Arylamine polymer including silicone, and electroluminescence device material and electroluminescence device using the polymer

Patent metadata

Field	Value
Publication number	US-11411188-B2
Application number	US-201916729628-A
Country	US
Kind code	B2
Filing date	Dec 30, 2019
Priority date	Dec 28, 2018
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

Abstract

An electroluminescent device with an improved luminous efficiency. The device includes a light emitting layer with an arylamine polymer including a structural unit (A) represented by Chemical Formula (1).

First claim

What is claimed is:

1. An arylamine polymer including a repeat unit (A) represented by Chemical Formula (1):

wherein, in Chemical Formula (1), Ar 1 is independently a C6 to C25 aromatic hydrocarbon group which is optionally substituted, or a C12 to C25 heterocyclic aromatic group which is optionally substituted;
Ar 2 is a C6 to C25 divalent aromatic hydrocarbon group which is optionally substituted, or a C12 to C25 divalent heterocyclic aromatic group which is optionally substituted; and
R 1 is independently a hydrogen atom, a C1 to C12 linear, branched, or cyclic hydrocarbon group, or a C6 to C25 aromatic hydrocarbon group, each of which is optionally substituted.

2. The arylamine polymer of claim 1 , wherein the repeat unit (A) is included in an amount of greater than equal to about 10 mole percent and less than or equal to about 100 mole percent, based on a total moles of repeat units of the polymer.

3. The arylamine polymer of claim 1 , wherein at least one Ar 1 is of the following groups:

wherein, in the above chemical formulae, R 111 to R 133 are independently a hydrogen atom, or a C1 to C12 linear or branched alkyl group, or a C6 to C25 aromatic hydrocarbon group, each of which is optionally substituted.

4. The arylamine polymer of claim 1 , wherein Are is a divalent group of the following groups:

wherein, in the above chemical formulae, R 211 to R 269 are independently, a hydrogen atom, or a C1 to C12 linear or branched alkyl group, or a C6 to C25 aromatic hydrocarbon group, each of which is optionally substituted.

5. An electroluminescence device material comprising the arylamine polymer including silicon of claim 1 .

6. An electroluminescence device comprising
a first electrode, a second electrode, and at least one organic film disposed between the first electrode and the second electrode,
wherein at least one layer of the organic film comprises the arylamine polymer of claim 1 .

7. The electroluminescence device of claim 6 , wherein the organic film comprising the arylamine polymer including silicon is a hole transport layer or a hole injection layer.

8. The electroluminescence device of claim 7 , further comprising light emitting layer comprising a semiconductor nanoparticle or an organic metal complex.

9. The arylamine polymer of claim 1 , wherein Ar 1 includes a substituent and the substituent is positioned at a ring carbon furthest from the chain nitrogen atom from which Ar 1 is linked to.

10. An electroluminescence device comprising
a first electrode, a second electrode, and at least one organic film disposed between the first electrode and the second electrode, wherein the organic film is a hole transport layer or a hole injection layer, and comprises the arylamine polymer of claim 1 , and
a light emitting layer comprising a semiconductor nanoparticle or an organic metal complex.

11. The electroluminescence devise of claim 10 , wherein at least one Ar 1 of the repeat unit (A) represented by Chemical Formula (1) is of the following groups:

wherein, in the above chemical formulae, R 111 to R 133 are independently a hydrogen atom, or a C1 to C12 linear or branched alkyl group, or a C6 to C25 aromatic hydrocarbon group, each of which is optionally substituted.

12. The electroluminescence device of claim 10 , wherein the substituent selected from R 111 , R 113 , R 116 , R 119 , R 120 or R 121 , R 122 or R 123 , R 124 , or R 125 to R 133 , is positioned at a ring carbon furthest from the chain nitrogen atom from which Ar 1 is linked to.

13. The electroluminescence device of claim 10 having an external quantum efficiency of 3.6% to 4.9% at luminance of 100 units.

14. The arylamine polymer of claim 1 having a weight average molecular weight from about 20,000 grams per mole to about 300,000 grams per mole, and a polydispersity of about 1.2 to about 3.5 as determined by size exclusion chromatography.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kato Fumiaki
• Tsuji Masashi
• Fujiyama Takahiro
• Furuta Keigo
• Motoyama Takao
• Konishi Yusaku

Classifications

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• C08G73/026 Primary

  Wholly aromatic polyamines · CPC title

• C09D5/24

  Electrically-conducting paints {(conductive materials H01B1/00)} · CPC title

• C09D179/02

  Polyamines · CPC title

• C08G73/0246

  Polyamines containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain · CPC title