JP2009126793A - New di(pyridylphenyl) derivative, electron transport material comprising the same and organic electroluminescent element containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new di(pyridylphenyl)derivative, an electron transport material comprising the same and an organic electroluminescent element containing the same. <P>SOLUTION: This di(pyridylphenyl)derivative expressed by general formula (1), the electron transport material comprising the same and the organic electroluminescent element containing the same are provided. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a novel di (pyridylphenyl) derivative, an electron transport material comprising the same, and an organic electroluminescence device (organic EL device) containing the same.

  The organic electroluminescence element emits light by itself, when excitation energy purified by recombination of holes injected from the electrode and the electrode is relaxed to a ground state through a light emission process. However, there are two types of excited states generated by recombination of holes and electrons, a singlet excited state and a triplet excited state, in a ratio of 1: 3. In many cases, a fluorescent material utilizing light emission from a singlet excited state has been used as a light emitting material, and therefore, the internal quantum efficiency is 25% at the maximum. The quantum efficiency was limited to 5%.

  In recent years, improvement in luminous efficiency has been reported by using light emission from a triplet excited state, that is, phosphorescence emission, using a complex compound utilizing a heavy atom effect such as iridium or platinum (for example, non-light emission). Patent Document 1). The maximum internal quantum efficiency can theoretically reach 100% by utilizing light emission from the triplet excited state in addition to the singlet excited state, and phosphorescent materials are attracting attention as light emitting materials (non Patent Document 3).

に示すトリス（２−フェニルピリジナト）イリジウム（III）［Ｉｒ（ｐｐｙ）_３］が広く利用されている。 For example, as a green material, the following formula

Tris (2-phenylpyridinato) iridium (III) [Ir (ppy) ₃ ] shown in FIG.

で示すビス［２−（４，６−ジフルオロフェニル）ピリジネート−Ｎ，Ｃ２′］イリジウム（III）ピコリネート（ＦＩｒｐｉｃ）が注目を浴びるようになり、それ以降ＦＩｒｐｉｃを用いた有機ＥＬ素子の高効率化検討および新規青色リン光錯体探索研究が盛んに行われるようになった。 In addition, the following formula, which is a blue light-emitting material according to Non-Patent Document 2 by Adachi et al.

Bis [2- (4,6-difluorophenyl) pyridinate-N, C2 ′] iridium (III) picolinate (FIrpic) shown in FIG. 1 has attracted attention, and since then, higher efficiency of organic EL devices using FIrpic Studies and exploration studies for new blue phosphorescent complexes have been actively conducted.

で示すトリス｛１−［４−（トリフルオロメチル）フェニル］−１Ｈ−ピラゾラート−Ｎ，Ｃ２′｝イリジウム（III）（Ｉｒｔｆｍｐｐｚ_３）やＭ．Ｅ．Ｔｈｏｍｐｓｏｎらによる非特許文献４では下記式

で示すビス［２−（４′，６′−ジフルオロフェニル）ピリジナト−Ｎ，Ｃ２′］テトラキス（１−ピラゾリル）ボレート（Ｆｉｒ６）が開発された。 As a result, S. R. Non-patent document 1 by Forrest et al.

Tris {1- [4- (trifluoromethyl) phenyl] -1H-pyrazolate-N, C2 ′} iridium (III) (Irtfmpppz ₃ ) and M. E. Non-Patent Document 4 by Thompson et al.

Bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] tetrakis (1-pyrazolyl) borate (Fir6) has been developed.

In order for these light emitting materials to emit light efficiently, a hole transport agent, an electron transport agent, and the like must be selected so that the injection balance of holes and electrons is adjusted and these carriers can be sufficiently combined in the light emitting layer.
In particular, for blue phosphorescent materials, since the energy gap is large, a hole transport agent or an electron transport material having a wide gap is required. For these phosphorescent materials, Alq ₃ [tris (8-hydroxyquinolinolato) aluminum] and BAlq ₂ [bis (2-methyl-8-hydroxyquinolinolato) (which are conventionally used for electron transport materials) ( 4-phenylphenoxy) aluminum] and the like are used, but since it does not have a sufficient energy gap for use in phosphorescent materials, it is necessary to develop a new wide gap electron transport material.
M.M. A. Baldo, S .; Lamansky, P.M. E. Burrows, M .; E. Thompson, S.M. R. Forrest Appl. Phys. Lett 1999 75 (1) 4-7 Appl. Phys. Lett. 79, 2082 (2001) J. et al. Appl. Phys. 90 5048 (2001) Polyhedron 23 (2004) 419-428

  An object of the present invention is to provide a novel di (pyridylphenyl) derivative, an electron transport material comprising the same, and an organic electroluminescence device including the same.

（式中、Ｑは

よりなる群から選ばれた基であり、Ｒ^１〜Ｒ^６およびＲ^１０〜Ｒ^１１は水素、炭素数１〜６の直鎖または分岐のアルキル基、炭素数１〜６の直鎖または分岐のアルコキシ基および炭素数１〜６の直鎖または分岐のモノ−またはジ−アルキルアミノ基よりなる群からそれぞれ独立して選ばれた基である）
で示されるジ（ピリジルフェニル）誘導体に関する。
本発明の第２は、請求項１記載のジ（ピリジルフェニル）誘導体よりなる電子輸送材料に関する。
本発明の第３は、請求項１記載のジ（ピリジルフェニル）誘導体を含む有機エレクトロルミネッセンス素子に関する。
なお、前記Ｑとしては、（ａ）で表される基が最も好ましい。 The first of the present invention is the following general formula (1)

(Where Q is

R ^{1 to} R ⁶ and R ^{10 to} R ¹¹ are groups selected from the group consisting of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, and a linear or branched group having 1 to 6 carbon atoms. Each independently selected from the group consisting of an alkoxy group and a linear or branched mono- or di-alkylamino group having 1 to 6 carbon atoms)
The di (pyridylphenyl) derivative shown by these.
The second of the present invention relates to an electron transport material comprising the di (pyridylphenyl) derivative according to claim 1.
3rd of this invention is related with the organic electroluminescent element containing the di (pyridylphenyl) derivative of Claim 1.
In addition, as said Q, group represented by (a) is the most preferable.

Examples of the linear or branched alkyl group having 1 to 6 carbon atoms in R ^{1 to} R ⁶ and R ^{10 to} R ¹¹ in the present invention include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, heptyl , Isoheptyl, n-hexyl and the like.

Examples of the linear or branched alkoxy group having 1 to 6 carbon atoms in R ^{1 to} R ⁶ and R ^{10 to} R ¹¹ in the present invention include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, Examples include heptoxy, isoheptoxy, n-hexyloxy and the like.

In the present invention, a linear or branched mono- or di-alkylamino group having 1 to 6 carbon atoms in R ^{1 to} R ⁶ and R ^{10 to} R ¹¹ is a part or all of hydrogen of —NH ₂ is the alkyl group. Is replaced with.

なお前記式中、Ｑは

よりなる群から選ばれた基であり、Ｒ^１〜Ｒ^６およびＲ^１０〜Ｒ^１１は水素、炭素数１〜６の直鎖または分岐のアルキル基、炭素数１〜６の直鎖または分岐のアルコキシ基および炭素数１〜６の直鎖または分岐のモノ−またはジ−アルキルアミノ基よりなる群からそれぞれ独立して選ばれた基であり、Ｘはハロゲンである。 The compound of the present invention can be produced by the following reaction.

In the above formula, Q is

R ^{1 to} R ⁶ and R ^{10 to} R ¹¹ are groups selected from the group consisting of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, and a linear or branched group having 1 to 6 carbon atoms. X is a group independently selected from the group consisting of an alkoxy group and a linear or branched mono- or di-alkylamino group having 1 to 6 carbon atoms.

  Specific examples of the compound of the present invention are illustrated below.

  The di (pyridylphenyl) derivative of the present invention has high electron transport performance. Therefore, it can be used as an electron injection material and an electron transport material.

