JP2003238516A - New condensed aromatic compound and organic electroluminescent element produced by using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new condensed aromatic compound giving an organic EL element having high luminance, light-emitting efficiency and color purity and emitting red light, and provide an organic electroluminescent element produced by using the compound. <P>SOLUTION: The new condensed aromatic compound has a fluoranthene skeleton at least having an amino group and an electron attracting group bonded to the skeleton. The electroluminescent element is composed of one or more organic thin layers sandwiched between a cathode and an anode, wherein at least one of the organic thin layers contains the condensed aromatic compound. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel condensed aromatic compound and an organic electroluminescence device (organic EL device) using the same, and more particularly, to high emission brightness and emission efficiency, high color purity, and red-based Organic E that emits light
The present invention relates to a novel condensed aromatic compound capable of providing an L element and an organic EL element using the same.

[0002]

2. Description of the Related Art An organic EL element using an organic substance is expected to be used as a solid-state light emitting inexpensive large area full color display element, and many developments have been made. In general,
The organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. In the light emission of the organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode side,
This is a phenomenon in which holes are injected from the anode side, electrons are recombined with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state. Recently, an organic EL element display has been put into practical use, but a full-color display element is under development.
In particular, there is a demand for an organic EL element that has high color purity and high emission efficiency and emits reddish light, and a light emitting material that realizes the same. As an attempt to solve these problems, for example, Japanese Unexamined Patent Publication (Kokai) No. 8-31142 discloses a red light emitting device in which a naphthacene or pentacene derivative is added to a light emitting layer. The light emitting device has excellent red purity. However, the applied voltage is as high as 11V and the half-life time of the brightness is about 15
It was 0 hours, which was insufficient. Japanese Unexamined Patent Publication (Kokai) No. 3-162481 discloses a device in which a dicyanomethylene compound is added to a light emitting layer, but the purity of red color is insufficient.
Japanese Unexamined Patent Publication No. 2001-81451 discloses a red light emitting device in which an amine-based aromatic compound is added to a light emitting layer, and this light emitting device has a color purity of CIE chromaticity (0.64, 0.33). However, the drive voltage was as high as 10 V or higher. Japanese Patent Application Laid-Open No. 2001-160489 discloses an element in which an azafluoranthene compound is added to a light emitting layer, but yellow to green light emission is not achieved, and sufficient red light is not emitted.

[0003]

SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and can provide an organic EL element which has high emission brightness and emission efficiency, high color purity, and emits reddish light. Another object of the present invention is to provide a novel fused aromatic compound and an organic EL device using the same.

[0004]

Means for Solving the Problems As a result of intensive studies for solving the above problems, the present inventors have found that a compound having a fluoranthene skeleton in which an amino group and an electron-withdrawing group are bonded is used as an organic thin film of an organic EL device. The present invention has been found to solve the above problems by using it as a layer material, and has led to the present invention.

That is, the present invention provides the following general formulas (1) to (1).
It is a novel condensed aromatic compound represented by any of (11).

[Chemical 3]

(In the formula, R _{1 to} R ₁₈ are, independently of each other,
Hydrogen atom, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, 3 to 20 carbon atoms A trialkylsilyl group, a substituted or unsubstituted alkenyl group having 4 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a cyano group, a perfluoroalkyl group, a nitro group, a halogen group or a group represented by the following general formula (A), which is represented by the general formula (1) to ( In 3) and (8), R ₁
To R ₁₄ , at least one is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and in the general formulas (4) and (10), R _{1 to} R ₁₆
At least one of them is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and in the general formula (5), at least one of R _{1 to} R ₁₆ is
One is a group represented by the following general formula (A), at least one is an electron-withdrawing group,
In (7), (9) and (11), at least one of R _{1 to} R ₁₈ is a group represented by the following general formula (A), and at least one is an electron-withdrawing group. In addition, R _{1 to} R ₁₈ may form a cyclic structure with adjacent groups. )

[0007]

[Chemical 4] (In the formula, X ₁ and X ₂ are each independently a hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a heterocyclic group having 3 to 40 carbon atoms A cyclic group, X ₁ and X
₂ may be connected to each other to form a ring structure. Also,
X ₁ or X ₂ and a fluoranthene skeleton group are linked to each other,
You may form a cyclic structure. )

Further, according to the present invention, in an organic electroluminescence device in which an organic thin film layer composed of one or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers has at least an amino group and electron withdrawing. The present invention provides an organic EL device containing a condensed aromatic compound having a fluoranthene skeleton bonded to a functional group.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION In the above general formula (1), R ₁
To R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted 6 to 40 carbon atoms Aryl group, C3-20 trialkylsilyl group, substituted or unsubstituted C4
30 alkenyl groups, substituted or unsubstituted carbon number 7 to
40 arylalkyl groups, substituted or unsubstituted aryloxy groups having 6 to 40 carbon atoms, cyano groups, perfluoroalkyl groups, nitro groups, halogen groups or groups represented by the following general formula (A): Formulas (1) to (3)
And (8), at least one of R _{1 to} R ₁₄
One is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and one of the general formulas (4) and (1
0), at least one of R _{1 to} R ₁₆ is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and in the general formula (5), R is
_At least one of _{1 to} R ₁₆ is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and the general formulas (6), (7), (9) and ( In 11), at least one of R _{1 to} R ₁₈ is a group represented by the following general formula (A), and at least one is an electron-withdrawing group. In addition, R _{1 to} R ₁₈ may form a cyclic structure with adjacent groups.

