JP2009001499A - Aromatic hydrocarbon compound and organic electroluminescent device containing the aromatic hydrocarbon compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a novel aromatic hydrocarbon compound and an organic electroluminescent device comprising the same. <P>SOLUTION: The aromatic hydrocarbon compound is represented by formula (1). In the formula, R<SB>1</SB>to R<SB>17</SB>each independently represents a hydrogen atom or a substituent, and Z represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

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

  Conventionally, an inorganic electroluminescent element has been used as a panel-type light source such as a backlight. However, in order to drive the light emitting element, an alternating high voltage is required. Recently, an organic electroluminescence element (organic electroluminescence element: organic EL element) using an organic material as a luminescent material has been developed [see, for example, Non-Patent Document 1].

An organic electroluminescent device has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, and electrons and holes are injected into the thin film and recombined to form an exciton (exington). ) And emits light using light emitted when the exciton is deactivated. The organic electroluminescence device can emit light at a low direct current voltage of about several V to several tens V, and various colors (for example, red, blue, green) can be selected by selecting the type of the fluorescent organic compound. Can emit light. In recent years, organic electroluminescent elements having such characteristics have been actively applied to various light emitting elements, display elements, and the like. However, generally, there is a demand for an organic electroluminescence device having low emission luminance, practically higher emission efficiency, and long-life emission.
Furthermore, in recent years, organic electroluminescent elements that emit red, blue, and green light with higher color purity are required with the colorization of various display elements. Among these, one problem of the organic electroluminescent device is to improve the performance of the red material, and there is a demand for an organic electroluminescent device that emits light with high color purity, high luminous efficiency, and long life.

  For example, Patent Document 1 discloses a red light-emitting element in which a naphthacene or pentacene derivative is added to a light-emitting layer. This light-emitting element has excellent red purity, but has a luminance half-life of about 150 hours. It was insufficient. Patent Document 2 discloses a device in which a dicyanomethylene compound is added to a light emitting layer, but red purity is insufficient. For example, Non-Patent Document 2 includes 5,10,15. , 20-tetraphenylbisbenzo [5,6] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-ln] perylene is described, and an organic electroluminescent device using this compound is disclosed in Japanese Patent It is described in Document 3, Patent Document 4, and Patent Document 5. However, the organic electroluminescent device using the compounds and derivatives thereof described in these documents has a maximum emission wavelength of 610 nm, and for a red organic electroluminescent device with a display specification, further longer wavelength emission, It is desired to increase the luminous efficiency, extend the lifetime, and emit light with high brightness at a low voltage.

Patent Document 6 describes an organic electroluminescence device using a 10- (benzo [k] fluoranthen-3′-yl) benzo [f] indeno [1,2,3-cd] benzo [o] perylene derivative. However, organic electroluminescence devices using these light emitting materials still require improvement in terms of light emission lifetime.
Appl.Phys.lett., 51,913 (1987) J. Amer. Chem. Soc. 118, 2374 (1996) Japanese Patent Laid-Open No. 8-311442 Japanese Patent Laid-Open No. 3-162481 JP 2000-86549 A Japanese Patent Laid-Open No. 10-330295 JP 2002-008867 A JP 2001-267078 A

  An object of the present invention is to provide an aromatic hydrocarbon compound and an organic electroluminescent device containing the compound. More specifically, an aromatic hydrocarbon compound that is suitable for a light emitting material of an organic electroluminescent device, has excellent vapor deposition properties, has high thermal stability and excellent color purity (emission wavelength is long), and the aromatic hydrocarbon compound It is to provide an organic electroluminescent device having excellent stability and durability, and excellent color purity.

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

[Wherein, R _{1 to} R ₁₇ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aromatic hydrocarbon. Group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, carboxyl group, substituted or unsubstituted A substituted amino group or a cyano group, and Z represents a substituted or unsubstituted aromatic hydrocarbon group having 19 or less nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group]

  <2>: In general formula (1), Z is a substituted or unsubstituted aromatic hydrocarbon group represented by general formula (2), or a substituted or unsubstituted aromatic group represented by general formula (3) The aromatic hydrocarbon compound according to <1>, which is an aromatic group heterocyclic (Chemical Formula 2),

[Wherein, Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ each independently represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, substituted or Substituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, Represents a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and the adjacent groups of Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ form a ring together with the adjacent groups to form an aromatic hydrocarbon ring , An aliphatic hydrocarbon ring, an aromatic heterocyclic ring, or an aliphatic heterocyclic ring, Y _{1 to} Y ₅ represent a carbon atom or a nitrogen atom, and at least one of Y _{1 to} Y ₅ represents nitrogen. When Y ₁ is a nitrogen atom, Rb ₅ is not present; when Y ₂ is a nitrogen atom, Rb ₄ is not present; and Y ₃ is a nitrogen atom. , Rb ₃ does not exist, and when Y ₄ is a nitrogen atom, Rb ₂ does not exist, and when Y ₅ is a nitrogen atom, Rb ₁ does not exist.

  <3>: The aromatic according to <2>, wherein the general formula (2) is a group (chemical formula 3) selected from the group consisting of the general formulas (2-A) to (2-E) and (2-G) Hydrocarbon compounds,

Wherein, Rc ₁ to Rc ₅ is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl Represents an oxy group, a substituted or unsubstituted arylthio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and Rd _{1 to} Rd ₁₀ , Re _{1 to} Re ₈ , Rf ₁ to Rf _10, Rg ₁ ~Rg _10, and, in Ri ₁ to Ri ₈ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted Substituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl Represents a thio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, _one of Rd _{1 to} Rd ₁₀ , one of Re _{1 to} Re ₈ , Rf one of the _{1 ~Rf 10,} one of Rg ₁ ~Rg _10, and, one of Ri ₁ to Ri ₈ represents a bond, _{X 1} is an oxygen atom, a sulfur atom or, , —C (R ′) (R ″) —, wherein R ′ and R ″ are each independently a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic group, A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group)

<4>: An organic electroluminescent device comprising at least one layer containing at least one kind of the aromatic hydrocarbon compound according to any one of <1> to <3> between a pair of electrodes,
<5>: The organic electroluminescent device according to <4>, wherein the layer containing the aromatic hydrocarbon compound according to any one of <1> to <3> is a light emitting layer.
<6>: The organic electroluminescent device according to <4>, wherein the layer containing the aromatic hydrocarbon compound according to any one of <1> to <3> is hole injection transport;
<7>: The organic electroluminescence device according to <4>, wherein the layer containing the aromatic hydrocarbon compound according to any one of <1> to <3> is an electron injecting and transporting layer.

  According to the present invention, it is possible to provide a novel aromatic hydrocarbon compound and an organic electroluminescence device using the aromatic hydrocarbon compound. More specifically, an aromatic hydrocarbon compound that is suitable for a light-emitting material of an organic electroluminescence device, has excellent vapor deposition properties, high thermal stability, and excellent color purity (emission wavelength is long), and the aromatic hydrocarbon compound It is possible to provide an organic electroluminescent device using the above, having excellent stability and durability and excellent color purity.

The present invention will be described in detail below.
The aromatic hydrocarbon compound of the present invention is a compound represented by the general formula (1) (chemical formula 4).

[Wherein, R _{1 to} R ₁₇ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aromatic hydrocarbon. Group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, carboxyl group, substituted or unsubstituted A substituted amino group or a cyano group, and Z represents a substituted or unsubstituted aromatic hydrocarbon group having 19 or less nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group]

In the aromatic hydrocarbon compound represented by the general formula (1), R _{1 to} R ₁₇ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic group. An alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group (including those composed of a single ring or a plurality of condensed rings; the same shall apply hereinafter), a substituted or unsubstituted aromatic heterocyclic group (a single ring or a plurality of condensed rings). The same shall apply hereinafter), substituted or unsubstituted aralkyl groups, substituted or unsubstituted aryloxy groups (wherein aryl represents an aromatic hydrocarbon group or an aromatic heterocyclic group), substituted Or an unsubstituted arylthio group (wherein aryl represents an aromatic hydrocarbon group or an aromatic heterocyclic group), a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, Or a cyano group, preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms. A substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 40 carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms A substituted or unsubstituted aryloxy group having 3 to 50 carbon atoms (wherein aryl represents an aromatic hydrocarbon group or an aromatic heterocyclic group), a substituted or unsubstituted group having 3 to 50 carbon atoms Arylthio group (wherein aryl represents an aromatic hydrocarbon group or an aromatic heterocyclic group), hydroxyl group, nitro group, carboxyl group, unsubstituted amino group, substituted amino group having 1 to 50 carbon atoms Alternatively, it represents a cyano group, and more preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, or a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms. A substituted or unsubstituted aromatic hydrocarbon group having 6 to 45 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 35 carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 35 carbon atoms A substituted or unsubstituted aryloxy group having 3 to 45 carbon atoms (wherein aryl represents an aromatic hydrocarbon group or an aromatic heterocyclic group), a substituted or unsubstituted group having 3 to 45 carbon atoms An arylthio group (wherein aryl represents an aromatic hydrocarbon group or an aromatic heterocyclic group), an unsubstituted amino group, a substituted amino group having 1 to 50 carbon atoms, or a cyano group; Like Or a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, or a 6 to 45 carbon atom. A substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group having 3 to 35 carbon atoms, an unsubstituted amino group, a substituted amino group having 1 to 30 carbon atoms, or cyano Represents a group.

