JP3175816B2 - Organic electroluminescence device - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device (hereinafter abbreviated as "organic EL device").
More specifically, the present invention relates to an organic EL device comprising a distyrylarylene derivative that can withstand long-term use.

[0002]

2. Description of the Related Art EL devices utilizing electroluminescence have the characteristics of high visibility due to self-luminescence and excellent impact resistance because they are completely solid devices. , Thin display elements, backlights for liquid crystal displays, flat light sources, and the like. An EL element currently in practical use is a dispersion-type EL element. This dispersion-type EL element has several tens of volts and 10 kHz.
Since the above AC voltage is required, the driving circuit is complicated. On the other hand, organic thin film EL devices can reduce the driving voltage to about 10 V and emit light with high luminance, and have been actively studied in recent years, and many organic thin film EL devices have been developed (CWTang and SAVAN Slyke, Appl.Phys.L
ett., vol. 51, pp. 913-915 (1987); JP-A-63-264.
629). These organic thin film EL devices are of a stacked type of a transparent electrode / a hole injection layer / a light emitting layer / a back electrode, and holes can be efficiently injected into the light emitting layer by the hole injection layer. Among the organic EL devices, those emitting blue light with high luminance are already known (Japanese Patent Publication No. 7-11940).
No. 7), in general, many compounds capable of emitting blue light have a small spread of π (pi) electrons, a low molecular weight, and therefore have a low glass transition temperature (Tg). Therefore, an EL element which emits blue light and has excellent thermal stability has been desired. In order to maintain thermal stability, there is an example in which the light-emitting material has a dimer structure or an oligomer structure. In such a case, the glass transition temperature Tg is high and the thermal stability is excellent, but the EL light-emitting characteristics are low. There was a problem that it became low. For these reasons, conventionally, it has been difficult to provide a blue light emitting device having excellent EL light emitting characteristics and excellent heat stability.

[0003]

Means for Solving the Problems Accordingly, the present inventors have:
As a result of intensive studies to develop a blue light emitting device having excellent EL light emitting characteristics and excellent heat stability, it was found that the above object can be achieved by using a distyryl arylene derivative having polyphenyl in the central skeleton. Was. The present invention has been completed based on such findings.

That is, the present invention provides a compound represented by the general formula (I)

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Wherein l, m and n are each 0 or 1
And (l + m + n) ≧ 1; (1) When l = 1 and m = n = 0, R ^{1 to} R ¹² each independently represent a hydrogen atom or a carbon atom
Alkyl group having 6 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, aryloxy group having 6 to 18 carbon atoms, aryl group having 6 to 20 carbon atoms, amino group, alkylamino group, arylamino group, cyano group, nitro group , Hydroxyl, halogen, or

Embedded image Is shown. However, at least ^one of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹¹ and R ¹² ,
It bonds to each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, a ring may be formed via a hetero atom. Further, all of R ^{1 to} R ¹² are hydrogen atoms and carbon atoms.
Except when it is a group selected from alkyl groups having a prime number of 1 to 6.
Good. (2) When l = m = 1, n = 0 R ^{1 to} R ¹² are the same as above, and R ³ ′, R ⁴ ′,
R ⁹ ′ and R ¹⁰ ′ are each independently a hydrogen atom or carbon atom 1
Alkyl group having 6 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, aryloxy group having 6 to 18 carbon atoms, aryl group having 6 to 20 carbon atoms, amino group, alkylamino group, arylamino group, cyano group, nitro group , Hydroxyl, halogen, or

Embedded image Is shown. However, R ¹ and R ^2, R ³ and R ^4, R ³ 'and R ^4', R ⁵
And R ⁶ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ⁹ ′ and R ¹⁰ ′, R ¹¹ and R
¹² may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, a ring may be formed via a hetero atom. Also, R ² and R ^3, R ⁴ and ^{R 3 ', R 4' R} 5 and, R ⁸ and R ^9, R ¹⁰ and R ⁹ ', R ^10' and R ¹¹
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
It may form a member ring. In that case, a ring may be formed via a hetero atom. (3) When l = m = n = 1 R ^{1 to} R ¹² , R ³ ′, R ⁴ ′, R ⁹ ′, R ¹⁰ ′ are the same as above, and R ³ ″, R ⁴ ″, R ⁹ ", R ^10" are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, atoms 1
To 6 alkoxy groups, 6 to 18 carbon atom aryloxy groups, 6 to 20 carbon atom aryl groups, amino groups, alkylamino groups, arylamino groups, cyano groups, nitro groups, hydroxyl groups, halogen atoms or

Embedded image Is shown. However, R ¹ and R ^2, R ³ and R ^4, R ³ 'and R ^4', R ³ "
And R ⁴ ", R ⁵ and R ^6, R ⁷ and R ^8, R ⁹ and R ^10, R ⁹ 'and R ^10', R ^9" and R ¹⁰ ", R ¹¹ and R ¹² are bonded to each other saturated Alternatively, it may form an unsaturated 5- or 6-membered ring, in which case a ring may be formed via a heteroatom, and R ² and R ³ , R ⁴ and R ³ ′, R ⁴ 'and R ³ ", R ^4" and R ^5, R ⁸ and R ^9, R ¹⁰ and R ^9', R ¹⁰ 'and R ⁹ ", R ^10" and R
¹¹ may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, a ring may be formed via a hetero atom. X and Y each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. The substituents of X and Y may combine with each other to form a substituted or unsubstituted saturated or unsaturated 5- or 6-membered ring. Here, the substituent means an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an amino group, an alkylamino group, It represents an arylamino group, a cyano group, a nitro group, a hydroxyl group or a halogen atom. These substituents may be single or plurally substituted. ] It is intended to provide an organic electroluminescence device containing a distyrylarylene derivative represented by the following formula: Further, the present invention provides an organic electroluminescent device comprising the distyrylarylene derivative sandwiched between a pair of electrodes, and
Another object of the present invention is to provide an organic electroluminescent device using the distyrylarylene derivative as a constituent material of a light emitting layer.