Examples of the alkyl group having 1 to 30 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group and n-
Butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group Group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,
3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1, 2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3
-Dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-
Bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group,
2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group,
1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3
-Triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino- group t-butyl group, 1,
2,3-triaminopropyl group, cyanomethyl group, 1-
Cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group,
1,2,3-tricyanopropyl group, nitromethyl group,
1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-tri Examples thereof include a nitropropyl group.

As the alkoxy group having 1 to 30 carbon atoms,
A group represented by -OY, and examples of Y include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and n.
-Pentyl group, n-hexyl group, n-heptyl group, n-
Octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-
Butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1, 3-dibromoisopropyl group, 2,3-
Dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodo Isopropyl group, 2,
3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2
-Aminoethyl group, 2-aminoisobutyl group, 1,2-
Diaminoethyl group, 1,3-diaminoisopropyl group,
2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group,
1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3
-Tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl Base 1,
2,3-trinitropropyl group and the like can be mentioned.

Examples of the aryl group having 6 to 40 carbon atoms include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, fluorenyl group, biphenyl group, terphenyl group and stilbene group. Examples of the trialkylsilyl group having 3 to 20 carbon atoms include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, tributylsilyl group, tripentylsilyl group, trihexylsilyl group and t-butyldimethylsilyl group. As the alkenyl group having 4 to 30 carbon atoms, vinyl group, allyl group, 1-butenyl group, 2-
Butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 2,2-ditolylvinyl group, 1,2-ditolylvinyl group, 1-methylallyl group , 1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group,
2-phenylallyl group, 3-phenylallyl group, 3,3
-Diphenylallyl group, 1,2-dimethylallyl group, 1
-Phenyl-1-butenyl group, 3-phenyl-1-butenyl group and the like can be mentioned.

The arylalkyl group having 7 to 40 carbon atoms includes benzyl group, α-methylbenzyl group, cinnamyl group, α-ethylbenzyl group, α, α-dimethylbenzyl group, 4-methylbenzyl group and 4-ethyl group. Benzyl group, 2
Examples thereof include a -tert-butylbenzyl group, a 4-n-octylbenzyl group, a naphthylmethyl group and a diphenylmethyl group. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group, a naphthyloxy group, an ankleoxy group, a pyrenyloxy group, a biphenyloxy group, a fluoranthenyloxy group, a chrysenyloxy group and a perylenyloxy group. Further, examples of the substituent of the alkyl group, alkoxy group, aryl group and alkenyl group include a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, and a substituted group. Or, an unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group,
Examples thereof include a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group and a carboxyl group.

In the above general formula (A), X ₁ and X ₂
Are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms. And a heterocyclic group having 3 to 40 carbon atoms, X ₁ and X ₂ may be linked to each other to form a cyclic structure. Further, X ₁ or X ₂ and the fluoranthene skeleton group may be connected to each other to form a cyclic structure.
Examples of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms include the same ones as described above. Examples of the substituted or unsubstituted aryl group having 6 to 40 carbon atoms include the same ones as described above.

As the heterocyclic group having 3 to 40 carbon atoms, 1-
Other indolizin-2-yl group, 1-aza-indolizin-3-yl group, 1-aza-indolizin-5-yl group, 1-aza-indolizin-6-yl group, 1-aza-
Indolizin-7-yl group, 1-aza-indolizine-
8-yl group, 2-aza-indolizin-1-yl group, 2
-Aza-indolizin-3-yl group, 2-aza-indolizin-5-yl group, 2-aza-indolizin-6-yl group, 2-aza-indolizin-7-yl group, 2-aza -Indolizin-8-yl group, 6-aza-indolizin-1-yl group, 6-aza-indolizin-2-yl group,
6-aza-indolizin-3-yl group, 6-aza-indolizin-5-yl group, 6-aza-indolizin-7-
Group, 6-aza-indolizin-8-yl group, 7-aza-indolizin-1-yl group, 7-aza-indolizin-2-yl group, 7-aza-indolizin-3-yl group , 7-aza-indolizin-5-yl group, 7-aza-
Indolizin-6-yl group, 7-aza-indolizine-
7-yl group, 7-aza-indolizin-8-yl group, 8
-Aza-indolizin-1-yl group, 8-aza-indolizin-2-yl group, 8-aza-isidoridin-3-yl group, 8-aza-indolizin-5-yl group, 8-aza- Indolizin-6-yl group, 8-aza-indolizin-7-yl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8
-Indolizinyl group, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group Group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7
-Indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7
-Isoindolyl group, 2-furyl group, 3-furyl group, 2
-Benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group Nyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group Group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group Group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group,
3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phen Nonthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-
Acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,
7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthroline-4
-Yl group, 1,7-phenanthrolin-5-yl group,
1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl Group, 1,8-phenanthrolin-2-yl group, 1,8-
Phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1, 8
-Phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthroline-10
-Yl group, 1,9-phenanthrolin-2-yl group,
1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl Group, 1,9-phenanthrolin-7-yl group, 1,9-
Phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2
-Yl group, 1,10-phenanthrolin-3-yl group,
1,10-phenanthrolin-4-yl group, 1,10-
Phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2, 9
-Phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthroline-7-
Yl group, 2,9-phenanthroline-8-yl group, 2,
9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthroline-
3-yl group, 2,8-phenanthrolin-4-yl group,
2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl Group, 2,8-phenanthrolin-10-yl group, 2,7
-Phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthroline-4-
Yl group, 2,7-phenanthrolin-5-yl group, 2,
7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthroline-9
-Yl group, 2,7-phenanthrolin-10-yl group,
1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrole- 1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, - methylpyrrole-5-yl group,
2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1
-Indolyl group, 4-methyl-1-indolyl group, 2-
Methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, 4-t- Butyl 3-indolyl group and the like.

