JPH04283574A - 1,2,5-thiadiazolopyrene derivative and organic electroluminescent element using the same - Google Patents

Abstract

PURPOSE:To obtain a new compound, having a high fluorescent intensity and excellent in light and heat resistance as a luminous material for organic electroluminescent elements. CONSTITUTION:A compound expressed by formula I (R<1> to R<8> are H, halogen, alkyl, aralkyl, etc.). The aforementioned compound is obtained by adding benzyltrimethylammonium bromide to a pyrene derivative expressed by formula II, reacting both in a mixture solution of an alkyl halide-based solvent such as dichloromethane and an alcohol such as methanol or ethanol at ambient temperature, providing a compound expressed by formula III, then adding sodium methoxide and copper iodide thereto, further refluxing the prepared mixture in an atmosphere of nitrogen in dry DMF solvent under heated conditions, affording a compound expressed by formula IV, subsequently refluxing the resultant compound expressed by formula IV in a mixed solution of hydrobromic acid and acetic acid under heated conditions, affording a compound expressed by formula V, further mixing the obtained compound expressed by formula V with N4S4 in an aromatic hydrocarbon-based solvent such as benzene or toluene and refluxing the resultant mixture under heated conditions.

Description

[Detailed description of the invention]

0001

FIELD OF THE INVENTION The present invention relates to a novel 1,2,5-thiadiazolopyrene derivative and an organic electroluminescent device using the same. More specifically, it relates to various fluorescent display materials, fluorescent dyes for resins, laser dyes, novel compounds with fluorescence that can be used as light-emitting materials for organic electroluminescent devices made of organic compounds, and organic electroluminescent devices using the same. It is something.

0002

[Prior Art] Conventionally, thin film type electroluminescent devices include:
ZnS, which is a II-VI group compound semiconductor of inorganic material, C
aS, SrS, etc., include Mn, which is the luminescent center, and rare earth elements (
Doped with Eu, Ce, Tb, Sm, etc.) was common. However, electroluminescent devices made from the above-mentioned inorganic materials require (1) AC drive (50 to 100
0Hz), (2) High driving voltage (~200V), (3
) It is difficult to make it full color (blue in particular is a problem), and (4) the cost of peripheral drive circuits is high.

In recent years, in order to improve the above-mentioned problems, electroluminescent devices using organic materials have been developed. In addition to anthracene and pyrene, which have been known for a long time, cyanine dyes (J. Chem.
Soc. , Chem. Commun. 557, 1985), pyrazoline (Mol. Cryst.
Liq. Cryst. , vol. 135, p. 355,
1986), Perylene (Jpn. J. Appl.
Phys. 25, page L773, 1986), or coumarin-based compounds and tetraphenylbutadiene (
JP-A No. 57-51781), etc. have been reported. In addition, in order to increase the luminous efficiency, we are optimizing the type of electrodes to improve the injection efficiency of carriers from the electrodes.
A device to provide a light-emitting layer consisting of a hole injection transport layer and an organic phosphor (JP-A-57-51781, JP-A-59-19)
No. 4393, JP-A No. 63-295695, A
ppl. Phys. Lett. 51, p. 913, 1987).

Furthermore, in order to improve the luminous efficiency of the device and change the luminescent color, various fluorescent dyes are doped using an aluminum complex of 8-hydroxyquinoline as a host material (J. Appl. Phys. Vol. 65, 3).
610, 1989) has also been carried out.

[0005]

However, the organic electroluminescent devices disclosed in these documents still have insufficient luminous performance, particularly luminous efficiency, and further improvement studies have been desired. In view of the above-mentioned circumstances, the present inventors conducted extensive studies with the aim of providing an organic electroluminescent device that can be driven stably over a long period of time, and as a result, discovered that a specific compound was suitable, and completed the present invention. I ended up doing it.

[0006]

[Means for Solving the Problems] That is, the gist of the present invention is that the following general formula (I)

[0007]

[Case 2]

(In the formula, R1 to R8 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an allyl group, a cyano group, an amino group, an amide group, a nitro group, an alkoxycarbonyl group) , a carboxyl group, an alkoxy group, an aromatic hydrocarbon ring group or a heterocyclic group which may have a substituent), an anode, an organic hole injection In a device in which a transport layer, an organic electron injection transport layer, and a cathode are laminated in this order, the organic hole injection transport layer and/or the organic electron injection transport layer is composed of 1,2,5-thiadiazole represented by the above general formula (I). An organic electroluminescent device characterized by containing a lopyrene derivative.

