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

Patent metadata

Field	Value
Publication number	US-9570689-B2
Application number	US-201615093126-A
Country	US
Kind code	B2
Filing date	Apr 7, 2016
Priority date	May 28, 2014
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

Provided herein are a compound of Formula 1, and an organic electric element comprised of a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode containing a compound of Formula 1, which has an improvement in driving voltage, luminous efficiency, color purity, stability, and life span.

First claim

The invention claimed is:

1. A compound represented by Formula 1 below:

in Formula 1 above,
S ring is a C 4 -C 8 heterocyclic group containing S(sulfer),
N ring is a C 4 -C 8 heterocyclic group containing N(nitrogen),
l, m, and n are each an integer from 0 to 4,
R 1 to R 3 are independently selected from the group consisting of halogen, deuterium, a cyano group, a C 6-60 aryl group, a C 2-60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P, a C 1 -C 30 alkoxy group, a C 1 -C 60 alkyl group, a C 2-60 alkenyl group, and -L 1 -N(R′)(R″), and any two adjacent groups of R 1 s to R 3 s are optionally linked together to form a fused ring,
L and L 1 are independently selected from the group consisting of a single bond, a C 6 -C 60 arylene group, and a C 2 -C 60 heteroarylene group containing at least one heteroatom selected from O, N, S, Si, and P, wherein, the arylene group, and the heteroarylene group are optionally substituted by 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 by deuterium, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from 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,
Ar is a C 6 -C 60 aryl group or a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P,
wherein the aryl group is substituted with one or more selected from the group consisting of 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 substituted by deuterium, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from 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,
with the proviso that where the aryl group is substituted with a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P, the heterocyclic group excludes a carbazolyl group; and
the heterocyclic group is optionally substituted with one or more selected from the group consisting of 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 by deuterium, a C 2 -C 6 heterocyclic group containing at least one heteroatom selected from 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,
with the proviso that the heterocyclic group excludes a carbazolyl group,

R′ and R″ are independently selected from the group consisting of a C 6 -C 60 aryl group, and a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P,
X and Y are independently selected from the group consisting of a single bond, C(R 4 )(R 5 ), N(R 4 ), O, S, Se, and Si(R 4 )(R 5 ),
R 4 and R 5 are independently selected from the group consisting of hydrogen, deuterium, a C 6-60 aryl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P, a C 1 -C 30 alkoxy group, a C 1 -C 60 alkyl group, and a C 2 -C 60 alkenyl group,
when R 1 to R 5 , R′, and R″ are an aryl group, a fluorenyl group or a heterocyclic group, R 1 to R 5 , R′, and R″ are optionally substituted by 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 2-20 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 60 heterocyclic group containing at least one heteroatom selected from 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 R 1 to R 5 are an alkyl group, alkenyl group or alkoxy, R 1 to R 5 are optionally substituted by 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 6-20 aryl group, a C 6 -C 20 aryl group substituted by deuterium, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from 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 as claimed in claim 1 , wherein the compound is represented by one of Formulas below:

in Formulas above, Ar, R 1 to R 3 , l, m, n, X and Y are as defined in Formula 1 of claim 1 .

3. The compound as claimed in claim 1 , wherein Z is any one of groups below:

in Formulas above, Ar, X and Y are as defined in Formula 1 of claim 1 .

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

in Formulas above, Ar, R 1 to R 3 , l, m and n are as defined in Formula 1 of claim 1 .

5. The compound as claimed in claim 1 , wherein Ar is any one of groups below:

6. The compound as claimed in claim 1 , being any one of compounds below:

Assignees

• Duk San Neolux Co Ltd
• Samsung Display Co Ltd

Inventors

• Park Junghwan
• Kim Wonsam
• Byun Jihun
• Park Jeongkeun
• Jung Hwasoon
• Choi Yeonhee
• Kim Seokhyun
• Lee Kwanhee
• Kim Mikyung

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C09K2211/1048

  with oxygen · CPC title

• H01L51/0073

  Electricity · mapped topic

• H01L51/5221

  Electricity · mapped topic