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

Patent metadata

Field	Value
Publication number	US-11233202-B2
Application number	US-201716310619-A
Country	US
Kind code	B2
Filing date	Apr 25, 2017
Priority date	Jun 17, 2016
Publication date	Jan 25, 2022
Grant date	Jan 25, 2022

Abstract

The present invention provides the compound represented by Formula 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 electronic device thereof, and by comprising the compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electronic device can be lowered, and the luminous efficiency and life time of the organic electronic device can be improved.

First claim

The invention claimed is:

1. A compound of Formula 1:

wherein:
Ar 1 to Ar 4 are each 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 fluorenyl group, a fused ring group of 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 alkoxyl group and a C 6 -C 30 aryloxy group, with the proviso that a triphenylene group is excluded from Ar 2 and a carbazole group is excluded from Ar 3 and Ar 4 ,
R 1 to R 3 are each independently selected from the group consisting of deuterium, tritium, halogen, a cyano group, a nitro group, 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 group of 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 alkoxyl group and a C 6 -C 30 aryloxy group,
m is an integer of 0, or 2 to 4, n is an integer of 0, 2 or 3, o is 0, and adjacent R 1 s or adjacent R 2 s are linked together to form at least one monocyclic ring when m or n is each an integer of 2 or more,
L 1 is selected from the group consisting of 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 an aliphatic hydrocarbon group, and
the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxyl group of Ar 1 to Ar 4 , R 1 to R 3 and L 1 are each optionally further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group substituted or unsubstituted with C 1 -C 20 alkyl group or C 6 -C 20 aryl 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 alkoxyl 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, wherein adjacent substituents may optionally be linked together to form a ring, with the proviso that where an aryl group of Ar 2 to Ar 4 is substituted with a heterocyclic group, a carbazole, a dibenzothienyl group or a dibenzofuryl group is excluded from the heterocyclic group.

2. The compound of claim 1 , wherein Formula 1 is represented by one of the following Formulas 2 to 4:

wherein Ar 1 to Ar 4 , R 1 to R 3 , L 1 , m, n and o are the same as defined in claim 1 .

3. The compound of claim 1 , wherein L 1 1 is represented by one of the following Formulas L1-1 to L1-7:

wherein:
X is S, O, C(R a )(R b ) or N(R c ), wherein R a , R b and R c are each independently selected from the group consisting of a C 6 -C 20 aryl group, 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 fused ring group of a C 3 -C 20 aliphatic ring and a C 6 -C 60 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 alkoxyl group and a C 6 -C 30 aryloxy group, and R a and R b may optionally be linked together to form a spiro compound together with a carbon to which they are bonded,
R 4 and R 5 are each independently selected from the group consisting of a C 6 -C 20 aryl group, 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 fused ring group of a C 3 -C 20 aliphatic ring and a C 6 -C 60 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 alkoxyl group and a C 6 -C 30 aryloxy group, and
a to b are each an integer of 0 to 4, c is an integer of 0 to 6, d is an integer of 0 to 5, e and f are each an integer of 0 to 3, and each of the plurality of R 4 s and each of the plurality of R 5 s are the same or different from each other where a, b, c, d, e and f are each an integer of 2 or more.

4. A compound of Formula 1:

wherein:
Ar 1 to Ar 4 are each 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 fluorenyl group, a fused ring group of 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 alkoxyl group and a C 6 -C 30 aryloxy group, with the proviso that a triphenylene group is excluded from Ar 2 and a carbazole group is excluded from Ar 3 and Ar 4 ,
R 1 to R 3 are each independently selected from the group consisting of deuterium, tritium, halogen, a cyano group, a nitro group, 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 group of 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 alkoxyl group and a C 6 -C 30 aryloxy group,
m and o are each an integer of 0 to 4, n is an integer of 0 to 3 and adjacent R 1 s, adjacent R 2 s or adjacent R 3 s may optionally be linked together to form a ring when m, n or o is each an integer of 2 or more,
L 1 is selected from the group consisting of 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 an aliphatic hydrocarbon group, and
the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxyl group of Ar 1 to Ar 4 , R 1 to R 3 and L 1 are each optionally further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group substituted or unsubstituted with C 1 -C 20 alkyl group or C 6 -C 20 aryl 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 alkoxyl 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

Assignees

• Duk San Neolux Co Ltd

Inventors

• Park Jonggwang
• Lee Yun Suk
• So Kiho
• Park Hyoung Keun
• Jeong Yeonseok
• Choi Yeon Hee
• Kwon Jae-Taek

Classifications

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/624

  containing six or more rings · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title