TW200916434A - Aromatic amine derivatives and organic electroluminescent device - Google Patents

Abstract

This invention provides an organic electroluminescent device having a long service lifetime, a high light emitting efficiency and capable of obtaining blue light emitting of high color purity, and aromatic derivatives having a specific structure for realizing the same. In the aforementioned organic electroluminescent device, one more organic film layer including a light emitting layer is located between a cathode and an anode, and at least one layer of the organic film layer includes the aforementioned aromatic derivatives.

Description

200916434 IX. Description of the Invention: The present invention relates to an aromatic amine derivative and an organic electroluminescent device (organic EL device) using the same, and particularly relates to a long life, high luminous efficiency and A blue-emitting organic rainbow element of high color purity and an aromatic amine derivative thereof are obtained.先前 [Prior Art] The organic EL device using an organic substance is expected to be used as a solid-state light-emitting large-area full-color display element, and a large number of developments are underway. In general, an EL element is composed of a light-emitting layer and a pair of counter electrodes sandwiching the layer. The following phenomenon occurs in the illuminating system: when an electric field is applied between the electrodes, electrons are injected from the cathode side to inject holes from the anode side, and further, the electrons are recombined with the holes in the opaque layer to form an excited state, and the excited state is excited. When returning to the ground state, energy is released in the form of light. In the case of the organic EL device, the driving voltage is lower than that of the inorganic light-emitting diode. Moreover, the characteristic deterioration is also clear and cannot be put into practical use. Recently, organic EL elements, although slowly improved, have required higher luminous efficiency and longer life. For example, there is disclosed a technique of using a mono-onion compound (_〇_anthrace (4) as an organic light-emitting material (Patent Document υ. However, in this technique, ν is only available at a current density of 1 65 niA/cm 2 ). The luminosity of I 650 Cd/m2 is extremely low in i Cd/A, and is not practical. Further, a technique of using a single bismuth compound as an organic luminescent material is disclosed (Patent Document 2) The technical order, the efficiency is about 3 cd/A and lower, 131739.doc 200916434 is thus seeking improvement for practical use. On the other hand, there is proposed a long-life organic EL element in which stilbene is used. The compound is used as an organic light-emitting material and a styrylamine or the like is added thereto (Patent Document 3). However, the life of the device is not satisfactory and further improvement is required. A technique in which a biguanide compound and a stilbene compound are used as an organic light-emitting medium layer (Patent Document 4). However, in these techniques, the luminescence spectrum is long-wavelength due to the conjugated structure of the styrene compound, Further, Patent Document 5 discloses a blue light-emitting element using a diaminochry Sene derivative. However, although the light-emitting efficiency of the element is excellent, the service life is not satisfactory. Patent Document 1. Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. [Patent 4] Japanese Patent Laid-Open Publication No. Hei. No. 2, No. 2, No. 4, No. 5, pp. It is an object of the invention to provide an organic EL device having a long lifetime, high luminous efficiency, and high color purity, and an aromatic amine derivative thereof. The present inventors have developed the above-mentioned preferred properties. The aromatic amine derivative and the organic EL product using the same were repeatedly studied. As a result, it was found that the fineness can be achieved by using the aromatic amine derivative represented by the following formula (1). 131739.doc 200916 434. The present invention has been completed based on this finding. That is, the present invention provides the following

物[化1] Η·*--I. , 彡 ^ not aromatic amine derived ω

An A 'B 2 'R, which is a substituted or unsubstituted valence group derived from the fluorene; r2 is a mono-, = or unsubstituted charcoal number 6 to 5 伸 of an extended aryl group, or a substituted or unsubstituted The divalent heterocyclic group having a number of 3 to 50 is independently a substituted or unsubstituted rabbit (IV) aryl group, or a substituted or unsubstituted carbon number of 3 to %, in R, a single bond and a side bond a chain structure ... or a "Lite" having at least one substituent other than _NAB in the fluorene structure. Further, in the present invention, the "substituted or unsubstituted carbon number a to b" X"' means "carbon number a to b and carbon number" does not include the carbon number of the substituent. Further, the present invention provides an organic EL device having an organic thin film layer containing a light-emitting layer or more between a cathode and an anode, and at least one layer of the organic thin film layer contains at least the above-mentioned aromatic amine derivative. The organic alloy element using the aromatic amine derivative of the present invention can obtain a practically preferable light-emitting luminance with a low applied voltage, and has high luminous efficiency, and is difficult to deteriorate even after long-term use, and has a long life. [Embodiment] The aromatic amine derivative of the present invention is represented by the following formula (1): 131739.doc 200916434 [Chemical 2]

ω The position of the carbon atom to be replaced by the chopsticks or the neutron of the yoke (_R, where R1 represents a valence group substituted by the following formula. For the substitution position of the free raw NAB on the chopsticks) There is no particular limitation, but it is preferably 2 digits or 6 digits, more preferably 2 or 3 digits: [Chemical 3]

2 3 Substituted substituents are selected from: substituted or unsubstituted aryl group having 6 to 5 carbon atoms, substituted or unsubstituted mono or di (aryl group having 6 to 5 fluorene) amine groups, substituted or not Substituted charcoal number 1 to 5G, substituted or unsubstituted cyclodextrin having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 5 carbon atoms, substituted or unsubstituted 50 alkoxy group, substituted or unsubstituted (tetra) group (carbon number of aryl moiety is 6 to 50, alkyl group knife has a reciprocal number of ~ 50), substituted or unsubstituted heteroaryl group (heterofang) The radical of the base moiety is 4 to 50, the carbon number of the alkyl moiety is 1 to 5 0), and the substituted or unsubstituted # ^ u mountain also has an anionic number of 6 to 50, substituted or unsubstituted. Stone annoyance 6~50 妒 妒 1 μ 八 瓜 瓜, substituted or unsubstituted alkoxycarbonyl (carbon number of the alkoxy moiety is ^50), substituted or unsubstituted carbon number 1~20 Alkyl, substituted or unsubstituted rabbits 6 to 50 aryl decyl, decane 13i739.doc 200916434

