JP4942448B2 - Anthracene compound and organic electroluminescence device containing the compound - Google Patents

Description

The present invention relates to an anthracene compound and an organic electroluminescent device containing the compound, and more specifically, an anthracene compound that can be suitably used for an organic electroluminescent device and has thin film stability, and a low voltage using the compound. The present invention relates to an organic electroluminescence device having high emission luminance and luminous efficiency, and a luminescent material for organic electroluminescence device that realizes high stability and long life.

In recent years, various organic compounds have been actively researched and developed as materials having various functions such as display materials and recording materials.
For example, recently Eastman Kodak's C.I. W. Tang et al. Developed an organic electroluminescence device (organic electroluminescence device; organic EL device) using an organic compound as a constituent material [see, for example, Non-Patent Document 1]. The organic electroluminescent element has a structure in which a thin film containing a fluorescent organic compound (light emitting material) is sandwiched between an anode and a cathode. When an electric field is applied to the thin film, excitons are generated by recombination of holes injected from the anode and electrons injected from the cathode, and the excitons are deactivated. It is a self-luminous element that utilizes the principle that a fluorescent organic compound emits light by the energy emitted to the. The organic electroluminescent element is driven at a low direct current voltage of about several volts to several tens of volts, and can emit light of various colors (for example, red, blue, green) by selecting a light emitting material. . The organic electroluminescent element having such characteristics is expected to be applied to various light emitting elements and display elements because of its energy saving, good visibility due to self-emission, and reduction in thickness and weight. . However, organic electroluminescence devices generally have practical problems such as low emission luminance and poor stability.
These problems will be described in detail below.

As an element structure of the organic electroluminescent element, there are a two-layer type of a hole (injection) transport layer and an electron transport light-emitting layer, or a three-layer type of a hole (injection) transport layer, a light-emitting layer, and an electron (injection) transport layer. well known. In such a stacked structure element, the element structure and the formation method are devised in order to increase the recombination efficiency of injected holes and electrons. Tang et al. Use a triphenyldiamine derivative for the hole transport layer and a tris (8-quinolinolato) aluminum complex for the light emitting layer. The advantages of the stacked structure are that it increases the efficiency of hole injection into the light-emitting layer, blocks the electrons injected from the cathode, increases the generation efficiency of excitons generated by recombination, and generates in the light-emitting layer For example, confining excitons.
Known light-emitting materials include chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, pyran derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, and the like [Patent Documents 1 to 3]. See 3 etc.].
As a method for improving the light emission luminance, an organic electroluminescent device using, for example, a tris (8-quinolinolato) aluminum complex as a host compound and a coumarin derivative or a pyran derivative as a guest compound (dopant) has been proposed [for example, Non-patent document 2]. However, it cannot be said that these light-emitting elements also have sufficient stability and light emission luminance. In addition, when a tris (8-quinolinolato) aluminum complex is used as a host compound, it is possible to obtain red light having a longer wavelength than green, which is the emission color of the compound itself, but to obtain light having a shorter wavelength. Is difficult considering the energy state. In view of the above, in recent years, there has been a demand for improvements in light emission luminance and stability on the shorter wavelength side, particularly in blue light-emitting elements, and new materials are strongly desired.

As a blue light emitting material, for example, a device using a phenylanthracene derivative [see Patent Document 4] and an anthracene derivative having a naphthyl group at the 9th and 10th positions [see Patent Document 5] has been reported. Such an anthracene derivative is still insufficient in the stability of the device, and further life extension of the device is desired.
Since an organic electroluminescent element emits light by applying an electric field to an organic compound thin film, the organic compound is easily damaged by the load. In order to further improve the stability of the device and extend the life of the device, a material that is difficult to receive such a load is desired. That is, the material is required to have high stability of the thin film.
In general, when the compound is asymmetrical, the stability of the thin film is improved. Devices using asymmetric anthracene derivatives as blue light-emitting materials have been reported [see Patent Document 6], but they have a styryl structure that is susceptible to thermal modification.

In addition, there are reports that various anthracene derivatives have been used as hole transport materials, but their synthesis has not been actually performed, and evaluation as a light emitting material has not been made [see Patent Document 7].
Appl. Phys. Lett., 51, 913 (1987). J. Appl. Phys., 65, 3610 (1989). JP-A-8-239655 JP 7-138561 A JP-A-3-200289 JP-A-8-012600 JP 11-003782 A JP 2003-306454 A JP 2000-182776 A

  An object of the present invention is to provide a novel compound and a long-life organic electroluminescence device containing the compound. More specifically, a compound that can be suitably used for an organic electroluminescent element, has a thin film stability, and an organic electroluminescent element that achieves high stability and long life with improved emission luminance using the compound. It is to provide.

As a result of intensive studies on various compounds and organic electroluminescent devices containing the compounds, the present inventors use an asymmetric anthracene compound having a good thin film stability represented by the following general formula (1). Thus, the present inventors have found that an organic electroluminescence device with improved emission luminance and high stability and long life can be obtained, and the present invention has been completed. That is, the present invention
[1] Anthracene compound represented by the following general formula (1) [Chemical Formula 1],
An anthracene compound represented by the following general formula (1) [Chemical Formula 1]

［式中、Ａｒ^１、Ａｒ^２およびＡｒ^３は炭素数６〜４８からなる置換もしくは無置換のアリール基であり、Ｒ_１〜Ｒ_１１はそれぞれ独立に水素原子または置換基を表し、これらは同一でも異なるものであってもよい。Ｘは酸素原子または硫黄原子を表す。ｎは１〜３の整数である。］
［２］一般式（１）で表されるアントラセン化合物において、Ａｒ^１が一般式（２）〜（１０）［化２］で表される［１］記載の化合物、

[In the formula, Ar ¹ , Ar ² and Ar ³ are substituted or unsubstituted aryl groups having 6 to 48 carbon atoms, and R _{1 to} R ₁₁ each independently represent a hydrogen atom or a substituent, and these are the same. But it may be different. X represents an oxygen atom or a sulfur atom. n is an integer of 1 to 3. ]
[2] The anthracene compound represented by the general formula (1), the compound according to [1], wherein Ar ¹ is represented by the general formulas (2) to (10) [Chemical Formula 2],

［式中、Ｒ_２１〜Ｒ_２９、Ｒ_３１〜Ｒ_３９、Ｒ_４１〜Ｒ_４９、Ｒ_５１〜Ｒ_５７、Ｒ_６１〜Ｒ_６９、Ｒ_７１〜Ｒ_７９、Ｒ_８１〜Ｒ_８７、Ｒ_９１〜Ｒ_９７およびＲ_１０１〜Ｒ_１０９はそれぞれ独立に水素原子または置換基を表し、Ｘ_５は酸素原子または硫黄原子を表す。］
［３］一対の電極間に、一般式（１）で表されるアントラセン化合物を少なくとも１種含有する層を少なくとも１層狭持してなる有機電界発光素子、
［４］一般式（１）で表されるアントラセン化合物を含有する層が、発光層である［３］記載の有機電界発光素子、
［５］一般式（１）で表されるアントラセン化合物を含有する層が、正孔注入輸送層である［３］記載の有機電界発光素子、
［６］発光層がホスト材料とドーパント材料より形成され、一般式（１）で表されるアントラセン化合物が発光層ホスト材料として含有されている［４］記載の有機電界発光素子、
［７］一対の電極間に、さらに正孔注入輸送層を有する［３］、［４］、［５］または［６］記載の有機電界発光素子、
［８］一対の電極間に、さらに電子注入輸送層を有する［３］〜［７］のいずれかに記載の有機電界発光素子、
に関するものである。

_{Wherein, R 21 ~R 29, R 31} ~R 39, R 41 ~R 49, R 51 ~R 57, R 61 ~R 69, R 71 ~R 79, R 81 ~R 87, R 91 ~R ₉₇ and R _{101 to} R ₁₀₉ each independently represent a hydrogen atom or a substituent, and X ₅ represents an oxygen atom or a sulfur atom. ]
[3] An organic electroluminescent device comprising at least one layer containing at least one anthracene compound represented by the general formula (1) between a pair of electrodes,
[4] The organic electroluminescent element according to [3], wherein the layer containing the anthracene compound represented by the general formula (1) is a light emitting layer.
[5] The organic electroluminescent device according to [3], wherein the layer containing the anthracene compound represented by the general formula (1) is a hole injection transport layer,
[6] The organic electroluminescent element according to [4], wherein the light emitting layer is formed of a host material and a dopant material, and the anthracene compound represented by the general formula (1) is contained as the light emitting layer host material.
[7] The organic electroluminescent device according to [3], [4], [5] or [6], further having a hole injection / transport layer between the pair of electrodes.
[8] The organic electroluminescence device according to any one of [3] to [7], further having an electron injection / transport layer between the pair of electrodes.
It is about.

Hereinafter, the present invention will be described in detail.
The anthracene compound of the present invention is a compound represented by the general formula (1) [Chemical Formula 3].

