JP2000053677A - Aromatic hydrocarbon compound and organic electroluminescence element by using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound of a sulfur atom-containing aromatic hydrocarbon compound, and useful as a constituent material of an organic electroluminescence element having high thermal stability, high luminescent characteristics and a low drive voltage. SOLUTION: This new compound is the one of formula I [X is a 21-60C arylene (substituted with a 1-30C alkyl or the like) or a polyarylene; Y1 and Y2 are each a 4-30C monovalent group comprising a heterocycle having a sulfur atom, or a sulfur atom-containing polyarylene of an aggregate of arylenes including the before heterocycle; R1 and R2 are each a 6-30C aryl (substituted with one or more kinds of H, a 1-30C alkyl and the like), a polyaryl of the aggregate of the before group, or the like], e.g. a compound of formula II. The compound of formula I is obtained, for example, by forming a compound of formula III into a Grignard reagent, and coupling the obtained Grignard reagent with a compound of the formula Br-X-Br (e.g. 9,10-dibromoanthracene).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel aromatic hydrocarbon compound and an organic electroluminescence device (hereinafter sometimes referred to as an organic EL device) using the compound. More specifically, the present invention relates to a sulfur atom-containing aromatic hydrocarbon compound which is highly useful as a constituent material of an organic EL device, and an organic EL device using this compound which is excellent in chemical stability and heat resistance.

[0002]

2. Description of the Related Art An organic EL device utilizing electroluminescence has characteristics of high visibility because it is self-luminous, and excellent impact resistance because it is a completely solid device. Therefore, it is used in fields such as thin film display elements, backlights of liquid crystal displays, and flat light sources.

[0003] The electroluminescent element currently put to practical use is a dispersion type electroluminescent element. Since this dispersion type electroluminescence element requires an AC voltage of several tens of volts or 10 kilohertz or more, its driving circuit is complicated. For these reasons, organic EL elements capable of reducing the driving voltage to about 10 volts and emitting light with high luminance have been actively studied in recent years. For example, C.I. W. T
ang and S.M. A. Van Slyke App
l. Phys. Lett. , Vol. 51 pp. 91
3-915 (1987) and JP-A-63-264629.
In Japanese Patent Application Laid-Open Publication No. H11-163, an organic thin-film EL device is proposed in which the configuration is a stacked type of a transparent electrode / a hole injection layer / a light emitting layer / a back electrode, and the hole injection layer used here is more efficient. Holes can be injected into the light emitting layer. The light-emitting layer used in such an organic EL element may be a single layer, but as described above, the balance between the electron transporting property and the hole transporting property was not good, so that the light-emitting layer was stacked in multiple layers. By doing so, the performance has been improved.

However, in order to form such a laminated structure, there are problems that the manufacturing process is complicated and the required time is long, and that there are many restrictions such as a requirement for each layer to be thin. Furthermore, in recent years, there has been an increasing demand for downsizing of information devices and the like and a shift to a portable type, and there has been an increasing demand for further lowering these drive voltages. Thus, various attempts have been made to lower the driving voltage by improving the hole injection layer, developing a hole transporting material, and the like, but they have not been sufficiently satisfactory.
In order to reduce the driving voltage, for example, Japanese Patent Application Laid-Open
JP-294959A proposes an organic EL device using a compound having a thiophene structural unit at the terminal of the molecule. By introducing the thiophene structural unit in this way, high luminance can be obtained and the driving voltage can be reduced, but the thiophene-based compound proposed here is not sufficient in chemical stability. However, there is a disadvantage that the heat resistance that can withstand continuous use for a long time is lacking.

[0005]

SUMMARY OF THE INVENTION In view of the above-mentioned circumstances, the present invention, when used as a constituent material of an organic EL device, satisfies the high emission characteristics of the organic EL device and the reduction in driving voltage. It is an object of the present invention to provide an organic compound having high heat resistance and an organic EL device using the same.

[0006]

Means for Solving the Problems As a result of various studies to solve the above problems, the present inventors have found that a sulfur atom-containing aromatic hydrocarbon compound having a specific chemical structure achieves the above object. This led to the completion of the present invention based on these findings. That is, the gist of the present invention is:
It is as follows. (1) An aromatic hydrocarbon compound represented by the following general formula [1].