Base, amine group, cyano group, nitro group, surface A & base, carboxyl group and the like. The position of the substituents may be a cup to a position of 1 to 12 bits, but particularly preferably 6 bits, 8 bits, 9 bits, and 12 bits. As for the aryl group having a carbon number of 6 to 50, such as 丄t 1 lac #, for example, a phenyl group, a 2-biphenyl group, a 3-hydrazone group, a 4-biphenyl group, a bis-group #44 纟二本- 4-Based, conjugated triphenyl-3-yl'-linked two-form-2-yl, cross-linked three stupid _ * _ | yl, meta-triphenyl-3-yl, cross-linked triphenyl-2-yl, 1_ Naphthyl, 2-naphthyl^"indenyl, 2-indenyl, 9-fluorenyl, 1-$indenyl, 2-indenyl, 4-indenyl, fluorenyl, etc.; An alkyl group such as a group or an ethyl group, a cyclohexyl group, etc. ^ ^ ^ t is substituted with a pit base, and a halogen is substituted by a halogen. The carbon number of the aryl group is preferably from 6 to 30, more preferably more than 6 to 20 Particularly preferred examples are phenyl, 2-biphenylyl, 3-linked floc. P + tertidine, 4-biphenyl, κ naphthyl, 2-naphthyl. As for substituted aryl ' There may be mentioned 2-methylphenyl, "phenyl", 4-anthracenyl, 4-ethylphenyl, 4-methylbiphenyl, 4-ethylbiphenyl, 4-cyclohexyl Phenyl, 3,5·dioxaphenyl, 5-methylnaphthyl and the like. The aryl group, the pot substituent, the particularly preferred substituted or unsubstituted aryl group having 6 to 5 carbon atoms in the soap or di(aryl group having 6 to 50 carbon atoms) are the same as described above. As the alkyl group of the carbon number, for example, a mercapto group, an ethyl group, a propyl group, an isopropyl S group, a butyl group, a second butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group are mentioned. And octadecyl group; and the like may be substituted by an aryl group such as a phenyl group, a halogenated alkyl group such as an aryloxy 'trifluorofluorenyl group such as a halogen 'phenoxy group such as chlorine or fluorine, or an alkoxy group such as a benzyloxy group. The carbon number of the alkyl group is preferably Buchuan, more preferably 1 to 20. Particularly preferred examples are anthracenyl, ethyl, propyl, isopropyl, butyl, t-butyl, tert-butyl. As the substituted alkyl group, for example, 2-phenylisopropyl, trimethylmethyl, trifluoromethyl, benzyl, phenoxybenzyl 131739.doc 200916434 α, α-bis(trifluoromethyl) α,α--methylbenzyl, α,α-ylphenylbenzyl)benzyl, diphenylindenyl, cardinyloxybenzyl and the like. Examples of the cycloalkyl group having 3 to 20 carbon atoms include a cyclopropyl group, a cyclopentyl group, a % pentyl group, and a cyclohexyl group. The cycloalkyl group may be substituted by an aryloxy group such as a phenyl group such as an aryloxy group such as a diphenyloxy group, a methyl group or the like, an alkoxy group such as a trimethyl group or the like, and an alkoxy group such as a methoxy group. Examples of the heterocyclic group having 3 to 50 carbon atoms include (iv) and benzene (tetra). Sitting, pyrrole, bite. South, sell pheno, benzophene, 噚 哇 哇 、, ° Π Π Π 、 ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° ° The base derived from imidaz〇ndine, Niangbite, etc. The position of the bond is not limited to (4). Examples of the substituent of the heterocyclic group include an alkyl group such as a methyl group, an ethyl group or a propyl group. The substituted position of H such as a substituted or unsubstituted phenyl group or a naphthyl group is not particularly (4). Particularly preferred substituted or unsubstituted heterocyclic groups are 2·-yl, 3+-based, 4+-based and the like. Examples of the alkoxy group having a slave number of 1 to 50 include, for example, an anthracenyloxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, and a third group. Butoxy, pentyloxy (including positional isomers), hexyloxy (including positional isomers), and the like. The carbon number of the alkoxy group is preferably from 1 to 30, more preferably it is from 20. The alkoxy group may be substituted by an aryl group such as a phenyl group, an element such as a gas or a gas, an aryloxy group such as a phenoxy group, or an alkoxy group such as a oxy group. . As the aralkyl group (the carbon number of the aryl moiety is 6 to 5 Å, and the carbon number of the alkyl moiety is 1 to 5 Å), for example, a benzyl group, a 1-phenylethyl group, a 2-phenyl group Base, 1-phenylisopropyl, 2-phenylisopropyl &, benzyl tertiary butyl, α-naphthylmethyl 131739.doc 10 200916434 base, 〗 〖-α- extraction 7 - 茇', soil , 2_α-naphthylethyl, 1-α-naphthylisopropyl, 2-α- is isopropyl isopropyl, β-negenyl, 丨-β-naphthylethyl, 2-β-naphthyl ^ ^ Nonyl isopropyl, 2-β-naphthyl isopropyl, etc.; which can be substituted by sulfhydryl and the like, such as chlorine, odor, dish and the like, by a base, a cis group, a cyano group or the like. The number of slaves of the sickle #父好 is 6~3〇, more preferably 6~2〇. The carbon number of the alkyl moiety is preferably (iv), more preferably, the aryl group is substituted for the aryl group, for example, "base group, intermediate T group, adjacent f group, pair:: Base, gas node group, o-chlorogang group, p-(di) group, meso-group, ortho-, n., hard base, inter-disc base, adjacent broken base, basal base, 7 (four) , ortho-base group, on-wall base group, inter-stone base group, adjacent stone base group, p-cyano group, m-cyano group, orthano-cyano group, base · 2_phenyl Isopropyl, L-chloro-2-phenylisopropyl, etc. As for the heteroaryl group (the carbon number of the heteroaryl moiety is 4 to 5 Å, and the hydrazine moiety is 1 to 5 Å), for example, Except: mercaptomethyl group, 2_(bubbi p group) ethyl group, etc. The carbon number of the #aryl group is preferably 4 to 3 Å, and the amount is preferably 4 to 20. The carbon of the alkyl group The number is preferably (10), more preferably (4). The aryloxy group having a carbon number of 6 to 5 Å is exemplified by a silyloxy group and a cai oxy group, which can be alkyl group or the like. The carbon number of the aryloxy group is preferably oxygen 3: etc. More preferably, it is 6 to 20. As for the substituted aryloxy group, for example, The toluene to the arylthio group having 6 to 50 carbon atoms may, for example, be a stupid thio group or a bismuth furnace, which may be substituted by a decyl group alkyl group. The arylthio group preferably has a carbon number of 6 to 30, more preferably It is a ruthenium-substituted arylthio group, and, for example, a thio group (tolylthio), etc., abundance 131739.doc 200916434 As for the alkoxy group of the oxy group Ik group (carbon number 1 to 5 Å), for example, 曱Oxy, ethoxy, propoxy, isopropoxy, butoxy, isobutyl decyl, second butoxy, tert-butoxy, pentyloxy (including positional isomers), hexyloxy (including a positional isomer group), etc. The carbon number of the alkoxy moiety is preferably from 1 to 30, more preferably from 1 to 2 Å. As for the substituted or unsubstituted carbon number dialkyl alkyl decyl group ( Including _, one and two base sulphur bases)', for example, preferably: trimethyl sulphate, diethyl decyl, tripropyl decyl, butyl decyl decyl, propyl fluorenyl a trialkylalkylene group such as a nonylalkyl group, a vinyl dimethyl fluorenyl group, or a tert-butyl dimethyl decyl group, and an arylalkyl group having 6 to 50 carbon atoms (including mono-, di-, and triaryl groups) As the decyl group, for example, an arylalkyl group such as a triphenylalkyl group, a phenyldimethylalkyl group or a diphenylmethyl fluorenyl group is preferred. In the formula (I), R2 represents a single bond, a substitution or An unsubstituted aryl group having 6 to 5 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 3 to 5 carbon atoms. For example, the exoaryl group having a stone anastonym of 6 to 50, for example, may be mentioned. a divalent group derived from benzene, biphenyl, hydrazine, naphthene, anthracene, anthracene, anthracene or the like; which may be an alkyl group such as a mercapto group or an ethyl group, a cycloalkyl group such as a cyclohexyl group, or the like. The number of % of the aryl group is preferably from 6 to 30, more preferably from 6 to 20. As the substituted or unsubstituted extended aryl group, for example, 丨, 4 phenyl, 2, 6 _Naphthyl, 2_fluorenylphenyl, 3-fluorenylphenyl, 4-fluorenylphenyl, 4-ethylphenyl, 4-mercaptophenyl, 4-ethylphenyl, 4- The cyclohexyl group is extended with a biphenyl group, a 3,5-dihydrophenylene group, a 5-quinone-based naphthyl group or the like. The position of the two bonding keys is not particularly limited. 131739.doc 12 200916434 As for the divalent heterocyclic group having 3 to 50 carbon atoms, for example, it can be exemplified by μ, stupid, and sputum, "Comparative, sputum, sputum, stupid and swearing" , ^ 啉 " card. sit,. Bivalent base derived from biting, 喧琳, 噎噎琳, benzene brewing, p-e, taste and setting. The carbon number of the divalent heterocyclic group is preferably from 3 to 30, more preferably from 3 to 2 Å. The position of the two bonding keys is not particularly limited. The above-mentioned aryl group and divalent heterocyclic group may be an aryl group having 6 to 5 carbon atoms, an alkyl group having 1 to 50 carbon atoms, an alkoxy group having a carbon number of 7 to 7%, and an aralkyl group having 7 to 5 carbon atoms. And an aryloxy group having 6 to 50 carbon atoms, an arylthio group having 6 to 5 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, a halogen atom, a cyano group, a nitro group, a trans group, a carboxyl group or the like. The above aryl group, alkyl group, alkoxy group, aralkyl group, aryloxy group, aryl group, and alkoxycarbonyl group may further be an alkyl group such as a mercapto group or an ethyl group, a halogenated alkyl group such as a trifluoromethyl group, or a cyclohexyl group. An alkoxy group such as a cycloalkyl group or a benzyloxy group, a chloro group such as a hydroxy group, a hydroxy group, a nitro group, a cyano group or the like, wherein the substituents of the above-mentioned extended aryl group and the divalent heterocyclic group do not include an amine group. And a substituted amino group. In the formula (I), hydrazine and hydrazine each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 5 carbon atoms. Examples of the aryl group having 6 to 50 carbon atoms include a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, an anthracenyl group, an anthracenyl group, an anthracenyl group, an anthracene-phenanthryl group, a 2-phenanthrenyl group, and a 3-phenyl group. Fisino, 4_phenanthryl, 9-phenanthryl, I chopsticks, 2. chopstick base, 2 fluoranthenyl, 3-fluorenyl group, etc.; it can be alkyl group such as sulfhydryl group, ethyl group, cycloalkyl group such as cyclohexyl group, gas cyclin, trimethyl decyl group The number of carbon atoms of the aryl group substituted by an alkylalkyl group is preferably 6 to 3 Å, more preferably 6 to 20. Particularly preferred examples are phenyl, biphenyl, 丨-naphthyl, 2_. Naphthyl group, 2_ chopstick base, 131739.doc -13- 200916434 3-fluorenyl group. As the substituted aryl group, for example, trimethyl decylphenyl group, 3,4-didecylphenyl group, 9,9-dimercapto-2-yl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, "based phenyl, 4- Ethylbiphenyl, 4-cyclohexylbiphenyl, 3,5-dichlorophenyl, %methylnaphthyl, etc. As for a heterocyclic group having a carbon number of 3 to 50, for example, opening with a mountain L, , 0 can be exemplified by imidazole, benzimidazole, D-pyrrole, furan, thiophene, benzophenanthrene, oxazoline, porphyrin, carbazole, pyridine, quinoline, isoquinoline, moth , pyral〇dine, imipenem, piperidine derived base. As for the substituents of the glutinous glutinous rice glutinous base, it can be mentioned: 曱An alkyl group such as a group, an ethyl group or a propyl group; the position of substitution on the substituted or unsubstituted heterocyclic ring is not particularly limited. Particularly, the heterocyclic group is a 2-pyridyl group or the like. A phenyl group, a naphthyl group or the like; Or a compound represented by the aromatic amine derivative (III) of the present invention: [Chemical Formula 4] Preferably, it is a formula (Π) or

(wherein, Α and Β are the same as above; R is a carbon number of 6 to 5. The aryl group is taken as follows: a substituted or unsubstituted or unsubstituted carbon number of 5 to 50 131739.doc -14 - 200916434 Divalent heterocyclic group; X1 and X2 are each independently selected from the above group as a substituent; a represents an integer of 0 to 5'b represents an integer of 0 to 6; X] can be linked to χ2 to form a saturated Or an unsaturated ring; when a is an integer of 2 or more, the plurality of x 1 may be the same or different, and may be connected to form a saturated or unsaturated ring; when b is an integer of 2 or more, the plurality of X2 may be the same or Different, can be connected to form a saturated or unsaturated ring). A more preferred aromatic amine derivative is represented by the following formula (IV), (V), (VI) or (νπ):

131739.doc 200916434

(VE〇(wherein, X1, R3, , and the above are the same; X3 and X4 are each independently selected from the above-mentioned groups as the chopsticks & _substituent' c represents an integer of 0 to 5, and d represents 0 to 5 An integer; X3 and Χ4 may be connected to each other to form a saturated or unsaturated ring; when c is an integer of 2 or more, the pleats may be the same or different, and may be connected to each other to form a saturated or unsaturated target. (1 is an integer of 2 or more, and a plurality of X4 may be the same or different, and J is connected to each other to form a saturated or unsaturated ring). In the formulae (IV), (V), (VI), and Γντ) (VII) Among them, it is preferable that one or both of c and d are integers of 2 or more. The traitor is double-day, preferably, [Chemical 6]

And/or

The substituent represented by I is o-dimethyl hydrazine, m-xylylene, p-nonylphenyl, 2,3,4-triphenylphenyl, 3 4 5 -field 4 w , and dimethyl 4 The base, 2,4,6-trimethylphenyl; the two of c and d are 2 or more, and the combination of the selected ones from the substituents. In the formulae (II) to (VII), a preferred av, 2 jt weight lamp, at least one of X 丨 and X 2 is a substituted or unsubstituted carbon number of 3 to 50, preferably a θ dry pair疋3~30, more preferably 3~20 bis 131739.doc • 16 - 200916434 grade or secondary base, the number of substituted or unsubstituted ^^ is 3~50, preferably 3~30, More preferably, it is a cycloalkyl group of 3 to 20; alternatively, a decyl group or an arylalkyl group having a carbon number of -20. As the secondary or tertiary alkyl group, for example, an isopropyl group, a second butyl group, a third butyl group or the like can be mentioned. As the cycloalkyl group, for example, a cyclohexyl group, a cyclopentyl group and the like can be given. As for the alkyl fluorenyl group, a preferred dimethyl dimethyl ketone 7 alkyl group, diethyl decyl group, tripropyl sulphur group, trityl sulphur group, tert-butyl dimethyl decyl group Or a trialkylalkylene group or a triarylsulfonyl group. In the formula (I), R2 is a single bond and -NAB is bonded to the 1-position or the 6-position of the chopstick structure. The defensive structure has at least one substituent other than -NAB. That is, when r2 is a single bond and -NAB is bonded to the 1 or 6 position of the chopstick structure, in the formula (1), at least one of a and b represents an integer other than zero. As the above substituent, a diarylamine group such as a diphenylamino group or a bis(2-mercaptophenyl)amino group is preferred. The aromatic amine derivative represented by the formula (I) of the present invention is shown below. Specific examples, but are not limited to the exemplified compounds: [Chem. 7]

131739.doc 200916434

[化8]

The method for producing the aromatic amine derivative represented by the formula (I) of the present invention is not particularly limited, and it may be produced by a known method, for example, by using a diarylamine or the like, by J. Chem. Soc. ,, Perkin Trans 2, Volume 2, 131739.doc -18- 200916434

Stry, vol. 65, pp. 1158~1174 (2000)). The aromatic amine derivative of the present invention is suitably used as a material for an organic EL device, and is preferably used as a light-emitting material, particularly a dopant material. The stacked EL element of the present invention is composed of a pair of electrodes and sandwiched between the pair of electrodes! The layer is composed of an organic compound layer or more. At least the layer of the organic compound layer is a light-emitting layer, and at least the i layer of the organic compound layer contains at least one aromatic amine derivative of the formula (1). Preferably, the light-emitting layer contains at least one of the above aromatic amine derivatives. The above-mentioned aromatic amine derivative in the above-mentioned light-emitting layer is preferably 0.0U0% by weight, more preferably 〇5 to 2% by weight, particularly preferably 1 to 20% by weight, particularly preferably. It is 5~2〇% by weight. In the case where the aromatic amine derivative of the present invention is used as a light-emitting material of an organic EL element, it is preferred that the above-mentioned light-emitting layer contains at least one of the above-mentioned aromatic salts and amines, and is selected from the following formulas (2d). At least one of the compounds represented by the above is more preferably at least one type of host material selected from the compounds represented by the following formulas (2a) to (2d).

