JP3520880B2 - Oxadiazole derivative and method for producing the same - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to novel oxadiazole derivatives useful as materials for organic EL devices and methods for producing them.

[0002]

2. Description of the Related Art Various oxadiazole derivatives are known as a light emitting component or an electron transporting component constituting an organic EL device. For example, The Chemical Society of Japan, 1991, N.
o. 11, p. 1540 to 1548 report that various oxadiazole derivatives are useful as a light emitting material or an electron transporting material. However, in addition to the stability of the device, sufficient values have not been obtained for light emission brightness and light emission efficiency, and further higher brightness is desired.

[0003]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel oxadiazole derivative useful as a constituent component of an organic EL device having high brightness and high luminous efficiency and a method for producing the same.

[0004]

Means for Solving the Problems As a result of intensive studies for solving the above problems, the present inventors have found that an oxadiazole derivative having a specific structure is effective as a constituent component of an organic EL device. The present invention has been completed. That is, according to the present invention, the following general formula (1)

[Chemical 1] [In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, which may be the same or different. R ₁ and R ₂ are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group,
It represents an alkoxy group, an aryl group, an amino group, a cyano group, and a hydroxyl group, which may be the same or different. n represents an integer of 2 or 3 (however, in the case of 3,
It is attached to the 1, 3 and 5 positions of the benzene ring). ] The oxadiazole derivative represented by the following is also provided, and according to the present invention, the following general formula (2)

[Chemical 2] [In the formula, R ₂ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aryl group, an amino group, a cyano group, or a hydroxyl group. X represents a halogen atom. n represents an integer of 2 or 3 (however,
In the case of 3, it is bonded to the 1, 3 and 5 positions of the benzene ring). ] The acid halide compound represented by the following general formula (3)

[Chemical 3] [In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, which may be the same or different. R ₁ is a hydrogen atom,
It represents a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aryl group, an amino group, a cyano group, or a hydroxyl group. ] In with a tetrazole compound is reacted represented method oxadiazole derivatives, characterized by producing an oxadiazole derivative represented by the general formula (1) is Ru are provided.

The specific structure of the oxadiazole derivative represented by the general formula (1) of the present invention is represented by the following general formula (6), (7), (8) or (9). .

[Chemical 6]

[Chemical 7]

[Chemical 8]

[Chemical 9] [In the formulas (6), (7), (8) and (9), A, R ₁ and R ₂ are the same as above. ]

In the oxadiazole derivative represented by the general formula (1), specific examples of the aromatic hydrocarbon group or aromatic heterocyclic group represented by A include styryl, phenyl, biphenyl, terphenyl and naphthyl. , Anthryl, acenaphthenyl, fluorenyl, phenanthryl,
Indenyl, pyrenyl, pyridyl, pyrimidyl, furanyl, pyronyl, thiophenyl, quinolyl, benzofuranyl, benzothiophenyl, indolyl, carbazolyl,
Examples thereof include benzoxazolyl, quinoxalyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl and oxadiazolyl groups. Further, as the substituent of these aromatic hydrocarbon groups or aromatic heterocyclic groups, halogen atom, hydroxyl group, cyano group, nitro group, amino group, trifluoromethyl group, alkyl group having 1 to 6 carbon atoms, alkoxy group , Aryloxy group, phenyl group, styryl group, naphthyl group, thiophenyl group, aralkyl group, biphenyl group, bithiophenyl group, furanyl group, bifuranyl group, pyronyl group, bipyronyl group and the like.

Specific examples of the group represented by A in the general formula (1) are shown in Table 1.

[Table 1- (1)]

[0008]

[Table 1- (2)]

