JPH03231970A - Aromatic dimethylidene compound and production thereof - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [R<1> to R<4> are each 1-6C alkyl, 7-8C aralkyl, (substituted) 6-18C aryl, (substituted) aromatic heterocycle, etc.; Ar is (substituted) 6-20C aryl; in case Ar is non-substituted phenylene, R<1> to R<4> are each 1-6C alkoxyl, 7-8C aralkyl, (substituted) naphthyl, etc.]. EXAMPLE:A compound of formula II. USE:A luminescent material for electroluminescence (EL) elements. Capable of giving high-luminance EL luminescence >=1000cd/m<2> in luminance in the case of blue violet to green (esp. blue). PREPARATION:An arylene group-contg. phosphorus compound of formula III (R is 1-4C alkyl or phenyl) is condensed with a ketone of formula IV (R<5> and R<6> are each of equal definition to R<1> to R<4>, except for alkyl, aralkyl, alkoxyl and aryloxy).

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an aromatic dimethylidine compound and a method for producing the same.
This invention relates to a ♀J% aromatic dimethylidine compound useful as a light-emitting material, etc., and an efficient method for producing the same.

[Prior Art and Problems to be Solved by the Invention] Research on high fluorescence efficiency of organic compounds [4L] Research on elements utilizing the EL performance of organic compounds has been conducted for a long time. For example, W, He1frish, DrcsmerlVi
lliams et al. used anthracene crystals to emit blue light? ! 1 (J. Chem. Ptvys, 44.
2902 (1966)).

In addition, Vineett, Barlow et al. are fabricating light emitting devices using a vacuum evaporation method using fused polycyclic aromatic compounds (Thin 5 Solid Films, 99.
171 (1982)).

However, in both cases, only low luminance and low luminous efficiency were obtained.

Recently, it has been reported that blue light emission of 100 cd/nf was obtained using Te1-raphenylbutadiene as a luminescent material (Japanese Patent Laid-Open Publication No. 194393/1983).

Furthermore, by laminating a hole-conducting diamine compound and a fluorescent aluminum ramylate complex as a light-emitting material, we have created a green light-emitting organic thin film E with a luminance of 1000 cd/n or more.
It is reported that the L element was developed (Appl, ys, Lett, 51.913 (1987)).
.

In addition, distyrylbenzene compounds, which are famous as laser dyes, have high fluorescence in the blue to blue-green region, and it was possible to obtain an EL emission of about 80 cd/rrf using a single layer of this as a light-emitting material. It has been reported (European Patent 0319
88]).

However, at present, a high-luminance and highly efficient light-emitting material with a luminance of 1000 Cd/rrf or more has not yet been obtained for colors other than green (particularly in the blue family).

Further, regarding a photoconductor characterized by containing a distyryl compound, the compound disclosed in JP-A No. 63-269158 or herein has an unsubstituted phenyl group in its center, and It is clear that when an EL element is produced using a light emitting material, crystallization progresses and the thin film properties are poor.

Therefore, the present inventors have conducted extensive research in order to develop a compound that can provide EL light emission with a high luminance of 1000 cd/n or more in the range from bluish-violet to green (particularly blue).

[Failure to solve the problem]

As a result, it has been found that a novel aromatic dimethylidine compound having a specific substituent can meet the above objectives. The present invention was completed based on this knowledge.

That is, the present invention −・Sailor [In the formula, R1-R4 are alkyl groups having 1 to 6 carbon atoms.

an aralkyl group having 7 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted cyclohexyl group,
It represents a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms and an alkoxy group having 1 to 6 carbon atoms. Here, the substituent represents 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, a phenyl group, a 21·ro group, a hydroxyl group, or a halogen. These substituents may be multiple or multiple. Also R I, R
1 may be the same or different from each other, and R1 and R2, R2 and R4 are bonded to the substituted groups to form a substituted or unsubstituted saturated five-membered ring or a substituted or unsubstituted saturated six-membered ring. may be formed.

Ar represents a substituted or unsubstituted aryl group having 6 to 2 carbon atoms, and may be singly substituted or multiply substituted, and the bonding site may be either ortho-para or meta. Note that the substituents are the same as above. Further, substituents of the aryl group may be bonded to each other to form a substituted or unsubstituted saturated five-membered ring or a substituted or unsubstituted saturated six-membered ring. However, in the case of Ar or unsubstituted phenylene, R'
-R' is an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted piphenyl group, a substituted or unsubstituted cyclohexyl group, a substituted or It is selected from an unsubstituted pyridyl group and a substituted or unsubstituted aryloxy group. The present invention provides an aromatic dimethylidene compound represented by Further, the present invention is directed to a compound of the general formula [wherein R represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and Ar is the same as above. ] The arylene group-containing phosphorus compound represented by the general formula % formula % ( ) [wherein R5 and R6 are the same as R1 to R4 above, respectively. However, alkyl groups, aralkyl groups, alkoxy groups, and aryloxy groups are excluded. [In the formula, Ar is the same as above. R5 and Rg are the same as R1 to R4 above. However, an alkyl group,
Excludes cases where it is an aralkyl group, an alkoxy group, or an aryloxy group. ] Method for producing an aromatic dimethylidine compound represented by (
(hereinafter referred to as "method"), and further provides a general formula [wherein R7 and Rs are the same as R1 to R4, respectively. ] A phosphorus compound represented by the general formula [wherein, Ar is the same as above]. [In the formula, Ar is the same as above. R7 and Rm are the same as R1 to R4, respectively. ] (hereinafter referred to as method B). Furthermore, the present invention provides a compound of the general formula [wherein R1 and R2, Ar, and R are the same as above.

] An arylene group-containing phosphorus compound represented by the general formula [wherein R3 and R4 are the same as above]. ] By condensing with a ketone represented by the above general formula (I)
The present invention provides a method for producing an aromatic dimethylidine compound represented by (hereinafter referred to as method C).

Here, R' to R4 in general formula (I) may be the same or different as described above, and each is an alkyl group having 1 to 6 carbon atoms (methyl group, ethyl group, n-propyl group, i-propyl group). group, n-butyl group, i-butyl group, 5eC-butyl group, tert-butyl group, isopentyl group, t-pentyl group, neopentyl group.

isohexyl group), aralkyl group having 7 to 8 carbon atoms (benzyl group, phenethyl group, etc.), phenyl group.

Alkoxy group, cyclohexyl group 2 biphenyl group.

Indicates a naphthyl group or a heterocyclic group (pyridyl group, carbazolyl group, quinolyl group, etc.). Further, R1 to R4 may have a substituent bonded thereto.

That is, R1 to R4 each represent a substituent-containing phenyl group, a substituent-containing aralkyl group, a substituent-containing cyclohexyl group, a substituent-containing biphenyl group, a substituent-containing naphthyl group, or a substituent-containing heterocyclic group. Here, the substituent is an alkyl group, an alkoxy group or an aryloxy group,
They are phenyl groups, nitro groups, hydroxyl groups, and halogens, and may be multiply substituted. Therefore, the substituent-containing aralkyl group includes an aralkyl group substituted with an argyl group (methylbenzyl group, methylphenethyl group, etc.), an aralkyl group substituted with an alkoxy group (methoxybenzyl group, ethoxyphenethyl group, etc.), an aralkyl group substituted with an aryloxy group (phenoxybenzyl group, etc.). The above substituent-containing phenyl groups include alkyl-substituted phenyl groups (tolyl, dimethylphenyl, ethylphenyl, etc.), alkoxy-substituted aralkyl groups (phenylphenethyl, etc.) Phenyl group (methoxyphenyl group, ethoxyphenyl group, etc.) Aryloxy group-substituted phenyl group (phenoxyphenyl group.

naphthyloxyphenyl group, etc.) or phenyl group-substituted phenyl group (that is, biphenylyl group). Also,
Substituent-containing cyclohexyl groups include alkyl group-substituted cyclohexyl groups (methylcyclohexyl group, dimethylcyclohexyl group, ethylcyclohexyl group, etc.), alkoxy group-substituted cyclohexyl groups (methoxycyclohexyl group,
ethoxycyclohexyl group, etc.), an aryloxy group-substituted cyclohexyl group (phenoxycyclohexyl group, naphthyloxycyclohexyl group), and a phenyl group-substituted cyclohexyl group (phenylcyclohexyl group). Substituent-containing naphthyl groups include alkyl group-substituted naphthyl groups (methylnaphthyl group, dimethylnaphthyl group, etc.), alkoxy group-substituted naphthyl groups (methoxynaphthyl group, ethoxynaphthyl group, etc.), or aryloxy group-substituted naphthyl groups (phenoxynaphthyl group, naphthyloxynaphthyl group), phenyl group-substituted naphthyl group. Furthermore, as examples of substituent-containing heterocyclic groups, for example, substituent-containing pyridyl groups include alkyl group-substituted pyridyl groups (methylpyridyl groups,
(dimethylpyridyl group, ethylpyridyl group, etc.), an alkoxy group-substituted pyridyl group (methoxypyridyl group, ethyloxypyridyl group, etc.), or an aryloxy group-substituted pyridyl group (phenoxypyridyl group, naphthyloxypyridyl group).