131739.doc, 19·200916434 to express. In the formula (10), each is independently a group derived from an aromatic ring having a substituted or unsubstituted carbon number (i). The upper aroma ring may be replaced by one or more substituents. The substituent of the above aromatic ring is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted carbon number, a substituted or unsubstituted carbon number of 3 to 50. a base group, a substituted or unsubstituted methoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group (the carbon number of the aryl moiety is 6 to 50, and the carbon number of the alkyl group is 1 to 5), a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted carbon number (tetra) arylthio group, a substituted or unsubstituted oxo group (the methoxy group moiety, substituted or not) Specific examples of the substituted sulphuric acid group, a few groups, a dentate atom, an aryl group, a nitro group and a phono group to R5 to R, 2 are selected from the groups described below. In the case where more than one substituent is substituted, the above substituents may be the same or different. The adjacent substituents are bonded to each other to form a morphologically or unsaturated cyclic structure. Preferably, eight and eight 〇 It is also preferred that at least one of the groups is a substituted or unsubstituted condensed ring group having a carbon number of 10 to 30, which is preferably a terpene substituent. a substituent of a substituted or unsubstituted naphthyl group. The substituents of the substituted or unsubstituted carbon number 6 to 2 of A9 and V include phenyl, oxime-caiji, 2-caiji, 2-enyl, 9-fluorenyl, "phenanthryl, 2-phenanthryl, phenanthryl, 4-phenanthryl," 'sweet base-hthacenyl', 2_thick four* base, 9_thick four two 1 ratio , 2, fluorenyl, 4 fluorenyl, 2-biphenyl, 3-biphenyl, 4_, tert-triphenyl-4-yl, p-triphenyl-3-yl, bis-triphenyl , 131739.doc -20- 200916434 Inter-triphenyl I-based, cross-linked tris-based 3-yl, m-triphenyl-2-yl, o-tolyl, m-tolyl, "stupid", to third Phenylphenyl, p-(2-phenyl:yl)phenyl, "yl·2_cainyl, methyl xiaocai," lycopene, 4'-methylbiphenyl, 4"_third Butyl _ couplet three stupid _4_ base and so on. More preferably, it is a group derived from a substituted or unsubstituted aromatic ring having 1 to 14 carbon atoms, and particularly preferably a naphthyl group, a 2-naphthyl group or a 9-phenanthryl group. V~^ are each independently a heteroaryl group selected from a hydrogen atom, a substituted or unsubstituted carbon number of 60, 50, a substituted or unsubstituted carbon number, a substituted or unsubstituted carbon number, a substituted or unsubstituted a substituted alkoxy group, a substituted or unsubstituted carbon number of 5 (5), an alkoxy group, a substituted or unsubstituted aralkyl group (the carbon number of the aryl moiety is 6 to 5 Å) The carbon number of the alkyl moiety is a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, an arylthio group substituted or unsubstituted, and having an anionic number of 6 to 50, a substituted or unsubstituted alkoxycarbonyl group. (The number of turns of the alkyl file is 丨~"), a substituted or unsubstituted fluorenyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxyl group.

Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms of R5 to R12 in the formula (2a) include a phenyl group, a naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and 9- Sulfhydryl, 1_phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthrenyl, 9-phenanthryl, fluorene-tetraphenyl, 2-condensed tetraphenyl, 9-fused tetraphenyl, 1 - mercapto, 2-indenyl, 4_yl, 2-biphenyl, 3-phenyl, 4-biphenyl, phenylene-4-yl, bis-terphenyl-3-yl, bis-triphenyl -2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl, m-triphenyl-2-yl, o-phenyl, m-phenyl, p-phenyl, p-third Butylphenyl, p-(2-phenylpropyl)phenyl, 3-indolyl-2-naphthyl, 4-mercapto-1-naphthyl, 4-methyl-1-indenyl, 4,- Indenylbiphenyl, 4,, _ 131739.doc -21 - 200916434 Third butyl-p-triphenyl-4-yl and the like. As the substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms of R5 to R12 in the formula (2a), there may be mentioned: 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridinyl, 2- ° ratio σ base, 3 - ° ratio α base, 4 -吼 ° base, 1 - ° lead π-based, 2-α-induced π-based, 3- - ° α-based, 4-° η, 5-σ-α-based, 6-° D-based, 7-°-introducing, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindole , 5-isoindolyl, 6-isoindolyl, 7-isodecyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzene And furyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5 -isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl, 3-quinolyl, 4-indolyl, 5-nonyl, 6-indolyl , 7-indolyl, 8-indolyl, 1-isoindolyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7- Isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-indole-4 6 - saliva 11 lin base, 1 - 吟 σ sitting base, 2 - ° card α sitting group, 3 - leaf σ sitting group, 4 - α card α sitting group, 9 -吟α sitting group, 1-morphine σ base (phenanthridinyl), 2-morphine. Stationary, 3-_σ-based, 4-morphinyl, 6-cyridinyl, 7-cyridinyl, 8-cyridinyl, 9-cyridinyl, 10-cyridinyl, 1-acridinyl, 2 - aridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 1,7-morpholin-2-yl, 1,7-morpholin-3-yl, 1,7-morphine Physin-4-yl, 1,7-morpholin-5-yl, 1,7-morpholin-6-yl, 1,7-morpholin-8-yl, 1,7-morpholin-9-yl, 1,7-morpholin-10-yl, 1,8-morpholin-2-yl, 1,8-morpholin-3-yl, 1,8-morpholin-4-yl, 1,8-morpholine -5-yl, 1,8-morpholin-6-yl, 1,8-morpholin-7-yl, 1,8-morpholin-9-yl, 1,8-morpholin-10-yl, 1 , 9- phenanthroline-2-yl, 1,9-morpholin-3-yl, 131739.doc -22 - 200916434 1,9-° non-forest-4-yl, 1,9-1#琳-5 -yl, 1,9-# lin-6-yl, 1,9-'# phenyl-7-yl, 1,9-morpholin-8-yl, 1,9-morpholin-10-yl, l, l-Phenanyl-2-yl, 1,10-morpholin-3-yl, 1,10-morpholin-4-yl, 1,1 quinone-phenanthr-5-yl, 2.9- morphine-1 -yl, 2,9-°-non-lin-3-yl, 2,9-#yet-4-yl, 2,9-° phenanthro-5-yl, 2,9-morpholin-6-yl, 2 , 9-morpholin-7-yl, 2,9-morpholin-8-yl, 2.9-morpholin-10-yl, 2,8-morpholin-1-yl, 2,8-morpholin-3- Base, 2,8-morpholin-4- , 2,8-morpholin-5-yl, 2,8-morpholin-6-yl, 2,8-morpholin-7-yl, 2,8-morpholin-9-yl, 2,8-morph Porphyrin-10-yl, 2,7-morpholin-1-yl, 2,7-morphin-3-yl, 2,7-σ-non-lin-4-yl, 2,7-°-non-lin-5- Base, 2,7-° non-leaved-6-yl, 2,7-morphine-8-yl, 2,7-17 non-lin-9-yl, 2,7-morpho-_1〇-yl, 1 - phenazinyl, 2-morphine, 1-phenylene, tiofen, 3-port non-thiophene, 4-phenylthiophenyl, 10-phenylthiol, morphine Phenoxazinyl, 2-morpho p cultivating base, 3-morpho p-saki, cultivating base, 1 0-morphine, 2-oxazolyl, 4-11, azolyl, 5- P-oxazolyl, 2-oxadiazolyl, 5--11 succinyl, 3-a-furfuranyl, 2-°-septyl, 3-per-phenyl, 2-methylpyrrole -1-yl, 2-mercaptopyrrol-3-yl, 2-mercaptopyrrol-4-yl, 2-mercaptopyrrole-5-yl, 3-mercaptopyrrol-1-yl, 3-mercaptopyrrole -2-yl, 3-mercaptopyrrol-4-yl, 3-mercaptopyrrole-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-p-propylpropyl)pyrrole- 1-yl, 2-methyl-1-indenyl, 4-mercapto-1-indenyl, 2-methyl-3-indanyl, 4-methyl-3-indolyl, 2- Tributyl-1-indenyl, 4-tert-butyl-1-decyl, 2-tert-butyl-3-indenyl, 4-tert-butyl-3-indenyl, etc. . With respect to the substituted or unsubstituted calcined group of 1 to 5 Å of R5 to R12 in the formula (2a), a mercapto group, an ethyl group, a propyl group, an isopropyl 'n-butyl group, and a second I31739 may be mentioned. Doc -23 - 200916434 Butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxydecyl, 1-hydroxyethyl, 2-hydroxyethyl, 2- Hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy third

