JP2010135799A - Organic light emitting element, and light emitting material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic EL (electroluminescence) element high in luminous efficiency, luminance and durability as a light emitting material used in the organic EL element and to provide the light emitting material. <P>SOLUTION: After a polymer composition containing a polymerizable light emitting compound having a light emitting part such as a metal complex structure that emits light from an excited triplet state and a polymer functional group is formed as a film, the film is polymerized to form a light emitting layer. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a flat display panel, an organic light emitting device (OLED) for a backlight used therein, a manufacturing method thereof, and a light emitting material thereof.

  The organic light-emitting device was manufactured by Kodak C.I. W. Since Tang et al. Showed high-luminance light emission (Appl. Phys. Lett., 51, 913, 1987), material development and device structure improvements have progressed rapidly. Practical use began with telephone displays. In order to further expand the applications of this organic EL, development of materials for improving luminous efficiency and durability, development of full-color display, and the like are being actively carried out. In particular, when considering expansion to medium-sized panels, large-sized panels, or lighting applications, it is necessary to further increase the luminance by improving the light emission efficiency.

  As these light-emitting materials, metal complexes such as aluminum quinolinium complex (Alq3) have been conventionally used because of their high light emission efficiency and high light emission intensity. However, in order to form these low molecular weight materials in the light emitting layer of the organic light emitting device, a technique such as vacuum vapor deposition is used, which has been a demerit in the device production process. Nature 397 (1999) 121 describes that a π-electron conjugated polymer such as polyparaphenylene vinylene (PPV) or its derivative (MEH-PPV) is used as a light-emitting material. Some have begun to be used. Since these polymer materials can be formed by a casting method, they have not only a merit in the production process but also a merit that durability is better than that of a low molecular weight light emitting material. However, these have a demerit that the luminous efficiency is lower than that of the low molecular weight light emitting material.

  The light-emitting materials studied in these studies are emission from excited singlet state, ie fluorescence, and according to the monthly display, October 1998, separate volume “Organic EL Display”, page 58, electrical Since the generation ratio of excitons in the excited singlet state and excited triplet state in the excitation is 1: 3, the upper limit of the internal quantum efficiency of light emission in the organic EL has been 25%.

  In contrast, M.M. A. Baldo et al. Obtained an external quantum efficiency of 7.5% (internal quantum efficiency was 37.5% when the external extraction efficiency was assumed to be 20%) by using an iridium complex that emits phosphorescence from an excited triplet state. It has been shown that the external quantum efficiency of 5% can be exceeded (Appl. Phys. Lett., 75, 4, p. 1999, WO 00/70655). However, materials that emit phosphorescence stably at room temperature, such as the iridium complex used here, are extremely rare, so the degree of freedom in material selection is narrow, and in actual use, it is doped with a specific host compound. For example, it is necessary to select a material for satisfying the display specifications.

  On the other hand, M. A. Baldo et al. Uses an iridium complex as a sensitizer, transfers energy from this excited triplet state to the excited singlet state of the fluorescent dye, and finally emits fluorescence from the excited singlet state of the fluorescent dye. It was shown that relatively good luminous efficiency can be obtained (Nature, 403, 750, 2000). This method has an advantage that a fluorescent material suitable for the purpose can be selected and used as a luminescent material. However, this method includes a spin-forbidden process of energy transfer from the excited triplet state of the sensitizer to the excited singlet state of the fluorescent dye, and thus has a major disadvantage of low emission quantum efficiency in principle. was there.

International Publication No. 00/70655

“Applied Physical Letter”, 1987, Vol. 51, p. 913 “Monthly Display“ Organic EL Display ””, October 1998, separate volume, p. 58 “Applied Physical Letter”, 1999, Vol. 75, p. 4 Nature, 403, 750, 2000

  As described above, as a light emitting material used for the organic light emitting element, there has not yet been a material exceeding 5% which is the limit value of the external quantum efficiency of fluorescence emission which has been conventionally known. In addition, a material with high luminous efficiency has been demanded from the viewpoint of improving the durability of the element because the energy loss is small and heat generation of the element is suppressed. An object of the present invention is to solve such problems of the prior art and provide an organic light-emitting device having high luminance and durability, and a light-emitting material used therefor.

  As a result of various studies to solve the above problems, the present inventors have found that a polymer light-emitting material obtained by polymerizing a polymerizable composition containing at least one light-emitting compound into a film is durable. The luminescent substance (light-emitting moiety) is immobilized with a polymer by this method, and high efficiency light emission from the excited triplet state or the excited triplet state is obtained. The inventors have found that high-efficiency light emission can be obtained, and have completed the present invention.

That is, the present invention relates to the following light emitting materials, organic light emitting elements, and methods for producing the same.
[1] A polymeric light-emitting material obtained by polymerizing a polymerizable composition containing at least one light-emitting compound into a film.

[2] The polymer light-emitting material according to [1], wherein the light-emitting compound is a polymerizable light-emitting compound.
[3] At least one of the polymerizable light-emitting compounds is a cross-linkable light-emitting compound having two or more polymerizable functional groups, and the polymer after polymerization is a cross-linkable polymer [2] A polymer-based light-emitting material described in 1.

[4] The polymeric light-emitting material according to any one of [1] to [3], wherein the polymerizable composition contains a polymerizable compound other than at least one light-emitting compound.
[5] The polymeric light-emitting material according to [4], wherein at least one of the polymerizable compounds other than the light-emitting compound is a polymerizable electron-transporting compound.

[6] The polymer light-emitting material according to [4], wherein at least one of the polymerizable compounds other than the light-emitting compound is a cross-linkable polymerizable compound having two or more polymerizable functional groups.
[7] The light-emitting mechanism of the light-emitting portion of the light-emitting compound is characterized by the transition from the excited triplet state to the ground state of the electron energy level or from the ground state via the excited triplet state. The polymer light-emitting material according to any one of [1] to [6].

[8] The polymer light-emitting material according to any one of [1] to [6], wherein the light-emitting mechanism of the light-emitting portion of the light-emitting compound is fluorescence due to a transition from an excited singlet state to a ground state .
[9] The polymer light-emitting material according to [7] or [8], wherein the light-emitting moiety has a metal complex structure.

[10] The polymer light-emitting material according to [7] or [8], wherein the light-emitting moiety has a transition metal complex structure.
[11] The polymer light-emitting material according to [7] or [8], wherein the light-emitting moiety has a light metal complex structure.

[12] The polymer light-emitting material according to [7] or [8], wherein the light-emitting portion has a rare earth metal complex structure.
[13] The polymer-based light-emitting material according to any one of [9] to [12], wherein the complex-structure-forming portion of the light-emitting portion contains a nitrogen atom.

