JP2007201219A - Organic electroluminescence element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a luminescent material for an organic electroluminescence which shows high luminescence efficiency and less luminescence deterioration, and high reliability, and also to provide an organic electroluminescence element. <P>SOLUTION: The organic electroluminescence element is provided by forming a plurality of layers of organic compound thin films including a luminescence layer, between an anode layer and a cathode layer both serving as electrodes. The luminescence layer is made of a host material and a dopant material. The host material is made of a copolymer including a unit of a specific structure, and the dopant material is made of a diarylamine naphthalene compound. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent element (hereinafter abbreviated as an organic EL element) having high luminous efficiency.

  An electric field EL element using an organic material is expected to be used as a solid light emitting type inexpensive large-area full-color display element, and many developments have been made. In general, an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side, holes are injected from the anode side, the electrons recombine with holes in the light emitting layer, and the energy level starts from the conduction band. It is a phenomenon in which energy is released as light when returning to the valence band.

Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic EL elements. Further, the characteristic deterioration has been remarkably not put into practical use.
In recent years, organic EL elements in which thin films containing organic compounds having high fluorescence quantum efficiency that emit light at a low voltage of 10 V or less have been reported and attracted interest (see Non-Patent Document 1). This method uses a metal chelate complex as a light emitting layer and an amine compound as a hole injection layer to obtain green light emission with high luminance. The luminance reaches several thousand cd / m ² at a DC voltage of 6 to 7V. ing. However, the production of an organic EL element accompanied by an organic compound vapor deposition operation has a problem in productivity, and it is desirable to create a coating type element from the viewpoint of simplifying the manufacturing process and increasing the area.

  A polyphenylene vinylene polymer is known as a light-emitting material of an organic EL element used for producing an organic EL element having a coating method advantageous for productivity (see Non-Patent Documents 2 and 3). Due to the main chain, there are problems such as difficulty in controlling the concentration of the light emitting material, and difficulty in delicate control of color tone and light emission intensity. Similarly, there is a dye-dispersed polymer as an organic electroluminescent element using a coating method. For example, it is an element (see Patent Document 1) in which a low molecular weight dye or the like is dispersed in polyvinyl carbazole, and these have various functions such as electron transport property, electron injection property, hole transport property, hole injection property, and light emission property. The material which has it can be mixed and used for multiple light emitting elements.

  Conventional polyvinyl carbazole has a relatively high durability because of its high glass transition point, but has a high driving voltage and insufficient hole mobility and film-forming properties, resulting in low luminous efficiency and practical problems. In order to improve these problems, various carbazole derivative polymers and copolymers have been proposed. For example, a copolymer of a carbazole derivative and a diamine derivative (see Patent Documents 2 and 3), a copolymer of a carbazole derivative and an oxadiazole derivative (see Patent Documents 4 to 7), and a polymer having a special carbazole unit (Patent Document) 8-10), but all have low luminance and luminous efficiency and short lifetime.

It has been proposed that the derivative having a naphthalene skeleton of the present invention is used as a hole transport material. As amine-based hole transport materials, (Patent Documents 11 and 17) are located at positions 1 and 4. It has been proposed as a hole transport material having a diarylamino group. As the luminescent material, (Patent Document 12) is a diaminonaphthalene derivative having two or more styryl groups, and (Patent Documents 13 and 14) is at least one α, α-methyl-4-phenyl-4. -As a luminescent material having a benzylene group, (Patent Document 15) is reported as a diaminonaphthalene derivative having two or more fluorenyl groups, and (Patent Document 16) is reported as a luminescent material comprising a naphthalene derivative having two or more amino groups. ing.
However, all of these are element fabrication by vacuum deposition, and are not coating-type organic EL element fabrication advantageous to productivity.

JP-A-4-212286 JP 2002-124390 A JP 2002-37817 A Japanese Patent Laid-Open No. 11-60660 JP-A-11-307253 JP 2000-159846 A JP 2001-126875 A JP 2002-105445 A JP 2002-363227 A JP 2002-302516 A JP-A-8-87122 JP-A-9-268284 Japanese Patent No. 3504033 Japanese Patent Laid-Open No. 11-74079 JP-A-11-35532 Japanese Patent Laid-Open No. 11-273860 JP 2003-238502 A Applied Physics Letters, 51, 913, 1987 Polymer Bulletin, 38, 167-176, 1997 Macromolecules, 32, 1476-11481, 1999

However, the organic EL devices up to now have improved light emission intensity due to the improvement of the structure, but do not yet have sufficient light emission luminance. Moreover, it has a big problem that it is inferior in stability during repeated use. This is because, for example, metal chelate complexes such as tris (8-hydroxyquinolinate) aluminum complex are chemically unstable during electroluminescence, poor adhesion to the cathode, and greatly deteriorated in a short time of light emission. It was. For the above reasons, in order to develop an organic EL device having high luminous brightness and luminous efficiency and excellent stability during repeated use, the development of a light-emitting material with excellent luminous ability and durability has been developed. The present invention is intended to provide an organic EL device having high emission luminance and excellent stability during repeated use. As a result of intensive studies by the present inventors, by using the light emitting material for an organic EL device represented by the general formula [1] for the light emitting layer, the organic EL device has high light emission luminance and light emission efficiency and is stable when repeatedly used. As a result, the present invention has been found.
An object of the present invention is to provide a coating type organic EL device having a low driving voltage and high luminous efficiency.

  The present invention relates to an organic electroluminescent device in which a plurality of organic compound thin films including a light emitting layer is formed between both electrodes of an anode layer and a cathode layer, wherein the light emitting layer comprises a host material and a dopant material, The present invention relates to an organic electroluminescence device in which a host material is composed of a polymer comprising a unit represented by the following general formula [1], and a dopant material is composed of a compound represented by the following general formula [4].

