Process for production of a thin film electrode and an electroluminescence device

• US 5,364,654 A
• Filed: 06/04/1991
• Issued: 11/15/1994
• Est. Priority Date: 06/14/1990
• Status: Expired due to Fees

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Hosokawa, Chishio, Kusumoto, Tadashi
• Primary Examiner(s): BELL, JANYCE A
• Application Number:
  US07/710,078
• Time in Patent Office: 1,260 Days
• Field of Search: 427/66, 427/69, 427/70, 427/255.2, 427/255
• US Class Current: 427/66
• CPC Class Codes: C23C 14/06 characterised by the coating material C23C14/0021 , C23C14/04 take precedence
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• CPC Class Codes: H05B 33/26 characterised by the composition or arrangement of the conductive material used as an electrode
• CPC Class Codes: H10K 50/82 Cathodes
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]

Abstract

Disclosed are

(1) a thin film electrode for devices comprising an electron-injectable metal and an organic compound and having an excellent uniformity and minuteness,

(2) a process for production of a thin film electrode for devices which comprises co-vapor depositing an electron-injectable metal and an organic compound, and

(3) a process for production of an electroluminescence device which comprises co-vapor depositing an electron-injectable metal and an organic compound to form a cathode.

The thin film electrode of the present invention has a small volume resistivity. An EL device using said thin film electrode has high luminous efficiency and can be expected to be utilized as a light emitting material for various display devices.

Claims

1. A process for production of a thin film electrode for devices which comprises co-vapor depositing an electron-injectable metal and an organic compound having an ability of forming complexes with the electron-injectable metal or an organic compound having an acceptor property at a pressure of not more than 10^-5 torr, the weight ratio of the organic compound to the electron-injectable metal being in the range from 1 to 30% by weight and the vapor deposition rate of the metal being 0.1 to 10 nm/second.

2. The process for production of a thin film electrode for devices as defined in claim 1 wherein the film thickness after co-vapor deposition is 10 nm to 500 nm.

3. The process for production of a thin film electrode for devices as defined in claim 1 wherein co-vapor deposition is conducted simultaneously.

4. The process for production of a thin film electrode for devices as defined in claim 2 wherein the electron-injectable metal is selected from the group consisting of Ba, Ca, Ce, Cs, Er, Eu, Gd, Hf, K, La, Mg, Na, Nd, Sc, Sm, Y, Yb, Zn and Li.

5. The process for production of a thin film electrode for devices as defined in claim 1 wherein the thin film electrode is a metal is selected from the group consisting of Gd, Zn, In, Ta, Ba, Ca, Ce, Er, Eu, Hf, La, Mg, Nd, Sc, Sm, Y, Yb and Zn.

6. The process for production of a thin film electrode for devices as defined in claim 4 wherein the organic compound is an electron-accepting group selected from the group consisting of --CN;

##STR25## wherein R is selected from the group consisting of an alkyl group, an aryl group an alkyl-substituted aryl group and a hydrogen atom;

--NO₂ ;

a halogen atom;

##STR26## wherein R₁ is selected from the group consisting. of an alkyl group, an aryl group, an alkyl-substituted aryl group, an alkoxy-substituted aryl group and a hydrogen atom; and

a compound having a quinoid structure.

7. The process for the production of a thin film electrode for devices as defined in claim 6 wherein the process is carried at a temperature of 0°

to 100°

C.

8. The process for the production of a thin film electrode for devices as defined in claim 7 wherein the organic compound is of the formula ##STR27## or the formula ##STR28## wherein R¹, R², R³, R⁴, R⁷, R⁸, R⁹ and R¹⁰ are individually an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a halogen, a nitro group, a cyano group, an alkoxy carbonyl group or an aryl group having 6 to 20 carbon atoms or R₁ and R², R³ and R⁴, R⁷ and R⁸ or R⁹ and R¹⁰ may combine with each other to form a saturated or unsaturated five- or six-membered ring;

R⁵ and R⁶ are individually a dicyanomethylene group, a dicyanocarbonylmethylene group;

an oxygen atom, a cyanoimino group, a cyanoalkoxycarbonylmethylene group, a dialkoxycarbonylmethylene group, a methylene dicarboxylate group or a methylene cyanocarboxylate group.

9. The process for the production of a thin film electrode for devices as defined in claim 8 wherein the organic compound is selected from the group consisting of ##STR29## wherein t-Bu is tert-butyl group.

10. The process for the production of a thin film electrode for devices as defined in claim 7 wherein the organic compound is of the formula ##STR30## wherein R¹¹ to R¹⁴ are each individually an aryl group having 6 to carbon atoms, an alkoxycarbonyl group, a nitro group, an alkylamino group, a carbonyl group, an arylalkyl group, an aryloxycarbonyl group, a benzyloxycarbonyl group, a phenethyloxycarbonyl group or an aminocarbonyl group, and R¹⁵ is a dicyanocarbonylmethylene group, an oxygen atom, a dicyanomethylene group, a cyanoimino group, a cyanoalkoxycarbonylmethylene group, a dialkoxycarbonylmethylene group, a methylene dicarboxylate group or a methylene cyanocarboxylate group.

11. The process for the production of a thin film electrode for devices as defined in claim 10 wherein the organic compound is selected from the group consisting of ##STR31## wherein Ph is phenyl group.

12. The process for the production of a thin film electrode for devices as defined in claim 7 wherein the organic compound is a 4-H-thiopyran-1,1-dioxide of the formula ##STR32## wherein R²³ is an electron-accepting group, R²¹ and R²⁵ are individually an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms,

R²² and R²⁴ are individually a hydrogen atom or an alkoxycarbonyl group or R²¹ and R²² or R²⁴ and R²⁵ may combine with each other to form a condensed unsaturated six-membered ring.

13. The process for the production of a thin film electrode for devices as defined in claim 12 wherein the organic compound is selected from the group consisting of ##STR33## wherein Ph is a phenyl group.

14. The process for the production of a thin film electrode for devices as defined in claim 7 wherein the compound is selected from the group consisting of ##STR34##

15. The process for the production of a thin film electrode for devices as defined in claim 7 wherein the organic compound is selected from the group consisting of ##STR35##

16. The process for the production of a thin film electrode for devices as defined in claim 7 wherein the organic compound is a porphyrin or phthalocyanine compound of the formula ##STR36## wherein Q is --N═

or --C(R)═

, R is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aralkyl group, an aryl group having 6 to 20 carbon atoms or a heterocyclic group,

T₁ and T₂ are each a hydrogen atom or combine with each other to form an unsaturated six-membered ring, which may be substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a halogen atom or a heterocyclic group.