［式中、Ａｒ^１、Ａｒ^２およびＡｒ^３は炭素数６〜４８からなる置換もしくは無置換のアリール基であり、Ｒ_１〜Ｒ_１１はそれぞれ独立に水素原子または置換基を表し、これらは同一でも異なるものであってもよい。Ｘは酸素原子または硫黄原子を表す。ｎは１〜３の整数である。］

[In the formula, Ar ¹ , Ar ² and Ar ³ are substituted or unsubstituted aryl groups having 6 to 48 carbon atoms, and R _{1 to} R ₁₁ each independently represent a hydrogen atom or a substituent, and these are the same. But it may be different. X represents an oxygen atom or a sulfur atom. n is an integer of 1 to 3. ]

In the present application, the aryl group represents a carbocyclic aromatic group or a heterocyclic aromatic group.
In the anthracene compound represented by the general formula (1), Ar ¹ , Ar ² and Ar ³ are substituted or unsubstituted aryl groups having 6 to 48 carbon atoms,
Here, the number of carbons means “the number of carbons of the aryl part forming Ar ¹ , Ar ² or Ar ³ ”, and when the aryl part is substituted with a substituent other than an aryl group, The carbon contained in is not included in the “carbon number” described above.
As used herein, substituted or unsubstituted means “straight-chain, branched or cyclic alkyl group, straight-chain, branched or cyclic alkoxy group, straight-chain, branched or cyclic alkyl group, or di-substituted. Substituted with a substituent such as an amino group substituted with an amino group, an aryl group, an amino group monocyclic or disubstituted with an aryl group, or an amino group substituted with a linear, branched or cyclic alkyl group and an aryl group, Or “unsubstituted”, preferably “a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 30 carbon atoms, carbon atom” A mono- or di-substituted amino group having a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, an aryl group having 3 to 20 carbon atoms, or an aryl group having 3 to 20 carbon atoms Amino group Or substituted with a substituent such as an amino group substituted with a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms and an aryl group having 4 to 20 carbon atoms, or unsubstituted " means.

Ar ¹ , Ar ² and Ar ³ represent a substituted or unsubstituted carbocyclic aromatic group having 6 to 48 carbon atoms, or a substituted or unsubstituted heterocyclic aromatic group.
Specific examples of the carbocyclic aromatic group include a phenyl group substituted or unsubstituted with an aryl group having 4 to 42 carbon atoms, or an unsubstituted naphthyl substituted with an aryl group having 4 to 38 carbon atoms. Group, azulenyl group, heptalenyl group, biphenyl group, biphenylenyl group, as-indacenyl group, s-indacenyl group, acenaphthylenyl group, fluorenyl group, phenalenyl group, phenanthrenyl group, pyrenyl group, fluoranthenyl group, acephenanthrenyl group , Aceanthrylenyl group, triphenylenyl group, pyrenyl group, chrycenyl group, naphthacenyl group, preadenyl group, picenyl group, perylenyl group, pentaphenyl group, pentacenyl group, rubicenyl group, coronenyl group, pyransrenyl group, obalenyl group, etc. I can do it.
Specific examples of the heterocyclic aromatic group include a furanyl group substituted with an aryl group having 4 to 44 carbon atoms, a thiophenyl group substituted with an aryl group having 4 to 44 carbon atoms, and a carbon atom having 4 to 44 carbon atoms. A pyrrole group substituted with an aryl group, a benzofuranyl group substituted with an aryl group having 4 to 42 carbon atoms, an isobenzofuranyl group substituted with an aryl group having 5 to 40 carbon atoms, an aryl group having 5 to 40 carbon atoms A dibenzofuranyl group substituted with an aryl group having 5 to 40 carbon atoms, a dibenzothiophenyl group substituted with an aryl group having 5 to 40 carbon atoms, an aryl having 5 to 40 carbon atoms Indolyl group substituted with a group, isoindolyl group substituted with an aryl group having 5 to 40 carbon atoms, indolizinyl group substituted with an aryl group having 5 to 40 carbon atoms, carbazolyl A pyridyl group substituted with an aryl group having 6 to 43 carbon atoms, a quinolyl group substituted with an aryl group having 5 to 39 carbon atoms, an isoquinolyl group substituted with an aryl group having 5 to 39 carbon atoms, Group, acridinyl group, oxazolyl group substituted with aryl group having 8 to 45 carbon atoms, isoxazolyl group substituted with aryl group having 8 to 45 carbon atoms, thiazolyl group substituted with aryl group having 8 to 45 carbon atoms An isothiazolyl group substituted with an aryl group having 8 to 45 carbon atoms, a furazanyl group substituted with an aryl group having 9 to 46 carbon atoms, an imidazolyl group substituted with an aryl group having 8 to 45 carbon atoms, A pyrazolyl group substituted with a 45 aryl group, a benzimidazolyl group substituted with an aryl group having 5 to 41 carbon atoms, and an aryl group having 5 to 40 carbon atoms. 1,8-naphthyridinyl group, pyrazinyl group substituted with an aryl group having 7 to 44 carbon atoms, pyrimidinyl group substituted with an aryl group having 7 to 44 carbon atoms, substituted with an aryl group having 7 to 44 carbon atoms Pyridazinyl group, quinoxalinyl group substituted with an aryl group having 5 to 40 carbon atoms, quinazolinyl group substituted with an aryl group having 5 to 40 carbon atoms, cinolinyl group substituted with an aryl group having 5 to 40 carbon atoms, carbon A phthalazinyl group substituted with an aryl group of 5 to 40, a purinyl group substituted with an aryl group of 6 to 43 carbon atoms, a pteridinyl group substituted with an aryl group of 5 to 42 carbon atoms, a perimidinyl group, 1,10 -Phenanthrolinyl group, thiantenyl group, phenoxathinyl group, phenoxazinyl group, phenothiazinyl group, phenazinyl group, etc. I can do it.

Specific examples of Ar ¹ include groups selected from the following general formulas (2) to (10) [Chemical Formula 4].

Ｒ_２１〜Ｒ_２９、Ｒ_３１〜Ｒ_３９、Ｒ_４１〜Ｒ_４９、Ｒ_５１〜Ｒ_５７、Ｒ_６１〜Ｒ_６９、Ｒ_７１〜Ｒ_７９、Ｒ_８１〜Ｒ_８７、Ｒ_９１〜Ｒ_９７およびＲ_１０１〜Ｒ_１０９はそれぞれ独立に水素原子または置換基を表し、好ましくは、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換または無置換のアミノ基、置換または無置換のエステル基、炭素数１〜１０の直鎖、分岐または環状のアルキル基、炭素数１〜１０の直鎖、分岐または環状のアルコキシ基、炭素数７〜２０の置換または無置換のアラルキル基、炭素数７〜２０の置換または無置換のアラルキルオキシ基、炭素数４〜２０の置換または無置換のアリール基あるいは炭素数４〜２０の置換または無置換のアリールオキシ基であり、より好ましくは、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換または無置換のアミノ基、炭素数１〜８の直鎖、分岐または環状のアルキル基、炭素数１〜８の直鎖、分岐または環状のアルコキシ基、炭素数７〜１６の置換または無置換のアラルキル基、炭素数７〜１６の置換または無置換のアラルキルオキシ基、炭素数４〜１６の置換または無置換のアリール基あるいは炭素数４〜１６の置換または無置換のアリールオキシ基を表す。
また、Ｒ_２１〜Ｒ_２９、Ｒ_３１〜Ｒ_３９、Ｒ_４１〜Ｒ_４９、Ｒ_５１〜Ｒ_５７、Ｒ_６１〜Ｒ_６９、Ｒ_７１〜Ｒ_７９、Ｒ_８１〜Ｒ_８７、Ｒ_９１〜Ｒ_９７およびＲ_１０１〜Ｒ_１０９の隣合う基は、それぞれ隣接する基と共に環を形成していてもよい。

_{R 21 ~R 29, R 31 ~R} 39, R 41 ~R 49, R 51 ~R 57, R 61 ~R 69, R 71 ~R 79, R 81 ~R 87, R 91 ~R 97 and _{R 101} ~ _R109 each independently represents a hydrogen atom or a substituent, preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted ester group, 10 linear, branched or cyclic alkyl groups, 1 to 10 linear, branched or cyclic alkoxy groups, 7 to 20 substituted or unsubstituted aralkyl groups, 7 to 20 carbon atoms substituted or An unsubstituted aralkyloxy group, a substituted or unsubstituted aryl group having 4 to 20 carbon atoms, or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, more preferably a hydrogen atom Child, halogen atom, cyano group, nitro group, substituted or unsubstituted amino group, linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms A substituted or unsubstituted aralkyl group having 7 to 16 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 16 carbon atoms, a substituted or unsubstituted aryl group having 4 to 16 carbon atoms, or a 4 to 16 carbon number A substituted or unsubstituted aryloxy group is represented.
_{Also, R 21 ~R 29, R 31} ~R 39, R 41 ~R 49, R 51 ~R 57, R 61 ~R 69, R 71 ~R 79, R 81 ~R 87, R 91 ~R 97 and The adjacent groups of R _{101 to} R ₁₀₉ may form a ring together with the adjacent groups.

  Specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and the like.

  Specific examples of the above-mentioned substituted or unsubstituted amino group include amino group, N-methylamino group, N-ethylamino group, Nn-propylamino group, N-iso-propylamino group, Nn- Butylamino group, N-iso-butylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentylamino group, Nn-hexylamino group, N-cyclohexylamino group, N-benzylamino group, N-phenethylamino group, N-phenylamino group, N- (1-naphthyl) amino group, N- (2-naphthyl) amino group, N- (4-phenyl) Phenyl) amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group, N- (4-methylphenyl) amino group, N- (2-methylphenyl) amino Group, N- (2-anthranyl) amino group, N- (9-anthranyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group, N , N-di-iso-propylamino group, N, N-di-n-butylamino group, N, N-di-iso-butylamino group, N, N-di-sec-butylamino group, N, N -Di-tert-butylamino group, N, N-di-n-pentylamino group, N, N-dicyclopentylamino group, N, N-dicyclohexylamino group, N, N-dibenzylamino group, N, N -Diphenethylamino group, N-methyl-N-ethylamino group, N-methyl-Nn-propylamino group, N-methyl-N-iso-propylamino group, N-methyl-Nn-butylamino Group, N-methyl-N-tert-butylamino group, N- Tyl-N-cyclopentylamino group, N-methyl-N-cyclohexylamino group, N-methyl-N-benzylamino group, N-methyl-N-phenethylamino group, N-ethyl-N-benzylamino group, N- Ethyl-N-phenethylamino group, N-ethyl-N-tert-butylamino group, N-ethyl-N-cyclopentylamino group, N-ethyl-N-cyclohexylamino group, N-iso-propyl-N-cyclopentylamino Group, N-iso-propyl-N-cyclohexylamino group, N-iso-propyl-N-benzylamino group, N-tert-butyl-N-cyclopentylamino group, N-tert-butyl-N-cyclohexylamino group, N-tert-butyl-N-benzylamino group, N-cyclopentyl-N-benzylamino group, N-cyclohexyl-N-benzyl Mino group, N-methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-cyclohexyl-N-phenylamino group, N, N-diphenylamino group, N, N-di (1-naphthyl) ) Amino group, N, N-di (2-naphthyl) amino group, N- (1-naphthyl) -N- (2-naphthyl) amino group, N, N- (4-phenylphenyl) amino group, N- (1-naphthyl) -N-phenylamino group, N- (2-naphthyl) -N-phenylamino group, N- (4-phenylphenyl) -N-phenylamino group, N- (4-tert-butylphenyl) ) -N-phenylamino group, N- (3-tert-butylphenyl) -N-phenylamino group, N- (4-methylphenyl) -N-phenylamino group, N- (1-naphthyl) -N- (4'-phenylphenyl) a Amino group, N-(2-naphthyl) such as-N-(4'-phenylphenyl) amino group and the like.