Examples of the substituents on the alkyl group and aryl group include halogen atom, hydroxyl group, substituted or unsubstituted amino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted group. An unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group,
A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted Examples thereof include a substituted alkoxycarbonyl group and a carboxyl group.

Specific examples of the novel fused aromatic compounds represented by the general formulas (1) to (11) of the present invention are shown below, but the present invention is not limited to these exemplified compounds.

[Chemical 5]

[0018]

[Chemical 6]

[0019]

[Chemical 7]

[0020]

[Chemical 8]

[0021]

[Chemical 9]

[0022]

[Chemical 10]

[0023]

[Chemical 11]

[0024]

[Chemical 12]

The condensed aromatic compounds of the general formulas (1) to (11) of the present invention are preferably used as an organic compound for an organic EL device. The organic EL element of the present invention is an organic EL element in which an organic thin film layer composed of one layer or a plurality of layers is sandwiched between a cathode and an anode, and at least one layer of the organic thin film layer is at least an amino group and an electron-withdrawing group. It contains a condensed aromatic compound having a fluoranthene skeleton in which and are bonded. The condensed aromatic compound having a fluoranthene skeleton in which at least an amino group and an electron-withdrawing group are bonded is preferably the novel condensed aromatic compound of any one of the above general formulas (1) to (11).

The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between the anode and the cathode as described above. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material for transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. Further, it is preferable that the light emitting material has extremely high fluorescence quantum efficiency, high hole transporting ability and electron transporting ability, and forms a uniform thin film. The multilayer organic EL device includes (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole injection layer / light emitting layer / electron injection layer). / Cathode) and the like.

In the light emitting layer, in addition to the compound of any one of the general formulas (1) to (11) of the present invention, further known host materials, light emitting materials, doping materials, hole injecting materials, and An electron injection material may be used and may be used in combination. The organic EL element can prevent a decrease in brightness and life due to quenching by having a multi-layer structure, and can improve emission brightness and emission efficiency and obtain red and white light emission by using other doping materials. By using it in combination with another doping material that contributes to phosphorescence, conventional light emission brightness and light emission efficiency can be improved. Further, the hole injection layer, the light emitting layer, and the electron injection layer in the organic EL device of the present invention may each be formed by a layer structure of two or more layers. In that case, in the case of a hole injection layer, a layer that injects holes from the electrode is called a hole injection layer, and a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer is called a hole transport layer. Similarly, in the case of the electron injection layer, the layer that injects electrons from the electrode is called an electron injection layer, and the layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on various factors such as the energy level of the material, heat resistance, and adhesion to the organic thin film layer or the metal electrode.

In the organic EL device of the present invention, the electron-transporting layer has a condensed aromatic compound having a fluoranthene skeleton in which at least an amino group and an electron-withdrawing group are bonded, preferably the above general formulas (1) to (11). May be contained, and the hole transport layer may have a fluoranthene skeleton in which at least an amino group and an electron-withdrawing group are bonded, preferably the above-mentioned general formula (1) ) To (11), the novel condensed aromatic compound may be contained.

Examples of the light emitting material or host material which can be used in the organic thin film layer together with the condensed aromatic compound of the present invention include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone. , Naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinyl Anthracene, diaminoanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oki Isoprenoid compounds, quinacridone,
Examples thereof include, but are not limited to, rubrene, stilbene-based derivatives, and fluorescent dyes.

The hole-injecting material has the ability to transport holes, has the effect of injecting holes from the anode, and has an excellent effect of injecting holes into the light-emitting layer or the light-emitting material. A compound that prevents excitons from moving to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivative, naphthalocyanine derivative, porphyrin derivative, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole,
Hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and their derivatives, and polyvinylcarbazole, polysilane, conductive polymers, etc. Examples thereof include polymeric materials, but the present invention is not limited thereto.

Among these hole injecting materials, the more effective hole injecting materials are aromatic tertiary amine derivatives or phthalocyanine derivatives. Specific examples of the aromatic tertiary amine derivative include triphenylamine, tritolylamine, tolyldiphenylamine, N, N′-diphenyl-
N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N, N', N '-(4
-Methylphenyl) -1,1'-phenyl-4,4'-
Diamine, N, N, N ', N'-(4-methylphenyl) -1,1'-biphenyl-4,4'-diamine,
N, N'-diphenyl-N, N'-dinaphthyl-1,
1'-biphenyl-4,4'-diamine, N, N'-
(Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N
-Bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane and the like, or oligomers or polymers having these aromatic tertiary amine skeletons, but not limited thereto. Specific examples of the phthalocyanine (Pc) derivative include H ₂ Pc, CuPc and Co.
Pc, NiPc, ZnPc, PdPc, FePc, Mn
Pc, ClAlPc, ClGaPc, ClInPc, C
lSnPc, Cl ₂ SiPc, (HO) AlPc, (H
O) GaPc, VOPc, TiOPc, MoOPc, G
It is a phthalocyanine derivative such as aPc-O-GaPc and a naphthalocyanine derivative, but is not limited thereto.

The electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode and an excellent electron injecting effect to the light emitting layer or the light emitting material, and the excitons generated in the light emitting layer are positively charged. A compound that prevents migration to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, quinoxaline, fluorenylidene methane, anthraquinodimethane, anthrone and the like. However, the present invention is not limited to these.