[0007]

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In the formula (1), X is an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms as a substituent. C21-C60 which may have one or more groups selected from the group consisting of an oxy group, an amino group, a cyano group, a nitro group, a hydroxyl group and a halogen atom.
Represents an arylene group or a polyarylene group of Y ¹ ,
Y ² each independently represents a sulfur atom-containing polyarylene group having a carbon number of 4 to 30 and a monovalent group consisting of a sulfur atom-containing heterocycle or an aggregate of arylene groups containing the heterocycle. , R ¹ and R ² each independently represent a hydrogen atom or a substituent as an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 20 carbon atoms, An aryl group having 6 to 30 carbon atoms which may have one or more groups selected from the group consisting of an aryloxy group, an amino group, a cyano group, a nitro group, a hydroxyl group, and a halogen atom, or the aryl group; It represents a polyaryl group which is an aggregate of groups or a monovalent group comprising a heterocyclic ring having 4 to 30 carbon atoms. (2) An organic electroluminescent device comprising an aromatic hydrocarbon compound represented by the general formula [1] sandwiched between a pair of electrodes. (3) An organic electroluminescent device having a light emitting layer provided between a pair of electrodes, wherein an aromatic hydrocarbon compound represented by the general formula [1] is used as a constituent material of the light emitting layer. Electroluminescence element. (4) In an organic electroluminescence device having a light emitting layer and at least a hole transport layer between a pair of electrodes, an aromatic hydrocarbon compound represented by the general formula [1] is used as a constituent material of the hole transport layer. An organic electroluminescent device, wherein the device is used. (5) The organic electroluminescent device according to (3) or (4), wherein the light emitting layer contains a recombination site forming substance. (6) The organic electroluminescent device according to (5), wherein a fluorescent material having a fluorescence quantum yield of 0.3 to 1.0 is used as the recombination site forming substance. (7) The material according to (5), wherein at least one compound selected from the group consisting of a styrylamine-based compound, a quinacridone derivative, a rubrene derivative, a coumarin derivative, and a pyran derivative is used as the recombination site-forming substance.
Or, the organic electroluminescent device according to (6).

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The aromatic hydrocarbon compound of the present invention is an aromatic hydrocarbon compound represented by the above general formula [1], wherein X and R ¹ , R ² As the alkyl group having 1 to 30 carbon atoms of the substituent represented by, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group , Pentyl group, hexyl group,
Examples include a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, and a tridecyl group. Examples of the alkoxy group having 1 to 30 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, te
rt-butoxy group and the like. And carbon number 6
Examples of the aryl group having from 20 to 20 include a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthranyl group, a styryl group, and a styrylphenyl group. As the aryloxy group having 6 to 18 carbon atoms, a phenyloxy group , A tolyloxy group, a styryloxy group, a biphenyloxy group, and a naphthyloxy group. The substituents in X and R ¹ and R ² may not be present, may be substituted by one, or may be substituted by two or more. There are no restrictions on the position of substitution on the aromatic ring or heterocyclic ring.

Examples of the arylene group having 21 to 60 carbon atoms represented by X which may have a substituent include a linear type such as quarter phenylene, kink phenylene, and sexiphenylene, pentacenediyl, and the like. Aromatic condensed ring type such as pentafendiyl, coronenediyl, pyranthylene diyl and the like can be mentioned. Examples of the polyarylene group having 21 to 60 carbon atoms include diphenylanthracenediyl, dibiphenylanthracenediyl,
Examples include diphenylbinaphthylene, dianthrylterphenylene, dibiphenylnaphthylene and the like.