[0006]

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an organic EL containing a distyrylarylene derivative represented by the above general formula (I).
Element. Here, in the general formula (I), l, m and n are each 0 or 1, and (l + m + n)
≧ 1. In the formula, R ^{1 to} R ¹² each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an aryl having 6 to 20 carbon atoms. Group, amino group, alkylamino group, arylamino group, cyano group, nitro group, hydroxyl group,
Halogen atom or

Embedded image Is shown. Here, the alkyl group having 1 to 6 carbon atoms includes a methyl group, an ethyl group, an n-propyl group, an i-propyl group,
n-butyl group, i-butyl group, sec-butyl group, t-
Examples thereof include a butyl group, an i-pentyl group, a t-pentyl group, a neopentyl group, an n-hexyl group, and an i-hexyl group. Examples of the alkoxy group having 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, i-propoxy, butyloxy, i-butyloxy, and se.
Examples thereof include a c-butyloxy group, an i-pentyloxy group, a t-pentyloxy group, and an n-hexyloxy group. Examples of the aryloxy group having 6 to 18 carbon atoms include a phenoxy group and a naphthyloxy group.
Examples of the aryl group 20 include a phenyl group and a naphthyl group. Further, an amino group, showed a -NH _2, alkylamino groups, -NR ₂ (R is an alkyl group having 1 to 6 carbon atoms) indicates, arylamino group, -NAr ₂ (Ar
Represents an aryl group having 6 to 20 carbon atoms). Examples of the halogen atom include fluorine, chlorine, bromine and iodine atoms. However, in the general formula (I), l = 1,
When m = n = 0 , all of R ^{1 to} R ¹² are hydrogen atoms
And a group selected from alkyl groups having 1 to 6 carbon atoms
Excludes Further, in the general formula (I), l = 1, m
= N = 0, R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ ,
At least one of R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , and R ¹¹ and R ¹² combine with each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, the hetero atom (N,
A ring may be formed via O, S). As a specific example of this, when R ¹ and R ⁷ , R ⁹ and R ¹⁰ , and R ⁵ and R ⁶ each form an unsaturated 6-membered ring,

[0007]

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And the like. R ⁷ and R ⁸ form a saturated 5-membered ring via a heteroatom O, R ¹¹ and R ¹² form a saturated 5-membered ring via a heteroatom N, and R ³ and R ⁴ , R ⁹ and R ^{9
When 10} forms a saturated 6-membered ring,

[0009]

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And the like. Furthermore, the general formula (I)
In the case where l = m = 1 and n = 0, the general formula is represented as follows.

[0011]

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(Where R ³ ′, R ⁴ ′, R ⁹ ′, R ¹⁰ ′ are
Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an amino group, an alkylamino group, Arylamino group, cyano group,
Nitro group, hydroxyl group, halogen atom or

Embedded imageIs shown. X and Y are the same as above. ) R¹And R^Two, R^ThreeAnd R^Four, R^Three'And R^Four', R^FiveAnd R⁶, R⁷When
R⁸, R⁹And R^Ten, R⁹'And R^Ten', R¹¹And R¹²Are connected to each other
Combine to form a saturated or unsaturated 5- or 6-membered ring
It may or may not be formed. That
Form a ring via a heteroatom (N, O, S)
Is also good. Also, R^TwoAnd R^Three, R^FourAnd R^Three', R^Four'And R^Five, R⁸
And R⁹, R^TenAnd R⁹', R^Ten'And R ¹¹Combine with each other
Forming a sum or unsaturated 5- or 6-membered ring,
Or may not be formed. In that case,
A ring may be formed via a terror atom (N, O, S).
Specific examples of these include R^TwoAnd R^Three, R^TenAnd R⁹',
R^Four'And R^FiveEach form a saturated 5-membered ring,

[0013]

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And the like. When R ⁴ and R ³ ′ and R ¹⁰ and R ⁹ ′ form a saturated 6-membered ring,

[0015]

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And the like. R ¹⁰ is

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In the case where R ⁹ ′ is hydrogen and forms a 5-membered ring,

[0018]

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And the like. Further, when l = m = n = 1 in the general formula (I), the general formula is represented as follows.

[0020]

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(Where R ³ ′, R ⁴ ′, R ³ ″, R ⁴ ″,
R ⁹ ′, R ¹⁰ ′, R ⁹ ″ and R ¹⁰ ″ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, An aryl group having 6 to 20 carbon atoms, an amino group, an alkylamino group,
Arylamino group, cyano group, nitro group, hydroxyl group, halogen atom or

Embedded image Is shown. ) R ¹ and R ^2, R ³ and R ^4, R ³ 'and R ^4', R ³ "and R ^4", R ⁵ and R ^6, R ⁷ and R ^8, R ⁹ and R ^10, R ⁹ ' And R ¹⁰ ′, R ⁹ ″ and R ¹⁰ ″, R ¹¹ and R ¹² are bonded to each other to form a saturated or unsaturated 5- or 6-membered ring, or
It may not be formed. In that case, the hetero atom (N,
A ring may be formed via O, S). Also, R ² and R ^3, R ⁴ and R ³ ', R ^4' and R ³ ", R ^4" and R ^5, R ⁸ and R ^9,
R ¹⁰ and R ⁹ ′, R ¹⁰ ′ and R ⁹ ″, and R ¹⁰ ″ and R ¹¹ are bonded to each other to form a saturated or unsaturated 5- or 6-membered ring, or It is not necessary. In that case, a ring may be formed via a hetero atom (N, O, S).

Specific examples of these are R ⁸ , R ⁹ ,
R ¹⁰ ", R ¹¹

Embedded image In the case where R ³ ′ and R ⁴ ′ each form an unsaturated 5-membered ring via a heteroatom N,

[0023]

Embedded image And the like.