  When using the di (pyridylphenyl) derivative of this invention for an organic electroluminescent element, it can also be used in combination with a suitable luminescent material (dopant).

  When the di (pyridylphenyl) derivative of the present invention is used for an electron transport layer, the compound of the present invention can be used as an electron injection material or an electron transport material. It can also be used in combination with other electron transport materials.

  Next, the organic electroluminescence element of the present invention will be described. The organic electroluminescence device of the present invention is a device in which a single layer or a multilayer organic compound is laminated between an anode and a cathode, and at least one layer of the organic compound layer contains the di (pyridylphenyl) derivative of the present invention. When the organic electroluminescence element is a single layer, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material and may contain a hole injecting material or an electron injecting material for the purpose of transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. . Examples of the configuration of the multi-layer organic electroluminescence element include, for example, ITO / hole transport layer / light-emitting layer / electron transport layer / cathode, ITO / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode, ITO / Hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, ITO / hole transport layer / light emitting layer / hole block layer / electron transport layer / cathode, ITO / hole injection layer / hole transport layer / light emitting layer / hole Block layer / electron transport layer / cathode, ITO / hole transport layer / light emitting layer / hole block layer / electron transport layer / electron injection layer / cathode, ITO / hole injection layer / hole transport layer / light emitting layer / hole block layer / electron Examples thereof include those laminated in a multilayer structure such as a transport layer / electron injection layer / cathode. Moreover, you may have a sealing layer on a cathode as needed.

  Each of the hole transport layer, the electron transport layer, and the light emitting layer may have a single layer structure or a multilayer structure. In addition, the hole transport layer and the electron transport layer should be provided separately with a layer responsible for the injection function (hole injection layer and electron injection layer) and a layer responsible for the transport function (hole transport layer and electron transport layer). You can also.

  The organic electroluminescence element of the present invention is not limited to the above configuration example, and can have various configurations. If necessary, a layer in which a hole transport layer component and a light emitting layer component or an electron transport layer component and a light emitting layer component are mixed may be provided.

  Hereinafter, the constituent elements of the organic electroluminescence element of the present invention will be described in detail by taking as an example an element structure comprising an anode / hole transport layer / light emitting layer / electron transport layer / cathode. The organic electroluminescence device of the present invention is preferably supported on a substrate.

  There is no restriction | limiting in particular about the raw material of a board | substrate, What is necessary is just used for the conventional organic electroluminescent element, For example, what consists of glass, quartz glass, a transparent plastic etc. can be used.

As an anode of the organic electroluminescence device of the present invention, an electrode material may be a single metal having a high work function (4 eV or more), an alloy of metals having a high work function (4 eV or more), a conductive substance, or a mixture thereof. preferable. Specific examples of such electrode materials include metals such as gold, silver, and copper, conductive transparent materials such as ITO (indium-tin oxide), tin oxide (SnO ₂ ), and zinc oxide (ZnO), polypyrrole, and polythiophene. Examples thereof include conductive polymer materials such as For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition, sputtering, or coating. The sheet electrical resistance of the anode is preferably several hundred Ω / cm ² or less. The thickness of the anode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm.

As the cathode, an electrode material is preferably a single metal having a small work function (4 eV or less), an alloy of metals having a small work function (4 eV or less), a conductive substance, or a mixture thereof. Specific examples of such electrode materials include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, magnesium, magnesium-silver alloy, magnesium-indium alloy, aluminum, aluminum-lithium alloy, and aluminum-magnesium alloy. Can be mentioned. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet electrical resistance of the cathode is preferably several hundred Ω / cm ² or less. The thickness of the cathode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm. In order to efficiently extract light emitted from the organic electroluminescence device of the present invention, at least one of the anode and the cathode is preferably transparent or translucent.

The hole transport layer of the organic electroluminescence device of the present invention is made of a hole transfer compound and has a function of transferring holes injected from the anode to the light emitting layer. When a hole transport compound is disposed between two electrodes to which an electric field is applied and holes are injected from the anode, a hole transport material having a hole mobility of at least 10 ⁻⁶ cm ² / V · second or more is obtained. preferable. The hole transport material used for the hole transport layer of the organic electroluminescence device of the present invention is not particularly limited as long as it has the above-mentioned preferable properties. It is possible to select and use any of the materials conventionally used as hole charge injection / transport materials in photoconductive materials and known materials used for the hole transport layer of organic electroluminescent devices. it can.

正孔輸送材料としては、下記化学式に示すＴＰＤ、ＤＴＡＳＩ、ｍ−ＤＴＡＴＰＢなどを挙げることができる。

Examples of the hole transfer material include phthalocyanine derivatives such as copper phthalocyanine, N, N, N ′, N′-tetraphenyl-1,4-phenylenediamine, and N, N′-di (m-tolyl) -N. , N′-diphenyl-4,4′-diaminobiphenyl (TPD), N, N′-di (1-naphthyl) -N, N′-diphenyl-4,4′-diaminobiphenyl (α-NPD), etc. And triarylamine derivatives, polyphenylenediamine derivatives, polythiophene derivatives, and water-soluble PEDOT-PSS (polyethylenedioxathiophene-polystyrenesulfonic acid). The hole transport layer may be composed of one or more of these other hole transport compounds, and a hole transport layer composed of a compound different from the hole transport material is laminated. Things may be used.
Examples of the hole injection material include PEDOT-PSS (polymer mixture) and DNTPD represented by the following chemical formula.

Examples of the hole transport material include TPD, DTASI, and m-DTATPB represented by the following chemical formula.

  The light emitting material of the light emitting layer of the organic electroluminescence device of the present invention is not particularly limited, and any one of conventionally known compounds can be selected and used.

Examples of the light-emitting material include perylene derivatives, naphthacene derivatives, quinacridone derivatives, coumarin derivatives (eg, coumarin 1, coumarin 540, coumarin 545, etc.), pyran derivatives (eg, DCM-1, DCM-2, DCJTB, etc.), organometallic complexes {Tris Fluorescent materials such as (8-hydroxyquinolinolato) aluminum (Alq ₃ ) and tris (4-methyl-8-hydroxyquinolinolato) aluminum (Almq ₃ ) and bis [2- (4,6-difluorophenyl) pyridinate -N, C2 '] iridium (III) picolinate (FIrpic), tris {1- [4- (trifluoromethyl) phenyl] -1H-pyrazolate-N, C2'} iridium (III) (Irtfmpppz ₃ ), bis [ 2- (4 ', 6'-difluorophenyl) pyridinato- , C2 '] tetrakis (1-pyrazolyl) borate (FIr6), tris (2-phenylpyridinato-), and the like iridium (III) [phosphorescent materials such as Ir _{(ppy) 3]}.}

  The light-emitting layer can also be formed of a host material and a guest material (dopant) [Appl. Phys. Lett. 65 3610 (1989)]. In particular, when a phosphorescent material is used for the light emitting layer, it is necessary to use a host material, and the host material used at this time is 4,4'-di (N-carbazolyl) -1,1'-biphenyl (CBP). 1,2-di (N-carbazolyl) benzene, 2,2′-di [4 ″-(N-carbazolyl) phenyl] -1,1′-biphenyl (4CzPBP) and the like.

The guest material is preferably 0.01 to 40% by weight, more preferably 0.1 to 20% by weight, based on the host material. Examples of guest materials include conventionally known FIrpic (Chemical Formula 4), Ir (ppy) ₃ (Chemical Formula 3), and Fir6 (Chemical Formula 6).

  As a material for the electron transport layer of the organic electroluminescence device of the present invention, the di (pyridylphenyl) derivative of the present invention is preferable. Although this thing can be used independently, you may use together with another electron transport material.