Among these electron injecting materials, a more effective electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specific examples of the metal complex compound include lithium 8-hydroxyquinolinate, bis (8-hydroxyquinolinate) zinc, and bis (8-hydroxyquinolinate).
Copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, Bis (10-hydroxybenzo [h] quinolinate) beryllium, bis (10-hydroxybenzo [h]
Quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinate) (2-
Examples thereof include, but are not limited to, naphtholate) gallium and the like.

The nitrogen-containing five-membered derivative is preferably an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative. In particular,
2,5-bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) ) -1,3,4-Oxadiazole, 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-oxadiazole, 1,4
-Bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-thiadiazole, 1,4-
Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-butylphenyl) -5- (
4 "-biphenyl) -1,3,4-triazole, 2,
5-bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)
Examples thereof include, but are not limited to, benzene and the like.

The charge injecting property can be improved by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material. As the conductive material used for the anode of the organic EL device of the present invention, those having a work function larger than 4 eV are suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum. , Palladium and alloys thereof, tin oxide used for ITO substrates, NESA substrates,
A metal oxide such as indium oxide, or an organic conductive resin such as polythiophene or polypyrrole is used. As the conductive material used for the cathode, one having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium,
Ruthenium, manganese, aluminum, etc., and alloys thereof are used, but not limited to these.
Typical examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, etc., but are not limited to these. The alloy ratio is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected as an appropriate ratio. The anode and the cathode may be formed in a layered structure of two or more layers if necessary.

At least one of the organic EL devices of the present invention is
Having an inorganic compound layer between the electrode and the organic thin film layer
You may stay. Preferred mineralization used for inorganic compound layers
Compounds include alkali metal oxides and alkaline earth oxides
Compounds, rare earth oxides, alkali metal halides, alkali
Re-earth halide, rare earth halide, SiO_X,
AlO_X, SiN_X, SiON, AlON, GeO_X,
LiO_X, LiON, TiO_X, TiON, TaO_X,
TaON, TaN_X, C, various oxides, nitrides, oxidation
It is a nitride. In particular, the component of the layer in contact with the anode is S
iO_X, AlO _X, SiN_X, SiON, AlON, G
eO_X, C form a stable injection interface layer, which is preferable. Well
In particular, as the component of the layer in contact with the cathode, LiF, Mg
F₂, CaF₂, MgF₂, NaF are preferred.

In order to make the organic EL device of the present invention emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the emission wavelength region of the device. It is also desirable that the substrate is transparent. The transparent electrode is made of the above-mentioned conductive material and is set by a method such as vapor deposition or sputtering so as to ensure a predetermined translucency. The electrodes on the light emitting surface are
It is desirable that the light transmittance is 10% or more. The board is
Although it is not limited as long as it has mechanical and thermal strength and transparency, examples thereof include a glass substrate and a transparent resin film. As a transparent resin film,
Polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethylmethacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone, polysulfone,
Polyether sulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidenefluor Ride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene and the like can be mentioned.

In the organic EL device of the present invention, a protective layer may be provided on the surface of the device or the entire device may be protected by silicone oil, resin or the like in order to improve stability against temperature, humidity, atmosphere and the like. Is. For formation of each layer of the organic EL device of the present invention, any one of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating and wet film forming methods such as spin coating, dipping and flow coating can be applied. You can Although the film thickness of each layer is not particularly limited, it is necessary to set an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, and the light emission efficiency deteriorates. If the film thickness is too thin, pinholes and the like will occur, and even if an electric field is applied, sufficient emission brightness cannot be obtained. The normal film thickness is preferably in the range of 5 nm to 10 μm, but 10 nm to
The range of 0.2 μm is more preferable.

In the case of the wet film forming method, the materials forming each layer are ethanol, chloroform, tetrahydrofuran,
The thin film is formed by dissolving or dispersing in a suitable solvent such as dioxane, and any solvent may be used. Also,
Appropriate resins and additives may be used in any of the layers in order to improve film-forming properties and prevent pinholes in the film. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethylmethacrylate, polymethylacrylate and cellulose, and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Further, examples of the additive include an antioxidant, an ultraviolet absorber, a plasticizer and the like. As described above, by using the novel condensed aromatic compound of the present invention for the organic thin film layer of an organic EL device, an organic EL device that has high color purity and luminous efficiency and emits red light can be obtained. EL elements are suitable for use in, for example, electrophotographic photoreceptors, flat light emitters such as flat panel displays for wall-mounted televisions, light sources such as copiers, printers, backlights of liquid crystal displays or instruments, display plates, marker lights, accessories, and the like. Used.

[0040]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Synthesis Example 1 (Synthesis of Compounds 1-7 and 1-8) The synthetic route of the condensed aromatic compound (Compounds 1-7 and 1-8) is shown below.

