JP2002212150A - Triarylamine compound, polymer film by using the triarylamine compound, organic light emission element and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic light emission element capable of providing a high-intensity optical output having a long life with extremely high efficiency. SOLUTION: This organic light emission element has at least a pair of electrodes composed of an anode and a cathode, and layers comprising one or a plurality of organic compounds supported between the pair of the electrodes. At least one layer of the layers comprising the organic compound is composed of a polymer film containing a triarylamine compound having at least a plurality of polymerizable double bonds in the same molecule.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a triarylamine compound, a polymer film using the triarylamine compound, an organic light-emitting device and a method for producing the same, and more particularly, to a method for applying an electric field to a thin film made of an organic compound. The present invention relates to an element that emits light.

[0002]

2. Description of the Related Art In an organic light emitting device, a thin film containing a fluorescent organic compound is supported between an anode and a cathode, and electrons and holes (holes) are injected from each electrode to exciton the fluorescent compound. It is an element that utilizes light emitted when this exciton is returned to the ground state.

In 1987, a study by Kodak Company (Appl.
Phys. Lett. 51, 913 (1987)), a function-separated type 2 using ITO as an anode, magnesium-silver alloy as a cathode, an aluminum quinolinol complex as an electron transporting material and a luminescent material, and a triphenylamine derivative as a hole transporting material. This device has a layered structure, and has an applied voltage of about 10 V and 1000 cd / m ^2.
A degree of luminescence has been reported. Related patents include U.S. Pat. No. 4,539,507 and U.S. Pat.
32, U.S. Pat. No. 4,885,211 and the like.

[0004] In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared can be achieved, and various compounds have recently been actively studied. For example, US Pat. No. 5,151,629 and US Pat.
No. 9,783, U.S. Pat. No. 5,382,4,77, JP-A-2-247278, JP-A-3-255190, JP-A-5-202356, JP-A-9-20
No. 2878, JP-A-9-227576, and the like.

[0005] In addition to the organic light-emitting device using the above low-molecular material, an organic light-emitting device using a conjugated polymer is also a group of Cambridge University (Nature,
347, 539 (1990)).
In this report, light emission was confirmed in a single layer by forming a film of polyphenylenevinylene (PPV) in a coating system.
Patents related to an organic light emitting device using a conjugated polymer include US Pat. No. 5,247,190 and US Pat.
No. 4,878, U.S. Pat. No. 5,672,678, JP-A-4-145192, JP-A-5-247460, and the like.

As described above, recent advances in organic light-emitting devices have been remarkable, and their characteristics are that high luminance, a variety of emission wavelengths, high-speed response, a thin and lightweight light-emitting device can be realized at a low applied voltage. It suggests potential for a wide range of applications.

However, at present, light output with higher luminance or higher conversion efficiency is required. In addition, there are still many problems in terms of durability such as a change with time due to long-term use and deterioration due to an atmospheric gas containing oxygen or moisture. Further, when application to a full-color display or the like is considered, light emission of blue, green, and red with good color purity is required, but this problem has not yet been sufficiently solved.

As an example of using a polymer film for an organic light-emitting device, see the 59th Annual Meeting of the Japan Society of Applied Physics, Proceedings No.
31090 (1998), Proc. 31257 (1999) and the like, but these are vapor deposition polymerization systems, and problems remain in terms of polymerization control and productivity.

[0009]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems of the prior art, and an organic light-emitting device having extremely high efficiency, high brightness, and long life light output has been developed. To provide. Another object of the present invention is to provide an organic light-emitting device that has various emission wavelengths, exhibits various emission hues, and is extremely durable. It is still another object of the present invention to provide an organic light emitting device which can be easily manufactured and can be manufactured at low cost.

[0010]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have completed the present invention.

That is, the triarylamine compound of the present invention is characterized by having at least a plurality of polymerizable double bonds in the same molecule.

In the triarylamine compound of the present invention, the polymerizable double bond is formed from a carbon-carbon double bond, preferably a substituted or unsubstituted vinyl group or a substituted or unsubstituted acrylate group. Preferably, the polymerizable double bond group has at least three or more polymerizable double bond groups.

The polymer film of the present invention is characterized by containing the above triarylamine compound.

Further, the organic light emitting device of the present invention is an organic light emitting device having at least a pair of electrodes comprising an anode and a cathode, and at least one layer of one or more organic compounds supported between the pair of electrodes. At least one layer of the layer containing an organic compound is characterized by comprising a polymer film containing a triarylamine compound having at least a plurality of polymerizable double bonds in the same molecule.