The oxa represented by the general formula (1)
In the diazole derivative, R₁~ R₂Substituent
The following may be mentioned. (1) Halogen atom, hydroxyl group, trifluoromethyl group,
Cyano group, nitro group. (2) Alkyl group: preferably C₁~ C₆, Especially C₁
~ C_FourA straight chain or branched chain alkyl group of
The alkyl group of is a fluorine atom, hydroxyl group, cyano group,
Coxy group, phenyl group, or halogen atom, alkyl
Substituted with a phenyl group or a substituted group or an alkoxy group
You may stay. (3) Aryl group: carbocyclic or heterocyclic aromatic ring
Yes, phenyl, naphthyl, anthryl, acenaphthenic
Le, fluorenyl, phenanthryl, indenyl, pyret
Nyl, pyridyl, pyrimidyl, furanyl, pyronyl, thiyl
Ophenyl, quinolyl, benzofuranyl, benzothiof
Phenyl, indolyl, carbazolyl, benzoxazoli
, Quinoxalyl, benzimidazolyl, pyrazolyl,
Dibenzofuranyl, dibenzothiophenyl, etc.
These aryl groups also include halogen atoms, hydroxyl groups, and
Group, nitro group, alkyl group, alkoxy group, amino group
Etc. may be substituted. (4) Alkoxy group (-OR³): R³Is defined in (2)
Represents an alkyl group. (5) Aryloxy group: The aryl group defined in (3)
The defined group is shown. (6) Alkylthio group (-SR³): R³Is defined in (2)
The group represented by Acyl group such as alkyl group, acetyl group, benzoyl group,
Or represents an aryl group defined in (3),
R such as piperidyl group and morpholyl group^FourAnd R^FiveToga
It may form a ring together with the elementary atom. Also, Yulorizil
Form a ring in cooperation with carbon atoms on the aryl group, such as
May be. (8) Alkoxycarbonyl group (-COOR⁶): R⁶Is
The alkyl group defined in (2) or defined in (3)
Represents an aryl group. R^FiveAnd R⁶Represents the meaning defined above. However, R
^FourAnd R^FiveForming a ring with a nitrogen atom in
except for. (10) such as methylenedioxy group or methylenedithio group
Indicates an alkylenedioxy group or alkylenedithio group
You (11) Styryl group (-CH = CH-C₆H_Five-R⁷):formula
Medium, R⁷Is a substituent or hydrogen defined in (1) to (10)
Indicates an atom.

The oxadiazole derivative represented by the general formula (1) in the present invention is an acid halide represented by the following general formula (2), specifically, the following general formula (10),
(11), (12) or (13)

[Chemical 10]

[Chemical 11]

[Chemical 12]

[Chemical 13] [Wherein (10), (11), (12), (13),
R ₂ is the same as above] and an acid halide compound represented by the following general formula (3)

[Chemical 3] It can be produced by reacting with a tetrazole compound represented by the formula: wherein A and R ₁ are the same as above.

Further, the oxadiazole derivative represented by the general formula (1) in the present invention has the general formula (4)
A tetrazole compound represented by, specifically, the following general formula (14), (15), (16) or (17)

[Chemical 14]

[Chemical 15]

[Chemical 16]

[Chemical 17] [In the formulas (14), (15), (16) and (17), R ₂
Is the same as the above] and a tetrazole compound represented by the following general formula (5)

[Chemical 5] It can be produced by reacting with an acid halide compound represented by the formula [wherein A, R ₁ and X are the same as above].

The tetrazole compound represented by the general formula (3) has the following general formula (18)

[Chemical 18] [Wherein A and R ₁ are the same as the above] in a tautomeric relationship with each other, which easily change each other and are difficult to take out separately. Is generally. Therefore, the tetrazole compounds of the general formula (3) and the general formula (18) can be used not only individually but also as a mixture of both. The same applies to the tetrazole compounds represented by the general formulas (14) to (17). Furthermore, the tetrazole compound represented by the general formula (3) has the following general formula (19):

[Chemical 19] [In the formula, A and R ₁ are the same as the above], and can be produced by forming a tetrazole using a cyano compound as a raw material. As the method, for example, Syn
The synthesis method described in thesis 71 (1973) can be applied. Further, the tetrazole compounds represented by the general formulas (14) to (17) can also be produced by the same method.

The method for producing these oxadiazole compounds of the present invention is described in R. D. It is performed according to the oxadiazole synthesis method by Huisgen et al. For example, Ange
w. Chem. , 72, 366 (1960), Che
m. Ber. , 93, 2106 (1960), Tetr
ahedron, 11, 241 (1960), Che
m. Ber. , 98, 2966 (1965).

Further, as an alternative method, the oxadiazole derivative represented by the general formula (1) is represented by the following general formula (2).

[Chemical 2] [In formula, R < ₂ >, X and n are the same as the above. ] The acid halide compound represented by the following general formula (20)

[Chemical 20] [In formula, A is the same as the above. ] It can also manufacture by making it react with the compound represented by these, and dehydrating the obtained product next.

As another alternative, the above-mentioned general formula (1)
The oxadiazole derivative represented by the following general formula (2
1)

[Chemical 21] [In formula, R < ₁ > and n are the same as the above. ] The compound represented by the following general formula (5)

[Chemical 5] [In the formula, A, R ₂ and X are the same as defined above. ] It can manufacture also by making it react with the compound represented by these, and then dehydrating the obtained product.

