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

Patent metadata

Field	Value
Publication number	US-2024381768-A1
Application number	US-202418741904-A
Country	US
Kind code	A1
Filing date	Jun 13, 2024
Priority date	Oct 26, 2020
Publication date	Nov 14, 2024
Grant date	—

Abstract

Provided are a compound for improving luminous efficiency, stability, and lifespan of an organic electronic 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:
X is O or S,
L 1 is a single bond; or a C 6 -C 60 arylene group,
Ar 1 is an 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,
Ar 2 is an 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; a C 1 -C 50 alkyl group,
R 1 , R 2 and R 4 are the same or different from each other and are independently hydrogen or deuterium,
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, and an adjacent plurality of R 3 may be bonded to each other to form a ring,
a and c are each independently an integer of 0 to 4, b is an integer of 0 to 3, d is an integer of 0 to 6,
wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy 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, and 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.

2 . The compound according to claim 1 , wherein Formula 1 is represented by Formula 1-1 or 1-2:

wherein X, L 1 , Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d are the same as defined in claim 1 .

3 . The compound according to claim 1 , wherein L 1 is a single bond or selected from the following formulas L-1 to L-19:

wherein:
R 5 , R 6 , R 7 , R 8 and R 9 are each the same or different, and each is 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; C 7 -C 20 arylalkyl group; C 8 -C 20 arylalkenyl group; and a C 7 -C 20 alkylaryl group, and an adjacent plurality of R 5 or plurality of R 6 or plurality of R 7 or plurality of R 8 or plurality of R 9 may be bonded to each other to form a ring, and hydrogen of R 5 , R 6 , R 7 , R 8 and R 9 may be substituted with one or more deuterium,
e is an integer of 0 to 4, f is an integer from 0 to 6, g and h are independently an integer of 0 to 4, i is an integer of 0 to 8, and
* means the position to be bonded.

4 . The compound according to claim 1 , wherein Ar 1 and Ar 2 are each any of Formulas A-1 to A-14:

wherein:
R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each the same or different, and each is 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; C 7 -C 20 arylalkyl group; C 8 -C 20 arylalkenyl group; and a C 7 -C 20 alkylaryl group, and an adjacent plurality of R 10 or plurality of R 11 or plurality of R 12 or plurality of R 13 or plurality of R 14 or plurality of R 15 or plurality of R 16 or plurality of R 17 may be bonded to each other to form a ring, and hydrogens of R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 may be further substituted with one or more deuterium,
X is O, S, NR or CR′R″ or N,
R is selected from the group consisting of an C 6 -C 20 aryl group; a fluorenyl 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 5 -C 20 aliphatic ring and a C 6 -C 20 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 20 alkoxy group; and a C 6 -C 20 aryloxy group;
R′ and R″ are selected from the group consisting of hydrogen; deuterium; a C 6 -C 20 aryl group; a fluorenyl 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; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 20 alkoxy group; and a C 6 -C 20 aryloxy group; or R′ and R″ can be bonded to each other to form a spiro;
j and o are independently an integers of 0 to 5, I is an integer of 0 to 7, m is an integer of 0 to 9, n, p and q are independently an integer of 0 to 4,
* means the position to be bonded, and where X is N, * combines with X.

5 . 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
• Kim Hyeong Su
• Lee Junggeun

Classifications

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/6576

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

• H10K85/654

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