X and Y each independently represent a substituted or unsubstituted phenyl group, naphthyl group, biphenyl group, terphenyl group, anthralyl group, phenanthryl group, pyrenyl group, perylenyl group or other aryl group having 6 to 20 carbon atoms. Show. Here, examples of the substituent include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group,
i-butyl group, sec-butyl group, t-butyl group, i-butyl group
An alkyl group having 1 to 6 carbon atoms such as pentyl group, t-pentyl group, neopentyl group, n-hexyl group, i-hexyl group, methoxy group, ethoxy group, propoxy group, i-propoxy group, butyloxy group, i- Butyloxy group, s
1 carbon atom such as ec-butyloxy group, i-pentyloxy group, t-pentyloxy group, n-hexyloxy group, etc.
An aryloxy group having 6 to 18 carbon atoms such as an alkoxy group, a phenoxy group, a naphthyloxy group, a phenyl group,
Amino group, alkylamino group, arylamino group, cyano group, nitro group, hydroxyl group or fluorine, chlorine, bromine,
Examples include a halogen atom such as an iodine atom. These substituents may be single or plurally substituted.

X and Y may combine with a substituent to form a substituted or unsubstituted saturated 5- or 6-membered ring. As a specific styryl compound having a saturated 5-membered ring or a 6-membered ring, when X and Y form a saturated 5-membered ring, the case where 1 = m = 1 and n = 0 is shown as an example,

[0026]

Embedded image When X and Y form a saturated 6-membered ring,

[0027]

Embedded image And the like.

The styryl compound represented by the above general formula (I) can be produced by various known methods. Specifically, there are the following three methods. [Method 1] General formula (a)

[0029]

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(Where l, m and n are each 0 or 1)
And (l + m + n) ≧ 1. Also, R¹
~ R¹², R^Three', R^Four', R⁹', R^Ten', R^Three", R^Four", R⁹"
And R ^Ten"Is the same as described above, and R is a group having 1 to 4 carbon atoms.
Shows an alkyl group or a phenyl group. )
A sulfonate and a compound of the general formula (b)

[0031]

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(Wherein X and Y are the same as described above) by condensing a carbonyl compound represented by the formula (Wittig reaction or Wittig-Horne).
r reaction). [Method 2] General formula (c)

[0033]

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(Where l, m and n are each 0 or 1
And (l + m + n) ≧ 1. Also, R¹
~ R¹², R^Three', R^Four', R⁹', R^Ten', R^Three", R^Four", R⁹"
And R ^Ten"Is the same as above.)
Dehydric compound and general formula (d)

[0035]

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(Wherein R, X, and Y are the same as described above) by condensing a phosphonate ester represented by the formula (Wittig reaction or Wittig-H).
The compound can be synthesized by an 反 応 orner reaction).

As the reaction solvent used in this synthesis, hydrocarbons, alcohols and ethers are preferable. Specifically, methanol; ethanol; isopropanol; butanol; 2-methoxyethanol; 1,2-dimethoxyethane; bis (2-methoxyethyl) ether; dioxane; tetrahydrofuran; toluene; xylene; dimethyl sulfoxide; N, N-dimethyl Formamide; N
-Methylpyrrolidone; 1,3-dimethyl-2-imidazolidinone; Particularly, tetrahydrofuran and dimethyl sulfoxide are preferred. As the condensing agent, alcoholates such as sodium hydroxide, potassium hydroxide, sodium amide, sodium hydride, n-butyllithium, sodium methylate and potassium tert-butoxide are preferred, and n-butyllithium and potassium tert-butoxide are particularly preferred.
Butoxide is preferred. The reaction temperature varies depending on the type of the reaction raw materials used and cannot be determined uniquely, but can be generally specified in a wide range from 0 ° C to about 100 ° C. Particularly preferably, it is in the range of 0 ° C. to room temperature.

[Method 3] General formula (e)

[0039]

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(Wherein X, Y, R ¹ , R ² , R ⁷ , R ⁸ or R ⁵ , R ⁶ , R ¹¹ and R ¹² are the same as described above) A Grignard reagent prepared by the reaction, and a general formula (f)

[0041]

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(Where l, m and n are each 0 or 1
And (l + m + n) ≧ 1. Also,
R^Three, R^Four, R⁹, R^Ten, R^Three', R^Four', R⁹', R^Ten',
R^Three", R^Four", R ⁹"And R^Ten"Is the same as above.)
The dibromoarylene represented is coupled with a metal catalyst.
Can be synthesized by a Grignard reaction.
The transition metal complex catalyst used for coupling is Ni
Kell's catalyst and palladium catalyst are preferred.
_Two(Dppp) (Tokyo Kasei), [NiCl_Two(PP
h_Three)_Two], PdcL_Two(Dppf), Pd (PPh
_Three)_FourAre used. The reaction solvent was dehydrated
Diethyl ether, THF, di-n-propyl ether
Di-n-butyl ether, di-τ-propyl ether
Diethylene glycol dimethyl ether (diglycol
), Dioxane, dimethoxyethane (DME)
Can be used. Preferably, diethyl ether
Or THF is good.

The following are specific examples (1) to (72) of the styryl compound used in the present invention, but the present invention is not limited thereto.

[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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[0052]

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[0053]

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[0054]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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The thus obtained distyryl arylene derivative represented by the general formula (I) of the present invention is
It is effective as a light emitting material in an L element. When the distyrylarylene derivative is used as the light emitting layer, it can be formed by thinning the distyrylarylene derivative of the general formula (I) by a known method such as a vapor deposition method, a spin coating method, and a casting method. Although it is possible, it is particularly preferable to use a molecular deposition film. Here, the molecular deposition film is a thin film formed by depositing the compound from a gaseous state or a film formed by solidifying the compound from a solution state or a liquid phase state. Shows,
Usually, this molecular deposition film can be distinguished from a thin film (molecule accumulation film) formed by the LB method. Further, as disclosed in JP-A-59-194393, the binder is prepared by dissolving a binder such as a resin and the compound in a solvent to form a solution. It can be formed into a thin film by the method described above. The thickness of the light emitting layer formed in this manner is not particularly limited and can be appropriately selected according to the situation, but is usually selected in the range of 5 nm to 5 μm.