Butyl, 1,2,3-trihydroxypropyl, methoxymethyl, 1-oxyethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-diethylethyl, 1,3- Dichloroisopropyl, 2,3-digas tert-butyl, 1,2,3-trimethylpropyl, bromomethyl, bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, l,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iron methyl, i-moth ethyl , 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3_diiodoisopropyl, 2,3-diiodotributyl, 1,2,3- Triiodopropyl, aminomethyl, [_aminoethyl, 2-aminoethyl, 2-aminoisobutyl, ι,2-diaminoethyl, hydrazine, 3-diamine Isopropyl, 2,3-diaminotributyl, i,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2- Cyanoisobutyl, 12-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-tert-butyl, anthracene, 2,3-tricyanopropyl, nitrate Base group, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2, 3_dinitro second butyl, 1 2,3 - trinitro-propyl and the like. The substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 5 () in the formula (2a) may, for example, be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group 1 hexyl group, a "cyclohexyl group, a fluorene-gold gangster Burning base, 2_金刚院基, r降宿基基(ι_ norbornyl), 2-降格基, etc. The substitution of R5 to R12 in the formula (2a) or the alkoxy group having the inverse of 1 to 5 乂 of the oxime is a group represented by -OY; and the Y system is selected from the above-mentioned substitution of R to R12 or an enemy. The alkyl group has a carbon number of 1 to 50. I take I3l739.doc •24- 200916434 As for the formula (2a), R5~ri2 is taken as ^^~虱 unsubstituted aralkyl (the number of slaves of the aryl moiety is 6~50, and the number of mosquitoes in the alkyl group is 1) ~50), which can be exemplified by benzylic acid 1-benylethyl, 2-phenylethyl, and its two beautifully whistling _ yl, fluorenyl-phenyl isopropyl, 2-phenyl isopropyl, benzyl Dibutyl, α• extraction^^7, 〒'ylmethyl, l-α-naphthylethyl, 2-α-nonylethyl, 1-α-naphthylisopropyl, W Λ 1 η ^ Α ^ t-naphthylisopropyl, β-naphthylmethyl^β-nylethyl, 2-β-茏7 甘-*田^ ', butyl, 〖-β-naphthylisopropyl Base, 2-β-nylisopropyl, 1-σ-bi-hammerimo "Gan & methyl, 2-U-pyrrolyl)ethyl, p-methylindenyl, m-decylbenzyl, ortho its

丞卞 丞卞, p-benzyl, m-chlorobenzyl, sterol, ketone, kiln, kiln, ketobenzyl, p-iodobenzyl, m- benzyl Mercapto, o-hard benzyl, oxol-gan to L-mercapto, m-hydroxybenzyl, o-hydroxyindenyl, p-aminoindenyl, m-aminobenzyl, o-aminobenzyl, p-nitro Benzyl 'internitro group, o-nitro group, p-aryl group, m-cyano group, o-cyanobenzyl, 1 - antelope 9 Α w & violent-2-yl isopropyl , 1-chloro-2-phenylisopropyl and the like. The substituted or unsubstituted atomic number 6 to aryloxy group and the arylthio group of RR in the formula (2a) are represented by -ΟΥ, and _SY, respectively, and γΐΑγ is selected from the above-mentioned substitution of R5 to R12. Or an unsubstituted aryl group having 6 to 5 atomic atoms. The substituted or unsubstituted alkoxycarbonyl group of R5 to R12 in the formula (2a) (the carbon number of the alkyl moiety is 1 to 50) is represented by -COOZ. z is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms selected from the above-mentioned r5 to R! 2. As the substituted alkylene group of R5 to R12 in the formula (2a), a trimethyl fluorenyl group is exemplified. a triethyl decyl group, a tert-butyl decyl fluorenyl group, an ethylene dimethyl fluorenyl group, a propyl dimethyl fluorene group, a trisyl group, and the like. Examples of the halogen atom of R5 to R12 include fluorine, gas, and 131739.doc-25-200916434 bromine, moth, etc. The above R5 to R12 and/or the above A9 to A10 may be halogen atom, hydroxyl group, nitro group, group, Hyun", substituted by an oxy group, an aromatic heterocyclic group, a dioxin group, a slow group, etc., a substituent of an aromatic ring, and further a cyano group, an alkyl group, an aryl group, a cycloalkyl aralkyl group, an aryloxy group , arylthio group, The anthracene derivative represented by the formula (2a) is preferably a compound having a structure represented by the following formula (5)): [Chemical 10]

(In the formula (20, A9, Ai (^R5~Ri2) is as defined in the formula (2a). Among them, the substituents A9 and ΑΙϋ of the 9-position and the 10-position of the 蒽 structure are non-positive with respect to the χ_γ axis. The symmetry of the anthracene derivative represented by the formula (2a) used in the organic EL device of the present invention is exemplified by Japanese Patent Laid-Open No. 2004-356-33 [0043] to [0063]. Any of various known anthracene derivatives having two anthracene skeletons in the disclosed molecule or a compound having one anthracene skeleton disclosed in pages 27 to 28 of International Publication No. 2005/06 1656. Specific examples of sexuality: [Chemistry 11] 131739.doc -26- 200916434

[化 12]

131739.doc 27- 200916434

[Chem. 13]

131739.doc 28- 200916434

[Chem. 14]

131739.doc 29- 200916434

化^Λσ ρφτ

¢,3⁄4 813⁄4 ΛνΆ. 131739.doc -30- 200916434 [Chem. 16]

[Chem. 17]

In 131739.doc 200916434

173⁄4

81-3⁄4

5ν·Λ 131739.doc -32- 200916434

Δι-'tt

i ft

81'n r - 9 11 ep$

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3.3⁄4 131739.doc -33 - 200916434 οό^Λα

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s·

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33⁄4 S3 type (2b) [Chem. 21]

In the compound of (Zb), Ar1 and Ar2 are respectively incubated, and another J is independently substituted or not taken from an aryl group of 6 to 50; Ll and . An unsubstituted unsubstituted erbium is selected from substituted or unsubstituted, substituted or unsubstituted stilbene naphthyl, substituted or unsubstituted 羝 丨 - 丨, and substituted or unsubstituted a group in the group of dibenZ〇sil〇iyiene; 111 is an integer of 〇~2, η is an integer of s, S is an integer of 〇~2, and t is an integer of 〇~4. L1 or Ar! is bonded to any of the 1 to 5 positions, and L2 or Ar2 is bonded to the 6 to 10 positions of 芘. The nuclear carbon number of Ar1 and Ar2 in the formula (2b) is 6~ The aryl group of 50 can be exemplified by 131739.doc -35- 200916434 phenyl, 1-nyl, 2-naphthyl, iota-yl, 2-indenyl, 9-fluorenyl, 9-( 10-phenyl ) anthracenyl, 9-(10-naphthyl-indenyl)indenyl, 9-(1〇-naphthyl-2-yl)indenyl 1phenanyl, phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1_thick tetraphenyl, 2-thick tetraphenyl, 9-thick tetraphenyl, fluorene-fluorenyl, 2-fluorenyl, fluorenyl, 2-biphenyl, 3-biphenyl '4-biphenyl, conjugated triphenyl-4-yl, conjugated triphenyl-3-yl, conjugated triphenyl-2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl, Cross-linked triphenyl-2-yl, o-tolyl 'm-decylphenyl, p-mentyl, p-t-butylphenyl, 3-mercapto-2-naphthyl, 4-methyl-1-naphthyl , 4-methyl-1-indenyl and the like. Preferred are aromatic ring groups having 6 to 16 carbon atoms, particularly preferably phenyl, 1-naphthyl, 2-naphthyl, 9-(10-phenyl)indenyl, 9-(10-naphthyl). -1-yl)fluorenyl, 9-(10-naphthyl-2-yl)indenyl, 9-phenanthryl, 1-indenyl 2-indolyl, 4-indenyl, 2-biphenylyl, 3 -biphenyl, 4-biphenylyl, o-tolyl, m-phenylene, p-tolyl, p-tert-butylphenyl. Further, the above aryl group may be further substituted by a substituent, and examples of the substituted oxime include an alkyl group (fluorenyl group, ethyl group, propyl group, isopropyl group, n-butyl group, second butyl group, isobutyl group, Third butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, benzyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxy Ethyl, i, 3-dihydroxyisopropyl, 2,3-dihydroxyt-butyl, 1,2,3-trihydroxypropyl, methoxymethyl, oxime-ethyl, 2-chloroethyl , 2-oxobutyl, iota, 2-diethylethyl, iota, 3-diisopropyl, 2,3-dichlorodibutyl, 1,2,3-trimethylpropyl, bromine Sulfhydryl, i_bromoethyl, 2-bromoethyl, 2-diisobutyl, iota, 2-dibromoethyl, i,3-dibromoisopropyl, 2,3-dibromo 2nd Base, 1,2,3-tribromopropyl, fluorenylmethyl, 1_hard ethyl, 2_block ethyl, acetobutyl, I,2-diethylidene, 1,3_dipyridyl Propyl, 2,3-diiodide 131739.doc -36« 200916434 Tributyl, 1,2,3-triiodopropyl, aminoguanidino, oxime-aminoethyl, 2-aminoethyl , 2-aminoisobutyl, 1,2-diaminoethyl, ι,3-di Isopropyl, 2,3-diaminotributyl, i,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2 -Cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-tert-butyl, iota, 2,3-tricyanopropane Base, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-Dinitro-t-butyl, 1,2,3-trinitropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 丨-adamantane Alkoxy group having a carbon number of 1 to 6 (ethoxy group, methoxy group, isopropylidene group, n-propoxy group, etc.), a 2, adamantyl group, a fluorene group, a 2-norbornyl group, or the like a second butoxy group, a third butoxy group, a pentyloxy group, a hexyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc.), an aryl group having an atomic number of 6 to 4, and an aromatic number of 6 to 40 An amine group substituted with a group, an aryl group having an aryl group having an atomic number of 6 to 4, an ester group having an alkyl group having a carbon number of 丨6, a cyano group, a nitro group, a halogen atom or the like. L1 and L2 in the formula (2b) are preferably a substituted or unsubstituted extended phenyl group and a substituted or unsubstituted extended group. The substituent is selected from the group exemplified as the substituent of the above aryl group. m in the formula (2b) is preferably an integer of 〇~. 11 is preferably an integer of u. s is preferably an integer of 〇~1. t is preferably an integer of 〇~2. Specific examples of the specific derivative represented by the formula (2b) used in the organic EL device of the present invention include International Publication No. 2/5 1 595 No. [〇〇20]~ Asymmetric anthracene derivatives as disclosed in [〇023]. Further, a symmetric fluorene derivative can also be used as the material for the organic EL device of the present invention. Representative examples of 131739.doc-37-200916434 are disclosed below. [化22]

m

[Chem. 23] 131739.doc -38 - 200916434

[Chem. 24]

131739.doc -39 - 200916434

[Chem. 25]

131739.doc -40- 200916434

Γ<|

[Chem. 26]

