Varnish containing good solvent and poor solvent

Patent metadata

Field	Value
Publication number	US-9251923-B2
Application number	US-57906605-A
Country	US
Kind code	B2
Filing date	Apr 28, 2005
Priority date	Apr 30, 2004
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

A varnish comprising a ground substance consisting of a polymer or oligomer of 200 to 50′104 molecular weight or organic compound of 200 to 1000 molecular weight and a solvent containing a good solvent and a poor solvent whose boiling point (under 760 mmHg) is at least 20° C. lower than that of the good solvent, wherein the ground substance is dissolved in the solvent. Any thin film prepared from this varnish is substantially from generation of foreign matter, so that it can appropriately be used as thin films for electronic devices and those for use in other technical fields.

First claim

The invention claimed is:

1. A charge-transporting varnish comprising:
a substrate comprising an oligomer having a molecular weight of from 200 to 2,000; and
a solvent comprising a good solvent and a poor solvent having a boiling point lower by at least 20° C. than said good solvent under 760 mmHg,
wherein said good solvent is 1,3-dimethyl-2-imidazolidinone and said poor solvent is at least one selected from the group consisting of ketones, glycol ethers and alcohols; and
wherein said substrate is dissolved in said solvents,
wherein said oligomer is an oligoaniline derivative represented by the following formula (4) or a quinonediimine derivative as an oxidation product of the formula (4):

wherein R 1 to R 7 each independently represents a hydrogen atom, halogen atom, a hydroxyl, amino, silanol, thiol, carboxyl, sulfonic acid, phosphoric acid, phosphate ester, ester, thioester, amido, nitro, monovalent hydrocarbon, organoxy, organoamino, organosilyl, organothio, acyl or sulfone group, and m and n are each independently an integer of at least 1 and satisfy m+n≦20.

2. The charge-transporting varnish according to claim 1 , wherein said substrate further comprises an electron-accepting dopant substance or hole-accepting dopant substance.

3. The charge-transporting varnish according to claim 2 , wherein said substrate comprises an electron-accepting dopant substance which is a sulfonic acid derivative represented by the following formula (5):

wherein D represents a benzene, naphthalene, anthracene or phenanthrene ring or a heterocycle, and R 12 and R 13 each independently represents a carboxyl or hydroxyl group.

4. The charge-transporting varnish according to claim 2 , wherein said substrate comprises an electron-accepting dopant substance which is a sulfonic acid derivative represented by the following formula (6):

wherein R 14 to R 18 each independently represents a hydrogen atom, a substituted or unsubstituted, monovalent hydroxyl group, or a halogen atom, X represents a single bond, O, S or NH, A represents a hydrogen or halogen atom, O, S, S(O) group, S(O 2 ) group, N with one or more substituted or unsubstituted groups bonded thereon, Si, P, P(O) group, or a mono- or higher valent, substituted or unsubstituted hydrocarbon group, y is an integer equal to a valence number of A and satisfies 1≦y, and x represents a number of sulfonic acid group(s) bonded on a benzene ring moiety in a 1,4-benzodioxane skeleton and satisfies 1≦x≦4.

5. A thin film fabricated from the varnish according to claim 1 .

6. A charge-transporting thin film fabricated from the charge-transporting varnish according to claim 2 .

7. An organic electroluminescence device comprising the charge-transporting thin film according to claim 6 .

8. The organic electroluminescence device according to claim 7 , wherein said charge-transporting thin film is a hole injection layer or hole transport layer.

9. A method for the fabrication of a thin film, comprising coating the varnish according to claim 1 on a substrate.

10. A method for the fabrication of a charge-transporting thin film, comprising coating the charge-transporting varnish according to claim 2 on a substrate.

11. The charge-transporting varnish according to claim 1 , wherein said poor solvent is selected from the group consisting of isobutanol and propylene glycol monoethyl ether.

12. The charge-transporting varnish according to claim 1 , wherein said alcohols are one or more selected from the group consisting of ethanol, isopropanol, tert-butanol, allyl alcohol, n-propanol, 2-methyl-2-butanol, isobutanol, n-butanol, 2-methyl-1-butanol, 1-pentanol, 2-methyl-1-pentanol, 2-ethylhexanol, 1-octanol, ethylene glycol, hexylene glycol, trimethylene glycol, 1-methoxy-2-butanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, propylene glycol and benzyl alcohol.

13. The varnish according to claim 1 , wherein a combination of said good solvent and poor solvent is 1,3-dimethyl-2-imidazolidinone and isobutanol, 1,3-dimethyl-2-imidazolidinone and cyclohexanol, or 1,3-dimethyl-2-imidazolidinone and propylene glycol monoethyl ether.

14. The varnish according to claim 1 , wherein a combination of said good solvent and poor solvent is 1,3-dimethyl-2-imidazolidinone and isobutanol or 1,3-dimethyl-2-imidazolidinone and propylene glycol monoethyl ether.

Assignees

• Kato Taku
• Yoshimoto Takuji
• Ono Go
• Nissan Chemical Ind Ltd

Inventors

• Kato Taku
• Yoshimoto Takuji
• Ono Go

Classifications

• H01B1/122 Primary

  Ionic conductors · CPC title

• C09D179/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/0266

  Polyanilines or derivatives thereof · CPC title

• C09D165/00

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• C09D179/02

  Polyamines · CPC title