It is a phenyl group-substituted pyridyl group.

Among the above-mentioned groups, R1 to R4 are preferably an alkyl group having 1 to 6 carbon atoms, an aryloxy group, a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, or a cyclohexyl group. These may be substituted or unsubstituted.

On the other hand, Ar in -Funenin (I) is a substituted or unsubstituted arylene group such as phenylene group, biphenylene group, p-tylphenylene, naphthylene group, anthracenediyl group, and whether it is singly substituted or multiple substituted may have been done. Furthermore, the bonding position of methylidine\C=CH-/ may be at any position such as ortho, meta, or rose.

However, when Ar is unsubstituted phenylene, R1-R4 are an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, or a substituted or unsubstituted naphthyl group.

biphenyl group, cyclohexyl group, pyridyl group.

It is selected from aryloxy groups. Substituents include alkyl groups (methyl group, ethyl group, n-propyl group, i-
Propyl group, n-butyl group, 1-butyl group, 5ee-
butyl group, t-butyl group, isopentyl group, t-pentyl group, neopentyl group, isohexyl group, etc.), alkoxy group (methoxy group).

Ethoxy group, propoxy group, i-propoxy group.

butyloxy group, i-butyloxy group, 5ee-butyloxy group, t-butyloxy group, isopentyloxy group, t-pentyloxy group), aryloxy group (phenoxy group, naphthyloxy group, etc.) phenyl group, hydroxyl group,
It is a nitro group or a halogen, and may be singly or multiply substituted.

The dimethylidene aromatic compound represented by the formula (I) has two methylidene\ (C=CH-) units in one molecule, and depending on the geometric isomerism of the methylidene/yne units, there are four combinations: , cis-cis, trans-cis, cis-trans and trans-trans; It can be anything. Particularly preferred are all trans-isomers.

The above-described novel aromatic dimethylidene compound of the present invention can be produced by various methods, but it can be efficiently produced by method A, B, or C of the present invention.

First, in the method of the present invention, by causing a condensation reaction between the arylene group-containing phosphorus compound represented by the above-mentioned general formula (I[) and the ketone represented by the general formula (I),
The desired aromatic dimethylidine compound of general formula (I') is produced. Here - Ar in Funenin (II) corresponds to Ar of the aromatic dimethylidine compound to be produced.

Further, R is an alkyl group having 1 to 4 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, a butyl group) and a phenyl group. This arylene group-containing phosphorus compound can be prepared by a known method, for example, the A rbsov reaction: that is, the general formula
2C-Ar-CH2X [In the formula, X represents a halogen atom, and Ar is the same as above. ] An aromatic bishalomethyl compound represented by
(RO)3P [In the formula, R is the same as above. ] It can be obtained by reacting a trialkylsulfite represented by:

Also, in the ketone of -Funenin (ITI), R4, R6
is R5R6 of the aromatic dimethylidene compound to be produced.
Selected according to Note that R5 and R6 are the same as R1 to R4 above (however, they are alkyl groups).

(excluding aralkyl groups, alkoxy groups, and aryloxy groups).

This condensation reaction between the arylene group-containing phosphorus compound of -Funenin (n) and the ketone of general formula (III) can be allowed to proceed under various conditions. Hydrocarbons, alcohols, and ethers are suitable as reaction solvents used here.

Specifically, methanol: ethanol: isoprobanol; butanol; 2methoxyethanol: 1,2-dimethoxyethane: bis(2-methoxyethyl) ether:
Diogysan: Tetrahydrofuran, l-luene, xylene dimethyl sulfoxide, N,N-dimethylformamide: N-methylpyrrolidone, 1,3-dimethyl-2-
Examples include imidazolidinone.

Among them, tetrahydrofuran and dimethyl sulfoxide are preferred.

In addition, as a condensing agent, caustic soda, caustic potassium sodium amide, thorium hydride, n-butyl lithium, sulfur
-Alcolades such as lium methylate and potassium t-butoxide are used as required. Among them, n-butyllithium, potassium j, and -t-butoxide are preferred.

The reaction temperature varies depending on the type of reaction raw materials used and other conditions, and cannot be unambiguously determined, but it is usually about 0°
It can be selected from a wide range from C to about 100'C.

Particularly preferably, the temperature is in the range of 10°C to 70°C.

The aromatic dimethylidine compound of the present invention can be efficiently produced by the method A described above, but certain aromatic dimethylidine compounds can also be efficiently produced by the method B. I can do two things.

In this method B, the target general formula (I''
) to produce an aromatic dimethylidene compound. Here-
R in Shipman (IV) is an argyl group having 1 to 4 carbon atoms (e.g., methyl group, ethyl group, propyl group, butyl group) or a phenyl group, and R7 and R8 are aromatic groups to be produced. Corresponds to R7 and RR of the dimethylideine compound. Also, -
Ar in Shipman (V) corresponds to Ar in the aromatic dimethylidine compound to be produced.

This condensation reaction between the phosphorus compound of Shipin (IV) and the dialdehyde of general formula (V) can proceed under various conditions. The first reaction solvent and condensing agent preferably used here are the same as those used in the above method. In addition, the reaction temperature varies depending on the type of reaction raw materials used and other conditions.
It is possible to select from a wide range of temperature ranges, usually from about 0°C to about 100'C. Particularly preferred is 0°C to 70°C.

The aromatic dimedyridine compound of the present invention can be prepared by the method A described above.
and ■ It can be manufactured more efficiently. Also,
Furthermore, it can also be produced by method C.

, 2-h Method C is to produce the desired aroma of general formula (I) by causing a condensation reaction between a phosphorus compound represented by -Funenin (VI) and a ketone represented by Funato (■). A group dimethylidine compound is produced.

Here, R in Funato (■) is an argyl group having 1 to 4 carbon atoms (e.g., methyl group, ethyl group, propyl group, butyl group) or phenyl group, and R1 and R2 are aromatic groups to be produced. It is selected corresponding to R1°R2 of the dimethylidine compound. Here, as a method for producing -Shipin (VI), a phosphorus compound represented by -Shipin (R', R2, R are the same as above) is prepared using the general formula % formula % [In the formula, Ar is the same as above. ] An aromatic methylidine compound which is removed by the general formula % formula % [wherein R', R2, and Ar are the same as above] by condensing an aldehyde represented by This can be obtained by a known method, for example, a halogenation reaction using N-haloamide, especially N-chloro and N-bromo-succinic acid amide, to obtain a compound of the general formula % [wherein X represents a halogen atom, Ar, R' and R2 are as defined above.] An aromatic halomethyl compound represented by the following formula is obtained.

This halomethyl compound has the general formula (RO) a P [wherein R is the same as above]. ] It can be obtained by reacting l.realgyl phosphite expressed as follows.

The above is the method for producing general formula (VI), but also, in the ketone of -Funenin (■), R' and R' correspond to R3R4 of the aromatic dimethylidine compound (I) to be produced. ,
Selected.

This condensation reaction between the phosphorus compound of Shipin (VI) and the ketone of general formula (■) can proceed under various conditions. Here, the reaction solvent and condensing agent suitably used are the same as those used in the above method. In addition, the reaction temperature varies depending on the type of reaction raw materials used and other conditions, and cannot be unambiguously determined, but it is usually about 0°C to about 10°C.
It is possible to select from a wide range up to 0°C. Particularly preferably, the temperature is in the range of 0°C to 70°C.

Specific examples of the compound represented by the general formula (I) include the following.

= 27 - 2 1 ■ 32 r 6 9 The aromatic dimethylidine compound of the present invention thus obtained can be effectively used as an EL element capable of emitting high-intensity light at low voltage.

This aromatic dimethylidine compound of the present invention has an EL element-
It has the essential electron injection function, electron transport function and light emitting function as a light emitting layer of R, and has excellent heat resistant thin film properties. Furthermore, this aromatic dimedyridine compound does not decompose or change in quality even when heated to the vapor deposition temperature, and has the advantage that it can form a dense film consisting of uniform microcrystalline grains and does not generate pinholes.

As already mentioned, the compound represented by the general formula (I) of the present invention is effective as a light emitting layer in an EL device. This light-emitting layer is formed by, for example, a vapor deposition method.

The compound of general formula (I) can be formed into a thin film by a known method such as a spin cord method or a casting method, or it is particularly preferable to form a molecular deposition film. Here, the term "molecularly deposited film" refers to a thin film formed by depositing the compound from the gas phase state, or a film formed by solidifying the compound from the solution state or liquid phase state, for example, a vapor deposited film, etc. However, this molecular deposition film can usually be distinguished from a thin film (molecular accumulation film) formed by the LB method. Furthermore, as disclosed in Japanese Patent Application Laid-Open No. 59-194393, the light-emitting layer is prepared by dissolving a binder such as a resin and the compound in a solvent to form a solution, and then using a spin code method to form a solution. It can be formed into a thin film by et al.

