JP4074611B2 - Anthracene compound and organic electroluminescent device containing the anthracene compound - Google Patents

Description

  The present invention relates to a novel anthracene compound and an organic electroluminescent device comprising the anthracene compound.

  Electroluminescent devices that use electroluminescence are self-luminous compared to liquid crystal displays and thus have high visibility and high-speed responsiveness, so that they can display clear images when used in displays. In addition, since it is an all solid-state device, it has characteristics such as excellent impact resistance. Therefore, in recent years, it is expected to be widely used for thin displays, liquid crystal display backlights, flat light sources, and the like.

  Here, the electroluminescent element can be roughly classified into an inorganic electroluminescent element and an organic electroluminescent element according to the constituent materials. The inorganic electroluminescent device is a dispersive electroluminescent device using an inorganic material such as zinc sulfide. The driving method of this dispersive electroluminescent device is that an accelerated electron collides and excites the emission center by applying a high electric field. Therefore, it is necessary to drive with a high AC voltage. Therefore, there are problems such as a complicated driving circuit and low luminance.

  On the other hand, an organic electroluminescence device (organic electroluminescence device: organic EL device) emits light by recombining charges (holes and electrons) injected from an electrode in a light emitting layer made of an organic compound. Because it is “light emission”, it can be driven at a low voltage (Non-patent Document 1 and Patent Document 1). Further, there is an advantage that an arbitrary emission color and characteristics can be easily changed by changing the molecular design of the organic compound. For this reason, various materials and element configurations have been proposed at present, and research and development has been activated.

  On the other hand, various problems and problems still remain in the organic electroluminescent devices using the materials proposed so far. For example, there is a problem in the light emission life that the function of the element deteriorates and the light emission luminance decreases only by storing, regardless of the drive state or the non-drive state. In general, the emission luminance is still low, which is not sufficient for practical use.

  As a method for improving emission luminance, an organic electroluminescence device using tris (8-quinolinolato) aluminum or the like as a host material in a light emitting layer, a coumarin derivative or a pyran derivative as a guest compound (Non-patent Document 2), and a guest compound An organic electroluminescent device using N, N-dimethylquinacridone (for example, Non-Patent Document 3) and an organic electroluminescent device using rubrene as a guest compound (for example, Non-Patent Document 4) have been proposed. In addition, organic electroluminescent elements using anthracene derivatives as the material of the light emitting layer have been proposed (Patent Documents 2 and 3). However, organic electroluminescent devices using these compounds still have problems in terms of stability and durability, and are not sufficient.

At present, there is a demand for an organic electroluminescence device that emits light with higher brightness, has a long emission life, and is excellent in stability and durability.
Appl.Phys.Lett., 51,913 (1987) J.Appl.Phys., 65,3610 (1989) Appl.Phys.Lett., 70,1665 (1997) Jpn.J.Appl.Phys., 34, L824 (1995) Japanese Unexamined Patent Publication No. 63-264692 JP-A-8-12600 Japanese Patent Laid-Open No. 10-36832

  An object of the present invention is to provide an anthracene compound and an organic electroluminescent device containing the compound. More specifically, it is an object to provide an anthracene compound suitable for a light emitting material of an organic electroluminescent element, and an organic electroluminescent element excellent in stability and durability using the compound.

  In order to solve the above-mentioned problems, the present inventors have intensively studied various anthracene compounds and organic electroluminescent elements, and as a result, have completed the present invention. That is, the present invention provides <1>: an anthracene compound represented by the general formula (1) (chemical formula 1),

[Wherein R _{1 to} R ₈ are a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, or a — (X ′) nZ ′ group (wherein Z ′ is a substituted or unsubstituted group) A linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, X ′ represents an oxygen atom or a sulfur atom, and n represents 0 or 1). Ar represents a substituted or unsubstituted aryl group, X represents an oxygen atom or a sulfur atom, Z represents a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, Or a substituted or unsubstituted aralkyl group)

<2>: Anthracene compound according to <1>, wherein Z is a substituted or unsubstituted aryl group,
<3>: An organic electroluminescent device comprising at least one layer containing at least one anthracene compound described in <1> or <2> between a pair of electrodes,
<4>: The organic electroluminescence device according to <3>, wherein the layer containing the anthracene compound according to <1> or <2> is a charge injection transport layer,
<5>: The organic electroluminescence device according to <4>, wherein the charge injection transport layer is a hole injection transport layer,
<6>: The organic electroluminescence device according to <4>, wherein the charge injection / transport layer is an electron injection / transport layer,
<7>: The organic electroluminescent element according to <3>, wherein the layer containing the anthracene compound according to <1> or <2> is a light emitting layer,
<8>: The organic electroluminescence device according to any one of <3> to <7>, further comprising a hole injection / transport layer between the pair of electrodes.
<9>: The organic electroluminescence device according to any one of <3> to <8>, further comprising an electron injection / transport layer between the pair of electrodes.

  According to the present invention, it is possible to provide a novel anthracene compound and an organic electroluminescence device having a long emission life and excellent durability using the anthracene compound.

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 2).

[Wherein R _{1 to} R ₈ are a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, or a — (X ′) nZ ′ group (wherein Z ′ is a substituted or unsubstituted straight group) A chain, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, X ′ represents an oxygen atom or a sulfur atom, and n represents 0 or 1). Ar represents a substituted or unsubstituted aryl group, X represents an oxygen atom or a sulfur atom, Z represents a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, Or a substituted or unsubstituted aralkyl group)

In the anthracene compound represented by the general formula (1), R _{1 to} R ₈ are each a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, or a — (X ′) nZ ′ group (wherein Z ′ represents a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, X ′ represents an oxygen atom or a sulfur atom, n represents 0 or 1.

R _{1 to} R ₈ are preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, a substituted or unsubstituted aryl group having 4 to 30 carbon atoms, or carbon A substituted or unsubstituted aralkyl group of 5 to 30 or an unsubstituted amino group, or a — (X ′) n—Z ′ group (wherein Z ′ represents a substituted or unsubstituted carbon) Represents a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, a substituted or unsubstituted aryl group having 4 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, and X ′ Represents an oxygen atom or a sulfur atom, and n represents 0 or 1, more preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, or 4 to 4 carbon atoms. 16 substituted or unsubstituted aryl groups Or a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, or an unsubstituted amino group, or a — (X ′) nZ ′ group (wherein Z ′ represents the number of carbon atoms) Represents a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aryl group having 4 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 5 to 20 carbon atoms, and X ′ represents oxygen. Represents an atom, and n represents 0 or 1.