  Specific examples of the above-mentioned substituted or unsubstituted ester group include, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, iso-propoxycarbonyl group, n-butoxycarbonyl group, iso-butoxycarbonyl group, sec -Butoxycarbonyl group, n-pentyloxycarbonyl group, iso-pentyloxycarbonyl group, neopentyloxycarbonyl group, cyclopentyloxycarbonyl group, n-hexyloxycarbonyl group, 2-ethylbutoxycarbonyl group, 3,3-dimethylbutoxy Carbonyl group, cyclohexyloxycarbonyl group, n-heptyloxycarbonyl group, cyclohexylmethyloxycarbonyl group, n-octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, n-nonyloxycal Nyl group, n-decyloxycarbonyl group, n-dodecyloxycarbonyl group, n-tetradecyloxycarbonyl group, n-hexadecyloxycarbonyl group, benzyloxycarbonyl group, phenyloxycarbonyl group, 1-naphthyloxycarbonyl group, 2-naphthyloxycarbonyl group, acetyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, iso-propylcarbonyloxy group, n-butylcarbonyloxy group, iso-butylcarbonyloxy group, sec-butylcarbonyloxy group N-pentylcarbonyloxy group, iso-pentylcarbonyloxy group, neopentylcarbonyloxy group, cyclopentylcarbonyloxy group, n-hexylcarbonyloxy group, 2-ethylbutylcarbonyloxy group, 3, 3 Dimethylbutylcarbonyloxy group, cyclohexylcarbonyloxy group, n-heptylcarbonyloxy group, cyclohexylmethylcarbonyloxy group, n-octylcarbonyloxy group, 2-ethylhexylcarbonyloxy group, n-nonylcarbonyloxy group, n-decylcarbonyloxy Group, n-dodecylcarbonyloxy group, ncarbonyl-tetradecyloxy group, n-hexadecylcarbonyloxy group, benzylcarbonyloxy group, phenylcarbonyloxy group, 1-naphthylcarbonyloxy group, 2-naphthylcarbonyloxy group, etc. Can be mentioned.

  Specific examples of the linear, branched or cyclic alkyl group having 1 to 10 carbon atoms include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and an iso-butyl group. , Sec-butyl group, tert-butyl group, n-pentyl group, iso-pentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2 -Ethylbutyl group, 2-ethylhexyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1-methylheptyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group, n-dodecyl group, 1-methyldecyl group, n-tridecyl 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-hexyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonylki, n-octadecyl group, n-nonyldecyl group, 1 -Decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, (2-isopropylcyclohexyl) ethyl group, cyclopentyl group, 2-ethylbutyl Group, 3,3-dimethylbutyl group, 1,1-dimethylhexyl group, bornel group, isobornel group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1- Adamantyl group, 3-noradamantyl group, 1-adamantyl group Til group, cyclobutyl group, 1-methylcyclopentyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6- Dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4- tert-butylcyclohexyl group, 3-tert-butylcyclohexyl group, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclododecyl group, cyclotetradecyl group,

Methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-iso-propoxyethyl group, 2-n-butoxyethyl group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2 -(2'-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group 2-n-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropiyl Group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-iso-propoxypropyl group, 3- (n-butoxy) propyl group, 3- (n-pentyloxy) propyl group 3- (n-hexyloxy) propyl group, 3- (2′-ethylbutoxy) propyl group, 3- (n-octyloxy) propyl group, 3- (2′-ethylhexyloxy) propyl group, 3- (n -Decyloxy) propyl group, 3- (n-dodecyloxy) propyl group, 3- (n-tetradecyloxy) propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4- n-propoxybutyl group, 4-iso-propoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4-n-o Tyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-ethoxypentyl group, 6-ethoxyhexyl group, 6 -Isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group 8-methoxyoctyl group, 10-methoxydecyl group, 10-n-butoxydecyl group, 12-ethoxydodecyl group, 12-isopropoxide decyl group, tetrahydrofurfuryl group,

2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butoxyethoxy) ethyl group, 3- (2′-ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4′-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2′-hexenyloxy) propyl group, 3- (2′-heptenyloxy) propyl group, 3 -(1'-cyclohexenyloxy) propyl group, 4-allyloxybutyl group,
Benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4′-methylbenzyloxy) ethyl group, 2- (2′-methylbenzyloxy) ethyl group, 2- (4 ′) -Fluorobenzyloxy) ethyl group, 2- (4'-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4'-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (Benzyloxymethoxy) ethyl group, 2- (4′-methylbenzyloxymethoxy) ethyl group,
Phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4-chlorophenyloxymethyl group Group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl group, 2- (4′-methoxyphenyl) Oxy) ethyl group, 2- (4′-chlorophenyloxy) ethyl group, 2- (4′-bromophenyloxy) ethyl group, 2- (1′-naphthyloxy) ethyl group, 2- (2′-naphthyloxy) ) Ethyl group, 3-phenyloxypropyl group, 3- (2′-naphthyloxy) propyl group, 4-phenyloxy Sibutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl group, 10-phenyloxydecyl group, 10- (3′-chlorophenyloxy) decyl group, 2- (2′-phenyloxyethoxy) ethyl group, 3- (2′-phenyloxyethoxy) propyl group, 4- (2 ′ -Phenyloxyethoxy) butyl group,

n-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2-n-octyl Thioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2 ′ -Methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl group, 2-allylthioethyl group, 2- N-dithioethyl group, 3- (4′-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2′-benzyloxyethylthio) ethyl group, 3- (3′-benzylthiopropylthio) propyl group ,
2-phenylthioethyl group, 2- (4′-methoxyphenylthio) ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) propyl group,
2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8-hydroxyoctyl group, 10- Examples thereof include a hydroxydecyl group, a 12-hydroxydodecyl group, and a 2-hydroxycyclohexyl group.

  Specific examples of the linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms include a linear, branched or cyclic alkoxy group derived from the linear, branched or cyclic alkyl group. Can do.

Specific examples of the substituted or unsubstituted aralkyl group include benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethyl. Benzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropyl Benzyl group, 4-tert-butylbenzyl group, 2-tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4 -Allylbenzyl group, 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, 4- (4'-methyl) Phenyl) benzyl, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxy benzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxy benzyl group,
4-n-decyloxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group,
3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl Group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group,
4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4-hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl Group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group and the like.

  Specific examples of the above substituted or unsubstituted aralkyloxy group include a substituted or unsubstituted aralkyloxy group derived from the above substituted or unsubstituted aralkyl group.

Specific examples of the above-mentioned substituted or unsubstituted aryl group include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-phenanthryl group, 2 -Phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-biphenyleneyl group, 2-biphenyleneyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group 5-acenaphthylenyl group, 3-fluoranthenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 3-perylenyl group,
4-quinolyl group, 5-pyridyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-pyrimidyl group, 4-pyrimidine group, 5-pyrimidyl group, 2-pyridazinyl group, 2-pyrazinyl group, 3-furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzothiophenyl group, 2-benzofuryl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, 3-carbazolyl group, 9-carbazolyl group o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, p-terphenyl-4-yl group, p -Terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,

4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl Group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4 -N-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-nonylphenyl group, 4- -Decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-n-hexadecylphenyl group, 4-n-octadecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group 4- (4′-tert-butylcyclohexyl) phenyl group, 4- (4′-methylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group,
4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group,
2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2, 3,5-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6- Diethylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5-di- tert-butylphenyl group, 2,4-dineopentylphenyl group, 2,5-di-tert-pentylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl- 2 Methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethyl-phenyl group,
5-indanyl group, 1,2,3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group,

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl Group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2 -Isopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2'-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyl Oxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxypheny Group, 4-n-hexadecyloxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group,
2-methoxy-1-naphthyl group, 4-methoxy-1-naphthyl group, 4-n-butoxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n -Butoxy-2-naphthyl group, 6-n-hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy-2-naphthyl group,
2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3, 5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3 -Methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3 , 4,5-trimethoxyphenyl group,