Next, as the heterocyclic ring in the monovalent group consisting of a heterocyclic ring having 4 to 30 carbon atoms and containing a sulfur atom represented by Y ¹ and Y ^{2 in} the general formula [1], thiophene, Benzothiophene, thiazole, thianthrene,
Phenoxatin, phenothiazine and the like, and as the sulfur atom-containing polyarylene group which is an aggregate of the arylene group containing the heterocycle, the sulfur atom-containing heterocycle and arylene, for example, phenylene, biphenylene,
Naphthylene, terphenylene, anthracenediyl, quarterphenylene or the following formula,

[0012]

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Wherein n and m are each an integer of 1 to 5. ) Are combined and linked, and include, for example, diphenylthiophenediyl, bianthrylbenzothiophenediyl, dibiphenylthiandienediyl, naphthylthiophenediyl and the like. Further, carbon atoms of ⁶ to 3 represented by R ¹ and R ^{2 in} the general formula [1].
Examples of the aryl group 0 include a phenyl group, a biphenyl group,
Examples include a naphthyl group, a terphenyl group, an anthranyl group, a styryl group, a styrylphenyl group, and the like.Examples of the polyaryl group that is an aggregate of the aryl groups include diphenylanthracene, binaphthyl, dianthril terphenyl, dibiphenylnaphthalene, and the like. Is mentioned. Examples of the heterocycle having 4 to 30 carbon atoms include furan, thiophene, pyrrole, 2-hydroxypyrrole, benzofuran, isobenzofuran, 1-benzothiophene, 2-benzothiophene, indole, isoindole, indolizine, carbazole, -Hydroxypyran, 2-hydroxychromene, 1-hydroxy-2-benzopyran, xanthene, 4-hydroxythiopyran, pyridine, quinoline, isoquinoline, 4-hydroxyquinolidine, phenanthridine, acridine, oxazole, isoxazole, thiazole, Isothiazole, furazane, imidazole, pyrazole, benzimidazole,
1-hydroxyindazole, 1,8-naphthyridine,
Pyrazine, pyrimidine, pyridazine, quinaxalin, quinazoline, sinoline, phthalazine, purine, teridine, perimidine, 1,10-phenanthroline, tianthrene, phenoxatin, phenoxazine, phenothiazine, phenazine, phenazine, and the like.

Next, specific examples of the aromatic hydrocarbon compound represented by the general formula [1] are as follows.

[0015]

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[0016]

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[0017]

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[0018]

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Next, the method for producing the aromatic hydrocarbon compound represented by the general formula [1] can be, for example, the following method. That is, the following general formula:

[0020]

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[R ¹ and Y ¹ in the formula are the same as those in the general formula [1]
Are the same as R ¹ and Y ¹ . Or a compound represented by the following general formula:

[0022]

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[In the formula, R ² and Y ² represent the above-mentioned general formula [1]
And R ² and Y ² are the same. After the compound represented by the Grignard reagent, the following general formula,

[0024]

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[X in the formula is the same as X in the general formula [1]. ], The aromatic hydrocarbon compound represented by the general formula [1] can be efficiently produced. Next, the organic EL device of the present invention is configured by sandwiching the aromatic hydrocarbon compound between a pair of electrodes. The aromatic hydrocarbon compound preferably has a structure used as a constituent material of a light emitting layer of an organic EL device having a light emitting layer provided between a pair of electrodes. In addition, the aromatic hydrocarbon compound is used in an organic EL device having a structure in which an electron injection layer, a hole injection layer, an electron transport layer, and a hole transport layer are provided in addition to a light emitting layer between a pair of electrodes. It may be used as a constituent material of the hole transport layer.

As described above, when the aromatic hydrocarbon compound is used as a constituent material of a light emitting layer or a hole transport layer of an organic EL device, the aromatic hydrocarbon compound has an electron transporting group in its molecule. Since the compound has a structure in which the compound and the hole transporting group are arranged in a well-balanced manner, even this compound monolayer efficiently expresses electroluminescence performance. That is, since there is a group consisting of a heterocyclic ring containing a sulfur atom in this aromatic hydrocarbon compound,
Holes can be efficiently injected and transported into the molecules of the compound. In addition, since the aromatic hydrocarbon compound has an aromatic condensed ring having 21 to 60 carbon atoms, it functions as a group for electron transport. Further, the heterocyclic ring containing a sulfur atom or the aromatic condensed ring having 21 to 60 carbon atoms present in the aromatic hydrocarbon compound lowers the ionization potential, so that holes can be efficiently injected. Thus, the driving voltage of the organic EL element can be reduced.

