JP4423022B2 - 2,1-Benzisothiazole compound and organic light emitting device using the same - Google Patents

Description

  The present invention relates to a novel organic compound and an organic light-emitting device using the same.

  An organic light-emitting device has a fluorescent compound or a phosphorescent compound by injecting electrons and holes from each electrode by sandwiching a thin film containing a fluorescent organic compound or a phosphorescent organic compound between an anode and a cathode. This is an element that utilizes the light emitted when the exciton is generated and the exciton returns to the ground state.

In 1987, Kodak Research (Non-patent Document 1) used ITO for the anode and magnesium silver alloy for the cathode, an aluminum quinolinol complex for the electron transport material and the light emitting material, and a triphenylamine derivative for the hole transport material. It has been reported that light emission of about 1000 cd / m ^{2 at} an applied voltage of about 10 V has been reported with an element having a function separation type two-layer structure. Examples of related patents include Patent Documents 1 to 3 and the like.

  In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively researched. For example, it describes in patent documents 4-11.

  In recent years, many studies have been made on using phosphorescent compounds as light emitting materials and using triplet state energy for EL light emission. A group of Princeton University reports that an organic light emitting device using an iridium complex as a light emitting material exhibits high luminous efficiency (Non-Patent Document 2).

  Furthermore, in addition to the organic light-emitting device using the low-molecular material as described above, an organic light-emitting device using a conjugated polymer has been reported by a group of Cambridge University (Non-Patent Document 3). In this report, light emission was confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system. Patents 12 to 16 and the like can be cited as related patents of organic light emitting devices using conjugated polymers.

  As described above, recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low profile, and light-emitting devices with low applied voltage. Suggests the possibility to.

  However, under the present circumstances, light output with higher brightness or higher conversion efficiency is required. In addition, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. Furthermore, it is necessary to emit blue, green, and red light with good color purity when considering application to a full color display or the like, but these problems are still not sufficient.

  On the other hand, benzoisothiazole compounds are used as charge transport materials and light-emitting materials because of their excellent charge transport properties and light-emitting properties. Examples of using a benzoisothiazole compound in an organic light emitting device include Patent Documents 17 to 20 and the like. However, 1,3-benzoisothiazole is used in an organic light emitting device, and characteristics when used as a light emitting layer material Is not enough.

US Pat. No. 4,539,507 US Pat. No. 4,720,432 US Pat. No. 4,885,211 US Pat. No. 5,151,629 US Pat. No. 5,409,783 US Pat. No. 5,382,477 JP-A-2-247278 JP-A-3-255190 JP-A-5-202356 JP-A-9-202878 JP-A-9-227576 US Pat. No. 5,247,190 US Pat. No. 5,514,878 US Pat. No. 5,672,678 JP-A-4-145192 Japanese Patent Application Laid-Open No. 5-247460 JP-A-11-283746 JP 11-185959 A Japanese Patent Laid-Open No. 10-298545 Japanese Patent Laid-Open No. 08-087123 Appl. Phys. Lett. 51,913 (1987) Nature, 395, 151 (1998) Nature, 347, 539 (1990)

  An object of the present invention is to provide a novel 2,1-benzisothiazole compound.

  It is another object of the present invention to provide an organic light-emitting device that uses a specific 2,1-benzoisothiazole compound and has an extremely high efficiency and high luminance light output. Another object of the present invention is to provide an extremely durable organic light emitting device. It is another object of the present invention to provide an organic light emitting device that is easy to manufacture and can be produced at a relatively low cost.

That is, the 2,1-benzisothiazole compound of the present invention is represented by the following general formulas [I] to [IV]. Of the 2,1-benzoisothiazole compounds represented by the following general formulas [I] to [IV], the compounds shown below correspond to the present invention.

Wherein R1 to R5 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic Represents a group, a substituted or unsubstituted condensed polycyclic heterocyclic group or a substituted amino group, at least one of which is a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic ring An aromatic group, a substituted or unsubstituted condensed polycyclic heterocyclic group, or a substituted amino group, R1 to R5 may be the same or different.

Wherein R6 to R8 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic Represents a group, a substituted or unsubstituted condensed polycyclic heterocyclic group, and a substituted amino group, and R6, R7, R8, and R9 bonded to different benzoisothiazole rings may be the same or different. The R6 to R8 bonded to the same benzoisothiazole ring may be the same or different.