General formula [1]

[Wherein A represents a non-conjugated trivalent organic residue,
B represents a direct bond or a divalent organic residue selected from the group consisting of a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, and a substituted or unsubstituted ethenylene group. Represent,
C represents a monovalent organic residue represented by the following general formula [2] or the following general formula [3]. ]

General formula [2]

[Wherein R ^{1 to} R ⁷ each independently represents a bonding site, a hydrogen atom or a substituent,
X is a direct bond, —O—, —S—, —Se—, —NH—, —NR ⁸ — (R ⁸ represents an alkyl group or an aryl group), —S (═O) ₂ —, — ( CO) -, - COO -, - OCO-, or, -CH ₂ - indicates,
R ^{1 to} R ⁷ may be bonded to each other to form an aryl ring, and further the aryl ring may have a substituent. ]

［式中Ｒ^１〜Ｒ^５およびＲ^９〜Ｒ^１２は、ぞれぞれ独立に、結合部位、水素原子もしくは置換基を表す。］ General formula [3]

[Wherein R ^{1 to} R ⁵ and R ^{9 to} R ¹² each independently represents a bonding site, a hydrogen atom, or a substituent. ]

[Wherein, R ^{13 to} R ²⁰ each independently represent —NR ²¹ R ²² (R ²¹ and R ²² represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and R ²¹ and R ²² And a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, It represents a substituted or unsubstituted arylthio group or a substituted or unsubstituted aryl group, and two or more of R ^{13 to} R ²⁰ represent —NR ²¹ R ²² . ]

The present invention comprises at least ^{R 13} and ^{R 16} are directed ^to the organic light emitting diode is a ^-NR 21 ^{R 22.}

The present invention comprises at least ^{R 13} and ^{R 17} are directed ^to the organic light emitting diode is a ^-NR 21 ^{R 22.}

  According to the present invention, a material for an organic EL element having a low driving voltage and a high luminous efficiency and an organic EL element using the same can be provided.

The host material used in the present invention is a polymer having a unit represented by the general formula [1].
In the general formula [1], A represents an arbitrary trivalent organic residue capable of forming a non-conjugated main chain skeleton having B and C in the side chain. Examples are shown in X-1 to X-12, but are not limited thereto.

  The light emitting layer forming material used in the present invention is a polymer including a unit represented by the general formula [1], and preferably has a unit represented by the general formula [1] and an amino group. A copolymer comprising units. Examples of other units that may be copolymerized include units having an electron transporting skeleton.

  The polymerization mode of the non-conjugated main chain skeleton monomer in forming the copolymer is to perform copolymer formation by vinyl polymerization such as radical polymerization, cationic polymerization, anionic polymerization, condensation polymerization, ring-opening polymerization, and various polymerization reactions. The polymerization method is not particularly limited, but in the present invention, a copolymer formation reaction by polymerization of a vinyl polymerization monomer is particularly preferable.

  In addition, the organic residue composed of B or C in the general formula [1], or the organic residue containing an amino group when the amino group of the unit having an amino group is in the side chain is a non-conjugated main chain skeleton monomer. Even if it is not introduced at the stage, it may be introduced / modified after the non-conjugated main chain skeleton is formed.

In the copolymer comprising the unit represented by the general formula [1] and the unit having an amino group, the amino group of the unit having an amino group is present in the main chain or side chain of the copolymer.
A unit having a structure represented by the following general formula [5] is preferable.

General formula [5]

Wherein E and F are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ]

Further, it is preferably a unit having a structure represented by the following general formula [6].
General formula [6]

[Wherein D represents a divalent organic residue selected from the group consisting of a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted ethenylene group (provided that And an ethenylene group is a case between two arylene groups or heteroarylene groups.) E and F are each independently a substituted or unsubstituted aryl group, substituted or unsubstituted Of the heteroaryl group. ]

The unit having an amino group is more preferably represented by the following general formula [7].
General formula [7]

[Wherein D represents a divalent organic residue selected from the group consisting of a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted ethenylene group (provided that And an ethenylene group is a case between two arylene groups or heteroarylene groups.) E and F are each independently a substituted or unsubstituted aryl group, substituted or unsubstituted And G represents a non-conjugated trivalent organic residue. ]

  Examples of G in the general formula [7] are the same as those in A in the above general formula [1].

  More preferably, the unit having an amino group includes, but is not limited to, the structures shown in Y-1 to Y-12 below.

  The arylene group in B and D of the present invention is preferably a monocyclic or condensed ring arylene group having 6 to 60 carbon atoms, more preferably an arylene group having 6 to 40 carbon atoms, still more preferably an arylene group having 6 to 30 carbon atoms. is there. Specific examples include phenylene, biphenylene, naphthalenediyl, anthracenediyl, phenanthroline diyl, pyrenediyl, triphenylenediyl, benzophenanthroline diyl, perylenediyl, pentaphenylenediyl, pentacenediyl, and the like. good.

  The heteroarylene group in B and D of the present invention is preferably a monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms, more preferably at least one of a nitrogen atom, an oxygen atom or a sulfur atom. It is a monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms, and more preferably a 5- or 6-membered aromatic heterocyclic group having 4 to 30 carbon atoms. Specific examples of the aromatic heterocyclic group include pyrrole diyl, furanyl, thienylene, pyridinediyl, pyridazinediyl, pyrimidinediyl, pyrazinediyl, quinolinediyl, isoquinolinediyl, cinnolinediyl, quinazolinediyl, quinoxalinediyl, phthalazinediyl, pteridinediyl, acridinediyl, phenidinediyl Examples thereof include diyl and phenanthroline diyl, and these groups may have a substituent.

  Examples of the ethenylene group in B and D of the present invention include an ethenylene group, a 1-methylethenylene group, a 1-ethylethenylene group, and the like, and these groups may have a substituent.