As a part of the constituent material of the light emitting layer of the organic EL device, a recombination site forming substance can be used. This recombination site-forming substance is a substance that positively provides a place where electrons and holes injected from both poles respectively recombine, or recombination energy of electrons and holes does not occur, but recombination energy is propagated. It is a substance that provides a place to emit light. Therefore, by adding this recombination site-forming substance, electrons and holes are more intensively recombined in the vicinity of the center of the light emitting layer than in the case where the aromatic hydrocarbon compound is used alone. The light emission luminance can be further increased.

From the above, as a material for forming a recombination site used as a constituent material of the light emitting layer of the organic EL device of the present invention, a substance having a high fluorescence quantum yield is preferable, and the value thereof is preferably 0.3. A value of from 1.0 to 1.0 is preferred. Examples of such a recombination site-forming substance include one or a mixture of two or more selected from the group of styrylamine compounds, quinacridone derivatives, rubrene derivatives, coumarin derivatives, and pyran derivatives. As the recombination site forming substance, a conjugated polymer can be used, and in particular, a polyarylenevinylene derivative, an alkyl-substituted or alkoxy-substituted polyarylene or vinylene derivative having 1 to 50 carbon atoms, and the like can be given. Can be

Specific examples of the above-mentioned recombination site-forming substance include the following compounds.

[0030]

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[0031]

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[0032]

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[N in the formula [12] is an integer of 50 or more. It is also desirable to select these recombination site forming substances in consideration of the coloring property of the light emitting layer. For example, when a blue color is desired, it is preferable to use perylene represented by the above formula [3] or amino-substituted distyryl arylene derivatives represented by the above formulas [4] and [5]. . When a green color is desired, it is preferable to use a quinacridone derivative represented by the above formula [6] or [7] or a coumarin derivative represented by the above formula [8]. When a yellow color is desired, the above formula is used.

It is preferable to use a rubrene derivative represented by [9]. Further, when orange or red-orange is desired, it is preferable to use a dicyanomethylpyran derivative represented by the above formula [10] or [11].

The compounding ratio of the recombination site forming substance is determined in consideration of the light emission luminance and the coloring property of the light emitting layer.
It is preferable to set the value in the range of 0.1 to 20 parts by weight with respect to 0 parts by weight. If the amount of the recombination site-forming substance is less than 0.1 part by weight, the emission luminance tends to decrease, while if it exceeds 20 parts by weight, the durability tends to decrease. Therefore, in order to better maintain the balance between the emission luminance and the durability in the organic EL element, the content of the aromatic hydrocarbon compound 100
The amount is preferably 0.5 to 20 parts by weight, more preferably 1.0 to 10 parts by weight based on parts by weight.

Next, the structure of the light emitting layer in the organic EL device of the present invention is not particularly limited, but is preferably a single layer which is easy to manufacture. However, if necessary, an electron injection layer, a hole injection layer, an electron transport layer, a hole transport layer, or the like may be provided in combination with the light emitting layer. The thickness of the light emitting layer is 100 to 10,000 as in the case of a normal organic EL device.
Preferably, the value is in the range of Angstroms. When the thickness of the light emitting layer is less than 100 angstroms, it becomes difficult to form a light emitting layer having a uniform thickness without pinholes, or mechanical strength tends to decrease,
On the other hand, if it exceeds 10,000 angstroms, it takes a long time to manufacture, and this is economically disadvantageous. Therefore, the thickness of this light emitting layer is 200 to 3,0
The value is more preferably in the range of 00 angstroms, and even more preferably in the range of 300 to 1,000 angstroms.

Next, the light emitting layer can be formed according to a conventional method. For example, a vacuum deposition method, a sputtering method, or an LB film method can be employed. Alternatively, the light emitting layer can be formed by dissolving the aromatic hydrocarbon compound or the recombination site forming substance in an organic solvent, applying the solution on an electrode, and drying the electrode.