The light emitting layer of this EL device has the following features. (1) When an electric field is applied, holes can be injected by an anode or a hole injection transport layer, and electrons can be injected by a cathode or an electron injection layer. Function, (2) transport function of moving injected charges (electrons and holes) by the force of an electric field, and (3) light emission that provides a field of recombination of electrons and holes inside the light emitting layer, which is connected to light emission. It has functions and the like. Note that there may be a difference between the ease with which holes are injected and the ease with which electrons are injected, and the transportability represented by the mobility of holes and electrons may be large or small. Is preferably transferred. The compound represented by the general formula (I) used for the light emitting layer generally has an ionization energy of 6.0 e.
Since it is smaller than about V, it is relatively easy to inject holes if an appropriate anode metal or anode compound is selected. Further, since the electron affinity is higher than about 2.8 eV, if an appropriate cathode metal or cathode compound is selected, it is relatively easy to inject electrons, and also excellent in the ability to transport electrons and holes. Further, since the solid-state fluorescence is strong, the ability to convert an excited state formed at the time of recrystallization of electrons and holes of the compound or its aggregate or crystal, to light is large.

The structure of the EL device using the compound of the present invention has various modes. Basically, the light emitting layer is sandwiched between a pair of electrodes (anode and cathode). If necessary, a hole injection / transport layer or an electron injection layer may be interposed. As an interposition method, there is mixing into a polymer or simultaneous sorption. Specifically, (1) anode / light-emitting layer / cathode, (2) anode / hole injection / transport layer / light-emitting layer / cathode,
Examples of (3) anode / hole injection / transport layer / light-emitting layer / electron injection layer / cathode, and (4) anode / light-emitting layer / electron injection layer / cathode, etc. The hole injecting and transporting layer and the electron injecting layer are not necessarily required, but the presence of these layers further improves the light emitting performance. In addition, in the device having the above-described structure, it is preferable that each of the devices is supported by a substrate, and the substrate is not particularly limited, and is made of a material conventionally used in an EL device, such as glass, transparent plastic, or quartz. Can be used.

As the anode in this EL element, a metal, an alloy, an electrically conductive compound having a large work function (4 eV or more) and a mixture thereof are preferably used as an anode material. A specific example of such an electrode material is A
u and a dielectric transparent material such as CuI, ITO, SnO ₂ , and ZnO. The anode can be produced by forming a thin film from these electrode substances by a method such as vapor deposition or sputtering. When light is extracted from this electrode, the transmittance is desirably higher than 10%, and the sheet resistance of the electrode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually 10 nm to 1 μm, preferably 10 to 1 μm.
It is selected in the range of 200 nm.

On the other hand, as the cathode, a metal, an alloy, an electrically conductive compound or a mixture thereof having a small work function (4 eV or less) as an electrode material is used. Specific examples of such an electrode material include sodium, sodium-potassium alloy, magnesium, lithium, a magnesium / copper mixture, Al / AlO ₂ , and indium. The cathode can be manufactured by forming a thin film of these electrode substances by a method such as vapor deposition or sputtering. Further, the sheet resistance as an electrode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm.
To 1 μm, preferably in the range of 50 to 200 nm. In this EL device, it is convenient that one of the anode and the cathode is transparent or translucent because it transmits light, so that the efficiency of extracting light is good.

As described above, the structure of the EL device using the compound of the present invention has various modes, and the hole injecting / transporting layer in the EL device having the structure (2) or (3) is as follows.
A layer made of a hole transporting compound, which has a function of transmitting holes injected from the anode to the light emitting layer, and has a hole injecting and transporting layer interposed between the anode and the light emitting layer. Many holes are injected into the light emitting layer at a low electric field. In addition, electrons injected from the cathode or the electron injection layer into the light emitting layer are accumulated near the interface in the light emitting layer due to the electron barrier existing at the interface between the light emitting layer and the hole injection transport layer, and the light emission of the EL element is reduced. Efficiency is improved and an EL element having excellent light emitting performance is obtained.

The hole transporting compound used in the hole injecting / transporting layer is disposed between two electrodes to which an electric field is applied, and when holes are injected from the anode, the holes are appropriately transferred to the light emitting layer. A compound capable of transmitting to, for example, 10 ⁴ to 10 ⁶ V
/ Cm when applying an electric field of at least 10 ^-6 cm ² / (V
(Seconds) is preferable. There is no particular limitation on such a hole transporting compound as long as it has the above-mentioned preferable properties. Conventionally, in a photoconductive material, a compound commonly used as a hole charge transport material or a hole transporting material of an EL device is used. Any of the known materials used for the injection transport layer can be selected and used.

Examples of the charge transporting material include triazole derivatives (as described in US Pat. No. 3,112,197) and oxadiazole derivatives (US Pat.
89,447), imidazole derivatives (described in JP-B-37-16096, etc.), polyarylalkane derivatives (US Pat. No. 3,611)
5,402, 3,820,989, 3,5
No. 42,544, Japanese Patent Publication No. 45-555, 5
1-110983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148, JP-A-55-108667, and JP-A-55-15695.
Nos. 3 and 56-36656), pyrazoline derivatives and pyrazolone derivatives (U.S. Pat. Nos. 3,180,729 and 4,278,746; No. 88064, 55-8806
No. 5, No. 49-105537, No. 55-51
Nos. 086 and 56-80051 and 56-8
Nos. 8141 and 57-45545 and 54-
And phenylenediamine derivatives (U.S. Pat. No. 3,615,404, JP-B-51-10105, JP-B-46-3712, and JP-A-47-47). JP-A-25-25336, JP-A-54-53435, JP-A-54-1105
Nos. 36 and 54-119925) and arylamine derivatives (U.S. Pat. No. 3,567,4).
50, 3,180,703, 3,24
Nos. 0,597, 3,658,520 and 4,2
No. 32,103, No. 4,175,961, No. 4,012,376, JP-B-49-35702, JP-A-39-27577, and JP-A-55-1442.
Nos. 50, 56-119132 and 56-2
No. 2437, West German Patent No. 1,110,518, etc.), amino-substituted chalcone derivatives (U.S. Pat. No. 3,526,501) and oxazole derivatives (U.S. Pat. No. 3,526,501). No. 3,257,203), styrylanthracene derivatives (described in JP-A-56-46234, etc.), and fluorenone derivatives (described in JP-A-54-110837). ), Hydrazone derivatives (US Pat. No. 3,71
No. 7,462, JP-A-54-59143, JP-A-55-52063, JP-A-55-52064,
JP-A-55-46760, JP-A-55-85495, JP-A-57-1350, and JP-A-57-148749.
And stilbell derivatives (JP-A-61-210363, JP-A-61-2284).
No. 51, No. 61-14642, No. 61-72
Nos. 255, 62-47646, 62-3
Nos. 6,674, 62-10652, 62-
Nos. 30255, 60-93445, 60
-94462, JP-A-60-174747, JP-A-60-175052) and the like.