  The organic electroluminescent device of the present invention may further include an electron injection layer composed of an insulator between the cathode and the organic layer for the purpose of further improving the electron injection property. As the conductor used here, it is preferable to use at least one metal compound selected from alkali metal halides and alkaline earth metal halides. Examples of the alkali metal halide include lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, and lithium chloride. Examples of the alkaline earth metal halide include magnesium fluoride, calcium fluoride, barium fluoride, and strontium fluoride.

  The method for forming the hole transport layer and the light emitting layer is not particularly limited. For example, a dry film forming method (for example, a vacuum deposition method, an ionization vapor deposition method, etc.) or a wet film forming method [a solution coating method (for example, a spin coating method, a casting method, an ink jet method, etc.)] can be used. As a method for forming the electron transport layer of the di (pyridylphenyl) derivative of the present invention, a dry film forming method (for example, a vacuum evaporation method or an ionization evaporation method) is preferable. In addition, the above-described film formation method may be used in combination for manufacturing the element.

When forming each layer such as a hole transport layer, a light emitting layer, and an electron transport layer by a vacuum deposition method, the vacuum deposition conditions are not particularly limited. Usually, a boat temperature (deposition source temperature) of about 50 to 500 ° C. under a vacuum of about 10 ⁻⁴ Pa or less, a substrate temperature of about −50 to 300 ° C., and 0.01 to 50 nm / sec. Vapor deposition is preferred. When forming each layer of a positive hole transport layer, a light emitting layer, and an electron carrying layer using a some compound, it is preferable to co-evaporate each boat which put the compound, temperature-controlling each.

  When forming the hole transport layer and the light emitting layer by a solvent coating method, the components constituting each layer are dissolved or dispersed in a solvent to obtain a coating solution. Solvents include hydrocarbon solvents (eg, heptane, toluene, xylene, cyclohexane, etc.), ketone solvents (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), halogen solvents (eg, dichloromethane, chloroform, chlorobenzene, dichlorobenzene, etc.) ), Ester solvents (eg, ethyl acetate, butyl acetate, etc.), alcohol solvents (eg, methanol, ethanol, butanol, methyl cellosolve, ethyl cellosolve, etc.), ether solvents (eg, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like), aprotic solvents (for example, N, N'-dimethylacetamide, dimethyl sulfoxide and the like), water and the like. The solvent may be used alone, or a plurality of solvents may be used in combination.

  The thickness of each layer such as the hole transport layer, the light emitting layer, and the electron transport layer is not particularly limited, but is usually 5 to 5,000 nm.

  The organic electroluminescence device of the present invention can be protected by providing a protective layer (sealing layer) for the purpose of blocking contact with oxygen, moisture, or the like, or by encapsulating the device in an inert substance. Examples of the inert substance include paraffin, silicon oil, and fluorocarbon. Examples of the material used for the protective layer include fluorine resin, epoxy resin, silicone resin, polyester, polycarbonate, and photocurable resin.

  The organic electroluminescence device of the present invention can be used as a normal DC drive device. When a DC voltage is applied, light emission is observed when a voltage of about 1.5 to 20 V is applied with the positive polarity of the anode and the negative polarity of the cathode. Moreover, the organic electroluminescent element of this invention can be used also as an element of an alternating current drive. When an AC voltage is applied, light is emitted when the anode is in a positive state and the cathode is in a negative state. The organic electroluminescent device of the present invention is, for example, a flat light emitter such as an electrophotographic photosensitive member or a flat panel display, a copying machine, a printer, a backlight of a liquid crystal display, a light source such as an instrument, various light emitting devices, various display devices, various signs. It can be used for various sensors and various accessories.

  The preferable example of the organic electroluminescent element of this invention is shown in FIGS.

  FIG. 1 is a cross-sectional view showing an example of the organic electroluminescence element 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-transporting property, electron-transporting property, and light-emitting function, or a mixture of compounds having the respective functions. It is.

  FIG. 2 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 2 shows a configuration in which an anode 2, a hole transport layer 5, a light emitting layer 3, and a cathode 4 are sequentially provided on a substrate 1. In this case, the light emitting layer is useful when it has an electron transporting function.

  FIG. 3 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 3 shows a configuration in which an anode 2, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the light emitting layer is useful when it has a hole transporting function.

  FIG. 4 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 4 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 separates the functions of carrier transport and light emission, and the degree of freedom in material selection increases, so that the efficiency of light emission and the degree of freedom in light emission color increase.

  FIG. 5 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 5 shows a structure in which an anode 2, a hole injection layer 7, 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. In this case, the provision of the hole injection layer 7 improves the adhesion between the anode 2 and the hole transport layer 5, improves the injection of holes from the anode, and is effective in driving the light emitting element at a low voltage.

  FIG. 6 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 6 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4 are sequentially provided on a substrate 1. In this case, injection of electrons from the cathode 4 is improved, which is effective for driving the light emitting element at a low voltage.

  FIG. 7 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 7 shows a structure in which an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4 are sequentially provided on a substrate 1. In this case, injection of holes from the anode 2 is improved and injection of electrons from the cathode 4 is improved, which is the most effective for low voltage driving.

  8 to 14 are sectional views of a device in which a hole blocking layer is inserted. The hole blocking layer has an effect of preventing holes injected from the anode or excitons generated by recombination in the light emitting layer 3 from escaping to the cathode 4, thereby improving the light emission efficiency of the organic electroluminescence device. effective. The hole blocking layer 9 can be inserted between the light emitting layer 3 and the cathode 4, between the light emitting layer 3 and the electron transport layer 6, or between the light emitting layer 3 and the electron injection layer 8. More preferred is between the light emitting layer 3 and the electron transport layer 6.

  8 to 14, each of the hole transport layer 5, the hole injection layer 7, the electron transport layer 6, the electron injection layer 8, the light emitting layer 3, and the hole blocking layer 9 has a single layer structure, A multilayer structure may be used.

  1-14 is a fundamental element structure to the last, and the structure of the organic electroluminescent element using the compound of this invention is not limited to this.

Examples of the electron injecting material used for the electron injecting layer include the compounds according to Japanese Patent Application No. 2006-292032 of the present applicant, for example, the following compound group.

The di (pyridylphenyl) derivative of the present invention has a very large electron transporting ability as compared with conventional electron transporting agents such as Alq ₃ . In addition, the mobility is large and the carrier balance with the holes in the element is excellent. Since the hand gap is wide and suitable for blue phosphorescent materials, the di (pyridylphenyl) derivative of the present invention is extremely important industrially.

  Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited thereto.

５００ｍｌ四つ口フラスコに、４，６−ジクロロ−２−フェニル−ピリミジン２．７０ｇ（１２．０ｍｍｏｌ）、３，５−ジクロロフェニルボロン酸５．０３ｇ（２６．４ｍｍｏｌ）、１Ｍ炭酸ナトリウム水溶液（１モル／リットル濃度の水溶液を指す）６０ｍｌ、アセトニトリル１９０ｍｌを加え、１時間窒素バブリングをした。ＰｄＣｌ_２（ＰＰｈ_３）_２０．４２ｇ（０．６ｍｍｏｌ）を加え、９時間還流した。反応混合物を室温に戻した後、白色固体を濾別し、水、メタノールで順次洗浄した。得られた有機層は水、飽和食塩水で順次洗浄、有機層を無水硫酸マグネシウムで乾燥、減圧下溶媒を留去した。得られた固体を先に得られた固体と併せ、トルエン４５０ｍｌに還流下で溶解させた。これを５０ｃｃのシリカゲルを通じて濾過することにより透明溶液を得た。得られた溶液を濃縮した後、析出した白色固体を濾別した。白色固体をヘキサンで洗浄することにより目的物を得た。目的物の確認は、^１Ｈ−ＮＭＲ、薄層クロマトグラフ〔Ｔｈｉｎ Ｌａｙｅｒ Ｃｈｒｏｍａｔｏｇｒａｐｈ，ＴＬＣ〕、ＭＳにより行った（収量３．７５ｇ、収率７０％）。
（２）２−フェニル−４，６−ビス〔３，５−ジ（ピリジン−３−イル）フェニル〕ピリミジン（略号Ｂ３ＰｙＰＰＭ）の合成