For the electrode in this organic EL device, a metal, an alloy, an electrically conductive compound or a mixture thereof having a large work function, for example, a value exceeding 4.0 eV is used for the anode. Is preferred. Specifically, indium tin oxide (IT
O), indium copper, tin, zinc oxide, gold, platinum, palladium and the like can be used alone or in combination of two or more. The thickness of this anode is
The value is preferably in the range of 10 to 1,000 nm, and more preferably in the range of 10 to 200 nm. The anode used here is preferably substantially transparent, and more specifically, has a light transmittance of 10% or more so that light emitted from the light emitting layer can be effectively extracted to the outside. .

On the other hand, for the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound or a mixture thereof having a small work function, for example, less than 4.0 eV. Specifically, one of magnesium, aluminum, indium, lithium, sodium, silver, etc.
The species can be used alone or in combination of two or more. And also about the thickness of this cathode, 10
Preferably, the value is in the range of ~ 1,000 nm,
More preferably, the value is in the range of 10 to 200 nm.

[0039]

Next, the present invention will be described in more detail with reference to examples. [Example 1] (1) Synthesis of aromatic hydrocarbon compound (1)

[0040]

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As shown in the above, 100 g (0.5 mol) of 2-benzoylthiophene [a] and 153 g (0.5 mol) of a phosphonate ester [b] were suspended in 200 ml of dimethyl sulfoxide. , Potassium-
56 g (0.5 mol) of t-butoxide were added. Then, the reaction was allowed to react for 6 hours at room temperature under an argon gas flow.

After the completion of the reaction, 100 ml of water: methyl alcohol = 2: 8 (volume ratio) was added to the reaction product, and the precipitated crystals were purified by a silica gel column.
As a result, 110 g (0.3 mol) of pale yellow powder [c]
I got Next, 17 g of the compound [c] obtained here was obtained.
(0.05 mol) was dissolved in 80 ml of anhydrous tetrahydrofuran. This solution was slowly dropped into 1.4 g (0.058 mol) of magnesium activated with iodine to produce a Grignard reagent. Further, the mixture was stirred under reflux for 1 hour to mature the Grignard reagent.

Next, 6 g (0.018 mol) of 9,10-dibromoanthracene [d] was dissolved in anhydrous tetrahydrofuran, and PdCl ₂ (Pph ₃ ) ₂ 0.7
g (9.8 × 10 ^-4 mol) was added. While stirring the solution, 2.0 ml of a 1 molar DIBAL toluene solution was added. The solution prepared in this way is
The mixture was heated to 0 ° C., and the Grignard reagent aged earlier was added dropwise thereto. The reaction solution was black. This reaction solution was stirred under reflux for 6 hours to carry out the following reaction.

[0044]

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After completion of the reaction, the product was allowed to cool, 50 ml of acetone, 50 ml of methyl alcohol and 20 ml of water were added thereto, and the precipitated crystals were collected by filtration. This compound was washed with 100 ml of toluene to obtain 2.3 g (0.003 mol) of a yellow powder. The yield was 17%. Next, when mass spectrometry (FD-MS) of the obtained compound was performed, m / Z =
It was 698 only, and it was confirmed that the target compound (1) was obtained.

2) Preparation of Organic EL Element A 100 nm thick indium tin oxide (I) was formed on a glass substrate having a length of 25 mm, a width of 75 mm and a thickness of 1.1 mm.
TO) A thin film was deposited to form an anode, which was used as a transparent support substrate. Next, the transparent support substrate was ultrasonically cleaned with isopropyl alcohol for 5 minutes, and then further cleaned with pure water for 5 minutes. Next, the washed transparent support substrate was fixed to a holder in a vacuum chamber of a vacuum evaporation apparatus (manufactured by Nippon Vacuum Engineering Co., Ltd.), and two molybdenum resistance heating boats also provided in the vacuum chamber, respectively, 200 mg of the aromatic hydrocarbon compound (1) obtained in the above (1) and 4,4′-bis [2- (4- (N, N
-Diphenylamino) phenyl) vinyl] biphenyl (abbreviated as DSBi in Table 1) in an amount of 200 mg.