4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-chloro-1 -Naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6- Difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3, 4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichloroph Group, 2,3,6-bromophenyl group, 3,4,5-trifluorophenyl group, 2,4-dichloro-1-naphthyl group, 1,6-dichloro-2-naphthyl group,
2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 3-fluoro-2-methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4-chloro-3-methylphenyl group, 2-chloro-4,6-dimethylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl Group, 3-fluoro-4-ethoxyphenyl group, 5-chloro-2-methoxyphenyl group, 6-chloro-3-methoxyphenyl group, 5-chloro-2,4- Methoxyphenyl group, 2-chloro-4-nitrophenyl group, 4-chloro-2-nitrophenyl group,
4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3,5-bis (trifluoromethyl) phenyl group,
4-trifluoromethyloxyphenyl group,
4-allylphenyl group, 2-allylphenyl group, 2-isopropenylphenyl group, 4-benzylphenyl group, 2-benzylphenyl group, 4- (4′-methylbenzyl) phenyl group, 4-cumylphenyl group, 4- (4′-methoxycumyl) phenyl group,
4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-ethylphenyl) phenyl group, 4- (4′-isopropylphenyl) ) Phenyl group, 4- (4′-tert-butylphenyl) phenyl group, 4- (4′-n-hexylphenyl) phenyl group, 4- (4′-n-octylphenyl) phenyl group,

4- (4′-methoxyphenyl) phenyl group, 4- (4′-ethoxyphenyl) phenyl group, 4- (4′-n-butoxyphenyl) phenyl group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-fluorophenyl) phenyl group, 4- (4′-chlorophenyl) phenyl group, 3-methyl-4-phenyl group, 2-methoxy-5-phenylphenyl group, 3-methoxy-4-phenylphenyl Group,
4-methoxymethylphenyl group, 4-ethoxymethylphenyl group, 4-n-butoxymethylphenyl group, 3-methoxymethylphenyl group, 4- (2′-methoxyethyl) phenyl group, 4- (2′-ethoxyethyl) Oxy) phenyl group, 4- (2′-n-butoxyethyloxy) phenyl group, 4- (3′-ethoxypropyloxy) phenyl group, 4-vinyloxyphenyl group, 4-allyloxyphenyl group, 3-allyl Oxyphenyl group, 4- (4′-pentenyloxy) phenyl group, 4-allyloxy-1-naphthyl group,
4-allyloxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group,
4-benzyloxyphenyl group, 2-benzyloxyphenyl group, 4-phenethyloxyphenyl group, 4- (4′-chlorobenzyloxy) phenyl group, 4- (4′-methylbenzyloxy) phenyl group, 4- ( 4′-methoxybenzyloxy) phenyl group, 4- (3′-ethoxybenzyloxy) phenyl group, 4-benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, 6 -Benzyloxy-2-naphthyl group, 6- (4'-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4- (2 ' -Benzyloxyethyloxy) phenyl group,
4-phenyloxyphenyl group, 3-phenyloxyphenyl group, 2-phenyloxyphenyl group, 4- (4′-methylphenyloxy) phenyl group, 4- (4′-methoxyphenyloxy) phenyl group, 4- ( 4′-chlorophenyloxy) phenyl group, 4-phenyloxy-1-naphthyl group, 6-phenyloxy-2-naphthyl group, 7-phenyloxy-2-naphthyl group, 4-phenyloxymethylphenyl group, 4- ( 2′-phenyloxyethyloxy) phenyl group, 4- [2 ′-(4′-methylphenyloxy) ethyloxy] phenyl group, 4- [2 ′-(4′-methoxyphenyloxy) ethyloxy] phenyl group, 4 -[2 '-(4'-chlorophenyloxy) ethyloxy] phenyl group,

4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4-ethylcarbonylphenyl group, 2-ethylcarbonylphenyl group, 4-n-butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1-naphthyl group, 6-acetyl-2-naphthyl group, 6-n-butylcarbonyl-2-naphthyl group, 4-allylcarbonyl Phenyl group, 4-benzylcarbonylphenyl group, 4- (4′-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4- (4′-methylphenyl) carbonylphenyl group, 4- (4′-chlorophenyl) ) Carbonylphenyl group, 4-phenylcarbonyl-1-na Methyl group,
4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propoxycarbonylphenyl group, 4-n-butoxycarbonylphenyl group, 4-n- Hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6-methoxycarbonyl-2-naphthyl group, 6-n-butoxycarbonyl 2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4′-chlorobenzyl) oxycarbonylphenyl group, 4-phenethyloxycarbonylphenyl group, 6-benzyloxycal Bonyl-2-naphthyl group, 4-phenyloxycarbonylphenyl group, 4- (4′-ethylphenyl) oxycarbonylphenyl group, 4- (4′-chlorophenyl) oxycarbonylphenyl group, 4- (4′-ethoxyphenyl) ) Oxycarbonylphenyl group, 6-phenyloxycarbonyl-2-naphthyl group,

4-acetyloxyphenyl group, 3-acetyloxyphenyl group, 2-acetyloxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2-ethylcarbonyloxyphenyl group, 4-n-propylcarbonyloxyphenyl group, 4-n -Pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 4-n-butylcarbonyloxy -1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyloxy Phenyl group 4- phenethyl carbonyloxy phenyl group, 6-benzyloxy carbonyloxy-2-naphthyl group,
4-phenylcarbonyloxyphenyl group, 4- (4′-methylphenyl) carbonyloxyphenyl group, 4- (2′-methylphenyl) carbonyloxyphenyl group, 4- (4′-chlorophenyl) carbonyloxyphenyl group, 4 -(2'-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 7-phenylcarbonyloxy-2-naphthyl group,
4-methylthiophenyl group, 2-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2-isopropylthiophenyl group, 4-n-butylthiophenyl group 2-isobutylthiophenyl group, 2-neopentylphenyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group,
4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group, 4- (4′-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2- Phenylthiophenyl group, 4- (4'-methylphenylthio) phenyl group, 4- (3'-methylphenylthio) phenyl group, 4- (4'-methoxyphenylthio) phenyl group, 4- (4'- Chlorophenylthio) phenyl group, 2-ethylthio-1-naphthyl group, 4-methylthio-1-naphthyl group, 6-ethylthio-2-naphthyl group, 6-phenylthio-2-naphthyl group,
4-nitrophenyl group, 3-nitrophenyl group, 2-nitrophenyl group, 3,5-dinitrophenyl group, 4-nitro-1-naphthyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formyl Phenyl group, 4-formyl-1-naphthyl group, 1-formyl-2-naphthyl group,

4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N-ethylpiperazino) phenyl group, 4-pyrrolidino-1-naphthyl group,
4-aminophenyl group, 3-aminophenyl group, 2-aminophenyl group,
4- (N-methylamino) phenyl group, 3- (N-methylamino) phenyl group, 4- (N-ethylamino) phenyl group, 2- (N-isopropylamino) phenyl group, 4- (Nn) -Butylamino) phenyl group, 2- (Nn-butylamino) phenyl group, 4- (Nn-octylamino) phenyl group, 4- (Nn-dodecylamino) phenyl group, 4- (N -Benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group,
4- (N, N-dimethylamino) phenyl group, 3- (N, N-dimethylamino) phenyl group, 4- (N, N-diethylamino) phenyl group, 2- (N, N-dimethylamino) phenyl group 2- (N, N-diethylamino) phenyl group, 4- (N, N-di-n-butylamino) phenyl group, 4- (N, N-di-n-hexylamino) phenyl group, 4- (N N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group, 4- (N, N-diphenyl) Amino) phenyl group, 4- [N-phenyl-N- (4-methylphenyl) amino] phenyl group, 4- [N, N-di (3′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methylphenol ) Amino] phenyl group, 4- [N, N-di (4'-methoxyphenyl) amino] phenyl group, 2-(N, N-diphenylamino) phenyl group,
4-hydroxyphenyl group, 3-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methyl-3-hydroxyphenyl group, 6-methyl-3-hydroxyphenyl group, 2-hydroxy-1-naphthyl group, 8-hydroxy -1-naphthyl group, 4-hydroxy-1-naphthyl group, 1-hydroxy-2-naphthyl group, 6-hydroxy-2-naphthyl group, 4-cyanophenyl group, 2-cyanophenyl group, 4-cyano-1 -A naphthyl group, 6-cyano- 2-naphthyl group, etc. can be mentioned.

  Specific examples of the above-mentioned substituted or unsubstituted aryloxy group include a substituted or unsubstituted aryloxy group derived from the above aryl group.

In the general formula (5), X ₅ represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
In the anthracene compound represented by the general formula (1), Ar ¹ is preferably a group represented by the general formulas (2) to (10), and more preferably the general formulas (2), (3), (5) and groups represented by (8).

In the anthracene compound represented by the general formula (1), Ar ² and Ar ³ are preferably a substituted or unsubstituted carbocyclic aromatic group having 6 to 42 carbon atoms, or a substituted or unsubstituted heterocyclic ring. Represents an aromatic group. More preferably, it represents a substituted or unsubstituted carbocyclic aromatic group having 6 to 36 carbon atoms, or a substituted or unsubstituted heterocyclic aromatic group.

In the anthracene compound represented by the general formula (1), R _{1 to} R ₁₁ each independently represent a hydrogen atom or a substituent, and these may be the same or different.
Here, the substituent is preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted ester group, a linear, branched or cyclic group having 1 to 10 carbon atoms. Alkyl group, linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, carbon A substituted or unsubstituted aryl group having 4 to 20 carbon atoms, or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, more preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, substituted or unsubstituted An amino group, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted group having 7 to 16 carbon atoms Aralkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl group or a C4-16 having 4 to 16 carbon atoms 7-16 carbon atoms.
Moreover, the adjacent groups of R _{1 to} R ₁₁ may form a ring together with the adjacent groups.
In the anthracene compound represented by the general formula (1), X represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
In the anthracene compound represented by the general formula (1), n represents an integer of 1 to 3, and preferably represents 1-2.
Specific examples of the anthracene compound represented by the general formula (1) of the present invention are illustrated below, but the present invention is not limited to these specific examples.