  As the aryl group in E and F of the present invention, a phenyl group, a biphenylenyl group, a triphenylenyl group, a tetraphenylenyl group, a 3-nitrophenyl group, a 4-methylthiophenyl group, a 3,5-dicyanophenyl group, o-, m- and p-tolyl groups, xylyl groups, o-, m- and p-cumenyl groups, mesityl groups, pentarenyl groups, indenyl groups, naphthyl groups, anthracenyl groups, azulenyl groups, heptalenyl groups, acenaphthylenyl groups, phenalenyl groups, fluorenyl groups Group, anthryl group, anthraquinonyl group, 3-methylanthryl group, phenanthryl group, pyrenyl group, chrysenyl group, 2-ethyl-1-chrysenyl group, picenyl group, perylenyl group, 6-chloroperenylenyl group, pentaphenyl group, pentacenyl group , Tetraphenylenyl group, hexa Eniru group, hexacenyl group, rubicenyl group, coronenyl groups, trinaphthylenyl groups, heptacenyl groups, pyranthrenyl groups, include ovalenyl group may have a substituent on these groups.

  The heteroaryl group in E and F of the present invention includes thionyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, quinolyl group, isoquinolyl group, phthalazinyl Group, quinoxalinyl group, quinazolinyl group, carbazolyl group, acridinyl group, phenazinyl group, furfuryl group, isothiazolyl group, isoxazolyl group, furazanyl group, phenoxazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, 2-methylpyridyl group , 3-cyanopyridyl group and the like, and these groups may have a substituent.

  The unit represented by the general formula [1] of the present invention and the substituent in the unit having an amino group are a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group. Thioalkoxy group, cyano group, amino group, mono- or di-substituted amino group, hydroxyl group, mercapto group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted aryl group, substituted or unsubstituted Represents a substituted heteroaryl group. The substituents may form a substituted or unsubstituted ring with adjacent substituents.

  Here, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  Examples of the substituted or unsubstituted alkyl group include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, Isooctyl group, stearyl group, trichloromethyl group, trifluoromethyl group, cyclopropyl group, cyclohexyl group, 1,3-cyclohexadienyl group, 2-cyclopenten-1-yl group, 2,4-cyclopentadiene-1-ylidenyl Groups and the like.

  Examples of the substituted or unsubstituted alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a 2-ethylhexyloxy group, Examples include stearyloxy group and trifluoromethoxy group.

  Examples of the substituted or unsubstituted thioalkoxy group include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, and an octylthio group. .

  Mono- or di-substituted amino groups include methylamino, dimethylamino, ethylamino, diethylamino, dipropylamino, dibutylamino, diphenylamino, bis (acetoxymethyl) amino, bis ( Acetoxyethyl) amino group, bis (acetoxypropyl) amino group, bis (acetoxybutyl) amino group, dibenzylamino group and the like.

  Examples of the substituted or unsubstituted aryloxy group include a phenoxy group, a p-tert-butylphenoxy group, and a 3-fluorophenoxy group.

  Examples of the substituted or unsubstituted arylthio group include a phenylthio group and a 3-fluorophenylthio group.

  Examples of the substituted or unsubstituted aryl group include a phenyl group, a biphenylenyl group, a triphenylenyl group, a tetraphenylenyl group, a 3-nitrophenyl group, a 4-methylthiophenyl group, a 3,5-dicyanophenyl group, o-, m- and p-tolyl groups, xylyl groups, o-, m- and p-cumenyl groups, mesityl groups, pentarenyl groups, indenyl groups, naphthyl groups, anthracenyl groups, azulenyl groups, heptalenyl groups, acenaphthylenyl groups, phenalenyl groups, fluorenyl groups Group, anthryl group, anthraquinonyl group, 3-methylanthryl group, phenanthryl group, pyrenyl group, chrysenyl group, 2-ethyl-1-chrysenyl group, picenyl group, perylenyl group, 6-chloroperenylenyl group, pentaphenyl group, pentacenyl group , Tetraphenylenyl group, hexa Eniru group, hexacenyl group, rubicenyl group, coronenyl groups, trinaphthylenyl groups, heptacenyl groups, pyranthrenyl groups, ovalenyl group and the like.

  Examples of the substituted or unsubstituted heteroaryl group include thionyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, quinolyl group, isoquinolyl group, phthalazinyl group. Group, quinoxalinyl group, quinazolinyl group, carbazolyl group, acridinyl group, phenazinyl group, furfuryl group, isothiazolyl group, isoxazolyl group, furazanyl group, phenoxazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, 2-methylpyridyl group , 3-cyanopyridyl group and the like.

  A preferable substituent in the unit having an amino group as the unit represented by the general formula [1] of the present invention is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group.

  Further, adjacent substituents form an aliphatic, carbocyclic aromatic, heterocyclic aromatic or heterocyclic ring which may contain a 5- to 7-membered oxygen atom, nitrogen atom, sulfur atom, etc. It may also have a substituent at any position of these rings.

The copolymer of the unit represented by the general formula [1] of the present invention and the unit having an amino group may be a random, block, or graft copolymer, and has an intermediate structure thereof. It may be a polymer having, for example, a random copolymer having block properties.
The copolymer of the unit represented by the general formula [1] and the unit having an amino group of the present invention is further co-polymerized with styrene and its derivatives, acrylic acid and its derivatives, maleic acid and its derivatives, organic acid vinyl ester and the like. It may be a polymer.

  Although the weight average molecular weight of the organic electroluminescent device material of the present invention is not particularly limited in consideration of heat resistance and stability in a thin film state, for example, 1000--1000000, particularly 3000 in terms of polystyrene by gel permeation chromatography measurement. -Preferably it is -500,000.

B in the general formula [1] of the present invention is selected from the group consisting of a direct bond, or a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, and a substituted or unsubstituted ethenylene group. This is a divalent organic residue. When the arylene group or heteroarylene group has a substituent, the substituents may be combined to form a new ring.
Although the structural example of the unit used for a polymer is specifically shown in Table 1, the polymer of this invention is not limited to the following representative examples. Table 1 shows only the structure of each unit monomer, and does not show its polymerization form. Moreover,% in a table | surface represents mol%.