The thin film of the light-emitting layer thus formed is not particularly limited and can be appropriately selected depending on the situation, but is usually selected in the range of 5 rim to 5 μm.

(1) When an electric field is applied, the light emitting layer in this EL element:
By injecting holes by an anode or a hole injection layer,
and an injection function that allows electrons to be injected from the cathode or electron injection layer, (2) a transport function that moves the injected charges (electrons and holes) by the force of an electric field, and (3) a function that allows recombination of electrons and holes. It has a light-emitting function that provides a field inside the light-emitting layer and connects this to light emission.

Note that there may be differences in the ease with which holes are injected and the ease with which electrons are injected, and there may be differences in the transport capacity expressed by the mobility of holes and electrons, but it is possible to Preferably, the charge is transferred.

The compound represented by Funato (I) used in this light-emitting layer generally has an ionization energy of 6. Since it is smaller than about OeV, if an appropriate anode metal or anode compound is selected,
It is relatively easy to inject holes.

Furthermore, since the electron affinity is greater than about 2.8 eV, if an appropriate cathode metal or cathode compound is selected, it is relatively easy to inject electrons and has excellent electron and hole transport ability. Furthermore, since it has strong fluorescence in the solid state, it has a great ability to convert into light the excited state formed during recrystallization of electrons and holes in the compound, its aggregates, or crystals.

The structure of the EL device using the compound of the present invention has various embodiments, but basically it has a structure in which the light-emitting layer is sandwiched between a pair of electrodes (anode and cathode), and if necessary, In this case, a hole injection layer or an electron injection layer may be interposed. Specifically, (1) anode/emissive layer/cathode, (2) anode/hole injection layer/emissive layer/cathode, (3) anode/hole injection layer/emissive layer/
Examples include configurations such as an electron injection layer/cathode. Although the hole injection layer and electron injection layer are not necessarily required,
The presence of these layers further improves luminescent performance.

Further, in the above-mentioned elements, it is preferable that all the elements be supported by a substrate, and the substrate is not particularly limited, and may be a substrate conventionally used for EL elements, such as glass or transparent plastic.

A material made of quartz can be used.

As the anode in this EL element, an electrode material containing a metal 1 alloy having a large work function (4 eV or more), an electrically conductive compound, or a mixture thereof is preferably used. Specific examples of such electrode materials include metals such as Au, CuL r"ro.

5n02. Examples include dielectric transparent materials such as ZnO.

The anode can be manufactured by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When emitting light from this electrode, it is desirable that the transmittance be greater than 10%, and the resistance of the electrode is several hundred Ω10]
m or less is preferable.

Furthermore, the film thickness depends on the material, but is usually 10 nm to 1 μ.
m, preferably selected in the range of 10 to 200 nm.

On the other hand, as a cathode, it has a small work function (4 eV or less).
Electrode materials containing metal 1 alloys, electrically conductive compounds, and mixtures thereof are used. A specific example of such an electrode material is sodium.

Sodium-potassium alloy, magnesium, lithium,
Magnesium/copper mixture, Aff/A, j? Examples include O7° indium. The cathode can be manufactured by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. In addition, the sheet resistance of the electrode is preferably several hundred Ω/mm or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 1 μm.
It is selected within a range of 200 nm. In addition, in this EL element, it is advantageous that either the anode or the cathode is transparent or semi-transparent so that the emitted light can be extracted with good efficiency since the emitted light is transmitted through the anode or the cathode.

As described above, there are various configurations of the EL device using the compound of the present invention, and the hole injection layer (hole injection transport layer) in the EL device having the configuration (2) or (3) is:
This layer is made of a hole transport compound and has the function of transmitting holes injected from the anode to the light emitting layer. By interposing this hole injection layer between the anode and the light emitting layer, Many holes are injected into the emissive layer by the electric field, and electrons injected into the emissive layer from the cathode or electron injection layer are suppressed by the electron barrier existing at the interface between the emissive layer and the hole injection layer. The element accumulates near the interface within the layer and improves luminous efficiency, resulting in an element with excellent luminous performance.

When the hole transfer compound used in the hole injection layer is placed between two electrodes to which an electric field is applied and holes are injected from the anode, the hole transfer compound can appropriately transfer the holes to the light emitting layer. Preferably, the compound has a hole mobility of at least 10 crd/V·sec when an electric field of, for example, 10 4 to 10′ V/cm is applied.

There are no particular limitations on such hole transport compounds as long as they have the above-mentioned preferable properties. Any material can be selected from among the known materials used for the injection layer.

Examples of the charge transporting material include triazole derivatives (described in U.S. Pat. No. 3,112,197) and oxadiazole derivatives (as described in U.S. Pat. No. 3,189).
447), imidazole derivatives (those described in Japanese Patent Publication No. 37-16096, etc.)
, polyarylalkane derivatives (U.S. Pat. No. 3,615
, No. 402 specification.

Specification No. 3,820.989, No. 3,542,544
Specification, Japanese Patent Publication No. 45-555, No. 511098
Publication No. 3, JP-A-51-93224, JP-A No. 55-1
Publication No. 7105, Publication No. 56-4148, Publication No. 55-5
No. 063 Publication No. 5F+-156953 Publication No. 56-
36656), pyrazoline derivatives and pyrazolone derivatives (U.S. Pat. No. 3,180,72)
Specification No. 9, Specification No. 4,278.746, Japanese Unexamined Patent Publication No. 1973
No. 5-88064, No. 5588065, No. 4
Publication No. 9-105537.

Publication No. 55-52063, Publication No. 56-80051,
Publication No. 56-88141, Publication No. 5745545,
Publication No. 51-112637.

55-74546, etc.), phenylenediamine derivatives (U.S. Pat.
12, 47-25336, JP-A-54-53435, and JP-A-54-110536.

51-119925), arylamine derivatives (U.S. Pat. No. 3,567,450, U.S. Pat. No. 3,180,703).

Specification No. 3,240.597, No. 3,658,520
Specification of No. 4,232.103.

7 Specification No. 4,175.961, No. 4,012,376
specification, Japanese Patent Publication No. 49-35702, No. 39-2
7577, JP 55-144250, JP 56-119132, JP 5622437,
(described in West German Patent No. 1.110.518 etc.), amino-substituted chalcone derivatives (US Pat. No. 3.52)
6.501, etc.), oxazole derivatives (described in U.S. Pat. No. 3,257,203, etc.), styryl anthracene derivatives (JP-A-5
6-46234, etc.), fluorenone derivatives (described in JP-A-54-110837, etc.), hydrazone derivatives (U.S. Pat. No. 3,717,
Specification No. 462, Japanese Unexamined Patent Publication No. 54-59143, No. 5
Publication No. 5-52063.

55-52063, 55-46760, 55-7546, 57-11350, 57-148749, etc.), stilbel derivatives (Japanese Patent Application Laid-open No. 1983 -210363 publication, 61-48-228451 publication, 61-14642 publication 61
-72255 publication, 61-47646 publication, 61-47646 publication
No. 2-36674, No. 6210652, No. 6
Publication No. 2-30255.

No. 60-93445, No. 60-94462, No. 60-174749, No. 60-175052
Examples include those described in the No. 1 gazette, etc.).

Although these compounds can be used as hole transport compounds, the following porphyrin compounds (Japanese Patent Application Laid-Open No. 1983-1999)
295695, etc.) and aromatic tertiary amine compounds and styrylamine compounds (U.S. Pat. No. 4.127.412, JP-A-53-27033)
No. 5458445, No. 54-14963
Publication No. 4.

No. 54-64299, No. 55-79450, No. 55-144250, No. 56119132, No. 63-29565, No. 61-98353
In particular, it is preferable to use the aromatic tertiary amine compounds described in Japanese Patent Application Publication No. 63-295695.

Representative examples of the porphyrin compounds include porphyrin;
23H-porphyrin copper (IF); 1°10, 1.5
．． 20-tetraphenyl-21N (23I~■-porphyrin zinc (IF); 5.10°15.20
-tetrakis(pentafluorophenyl)-21H,2
3I (-Porphyrin: Silicon phthalocyanine oxide: Aluminum phthalocyanine chloride: Phthalocyanine (metal-free) Nidilithium phthalocyanine; Copper tetramethyl phthalocyanine: Copper phthalocyanylomphthalocyanine; Zinc phthalocyanine: Lead phthalocyanine titanium phthalocyanine oxide; Magnesium phthalocyanine; Copper octamethyl phthalocyanine, etc. Representative examples of the aromatic tertiary compounds and styrylamine compounds include N.

N, N', N'-tetraphenyl-4,4'-diaminobiphenyl; N, N"-diphenyl-N, N' di(3-methylphenyl)-4,4-diaminobiphenyl, 2,2-bis (4-di-p-tolylaminophenyl)
Propane; 1. ! -bis(4-di p -1-lylaminophenyl)cyclohexane.

N, N, N', N'-tetra-p-1-liru 4
,4diaminobiphenyl,l,1-bis(4-zyl-1
~lylaminophenyl)-4-phenylcyclohexane: bis(4-dimethylamino-2-methylphenyl)phenylmethane: bis(4-di-ptolylaminophenyl)phenylmethane, N.