In the organic light emitting device of the present invention, the polymer film is used for a hole injection layer, a hole transport layer, or a light emitting layer, and the polymerizable double bond is a carbon-carbon double bond; Preferably, it is composed of a substituted or unsubstituted vinyl group or a substituted or unsubstituted acrylate group, and has at least three polymerizable double bond groups.

Further, the first of the methods for manufacturing an organic light-emitting device of the present invention is a method for manufacturing the organic light-emitting device, wherein the triarylamine compound is dissolved in a solvent, and a film is formed by a coating method. Alternatively, a polymer film is formed by an electron beam.

The second method of the present invention for producing an organic light-emitting device is a method for producing the above-mentioned organic light-emitting device, wherein the above-mentioned triarylamine compound is dissolved in a solvent to form pixels by a printing method. Alternatively, a polymer film is formed by an electron beam.

A third method of manufacturing an organic light emitting device according to the present invention is a method of manufacturing the organic light emitting device, wherein the triarylamine compound is dissolved in a solvent to form a pixel by an ink jet printing method, and light, heat, Or a polymer film formed by an electron beam.

In the present invention, the organic compound having a charge transporting property or a luminescent property itself has a plurality of polymerizable double bonds, and a film is formed in a state of a single molecule or an oligomer. Since a cured polymer film is formed, aggregation and crystallization of organic compounds do not occur, and an organic light-emitting device having extremely stable and excellent durability can be provided.

[0020]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.

The triarylamine compound of the present invention has at least a plurality, preferably three or more polymerizable double bonds in the same molecule.

Specific examples of the triarylamine constituting the skeleton of the triarylamine compound of the present invention include triphenylamine, 4,4 ′, 4 ″ -tris (4-biphenyl) amine, 4,4 ′, 4 "-tris (4-terphenyl) amine, N, N-diphenyl-1-naphthylamine, N, N-di (4-biphenyl) -1-naphthylamine, N, N-diphenyl-1-pyrenylamine, N, N
3 substituted with an aromatic hydrocarbon ring or an aromatic heterocyclic ring such as -di (1-naphthyl) aniline, N, N-di (4-biphenyl) aniline, N, N-di (2-pyridyl) aniline;
Secondary amines. These aromatic hydrocarbon rings can have a substituent.

Further, specific examples of the polymerizable double bond include vinyl, allyl, isopropenyl, 1,3-butadienyl, acroyl, and methacryloyl, and these may be substituted or unsubstituted. Among these, a substituted or unsubstituted vinyl group and a substituted or unsubstituted acrylate group are preferred. This polymerizable double bond is directly or indirectly substituted by the above-mentioned tertiary amine substituted with an aromatic hydrocarbon ring or an aromatic heterocycle, or through an aliphatic hydrocarbon, an oxygen atom or the like.

The above examples are the most typical ones, and are not limited to them.

Next, the polymer film of the present invention will be described.

The polymer film of the present invention contains the triarylamine compound of the present invention. Specifically, a homopolymer film obtained by polymerizing the triarylamine compound of the present invention, a hole transporting compound, a light emitting compound, and a triarylamine compound of the present invention containing other compounds such as an electron transporting compound And a composite polymerized film obtained by polymerizing the same.

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

In the organic light-emitting device of the present invention, at least one of the layers containing the organic compound comprises a polymer film containing a triarylamine compound having at least a plurality of polymerizable double bond groups in the same molecule. The layer containing another organic compound is formed between the anode and the cathode by a sol-gel method, a vacuum evaporation method, or a solution coating method. The thickness of the organic layer is thinner than 10 μm, preferably 0.5 μm or less, more preferably 0.05 to 0.5 μm.

Hereinafter, the present invention will be described in more detail with reference to the drawings.

FIG. 1 is a 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. The light-emitting element used here is useful when it has a single hole-transporting ability, electron-transporting ability, and light-emitting performance, or when a mixture of compounds having the respective properties is used.

FIG. 2 is a 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, when the luminescent material has either the hole transporting property or the electron transporting property or a material having both functions in each layer, and is used in combination with a mere hole transporting substance having no luminescent property or an electron transporting substance Useful for In this case, the light emitting layer 3 is made of either the hole transport layer 5 or the electron transport layer 6.

FIG. 3 is a 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. It separates the functions of carrier transport and light emission, and is used in a timely combination with a compound having hole transport, electron transport, and light emitting properties. Can be used, so that the emission hue can be diversified. Furthermore, it is possible to effectively confine each carrier or exciton in the central light emitting layer to improve the light emission efficiency.