In this state, the pressure in the vacuum chamber is set to 1 × 1
After reducing the pressure to 0 ⁻⁴ Pa, the two resistance heating boats were simultaneously heated to form a light emitting layer having a thickness of 80 nm, which was composed of the aromatic hydrocarbon compound and the recombination site forming substance. It was separately confirmed that the mixing ratio of the aromatic hydrocarbon compound and the recombination site forming substance in the light emitting layer was 40: 1 by weight.

Next, the transparent support substrate on which the light emitting layer is formed is taken out of the vacuum chamber, and a stainless steel mask is mounted on the light emitting layer surface. Fixed again. Also,
0.5 g of silver wire was housed in a tungsten basket provided in the vacuum chamber, and 1 g of magnesium ribbon was housed in a resistance heating boat. In this state, after reducing the pressure of the vacuum chamber to 1 × 10 ⁻⁴ Pa, the basket and the resistance heating boat were simultaneously heated,
Silver was 0.1 nm / sec. Deposition rate, magnesium is 1.8 nm / sec. At a deposition rate of. Thus, a cathode (mixed electrode of magnesium and silver) having a thickness of 200 nm was formed, and an organic EL device of the present invention was obtained.

(3) Evaluation of organic EL device A voltage of 10 V was applied between the anode and the cathode of the organic EL device obtained in the above (2), and the current density was 2.5 mA / c.
When applied under the condition of m ² and the initial evaluation was performed, blue uniform light emission having a peak wavelength of 470 nm was obtained. The luminance of the blue light emitted from the device measured using a luminance meter was 180 cd / m ² , and the luminous efficiency was 2.3 lumen / W. In addition, the organic E for which the initial evaluation was completed
The L element was placed in a nitrogen stream, and the emission luminance was 100 cd /
The value of the applied voltage was set so as to be m ² . When the constant current driving was continued in this state, it took a long time of about 1000 hours for the emission luminance to reach 50 cd / m ² , which is a half of the initial value. Therefore, it was confirmed that the organic EL device of the present invention had excellent durability.

Example 2 (1) Synthesis of Aromatic Hydrocarbon Compound (2) The procedure of Example 1 was repeated except that the compound [e] was used in place of the compound [d] used in (1). In the same manner as in Example 1, (1),

[0051]

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The reaction was carried out to obtain 1.8 g of a yellow compound. Then, mass spectrometry (F
When D-MS) was performed, m / Z was only 874, and it was confirmed that the target compound (2) was obtained. (2) Preparation of Organic EL Device Instead of the aromatic hydrocarbon compound (1) used in Example 1, the aromatic hydrocarbon compound (2) synthesized in (1) was used. 4,4'-bis [2- (4- (N, N-diphenylamino) phenyl)
An organic EL device was produced in the same manner as in Example 1 except that the dicyanomethylpyran derivative represented by the above formula [10] (abbreviated as DCM1 in Table 1) was used instead of [vinyl] biphenyl. . (3) Evaluation of Organic EL Device The organic EL device obtained in the above (1) was evaluated in the same manner as in Example 1. Table 1 shows the results of the evaluation.

Example 3 (1) Synthesis of aromatic hydrocarbon compound (3) The procedure of Example 1 was repeated except that the compound [f] was used instead of the compound [d] used in (1). In the same manner as in Example 1, (1),

[0054]

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The above reaction was carried out to obtain 1.2 g of a yellow compound. Then, mass spectrometry (F
D-MS), it was only m / Z = 950, and it was confirmed that the target compound (3) was obtained. (2) Production of organic EL element Example 1 was repeated except that the aromatic hydrocarbon compound (3) synthesized in (1) was used instead of the aromatic hydrocarbon compound (1) used in Example 1. Organic EL
An element was manufactured. (3) Evaluation of Organic EL Device The organic EL device obtained in the above (1) was evaluated in the same manner as in Example 1. Table 1 shows the results of the evaluation.