No-diphenyl-N, N'-di(4-methoxyphenyl)-4,4'-diaminobiphenyl; N,N.

N', N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)lyautotriphenyl, N,N,N-1-ly(p-tolyl)amine: 4-( p-tolylamine)-4'-(
4(di-p-tolylamine)styryl]stilbene, 4
-N,N-diphenylamino (2-diphenylvinyl)
Examples include benzene; 3-methoxy-4'-N, N-diphenylaminostilbene: 1-N-phenylcarbazole.

The hole injection layer in the above E L element may be composed of a single layer composed of one or more of these hole transport compounds, or may be composed of a hole injection layer composed of a compound different from the above layer. It may be a layered structure.

On the other hand, the electron injection layer (electron injection transport layer) in the EL element having the configuration (3) above is made of an electron transfer compound and has the function of transferring electrons injected from the cathode to the light emitting layer. There is. There are no particular limitations on such electron transfer compounds, and any one can be selected and used from conventionally known compounds. Preferred examples of the electron transfer compound include nitro-substituted fluorenone derivatives such as and thiopyrane dioxide derivatives such as.

Diphenylquinone derivatives such as
8), etc.], or compounds described in [Journal of Applied Physics (J, Apply, Phys.), Vol. 27, p. 269 (1988), etc.] ] and anl-laquinodimethane derivatives (Japanese Patent Application Laid-Open No. 57149259
Publication No. 58-55450, Publication No. 61-22515
No. 1, No. 61 233750, No. 6:3-104061, etc.), fluorenylidene methane derivatives (Japanese Patent Application Laid-open No. 60-69657, No. 61143764, No. 61-148159) (as stated in official bulletins, etc.),
Anthrone derivatives (JP-A No. 61-225151,
Examples include those described in Publication No. 61233750, etc.).

Next, an example of a suitable method for manufacturing an EL device using the compound of the present invention will be explained for each component of the device. To explain, first, a thin film of a desired electrode material, such as an anode material, is deposited on a suitable substrate to a thickness of 1 μm.
After forming an anode by a method such as vapor deposition or sputtering to a film thickness of η or less, preferably in the range of 10 to 200 nm, a luminescent material expressed by the general formula (1) is added to the anode. forming a thin film of a first compound;
A light emitting layer is provided. As a method for thinning the luminescent material,
For example, there are spin code methods, gearst methods, vapor deposition methods, etc., and the vapor deposition method is preferable because a homogeneous film is easily obtained and pinholes are less likely to be generated.

When this vapor deposition method is adopted for thinning the light emitting material, the vapor deposition conditions vary depending on the type of organic compound used in the light emitting layer, the crystal structure and association structure of the 9-molecule deposited film, etc. Boat heating temperature 50-400°C
4 Vacuum degree 1O-S-10-3Pa, deposition rate 0.01~
50 nm/sec, substrate temperature -50 to +300°C1
It is desirable that the film thickness be appropriately selected within the range of 5nrn to 5μm. Next, after forming this light emitting layer, a thin film made of a cathode material is deposited on it to a thickness of 1 μm or less, preferably 50 to 200 nm.
A desired EL element can be obtained by forming the film by a method such as vapor deposition or sputtering so as to have a film thickness in the range of m, and by providing a cathode. In the production of this EL element, it is also possible to reverse the production order and fabricate the cathode 4 light-emitting layer and the anode in this order.

Next, to explain the method for manufacturing an EL device consisting of an anode/hole injection layer/light emitting layer/cathode, first, the anode is
After forming the I7 element in the same manner as in the case of the I7 element, a thin film made of a hole transporting compound is formed on the substrate by vapor deposition or the like to provide a hole injection layer.

The vapor deposition conditions at this time may be based on the vapor deposition conditions for forming a thin film of the luminescent material. Next, a light-emitting layer and a cathode are sequentially provided on this hole injection layer in the same manner as in the production of the EL device, thereby obtaining a desired EL device.

In the production of this EL element, it is also possible to reverse the production order and fabricate the cathode 1 light-emitting layer, the hole injection layer, and the anode in this order.

Furthermore, a method for manufacturing an EL device consisting of an anode/hole injection layer/light emitting layer/electron injection layer/cathode will be explained. Layer 2 After the emissive layers are sequentially provided, a thin film made of an electron transfer compound is formed on the emissive layer by vapor deposition or the like, an electron injection layer is provided, and then, on this layer,
A desired EL element can be obtained by providing a cathode in the same manner as in the production of the EL element. Furthermore, this E
In the production of the L element, the production order may be reversed and the cathode, electron injection layer 1 light emitting layer, hole injection layer, and anode may be produced in this order.

When applying a DC voltage to the EL element obtained in this way, the anode is set to + and the cathode is set to - and the voltage is 5.
When approximately 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side. Furthermore, even if a voltage with the opposite polarity is applied, no current flows and no light is emitted at all. Furthermore, when an alternating current voltage is applied, light is emitted only when the anode is earth and the cathode is negative. Note that the waveform of the applied alternating current may be arbitrary.

Next, the light emitting mechanism of the EL element will be explained using an example of a structure of anode/hole injection/transport layer/light emitting layer/cathode. When a voltage is applied with the anode as the positive polarity and the cathode as the positive polarity, holes are injected from the anode into the hole injection layer by an electric field. The injected holes are transported within the hole injection transport layer toward the interface with the light-emitting layer, and are injected or transported from this interface to a region where a light-emitting function is expressed (for example, the light-emitting layer).

On the other hand, electrons are injected from the cathode into the light-emitting layer by an electric field, are further transported, and recombine with holes in the region where the holes exist, that is, the region where the light-emitting function is expressed (in this sense,
The above region may also be called a recombination region). When this recombination occurs, an excited state of molecules, aggregates thereof, crystals, etc. is formed, and this is converted into light. Note that the recombination region may be the interface between the hole injection transport layer and the light-emitting layer, the interface between the light-emitting layer and the cathode, or the central part of the light-emitting layer away from both interfaces. This varies depending on the type of compound used, its association and crystal structure.

〔Example〕

Next, the present invention will be explained in more detail based on examples and application examples.

Example 1 (1) Production of arylene group-containing phosphorus compound 25 g of 5-his(chloromethyl)xylene and 45 g of triethyl phosphite were heated at a temperature of 150° in an irbath under an argon stream.
The mixture was heated and stirred at C for 7 hours.

Thereafter, excess triethyl phosphite and by-produced ethyl chloride were distilled off under reduced pressure. - After standing overnight, 50 g (quantitative) of white crystals were obtained. The melting point of this product is 59.0-60.5°
There was C. Moreover, 'H-NMR analysis is as follows.

'H-NMR (CD(13) δ=6.9ppm (s + 2H, central xylene ring -
H) δ = 3.9 ppm (q; 8H, ethoxy group methylene-CH2) δ = 3.1 ppm (d; 4H, J = 20 Hz (“P
-6〇-H coupling)P-CH,) δ=2.2ppm (s; 6H, xylene ring-CH
,,) δ = 1.1 ppm (t; 12H, ethoxy group methyl-CH5) From the above results, it was confirmed that the above product is an arylene group-containing phosphorus compound (phosphonate) represented by the following formula. Ta.

(2) Production of aromatic dimethylidine compound 5.3 g of the phosphonate obtained in the above (1) and 5.2 g of 2-benzoylbiphenyl are dissolved in 100 ml of tetrahydrofuran, and n-butyllithium is contained in this (concentration 15%). 12.3 g of a hexane solution was added thereto, and the mixture was stirred at room temperature under an argon atmosphere for 6 hours, and then left in the apparatus overnight.

300 ml of methanol was added to the resulting mixture, and the precipitated crystals were filtered. The filtered product was then mixed with 100 ml of water.
The mixture was thoroughly washed three times with 100 ml of methanol and then three times with 100 ml of methanol to obtain 5.5 g of pale yellow powder (yield: 44%). The melting point of this product was 187-188°C. Further, 'H-NMR analysis of this powder is as follows.

'H-NMR (CDCA3) δ=7.7-7.0 ppm (m; 30 H,
aromatic ring) δ = 6.7 ppm (s; 2 H, methylidine 2CH=C-) δ = 2.0 ppm (s;
6 H, xylene ring -CH,) Furthermore, the elemental analysis results are as follows as a composition formula C4*H2*. Note that the values in parentheses are theoretical values.

C: 93.79% (93,82%) H: 6.06% (6,18%) N: 0. O0% (0%) Also, infrared (JR) absorption spectrum (KBr tablet method)
is as follows.

From the above results, it was confirmed that the above-mentioned product, a pale yellow powder, was a 2,5-quizylene dimethylidine derivative represented by the following formula.

Examples 2 to 7 In Example 1 (2), except that the ketone shown in Table 1 was used instead of 2-benzoyl biphenyl, Example 1 (
The same procedure as in 2) was carried out to obtain the 2.5 quizylene dimethylidine derivatives shown in Table 1.