[Chemical 13]

Mixture of compound (A) and compound (B) in a 100 ml three-necked flask (mixing ratio 8: 2).
3.0 g (5.64 mmol), 4-methoxy-4'-
2.75 g of methyl-N, N-diphenylamine (12.
9 mmol), tris (dibenzylideneacetone) dipalladium (0) 103 mg (0.113 mmol),
(S)-(-)-BINAP (2,2'-bis- (diphenylphosphino) -1,1'-binaphthyl) 140 mg
(0.226 mmol), 4.43 g of cesium carbonate (1
(3.6 mmol) was added and the atmosphere was replaced with argon, 70 ml of toluene was added, the temperature was raised to 115 ° C. with stirring, and the mixture was further stirred for 9 hours. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried, and 2.7 g (3.3
8 mmol) of the target compounds 1-7 and 1-8 were obtained (yield 60%). Identification was performed using NMR, and as a result of analysis,
The mixing ratio of 1-7 and 1-8 was about 8: 2. FD mass analysis: 798 (M ⁺ , bp)

Synthesis Example 2 (Synthesis of Compounds 1-13 and 1-14) The synthetic route of the fused aromatic compound (Compounds 1-13 and 1-14) is shown below.

[Chemical 14]

Mixture of compound (C) and compound (D) in a 100 ml three-necked flask (mixing ratio 8: 2).
2.4 g (5.25 mmol), 4-dimethylamino-
4'-methyl-N, N-diphenylamine 1.35 g
(6.0 mmol), tris (dibenzylideneacetone) dipalladium (0) 96 mg (0.105 mmo
l), (S)-(-)-BINAP (2,2'-bis-
(Diphenylphosphino) -1,1'-binaphthyl) 13
0 mg (0.210 mmol), cesium carbonate 2.05
After adding g (6.3 mmol) and purging with argon, 60 ml of toluene was added and stirred at 115 ° C.
The temperature was raised to 0 and the mixture was further stirred for 7 hours. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried to 2.9 g.
(4.80 mmol) of the desired compound 1-13, 1-1
4 was obtained (yield 92%). Identification is performed using NMR,
As a result of the analysis, the mixing ratio of 1-13 and 1-14 was about 8: 2. FD mass analysis: 603 (M ⁺ , bp)

Synthesis Example 3 (Synthesis of Compound 2-3) The synthetic route of the condensed aromatic compound (Compound 2-3) is shown below.

[Chemical 15]

Compound (E) 2.0 g (3.76 mmol), N, N-ditolylamine 1.63 g (8.27 mmol), tris (dibenzylideneacetone) dipalladium (0) 69 m were placed in a 100 ml three-necked flask.
g (0.075 mmol), (S)-(-)-BINA
P (2,2'-bis- (diphenylphosphino) -1,1 '
-Binaphtyl) (93 mg, 0.150 mmol) and cesium carbonate (2.82 g, 8.65 mmol) were added and the atmosphere was replaced with argon. Then, 50 ml of toluene was added and the temperature was raised to 115 ° C with stirring, and the mixture was further stirred for 9 hours.
After the reaction is complete, cool to room temperature, add dichloromethane,
After stirring at room temperature for a while, it was filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried to obtain 1.6 g (2.09 mmol) of the target compound 2-3 ( Yield 56%). Identification was performed using NMR. FD mass analysis: 766 (M ⁺ , bp)

Synthesis Example 4 (Synthesis of Compound 3-3) The synthetic route of the condensed aromatic compound (Compound 3-3) is shown below.

[Chemical 16]

In a 100 ml three-necked flask, 1.6 g (3.00 mmol) of compound (F), 1.30 g (6.60 mmol) of N, N-ditolylamine, and 55 m of tris (dibenzylideneacetone) dipalladium (0).
g (0.06 mmol), (S)-(-)-BINAP
(2,2'-bis- (diphenylphosphino) -1,1'-
Binaphthyl) (75 mg, 0.12 mmol) and cesium carbonate (2.28 g, 7.00 mmol) were added and the atmosphere was replaced with argon. Then, 40 ml of toluene was added and the temperature was raised to 115 ° C. with stirring, followed by further stirring for 9 hours. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, the precipitated crystals were separated by filtration and dried, and 1.8 g (2.34 mmol) of the desired compound 3-
3 was obtained (yield 78%). Identification was performed using NMR. FD mass analysis: 766 (M ⁺ , bp)

Synthesis Example 5 (Synthesis of Compounds 4-1 and 4-2) A synthetic route of the condensed aromatic compound (Compounds 4-1 and 4-2) is shown below.

[Chemical 17]

Mixture of compound (G) and compound (H) in a 100 ml three-necked flask (mixing ratio 7: 3).
1.6 g (2.75 mmol), N, N-ditolylamine 1.25 g (6.32 mmol), tris (dibenzylideneacetone) dipalladium (0) 50 mg (0.0
55 mmol), (S)-(-)-BINAP (2,2 '
-Bis- (diphenylphosphino) -1,1'-binaphthyl) 68 mg (0.11 mmol), cesium carbonate 2.
After adding 15 g (6.60 mmol) and substituting with argon, 40 ml of xylene was added and stirred to 1
The temperature was raised to 30 ° C., and the mixture was further stirred for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried,
1.6 g (1.96 mmol) of the desired compound 4-1,
4-2 was obtained (71% yield). Identification was performed using NMR, and as a result of analysis, the mixing ratio of 4-1 and 4-2 was about 7: 3. FD mass analysis: 816 (M ⁺ , bp)

Synthesis Example 6 (Synthesis of Compound 5-7) The synthetic route of the condensed aromatic compound (Compound 5-7) is shown below.