The anthracene compound represented by the general formula (1) of the present invention can be produced by, for example, the following steps.
Production of anthracene compound represented by general formula (1)

〔式中、Ａｒ^１、Ａｒ^２、Ａｒ^３、Ｒ_１〜Ｒ_１１、Ｘおよびｎは一般式（１）と同様の意味を示し、Ｒ_１２は水素原子またはハロゲン原子を表す。Ｌ_３およびＬ_４はハロゲン原子またはトリフルオロメタンスルホニルオキシ基等の脱離基を表す。Ｌ_１およびＬ_２はハロゲン原子またはトリフルオロメタンスルホニルオキシ基等の脱離基、あるいはボロン酸基またはボロン酸エステル基を表し、Ｌ_１およびＬ_２のどちらか一方がハロゲン原子またはトリフルオロメタンスルホニルオキシ等の脱離基であり、他方はボロン酸基またはボロン酸エステル基である〕
すなわち、一般式（Ａ）で表される化合物に一般式（Ｂ）で表される化合物をパラジウム触媒〔例えば、トリフェニルホスフィン／酢酸パラジウム、トリtert-ブチルホスフィン／酢酸パラジウム〕および塩基（例えば、炭酸ナトリウム、炭酸カリウム、リン酸カリウム、炭酸セシウム等の無機塩基、トリエチルアミン、ピリジン等の有機塩基）の存在下に縮合、環化させることで一般式（Ｃ）で表されるベンゾフラン化合物を得る。次いで、例えば、アルキルリチウム等の有機金属試薬を用いてボロン酸エステルやハライド等と反応させることで脱離基を組み込んだ一般式（Ｄ）を製造する。さらに、一般式（Ｄ）で表される化合物に一般式（Ｅ）で表される化合物をパラジウム触媒〔例えば、テトラキス（トリフェニルホスフィン）パラジウム、トリtert-ブチルホスフィン／酢酸パラジウム〕および塩基（例えば、炭酸ナトリウム、炭酸カリウム、リン酸カリウム等の無機塩基、トリエチルアミン、ピリジン等の有機塩基）の存在下に反応させることで一般式（１）で表されるアントラセン化合物を製造することができる。

[Wherein Ar ¹ , Ar ² , Ar ³ , R _{1 to} R ₁₁ , X and n represent the same meaning as in general formula (1), and R ₁₂ represents a hydrogen atom or a halogen atom. L ₃ and L ₄ represent a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group. L ₁ and L ₂ represent a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group, or a boronic acid group or a boronic ester group, and either one of L ₁ and L ₂ is a halogen atom, trifluoromethanesulfonyloxy, or the like And the other is a boronic acid group or a boronic ester group]
That is, the compound represented by the general formula (B) is converted into a compound represented by the general formula (A) by using a palladium catalyst [for example, triphenylphosphine / palladium acetate, tritert-butylphosphine / palladium acetate] and a base (for example, A benzofuran compound represented by the general formula (C) is obtained by condensation and cyclization in the presence of an inorganic base such as sodium carbonate, potassium carbonate, potassium phosphate and cesium carbonate, or an organic base such as triethylamine and pyridine. Next, for example, a general formula (D) in which a leaving group is incorporated is produced by reacting with a boronic acid ester or a halide using an organometallic reagent such as alkyl lithium. Further, the compound represented by the general formula (E) is converted into a compound represented by the general formula (D) by using a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, tritert-butylphosphine / palladium acetate] and a base (for example, And an anthracene compound represented by the general formula (1) can be produced by the reaction in the presence of an inorganic base such as sodium carbonate, potassium carbonate or potassium phosphate, or an organic base such as triethylamine or pyridine.

  Next, the organic electroluminescent element of the present invention will be described. The organic electroluminescent element of the present invention comprises at least one layer containing at least one anthracene compound represented by the general formula (1) between a pair of electrodes. An organic electroluminescent element is usually formed by sandwiching at least one light emitting layer containing at least one light emitting component between a pair of electrodes. A hole injection / transport layer and / or an electron injection containing a hole injection component as desired, considering the functional level of the hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer. An electron injecting and transporting layer containing a transporting component can also be provided.

  For example, when the hole injection function, the hole transport function and / or the electron injection function, and the electron transport function of the compound used in the light emitting layer are good, the light emitting layer is a hole injection transport layer and / or an electron injection transport layer. As a type of element configuration that also serves as a single layer type element configuration. Further, when the light emitting layer is poor in the hole injection function and / or the hole transport function, a two-layer device configuration in which a hole injection transport layer is provided on the anode side of the light emitting layer, the light emitting layer has an electron injection function and / or Alternatively, when the electron transport function is poor, a two-layer device structure in which an electron injection transport layer is provided on the cathode side of the light emitting layer can be obtained. Furthermore, a three-layer device structure in which the light-emitting layer is sandwiched between a hole injection transport layer and an electron injection transport layer can be used.

  In addition, each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single layer structure or a multilayer structure, and the hole injecting and transporting layer and the electron injecting and transporting layer The layer having an injection function and the layer having a transport function can be separately provided.

In the organic electroluminescent element of the present invention, the anthracene compound represented by the general formula (1) is preferably used as a component of the hole injection transport layer and / or the light emitting layer, and is used as a component of the light emitting layer. It is more preferable.
In the organic electroluminescent element of the present invention, the anthracene compound represented by the general formula (1) may be used alone or in combination.

  The configuration of the organic electroluminescent device of the present invention is not particularly limited. For example, (EL-1) anode / hole injection transport layer / light emitting layer / electron injection transport layer / cathode type device (FIG. 1). ), (EL-2) anode / hole injection transport layer / light emitting layer / cathode type device (FIG. 2), (EL-3) anode / light emitting layer / electron injection transport layer / cathode type device (FIG. 3), EL-4) Anode / light emitting layer / cathode type element (FIG. 4), and the like. Further, an EL (EL-5) anode / hole injection / transport layer / electron injection / transport layer / light-emitting layer / electron injection / transport layer / cathode-type device (FIG. 5) in which the light-emitting layer is sandwiched between electron injection / transport layers. You can also. The (EL-4) type element structure includes an element of a type in which a light emitting component is sandwiched between a pair of electrodes as a light emitting layer, (EL-6) a hole injection transport component as a light emitting layer, A device of a type sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injecting and transporting component are mixed (FIG. 6), (EL-7) A hole injecting and transporting component and a light emitting component are mixed as a light emitting layer. A device of a type sandwiched between a pair of electrodes in a single layer form (FIG. 7), (EL-8) A type sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injection / transport component are mixed as a light emitting layer Any of these elements (FIG. 8) may be used.

  The organic electroluminescent device of the present invention is not limited to these device configurations, and each type of device can be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers. Further, in each type of device, the hole injection / transport layer is disposed between the light emitting layer, the hole injection / transport component and the light emitting component mixed layer and / or the light emitting layer and the electron injection / transport layer between the light emitting component and the light emitting component. And a mixed layer of electron injecting and transporting components can be provided.

  A preferred organic electroluminescent element is an (EL-1) type element, an (EL-2) type element, an (EL-5) type element, an (EL-6) type element or an (EL-7) type element. More preferably, it is an (EL-1) type element, an (EL-2) type element or an (EL-7) type element.

Hereinafter, the components of the organic electroluminescence device of the present invention will be described in detail. As an example, (EL-1) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode type device shown in FIG. 1 will be described.
In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injecting and transporting layer, 4 is a light emitting layer, 5 is an electron injecting and transporting layer, 6 is a cathode, and 7 is a power source.

  The organic electroluminescent element of the present invention is preferably supported by the substrate 1, and the substrate is not particularly limited, but a transparent or translucent substrate is preferable, and the material is soda lime glass, Examples thereof include glass such as borosilicate glass and transparent polymers such as polyester, polycarbonate, polysulfone, polyethersulfone, polyacrylate, polymethyl methacrylate, polypropylene, and polyethylene. Further, a substrate made of a translucent plastic sheet, quartz, transparent ceramics, or a composite sheet in which these are combined can also be used. Furthermore, for example, a color filter film, a color conversion film, and a dielectric reflection film can be combined with the substrate to control the emission color.

  As the anode 2, it is preferable to use a metal, an alloy or a conductive compound having a relatively large work function as an electrode material. Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In 2 O 3), tin oxide (SnO 2), zinc oxide, and ITO (indium / tin / tin). Examples thereof include oxide (Indium Tin Oxide), polythiophene, and polypyrrole. These electrode materials may be used alone or in combination.

For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition or sputtering.
Further, the anode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the anode is preferably set to several hundred Ω / □ or less, more preferably about 5 to 50 Ω / □.
The thickness of the anode is generally about 5 to 1000 nm, more preferably about 10 to 500 nm, although it depends on the material of the electrode material used.

The hole injection transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes.
The hole injecting and transporting layer is formed of an anthracene compound represented by the general formula (1) or other compounds having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazole derivatives, hydrazones). Derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, and the like).
The compounds having a hole injecting and transporting function may be used alone or in combination.

  The organic electroluminescent element of the present invention preferably contains an anthracene compound represented by the general formula (1) in the hole injection transport layer. Examples of the compound having a hole injecting and transporting function other than the anthracene compound represented by the general formula (1) of the present invention that can be used in the organic electroluminescent device of the present invention include triarylamine derivatives (for example, 4,4 '-Bis [N-phenyl-N- (4 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] biphenyl, 4,4'- Bis [N-phenyl-N- (3 ″ -methoxyphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl, 3,3′-dimethyl-4 , 4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, 1,1-bis [4 ′-[N, N-di (4 ″ -methylphenyl) amino] phenyl] cyclo Xanthine, 9,10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenyl Phenanthridine, 4-methyl-N, N-bis [4 ", 4" '-bis [N', N'-di (4-methylphenyl) amino] biphenyl-4-yl] aniline, N, N ' -Bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,3-diaminobenzene, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1 , 4-diaminobenzene, 5,5 "-bis [4- (bis [4-methylphenyl] amino] phenyl-2,2 ': 5', 2" -terthiophene, 1,3,5-tris (diphenyl Amino) benzene, 4,4 ' 4 "-tris (N-carbazolyl) triphenylamine, 4,4 ', 4" -tris [N, N-bis (4 "'-tert-butylbiphenyl-4" "-yl) amino] triphenylamine 1,3,5-tris [N- (4′-diphenylamino] benzene and the like, polythiophene and its derivatives, and poly-N-vinylcarbazole and its derivatives are more preferable.