[14] The polymer light-emitting material according to [13], wherein the light-emitting moiety contains a pyridine skeleton, a pyrimidine skeleton, and / or a quinoline skeleton in the complex structure forming portion.
[15] An organic light emitting device using the polymer light emitting material according to any one of [1] to [14].

  [16] A coating film forming type electron transport layer and / or a coating film forming type hole transport layer are formed on both surfaces and / or one surface of the light emitting layer made of the polymer light emitting material according to any one of [1] to [14]. The organic light-emitting device according to [15], wherein the organic light-emitting device is formed.

  [17] A light-emitting layer is formed by polymerizing a polymerizable composition containing at least one light-emitting compound on an electrode or a charge transport layer and then polymerizing the polymerizable composition. Manufacturing method of organic light emitting element.

[18] The method for producing an organic light-emitting element according to [17], wherein the light-emitting compound is a polymerizable light-emitting compound.
[19] At least one of the polymerizable light-emitting compounds is a cross-linkable light-emitting compound having two or more polymerizable functional groups, and the polymer after polymerization is a cross-linkable polymer [18] The manufacturing method of the organic light emitting element of description.

[20] The method for producing an organic light-emitting element according to any one of [17] to [19], wherein the polymerizable composition contains a polymerizable compound other than at least one light-emitting compound.
[21] The method for producing an organic light-emitting element according to [20], wherein at least one of the polymerizable compounds other than the light-emitting compound is a polymerizable electron-transporting compound.

  [22] The method for producing an organic light-emitting element according to [20], wherein at least one of the polymerizable compounds other than the light-emitting compound is a crosslinked polymerizable compound having two or more polymerizable functional groups.

  [23] The emission mechanism of the light-emitting portion of the luminescent compound is characterized by the transition from the excited triplet state to the ground state of the electronic energy level or the transition to the ground state via the excited triplet state. The method for producing an organic light-emitting device according to any one of [17] to [22].

  [24] The organic light-emitting device according to any one of [17] to [22], wherein the light-emitting mechanism of the light-emitting portion of the light-emitting compound is fluorescence due to a transition from an excited singlet state to a ground state. Method.

[25] The method for producing an organic light-emitting element according to [23] or [24], wherein the light-emitting moiety has a metal complex structure.
[26] The method for producing an organic light-emitting element according to [23] or [24], wherein the light-emitting moiety has a transition metal complex structure.

[27] The method for producing an organic light-emitting element according to [23] or [24], wherein the light-emitting portion has a light metal complex structure.
[28] The method for producing an organic light-emitting element according to [23] or [24], wherein the light-emitting portion has a rare earth metal complex structure.

[29] The method for producing an organic light-emitting element according to any one of [25] to [28], wherein the complex structure forming portion of the light-emitting portion contains a nitrogen atom.
[30] The method for producing an organic light-emitting element according to [29], wherein the complex structure-forming portion of the light-emitting portion contains a pyridine skeleton, a pyrimidine skeleton and / or a quinoline skeleton.

  [31] After forming a polymerizable composition in which at least one of the polymerizable compounds in the polymerizable composition is a cross-linkable polymerizable compound having two or more polymerizable functional groups on the anode or the hole transport layer in a film form The organic material according to any one of [17] to [30], wherein an electron transport layer is further formed by coating on an insoluble crosslinked polymer light emitting material layer formed by crosslinking polymerization. Manufacturing method of light emitting element.

  By using a non-crosslinked and / or crosslinked polymer light emitting material obtained by forming a film of the polymerizable light emitting compound of the present invention, an organic light emitting device having good processability can be provided. Furthermore, it becomes possible to efficiently convert the energy of the excited triplet state into light emission, and it is possible to provide an organic light emitting device having high luminance and durability.

It is an example of sectional drawing of the organic light emitting element of this invention.

Hereinafter, embodiments of the present invention will be described with reference to the drawings.
FIG. 1 is a cross-sectional view showing an example of the configuration of the organic light emitting device of the present invention, in which a hole transport layer, a light emitting layer, and an electron transport layer are sequentially provided between an anode and a cathode provided on a transparent substrate. Further, the organic light-emitting device configuration of the present invention is not limited to the example of FIG. 1, and any one of 1) hole transport layer / light-emitting layer and 2) light-emitting layer / electron transport layer is sequentially formed between the anode and the cathode. Further, 3) a layer containing a hole transport material, a light emitting material, an electron transport material, 4) a layer containing a hole transport material, a light emitting material, 5) a layer containing a light emitting material, an electron transport material, 6) Any one of the single layers of the light emitting material may be provided. Moreover, although the light emitting layer shown in FIG. 1 is one layer, two or more layers may be laminated | stacked.

  In the polymer light-emitting material of the present invention, a polymerizable composition containing at least one light-emitting compound is formed (for example, coated) on the base layer of the organic EL device, and then the polymerizable composition is used. It is characterized by being polymerized into a polymer. The polymerizable composition means that the composition contains at least one polymerizable compound having a polymerizable functional group such as a (meth) acryl group, a vinyl group, a styryl group, an isocyanate group, or a thioisocyanate group. If the number of polymerizable functional groups in the polymerizable compound is 2 or more, the polymerized polymer has a cross-linked structure, so that at least one of the polymerizable compounds to be used has two or more polymerizable functional groups. A cross-linkable polymerizable compound is preferred. In addition, although the layer used as a base means an electrode, a charge transport layer (a hole transport layer, an electron transport layer), etc., it changes with structures and manufacturing methods of an organic EL element.

  The polymerizable compound in the polymerizable composition used in the polymer light-emitting material of the present invention may be a light-emitting compound having a polymerizable functional group, an electron transporting compound having a polymerizable functional group, and a polymerizable compound. A hole transporting compound having a functional group may be used, and other polymerizable compounds and a mixture thereof may be used. The light emitting compound of the present invention is preferably a light emitting compound having the above polymerizable functional group. When the polymerizable composition used in the polymer light-emitting material of the present invention contains a polymerizable compound other than the light-emitting compound having a polymerizable functional group, the polymer light-emitting material of the present invention is a copolymer of these compounds. Combined.

  Examples of the light-emitting moiety include conjugated structures such as a stilbene structure, light metal complexes such as an aluminum quinolium complex, and transition metal complex structures. A metal complex structure is preferable in terms of stability and design freedom.

  In the polymer light-emitting material of the present invention, a portion that emits light from an excited singlet state, that is, a fluorescent portion and / or a portion that emits light from an excited triplet state, that is, a phosphorescent portion, or an excited triplet state. It is preferable to form a polymerizable composition containing a polymerizable light-emitting compound having a portion that emits light via a film on the base layer, and then polymerize the composition to polymerize it. In particular, a polymerizable composition containing a polymerizable light-emitting compound having a portion that emits light from an excited triplet state, that is, a phosphorescent portion, or a portion that emits light via an excited triplet state is formed on the base layer. It is preferable to polymerize and form a polymer after forming into a film. The light emission via the excited triplet state here means energy transfer from the excited triplet state corresponding to the phosphorescent first compound to the excited triplet state corresponding to the fluorescent second organic compound. After that, the fluorescence emitted from the part which hits a 2nd organic compound is pointed out.

