved luminous efficiency, stability, and life span.

Claims (31)

1. A compound of Formula 1:

wherein,

Ar 1 to Ar 3 are each independently selected form the group consisting of a C 6 -C 18 aryl group; a fluorenyl group; and a C 2 -C 16 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N and S,

L is

 wherein * indicates the position to which the nitrogen atom(N) of the amine group in Formula 1 is linked,

a, b and m are each an integer of 0 to 4, and n is an integer of 0 to 3,

R 1 to R 4 are each independently selected from the group consisting of deuterium; a C 6 -C 18 aryl group; a fluorenyl group; a C 2 -C 14 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N and S; and a C 2 -C 20 alkenyl group; or adjacent groups of R 1 s to R 4 s may be linked to form benzene ring, and the group(s) not forming the ring is(are) the same as defined in the above, and

each of the above aryl group, fluorenyl group, heterocyclic group, alkenyl group, may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group; a siloxane group; a cyano group; a nitro group; a C 1 -C 20 alkylthio group; a C 1 -C 20 alkoxy group; a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 6 -C 20 aryl group; a C 6 -C 20 aryl group substituted with deuterium; a fluorenyl group; a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N and S, a C 3 -C 20 cycloalkyl group; a C 7 -C 20 arylalkyl group; and a C 8 -C 20 arylalkenyl group.

2. The compound of claim 1 , wherein a and b are each 0 (zero), or R 3 and R 4 are each independently selected from the following structures:

3. The compound of claim 1 , wherein at least one of R 1 s or R 2 s is linked to form benzene ring between adjacent groups.

4. The compound of claim 3 represented by one of Formulas below:

wherein, Ar 1 to Ar 3 , L, R 1 , R 2 , m and n are the same as defined in claim 1 .

5. The compound of claim 1 , wherein Ar 1 is selected from the following structures:

wherein X is O, S or C(R′)(R″),

R′ and R″ are each independently selected from the group consisting of a C 6 -C 20 aryl group; and a C 1 -C 20 alkyl group, or

R′ and R″ may be linked together to form a spiro compound with the carbon to which they are attached,

o is an integer of 0 to 4, and p is an integer of 0 to 3,

R 5 and R 6 are each independently selected from the group consisting of deuterium; a C 6 -C 20 aryl group; a fluorenyl group; a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N and S, a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxy group; and a C 6 -C 30 aryloxy group, or adjacent groups of R 5 s and R 6 s may be linked to form benzene ring, and the group(s) not forming the ring is(are) the same as defined in the above.

6. The compound of claim 5 ,

wherein Ar 1 is

 and

Formula 1 is represented by one of Formulas 11 to 20 below:

in Formulas 11 to 20, Ar 2 , Ar 3 , L, R 1 , R 2 , m and n are the same as defined in claim 1 , and X, R 5 , R 6 , o and p are the same as defined in claim 5 .

7. The compound of claim 1 , wherein Ar 2 and Ar 3 are each independently selected from the following structures:

8. The compound of claim 1 , wherein Formula 1 is any one of the compounds below:

9. An organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of claim 1 .

10. The organic electric element of claim 9 , wherein the organic material layer comprises one or more of a hole injection layer, a hole transport layer, an emission-auxiliary layer and an emitting layer, the one or more layer(s) comprising the compound.

11. The organic electric element of claim 9 , wherein the organic electric element further comprises an additional layer(s) formed on at least one of the sides of the first and second electrodes opposite to the organic material layer.

12. The organic electric element of claim 9 , wherein the organic material layer is formed by any one of the processes of spin coating, nozzle printing, inkjet printing, slot coating, dip coating and roll-to-roll.

13. An electronic device comprising a display device, which comprises the organic electric element of claim 9 , and a control unit for driving the display device.

14. The electronic device of claim 13 , wherein the organic electric element comprises at least one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 19, 2016
From: MUN, SOUNG YUN; LEE, SUN-HEE; PARK, JUNG CHEOL; KIM, DAESUNG; LEE, BUM SUNG; KIM, SEOK HYUN
To: DUK SAN NEOLUX CO., LTD.
Reel/Frame 039485/0044 →
Priority Claims (2)
KR 10-2014-0018889 · Feb 19, 2014 · national
KR 10-2014-0072377 · Jun 13, 2014 · national
Continuity (1)
Related Publication 20170062728A1 · Mar 2, 2017