Organic electroluminescent device

• US 6,800,382 B2
• Filed: 10/28/2002
• Issued: 10/05/2004
• Est. Priority Date: 12/09/1998
• Status: Expired due to Fees

• Current Assignee: Sony Corporation (Sony Group Corp.)
• Original Assignee: Sony Corporation (Sony Group Corp.)
• Inventors: Tamura, Shinichiro, Ishibashi, Tadashi, Ichimura, Mari
• Primary Examiner(s): Jones, Deborah
• Assistant Examiner(s): Xu, Ling X.
• Application Number:
  US10/281,583
• Publication Number:
  US 20030099863A1
• Time in Patent Office: 708 Days
• Field of Search: 428/690, 428/701, 428/917, 313/504-506, 252/301.16, 252/301.26, 257/40, 257/103
• US Class Current: 428/690
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 2102/3026 Top emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• 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 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic electroluminescent device comprises an organic layer 5, 5a or 5b having a luminescent region and provided between an anode 2 and a cathode 3. The organic layer contains at least one distyryl compound represented by the following general formula (1).

General formula (1):

wherein R¹ and R2 are, respectively, groups which may be the same or different and independently represent an aryl group of the following general formula (2).

General formula (2)

in which R⁴ to R⁸ may be the same or different and, respectively, represent a hydrogen atom, or at least one of them is a specified group such as a methoxy group, R³ represents a hydrogen atom or a specified group, and X represents a substituted or unsubstituted aryl group or hydrocarbon ring group.

Claims

1. An organic electroluminescent device of the type which comprises an organic layer having a luminescent region and provided between an anode and a cathode, wherein said organic layer comprises, as an organic luminescent material, at least one distyryl compound of the following general formula (1)

General formula (1):

wherein R¹ and R² are, respectively, groups which may be the same or different and independently represent an aryl group of the following general formula (2)

General formula (2);

in which R⁴, R⁵, R⁶, R⁷ and R⁸ may be the same or different and, respectively, represent a hydrogen atom, or at least one of them is a saturated or unsaturated alkoxyl group, and alkyl group, an amino group, an alkylamino group or an aryl group, R³ represents a hydrogen atom, a saturated or unsaturated alkoxyl group, an alkyl group, an alkylamino group, a naphthyl group, an anthryl group, or a phenanthryl group, X is selected from the group consisting of aryl, quinyl, and cyclic hydrocarbon, A is selected from the group consisting of hydrogen, halogen, cyano and nitro, and B is selected from the group consisting of halogen, cyano and nitro.

2. An organic electroluminescent device according to claim 1, wherein X in the formula (1) represents a group of general formula (4)

General formula (4):

wherein R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ may be the same or different and independently represent a hydrogen atom, or at least one of them represents a cyano group, a nitro group or a halogen atom.

3. An organic electroluminescent device according to claim 1, wherein X in the formula (1) represents a group of general formula (5)

General formula (5):

wherein R¹⁹, R²⁰, R²¹, R²², R²³, R²⁴, R²⁵ and R²⁶ may be the same of different and independently represent a hydrogen atom, or at least one of them represents a cyano group, a nitro group or a halogen atom.

4. An organic electroluminescent device according to claim 1, wherein X in the formula (1) represents a group of general formula (6)

General formula (6):

wherein R²⁷, R²⁸, R²⁹, R³⁰, R³¹, R³², R³³ and R³⁴ may be the same or different and independently represent a hydrogen atom, or at least one of them represents a cyano group, a nitro group or a halogen atom.

5. An organic electroluminescent device according to claim 1, wherein X in the formula (1) represents a group of the following general formula (7)

General formula (7):

wherein R³⁵, R³⁶, R³⁷, R³⁸, R³⁹, R⁴⁰, R⁴¹ and R⁴² may be the same or different and independently represent a hydrogen atom, or at least one of them represents a cyano group, a nitro group or a halogen atom.

6. An organic electroluminescent device according to claim 1, wherein X in the general formula (1) represents a group of structural formula (8)

Structural formula (8):

7. An organic electroluminescent device according to claim 1, wherein X in the formula (1) represents a group of structural formula (9)

Structural formula (9):

8. An organic electroluminescent device of the type which comprises an organic layer having a luminescent region and provided between an anode and a cathode, wherein said organic layer comprises, as an organic luminescent material, at least one of distyryl compounds represented by the following structural formulae (10)-1, (10)-2, (10)-3, (10)-4, (10)-5, (10)-6, (10)-7, (10)-8, (10)-9, (10)-10, (10)-11, (10)-12, (10)-13, (10)-14, (10)-15, (10)-16, (10)-17 and (10)-18:

Structural formula (10)-1;

Structural formula (10)-2;

Structural formula (10)-3;

Structural formula (10)-4;

Structural formula (10)-5;

Structural formula (10)-6;

Structural formula (10)-7;

Structural formula (10)-8;

Structural formula (10)-9;

Structural formula (10)-10;

Structural formula (10)-11;

Structural formula (10)-12;

Structural formula (10)-13;

Structural formula (10)-14;

Structural formula (10)-15;

Structural formula (10)-16;

Structural formula (10)-17;

Structural formula (10)-18;

9. An organic electroluminescent device according to claim 8, wherein said organic layer has an organic built-up structure wherein a hole transport layer and an electron transport layer are built up, and said distyryl compound is used as a material for forming said hole transport layer.

10. An organic electroluminescent device according to claim 8, wherein said organic layer has an organic built-up structure wherein a hole transport layer and an electron transport layer are successively built up, and said distyryl compound is used as a material for forming said electron transport layer.

11. An organic electroluminescent device according to claim 8, wherein said organic layer has an organic built-up structure wherein a hole transport layer, a luminescent layer, and an electron transport layer are built up, and said distyryl compound is used as a material for forming said luminescent layer.