  The value of the quantum efficiency of the excited triplet state of the phosphorescent portion is preferably 0.1 or more, more preferably 0.3 or more, and still more preferably 0.5 or more. Examples of the compound structure having high quantum efficiency in the excited triplet state that can be applied to these phosphorescent portions can include metal complex structures, but are not limited thereto. Specific examples of the metal complex structure include transition metal complex structures having iridium, platinum or the like as a central atom, and transition metal complex structures such as derivatives thereof. These are preferable in that they have a relatively stable excited triplet state even near room temperature. Moreover, it is preferable also from the point which can be complexed easily by coordinating the polymer which has a functional group with coordination ability to a transition metal atom so that it may mention later. Other compound structures with high quantum efficiency of excited triplet states that can be applied to these phosphorescent moieties include, for example, “Handbook of Photochemistry, Second Edition (written by Steven L. Murov et al., Marcel Decker Inc., 1993). You can choose from.

  As the transition metal used in the above transition metal complex structure, in the periodic table, the first transition element series is from Sc of atomic number 21 to Zn of atomic number 30, and the second transition element series is from Y of atomic number 39. Up to Cd of atomic number 48, the third transition element series includes from Hf of atomic number 72 to Hg of atomic number 80.

  In addition, a rare earth metal complex structure can be exemplified as another specific example of the metal complex structure that can be applied to the above phosphorescent light emitting portion, but the present invention is not limited thereto. The rare earth metal used in this rare earth metal complex structure includes La of atomic number 57 to Lu of atomic number 71 in the periodic table.

  In addition, a light metal complex structure can be exemplified as another specific example of the metal complex structure that can be applied to the light-emitting portion, but the present invention is not limited thereto. Examples of the light metal used in the light metal complex structure include alkali metals such as lithium, sodium and potassium, alkaline earth metals such as magnesium and calcium, and aluminum.

  The luminescent moiety in the present invention is preferably nonionic. This is because when the luminescent portion is ionic, electrochemiluminescence occurs when a voltage is applied to the luminescent layer containing the luminescent portion, and this luminescence has a very slow response speed, for example, on the order of minutes. This is because it is inappropriate.

  The metal atom that becomes the central metal of the metal complex structure used in the light-emitting moiety of the present invention is constrained by one or more sites of the polymer. A method for achieving this is not particularly limited, and examples thereof include complexation by coordination bond, covalent bond, complexation by charge transfer, and ionic bond. In this case, a method in which a ligand is bonded to a polymer to form a complex is particularly preferable because the material can be easily designed and synthesized. In addition, when the metal atom serving as the central metal is an ion, a method in which the luminescent portion is neutral (nonionic) is adopted for the above-described reason, not a metal complex structure consisting solely of coordination bonds. And a method of forming a metal complex structure (organometallic compound structure) having a covalent bond sufficient to neutralize the valence of the metal ion together with the coordination bond, and the like, but is not limited thereto.

  Examples of the structure of the ligand used in the transition metal complex structure and the rare earth metal complex structure described above include acetylacetonate, 2,2′-bipyridine, 4,4′-dimethyl-2,2′-bipyridine, Examples thereof include 1,10-phenanthroline, 2-phenylpyridine, porphyrin, phthalocyanine, pyrimidine, quinoline and / or derivatives thereof, but are not limited thereto. One or more kinds of these ligands are coordinated with respect to one complex. In addition, a binuclear complex structure or a polynuclear complex structure, or a complex structure of two or more complexes can be used as the complex compound.

  The light emission mechanism in the phosphorescent metal complex structure which is a preferred light emitting material of the present invention is as follows. That is, the lowest excited singlet state is generated by electrical excitation at a rate of 25% and the lowest excited triplet state is generated by 75%. In the case of a transition metal complex structure or a rare earth metal complex structure, the lowest excited singlet state is generated by the heavy atom effect. Since intersystem crossing from the term state to the lowest excited triplet state easily occurs, the ratio of the lowest triplet state increases to 75% or more. In the case of a transition metal complex structure that emits phosphorescence from the lowest excited triplet state, a non-radiative transition exists together with a radiative transition that emits phosphorescence. In the case of a rare earth metal complex structure, the excitation energy of the lowest excited triplet state of the ligand is transferred to the central metal ion, and light is emitted from the excited level of the central metal ion. There is a non-radiative transition along with the transition. These non-radiative transitions cannot be suppressed unless the temperature is extremely low, and usually the light emission of the above compounds at room temperature is extremely weak.

However, in the luminescent material having the preferred phosphorescent metal complex structure of the present invention, the vibration of the molecule can be suppressed by fixing the luminescent portion to the polymer at the molecular level, so that the excitation energy is lost as the vibration of the molecule. Nothing will happen. In addition, although the excited triplet state is deactivated by oxygen, in the light-emitting material having a preferable phosphorescent metal complex structure of the present invention, it is possible to suppress the entry of oxygen by confining the light-emitting portion in the polymer. is there.
Specific examples of the polymerizable light-emitting compound used in the present invention include

のようなフェニルピリジン構造に重合性官能基が導入された金属錯体が挙げられる。

And a metal complex in which a polymerizable functional group is introduced into the phenylpyridine structure.

The polymerizable light-emitting compound composition used in the polymer light-emitting material of the present invention may contain an electron transport compound that forms an electron transport layer. As the electron transporting compound, known electron transporting materials such as quinolinol derivative metal complexes such as Alq ₃ (trisquinolinol aluminum), oxadiazole derivatives, and triazole derivatives can be used, but are not particularly limited thereto. These electron transport materials may be used alone or in combination with different electron transport materials.

  The electron transporting compound contained in the polymerizable light emitting compound composition used in the polymer light emitting material of the present invention may be a polymerizable electron transporting compound having polymerizability. If the electron transporting compound is polymerizable, it is more preferable because the degree of freedom in selecting a polymerizable light emitting compound composition used for the polymer light emitting material of the present invention is increased.

Examples of the polymerizable electron transport compound include at least one (meth) acryl group, vinyl, and other known electron transport compounds such as quinolinol derivative metal complexes such as Alq ₃ (triskinolinol aluminum), oxadiazole derivatives, and triazole derivatives. And compounds having a polymerizable functional group such as a group, a styryl group, an isocyanate group or a thioisocyanate group bonded thereto. Specific examples include bisquinolinol methacryloyloxyquinolinol aluminum, quinolinol bismethacryloyloxyquinolinol aluminum, methacryloyloxyoxadiazole, styryloxadiazole, and bisstyryloxadiazole. Also in the polymerizable electron transporting compound, a crosslinkable polymerizable electron transporting compound such as quinolinol bismethacryloyloxyquinolinol aluminum or bisstyryloxadiazole is preferable.