The dopant material used in the present invention is a compound represented by the general formula [4].
In the formula of the compound represented by the general formula [4] in the present invention, R ^{13 to} R ²⁰ are each independently —NR ²¹ R ²² (R ²¹ and R ²² are each a substituted or unsubstituted alkyl group, substituted or unsubstituted Represents a substituted aryl group, and R ²¹ and R ²² may be combined.), A hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl An oxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted aryl group is represented.
However, two or more of R ^{13 to} R ²⁰ are —NR ²¹ R ²² . More preferably, at least R ¹³ and R ¹⁶ , or at least R ¹³ and R ¹⁷ are —NR ²¹ R ²² .

In the general formula [4] of the present invention, examples of the alkylamino group represented by —NR ²¹ R ²² include a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, a benzylamino group, and a dibenzylamino group. Specific examples of the arylamino group include phenylmethylamino group, diphenylamino group, ditolylamino group, dibiphenylamino group, di (4-methylbiphenyl) amino group, and di (3-methylphenyl) amino. Group, di (4-methylphenyl) amino group, naphthylphenylamino group, bis [4- (α, α′-dimethylbenzyl) phenyl] amino group, and the like.

R ²¹ and R ²² are combined to form a morpholine ring, piperazine ring, piperidine ring, benzopiperazine ring, acridine ring, phenazine ring, pyrenyl ring, carbazole ring, benzopyranyl ring, xanthene ring, thiazolyl ring, thiazine ring, A saturated or unsaturated ring such as a fanothiazine ring may be formed.

  The halogen atom includes fluorine, chlorine, bromine and iodine.

  Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a stearyl group. In addition to an unsubstituted alkyl group having 1 to 20 carbon atoms, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α- There are substituents of alkyl groups having 1 to 20 carbon atoms such as methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group. Further, adjacent alkyl groups may be bonded to form a cycloalkyl ring.

  Moreover, as a substituted or unsubstituted alkoxyl group, it is C1-C20, such as a methoxy group, an ethoxy group, a propoxy group, n-butoxy group, t-butoxy group, n-octyloxy group, t-octyloxy group. In addition to unsubstituted alkoxyl groups, there are substituted products of C1-C20 alkoxyl groups such as 1,1,1-tetrafluoroethoxy group, phenoxy group, benzyloxy group, octylphenoxy group and the like.

  Examples of the substituted or unsubstituted aryloxy group include a phenoxy group, a p-nitrophenoxy group, a p-tert-butylphenoxy group, a 3-fluorophenoxy group, a pentafluorophenyl group, and a 3-trifluoromethylphenoxy group. There is.

  Examples of the substituted or unsubstituted alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and a trifluoromethylthio group.

  Examples of the substituted or unsubstituted arylthio group include phenylthio group, p-nitrophenylthio group, p-tert-butylphenylthio group, 3-fluorophenylthio group, pentafluorophenylthio group, and 3-trifluoromethylphenyl group. There are thio groups and the like.

  Examples of the substituted or unsubstituted aryl group include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group, 4-methylbiphenyl group, 4- Substituted or unsubstituted aryl having 6 to 18 aromatic carbon atoms such as ethylbiphenyl group, 4-cyclohexylbiphenyl group terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group In addition, the aryl group may have an aromatic carbon atom substituted by a nitrogen atom, an oxygen atom and / or a sulfur atom. Such aryl groups include furanyl, thiophenyl, pyrrole, pyranyl, thiopyranyl, pyridinyl, thiazolyl, imidazolyl, pyrimidinyl, pyridinyl, triazinyl, indolinyl, quinolyl, purinyl Etc.

  Among these compounds, a compound having a substituent having an aryl group as represented by the general formula [4] has a high glass transition point and melting point in an organic layer, an organic layer or an organic layer during electroluminescence. Since resistance to Joule heat generated between the organic layer and the metal electrode (heat resistance) is improved, when used as a light-emitting material of an organic EL element, it exhibits high emission luminance and is advantageous when emitting light for a long time. . The compounds of the present invention are not limited to these substituents.

  In the present invention, the compound represented by the general formula [4] can be synthesized, for example, by the following method. In a nitrobenzene solvent, dibromonaphthalene or diiodonaphthalene and an aromatic diamine compound are reacted with a catalyst such as potassium carbonate or copper for 50 hours at 200 ° C. to synthesize an aromatic amine compound represented by the general formula [4]. Alternatively, it can be synthesized in the same manner by reacting diaminonaphthalene and a halogen-substituted aryl derivative in 1,3-dimethyl-2-imidazolidinone using potassium hydroxide or a copper catalyst. Instead of potassium carbonate, sodium carbonate, sodium hydroxide, or the like can be used. Examples of the catalyst include copper powder, cuprous chloride, tin, and stannous chloride. Examples of the solvent include N, N-dimethylformamide and dimethyl sulfoxide.

  Although the typical example of a compound shown by General formula [4] is specifically illustrated in Table 2, it is not limited to these.

  The compound represented by the general formula [4] of the present invention is a compound having strong fluorescence in the solid state and excellent in electroluminescence, and is therefore used as a doping material in the light emitting layer. In addition, the compound of the general formula [4] can be optimally selected for high emission efficiency and emission wavelength by doping at an optimal ratio in the light emitting layer.

The compound of the general formula [4] is contained in the light emitting layer in the range of 0.001 wt% to 50 wt% with respect to the host material, preferably in the range of 0.01 wt% to 10 wt%. It is effective.

  As the doping material used in the present invention, the general formula [4] may be used alone or in combination with other organic materials. The organic material used in combination may be a low molecular organic material or a high molecular organic material. Moreover, it is also possible to use it by laminating and coating with other polymer organic materials. Furthermore, it can be used by mixing with a low molecular weight compound or by laminating. In this case, the low molecular weight compound may be mixed with a polymer binder and applied, or may be laminated by a method such as vacuum deposition or sputtering.

