Organic electroluminescence device and phenylenediamine derivative

• US 6,541,129 B1
• Filed: 05/09/2000
• Issued: 04/01/2003
• Est. Priority Date: 09/09/1998
• Status: Expired due to Term

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Kawamura, Hisayuki, Hosokawa, Chishio
• Primary Examiner(s): Jones, Deborah
• Assistant Examiner(s): XU, LING X
• Application Number:
  US09/530,597
• Time in Patent Office: 1,057 Days
• Field of Search: 428/690, 428/917, 428/704, 313/504, 313/506, 257/40, 257/103, 564/307, 564/308, 564/427, 564/428, 564/433, 564/429
• US Class Current: 428/690
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/58 Naphthylamines; N-substituted derivatives thereof
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 217/92 the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 2603/24 Anthracenes; Hydrogenated anthracenes
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H05B 33/22 characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
• 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 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-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: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/649 : Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/655 : comprising only sulfur as heteroatom
• CPC Class Codes: H10K 85/656 : comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6565 : Oxadiazole compounds
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

The invention is to provide an organic EL device having a long life time that can reduce the driving voltage of the organic EL device, and to provide a material having a small ionization potential and exhibiting a large hole mobility by using as a layer or a zone. The organic electroluminescence device comprises a pair of electrodes and an organic light emitting layer sandwiched in the electrodes, characterized in that a hole transporting zone provided between the electrodes comprises the phenylenediamine derivative represented by the specific structural formulae, and the phenylenediamine derivative has a hole mobility of 10⁻⁴ cm²/V·s or more upon using as a layer or a zone, with the organic light emitting layer containing a charge injection auxiliary.

Claims

1. A phenylenediamine derivative represented by the general formula (III)

wherein Ar¹³ to Ar¹⁸ represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with a hydrogen atom, an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl group;

X represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, a substituted or unsubstituted vinyl bond, or an aromatic heterocyclic ring;

R⁷ and R⁸ represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring, provided that at least one of Ar¹³ to Ar¹⁶ and X represents an aryl group containing a styryl group;

or one of Ar¹⁵, Ar¹⁸ and a basic skeleton shown by the following chemical formula (1) contains a condensed aromatic ring, an aromatic heterocyclic ring or a substituted or unsubstituted vinyl group;

2. A phenylenediamine derivative represented by the general formula (III) according to claim 1, wherein Ar¹³ to Ar¹⁸ represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with an alkyl or an alkoxy group having from 1 to 6 carbon atom(s), an aryl group having from 6 to 24 nucleus carbon atoms, or a styryl, group, X reprsents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), diphenylmethylene, an ether bond, a thioether bond, a substituted or unsubstituted vinyl bond, or an aromatic heterocyclic ring;

R⁷ and R⁸ represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring, provided that one of Ar¹⁵, Ar¹⁸ and a basic skeleton shown by the following chemical formula (1) is a naphthyl group, an anthranyl group, a pyrenyl group or phenoanthryl group;

3. A phenylenediamine derivative represented by the general formula (III) according to claim 1, wherein Ar¹³ to Ar¹⁸ represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with an aryl group having from 6 to 24 nucleus carbon atoms;

X represents a linking group, which is a single bond, arylene having from 6 to 24 nucleus carbon atoms, alkylene having from 1 to 6 carbon atom(s), or an aromatic heterocyclic ring;

R⁷ and R⁸ represent an alkyl group having from 1 to 6 carbon atom(s), an alkoxy group, or a hydrogen atom, which may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a saturated 6-membered ring, provided that one of Ar¹⁵, Ar¹⁸ and a basic skeleton shown by the following chemical formula(1) contains a condensed aromatic ring, an aromatic heterocyclic ring or a substituted or unsubstituted vinyl group;

4. A phenylenediamine derivative represented by the general formula (III) according to claim 1, wherein Ar¹³ to Ar¹⁸ represent an aryl group having from 6 to 24 nucleus carbon atoms, which may be substituted with an aryl group having from 6 to 24 nucleus carbon atoms;

X represents a linking group, which is a single bond or arylene group having from 6 to 24 nucleus carbon atoms;

R⁷ and R⁸ represent a hydrogen atom, provided that Ar¹⁵ and Ar¹⁸ are a naphthyl group.

5. A phenylenediamine derivative of claim 1, of the formula:

6. An organic electroluminescence device comprising a pair of electrodes and an organic light emitting layer or zone sandwiched in said electrodes, characterized in that a hole transporting layer or, zone provided between said electrodes comprises a phenylenediamine derivative represented by the general formula (III), as defined in claim 1.

7. An organic electroluminescence device according to claim 6, wherein the phenylenediamine derivative is of the formula

8. An organic electroluminescence device comprising a pair of electrodes and an organic light emitting layer or zone sandwiched in said electrodes, characterized in that a hole transporting layer or zone provided between said electrodes comprises a phenylenediamine derivative of the formula (I):