Compound for organic electrical element, organic electrical element using same, and electronic device thereof

Patent metadata

Field	Value
Publication number	US-2023104183-A1
Application number	US-202117758382-A
Country	US
Kind code	A1
Filing date	Jan 12, 2021
Priority date	Jan 14, 2020
Publication date	Apr 6, 2023
Grant date	—

Abstract

Provided are a compound capable of improving the luminous efficiency, stability and lifespan of an organic electronic device employing the same, an organic electronic element employing the same, and an electronic device thereof.

First claim

What is claimed is:

1 . A compound represented by Formula 1:

wherein:
X is O or S,
R 1 and R 2 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxyl group; a C 6 -C 60 aryloxy group; and where a and b are 2 or more, R 1 and R 2 are each in plural being the same or different,
L 1 and L 2 are each independently selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a C 2 -C 60 heteroarylene group including at least one heteroatom of O, N, S, Si or and where q and w are 2 or more, L 1 and L 2 are each in plural being the same or different,
Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently selected from the group consisting of a C 6 -C 60 aryl group, a substituent represented by Formula 1-a, and a substituent represented by Formula 1-b, with the proviso that at least one pair of Ar 1 and Ar 2 , and Ar 3 and Ar 4 is a substituent represented by Formula 1-a,
a and b are each independently an integer of 0 to 4, q and w are each independently an integer of 0 to 2, with the proviso that q+w is 2 or more,
Y is NR a , O or S,
R a is selected from the group consisting of a C 6 -C 60 aryl group; a C 2 -C 60 heteroaryl group including at least one heteroatom of O, N, S, Si or F; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or F; and —L′—N(R c )(R d ),
L′ is selected from the group consisting of a C 6 -C 60 arylene group; a fluorenylene 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 60 heterocyclic group including at least one heteroatom of O, N, S, Si or F;
R c and R d are each independently selected from the group consisting of a C 6 -C 60 aryl group; 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 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or F;
R 3 , R 4 , R 7 and R 8 are each independently selected from the group consisting of a C 6 -C 60 aryl group; a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si or F; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; a C 1 -C 60 alkyl group; an C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxyl group; and a C 6 -C 60 aryloxy group, and where a, b, c and d are 2 or more, R 3 , R 4 , R 7 and R 8 are each in plural being the same or different,
d, g and h are each independently an integer from 0 to 4, c is an integer from 0 to 3,
L 5 and L 5 are each independently selected from the group consisting of a single bond; a C 6 -C 60 arylene group; a C 2 -C 60 heteroarylene group including at least one heteroatom of O, N, S, Si or F;
R′ and R″ are independently of each other hydrogen; deuterium; halogen; cyano group; C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxyl group; a C 6 -C 60 aryloxy group; a C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heteroaryl group including at least one heteroatom of O, N, S, Si or F; a fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring; and R′ and R″ are bonded to each other to form a spiro,
* indicates the position to be bonded,
wherein the aryl group, arylene group, heteroarylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxyl group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; C 6 -C 20 aryl group substituted with deuterium; a fluorenyl group; C 2 ˜C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; C 7 -C 20 arylalkyl group;
and C 8 -C 20 arylalkenyl group; and —L′—N(R c )(R d ); wherein 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 combination thereof.

2 . The compound of claim 1 , wherein Formula 1 includes a compound represented by Formula 2:

wherein:
X, R 1 , R 2 , R 3 , R 4 , L 2 , L 5 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R′ and R″ are the same as defined in claim 1 ,
a′, c and e are each independently an integer of 0 to 3, b, d and f are each independently an integer of 0 to 4,
x is an integer of 0 or 1, y is an integer of 0 to 2, provided that x+y is 1 or more,
R 5 and R 6 are the same as the definition of R 1 to R 2 in claim 1 ,
L 3 and L 4 are the same as the definition of L 2 and L 5 in claim 1 ,
R′″ and R″″ are the same as the definitions of R′ and R″ in claim 1 .

3 . The compound of claim 2 , wherein Formula 2 is represented by any one of Formulas 2-1 to 2-5:

wherein:
X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 1 , L 2 , L 3 , L 4 , L 5 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R′, R″, R′″, R″″, b, c, d, e and f are the same as defined in claim 2 ,
L 6 is the same as the definition of L 1 to L 5 in claim 2 ,
Ar 5 and Ar 6 are the same as the definitions of Ar 1 to Ar 4 in claim 2 ,
a″ and b″ are independently an integer of 0 to 2, and a′ and b′ are independently an integer of 0 to 3.

4 . The compound of claim 2 , wherein Formula 2 is represented by Formula 2-6 or Formula 2-7:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 1 , L 2 , L 3 , L 4 , L 5 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R′, R″, R′″, R″″, a′, b, c, d, e, f, x and y are the same as defined in claim 2 .

5 . The compound of claim 2 , wherein Formula 2 is represented by any one of Formulas 2-8 to 2-11:

wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 1 , L 2 , L 3 , L 4 , L 5 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R′, R″, R′″, R″″, a′, b, c, d, e, f, x and y are the same as defined in claim 2 .

6 . The compound of claim 2 , wherein Formula 2 is represented by any one of Formulas 2-12 to 2-15:

wherein:
X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , L 1 , L 2 , L 3 , L 4 , Ar 1 , Ar 2 , R′, R″, R′″ and R″″ are the same as defined in claim 2 , and
a′, b′, c and e are independently an integer of 0 to 3, and b and f are independently an integer of 0 to 4.

7 . The compound of claim 2 , wherein Formula 2 is represented by any one of Formulas 2-16 to 2-19:

Assignees

• Duk San Neolux Co Ltd

Inventors

• Oh Dae Hwan
• Park Jong Gwang
• Kim Won Sam
• Lee Sun Hee
• Mun Soung Yun
• Park Chi Hyun

Classifications

• H10K50/17

  Carrier injection layers · CPC title

• H10K30/00

  Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation (integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20) · CPC title

• H10K10/40

  Organic transistors · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title