  When the anthracene compound represented by the general formula (1) and another compound having a hole injection function are used in combination, the content of the anthracene compound represented by the general formula (1) in the hole injection transport layer is as follows: Preferably, it is 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, still more preferably 3 to 97% by weight.

The light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.
The light emitting layer is formed using an anthracene compound represented by the general formula (1) as a host material and at least one compound having a light emitting function other than the anthracene compound represented by the general formula (1) as a guest material. In addition, a compound having a light emitting function other than the anthracene compound represented by the general formula (1) is used as at least one host material, and the anthracene compound represented by the general formula (1) is used as a guest material. It can also be formed.

  As a compound (guest material / host material) having a light emitting function other than the anthracene compound represented by the general formula (1), for example, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [for example, Rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis ( 9'-ethynylanthcenyl) benzene, 4,4'-bis (9 "-ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1,2,3-cd: 1 ', 2', 3 '-lm] perylene derivatives], triarylamine derivatives (eg, hole injection and transport functions) Examples of the compound having the above-mentioned compounds), organometallic complexes [for example, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2- (2′-hydroxyphenyl) benzothiazole Zinc salt, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], phosphorescent organometallic complex [for example, phenylpyridine iridium complex , Fluorine-substituted phenylpyridine iridium complexes, tetraazaporphyrin platinum complexes] stilbene derivatives [eg 1,1,4,4-tetraphenyl-1,3-butadiene, 4,4′-bis (2,2-diphenyl) Vinyl) biphenyl, 4,4′-bis [( , 1,2-triphenyl) ethenyl] biphenyl], coumarin derivatives (eg, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin 153, coumarin 307, coumarin 311. , Coumarin 314, Coumarin 334, Coumarin 338, Coumarin 343, Coumarin 500), pyran derivatives (eg DCM1, DCM2), oxazone derivatives (eg Nile Red), benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives Cinnamate derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, poly Enirenbiniren and its derivatives, poly-biphenylene vinylene and derivatives thereof, poly terpolymers phenylene vinylene and derivatives thereof, poly naphthylene vinylene and its derivatives, and polythienylenevinylene and derivatives thereof. Compounds having a light emitting function other than the anthracene compound represented by the general formula (1) (guest material / host material) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes, and stilbenes. Derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.

The organic electroluminescent element of the present invention preferably contains an anthracene compound represented by the general formula (1) as a host material in the light emitting layer.
When the anthracene compound represented by the general formula (1) is used as a host material in combination with another compound having a light emitting function (guest material), the inclusion of the anthracene compound represented by the general formula (1) in the light emitting layer The rate is preferably 99.9-80% by weight, more preferably 99.9-90% by weight.
A host material may be used independently and may be used together.
Moreover, a guest material may be used independently and may be used together.

  When a plurality of host materials are used in combination, the ratio of the anthracene compound represented by the general formula (1) of the present invention to the entire host material is preferably 99 to 10% by weight, more preferably 90 to 20% by weight. It is.

The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating injection of electrons from the cathode and / or a function of transporting injected electrons.
Examples of the compound having an electron injecting and transporting function used in the electron injecting and transporting layer include, for example, organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, phenanthroline derivatives. Nitro-substituted fluorenone derivatives, thiopyrandioxide derivatives, and the like. Examples of the organometallic complex include an organoaluminum complex such as tris (8-quinolinolato) aluminum, an organic beryllium complex such as bis (10-benzo [h] quinolinolato) beryllium, a beryllium salt of 5-hydroxyflavone, 5- Examples thereof include an aluminum salt of hydroxyflavone. An organoaluminum complex is preferable, and an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand is more preferable. Examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolylate ligand include compounds represented by general formula (a) to general formula (c).

(Q) ₃ -Al (a)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)
(Q) ₂ -Al-OL '(b)
(In the formula, Q represents a substituted or unsubstituted 8-quinolinolate ligand, OL ′ represents a phenolate ligand, and L ′ represents a hydrocarbon group having 6 to 24 carbon atoms having a phenyl group. )
(Q) _2- Al-O-Al- (Q) ₂ (c)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)

Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand include, for example, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl- 8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum,
Bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolato) (4-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) ) (3-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,3-dimethylphenolate) aluminum, Bis (2-methyl-8-quinolinolate) ( , 6-Dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-diphenylphenolato) aluminum, bis (2 -Methyl-8-quinolinolato) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolato) aluminum, bis (2-methyl- 8-quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, (2-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenyl) Phenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2 , 4-dimethyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-di-tert-butylphenolate) aluminum,
Bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2, 4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2- Methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum-μ- Oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bi (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum.
A compound having an electron injecting and transporting function may be used alone or in combination.

  As the cathode 6, it is preferable to use a metal, an alloy or a conductive compound having a relatively small work function as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, yttrium, and aluminum. , Aluminum-lithium alloys, aluminum-calcium alloys, aluminum-magnesium alloys, and graphite thin films. These electrode materials may be used alone or in combination.

It is also possible to insert an insulating thin film layer between the cathode and the electron injecting and transporting layer for the purpose of improving the electron injection efficiency or preventing defects due to leakage or short circuit.
Examples of the material used for the insulating layer material include lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium fluoride, calcium fluoride, calcium oxide, aluminum oxide, aluminum nitride, titanium oxide, silicon oxide, and oxide. Examples thereof include germanium, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. These may be used alone, or may be used in a mixed system or a stacked system.

  For the cathode, these electrode materials can be formed on the electron injecting and transporting layer by, for example, vapor deposition, sputtering, ion vapor deposition, ion plating, or cluster ion beam.

  The cathode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the cathode is preferably several hundred Ω / □ or less. The thickness of the cathode is usually 5 to 1000 nm, preferably 10 to 500 nm, although it depends on the electrode material used. In order to take out light emitted from the organic electroluminescence device of the present invention with high efficiency, at least one of the anode and the cathode is preferably transparent or translucent, and generally has a transmittance of emitted light of 70% or more. Thus, it is preferable to set the material and thickness of the anode or cathode.

  The organic electroluminescent device of the present invention may contain a singlet oxygen quencher in at least one of the hole injection transport layer, the light emitting layer, and the electron injection transport layer. Although it does not specifically limit as a singlet oxygen quencher, For example, rubrene, a nickel complex, diphenylisobenzofuran is mentioned, Preferably it is rubrene.

The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer. When a singlet oxygen quencher is contained in the hole injecting and transporting layer, it may be uniformly contained in the hole injecting and transporting layer. May be contained in the vicinity of the electron injecting and transporting layer).
The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.05 to 30% by weight of the total amount constituting the layer to be contained (for example, hole injection transport layer). Preferably, it is 0.1 to 20% by weight.

The formation method of the hole injection transport layer, the light emitting layer, and the electron injection transport layer is not particularly limited. For example, a vacuum deposition method, an ionization deposition method, a solution coating method (for example, a spin coating method, a casting method, A dip coat method, a bar coat method, a roll coat method, a Langmuir-Blodget method, an ink jet method) can be used. When forming each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer by a vacuum deposition method, the conditions for vacuum deposition are not particularly limited, but a vacuum of about 10 ⁻⁴ Pa or less is usually used. Below, it is preferable to carry out at a boating temperature (deposition source temperature) of about 50 to 500 ° C. and a substrate temperature of about −50 to 300 ° C. at a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer is preferably formed continuously under vacuum. It becomes possible to manufacture an organic electroluminescent element excellent in various characteristics by forming continuously. When each layer such as hole injection transport layer, light emitting layer, electron injection transport layer, etc. is formed using a plurality of compounds by vacuum deposition, the temperature of each boat containing the compounds is individually controlled and co-evaporated. It is preferable to do.

  When each layer is formed by a solution coating method, the component forming each layer or the component and a binder resin are dissolved or dispersed in a solvent to obtain a coating solution. Examples of the solvent include organic solvents (hydrocarbon solvents such as hexane, octane, decane, toluene, xylene, ethylbenzene, 1-methylnaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform, and the like. , Halogenated hydrocarbon solvents such as tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, ester solvents such as ethyl acetate, butyl acetate, amyl acetate, ethyl lactate, methanol, propanol, butanol Alcohol solvents such as pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, ethylene glycol, dibutyl ether, tetrahydro Ether solvents such as ethylene, dioxane, dimethoxyethane, anisole, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide And polar solvents) and water. A solvent may be used independently and may be used together. When the components of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are dispersed in a solvent, for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like is used as a dispersion method. Can be used.

Examples of binder resins that can be used in each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl methacrylate, poly Methyl acrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polyfluorene and derivatives thereof, Examples thereof include polymer compounds such as polythienylene vinylene and its derivatives. Binder resins may be used alone or in combination. The concentration of the coating solution is not particularly limited, but can be set to a concentration range suitable for producing a desired thickness by the coating method to be carried out, usually 0.1 to 50% by weight, preferably 1 to 30% by weight. When a binder resin is used, the amount used is not particularly limited, but it is usually based on the total amount of components and binder resin that form each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer. It is used such that the content of the binder resin is 5 to 99.9% by weight, preferably 10 to 99% by weight (relative to the total amount of each component in the case of forming a single-layer element).
The film pressure of each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, but is usually 5 nm to 5 μm.