Specific examples of the halogen atom for R _{1 to} R ₈ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Specific examples of the substituted or unsubstituted amino group of R _{1 to} R ₈ include an amino group, N-methylamino group, N-ethylamino group, Nn-propylamino group, N-isopropylamino group, N- n-butylamino group, N-isobutylamino 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) Mino 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-isopropylamino group, N, N-di-n-butylamino group, N, N-di-isobutylamino group, N, N-di-sec-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-isopropylamino group, N-methyl-Nn-butylamino group, N-methyl-N-tert-butylamino group, N-methyl -N-cyclopentylami Group, N-methyl-N-cyclohexylamino group, N-methyl-N-benzylamino group, N-methyl-N-phenethylamino group, N-ethyl-N-tert-butylamino group, N-ethyl-N- Cyclohexylamino group, N-ethyl-N-benzylamino group, N-isopropyl-N-cyclopentylamino group, N-isopropyl-N-cyclohexylamino group, N-isopropyl-N-benzylamino group, N-tert-butyl-N -Cyclohexylamino group, N-tert-butyl-N-benzylamino group, N-cyclopentyl-N-benzylamino group, N-cyclohexyl-N-benzylamino group, N, N-diphenylamino group, N, N-di (1-naphthyl) amino group, N, N-di (2-naphthyl) amino group, N, N-di (4-phenylphenyl) amino group, N , N- (4-methylphenyl) amino group, N, N-di (3-methylphenyl) amino group, N-phenyl-N- (1-naphthyl) amino group, N-phenyl-N- (2-naphthyl) ) Amino group, N-phenyl-N- (4-phenylphenyl) amino group, N-phenyl-N- (4-methylphenyl) amino group, N- (1-naphthyl) -N- (4′-phenylphenyl) And a substituted or unsubstituted amino group such as an amino group.

Specific examples of the substituted or unsubstituted linear, branched or cyclic alkyl group which is Z ′ of the — (X ′) nZ ′ group of R _{1 to} R ₈ include, for example, a methyl group, an ethyl group, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methyl Pentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1-methylheptyl group, 2-ethylhexyl 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-undecyl group, 1 Methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group N-octadecyl group, 1-nonyldecyl group, 1-decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2-cyclohexylethyl 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-adamantylmethyl group, cyclobutyl group, Cyclopentyl group, 1-methylcyclopentyl group, cyclo Xyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethyl group Cyclohexyl 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, cyclodecyl 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-isopropoxyethyl 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-methoxypropoxy Group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-isopropoxypropyl 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-isopropoxybutyl 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-propoxypentyl 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- Enyloxybutyl 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, -Benzylthioethyl 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,

  Fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8-fluorooctyl group, difluoromethyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro -N-propyl group, 1,1,3-trihydro-perfluoro-n-propyl group, 1,1-dihydro-perfluoro-n-butyl group, 1,1-dihydro-perfluoro-n-pentyl group, 1,1-dihydro-perfluoro-n-hexyl group, 6-fluorohexyl group, 4-fluorocyclohexyl group, 1,1-dihydro-perfluoro-n-octyl group, 1,1-dihydro-perfluoro-n -Decyl group, 1,1-dihydro-perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro-n-tetradecyl group, 1 1-dihydro-perfluoro-n-hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chloro Octyl group, 2,2,2-trichloroethyl 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, but are not limited to, a substituted or unsubstituted linear, branched or cyclic alkyl group such as a hydroxydecyl group, a 12-hydroxydodecyl group and a 2-hydroxycyclohexyl group.

Specific examples of the substituted or unsubstituted aryl group that is Z ′ of the — (X ′) nZ ′ group of R _{1 to} R ₈ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, 2 -Anthracenyl group, 9-anthracenyl group, 9-methyl-10-anthracenyl group, 9-phenyl-10-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group Group, 9-methyl-10-phenanthryl group, 9-phenyl-10-phenanthryl group, 1-methyl-9-phenanthryl group, 1-phenyl-9-phenanthryl group, 2-methyl-9-phenanthryl group, 2-phenyl -9-phenanthryl group, 1,8-dimethyl-9-phenanthryl group, 1,8-diphenyl-9-phenanthryl group, 2- Loro-9-phenanthryl group, 2-fluoro-9-phenanthryl group, 2,7-dichloro-9-phenanthryl group, 2,7-dimethyl-9-phenanthryl group, 2,7-diphenyl-9-phenanthryl group, 2 , 7,9-trimethyl-10-phenanthryl group, 2,7,9-triphenyl-10-phenanthryl group,
5-acenaphthylene group, 9,9-dimethyl-9H-fluoren-2-yl group,

  1-pyrenyl group, 2-pyrenyl group, 1-phenyl-2-pyrenyl group, 1-methyl-2-pyrenyl group, 2-phenyl-1-pyrenyl group, 2-methyl-1-pyrenyl group, 4,5-dimethyl -1-pyrenyl group, 6-phenyl-1-pyrenyl group, 6-methyl-1-pyrenyl group, 6-tert-butyl-1-pyrenyl group, 6-cyclohexyl-1-pyrenyl group, 7-phenyl-1- Pyrenyl group, 7-methyl-1-pyrenyl group, 7-phenyl-2-pyrenyl group, 7-methyl-2-pyrenyl group, 7-tert-butyl-2-pyrenyl group, 1,8-diphenyl-2-pyrenyl group Group, 1,8-dimethyl-2-pyrenyl group, 5,9-dicyclohexyl-2-pyrenyl group, 3,6-diphenyl-1-pyrenyl group, 3,6-dimethyl-1-pyrenyl group, 3,6- Di-tert-butyl-1-pyre Nyl group, 8-methyl-1-pyrenyl group, 8-tert-butyl-1-pyrenyl group, 8-phenyl-1-pyrenyl group, 9-phenyl-1-pyrenyl group, 9-phenyl-2-pyrenyl group, 9-methyl-2-pyrenyl group, 10-phenyl-1-pyrenyl group, 10-methyl-1-pyrenyl group, 10-phenyl-2-pyrenyl group, 10-methyl-2-pyrenyl group, 9-methyl-1 -Pyrenyl group, 3,6,8-trimethyl-1-pyrenyl group, 3,6,8-triphenyl-1-pyrenyl group, 3,6-dimethyl-8-phenyl-1-pyrenyl group, 9,10- Dimethyl-1-pyrenyl group, 9,10-diphenyl-1-pyrenyl group, 4,9-dimethyl-1-pyrenyl group, 4,9-diphenyl-1-pyrenyl group, 9,5-dimethyl-2-pyrenyl group 4,5,9,10-tri Tyl-2-pyrenyl group, 8-quinolinyl group, 4-quinolinyl group, 3-quinolinyl group, 2-quinolinyl group, 4-pyridinyl group, 3-pyridinyl group, 2-pyridinyl group, 2-pyrimidinyl group, 2-pyridazinyl group Group, 2-pyrazinyl group, 3-furanyl group, 2-furanyl group, 3-thienyl group, 2-thienyl group, 2-benzofuranyl group, 2-benzothiophenyl group, 1-dibenzofuranyl group, 3-dibenzothio group Phenyl group, 1-dibenzothiophenyl group, 3-dibenzothiophenyl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl 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-tertbutylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 2-neopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4- ( 2'-ethylbutyl) phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) pheny Group, 4-tert-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4′-methylcyclohexyl) phenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-cyclohexyl-1-naphthyl group, 4-methyl-1 -Naphthyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2, 4-diethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group Nyl group, 2,6-diethylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl-2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group,