  Here, as a substituent of a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group and a substituted or unsubstituted aralkyl group, a halogen atom, a linear, branched or cyclic alkyl group A linear, branched or cyclic alkoxy group, a linear, branched or cyclic alkenyl group, an aromatic hydrocarbon group (which may be mono- or polysubstituted by an alkyl group, an alkoxy group or an aromatic hydrocarbon group). Good), an aromatic heterocyclic group (which may be mono- or polysubstituted by an alkyl group, an alkoxy group, or an aromatic hydrocarbon group), an aryloxy group (wherein aryl is an aromatic carbon group) And a substituted or unsubstituted amino group, preferably a linear, branched or cyclic alkyl group, linear, branched or A cyclic alkoxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group, an unsubstituted amino group, and a substituted amino group having 1 to 50 carbon atoms, more preferably a straight chain having 1 to 20 carbon atoms. A branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 50 carbon atoms, and an aromatic heterocyclic group having 3 to 40 carbon atoms And an unsubstituted amino group and a substituted amino group having 1 to 50 carbon atoms.

  In addition, as a substituent in a substituted or unsubstituted amino group, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic hydrocarbon group (substitution or unsubstituted here is the same as described above) Or a substituted or unsubstituted aromatic heterocyclic group (wherein substituted or unsubstituted is the same as above), preferably a linear, branched or cyclic group having 1 to 20 carbon atoms An alkyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocyclic group having 3 to 50 carbon atoms.

Specific examples of the halogen atom for R _{1 to} R ₁₇ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Specific examples of the linear, branched or cyclic alkyl group represented by R _{1 to} R ₁₇ include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl 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, 3,5,5-trimethylhexyl, n-decyl, 1-ethyloctyl, n-undecyl, 1-methyldecyl, n-dodecyl, 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, isobornyl 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, cyclohexyl group 4-methylcyclohexyl group, 3-methyl Rucyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3-tert-butylcyclohexyl group, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl group, 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-methoxypropyl 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-octyl Xylbutyl, 4-n-decyloxybutyl, 4-n-dodecyloxybutyl, 5-methoxypentyl, 5-ethoxypentyl, 5-n-propoxypentyl, 6-ethoxyhexyl, 6-iso Propoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8 -Methoxyoctyl group, 10-methoxydecyl group, 10-n-butoxydecyl group, 12-ethoxydodecyl group, 12-isopropoxide decyl group, tetrahydrofurfuryl group,
2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butoxyethoxy) ethyl group, 3- (2′-ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4′-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2′-hexenyloxy) propyl group, 3- (2′-heptenyloxy) propyl group, 3 -(1'-cyclohexenyloxy) propyl group, 4-allyloxybutyl group,
Benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4′-methylbenzyloxy) ethyl group, 2- (2′-methylbenzyloxy) ethyl group, 2- (4 ′) -Fluorobenzyloxy) ethyl group, 2- (4'-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4'-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (Benzyloxymethoxy) ethyl group, 2- (4′-methylbenzyloxymethoxy) ethyl group,
Phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4-chlorophenyloxymethyl group Group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl group, 2- (4′-methoxyphenyl) Oxy) ethyl group, 2- (4′-chlorophenyloxy) ethyl group, 2- (4′-bromophenyloxy) ethyl group, 2- (1′-naphthyloxy) ethyl group, 2- (2′-naphthyloxy) ) Ethyl group, 3-phenyloxypropyl group, 3- (2′-naphthyloxy) propyl group, 4-phenyloxy Sibutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl group, 10-phenyloxydecyl group, 10- (3′-chlorophenyloxy) decyl group, 2- (2′-phenyloxyethoxy) ethyl group, 3- (2′-phenyloxyethoxy) propyl group, 4- (2 ′ -Phenyloxyethoxy) butyl group,
n-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2-n-octyl Thioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2 ′ -Methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl group, 2-allylthioethyl group, 2- N-dithioethyl group, 3- (4′-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2′-benzyloxyethylthio) ethyl group, 3- (3′-benzylthiopropylthio) propyl group ,
2-phenylthioethyl group, 2- (4′-methoxyphenylthio) ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) propyl group,
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 aromatic hydrocarbon group or the substituted or unsubstituted aromatic heterocyclic group represented by R _{1 to} R ₁₇ include, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, 4- Phenyl-1-naphthyl group, 6-phenyl-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, 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, -Dimethyl-9-phenanthryl group, 1,8-diphenyl-9-phenanthryl group, 2-chloro-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, 1,2 , 3,4-tetrahydronaphthalen-6-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, 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-pyret 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-teto Methyl-2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, 4-quinolinyl group, 3-quinolinyl group, 2-quinolinyl group, 1-phenyl-isoquinolin-3-yl group, 2-phenyl-7-naphthyridinyl group, 2-phenanthrolinyl group, 4-pyridinyl group, 3-pyridinyl group, 2- Pyridinyl group, 2-phenyl-5-pyridyl group, 2-phenyl-4-pyridyl group, 2,5-diphenyl-4-pyridyl group, 2- (2′-pyridyl) -5-pyridyl group, 2,5- Di (2′-pyridyl) -4-pyridyl group, 2-ethyl-6-phenyl-4-pyridyl group, 2,3,4-triphenyl-6-pyridyl group, 3-ethyl-4-pyridyl group, 2 - Midinyl group, 2-phenyl-5-pyrimidinyl group, 2- (2 ′, 6′-dimethylphenyl) -5-pyrimidinyl group, 4,5-diphenyl-2-pyrimidinyl group, 2-pyridazinyl group, 2-pyrazinyl group 4,6-diphenyl-1,3,5-triazin-2-yl group, 4,6-di (2′-naphthyl) -1,3,5-triazin-2-yl group, 4,6-di (1′-naphthyl) -1,3,5-triazin-2-yl group, 3-furanyl group, 2-furanyl group, 3-thienyl group, 2-thienyl group, 2-benzofuranyl group, 2-benzothiophenyl 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- ethyl Phenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 2-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, 2-tert-butylphenyl group, 4-n -Pentylphenyl group, 4-isopentylphenyl group, 2-neopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 3-n-hexylphenyl group, 4- (2'-ethylbutyl) ) Phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2′-ethylhexyl) phenyl group, 4-tert-octyl Ruphenyl 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-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, 2,6-diethylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisobutene Ruphenyl 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, 4-n-hexyloxyphenyl group, 2- (2 '-Ethylbutyloxy) phenyl group, 4-n-octyloxyphenyl group, 4-n-de Siloxyphenyl 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, 2-phenyloxyphenyl group, 3-phenyloxyphenyl group, 4-phenyloxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 2,6-diphenylphenyl group, 3 , 5-diphenylphenyl group, 2,4-diphenylphenyl group, 2,3-diphenylphenyl group, 2,5-diphenyl Phenyl group, 3,4-diphenylphenyl group, 2,4,6-triphenylphenyl group, 3,4,5-triphenylphenyl group, 2,4,5-triphenylphenyl group, 2- (2′- Pyridyl) phenyl group, 3- (2′-pyridyl) phenyl group, 4- (2′-pyridyl) phenyl group, 4- (4′-methylphenyl) phenyl group, 4- (3′-methylphenyl) phenyl group 4- (4′-methoxyphenyl) phenyl group, 4- (4′-n-butoxyphenyl) phenyl group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-chlorophenyl) phenyl group, 3-methyl-4-phenylphenyl group, 2-ethyl-4-phenylphenyl group, 3-fluoro-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group, 2- (1′-naphthyl) phenyl 2- (2′-naphthyl) phenyl group, 3- (1′-naphthyl) phenyl group, 3- (2′-naphthyl) phenyl group, 4- (1′-naphthyl) phenyl group, 4- (2 ′ -Naphthyl) phenyl group, 4- (2'-naphthyl) -1-naphthyl group, 2-phenyl-1-naphthyl group, 1-phenyl-2-naphthyl group, 4- (1'-naphthyl) -1-naphthyl Group, 6- (2′-naphthyl) -2-naphthyl group, 6- (1′-naphthyl) -2-naphthyl group, 6-N, N-diphenylamino-2-naphthyl group, 4-N, N— Diphenylamino-1-naphthyl group, 4-cyanophenyl group, 3-cyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2- Chlorophenyl group, 4-bromoph An phenyl group, a 3-bromophenyl group, a 2-bromophenyl group, a 4-chloro-1-naphthyl group, a 4-chloro-2-naphthyl group, a 6-bromo-2-naphthyl group, a 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-naphthyl group, 1,6- Dichloro-2-naphthyl group, 2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 3-fluoro-2-methylphenyl group, -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-methoxyphenyl group, 2-fluoro -4-ethoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 3-chloro-4-meth Siphenyl group, 2-methoxy-5-chlorophenyl group, 3-methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl group, 3-N, N-diphenylaminophenyl group, 4-N, N- Diphenylaminophenyl group, 9,9-dimethyl-9H-fluoren-2-yl group, 9,9-diethyl-9H-fluoren-2-yl group, 9,9-di-n-hexyl-9H-fluorene-2 -Yl group, 9,9-di-n-octyl-9H-fluoren-2-yl group, 9,9-diphenyl-9H-fluoren-2-yl group, 9,9-dicyclohexyl-9H-fluoren-2- Yl group, 9,9-dibenzyl-9H-fluoren-2-yl group, 7-N, N-diphenylamino-9,9-dimethyl-9H-fluoren-2-yl group, dibenzofuran- 2-yl group, dibenzofuran-4-yl group, dibenzofuran-3-yl group, dibenzofuran-2-yl group, dibenzothiophen-4-yl group, dibenzothiophen-3-yl group, dibenzothiophen-2-yl group It can be mentioned, but is not limited to these.