(Margins below) Table 1 (Continued) Example 8 (Method B) (1) Production of phosphorus compound (1-bromoethyl) 25.1 g of benzene and 24.7 g of triethyl phosphite were placed in an irbath under an argon atmosphere.
The mixture was heated and stirred at a temperature of 150°C for 7 hours. Thereafter, excess triethyl phosphite and by-produced bromoethyl were distilled off under reduced pressure to obtain 22.3 g of a clear solution. This thing'
The H-NMR analysis results are as follows.

δ=7.2ppm (s; 5H, benzene ring-H
) δ = 3.9 ppm (q; 4 H, ethoxy group -0CR2-) δ = 2.9 to 3.5 ppm (m;
IH,=CH-)δ=], O~2.0ppm (
m; 9H, methyl of ethoxy and -C84) From the above, it was confirmed that the above product was a phosphorus-containing compound (phosphonate) represented by the following formula.

-66= (2) Production of aromatic dimethylidine compound 9.7 g of the phosphonate obtained in (1) above and 30 g of 2°5-xylene dicarboxaldehyde were added to 1 ml of tetrahydrofuran.
00ml, and to this was added n-butyllithium (concentration 1
3.0 g of a hexane solution containing 5%) was added thereto, and the mixture was stirred at room temperature under an argon atmosphere for 5 hours, and then left in the apparatus overnight.

100% of methanol was added to the resulting mixture, and the precipitated crystals were filtered. The filtered product was thoroughly washed three times with 100 ml of water and then three times with 100 ml of methanol to obtain 1.3 g of white flaky crystals (yield 20%).

The melting point of this product was 137.0-137.8°C. Further, 'H-NMR analysis of this crystal is as follows.

H-NMR (CDCβ3) δ = 7.2 to 7.5 ppm (m; 12H, benzene ring-H1 centered xylene ring-H) δ = 6.8 ppm (s + 28. Methyridine C
CH=C-)δ=2.3ppm (s + 6H, methyl group)7 δ=2. lppm (s; 6H, central xylene ring -C84) Furthermore, the elemental analysis results show that the composition formula is C26H2
g is as follows. Note that the values in parentheses are theoretical values.

C・92.26% (92,31%) H: 7.50% (7,69%) N: 0.00% (0%) Also, from the mass spectrum, the molecular ion peak of the target object m/Z= 318 was detected.

From the above, it was confirmed that the white scaly crystals that were the above product were 2,5-quizylene dimethylidine derivatives represented by the following formula.

Example 9 (1) Production of arylene group-containing phosphorus compound 4.9.0 g of 4-bis(bromomethyl)biphenyl and 1 g of triethyl phosphite were heated in an oil bath under an argon stream at a temperature of 14.
The mixture was heated and stirred at 0°C for 6 hours.

Thereafter, excess l.ethyl phosphite and by-produced ethyl bromide were distilled off under reduced pressure. -9.5g of white crystals after standing overnight
(yield 80%). The melting point of this thing is 97.0-1
It was 00.0°C. Moreover, the 'H-NMR analysis results are as follows.

'H-NMR (CDCI!3) δ = 7.0 to 7.6 ppm (m; 8 H, biphenylene ring-H) δ = 4.0 ppm (q: 8
8. Ethoxy group methylene=CH,)δ=3. lppm
(d: 48. J = 20 Hz ("P-'H
Coupling) P-CH2) δ=1.3ppm (t: 12H, ethoxy group methyl-CH5) From the above results, the above product is an arylene group-containing phosphorus compound (phosphonate) represented by the following formula. was confirmed.

(2) Production of aromatic dimethylidine compound 4.0 g of the phosphonate obtained in (1) above and 5.0 g of cyclohexylphenyl ketone were dissolved in 60 ml of dimethyl sulfoxide, and 2.0 g of potassium t-butoxide was added. The mixture was stirred under reflux under an argon atmosphere, and then kept in the apparatus overnight.

After distilling off the solvent of the resulting mixture, methanol 200
mj was added, and the precipitated crystals were filtered. The filtered product was then washed three times with 100 ml of water followed by 100 T of methanol.
After thorough washing with A1 three times and recrystallization with benzene, 1.0 g of pale yellow powder was obtained (yield: 22%). The melting point of this product was 153-155°C. Further, the 'H-NMR analysis results of this powder are as follows.

H-NMR (CD(1,) δ = 6.3 ~ 7° 5 ppm (b; 18 H, aromatic ring and methylidine) CH = C-) δ = 1.0 ~ 2.0 ppm (b; 22 H, cyclohexane ring) Further, the elemental analysis results are as follows as a composition formula C4oH42. Note that the values in parentheses are theoretical values.

C: 91.74% (91.90%) H. 8.2
5% (8,10%) N・ 0.00% (0%
) Also, infrared (IR) absorption spectrum (kBr tablet method)
is as follows.

vc-c 1520+ 1610cm Also,
From the mass spectrum, the molecular ion peak rn/
Z=522 was detected.

From the above, it was confirmed that the above-mentioned product, a pale yellow powder, was a 4,4'-biphenylene dimethylidine derivative represented by the following formula.

Example 1O Same as Example 9(2) except that 4,4゛-dimethylbenzophenone was used instead of cyclohexyl phenyl ketone and tetrahydrofuran was used instead of dimethyl sulfoxide. Operate and
A 4,4'-biphenylene dimethylidine derivative shown below was obtained.

to The results of this analysis are as follows.

Melting point = 228-230°C H-NMR (CDCj?2) δ = 6.7-7.3 ppm (m + 268. Aromatic ring -H and methylidine; CH=C-) δ = 2.4 ppm (s; 12H, p-tolylmethyl group CH3) Properties: Pale yellow powder Mass spectrum molecular ion peak: m/Z=566 Elemental analysis value 6 Composition 2 C44H38 as follows. Note that the values in parentheses are theoretical values.

C: 93.10% (93,24%) H near, 04% (6,76%) N: 0.00% (0%) Example 11 (1) Production of arylene group-containing phosphorus compound 2.6- 24.3 g of bis(bromomethyl)naphthalene and phosphorous acid I.
50 g of ethyl was heated and stirred at a temperature of 120° C. for 7 hours in an irbath under an argon stream.

Thereafter, excess l.ethyl phosphite and by-produced ethyl bromide were distilled off under reduced pressure. - Pale yellow crystals after standing overnight 32.
5 g (yield quantitative) was obtained. The melting point of this substance is 144.
The temperature was 5-146.0°C. Moreover, the H-NMR analysis results are as follows.

H-NMR (CDCffi3) δ = 7.2-7.8 ppm (rn + 68. Naphthylene ring-H) δ”4- Oppm (q; s
H, ethoxy group methylene CH2) δ = 3.3 ppm (d: 4H, J = 20Hz ("P
-'H coupling) P-C) (2) δ = 1.2 ppm (t: 12H, ethoxy group methyl CH3) From the results of -1- below, the above-mentioned product contains an arylene group represented by the following formula It was confirmed to be a phosphorus compound (phosphone-1.).

(2) Production of aromatic dimethylidine compound 5.0 g of phosphone-1 obtained in the above (1) and 5.0 g of cyclohexylphenyl ketone. Og, tetrahydrofuran 100ml
2.5 g of potassium 1-fluoride oxide was added thereto, and the mixture was stirred under reflux under an argon atmosphere, and then left in the apparatus overnight.

After distilling off the solvent of the resulting mixture, methanol 100
il was added, and the precipitated crystals were filtered. The filtered product was then thoroughly washed twice with 100 mj of water and then twice with methanol OOJ, and recrystallized from benzene to obtain 1.0 g of pale yellow powder (yield 20%). The melting point of this product was 215-216°C. Further, the results of 'H-NMR analysis of this powder are as follows.

'H-NMR (CDC1,) δ=6.2-7.2 ppm (m; I8H,
Aromatic ring and naphthalene ring -H and methyl 75~den>cI (=c->δ=1.0-2.0 ppm cb: 22 H,
cyclohexane ring) Further, the elemental analysis results are as follows with the composition formula C, , H4o. Note that the values in parentheses are theoretical values.

C: 91.63% (91,88%) H: 8.20% (8,12%) N: 0.00% (09a) From the above, the pale yellow powder that is the above product is as follows. It was confirmed that the compound is a 2,6-naphdylene dimethylideine derivative with the following formula:

Example 12 In Example 11 (2), 4,4'-dimethylbenzophenone was used instead of cyclohegysylphenyl ketone,
Example 11 except that n-butyllithium chloride was used instead of potassium t-butoxide. By operating in the same manner as in (2), the following 2,6 naphthylene dimethylidene derivative was obtained.

The results of this analysis are as follows.

Melting point: 269-271°C HNMR (CD CI! 3) δ = 6.7-7.2 ppm (m; 248. Aromatic ring -
H and methylidine'CCH=C δ=2.4ppm (s; 12H, p-tolylmethyl group CH3) Properties: Yellow powder elemental analysis values of two sets of Weiwu C42H3g are as follows. Note that the values in parentheses are theoretical values.