These compounds can be used as a hole transporting compound, and the following porphyrin compounds (those described in JP-A-63-295695 and the like)
And aromatic tertiary amine compounds and styrylamine compounds (US Pat. No. 4,127,412;
Nos. 27033, 54-58445, 54
Nos. 149634, 54-64299, 55-79450, 55-144250, 56-119132, and 61-29555.
No. 8, No. 61-98353, No. 63-295
No. 695), particularly, the aromatic tertiary amine compound is preferably used.

Typical examples of the porphyrin compound include:
Porphyrin; 5,10,15,20-tetraphenyl-21H, 23H-porphyrin copper (II);
15,20-tetraphenyl-21H, 23H-porphyrin zinc (II); 5,10,15,20-tetrakis (pentafluorophenyl) -21H, 23H-porphyrin; silicon phthalocyanine oxide; aluminum phthalocyanine chloride; phthalocyanine (metal-free Dilithium phthalocyanine; copper tetramethyl phthalocyanine; copper phthalocyanine; chromium phthalocyanine; zinc phthalocyanine; lead phthalocyanine; titanium phthalocyanine oxide; magnesium phthalocyanine;
Representative examples of the aromatic tertiary compound and styrylamine compound include N, N, N ′, N′-tetraphenyl- (1,1′-biphenyl) -4,4′-diamine;
N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine; 2,2-bis (4-di-p-tolylamino Phenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl- (1,1′-biphenyl) -4,
4'-diamine; 1,1-bis (4-di-p-tolylaminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p- Tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N'-di (4-methoxyphenyl)-(1,1'-biphenyl)
-4,4'-diamine; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether;
4'-bis (diphenylamino) quadriphenyl;
N, N, N-tri (p-tolyl) amine; 4- (di-p
-Tolylamine) -4 '-[4 (di-p-tolylamine) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4'-N, N-diphenylamino Stilbene; N-
Phenylcarbazole and the like.

The hole injecting / transporting layer in the EL device may be composed of one or more of these hole transporting compounds, or may be a hole transporting compound of a different kind from the layer. It may be a laminate of injection and transport layers. On the other hand, the electron injecting layer (electron injecting and transporting layer) in the EL device having the constitution (3) is made of an electron transfer compound, and has a function of transferring electrons injected from the cathode to the light emitting layer. I have. There is no particular limitation on such an electron transfer compound, and any one of conventionally known compounds can be selected and used. Preferred examples of the electron transfer compound include:

[0074]

Embedded image Nitro-substituted fluorenone derivatives, such as

[0075]

Embedded image

Thiopyran dioxide derivatives such as

[0077]

Embedded image

Diphenylquinone derivatives (those described in Polymer Preprints, Japan, Vol. 37, No. 3, page 681 (1988)), or

[0079]

Embedded image

[Journal of Applied Physics], vol. 27,
269 (1988)] and anthraquinodimethane derivatives (JP-A-57-149259, JP-A-58-55450, and 61-22515).
No. 1, No. 61-233750, No. 63-10
4061), fluorenylidenemethane derivatives (JP-A-60-69657 and JP-A-60-69657).
143,768, 61-148159, etc.), anthrone derivatives (JP-A-61-2).
Nos. 25151 and 61-233750) and the following general formula (II) or (III)

[0081]

Embedded image

[0082] (wherein, Ar ¹ to Ar ³ and Ar ⁵ each independently represent a substituted or unsubstituted aryl group, Ar ⁴
Represents a substituted or unsubstituted arylene group. )). Here, the aryl group includes a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, a pyrenyl group, and the like. And the like. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group. The compound represented by formula (II) or (III) is preferably a thin film-forming compound. Specific examples of the compound represented by the general formula (II) or (III) include:

[0083]

Embedded image

[0084]

Embedded image

[0085]

Embedded image And the like.

"Appl. Phys. Lett." Vol. 55, No. 148
Oxadiazole derivatives disclosed on page 9 (1989) can be mentioned. The hole injecting / transporting layer and the electron injecting layer are layers having any one of an injecting property, a transporting property, and a barrier property of electrification. In addition to the above-described organic materials, crystalline materials such as Si-based, SiC-based, and CdS-based Alternatively, an inorganic material such as an amorphous material can be used. The hole injection transport layer and the electron injection layer using an organic material can be formed in the same manner as the light emitting layer, and the hole injection transport layer and the electron injection layer using an inorganic material are formed by a vacuum evaporation method, sputtering, or the like. Although it is possible to use any of organic and inorganic materials, it is preferable to form by a vacuum deposition method for the same reason as in the light emitting layer.

Next, an example of a preferred method for manufacturing the EL element of the present invention will be described for each element of each constitution.
The method of manufacturing the EL element comprising the anode / light-emitting layer / cathode will be described. First, a thin film made of a desired electrode material, for example, a material for an anode, is formed on an appropriate substrate in a thickness of 1 μm or less, preferably 10 to 200 nm. So that
After forming the anode by a method such as vapor deposition or sputtering to form an anode, the light emitting material represented by the general formula (I)
Is formed, and a light emitting layer is provided. Examples of the method for thinning the light emitting material include a spin coating method, a casting method, and a vapor deposition method. The vapor deposition method is preferable because a uniform film is easily obtained and pinholes are hardly generated. . When this vapor deposition method is used for thinning the light emitting material, the vapor deposition conditions vary depending on the type of the organic compound used for the light emitting layer to be used, the target crystal structure of the molecular deposition film, the association structure, and the like. Boat heating temperature 50-400 ° C, degree of vacuum 10 ^-5 -10
^-3 Pa, a deposition rate of 0.01 to 50 nm / sec, a substrate temperature of -50 to +300 [deg.] C., and a thickness of 5 nm to 5 [mu] m. Next, after forming this light emitting layer, a thin film made of a material for a cathode is formed thereon by a method such as vapor deposition or sputtering so as to have a thickness of 1 μm or less, preferably 50 to 200 nm. Is provided, a desired EL element is obtained. In the production of this EL element, the production order can be reversed, and the cathode, the light emitting layer, and the anode can be produced in this order.