[Chemical 18]

Compound (I) (2.0 g, 4.15 mmol), 3,3 ', was added to a 200 ml three-necked flask.
4,4'-Tetramethyl-N, N-diphenylamine 2.15 g (9.55 mmol), tris (dibenzylideneacetone) dipalladium (0) 73 mg (0.08)
mmol), (S)-(-)-BINAP (2,2'-bis- (diphenylphosphino) -1,1'-binaphthyl)
100 mg (0.16 mmol), cesium carbonate 3.2
After adding 4 g (9.96 mmol) and purging with argon, 80 ml of toluene was added and stirred to 1
The temperature was raised to 15 ° C., and the mixture was further stirred for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried,
2.3 g (2.98 mmol) of the target compound 5-7 was obtained (yield 72%). Identification was performed using NMR. FD mass analysis: 772 (M ⁺ , bp)

Synthesis Example 7 (Synthesis of Compound 6-5) The synthetic route of the condensed aromatic compound (Compound 6-5) is shown below.

[Chemical 19]

Compound (J) (1.5 g, 2.37 mmol) and N- (2-
927 mg (5.45 mmol) of pyridyl) aniline,
Tris (dibenzylideneacetone) dipalladium (0)
37 mg (0.04 mmol), (S)-(-)-BI
NAP (2,2'-bis- (diphenylphosphino) -1,
1'-Binaphthyl) 50 mg (0.08 mmol) and cesium carbonate 1.86 g (5.70 mmol) were added and the atmosphere was replaced with argon, 40 ml of toluene was added and the temperature was raised to 115 ° C with stirring, and stirring was continued for 10 hours. did. After completion of the reaction, the mixture was cooled to room temperature, dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated and the target product was separated by silica gel column chromatography. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystals were separated by filtration and dried to obtain 1.4 g (1.72 mmol) of the target compound 6-5 ( Yield 73%). Identification was performed using NMR. FD mass analysis: 812 (M ⁺ , bp)

Synthesis Example 8 (Synthesis of Compounds 7-1 and 7-2) The synthetic route of the condensed aromatic compound (Compounds 7-1 and 7-2) is shown below.

[Chemical 20]

Mixture of compound (K) and compound (L) in a 100 ml three-necked flask (mixing ratio 6: 4).
1.8 g (2.85 mmol), 4-methoxy-4'-
Methyl-N, N-diphenylamine 1.40 g (6.5
6 mmol), tris (dibenzylideneacetone) dipalladium (0) 52 mg (0.057 mmol),
(S)-(-)-BINAP (2,2'-bis- (diphenylphosphino) -1,1'-binaphthyl) 68 mg
(0.11 mmol) and 2.23 g of cesium carbonate (6.
(84 mmol) was added and the atmosphere was replaced with argon, 40 ml of xylene was added, the temperature was raised to 130 ° C. with stirring, and the mixture was further stirred for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added and the precipitate was filtered. The obtained solid was further recrystallized with a toluene solvent, and the precipitated crystals were separated by filtration and dried to obtain 1.3 g (1.45 mmol) of target compounds 7-1 and 7-2 (yield 51% ). Identification was performed using NMR, and as a result of analysis, the mixture ratio of 7-1 and 7-2 was 5: 5. FD mass analysis: 898 (M ⁺ , bp)

Synthesis Example 9 (Synthesis of Compounds 8-1 and 8-2) The synthetic route of the condensed aromatic compound (Compounds 8-1 and 8-2) is shown below.

[Chemical 21]

Mixture of compound (M) and compound (N) in a 100 ml three-necked flask (mixing ratio 7: 3).
1.8 g (4.20 mmol), N, N-ditolylamine 992 mg (5.03 mmol), tris (dibenzylideneacetone) dipalladium (0) 46 mg (0.0
5 mmol), (S)-(-)-BINAP (2,2'-
Bis- (diphenylphosphino) -1,1'-binaphthyl) 63 mg (0.10 mmol), cesium carbonate 1.
After adding 89 g (5.80 mmol) and substituting with argon, 60 ml of xylene was added and stirred to 1
The temperature was raised to 30 ° C., and the mixture was further stirred for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added and the precipitate was filtered. The obtained solid was recrystallized with a toluene solvent, and the precipitated crystals were separated by filtration and dried to obtain 1.2 g (2.20 mmol) of target compounds 8-1 and 8-2 (yield 52%). . Identification was performed by using NMR, and as a result of analysis, the mixing ratio of 8-1 and 8-2 was 7: 3. FD mass analysis: 546 (M ⁺ , bp)

Synthesis Example 10 (Synthesis of Compound 9-2) The synthetic route of the condensed aromatic compound (Compound 9-2) is shown below.

[Chemical formula 22]

In a 100 ml three-necked flask, compound (O) (1.5 g, 2.09 mmol), 4-methoxy-4'-methyl-N, N-diphenylamine (1.02) was added.
g (4.81 mmol), tris (dibenzylideneacetone) dipalladium (0) 46 mg (0.05 mmo
l), (S)-(-)-BINAP (2,2'-bis-
(Diphenylphosphino) -1,1'-binaphthyl) 62
mg (0.10 mmol), 1.64 g of cesium carbonate
After adding (5.02 mmol) and purging with argon, 60 ml of xylene was added and stirred at 130 ° C.
The temperature was raised to, and the mixture was further stirred for 9 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the residue was filtered. The obtained solid was recrystallized with a toluene solvent, and the precipitated crystals were separated by filtration and dried to obtain 1.0 g (1.02 mmol) of the target compound 9-2 (yield 49%). Identification was performed using NMR. FD mass analysis: 984 (M ⁺ , bp), 492 (M ²⁺ ).

Synthesis Example 11 (Compounds 10-3 and 10-4
The synthesis route of the condensed aromatic compound (compounds 10-3 and 10-4) is shown below.