  4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl Group, 4-isopropoxyphenyl group, 3-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n- Pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2-nepentyloxyphenyl group, 3-n-hexyloxyphenyl group, 4-n- Hexyloxyphenyl group, 2- (2'-ethylbutyloxy) phenyl group, 4-n- Cutyloxyphenyl group, 4-n-decyloxyphenyl group, 3-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl 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-methoxy-2- 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-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3 Ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl 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-ethoxyphenyl group, 2 -Methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (3′-methylphenyl) phenyl group, 4- (4′-methoxyphenyl) phenyl group, 4- (4′-n-butoxyphenyl) pheny Group, 2- (2'-methoxyphenyl) phenyl group, 4- (4'-chlorophenyl) phenyl group, 3-methyl-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group,

4- (2′-pyridinyl) phenyl group, 3- (2′-pyridinyl) phenyl group, 4- (2′-pyrimidinyl) phenyl group, 1,2,3,4-tetrahydro-6-naphthyl group,
4- (4′-phenylphenyl) phenyl group, 2,4-diphenylphenyl group, 3,5-diphenylphenyl group, 2-phenyl-4-methylphenyl group, 3-phenyl-3-methylphenyl group, 3- Phenyl-4,5-dimethylphenyl group, 4-phenyl-1-naphthylphenyl group, 6-phenyl-2-naphthyl group,

  4-N, N-diphenylaminophenyl group, 3-N, N-diphenylaminophenyl group, 4-phenoxy-1-naphthyl group, 2-methoxy-6-phenyl-1-naphthyl group, 4-N-phenyl- N-methyl-1-naphthyl group, 4-phenoxyphenyl group, 4- (1′-naphthyloxy) phenyl group, 3-phenoxyphenyl group, 3- (1′-naphthyloxy) phenyl group,

  4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 3-bromophenyl group, 2-bromophenyl group 4-chloro-1-naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,5-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, 3,4-dichlorophenyl group, 3,5- Dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,4-dichloro-1-naphth 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, 2-methyl-4-fluorophenyl group, 2-methyl-5-fluorophenyl group, 3-methyl-4-fluorophenyl group, 2-chloro-4-methylphenyl group, 2-chloro-4- Methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methyl-3-chlorophenyl group, 2-methyl-4-chlorophenyl group 3-methyl-4-chlorophenyl group, 2-chloro-4,6-dimethylphenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-meth Siphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-methoxy-5-chlorophenyl Group, 3-methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl group, but is not limited thereto.

Specific examples of the substituted or unsubstituted aralkyl group of R ₁ over the _{~R 8 (X ') n-} Z' group Z 'is, for example, benzyl group, alpha-methylbenzyl group, alpha-ethylbenzyl group, α-fluorobenzyl group, α, α-difluorobenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2-tert-butyl Benzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4-allylbenzyl 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, 4- (4′-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4 -N-butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxy Benzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyl An oxybenzyl group, a 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 And an aralkyl group such as a group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group.

  Further, X ′ in the — (X ′) n—Z ′ group represents an oxygen atom or a sulfur atom, and preferably represents an oxygen atom. N 'in the-(X') n-Z 'group represents 0 or 1, preferably 1.

  In the anthracene compound represented by the general formula (1), Ar represents a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted condensed polycyclic aromatic carbon Represents a hydrogen group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic heterocyclic group, more preferably a substituted or unsubstituted aromatic carbon group having 6 to 40 carbon atoms; A hydrogen group, a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group having 10 to 40 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 40 carbon atoms, or 5 to 40 carbon atoms A substituted or unsubstituted condensed polycyclic heterocyclic group, more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a condensed polycyclic aromatic group having 10 to 30 carbon atoms. Hydrocarbon group Represent.

Specific examples of Ar include the substituted or unsubstituted aryl groups listed as specific examples of the substituted or unsubstituted aryl group of Z ′ of the — (X ′) nZ ′ group of R _{1 to} R _8. be able to.

  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), Z represents a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, Preferably, it represents a substituted or unsubstituted aryl group.

  Moreover, 1-40 are preferable and, as for carbon number of a substituted or unsubstituted linear, branched or cyclic alkyl group, 1-30 are more preferable. 4-40 are preferable and, as for carbon number of a substituted or unsubstituted aryl group, 6-30 are more preferable. 7-40 are preferable and, as for carbon number of a substituted or unsubstituted aralkyl group, 7-30 are more preferable.

Specific examples of the substituted or unsubstituted linear, branched or cyclic alkyl group of Z include a substituted or unsubstituted linear group of Z ′ of the — (X ′) nZ ′ group of R _{1 to} R ₈ , The substituted or unsubstituted linear, branched or cyclic alkyl group mentioned as the specific example of the branched or cyclic alkyl group can be mentioned.

Specific examples of the substituted or unsubstituted aryl group of Z include the substituents listed as specific examples of the substituted or unsubstituted aryl group of Z ′ of the — (X ′) nZ ′ group of R _{1 to} R _8. Or an unsubstituted aryl group can be mentioned.

Specific examples of the substituted or unsubstituted aralkyl group of Z include the substituents listed as specific examples of the substituted or unsubstituted aralkyl group of Z ′ of the — (X ′) nZ ′ group of R _{1 to} R _8. Or an unsubstituted aralkyl group can be mentioned.

  Specific examples of the anthracene compound represented by the general formula (1) according to the present invention include, for example, the following compounds (Chemical Formula 3) to (Chemical Formula 15), but the present invention is limited to these. It is not something.

  The anthracene compound represented by the general formula (1) of the present invention can be produced by a method known per se.

  Production of anthracene compound represented by general formula (1)

[Wherein R _{1 to} R ₈ , X, Z and Ar represent the same meaning as in general formula (1), and L ₁ and L ₂ represent a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group]
That is, an anthracene derivative represented by the general formula (A) and a phenol derivative or thiophenol derivative represented by the general formula (B) are reacted to produce an anthracene derivative represented by the general formula (C). An anthracene derivative represented by the formula (C) is halogenated with a halogenating agent (for example, bromine, N-bromosuccinimide) to produce a compound represented by the general formula (D). Then, the anthracene compound represented by the general formula (1) can be produced by reacting the compound represented by the general formula (D) with the boronic acid derivative represented by the general formula (E).

  The reaction between the anthracene derivative represented by the general formula (A) and the phenol derivative or thiophenol derivative represented by the general formula (B) is performed using a base (for example, sodium hydroxide, potassium hydroxide, sodium carbonate, carbonate Potassium) and a copper catalyst (eg, copper powder, copper chloride, copper bromide), optionally in a solvent (eg, pyridine, N, N-dimethylformamide, N, N′-dimethylimidazolidinone), or It can be produced by heating and reacting without a solvent.