５００ｍｌ四つ口フラスコに、２−フェニル−４，６−ビス（３，５−ジクロロフェニル）ピリジン（ＤＣＰＰＰＭ）１．７８ｇ（４．０ｍｍｏｌ）、３−（４，４，５，５−テトラメチル−１，３，２−ジオキサボロラン−２−イル）ピリジン（３ＰｙＤＯＢ）３．６１ｇ（１７．６ｍｍｏｌ）、１．３５Ｍリン酸カリウム水溶液２０ｍｌ、ジオキサン５０ｍｌを加え、１時間窒素バブリングをした。トリスジベンジリデンアセントンジパラジウム〔ｔｒｉｓ（ｄｉｂｅｎｚｙｌｉｄｅｎｅａｃｅｔｏｎｅ）ｄｉｐａｒａｄｉｕｍ，Ｐｄ_２（ｄｂａ）_３〕０．１５ｇ（０．１６ｍｍｏｌ）、ＰＣｙ_３０．１１ｇ（０．３８ｍｍｏｌ）を加え４８時間還流した。ここで、反応の進行をＴＬＣで確認したところ、多量の原料が見られたので室温まで冷却し、３ＰｙＤＯＢ３．６１ｇ（１７．６ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３０．１５ｇ（０．１６ｍｍｏｌ）、トリシクロヘキシルホスフィン〔ｔｒｉｃｙｃｌｏｈｅｘｙｌｐｈｏｓｐｈｉｎｅ，ＰＣｙ_３〕０．１１ｇ（０．３８ｍｍｏｌ）を加え、更に２２時間還流した。反応混合物を室温に戻した後、有機層をクロロホルムで抽出、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥し、濾別、濃縮した。シリカゲルカラム（展開溶媒：クロロホルム／メタノール＝１００／１．５→１００／２．０→１００／２．５→１００／５）にて精製することにより黄白色固体を得た。目的物の確認は、ＴＬＣ、^１Ｈ−ＮＭＲ、ＭＳにより行った（Ｂ３ＰｙＰＰＭ：収量１．６０ｇ、収率６５％、三置換体〔例えば化３９や化４０にみられるように分子中にピリジン環が３つあるが塩素が１つ残っている化合物を指す〕：収量０．３０ｇ、収率１２％）。
この化合物の蒸着膜のＵＶスペクトルを図１５に示す。 Example 1
(1) Synthesis of 2-phenyl-4,6-bis (3,5-dichlorophenyl) pyrimidine [4,6-Bis- (3,5-dichloro-phenyl) -2-phenyl-pyridine] (abbreviated DCPPPM)

In a 500 ml four-necked flask, 2.70 g (12.0 mmol) of 4,6-dichloro-2-phenyl-pyrimidine, 5.03 g (26.4 mmol) of 3,5-dichlorophenylboronic acid, 1M aqueous sodium carbonate solution (1 mol) 60 ml and acetonitrile 190 ml were added and nitrogen bubbling was performed for 1 hour. 0.42 g (0.6 mmol) of PdCl ₂ (PPh ₃ ) ₂ was added and refluxed for 9 hours. After returning the reaction mixture to room temperature, the white solid was filtered off and washed successively with water and methanol. The obtained organic layer was washed successively with water and saturated brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was combined with the previously obtained solid and dissolved in 450 ml of toluene under reflux. This was filtered through 50 cc of silica gel to obtain a clear solution. After concentrating the resulting solution, the precipitated white solid was filtered off. The desired product was obtained by washing the white solid with hexane. The target product was confirmed by ¹ H-NMR, thin layer chromatograph [Thin Layer Chromatography, TLC], and MS (yield 3.75 g, yield 70%).
(2) Synthesis of 2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (abbreviation B3PyPPM)

In a 500 ml four-necked flask, 1.78 g (4.0 mmol) of 2-phenyl-4,6-bis (3,5-dichlorophenyl) pyridine (DCPPPM), 3- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) pyridine (3PyDOB) 3.61 g (17.6 mmol), 1.35 M aqueous potassium phosphate solution 20 ml and dioxane 50 ml were added and nitrogen bubbling was performed for 1 hour. 0.15 g (0.16 mmol) of trisdibenzylidene acenetondipalladium [tris (dibenzylideneacetone) diparadium, Pd ₂ (dba) ₃ ] and 0.11 g (0.38 mmol) of PCy ₃ were added and refluxed for 48 hours. Here, the progress of the reaction was confirmed by TLC. As a result, a large amount of raw material was found, so it was cooled to room temperature, 3PyDOB 3.61 g (17.6 mmol), Pd ₂ (dba) ₃ 0.15 g (0.16 mmol), Tricyclohexylphosphine [tricycyclohexylphosphine, PCy ₃ ] 0.11 g (0.38 mmol) was added, and the mixture was further refluxed for 22 hours. After returning the reaction mixture to room temperature, the organic layer was extracted with chloroform and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by a silica gel column (developing solvent: chloroform / methanol = 100 / 1.5 → 100 / 2.0 → 100 / 2.5 → 100/5) gave a yellowish white solid. The target product was confirmed by TLC, ¹ H-NMR, and MS (B3PyPPM: Yield 1.60 g, Yield 65%, trisubstituted [for example, pyridine ring in the molecule as seen in Chemical Formula 39 and Chemical Formula 40] Refers to a compound having three chlorines but one chlorine remaining]: yield 0.30 g, yield 12%).
The UV spectrum of the deposited film of this compound is shown in FIG.

２−フェニル−４，６−ビス（３，５−ジクロロフェニル）ピリミジン（ＤＣＰＰＰＭ）１．７８ｇ（４．０ｍｍｏｌ）、４−（４，４，５，５−テトラメチル−１，３，２−ジオキサボロラン−２−イル）ピリジン（４ＰｙＤＯＢ）９．８０ｇ（４８．０ｍｍｏｌ）、１．３５Ｍリン酸カリウム水溶液２０ｍｌ、ジオキサン５０ｍｌを加え、１時間窒素バブリングをした。Ｐｄ_２（ｄｂａ）_３０．４５ｇ（０．４８ｍｍｏｌ）、ＰＣｙ_３０．３３ｇ（１．１４ｍｍｏｌ）を加え３６時間還流した。反応混合物を室温に戻した後、析出した固体を濾別し、水、メタノールで洗浄した。得られた固体をクロロホルム／メタノール混合溶媒（１００／３ｖ／ｖ）に溶解させた後、シリカゲルカラムに充填した。そのままシリカゲルカラム〔５００ｃｃ、展開溶媒：クロロホルム／メタノール＝１００／３（２．０Ｌ）→１００／４（１．５Ｌ）→１００／１０（１．０Ｌ）〕にて精製することにより白色固体を得た。目的物の確認は、^１Ｈ−ＮＭＲ、ＭＳにより行った（Ｂ４ＰｙＰＰＭ：収量１．６７ｇ、収率６８％、三置換体：収量０．２０ｇ、収率９％）。
なお、前記精製は触媒由来の黒色の不純物が混ざるため、二回行った。Ｂ４ＰｙＰＰＭの蒸着膜のＵＶスペクトルを図１６に示す。 Example 2
Synthesis of 2-phenyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (abbreviation B4PyPPM)

2-phenyl-4,6-bis (3,5-dichlorophenyl) pyrimidine (DCPPPM) 1.78 g (4.0 mmol), 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-yl) pyridine (4PyDOB) 9.80 g (48.0 mmol), 1.35 M aqueous potassium phosphate solution 20 ml and dioxane 50 ml were added and nitrogen bubbling was performed for 1 hour. 0.45 g (0.48 mmol) of Pd ₂ (dba) _{3 and} 0.33 g (1.14 mmol) of PCy ₃ were added and refluxed for 36 hours. After returning the reaction mixture to room temperature, the precipitated solid was filtered off and washed with water and methanol. The obtained solid was dissolved in a chloroform / methanol mixed solvent (100/3 v / v) and then packed in a silica gel column. The white solid was obtained by purifying with a silica gel column [500 cc, developing solvent: chloroform / methanol = 100/3 (2.0 L) → 100/4 (1.5 L) → 100/10 (1.0 L)]. It was. The target product was confirmed by ¹ H-NMR and MS (B4PyPPM: yield 1.67 g, yield 68%, trisubstituted: yield 0.20 g, yield 9%).
The purification was performed twice because black impurities derived from the catalyst were mixed. The UV spectrum of the deposited film of B4PyPPM is shown in FIG.

