Organic electronic element using a compound for organic electronic element, and an electronic device thereof

Patent metadata

Field	Value
Publication number	US-10326092-B2
Application number	US-201515327429-A
Country	US
Kind code	B2
Filing date	Jul 17, 2015
Priority date	Jul 21, 2014
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

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 luminescent efficiency, stability, and life span.

First claim

The invention claimed is:

1. 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 comprising at least an emission-auxiliary layer and a hole transport layer, wherein the emission-auxiliary layer comprises a compound represented by Formula 1 below,

wherein,
Ar 1 to Ar 5 are each independently selected from the group consisting of a C 6 -C 24 aryl group; a fluorenyl group; a C 2 -C 25 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 3 -C 24 aliphatic ring and a C 6 -C 24 aromatic ring; 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; a C 6 -C 30 aryloxy group and the combination thereof,
L 1 and L 2 are each independently selected from the group consisting of a single bond, a C 6 -C 24 arylene group, a fluorenylene group, a C 2 -C 24 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 3 -C 24 aliphatic ring and a C 6 -C 24 aromatic ring and the combination thereof,
when Ar 1 to Ar 5 are each independently an aryl group, a fluorenyl group, a heterocyclic group, a fused ring, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an aryloxy group, each of Ar 1 to Ar 5 may be 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, and
when L 1 and L 2 are each independently an arylene group, a fluorenylene group, a heterocyclic group or a fused ring, each of L 1 and L 2 may be 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 organic electric element of claim 1 , wherein Formula 1 is represented by one of Formulas 2 to 6 below:

in formulas 2 to 6, Ar 1 to Ar 5 , L 1 and L 2 are each the same as defined in claim 1 .

3. The organic electric element of claim 1 , wherein Ar 1 to Ar 5 are each independently a C 6 -C 12 aryl group and both L 1 and L 2 are a single bond.

4. The organic electric element of claim 1 , wherein Ar 1 to Ar 4 are each phenyl, Ar 5 is biphenyl, and L 1 and L 2 are each independently a single bond or phenylene.

5. The organic electric element of claim 1 , wherein the compound represented by Formula 1 is any one of the compounds below:

6. The organic electric element of claim 1 , wherein the compound is a single compound or a mixture of two or more different compounds.

7. 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 comprising at least one of a hole transport layer, an emission-auxiliary layer and a light emitting layer, wherein the emission-auxiliary layer comprises a compound represented by Formula 1 below, and the light emitting layer comprises a compound represented by Formula 7 below,

wherein,
Ar 1 to Ar 5 are each independently selected from the group consisting of a C 6 -C 24 aryl group; a fluorenyl group; a C 2 -C 25 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 3 -C 24 aliphatic ring and a C 6 -C 24 aromatic ring; 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; a C 6 -C 30 aryloxy group and the combination thereof,
L 1 and L 2 are each independently selected from the group consisting of a single bond, a C 6 -C 24 arylene group, a fluorenylene group, a C 2 -C 24 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 3 -C 24 aliphatic ring and a C 6 -C 24 aromatic ring and the combination thereof,
i) Ar 6 and Ar 7 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 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic 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, and ii) Ar 6 and Ar 7 may be linked together to form a ring,
Ar 8 is any one of Formulas 7-a, 7-b and 7-c below,

in formulas 7-a, 7-b and 7-c,
Ar 9 to Ar 11 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 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic 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,
i) R 1 to R 3 are each independently selected from the group consisti

Assignees

• Duk San Neolux Co Ltd

Inventors

• Lee Bumsung
• Lee Sunhee
• Mun Soungyun
• Kim Daesung
• Lee Gyumin

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C07C211/57

  having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title