  Doping materials include those that emit light from singlet excitons, those that emit light from triplet excitons, and those that emit light from both, and any of these light emitting materials can be used in the organic EL device of the present invention. is there. As a doping material that can be used in the present invention, polyalkylfluorene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, polythiophene derivatives, and other light-emitting polymers can be used. In addition, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bis Benzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelating oxinoid compound, Examples include, but are not limited to, quinacridone, rubrene, and fluorescent dyes for dye laser and sensitization. Not shall.

  Hereinafter, although the organic EL element of this invention is demonstrated in detail, they do not limit this invention.

  The organic EL element is composed of an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode. Here, the single layer type organic EL element is an element composed of only a light emitting layer between an anode and a cathode. Point to. On the other hand, the multilayer organic EL element facilitates injection of holes and electrons into the light emitting layer in addition to the light emitting layer, and facilitates recombination of holes and electrons in the light emitting layer. In order to do so, it refers to a layer in which a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and the like are laminated. Therefore, typical element configurations of the multilayer organic EL element include (1) anode / hole injection layer / light emitting layer / cathode, and (2) anode / hole injection layer / hole transport layer / light emitting layer / cathode. (3) Anode / hole injection layer / light emitting layer / electron injection layer / cathode, (4) Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode, (5) Anode / positive Hole injection layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (6) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (7) An element structure in which a multilayer structure of anode / light emitting layer / hole blocking layer / electron injection layer / cathode, (8) anode / light emitting layer / electron injection layer / cathode, etc., is considered.

    Moreover, each organic layer mentioned above may be formed by the layer structure of two or more layers, respectively, and several layers may be laminated | stacked repeatedly.

    As a hole injection material or a hole transport material, it has the ability to transport holes, has a hole injection effect from the anode, and has an excellent hole injection effect for the light emitting layer or light emitting material. Examples thereof include compounds that prevent the generated excitons from moving to the electron injection zone or the electron injection material and have an excellent thin film forming ability. Specifically, PEDOT, phthalocyanine derivative, naphthalocyanine derivative, porphyrin derivative, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, hydrazone, acyl hydrazone, polyarylalkane, stilbene, There are butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and their derivatives, and polymer materials such as polyvinyl carbazole, polysilane, conductive polymer, etc. Is not to be done.

  Examples of the hole blocking material include compounds having a HOMO level higher than the HOMO level of the light emitting layer. That is, for the hole blocking layer, a hole blocking material capable of preventing holes that have passed through the light emitting layer from reaching the electron injection layer and forming a layer having excellent thin film formability is used. Examples of the material having such a role include a compound having an oxadiazolyl group, a compound having a triazolyl group, a compound having a pyrazolyl group, a compound having an oxazolyl group, bis (8-hydroxyquinolinate) (4-phenolate) Aluminum, bis (8-hydroxyquinolinato) (4-phenylphenolate) aluminum complex compounds such as aluminum, bis (2-methyl-8-hydroxyquinolinato) (4-cyano-1-naphtholato) gallium, Gallium complex compounds such as bis (2-methyl-8-hydroxyquinolinate) (4-phenylphenolate) gallium, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl -1,10-phenanthroline (BCP), etc. Family compound, and the like.

  Furthermore, preferable nitrogen-containing five-membered ring derivatives include oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and triazole derivatives. Specifically, 2,5-bis (1-phenyl) -1, 3,4-oxazole, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) -1,3,4-oxadiazole, 2- (4 '-Tert-butylphenyl) -5- (4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, 1,4 -Bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4'-tert-butyl) Phenyl) -5- (4 ″ -biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) -1,3,4-thiadiazole, 1,4-bis [2- (5- Phenylthiadiazolyl)] benzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) -1, Examples include 3,4-triazole and 1,4-bis [2- (5-phenyltriazolyl)] benzene, but are not particularly limited thereto.

  As an electron injection material, it has the ability to transport electrons, has a hole injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or light emitting material, and adheres to the cathode interface and forms a thin film. An electron injection material capable of forming an excellent electron injection layer is used. Examples of such electron injection materials include metal complex compounds, nitrogen-containing five-membered ring derivatives, fluorenone derivatives, anthraquinodimethane derivatives, diphenoquinone derivatives, thiopyrandioxide derivatives, perylenetetracarboxylic acid derivatives, fluorenylidenemethane. Derivatives, anthrone derivatives, silole derivatives, triarylphosphine oxide derivatives, calcium acetylacetonate, sodium acetate and the like. In addition, inorganic / organic composite materials doped with metal such as cesium in bathophenanthroline (Proceedings of the Society of Polymer Science, Vol. 50, No. 4, 660, published in 2001), and the 50th Applied Physics Related Lecture Lecture Proceedings, No. Examples of electron injection materials include BCP, TPP, T5MPyTZ, etc. published on page 3, 1402, 2003. Electrons can be transported by forming a thin film necessary for device fabrication and injecting electrons from the cathode. If it is material, it will not specifically limit to these.