Ｔｄ：分解温度、Ｔｇ：二次転移温度、Ｔｍ：融点、Ｉｐ：イオン化ポテンシャル、Ｅｇ：エネルギーギャップ、Ｅａ：エレクトロアフィニティ（電子親和力）、ｎ．ｄ．：検出されず。
Ｔｇ（二次転移温度）については、ＤＳＣ（Ｄｉｆｆｉｒｅｎｔｉａｌ Ｓｃａｎｎｉｎｇ Ｃａｌｏｒｉｍｅｔｅｒ 示差熱量計）中にサンプルを加え、溶融させたものを急冷し、２〜３回繰り返すとガラス転移を表すカーブがチャート上に現れるので、そのカーブを接線で結び、その交点の温度をＴｇとして採用する。
Ｔｍ（融点）は、同じくＤＳＣにサンプルを加え、昇温していくと吸熱カーブが現れるのでその極大のところとの温度を読んで、その温度をＴｍとする。
Ｔｄ（分解温度）は、ＤＴＡ（Ｄｉｆｆｅｒｅｎｔｉａｌ ｔｈｅｒｍａｌ ａｎａｌｙｚｅｒ 示差熱分析装置）にサンプルを加え、加熱していくとサンプルが熱によって分解し、重量が減少しだす。その減少が開始しだしたところの温度を読んで、その温度をＴｄとする。
エネルギーギャップ（Ｅｇ）については、蒸着機で作成した薄膜を紫外−可視吸光度計で薄膜の吸収曲線を測定する。その薄膜の短波長側の立ち上がりの所に接線を引き、求まった交点の波長Ｗ（ｎｍ）を次の式に代入し目的の値を求める。それによって得た値がＥｇになる。
Ｅｇ＝１２４０÷Ｗ
例えば接線を引いて求めた値Ｗ（ｎｍ）が４７０ｎｍだったとしたらこの時のＥｇの値は
Ｅｇ＝１２４０÷４７０＝２．６３（ｅＶ）
と言うことになる。
Ｉｐ（イオン化ポテンシャル）は、イオン化ポテンシャル測定装置（例えば理研計器ＡＣ−１）を使用して測定し、測定するサンプルがイオン化を開始しだしたところの電圧（ｅＶ）の値を読む。
Ｅａ（電子親和力）は、ＩｐからＥｇを引いた値である。
本明細書における波長に対する強度（ｉｎｔｅｎｓｉｔｙ ａ．ｕ．）の測定は、浜松ホトニクス社製ストリークカメラを用いて、クライオスタット中で４．２Ｋにおいて測定した。
ついで、ＵＶおよびＡＣ−３測定を行い、電気化学特性を評価した。２５０ｎｍの励起波長におけるＰＬスペクトルの測定を試みたが、Ｂ３ＰｙＰＰＭ、Ｂ４ＰｙＰＰＭともに発光は観測されなかった。 Thermal characteristics of the novel electron transport material were evaluated using a thermogravimetric analyzer (TGA) and a differential scanning calorimeter (DSC). As a result, 2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (B3PyPPM) obtained in Example 30 was found to have a Tg = n. d. Tm = 318 ° C. and Td = 451 ° C.
2-Phenyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (B4PyPPM) obtained in Example 2 has a Tg = n. d. Tm = 356 ° C. and Td = 467 ° C.
The ionization potential (Ip), electron affinity (Ea) and energy gap (Eg) of these compounds were also measured. The results are as shown in the table below.

Td: decomposition temperature, Tg: secondary transition temperature, Tm: melting point, Ip: ionization potential, Eg: energy gap, Ea: electroaffinity (electron affinity), n. d. : Not detected.
As for Tg (secondary transition temperature), a sample is added to DSC (Differential Scanning Calorimeter), the melted sample is rapidly cooled, and a curve representing the glass transition appears on the chart when repeated 2-3 times. The curves are connected by tangent lines, and the temperature at the intersection is adopted as Tg.
As for Tm (melting point), an endothermic curve appears when a sample is added to the DSC and the temperature is raised, so the temperature at the maximum is read and the temperature is defined as Tm.
As for Td (decomposition temperature), when a sample is added to DTA (Differential Thermal Analyzer) and heated, the sample is decomposed by heat and the weight starts to decrease. The temperature at which the decrease starts is read and the temperature is defined as Td.
Regarding the energy gap (Eg), an absorption curve of the thin film prepared with a vapor deposition machine is measured with an ultraviolet-visible absorptiometer. A tangent line is drawn at the rising edge of the thin film on the short wavelength side, and the wavelength W (nm) at the obtained intersection is substituted into the following equation to obtain the target value. The value obtained thereby becomes Eg.
Eg = 1240 ÷ W
For example, if the value W (nm) obtained by drawing a tangent is 470 nm, the value of Eg at this time is Eg = 1240 ÷ 470 = 2.63 (eV)
It will be said.
Ip (ionization potential) is measured using an ionization potential measuring apparatus (for example, Riken Keiki AC-1), and the value of the voltage (eV) at which the sample to be measured starts ionization is read.
Ea (electron affinity) is a value obtained by subtracting Eg from Ip.
Intensity au in this specification was measured at 4.2K in a cryostat using a streak camera manufactured by Hamamatsu Photonics.
Subsequently, UV and AC-3 measurements were performed to evaluate the electrochemical properties. Attempts were made to measure the PL spectrum at an excitation wavelength of 250 nm, but no emission was observed for either B3PyPPM or B4PyPPM.

５００ｍｌ四つ口フラスコに３，５−ジクロロフェニルボロン酸（８．１ｇ ４２．３ｍｍｏｌ）、４，６−ジクロロ−２−メチルピリミジン（３．１ｇ １９．２ｍｍｏｌ）、炭酸ナトリウム（１２．２ｇ １１５．２ｍｍｏｌ）の７００ｍｌ水溶液、アセトニトリル３００ｍｌを投入し、撹拌しながら４０分間窒素フローした。この溶液を６０℃に加熱し、ビストリフェニルホスフィンパラジウムジクロリド（６６８ｍｇ ０．９５ｍｍｏｌ）を投入して、１２時間反応させた。その後反応液を３０℃まで冷却し、クロロホルムで抽出したのち、クロロホルム層を水で３回洗浄した。有機層を硫酸マグネシウムで乾燥後、ろ過して濃縮し、淡黄色固体を得た。これをシリカゲルカラムにより精製（展開溶媒：クロロホルム／ヘキサン＝２／１のものを使用）し、ＢＣＰＭＰＭの白色結晶６．０ｇを得た（収率８１．４％ 理論収量７．４ｇ）。
（２）２−メチル−４,６−ビス〔３，５−ジ（ピリジン−３−イル）フェニル〕ピリミジン（略号Ｄ３ＰｙＰＭＰＭ）の合成