Specific examples of the linear, branched or cyclic alkoxy group represented by R _{1 to} R ₁₇ include an alkoxy group derived from the above linear, branched or cyclic alkyl group.

Specific examples of the substituted or unsubstituted aralkyl group of R _{1 to} R ₁₇ include, for example, benzyl group, α-methylbenzyl group, α-ethylbenzyl 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-ethyl Benzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2-tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert -Octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl 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-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group,
4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4-hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl And aralkyl groups such as a group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group.

Specific examples of the substituted or unsubstituted aryloxy group for R _{1 to} R ₁₇ include the above-described substituted or unsubstituted aromatic hydrocarbon groups, or substitutions derived from substituted or unsubstituted aromatic heterocyclic groups. Or an unsubstituted aryloxy group can be mentioned.

Specific examples of the substituted or unsubstituted arylthio group represented by R _{1 to} R ₁₇ include a substituted or unsubstituted aromatic hydrocarbon group described above or a substituted or unsubstituted aromatic heterocyclic group derived from An unsubstituted arylthio group can be mentioned.

Specific examples of the substituted or unsubstituted amino group of R _{1 to} R ₁₇ include, for example, an amino group, an N-methylamino group, an N-ethylamino group, an Nn-propylamino group, an N-isopropylamino group, Nn-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 -Phenylphenyl) amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group, N- (4-methylphenyl) amino group, N- (2-methyl) Ruphenyl) amino group, N- (2-anthranyl) amino group, N- (9-anthranyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino Group, N, N-di-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-ethyl Amino 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-cycl Lopentylamino 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- Phenyl-N- (4-methylphenyl) amino group, N-phenyl-N- (3-methylphenyl) amino group N-phenyl-N- (2-methylphenyl) amino group, N-phenyl-N- (4-methoxyphenyl) amino group, N-phenyl-N- (3-methoxyphenyl) amino group, N-phenyl-N -(2-methoxyphenyl) amino group, N-phenyl-N- (1-naphthyl) amino group, N-phenyl-N- (2-naphthyl) amino group, N-phenyl-N- (4-phenyl-1) -Naphtyl) amino group, N-phenyl-N- (4-phenylphenyl) amino group, N-phenyl-N- (3-phenylphenyl) amino group, N-phenyl-N- (2-phenylphenyl) amino group N-phenyl-N- (4-cyclohexylphenyl) amino group, N-phenyl-N- (3-cyclohexylphenyl) amino group, N-phenyl-N- (2-cyclohexylphenyl) Nyl) amino group, N-phenyl-N- [4- (2′-pyridinyl) phenyl] amino group, N-phenyl-N- [4- (4′-pyridinyl) phenyl] amino group, N-phenyl-N -(4-phenoxyphenyl) amino group, N-phenyl-N- (3-phenoxyphenyl) amino group, N-phenyl-N- (9-phenanthrenyl) amino group, N-phenyl-N- (9-phenyl- 10-phenanthrenyl) amino group, N-phenyl-N- (9,9-dimethyl-9H-fluoren-2-yl) amino group, N-phenyl-N- (2′-pyridinyl) amino group, N-phenyl- N- (3′-pyridinyl) amino group, N-phenyl-N- (4′-pyridinyl) amino group, N- (1-naphthyl) -N- (4′-phenylphenyl) amino group, N- (1 -Naphthyl) -N- (3'-phenylphenyl) amino group, N- (1-naphthyl) -N- (2'-phenylphenyl) amino group, N- (2-naphthyl) -N- (4'-phenylphenyl) An amino group, N- (2-naphthyl) -N- (3′-phenylphenyl) amino group, N- (2-naphthyl) -N- (2′-phenylphenyl) amino group,
N, N-di (4-methylphenyl) amino group, N, N-di (3-methylphenyl) amino group, N, N-di (2-methylphenyl) amino group, N, N-di (4- Methoxyphenyl) amino group, N, N-di (3-methoxyphenyl) amino group, N, N-di (2-methoxyphenyl) amino group, N, N-di (1-naphthyl) amino group, N, N -Di (2-naphthyl) amino group, N- (1-naphthyl) -N- (2-naphthyl) amino group, N, N-di (4-phenylphenyl) amino group, N, N-di (3- Phenylphenyl) amino group, N, N-di (2-phenylphenyl) amino group, N, N-di (4-cyclohexylphenyl) amino group, N, N-di (3-cyclohexylphenyl) amino group, N, N-di (2-cyclohexylphenyl) amino group, N N- di (4-phenoxyphenyl) amino group, N, N- di (3-phenoxyphenyl) amino group, N, N- di (9-phenanthryl) amino group,
N-carbazolyl group, 3,6-dimethyl-N-carbazolyl group, 3,6-diphenyl-N-carbazolyl group, 3,6-bis (N, N-diphenylamino) -N-carbazolyl group, 3,6- Bis [N-phenyl-N- (1′-naphthyl) amino] -N-carbazolyl group, 3,6-bis [N-phenyl-N- (4′-phenylphenyl) amino] -N-carbazolyl group, 3 , 6-Bis [N-carbazolyl] -N-carbazolyl group, 3- (N, N-diphenylamino) -N-carbazolyl group, 3- (N, N-diphenylamino) -6-phenyl-N-carbazolyl group 3- [N-phenyl-N- (1′-naphthyl) amino] -N-carbazolyl group, 1,8-diphenyl-3,6-bis (N, N-diphenylamino) -N-carbazolyl group, 3 − (N, N Diphenylamino) -6- [N- phenyl-N-(1'-naphthyl) amino] carbazolyl group, N- phenothiazinyl group, and a substituted or unsubstituted amino group, such as N- phenoxazinyl group.

In the aromatic hydrocarbon compound represented by the general formula (1), Z is an aromatic hydrocarbon group having 19 or less substituted or unsubstituted nuclear carbon atoms (referring to the number of carbon atoms forming a ring including a bond), Alternatively, it represents an aromatic heterocyclic group, wherein the substituent for Z includes a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aromatic carbonization A hydrogen group (wherein the substituents have the same meaning as the substituent of the substituted or unsubstituted aromatic hydrocarbon group of R _{1 to} R ₁₇ ), a substituted or unsubstituted aromatic heterocyclic group (here And the substituent is the same as the substituent of the substituted or unsubstituted aromatic heterocyclic group represented by R _{1 to} R ₁₇ , or a substituted or unsubstituted aryloxy group (wherein the substituent is a substituted or unsubstituted R ₁ to R ₁₇ Represents the same meaning as the substituent of the aryloxy group), a substituted or unsubstituted arylthio group (here, the substituent represents the same meaning as the substituent of the substituted or unsubstituted arylthio group R ₁ to R ₁₇ ), A hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group (wherein the substituent is a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted group) Or an unsubstituted aromatic heterocyclic group), or a cyano group, preferably a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, or a C 1-20 carbon atom. linear, branched or cyclic alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group (wherein 6 to 40 carbon atoms, examples of the substituent, a substituted or non-location of the R ₁ to R ₁₇ Represents the same meaning as the substituent of the aromatic hydrocarbon group), a substituted or unsubstituted aromatic Hajime Tamaki having a carbon number of 3 to 40 (where, as the substituent, the substitution of R ₁ to R ₁₇ Or the same meaning as the substituent of the unsubstituted aromatic heterocyclic group), a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms (wherein the substituents are those of R _{1 to} R ₁₇ ) The same meaning as the substituent of the substituted or unsubstituted aryloxy group), a substituted or unsubstituted arylthio group having 6 to 40 carbon atoms (wherein the substituents are substituted or unsubstituted R _{1 to} R ₁₇ ). The same meaning as the substituent of the substituted arylthio group), a hydroxyl group, a nitro group, a carboxyl group, an unsubstituted amino group, a substituted amino group having 1 to 50 carbon atoms (wherein, Linear, branched or cyclic al Represents a kill group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group), or a cyano group, more preferably a halogen atom or a C 1-10 carbon atom. A linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms (wherein the substituent as represents a substituted or same meaning as the substituent of unsubstituted aromatic hydrocarbon groups R ₁ to R _17), substituted or unsubstituted aromatic Hajime Tamaki having a carbon number of 3 to 30 (where And the substituents represent the same meaning as the substituents of the substituted or unsubstituted aromatic heterocyclic group represented by R _{1 to} R ₁₇ ), an unsubstituted amino group, and a substituted amino group having 1 to 40 carbon atoms. (Here, the substituents are linear, branched, There represents a cyclic alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group), or a cyano group.

  In the aromatic hydrocarbon compound represented by the general formula (1), a substituted or unsubstituted aromatic hydrocarbon group having 19 or less nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group represented by Z As specific examples of these, among the specific examples of substituted or unsubstituted aromatic hydrocarbon groups or substituted or unsubstituted aromatic heterocyclic groups given as specific examples of R1 to R17, substituted or unsubstituted nuclear carbon An aromatic hydrocarbon group having a number of 19 or less, or a substituted or unsubstituted aromatic heterocyclic group can be exemplified.