  Among the electron injection materials, particularly effective electron injection materials include metal complex compounds, nitrogen-containing five-membered ring derivatives, silole derivatives, and triarylphosphine oxide derivatives. As a preferable metal complex compound that can be used in the present invention, a metal complex of 8-hydroxyquinoline or a derivative thereof is suitable. Specific examples of the metal complex of 8-hydroxyquinoline or a derivative thereof include tris (8-hydroxyquinolinate) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (4-methyl-8- Hydroxyquinolinato) aluminum, tris (5-methyl-8-hydroxyquinolinato) aluminum, tris (5-phenyl-8-hydroxyquinolinato) aluminum, bis (8-hydroxyquinolinato) (1-naphtholate) ) Aluminum, bis (8-hydroxyquinolinate) (2-naphtholate) aluminum, bis (8-hydroxyquinolinate) (phenolate) aluminum, bis (8-hydroxyquinolinato) (4-cyano-1-naphtholate) ) Aluminum, bis (4-methyl-8) Hydroxyquinolinato) (1-naphtholato) aluminum, bis (5-methyl-8-hydroxyquinolinato) (2-naphtholato) aluminum, bis (5-phenyl-8-hydroxyquinolinato) (phenolate) aluminum, Bis (5-cyano-8-hydroxyquinolinate) (4-cyano-1-naphtholato) aluminum, bis (8-hydroxyquinolinato) chloroaluminum, bis (8-hydroxyquinolinato) (o-cresolate) Aluminum complex compounds such as aluminum, tris (8-hydroxyquinolinato) gallium, tris (2-methyl-8-hydroxyquinolinato) gallium, tris (4-methyl-8-hydroxyquinolinato) gallium, tris ( 5-Methyl-8-hydroxyquinolinate Gallium, tris (2-methyl-5-phenyl-8-hydroxyquinolinato) gallium, bis (2-methyl-8-hydroxyquinolinato) (1-naphtholato) gallium, bis (2-methyl-8-hydroxy) Quinolinate) (2-naphtholato) gallium, bis (2-methyl-8-hydroxyquinolinato) (phenolate) gallium, bis (2-methyl-8-hydroxyquinolinato) (4-cyano-1-naphtholate) ) Gallium, bis (2,4-dimethyl-8-hydroxyquinolinato) (1-naphtholate) gallium, bis (2,5-dimethyl-8-hydroxyquinolinato) (2-naphtholato) gallium, bis (2 -Methyl-5-phenyl-8-hydroxyquinolinate) (phenolate) gallium, bis (2-methyl-5- Cyano-8-hydroxyquinolinate) (4-cyano-1-naphtholate) gallium, bis (2-methyl-8-hydroxyquinolinate) chlorogallium, bis (2-methyl-8-hydroxyquinolinate) ( In addition to gallium complex compounds such as o-cresolate) gallium, 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, bis (10-hydroxybenzo [h And quinolinato) beryllium, bis (8-hydroxyquinolinato) zinc, and bis (10-hydroxybenzo [h] quinolinato) zinc.

Examples of preferable silole derivatives that can be used in the present invention include the following silole derivatives.

Of the electron injecting materials that can be used in the present invention, preferred triarylphosphine oxide derivatives include those disclosed in JP-A-2002-63989, JP-A-2004-95221, JP-A-2004-203828, and JP-A-2004. -204140, for example, the following triarylphosphine oxide derivatives are listed.

  The method for forming an organic compound thin film used in the present invention is not particularly limited. For example, a vacuum deposition method from a powder state, a method of applying after dissolving in a solvent (for example, an inkjet method, a spray method, a printing method, A spin coating method, a casting method, a dipping method, a bar coating method, a roll coating method and the like can be used, but a coating method is preferable from the viewpoint of simplification of the element manufacturing process, workability, and increase in area. Solvents used for film formation by the coating method include organic halogen solvents such as dichloroethane, dichloromethane and chloroform, ether solvents such as tetrahydrofuran and 1,4-dioxane, and aromatic hydrocarbon solvents such as toluene and xylene. An amide solvent such as dimethylformamide and dimethylacetamide, an ester solvent such as ethyl acetate and butyl acetate, or a mixed solvent thereof may be used. Although it depends on the structure and molecular weight of the polymer, the film is usually formed using a solution of 0.01 to 10% by weight, preferably 0.1 to 5% by weight, of a solvent. The film thickness of each layer is not particularly limited, but if the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. Conversely, if the film thickness is too thin, pinholes, etc. And it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied. Accordingly, the thickness of each layer is suitably in the range of 1 nm to 1 μm, but more preferably in the range of 10 nm to 0.2 μm.

  In addition, in order to improve the stability of the organic EL element with respect to temperature, humidity, atmosphere, etc., a protective layer may be provided on the surface of the element, or the entire element may be covered or sealed with a resin or the like. In particular, when the entire element is covered or sealed, a photocurable resin that is cured by light is preferably used.

  The current applied to the organic EL element of the present invention is usually a direct current, but a pulse current or an alternating current may be used. The current value and the voltage value are not particularly limited as long as the element is within a range not destroying the element. However, considering the power consumption and life of the element, it is desirable to efficiently emit light with as little electrical energy as possible.

  The organic EL device driving method of the present invention can be driven not only by the passive matrix method but also by the active matrix method. Further, the method for extracting light from the organic EL device of the present invention is applicable not only to the method of bottom emission for extracting light from the anode side but also to the method of top emission for extracting light from the cathode side. These methods and techniques are described in Shinji Kido, “All about organic EL”, published by Nihon Jitsugyo Shuppansha (published in 2003).

  Furthermore, the organic EL element of the present invention may adopt a microcavity structure. This is because the organic EL element has a structure in which the light emitting layer is sandwiched between the anode and the cathode, and the emitted light causes multiple interference between the anode and the cathode, but the reflectance and transmission of the anode and the cathode. This is a technology that actively uses the multiple interference effect and controls the emission wavelength extracted from the device by appropriately selecting the optical characteristics such as the rate and the film thickness of the organic layer sandwiched between them. . Thereby, it is also possible to improve the emission chromaticity. For the mechanism of this multiple interference effect, see J.A. Yamada et al., AM-LCD Digest of Technical Papers, OD-2, p. 77-80 (2002).

As the conductive material used for the anode of the organic electroluminescence device, a material having a work function larger than 4 eV is preferable, and carbon, aluminum, cesium, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Further, palladium, etc. and alloys thereof, ITO substrate, metal oxide such as tin oxide and indium oxide called NESA substrate, and organic conductive resin such as polythiophene and polypyrrole are used.
As the conductive material used for the cathode, those having a work function smaller than 4.0 eV are preferable, such as magnesium, barium, calcium, cesium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, and the like. However, it is not limited to these. If necessary, the anode and the cathode may be formed of two or more layers.