  The polymerizable light emitting compound composition used for the polymer light emitting material of the present invention may contain other polymerizable compounds. The degree of freedom in selecting the polymerizable light-emitting compound composition used for the polymer light-emitting material of the present invention by including other polymerizable compounds in the polymerizable light-emitting compound composition used for the polymer light-emitting material of the present invention. Is preferable.

  The other polymerizable compound is not particularly limited as long as it does not inhibit the light emission of the polymer light emitting material of the present invention. For example, methyl methacrylate, ethyl acrylate, ethylene glycol dimethacrylate, propylene glycol diacrylate, Examples include methylolpropane triacrylate, styrene, and stilbene. Among other polymerizable compounds, cross-linkable polymerizable compounds such as ethylene glycol dimethacrylate, propylene glycol diacrylate, trimethylolpropane triacrylate, and stilbene are preferable.

  The polymerizable composition used for the polymer light-emitting material of the present invention may contain a polymerization initiator. Any polymerization initiator can be used without particular limitation as long as it can initiate polymerization of the polymerizable functional group. Further, radical polymerization initiators, cationic polymerization initiators, anionic polymerization initiators and the like can be used depending on the polymerization mechanism of the polymerizable functional group, but radical polymerization initiators are preferred. Furthermore, if classified according to the activation mechanism of the polymerization initiator, a thermal polymerization initiator, a photopolymerization initiator, or the like can be used. Here, the photopolymerization initiator means one that initiates polymerization with so-called active energy rays such as visible light, ultraviolet rays, electron beams, and gamma rays.

  Thermal radical polymerization initiators include azo compounds such as 2,2′-azobisisobutyronitrile (AIBN) and 2,2′-azobisisovaleronitrile, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone Ketone peroxides such as peroxides, diacyl peroxides such as benzoyl peroxide, decanoyl peroxide, lauroyl peroxide, dialkyls such as dicumyl peroxide, t-butylcumyl peroxide, di-t-butyl peroxide Peroxides, 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, 1,1-di-t-butylperoxycyclohexane, 2,2-di (t-butylperoxy) Peroxyketals such as butane, t-butyl peroxy Pivalate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisobutyrate, di-t-butylperoxyhexahydroterephthalate, di-t-butylperoxyazelate, t-butylperoxy -3,5,5-trimethylhexanoate, t-butylperoxyacetate, t-butylperoxybenzoate, di-t-butylperoxytrimethyladipate, t-butylperoxy 2-ethylhexanoate, t- Hexylperoxy alkyl peroxyesters such as 2-ethylhexanoate, and percarbonates such as diisopropyl peroxydicarbonate, di-sec-butyl peroxydicarbonate, and t-butyl peroxyisopropyl carbonate.

  Examples of the radical photopolymerization initiator include acetophenone, 2,2-dimethoxy-2-phenylacetophenone, diethoxyacetophenone, 1-hydroxy-cyclohexyl-phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl]. 2-Montholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 2-hydroxy-2-methyl-1-phenyl-propane-1- Acetophenone derivatives such as ON, benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4-trimethylsilylbenzophenone, 4-benzoyl-4′-methyl-diphenyl sulfide and other benzophenone derivatives, benzoin, benzoin ethyl ether, benzoin propyl ether Ben In isobutyl ether, benzoin derivatives such as benzoin isopropyl ether, methylphenyl glyoxylate, benzoin dimethyl ketal, etc. 2,4,6-trimethylbenzoyl diphenylphosphine oxide.

The amount of these polymerization initiators used is in the range of 0.001% to 5% by weight, preferably 0.01% to 1% by weight, based on the weight of the polymerizable composition of the present invention.
The polymerizable composition containing at least one luminescent compound of the present invention can be formed into a film on the base layer by a coating method. The base layer varies depending on the configuration of the organic light emitting device, but in the case of FIG. 1, the hole transport layer is 3, and in Examples 11 to 14, the ITO anode is the base layer. In addition, when the polymerizable composition containing at least one luminescent compound of the present invention is coated on the base layer, the composition can be diluted with a solvent and applied. By solvent dilution, the viscosity of the composition can be lowered and the film thickness can be reduced. The solvent used can be removed by a treatment such as heating or decompression before, during or after the polymerization.

Although the thickness of the light emitting layer made of the polymer light emitting material of the present invention cannot be generally limited, it is preferably 1 nm to 10 μm, and more preferably 5 nm to 1 μm.
In the organic light-emitting device according to the present invention, the luminous efficiency and / or durability can be further improved by forming the hole transport layer and the electron transport layer on both sides or one side of the light-emitting layer.

  As a hole transport material for forming the hole transport layer, TPD (N, N′-dimethyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′diamine), α-NPD ( 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl), m-MTDATA (4,4 ′, 4 ″ -tris (3-methylphenylphenylamino) triphenylamine), etc. Known hole transport materials such as triphenylamine derivatives, polyvinylcarbazole, and polyethylenedioxythiophene can be used, but are not particularly limited thereto. These hole transport materials may be used alone, but may be mixed or laminated with different hole transport materials. Although the hole transport layer is formed by vapor deposition or the like, the thickness of the hole transport layer depends on the conductivity of the hole transport layer and cannot be generally limited, but is preferably 10 nm to 10 μm, preferably 10 nm to 1 μm. Further preferred.

As the electron transporting material forming the electron transporting layer, known electron transporting materials such as the above-described quinolinol derivative metal complexes such as Alq ₃ (triskinolinol aluminum), oxadiazole derivatives, and triazole derivatives can be used. It is not limited to. These electron transport materials are used alone, but may be mixed or laminated with different electron transport materials. The electron transport layer is formed by depositing the above electron transport material by a method such as vapor deposition. The thickness depends on the conductivity of the electron transport layer and cannot be generally limited, but is preferably 10 nm to 10 μm, preferably 10 nm to 1 μm. Further preferred.

  In addition to the light emitting material, the hole transport material, and the electron transport material used for the light emitting layer, each layer can be formed independently, and each layer can be formed using a polymer material as a binder. Examples of the polymer material used for this include, but are not limited to, polymethyl methacrylate, polycarbonate, polyester, polysulfone, polyphenylene oxide, and the like.

  As a method for forming a light emitting material, a hole transport material, and an electron transport material of a light emitting element using the polymer light emitting material of the present invention, a resistance heating vapor deposition method, an electron beam vapor deposition method, a sputtering method, a coating method, or the like can be used. Thus, there is no particular limitation thereto. When each material is a low molecular compound, resistance heating vapor deposition and electron beam vapor deposition are mainly used, and when the material is a polymer material such as a polymer light emitting material, a coating method is mainly used.