C: 93.03% (93,29%) H: 6.81% (6,71%) N: 0.00% (0%) Example 13 (1) Production of arylene group-containing phosphorus compound 9.10 - 10 g of his(chloromethyl)anthracene and 35 g of triethyl arsenite were added in an oil bath under an argon stream at a temperature of 1.
The mixture was heated and stirred at 30°C for 6 hours.

Thereafter, excess l.ethyl phosphite and by-produced ethyl chloride were distilled off under reduced pressure. - After standing overnight, the obtained pale green crystals were recrystallized from benzene-hexane to obtain 16 g of pale yellow flakes (yield 92%).

The results of this analysis are as follows.

Melting point: 160-161.5°C 'H-NMR (CDC13) δ=7.3-8.4 ppm (m; 8H, acetracene ring-H) δ=4. lppm (d: 4H, J=20Hz(”
P-'H coupling) P-CH2) δ=3.7 ppm (q + 8 H, ethoxy group methylene C) (2) δ=1. Oppm (t; 12H, ethoxy group methyl CH3) From the above results, it was confirmed that the above-mentioned product was an arylene group-containing phosphorus compound (phospone) represented by the following formula.

(2) Production of aromatic dimethylidine compound - (1) above
3.0 g of phosphone-1 and 2.5 g of 4.4'dimethylben'siphenone obtained in
00ml, and to this was added n-butyllithium (concentration 1
5%) of hexane solution was added thereto, and the mixture was stirred at room temperature under an argon atmosphere for 4 hours, and then left in the apparatus overnight.

Add 100 mt of methanol to the resulting mixture! was added, and the precipitated crystals were filtered. The filtered product was washed three times with 100 ml of water, then three portions with 100 ml of methanol, and recrystallized from toluene to obtain 0.7 g of a yellow-orange powder (yield: 19%).

The results of this analysis are as follows.

Melting point: 297-298°C 'H-NMR (CD(1,) δ = 6.5-7.5 ppm (m; 268. Aromatic ring-[■acetracene-11 and methylidei: z>CH=C-) δ ”'2-21111m (d: 12H, p -)
Lylemethyl group CH3) Elemental analysis value: Composition formula 〇 a 68311, as follows. Note that the values in parentheses are theoretical values.

C: 93.42% (93,52%) H: 6.53% (6,48%) N: 0.00% (0%) Also, from the mass spectrum, the molecular ion peak m of the target object
/Z=590 was detected.

From the above, it was confirmed that the above-mentioned product, a yellow-orange powder, was a 9°■ acetracenediyldimethylideine derivative represented by the following formula.

Examples 14 to 26 The compounds shown in Table 2 were synthesized using the corresponding compounds and phosphonic acid esters.

(Margins below) -85- -87- -89= Application example 1 ITO was formed into a film with a thickness of 1100 nm by vapor deposition on a 25 mm x 75 mm x 1.1 mm glass substrate (
(manufactured by HOY A) was used as a transparent support substrate.

This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Co., Ltd.), 200 μm of TPDA was placed in a resistance heating boat made of molybdenum, and the TPDA obtained in Example 1 was placed in another boat made of molybdenum. 2,5-His(2-phenyl-2-
200 μm of biphenylvinyl)xylene (BPVX) was added, and the pressure in the vacuum chamber was reduced to I×10′-′Pa.

After that, the boat containing TPDA was heated at 215-220°.
TPDA at a deposition rate of 0.1 to 0.3 nm.
/second to form a hole injection layer with a thickness of 60 nm. The substrate temperature at this time was room temperature.

Next, without taking it out of the vacuum chamber, a 80 nm layer of BPVX was deposited as a light-emitting layer on the hole injection layer from another boat. The deposition conditions were a boat temperature of 184°C, a deposition rate of 0.2 to 0.4 nm/sec, and a substrate temperature of room temperature.

This was taken out from the vacuum chamber, a stainless steel mask was placed north of the light emitting layer, and it was again fixed to the substrate holder.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat 1 made of molybdenum, and 500 μm of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2X10-'Pa, and then indium was deposited at a deposition rate of 0.03 to 0.08 nm/sec, and magnesium was simultaneously deposited from the other boat at a rate of 1.7 to 0.7 nm/sec.
Deposition was started at a deposition rate of 2.8 nm/sec. The temperature of the boats was approximately 800'C and 500'C for the boats containing indium and magnesium, respectively. Under the above conditions, a mixed metal electrode of magnesium and indium was deposited to a thickness of 150 nm on the light emitting layer to form a counter electrode, thereby forming a device.

A DC voltage of 20 V was applied to the obtained device using the rTOt electrode as an anode and the mixed metal electrode of magnesium and indium as a cathode.
Is there a current when I apply it? The current was about 70 mA/d, and Bluish Green luminescence was obtained in chromaticity coordinates.

The peak wavelength is 499 nm from spectroscopic measurement, and the luminance is 1000 cd/rr? That was it.

Application example 2 25 mm x 75 mm x 1. A transparent supporting substrate was prepared by forming a film of ITO to a thickness of 1100 nm on a glass substrate of Im by vapor deposition (manufactured by HOYA).

This transparent support substrate was subjected to UV ozone cleaning for 2 minutes using a UV ozone treatment device (manufactured by Nippon Battery Co., Ltd.).

Next, the TP was fixed to the substrate holder of a commercially available evaporation device (Japan Vacuum Technology Co., Ltd.) and placed on a resistance heating boat made of molybdenum.
In another molybdenum boat, 200 μl of DA was added, and 2,5-bis(2,2-di-p-)lylvinyl), the 2,5-quizylene dimethylidine derivative obtained in Example 2, was placed in another molybdenum boat.
Put 200μ of xylene (DTVX) into the vacuum chamber.
The pressure was reduced to 10-'Pa.

After that, the boat containing TPDA was moved to 215-220°.
TPDA at a deposition rate of 0.1 to 0.3 nm.
/second on a transparent support substrate to form a hole injection layer having a film size of 92 and a thickness of 60 nm. The substrate temperature at this time was room temperature.

Next, without taking it out of the vacuum chamber, DTVX was deposited as a light-emitting layer in a layer of 80 nm on the hole injection layer from another boat. The vapor deposition conditions are a boat temperature of 2
At 15°C, the deposition rate was 0.2-0.4 nm/sec, and the substrate temperature was room temperature.

This was taken out from the vacuum chamber, a stainless steel mask was placed on top of the light emitting layer, and it was fixed to the substrate holder again.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat made of molybdenum, and 500 square meters of indium was placed in another resistance heating boat made of molybdenum.

Afterwards, while reducing the pressure in the vacuum chamber to 2 × 10-'Pa, indium was deposited at a rate of 0.03 to 0.08 nrn/sec, and at the same time, magnesium was deposited at 1 liter from the other boat.
．． Deposition was started at a deposition rate of 7-2.8 nm/sec. The temperature of the boats was approximately 800°C and 500°C for the boats containing indium and magnesium, respectively. Under the above conditions, a 150 nm-thick mixed metal electrode of magnesium and ink was deposited on the light emitting layer to form a counter electrode, thereby forming a device.

When a DC voltage of 5 V is applied to the obtained device using the ITO electrode as the anode and the mixed metal electrode of magnesium and indium as the cathode, a current of about 6.3 mA/ad flows, and the luminance is 300 cd/rr? , Greenish B in chromaticity coordinates
A blue luminescence was obtained. The peak wavelength is 486n from spectroscopic measurement.
It was m. The luminous efficiency at this time is 2.91! m/W. Furthermore, when DC 7V is applied, the luminance is 1000 cd.
/rr? I confirmed that the above is true.

Application example 3 ITO was formed into a film with a thickness of 1100 nm by vapor deposition on a glass substrate of 25 cm x 75 cm x 1.1 cm (HOY A).
) was used as a transparent support substrate.

This transparent supporting substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Co., Ltd.), 200 μm of TPDA was placed in a molybdenum resistance heating boat, and the TPDA obtained in Example 3 was placed in another molybdenum boat. 2,5-bis[2-phenyl-2-
(2-naphthyl)vinyl]xylene (NPVX) at 20
0 ■, and the vacuum chamber was depressurized to I x 10-'Pa.

After that, the boat containing TPDA was moved to 215-220°.
TPDA at a deposition rate of 0.1 to 0.3 nm.
/second to form a hole injection layer with a thickness of 60 nm on a transparent support substrate. The substrate temperature at this time was room temperature.

Next, without taking this out from the vacuum chamber, a 80 nm layer of NPVX was deposited as a light emitting layer on the hole injection layer from another boat. The deposition conditions are boat temperature 1
At 47°C, the deposition rate was 0.2-0.4 nrn/sec, and the substrate temperature was room temperature.