The present invention will be explained in detail below. The 1,2,5-thiadiazolopyrene derivative of the present invention has the above general formula (
This is a compound represented by I). In general formula (I), R1 to R8 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an allyl group, a cyano group, an amino group, an amide group, a nitro group, an alkoxycarbonyl group. , a carboxyl group, an alkoxy group, an aromatic hydrocarbon ring group which may have a substituent, or an aromatic heterocyclic group.

Among these, R1, R2, R3, R7
and R8 is preferably a halogen atom such as a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group,
Alkyl group having 1 to 6 carbon atoms such as ethyl group; methoxy group,
Alkoxy group having 1 to 6 carbon atoms such as ethoxy group; 1 to 6 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group
alkoxysulfonyl groups such as methoxysulfonyl group and ethoxysulfonyl group; cyano group, amino group, dimethylamino group, nitro group, etc., but a hydrogen atom is particularly preferably selected.

R4, R5, and R6 are preferably hydrogen atoms, halogen atoms such as chlorine atoms, bromine atoms, and iodine atoms, cyano groups, amino groups, dimethylamino groups,
a nitro group or a methyl group which may have a substituent,
Alkyl group having 1 to 6 carbon atoms such as ethyl group; methoxy group,
Alkoxy group having 1 to 6 carbon atoms such as ethoxy group; 1 to 6 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group
alkoxycarbonyl group; alkoxysulfonyl group such as methoxysulfonyl group and ethoxysulfonyl group; aralkyl group such as benzyl group and phenethyl group; phenyl group,
Examples include aromatic hydrocarbon groups such as naphthyl, acenaphthyl, and anthryl; and heterocyclic groups such as thienyl, carbazole, indolyl, and furyl.

Substituents for these include alkyl groups having 1 to 6 carbon atoms such as methyl group and ethyl group; lower alkoxy groups such as methoxy group; aryloxy groups such as phenoxy group and trioxy group; benzyloxy group aryl alkoxy groups such as phenyl groups and naphthyl groups; substituted amino groups such as dimethylamino groups; particularly preferred are halogen atoms such as hydrogen atoms and chlorine atoms;
An alkyl group having 1 to 6 carbon atoms and an alkoxy group having 1 to 6 carbon atoms are selected.

1,2 represented by the general formula (I) of the present invention
, 5-thiadiazolopyrene derivatives include Compound No. 1 shown in Table 1 below. 1~No
．． I can list 9. These compounds have high fluorescence intensity and good light resistance and heat resistance.

[0014]

[Table 1]

1,2,5 represented by the above general formula (I)
-Thiadiazolopyrene derivatives can be produced by the following method. For example, the following general formula (II)

00
16]

[Chemical formula 3]

(wherein R1 to R8 represent the general formula (I
) has the same meaning as in ) is reacted with tribromine benzyltrimethylammonium in a mixture of a halogenated alkyl solvent such as dichloromethane or chloroform and an alcohol such as methanol or ethanol at room temperature to obtain the following general formula (III) ( In the formula, R1 to R8 represent the general formula (
It has the same meaning as in I). ) is obtained.

[0018]

[C4]

This compound (III) was prepared by adding sodium methoxide and copper iodide in a dry dimethylformamide solvent and heating to reflux in a nitrogen atmosphere to form the following general formula (IV) (wherein R1 to R8 are A compound represented by the formula (having the same meaning as in general formula (I)) is obtained.

[0020]

[C5]

By heating and refluxing this compound (IV) in a mixture of hydrobromic acid and acetic acid, the following general formula (V) is obtained.
A compound represented by the formula (wherein R1 to R8 have the same meanings as in general formula (I)) is obtained.

[0022]

[C6]

This compound (V) is dissolved in tetranitrogen tetrasulfide (N4 S4
) and heating under reflux, the general formula (I)
A 1,2,5-thiadiazolopyrene derivative represented by the formula can be obtained. These compounds exhibit strong fluorescence in a solution state and are suitable as fluorescent dyes for doping organic electroluminescent devices, and at the same time have the ability as fluorescent dyes for resin dispersion.

