Organic electroluminescent devices and panels

• US 6,456,003 B1
• Filed: 01/31/2000
• Issued: 09/24/2002
• Est. Priority Date: 01/28/1999
• Status: Expired due to Term

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: NEC Corporation
• Inventors: Mori, Kenji, Sakaguchi, Yoshikazu
• Primary Examiner(s): Kim, Robert H.
• Assistant Examiner(s): YUN, JURIE
• Application Number:
  US09/494,766
• Time in Patent Office: 967 Days
• Field of Search: 313/498, 313/499, 313/500-512, 313/504, 252/506, 428/690, 428/917, 428/457
• US Class Current: 313/504
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/805 Electrodes
• CPC Class Codes: H10K 59/805 Electrodes
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

A super thin film is composed of an organic compound having a sulfur-atom-containing substituent in a specific structure, such as mercapto, sulfide and disulfide groups. Among them, the most preferred one is an alkyl mercapto group represented by —(CH₂)_nSH in which n is an integer of 1-10. The super thin film is then introduced into the interface between at least one electrode and an organic layer being in contact therewith for receiving carriers from the electrode and delivering the carriers to the organic layer to provide organic EL devices and EL panels. The compound also has a molecular structure similar to that of an organic material at forms the organic layer. The compound can suppress the generation of dark spots and the increase of power consumption. Therefore, it is possible to manufacture organic EL devices with an excellent durability and a smaller increase in power consumption and also panels using the devices.

Claims

1. An organic electroluminescent device comprising:

a negative electrode;

a positive electrode; and

at least a one-layered organic compound thin film including a light emission layer between said electrodes,

wherein at least one of said electrodes is composed of one of a metal oxide, a metal selected from the group consisting of copper and noble metals and alloys thereof, and a semiconductor compound,

wherein a thin film composed of an organic compound having a sulfur-atom-containing substituent is sandwiched between at least one of said electrodes and said organic compound thin film, and

wherein said organic compound having the sulfur-atom-containing substituent comprises at least one of;

an organic compound having an alkyl mercapto group represented by —

(CH₂)_nSH wherein n is an integer of 1-10;

N,N′

-bis(4-(6-mercaptohexyl)phenyl)-N,N′

-bis(α

-naphthyl)-1,1′

-biphenyl-4,4′

-diamine; and

3-(4-biphenylyl)-4-(4-(6-mercaptohexyl)phenyl)-5-(4-t-butylphenyl)-1,2,4-triazole.

2. An organic electroluminescent device comprising:

a negative electrode;

a positive electrode; and

at least a one-layered organic compound thin film including a light emission layer between said electrodes,

wherein at least one of said electrodes is composed of one of a metal oxide, a metal selected from the group consisting of copper and noble metals and alloys thereof, and a semiconductor compound,

wherein a thin film composed of an organic compound having a sulfur-atom-containing substituent is sandwiched between at least one of said electrodes and said organic compound thin film, and

wherein said organic compound having the sulfur-atom-containing substituent comprises at least one of;

an organic compound having an alkyl mercapto group;

an organic compound having a sulfide group; and

an organic compound having a disulfide group.

3. An organic electroluminescent device comprising:

a negative electrode;

a positive electrode; and

at least a one-layered organic compound thin film including a light emission layer between said electrodes,

wherein at least one of said electrodes is composed of one of a metal oxide, a metal selected from the group consisting of copper and noble metals and alloys thereof, and a semiconductor compound,

wherein a thin film composed of an organic compound having a sulfur-atom-containing substituent is sandwiched between at least one of said electrodes and said organic compound thin film, and

the device further comprising an auxiliary electrode with a light transmissivity of 70% or more provided on the rear surface of said electrode which is surface-reformed using said organic compound having the sulfur-atom-containing substituent.