  The organic electroluminescent element of the present invention can be applied to flat panel displays such as wall-mounted televisions, flat light emitters, light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. And its industrial value is very large.

Hereinafter, the present invention will be described in more detail based on examples. In the description, parts represent parts by weight and% represents% by weight.
Hereinafter, the present invention will be described in more detail based on examples.
Synthesis Method of Compound (2) In 50 parts of 1,3-dimethyl-2-imidazolidinone, 6.5 parts of 1,4-dibromonaphthalene, 16.2 parts of p, p'-ditolylamine, and 12 parts of potassium carbonate Then, 0.5 part of copper powder was added, and the mixture was heated and stirred at 200 ° C. for 50 hours. Thereafter, it was diluted with 500 parts of water. Extraction with ethyl acetate, concentration, and purification by column chromatography using silica gel gave 12 parts of a powder having white fluorescence. It was confirmed to be the compound (2) by molecular weight analysis by FD-MS.

Synthesis method of compound (5) In 50 parts of 1,3-dimethyl-2-imidazolidinone, 5.5 parts of 1,4-dibromonaphthalene, 12.2 parts of 2-naphthyl-phenylamine, and 8 parts of potassium carbonate Then, 0.5 part of copper powder was added, and the mixture was heated and stirred at 200 ° C. for 50 hours. Thereafter, it was diluted with 500 parts of water. Extraction with ethyl acetate, concentration, and purification by column chromatography using silica gel gave 13 parts of a powder having white fluorescence. It was confirmed to be the compound (5) by molecular weight analysis by FD-MS.

Method for synthesizing compound (15) In 20 parts of nitrobenzene, 5 parts of 1,5-diaminonaphthalene, 45 parts of 4-methyliodobenzene, 28 parts of sodium hydroxide and 0.5 part of cuprous chloride were added. The mixture was heated and stirred at 200 ° C. for 50 hours. Then, it was diluted with 500 parts of water, and then extracted with ethyl acetate, concentrated, and purified by column chromatography using silica gel to obtain 3 parts of powder having white fluorescence. It was confirmed to be the compound (15) by molecular weight analysis by FD-MS.

Synthesis method of compound (26) In 30 parts of 1,3-dimethyl-2-indazolidinone, 8 parts of 2,6-dibromonaphthalene, 15 parts of 2-naphthyl-phenylamine, 10 parts of potassium carbonate, copper powder 0.5 The mixture was added and stirred at 200 ° C. for 50 hours. Then, it was diluted with 500 parts of water, and then extracted with ethyl acetate, concentrated, and purified by column chromatography using silica gel to obtain 15 parts of powder having white fluorescence. It was confirmed to be the compound (26) by molecular weight analysis by FD-MS.

EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example. In the examples, all mixing ratios are weight ratios unless otherwise specified. The vacuum deposition method was performed in a vacuum of 10 ⁻⁶ Torr under conditions without temperature control such as substrate heating and cooling. In the evaluation of the light emission characteristics of the element, the characteristics of an organic EL element having an electrode area of 2 mm × 2 mm were measured.

Example 1
A PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) on a cleaned glass plate with an ITO electrode was spin-coated at 40 nm. The film was formed into a film thickness, and P-5 shown in Table 2 and the compound (2) shown in Table 1 as a luminescent material (3% by weight) were dissolved and dispersed in dichloroethane at a concentration of 1.0 wt%, and spin coating was used. A light emitting layer having a thickness of 60 nm was obtained. Further, an Alq3 film having a thickness of 40 nm was formed by vacuum deposition to form an electron transport layer. Furthermore, an electrode was formed with a film thickness of 1 nm for LiF and 200 nm for Al, thereby producing an organic EL element 1.
The light emission characteristics of this device were a blue-green light emission of 150 (cd / m ² ), a maximum luminance of 3500 (cd / m ² ), and a luminous efficiency of 0.80 (lm / W) at a DC voltage of 5V.

Example 2
PEDOT / PSS was formed into a film thickness of 40 nm by spin coating on the cleaned glass plate with ITO electrode, and P-14 and compound (2) shown in Table 2 were (3% by weight) and 2,5- Bis (1-naphthyl) -1,3,4-thiadiazole (35 wt%) was dissolved and dispersed in dichloroethane at a concentration of 1.0 wt%, and a light emitting layer having a thickness of 50 nm was obtained by spin coating. A hole blocking layer having a thickness of 7 nm was obtained from bis (8-hydroxyquinolinate) (phenolate) aluminum by vacuum deposition on this coated substrate. Further, an Alq3 film having a thickness of 40 nm was formed by vacuum deposition to form an electron transport layer. Furthermore, an electrode was formed with a film thickness of 1 nm for LiF and 200 nm for Al, thereby producing an organic EL element 2.
This device produced blue light emission with a direct current voltage of 5V and an emission luminance of 350 (cd / m ² ), a maximum emission luminance of 5000 (cd / m ² ), and an emission efficiency of 2.8 (lm / W) at 5V.

Example 3
PEDOT / PSS was formed into a film thickness of 40 nm by spin coating on the cleaned glass plate with ITO electrode, and P-21 and compound (20) shown in Table 2 (1.0 wt%) were 1.0 wt%. A light-emitting layer having a thickness of 80 nm was obtained by spin coating. By applying vacuum deposition to this coated substrate, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazole was obtained as a 7 nm thick hole blocking layer. Furthermore, an electron transport layer was formed by depositing Alq3 with a thickness of 40 nm by vacuum evaporation, and an electrode was formed with a film thickness of LiF of 1 nm and Al of 200 nm to produce an organic EL element 3.
This device produced a blue-green light emission of 360 (cd / m ² ), a maximum luminance of 4500 (cd / m ² ), and a luminous efficiency of 2.85 (lm / W) at a DC voltage of 5V.