  The organic electroluminescent device of the present invention produced under the above conditions is provided with a protective layer (sealing layer) for the purpose of preventing contact with oxygen, moisture, etc. For example, it can be protected by enclosing it in paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite-containing fluorocarbon oil). Examples of the material used for the protective layer include organic polymer materials (for example, fluorine resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide, metal sulfide), and photocurable resin. The material used for the protective layer may be used alone or in combination. The protective layer may have a single layer structure or a multilayer structure.

  The organic electroluminescent element of the present invention can also be provided with an interface layer (intermediate layer) on the surface of the anode. Examples of the material for the interface layer include organic phosphorus compounds, polysilanes, aromatic amine derivatives, phthalocyanine derivatives, fluorocarbon polymers, and the like.

Furthermore, the surface of an electrode, for example, an anode, can be used by treating the surface with acid, ammonia / hydrogen peroxide, UV ozone, or plasma.
The organic electroluminescent element of the present invention can be usually used as a DC drive type element, but can also be used as an AC drive type element. Further, the organic electroluminescence device of the present invention may be a segment type, a passive drive type such as a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or an MIM (metal-insulator-metal) type. It may be. The driving voltage is usually 2 to 30V. The organic electroluminescent element of the present invention includes a panel-type light source (for example, a backlight for a clock, a liquid crystal panel, etc.), various light-emitting elements (for example, an alternative to a light-emitting element such as an LED), and various display elements [for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], various signs, various sensors, and the like.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to a following example.

Production of Exemplified Compound (2) -1 benzyl phenyl ketone 41.6 g (212 mmol), o-dibromobenzene 50.0 g (212 mmol), Pd (OAc) ₂ 2.38 g (10.6 mmol), PPh ₃ 11.1 g ( 42.4 mmol), 138 g (424 mmol) of Cs ₂ CO _{3 and} 820 ml of xylene were charged, and the mixture was heated to reflux at 160 ° C. for 24 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extract was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The concentrated residue was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain 38.9 g of a colorless solid of diphenylbenzofuran.
Next, 113 ml (158 mmol) of a 1.4 N sec-butyllithium cyclohexane solution was added dropwise to 18.7 g (158 mmol) of tetramethylethylenediamine dissolved in 400 ml of tetrahydrofuran under a nitrogen atmosphere at −78 ° C., followed by tetrahydrofuran. 38.9 g (144 mmol) of diphenylbenzofuran dissolved in 200 ml was added dropwise. After reacting at the same temperature for 3 hours, 30.0 g (288 mmol) of trimethyl borate dissolved in 20 ml of tetrahydrofuran was dropped, and the temperature was naturally raised to room temperature. Next, 165 ml of a 10% aqueous sulfuric acid solution was added dropwise, and after stirring at room temperature for 3 hours, a 10% aqueous sodium hydroxide solution was added dropwise to adjust the pH of the aqueous phase to 4-5. The organic phase was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentration, 200 ml of toluene was added to the residue and stirred, and then the deposited residue was collected by filtration to obtain 38.0 g of 2,3-diphenylbenzofuran-7-boronic acid.

On the other hand, in a mixture consisting of 18.7 g (72.7 mmol) of 9-bromo-anthracene, 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 8.0 g (75.0 mmol) of sodium carbonate, 60 g of toluene and 45 g of water. Under a nitrogen atmosphere, 0.6 g of tetrakis (triphenylphosphine) palladium was added, and the mixture was heated and stirred at 83 ° C. for 6 hours. The reaction mixture was cooled to room temperature and extracted with toluene. The extract was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. This was concentrated, and the resulting solid was washed with a small amount of toluene, 200 ml of isopropanol was added, and the mixture was heated to reflux. The precipitated solid was collected by filtration and heated with sludge with methanol to obtain 21.5 g of 9- (biphenyl-2-yl) -anthracene white solid.
Next, 21.2 g (64.2 mmol) of 9- (biphenyl-2-yl) -anthracene was dissolved in 250 ml of tetrahydrofuran, charged with 11.4 g (64.2 mmol) of N-bromosuccinimide, and reacted at room temperature for 6 hours. I let you. The reaction solution was concentrated, charged with 250 ml of methanol and heated to reflux. After cooling, the residue was collected by filtration to obtain 24.4 g of 9- (biphenyl-2-yl) -10-bromo-anthracene yellow solid.
Finally, 5.32 g (13.0 mmol) of 9- (biphenyl-2-yl) -10-bromo-anthracene, 5.12 g (16.3 mmol) of 2,3-diphenylbenzofuran-7-boronic acid, 50 ml of toluene, After charging 5 ml of dimethyl sulfoxide, 3.44 g (32.6 mmol) of sodium carbonate and 17.2 g of water, and substituting nitrogen in the system, 1.0 g of tetrakistriphenylphosphine palladium (0) was added, and the temperature was 48 at 83 degrees. Heated to reflux for hours.
After cooling the reaction solution to room temperature, the organic phase was extracted, washed with water and saturated brine in that order, and then dried over anhydrous magnesium sulfate. The residue obtained by concentrating this was purified by silica gel column chromatography (toluene / hexane) and then sludged with isopropanol-hexane to obtain 4.0 g of a pale yellowish white solid of exemplary compound (2) -1.
Further, this compound was purified by sublimation under conditions of 350 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 599 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.28; H, 5.05
Analytical value (%); C, 92.3; H, 5.1

Production of Illustrative Compound (2) -3 In Example 1, instead of using 41.6 g (212 mmol) of benzyl phenyl ketone, 1- (3,4-dimethoxyphenyl) -2-phenylethane-1-one 54. Except for using 4 g (212 mmol), 3.6 g of the compound of exemplary compound (2) -3 was obtained according to the procedure described in Example 1. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 659 (M ⁺ )
Elemental analysis: calculated value (%); C, 87.51; H, 5.20
Analytical value (%); C, 875.7; H, 5.2

Production of Exemplified Compound (3) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 14.4 g (72.7 mmol) of 3-biphenylboronic acid was used. 4.9 g of the compound of exemplary compound (3) -1 was obtained according to the procedure described in Example 1. Further, this compound was purified by sublimation at 370 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 599 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.28; H, 5.05
Analytical value (%); C, 92.3; H, 5.1

Production of Exemplary Compound (3) -6 In Example 1, instead of using 41.6 g (212 mmol) of benzyl phenyl ketone, 61.2 g of 2- (4-phenoxyphenyl) -1-phenylethane-1-one ( 212 mmol) of Exemplified Compound (3) -6, except that 14.4 g (72.7 mmol) of 3-biphenylboronic acid was used instead of 14.4 g (72.7 mmol) of 2-biphenylboronic acid. 3.8 g of compound was obtained. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 675 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.55; H, 5.08
Analytical value (%); C, 92.6; H, 5.1

Production of Exemplary Compound (4) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 14.4 g (72.7 mmol) of 4-biphenylboronic acid was used. Obtained 4.9 g of the compound of exemplary compound (4) -1 according to the procedure described in Example 1. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 599 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.28; H, 5.05
Analytical value (%); C, 92.3; H, 5.1

Production of Exemplified Compound (5) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 15.4 g (72.7 mmol) of 4-dibenzofuranboronic acid was used. In accordance with the procedure described in Example 1, 4.6 g of the compound of exemplary compound (5) -1 was obtained. Further, this compound was purified by sublimation under conditions of 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 612 (M ⁺ )
Elemental analysis: calculated value (%); C, 90.17; H, 4.61
Analytical value (%); C, 90.2; H, 4.6

Production of Exemplified Compound (5) -2 In Example 1, instead of using 41.6 g (212 mmol) of benzyl phenyl ketone, 54.3 g (212 mmol) of desoxyanisoin was converted to 14.4 g of 2-biphenylboronic acid (212 mmol). Instead of using 72.7 mmol), the compound of Exemplified Compound (5) -2 was prepared according to the procedure described in Example 1, except that 15.4 g (72.7 mmol) of 4-dibenzofuranboronic acid was used. 4 g was obtained. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 673 (M ⁺ )
Elemental analysis: calculated (%); C, 85.69; H, 4.79
Analytical value (%); C, 85.7; H, 4.8

Production of Exemplified Compound (5) -11 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 15.4 g (72.7 mmol) of 4-dibenzofuranboronic acid was converted to benzylphenyl Instead of using 41.6 g (212 mmol) of ketone, the procedure described in Example 1 was used except that 61.2 g (212 mmol) of 1- (2,6-difluorophenyl) -2-phenylethane-1-one was used. According to operation, 3.5g of compounds of exemplary compound (5) -11 were obtained. Further, this compound was purified by sublimation at 450 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 649 (M ⁺ )
Elemental analysis: calculated value (%); C, 85.17; H, 4.04
Analytical value (%); C, 85.2; H, 4.0

Production of Exemplified Compound (6) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 16.1 g (72.7 mmol) of 9-phenanthreneboronic acid was used. 4.9 g of the compound of exemplary compound (6) -1 was obtained according to the procedure described in Example 1. Further, this compound was purified by sublimation at 370 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 622 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.58; H, 4.86
Analytical value (%); C, 92.6; H, 4.9

Production of Exemplified Compound (7) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 17.9 g (72.7 mmol) of 1-pyreneboronic acid was used. According to the procedure described in Example 1, 5.0 g of the compound of exemplary compound (7) -1 was obtained. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 646 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.85; H, 4.68
Analytical value (%); C, 92.8; H, 4.7

Production of Exemplified Compound (8) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 12.5 g (72.7 mmol) of 2-naphthaleneboronic acid was used. Followed the procedure described in Example 1 to obtain 4.8 g of the compound of exemplary compound (8) -1. Further, this compound was purified by sublimation under conditions of 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 572 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.28; H, 4.93
Analytical value (%); C, 92.3; H, 4.9