  R9 and R10 are a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted condensed polycyclic heterocyclic group, and a substituted amino group. May be the same or different.

  n is an integer of 2 or more. )

Wherein R11 to R14 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic Represents a group, a substituted or unsubstituted condensed polycyclic heterocyclic group, and a substituted amino group, and R11, R12, R13, and R14 bonded to different benzoisothiazole rings may be the same or different. The R11 to R14 bonded to the same benzoisothiazole ring may be the same or different.

  R15 represents any of a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted condensed polycyclic heterocyclic group, and a substituted amino group. Represents.

  m represents an integer of 2 to 6. )

Wherein R17 to R20 are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic Represents a group, a substituted or unsubstituted condensed polycyclic heterocyclic group, and a substituted amino group, and R17, R18, R19, and R20 bonded to different benzoisothiazole rings may be the same or different. The R17 to R20 bonded to the same benzoisothiazole ring may be the same or different.

  R16 represents any of a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted condensed polycyclic heterocyclic group, and a substituted amino group. Represents.

  L represents an integer of 2 to 6. )

  Here, in the 2,1-benzisothiazole compound represented by the general formula [I], at least one of R1, R2, and R5 is preferably a substituted amino group.

Further, the organic light-emitting device of the present invention comprises a pair of electrodes including an anode and a cathode, being interposed between the pair of electrodes has a, and an organic compound layer including at least a light emitting layer, the light-emitting layer is lower SL 2, It contains at least one of 1-benzothiazole compounds.

  The organic light-emitting device using the benzoisothiazole compound of the present invention can emit light with high luminance at a low applied voltage and has excellent durability. In particular, an organic layer containing the benzoisothiazole compound of the present invention is excellent as a light emitting layer.

  Furthermore, the device can be formed using vacuum deposition, casting method, or the like, and a device with a large area can be easily manufactured at a relatively low cost.

  Hereinafter, the present invention will be described in detail.

  First, the 2,1-benzisothiazole compound of the present invention will be described.

  Specific examples of the substituents in the general formulas [I] to [IV] are shown below.

  Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a ter-butyl group, and an octyl group.

  Examples of the aryl group and the divalent to hexavalent aromatic group include a phenyl group, a biphenyl group, and a terphenyl group.

  Examples of the heterocyclic group include thienyl group, pyrrolyl group, pyridyl group, bipyridyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, and tertenyl group.

  Examples of the condensed polycyclic aromatic group include a fluorenyl group, a naphthyl group, a fluoranthenyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a triphenylenyl group, and a perylenyl group.

  Examples of the condensed polycyclic heterocyclic group include a carbazolyl group, a phenanthroyl group, and an acridinyl group.

  Examples of the substituted amino group include a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, and a dianisolylamino group.

  Examples of the substituent that the substituent may have include an alkyl group such as a methyl group, an ethyl group, and a propyl group, an aralkyl group such as a benzyl group and a phenethyl group, an aryl group such as a phenyl group and a biphenyl group, a thienyl group, Heterocyclic groups such as pyrrolyl group and pyridyl group, amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, and dianisolylamino group, methoxyl group, ethoxyl group, propoxyl group, Examples include alkoxyl groups such as phenoxyl groups, cyano groups, halogen atoms such as fluorine, chlorine, bromine and iodine.

Next, typical examples of the 2,1-benzoisothiazole compound of the present invention will be given below, but the present invention is not limited thereto.
Compound represented by general formula [I]

Compound represented by general formula [II]

Compound represented by general formula [III]

Compound represented by general formula [IV]

  The 2,1-benzisothiazole compound of the present invention can be synthesized by a generally known method, for example, Advanced Heterocyclic. Chemisty. , 38, 105-133 (1985), an intermediate of 2,1-benzisothiazole compound can be obtained. Further, a 2,1-benzoisothiazole compound can be obtained by a synthesis method such as Suzuki Coupling method using a palladium catalyst (for example, Chem. Rev. 1995, 95, 2457.).

  The 2,1-benzisothiazole compound of the present invention is a compound having excellent light-emitting property, charge transporting property and durability as compared with conventional compounds, and is useful for a layer containing an organic compound in an organic light-emitting device. A layer formed by a vapor deposition method or a solution coating method is less likely to be crystallized and has excellent temporal stability.