  As the anode material of the organic light emitting device according to the present invention, known transparent conductive materials such as conductive polymers such as ITO (indium tin oxide), tin oxide, zinc oxide, polythiophene, polypyrrole, and polyaniline can be used. It is not limited to these. The surface resistance of the electrode made of this transparent conductive material is preferably 1 to 50Ω / □. As a method for forming these anode materials, an electron beam vapor deposition method, a sputtering method, a chemical reaction method, a coating method, and the like can be used, but there is no particular limitation thereto. The thickness of the anode is preferably 50 to 300 nm.

  Further, a buffer layer may be inserted between the anode and the hole transport layer or the organic layer laminated adjacent to the anode for the purpose of relaxing the injection barrier against hole injection. For this, a known material such as copper phthalocyanine is used, but it is not particularly limited thereto.

  As the cathode material of the organic light emitting device according to the present invention, known cathode materials such as Al, MgAg alloys, alkali metals such as Ca, and alloys of Al and alkali metals such as AlCa can be used, but are particularly limited thereto. There is nothing. As a film forming method for these cathode materials, a resistance heating vapor deposition method, an electron beam vapor deposition method, a sputtering method, an ion plating method, or the like can be used, but is not particularly limited thereto. The thickness of the cathode is preferably 10 nm to 1 μm, and more preferably 50 to 500 nm.

  An insulating layer having a thickness of 0.1 to 10 nm may be inserted between the cathode and the electron transport layer or the organic layer stacked adjacent to the cathode for the purpose of improving the electron injection efficiency. . As this insulating layer, known cathode materials such as lithium fluoride, magnesium fluoride, magnesium oxide, and alumina can be used, but are not particularly limited thereto.

  Further, a hole block layer may be provided adjacent to the cathode side of the light emitting layer in order to prevent holes from passing through the light emitting layer and to efficiently recombine with electrons in the light emitting layer. For this, a known material such as a triazole derivative or an oxadiazole derivative is used, but it is not particularly limited thereto.

  As the substrate of the organic light emitting device according to the present invention, an insulating substrate transparent to the emission wavelength of the light emitting material can be used. Besides glass, known transparent plastics such as PET (polyethylene terephthalate) and polycarbonate are known. Although materials can be used, it is not limited to these.

  The organic light emitting device of the present invention can form a pixel by a matrix method or a segment method by a known method, and can also be used as a backlight without forming a pixel.

  The present invention will be described in more detail below with typical examples. Note that these are merely examples for description, and the present invention is not limited thereto.

Example 1 Synthesis of Polymerizable Luminescent Compound: Ir (MPPy) (PrCOPPy) ₂ Methoxyphenylpyridine (MeOPPy) was synthesized according to a conventional method (Scheme (1)). That is, 3-methoxyphenylmagnesium bromide was synthesized by using Mg in 60 ml of dehydrated THF (tetrahydrofuran) from 8.98 g (48 mmol) of 3-bromoanisole by a conventional method. Next, a solution obtained by dissolving 6.32 g (40 mmol) of 2-bromopyridine and 0.74 g of [1,2-bis (diphenylphosphino) ethane] dichloronickel (0) (Ni (dppe) Cl ₂ ) in 40 ml of dehydrated THF. The 3-methoxyphenylmagnesium bromide obtained previously was added and reacted at room temperature for 12 hours to obtain 6.03 g (32.4 mmol) of colorless and transparent 3-methoxyphenylpyridine (MeOPPy). Identification was performed by C, H, N elemental analysis, NMR, and IR.

次いでこのMeOPPyとトリス（アセチルアセトナート）イリジウム(ＩＩＩ)（Ir(acac)₃）を下記スキーム(2)で示す如く、高温で反応させ、トリス（３−メトキシフェニルピリジン）イリジウム(ＩＩＩ)（Ir(MeOPPy)₃）を合成した。即ち、MeOPPy５．００ｇ（２７．０ｍｍｏｌ）とIr(acac)₃２．０g（４．１ｍｍｏｌ）をグリセロール２００ｍｌ中、２５０℃で９時間反応させ、カラムで精製することにより、蛍光性黄色粉末としてIr(MeOPPy)₃を０．４００ｇ（０．５４ｍｍｏｌ）得た。同定はＣ、Ｈ、Ｎ及びIr元素分析、ＩＲで行った。

Next, this MeOPPy and tris (acetylacetonato) iridium (III) (Ir (acac) ₃ ) are reacted at a high temperature as shown in the following scheme (2) to obtain tris (3-methoxyphenylpyridine) iridium (III) (Ir (MeOPPy) ₃ ) was synthesized. That is, 5.00 g (27.0 mmol) of MeOPPy and 2.0 g (4.1 mmol) of Ir (acac) ₃ were reacted in 200 ml of glycerol for 9 hours at 250 ° C. and purified by a column to obtain Ir as a fluorescent yellow powder. 0.400 g (0.54 mmol) of (MeOPPy) ₃ was obtained. Identification was carried out by C, H, N and Ir elemental analysis and IR.

上記と同様にして、合計３．２０ｇ（４．３２ｍｍｏｌ）のIr(MeOPPy)₃を得た。
このIr(MeOPPy)₃を常法に従い、塩酸水溶液中でMeO基を加水分解させ、OH基にし、粉末としてトリス（３−ヒドロキシフェニルピリジン）イリジウム(ＩＩＩ)（Ir(HOPPy)₃）を得た（スキーム(3)）。

In the same manner as described above, a total of 3.20 g (4.32 mmol) of Ir (MeOPPy) ₃ was obtained.
This Ir (MeOPPy) ₃ was hydrolyzed to form an OH group in an aqueous hydrochloric acid solution according to a conventional method to obtain tris (3-hydroxyphenylpyridine) iridium (III) (Ir (HOPPy) ₃ ) as a powder. (Scheme (3)).

次いでIr(HOPPy)₃を下記スキーム(4)に従い、メタクリル酸クロライドとモル比１：１で反応させることにより、OH基の一部分をメタクリル化させIr(MPPy)(HOPPy)₂が主成分となる錯体を合成した。次いで残りのOH基をプロピオン酸クロライド(PrCOCl)と反応させ、Ir(MPPy)(PrCOPPy)₂が主成分となる錯体を得た。

Next, Ir (HOPPy) ₃ is reacted with methacrylic acid chloride in a molar ratio of 1: 1 according to the following scheme (4) to methacrylate a part of the OH group, and Ir (MPPy) (HOPPy) ₂ becomes the main component. A complex was synthesized. Next, the remaining OH group was reacted with propionic acid chloride (PrCOCl) to obtain a complex mainly composed of Ir (MPPy) (PrCOPPy) ₂ .