  In addition, the reaction between the compound represented by the general formula (D) and the boronic acid derivative represented by the general formula (E) is performed under the conditions of so-called Suzuki coupling reaction [for example, in an organic solvent such as an aqueous solution of sodium carbonate and toluene. The reaction is carried out in the presence of a palladium catalyst such as tetrakis (triphenylphosphine) palladium, and the reaction is carried out in the presence of a palladium catalyst such as tetrakis (triphenylphosphine) palladium using an organic base such as pyridine or triethylamine as a solvent. ] Can be carried out below.

  The anthracene compound represented by the general formula (1) can also be produced by the following step (Chemical Formula 17).

[Wherein R _{1 to} R ₈ , X, Z and Ar represent the same meaning as in general formula (1), and L ₁ and L ₂ represent a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group]
That is, an anthracene derivative represented by the general formula (F) and a phenol derivative or thiophenol derivative represented by the general formula (B) as a base (for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate) and In the presence of a copper catalyst (eg, copper powder, copper chloride, copper bromide), optionally in a solvent (eg, pyridine, N, N-dimethylformamide, N, N′-dimethylimidazolidinone) or without solvent. The compound represented by the general formula (D) is heated and reacted to be further reacted with the boronic acid derivative represented by the general formula (E), and then the anthracene represented by the general formula (1) Compounds can be produced.

  Furthermore, an anthracene compound represented by the general formula (1) can be produced by the following step (Chemical Formula 18).

[Wherein R _{1 to} R ₈ , X, Z and Ar represent the same meaning as in general formula (1), and L ₁ and L ₂ represent a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group]
That is, the anthracene derivative represented by the general formula (F) is reacted with the boronic acid derivative represented by the general formula (E), and then the phenol derivative or thiophenol derivative represented by the general formula (B) is reacted. The anthracene compound represented by the general formula (1) can also be produced by the method.

  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. A charge injection transport layer such as an electron injection transport layer containing a transport 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 injecting and transporting layer is provided on the cathode side of the light emitting layer can be obtained. Furthermore, a three-layer device configuration 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 electroluminescence device of the present invention, the anthracene compound represented by the general formula (1) is used as a component of the charge injection / transport layer (hole injection / transport layer and / or electron injection / transport layer) and / or the light-emitting layer. It is preferable to use it as a constituent of the light emitting layer.

  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 in which a light emitting component and an electron injection component are mixed and sandwiched between a pair of electrodes (FIG. 6), (EL-7) a layer in which a hole injection transport component and a light emitting component are mixed as a light emitting layer Type element sandwiched between a pair of electrodes in a form (FIG. 7), (EL-8) type element sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injection component are mixed as a light emitting layer Any of (FIG. 8) may be sufficient.

  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, ITO ( Indium tin oxide (Indium Tin Oxide), polythiophene, polypyrrole, etc. can be mentioned. 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 of the electroluminescent device of the present invention comprises an anthracene compound represented by the general formula (1) and / or another compound having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, tria At least one kind of a reel methane derivative, an oxazole derivative, a hydrazone derivative, a stilbene derivative, a pyrazoline derivative, a polysilane derivative, polyphenylenevinylene and its derivative, polythiophene and its derivative, poly-N-vinylcarbazole, etc. .
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] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino]- 1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methoxyphenyl) amino] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (1 ″ -Naphtyl) amino] -1,1′-biphenyl, 3,3′-dimethyl-4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] -1,1 ′ -Biphenyl, 1,1-bis [4'- N, N-di (4 ″ -methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] phenanthrene, 3, , 8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 ", 4" '-bis [N', N'-di (4-methyl) Phenyl) 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 "-Terthiofe 1,3,5-tris (diphenylamino) 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, etc., polythiophene and its derivatives, poly-N-vinylcarbazole And its derivatives are more preferred.

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 can be formed using at least one anthracene compound represented by the general formula (1) and / or another compound having a light emitting function.

  Examples of the compound having a light emitting function other than the anthracene compound represented by the general formula (1) include 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] A triarylamine derivative (eg, a compound having a hole injection / transport function described above) Compounds), organometallic complexes [eg, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, 4 -Zinc salt of hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [for example, 1,1,4,4-tetraphenyl-1, 3-butadiene, 4,4′-bis (2,2-diphenylvinyl) biphenyl, 4,4′-bis [(1,1,2-triphenyl) ethenyl] biphenyl], coumarin derivatives (eg, coumarin 1, Coumarin 6, Coumarin 7, Coumarin 30, Coumarin 106, Coumarin 138, Coumarin 1 1, Coumarin 152, Coumarin 153, Coumarin 307, Coumarin 311, Coumarin 314, Coumarin 334, Coumarin 338, Coumarin 343, Coumarin 500), pyran derivatives (for example, DCM1, DCM2), oxazone derivatives (for example, Nile Red), benzo Thiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene vinylene and derivatives thereof Derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, poly Enirenbiniren and its derivatives, and the like. As the compound having a light emitting function other than the anthracene compound represented by the general formula (1), an acridone derivative, a quinacridone derivative, a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex, and a stilbene derivative are preferable. More preferred are group compounds and organometallic complexes.

  In addition, a phosphorescent (triplet luminescent) compound can be used as the compound having a light emitting function other than the anthracene compound represented by the general formula (1) in the light emitting layer of the organic electroluminescent element of the present invention. It is.

  Here, examples of phosphorescent compounds include tris (2-phenylpyrimidyl) iridium complex, tris [2- (2′-fluorophenyl) pyridyl] iridium complex, and bis (2-phenylpyridyl) acetylacetonate. Iridium complex, bis [2- (2 ′, 4′-difluorophenyl) pyridyl] acetylacetonatoiridium complex, 2,3,7,8,12,13,17,18-octaethyl-21H, 23H porphyrin platinum complex, etc. Can be mentioned.

The organic electroluminescent element of the present invention preferably contains an anthracene compound represented by the general formula (1) in the light emitting layer.
When an anthracene compound represented by the general formula (1) and a compound having a light emitting function other than the anthracene compound represented by the general formula (1) are used in combination, the anthracene represented by the general formula (1) in the light emitting layer The proportion of the compound is preferably adjusted to 0.001 to 99.999% by weight.

The light-emitting layer can also be formed from a host compound and a guest compound (dopant) as described in J. Appl. Phys., 65 , 3610 (1989) and Japanese Patent Application Laid-Open No. 5-214332.

  The anthracene compound represented by the general formula (1) can be used as a host compound of the light emitting layer, and can also be used as a guest compound. When the light emitting layer is formed using the anthracene compound represented by the general formula (1) as a host compound, examples of the guest compound include compounds having other light emitting functions described above, and among them, polycyclic aromatic compounds. Is preferred.