Next, an organic electroluminescent device using the 1,2,5-thiadiazolopyrene derivative of the present invention will be explained with reference to the accompanying drawings. FIG. 1 is a cross-sectional view schematically showing a structural example of an organic electroluminescent device of the present invention, in which 1 is a substrate, 2
a and 2b each represent a conductive layer, 3 an organic hole injection transport layer, and 4 an organic electron injection transport layer.

The substrate 1 serves as a support for the organic electroluminescent element, and may be a quartz or glass plate, a metal plate or metal foil, a plastic film or sheet, and may be a glass plate, polyester, polymethacrylate,
A transparent synthetic resin substrate such as polycarbonate or polysulfone is preferred.

A conductive layer 2a is provided on the substrate 1,
This conductive layer 2a is usually made of aluminum, gold, silver,
It is composed of metals such as nickel, palladium, and tellurium, metal oxides such as oxides of indium and/or tin, and conductive resins such as copper iodide, carbon black, and poly(3-methylthiophene).

[0027] The conductive layer is usually formed by sputtering method,
This is often done by vacuum evaporation, but in the case of fine metal particles such as silver, copper iodide, carbon black, conductive metal oxide fine particles, conductive resin fine powder, etc., it is necessary to use a suitable binder resin solution. It can also be formed by dispersing and coating on a substrate. Furthermore, in the case of conductive resin, a thin film can be formed directly on the substrate by electric field polymerization. The above conductive layer can also be formed by laminating different materials.

The thickness of the conductive layer 2a varies depending on the required transparency, but if transparency is required, it is desirable that the visible light transmittance is 60% or more, preferably 80% or more. In this case, the thickness is usually 50 to 1000
The thickness is about 0 Å, preferably about 100 to 5000 Å. The conductive layer 2a may be the same as the substrate 1 if it is opaque. In the example of FIG. 1, the conductive layer 2a serves as an anode to inject holes.

On the other hand, the conductive layer 2b serves as a cathode to inject electrons into the organic electron injection and transport layer 4. The material used for the conductive layer 2b is the same as the conductive layer 2a.
However, for efficient electron injection, metals with low work functions are preferred, and metals such as tin, magnesium, indium, aluminum, silver, etc., or alloys thereof are used. It will be done. Conductive layer 2b
The film thickness of the conductive layer 2a is usually the same as that of the conductive layer 2a.

Furthermore, although not shown in FIG. 1, a substrate similar to substrate 1 may be further provided on conductive layer 2b. However, as an electroluminescent device, it is necessary that at least one of the conductive layers 2a and 2b has good transparency. From this, one of the conductive layers 2a and 2b has a 100 to 500
The film thickness is preferably 0 Å, and good transparency is desired.

An organic hole injection transport layer 3 is formed on the conductive layer 2a.
The organic hole injection transport layer 3 is formed of a compound that can efficiently transport holes from the anode toward the organic electron injection transport layer 4 between the electrodes to which an electric field is applied. The organic hole injection/transport compound needs to be a compound that has high hole injection efficiency from the conductive layer 2a and can efficiently transport the injected holes. To this end, it is required that the compound has a low ionization potential, high hole mobility, excellent stability, and is unlikely to generate trapping impurities during production or use.

[0032] Such hole injection transport compounds include:
Examples include those described in pages 5 to 6 of Japanese Patent Application Laid-open No. 59-194393 and columns 13 to 14 of US Pat. No. 4,175,960. Preferred specific examples of these compounds include N,N'-diphenyl-N,N'-(
3-methylphenyl)-1,1'-biphenyl-4,4
Examples include aromatic amine compounds such as '-diamine, 1,1'-bis(4-di-p-tolylaminophenyl)cyclohexane, and 4,4'-bis(diphenylamino)quadrophenyl. In addition to aromatic amine compounds, hydrazone compounds disclosed in JP-A-2-311591 may be mentioned. These aromatic amine compounds or hydrazone compounds may be used alone or as a mixture, if necessary.