A reaction between the acid halide compound represented by the general formula (2) and the compound represented by the general formula (20),
And the reaction of the compound represented by the general formula (21) with the compound represented by the general formula (5) is usually carried out in the presence of a basic catalyst. Examples thereof include derivatives, organic bases such as triethylamine, tributylamine, triethanolamine, quinoline, piperazine and morpholine, and inorganic bases such as sodium hydroxide, potassium hydroxide and sodium carbonate, and organic basic catalysts are particularly preferable. As the reaction solvent in this step, any solvent can be used as long as it dissolves the raw materials, but alcohol solvents such as ethanol and butanol, ether solvents such as dioxane and tetrahydrofuran, benzene, toluene, chlorobenzene, nitrobenzene and the like. The aromatic solvents, N, N-dimethylformamide, dimethylsulfoxide and the like are preferable. Further, an organic basic catalyst such as pyridine may be used in excess and used as a solvent.

The reaction for synthesizing the oxadiazole derivative from the product thus obtained by a dehydration reaction is carried out in the presence of a dehydrating agent such as phosphorus oxychloride, thionyl chloride, polyphosphoric acid, boric acid, toluene and sulfonic acid. To do.
As the reaction solvent at this time, the solvent shown in the above step can be used, but aromatic solvents such as chlorobenzene, dichlorobenzene, xylene and nitrobenzene, and halogen solvents such as trichloromethane are particularly preferable. The amount of the dehydrating agent to be used is appropriately about 1 mol to 10 mol with respect to 1 mol of the starting material compound, but, for example, phosphorus oxychloride may be used in a large excess as a solvent. Usually the reaction is from 50 ° C to 3
Completed in minutes to 10 hours at 00 ° C.

The oxadiazole derivative represented by the above general formula (1) of the present invention is particularly excellent as a constituent component of an organic electroluminescent device. For example, it is formed into a thin film by a vacuum deposition method, a solution coating method or the like, And the device can be obtained by sandwiching directly or indirectly with the cathode.

[0019]

The present invention will be described in more detail based on the following examples. The present invention is not limited to these examples.

Synthesis Example 1 Synthesis of compound represented by structural formula (22) below

[Chemical formula 22] N, N-diphenylaminobenzaldehyde 15.00
g, hydroxylamine hydrochloride 4.60 g, acetic anhydride 1
1.30 g and 40 ml of dry DMF were placed in a reaction vessel, 6.51 g of pyridine as a solvent was gradually added, and the mixture was heated under reflux at 138 ° C. for 2.5 hours. After allowing to cool, the reaction product was poured into 500 ml of water, made alkaline with an aqueous sodium hydroxide solution, and the precipitate was filtered and washed with water. The obtained precipitate was extracted with toluene, washed with water and dried to obtain a crude product 13.4.
9 g (yield 90.9%) was obtained. The obtained crude product was purified by column chromatography (developing solvent: toluene) and further recrystallized from hexane to obtain 12.66 g (yield 85.2%) of transparent needle crystals. . The melting point is 125.8 to 126.5 ° C. and C≡N over 2200 cm ^{−1 according} to the infrared absorption spectrum.
A peak attributed to stretching vibration was observed, and it was confirmed to be the target product.

Synthesis Example 2 Synthesis of compound represented by structural formula (23) below

[Chemical formula 23] 4-Cyanotriphenylamine 1 obtained in Synthesis Example 1
1.50 g, sodium azide 5.40 g, ammonium chloride 4.44 g, and dry DMF 50 ml as a solvent were added, and the mixture was heated under reflux at 115 to 120 ° C. for 75 hours. After cooling, DMF was removed and the mixture was poured into 500 ml of water and acidified with concentrated hydrochloric acid. The precipitate was filtered, washed with water until it became neutral, and dried to obtain 13.28 g of a crude product (yield 99.6).
%) Was obtained. The obtained crude product was recrystallized from toluene to obtain 12.21 g (yield 91.5%) of white brown powder. The melting point is 216.3 to 217.3 ° C., and the peak attributed to the C≡N stretching vibration at 2200 cm ⁻¹ disappears due to the infrared absorption spectrum.
A peak attributed to N—H stretching vibration up to m ⁻¹ was observed. Furthermore, it was confirmed by the results of elemental analysis that the product was the target.

