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

Patent metadata

Field	Value
Publication number	US-2025031567-A1
Application number	US-202418814978-A
Country	US
Kind code	A1
Filing date	Aug 26, 2024
Priority date	Jul 21, 2021
Publication date	Jan 23, 2025
Grant date	—

Abstract

Provided is a compound of Formula 1 capable of improving the light-emitting efficiency, stability, and lifespan of an organic electronic element, a composition comprising the same, an organic electronic element using same, and an electronic device thereof.

First claim

What is claimed is:

1 . A compound of Formula 1:

wherein:

1) A is

2) B is
3) X is O or S,
4) R 1 , R 2 , R 3 and R 4 are each independently the same or different, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; an C 6 -C 60 aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group including at least one heteroatom 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 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; and a C 6 -C 60 aryloxy group, and an adjacent plurality of R 1 s or of plurality of R 2 s or of plurality of R 3 s or of plurality of R 4 s may be bonded to each other to form a ring,
5) R′ and R″ are each independently selected from the group consisting of an C 6 -C 60 aryl group; a C 1 -C 60 alkyl group, and R′ and R″ can be bonded to each other to form a spiro,
6) a, b, c and d are each independently an integer of 0 to 3,
7) Ar 1 is a hydrogen; or deuterium,
8) Ar 2 is an C 6 -C 60 aryl group; or a C 1 -C 60 alkyl group,
9) Ar 3 is a substituent represented by Formula Ar-5:

wherein R 13 and R 14 are the same as the definition of R 1 above,
o is an integer of 0 to 3, p is an integer of 0 to 4,
Y is O, S, CR x R y or NR z ,
R x , R y and R z are the same as the definition of R′ above, or R x and R y can be bonded to each other to form a ring,
10) L 1 , L 2 and L 3 are each independently a single bond or a C 6 -C 60 arylene group,)
11) * refers to the position to be bonded to L 1 of Formula 1, or refers to the position to be bonded to L 3 of Formula Ar-5,
12) refers to the position to be bonded to L 2 of Formula 1,
13) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring 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 alkoxy 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 cycloalkyl group; a C 1 -C 20 heteroalkyl group; a C 7 -C 20 arylalkyl group; and a C 8 -C 20 arylalkenyl group, 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 of claim 1 , wherein at least one of L 1 to L 3 is represented by any of Formulas L-1 to L-3:

wherein:
1) R 17 is the same as the definition of R 1 ,
2) s is an integer of 0 to 4,
3) * means the position to be bonded.

3 . The compound of claim 1 , wherein both L 1 and L 2 are a single bond.

4 . An organic electronic element comprising a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode: wherein the organic material layer comprises a compound represented by Formula 1 according to claim 1 .

5 . The organic electronic element of claim 4 , wherein the organic material layer comprises an emitting layer; and a hole transport band formed between the first electrode and the emitting layer; wherein the hole transport band comprises the compound represented by Formula 1.

6 . The organic electronic element of claim 5 , wherein the hole transport band comprises an emitting auxiliary layer and the emitting auxiliary layer comprises a compound represented by Formula 1.

7 . The organic electronic element of claim 6 , wherein the emitting-auxiliary layer comprises a first emitting-auxiliary layer adjacent to the hole transport layer and a second emitting-auxiliary layer adjacent to the emitting layer, wherein the first emitting-auxiliary layer and/or the second emitting-auxiliary layer comprise the compound represented by Formula 1.

8 . The organic electronic element of claim 4 , wherein the organic material layer comprises an emitting layer; a hole transport layer formed between the first electrode and the emitting layer; and a plurality of emitting-auxiliary layers formed between the emitting layer and the hole transport layer,
wherein the emitting-auxiliary layer comprises a first emitting-auxiliary layer adjacent to the hole transport layer and a second emitting-auxiliary layer adjacent to the emitting layer, and wherein the first emitting-auxiliary layer comprises the compound of Formula 1.

9 . The organic electronic element of claim 4 , wherein the organic material layer comprises an emitting layer; a hole transport layer formed between the first electrode and the emitting layer; and a plurality of emitting-auxiliary layers formed between the emitting layer and the hole transport layer,
wherein the emitting-auxiliary layer comprises a first emitting-auxiliary layer adjacent to the hole transport layer and a second emitting-auxiliary layer adjacent to the emitting layer, and wherein the second emitting-auxiliary layer comprises the compound of Formula 1.

10 . The organic electronic element of claim 4 , further comprising a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

11 . The organic electronic element of claim 10 , wherein the light efficiency enhancing layer comprises a compound of Formula 1.

12 . The organic electronic element of claim 4 , wherein the organic material layer comprises 2 or more stacks comprising a hole transport layer, an emitting layer and an electron transport layer sequentially formed on the first electrode.

13 . The organic electronic element of claim 12 , wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.

14 . An electronic device comprising a display device comprising the organic electronic element of claim 4 ; and a control unit for driving the display device.

15 . The electronic device according to claim 14 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor (OPC), organic transistor (organic TFT) and an element for monochromic or white illumination.

Assignees

• Duk San Neolux Co Ltd

Inventors

• Kim Won Sam
• Lee Jung Geun
• Lee Je Woo
• Lee Sun Hee
• Mun Soung Yun
• Lee Jung Wook
• Lee Hyung Dong

Classifications

• H10K85/615

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

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/12

  comprising dopants · CPC title