JP2005054075A - Material for organic electroluminescent element, and organic electroluminescent element using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a light-emitting material for an organic electroluminescent element having high light-emitting luminance and a long light-emitting life, and to provide the organic electroluminescent element using the light-emitting material. <P>SOLUTION: The material for the organic electroluminescent element contains a non-conjugated polymer, an amine compound and a phosphorescent compound. The non-conjugated polymer contains at least one unit represented by general formula (1) and obtained by bonding a group B (a substituted or unsubstituted arylene or heteroarylene group, or a direct bond) to a group A (a non-conjugated trivalent organic residue), and further bonding a group C (a monovalent organic residue) represented by formula (2) to the group B. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a light-emitting material and a high-luminance light-emitting element used for a planar light source, an organic electroluminescence (EL) element used for display, and the like.

  An electroluminescent element using an organic substance is promising for use as a solid light emitting type inexpensive large-area full-color display element, and many developments have been made. In general, an organic electroluminescent 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 electroluminescent elements have a higher driving voltage and lower luminance and luminous efficiency than inorganic EL elements. Further, the characteristic deterioration has been remarkably not put into practical use.

In recent years, an organic electroluminescent device in which a thin film containing an organic compound having a high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less has been reported and attracted attention (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 electroluminescent element involving an organic compound vapor deposition operation has a problem in productivity, and it is desirable to create a coating method 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 electroluminescent element used in the production of an organic electroluminescent element of a coating method advantageous for productivity (see Non-Patent Documents 2 and 3), but a light emitting part. Has a problem in that it is difficult to control the concentration of the light-emitting material and to delicately control the color tone and light emission intensity. Similarly, as an organic electroluminescent element using a coating method, for example, there is an element that disperses a low molecular weight dye or the like in polyvinyl carbazole (see Patent Document 1), but it has been found that there is a problem in performance. In addition, organic electroluminescent devices using a copolymer comprising a hole transporting monomer and an electron transporting monomer have been reported (Patent Documents 2 and 3).

  In a device using a phosphorescent light emitting material as a light emitting material, extremely high luminous efficiency has been reported (see Non-Patent Document 4), but a polyphenylene vinylene-based polymer light emitting material is used. Higher than an organic electroluminescent device (see Comparative Example 4 of this patent). This is because the mobility of holes in non-conjugated polymers typified by polyvinylcarbazole is low compared to polyphenylene vinylene-based polymer light-emitting materials. The voltage is considered to have increased. In the phosphorescent light emitting organic electric field element using a low molecular material, there is a report (see Non-Patent Document 5) that the driving voltage is lowered by doping a light emitting layer with a low molecular amine material. In the phosphorescent light-emitting organic electric field device using, there is no report to improve this problem.

JP-A-4-212286 Applied Physics Letters, 51, 913, 1987 Advanced Materials, Volume 2, Page 4 1992 Advanced Material 9, 551 pages 1997 JP 2000-159846 A JP 2001-104580 A Applied Physics Letters, 77, 2280 pages, 2000 The 50th Applied Physics-related Joint Lecture Proceedings (2003.3), Lecture number 28p-A-1, 1411 pages, 2003

  An object of the present invention is to provide an electroluminescent element material having high emission luminance and a long emission lifetime, and an electroluminescent element using the same. As a result of intensive studies by the present inventors, in an organic electroluminescent device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes, a non-conjugated polymer and a phosphorus are included in the light emitting layer. It has been found that the light emission starting voltage and the light emission efficiency of the electroluminescent device are improved by using a material containing a photoluminescent compound and an amine compound.

  The present invention has been achieved by the following materials and a light emitting device using the same.

  That is, the present invention relates to a material for an organic electroluminescent device comprising a non-conjugated polymer, an amine compound, and a phosphorescent compound.

  The present invention further relates to the material for an organic electroluminescent element containing an electron transporting compound.

  Moreover, this invention relates to the said organic electroluminescent element material in which a nonconjugated polymer contains at least 1 unit represented by following General formula [1].

General formula [1]

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

[Wherein R ^{1 to} R ⁷ represent 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 -, - CH 2 - represents,
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. ]

Moreover, this invention relates to the said organic electroluminescent element material whose general formula [2] is a monovalent organic residue represented by the following general formula [3].
General formula [3]

[Wherein R ^{18 to} R ²⁶ represent a bonding site, a hydrogen atom or a substituent. ]
The present invention also relates to the material for an organic electroluminescent element, wherein the electron transporting compound is an oxadiazole derivative.

  Moreover, this invention relates to the said material for organic electroluminescent elements whose phosphorescence-emitting compound is an iridium complex.

  Further, the present invention provides an organic electroluminescent device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes, wherein the light emitting layer contains the material for an organic electroluminescent device. The present invention relates to an organic electroluminescent device.