That is, 32 ml of dehydrated THF, 3.224 g (4 mmol) of Ir (HOPPy) _{3 and} 2.40 g (23.6 mmol) of triethylamine as a deoxidizer were charged in a reaction vessel, and then 0.424 g (4 mmol) of methacrylic acid chloride was added to 16 ml of dehydrated THF. The solution dissolved in was dropped over 30 minutes and reacted at 20 ° C. for 5 hours. A solution obtained by further dissolving 2.680 g (16 mmol) of propionic acid chloride in 16 ml of dehydrated THF was added dropwise to this reaction solution over 30 minutes, and the remaining OH group was reacted by reacting at 20 ° C. for 5 hours to obtain triethylamine hydrochloride. Was filtered off. The solvent of the filtrate was evaporated to dryness, and the resulting solid component was purified by recrystallization twice with a chloroform / methanol mixed solvent to obtain 2.305 g of target Ir (MPPy) (PrCOPPy) ₂ (2. 60 mmol) was obtained as a powder. This identification was performed by elemental analysis of C, H, N and Ir and IR.

（実施例２）重合性発光化合物：Ir(MiPPy)(PrCOPPy)₂
実施例１と同様にして合成したモノマー中間体Ir(HOPPy)₃を下記スキーム(５)で示す如く、メタクリロイルオキシエチルイソシアネート(MOI、昭和電工製)と1:1（モル比）で反応させ、次いで残りのOH基をPrCOClと反応させ、Ir(MiPPy)(PrCOPPy)₂が主成分となる錯体を得た。

Example 2 Polymerizable Luminescent Compound: Ir (MiPPy) (PrCOPPy) ₂
The monomer intermediate Ir (HOPPy) ₃ synthesized in the same manner as in Example 1 was reacted with methacryloyloxyethyl isocyanate (MOI, manufactured by Showa Denko) at 1: 1 (molar ratio) as shown in the following scheme (5). Subsequently, the remaining OH group was reacted with PrCOCl to obtain a complex containing Ir (MiPPy) (PrCOPPy) ₂ as a main component.

That is, 32 ml of dehydrated THF, 3.224 g (4 mmol) of Ir (HOPPy) _{3 and} 0.636 g (4 mmol) of MOI were charged in a reaction vessel, and a catalytic amount of dibutyltin dilaurate was added and reacted at 20 ° C. for 5 hours. After adding 2.400 g (24.5 mmol) of triethylamine as a deoxidizer to this reaction solution, a solution prepared by dissolving 2.68 g (16 mmol) of propionic acid chloride in 16 ml of dehydrated THF was added dropwise over 30 minutes, and further 20 ° C. The remaining OH group was reacted by reacting for 5 hours, and triethylamine hydrochloride was filtered off. The solvent of the filtrate was evaporated to dryness, and the obtained solid component was purified by recrystallization twice with a chloroform / methanol mixed solvent to obtain 2.62 g of target Ir (MiPPy) (PrCOPPy) ₂ (2. 70 mmol) as a powder. Identification was performed by elemental analysis of C, H, N and Ir and IR.

（実施例３）重合性発光化合物：Ir(MPPy)₃の合成
実施例１で合成したと同様の方法でIr(MeOPPy)₃を常法に従い、塩酸水溶液中でMeO基を加水分解させ、OH基にし、粉末としてトリス（３−ヒドロキシフェニルピリジン）イリジウム(ＩＩＩ)（Ir(HOPPy)₃）を得た（スキーム(3)）。次いでIr(HOPPy)₃を下記スキーム(６)に従い、メタクリル酸クロライドとモル比１：３で反応させることにより、すべてのOH基をメタクリル化させIr(MPPy)₃錯体を合成した。

(Example 3) Synthesis of polymerizable light-emitting compound: Ir (MPPy) ₃ Ir (MeOPPy) ₃ was hydrolyzed in a hydrochloric acid aqueous solution in the same manner as Ir (MeOPPy) ₃ in the same manner as in Example 1, and OH Based on this, tris (3-hydroxyphenylpyridine) iridium (III) (Ir (HOPPy) ₃ ) was obtained as a powder (Scheme (3)). Then accordance Ir (HOPPY) ₃ the following scheme (6), methacrylic acid chloride and molar ratio of 1: by reacting 3, all OH groups was synthesized Ir (mppy) ₃ complexes were methacrylated.

That is, 32 ml of dehydrated THF, 3.224 g (4 mmol) of Ir (HOPPy) _{3 and} 2.40 g (23.6 mmol) of triethylamine as a deoxidizing agent were charged in a reaction vessel, and then 1.293 g (12.2 mmol) of methacrylic acid chloride was added. A solution dissolved in 32 ml of dehydrated THF was added dropwise over 90 minutes and reacted at 20 ° C. for 5 hours. The precipitated triethylamine hydrochloride is filtered off, the solvent of the filtrate is evaporated to dryness, and the resulting solid component is purified by recrystallization twice with a mixed solvent of hexafluoroisopropanol / methanol. Trifunctional Ir (MPPy) ₃ 2.805 g (3.08 mmol) was obtained as a powder. This identification was performed by elemental analysis of C, H, N and Ir and IR.

（実施例４）重合性発光化合物：Ir(MiPPy) ₂(PrCOPPy)の合成
実施例１と同様にして合成したモノマー中間体Ir(HOPPy)₃を下記スキーム(７)で示す如く、メタクリロイルオキシエチルイソシアネート(MOI、昭和電工製)と1:２（モル比）で反応させ、次いで残りのOH基をPrCOClと反応させ、Ir(MiPPy) ₂(PrCOPPy)錯体を得た。

Example 4 Synthesis of Polymerizable Luminescent Compound: Ir (MiPPy) ₂ (PrCOPPy) As shown in the following scheme (7), a monomer intermediate Ir (HOPPy) ₃ synthesized in the same manner as Example 1 was subjected to methacryloyloxyethyl. It reacted with isocyanate (MOI, Showa Denko) at 1: 2 (molar ratio), and then the remaining OH group was reacted with PrCOCl to obtain an Ir (MiPPy) ₂ (PrCOPPy) complex.

That is, 48 ml of dehydrated THF, 3.224 g (4 mmol) of Ir (HOPPy) _{3, and} 1.272 g (8 mmol) of MOI were charged in a reaction vessel, and a catalytic amount of dibutyltin dilaurate was added and reacted at 20 ° C. for 5 hours. After adding 2.400 g (24.5 mmol) of triethylamine as a deoxidizer to this reaction solution, a solution prepared by dissolving 1.01 g (6 mmol) of propionic acid chloride in 8 ml of dehydrated THF was added dropwise over 30 minutes, and further 20 ° C. The remaining OH group was reacted by reacting for 5 hours, and triethylamine hydrochloride was filtered off. The solvent of the filtrate was evaporated to dryness, and the obtained solid component was purified by recrystallization twice with a chloroform / methanol mixed solvent to obtain 2.75 g of target Ir (MiPPy) ₂ (PrCOPPy) (2. 80 mmol) was obtained as a powder. This identification was performed by elemental analysis of C, H, N and Ir and IR.