[Table 2]

Example 1 Synthesis of compound represented by structural formula (24) below

[Chemical formula 24] The following structural formula (25)

[Chemical 25] 1.10 g of the acid chloride compound represented by and 3.14 g of the tetrazole compound obtained in Synthesis Example 2 were placed in a reaction vessel, 90 ml of dry pyridine was added as a solvent, and 107 ° C.
Heated to reflux for 58 hours. After cooling, 700 ml of water
Then, the precipitate was filtered and dried to obtain 2.71 g (yield 77.2%) of a crude product. The crude product thus obtained was subjected to column chromatography (developing solvent: chloroform / THF = 30).
/ 1) twice, recrystallized with triene / ethanol, and washed with methanol to obtain 1.39 g (yield 39.6%) of a milky white powder. The melting point is 240.0-241.0 ° C.,
2600-3100c depending on infrared absorption spectrum
The peak attributed to N—H stretching vibration over m ⁻¹ disappeared, and the peak attributable to C═C stretching vibration was observed.
Furthermore, it was confirmed by the results of elemental analysis that the product was the target.

[Table 3]

Example 2 Synthesis of compound represented by structural formula (26) below

[Chemical formula 26] The following structural formula (27)

[Chemical 27] 1.10 g of the acid chloride compound represented by and 3.14 g of the tetrazole compound obtained in Synthesis Example 2 were placed in a reaction vessel, 90 ml of dry pyridine was added as a solvent, and 107 ° C.
Heated to reflux for 57 hours. After cooling, 700 ml of water
Then, the precipitate was filtered and dried to obtain 2.72 g of a crude product (yield 77.5%). The obtained crude product was subjected to column chromatography (developing solvent: chloroform / THF = 20).
/ 1) and recrystallized from toluene / ethanol to obtain 1.85 g (yield 52.7%) of milky white powder. The melting point is 270.0 to 271.0 ° C., which is 2600 to 31 by infrared absorption spectrum.
The peak attributed to the NH stretching vibration up to 00 cm ^-1 disappeared, the peak attributed to the C = C stretching vibration was observed, and the result of elemental analysis confirmed that it was the desired product.

[Table 4]

Example 3 Synthesis of compound represented by structural formula (28) below

[Chemical 28] The following structural formula (29)

[Chemical 29] 1.02 g of the acid chloride compound represented by and the tetrazole compound 3.14 g obtained in Synthesis Example 2 were placed in a reaction vessel, 90 ml of dry pyridine was added as a solvent, and 106 ° C.
Heated at reflux for 51 hours. After cooling, 600 ml of water
And the precipitate is filtered and dried to give 2.11 g of crude product.
(Yield 60.1%) was obtained. The obtained crude product was subjected to column chromatography (developing solvent: chloroform / THF =
30/1) and then column chromatography (developing solvent: toluene / ethyl acetate = 5 /) again.
Purification was performed twice according to 1). The obtained purified product was washed with methanol and recrystallized with toluene / hexane to obtain 0.70 g (yield 20.0%) of a pale green powder. The melting point is 217.0 to 218.0 ° C., which is 2600 to 3100 cm according to the infrared absorption spectrum.
^The peak attributed to N—H stretching vibration over ⁻¹ disappeared, and the peak attributed to C═C stretching vibration was observed. Furthermore, it was confirmed by the result of elemental analysis that the product was the target.

[Table 5]

Example 4 Synthesis of compound represented by structural formula (30) below

[Chemical 30] The following structural formula (31)

[Chemical 31] Into a reaction vessel, 0.76 g of the acid chloride compound represented by the formula and 2.69 g of the tetrazole compound obtained in Synthesis Example 2 were added, and 35 ml of dry pyridine was added as a solvent.
Heated to reflux for 72 hours. After cooling, 600 ml of water
2.53g of crude product
(Yield 87.2%) was obtained. The obtained crude product was subjected to column chromatography (developing solvent: chloroform / THF =
After purification by 30/1), washing with methanol was performed, and purification was performed again by column chromatography (developing solvent: chloroform / THF = 30/1).
The obtained purified product was recrystallized twice with toluene / methanol to obtain 0.81 g (yield 27.9%) of a pale green powder. The melting point is 237.0 to 238.0 ° C., and it is 2600 to 310 according to the infrared absorption spectrum.
The peak attributed to the NH stretching vibration at 0 cm ^-1 disappeared, the peak attributed to the C = C stretching vibration was observed, and the result of elemental analysis confirmed that it was the desired product.