  According to the present invention, it is possible to obtain an organic EL element having a lower driving voltage, higher luminance, and longer life than conventional ones.

  The present invention is characterized in that, in the organic electroluminescence device, the light emitting layer contains a non-conjugated polymer, a phosphorescent compound, and an amine compound.

  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 E-1 to E-12, but are not limited thereto.

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

  Further, B and / or C in the general formula [1] may be introduced / modified after the non-conjugated main chain skeleton is formed, even though it is not introduced at the stage of the non-conjugated main chain skeleton monomer.

  The arylene group in the general formulas [1] to [3] is preferably a monocyclic or condensed arylene group having 6 to 60 carbon atoms, more preferably 6 to 40 carbon atoms, still more preferably 6 to 30 carbon atoms. An arylene group. Specific examples include phenylene, biphenylene, naphthalenediyl, anthracenediyl, phenanthroline diyl, pyrenediyl, triphenylenediyl, benzophenanthroline diyl, perylenediyl, pentaphenylenediyl, pentacenediyl, and the like. good.

  The heteroarylene group in the general formulas [1] to [3] is preferably a monocyclic or condensed aromatic heterocyclic group having 4 to 60 carbon atoms, and more preferably at least 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 containing one, 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, furandyl, 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.

  The substituent of the compound in the present invention is a halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted. Substituted 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 Alternatively, it represents an unsubstituted heteroaryl group, and the substituents may form a substituted or unsubstituted ring with adjacent substituents.

  Examples of the substituted or unsubstituted aryl group include phenyl group, biphenylenyl group, triphenylenyl group, tetraphenylenyl group, 3-nitrophenyl group, 4-methylthiophenyl group, 3,5-dicyanophenyl group, o-, m- And p-tolyl group, xylyl group, o-, m- and p-cumenyl group, mesityl group, pentarenyl group, indenyl group, naphthyl group, anthracenyl group, azulenyl group, heptaenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, Anthryl group, anthraquinonyl group, 3-methylanthryl group, phenanthryl group, pyrenyl group, chrysenyl group, 2-ethyl-1-chrysenyl group, picenyl group, perylenyl group, 6-chloroperylenyl group, pentaphenyl group, pentacenyl group, tetra Phenylenyl group, hexaphenyl Group, hexacenyl group, rubicenyl group, coronenyl groups, trinaphthylenyl groups, heptacenyl groups, pyranthrenyl groups, there is ovalenyl group.

  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, 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 -A cyanopyridyl group and the like.

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

  Substituted or unsubstituted alkyl groups include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, isooctyl , Stearyl group, trichloromethyl group, trifluoromethyl group, cyclopropyl group, cyclohexyl group, 1,3-cyclohexadienyl group, 2-cyclopenten-1-yl group, 2,4-cyclopentadiene-1-ylidenyl group, etc. There is.

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

  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.

  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.

  Preferred substituents are 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.

  In addition, the polymer having a unit represented by the general formula [1] of the present invention may be a homopolymer, a random, block, or graft copolymer, and has an intermediate structure thereof. The polymer may be a random copolymer having block property.

  When the unit represented by the general formula [1] is based on vinyl polymerization, it may be a copolymer with styrene and its derivatives, acrylic acid and its derivatives, maleic acid and its derivatives, organic acid vinyl ester, and the like. .

The amine compound used in the present invention is a low molecular weight amine compound, a conjugated amine polymer, or a non-conjugated amine polymer. Typical examples of these are shown in Table 1, but the polymer of the present invention is limited to the following representative examples. Is not to be done.
Table 1

Although the typical example of the nonconjugated polymer of this invention is specifically shown in Table 2, the nonconjugated polymer of this invention is not limited to the following representative examples. In addition, although 24 and 26-30 are copolymers, they show only the structure of each unit monomer, and do not show the polymerization form. N and m represent natural numbers.
Table 2

The phosphorescent light emitting material used in the present invention is particularly preferably a triplet light emitting metal complex, and the light emitting material capable of emitting light from triplet excitons is iridium complex Ir (ppy) ₃ (Tris-Ortho- Metalated Complexof Iridium (III) with 2-Phenylpyridine) is known. Moreover, experience has shown that in addition to iridium, rhodium, ruthenium, osmium, and rhenium metal coordination compounds are all hexacoordinate heavy metal compounds, and these have strong spin-orbit interaction. Since phosphorescence is strong, it is particularly preferable as the central metal of the phosphorescence-emitting compound of the present invention.
Table 3 shows typical examples of the phosphorescent material of the present invention.
Table 3

The compounds shown in Table 3 include those that are not electrically neutral. In this case, the compounds can be neutralized with counter ions (halogen ions, PF ₆ ⁻ , CIO ₄ ⁻ ).
The green light emitting device using Ir (ppy) ₃ achieves an external quantum yield of 8%, surpassing the external quantum yield of 5%, which was previously considered the limit of organic light emitting devices (Applied Physics Letters 75, 4 (1999)). Other Ir complex compounds and metal coordination porphyrin compounds can be used in the device configuration of the present invention, but are not limited thereto.