This was taken out from the vacuum chamber, a stainless steel mask was placed on top of the light emitting layer, and it was fixed to the substrate holder again.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat made of molybdenum, and 500 square meters of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2X10-'Pa, and then indium was deposited at a deposition rate of 0.03 to 0.08 nm/sec, and magnesium was simultaneously deposited from the other boat at a rate of 1.7 to 0.7 nm/sec.
Deposition was started at a deposition rate of 2.8 nm/sec. The temperature of the boat was approximately 800°C and 500°C for the indium-containing boat and the magnesium-containing boat, respectively. Under the above conditions, place a mixed metal electrode of magnesium and indium on the light emitting layer.
A 50 nm layer was deposited to form a counter electrode, and a device was formed.

Using the ITO electrode as the anode and the magnesium and indium mixed metal electrode as the cathode, apply a DC voltage to the obtained element] 7
．． When 5 V was applied, a current of about 220 mA/a [r] flowed, and a Bluish Green luminescence was obtained based on the chromaticity coordinates.

The peak wavelength was 502 nm according to spectroscopic measurements, and the luminance was 1000 cd/rd.

Application Example 4 A glass substrate of 25mm+X75mmX1.1mm was made into a film of ITO to a thickness of 1100 nm by vapor deposition (manufactured by HOYA) and was used as a transparent support substrate.

This transparent supporting substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Co., Ltd.), 200 μm of TPDA was placed in a resistance heating boat made of molybdenum, and the TPDA obtained in Example 5 was placed in another boat made of molybdenum. 2,5-bis[2-phenyl-2-
(2-pyridyl)vinyl]xylene (PPVX) at 20
0 ■, and the pressure in the vacuum chamber was reduced to I x 10''Pa.

After that, the boat containing TPDA was heated to 215-220℃.
TPDA at a deposition rate of 0.1 to 0.3 nm/
A hole injection layer having a thickness of 60 nm was formed by vapor deposition on a transparent support substrate in seconds. The substrate temperature at this time was room temperature.

Without taking it out of the vacuum chamber, 80 nm of PPVX was placed on the hole injection layer from another boat as a light emitting layer.
m layers were deposited. The deposition conditions were a boat temperature of 198°C.
The deposition rate was 0.2 to 0.4 nm/sec, and the substrate temperature was room temperature.

This was taken out from the vacuum chamber, a stainless steel mask was placed on top of the light emitting layer, and it was fixed to the substrate holder again.

Next, 1 g of ram ribbon with 6 mag screws was placed in a resistance heating boat made of molybdenum, and 500 mm of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2X10-'Pa, and then indium was deposited at a deposition rate of 0.03 to 0.08 nm/sec, and magnesium was simultaneously deposited from the other boat at a rate of 1.7 to 0.7 nm/sec.
The deposition started at a deposition rate of 2.8 nm/sec.

The temperatures of the boats containing indium and magnesium were approximately 800°C and 500°C, respectively. Under the above conditions, a mixed metal electrode of magnesium and indium was deposited to a thickness of 150 nm on the light emitting layer to form a counter electrode, thereby forming a device.

The TTO electrode was used as an anode and the mixed metal electrode of magnesium and indium was used as a cathode, and a DC voltage of 12.
When 5V was applied, a current of about 50 mA/d flowed, and green light emission was obtained in chromaticity coordinates. The peak wavelength was 531 nm according to spectroscopic measurements, and the luminance was 100 cd/+1.

Application example 5 I on a 25mm x 75mm x 1.1mm glass substrate
A film made of To with a thickness of 1100 nm by vapor deposition method (H
(manufactured by OYA) was used as a transparent support substrate.

This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Co., Ltd.), 200 μm of TPDA was placed in a resistance heating boat made of molybdenum, and the TPDA obtained in Example 8 was placed in another boat made of molybdenum. 2,5-bis(2-phenyl-2-
200 μm of methylvinyl)xylene (MePVX) was added, and the pressure in the vacuum chamber was reduced to I.times.10-'Pa.

After that, the boat containing TPDA was
Heating to °C, TPDA was deposited at a rate of 0.1-0.3n.
A hole injection layer having a thickness of 60 nm was formed by vapor deposition on a transparent support substrate at a rate of m/sec. The substrate temperature at this time was room temperature.

Next, without taking it out of the vacuum chamber, MePVX was deposited in a layer of 80 nm as a light emitting layer on the hole injection layer from another boat.

The deposition conditions were a boat temperature of 152°C and a deposition rate of 0.2.
~0.4 nm/sec, substrate temperature was room temperature.

This was taken out from the vacuum chamber, a stainless steel mask was placed over (1) of the light emitting layer, and it was again fixed to the substrate holder.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat 1 made of molybdenum, and 500 mm of indium was placed in another resistance heating boat made of molybdenum.

Thereafter, the pressure in the vacuum chamber was reduced to 2 X 10-'Pa, and then indium was added at 0.03-0. At the same time, 1.7% of magnesium was deposited from the other boat at a deposition rate of 08nm for 7 seconds.
Deposition started at a deposition rate of ~2.8 nm/sec. baud)·
The temperature of the indium-containing boat and the magnesium-containing boat are about 800°C and 500°C, respectively. Under the above conditions, a mixed metal electrode of magnesium and indium was deposited on the light emitting layer at 150 nrr+ to form a counter electrode, thereby forming a device.

The ITO electrode was used as an anode, and the mixed metal electrode of magnesium and indium was used as a cathode, and a DC voltage of 10 V was applied to the resulting device.
When applied, a current of about 140 mA/d flowed, and Purplish Blue light emission was obtained in chromaticity coordinates. The peak wavelength is 438 nm from spectroscopic measurement, and the luminance is 20 ed.
/rd.

Application example 6 ITO was deposited to a thickness of 1100 nm on a 25 mm x 75 mm x 1.1 mm glass substrate (
(manufactured by HOYA) was used as a transparent support substrate. This transparent support substrate was subjected to UV ozone cleaning for 2 minutes using a UV ozone treatment device.

This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Ltd.), 200 μm of TPDA was placed in a molybdenum resistance heating boat, and the TPDA obtained in Example 9 was placed in another molybdenum boat. 4,4′-bis(2-cyclohexyl-2=phenylvinyl)biphenyl (CPVB), which is a 4,4′-biphenylene dimethylidine derivative
Put 200■ of i) into the vacuum chamber.
The pressure was reduced to

After that, the boat containing TPDA was
Heating to °C, TPDA was deposited at a rate of 0.1-0.3n.
A hole injection layer having a thickness of 60 nm was formed by vapor deposition on a transparent support substrate at a rate of m/sec. The substrate temperature at this time was room temperature.

Next, without taking it out of the vacuum chamber, CPvBi was deposited as a light-emitting layer in a layer of 80 nm on the hole injection layer from another boat. The deposition conditions are boat temperature 2.
The deposition rate was 0.1-0.3 nm/sec at 10°C, and the substrate temperature was room temperature.

This was taken out from the vacuum chamber, a stainless steel mask was placed on top of the light emitting layer, and it was fixed to the substrate holder again.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat made of molybdenum, and 500 square meters of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2XIO-'Pa, and then indium was added to 0.03~0. At a deposition rate of 08 nm and 7 seconds,
At the same time, take 1.7 to 2 magnesium from the other boat.
．． Deposition was started at a deposition rate of 8 nm/sec. The temperature of Boat 1- was approximately 800°C and 500°C for the indium-containing boat and the magnesium-containing boat, respectively. A mixed metal electrode of magnesium and indium was deposited to a thickness of 1.50 nm on the light emitting layer under the above conditions to form a counter electrode, thereby forming a device.

Using the TTO electrode as the anode and the magnesium and indium mixed metal electrode as the cathode, the resulting device was applied with a DC voltage of 7.5
When V was applied, a current of about 14 mA/d flowed, and Purplish Blue light emission was obtained in chromaticity coordinates. The peak wavelength was 441 nm from spectroscopic measurements, and the luminance was 200 c.
It was about d/rd.

Application example 7 ITO was formed into a film with a thickness of 1100n by vapor deposition on a 25mm x 75mm x 1.1mm glass substrate-F (HOYA
) was used as a transparent support substrate. This transparent support substrate was subjected to UV ozone cleaning for 2 minutes using a UV ozone treatment device.

This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Ltd.), 200 μm of TPDA was placed in a molybdenum resistance heating boat, and the TPDA obtained in Example 10 was placed in another molybdenum boat. 4,4゛-bis(2,2-
p-tolylvinyl)biphenyl (DTVBi) 2
00■, and the vacuum chamber was depressurized to IXIO-'Pa.

After that, the boat containing TPDA was
°C and evaporate TPDA at a rate of 0.1-0.3n.
A hole injection layer having a thickness of 60 nm was formed by vapor deposition on a transparent support substrate at a rate of m/sec. The substrate temperature at this time was room temperature.

Next, without taking it out of the vacuum chamber, a light emitting layer of DTVBi was deposited on top of the hole injection layer from another boat to a thickness of 80 nm. The deposition conditions are boat temperature 2.
The deposition rate was 0.1-0.3 nm/sec at 53-271°C, and the substrate temperature was room temperature. This was taken out from the vacuum chamber, a stainless steel mask was placed on top of the light emitting layer, and it was fixed to the substrate holder again.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat made of molybdenum, and 500 square meters of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2X10-'Pa, and then indium was evaporated from O403 at a deposition rate of 0.08 nm/sec, and at the same time, magnesium was evaporated from the other boat at a rate of 1.7~0.
Deposition was started at a deposition rate of 2.8 nm/sec. The temperatures of boats 1 to 1 were approximately 800°C and 500°C for the boats containing indium and magnesium, respectively. Under the above conditions, a mixed metal electrode of magnesium and indium was deposited to a thickness of 150 nm on the light emitting layer to form a counter electrode, thereby forming a device.