A hole injection / transport material is provided between a pair of electrodes.
In the case of a device comprising an anode / light-emitting layer / cathode in which a light-emitting material and an electron-injecting material are mixed and sandwiched between electrodes to form a light-emitting layer, for example, a material for the anode may be provided on a suitable substrate. A thin film composed of a hole injecting and transporting material, a light emitting material, an electron injecting material, a binder such as polyvinyl carbazole or the like, or forming a thin film from this solution by a dip coating method to form a light emitting layer. And a thin film made of a cathode material is formed thereon. Here, an element material to be a material of the light emitting layer may be further vacuum-deposited on the manufactured light emitting layer, and a thin film made of a cathode material may be formed thereon. Alternatively, a hole injecting and transporting material, an electron injecting material, and a light emitting material are simultaneously deposited to form a light emitting layer,
A thin film made of a cathode material may be formed thereon.

Next, a method for manufacturing an EL device comprising an anode / a hole injection / transport layer / a light emitting layer / a cathode will be described. First, an anode is formed in the same manner as in the case of the above-mentioned EL device, and then formed thereon. Then, a thin film made of a hole transport compound is formed by a spin coating method or the like, and a hole injection / transport layer is provided.
The conditions at this time may be in accordance with the conditions for forming the thin film of the light emitting material. Next, a desired EL element can be obtained by sequentially providing a light emitting layer and a cathode on the hole injecting and transporting layer in the same manner as in the case of manufacturing the EL element. In addition,
Also in the production of this EL element, the production order is reversed,
It is also possible to produce a cathode, a light emitting layer, a hole injection / transport layer, and an anode in this order. Further, a method of manufacturing an EL device composed of an anode / a hole injection / transport layer / a light emitting layer / an electron injection layer / a cathode will be described. First, as in the case of the EL device, the anode, the hole injection / transport layer are formed. After sequentially providing a layer and a light emitting layer, a thin film made of an electron transfer compound is formed on the light emitting layer by a spin coating method or the like, an electron injection layer is provided, and then a cathode is formed on the EL element. By providing the EL device in the same manner as in the case of manufacturing, a desired EL element can be obtained. In the production of this EL element, the production order may be reversed, and the anode, the electron injection layer, the light emitting layer, the hole injection transport layer, and the anode may be produced in this order.

The organic EL of the present invention thus obtained
When a DC voltage is applied to the device, when a voltage of about 1 to 30 V is applied with the anode having a positive polarity and the cathode having a negative polarity, light emission can be observed from the transparent or translucent electrode side. Also, even if a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state. In addition,
The waveform of the applied alternating current may be arbitrary.

[0091]

Now, the present invention will be described in further detail with reference to Production Examples, Examples and Comparative Examples. Production Example 1

[0092]

Embedded image

In an Ar gas atmosphere, 1.0 g of benzophenone (0.0054) was placed in a 100 ml three-necked flask.
9 mol) and 1.2 g (0.00198) of a phosphonate ester
Mol) was suspended in 30 ml of dimethyl sulfoxide dried over molecular sieves. This suspension was added at room temperature to 0.5 g (0.004) of potassium t-butoxide.
(46 mol) was added and reacted. The reaction immediately showed a red-brown suspension. After stirring for about 1 hour while maintaining the reaction temperature at 27 ° C., the reaction product showed a yellow suspension.
After further stirring for 2 hours, 40 ml of methanol was added, and the yellow precipitate was collected by filtration. Next, the yellow precipitate was suspended in 100 ml of toluene, and the target substance was extracted by heating, and then toluene was distilled off.
0.44 g of a white powder was obtained. The yield was 34% and the melting point of the obtained powder was 292 ° C. Further, the obtained white powder was purified by sublimation at a board temperature of 320 ° C. to obtain 0.32 g of a purified powder.

The mass spectrometry (FD-MS) of this purified powder showed that m / z = 662 (M ⁺ : z = 1), 331
(M ²⁺ : z = 1). When the absorption spectrum was measured in a toluene solvent, λ max = 350.6 nm (ε
= 69900), and when the fluorescence spectrum was measured at 350 nm excitation, λmax (EM) = 430,443,470.
nm. In addition, atmospheric photoelectron spectroscopy (AC-
1: RIKEN KEIKI), and the ionization potential of the powder was 5.86 eV (500 nW). From the above results, it was confirmed that the obtained purified powder was the intended styryl compound (1). This styryl compound (1), 4,4 ′ ″-bis (2,2-diphenylvinyl) quarterphenyl (hereinafter, abbreviated as DPVQP) had a melting point of 292 ° C. The glass transition temperature was 104 ° C.

Production Examples 2 to 9 Compounds 2 to 9 were synthesized in the same manner as in Production Example 1 except that the raw materials shown in Table 1 were used. The measured physical property values are
It is shown in the table.

[0096]

[Table 1]

[0097]

[Table 2]

[0098]

[Table 3]

Production Example 10 (Compound (27), DPVD
Synthesis of PDMBi)

Embedded image

Diphenylbromomethane 200 g (0.8 m
ol) and 146 g (1 mol) of triethyl phosphite in 1
The mixture was heated and stirred at 20 to 130 degrees for 8 hours. Cool after the reaction,
Perform decantation with 500 ml of n-hexane,
The solvent was distilled off to obtain 284 g (quantitative) of a yellow liquid. Next, 284 g of the above phosphonic acid ester and 182 g (0.9 mol) of p-bromobenzaldehyde were dissolved in 1 liter of DMSO, and 113 g of potassium-t-butoxide was added in several portions at room temperature. Then, after stirring at room temperature for 8 hours, 3.
The reaction product was put into 5 liters of water, and extracted three times with 1 liter of chloroform. This was further purified by a silica gel column to give 206 g of a white powder (62% yield).
I got