When the light-emitting layer is formed using the anthracene compound represented by the general formula (1) as a host compound, the guest compound is preferably 0.001 to 40 weights with respect to the anthracene compound represented by the general formula (1). %, More preferably 0.01 to 30% by weight, still more preferably 0.1 to 20% by weight. The organic electroluminescent element of the present invention is preferably represented by the general formula (1) in the light emitting layer. An anthracene compound is contained as a host material.

  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, the anthracene compound represented by the general formula (1) in the light emitting layer is preferably 40 It is 0.0% to 99.9%, and more preferably 60.0 to 99.9% by weight.

  The amount of the guest material used is 0.001 to 40% by weight, preferably 0.05 to 30% by weight, more preferably 0.1 to 20% by weight based on the anthracene compound represented by the general formula (1). %. Moreover, a guest material may be used independently and may be used together.

  In the case where the light-emitting layer is formed using the anthracene compound represented by the general formula (1) as a guest material, the host material includes a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex, and a stilbene derivative. Preferably, a polycyclic aromatic compound and an organometallic complex are more preferable.

  When the anthracene compound represented by the general formula (1) is used as a guest material, the anthracene compound represented by the general formula (1) is preferably 0.001 to 40% by weight, more preferably 0.01%. -30% by weight, more preferably 0.1-20% by weight.

  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.

  The organic electroluminescent element of the present invention preferably contains an anthracene compound represented by the general formula (1) in the electron injecting and transporting layer. Examples of the compound having an electron 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 element of the present invention include, for example, organometallic complexes, oxadiazole derivatives, Examples thereof include triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenone derivatives, and thiopyrandioxide derivatives. Examples of the organometallic complex include organoaluminum complexes such as tris (8-quinolinolato) aluminum, organic beryllium complexes such as bis (10-benzo [h] quinolinolato) beryllium, beryllium salts of 5-hydroxyflavone, 5- Examples thereof include an aluminum salt of hydroxyflavone. Preferably, it is an anthracene compound or an organoaluminum complex represented by the general formula (1) of the present invention. Here, the organoaluminum complex is an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand. 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-quinolinolato) (2,4,5,6-tetramethylphenolate) aluminum, bi (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 injection 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 salts of organic acids such as lithium, lithium-indium alloy, lithium fluoride, lithium benzoate, lithium acetate, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver. Examples include alloys, magnesium-indium alloys, indium, ruthenium, titanium, manganese, yttrium, aluminum, aluminum-lithium alloys, aluminum-calcium alloys, aluminum-magnesium alloys, and graphite thin films. These electrode materials may be used alone or in combination.

  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, and a layer adjacent to the hole injecting and transporting layer (for example, a light emitting layer, a light emitting function). 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, based on 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 ⁻⁵ Torr 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., a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as the hole injecting and transporting layer, the light emitting layer, and the 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 a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer 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 thickness of each layer such as the hole injection transport layer, the light emitting layer, and the electron injection transport 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 preferably provided with a protective layer (sealing layer) for the purpose of preventing contact with oxygen, moisture, etc., and the device is made of an inert substance. It can also be protected by enclosing it in a medium (for example, paraffin, liquid paraffin, silicone 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.

  Moreover, the organic electroluminescent element of this invention can also provide a metal oxide film (for example, aluminum oxide film) and a metal fluoride film as a protective film in an electrode.

  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, and phthalocyanine derivatives.

  Furthermore, the surface of an electrode, for example, an anode, can be used by treating the surface with acid, ammonia / hydrogen peroxide, 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 a 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.

[Reference Example 1]
Production of Illustrative Compound 2 [1] Production of 9- (4′-methylphenoxy) anthracene 25.7 g (0.1 mol) of 9-bromoanthracene, 32.7 g (0.3 mol) of 4-methylphenol, ground hydroxide A mixture consisting of 16.8 g (0.3 mol) of potassium and 9 g of copper powder was heated and stirred at 230 ° C. for 6 hours under an argon stream. The reaction mixture was then cooled to room temperature, aqueous sodium hydroxide and toluene were added, and washed with aqueous sodium hydroxide until there was no excess phenol in the toluene phase. Thereafter, the toluene phase was washed with water and separated, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography to obtain 20.4 g of 9- (4′-methylphenoxy) anthracene as colorless crystals.

[2] Preparation of 9- (4′-methylphenoxy) -10-bromoanthracene To a mixture of 14.2 g (50 mmol) of 9- (4′-methylphenoxy) anthracene and 30 g of N, N-dimethylformamide was added N-bromo. Succinimide 8.9g was added and it heat-stirred at 40 degreeC for 8 hours. Thereafter, the reaction mixture is discharged into methanol, and the resulting solid is filtered off and recrystallized from methyl cellosolve to give the desired 9- (4′-methylphenoxy) -10-bromoanthracene as pale yellow crystals. 15.1 g was obtained.

[3] Preparation of Exemplary Compound 2 9- (4′-methylphenoxy) -10-bromoanthracene 3.64 g (10 mmol), 1.22 g (10 mmol) phenylboronic acid, 2.12 g sodium carbonate, 50 g water, and 50 g toluene Under an argon stream, 0.5 g of tetrakis (triphenylphosphine) palladium was added to the resulting mixture, and the mixture was heated and stirred at 100 ° C. for 3 hours. Thereafter, the reaction mixture was cooled to room temperature, the toluene phase was separated and washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography and further recrystallized from toluene / methyl cellosolve to obtain 2.66 g of Compound of Illustrative Compound 2 as colorless crystals.
Further, the compound was purified by sublimation at 320 ° C. and 2.0 × 10 ⁻⁴ Pa.
FD-MS: 360 (M ⁺ )
Elemental analysis: calculated value (%); C, 89.97; H, 5.59; O, 4.44
Analytical value (%); C, 90.0; H, 5.6;

Production of Exemplified Compound 21 [1] Production of 9-bromo-10-phenoxyanthracene 33.6 g (0.1 mol) 9,10-dibromoanthracene, 28.2 g (0.3 mol) phenol, 16.8 g potassium hydroxide and A mixture consisting of 3.0 g of copper powder was heated to 230 ° C. and stirred at the same temperature for 4 hours. Thereafter, the reaction mixture was cooled to room temperature, 100 g of N, N-dimethylformamide was added, and the reaction mixture was dissolved at 120 ° C. The mixture was then cooled to room temperature and discharged into methanol. The produced solid was separated by filtration, purified by silica gel column chromatography, and recrystallized from toluene to obtain 18.6 g of 9-bromo-10-phenoxyanthracene as pale yellow crystals.