[Chemical formula 23]

Mixture of compound (P) and compound (Q) in a 100 ml three-necked flask (mixing ratio 8: 2).
1.5 g (2.58 mmol), 4-methoxy-4'-
Methyl-N, N-diphenylamine 1.27 g (5.9
3 mmol), tris (dibenzylideneacetone) dipalladium (0) 55 mg (0.06 mmol), (S)
-(-)-BINAP (2,2'-bis- (diphenylphosphino) -1,1'-binaphthyl) 75 mg (0.12
mmol), 2.02 g of cesium carbonate (6.20 mmo)
After l) was charged and the atmosphere was replaced with argon, 60 ml of xylene was added and the temperature was raised to 130 ° C. with stirring, followed by stirring for 9 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added and the precipitate was filtered. The obtained solid is recrystallized with a toluene solvent, and the precipitated crystals are separated by filtration and dried to give 1.6 g.
(1.89 mmol) of the target compound 10-3, 10-
4 was obtained (yield 73%). Identification is performed using NMR,
As a result of the analysis, the mixing ratio of 10-3 and 10-4 was 2: 8. FD mass analysis: 848 (M ⁺ , bp)

Synthesis Example 12 (Compounds 11-1 and 11-2
The synthesis route of the condensed aromatic compounds (Compounds 11-1 and 11-2) is shown below.

[Chemical formula 24]

Mixture of compound (R) and compound (S) in a 100 ml three-necked flask (mixing ratio 1: 9).
2.3 g (2.93 mmol), N, N-diphenylamine 1.10 g (6.50 mmol), tris (dibenzylideneacetone) dipalladium (0) 46 mg (0.
05mmol), (S)-(-)-BINAP (2,2 '
-Bis- (diphenylphosphino) -1,1'-binaphthyl) 63 mg (0.1 mmol), cesium carbonate 2.3
After adding 0 g (7.00 mmol) and substituting with argon, 70 ml of xylene was added and stirred to 1
The temperature was raised to 30 ° C., and the mixture was further stirred for 9 hours. After the reaction,
After cooling to room temperature, water was added and the precipitate was filtered. The obtained solid was recrystallized with a toluene solvent, and the precipitated crystals were separated by filtration and dried to obtain 2.0 g (2.08 mmol) of target compounds 11-1 and 11-2 (yield 71%). . Identification was performed using NMR, and as a result of analysis, 11-1 and 11-2
The mixing ratio was 9: 1. FD mass analysis: 962 (M ⁺ , bp), 481 (M ²⁺ )

Example 1 A transparent electrode made of indium tin oxide having a film thickness of 120 nm was provided on a glass substrate having a size of 25 × 75 × 1.1 mm. The glass substrate was irradiated with ultraviolet rays and ozone to be washed, and then the glass substrate was placed in a vacuum vapor deposition apparatus. First, the following TPD74 was deposited to a thickness of 60 nm, and then the following NPD was deposited to a thickness of 20 nm thereon. Then, a compound 1-7 as a light emitting material and a light emitting medium
1-8 (1: 1 mixture) and Alq (aluminum complex of 8-hydroxyquinoline) were co-evaporated at a weight ratio of 2:40 to form a light-emitting medium layer having a thickness of 50 nm. Then Alq
Was evaporated to a thickness of 10 nm. Next, an alkali metal halide, LiF, is vapor-deposited to a thickness of 0.2 nm, and then aluminum is vapor-deposited to a thickness of 150 nm.
A device was produced. Next, when an energization test was conducted on this element, the voltage was 7.0 V and the current density was 5.5 mA /
A red emission of 162 cd / m ² was obtained at cm ² .

[0065]

[Chemical 25]

Examples 2 to 11 Organic EL devices were prepared in the same manner as in Example 1 except that the compounds shown in Table 1 were used instead of the compounds 1-7 and 1-8.
A device was produced. The current density, light emission luminance, and light emission color of this device at a DC voltage of 7.0 V were measured and shown in Table 1.

[0067]

[Table 1]

Examples 12 to 22 Alq used as the light emitting medium in Examples 1 to 11
DPVDPA which is an anthracene derivative instead of
An organic EL device was produced in the same manner except that N was used.
Current density of this device at DC voltage of 7.0V, emission brightness,
The emission color was measured and is shown in Table 2.

[Chemical formula 26]

[0069]

[Table 2]

Comparative Example 1 Compound 1-as the light emitting material and the light emitting medium described in Example 1
1, 1-2 (1: 1 mixture) and Alq instead of the following R
An organic EL device was produced in the same manner as in Example 1 except that u2 and Alq were co-evaporated at a weight ratio of 2:40. When the performance of this element was evaluated, it was 28.0 at a voltage of 10V.
A current of mA / cm ² was flown, and red light emission with a brightness of 116 cd / m ² was obtained. However, this device has high voltage and low luminous efficiency.

[Chemical 27]

Comparative Example 2 Compound 1-as the light emitting material and the light emitting medium described in Example 1
An organic EL device was produced in the same manner as in Example 1 except that the following compound 12 and Alq were co-evaporated at a weight ratio of 2:40 instead of 1, 1-2 (1: 1 mixture) and Alq. When the performance of this device was evaluated, it was found that the voltage was 3V at a voltage of 7V.
A current of 8 mA / cm ² was flown, and yellow-green light emission with a brightness of 98 cd / m ² was obtained. However, this device is not red in color.