５００ｍｌ四つ口フラスコにＢＣＰＭＰＭ（２．０ｇ ５．２ｍｍｏｌ）、３−ピリジン ＤＯＢ（４．７ｇ ２２．９ｍｍｏｌ）、ジオキサン２５０ｍｌ、リン酸カリウム（１３．３ｇ ６２．５ｍｍｏｌ）の７０ｍｌ水溶液を投入し、撹拌しながら４０分間窒素フローした。この溶液を８５℃に加熱し、Ｐｄ_２（ｄｂａ）_３（１９１ｍｇ ０．２１ｍｍｏｌ）、トリシクロヘキシルホスフィン（１４０ｍｇ ０．５０ｍｍｏｌ）を投入し、１２時間反応させた。反応終了後液を３０℃まで冷却し、析出物をろ過した。この固体を水で分散洗浄し、次にアセトン分散洗浄し、灰色の組成物を得た。これを加熱したクロロホルム／メタノール（５０／１）に溶解させ、シリカゲルカラムで精製（展開溶媒：クロロホルム／メタノール＝５０／１→４０／１→３０／１の比率で順次使用）した。得られた固体をアセトンで分散洗浄してＤ３ＰｙＰＭＰＭの白色結晶２．２ｇを得た（収率７６．７％ 理論収量２．９ｇ）。 Reference example 1
(1) Synthesis of 2-methyl-4,6-bis- (3,5-dichlorophenyl) pyrimidine (abbreviation BCPMPM)

In a 500 ml four-necked flask, 3,5-dichlorophenylboronic acid (8.1 g 42.3 mmol), 4,6-dichloro-2-methylpyrimidine (3.1 g 19.2 mmol), sodium carbonate (12.2 g 115.2 mmol) ) And 300 ml of acetonitrile were added and nitrogen flowed for 40 minutes with stirring. This solution was heated to 60 ° C., bistriphenylphosphine palladium dichloride (668 mg 0.95 mmol) was added, and the mixture was reacted for 12 hours. Thereafter, the reaction solution was cooled to 30 ° C. and extracted with chloroform, and then the chloroform layer was washed with water three times. The organic layer was dried over magnesium sulfate, filtered and concentrated to give a pale yellow solid. This was purified with a silica gel column (developing solvent: chloroform / hexane = 2/1) to obtain 6.0 g of BCPMPM white crystals (yield 81.4%, theoretical yield 7.4 g).
(2) Synthesis of 2-methyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (abbreviation D3PyPMPM)

A 500 ml four-necked flask was charged with 70 ml aqueous solution of BCPMPM (2.0 g 5.2 mmol), 3-pyridine DOB (4.7 g 22.9 mmol), dioxane 250 ml, potassium phosphate (13.3 g 62.5 mmol), Nitrogen flow for 40 minutes with stirring. This solution was heated to 85 ° C., Pd ₂ (dba) ₃ (191 mg 0.21 mmol) and tricyclohexylphosphine (140 mg 0.50 mmol) were added, and reacted for 12 hours. After completion of the reaction, the liquid was cooled to 30 ° C., and the precipitate was filtered. This solid was dispersed and washed with water and then dispersed and washed with acetone to obtain a gray composition. This was dissolved in heated chloroform / methanol (50/1) and purified with a silica gel column (developing solvent: chloroform / methanol = 50/1 → 40/1 → 30/1 in order). The obtained solid was dispersed and washed with acetone to obtain 2.2 g of white crystals of D3PyPMPM (yield 76.7%, theoretical yield 2.9 g).

原料を３−ピリジンＤＯＢから４−ピリジンＤＯＢに変更した以外は仕込み量、反応条件、精製条件は全て参考例１のＤ３ＰｙＰＭＰＭの場合と同様に行いＤ４ＰｙＰＭＰＭの白色結晶１．９２ｇ（収率：６６．７％ 理論収量２．９ｇ）を得た。 Reference example 2
Synthesis of 2-methyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (abbreviation D4PyPMPM)

Except for changing the raw material from 3-pyridine DOB to 4-pyridine DOB, the charged amount, reaction conditions, and purification conditions were all the same as in the case of D3PyPMPM of Reference Example 1, and 1.92 g of white crystals of D4PyPMPM (yield: 66. 7% theoretical yield 2.9 g) was obtained.

３−（４，４，５，５−テトラメチル−１，３，２−ジオキサボロラン−２−イル）ピリジン（３ＰｙＤＯＢ）１５．００ｇ（７３．１ｍｍｏｌ）、トリブロモベンゼン１１．３０ｇ（３５．９ｍｍｏｌ）、２Ｍ炭酸ナトリウム水溶液（２モル／リットル濃度の水溶液のこと、以下同様の表現方法である）３０ｍｌ、トルエン１５０ｍｌ、エタノール１００ｍｌを加え、１時間窒素バブリングをした。テトラキス（トリフェニルホスフィン）パラジウム〔Ｐｄ（ＰＰｈ_３）_４〕０．７８ｇ（０．６７ｍｍｏｌ）を加え、１９時間還流した。反応混合物を室温に戻し、クロロホルムで希釈した後、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥し、濾別、濃縮後、シリカゲルカラムクロマトグラフィ−（展開溶媒：クロロホルム／酢酸エチル＝１／２のものを使用し、ついでクロロホルム／酢酸エチル／メタノール＝１０／２０／１のものを使用）にて精製することにより白色固体を得た。この目的物の確認は、^１Ｈ−ＮＭＲ，ＭＳにより行った（収量５．５０ｇ、収率４９％）。
（２）３，３″，５，５″−テトラ（ピリジン−３−イル）−１：１′，３′：１″−タ−フェニル（略号ＢｍＰｙＢＢ）の合成

ＢＰｙＢＢｒ２．４８ｇ（８．０ｍｍｏｌ）、１，３−ジ（４，４，５，５−テトラメチル−１，３，２−ジオキサボロラン−２−イル）ベンゼン（ｍＢＤＯＢＢ）１．１６ｇ（３．５ｍｍｏｌ）、２Ｍ炭酸カリウム水溶液６ｍｌ、トルエン５０ｍｌ、エタノール２５ｍｌを加え、１時間窒素バブリングをした。Ｐｄ（ＰＰｈ_３）_４０．４０ｇ（０．３５ｍｍｏｌ）を加え、２６時間還流した。反応混合物を室温に戻し、トルエンで希釈した後、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥し、濾別、濃縮後、シリカゲルカラムクロマトグラフィー（展開溶媒：クロロホルム／酢酸エチル／メタノール＝１０／２０／１のものを使用し、ついでクロロホルム／メタノール＝１００／７のものを使用）にて精製することによりＢｍＰｙＢＢの白色固体を得た。この目的物の確認は、^１Ｈ−ＮＭＲ，ＭＳにより行った（収量１．５９ｇ、収率８４％）。
参考例１〜３は、特願２００６−３１３３８５の実施例９、１０および実施例１に対応しているので、前記出願明細書を参照。 Reference example 3
(1) Synthesis of 3,5-di (pyridin-3-yl) -1-bromobenzene (abbreviation BPyBBr)

3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine (3PyDOB) 15.00 g (73.1 mmol), tribromobenzene 11.30 g (35.9 mmol) 30 ml of 2M sodium carbonate aqueous solution (2 mol / liter concentration aqueous solution, hereinafter the same expression method), 150 ml of toluene and 100 ml of ethanol were added, and nitrogen bubbling was performed for 1 hour. Tetrakis (triphenylphosphine) palladium [Pd (PPh ₃ ) ₄ ] (0.78 g, 0.67 mmol) was added, and the mixture was refluxed for 19 hours. The reaction mixture was returned to room temperature, diluted with chloroform, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel column chromatography (developing solvent: chloroform / ethyl acetate = 1/2, then chloroform / ethyl acetate / methanol = 10/20 / 1 was used) to obtain a white solid. This target product was confirmed by ¹ H-NMR and MS (yield 5.50 g, yield 49%).
(2) Synthesis of 3,3 ″, 5,5 ″ -tetra (pyridin-3-yl) -1: 1 ′, 3 ′: 1 ″ -terphenyl (abbreviation BmPyBB)

2.48 g (8.0 mmol) of BPyBBr, 1.16 g (3.5 mmol) of 1,3-di (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene (mBDOBB) 6 ml of 2M potassium carbonate aqueous solution, 50 ml of toluene and 25 ml of ethanol were added and nitrogen bubbling was performed for 1 hour. 0.40 g (0.35 mmol) of Pd (PPh ₃ ) ₄ was added and refluxed for 26 hours. The reaction mixture was returned to room temperature, diluted with toluene, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel column chromatography (developing solvent: chloroform / ethyl acetate / methanol = 10/20/1, then chloroform / methanol = 100/7). The white solid of BmPyBB was obtained. This target product was confirmed by ¹ H-NMR and MS (yield 1.59 g, yield 84%).
Since Reference Examples 1 to 3 correspond to Examples 9 and 10 and Example 1 of Japanese Patent Application No. 2006-313385, refer to the specification of the application.