In the compound, 'Ar and Ar5 are separated from each other. The knife is independently selected from the group consisting of a base with a phenanthrene structure, and a base with a right-handed structure, and a base with a specific structure; R〗, R" is a hydrogen atom or a substituent. Ar, Ar5 in the formula (2C), preferably selected from substituted or unsubstituted thiophenyl, fluorenyl: phenanthryl, perylenyl and ketone, more preferably selected from Alkyl-substituted or unsubstituted nonylphenyl, phenanthryl and anthracenyl groups, particularly good 131,739.doc 200916434 Describes self-favoring and phenanthryl. As for R"~R"' in the formula (2c), it can be mentioned that the hydrogen atom is a carbon number of 30, more preferably the carbon number is good, and the carbon number is a carbon number of 10; For example, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, an n-octyl group, a n-decyl group, a n-hexadecanyl group, a cyclopropyl group, a cyclopentyl group, a ring=etc. It is preferred that the carbon number is 2 to 3 Å, and more preferably carbon or soil is particularly preferably a carbon number of 2 to 10; for example, an ethylene group: a diyl group, a 3-pentenyl group, etc.) , block base (preferably, the carbon number is Μ.: good 疋 carbon number is 2~20, especially good county 铋 铋 more acetylene", (4) good ochre inverse number is 2~10; for example, Mercaptopropyl, 3-pentynyl, etc., aryl (compared with a carbon number of 6 to 20, particularly preferably a gas number of 6 to 30, and a better number of bamboo pairs of 6 to 2) Phenyl, p-methylphenyl 'naphthyl, window based 箄) ^: ~3〇' is better for the carbon number. 〜2 is a good carbon number, for example, an amine group, a methylamino group, a _; = the number of hearts is (4); a base amino group, a diphenylamino group, a dioxin amine, a second, a ethylamine The base and the second quarter are carbon numbers! ~%,更更# θ ώ ώ 胺 # ) ) ) 烷 烷 烷 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好 较好The number is an oxy group, etc., an aryloxy group (preferably a diterpene; a ethyl ethyl group is particularly preferably a carbon number of 6 to 2) 2 to 3 Å. More preferably, the carbon number is

For example, a naphthyloxy group, a naphthyloxy group or the like, and a phenoxy group, and a carbon number is preferably a 2Q quaternary oxy group (preferably, the carbon number is 邛~邛, & The number of extinctions is 丨~20, especially: the mouth is more than the bite oxy...the idiot is 】~]2 ' For example, the base can be used (preferably, the number of breaks is 2~3〇, 疋=base, porphyrin oxygen) Base, etc.), acid has a carbon number of 2 to 12; for example, it is preferably a carbon number of 2 to 20' particularly good cattle • ethyl group, alum, and formic acid I3I739.doc -42- 200916434 two cups: Γ基乙 SS基等), 炫氧M基 (preferably, the carbon number is 2~30, and the output: the number of bismuth is 2~2G' is particularly good, and the reliance is 2~12; for example, 7 3i ) W-based 'ethoxy group, etc.), aryloxy group (preferably, the number of breaks is 7 7 to 30, more preferably the carbon number Α 7 # 厌 为 如 如 如 如 如 特别 特别 特别The number is 7 to 12; for example, the carbon number is 2 2 Γ "base (preferably, the carbon number is 2 to be different, more preferably ethoxylated, 'excellently, the carbon number is 2 to 10; for example For example: 2 3〇"this milk base, etc., amidino group (preferably, the carbon number is 2~30, more preferably < the number of turns is as士士: 7 is particularly good, the carbon number is 2~10; for example, n a16 base, benzene? awakening amine, etc.), silk (tetra) amine group (the better meteorite disgust is 2~3 〇, The number of 乂 为 is 2 丨, and the number of 疋 slaves is 2 to 20, and particularly preferably, the carbon number is Μ, for example, an oxyamino group (preferably, the carbon number is 7 to 3 Å, more preferably The base group has a carbon number of 7 to 2; for example, it is particularly preferable (preferably, the carbon number is U: "makeup base, etc.", sulfonamide, etc.), and the amine sulfonamide. The base (better β-bearing amine group, benzene-continuating amine group. 〜2., particularly preferably, the carbon number is methylamine fluorenyl group, dimethylamino fluorenyl group, benzene aryl group, formazan group (preferably, the carbon number is (tetra) amide, etc.), and the amine is preferably a carbon number of 1 to 12, for example, the carbon number is 1 to 20, and the specific number is 0, and the -r I flA m • Aminomethyl sulfhydryl, methylamine carbhydryl, monoethyl carbamoyl, and phenyl carbamide are those having a charcoal number of 1 to 3 G, more preferably a thiol group (preferably 1 to 12; for example, a thiol group or a shovel can be mentioned, and it is particularly preferable that the carbon number is (1). 'Better is: =:, Fang Fine is particularly good, the carbon number is 131,739.doc •43·200916434 ~... For example, stupid sulfur 1~3〇' is better, the number is 〜20, and the material is: "(It is better that the carbon number is For example, ... base, 2_ cage is good carbon number is 1~u, · example base, 2_benzothiazolylthio group, etc. sit-base, 2~ benzopyrene is better carbon The number is 丨~2〇 (the preferred carbon number is 丨~%, ώ · Ψ Ά The temple is good for carbon number 1~12. & Λ.h醯基,甲笨磺3 12' It is preferable that it is 1 to 30'. More preferably, the carbon number is a broad base (preferably, the carbon number is, for example, h ^ 2 2 G' is particularly preferably a carbon number of i 12 12; ((4) ld〇) Preferably, the carbon number is = base 4), and the gland group is preferably a carbon number, for example, a number of two is "1". , thiourea, etc.), dish amide (preferably broken ", methyl serving base, benzene is 1~20" is particularly good, the carbon number is i ^ 〜 3 〇 'better carbon number 醯Amine, phenyl flavonoid, etc.), and a thiol group: a fluorine atom, a gas base group, a south atom (for example, a base group, a several group, a stone atom, etc.) An alkoxy group, a sulphate, a sulphonic acid group, a sulfinyl group, a sulfinyl group, a sulfonyl group, preferably a fluorenyl group (preferably a carbon number) fluorenyl group; hydrazine; and a hetero atom, for example, nitrogen The atomic number is earlier and the two ' ' ' oxygen atom, sulfur

Li l: A can be exemplified by, for example, a base, a base, a base, a sulphate, a piperidine, a morpholinyl group, a benzophenanthine, a basic sputum, and the like. The carbon number is 3~in and the anodic two 40, more ''', especially the carbon number is 3~24, for example, the trimethyl decyl group, the three cages And can be replaced. * Μji Temple) and so on. The substituents W5 of the substituents in the formula (IV) are preferably selected from the group consisting of a leukoyl group and an aryl group. I3l739.doc -44 - 200916434 A specific example of the amine derivative represented by the formula (2c) used in the organic EL device of the present invention is exemplified by Japanese Patent Laid-Open Publication No. 2002-324678 [0079] [0083] A known various amine derivatives such as amine derivatives disclosed herein. Representative examples of the representative are disclosed below. [化27]

[化 28] 131739.doc -45 - 200916434

Π厶t

I Formula (2d): [Chem. 29]

ArJ1 f ^Ar (2d)