The electron injecting material used in the present invention has the ability to transport electrons, has a hole injecting effect from the cathode, an excellent electron injecting effect for the light emitting layer or the light emitting material, and the excitation generated in the light emitting layer. Examples thereof include compounds that prevent migration of a child to a hole injection zone and have an excellent thin film forming ability. For example,
Oxazole derivatives, triazole derivatives, oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, diphenoquinone derivatives, thiopyrandioxide derivatives, imidazole derivatives, perylenetetracarboxylic acid, fluorenylidenemethane derivatives, anthrone derivatives, phthalocyanine derivatives, metals Complexes (metal complexes of 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as a ligand, etc.) may be mentioned, but are not limited thereto.

  As a film forming method of the organic electroluminescent element material of the present invention, a coating method (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, etc.), etc. Can be used. Solvents used in the coating method include organic halogen solvents such as dichloroethane, dichloromethane and chloroform, ether solvents such as tetrahydrofuran and 1.4-dioxane, aromatic hydrocarbon solvents such as toluene and xylene, dimethyl An amide solvent such as formamide 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.

An organic EL element is an element in which a single-layer or multilayer organic thin film is formed between an anode and a cathode.
In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and in addition, contains a hole injecting material or an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material. The multi-layer type includes (anode / hole injection band / light emitting layer / cathode), (anode / light emitting layer / electron injection band / cathode), and (anode / hole injection band / light emitting layer / electron injection band / cathode). There are organic EL elements stacked in a configuration.

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

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

Hereinafter, the present invention will be described in more detail based on examples.
Example 1
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Furthermore, the compound (16) shown in Table 2, the compound (1) shown in Table 1, the following compound (41), and the compound (31) shown in Table 3 were mixed at a ratio of 52: 8: 37: 3 by weight%. Then, a solution dissolved in 1,2-dichloroethane at a concentration of 0.75 wt% was formed to a thickness of 80 nm on the previously prepared PEDOT layer by a spin coating method to obtain a light emitting layer. An electrode was formed on the coated substrate by a vacuum deposition method with a film thickness of Ca of 40 nm and Al of 120 nm to produce an organic EL element 1. The luminance-voltage curve of this element is shown in FIG.
Compound (41)

Example 2
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Furthermore, the compound (17) described in Table 2, the compound (1) described in Table 1, the compound (41), and the compound (31) described in Table 3 were mixed at a ratio of 52: 8: 37: 3 by weight%, A solution dissolved in 1,2-dichloroethane at a concentration of 0.75 wt% was formed to a thickness of 80 nm on the previously prepared PEDOT layer by a spin coating method to obtain a light emitting layer. An electrode was formed on the coated substrate by a vacuum deposition method with a film thickness of Ca of 40 nm and Al of 120 nm, thereby producing an organic EL element 2. The luminance-voltage curve of this element is shown in FIG.

Example 3
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Further, the compound (18) shown in Table 2, the compound (1) shown in Table 1, the following compound (42), and the compound (31) shown in Table 3 were mixed at a ratio of 52: 8: 37: 3 by weight%. Then, a solution dissolved in 1,2-dichloroethane at a concentration of 0.75 wt% was formed to a thickness of 80 nm on the previously prepared PEDOT layer by a spin coating method to obtain a light emitting layer. An electrode was formed on the coated substrate by a vacuum vapor deposition method with a film thickness of Ca of 40 nm and Al of 120 nm to produce an organic EL element 3. The luminance-voltage curve of this element is shown in FIG.
Compound (42)

Comparative Example 1
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Further, the compound (16), the compound (41) described in Table 2 and the compound (31) described in Table 3 were mixed at a ratio of 60: 37: 3 by weight%, and 1,2-at a concentration of 0.75 wt%. A solution dissolved in dichloroethane was formed to a thickness of 80 nm on the previously prepared PEDOT layer by a spin coating method to obtain a light emitting layer. An electrode was formed on the coated substrate by a vacuum deposition method with a film thickness of Ca of 40 nm and Al of 120 nm, thereby producing an organic EL element 4. The luminance-voltage curve of this element is shown in FIG.

Comparative Example 2
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Further, the compound (17), the compound (41) and the compound (31) described in Table 2 were mixed at a weight ratio of 60: 37: 3, and 1,2- A solution dissolved in dichloroethane was formed to a thickness of 80 nm on the previously prepared PEDOT layer by a spin coating method to obtain a light emitting layer. On this coated substrate, an electrode was formed with a film thickness of Ca of 40 nm and Al of 120 nm by a vacuum deposition method, and an organic EL element 5 was produced. The luminance-voltage curve of this element is shown in FIG.

