Composition for anode buffer layer, high-molecular weight compound for anode buffer layer, organic electroluminescence element, and production process and uses of the same

Patent metadata

Field	Value
Publication number	US-9644048-B2
Application number	US-201013504076-A
Country	US
Kind code	B2
Filing date	Oct 27, 2010
Priority date	Oct 27, 2009
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

There is provided a material for an anode buffer lay which permits the use of an organic solvent as a solvent an anode buffer layer-forming solution, and is capable forming an anode buffer layer that does not dissolve even win coated with a luminescent layer-forming material solution containing an organic solvent as a solvent, and which is capable of producing an organic EL element having high electrical power efficiency and long life.

First claim

The invention claimed is:

1. A composition for an anode buffer layer comprising:
an electron-accepting compound;
a high-molecular weight compound having a structural unit represented by the following formula (1) or the following formula (2) and having a weight average molecular weight of 20,000 to 1,000,000 as measured by GPC:

wherein in each of the formulae (1) and (2);
plural R a s are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, with at least one R a being the alkyl group having 1 to 10 carbon atoms, and
in a benzene ring having R a in the formulae (1) and (2), at least one R a present at an ortho position with respect to a nitrogen atom is an alkyl group;
plural R b s are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
plural R c s are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, R c s each bonded to neighboring carbon atoms in the same phenyl group may be bonded to one another to form a condensed ring, and at least one of R c s in the same phenyl group is an alkyl group having 1 to 10 carbon atoms;
X is a single bond, —O—, —S—, —SO—, —SO 2 —, —NR 1 — wherein R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, —CO—, —COO—, or a divalent organic group having 1 to 20 carbon atoms, wherein the organic group may contain an atom or a group selected from the group consisting of —O—, —S—, —SO—, —SO 2 —, —NR 2 — wherein R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, —CO— and —COO—;
Y—X— is a group represented by:

wherein R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and p is 0, 1, or 2; and
an organic solvent, the organic solvent being an aromatic solvent comprising toluene, xylene, and/or anisole or a halogenated alkyl solvent comprising chloroform and/or dichloroethane, or a combination thereof.

2. A high-molecular weight compound for an anode buffer layer comprising:
a structural unit represented by the following formula (1) or the following formula (2), and
a structural unit derived from an electron-accepting compound having a polymerizable functional group, the polymerizable functional group being represented by at least one of the following formulae (A1) to (A13), the said high-molecular weight compound for an anode buffer layer having a weight average molecular weight of 20,000 to 1,000,000 as measured by GPC:

wherein in each of the formulae (1) and (2);
plural R a s are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, with at least one R a being the alkyl group having 1 to 10 carbon atoms;
plural R b s are each independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
plural R c s are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, and R c s each bonded to neighboring carbon atoms in the same phenyl group may be bonded to one another to form a condensed ring;
X is a single bond, —O—, —S—, —SO—, —SO 2 —, —NR 1 — wherein R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, —CO—, —COO—, or a divalent organic group having 1 to 20 carbon atoms, wherein the organic group may contain an atom or a group selected from the group consisting of —O—, —S—, —SO—, —SO 2 —, —NR 2 — wherein R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, —CO— and —COO—;
Y—X— is a group represented by:

wherein R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and p is 0, 1, or 2.

3. A composition for an anode buffer layer comprising the high-molecular weight compound for an anode buffer layer of claim 2 and an organic solvent.

4. An organic electroluminescence element comprising an anode, an anode buffer layer, a luminescent layer and a cathode that are laminated in this order, wherein the anode buffer layer is formed by heating the composition for an anode buffer layer of claim 1 .

5. The organic electroluminescence element according to claim 4 , further comprising a cathode buffer layer.

6. A display apparatus comprising the electroluminescence element of claim 4 .

7. A light irradiating apparatus comprising the electroluminescence element of claim 4 .

8. An organic electroluminescence element comprising an anode, an anode buffer layer, a luminescent layer and a cathode that are laminated in this order, wherein the anode buffer layer is formed by heating the high-molecular weight compound for an anode buffer layer of claim 2 .

9. The organic electroluminescence element according to claim 8 , further comprising a cathode buffer layer.

10. A display apparatus comprising the electroluminescence element of claim 8 .

11. A light irradiating apparatus comprising the electroluminescence element of claim 8 .

Assignees

• Osako Haruka
• Natori Nobuhiro
• Katoh Tsuyoshi
• Kondo Kunio
• Fukuchi Yosuke
• Samsung Electronics Co Ltd

Inventors

• Osako Haruka
• Natori Nobuhiro
• Katoh Tsuyoshi
• Kondo Kunio
• Fukuchi Yosuke

Classifications

• C08F12/32 Primary

  containing two or more rings · CPC title

• C08F12/26

  Nitrogen · CPC title

• B32B2457/202

  LCD, i.e. liquid crystal displays · CPC title

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title