4. An organic electroluminescent panel comprising an electroluminescent device, said device including:

a negative electrode;

a positive electrode; and

at least a one-layered organic compound thin film including a light emission layer between said electrodes,

wherein at least one of said electrodes is composed of one of a metal oxide, a metal selected from the group consisting of copper and noble metals and alloys thereof, and a semiconductor compound,

wherein a thin film composed of an organic compound having a sulfur-atom-containing substituent is sandwiched between at least one of said electrodes and said organic compound thin film, and

wherein said organic compound having the sulfur-atom-containing substituent comprises at least one of;

an organic compound having an alkyl mercapto group represented by —

(CH₂)_nSH wherein n is an integer of 1-10;

N,N′

-bis(4-(6-mercaptohexyl)phenyl)-N,N′

-bis(α

-naphthyl)-1,1′

-biphenyl-4,4′

-diamine; and

3-(4-biphenylyl)-4-(4-(6-mercaptohexyl)phenyl)-5-(4-t-butylphenyl)-1,2,4-triazole.

5. An organic electroluminescent panel comprising an electroluminescent device, said device including:

a negative electrode;

a positive electrode; and

at least a one-layered organic compound thin film including a light emission layer between said electrodes,

wherein at least one of said electrodes is composed of one of a metal oxide, a metal selected from the group consisting of copper and noble metals and alloys thereof, and a semiconductor compound,

wherein a thin film composed of an organic compound having a sulfur-atom-containing substituent is sandwiched between at least one of said electrodes and said organic compound thin film, and

wherein said organic compound having the sulfur-atom-containing substituent comprises at least one of;

an organic compound having an alkyl mercapto group;

an organic compound having a sulfide group; and

an organic compound having a disulfide group.

6. An organic electroluminescent panel comprising an electroluminescent device, said device including:

a negative electrode;

a positive electrode; and

at least a one-layered organic compound thin film including a light emission layer between said electrodes,

wherein at least one of said electrodes is composed of one of a metal oxide, a metal selected from the group consisting of copper and noble metals and alloys thereof, and a semiconductor compound,

wherein a thin film composed of an organic compound having a sulfur-atom-containing substituent is sandwiched between at least one of said electrodes and said organic compound thin film, and

the electroluminsecent panel further comprising an auxiliary electrode with a light transmissivity of 70% or more provided on the rear surface of said electrode which is surface-reformed with said organic compound having the sulfur-atom-containing substituent.

7. A process of manufacturing an organic electroluminescent device, comprising the steps of:

immersing an electrode into a solution of an organic compound having a sulfur-atom-containing substituent to reform the surface of said electrode; and

forming a thin film composed of said organic compound having the sulfur-atom-containing substituent between said electrode and an organic compound thin film,

wherein the sulfur-atom-containing substituent comprises at least one of;

an organic compound having an alkyl mercapto group represented by —

(CH₂)_nSH wherein n is an integer of 1-10;

N,N′

-bis(4-(6-mercaptohexyl)phenyl)-N,N′

-bis(α

-naphthyl)-1,1′

-biphenyl-4,4′

-diamine; and

3-(4-biphenylyl)-4(4-(6-mercaptohexyl)phenyl)-5-(4-t-butylphenyl)-1,2,4-triazole.

8. A process of manufacturing an organic electroluminescent panel, comprising the steps of:

immersing an electrode into a solution of an organic compound having a sulfur-atom-containing substituent to reform the surface of said electrode; and

forming a thin film composed of said organic compound having the sulfur-atom-containing substituent between said electrode and an organic compound thin film,

wherein the sulfur-atom-containing substituent comprises at least one of;

an organic compound having an alkyl mercapto group represented by —

(CH₂)_nSH wherein n is an integer of 1-10;

N,N′

-bis(4-(6-mercaptohexyl)phenyl)-N,N′

-bis(α

-naphthyl)-1,1′

-biphenyl-4,4′

-diamine; and

3-(4-biphenylyl)-4-(4-(6-mercaptohexyl)phenyl)-5-(4-t-butylphenyl)-1,2,4-triazole.