Example 4 (1) Synthesis of aromatic hydrocarbon compound (4) In place of compound [c] used in (1) of Example 1, compound [g] was used, and compound [d] was used. ]
Except that the compound [h] was used, the same procedures as in (1) of Example 1 were carried out to obtain

[0057]

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The above reaction was carried out to obtain 1.2 g of a yellow compound. Then, mass spectrometry (F
D-MS), it was m / Z = 938 only, and it was confirmed that the target compound (4) was obtained. (2) Preparation of Organic EL Device An organic EL device was prepared in the same manner as in Example 1 except that the aromatic hydrocarbon compound synthesized in (1) was used instead of the aromatic hydrocarbon compound used in Example 1. An EL device was manufactured. (3) Evaluation of Organic EL Device The organic EL device obtained in the above (1) was evaluated in the same manner as in Example 1. Table 1 shows the results of the evaluation.

Example 5 (1) Synthesis of Aromatic Hydrocarbon Compound (5) The procedure of Example 1 was repeated except that the compound [i] was used in place of the compound [c] used in (1). In the same manner as in Example 1, (1),

[0060]

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The above reaction was carried out to obtain 1.0 g of a yellow compound. Then, mass spectrometry (F
D-MS), it was m / Z = 950 only, and it was confirmed that the target compound (5) was obtained. (2) Production of Organic EL Device Instead of the aromatic hydrocarbon compound (1) used in Example 1, the aromatic hydrocarbon compound (5) synthesized in the above (1) was used, and the recombination site forming substance was An organic EL device was manufactured in the same manner as in Example 1 except that the device was not used. (3) Evaluation of Organic EL Device The organic EL device obtained in the above (1) was evaluated in the same manner as in Example 1. Table 1 shows the results of the evaluation.

Example 6 (1) Synthesis of aromatic hydrocarbon compound (6) In place of compound [c] used in (1) of Example 1, compound [j] was used. In the same manner as in Example 1, (1) except that the compound [k] was used in place of d),

[0063]

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The above reaction was carried out to obtain 1.1 g of a yellow compound. Then, mass spectrometry (F
D-MS), the m / Z was only 1482, and it was confirmed that the desired compound (6) was obtained. (2) Production of organic EL device Example 1 was repeated except that the aromatic hydrocarbon compound (6) synthesized in (1) was used instead of the aromatic hydrocarbon compound (1) used in Example 1. Organic EL
An element was manufactured. (3) Evaluation of Organic EL Device The organic EL device obtained in the above (1) was evaluated in the same manner as in Example 1. Table 1 shows the results of the evaluation.

Example 7 (1) Synthesis of Aromatic Hydrocarbon Compound (7) In place of compound [c] used in (1) of Example 1, compound [m] was used. In the same manner as in Example 1, (1) except that the compound [n] was used in place of d),

[0066]

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The above reaction was carried out to obtain 1.0 g of a yellow compound. Then, mass spectrometry (F
When D-MS) was performed, the m / Z was only 1166, and it was confirmed that the desired compound (7) was obtained. (2) Production of Organic EL Element Instead of the aromatic hydrocarbon compound (1) used in Example 1, the aromatic hydrocarbon compound (7) synthesized in (1) above was used, and the recombination site forming substance was An organic EL device was manufactured in the same manner as in Example 1 except that the device was not used. (3) Evaluation of Organic EL Device The organic EL device obtained in the above (1) was evaluated in the same manner as in Example 1. Table 1 shows the results of the evaluation.

[0068]

[Table 1]

Example 8 (1) Production of Organic EL Element A 100 nm thick indium tin oxide (I) was formed on a glass substrate having a length of 25 mm, a width of 75 mm and a thickness of 1.1 mm.
TO) A thin film was deposited to form an anode, which was used as a transparent support substrate. Next, the transparent support substrate was ultrasonically cleaned with isopropyl alcohol for 5 minutes, and then further cleaned with pure water for 5 minutes.