[2] Preparation of Exemplary Compound 21 9-Bromo-10-phenoxyanthracene 6.98 g (20 mmol), naphthalene-1-boronic acid 3.44 g (20 mmol), sodium carbonate 4.24 g, water 100 g and toluene 100 g Under an argon stream, 0.8 g of tetrakis (triphenylphosphine) palladium was added, and the mixture was heated and stirred at 100 ° C. for 3 hours. Thereafter, the reaction mixture was cooled to room temperature, the toluene phase was separated and washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography and further recrystallized from toluene / methyl cellosolve to obtain 4.85 g of the compound of Exemplary Compound 21 as colorless crystals.
Further, this compound was purified by sublimation at 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 396 (M ⁺ )
Elemental analysis: calculated value (%); C, 90.88; H, 5.08; O, 4.04
Analytical value (%); C, 91.0; H, 5.0;

Production of Exemplary Compound 23 [1] Consisting of 77.1 g (0.3 mol) of 9-bromoanthracene, 153.0 g (0.9 mol) of 4-phenylphenol, 30.0 g of pulverized sodium hydroxide and 9.0 g of copper powder The mixture was heated to 230 ° C. and stirred at the same temperature for 8 hours. Thereafter, the reaction mixture was cooled to room temperature, 500 g of N, N-dimethylformamide was added, and the reaction mixture was dissolved at 120 ° C. 2 liters of toluene was added here, washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was recrystallized from methyl cellosolve to obtain 67.2 g of 9- (4′-phenylphenoxy) anthracene as colorless crystals.

[2] 34.6 g (81 mmol) of 9- (4′-phenylphenoxy) anthracene was dissolved in 100 g of N, N-dimethylformamide and cooled to 5 ° C. with an ice bath. To this solution, a mixture of 14.4 g (81 mmol) of N-bromosuccinimide and 180 g of N, N-dimethylformamide was added dropwise over 3 hours. Thereafter, the reaction mixture was warmed to room temperature and further stirred for 8 hours. N, N-dimethylformamide was distilled off from the reaction mixture under reduced pressure, and isopropanol was added to the residue to obtain crystals. Thereafter, recrystallization from methyl cellosolve gave 18.9 g of 9-bromo-10- (4'-phenylphenoxy) anthracene as pale yellow crystals.

[3] 9-bromo-10- (4′-phenylphenoxy) anthracene 1.28 g (3 mmol), naphthalene-1-boronic acid 0.52 g (3 mmol), sodium carbonate 0.7 g, water 20 g and toluene 30 g Under an argon stream, 220 mg of tetrakis (triphenylphosphine) palladium was added to the mixture, and the mixture was heated and stirred at 110 ° C. for 8 hours. Thereafter, crystals generated from the reaction mixture were filtered off, washed with water, and recrystallized from tetralin to obtain 1.2 g of the compound of Exemplary Compound 23 as colorless crystals.
Further, this compound was purified by sublimation at 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 472 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.50; H, 5.12; O, 3.39
Analytical value (%); C, 91.5; H, 5.1;

Production of Exemplified Compound 26 In [3] of Example 3, except that 0.57 g (3 mmol) of naphthalene-1-boronic acid was used instead of 0.67 g (3 mmol) of phenanthrene-9-boronic acid, According to the operation described in [3] of Example 3, 1.4 g of the compound of Exemplary Compound 26 was obtained as colorless crystals.
Further, this compound was purified by sublimation at 380 ° C. and 1.5 × 10 ⁻⁴ Pa.
FD-MS: 522 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.92; H, 5.01; O, 3.06
Analytical value (%); C, 91.9; H, 5.0;

Preparation of Exemplified Compound 27 In [3] of Example 3, 1.28 g (3 mmol) of 9-bromo-10- (4′-phenylphenoxy) anthracene and 0.52 g (3 mmol) of naphthalene-1-boronic acid are used. Instead of Example 3 [3] except that 1.28 g (3 mmol) of 9-bromo-10- (3′-phenylphenoxy) anthracene and 0.67 g (3 mmol) of phenanthrene-9-boronic acid were used. According to the operation described, 1.6 g of Compound of Exemplified Compound 27 was obtained as colorless crystals.
Further, this compound was purified by sublimation at 360 ° C. and 1.5 × 10 ⁻⁴ Pa.
FD-MS: 522 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.92; H, 5.01; O, 3.06
Analytical value (%); C, 91.9; H, 5.0;

Preparation of Exemplary Compound 29 In [3] of Example 3, instead of using 1.28 g (3 mmol) of 9-bromo-10- (4′-phenylphenoxy) anthracene and 0.52 g (3 mmol) of naphthalene-1-boronic acid Example 3 [3] except that 1.20 g (3 mmol) of 9-bromo-10- (1′-naphthyloxy) anthracene and 0.52 g (3 mmol) of naphthalene-2-boronic acid were used. According to the procedure, 1.2 g of the compound of Exemplary Compound 29 was obtained as colorless crystals.
Further, this compound was purified by sublimation at 340 ° C. and 1.5 × 10 ⁻⁴ Pa.
FD-MS: 446 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.45; H, 4.97; O, 3.58
Analytical value (%); C, 91.5; H, 5.0;

Production of Exemplified Compound 34 In [3] of Example 3, 1.28 g (3 mmol) of 9-bromo-10- (4′-phenylphenoxy) anthracene and 0.52 g (3 mmol) of naphthalene-1-boronic acid are used. Instead, according to the procedure described in [3] of Example 3 except that 1.04 g (3 mmol) of 9-bromo-10-phenoxyanthracene and 0.74 g (3 mmol) of pyrene-1-boronic acid were used, the exemplified compound 1.3 g of 34 compounds were obtained as colorless crystals. Further, this compound was purified by sublimation at 380 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 470 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.89; H, 4.71; O3.40
Analytical value (%); C, 91.9; H, 4.7;

Preparation of Exemplified Compound 37 In Example 3-3, instead of using 1.28 g (3 mmol) 9-bromo-10- (4′-phenylphenoxy) anthracene and 0.52 g (3 mmol) naphthalene-1-boronic acid , 9-bromo-10- (4′-methylphenoxy) anthracene 1.09 g (3 mmol) and phenanthrene-9-boronic acid 0.67 g (3 mmol) were used as described in [3] of Example 3. As a result, 1.2 g of the compound of Exemplified Compound 37 was obtained as colorless crystals. Further, this compound was purified by sublimation at 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 460 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.27; H, 5.25; O, 3.47
Analytical value (%); C, 91.3; H, 5.2;

Production of Illustrative Compound 45 In [3] of Example 3, instead of using 0.52 g (3 mmol) of naphthalene-1-boronic acid, 0.73 g (3 mmol) of 2-phenylnaphthalene-6-boronic acid was used. Except for the above, according to the procedure described in [3] of Example 3, 1.2 g of the compound of exemplary compound 45 was obtained as colorless crystals. Further, this compound was purified by sublimation at 360 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 548 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.94; H, 5.14; O, 2.92
Analytical value (%); C, 92.0; H, 5.1;