[Chemical 28]

Comparative Example 3 Compound 1-as the light emitting material and the light emitting medium described in Example 1
An organic EL device was manufactured in the same manner as in Example 1 except that the following compound 13 and Alq were co-deposited at a weight ratio of 2:40 instead of 1, 1-2 (1: 1 mixture) and Alq. When the performance of this element was evaluated, a current of 52 mA / cm ² at a voltage of 9.5 V and a luminance of 102 cd / m 2
A red-orange emission of ² was obtained. However, this device has high voltage and low luminous efficiency.

[Chemical 29]

Comparative Example 4 Compound 1 as a light emitting material and a light emitting medium described in Example 10
-1, 1-2 (1: 1 mixture) and DPVDPAN in place of the compound 12 and DPVDPAN in a weight ratio of 2:40.
An organic EL device was produced in the same manner as in Example 1, except that the simultaneous vapor deposition was carried out in. When the performance of this device was evaluated, a current of 4.4 mA / cm ² was applied at a voltage of 7 V, and a green light emission with a luminance of 120 cd / m ² was obtained. However, the emission color is not red.

Comparative Example 5 Compound 1 as a light emitting material and a light emitting medium described in Example 10
-1, 1-2 (1: 1 mixture) and DPVDPAN in place of the compound 13 and DPVDPAN in a weight ratio of 2:40.
An organic EL device was produced in the same manner as in Example 1, except that the simultaneous vapor deposition was carried out in. When the performance of this device was evaluated, a current of 44 mA / cm ^{2 was} passed at a voltage of 9.5 V, and orange light emission with a brightness of 171 cd / m ² was obtained. However, this device has a high voltage and does not emit red light.

[0075]

As described above in detail, the use of the novel fused aromatic compound of the present invention provides an organic electroluminescent device which emits red light with high emission brightness and emission efficiency, high color purity. To be Therefore, the organic electroluminescent element of the present invention is extremely useful as a light source for various electronic devices.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C07D 213/74 C07D 213/74 C09K 11/06 620 C09K 11/06 620 630 630 H05B 33/14 H05B 33 / 14 B 33/22 33/22 BD (72) Inventor Takashi Aragane 1280, Kamizumi, Sodegaura-shi, Chiba (72) Inventor Hosokawa Chiho, 1280, Kamizumi, Sodegaura, Chiba (72) Inventor Masaru Kusumoto Chiba Sodegaura City, Kamizumi 1280 F Term (reference) 3K007 AB02 AB03 AB04 DB03 4C055 AA01 BA02 BA52 BB04 BB19 CA01 DA01 EA01 4H006 AA01 AA03 AB92

Claims (10)

[Claims] 1. A novel condensed aromatic compound represented by any one of the following general formulas (1) to (11). [Chemical 1] (In the formula, R _{1 to} R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted An aryl group having 6 to 40 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 4 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a cyano group, a perfluoroalkyl group, a nitro group, a halogen group or a group represented by the following general formula (A), which is represented by the general formula (1) to ( In 3) and (8), at least one of R _{1 to} R ₁₄ is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and a general formula (4) And to (10) Information, at least one of R ₁ to R ₁₆ is a group represented by the following general formula (A),
At least one is an electron-withdrawing group and has the general formula (5)
In, at least one of R _{1 to} R ₁₆ is a group represented by the following general formula (A), at least one is an electron-withdrawing group, and the general formulas (6), (7), ( In 9) and (11), at least 1 of R _{1 to} R ₁₈
One is a group represented by the following general formula (A), and at least one is an electron-withdrawing group. In addition, R _{1 to} R ₁₈ may form a cyclic structure with adjacent groups. ) [Chemical 2] (In the formula, X ₁ and X ₂ are each independently a hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a hetero group having 3 to 40 carbon atoms A cyclic group, X ₁ and X
₂ may be connected to each other to form a ring structure. Also,
X ₁ or X ₂ and a fluoranthene skeleton group are linked to each other,
You may form a cyclic structure. ) 2. The condensed aromatic compound according to claim 1, which is an organic compound for an organic electroluminescence device. 3. In an organic electroluminescence device in which an organic thin film layer consisting of one or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers comprises
An organic electroluminescence device containing a condensed aromatic compound having a fluoranthene skeleton in which at least an amino group and an electron-withdrawing group are bonded. 4. In an organic electroluminescent device having at least a light emitting layer and an electron transport layer sandwiched between a cathode and an anode, the electron transport layer has a fluoranthene skeleton in which at least an amino group and an electron withdrawing group are bonded. An organic electroluminescence device containing a condensed aromatic compound. 5. In an organic electroluminescence device having at least a light emitting layer and a hole transport layer sandwiched between a cathode and an anode, the hole transport layer has a fluoranthene skeleton in which at least an amino group and an electron-withdrawing group are bonded. An organic electroluminescence device containing a condensed aromatic compound having: 6. In an organic electroluminescence device in which an organic thin film layer consisting of one layer or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers comprises
An organic electroluminescence device containing the condensed aromatic compound according to claim 1. 7. An organic electroluminescence device having at least a light emitting layer and an electron transport layer sandwiched between a cathode and an anode, wherein the electron transport layer contains the fused aromatic compound according to claim 1. element. 8. In an organic electroluminescence device in which at least a light emitting layer and a hole transport layer are sandwiched between a cathode and an anode, the hole transport layer is an organic compound containing the fused aromatic compound according to claim 1. Electroluminescent device. 9. The organic electroluminescence device according to claim 3, further comprising an inorganic compound layer between at least one electrode and the organic thin film layer. 10. The organic electroluminescence device according to claim 3, which emits reddish light.