[Table 6]

[0026]

[Application example]

Application Example 1 On a glass substrate on which indium tin oxide (ITO) having a size of 2 mm × 2 mm and a thickness of 170 mm is formed as an anode, a hole transport layer 40 nm composed of a compound represented by the following structural formula (32), the above structure A light emitting layer 35 nm composed of an oxadiazole derivative represented by the formula (26), an electron transporting layer 25 nm composed of an 8-hydroxyquinoline complex represented by the following structural formula (33), and further 10: 1 atomic ratio of Mg.
An electroluminescent device was produced by sequentially stacking 200 nm of Ag electrodes by vacuum vapor deposition. The degree of vacuum during vapor deposition is approximately 1 × 10 ^-4
Pa and the substrate temperature is room temperature. The ITO substrate was plasma-treated before vapor deposition. When a direct current power supply was connected to the anode and the cathode of the element thus manufactured through a lead wire to drive the element, the current density was 30 mA /
In cm ² , the applied voltage is 5.6 V and the brightness is 1450
cd / m ² (luminous efficiency: 2.71 lm / W) Green light emission with a light emission wavelength of 490 nm was observed, and high luminance of light emission was realized. In addition, it was confirmed that the device emitted light clearly even after storage for 3 months.

[Chemical 32]

[Chemical 33]

Application Example 2 Application Example 1 except that the oxadiazole derivative represented by the structural formula (24) is used as a light emitting material instead of the oxadiazole derivative represented by the structural formula (26).
An electroluminescent device was produced in the same manner as in. When a direct current power supply was connected to the anode and the cathode of the element thus manufactured through a lead wire to drive the element, the current density was 30 mA.
/ Cm ² , applied voltage is 7.0 V, brightness is 620
cd / ^{m 2} (luminous efficiency: 0.93lm / W), the emission wavelength was observed the emission of 460nm blue color, high brightness light was achieved. In addition, it was confirmed that the device emitted light clearly even after storage for 3 months.

Application Example 3 On a glass substrate on which indium tin oxide (ITO) having a size of 2 mm × 2 mm and a thickness of 170 mm was formed as an anode, a hole transport layer 40 nm composed of the compound represented by the structural formula (32) was used. A light emitting layer 15 nm composed of the oxadiazole derivative represented by the structural formula (26), an electron transport layer 20 nm composed of the oxadiazole compound represented by the following structural formula (34), and 8 represented by the structural formula (33).
-Electron injection layer 25n made of hydroxyquinoline complex
m, and a MgAg electrode with a 10: 1 atomic ratio of 200 nm
Were sequentially laminated by vacuum vapor deposition to fabricate an electroluminescent device. The degree of vacuum during vapor deposition is about 1 × 10 ⁻⁴ Pa, and the substrate temperature is room temperature. The ITO substrate was plasma-treated before vapor deposition. When a direct current power supply was connected to the anode and cathode of the device thus manufactured through a lead wire to drive the device, the applied voltage was 9.1 V and the brightness was 1800 cd / m ² at a current density of 30 mA / cm ² . (Emission efficiency: 2.07 lm / W), green emission with an emission wavelength of 490 nm was observed, and higher luminance of emission was realized. In addition, it was confirmed that the device emitted light clearly even after storage for 3 months.

[Chemical 34]

Application Example 4 Instead of the compound represented by the structural formula (32) as the hole transport material, the compound represented by the following structural formula (35) is used, and as the light emitting material, the compound represented by the structural formula (26) is represented. Instead of the oxadiazole derivative, the above structural formula (2
An electroluminescent device was produced in the same manner as in Application Example 3, except that the oxadiazole derivative represented by 8) was used. When a direct current power supply was connected to the anode and cathode of the element thus produced through a lead wire to drive the element, the applied voltage was 12.0 at a current density of 30 mA / cm ² .
V, brightness 720 cd / m ² (luminous efficiency: 0.63 lm
/ W), blue light emission with an emission wavelength of 470 nm was observed, and higher luminance of light emission was realized. This element is 3
Even after storage for a month, luminescence was clearly confirmed.

[Chemical 35]

Application Example 5 Application Example 4 except that the oxadiazole derivative represented by the above structural formula (30) is used as the light emitting material instead of the oxadiazole derivative represented by the above structural formula (28).
An electroluminescent device was produced in the same manner as in. When a direct current power supply was connected to the anode and the cathode of the element thus manufactured through a lead wire to drive the element, the current density was 30 mA.
/ Cm ² , the applied voltage is 13.5 V and the brightness is 45
3 cd / m ² (emission efficiency: 0.35 lm / W), green emission having an emission wavelength of 500 nm was observed, and high luminance of emission was realized. In addition, it was confirmed that the device emitted light clearly even after storage for 3 months.