Low temperature phosphorescence spectrum measurement of 2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (B3PyPPM) as the electron transport material obtained in Example 1 was performed. However, the rise of the phosphorescence spectrum is 440 nm (T ₁ = 2.81 eV), and the low-temperature phosphorescence spectrum (T = 4.2 K) is shown in FIG.

これらの各素子のエネルギーダイアグラムを図１８に示す。
また、各素子の構成は下記に示す。
実施例３：［ＩＴＯ／ＴＰＤＰＥＳ（〔化４６〕参照）：１０ｗｔ％ＴＢＰＡＨ（〔化４６〕参照）（２０ｎｍ）／ＴＡＰＣ（〔化４６〕参照）（３０ｎｍ）／ＣＢＰ（〔化４６〕参照）：８ｗｔ％Ｉｒ（ｐｐｙ）_３（〔化３〕参照）（１０ｎｍ）／Ｂ３ＰｙＰＰＭ（５０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
参考例４：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：８ｗｔ％Ｉｒ（ｐｐｙ）_３（１０ｎｍ）／Ｄ３ＰｙＰＭＰＭ（５０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
参考例５：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：８ｗｔ％Ｉｒ（ｐｐｙ）_３（１０ｎｍ）／ＢｍＰｙＢＢ（〔化４６〕参照）（５０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
前記各素子の
電流密度 −電圧特性は図１９に、
輝度 −電圧特性は図２０に、
視感効率 −電圧特性は図２１に、
電流効率 −電圧特性は図２２に、
量子効率 −輝度特性は図２３に、
ＥＬスペクトル は図２４に、
それぞれ示す。
また、前記緑色リン光素子の特性とその電子輸送層の効果を下記表に示す。

Example 3, Reference Examples 4, 5
2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (B3PyPPM) obtained in Example 1, compound D3PyPMPM obtained in Reference Example 1, and Reference Example 3 Green phosphorescent devices each using the obtained compound BmPyBB as an electron transport material were prepared, and the performance of each device was evaluated.

An energy diagram of each of these elements is shown in FIG.
The configuration of each element is shown below.
Example 3: [ITO / TPDPES (refer to [Chemical 46]): 10 wt% TBPAH (refer to [Chemical 46]) (20 nm) / TAPC (refer to [Chemical 46]) (30 nm) / CBP (refer to [Chemical 46]) : 8 wt% Ir (ppy) ₃ (see [Chemical Formula 3]) (10 nm) / B3PyPPM (50 nm) / LiF (0.5 nm) / Al (100 nm)]
Reference Example 4: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (30 nm) / CBP: 8 wt% Ir (ppy) ₃ (10 nm) / D3PyPMPM (50 nm) / LiF (0.5 nm) / Al (100 nm) ]
Reference Example 5: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (30 nm) / CBP: 8 wt% Ir (ppy) ₃ (10 nm) / BmPyBB (see [Chemical Formula 46]) (50 nm) / LiF (0. 5 nm) / Al (100 nm)]
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency vs. luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
The characteristics of the green phosphor element and the effect of the electron transport layer are shown in the following table.

本実施例の素子構成を下記に示す。
実施例４：［ＩＴＯ／ＴＰＤＰＥＳ（〔化４６〕参照）：１０ｗｔ％ＴＢＰＡＨ（〔化４６〕参照）（２０ｎｍ）／ＴＡＰＣ（〔化４６〕参照）（３０ｎｍ）／ＣＢＰ（〔化４６〕参照）：８ｗｔ％Ｉｒ（ｐｐｙ）_３（１０ｎｍ）／Ｂ４ＰｙＰＰＭ（５０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
参考例６：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：８ｗｔ％Ｉｒ（ｐｐｙ）_３（１０ｎｍ）／Ｄ４ＰｙＰＭＰＭ（５０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
１００ｃｄ／ｍ^２時の視感効率はＢ４ＰｙＰＰＭ（１２７．０ ｌｍ／Ｗ）＞Ｄ４ＰｙＰＭＰＭ（１１７．９ ｌｍ／Ｗ）の方がフェニル基で置換した化合物Ｄ４ＰｙＰＭＰＭに比べて高効率となった。
これらの各素子のエネルギーダイアグラムを図２５に示す。
実施例４と参考例６の緑色リン光素子の特性と電子輸送層の効果は下記表に示すとおりである。

前記各素子の
電流密度 −電圧特性は図２６に、
輝度 −電圧特性は図２７に、
視感効率 −電圧特性は図２８に、
電流効率 −電圧特性は図２９に、
量子効率 −輝度特性は図３０に、
ＥＬスペクトル は図３１に、
それぞれ示す。 Example 4, Reference Example 6
2-phenyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (B4PyPPM), which is the compound obtained in Example 2, and 2 which is the compound obtained in Reference Example 2. A green phosphorescent device using -methyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (D4PyPMPM) as an electron transport layer was prepared.

The element configuration of this example is shown below.
Example 4: [ITO / TPDPES (refer to [Chemical 46]): 10 wt% TBPAH (refer to [Chemical 46]) (20 nm) / TAPC (refer to [Chemical 46]) (30 nm) / CBP (refer to [Chemical 46]) : 8 wt% Ir (ppy) ₃ (10 nm) / B4PyPPM (50 nm) / LiF (0.5 nm) / Al (100 nm)]
Reference Example 6: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (30 nm) / CBP: 8 wt% Ir (ppy) ₃ (10 nm) / D4PyPMPM (50 nm) / LiF (0.5 nm) / Al (100 nm) ]
The luminous efficiency at 100 cd / m ² was higher when B4PyPPM (127.0 lm / W)> D4PyPMPM (117.9 lm / W) than the compound D4PyPMPM substituted with a phenyl group.
An energy diagram of each of these elements is shown in FIG.
The characteristics of the green phosphor elements of Example 4 and Reference Example 6 and the effect of the electron transport layer are as shown in the following table.

The current density-voltage characteristic of each element is shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency-luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.

Examples 5-7
An orange phosphorescent element using BPyPPMs which are the compounds of Examples 1 and 2 in the electron transport layer was evaluated. TAPC or 3DTAPBP (see [Chemical Formula 46]) was used for the hole transport layer. As a result, the luminous efficiency at 100 cd / m ² was B4PyPPM (Example 2) / TAPC (50.5 lm / W)> B4PyPPM / 3DTAPBP (48.4 lm / W)> B3PyPPM (Example 1) / TAPC. (45.9 lm / W).
The element configuration of this example is shown below.
Example 5: [ITO / TPDPES (refer to [Chemical Formula 46]): 10 wt% TBPAH (refer to [Chemical Formula 46]) (20 nm) / 3DTAPBP (refer to [Chemical Formula 46]) (35 nm) / CBP (refer to [Chemical Formula 46]) : 4 wt% PQ ₂ Ir (dpm) (10 nm) / B4PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 6: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% PQ ₂ Ir (dpm) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm ]]
Example 7: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (see [Chemical Formula 46]) (35 nm) / CBP: 4 wt% PQ ₂ Ir (dpm) (10 nm) / B4PyPPM (65 nm) / LiF (0 .5 nm) / Al (100 nm)]
An energy diagram of each of these elements is shown in FIG.
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
Luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency vs. luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
The characteristics of the green phosphor element and the effect of the electron transport layer are shown in the following table.