Specific examples of the substituents of Z are, for example, a halogen atom mentioned as specific examples of the halogen atom of R ₁ to R _17, straight-chain R ₁ to R _17, specific examples of the alkyl group branched or cyclic include straight, branched or cyclic alkyl group, mentioned as specific examples of straight-chain, branched or cyclic alkoxy group of R ₁ to R _17, straight-chain, branched or cyclic alkoxy group, the R ₁ to R ₁₇ A substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group, as a specific example of a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, R listed as specific examples of the substituted or unsubstituted aryloxy group ₁ to R _17, a substituted or unsubstituted aryloxy group, and specific examples of the substituted or unsubstituted arylthio group R ₁ to R ₁₇ A substituted or unsubstituted arylthio group mentioned Te, a hydroxyl group, a nitro group, a carboxyl group, a substituted or a substituted or unsubstituted amino group mentioned as specific examples of the unsubstituted amino group of R ₁ to R _17, a cyano group Can be mentioned.

  In the aromatic hydrocarbon compound represented by the general formula (1), Z is preferably a substituted or unsubstituted aromatic hydrocarbon group represented by the general formula (2), or represented by the general formula (3). Represents a substituted or unsubstituted aromatic heterocyclic group (Formula 5).

[Wherein, Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or an Substituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, Represents a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and the adjacent groups of Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ form a ring together with the adjacent groups, and are aromatic hydrocarbon rings. aliphatic hydrocarbon ring, aromatic heterocyclic ring, or may form an aliphatic heterocyclic ring, Y ₁ to Y ₅ represents a carbon atom or a nitrogen atom, the Y ₁ to Y ₅ One even without represents a nitrogen atom, when Y ₁ is a nitrogen atom, Rb ₅ is absent, when Y ₂ is a nitrogen atom, Rb ₄ is absent, Y ₃ is a nitrogen atom Rb ₃ is not present, Y ₄ is a nitrogen atom, Rb ₂ is not present, and Y ₅ is a nitrogen atom, Rb ₁ is not present.]

In general formula (2) and general formula (3), Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or Cyclic alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio Represents a group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and the adjacent groups of Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ each form a ring together with the adjacent group. formed, an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, aromatic heterocyclic ring, or may form an aliphatic heterocyclic ring, Y ₁ to Y ₅ is or a carbon atom Represents _atom, represent at least one nitrogen atom of Y 1 to Y _5, when _{Y 1} is a nitrogen atom, Rb ₅ is absent, when _{Y 2} is a nitrogen atom, Rb ₄ When Y ₃ is a nitrogen atom, Rb ₃ is not present. When Y ₄ is a nitrogen atom, Rb ₂ is not present and Y ₅ is a nitrogen atom. Rb ₁ does not exist.

_Ra 1 to Ra ₅ and _Rb 1 _{~Rb 5} in the general formula (2) and the general formula (3), preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms , A linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic group having 3 to 40 carbon atoms A heterocyclic group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 3 to 50 carbon atoms, A hydroxyl group, a nitro group, a carboxyl group, an unsubstituted amino group, a substituted amino group having 1 to 50 carbon atoms (wherein, the substituent includes a linear, branched or cyclic alkyl group, substituted or unsubstituted Aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group), or a cyano _group, adjacent groups of Ra 1 to Ra ₅ and _Rb 1 _{~Rb 5} are adjacent respectively A ring may be formed together with a group to form an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic heterocycle, or an aliphatic heterocycle, and more preferably a hydrogen atom, a halogen atom, or one carbon atom. -10 linear, branched or cyclic alkyl group, linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 45 carbon atoms, carbon atom A substituted or unsubstituted aromatic heterocyclic group having 3 to 35, a cyano group, an unsubstituted amino group, or a substituted amino group having 1 to 40 carbon atoms (wherein, the substituent is a straight chain, Branched or cyclic alkyl , A substituted or unsubstituted aromatic hydrocarbon group, a represents) a substituted or unsubstituted aromatic heterocyclic group, adjacent groups of Ra ₁ to Ra ₅ and Rb ₁ ~Rb _5, together with the respective adjacent groups A ring may be formed to form an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic heterocyclic ring, or an aliphatic heterocyclic ring.

Here, specific examples of Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ include, for example, the substituents exemplified as specific examples of the substituent of Z.

  The substituted or unsubstituted aromatic hydrocarbon group represented by the general formula (2) is preferably represented by the following general formulas (2-A) to (2-E) and (2-G). Group (Chemical Formula 6).

Wherein, Rc ₁ to Rc ₅ is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl Represents an oxy group, a substituted or unsubstituted arylthio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and Rd _{1 to} Rd ₁₀ , Re _{1 to} Re ₈ , Rf ₁ to Rf _10, Rg ₁ ~Rg _10, and, in Ri ₁ to Ri ₈ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted Substituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl Represents a thio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, _one of Rd _{1 to} Rd ₁₀ , one of Re _{1 to} Re ₈ , Rf one of the _{1 ~Rf 10,} one of Rg ₁ ~Rg _10, and, one of Ri ₁ to Ri ₈ represents a bond, _{X 1} is an oxygen atom, a sulfur atom or, , —C (R ′) (R ″) —, wherein R ′ and R ″ are each independently a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic group, A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group)

In formula _{(2-A), Rc 1} ~Rc 5 is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, a substituted Or an unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, preferably a halogen atom or 1 carbon atom -20 linear, branched or cyclic alkyl groups, linear, branched or cyclic alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 6 to 50 carbon atoms, 3 to 3 carbon atoms 50 substituted or unsubstituted aryloxy groups, substituted or unsubstituted arylthio groups having 3 to 50 carbon atoms, hydroxyl group, nitro group, carboxyl A group, an unsubstituted amino group, a substituted amino group having 1 to 50 carbon atoms (wherein the substituent includes a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or Represents a substituted or unsubstituted aromatic heterocyclic group) or a cyano group, more preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, or a carbon atom. A linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, an unsubstituted amino group, or a substituted amino group having 1 to 40 carbon atoms (wherein the substituent is a linear, branched or cyclic group) Represents an alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group).

Specific examples of the rc ₁ to Rc ₅ is, for _example, mentioned as examples of straight-chain, branched or cyclic alkyl group of R 1 halogen atom exemplified as the specific examples of the halogen atom _{to R 17,} R 1 _{to R 17} straight, branched or cyclic alkyl group, mentioned as specific examples of straight-chain, branched or cyclic alkoxy group of R ₁ to R _17, straight-chain, branched or cyclic alkoxy group, substituted of R ₁ to R ₁₇ Or a substituted or unsubstituted aryloxy group listed as a specific example of an unsubstituted aryloxy group, a substituted or unsubstituted arylthio group listed as a specific example of a substituted or unsubstituted arylthio group of R _{1 to} R ₁₇ , Examples of the substituted or unsubstituted amino group and cyano group mentioned as specific examples of the hydroxyl group, nitro group, carboxyl group, and substituted or unsubstituted amino groups of R _{1 to} R ₁₇ be able to.

In the general formulas (2-B) to (2-E) and (2-G), Rd _{1 to} Rd ₁₀ , Re _{1 to} Re ₈ , Rf _{1 to} Rf ₁₀ , Rg _{1 to} Rg ₁₀ , and Ri ₁ to Ri ₈ each independently represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic group. Heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, carboxyl group, substituted or unsubstituted amino group, or cyano Represents a group, preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, carbon A substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 40 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, Substituted or unsubstituted aryloxy group having 3 to 50 carbon atoms, substituted or unsubstituted arylthio group having 3 to 50 carbon atoms, hydroxyl group, nitro group, carboxyl group, unsubstituted amino group, 1 carbon atom -50 substituted amino groups (wherein the substituent represents a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group) Or a cyano group, more preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a linear, branched or cyclic group having 1 to 10 carbon atoms. Alkoxy groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 45 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 35 carbon atoms, unsubstituted amino groups, or carbon atoms The substituted amino group of number 1-40 is represented.

One of Rd _{1 to} Rd ₁₀ , one of Re _{1 to} Re ₈ , one of Rf _{1 to} Rf ₁₀ , one of Rg _{1 to} Rg ₁₀ , and Ri ₁ One of .about.Ri ₈ represents a bond.

Specific examples of Rd _{1 to} Rd ₁₀ , Re _{1 to} Re ₈ , Rf _{1 to} Rf ₁₀ , Rg _{1 to} Rg ₁₀ , and Ri _{1 to} Ri ₈ include specific examples of halogen atoms of R _{1 to} R ₁₇ , for example. Specific examples of the halogen atom, R _{1 to} R ₁₇ linear, branched or cyclic alkyl groups mentioned as R _{1 to} R ₁₇ linear, branched or cyclic alkyl groups, R _{1 to} R ₁₇ linear, branched or cyclic Specific examples of linear, branched or cyclic alkoxy groups, substituted or unsubstituted aromatic hydrocarbon groups of R _{1 to} R ₁₇ or substituted or unsubstituted aromatic heterocyclic groups mentioned as specific examples of alkoxy groups The substituted or unsubstituted aromatic hydrocarbon group or the substituted or unsubstituted aromatic heterocyclic group or the substituted or unsubstituted aryloxy group of R _{1 to} R ₁₇ listed as specific examples. Ario Shi group, a substituted or substituted or unsubstituted arylthio group mentioned as specific examples of the unsubstituted arylthio group R ₁ to R _17, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted R ₁ to R ₁₇ Examples of the amino group include substituted or unsubstituted amino groups and cyano groups.

X ₁ represents an oxygen atom, a sulfur atom, or a —C (R ′) (R ″) — group (where R ′ and R ″ are independently a hydrogen atom, straight chain, branched or cyclic). An alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, preferably an oxygen atom or —C (R ′) ( R ″) — represents a group.