Comparative Example 1 On a glass substrate on which indium-tin oxide (ITO) having a size of 2 mm × 2 mm and a thickness of 170 mm was formed as an anode, a hole transfer consisting of a compound represented by the following structural formula (36) was carried out. Layer 40 nm, light emitting layer 15 nm composed of aminopyrene derivative represented by the following structural formula (37), electron transport layer 20 nm composed of oxadiazole compound represented by the following structural formula (38), and 8 represented by the structural formula (33).
-Electron injection layer 25n made of hydroxyquinoline complex
m, and a MgAg electrode with a 10: 1 atomic ratio of 200 nm
Were sequentially laminated by vacuum vapor deposition to fabricate an electroluminescent device. The degree of vacuum during vapor deposition is about 1 × 10 ⁻⁴ Pa, and the substrate temperature is room temperature. When a direct current power supply was connected to the anode and cathode of the device thus produced through a lead wire to drive the device, the applied voltage was 5.8 V and the brightness was 325 cd / m ² at a current density of 30 mA / cm ² . A green emission with an emission wavelength of 500 nm was observed.

[Chemical 36]

[Chemical 37]

[Chemical 38]

Comparative Example 2 As a positive electrode, on a glass substrate on which indium-tin oxide (ITO) was formed, a hole transport layer of 60 nm composed of the compound represented by the structural formula (32), the following structural formula (3)
9) Emissive layer made of oxadiazole compound represented by 10 nm, electron transport layer made of oxadiazole compound represented by the following structural formula (40) 30 nm, further 10:
An electroluminescent device was prepared by sequentially laminating 200 nm of MgAg electrodes having a one-atom ratio by vacuum evaporation. The degree of vacuum during vapor deposition is about 1 × 10 ⁻⁴ Pa, and the substrate temperature is room temperature. When a direct current power supply was connected to the anode and the cathode of the device thus manufactured through a lead wire to drive the device, the applied voltage was 17 V at a current density of 300 mA / cm ² .
Luminance is 4000 cd / m ² , (luminous efficiency: 0.25 lm
/ W), green light emission with an emission wavelength of 521 nm was observed.

[Chemical Formula 39]

[Chemical 40]

[0033]

The oxadiazole derivative of the present invention is a novel compound, which is a bipolar compound having both an oxadiazole ring having an electron transport function and an arylamine structure having an electron donating function, It has a high fluorescence intensity and particularly has excellent properties as a light emitting component of an organic EL device. Thus, using the oxadiazole derivative of the present invention as a light emitting component of a light emitting layer, it has been conventionally known as a charge transporting component of a charge transporting layer. An electroluminescent device using a material has extremely excellent emission brightness and emission efficiency.

─────────────────────────────────────────────────── --- Continuation of the front page (56) Reference JP-A-4-363891 (JP, A) JP-A-6-65569 (JP, A) JP-A-4-115487 (JP, A) JP-A-7- 109451 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) C07D 271/10 C07D 413 / 12,473 / 14 C09K 11/06 H05B 33 / 14,33 / 22 REGISTRY (STN) CA ( STN) CAOLD (STN)

Claims (2)

(57) [Claims] 1. The following general formula (1): [In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, which may be the same or different. R ₁ and R ₂ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aryl group, an amino group, a cyano group and a hydroxyl group, and may be the same or different. n is
It represents an integer of 2 or 3 (however, in the case of 3, it is bonded to the 1, 3 and 5 positions of the benzene ring). ] The oxadiazole derivative represented by these. 2. The following general formula (2): [In the formula, R ₂ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, an aryl group, an amino group,
Represents a cyano group and a hydroxyl group. X represents a halogen atom. n represents an integer of 2 or 3 (however, in the case of 3, it is bonded to the 1, 3, and 5 positions of the benzene ring). ] And an acid halide compound represented by the following general formula (3): [In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, which may be the same or different. R ₁ is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group,
It represents an aryl group, an amino group, a cyano group or a hydroxyl group. ] By reacting with a tetrazole compound represented by
A method for producing an oxadiazole derivative, which comprises producing the oxadiazole derivative represented by the general formula (1) according to claim 1 .