[Reference Example 2]
Preparation of Exemplary Compound 47 In [3] of Example 3, instead of using 1.28 g (3 mmol) of 9-bromo-10- (4′-phenylphenoxy) anthracene and 0.52 g (3 mmol) of naphthalene-1-boronic acid In Example 3 except that 1.28 g (3 mmol) of 9- (3′-phenylphenoxy) anthracene and 0.71 g (3 mmol) of 9,9-dimethyl-9H-fluorene-2-boronic acid were used. 3], 1.1 g of the compound of Exemplified Compound 47 was obtained as colorless crystals.
Further, this compound was purified by sublimation at 380 ° C. and 1.5 × 10 ⁻⁴ Pa.
FD-MS: 538 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.42; H, 5.61; O, 2.97
Analytical value (%); C, 91.4; H, 5.6;

Preparation of Exemplary Compound 50 In [3] of Example 3, instead of using 1.28 g (3 mmol) of 9-bromo-10- (4′-phenylphenoxy) anthracene and 0.52 g (3 mmol) of naphthalene-1-boronic acid Example 3 [3] except that 1.28 g (3 mmol) of 9-bromo-10- (2′-phenylphenoxy) anthracene and 0.59 g (3 mmol) of acenaphthene-5-boronic acid were used. According to the procedure, 1.3 g of the compound of Exemplary Compound 50 was obtained as colorless crystals.
Further, this compound was purified by sublimation at 380 ° C. and 1.5 × 10 ⁻⁴ Pa.
FD-MS: 498 (M ⁺ )
Elemental analysis: calculated value (%); C, 91.54; H, 5.26; O, 3.21
Analytical value (%); C, 91.5; H, 5.3;

[Reference Example 3]
Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was ultrasonically cleaned using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried with nitrogen gas, further UV / ozone cleaned, fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁴ Pa. First, N, N′-diphenyl-N, N′-di (2-naphthyl) -4,4′-diamino-1,1′-biphenyl is deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec to 75 nm. To form a hole injection transport layer. Next, as a light emitting layer on the hole injecting and transporting layer, the compound of Exemplary Compound 2 and 4,4′-bis [2 ″-(4 ″ ′-N, N-diphenylaminophenyl) vinyl] -1, 1′-biphenyl was co-deposited to a thickness of 40 nm from different deposition sources at a deposition rate of 0.2 nm / sec and a deposition rate of 0.01 nm / sec to form a light emitting layer. Further, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 30 nm to form a light emitting layer having an electron injecting and transporting layer. Further, lithium fluoride is deposited thereon as an electron injection layer at a deposition rate of 0.2 nm / sec to a thickness of 1 nm, and then aluminum is deposited at a deposition rate of 2.0 nm / sec to a thickness of 200 nm. Thus, an organic electroluminescent element was produced as a cathode. In addition, vapor deposition was implemented, maintaining the pressure reduction state of a vapor deposition tank. 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 10 mA / cm ^{2 in} a dry atmosphere at room temperature. Initially, blue light emission of 5.4 V and luminance of 920 cd / m ² was confirmed. The half life of luminance was 2300 hours. Note that no change in color tone was observed even after half-life.

In Example 12, an organic electroluminescent element was produced according to the procedure described in Example 12 except that the compound of Illustrative Compound 2 was used instead of the compound of Illustrative Compound 2 in forming the light emitting layer. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1) .

In Example 12, an organic electroluminescent device was produced according to the procedure described in Example 12 except that the compound of Illustrative Compound 2 was used instead of the compound of Illustrative Compound 2 in forming the light emitting layer. Blue light emission was confirmed from the element. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

In Example 12, an organic electroluminescent device was produced according to the procedure described in Example 12 except that the compound of Exemplified Compound 26 was used instead of the compound of Illustrated Compound 2 in forming the light emitting layer. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

In Example 12, an organic electroluminescent element was produced according to the procedure described in Example 12 except that the compound of Exemplified Compound 34 was used instead of the compound of Illustrated Compound 2 in forming the light emitting layer. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

In Example 12, an organic electroluminescent device was produced according to the procedure described in Example 12 except that the compound of Illustrative Compound 45 was used instead of the compound of Illustrative Compound 2 in forming the light emitting layer. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

[Reference Example 4]
In Example 12, an organic electroluminescent element was produced according to the procedure described in Example 12 except that the compound of Exemplified Compound 47 was used instead of the compound of Illustrated Compound 2 in forming the light emitting layer. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

Comparative Example 1:
In Example 12, the formation of the light emitting layer was carried out except that 9,10-bis (9,9-dimethyl-9H-fluoren-2-yl) anthracene was used instead of using the compound of Exemplary Compound 2. According to the operation described in Example 12, an organic electroluminescent device was produced. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

Comparative Example 2:
In Example 12, in the formation of the light emitting layer, an organic compound was prepared according to the procedure described in Example 12, except that 9,10-di (2′-naphthyl) anthracene was used instead of the compound of Exemplary Compound 2. An electroluminescent element was produced. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1). Further, when the organic electroluminescent device was left at 100 ° C. for 1 hour, it was confirmed that light emission from the device was attenuated.

A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was subjected to ultrasonic cleaning using a neutral detergent, semi-coclean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and isopropanol, and further washed by boiling with isopropanol. . The substrate was dried with nitrogen gas, further UV / ozone cleaned, fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa.

First, 4,4 ′, 4 ″ -tris (2 ″ ′-naphthylphenylamino) triphenylamine is deposited on the ITO transparent electrode to a thickness of 60 nm at a deposition rate of 0.1 nm / sec, and the first hole is formed. An injection transport layer was formed. Next, N, N′-diphenyl-N, N′-di (2′-naphthyl) -4,4′-diamino-1,1′-biphenyl was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec. The second hole injecting and transporting layer was formed. Next, Exemplified Compound 37 was deposited on the hole injecting and transporting layer to a thickness of 40 nm at a deposition rate of 0.2 nm / sec to form a light emitting layer. On the light-emitting layer, tris (8-quinolinolato) aluminum was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. An aluminum / lithium alloy was deposited thereon as a cathode to a thickness of 10 nm at a deposition rate of 2.0 nm / sec. Finally, aluminum was deposited to a thickness of 200 nm at a deposition rate of 2.0 nm / sec to form an electrode. A light emitting element was manufactured.
In addition, vapor deposition was implemented, maintaining the pressure reduction state of a vapor deposition tank. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a current density of 10 mA / cm ² in a dry atmosphere. Initially, blue light emission of 5.4 V and luminance of 530 cd / m ² was confirmed. The half life of luminance was 950 hours. Note that no change in color tone was observed even after half-life.