[0033] The organic hole injection and transport layer 3 is formed by laminating it on the conductive layer 2a by a coating method or a vacuum evaporation method. For example, in the case of a coating method, one or more organic hole injecting and transporting compounds and, if necessary, additives such as a binder resin that does not become a hole trap and a coating properties improver such as a leveling agent are added. The conductive layer 2 is prepared by adjusting the dissolved coating solution and applying a method such as spin coating.
a and dried to form an organic hole injection transport layer 3. Examples of the binder resin include polycarbonate, polyarylate, polyester, and the like. If the binder resin is added in a large amount, the hole mobility will be reduced, so a smaller amount is preferable, and 50% by weight or less is preferable.

In the case of the vacuum evaporation method, the organic hole injecting and transporting material is placed in a crucible placed in a vacuum container, and after the inside of the vacuum container is evacuated to 10-6 Torr using a suitable vacuum pump, the crucible is is heated to evaporate the hole injection transport material and form a layer on a substrate placed opposite the crucible. The film thickness of the organic hole injection transport layer is usually 100 to 3
000 Å, preferably 300 to 1000 Å. Vacuum deposition is often used to uniformly form such thin films.

The organic electron injection and transport layer 4 is provided on the organic hole injection and transport layer 3, and the organic electron injection and transport layer efficiently transfers electrons from the cathode to organic holes between the electrodes to which an electric field is applied. It is formed from a compound that can be transported in the direction of the injection transport layer 3. The organic electron injection/transport compound needs to be a compound that has high electron injection efficiency from the conductive layer 2b and can efficiently transport the injected electrons. To this end, it is required that the compound has a high electron affinity, a high electron mobility, and is also highly stable and does not easily generate trapping impurities during production or use.

Examples of materials that satisfy these conditions include aromatic compounds such as tetraphenylbutadiene and coumarin (Japanese Patent Application Laid-Open No. 57-51781) and metal complexes such as aluminum complexes of 8-hydroxyquinoline (Japanese Patent Application Laid-Open No. 59-1989).
-194393), etc. When these compounds are used, the organic electron injection/transport layer simultaneously plays the role of transporting electrons and the role of producing light emission upon recombination of holes and electrons. The film thickness of the organic electron injection transport layer 4 is usually 100 to 2000 Å, preferably 300 to 10 Å.
00 Å. The organic electron injection transport layer can also be formed by the same method as the organic hole injection transport layer, but usually a vacuum evaporation method is used.

[0037] In order to improve the luminous efficiency of organic light emitting devices and change the luminescent color, various fluorescent dyes have been doped using an aluminum complex of 8-hydroxyquinoline as a host material (US Pat. ,7
No. 69,292). The advantages of this doping method include: ■ Improved luminous efficiency due to highly efficient fluorescent dye; ■
The emission wavelength can be selected by selecting the fluorescent dye, (1) Fluorescent dyes that cause concentration quenching can also be used, and (2) Fluorescent dyes with poor film properties can also be used.

[0038] The fluorescent dye is usually used in the organic electron injection transport layer 4.
(see Figure 1). However, depending on the properties of the fluorescent dye to be doped, the layer to be doped may be an organic hole injection transport layer 3, and furthermore, as in the structure shown in FIG. It may be near the interface 3b on the injection transport layer 4 side. Further, both the organic hole injection transport layer 3 and the organic electron injection transport layer 4 may be doped. The amount of fluorescent dye doped into the host material is preferably 10-3 to 10 mol%. As described above, when the compound according to the present invention is used as a dope material for an organic electroluminescent device, it can provide excellent luminescent properties and long-term stability.

It is also possible to have a structure opposite to that shown in FIG. 2, that is, to stack the conductive layer 2b, organic electron injection transport layer 4, organic hole injection transport layer 3, and conductive layer 2a on the substrate in this order.
As mentioned above, it is also possible to provide an organic electroluminescent element between two substrates, at least one of which is highly transparent. Similarly, a structure opposite to that of FIG. 2 is provided, that is, a conductive layer 2b, an organic electron injection and transport layer 4, a doped organic hole injection and transport layer 3b, and an undoped organic hole injection and transport layer on the substrate. It is also possible to stack the conductive layer 3a and the conductive layer 2a in this order.

[0040]

EXAMPLES Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the description of the following examples unless it exceeds the gist thereof.