The ITO electrode was used as an anode, and the mixed metal electrode of magnesium and indium was used as a cathode, and a DC voltage of 15 V was applied to the resulting device.
When applied, a current of about 32 mA/ad flowed, and blue light emission was obtained in chromaticity coordinates. The peak wavelength is 47 from spectroscopic measurement.
3nm, maximum luminance is 1000Cd/r111
That was it.

Application example 8 I on a 25mm x 75mm x 1.1mm glass substrate
A film made of TO with a thickness of 1100 nm by vapor deposition method (H
(manufactured by OYA) was used as a transparent support substrate. This transparent support substrate was subjected to UV ozone cleaning for 2 minutes using a UV ozone treatment device.

This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (Japan Vacuum Technology Reihitsu), 200 μm of TPDA was placed in a resistance heating boat made of molybdenum, and the TPDA obtained in Example 12 was placed in another boat made of molybdenum. 2,6-bis(2,2-di-p), a 2,6-naphthylenecymethylideine derivative
-tolylvinyl)naphthalene (DTVN) was charged at 200 μm, and the vacuum chamber was evacuated to I×10−’Pa.

After that, the boat containing TPDA was
Heating to 0°C, TPDA deposition rate 0.1-0.3
A hole injection layer having a thickness of 60 nm was formed by vapor deposition on a transparent support substrate at a rate of nm/sec. The substrate temperature at this time was room temperature.

Next, without taking this out from the vacuum chamber, a 80 nm thick layer of DTVN was deposited as a light emitting layer on the hole injection layer from another boat. The deposition conditions are boat temperature or 27
6-278°C, deposition rate O, 1-0.3 nm/sec,
The substrate temperature was room temperature. Remove this from the vacuum chamber,
A stainless steel mask was placed on top of the light emitting layer, and the mask was fixed to the substrate holder again.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat made of molybdenum, and 500 mm of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2X10-'Pa, and then indium was deposited at a deposition rate of 0.03 to 0.08 nm/sec, and magnesium was simultaneously deposited from the other boat at a rate of 1.7 to 0.7 nm/sec.
Deposition was started at a deposition rate of 2.8 nm/sec. The temperature of the boat was approximately 800°C and 500°C for the indium-containing boat and the magnesium-containing boat, respectively. Under the above conditions, place a mixed metal electrode of magnesium and indium on the light emitting layer.
A 50 nm layer was deposited to form a counter electrode, and a device was formed.

The ITO electrode was used as an anode, and the mixed metal electrode of magnesium and indium was used as a cathode, and a DC voltage of +2V was applied to the resulting device.
When applied, a current of about 350 mA/d flowed, and Greenish Blue light emission was obtained in chromaticity coordinates. The peak wavelength is 486 nm from spectroscopic measurement, and the luminance is 20 cd.
/rd.

Application example 9 ITO was formed into a film with a thickness of 1100 nm on a 25 mm x 75 mm x 1.1 mm glass substrate by vapor deposition (
(manufactured by HOYA) was used as a transparent support substrate. This transparent support substrate was subjected to UV ozone cleaning for 2 minutes using a UV ozone treatment device.

This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Japan Vacuum Technology Ltd.), 200 μm of TPDA was placed in a molybdenum resistance heating boat, and the TPDA obtained in Example 13 was placed in another molybdenum boat. 9,10-bis(2
,2-di-lytriruvinyl)anthracene (DTVA)
The pressure of the vacuum chamber was reduced to 1 x l O-'Pa.

After that, change the port containing the TPDA to 215-220.
℃ and deposited TPDA at a rate of 0.1-0.3 nm.
/second to form a hole injection layer with a thickness of 60 nm on a transparent support substrate. The substrate temperature at this time was room temperature.

Next, without taking it out of the vacuum chamber, a 80 nm layer of DTVA was deposited as a light emitting layer on the hole injection layer from another port. The deposition conditions are a boat temperature of 27
At 0'C, the deposition rate was 0.1-0.3 nm/sec, and the substrate temperature was room temperature. This was taken out from the vacuum chamber, a stainless steel mask was placed on top of the light emitting layer, and it was fixed to the substrate holder again.

Next, 1 g of magnesium ribbon was placed in a resistance heating boat made of molybdenum, and 500 square meters of indium was placed in another resistance heating boat made of molybdenum.

After that, the pressure in the vacuum chamber was reduced to 2xlO-'Pa, and then indium was added to 0.03~0. With a deposition rate of O8 nm/sec,
At the same time, add 1.7 to 2 magnesium from the other port.
．． Deposition was started at a deposition rate of 8 nm/sec. The temperature of the port was approximately 800°C and 500°C for the indium-containing port and the magnesium-containing port, respectively. Under the above conditions, place a mixed metal electrode of magnesium and indium on the light emitting layer.
A 50 nm layer was deposited to form a counter electrode, and a device was formed.

The ITO electrode was used as an anode, and the mixed metal electrode of magnesium and indium was used as a cathode, and a DC voltage of 10 V was applied to the resulting device.
When applied, a current of about 350 mA/d flowed, and green light emission was obtained in chromaticity coordinates. The optical wavelength is 526 nm from spectroscopic measurements, and the luminance is 4.
00 cd/endurance or higher.

Application Examples 10 to 19 In Application Example 9, an EL element was formed in the same manner as in Application Example 9 except that the light emitting material was changed. Table 3 shows these EL emission characteristics.

(The following is a blank space) -109 [Effects of the Invention] The aromatic dimethylidine compound of the present invention is a novel compound, and has a luminance of 1000 Cd/r in the region ranging from blue-violet to green.
It is possible to obtain EL light emission with a high luminance equal to or higher than rl', and at the same time, to obtain efficient EL light emission at a practical level of luminance (50 to 200 cd/I).

Therefore, the aromatic dimethylidine compound of the present invention is
It is expected that it will be effectively used in various light emitting materials, including light emitting materials for EL devices.

Shinny

Claims (5)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 to R^4 are alkyl groups having 1 to 6 carbon atoms,
Aralkyl group having 7 to 8 carbon atoms, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted cyclohexyl group,
It represents a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms and an alkoxy group having 1 to 6 carbon atoms. Here, the substituent represents 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, a phenyl group, a nitro group, a hydroxyl group, or a halogen. These substituents may be single or plural. Also R^1~R^4
may be the same or different from each other, and R^1 and R^2, R^3 and R^4 are bonded to the substituent group,
A substituted or unsubstituted saturated five-membered ring or a substituted or unsubstituted saturated six-membered ring may be formed. Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and may be singly substituted or multiply substituted, and the bonding site may be any of ortho, para, and meta. Note that the substituents are the same as above. Further, the substituents of the aryl group may be bonded to each other to form a substituted or unsubstituted saturated five-membered ring or a substituted or unsubstituted saturated six-membered ring. However, when Ar is unsubstituted phenylene,
R^1 to R^4 are each an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted cyclohexyl group. group, substituted or unsubstituted pyridyl group, substituted or unsubstituted aryloxy group. ] An aromatic dimethylidine compound represented by (2) R^1 to R^4 are each an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted Aryloxy group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted pyridyl group, Ar is substituted phenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted p - Terphenylene group, substituted or unsubstituted anthracenediyl group (However, the substituent may be an alkyl group, an alkoxy group, an aryloxy group, a phenyl group, a nitro group, or a halogen, and may be single or multiple.) The aromatic dimethylidine compound according to claim 1. (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and Ar is the same as above. ] An arylene group-containing phosphorus compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^5 and R^6 are the above R^1 to R, respectively.
It is the same as ^4. However, alkyl groups, aralkyl groups,
Excludes cases where it is an alkoxy group or an aryloxy group. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by condensation with a ketone represented by ▼ [In the formula, Ar is the same as above. R^5, R^6 are
Each of them is the same as R^1 to R^4 above. However, alkyl groups, aralkyl groups, alkoxy groups, and aryloxy groups are excluded. ] A method for producing an aromatic dimethylidine compound represented by: (4) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^7 and R^8 are the above R^1 to R, respectively.
It is the same as ^4. ] A phosphorus compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, Ar is the same as above. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by condensation with a dialdehyde represented by ▼ [In the formula, Ar is the same as above. R^7, R^8 are
Each of them is the same as R^1 to R^4 above. ] A method for producing an aromatic dimethylidine compound represented by (5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1, R^2, Ar, and R are the same as above. [In the formula, R^3 and R^4 are the same as above. ] Claim 1 characterized in that it is condensed with a ketone represented by
Or the method for producing an aromatic dimethylidine compound according to claim 2.