Among the compounds represented by Ar31 \r81, Ar11 to Ar31 independently represent the aryl group having a nuclear carbon number of 6 to 50, 131739.doc -46- 200916434. The above aryl group may be substituted by one or more substituents. AjJ, and at least "solid" of the substituents possessed by the aryl group, having a stone inverse number of 10 20 , a % ylidene aryl structure or a carbon number of 6 to another fused ring heteroaryl structure. Ar represents a trivalent group derived from an aromatic ring or a heteroaromatic ring. The carbon number of the aryl group of Ar to Ar of 弋() is preferably 6~chuan, more preferably 2(4)' especially preferably 6~16 As the aryl group, a phenyl group, a naphthyl group, a thiol group, a phenanthryl group, a ketone group, a aryl group, a benzyl group, a biphenyl group, a triphenyl fluorene group, a thiol group, a triphenyl phenyl group, and a triphenyl phenyl group are mentioned. The benzoinyl group and the benzene are not: -phenyl fluorenyl group or the like. The aryl group may further have a substituent. The substituent on the number group may, for example, be an alkyl group (preferably, the carbon number is 1 to 1). 30, more preferably, the carbon number is 1 1Λ. ^ The sigh is 1 to 20, and particularly preferably the carbon number is Π:: cite: methyl, ethyl, isopropyl, tert-butyl, plus twenty-six The base, the base, the cyclopentyl group, the cyclohexyl group, the carbon number is 2~3°. More preferably, the carbon number is 2~2. The particularly good carbon number is 2~1〇; For example, 2-butenyl, 3-pentyl, etc.), _:·ethylidene Dilyl, preferably a carbon number of 2 2 () M is a carbon number of 2 to 3 〇, more: alkyne propylene, and preferably a carbon number of 2 to 10; for example, a better It is a di number and an aryl group (preferably, the carbon number is 6 to 3 Å, and the number of better rabbits is 6 to 20' is particularly good: phenyl, p-methylphenyl, Caiji, to: two' For example, the carbon number 〜 0 〜 30 s ... ji Temple), the amine group (preferably, the number is 〇30, more preferably the carbon number is 〇~^ 〇~10, and, for example, an amine group is exemplified. , methylamino...-, vermiculite anthraquinone, bis-amino group, diphenylamino group, indole methyl group, its methylamino group, diethylamino group (preferably, the number of breaks is 1, more) Good is the number of carbon =), the number of people burning oxygen is 1~20 'Specially good 131739.doc -47- 200916434 is the carbon number is 1~〗 〇. n, base, 2-ethyl has two, ::: cite : f oxy, ethoxy, butoxy is preferably a carbon number of 6 ;), a aryloxy group (preferably, the carbon number is 6 to 30, more: phenoxyl meaning; particularly preferred is the carbon number It is Μ; for example, 1-naphthyloxy, 2-extracted oxygen, carbon number is 丨~3(),, fluorenyl), heteroaryloxy (better) Preferably, the carbon number is 1 to 20, 1 to 丨2; for example, it is particularly preferable that the carbon number is U: a pyridyloxy group, a phenyloxy group, etc.), a sulfonyl group, a pyrimidinyl group, or a quinine; Sulfhydryl (preferably, the carbon number is 丨~如, 1~20, and particularly preferably, the carbon number is divination. "The number of good gorges is formazan, formic acid A, ..., for example, acetyl group. Benzene-methyl-ethyl ketone, the carbon number is 2 to 3 〇, more preferably # s mountain, alkoxycarbonyl (preferably 2 to 12; for example, ^ 2 〇 ' special Preferably, the carbon number is (preferably, the carbon number is 7 to 3. , the second number is -I can be exemplified by phenoxysilane), ::,: The other is that the carbon number is 2~3〇, and the better the carbon number is 2~2〇, the base of the milk is good. Carbon 2 to 10, for example, ethoxylated, benzene = preferably carbon number (preferably, carbon number is 2 to 3 Å, two methyl methoxy groups, etc.), The guanamine group has a carbon number of 2 to 1 〇; for example, it can be combined with a mountain horse 2 to 20 'very good + out. acetic acid face and the like), an alkoxycarbonylamino group (preferably, the carbon number is 2 benzene). The methionine group is 2 to 20, particularly preferably the carbon number is 2 to 12 丨 = 2 to 30, more preferably a carbon number group, etc.) aryloxycarbonylamino group (preferably π 彳The number of oxocarbonylamines is from 7 to 20, particularly preferably from 7 to 2, from 7 to 30, more preferably from a carboamine group, or a sulfonamide group (preferably, the carbon number is For example, the phenoxycarbonyl group is 1 to 20, and particularly preferably, the carbon number is 〖I2'', more preferably a carbon number group or a benzenesulfonylamino group, and the amine group is exemplified by: Sulfonamide Κ 4 (preferably the carbon number is ~3 〇, more 13I739.doc -48- 200916434 !~2. ' Particularly good is the carbon number. ~i2· For example, it can be used as an enemy base, etc., and an amine group (preferably, a base group, a base number of a base group) is particularly preferably a 2;:/3: a good one is a base, a methylamine Base, dimethylamine yak, amine guanidine, etc.), burnt stone * its fpkk, benzylamine, hydrazine, hydrazine, base (the good carbon number is 1 to 30, better θ I , particularly preferably, the carbon number is W2; the carbon number is equal to), the arylthio group (preferably, the number of discs is 6 to 3 Torr, more preferably: the ethyl thio group 6 is particularly preferably a carbon number of 6 to 12, for example, the carbon number is heteroaryl fluorenyl (preferably, the carbon number is H0, more + b sulfenyl, etc.), and particularly preferably, the carbon number is 丨~12, and the number of slaves is 1 to 20 , imiphathiol, A than thiol, 2 benzopyrene, triazole thiol, 2 benzothiazole, 较好, (better carbon number is better! The number of the two is 1 to 12', for example, a continuous base, a toluene, ... a carbon number is a diyl group, a sulfinyl group, etc., a urea group (preferably a carbon number 丨) ~30, more carbon number 1~20, especially good carbon methyl base, purchase _" For example, gem base, better ΘΑ ), decylamine (preferably, the carbon number is 1 to 3 0, h is & the number (four) is good, the carbon number is 〜~... 乙·乙乙苯胺, phenyl aryl amine, etc.), Meridian, 1 atom (for example, chaotic atoms, chlorinated bismuth, etc.), aryl group, contiguous group, several groups, deterministic group, jing (4) original: broken atomic base, G face Work 驮 、, sulfinyl, fluorene nucleobase (preferably carbon number is 1~30, more preferably carbon i31739.doc ►49- 200916434 number is 1~12; as for the temple; stone six atoms. Examples thereof include a nitrogen atom, an oxygen atom, and an atom, and specifically, for example, A, sulphate, imidazolyl, pyridyl, quinolyl, benzo (tetra), benzyl,琳琳基, 苯十坐基, 苯和 ^ ^ 3.40^ (a2ePinyl) f } ' It is good that the carbon number is... the second is 3~Μ J ♦ dimethyl shi 妓 妓 · its, two #基矽alkyl, etc.). These substitutions " two substituents can in turn be substituted. In the formula (2d), Ar]i~Ar" and ws] s are at least one of the substituents of the Shisi square, and have a carbon number of 10 to 2, a main ring, a 5 ^ group structure or a Wei 1 2 3 The shrinkage of the carbon nanotubes is as follows: for the carbon number iq~Μ, the naphthalene structure, the 蒽 structure, the 构 structure, the a structure, the 构 structure, the 茈 structure, etc. Pregnancy, good naphthalene structure, 蒽 structure, * deficit structure, 4 ring or more, its social structure, phenanthrene structure, better is Philip. #土, 0结构; particularly good is 芘 structure. As for # a fused ring heteroaryl structure having a number of 6 to 20, a structure of a porphyrin structure, a quinazoline structure + a porphyrin structure, a quinoxaline structure, etc., preferably a phthalocyanine::, a German structure, a (four) structure, a structure , 酞 结构 结构 structure, morphine structure. 上 啉 啉 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 It is 6~16. As for the trivalent group derived from 3〇, more preferably 3~2〇, especially derived from the m-fragrance ring, it can be cited as ···" Xinfei, Cheng, and extension triphenyl derivative The bivalent A and other aromatic rings are preferably contained There are € from &A, a secret base, etc. The hetero--50. 1 , as a nitrogen atom of a hetero atom, 2 milk ', ', ',,, preferably, contains a nitrogen atom: * 3 is preferably 2~ 30, more preferably 3~2〇, "Fangxiang% is especially good 3~16. As for the specific example of the 2#1 Becky derived from the I31739.doc 200916434 heteroaromatic ring, : a trivalent group derived from pyridine, pyridin, thiopyran, quinoline, geniline, and tricotyl. The trivalent group derived from the aromatic ring or heterocyclic ring may have a

Substituents for Ar, Ar2 and Ar" r. Such substituents are selected from

The base on the aryl group of Ar is taken from the substituents of your recovery. Ar is preferably a benzenetriyl group, a natriuret group, a bismuth group, a ++ one-to-two-base group, a trivalent group derived from a linked triphenyl group, and more: a benzenetriyl group is particularly good. An unsubstituted benzenetriyl group (having no substituents other than Ar, A21, and Ar3), an alkyl-substituted benzenetriyl group. Specific examples of the stupid organism represented by the formula (2d) used in the organic EL device of the present invention include benzene disclosed in JP-A No. 2 [0079] to [0083]. A well-known various benzene derivatives such as derivatives. Representative examples of the representative are disclosed below. [化30]

131739.doc 51 200916434

[化31]

131739.doc 52- 200916434 [Chem. 32]

In the present invention, as for the organic EL element of the plural layer type, the organic layer is a (anode/ray, 円, + pen hole injection layer/light-emitting layer/cathode), The anode/light-emitting layer/electron injection layer/cathode, w-, (anode/hole injection layer/light-emitting layer/electron>main-in layer/cathode), etc., are laminated, and the above-mentioned plural layers are removed as needed. In addition to the aromatic amine derivative 131739.doc-53-200916434 of the present month, a known luminescent material or an electron injecting material may be used. The organic EL element may be formed of a material or a hole injecting a plurality of layers. And prevent the organic film layer from being low. If there is, the brightness or life drop of the formation or the electron, the 'main input ^1 miscellaneous material, the hole injection material 4 are used in combination with the Zhuangcheng material. τ illuminating brightness or illuminating The improvement of efficiency: the two-doped material can also obtain the hole injection layer, the luminescent layer, the second color, the luminescence, and the electric layer is formed. At this time, the exhibition of the electric hole above the tiantian-layer For the case of the second entry layer, the self-electrode is injected with nt ^ ^ · 4 ΐ ^ ^ . Electrical / receiving with a hole injection layer again:!: = Layer of the light-emitting layer is called a hole transport layer round the same, the electronic.

In the case of =, the layer in which electrons are injected from the electrode is referred to as an electron injecting layer, and the electron injecting layer is received from the electron injecting layer. The layer transported to the luminescent layer is called Moon 仏曰 / / : each layer can be selected according to various factors such as the energy level of the material, the tamper resistance, the adhesion of the plaque organic layer or the metal electrode. - As for the host material or the doping material other than the above formulas (2a) to (2d) which can be used together with the aromatic amine derivative of the present invention, for example, naphthalene, phenanthrene, and red fluorite Alkene (10) rene), onion, thick tetraphenyl (10) (10) (four), =, court,?矣, 十环稀(d(10)咖ene), 蔻(c〇r〇nene), tetraphenylpentenepentapentaphene pentoxide, the first, the snail (Cai (10) please call, 9,H)_diphenyl Condensed polyaromatic compounds such as fluorene, 91 bis(phenylethyl) fluorene, bis-ethyl fluorenyl phenyl) and the like _8_喧琳)_4_(phenyl phenyl) Shao and other organic metal complexes, diaminoamine Ho, styrene derivatives, stilbene (sUlbene) derivatives, coumarin derivatives... Bitan (four) is called derivative " No. 131739.doc •54· 200916434 oxane derivative, benzothiazole derivative, benzoxazole derivative, present open imidazole derivative, pyridin derivative, cinnamate A derivative, a diketopyrrolopyrrole derivative, a quaternary quinacridone derivative, or the like, but is not limited thereto. As for the hole injecting material, a compound having the following properties, that is, having the ability to transport a hole, having an effect of injecting a hole from the anode, having an excellent hole injecting effect to the light emitting layer or the light emitting material, and preventing light emission are preferable. The excitons generated in the layer move toward the electron injecting layer or the electron injecting material, and the film forming ability is excellent. Specific examples thereof include a phthalocyanine derivative, a naphthalocyanine derivative, a porphyrin derivative, carbazole, oxadiazole, and trisole. Sit, sniffing, misoprostol, imidaz〇lethi〇ne, pyridoxine. Pyrazolone (pyraz〇l〇ne), tetrahydroimidazole, anthraquinone, acylhydrazone, polyarylalkane, stilbene, butyl diphenyl, benzidine triphenylamine, styrylamine triphenylamine, A diamine type triphenylamine or the like, a derivative thereof, and a polymer material such as polyvinyl carbazole, polydecane, or a conductive polymer; however, it is not limited thereto. Among the hole injecting materials which can be used in the organic EL device of the present invention, a more effective hole injecting material is an aromatic tertiary amine derivative and a phthalocyanine derivative. As the aromatic tertiary amine derivative, for example, triphenylamine, tridecylphenylamine, nonylphenyldiphenylamine, N,N'-diphenyl-N,N'-(3- Nonylphenyl)-1, fluorene-biphenyl-4,4.-diamine, hydrazine, hydrazine, hydrazine, Νι_(4-mercaptophenyl)phenyl-4,4-diamine, hydrazine, hydrazine ,Ν',Ν'-(4-mercaptophenyl)-1,1'-biphenyl-4,4,-di 131739.doc 200916434 Amine, hydrazine, hydrazine-a stupid-N,N'- Nylidene biphenyl_4,4i_diamine, n,n,_(methylphenyl)-N,N'-(4-n-butylphenyl)-phenanthrene-9, ι〇_diamine, N, Nj(4-di-4-methylaminophenyl)-4-phenyl-cyclohexane or the like, or a valence polymer or polymer having the aromatic secondary amine skeleton, but is not limited thereto . As for the phthalocyanine (Pc) derivative, for example, h2Pc, CuPc, CoPc,

NiPa, ZnPc, PdPc, FePc, MnPc, ClAlPc, CIGaPc, CllnPc, CISnPc, Cl2SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc, GaPC-〇-GaPc and other phthalocyanine derivatives and naphthalocyanine Derivatives, but are not limited to these. Further, in the organic EL device of the present invention, it is preferred that a layer containing the aromatic tertiary amine derivative and/or a phthalocyanine derivative, for example, the above-mentioned hole transport layer or electricity, is formed between the light-emitting layer and the anode. Hole injection layer. As for the electron injecting material, a compound having the following properties, that is, having the ability to transport electrons, having an effect of injecting electrons from the cathode, having an excellent electron injecting effect on the light emitting layer or the light emitting material, and preventing generation in the light emitting layer are preferable. The excitons move toward the hole injection layer and have excellent film forming ability. Specifically, it can be mentioned: g酉tong, onion s Kunming, bis-benzene, thiopyran dioxide "carbazole" Sitting, triazole,. Meter. It is not limited to these, such as tetradecylic acid, decylene methane, hydrazine, etc., and the like. Further, it is also possible to add an electron acceptor substance to the electron injecting material by adding an electron acceptor substance to the hole injecting material to sensitize it. Among the organic EL elements of the present invention, more effective electron injecting materials are metal complexes and nitrogen-containing five-membered ring derivatives. As the above metal complex, for example, lithium 8-hydroxyquinolate can be mentioned.