Example 1 4.93 g of pyrene was added to a mixed solution of 200 ml of dichloromethane and 20 ml of methanol, and 10.45 g of benzyltrimethylammonium tribromination was added little by little over 2 minutes at room temperature, followed by stirring for 5 hours. The reaction mixture was diluted with NaHCO
3 Washed with aqueous solution and saturated brine, dried, and then the solvent was distilled off under reduced pressure to obtain 5.13 g of 1-bromopyrene.

15.00 g of the obtained 1-bromopyrene,
A mixed solution of 28.82 g of sodium methoxide, 250 ml of dry dimethylformamide, and 11.2 g of copper iodide was heated under reflux for 24 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, filtered, poured into ice water, neutralized with an aqueous hydrochloric acid solution, and filtered again. The filtrate was extracted with dichloromethane, the organic layer was washed with saturated brine, and after drying, the solvent was distilled off under reduced pressure, and the filtrate was subjected to silica gel column chromatography, and developed with hexane:benzene (6:1). ．．
59 g of 1-methoxypyrene were obtained. This was recrystallized from hexane to obtain 6.73 g of 1-methoxypyrene.

10.00 g of the obtained 1-methoxypyrene
, 30 ml of HBr (47%), and 100 ml of acetic acid was heated under reflux for 9 hours. The reaction mixture was cooled to room temperature, filtered, and the residue was dissolved in ether, dried, and then evaporated under reduced pressure. The residue was dissolved in benzene and filtered to obtain the following 1-hydroxypyrene. Recrystallized in chloroform, 5.93
g of 1-hydroxypyrene was obtained.

Obtained 1-hydroxypyrene 0.505
A mixed solvent of 20 ml of toluene, 0.47 g of tetranitrogen tetrasulfide (N4 S4), and 20 ml of toluene was heated under reflux for 24 hours. The reaction mixture was cooled to room temperature and filtered, and the filtrate was distilled off under reduced pressure. The residue was subjected to silica gel chromatography, and sulfur was obtained from the hexane fraction. Next, hexane:benzene (2:1)
1,2,5- of the following structural formula (1) which is the target product from the fraction
A thiadiazolopyrene derivative was obtained. Add this to ethanol:
Recrystallized with a mixed solvent of toluene (9:1) to give 0.223
g (yield 38%) of a 1,2,5-thiadiazolopyrene derivative was obtained.

[0045]

[C7]

This compound is a brown plate-shaped crystal with a melting point of 1.
The temperature was 80-183°C. The analysis results for this compound are shown below. Elemental analysis (molecular formula is C16H8N2S) calculated value
C. 73.82; H. 3.10;N. 1
0.76 analysis value C. 73.34; H. 3
．． 53;N. 10.56 infrared spectrum absorption wave number (
KBr) 3050, 1590, 1490, 1475
, 1440, 1395, 1370, 1
335, 1280, 1235, 1175,
1145, 910, 860, 850,
840, 825, 760, 680 cm
-1 Mass spectrometry Analysis of m/z=260 (M+) or higher confirmed that this product was the target compound.

Example 2 Using the 1,2,5-thiadiazolopyrene derivative obtained in Example 1, an organic electroluminescent device having the structure shown in FIG. 1 was produced. Indium tin oxide (ITO) on a glass substrate
) After washing the transparent conductive film deposited with a thickness of 1200 Å with water and ultrasonic cleaning with isopropyl alcohol, it was placed in a vacuum evaporation device, and an oil diffusion pump was used until the degree of vacuum in the device became 2 × 10-6 Torr or less. It was exhausted. As an organic hole injection transport layer material, hydrazone compounds represented by the following structural formulas (2) and (3) were mixed at a molar ratio of 1:0.3.

[0048]

[Chemical formula 8]

[0049] This was placed in a ceramic crucible, heated with a Ta ray heater around the crucible, and evaporated in a vacuum container. The temperature of the crucible was in the range of 160 to 180°C, and the degree of vacuum during vapor deposition was 2 x 10-6 to 8 x 10-7 Torr. An organic hole injection transport layer was thus deposited to a thickness of 520 Å. The deposition time was 4 minutes.