（実施例５〜１０） 重合性組成物を用いた有機発光素子の作製、評価
実施例１、２、３、４で合成した４種の重合性燐光発光化合物：単官能Ir(MPPy)(PrCOPPy)₂ 、単官能Ir(MiPPy)(PrCOPPy)₂、３官能Ｉr(MPPy)₃、２官能Ｉr(MiPPy) ₂(PrCOPPy)を表１の如く組み合わせて１０質量％のクロロホルム溶液を作製し、重合開始剤としてＡＩＢＮ（アゾビスイソブチロニトリル）をモノマー総量に対し、０．０２質量部添加後、PEDOT(ポリエチレンジオキシチオフェン；バイエル社製)を５００Åの厚さで予め塗布成膜したＩＴＯ陽極上にスピンコート法で５ｍｍ×５ｍｍの面に塗布後、６０℃加熱２時間行うことにより、各モノマーを重合硬化させた。さらに８０℃減圧で８時間乾燥し、厚さ約１０００Åの燐光高分子膜をＰＥＤＯＴ/ＩＴＯ陽極上に各２個ずつ成膜した。

Examples 5 to 10 Production and Evaluation of Organic Light-Emitting Device Using Polymerizable Composition Four kinds of polymerizable phosphorescent compounds synthesized in Examples 1, 2, 3, and 4: monofunctional Ir (MPPy) (PrCOPPy ) ₂ , Monofunctional Ir (MiPPy) (PrCOPPy) ₂ , Trifunctional Ir (MPPy) ₃ , Bifunctional Ir (MiPPy) ₂ (PrCOPPy) are combined as shown in Table 1 to prepare a 10% by mass chloroform solution and polymerized An ITO anode in which AIBN (azobisisobutyronitrile) as an initiator was added in an amount of 0.02 parts by mass with respect to the total amount of monomer, and then PEDOT (polyethylenedioxythiophene; manufactured by Bayer) was applied in advance to a thickness of 500 mm. Each monomer was polymerized and cured by applying it to a surface of 5 mm × 5 mm by spin coating and heating at 60 ° C. for 2 hours. Further, it was dried at 80 ° C. under reduced pressure for 8 hours, and two phosphorescent polymer films each having a thickness of about 1000 mm were formed on the PEDOT / ITO anode.

  TAZ (3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1, as an electron transport layer on these 6 types (total 12) of phosphorescent polymer / PEDOT / ITO electrodes 2,4-triazol) was deposited by vacuum deposition to a thickness of about 500 mm. Subsequently, Ag / Mg was formed into a film with a mass ratio of 9/1 to a thickness of about 1000 mm as a cathode, and six types of organic light emitting elements (two each) were prepared. These devices were attached with lead wires in a glove box in an argon atmosphere and sealed in a glass container in an argon atmosphere, and used for evaluation of light emission.

  Luminance is supplied as a power source by using a programmable DC voltage / current source TR6143 manufactured by Advantest Co., Ltd., and voltage is applied to the organic light-emitting devices obtained in the examples, and the luminance is measured by a luminance meter BM- manufactured by Topcon Corporation. 8 was measured.

  When a direct current power supply was applied to the light emitting element, the initial luminance at the light emission starting voltage of 10 V, and the luminance after 240 hours when continuously emitting light at a fixed voltage of 10 V were as shown in Table 1 (each polymer system 2 Average).

（実施例１１〜１４、比較例１） 重合性組成物を用いた有機発光素子の作製、評価
常法に従いフェニルピリジン（PPy）とトリス（アセチルアセトナト）イリジウム(ＩＩＩ)（Ir(acac)₃）を３００℃で反応させ、燐光発光化合物トリス（フェニルピリジン）イリジウム(ＩＩＩ)（Ir(PPy)₃）を合成した。このIr(PPy)₃、実施例１、３で合成した２種の重合性燐光発光化合物：単官能Ir(MPPy)(PrCOPPy)₂ 、３官能Ｉr(MPPy)₃と２官能重合性電子輸送性化合物：ビススチリルオキサジアゾール（BSODA）、及び比較として電子輸送性化合物：オキサジアゾール(ODA)を表２の如く組み合わせて発光化合物１０質量％のクロロホルム溶液として電子輸送性化合物添加重合性発光化合物組成物を作製し、重合開始剤としてＡＩＢＮ（アゾビスイソブチロニトリル）をモノマー総量に対し、０．０２質量部添加後、PEDOT(バイエル社製)を５００Åの厚さで予め塗布成膜したＩＴＯ陽極上にスピンコート法で５ｍｍ×５ｍｍの面に塗布後、６０℃加熱２時間行うことにより、各モノマーを重合硬化させた。さらに８０℃減圧で８時間乾燥し、厚さ約１０００Åの燐光高分子膜をＰＥＤＯＴ/ＩＴＯ陽極上に各２個ずつ成膜した。

(Examples 11-14, Comparative Example 1) Preparation of the organic light emitting device using a polymerizable composition, evaluation routine manner and phenylpyridine (PPy) tris (acetylacetonato) iridium (III) (Ir (acac) ₃ ) Was reacted at 300 ° C. to synthesize a phosphorescent compound tris (phenylpyridine) iridium (III) (Ir (PPy) ₃ ). This Ir (PPy) ₃ , two polymerizable phosphorescent compounds synthesized in Examples 1 and 3: monofunctional Ir (MPPy) (PrCOPPy) ₂ , trifunctional Ir (MPPy) ₃ and bifunctional polymerizable electron transport properties Compound: Bisstyryl oxadiazole (BSODA) and, as a comparison, electron transporting compound: oxadiazole (ODA) in combination as shown in Table 2 to form a 10% by mass chloroform solution of 10% by weight of the light transporting compound-added polymerizable light emitting compound A composition was prepared, and 0.02 parts by mass of AIBN (azobisisobutyronitrile) as a polymerization initiator was added to the total amount of the monomer, and then PEDOT (manufactured by Bayer) was applied in advance to a thickness of 500 mm. Each monomer was polymerized and cured by applying it on a surface of 5 mm × 5 mm by spin coating on the ITO anode and heating at 60 ° C. for 2 hours. Further, it was dried at 80 ° C. under reduced pressure for 8 hours, and two phosphorescent polymer films each having a thickness of about 1000 mm were formed on the PEDOT / ITO anode.