  Next, the organic light emitting device of the present invention will be described in detail.

  The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a layer including a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers contains at least one 2,1-benzisothiazole compound of the present invention.

  In the organic light-emitting device of the present invention, the 2,1-benzoisothiazole compound of the present invention is formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is less than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.

  1 to 6 show preferred examples of the organic light emitting device of the present invention.

  FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light-emitting element used here is useful when it has a single hole transport ability, electron transport ability, and light-emitting performance, or when a compound having each characteristic is mixed.

  FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an anode 2, a hole transport layer 5, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the luminescent material is either a hole transporting material or an electron transporting material, or a material having both functions is used for each layer, and it is combined with a simple hole transporting material or electron transporting material having no light emitting property. Useful when used. In this case, the light emitting layer is composed of either the hole transport layer 5 or the electron transport layer 6.

  FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. This is a separation of carrier transport and light emission functions. It is used in combination with compounds having hole transport properties, electron transport properties, and light emission properties in a timely manner. Since various compounds having different values can be used, it is possible to diversify the emission hue. Further, it is possible to effectively confine each carrier or exciton in the central light emitting layer 3 to improve the light emission efficiency.

  FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a structure in which a hole injection layer 7 is inserted on the anode 2 side with respect to FIG. 3, which is effective in improving the adhesion between the anode 2 and the hole transport layer 5 or improving the hole injection property, and is effective in lowering the voltage. Is.

  5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. 5 and FIG. 6 show a layer (hole / exciton blocking layer 8) that prevents holes or excitons (excitons) from passing to the cathode 4 side as compared with FIG. 3 and FIG. It is the structure inserted between 6. By using a compound having a very high ionization potential as the hole / exciton blocking layer 8, the structure is effective in improving the light emission efficiency.

  However, FIGS. 1 to 6 are very basic device configurations, and the configuration of the organic light-emitting device using the 2,1-benzoisothiazole compound of the present invention is not limited to these. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or interference layer, and the hole transporting layer are composed of two layers having different ionization potentials can be employed.

  The 2,1-benzoisothiazole compound of the present invention is a compound having excellent charge transporting property, light emitting property and durability as compared with conventional compounds, and can be used in any form of FIGS.

  When the organic layer using 2,1-benzoisothiazole of the present invention is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur, and the stability over time is excellent.

  In the present invention, a 2,1-benzoisothiazole compound represented by the general formulas [I] to [IV] is used as a constituent component of the organic layer. A compound, an electron transporting compound, or the like can be used together as necessary.

  Examples of these compounds are given below.

  In the organic light-emitting device of the present invention, the layer containing the 2,1-benzisothiazole compound represented by the general formulas [I] to [IV] and the layer containing another organic compound are generally deposited by vacuum evaporation or A thin film is formed by a coating method after dissolving in an appropriate solvent. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.

  The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate resin. , Phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin and the like, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.

  As the anode material, a material having a work function as large as possible is good. For example, simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO), A metal oxide such as zinc indium oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.

  On the other hand, the cathode material preferably has a small work function, and can be used as a single metal or a plurality of alloys such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium. A metal oxide such as indium tin oxide (ITO) can also be used. Further, the cathode may have a single layer structure or a multilayer structure.

  Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.

  Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of the protective layer include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluorine resin, polyparaxylene, polyethylene, silicone resin, polystyrene resin, and photo-curing resins. It is done. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.

  EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.

  <Example 1> [Exemplary Compound No. 1] Synthesis of 4]

*) Gary M.M. Singerman,
Journal of Heterocyclic Chemistry, 12, 877 (1975)

In a 200 ml three-necked flask, 25.4 g (259 mmol) of methanesulfonamide [1] and 80 ml of benzene were placed, and 20.8 ml (285 mmol) of thionyl chloride was added dropwise with stirring at 0 degree in a nitrogen atmosphere. After gradually raising the temperature to room temperature, the mixture was stirred for 10 hours under reflux to prepare N-sulfinylmethanesulfonamide [2] ^* .