However, FIGS. 1 to 3 show only very basic device configurations, and the configuration of the organic light emitting device of the present invention is not limited to these. For example, providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer,
Various layer configurations can be adopted such that the hole transport layer is composed of two layers having different ionization potentials.

In the present invention, the layer composed of the polymer film containing the above-mentioned triarylamine compound can be applied to any of the hole injection transport layer, the electron transport layer and the light emitting layer. Hole-transporting compound (for example, a compound represented by Chemical Formula 1 or 2) or a luminescent compound (for example, a compound represented by Chemical Formula 3) or an electron-transporting compound (for example, a compound represented by Chemical Formula 4 to 6)
Can be used together if necessary.

[0035]

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[0036]

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[0037]

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[0038]

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[0039]

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[0040]

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The method for forming the layer composed of the polymer film containing the above triarylamine compound is not particularly limited.
Dissolve the triarylamine compound of the present invention in a solvent,
It can be formed by forming a film or forming a pixel by a coating method, a printing method, or an inkjet printing method, and polymerizing the film with light, heat, or an electron beam.

In the organic light-emitting device of the present invention, a layer composed of an organic compound other than the layer composed of the polymer film containing the triarylamine compound is generally formed by a vacuum evaporation method or a coating method after dissolving in a suitable solvent. Form a thin film. In particular, when forming a film 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, for example, polyvinyl carbazole resin,
Polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin,
Examples include, but are not limited to, diallyl phthalate resin, phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin, and the like. These may be used alone or as a copolymer, alone or as a mixture of two or more.

The anode material preferably has a work function as large as possible. For example, a simple metal such as gold, platinum, nickel, palladium, cobalt, selenium, and vanadium, or an alloy thereof, tin oxide, zinc oxide, indium tin oxide ( Metal oxides such as ITO) and indium zinc oxide can be used. Further, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode substances may be used alone or in combination of two or more.

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

The substrate used in the present invention is not particularly limited, but an opaque substrate such as a metal substrate or a ceramic substrate, or a transparent substrate such as glass, quartz, or a plastic sheet is used. Further, it is also possible to control the emitted light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film or the like on the substrate.

It is to be noted that a protective layer or a sealing layer may be provided on the manufactured device for the purpose of preventing contact with oxygen, moisture, or the like. Examples of the protective layer include an inorganic material film such as a diamond thin film, a metal oxide, and a metal nitride; a polymer film such as a fluorine resin, polyparaxylene, polyethylene, a silicone resin, and a polystyrene resin; and a photocurable resin. Can be Alternatively, the device itself can be covered with glass, a gas impermeable film, metal, or the like, and the element itself can be packaged with an appropriate sealing resin.

[0048]

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

Example 1 <Synthesis of 4,4 ′, 4 ″ -trivinyltriphenylamine> 600 g of DMF was charged into a 3-liter three-necked flask, and cooled and stirred in an ice water bath.
g was added dropwise while maintaining the temperature at 10 ° C. or lower, and stirring was continued for 15 minutes after completion of the addition. Next, 50 g of triphenylamine
(0.204 mol) was suspended and dispersed in 250 ml of DMF and poured into the previously prepared stirring liquid. The reaction temperature was gradually raised, and heating and stirring were continued at 80 ° C. for 100 hours. A solution prepared by dissolving 4000 g of sodium acetate in 40 liters of water was prepared, and the reaction solution was poured into the solution to precipitate crystals. After filtering the crystals, they were dissolved in toluene and washed three times with water. Toluene was concentrated under reduced pressure, and hexane was added to precipitate crystals, which were filtered and dried to obtain 4,
55.2 g of crude crystals of 4 ', 4 "-triformyltriphenylamine were obtained. The obtained crude crystals were purified using a silica gel column to give 4,4', 4" -triformyltriphenylamine. Product, green yellow crystals 16.5g
I got

DMF 200 in a 500 ml four-neck flask
Then, the mixture was cooled to 5 ° C. or lower in an ice water bath. To this solution, 18.4 g of sodium methoxide was added, and 73.0 g of triphenylphosphine methyl bromide was further added.
Was added and stirring was continued for 30 minutes. Next, 4,4 ', 4 "-
15.0 g of triformyltriphenylamine was added to DMF2
A solution dissolved in 00 ml was added dropwise over 1 hour while maintaining the dropping temperature at 10 ° C. or lower. Further, at 30 ° C., 2
Heating and stirring were continued at 60 ° C. for 4 hours. The obtained reaction solution was diluted with 500 ml of water, extracted with toluene and washed with water three times.
Crude crystal 1 of 4 ', 4 "-trivinyltriphenylamine
2.5 g were obtained. 7. The resulting crude crystals are purified using a silica gel column to give the target 4,4 ', 4 "-trivinyltriphenylamine purified product, white needle crystals.
9 g were obtained. FIG. 4 shows the infrared absorption spectrum of this compound.