131739.doc -56- 200916434 (8_Jie Kelin) Zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, bis(8-hydroxyquinoline) aluminum, three (2 -mercapto-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)indole, bis(10-hydroxybenzo[h]quinoline) Zinc, bis(2-methyl-8-quinoline) gallium hydride, bis(2-methyl-8-quinoline) (o-cresol) gallium, bis(2-methyl-8-quinoline) 1-naphthol) aluminum, bis(2-methyl-8-pyroline) (2-naphthol) gallium, etc., but is not limited thereto. / \ ; This & nitrogen pentoxide derivative ' For example, preferably P number. Sitting, D plug, sitting on a azole, thiadiazole, triazole derivative. Specifically, 2'5-bis(1-phenyl)_13, 4 sitting, dimethyl ρ〇ρ〇ρ, 2,5 bis (!_phenyl)-1,3,4 -thiazole, 2,5-biguanide-phenyl bromide, bis(4-butylphenyl)-5-(4"-biphenyloxadiazole, 2,5-double (丨_naphthyl)_ '3,4-azole, anthracene, 4_bis[2_(5-phenyloxadiazolyl)]benzene, I〆·bis(5-stupyloxadiazolyl)- 4_T-butyl stupid], 2-(4,-t-butylphenyl)_5_(4 such as phenyl)Ίρ stopper diazole, 2,5-bis(1-naphthyl)_1,3, heart Selling di-salt, 1,4-bis[2-(5-phenylthiadiazolyl)]benzene, 2-(4,_t-butylphenylphosphonium biphenyl)-1,3,4-triazole 2,5_biguanide_naphthyl anthracene, 3,4_triazole, anthracene, 'also [(5phenyldiazolyl))benzene, etc.; but not limited to these. In the light-emitting layer, in addition to the at least one aromatic amine derivative represented by the formula (1), the first layer may contain the precursor material, the dopant material, the hole injection material, and the electron injecting material to the same layer. In order to enhance the pair of organic EL elements obtained according to the present invention: degree, 4 degrees, environment, etc. The stability of the component may be protected by the surface of the component or by the use of crushed oil, resin, etc. The conductive material used in the anode of the organic EL device of the present invention is 131739.doc -57- 200916434 For those having a work function of more than 4 eV, it is possible to use alloys such as ruthenium, methane, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc., which are used in ITO substrates and NESA substrates. An oxidized metal such as tin oxide or indium oxide, or an organic conductive resin such as polythiophene or polypyrrole. As for the conductive material used in the cathode, it is preferred to use a work function of less than 4 eV, which can use magnesium or calcium. Tin, lead, titanium, tantalum, lithium, lanthanum, manganese, aluminum, chaotic clock, etc., and the like, but are not limited thereto. As for the alloy, magnesium/silver, magnesium/indium, lithium/ Aluminum or the like is a representative example thereof, but is not limited to the crucible, etc. The ratio of the alloy can be controlled according to the temperature of the distilled source, the ambient gas, the degree of vacuum, etc., and is selected at an appropriate ratio. If necessary, it may be two or more layers. The layers form the anode and the cathode. In order to make it efficiently emit light, it is preferable to make at least one surface sufficiently transparent in the light-emitting wavelength region of the device. It is preferable that the substrate is also transparent. The transparent electrode uses the above conductivity. The material is set in such a manner as to ensure a specific light transmittance by means of steaming or the like. The electrode of the light-emitting surface preferably has a light transmittance of 1 (eight). If the substrate has mechanical, thermal strength and phase properties: ΓThere is a glass substrate and a transparent resin film. As for the transparent resin film: 牛牛·β ethylene, ethylene-vinyl acetate copolymer polymer, polypropylene, tactical r method s vinyl alcohol 碲 t vinyl 1 methacrylic acid "thin, polyethylene, polyethylene, nylon, poly-ketone, poly: π (four), four gas ethylene - full gas-based ethyl ether ether copolymer, polygas B : tetrafluoroethylene-ethylene copolymer, tetradecene ethylene, trifluoroethylene, poly-vinyl-fluoroethylene M: propylene copolymer, polychlorinated ethylene, polyester, polycarbonate, polyamine phthalic acid I3I739. Doc •58- 200916434 Ethyl ester, polyethylenimine, polyetherimide, etc. The formation of each layer of the ship component of the invention can be sputtered, plasma, ion thunder ... money (four), ... '胄 plating special dry film forming method' or spin coating, dipping, flow box wet film forming method φ > k ^ ^ ^ method. The thickness of the film is not particularly limited, but it must be set to be an alternative. If the film thickness is too thick, it is necessary to apply a large electric rhyme for the light output obtained. decline. If the film thickness is too high, the yoke is not charged to obtain sufficient illuminance. Generally, the thickness is preferably in the range of 5 nm to φ υ μηι, more preferably in the range of 10 nm to 0.2 4 〇 1 . In the wet film forming method, the material of the layer is immersed in each layer to dissolve or disperse in a solvent such as methanol, imitation, tetrachlorofuran, or a solvent suitable for the purpose of forming a thin sputum. However, the solvent may use any of the above solvents. For the solution to be used in the middle, a solution containing an organic EL material containing the present method and a compound of the formula can be used. Further, the above organic anal material ^ 2 body material is mixed and replaced. The agent material, the above-mentioned impurity agent material is the aromatic amine derivative of the present invention. The above-mentioned host material is selected from the group consisting of the formula (2a), the formula (2b), and the formula (2c). It is of the formula (2d). At least at least one of the compounds may be used, or a tree sputum or an additive for improving film formation properties, r ^ -a pancreatic pinholes, or the like may be used. As for the resin that can be used, ^ cites: polystyrene, polyphthalate, polyaryl vinegar, polyester, polyamine, 'mt ethyl methacrylate, poly wind, decyl decyl acrylate, poly Acrylic lysine, cellulose and other insulating trees and their copolymers; poly (ice vinyl edge ^ electrical resin; poly (four), poly (tetra) and other conductive, W-fired light-guide resin. Also, as for the addition of 131,739. Doc-59·200916434 The agent can be exemplified by an antioxidant, an ultraviolet absorber, a plasticizer, etc. The organic EL device of the present invention can be applied to a flat panel display of a wall-mounted television: an isometric illuminator, a photocopier, and a print A light source, a display panel, a marker lamp, etc. of a backlight or a meter of a night crystal display. Further, the material of the present invention can be used not only in an organic rainbow element but also in an electrophotographic photoreceptor, a photoelectric conversion element, and a sun. Field of the battery, image sensor, etc. Example Synthesis Example 1 Synthesis of Compound (D-2) (1-1) Synthesis of 2-(2-bromonaphthalene-6-yl)benzaldehyde in an argon gas stream Add 2,6-dibromonaphthalene to the 〇^ e^ three-necked flask of the condensing camp 10.3 g (36 mmol), 2- formazan: a: — w ^ Τ ® basic group acid 5.4 g (36 mm 〇 1), (tetrakis(triphenylphosphine)) 〇 · 7 g (〇6 _〇 ι), 2 n sodium carbonate aqueous solution 45 mL, a f-oxygen aldehyde 9 〇 mL, heated under reflux for 8 hours. After the reaction is completed, water _ mL is added to the reaction solution, and the organic layer is separated and washed with saline. The first 1 sulfuric acid material is dried. After the solvent is removed by a rotary evaporator, the obtained crude product is purified by tube chromatography (tetra), hexane/dichlorodecane = 60/40). a The target compound was 8·9 g (white crystal) (yield 80°/〇). (1-2) Synthesis of 2-Mo-6-((2-methoxyethenyl)phenyl)naphthalene in an argon flow, adding a naphthene to a 5〇〇眺 three-necked flask with a condenser Benzoyl red 8 g (25 mm. 丨), (methoxymethyl)triphenyl chloride g (30 mmol), after drying four reactions, to the reaction scales 11 g (30 mmol), third Potassium butanol 3 8 Hydrofuran 250 mL, stirred at room temperature overnight. I31739.doc -60- 200916434 Add 1 〇〇 mL of water to the solution, and divide the organic layer to dryness with magnesium sulfate. After distilling off the solvent by a rotary evaporator, the obtained crude product was purified by column chromatography (hexane, hexane/dihexane methane = 10/90) to afford 6.7 g (yel 〇%). (1 - 3) 2 - Moisture in a flow of argon in a '50 liter mL three-necked flask with a condenser tube. Add 2_filled '6 ((2-methoxyethenyl)phenyl) naphthalene 6.7 g (20 mmol) ), a few drops of methamphic acid, dry dichloromethane 1 00 mL ' and then stirred at room temperature for 8 hours. After the reaction was completed, an aqueous solution of sodium hydrogencarbonate 丨〇〇 mL was added to the reaction mixture, and the crystals were filtered. The obtained crude product was washed with water and methanol, and then dried. The underarm was subjected to vacuum drying for 8 hours to obtain the target compound 5·5 g (white crystal) (yield: 90%). (1-4) Synthesis of Compound (D-2) in a stream of argon, adding 2-bromo chopsticks to a 3〇〇mL three-necked flask with a condenser tube, 3 g (l〇mm〇l), N-phenylnaphthalene -2-amine 2.6 g (12 mm ο 1), acetic acid 0.03 g (1.5 mol%), tri-tert-butylphosphine 0.06 g (3 mol%), sodium butoxide sodium 1.2 g (12 mmol) Dry toluene loo mL, then at 1 Torr. (: The mixture was heated and stirred overnight. After the reaction was completed, the precipitated crystals were collected by filtration, washed with hydrazine 5 〇mL and decyl alcohol 1 〇〇 mL to obtain 3.5 g of pale yellow powder by FD-MS (% desorption mass spectrometry) Field Desorption-Mass Spectrum) was identified as Compound (D-2) (yield 90%). Example 1 (1) Organic EL element was fabricated on a glass substrate of 25 mm x 75 mm x 1.1 mm thick, and a film was provided. The thickness is 131739.doc -61 · 200916434 130 η is a transparent electrode formed of indium tin oxide. The glass substrate is ultrasonically cleaned in isopropyl alcohol, and then irradiated with ultraviolet rays and ozone to be cleaned. The glass substrate with the transparent electrode is mounted on the substrate holder in the vacuum chamber of the vacuum evaporation apparatus, and the degree of vacuum in the vacuum chamber is reduced to lxlO·3 Pa. First, the surface on the side where the transparent electrode is formed On the other hand, a layer of N''N"_bis[4.(diphenylamino)phenyl]diphenyl _4,4'-diamine was formed at a vapor deposition rate of 2 = m/see. The film has a thickness of 6 〇 nm so as to cover the transparent electrode. The film functions as a hole injection layer. Eight people in the hole injection On the layer, a layer of 'N'N N -tetrakis(4-diphenyl)benzidine was formed at a deposition rate of 2 nm/sec to a film thickness of 2 〇 nm. The film functions as a hole transport layer. Simultaneous vapor deposition of the above compound (2a, -55) [luminescent material 1] and compound (D-2) [luminescent material] at the vapor transport rate of 2 nm/sec and 0.2 nm/sec, respectively. To the film thickness of 40 nm 'and the weight ratio (2a'-55): (D-2) = 40: 2. The film functions as a light-emitting layer. Three (8-Cycle. 啥琳)|Lv is evaporated to a film thickness of 20 nm to form an electron transport layer. ~τ~ ^ The lithium fluoride is steamed at a steaming rate of nm·1 nm/sec. The film thickness was set to 1 _ to form an electron injecting layer. I: After the aluminum was vapor-deposited at a deposition rate of 2 nm/Sec to a film thickness of 200 nm 'to form a cathode layer' to fabricate an organic EL device. Evaluation of organic el element 131739.doc •62- 200916434 Then, the component was subjected to a power-on test, and it was confirmed that the luminance was 300 cd/m2 at a voltage of 6.3 v, and the illuminating color was blue. It is 1 00 cd/m2 to In the case of a constant current drive, it is an ideal and practical organic EL device. The organic EL device of the aromatic amine derivative of the present invention is used as described above in detail. A lower applied voltage can obtain a practically preferable light-emitting redundancy, and has high luminous efficiency, and is not easily deteriorated even after long-term use, and has a long life. Therefore, it can be used as a light source for a planar illuminator of a wall-mounted television or a backlight of a display or the like. 131739.doc •63 ·