  Here, R ′ and R ″ are preferably a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or Represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 20 carbon atoms, more preferably a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a substituted or substituted group having 6 to 15 carbon atoms, or It represents an unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group having 3 to 15 carbon atoms.

Specific examples of R 'and R ", substitution of the R ₁ linear to R _17, mentioned as specific examples of the alkyl group branched or cyclic, straight-chain, branched or cyclic alkyl group, R ₁ to R ₁₇ Or a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group listed as specific examples of an unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group be able to.

  Here, the substituent of “substituted or unsubstituted” has the same meaning as the substituent of Z in the general formula (1).

  The group represented by the general formula (2) preferably represents a group selected from the group consisting of (2-A), (2-B), (2-C), and (2-G).

  Specific examples of the aromatic hydrocarbon compound represented by the general formula (1) according to the present invention include the following compounds (Exemplary compounds A-1 to A-54, B-1). -B-76, B-79-B-120, C-1 to C-23) (Chemical Formula 7)-(Chemical Formula 22), the present invention is not limited to these. In the formula, n- represents normal.

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

[Wherein R _{1 to} R ₁₇ and Z represent the same meaning as in general formula (1)]
That is, an anthracene derivative represented by the general formula (A) is converted into an oxidizing agent (for example, aluminum chloride, aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, lead tetraacetate). , Or ferric chloride) to effect ring closure (for example, J. Amer. Chem. Soc., 102, 6504 (1980), Chem. Rev., 87, 357 (1987)). Can be referred to).

  Moreover, the aromatic hydrocarbon compound represented by General formula (1) can also be manufactured by the following process (Formula 24).

[Wherein, R _{1 to} R ₁₇ and Z represent the same meaning as in general formula (1), and L ₁ and L ₂ are both a leaving group such as a halogen atom or a trifluoromethylsulfonyloxy group, or Either one is a leaving group such as a halogen atom or a trifluoromethylsulfonyloxy group, and the other is a hydrogen atom. ]

That is, in the anthracene derivative represented by the general formula (B), when both L ₁ and L ₂ are a leaving group such as a halogen atom or trifluoromethanesulfonyloxy, the compound represented by the general formula (B) For example, nickel chloride, triphenylphosphine and zinc, and optionally in the presence of sodium bromide [see, for example, J. Org. Org. Chem. 81, 2627 (1988)], in the presence of a nickel catalyst [for example, bis (1,5-cyclooctadiene) nickel], optionally 2,2′- The reaction is carried out in the presence of bipyridyl and 1,5-cyclooctadiene [see, for example, the method described in J. Amer. Chem. Soc., 103, 6460 (1981), Macromolecules, 25, 1214 (1992). Can be produced by a method or the like.

In the general formula (B), when _one of L ₁ and L ₂ is a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group and the other is a hydrogen atom, for example, presence of potassium hydroxide Then, the reaction is performed in quinoline [for example, J. Chem. Soc. , 1108, (1954) can be referred to].

  Furthermore, the aromatic hydrocarbon compound represented by the general formula (1) can also be produced, for example, by the following step (Chemical Formula 25).

[Wherein R _{1 to} R ₁₇ and Z represent the same meaning as in general formula 1, one of L ₃ and L ₄ is a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group, and the other is Represents a boronic acid ester group such as a boronic acid group or a boron pinacolate group)

  That is, a compound represented by the general formula (C) and a compound represented by the general formula (D) are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, tritert-butylphosphine / palladium acetate] and a base ( For example, the compound represented by the general formula (1) can be produced by reacting in the presence of an inorganic base such as sodium carbonate or potassium carbonate, or an organic base such as triethylamine or pyridine.

  In addition, the compound represented by general formula (C) can be manufactured according to the following processes (Formula 26), for example.

[Wherein R _{1 to} R ₁₇ represent the same meaning as in general formula 1, and L ₅ represents a leaving group such as a halogen atom or a trifluoromethanesulfonyloxy group]

  That is, an anthracene derivative represented by the general formula (E) is converted into an oxidizing agent (for example, aluminum chloride, aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, lead tetraacetate). , Or ferric chloride) to cause ring closure [eg, J. Amer. Chem. Soc., 102, 6504 (1980), Chem. Rev., 87, 357 (1987), J. Mater]. . Chem. , 16, 1053 (2006) can be referred to].

  Similarly, an anthracene derivative represented by the general formula (E ′) is converted into an oxidizing agent (for example, aluminum chloride, aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate). , Lead tetraacetate, or ferric chloride) to produce a compound represented by the general formula (F), and then a halogenating agent (for example, N-bromosuccinimide, N- The compound represented by the general formula (C) can be produced by halogenation with iodosuccinimide).

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 aromatic hydrocarbon 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, if 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. In addition, when the light emitting layer is poor in hole injection function and / or 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 electroluminescent device of the present invention, the aromatic hydrocarbon compound represented by the general formula (1) is used as at least one of the constituent components of the hole injection transport layer, the electron injection transport layer, and the light emitting layer. And is more preferably used as a constituent of the light emitting layer.
In the organic electroluminescent element of the present invention, the aromatic hydrocarbon 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 2 / hole injection transport layer 3 / light emitting layer 4 / electron injection transport layer 5 / cathode 6 Type device (FIG. 1), (EL-2) anode 2 / hole injection transport layer 3 / light emitting layer 4 / cathode 6 type device (FIG. 2), (EL-3) anode 2 / light emitting layer 4 / electron injection transport Layer 5 / cathode 6 type element (FIG. 3), (EL-4) anode 2 / light emitting layer 4 / cathode 6 type element (FIG. 4), and the like. Further, (EL-5) anode 2 / hole injection / transport layer 3 / electron injection / transport layer 5 ″ / light-emitting layer 4 / electron injection / transport layer in which the light-emitting layer 4 is sandwiched between electron injection / transport layers 5 ″ and 5 5 / Cathode 6 type element (FIG. 5) can also be used. In addition, 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 the light emitting layer 4, and (EL-6) hole injection transport as the light emitting layer 4. A device of a type sandwiched between a pair of electrodes in a single layer form in which a component 3a, a light emitting component 4a and an electron injection component 5a are mixed (FIG. 6), (EL-7) as a light emitting layer 4, a hole injection transport component 3a and An element of a type in which a light emitting component 4a is mixed and sandwiched between a pair of electrodes (FIG. 7), (EL-8) as a light emitting layer 4, a light emitting component 4a and an electron injection component 5a are mixed in a single layer form. Any of the elements (FIG. 8) of the type sandwiched between a pair of electrodes may be used.

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

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

  Hereinafter, the components of the organic electroluminescence device of the present invention will be described in detail. As an example, (EL-1) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode type device shown in FIG. 1 will be described.

  In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injecting and transporting layer, 4 is a light emitting layer, 5 is an electron injecting and transporting layer, 6 is a cathode, and 7 is a power source.

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

As the anode 2, it is preferable to use a metal, an alloy or a conductive compound having a relatively large work function as an electrode material. Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In ₂ O ₃ ), tin oxide (SnO ₂ ), zinc oxide, 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 organic electroluminescent device of the present invention comprises an aromatic hydrocarbon compound represented by the general formula (1) and / or other compounds having a hole injecting and transporting function (for example, phthalocyanine derivatives, triaryls) An amine derivative, a triarylmethane 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.) can do.
The compounds having a hole injecting and transporting function may be used alone or in combination.

  Examples of the compound having a hole injecting and transporting function other than the aromatic hydrocarbon 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 "-naphthyl) 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 "-me Ruphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenyl) Amino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 ", 4" '-bis [N', N'-di (4-methylphenyl) amino] biphenyl-4-yl] Aniline, N, N′-bis [4- (diphenylamino) phenyl] -N, N′-diphenyl-1,3-diaminobenzene, N, N′-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,4-diaminobenzene, 5,5 "-bis [4- (bis [4-methylphenyl] amino] phenyl-2,2 ': 5', 2" -terthiophene, 1,3 , 5-Tris (diphenylamino) 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine, 4,4', 4" -tris [N, N-bis (4 "'-tert-butylbiphenyl-4" "-yl ) Amino] triphenylamine, 1,3,5-tris [N- (4′-diphenylamino] benzene, and the like, polythiophene and derivatives thereof, and poly-N-vinylcarbazole and derivatives thereof are more preferable.

  When the aromatic hydrocarbon compound represented by the general formula (1) and another compound having a hole injection function are used in combination, the aromatic hydrocarbon represented by the general formula (1) in the hole injection transport layer The content of the compound is preferably 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, and 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 aromatic hydrocarbon compound represented by the general formula (1) and / or another compound having a light emitting function.

  As the compound having a light emitting function other than the aromatic hydrocarbon compound represented by the general formula (1), for example, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [for example, rubrene, anthracene, Tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynyl) Anthenyl) benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] Perylene derivatives], triarylamine derivatives (for example, the compounds described above as compounds having a hole injecting and transporting function) Compounds), organometallic complexes [eg, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, Zinc salt of 4-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 (for example, coumarin 1 , Coumarin 6, Coumarin 7, Coumarin 30, Coumarin 106, Coumarin 138, Coumarin 151, Marine 152, Coumarin 153, Coumarin 307, Coumarin 311, Coumarin 314, Coumarin 334, Coumarin 338, Coumarin 343, Coumarin 500), pyran derivatives (for example, DCM1, DCM2), anthracene derivatives [for example, 9,10-bis (2 '-Naphthyl) anthracene derivative, 9,10-bis (1', 1 "-bis-3'-biphenyl) anthracene derivative], oxazone derivative (eg Nile Red), benzothiazole derivative, benzoxazole derivative, benzimidazole derivative , Pyrazine derivatives, cinnamic ester derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene vinylene and It derivatives, poly-biphenylene vinylene and derivatives thereof, poly terpolymers phenylene vinylene and derivatives thereof, poly naphthylene vinylene and its derivatives, and the like polythienylenevinylene and derivatives thereof. As the compound having a light emitting function other than the aromatic hydrocarbon 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. Polycyclic aromatic compounds, triarylamine derivatives, and organometallic complexes are more preferable.

