Compound for organic electric device, organic electric device using the same, and electronic device thereof

Patent metadata

Field	Value
Publication number	US-12466837-B2
Application number	US-202017597873-A
Country	US
Kind code	B2
Filing date	Jul 29, 2020
Priority date	Jul 31, 2019
Publication date	Nov 11, 2025
Grant date	Nov 11, 2025

Abstract

Provided are a compound for an organic electric device, an organic electric device using the same, and an electronic device including the organic electric device. According to the presently claimed subject matter, an organic electric device with high luminous efficiency, low driving voltage, and high heat resistance can be provided, and the color purity and lifetime of the organic electric device can be improved.

First claim

What is claimed is:

1 . A compound represented by Formula 1:

wherein:
1) R 1 to R 3 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a C 6-60 aryl group; a fluorenyl group; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring group between a C 3-60 aliphatic ring and a C 6-60 aromatic ring; a C 1-50 alkyl group; a C 2-20 alkenyl group; a C 2-20 alkynyl group; a C 1-30 alkoxyl group; a C 6-30 aryloxy group; Formula 1-1; Formula 1-2; and Formula 1-3, or adjacent groups thereof can bind to one another to form a ring, wherein at least one of R 1 to R 3 is any one of Formula 1-1 to Formula 1-3:

2) L′ is selected from the group consisting of a single bond; a C 6-60 arylene group; a fluorenylene group; a fused ring group between a C 3-60 aliphatic ring and a C 6-60 aromatic ring; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof; and
3) R a and R b are each independently selected from the group consisting of a C 6-60 aryl group; a fluorenyl group; a C 3-60 aliphatic ring group; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof;
4) A is an integer of 0 to 4; b is an integer of 0 to 6; c is an integer of 0 to 3; and a+b+c is greater than or equal to 1;
5) When a, b, and care 2 or greater, a plurality of R 1 to R 3 are the same as or different from one another, and a plurality of R 1 , or a plurality of R 2 , or a plurality of R 3 may bind to one another to form a ring;
6) X 1 to X 9 are each independently N or C(R c );
7) at least one of X 1 to X 5 and at least one of X 6 to X 9 are N;
8) L 1 is selected from the group consisting of a single bond; a C 6-60 arylene group; a fluorenylene group; a fused ring group between a C 3-60 aliphatic ring and a C 6-60 aromatic ring; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof;
9) R c is selected from the group consisting of hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a C 6-60 aryl group; a fluorenyl group; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring group between a C 3-60 aliphatic ring and a C 6-60 aromatic ring; a C 1-50 alkyl group; a C 2-20 alkenyl group; a C 2-20 alkynyl group; a C 1-30 alkoxyl group; a C 6-30 aryloxy group; and —L′—N(R c )(R d );
10) the definitions of R c and R d are the same as those of R a and R b above;
11) the ring A of Formula 1-2 is selected from the group consisting of Formula A-1 to Formula A-16:

wherein:
11-1) * is a site to be bound to a ring comprising X 6 to X 9 ;
11-2) V is N or C(R e );
11-3) W 1 and W 2 are each independently a single bond, —N—L 3 -Ar 3 , S, O, or CR′R″, with the proviso that W 1 and W 2 are not a single bond at the same time;
11-4) L 3 is the same as the definition of L 1 in Formula 1;
11-5) Ar 3 is selected from the group consisting of a C 6-60 aryl group; a fluorenyl group; a fused ring group between a C 3-60 aliphatic ring and a C 6-60 aromatic ring; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof; and
11-6) R e , R′, and R″ are each selected from the group consisting of hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a C 6-60 aryl group; a fluorenyl group; a C 2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring group between a C 3-60 aliphatic ring and a C 6-60 aromatic ring; a C 1-50 alkyl group; a C 2-20 alkenyl group; a C 2-20 alkynyl group; a C 1-30 alkoxyl group; a C 6-30 aryloxy group; or —L′—N(R c )(R d ); or these groups can bind to one another to form a ring; or R′ and R″ can bind to one another to form a spiro ring; and
12) The rings formed by R 1 to R 3 , L 1 , L′, L 3 , Ar 3 , R a to R d , R c , R e , R′, R″, and adjacent groups thereof can be each further substituted with one or more substituents selected from the group consisting of deuterium; a halogen; a silane group substituted or unsubstituted with a C 1-20 alkyl group or a C 6-20 aryl group; a siloxane group; a boron group; a germanium group; a cyano group; an amino group; a nitro group; a C 1-20 alkylthio group; a C 1-20 alkoxy group; a C 6-20 arylalkoxy group; a C 1-20 alkyl group; a C 2-20 alkenyl group; a C 2-20 alkynyl group; a C 6-20 aryl group; a C 6-20 aryl group substituted with a deuterium; a fluorenyl group; a C 2-20 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a C 3-20 aliphatic ring group; a C 7-20 arylalkyl group; a C 8-20 arylalkenyl group; and a combination thereof; or adjacent groups thereof can form a ring with one another.

2 . The compound of claim 1 , wherein the compound of Formula 1-1 or Formula 1-2 is represented by one of Formula B-1 to Formula B-12:

wherein:
1) R 4 is the same as the definition of R 1 of Formula 1 of claim 1 ;

2) Y 1 and Y 2 are each independently —N—L 3 —Ar 3 , S, O, or CR′R″;
3) d is an integer of 0 to 4; e is an integer of 0 to 3; f is an integer of 0 to 2; g is an integer of 0 to 5; h is an integer of 0 to 8; and i is an integer of 0 to 7; and
4) L 1 , L 3 , Ar 3 , R′, and R″ are the same as defined in Formula 1 of claim 1 .

3 . The compound of claim 1 , wherein the compound of Formula 1 is represented by one of Formula P-1 to Formula P-212:

Assignees

• Duksan Neolux Co Ltd
• Duk San Neolux Co Ltd

Inventors

• Lee Je Woo
• Kim Dae Sic
• Oh Hyun Ji
• Kim Won Sam
• Lee Jung Geun

Classifications

• H10K50/844

  Encapsulations · CPC title

• H10K59/873

  Encapsulations · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/13

  comprising stacked EL layers within one EL unit · CPC title