[Example 2] <Preparation of element shown in FIG. 2> Indium tin oxide (ITO) formed on a glass substrate by sputtering to a thickness of 120 nm was used as a transparent conductive support substrate 1. Was. This was ultrasonically washed sequentially with acetone and isopropyl alcohol (IPA), boiled and washed with IPA, and dried. Further, the substrate subjected to UV / ozone cleaning was used as a transparent conductive support substrate.

A solution was prepared by dissolving 0.10 g of 4,4 ′, 4 ″ -trivinyltriphenylamine in 5.0 g of toluene. The solution was used to spin coat a transparent support substrate. (2000 rpm), and after irradiating with ultraviolet rays for 3 minutes, under nitrogen atmosphere at 80 ° C. for 10 minutes.
Heat treatment at 120 ° C. for 2 hours to form a triphenylamine polymer film having a thickness of 55 nm.

Further, aluminum quinolinol (Aq
13) was formed into a 50 nm-thick electron-transporting / light-emitting layer by a vacuum evaporation method. The degree of vacuum during the deposition is 1.0 × 10 ⁻⁴ Pa,
The film was formed under the conditions of a film forming speed of 0.3 nm / sec.

Next, a 200 nm-thick metal layer film was formed on the above organic layer by a vacuum evaporation method using an evaporation material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was prepared. The degree of vacuum at the time of deposition is 1.0 × 10 ⁻⁴ Pa, and the film formation rate is 1.0 to
The film was formed under the condition of 1.2 nm / sec.

When a DC voltage of 7 V is applied to the device thus obtained with the ITO electrode serving as a positive electrode and the Al-Li electrode serving as a negative electrode, a current flows at a current density of 5.3 mA / cm ² , and the initial luminance is reduced. Green emission of 230 cd / m ² was observed.

[Example 3] <Preparation of device shown in FIG. 1> Indium tin oxide (ITO) formed on a glass substrate to a thickness of 120 nm by a sputtering method was used as a transparent conductive support substrate. . This was ultrasonically washed sequentially with acetone and isopropyl alcohol (IPA), boiled and washed with IPA, and dried. further,
The substrate washed with UV / ozone was used as a transparent conductive support substrate.

A solution was prepared by dissolving 0.10 g of 4,4 ′, 4 ″ -trivinyltriphenylamine and 0.050 g of CN-PPV in 10 ml of xylene. Spin coating method (200
0 rpm) at 80 ° C. under a nitrogen atmosphere.
Heat treatment was performed at 120 ° C. for 2 hours to form a composite film of a triphenylamine polymer and CN-PPV having a thickness of 110 nm.

Next, a metal layer film having a thickness of 150 nm was formed on the above-mentioned organic layer by a vacuum evaporation method using an evaporation material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was prepared. The degree of vacuum at the time of vapor deposition is 1.0 × 10 ⁻⁴ Pa, and the film formation rate is 1.0 to 10
The film was formed under the condition of 1.2 nm / sec.

When a DC voltage of 11 V was applied to the device thus obtained with an ITO electrode serving as a positive electrode and an Al-Li electrode serving as a negative electrode, a current flowed at a current density of 21.8 mA / cm ² and an initial luminance Blue light emission of 170 cd / m ² was observed.

[Example 4] <Preparation of device shown in FIG. 3> Indium tin oxide (ITO) formed on a glass substrate to a thickness of 120 nm by sputtering was used as a transparent conductive support substrate. . This was ultrasonically washed sequentially with acetone and isopropyl alcohol (IPA), boiled and washed with IPA, and dried. further,
The substrate washed with UV / ozone was used as a transparent conductive support substrate.

A solution was prepared by dissolving 0.10 g of 4,4 ′, 4 ″ -trivinyltriphenylamine in 5.0 g of toluene. The solution was used to spin coat a transparent support substrate. (2000 rpm), and after irradiating with ultraviolet rays for 3 minutes, under nitrogen atmosphere at 80 ° C. for 10 minutes.
Heat treatment at 120 ° C. for 2 hours to form a triphenylamine polymer film having a thickness of 55 nm. A co-evaporation film of coumarin 6 (1.0 wt%) and aluminum quinolinol was formed thereon to a thickness of 200 nm, and aluminium quinolinol was formed to a thickness of 300 nm by an evaporation method.