  In the organic electroluminescent device of the present invention, a phosphorescent (triplet luminescent) compound is also used as the compound having a light emitting function other than the aromatic hydrocarbon compound represented by the general formula (1). It is possible.

  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 aromatic hydrocarbon compound represented by the general formula (1) in the light emitting layer.

  When the aromatic hydrocarbon compound represented by the general formula (1) and the compound having a light emitting function other than the aromatic hydrocarbon compound represented by the general formula (1) are used in combination, the general formula (1 ) 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 Laid-Open No. 5-214332.

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

  When the light-emitting layer is formed using the aromatic hydrocarbon 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. A triarylamine derivative, a polycyclic aromatic compound, and an organometallic complex are more preferable, and a rubrene derivative, a triarylamine derivative having a condensed polycyclic skeleton, and a condensed polycyclic aromatic compound are further preferable.

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

  The organic electroluminescent element of the present invention preferably contains an aromatic hydrocarbon compound represented by the general formula (1) as a guest material in the light emitting layer.

  On the other hand, when the light emitting layer is formed using the aromatic hydrocarbon compound represented by the general formula (1) as a host compound, the guest compound is preferable to the aromatic hydrocarbon compound represented by the general formula (1). Is 0.001 to 40% by weight, more preferably 0.01 to 30% by weight, still more preferably 0.1 to 20% by weight.

  When the amine compound represented by the general formula (1) is used as a host material in combination with another compound having a light emitting function, the aromatic hydrocarbon compound represented by the general formula (1) in the light emitting layer is preferably Is 40.0% to 99.9%, 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 the aromatic hydrocarbon compound represented by the general formula (1). -20% by weight. Aromatic hydrocarbon materials may be used alone or in combination.

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 device of the present invention is a compound having an electron injecting and transporting function other than the aromatic hydrocarbon compound represented by the general formula (1) of the present invention that can be used in the organic electroluminescent device of the present invention. Examples include organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenone derivatives, thiopyrandioxide derivatives, and the like. 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 amine compound or 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. To express)

(Q) _2- Al-O-Al- (Q) ₂ (c)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)

Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand include, for example, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl- 8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum,
Bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolato) (4-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) ) (3-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,3-dimethylphenolate) aluminum, Bis (2-methyl-8-quinolinolate) ( , 6-Dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-diphenylphenolato) aluminum, bis (2 -Methyl-8-quinolinolato) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolato) aluminum, bis (2-methyl- 8-quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, 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 foil. 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. The hole injection transport layer by a vacuum deposition method, the light-emitting layer, when forming the respective layers such as an electron injection transport layer, the conditions of the vacuum deposition is not particularly limited, usually, 10 -3 ^Pa about a vacuum below Below, it is preferable to carry out at a deposition rate of about 0.005 to 50 nm / sec at a boat temperature (deposition source temperature) of about 50 to 500 ° C. and a substrate temperature of about −50 to 300 ° C. 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, and 1-methylnaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, dichloromethane, and chloroform. , 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 an MIM (metal-insulator-metal) type. It may be. The driving voltage is usually 2 to 30V. The organic electroluminescent element of the present invention includes a panel-type light source (for example, a backlight for a clock, a liquid crystal panel, etc.), various light-emitting elements (for example, an alternative to a light-emitting element such as an LED), and various display elements [for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], various signs, various sensors, and the like.

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

(Example 1)
Production of Exemplary Compound A-3 (Chemical Formula 27)

560 mg (1 mmol) of the anthracene derivative represented by the formula (a) was dissolved in 50 ml of chlorobenzene, 659 mg of aluminum chloride was added thereto, and the mixture was heated and stirred at 90 ° C. for 30 minutes. Thereafter, 10 ml of methanol was added, the chlorobenzene layer was washed with water and separated, and then chlorobenzene was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 232 mg of the compound of exemplary compound A-3.
Further, this compound was purified by sublimation at 420 ° C. and × 10 ⁻⁴ Pa.
FD-MS: 558 (M ⁺ )
Elemental analysis: calculated value (%); C94.59, H5.41
Analytical value (%); C94.6; H5.4
Maximum emission wavelength (toluene): 618 nm

(Example 2)
Production of Exemplified Compound B-1 (Chemical Formula 28)

656 mg (1 mmol) of the anthracene derivative represented by the formula (b) was dissolved in 20 ml of 1,2-dichloroethane and cooled to 5 ° C. To this solution, 0.25 g of anhydrous iron chloride was added under a nitrogen stream and stirred at a temperature of 10 ° C. or lower for 1 hour. Thereafter, methanol was added to the reaction mixture, and 1,2-dichloroethane and methanol were distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 423 mg of the compound of Exemplary Compound B-1.
Further, this compound was purified by sublimation at 490 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS: 654 (M ⁺ )
Elemental analysis: calculated value (%); C95.38, H4.62
Analytical value (%); C95.4; H4.6
Maximum emission wavelength (toluene): 620 nm

(Example 3)
Production of Exemplified Compound B-38 (Chemical Formula 29)

In Example 1, instead of using 560 mg (1 mmol) of the anthracene derivative represented by the formula (a), it is described in Example 1 except that 733 mg (1 mmol) of the anthracene derivative represented by the formula (c) was used. According to the procedure, 484 mg of the compound of Exemplary Compound B-38 was obtained.
Further, this compound was purified by sublimation at 490 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 730 (M ⁺ )
Elemental analysis: calculated value (%); C95.31, H4.69
Analytical value (%); C95.3, H4.7
Maximum emission wavelength (toluene): 621 nm

Example 4
Production of Exemplary Compound B-40 (Chemical Formula 30)

Instead of using 560 mg (1 mmol) of the anthracene derivative represented by the formula (a) and 50 ml of chlorobenzene in Example 1, 707 mg (1 mmol) of the anthracene derivative represented by the formula (d) and 100 ml of orthodichlorobenzene were used. Except that, in accordance with the procedure described in Example 1, 512 mg of Compound of Exemplary Compound B-40 was obtained.
Further, this compound was purified by sublimation at 520 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 704 (M ⁺ )
Elemental analysis: calculated value (%); C95.42, H4.58
Analytical value (%); C95.4; H4.6
Maximum emission wavelength (toluene): 624 nm

(Example 5)
Production of mixture of exemplary compounds B-51 and B-52 (Chemical Formula 31)

A mixture consisting of 888 mg (1 mmol) of the anthracene derivative represented by the formula (e), 2.5 g of potassium hydroxide and 3 ml of quinoline was heated to reflux for 1 hour. Thereafter, the reaction mixture was cooled to room temperature, diluted hydrochloric acid was added, and the precipitate was collected by filtration. The obtained solid was washed with dilute hydrochloric acid, purified by silica gel column chromatography, and further recrystallized from toluene to obtain 454 mg of the compounds of Exemplified Compound B-51 and B-52 as an isomer mixture.
Further, this compound was purified by sublimation at 520 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 806 (M ⁺ )
Elemental analysis: calculated value (%); C95.25, H4.75
Analytical value (%); C95.2; H4.8
Maximum emission wavelength (toluene): 618 nm

(Example 6)
Production of a mixture of Exemplified compounds B-49 and B-50 (Chemical Formula 32)

[1] Production of Compound Mixture Represented by Formula (g) and Formula (g ′) 7.34 g (10 mmol) of an anthracene derivative represented by formula (f) was dissolved in 400 ml of chlorobenzene. Under a nitrogen stream, 6.59 g of anhydrous iron chloride was added to this solution and stirred at a temperature of 10 ° C. or lower for 2 hours. Thereafter, 20 ml of methanol was added to the reaction mixture, the organic layer was washed with water, and chlorobenzene was distilled off under reduced pressure. The residue was recrystallized from toluene, and represented by the formulas (g) and (g ′). As a mixture of isomers, 6.20 g was obtained.

