Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Patent metadata

Field	Value
Publication number	US-12245505-B2
Application number	US-202418746317-A
Country	US
Kind code	B2
Filing date	Jun 18, 2024
Priority date	Oct 26, 2020
Publication date	Mar 4, 2025
Grant date	Mar 4, 2025

Abstract

Provided are a compound for use in an organic electronic element that improves luminous efficiency, stability, and lifespan of the element, a composition comprising the compound, an organic electronic element employing the compound, and an electronic device thereof.

First claim

What is claimed is:

1. A compound represented by Formula 1:

wherein:
R 1 and R 2 are the same or different from each other and are independently selected from the group consisting of hydrogen; deuterium; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si or 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 alkoxy group; and a C 6 -C 30 aryloxy group, wherein adjacent groups are not bonded to each other to form a ring,
R 3 is selected from the group consisting of hydrogen; deuterium; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one hetero atom of O, N, S, Si or 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 alkoxy group; and a C 6 -C 30 aryloxy group, wherein an adjacent plurality of R 3 may be bonded to each other to form a ring,
R 4 is hydrogen; deuterium; or a C 6 -C 60 aryl group, and at least one of R 4 is a C 6 -C 60 aryl group,
L 1 is a single bond; or a C 6 -C 60 arylene group,
Ar 1 is a C 6 -C 60 aryl group; or a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or P,
X is O or S,
a and c are independently an integer of 0 to 4, b is an integer of 0 to 3, d is an integer of 1 to 7,
wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group 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 alkoxyl group; a C 6 -C 20 aryloxy 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; a C 3 -C 20 aliphatic ring; a C 7 -C 20 arylalkyl group; a C 8 -C 20 arylalkenyl group; and a C 7 -C 20 alkylaryl group, where hydrogen of the substituents may be substituted with one or more deuterium, and the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C 3 -C 60 aliphatic ring or a C 6 -C 60 aromatic ring or a C 2 -C 60 heterocyclic group or a fused ring formed by the combination thereof with the proviso that the aryl group of R 4 does not have a substituent(s) forming the heterocyclic group.

2. The compound according to claim 1 , wherein L 1 is represented by any of formulas <L-1>to <L-19>:

wherein:
R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are each the same or different, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a C 1 -C 20 alkoxyl group; a C 6 -C 20 aryloxy 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; a C 3 -C 20 aliphatic ring; a C 7 -C 20 arylalkyl group; a C 8 -C 20 arylalkenyl group; and a C 7 -C 20 alkylaryl group, or adjacent groups thereof can be bonded to each other to form an aromatic ring,
g, j and k are independently an integer of 0 to 4, h and i are independently an integer of 0 to 6, and
* means the position to be bonded.

3. The compound according to claim 1 , wherein Ar 1 is any of Formulas A-1 to A-11:

wherein:
Z is O, S or C(R′) (R″),
R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R′, and R″ are each the same or different, and each independently selected from the group consisting of hydrogen; deuterium;
halogen; a cyano group; a nitro group; a C 1 -C 20 alkoxyl group; a C 6 -C 20 aryloxy 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; a C 3 -C 20 aliphatic ring; a C 7 -C 20 arylalkyl group; a C 8 -C 20 arylalkenyl group; and a C 7 -C 20 alkylaryl group, or adjacent groups thereof can be bonded to each other to form an aromatic ring,
R b is selected from the group consisting of a single bond; a C 6 -C 20 arylene group; a C 2 -C 20 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C 3 -C 20 aliphatic ring and a C 6 -C 20 aromatic ring; a C 1 -C 20 alkylene group; and
a C 2 -C 20 alkenylene group;
R c is selected from the group consisting of hydrogen; deuterium; a C 6 -C 20 aryl group; a C 2 -C 20 heterocyclic group including at least one hetero atom of O, N, S, Si or P; a fused ring group of a C 3 -C 20 aliphatic ring and a C 6 -C 20 aromatic ring; a C 1 -C 20 alkyl group; and a C 2 -C 20 alkenyl group;
R b and R c can be bonded to each other to form a ring,
hydrogens of R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 , R′, R″, R b and R c may be substituted with one or more deuterium, and
* means the position to be bonded.

4. The compound according to claim 1 , wherein the compound represented by Formula 1 is any of Compounds P-1 to P-100:

Assignees

• Duk San Neolux Co Ltd

Inventors

• Hahn Seung Hoon
• Park Jae Doh
• Lee Junggeun

Classifications

• Y02E10/549

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• H10K50/16

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