Example 4
A PEDOT / PSS film was formed into a film thickness of 40 nm by spin coating on a cleaned glass plate with an ITO electrode, and P-1 and compound (8) shown in Table 2 were (3 wt%) and the following compound ( 37) (20%) was dissolved and dispersed in dichloroethane at a concentration of 1.0 wt%, and a light emitting layer having a thickness of 50 nm was obtained by a spin coating method. A hole blocking layer having a thickness of 7 nm was obtained from bis (2-methyl-8-quinolinato) (1-naphtholate) gallium on this coated substrate by vacuum deposition. Further, an Alq3 film having a thickness of 40 nm was formed by vacuum deposition to form an electron transport layer. Further, an electrode was formed with a film thickness of 1 nm for LiF and 200 nm for Al, and an organic EL element 4 was produced.
This device produced blue light emission of 300 (cd / m ² ), a maximum luminance of 5200 (cd / m ² ), and a luminous efficiency of 2.70 (lm / W) at a DC voltage of 5V.
Compound (37)

Example 5
A PEDOT / PSS film was formed into a film thickness of 40 nm by spin coating on a cleaned glass plate with an ITO electrode, and the compounds shown in Table 1 (3 wt%) were used as P-4 in Table 2 and the light emitting material. And the following compound (38) (20% by weight), an electron transporting material (2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-thiadiazole) (25% by weight) %) Was dissolved in toluene at a concentration of 1.0 wt%, and a light emitting layer having a thickness of 80 nm was obtained by spin coating, and an electron transport layer was formed by depositing Alq3 by 30 nm by vacuum deposition. Furthermore, an electrode was formed with a film thickness of 1 nm for LiF and 200 nm for Al, thereby producing an organic EL element 5.
This device obtained blue light emission with a direct current voltage of 5 V and an emission luminance of 210 (cd / m ² ), a maximum emission luminance of 3500 (cd / m ² ), and an emission efficiency of 2.8 (lm / W).
Compound (38)

Examples 6 to 36
PEDOT / PSS was formed into a film thickness of 40 nm by spin coating on the cleaned glass plate with ITO electrode, and P-16 and compound (2) shown in Table 2 (1.0 wt%) were 1.0 wt%. A light-emitting layer having a thickness of 80 nm was obtained by spin coating. Furthermore, an electrode was formed with a film thickness of 20 nm for Ca and 200 nm for Al, and organic EL elements 6 to 36 were produced.
Table 3 shows the light emission characteristics of the device. The light emission luminance here is the luminance when a DC voltage of 5 V is applied. The organic EL elements of this example all had high luminance characteristics with a maximum luminance of 3000 (cd / m ² ) or more, and a blue emission color could be obtained.

In the organic EL device shown in this example, light emission with a maximum light emission luminance of 3000 (cd / m ² ) or more was obtained in a two-layer or higher device configuration, and all of the light emission efficiency could be obtained. When the organic EL element shown in this example was allowed to emit light continuously at 3 (mA / cm ² ), stable light emission could be observed for 1000 hours or more. The organic EL device of the present invention achieves improvement in light emission efficiency, light emission luminance and long life, and is used together with light emitting materials, doping materials, hole injection materials, electron injection materials, sensitizers, resins. The electrode material and the element manufacturing method are not limited.

  The organic EL element using the light emitting material for organic EL of the present invention as a light emitting material showed high luminance and higher luminance than conventional ones, and a long-life organic EL element could be obtained.

  The organic EL device of the present invention achieves low driving voltage, light emission efficiency, and improvement of light emission luminance. Light emitting material, hole transport material, electron transport material, electrode material, etc. used together and device manufacturing method It is not intended to limit.

  An organic EL element having a low driving voltage and high luminous efficiency can be obtained as compared with the prior art.

Claims (3)

In an organic electroluminescent device in which a plurality of organic compound thin films including a light emitting layer are formed between both electrodes of an anode layer and a cathode layer, the light emitting layer is composed of a host material and a dopant material, and the host material is An organic electroluminescent device comprising a polymer comprising a unit represented by the general formula [1], wherein the dopant material comprises a compound represented by the following general formula [4].
General formula [1]

[Wherein A represents a non-conjugated trivalent organic residue,
B represents a direct bond or a divalent organic residue selected from the group consisting of a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, and a substituted or unsubstituted ethenylene group. Represent,
C represents a monovalent organic residue represented by the following general formula [2] or the following general formula [3]. ]
General formula [2]

[Wherein R ^{1 to} R ⁷ each independently represents a bonding site, a hydrogen atom or a substituent,
X is a direct bond, —O—, —S—, —Se—, —NH—, —NR ⁸ — (R ⁸ represents an alkyl group or an aryl group), —S (═O) ₂ —, — ( CO) -, - COO -, - OCO-, or, -CH ₂ - indicates,
R ^{1 to} R ⁷ may be bonded to each other to form an aryl ring, and further the aryl ring may have a substituent. ]
General formula [3]

[Wherein R ^{1 to} R ⁵ and R ^{9 to} R ¹² each independently represents a bonding site, a hydrogen atom, or a substituent. ]
General formula [4]

[Wherein, R ^{13 to} R ²⁰ each independently represent —NR ²¹ R ²² (R ²¹ and R ²² represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and R ²¹ and R ²² And a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, It represents a substituted or unsubstituted arylthio group or a substituted or unsubstituted aryl group, and two or more of R ^{13 to} R ²⁰ represent —NR ²¹ R ²² . ] The organic electroluminescent element according to claim 1, wherein at least R ¹³ and R ¹⁶ are —NR ²¹ R ²² . The organic electroluminescent element according to claim 1, wherein at least R ¹³ and R ¹⁷ are —NR ²¹ R ²² .