[2] Production of Mixture of Exemplified Compounds B-49 and B-50 732 mg (1 mmol) of isomer mixture of compounds represented by formula (g) and formula (g ′), 198 mg (1 mmol) of 2-phenylphenylboronic acid Then, 2.5 mg of tetrakis (triphenylphosphine) palladium was added to a mixture of 212 mg (2 mmol) of sodium carbonate, 10 ml of toluene and 10 ml of water under an argon stream, and the mixture was heated and stirred at 90 ° C. for 8 hours. Thereafter, the reaction mixture was cooled to room temperature, the organic layer was separated and washed with water, and toluene was distilled off from the organic layer under reduced pressure. The residue was purified by silica gel column chromatography and further recrystallized from toluene to obtain 540 mg of Exemplified Compounds B-49 and B-50 as an isomer mixture.
Further, this compound was purified by sublimation at 490 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS: 806 (M ⁺ )
Elemental analysis: calculated value (%); C95.25, H4.75
Analytical value (%); C95.3, H4.7
Maximum emission wavelength (toluene): 621 nm

(Example 7)
Production of Mixture of Exemplified Compounds B-57 and B-58 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 172 mg (1 mmol) of 1-naphthylboronic acid was used. Except for the above, according to the procedure described in [2] of Example 6, 491 mg of Exemplified Compounds B-57 and B-58 were obtained as an isomer mixture.
Further, this compound was purified by sublimation at 510 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS: 780 (M ⁺ )
Elemental analysis: calculated value (%); C95.35, H4.65
Analytical value (%); C95.3, H4.7
Maximum emission wavelength (toluene): 622 nm

(Example 8)
Preparation of Mixture of Exemplified Compounds B-61 and B-62 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 222 mg (1 mmol) of 9-phenanthrylboronic acid was used. Except that it was used, 557 mg of Exemplified Compounds B-61 and B-62 were obtained as an isomer mixture according to the procedure described in [2] of Example 6.
Further, this compound was purified by sublimation at 530 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS: 830 (M ⁺ )
Elemental analysis: calculated value (%); C95.39, H4.61
Analytical value (%); C95.4; H4.6
Maximum emission wavelength (toluene): 624 nm

Example 9
Production of Mixture of Exemplified Compounds B-65 and B-66 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 246 mg (1 mmol) of 1-pyreneboronic acid was used. Produced 523 mg of Exemplified Compounds B-65 and B-66 as an isomer mixture according to the procedure described in Example 6, [2].
Further, this compound was purified by sublimation at 530 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 856 (M ⁺ )
Elemental analysis: calculated value (%); C95.30, H4.70
Analytical value (%); C95.3, H4.7
Maximum emission wavelength (toluene): 625 nm

(Example 10)
Production of Mixture of Exemplified Compounds B-79 and B-80 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 9,9-dimethyl-9H-fluorene-2- Except for using 238 mg (1 mmol) of boronic acid, 550 mg of Exemplified Compounds B-79 and B-80 were obtained as an isomer mixture according to the procedure described in [2] of Example 6.
Further, this compound was purified by sublimation at 510 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS: 846 (M ⁺ )
Elemental analysis: calculated value (%); C95.00, H5.00
Analytical value (%); C95.0, H5.0
Maximum emission wavelength (toluene): 623 nm

Example 11
Production of Mixture of Exemplified Compounds B-81 and B-82 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 212 mg (1 mmol) of dibenzofuran-4-boronic acid was used. 476 mg of Exemplified Compounds B-81 and B-82 were obtained as an isomer mixture according to the procedure described in [2] of Example 6.
Further, this compound was purified by sublimation at 510 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 820 (M ⁺ )
Elemental analysis: calculated value (%); C93.63, H4.42
Analytical value (%); C93.6; H4.4
Maximum emission wavelength (toluene): 624 nm

Example 12
Preparation of Mixture of Exemplified Compounds B-95 and B-96 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 289 mg of 4-N, N-diphenylaminophenylboronic acid 440 mg of Exemplified Compounds B-95 and B-96 were obtained as an isomer mixture according to the procedure described in [2] of Example 6 except that (1 mmol) was used.
Further, this compound was purified by sublimation at 520 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS: 897 (M ⁺ )
Elemental analysis: calculated value (%); C93.61, H4.83, N1.56
Analytical value (%); C93.6; H4.8, N1.6
Maximum emission wavelength (toluene): 629 nm

(Example 13)
Preparation of Mixture of Exemplified Compounds B-109 and B-110 In [2] of Example 6, instead of using 198 mg (1 mmol) of 2-phenylphenylboronic acid, 140 mg (1 mmol) of 4-fluorophenylboronic acid was used. 427 mg of Exemplified Compounds B-109 and B-110 were obtained as an isomer mixture according to the procedure described in [2] of Example 6.
Further, this compound was purified by sublimation at 490 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 748 (M ⁺ )
Elemental analysis: calculated value (%); C93.02; H4.44
Analytical value (%); C93.0, H4.4
Maximum emission wavelength (toluene): 617nm

(Example 14)
Production of Exemplified Compound C-9 (Chemical Formula 33)

A mixture of 657 mg (1 mmol) of an anthracene derivative represented by the general formula (h), 173 mg (1 mmol) of 2-quinolineboronic acid, 212 mg (2 mmol) of sodium carbonate, 10 ml of toluene and 10 ml of water was added to tetrakis (triphenyl) under an argon stream. Phosphine) palladium (2.5 mg) was added, and the mixture was stirred with heating at 90 ° C. for 8 hours. Thereafter, the reaction mixture was cooled to room temperature, the organic layer was separated and washed with water, and toluene was distilled off from the organic layer under reduced pressure. The residue was purified by silica gel column chromatography, and further recrystallized from toluene to obtain 420 mg of Exemplified Compound C-9.
Further, this compound was purified by sublimation at 480 ° C. and 1 × 10 ⁻⁴ Pa.
FD-MS: 705 (M ⁺ )
Elemental analysis: calculated value (%); C93.59 ,; H4.43 ,; N1.98
Analytical value (%); C93.6; H4.4, N2.0

(Example 15)
Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was subjected to ultrasonic cleaning using a neutral detergent, Semicoclean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and isopropyl alcohol. The substrate was dried with nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁵ Pa. First, N ′, N ″ -bis [4- (N, N-diphenylamino) phenyl] -N ′, N ″ -diphenyl-1,1′-biphenyl-4,4′-diamine is placed on the ITO transparent electrode. Was deposited to a thickness of 60 nm at 0.3 nm / sec to form a first hole injecting and transporting layer. Next, N, N′-diphenyl-N, N′-di (1 ″ -naphthyl) -1,1′-biphenyl-4,4′-diamine was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec. After that, the second hole injecting and transporting layer was formed, and rubrene and the compound of exemplary compound B-1 were deposited from different vapor deposition sources to a thickness of 40 nm at a vapor deposition rate of 0.3 nm / sec and a vapor deposition rate of 0.01 nm / sec. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm to form an electron injecting and transporting layer. In addition, lithium fluoride is deposited to a thickness of 0.5 nm at a deposition rate of 0.02 nm / sec, and finally aluminum is deposited to a thickness of 100 nm at a deposition rate of 2.0 nm / sec to form a cathode. Make And. Incidentally, deposition, a DC voltage was applied to the organic electroluminescent element in which. Manufactured performed while maintaining the vacuum of the deposition chamber, at room temperature, under a dry atmosphere, was driven at a constant current density of 10 mA / cm ² Initially, red light emission of 4.8 V and a luminance of 623 cd / m ² was confirmed, and when the organic electroluminescence device was continuously driven at a constant current density of 80 mA / cm ² , the luminance was 80 at the initial value. The time to decay to% was 2100 hours.

(Example 16)
In Example 15, an organic electroluminescent device was formed according to the procedure described in Example 15 except that the compound of Exemplified Compound A-3 was used instead of the compound of Illustrated Compound B-1 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 17)
In Example 15, in forming the light emitting layer, instead of using the compound of Exemplified Compound B-1, the compound of Exemplified Compound B-38 was used in accordance with the procedure described in Example 15, except that the organic electroluminescent element was used. Was made. Red light emission was confirmed from the element. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 18)
In Example 15, in forming the light emitting layer, instead of using the compound of Exemplified Compound B-1, the compound of Exemplified Compound B-40 was used in accordance with the operation described in Example 15 except that the compound of Illustrated Compound B-40 was used. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

Example 19
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-51 and B-52 was used according to the procedure described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 20)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-49 and B-50 was used in accordance with the operation described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 21)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-57 and B-58 was used, according to the procedure described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 22)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-61 and B-62 was used, according to the procedure described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 23)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-65 and B-66 was used in accordance with the operation described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 24)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-79 and B-80 was used in accordance with the operation described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 25)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-81 and B-82 was used in accordance with the operation described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 26)
In Example 15, in the formation of the light emitting layer, instead of using the compound of Exemplified Compound B-1, instead of using the compound of Exemplified Compound B-95 and B-96, according to the procedure described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 27)
In Example 15, in forming the light emitting layer, instead of using the compound of Exemplified Compound B-1, a mixture of Exemplified Compounds B-109 and B-110 was used in accordance with the operation described in Example 15, An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

(Example 28)
In Example 15, in forming the light emitting layer, an organic electroluminescence device was prepared according to the procedure described in Example 15 except that the compound of exemplary compound C-9 was used instead of the compound of exemplary compound B-1. Was made. Red 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 15, the procedure described in Example 15 was followed except that the following compound (R-1) (Chemical Formula 34) was used in place of the compound of Exemplary Compound B-1 in forming the light emitting layer. An organic electroluminescent element was produced. In the preparation of the organic electroluminescent device, a slight decrease in the degree of reduced pressure was observed when the following compounds were deposited. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

  It can be seen from Table 1 that the organic electroluminescence device using the aromatic hydrocarbon compound represented by the general formula (1) has high efficiency and also has a long luminance decay time. Further, when the aromatic hydrocarbon compound represented by the general formula (1) is deposited, the above-described decrease in the degree of reduced pressure is not confirmed, and the compound of the present invention is excellent in terms of thermal stability. I understand that.

(Comparative Example 2)
In Example 15, in the formation of the light emitting layer, the following compound (R-2) (Chemical Formula 35) was used instead of the compound of Exemplary Compound B-1, and the operation described in Example 15 was followed. An organic electroluminescent element was produced. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

  From the results shown in Table 1, it can be seen that the organic electroluminescence device using the aromatic hydrocarbon compound represented by the general formula (1) has high efficiency and also has a long luminance decay time.