Production of Exemplified Compound (8) -2 In Example 1, instead of using 41.6 g (212 mmol) of benzyl phenyl ketone, 54.3 g (212 mmol) of desoxyanisoin was converted to 14.4 g of 2-biphenylboronic acid (212 mmol). Instead of using 72.7 mmol), the compound of Exemplified Compound (8) -2 was prepared according to the procedure described in Example 1 except that 12.5 g (72.7 mmol) of 2-naphthaleneboronic acid was used. 8 g was obtained. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 633 (M ⁺ )
Elemental analysis: calculated value (%); C, 87.32; H, 5.10
Analytical value (%); C, 87.3; H, 5.1

Production of Illustrative Compound (8) -6 In Example 1, instead of using 41.6 g (212 mmol) of benzyl phenyl ketone, 30.6 g of 2- (4-phenoxyphenyl) -1-phenylethane-1-one ( 106 mmol) according to the procedure described in Example 1 except that 12.5 g (72.7 mmol) of 2-naphthaleneboronic acid was used instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid. 3.9 g of the compound of exemplary compound (8) -6 was obtained. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 665 (M ⁺ )
Elemental analysis: calculated value (%); C, 90.33; H, 4.85
Analytical value (%); C, 90.3; H, 4.9

Production of Exemplified Compound (8) -14 In Example 1, instead of using 50.0 g (212 mmol) of o-dibromobenzene, 57.6 g (212 mmol) of 1,2-dibromo-4,5-difluorobenzene was used. Instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, according to the procedure described in Example 1, except that 12.5 g (72.7 mmol) of 2-naphthaleneboronic acid was used, 8) 4.5g of -14 compounds were obtained. Further, this compound was purified by sublimation under conditions of 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 609 (M ⁺ )
Elemental analysis: calculated value (%); C, 86.82; H, 4.31
Analytical value (%); C, 86.8; H, 4.3

Production of Exemplified Compound (9) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 12.5 g (72.7 mmol) of 1-naphthaleneboronic acid was used. Produced 4.2 g of the compound of exemplary compound (9) -1 according to the procedure described in Example 1. Further, this compound was purified by sublimation under conditions of 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 572 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.28; H, 4.93
Analytical value (%); C, 92.3; H, 4.9

Production of Exemplified Compound (10) -1 In Example 1, instead of using 14.4 g (72.7 mmol) of 2-biphenylboronic acid, 17.9 g (72.7 mmol) of 3-fluorantheneboronic acid was used. Except that, in accordance with the operation described in Example 1, 4.6 g of the compound of exemplary compound (10) -1 was obtained. Further, this compound was purified by sublimation under conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 646 (M ⁺ )
Elemental analysis: calculated value (%); C, 92.85; H, 4.68
Analytical value (%); C, 92.8; H, 4.7
<< Production of organic electroluminescent element >>

A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was washed with a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and isopropanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, and then fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1 × 10 ⁻⁵ Pa. First, on the ITO transparent electrode, copper phthalocyanine was evaporated at a deposition rate of 0.3 nm / sec to a thickness of 20 nm to form a hole injection layer. Next, 4,4′-bis (N-phenyl-N-1 ″ -naphthylamino) -1,1′-biphenyl was deposited to a thickness of 20 nm at a deposition rate of 0.3 nm / sec, and a hole transport layer was formed. Next, as a light emitting layer on the hole injecting and transporting layer, the compound of exemplary compound (2) -1 and the following compound D1 [Chemical Formula 39] were deposited at a deposition rate of 0.3 nm / sec and 0.03 nm / A light emitting layer was formed by co-evaporation from a different vapor deposition source in 30 seconds, and tris (8-quinolinolato) aluminum was deposited on the light emitting layer to a thickness of 15 nm at a deposition rate of 0.2 nm / sec. Then, an electron injecting and transporting layer was formed, on which lithium fluoride was deposited at a deposition rate of 0.2 nm / sec to a thickness of 0.5 nm, and finally aluminum was deposited as a cathode at a deposition rate of 2.0 nm / sec to 100 nm. To the thickness of Wear was manufactured an organic electroluminescence device. In addition, deposition was performed while maintaining the vacuum of the deposition chamber.

[Examples 18 to 32]
In Example 17, an organic electroluminescent element was produced according to the procedure described in Example 17 except that the compound shown in Table 2 was used instead of the compound of Exemplary Compound (2) -1.

[Comparative Examples 1-3]
In Example 19, according to the operation described in Example 19, except that the following compounds H1 [Chemical 29] to H3 [Chemical 31] were used instead of the compound of Exemplary Compound (2) -o-1, An electroluminescent element was produced.

<< Evaluation of organic electroluminescence element >>
With respect to the organic electroluminescent devices obtained in Examples 17 to 32 and Comparative Examples 1 to 3, a direct current voltage was applied, and the device was continuously driven at a constant current density of 50 mA / cm ² at room temperature in a dry atmosphere. The initial voltage value, luminance, emission color, and half-life of luminance were measured. The evaluation results are shown in Table 1.

<< Production and evaluation of organic electroluminescent elements >>
[Example 33]
A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was washed with a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and isopropanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, and then fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1 × 10 ⁻⁵ Pa. First, 4,4 ′, 4 ″ -tris [N- (3 ″ -methylphenyl) -N-phenylamino] triphenylamine is deposited on an ITO transparent electrode at a deposition rate of 0.1 nm / sec and a thickness of 50 nm. To form a hole injection layer. Next, 4,4′-bis [N-phenyl-N- (1-naphthyl) amino] was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec to form a hole transport layer. Furthermore, the compound represented by Exemplified Compound (2) -1 and the compound represented by Illustrated Compound (8) -1 were further separated from the vapor deposition source at 0.2 nm / sec and 0.2 nm / sec from 40 nm. A light emitting layer was formed by co-evaporation to a thickness. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 50 mA / cm ² in a dry atmosphere. Initially, blue light emission of 5.1 V and luminance of 3450 cd / m ² was confirmed. The half life of luminance was 2950 hours.

[Example 34]
A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was washed with a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and isopropanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, and then fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1 × 10 ⁻⁵ Pa. First, poly (thiophene-2,5-diyl) was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injection transport layer. After returning a vapor deposition tank to atmospheric pressure, the vapor deposition tank was pressure-reduced to 1 * 10 < ^-5 > Pa again. Next, the compound of Exemplified Compound (5) -18 and rubrene were co-deposited from different deposition sources to a thickness of 55 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1), and the second hole injection transport A light emitting layer having both layers was formed. Next, while maintaining the reduced pressure state, tris (8-quinolinolato) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. While maintaining the reduced pressure state, magnesium and silver were further co-deposited as a cathode to a thickness of 200 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1) to form a cathode, and an organic electroluminescent device Was made. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 50 mA / cm ² in a dry atmosphere. Initially, yellow light emission of 5.4 V and luminance of 5900 cd / m ² was confirmed. This element had a luminance decrease of 10% or less even after 1000 hours.

[Example 35]
In Example 34, an organic compound was prepared according to the procedure described in Example 35 except that the compound of exemplary compound (8) -1 was used instead of the compound of exemplary compound (5) -1 in forming the light emitting layer. An electroluminescent element was prepared. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 50 mA / cm ² in a dry atmosphere. Initially, yellow light emission of 5.1 V and luminance of 6000 cd / m ² was confirmed. This element had a luminance decrease of 10% or less even after 1000 hours.

According to the present invention, it has become possible to provide a novel anthracene compound and an organic electroluminescence device having a long emission lifetime and high emission efficiency.

It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element.

Explanation of symbols

1: substrate 2: anode 3: hole injection transport layer 3a: hole injection transport component 4: light emitting layer 4a: light emission component 5: electron injection transport layer 5 ": electron injection transport layer 5a: electron injection transport component 6: cathode 7: Power supply

Claims (8)

An anthracene compound represented by the following general formula (1 ) .

Wherein Ar ¹ , Ar ² and Ar ³ are substituted or unsubstituted carbocyclic aromatic groups or heterocyclic aromatic groups having 6 to 48 carbon atoms, and R ^{1 to} R ¹¹ are each independently Hydrogen atom , halogen atom, cyano group, nitro group, substituted or unsubstituted amino group, substituted or unsubstituted ester group, linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, 1 to 10 carbon atoms Linear, branched or cyclic alkoxy group, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, substituted or unsubstituted group having 4 to 20 carbon atoms It represents an aryl group, or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms , and these may be the same or different.
X represents an oxygen atom or a sulfur atom. n is an integer of 1 to 3. ] The anthracene compound represented by the general formula (1), the compound according to claim ¹ , wherein Ar ¹ is represented by the general formulas (2) to (10 ) .

_{Wherein, R 21 ~R 29, R 31} ~R 39, R 41 ~R 49, R 51 ~R 57, R 61 ~R 69, R 71 ~R 79, R 81 ~R 87, R 91 ~R ₉₇ and R _{101 to} R ₁₀₉ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted ester group, a straight chain having 1 to 10 carbon atoms, branched or A cyclic alkyl group, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, A substituted or unsubstituted aryl group having 4 to 20 carbon atoms or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms is represented, and X ₅ represents an oxygen atom or a sulfur atom. ] The organic electroluminescent element formed by pinching at least 1 layer containing at least 1 sort (s) of the anthracene compound represented by the said General formula (1) of Claim 1 between a pair of electrodes. Layer containing an anthracene compound represented by the general formula (1) is an organic electroluminescent device of claim 3, wherein the light emitting layer. Layer containing an anthracene compound represented by the general formula (1) is an organic electroluminescent device of claim 3, wherein a hole injection transport layer. The organic electroluminescent element according to claim 4, wherein the light emitting layer is formed of a host material and a dopant material, and the anthracene compound represented by the general formula (1) is contained as the light emitting layer host material. Between a pair of electrodes, the organic electroluminescent element according to any one of claims 3-6, further comprising a positive hole injection transport layer. The organic electroluminescent element according to any one of claims 3 to 7, further comprising an electron injecting and transporting layer between the pair of electrodes.

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