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

Patent metadata

Field	Value
Publication number	US-10249825-B2
Application number	US-201314650078-A
Country	US
Kind code	B2
Filing date	Dec 3, 2013
Priority date	Dec 6, 2012
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

Provided are a compound capable of improving light emitting efficiency, stability, and lifespan of the element, an organic element using the same, and an electric device for the same.

First claim

The invention claimed is:

1. A compound represented by Formula 1 below:

wherein,
m is an integer from 1 to 4,
n is an integer from 1 to 3,
R 1 and R 2 are independently selected from the group consisting of hydrogen, deuterium, tritium, 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 C1-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,
Ar 1 is selected from the group consisting of a fluorenyl group, a C 6 -C 60 aryl group, a C 2 -C 20 alkenyl 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 C1-C 50 alkyl group, -L 2 -N(Ar 2 )(Ar 3 ), and a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring,
L 1 and L 2 are independently selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a C 2 -C 60 bivalent heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a bivalent fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and a bivalent aliphatic hydrocarbon group,
Ar 2 and Ar 3 are 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 C 1 -C 50 alkyl group, a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and a C 2 -C 20 alkenyl group, and
the aryl group, heterocyclic group, fluorenyl group, alkyl group, alkenyl group, fused ring group, alkoxy group, aryloxy group, arylene group, fluorenylene group and aliphatic hydrocarbon group may be substituted by one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a boron group, a germanium group, a cyano group, a nitro group, -L′-N(R′)(R″), a C 1 -C 20 alkylthio group, a C1-C 20 alkoxy group, a C1-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 by 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, wherein L′ is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene 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 group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, and a C2-C 60 bivalent aliphatic hydrocarbon group, and R′ and R″ are independently from each other 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 C 1 -C 20 alkyl group, and a C 2 -C 20 alkenyl group,
with the proviso that: where Ar 1 is a substituted C 6 -C 60 aryl group, the substituent is selected from the group consisting of deuterium, halogen, a silane group, a boron group, a germanium group, a cyano group, a nitro group, -L′-N(R′)(R″), 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 14 aryl group, a C 6 -C 20 aryl group substituted by 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; and where R 1 or R 2 is a substituted C 6 -C 60 aryl group, the substituent is selected from the group consisting of deuterium, halogen, a silane 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 by 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, and
with the proviso that:
where Ar 1 is a C 6 -C 60 aryl group, L 1 is a single bond, and one of Ar 2 and Ar 3 is a C 6 -C 60 aryl group or a fluorenyl group, the other of Ar 2 and Ar 3 is selected from the group consisting of:

wherein Q 1 is C(R a );

wherein Q 1 is C(R a );

wherein Q 2 is C(R b )(R c ), N(R d ), S, or O;

wherein R a and R e are independently selected from the group consisting of hydrogen, deuterium, a C 6 -C 60 aryl 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 C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 30 alkoxy group, and a fluorenyl group, or any two adjacent groups of R e s can be optionally linked together to form at least one aromatic ring,
R b to R d 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 selected from the group consisting of O, N, S, Si, and P, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, and a C 1 -C 30 alkoxy group, wherein R b and R c are optionally linked together to form at least one spiro compound.

2. The compound as claimed in claim 1 , wherein L 1 is any one of the compounds below:

3. The compound as claimed in claim 1 , wherein Ar 2 and Ar 3 each are independently any one of compounds below:

wherein,
Q 1 is C(R a ) or N,
Q 2 is selected form the group consisting of C(R b )(R c ), N(R d ), S and O,
k is an integer from 1 to 4,
R a and R e are independently selected from the group consisting of hydrogen, deuterium, a C 6 -C 60 aryl 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 C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 30 alkoxy group, and a fluorenyl group, wherein any two adjacent groups of R e s are optionally linked together to form at least one aromatic ring,
R b to R d 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 selected from the group consisting of O, N, S, Si, and P, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, and a C 1 -C 30 alkoxy group, wherein R b and R c are optionally linked together to form at least one spiro compound.

4. The compound as claimed in claim 1 , wherein the compound is represented by one of Formulas below:

wherein,
Ar 2 , Ar 3 , R 1 , R 2 , m and n are as defined for Formula 1 in claim 1 ,
X is selected from

Assignees

• Duk San Neolux Co Ltd
• Samsung Display Co Ltd

Inventors

• Lee Bumsung
• Choi Yeonhee
• Kim Daesung
• Mun Soungyun
• Park Jungcheol
• So Kiho
• Yun Jinho
• Oh Daehwan
• Yeo Seungwon
• Kim Mikyung
• Lee Kwanhee

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title