  On these 5 types (total 10) phosphorescent polymer / PEDOT / ITO electrodes, Ag / Mg as a cathode was formed into a film with a mass ratio of 9/1 to a thickness of about 1000 mm, and 5 types of organic light emitting elements (each 2 Created). These devices were attached with lead wires in a glove box in an argon atmosphere, sealed in a glass container in an argon atmosphere, and evaluated for luminous properties in the same manner as in Examples 5-10.

（実施例１５） 重合性組成物を用いた有機発光素子の作製、評価
蛍光発光材料：トリスキノリノールアルミニウム(Alq₃)と２官能重合性電子輸送性化合物：ビススチリルオキサジアゾール（BSODA）をモル比１：１でクロロホルム中で混合し、１５質量％のクロロホルム溶液として電子輸送性化合物添加重合性発光化合物組成物を作製し、重合開始剤としてＡＩＢＮ（アゾビスイソブチロニトリル）をビススチリルオキサジアゾール総量に対し、０．０２質量部添加後、PEDOT(バイエル社製)を５００Åの厚さで予め塗布成膜したＩＴＯ陽極上にスピンコート法で５ｍｍ×５ｍｍの面に塗布後、６０℃加熱２時間行うことにより、各モノマーを重合硬化させた。さらに８０℃減圧で８時間乾燥し、厚さ約１０００Åの電子輸送性化合物添加蛍光高分子膜をＰＥＤＯＴ/ＩＴＯ陽極上に２個成膜した。次に、実施例１１〜１４と同様にして有機発光素子２個を作製し、発光性評価を行った。

Preparation of organic light-emitting device (Example 15) the polymerizable composition, evaluated fluorescent material: tris-quinolinol aluminum (Alq ₃₎ and difunctional polymerizable electron-transporting compound molar bis styryl oxadiazole (BSODA) The mixture was mixed in chloroform at a ratio of 1: 1 to prepare an electron transport compound-added polymerizable light-emitting compound composition as a 15% by mass chloroform solution, and AIBN (azobisisobutyronitrile) as a polymerization initiator was bisstyryl oxalate. After adding 0.02 parts by mass with respect to the total amount of diazole, PEDOT (manufactured by Bayer) was applied in advance to a thickness of 500 mm on an ITO anode and applied to a 5 mm × 5 mm surface by spin coating, and then 60 ° C. Each monomer was polymerized and cured by heating for 2 hours. Further, the film was dried at 80 ° C. under reduced pressure for 8 hours, and two electron transporting compound-added fluorescent polymer films having a thickness of about 1000 mm were formed on the PEDOT / ITO anode. Next, two organic light emitting elements were produced in the same manner as in Examples 11 to 14, and the light emitting property was evaluated.

When a direct current power supply was applied to the organic light emitting device, the light emission starting voltage was 4 V, the initial luminance at 10 V was 980 Cd / m ² , and the luminance after 240 hours when the light was fixed continuously at 10 V and continuously emitted was 830 Cd / m ² . m ² (average of 2).

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

Claims (18)

An organic light emitting device using a polymer light emitting material obtained by polymerizing after forming a polymerizable composition containing at least one light emitting compound into a film,
The light emitting compound is a polymerizable light emitting compound;
At least one of the polymerizable light-emitting compounds is a cross-linkable light-emitting compound having two or more polymerizable functional groups, and the polymer after polymerization is a cross-linkable polymer,
Organic, characterized in that the emission mechanism of the light-emitting part of the luminescent compound is due to the transition from the excited triplet state to the ground state of the electronic energy level or to the ground state via the excited triplet state Light emitting element.   The organic light-emitting device according to claim 1, wherein the polymerizable composition contains a polymerizable compound other than at least one light-emitting compound.   The organic light emitting device according to claim 2, wherein at least one of the polymerizable compounds other than the light emitting compound is a polymerizable electron transporting compound.   The organic light-emitting device according to claim 2, wherein at least one of the polymerizable compounds other than the light-emitting compound is a cross-linkable polymerizable compound having two or more polymerizable functional groups.   The light emitting part has a metal complex structure, and the polymer light emitting material according to any one of claims 1 to 4.   6. The polymer light-emitting material according to claim 5, wherein the light-emitting moiety has a transition metal complex structure.   The polymer light-emitting material according to claim 5 or 6, wherein the light-emitting moiety contains a nitrogen atom in the complex structure forming portion.   The polymer light-emitting material according to claim 7, wherein the light-emitting moiety includes a pyridine skeleton, a pyrimidine skeleton, and / or a quinoline skeleton in the complex structure forming portion.   9. The coating film forming type electron transport layer and / or the coating film forming type hole transport layer are formed on both surfaces and / or one surface of the light emitting layer made of a polymer light emitting material. The organic light emitting element in any one. An organic light emitting device manufacturing method comprising forming a light emitting layer by polymerizing a polymerizable composition containing at least one light emitting compound on an electrode or a charge transport layer and then polymerizing the polymerizable composition. And
The light emitting compound is a polymerizable light emitting compound;
At least one of the polymerizable light-emitting compounds is a cross-linkable light-emitting compound having two or more polymerizable functional groups, and the polymer after polymerization is a cross-linkable polymer,
Organic, characterized in that the emission mechanism of the light-emitting part of the luminescent compound is due to the transition from the excited triplet state to the ground state of the electronic energy level or to the ground state via the excited triplet state Manufacturing method of light emitting element.   The method for producing an organic light-emitting element according to claim 10, wherein the polymerizable composition contains a polymerizable compound other than at least one light-emitting compound.   The method for producing an organic light-emitting element according to claim 11, wherein at least one of the polymerizable compounds other than the light-emitting compound is a polymerizable electron-transporting compound.   The method for producing an organic light emitting device according to claim 11, wherein at least one of the polymerizable compounds other than the light emitting compound is a crosslinkable polymerizable compound having two or more polymerizable functional groups.   The method for producing an organic light-emitting element according to claim 10, wherein the light-emitting portion has a metal complex structure.   The method for producing an organic light-emitting device according to claim 14, wherein the light-emitting moiety has a transition metal complex structure.   The method for producing an organic light-emitting element according to claim 14, wherein a nitrogen atom is contained in the complex structure-forming portion of the light-emitting portion.   The method for producing an organic light-emitting device according to claim 16, wherein the complex structure-forming portion of the light-emitting portion contains a pyridine skeleton, a pyrimidine skeleton, and / or a quinoline skeleton.   After forming a polymerizable composition in which at least one of the polymerizable compounds in the polymerizable composition is a cross-linkable polymerizable compound having two or more polymerizable functional groups on the anode or the hole transport layer, cross-linking polymerization 18. The method for producing an organic light-emitting device according to claim 10, further comprising forming an electron transport layer on the insoluble cross-linked polymer light-emitting material layer formed by coating. .

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