  In a 300 ml three-necked flask, 30.2 g (162 mmol) of 3-bromo-2-methylaniline [3] and 120 ml of benzene were placed, and 12.4 ml (170 mmol) of thionyl chloride was added dropwise with stirring at 0 degree in a nitrogen atmosphere. The mixture was gradually warmed to room temperature and stirred for 10 hours under reflux.

  To this reaction liquid, the reaction dispersion liquid of N-sulfinylmethanesulfonamide [2] prepared by the above method was added with stirring at 0 degree in a nitrogen atmosphere, and then a solution of 19.0 ml (232 mmol) of pyridine and 20 ml of benzene. Was dripped. The mixture was gradually warmed to room temperature and stirred for 15 hours under reflux. The reaction solution was poured into 800 ml of water, and the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and then purified with a silica gel column (toluene developing solvent) to obtain 7.3 g of benzoisothiazole intermediate [4] (transparent liquid) ( Yield 21%).

  A 200 ml three-necked flask was charged with 3.0 g (14.0 mmol) of benzoisothiazole intermediate [4], 3.04 g (15.4 mmol) of 4,4′-ditolylamine [5] and 100 ml of xylene in a nitrogen atmosphere at room temperature. Then, 1.48 g (15.4 mmol) of tBuONa was added with stirring. After raising the temperature to 60 ° C, a separately prepared dispersion of 0.05 g (0.23 mmol) of palladium acetate, 0.10 g (0.48 mmol) of tri-t-butylphosphine and 5 ml of xylene was added and stirred at 130 ° C for 2 hours. .

  100 ml of water was added to the reaction solution, and the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and then purified with an alumina column (toluene + ethyl acetate mixed developing solvent). 4.79 g (82% yield) of 4 (yellow crystals) was obtained.

  <Example 2> [Exemplary Compound No. Synthesis of 11]

  In a 200 ml three-necked flask, Exemplified Compound No. 4 Add 3.0 g (9.08 mmol) and 80 ml of chloroform, add 0.07 g (0.45 mmol) of iron (III) chloride with stirring at 0 degree, then add 1.45 g (9.08 mmol) of bromine and chloroform 30 ml of solution was added dropwise.

  After stirring at room temperature for 5 hours, 100 ml of water was poured into the reaction solution, the organic layer was extracted with chloroform, then washed with an aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and then an alumina column (toluene + ethyl acetate mixed developing solvent). To obtain 3.16 g (yield: 85%) of benzoisothiazole intermediate [6] (yellow crystals).

  A 200 ml three-necked flask is charged with boronic acid compound [7] 0.54 g (2.22 mmol), benzoisothiazole intermediate [6] 2.0 g (4.89 mmol) toluene 40 ml and ethanol 20 ml at room temperature in a nitrogen atmosphere. Under stirring, 4.0 g (37.7 mmol) of sodium carbonate and a 20 ml aqueous solution of water were added dropwise. Further, 0.13 g (0.11 mmol) of tetrakistriphenylphosphine was added, followed by stirring under reflux for 3 hours. 50 ml of water was poured into the reaction solution, and the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (toluene + ethyl acetate mixed developing solvent). 11.40 g (yield 78%) of 11 (yellow crystal) was obtained.

<Example 3>
An element having the structure shown in FIG. 3 was prepared.

  What formed indium tin oxide (ITO) as an anode 2 with a film thickness of 120 nm on a glass substrate as a substrate 1 by a sputtering method was used as a transparent conductive support substrate. This was ultrasonically washed successively with acetone and isopropyl alcohol (IPA), then boiled and washed with IPA and then dried. Furthermore, what was UV / ozone cleaned was used as a transparent conductive support substrate.

  A hole transport layer 5 was formed by depositing a chloroform solution of a compound represented by the following structural formula on a transparent conductive support substrate with a film thickness of 30 nm by spin coating.

Furthermore, Exemplified Compound No. 11 was formed to a thickness of 20 nm by vacuum deposition to form the light emitting layer 3. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.3 nm / sec.

Furthermore, the phenanthroline compound shown by the following general formula was formed into a film with a film thickness of 40 nm by the vacuum evaporation method, and the electron carrying layer 6 was formed. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.3 nm / sec.

Next, a metal layer film having a thickness of 50 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%) as the cathode 4, and further a vacuum deposition method. Thus, an aluminum layer having a thickness of 150 nm was formed. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 1.0 to 1.2 nm / sec.

