Compound for organic electronic element, organic electronic element comprising the same and electronic device thereof

Patent metadata

Field	Value
Publication number	US-10319922-B2
Application number	US-201815977327-A
Country	US
Kind code	B2
Filing date	May 11, 2018
Priority date	Oct 6, 2014
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

Provided are a compound of Formula 1 and an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and electronic device comprising the organic electric element, wherein the luminous efficiency and life span can be improved and the driving voltage of the organic electronic device can be lowered by comprising the compound represented by Formula 1 in the organic material layer.

First claim

The invention claimed is:

1. A compound of Formula 1:

wherein
one of A and B is a compound of Formula 1-1 and the other is a compound of Formula 1-2 or Formula 1-3 , with the proviso that the compound where Ar 1 to Ar 3 are phenyl and L 1 is m-phenylene when one of A and B is Formula 1-1 is excluded:

Ar 1 to Ar 4 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C 6 -C 60 aromatic ring and a C 3 -C 60 aliphatic ring; —L′—N(R a )(R b ); and the combination thereof,
L 1 to L 3 are each independently selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a fused ring formed by a C 6 -C 60 aromatic ring and a C 3 -C 60 aliphatic ring; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and the combination thereof,
R 1 to R 16 are each independently i) selected from the group consisting of hydrogen; deuterium; halogen; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; a fused ring formed by a C 6 -C 60 aromatic ring and a C 3 -C 60 aliphatic ring; a C 1 -C 50 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 30 alkoxy group; a C 6 -C 30 aryloxy group; —L′—N(R a )(R b ); and the combination thereof, or ii) neighboring groups of R 1 s to R 16 s may be linked to each other to form a ring together with a benzene ring to which they are bonded, and wherein R 1 s to R 16 s not forming a ring are each the same as defined in the above i),
L′ is selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a fluorenylene group; a fused ring formed by a C 6 -C 60 aromatic ring and a C 3 -C 60 aliphatic ring; and a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P,
R a and R b are each independently selected from the group consisting of a C 6 -C 60 aryl group; a fluorenyl group; a fused ring formed by a C 6 -C 60 aromatic ring and a C 3 -C 60 aliphatic ring; and a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, and
the above aryl group, fluorenyl group, heterocyclic group, fused ring, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group and fluorenylene group may be each substituted with one or more substituents 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 fluorenyl group; a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; 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 Formula 1 is represented by one of Formulas 3 to 5 and 8 below:

wherein Ar 1 to Ar 4 , L 1 to L 3 and R 1 to R 16 are each the same as defined in claim 1 .

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

4. 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 .

5. The organic electric element of claim 4 , wherein at least one of a hole injection layer, a hole transport layer, an emission-auxiliary layer and an light emitting layer of the organic material layer comprises one kind or two or more kinds of compounds represented by Formula 1.

6. The organic electric element of claim 4 , wherein the organic electric element further including at least one layer to improve luminous efficiency which is formed on at least one of the sides the first and second electrodes, which is opposite to the organic material layer.

7. The organic electric element of claim 4 , 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.

8. An electronic device comprising:
a display device comprising the organic electric element of claim 1 ; and
a control unit for driving the display device.

9. The electronic device of claim 8 , 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.

Assignees

• Duk San Neolux Co Ltd

Inventors

• Lee Bumsung
• Lee Sun-Hee
• Kim Daesung
• Lee Yun Suk
• Lee Gyumin

Classifications

• H01L51/5092

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• C07D209/82 Primary

  Carbazoles; Hydrogenated carbazoles · CPC title

• H01L51/5056

  Electricity · mapped topic