Claims (1)

200916434 X. Patent application scope: It is expressed by the following formula (1): 1. An aromatic amine derivative [Chemical 1] (D (wherein R is a substituted or unsubstituted valence group derived from chopsticks; r2 is a single bond substituted or unsubstituted carbon number 6 to 5 Å of an extended aryl group, or a substituted or unsubstituted inverse number 3~ a divalent heterocyclic group of 50; 8 and 6 are each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted oxime number of 3, 50, which is a single bond at R2 and The one or six-position chopstick structure of the chopstick structure has at least one substituent other than -ΝΑΒ. 2. The aromatic amine derivative of claim 1, wherein the above aromatic amine derivative is Formula (π) or (III) to represent: [Chemical 2] (wherein, Α and Β are the same as above; R3 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms of the above R 2 ' or a substituted or unsubstituted carbon number 131739.doc 200916434 3 to 50 bis a valent heterocyclic group; χ^χ2 substituted carbon number 6 to 5. The aryl group, substituted two means an "aryl group or a 6 to 5. aryl group", an amino group, a substitution or an early or - (carbon number generation) An alkyl group having an inverse number of 50, a substituted or unsubstituted carbon number of 3 to 2 G, a substituted or unsubstituted 5 fluorene heterocyclic group, a substituted or unsubstituted carbon U group, and a subsequent substitution The aromatic base (the aryl group has a carbon number of 6 to 5 Å, the base portion has an anisotropy of 1 to 50), and the substituted or unsubstituted heteroarylalkyl group (the heteroaryl portion has a carbon number of 4 to 50). , the thiol moiety has a carbon number of 1 to 5 Å), a substituted or unsubstituted aryloxy group having 6 to 5 Å, a substituted or unsubstituted aryl sulphur-substituted or unsubstituted alkane having a carbon number of 6 to 50 An oxycarbonyl group (having a carbon number of the alkoxy moiety of 50), a substituted or unsubstituted alkyl group having a carbon number of 丨~2〇, a substituted or unsubstituted arylalkyl group of 6 to 50, a decyl group , amine, cyano, nitro, a substituent in a hydroxyl group or a carboxyl group; a represents an integer of 0 to 5, and b represents an integer of 0 to 6; χ1 and π may be bonded to form a saturated or unsaturated ring 'a when an integer of 2 or more' is plural. The same or different, can be connected to form a saturated or unsaturated ring; b is an integer of 2 or more, a plurality of X2 can be the same or different, can be connected to form a saturated or unsaturated ring). Or an aromatic amine derivative wherein the -NAB group, the -R2-NAB group, or the _R3_NAB group is substituted at the 2 or 3 position of the chopstick structure. 4. The aromatic amine derivative of claim 3, Wherein it is represented by the following formula (IV), (V), (VI) or (VII) · [Chemical 3] 131739.doc 200916434 Νν> <y) CVD VIII (in the formula, x a and b are the same as above, and a long time is not selected from the substituted or unsubstituted aryl group having 6 to 5 carbon atoms, substituted or not: instead of a single or - (carbon number 6 to 5 〇) Alkyl)amino, substituted or unsubstituted carbon number 1 "5〇 alkyl, substituted or unsubstituted cycloalkyl 3~20, substituted or unsubstituted carbon number 3~5〇 a cyclic, substituted or unsubstituted carbon #=~ an alkoxy group, a substituted or unsubstituted anaryl group (the carbon number of the ～50' alkyl moiety of the aryl moiety is 丨, a heteroaryl moiety The carbon number is - the base part of the two (four), substituted or unsubstituted "number", the carbon number of 6~5G, the carbon number of the substituted or unsubstituted part is 2) the substituted or unsubstituted carbon Number 1~20 of the burnt group 131739.doc 200916434 Shi Xiyuan base substituted or unsubstituted carbon number 6~50 of aryl sylvestre, phenyl group, amine group, cyano group, nitro group, hydroxyl group, carboxyl group Substituent; 4 is not an integer of 55, d is an integer of 〇~5; and X and X4 may be mutually connected to form a saturated or unsaturated ring; when the above integer is used, plural 乂3 may be the same or different. mutual Connecting to form a saturated or unsaturated ring; when d is an integer of 2 or more, a plurality of X4 may be the same or different and may be linked to each other to form a saturated or unsaturated ring.) 5. Aromatic amine derivative according to claim 4 And an aromatic amine derivative according to any one of the above items (1), wherein at least one of the above X1 and the substituent is substituted or unsubstituted. a secondary or primary alkyl group having a carbon number of 3 to 50, or a substituted or unsubstituted 7th alkyl group as defined in claims 2 to 5, and an aromatic group, and an aromatic amine. The derivative 'wherein the above X1> is a substituted or unsubstituted alkyl or arylalkylalkyl group. 20 alkyl oxime 8. The aromatic amine derivative electromechanical as claimed in the claim 7 to 7 Doping (4) for the excitation light element. 〃中/, has a 9.-type organic electroluminescent device, which includes a hairpin; g + = & an organic film including one or more layers of the first layer The layer, ]/, has one layer containing at least one kind of derivative such as a thin film layer of the request material. The organic electroluminescent device of claim 9, wherein the layer of the octaamine derivative is a light-emitting layer. The above aromatic n. The organic electroluminescent device of claim 9 or 10, wherein the above-mentioned light-emitting layer 131739. Doc 200916434 contains the above aromatic amine derivative and a structure having a quinone compound: a central skeleton and represented by the following formula (2a) [Chemical Formula 4] (where Α9 and Α10 are independent ^ is a substituted or unsubstituted aryl group derived from a 6- to 20-membered aromatic ring, and is independently an aryl group selected from the group consisting of hydrogen®, substituted or unsubstituted carbonaceous mountain. Or unsubstituted heteroaryl group having 4 to 50 carbon atoms, a left, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 5 carbon atoms, substituted or not a substituted alkoxy group, a substituted or unsubstituted aryl group (the carbon number of the aryl moiety is 6 to 50, the carbon number of the alkyl moiety is 1 to 50), and the substituted or unsubstituted carbon number is 6 5050 aryloxy, substituted or unsubstituted arylthio group having 6 to aryl, substituted or unsubstituted alkoxycarbonyl group (carbon number of alkyl moiety is 1 to 5 Å), substituted or unsubstituted residue , silk, _ atom, cyano group, exact group and base in hydroxy group). 12. The organic electroluminescent device of claim 11, wherein in the above formula (2), Ar9 and Ar1() are different bases. 13. The organic electroluminescent device of claim 9 or 10, wherein said illuminating The layer contains the above-mentioned sulphate derivative and a compound having a structure containing a fluorene center skeleton and represented by the following formula (2b): [Chem. 5] 131739.doc 200916434 t(L%Ar% m (wherein t, Ar^Ar2 are each independently substituted aryl, and (10)w is independently selected from the group consisting of: substituted or unsubstituted anthranyl group, substituted by a stretching base, Open the 矽 矽 heterocyclopentadienyl (-e) base, · 2 integer, ... ~ 4 of the whole two, ::: 〜2 integer, 鹄. ~ 4 integer; l1 or ~ bond In either position, L2 or Ar2 is bonded to any of the 6 to 1 芘 positions of 芘. 14. The organic electroluminescent device of claim 9 or 10, which contains the above aromatic amine a derivative, and a compound having a structure containing a tris-amine skeleton; represented by the following formula (2c): [Chem. 6] , with a table — 4 π W must be 仴 仴 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有 有131739.doc 200916434 15. In the organic electroluminescent device of claim 9 or 1 会, the ancient μ, +, # 4 , the upper luminescent layer each has the above-mentioned flavonoid derivative, and a Μ Μ (2d) Compounds of the structure shown: V q Table [Chemical 7] (2d) (wherein ΑΓ"~^3, respectively, independently represents an aryl group having a core carbon number of 6 to 50, and the core is a trivalent ruthenium derived from an aromatic ring or a heteroaromatic ring. 1 has an organic electroluminescent material. a solution containing an organic electro-excitation material and a solvent and wherein the above-mentioned organic electroluminescent material contains at least one of the aromatic amine derivatives according to any one of claims 1 to 7. 17. The organic electrophoresis of claim 16 a solution of the material, the organic electroluminescent material in the pot contains a host material and a replacement material, and the above-mentioned impurity material is an aromatic material organism according to any one of claims 1 to 7, and the host material is selected from the request item u The compound represented by the formula (4), the compound represented by the formula (10) in the claim 13, the compound represented by the formula (2C) in the claim 14, and the formula (in the claim 15) 2d) at least one of the compounds indicated. 131739.doc 200916434 VII. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbol of the symbol of the representative figure is simple: 8. If there is a chemical formula in this case, please reveal the best indication of the characteristics of the invention. Chemical formula: 131739.doc