  Further, a protective glass plate was placed in a nitrogen atmosphere and sealed with an acrylic resin adhesive.

When a 4V DC voltage was applied to the device thus obtained, with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, the current flowed at a current density of 80 mA / cm ^2. A green emission was observed at a luminance of 10,000 cd / m ² .

Further, when a voltage was applied for 100 hours while a current density was kept to 30 mA / cm ^2, after the initial luminance 4000 cd / m ² 100 hours 3300cd / m ² and luminance degradation was small.

<Examples 4 to 14>
Exemplified Compound No. A device was prepared in the same manner as in Example 3 except that the exemplified compounds shown in Table 1 were used in place of 11, and the same evaluation was performed. The results are shown in Table 1.

<Comparative Examples 1-2>
Exemplified Compound No. In place of Comparative compound No. 11 A device was prepared in the same manner as in Example 3 except that 1 and 2 were used, and the same evaluation was performed. The results are shown in Table 1.

<Example 15>
An element having the structure shown in FIG. 3 was prepared.

  In the same manner as in Example 3, a hole transport layer 5 was formed on a transparent conductive support substrate.

Further, Coumarin 6 and Exemplified Compound No. 2 (weight ratio 1:20) was formed into a film with a thickness of 20 nm by a vacuum vapor deposition method to form the light emitting layer 3. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.3 nm / sec.

  Further, an electron transport layer 6 and a cathode 4 were formed and sealed in the same manner as in Example 3.

When a 10V DC voltage was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, a current was generated at a current density of 1000 mA / cm ^2. And emission of green light was observed at a luminance of 60000 cd / m ² .

Further, when a voltage was applied for 100 hours while keeping the current density at 200 mA / cm ² , the luminance deterioration was small, from an initial luminance of 10000 cd / m ² to 8500 cd / m ² after 100 hours.

<Examples 16 to 18>
Exemplified Compound No. A device was prepared in the same manner as in Example 15 except that the exemplified compounds shown in Table 2 were used instead of 2, and the same evaluation was performed. The results are shown in Table 2.

<Comparative Example 3>
Exemplified Compound No. In place of Comparative Compound No. 2 A device was prepared in the same manner as in Example 15 except that 1 was used, and the same evaluation was performed. The results are shown in Table 2.

<Example 19>
An element having the structure shown in FIG. 3 was prepared.

  In the same manner as in Example 1, a hole transport layer 5 was formed on a transparent conductive support substrate.

Furthermore, Exemplified Compound No. 3 and a carbazole compound (weight ratio 20: 100) represented by the following general formula were formed into a film having a thickness of 20 nm by a vacuum deposition method, thereby forming a light emitting layer 3. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.3 nm / sec.

  Next, in the same manner as in Example 3, the electron transport layer 6 and the cathode 4 were formed and sealed.

When a 4V DC voltage was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, a current was applied at a current density of 90 mA / cm ^2. And emission of green light was observed at a luminance of 9000 cd / m ² .

Further, when a voltage was applied for 100 hours while maintaining the current density at 30 mA / cm ² , the luminance deterioration was small, from the initial luminance of 3800 cd / m ² to 2700 cd / m ² after 100 hours.

<Examples 20 to 22>
Exemplified Compound No. A device was prepared in the same manner as in Example 19 except that the exemplified compounds shown in Table 3 were used instead of 3, and the same evaluation was performed. The results are shown in Table 3.

<Comparative Examples 4-5>
Exemplified Compound No. In place of Comparative compound No. 3 1 and no. A device was prepared in the same manner as in Example 19 except that 2 was used, and the same evaluation was performed. The results are shown in Table 3.

It is sectional drawing which shows an example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention.

Explanation of symbols

1 Substrate 2 Anode 3 Light-Emitting Layer 4 Cathode 5 Hole Transport Layer 6 Electron Transport Layer 7 Hole Injection Layer 8 Hole / Exciton Blocking Layer

Claims (2)

Characterized in that it is shown below 2,1 benzisothiazole compounds.

A pair of electrodes composed of an anode and a cathode, has a, and an organic compound layer including at least a light emitting layer sandwiched between the pair of electrodes, 2,1 benzisothiazole compounds of the light-emitting layer according to claim 1 And an organic light-emitting device comprising at least one of the following 1,1-benzisothiazole compounds .

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