IP Library › Granted Patent US 10,381,574
Granted Patent B2
US 10,381,574 · App. 15/507,036 · Granted Aug 13, 2019

Compound for organic electronic element, organic electrical element using compound, and electronic device comprising same

Inventors: Jae Wan Jang (Cheonan-si, KR); Ho Young Jung (Cheonan-si, KR); Seul-gi Kim (Daejeon, KR); Won Sam Kim (Hwaseong-Si, KR); Ji Hun Byun (Cheonan-Si, KR); Jung Hwan Park (Hwaseong-si, KR); Sun Pil Hwang (Ansan-si, KR)
Assignee: Duk San Neolux Co., Ltd.
H01L51/0071C07B59/002C07D495/14C07D495/22C07D519/00C09K11/06H01L51/0058H01L51/0067H01L51/0072H01L51/0073H01L51/0074H01L51/50H05B33/20C07B2200/05C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H01L51/0052H01L51/0081H01L51/0085H01L51/5016Y02E10/549
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Quick Facts
Patent No.
US 10,381,574
App. No.
15/507,036
Granted
Aug 13, 2019
Kind
B2
Abstract

The objective of the present invention is to provide: a compound capable of ensuring high light-emitting efficiency and low driving voltage of an element, and increasing the lifespan thereof; an organic electrical element using compound; and an electronic device comprising the same.

Claims (31)

1. A compound represented by Formula 1:

wherein in Formula 1,

Ar 1 and Ar 2 each are independently selected from the group consisting of a C 6 -C 60 aryl group, a fused ring group of a C 3 -C 60 aliphatic group and a C 6 -C 60 aromatic group, a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C 1 -C 50 alkyl group, and —N(R′)(R″);

R′ and R″ each are independently selected from the group consisting of a C 6 -C 60 aryl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C 1 -C 50 alkyl group;

L 1 and L 2 each are selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a C 2 -C 60 bivalent heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a fused ring group of a C 3 -C 60 bivalent aliphatic group and a C 6 -C 60 bivalent aromatic group, and a bivalent aliphatic hydrocarbon group, each of which (excluding the single bond) may be substituted with at least one substituent selected from the group consisting of deuterium, a nitro group, a nitrile group, a halogen group, a C 1 -C 20 alkyl group, a C 6 -C 20 aryl group, a C 2 -C 20 heterocyclic group, a C 1 -C 20 alkoxy group, and an amino group;

X 1 to X 8 each are independently CR 1 or N;

i) R 1 is selected from the group consisting of hydrogen, deuterium, halogen, a C 6 -C 60 aryl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a fused ring group of a C 6 -C 60 aromatic group and a C 3 -C 60 aliphatic group, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 30 alkoxy group, and a C 6 -C 30 aryloxy group, or ii) in the presence of a plurality of R 1 's, the plurality of R 1 's are different from or the same as each other and adjacent R 1 's may be linked to each other to form at least one ring (provided that R 1 forming no ring is the same as defined in i) above);

the aryl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, and aryloxy group each may be substituted with at least one substituent selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium 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 C 2 -C 20 heterocyclic group, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 arylalkyl group, a C 8 -C 20 arylalkenyl group, and —N(R a )(R b );

R a and R b each are independently selected from the group consisting of a C 6 -C 60 aryl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C 1 -C 50 alkyl group; and

ring A is represented by one of the formulas below:

wherein in A4 to A6,

's are binding positions at which any one side of each of rings (thiophene and pyrrole) adjacent to ring A is shared and condensed;

m is an integer of 0 to 4;

R 3 is i) selected from the group consisting of deuterium, halogen, a C 6 -C 60 aryl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a fused ring group of a C 6 -C 60 aromatic group and a C 3 -C 60 aliphatic group, a C 2 -C 20 alkenyl group, a C 1 -C 30 alkoxy group, and a C 6 -C 30 aryloxy group, or ii) in the presence of a plurality of R 3 's, the plurality of R 3 's are different from or the same as each other and adjacent R 3 's may be linked to each other to form at least one ring (provided that R 3 forming no ring are the same as defined in i) above); and

the aryl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, and aryloxy group each may be substituted with at least one substituent selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium 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 C 2 -C 20 heterocyclic group, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 arylalkyl group, and a C 8 -C 20 arylalkenyl group.

2. An organic electronic element comprising:

a first electrode;

a second electrode; and

an organic material layer positioned between the first electrode and the second electrode,

wherein the organic material layer contains a compound of claim 1 .

3. The organic electronic element of claim 2 ,

wherein the organic material layer contains a mixture of two or more compounds according to claim 1 .

4. The organic electronic element of claim 2 , further comprising a light efficiency improving layer formed on at least one of one surface of the first electrode and one of the second electrode, which is opposite to the organic material layer.

5. The organic electronic element of claim 2 , wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process.

6. The compound of claim 1 , wherein at least one of Ar 1 and Ar 2 is a fluorenyl group.

7. The compound of claim 1 , wherein at least one of R′ and R″ is a fluorenyl group.

8. The compound of claim 1 , wherein at least one of L 1 and L 2 is a fluorenylene group.

9. An electronic device comprising:

a display device comprising the organic electronic element of claim 2 ; and

a controller driving the display device.

10. The electronic device of claim 9 , wherein the organic electric element is one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for a monochromatic or white illumination.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2017
From: JANG, JAE WAN; JUNG, HO YOUNG; KIM, SEUL-GI; KIM, WON SAM; BYUN, JI HUN; PARK, JUNG HWAN; HWANG, SUN PIL
To: DUK SAN NEOLUX CO., LTD
Reel/Frame 041385/0419 →
Priority Claims (1)
KR 10-2014-0114083 · Aug 29, 2014 · national
Continuity (1)
Related Publication 20170256719A1 · Sep 7, 2017
Cited By (1)
US 12,232,420