[0101]

Embedded image

50 g of the starting diamine compound (0.23 mol
l) was suspended in 320 ml of 48% HBr water, 960 ml of water, and 560 ml of acetic acid, and cooled to 5 ° C or lower. Na after cooling
The NO ₂ 35 g / water 430ml was added dropwise in 20 minutes at 5 ° C. or less, and stirred at the same temperature for 1 hour. Thereafter, an aqueous solution of a diazonium salt was poured into the aqueous solution of CuBr and reacted at 60 ° C. for 3 hours. After the reaction, the mixture was cooled, extracted three times with 1 liter of ethyl acetate, washed with water and dried over MgSO ₄ . Further purification by silica gel column yielded 32 g of white powder (yield%).
I got

[0103]

Embedded image

68 g of the bromo compound synthesized in the above (1) (0.
2 mol) was dissolved in 600 ml of dehydrated THF (manufactured by Kanto Kagaku), and this was added to Mg 7.2 g / 80 ml THF at 50 ° C.
It was added dropwise at ６０60 ° C. After the addition is completed, the reaction product is
The mixture was refluxed for hours to prepare a Grignard reagent. Next, 23 g (0.07 mol) of the dibromo compound synthesized in (2) and 1,3-bis (diphenylphosphino) propane nickel (II) chloride [Ni
(Dppp) Cl ₂ ] 2.0 g (3.7 × 10 ⁻³ mol) and 230 ml of dehydrated THF were added. The above Grignard reagent was added dropwise over 1 hour while maintaining the internal temperature at 50 to 60 ° C. in an Ar gas atmosphere. After the completion of the dropwise addition, the reaction product was reflux-stirred for 8 h, allowed to cool, and then poured into 500 ml of a 3N HCl aqueous solution. The resulting precipitate was washed with water and dried, and then purified using a silica gel column with a developing solvent of methylene chloride. A white powder 21.6 (46% yield) was obtained. This was further purified by sublimation to obtain 18 g of a purified sublimation product. This compound had a melting point of 241 ° C. and a glass transition temperature (Tg) of 74 ° C.

Production Examples 11 to 14 Compounds 11 to 14 were synthesized in the same manner as in Production Example 10 except that the starting materials shown in Table 2 were used. Table 2 shows the measured physical property values.

[0106]

[Table 4]

[0107]

[Table 5]

[0108]

[Table 6]

Example 1 An ITO (indium tin oxide) electrode having a thickness of 100 nm was formed on a glass substrate having a size of 25 mm × 75 mm × 1.1 mm.
The transparent indicator substrate was formed to have a thickness of 3 mm. This was ultrasonically washed with isopropyl alcohol for 5 minutes, then with pure water for 5 minutes, and finally again with isopropyl alcohol for 5 minutes. Next, this transparent indicating substrate was fixed to a substrate holder of a commercially available vacuum vapor deposition device (manufactured by Nippon Vacuum Technology Co., Ltd.), and the compound 4,4′-bis (N, 500 mg of N-di- (3-tolyl) amino) -4 ″ -phenyl-triphenylamine (TAPPTPA), N, N′-diphenyl-N, N′-bis (1-naphthyl)-[1,1 '-Biphenyl] -4,4'-diamine (NPD) 200 mg,
200 mg of DPVQP obtained in Production Example 1, 4,4 ′
-Bis [2- {4- (N, N-diphenylamino) phenyl} vinyl] biphenyl (DPAVBi) 200 mg
And 100 mg of tris (8-hydroxyquinoline) aluminum (Alq).

After the pressure in the vacuum chamber was reduced to 1 × 10 ⁻⁴ Pa, first, a boat containing TAPTAPA was heated to deposit TAPPTPA on the substrate, and a hole injection layer having a thickness of 60 nm was formed. Next, the boat containing the NPD was heated to evaporate the NPO to form a hole transport layer having a film pressure of 40 nm. Next, the boat with DPVQP and DPAV
The boat containing Bi was heated and evaporated at the same time, and 40 nm was deposited as a mixed light emitting layer on the hole transporting layer [mixing ratio was DPVBi: DPAVBi = 40: 1 (weight ratio)].
Finally, the Alq-containing boat was heated to make Alq have a volume on the light emitting layer, and a 20-nm-thick electron injection layer was formed.

Next, this was taken out of the vacuum layer, and
A stainless steel mask is placed on the child injection layer
Then, it was fixed to the substrate holder again. Tungsten bath
Insert 0.5g of silver wire into the ket and add another molybdenum
After putting 1g of magnesium ribbon in the plate, in the vacuum chamber
Is 1 × 1010^-FourReduce the pressure to Pa and reduce magnesium to 1.
A deposition rate of 8 nm / sec and silver at 0.1 nm / sec.
Simultaneous deposition at the deposition rate, and a magnesium: silver mixed electrode
Produced. An ITO electrode was placed on the obtained device with an anode and a magnet.
The cathode of the mixed electrode of silver and silver is applied with a voltage of 8 V,
When the luminescence test was performed, a uniform blue luminescence was obtained.
Was. The initial performance was 1.9 mA / current density at an applied voltage of 8.9 V.
cm^Two, Brightness 94.4 cd / m ^Two, Luminous efficiency 1.71 lumens
/ W. This element has an initial luminance of 100 cd / m.^Two
When driven at a constant current in a nitrogen stream, the brightness becomes 50
cd / m^TwoWas 1000 hours. This
The element is provided with a glass housing, in which it is inert
It was sealed by adding liquid. Constant temperature of sealed element
Store in a constant humidity tester at 70 ° C, 90%
Was. It was taken out for an arbitrary time, and the chromaticity was measured with a luminance meter.
As a result, this element does not change color for 500 hours or more.
It was stable. In this way, the light emission characteristics are good and the heat resistance
Thus, an organic EL device excellent in the above was provided.

Examples 2 to 14 In the same manner as in Example 1, except that the luminescent material compounds described in Table 3 obtained in Production Examples 2 to 14 were used instead of DPVQP obtained in Production Example 1, An element having the same configuration as in Example 1 was produced, and the performance of the element was measured in the same manner. The results are shown in Table 3. In addition, the sealing method and heat resistance test conditions (70
(C, 90%) are shown in Table 3 below. However, the measurement was performed up to 500 hours.