Next, a 200-nm-thick metal layer film was formed on the above-mentioned organic layer by a vacuum evaporation method using an evaporation material composed of aluminum and lithium (lithium concentration 1 atomic%). An element having the structure shown was prepared. The degree of vacuum at the time of deposition is 1.0 × 10 ⁻⁴ Pa, and the film formation rate is 1.0 to
The film was formed under the condition of 1.2 mn / sec.

When a DC voltage of 8 V was applied to the device thus obtained with an ITO electrode serving as a positive electrode and an Al-Li electrode serving as a negative electrode, a current flowed at a current density of 5.1 mA / cm ² , resulting in an initial luminance. Green light emission of 370 cd / m ² was observed.

[0064] Further, the device in the lower 80 ° C. nitrogen atmosphere, keeping the current density 3.0 mA / cm ^2, was applied to 1000 hours voltages, from an initial luminance 200 cd / m ² and 1000 hours after the luminance 175cd / m ² The luminance deterioration was very small.

[0065]

As shown in the examples, the organic light-emitting device using the polymer film of triarylamine of the present invention can emit light with high luminance at a low applied voltage and has excellent durability. Further, the device can be prepared by using a coating method, a printing method, or an ink-jet printing method, as well as a vacuum deposition or casting method, so that a relatively inexpensive and large-area device can be easily prepared.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view illustrating an example of an organic light emitting device according to the present invention.

FIG. 2 is a cross-sectional view illustrating another example of the organic light emitting device according to the present invention.

FIG. 3 is a cross-sectional view illustrating another example of the organic light emitting device according to the present invention.

FIG. 4 is an infrared absorption spectrum of 4,4 ′, 4 ″ -trivinyltriphenylamine.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Light emitting layer 4 Cathode 5 Hole transport layer 6 Electron transport layer

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (Reference) H05B 33/22 H05B 33/22 D (72) Inventor Kazunori Ueno 3- 30-2 Shimomaruko, Ota-ku, Tokyo Canon stock Inside the company (72) Inventor Hiroshi Tanabe 3-30-2 Shimomaruko, Ota-ku, Tokyo Within Canon Inc. (72) Inventor Tatsuto 3-30-2 Shimomaruko, Ota-ku, Tokyo F-term within Canon Inc. (Reference) 3K007 AB02 AB03 AB11 DA02 DA06 EB00 FA01 4H006 AA01 AB46 AB92

Claims (13)

[Claims] 1. A triarylamine compound having at least a plurality of polymerizable double bonds in the same molecule. 2. The triarylamine compound according to claim 1, wherein the polymerizable double bond comprises a carbon-carbon double bond. 3. The triarylamine compound according to claim 2, wherein the carbon-carbon double bond comprises a substituted or unsubstituted vinyl group or a substituted or unsubstituted acrylate group. . 4. The method according to claim 1, wherein the polymerizable double bond group has at least 3
The triarylamine compound according to any one of claims 1 to 3, wherein the compound has at least one compound. 5. A polymer film comprising the triarylamine compound according to claim 1. 6. An organic light-emitting element having at least a pair of electrodes comprising an anode and a cathode and one or more organic compound layers supported between the pair of electrodes, wherein at least one of the layers containing the organic compound is provided. Is an organic light-emitting device comprising a polymer film containing a triarylamine compound having at least a plurality of polymerizable double bonds in the same molecule. 7. The organic light emitting device according to claim 6, wherein the polymer film is used for a hole injection layer, a hole transport layer, or a light emitting layer. 8. The organic light emitting device according to claim 6, wherein the polymerizable double bond comprises a carbon-carbon double bond. 9. The organic light emitting device according to claim 8, wherein the carbon-carbon double bond comprises a substituted or unsubstituted vinyl group or a substituted or unsubstituted acrylate group. 10. The organic light emitting device according to claim 6, wherein the organic light emitting device has at least three polymerizable double bond groups. 11. The method for producing an organic light-emitting device according to claim 6, wherein the triarylamine compound is dissolved in a solvent, and a film is formed by a coating method.
A method for manufacturing an organic light emitting device, wherein a polymer film is formed by heat or an electron beam. 12. The method for manufacturing an organic light emitting device according to claim 6, wherein the triarylamine compound is dissolved in a solvent to form pixels by a printing method.
A method for manufacturing an organic light emitting device, comprising forming a polymer film by light, heat, or electron beam. 13. The method for manufacturing an organic light emitting device according to claim 6, wherein the triarylamine compound is dissolved in a solvent to form a pixel by an inkjet printing method, and the light, heat, or light is applied. A method for manufacturing an organic light-emitting device, wherein a polymer film is formed by an electron beam.