(Comparative Example 3)
In Example 15, in the formation of the light emitting layer, the following compound (R-3) (Chemical Formula 36) was used instead of using the compound of Exemplary Compound B-1, and the operation described in Example 15 was followed. An organic electroluminescent element was prepared. In the preparation of the organic electroluminescent device, a slight decrease in the degree of reduced pressure was observed when the following compounds were deposited. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

  From the results shown in Table 1, it can be seen that the organic electroluminescence device using the aromatic hydrocarbon compound represented by the general formula (1) has high efficiency and also has a long luminance decay time. Further, when the aromatic hydrocarbon compound represented by the general formula (1) is deposited, the above-described decrease in the degree of reduced pressure is not confirmed, and the compound of the present invention is excellent in terms of thermal stability. I understand that.

(Example 29)
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 the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa.

  First, N ′, N ″ -bis [4- (N, N-diphenylamino) phenyl] -N ′, N ″ -diphenyl-1,1′-biphenyl-4,4′-diamine is placed on the ITO transparent electrode. Was deposited at a deposition rate of 0.2 nm / sec to a thickness of 60 nm to form a first hole injection transport layer. Next, N, N′-diphenyl-N, N′-di (1 ″ -naphthyl) -1,1′-biphenyl-4,4′-diamine and Exemplified Compound B-38 were deposited from different deposition sources, respectively. Vapor deposition was performed at a rate of 0.2 nm / sec and a deposition rate of 0.01 nm / sec to a thickness of 40 nm to form a light emitting layer that also served as a second hole injection transport layer, and then tris (8-quinolinolato) aluminum was deposited. An electron injecting and transporting layer was formed by vapor deposition at a rate of 0.2 nm / sec to a thickness of 20 nm, on which an aluminum / lithium alloy was deposited as a cathode to a thickness of 10 nm at a vapor deposition rate of 2.0 nm / sec. Aluminum was vapor-deposited at a deposition rate of 2.0 nm / sec to a thickness of 100 nm to form an electrode to produce an organic electroluminescent device.

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 device was driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, red light emission of 5.0 V and luminance of 570 cd / m ² was confirmed.
(Example 30)
Production of Organic Electroluminescent Device 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.
Deposition rate of N ', N "-bis [4- (N, N-diphenylamino) phenyl] -N', N"-diphenyl-1,1'-biphenyl-4,4'-diamine on ITO transparent substrate Vapor deposition was performed at 0.2 nm / sec to a thickness of 50 nm to form a first hole injection transport layer. Next, N, N′-diphenyl-N, N′-di (1 ″ -naphthyl) -1,1′-biphenyl-4,4′-diamine was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec. After that, a second hole injecting and transporting layer was formed, and then the compound of tris (8-quinolinolato) aluminum and exemplary compound C-9 were deposited from different deposition sources at a deposition rate of 0.2 nm / sec and a deposition rate of 0.02 nm / sec. A light emitting layer that doubles as an electron injecting and transporting layer was formed by co-evaporation to a thickness of 40 nm, and tris (8-quinolinolato aluminum) was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec. After forming the second electron injecting and transporting layer, lithium fluoride was deposited at a deposition rate of 0.2 nm / sec to a thickness of 1 nm, and aluminum was further deposited at a deposition rate of 2.0 nm / sec. An organic electroluminescent device was produced by vapor deposition to a thickness of nm to form a cathode, and the deposition was carried out while maintaining the reduced pressure of the vapor deposition tank. It was driven at a constant current density of 10 mA / cm ² at room temperature, and red light emission of 5.1 V, 550 cd / m ² was confirmed in the initial stage.

(Example 31)
Production of Organic Electroluminescent Device 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.
Deposition rate of N ', N "-bis [4- (N, N-diphenylamino) phenyl] -N', N"-diphenyl-1,1'-biphenyl-4,4'-diamine on ITO transparent substrate Vapor deposition was performed at a thickness of 60 nm at 0.2 nm / sec to form a first hole injection transport layer. Next, N, N′-diphenyl-N, N′-di (1′-naphthyl) -4,4′-diamino-1,1′-biphenyl was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec. The second hole injecting and transporting layer was formed. Thereafter, a mixture of the following compound (H-1) and exemplary compounds B-51 and B-52 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. A light emitting layer was formed. Further, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm to form an electron injecting and transporting layer. Thereafter, lithium fluoride was deposited at a deposition rate of 0.2 nm / sec to a thickness of 0.5 nm, and aluminum was deposited at a deposition rate of 2.0 nm / sec to a thickness of 150 nm to form a cathode. A light emitting element was manufactured. The vapor deposition was carried out while maintaining the reduced pressure in the vapor deposition tank. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was driven at a constant current density of 10 mA / cm ² at room temperature in a dry atmosphere. Initially, red light emission of 4.6 V and 720 cd / m ² was confirmed. The 80% luminance decay time when continuously driven at a constant current density of 80 mA / cm ² was 2200 hours. Note that no change in the color tone was observed even after the luminance was attenuated.

(Example 32)
Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was subjected to ultrasonic cleaning 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, 3 wt% containing polymethyl methacrylate (weight average molecular weight 25000), the compound of Exemplified Compound B-40, and tris (8-quinolinolato) aluminum in a weight ratio of 100: 30: 40 on the ITO transparent electrode, respectively. A 120 nm light-emitting layer was formed by spin coating using a% dichloroethane solution. Then the glass substrate having the light-emitting layer, was fixed to a substrate holder of the vapor deposition apparatus, followed by vacuum evaporation layer 2 × 10 -4 ^Pa. On the light emitting layer, magnesium and silver were co-evaporated to a thickness of 200 nm at a deposition rate of 2.0 nm / sec (weight ratio 10: 1) to form a cathode, thereby preparing an organic electroluminescent device. When a DC voltage of 12 V was applied to the produced organic electroluminescent device at room temperature in a dry atmosphere, a current of 86 mA / cm ² flowed. Red light emission with a luminance of 490 cd / m ² was confirmed.

  According to the present invention, it has become possible to provide a novel aromatic hydrocarbon compound and an organic electroluminescence device using the aromatic hydrocarbon compound. More specifically, an aromatic hydrocarbon compound that is suitable for a light emitting material of an organic electroluminescent device, has excellent vapor deposition properties, has high thermal stability, and has excellent color purity (emission wavelength is long), and the aromatic hydrocarbon compound It has become possible to provide an organic electroluminescent device that uses a material having excellent stability and durability and excellent color purity.

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 (7)

An aromatic hydrocarbon compound represented by the general formula (1).

[Wherein, R _{1 to} R ₁₇ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aromatic hydrocarbon. Group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, carboxyl group, substituted or unsubstituted A substituted amino group or a cyano group, and Z represents a substituted or unsubstituted aromatic hydrocarbon group having 19 or less nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group] In General Formula (1), Z is a substituted or unsubstituted aromatic hydrocarbon group represented by General Formula (2), or a substituted or unsubstituted aromatic heterocyclic group represented by General Formula (3) The aromatic hydrocarbon compound according to claim 1.

[Wherein, Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ each independently represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, substituted or Substituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, hydroxyl group, nitro group, Represents a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and the adjacent groups of Ra _{1 to} Ra ₅ and Rb _{1 to} Rb ₅ form a ring together with the adjacent groups to form an aromatic hydrocarbon ring , An aliphatic hydrocarbon ring, an aromatic heterocyclic ring, or an aliphatic heterocyclic ring, Y _{1 to} Y ₅ represent a carbon atom or a nitrogen atom, and at least one of Y _{1 to} Y ₅ represents nitrogen. When Y ₁ is a nitrogen atom, Rb ₅ is not present; when Y ₂ is a nitrogen atom, Rb ₄ is not present; and Y ₃ is a nitrogen atom. , Rb ₃ does not exist, and when Y ₄ is a nitrogen atom, Rb ₂ does not exist, and when Y ₅ is a nitrogen atom, Rb ₁ does not exist. The aromatic hydrocarbon compound according to claim 2, wherein the general formula (2) is a group selected from the group consisting of the general formulas (2-A) to (2-E) and (2-G).

Wherein, Rc ₁ to Rc ₅ is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl Represents an oxy group, a substituted or unsubstituted arylthio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, and Rd _{1 to} Rd ₁₀ , Re _{1 to} Re ₈ , Rf ₁ to Rf _10, Rg ₁ ~Rg _10, and, in Ri ₁ to Ri ₈ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted Substituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryl Represents a thio group, a hydroxyl group, a nitro group, a carboxyl group, a substituted or unsubstituted amino group, or a cyano group, _one of Rd _{1 to} Rd ₁₀ , one of Re _{1 to} Re ₈ , Rf one of the _{1 ~Rf 10,} one of Rg ₁ ~Rg _10, and, one of Ri ₁ to Ri ₈ represents a bond, _{X 1} is an oxygen atom, a sulfur atom or, , —C (R ′) (R ″) —, wherein R ′ and R ″ are each independently a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aromatic group, A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group) An organic electroluminescence device comprising at least one layer containing at least one kind of the aromatic hydrocarbon compound according to any one of claims 1 to 3 between a pair of electrodes. The organic electroluminescent element according to claim 4, wherein the layer containing the aromatic hydrocarbon compound according to claim 1 is a light emitting layer. The organic electroluminescent device according to claim 4, wherein the layer containing the aromatic hydrocarbon compound according to any one of claims 1 to 3 is a hole injection transport layer. The organic electroluminescent element according to claim 4, wherein the layer containing the aromatic hydrocarbon compound according to any one of claims 1 to 3 is an electron injecting and transporting layer.

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