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, Semicoclean (manufactured by Furuuchi Chemical), ultrapure water, and isopropanol boiling washing. The substrate was dried with nitrogen gas, further washed with U / V ozone, fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa.
On the ITO transparent substrate, N, N′-diphenyl-N, N ′-(2′-naphthyl) -4,4′-diamino-1,1′-biphenyl is deposited to a thickness of 40 nm at a deposition rate of 0.2 nm / sec. To form a first hole injection transport layer. Subsequently, the compound of the exemplary compound 27 was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec to form a second hole injecting and transporting layer. Thereafter, the compound of Exemplified Compound 50 and coumarin 6 were co-deposited from different vapor deposition sources to a thickness of 40 nm at a vapor deposition rate of 0.2 nm / sec and a vapor deposition rate of 0.02 nm / sec to form a light emitting layer. Further, tris (8-quinolinolato) aluminum was deposited on the light emitting layer to a thickness of 30 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Thereafter, lithium fluoride is deposited to a thickness of 1 nm at a deposition rate of 0.2 nm / sec, and aluminum is deposited to a thickness of 150 nm at a deposition rate of 2.0 nm / sec to form a cathode. Was made. The vapor deposition was carried out while maintaining the reduced pressure in the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescent element, and it was continuously driven at a low current density of 10 mA / cm ² in a dry atmosphere at room temperature. Initially, green light emission of 5.6 V, 1400 cd / m ² was confirmed. The luminance half-life was 3200 hours. Note that no change in color tone was observed even after half-life.

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, Semicoclean (manufactured by Furuuchi Chemical), ultrapure water, and isopropanol boiling washing. The substrate was dried with nitrogen gas, further washed with U / V ozone, fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa.
N, N′-diphenyl-N, N ′-(2′-naphthyl) -4,4′-diamino-1,1′-biphenyl is deposited on an ITO transparent substrate to a thickness of 50 nm at a deposition rate of 0.2 nm / sec. To form a first hole injection transport layer. Next, the compound of Exemplified Compound 29 and rubrene were co-evaporated from different vapor deposition sources to a thickness of 40 nm at a vapor deposition rate of 0.2 nm / sec and a vapor deposition rate of 0.02 nm / sec to form a light emitting layer. On top of this, tris (8-quinolinolato) aluminum was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Thereafter, lithium fluoride is deposited to a thickness of 1 nm at a deposition rate of 0.2 nm / sec, and aluminum is deposited to a thickness of 150 nm at a deposition rate of 2.0 nm / sec to form a cathode. Was made. The vapor deposition was carried out while maintaining the reduced pressure in the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescent element, and it was continuously driven at a low current density of 10 mA / cm ² in a dry atmosphere at room temperature. Initially, yellow light emission of 5.6 V and 1300 cd / m ² was confirmed. The half life of luminance was 2500 hours. Note that no change in color tone was observed even after half-life. .

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, Semicoclean (manufactured by Furuuchi Chemical), ultrapure water, and isopropanol boiling washing. The substrate was dried with nitrogen gas, further washed with U / V ozone, fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa.
4,4 ′, 4 ″ -tris (2 ″ ′-naphthylphenylamino) triphenylamine is deposited on an ITO transparent substrate to a thickness of 60 nm at a deposition rate of 0.1 nm / sec to form a first hole injecting and transporting layer. Formed. Next, N-phenyl-N- (1 ″ -naphthyl) -4,4′-diamino-1,1′-biphenyl was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec to provide a second hole transport. On top of that, Exemplified Compound 27 and 2,5,8,11-tetra-tert-butylperylene were deposited from different deposition sources at a deposition rate of 0.2 nm / sec and a deposition rate of 0.01 nm / sec to 40 nm. A light-emitting layer was formed by co-evaporation to a thickness of 1. The compound of the exemplary compound 47 was deposited on the light-emitting layer to a thickness of 10 nm at a deposition rate of 0.2 nm / sec to form a second electron injecting and transporting layer. Further, tris (8-quinolinolato) aluminum was vapor-deposited to a thickness of 10 nm at a vapor deposition rate of 0.2 nm / sec to form a first electron injection / transport layer, and then lithium fluoride was vapor-deposited at a vapor deposition rate of 0.2 nm / sec. 1 In addition, an organic electroluminescence device was produced by depositing aluminum to a thickness of m and further depositing aluminum at a deposition rate of 2.0 nm / sec to a thickness of 150 nm to form a cathode. A DC voltage was applied to the produced organic electroluminescent device, and it was continuously driven at a low current density of 10 mA / cm ² at room temperature in a dry atmosphere, initially 5.9 V and 640 cd / m ² . Blue light emission was confirmed, and the luminance half-life was 1200 hours, and no change in color tone was observed even after half-life.

[Reference Example 5]
Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was ultrasonically cleaned using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried with nitrogen gas and further UV / ozone cleaned. Next, on the ITO transparent electrode, polymethyl methacrylate (weight average molecular weight 25000), N, N′-diphenyl-N, N ′-(2′-naphthyl) -4,4′-diamino-1,1′- 120 nm light emitting layer by spin coating using 3 wt% dichloroethane solution containing biphenyl, compound of exemplified compound 47, and tris (8-quinolinolato) aluminum in a weight ratio of 100: 50: 30: 0.5, respectively Formed. Next, the glass substrate having the light emitting layer was fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition layer was decompressed to 2 × 10 ⁻⁴ Pa. On the light emitting layer, magnesium and silver were co-deposited as a cathode at a deposition rate of 2.0 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, thereby producing an organic electroluminescent device. When a DC voltage of 15 V was applied to the produced organic electroluminescent element at room temperature in a dry atmosphere, a current of 84 mA / cm ² flowed, and blue-green light emission with a luminance of 430 cd / m ² was confirmed. The half life of luminance was 410 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 excellent durability.

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 general formula (1) (Chemical formula 1).

[Wherein R _{1 to} R ₈ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, or a — (X ′) nZ ′ group (wherein Z ′ represents a substituted or unsubstituted straight group). Represents a chain, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, X ′ represents an oxygen atom or a sulfur atom, and n represents 0 or 1) , Ar represents a substituted or unsubstituted aryl group (excluding 9-anthracenyl group, fluorenyl group, and phenyl group) , X represents an oxygen atom or a sulfur atom, Z represents a substituted or unsubstituted aryl group ] An organic electroluminescence device comprising at least one layer containing at least one anthracene compound represented by the following general formula (1) between a pair of electrodes.

[ Wherein R _{1 to} R ₈ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, or a — (X ′) nZ ′ group (wherein Z ′ represents a substituted or unsubstituted straight group). Represents a chain, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, X ′ represents an oxygen atom or a sulfur atom, and n represents 0 or 1) , Ar represents a substituted or unsubstituted aryl group (excluding 9-anthracenyl group), X represents an oxygen atom or a sulfur atom, and Z represents a substituted or unsubstituted aryl group ] The organic electroluminescence device according to claim 2 , wherein the layer containing the anthracene compound is a charge injection transport layer. The organic electroluminescent device according to claim 3 , wherein the charge injection transport layer is a hole injection transport layer. 4. The organic electroluminescent device according to claim 3 , wherein the charge injection / transport layer is an electron injection / transport layer. The organic electroluminescent element according to claim 2 , wherein the layer containing the anthracene compound is a light emitting layer. The organic electroluminescent element according to claim 2 , further comprising a hole injecting and transporting layer between the pair of electrodes. The organic electroluminescent element according to claim 2 , further comprising an electron injecting and transporting layer between the pair of electrodes.

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