[0113]

[Table 7]

[0114]

[Table 8]

Comparative Example 1 In Example 1, the following formula was used instead of DPVQP obtained in Production Example 1.

Embedded image A device having the same configuration as in Example 1 was produced except that DPVBi represented by the following formula was used as the light emitting material compound, and the performance of the device was measured in the same manner. The results are shown in Table 3. Table 3 shows the storage life until the color change starts when the sealing method and the heat resistance test conditions (70 ° C., 90%) are also the same. However, the measurement was performed up to 500 hours.

As is clear from Comparative Example 1, the DPV
Even with Bi, the emission characteristics are good to some extent, but 70 ° C, 9
When stored at 0% humidity for 100 hours, the color changed.
On the other hand, in Examples 1 to 14, the luminous efficiency was 1.0.
When stored at 70 ° C. and 90% humidity, the color changed after 260 to 500 hours. These results indicate that the light-emitting material DPVBi used in Comparative Example 1 had a glass transition temperature (Tg) of 6
While the temperature is as low as 3.6 ° C., the luminescent materials of Production Examples 1 to 14 are:
It is considered that, since the glass transition temperature is as high as 74 ° C. to 112 ° C., the time until the color change in the examples when stored at 70 ° C. and 90% humidity is also prolonged.

[0117]

As described above, the organic EL device containing the distyrylarylene derivative used in the present invention is superior in the EL light emission characteristics and the heat stability as compared with the conventional device containing a styryl compound or the like. It is a long-life element with excellent performance. Therefore, the EL device of the present invention can be effectively used in various industrial fields.

────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-7-26254 (JP, A) JP-A-4-332787 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C09K 11/06 CA (STN) REGISTRY (STN)

Claims (6)

(57) [Claims] 1. A compound of the general formula (I) [Wherein, l, m and n are each 0 or 1, and (l + m + n) ≧ 1; (1) When l = 1 and m = n = 0, R ^{1 to} R ¹² are each independently Hydrogen atom or carbon number 1
Alkyl group having 6 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, aryloxy group having 6 to 18 carbon atoms, aryl group having 6 to 20 carbon atoms, amino group, alkylamino group, arylamino group, cyano group, nitro group , Hydroxyl group, halogen atom or Is shown. However, at least ^one of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹¹ and R ¹² ,
It bonds to each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, a ring may be formed via a hetero atom. Further, all of R ^{1 to} R ¹² are hydrogen atoms and carbon atoms.
Except when it is a group selected from alkyl groups having a prime number of 1 to 6.
Good. (2) When l = m = 1, n = 0 R ^{1 to} R ¹² are the same as above, and R ³ ′, R ⁴ ′,
R ⁹ ′ and R ¹⁰ ′ are each independently a hydrogen atom or carbon atom 1
Alkyl group having 6 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, aryloxy group having 6 to 18 carbon atoms, aryl group having 6 to 20 carbon atoms, amino group, alkylamino group, arylamino group, cyano group, nitro group , Hydroxyl group, halogen atom or Is shown. However, R ¹ and R ^2, R ³ and R ^4, R ³ 'and R ^4', R ⁵
And R ⁶ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ⁹ ′ and R ¹⁰ ′, R ¹¹ and R
¹² may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, a ring may be formed via a hetero atom. Also, R ² and R ^3, R ⁴ and ^{R 3 ', R 4' R} 5 and, R ⁸ and R ^9, R ¹⁰ and R ⁹ ', R ^10' and R ¹¹
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
It may form a member ring. In that case, a ring may be formed via a hetero atom. (3) When l = m = n = 1 R ^{1 to} R ¹² , R ³ ′, R ⁴ ′, R ⁹ ′, R ¹⁰ ′ are the same as above, and R ³ ″, R ⁴ ″, R ⁹ ", R ^10" are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, atoms 1
To 6 alkoxy groups, 6 to 18 carbon atoms, aryloxy groups, 6 to 20 carbon atoms, amino groups, alkylamino groups, arylamino groups, cyano groups, nitro groups, hydroxyl groups, halogen atoms or ] Is shown. However, R ¹ and R ^2, R ³ and R ^4, R ³ 'and R ^4', R ³ "
And R ⁴ ", R ⁵ and R ^6, R ⁷ and R ^8, R ⁹ and R ^10, R ⁹ 'and R ^10', R ^9" and R ¹⁰ ", R ¹¹ and R ¹² are bonded to each other saturated Alternatively, it may form an unsaturated 5- or 6-membered ring, in which case a ring may be formed via a heteroatom, and R ² and R ³ , R ⁴ and R ³ ′, R ⁴ 'and R ³ ", R ^4" and R ^5, R ⁸ and R ^9, R ¹⁰ and R ^9', R ¹⁰ 'and R ⁹ ", R ^10" and R
¹¹ may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. In that case, a ring may be formed via a hetero atom. X and Y each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. The substituents of X and Y may combine with each other to form a substituted or unsubstituted saturated or unsaturated 5- or 6-membered ring. Here, the substituent means an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an amino group, an alkylamino group, It represents an arylamino group, a cyano group, a nitro group, a hydroxyl group or a halogen atom. These substituents may be single or plurally substituted. An organic electroluminescent device containing a distyrylarylene derivative represented by the following formula: 2. An organic electroluminescence device comprising the distyryl arylene derivative according to claim 1 sandwiched between a pair of electrodes. 3. An organic electroluminescence device using the distyryl arylene derivative according to claim 1 as a constituent material of a light emitting layer. 4. An organic electroluminescence device using a compound of l = 1 and m = n = 0 among the distyryl arylene derivatives according to claim 1 as a constituent material of a light emitting layer. 5. An organic electroluminescent device using a compound of l = m = 1, n = 0 among the distyryl arylene derivatives according to claim 1 as a constituent material of a light emitting layer. 6. An organic electroluminescent device using a compound of l = m = n = 1 among the distyryl arylene derivatives according to claim 1 as a constituent material of a light emitting layer.