Next, as a material for the organic electron injection transport layer,
8-hydroxyquinoline complex of aluminum represented by the following structural formula (4)

[0051]

[Chemical formula 9]

[0052] The 1,2,5-thiadiazolopyrene derivative obtained above as a fluorescent dye to be doped was heated and vapor-deposited at the same time using separate crucibles. At this time, the temperature of each crucible was 150 to 180°C, 1,2
, 5-thiadiazolopyrene derivatives were controlled at 70°C. The degree of vacuum during vapor deposition was 6 x 10-7 Torr, and the vapor deposition time was 2 minutes. As a result, 1 with a film thickness of 520 Å
An organic electron injection transport layer doped with 5 mol % of ,2,5-thiadiazolopyrene derivative was obtained.

Finally, as a cathode, an alloy electrode of magnesium and silver was deposited to a thickness of 1500 Å by a binary simultaneous deposition method. A glossy film was obtained using a molybdenum boat for vapor deposition at a vacuum level of 8 x 10-6 Torr and a vapor deposition time of 8 minutes. The atomic ratio of magnesium and silver is 10:1 ~
It was in the range of 2. In this way, organic electroluminescent device A was obtained.

Example 3 An organic electroluminescent device having the structure shown in FIG. 2 was produced. On the anode substrate (ITO glass) cleaned in the same manner as in Example 2, the same mixture of hydrazone compounds as in Example 2 was deposited in the same manner as in Example 2 to form an organic hole injection transport layer 3 with a thickness of 300 Å.
A was formed. Next, the above hydrazone mixture and Example 1
and the 1,2,5-thiadiazolopyrene derivative obtained in (1) were simultaneously vapor-deposited to form an organic hole injection transport layer 3b doped with 9 mol % of the above derivative (1) and having a thickness of 300 Å.

Furthermore, as an organic electron injection and transport layer, an 8-hydroxyquinoline complex of aluminum was laminated to a thickness of 530 Å in the same manner as in Example 2, and finally a magnesium and silver alloy cathode was formed to form an organic electric field. A light emitting element B was obtained. The ITO electrode of the organic electroluminescent device thus obtained (
Table 2 shows the results of the luminescence characteristics measured by applying a positive DC voltage to the anode (anode) and a negative DC voltage to the magnesium/silver electrode (cathode).

[0056]

[Table 2]

These devices exhibited uniform green light emission with an emission peak around 520 nm. Furthermore, after storing these elements in vacuum for one month, the luminescent properties were evaluated again, and no significant decrease in brightness or luminous efficiency was observed.

[0058]

[Effects of the Invention] The compounds of the present invention have high fluorescence intensity and good light resistance and heat resistance. This compound may be used as an organic hole injection transport layer and/or of an organic electroluminescent device in which an anode, an organic hole injection transport layer, an organic electron injection transport layer, and a cathode are sequentially provided on a substrate. When used as an organic electron injecting and transporting layer, or by doping a portion thereof as a fluorescent dye, when a voltage is applied using both conductive layers as electrodes, luminescence with sufficient luminance for practical use can be obtained with a low driving voltage.

Therefore, the compounds of the present invention can be used in the field of flat panel displays (for example, wall-mounted televisions) and light sources that take advantage of their characteristics as surface light emitters (for example, light sources for copying machines, backlight sources for liquid crystal displays and instruments). It can be applied to display boards, sign lights, and is extremely useful industrially.

[Brief explanation of the drawing]

FIG. 1 is a cross-sectional view showing the structure of an organic electroluminescent device manufactured in Example 2.

FIG. 2 is a cross-sectional view showing the structure of the organic electroluminescent device manufactured in Example 3.

[Explanation of symbols]

1 Substrates 2a, 2b Conductive layer 3a Organic hole injection transport layer 3b Organic hole injection transport layer doped with fluorescent dye 4 Organic electron injection transport layer

Claims (2)

[Claims] Claim 1: 1,2,5 represented by general formula (I)
- Thiadiazolopyrene derivatives. [Formula 1] (wherein R1 to R8 are each independently a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an allyl group, a cyano group, an amino group, an amide group, a nitro group, an alkoxycarbonyl group) group, carboxyl group, alkoxy group, aromatic hydrocarbon ring group or heterocyclic group that may have a substituent.) 2. An element in which an anode, an organic hole injection transport layer, an organic electron injection transport layer, and a cathode are laminated in this order, wherein the organic hole injection transport layer and/or the organic electron injection transport layer are , 5-thiadiazolopyrene derivative.