Next, the aromatic hydrocarbon compound (5) synthesized in (1) of Example 5 and the butylethylhexyl polyphenylene derivative represented by the above formula (12) as a recombination site-forming substance were placed in a container. And uniformly dissolved in toluene to obtain a coating solution. Next, a coating solution was applied on the transparent support substrate using a spin coater under a rotation condition of 1000 rpm, and then dried by heating to a thickness of 9 mm.
A 5 nm light emitting layer was formed. Further, in the same manner as in Example 1, a cathode (mixed electrode of magnesium and silver) having a thickness of 200 nm was formed on the light emitting layer to obtain an organic EL device.

(2) Evaluation of the organic EL device A voltage of 8 V was applied between the anode and the cathode of the organic EL device obtained in the above (1), and the initial evaluation was performed. Obtained. In addition, when the light emission luminance was measured using a luminance meter, it was 150 cd / m ² , and the light emission efficiency was 2.4 lumen / W.

[0072]

Industrial Applicability The aromatic hydrocarbon compound of the present invention is highly useful as a constituent material of a light emitting layer or a hole transport layer of an organic EL device, and the aromatic hydrocarbon compound is used as a light emitting layer or a hole transport layer. The driving voltage of the organic EL element used as the constituent material of (1) can be reduced. In addition, since the aromatic hydrocarbon compound has high heat resistance, the organic EL element has excellent durability even when the organic EL element is continuously driven for a long period of time without deterioration in performance.
An L element can be provided.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 339/08 C07D 339/08 409/14 241 409/14 241 333 333 C09K 11/06 635 C09K 11/06 635 H05B 33/14 H05B 33/14 B 33/22 33/22 DF term (reference) 3K007 AB00 AB04 AB06 AB14 CA01 CB01 DA00 DB03 EB00 FA01 4C023 PA08 4C033 AA04 AA17 AD09 AD17 4C036 AA02 AA05 AA17 4C063 AA97 DD09 DD92 EE10

Claims (7)

[Claims] 1. An aromatic hydrocarbon compound represented by the following general formula [1]. Embedded image [In Formula [1], X is a C1-C30 alkyl group, a C1-C30 alkoxy group, a C6-C3 as a substituent.
It may have one or two or more groups selected from the group consisting of 20 aryl groups, aryloxy groups having 6 to 18 carbon atoms, amino groups, cyano groups, nitro groups, hydroxyl groups and halogen atoms. Represents an arylene group or a polyarylene group having 21 to 60 carbon atoms, and Y ¹ and Y ² each independently represent a monovalent group having a carbon number of 4 to 30 and comprising a heterocyclic ring containing a sulfur atom or Represents a sulfur atom-containing polyarylene group which is an aggregate of a ring-containing arylene group, wherein R ¹ and R ² each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms as a substituent,
One or more selected from the group consisting of 30 alkoxy groups, C6-20 aryl groups, C6-18 aryloxy groups, amino groups, cyano groups, nitro groups, hydroxyl groups and halogen atoms Represents an aryl group having 6 to 30 carbon atoms which may have a group, a polyaryl group which is an aggregate of the aryl groups, or a monovalent group having a heterocyclic ring having 4 to 30 carbon atoms. ] 2. An organic electroluminescent device comprising an aromatic hydrocarbon compound represented by the general formula [1] sandwiched between a pair of electrodes. 3. An organic electroluminescence device having a light emitting layer provided between a pair of electrodes, wherein an aromatic hydrocarbon compound represented by the general formula [1] is used as a constituent material of the light emitting layer. Organic electroluminescent element. 4. An organic electroluminescence device having a light emitting layer and at least a hole transport layer between a pair of electrodes, wherein an aromatic hydrocarbon represented by the general formula [1] is used as a constituent material of the hole transport layer. An organic electroluminescence device comprising a compound. 5. The organic electroluminescent device according to claim 3, wherein the light emitting layer contains a substance for forming a recombination site. 6. The organic electroluminescence device according to claim 5, wherein a fluorescent material having a fluorescence quantum yield of 0.3 to 1.0 is used as the recombination site forming substance. 7. The method according to claim 5, wherein at least one compound selected from the group consisting of a styrylamine compound, a quinacridone derivative, a rubrene derivative, a coumarin derivative and a pyran derivative is used as the recombination site-forming substance. The organic electroluminescent device according to the above.