Comparative Example 3
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Further, the compound (18), the compound (42) described in Table 2 and the compound (31) described in Table 3 were mixed at a ratio of 60: 37: 3 by weight%, and 1,2- A solution dissolved in dichloroethane was formed to a thickness of 80 nm on the previously prepared PEDOT layer by a spin coating method to obtain a light emitting layer. An electrode was formed on the coated substrate by a vacuum deposition method with a film thickness of Ca of 40 nm and Al of 120 nm, thereby producing an organic EL element 6. The luminance-voltage curve of this element is shown in FIG.

Comparative Example 4
On the washed glass plate with an ITO electrode, PEDOT was formed into a film thickness of 50 nm by a spin coat method, and vacuum-dried at 100 ° C. Further, a solution in which the following compound (43) was dissolved in 1,2-dichloroethane at a concentration of 0.5 wt% was formed into a film with a thickness of 80 nm on the previously prepared PEDOT layer by spin coating. A light emitting layer was obtained. An electrode was formed on this coated substrate with a film thickness of Ca of 40 nm and Al of 120 nm by a vacuum deposition method, and an organic EL element 7 was produced. The luminance-voltage curve of this element is shown in FIG.
Compound (43)

From the luminance-voltage curves of Example 1 and Comparative Example 1 shown in FIG. 1 in this Example, the luminance of 300 cd / m ² is obtained in Example 1 at 6 V which is a practical voltage. 1 is 30 cd / m ² and a luminance of about 1/10. Similarly, from the luminance-voltage curves of Example 2 and Comparative Example 2 in FIG. 2, the luminance of 300 cd / m ² is obtained in Example 2 at 8 V, which is a practical voltage range. Less than / m ² , this is also about 1/100 of the brightness. Further, from the luminance-voltage curves of Example 3 and Comparative Example 3 in FIG. 3, the luminance of 1000 cd / m ² is obtained in Example 3 at 10 V, which is a practical voltage range. The brightness is m ² and about 1/100. From these results, the organic EL device of the present invention achieved a low driving voltage. Further, since Comparative Example 4 in FIG. 4 uses a light emitting material having a polyphenylene vinylene skeleton, a luminance of 20000 cd / m ² is obtained from this luminance-voltage curve at 6 V which is a practical voltage range. However, since the current value is very high, the light emission efficiency is 1.5 cd / A, which is very low compared to the light emission efficiency 10-20 cd / A of Example 1-3.

  When all the organic EL devices shown in this example were continuously emitted, a luminance of 50% or more of the initial luminance could be observed for 1000 hours or more. However, the device of Comparative Example 1 was allowed to continuously emit light under the same conditions. As a result, the luminance was 50% or less of the initial luminance in 20 hours, and the number of dark spots was extremely large. Since the hole transport material of the present invention has a high molecular weight, the heat resistance as an organic EL device is extremely improved. All of the compounds of the present invention have glass transition temperatures and melting points of 100 ° C. or more, indicating that the luminescent material of the present invention is greatly improved.

  The organic EL device of the present invention achieves improvement in luminous efficiency, luminous luminance and longevity, and is used together with a luminescent substance, a luminescent auxiliary material, a hole transport material, an electron transport material, a sensitizer, The resin, the electrode material, etc. and the element manufacturing method are not limited.

Luminance-voltage curves of Example 1 and Comparative Example 1 Luminance-voltage curves of Example 2 and Comparative Example 2 Luminance-voltage curves of Example 3 and Comparative Example 3 Luminance-voltage curve of Comparative Example 4

Claims (7)

A material for an organic electroluminescent device comprising a non-conjugated polymer, an amine compound, and a phosphorescent compound. Furthermore, the material for organic electroluminescent elements of Claim 1 containing an electron transport compound. The organic electroluminescent element material according to claim 1 or 2, wherein the non-conjugated polymer contains at least one unit represented by the following general formula [1].
General formula [1]

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

[Wherein R ^{1 to} R ⁷ represent 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 -, - CH 2 - represents,
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. ] The organic electroluminescent element material according to claim 3, wherein the general formula [2] is a monovalent organic residue represented by the following general formula [3].
General formula [3]

[Wherein R ^{18 to} R ²⁶ represent a bonding site, a hydrogen atom or a substituent. ] The organic electroluminescent element material according to claim 2, wherein the electron transporting compound is an oxadiazole derivative. The material for an organic electroluminescent element according to claim 1, wherein the phosphorescent compound is an iridium complex. 7. The organic electroluminescent element material according to claim 1, wherein the light emitting layer is an organic electroluminescent element formed by forming a light emitting layer or a plurality of organic compound thin films including a light emitting layer between a pair of electrodes. Organic electroluminescent device containing

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