Examples 8 and 9
An orange phosphor using the compound 2-phenyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (B4PyPPM) obtained in Example 2 as an electron transport layer Evaluation was performed. TAPC was used for the hole transport layer, and devices with different dope concentrations were produced. As a result, the luminous efficiency at 100 cd / m ² was in the order of 4 wt% (50.5 lm / W)> 6 wt% (39.1 lm / W).
Element Configuration Example 8: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% PQ ₂ Ir (dpm) (10 nm) / B4PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 9: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 6 wt% PQ ₂ Ir (dpm) (10 nm) / B4PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm ]]
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency vs. luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
The following table shows the effects of the orange phosphor element using BPyPPM as an electron transport material and the effect of the doping concentration.

素子の構成
実施例１０：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３５ｎｍ）／ＣＢＰ：４ｗｔ％Ｉｒ（ｐｉｑ）（１０ｎｍ）／Ｂ３ＰｙＰＰＭ（６５ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
実施例１１：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３５ｎｍ）／ＣＢＰ：４ｗｔ％Ｉｒ（ｐｉｑ）（１０ｎｍ）／Ｂ４ＰｙＰＰＭ（６５ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
参考例７：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３５ｎｍ）／ＣＢＰ：４ｗｔ％Ｉｒ（ｐｉｑ）（１０ｎｍ）／ＢｍＰｙＢＢ（６５ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
これらの各素子のエネルギーダイアグラムを図４５に示す。
前記各素子の
電流密度 −電圧特性は図４６に、
輝度 −電圧特性は図４７に、
視感効率 −電圧特性は図４８に、
電流効率 −電圧特性は図４９に、
量子効率 −輝度特性は図５０に、
ＥＬスペクトル は図５１に、
それぞれ示す。
実施例１で得られたＢ３ＰｙＰＰＭを電子輸送層に用いた実施例１０の赤色リン光素子の特性、実施例２で得られた化合物Ｂ４ＰｙＰＰＭを電子輸送層に用いた実施例１１の赤色リン光素子の特性、および参考例３で得られたＢｍＰｙＢＢを電子輸送層に用いた参考例７の赤色リン光素子の特性をそれぞれ下記表に示す。

Examples 10-11, Reference Example 7
2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (B3PyPPM) obtained in Example 1 and the compound 2-phenyl-4, obtained in Example 2. 6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (B4PyPPM), 3,3 ″, 5,5 ″ -tetra (pyridin-3-yl) -1 obtained in Reference Example 3 1 ′, 3 ′: 1 ″ -tert-phenyl (BmPyBB) was evaluated for a red phosphorescent device. As a result, the luminous efficiency at 100 cd / m ² was B3PyPPM (12. 4 lm / W)> B4PyPPM (9.6 lm / W)> BmPyBB (7.9 lm / W).
The structures of the elements used in these examples and reference examples are shown below.
Ir (piq) is a compound represented by the following formula.

Element Configuration Example 10: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% Ir (piq) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al ( 100 nm)]
Example 11: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% Ir (piq) (10 nm) / B4PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm)]
Reference Example 7: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% Ir (piq) (10 nm) / BmPyBB (65 nm) / LiF (0.5 nm) / Al (100 nm)]
An energy diagram of each of these elements is shown in FIG.
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency vs. luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
Characteristics of the red phosphorescent device of Example 10 using B3PyPPM obtained in Example 1 for the electron transport layer, and the red phosphorescent device of Example 11 using compound B4PyPPM obtained in Example 2 for the electron transport layer And the characteristics of the red phosphor element of Reference Example 7 using BmPyBB obtained in Reference Example 3 for the electron transport layer are shown in the following tables, respectively.

Example 12, Reference Example 8
In Example 12, the compound B3PyPPM obtained in Example 1 was used for the electron transport layer, and a red phosphorescent device was made using TAPC for the hole transport layer. In Reference Example 8, a reference example was used for the electron transport layer. Using the compound BmPyBB obtained in 3, a red phosphorescent device was prepared using α-NPD for the hole transport layer. As a result, the luminous efficiency at 100 cd / m ² was in the order of TAPC (12.4 lm / W)> α-NPD% (8.4 lm / W).
In addition, the structure of an element is as follows.
Example 12: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% Ir (piq) (10 nm) / B3PyPPM (compound of Example 1) (65 nm) / LiF (0.5 nm ) / Al (100 nm)]
Reference Example 8: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / α-NPD: (35 nm) / CBP: 4 wt% Ir (piq) (10 nm) / BmPyBB (compound of Reference Example 3) (65 nm) / LiF ( 0.5 nm) / Al (100 nm)]
An energy diagram of each of these elements is shown in FIG.
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency vs. luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
The characteristics of the two red phosphor elements are shown in the following table.

Examples 13 and 14
The effect of the doping concentration of the red phosphor using the B3PyPPM obtained in Example 1 as the electron transport layer and CBP as the host was examined. As a result, the luminous efficiency at 100 cd / m ² was in the order of 4 wt% (12.4 lm / W)> 6 wt% (11.8 lm / W).
Element Configuration Example 13: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 4 wt% Ir (piq) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al ( 100 nm)]
Example 14: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / CBP: 6 wt% Ir (piq) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm)]
An energy diagram of each of these elements (the energy diagram is independent of concentration) is shown in FIG.
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency-luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
The effect of the doping concentration of the red phosphor element using the above two CBPs as hosts is shown in the following table.

素子の構成
実施例１５：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３５ｎｍ）／ＢＡｌｑ：４ｗｔ％Ｉｒ（ｐｉｑ）（１０ｎｍ）／Ｂ３ＰｙＰＰＭ（６５ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
実施例１６：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３５ｎｍ）／ＢＡｌｑ：６ｗｔ％Ｉｒ（ｐｉｑ）（１０ｎｍ）／Ｂ３ＰｙＰＰＭ（６５ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
実施例１７：［ＩＴＯ／ＴＰＤＰＥＳ：１０ｗｔ％ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３５ｎｍ）／ＢＡｌｑ：８ｗｔ％Ｉｒ（ｐｉｑ）（１０ｎｍ）／Ｂ３ＰｙＰＰＭ（６５ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）］
これらの各素子のエネルギーダイアグラムを図６６に示す。
前記各素子の
電流密度 −電圧特性は図６７に、
輝度 −電圧特性は図６８に、
視感効率 −電圧特性は図６９に、
電流効率 −電圧特性は図７０に、
量子効率 −輝度特性は図７１に、
ＥＬスペクトル は図７２に、
それぞれ示す。
上記２つのＢＡｌｑをホストに用いた赤色リン光素子のドープ濃度の効果を下記表に示す。

Examples 15-17
The effect of the doping concentration of the red phosphor element using B3PyPPM obtained in Example 1 as the electron transport layer and BAlq as the host was examined. As a result, the luminous efficiency at 100 cd / m ² was in the order of 4 wt% (12.3 lm / W)> 6 wt% (12.2 lm / W)> 8 wt% (11.1 lm / W). .

Element Structure Example 15: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / BAlq: 4 wt% Ir (piq) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al ( 100 nm)]
Example 16: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / BAlq: 6 wt% Ir (piq) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 17: [ITO / TPDPES: 10 wt% TBPAH (20 nm) / TAPC (35 nm) / BAlq: 8 wt% Ir (piq) (10 nm) / B3PyPPM (65 nm) / LiF (0.5 nm) / Al (100 nm)]
An energy diagram of each of these elements is shown in FIG.
The current density-voltage characteristics of each element are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency vs. voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The quantum efficiency-luminance characteristics are shown in FIG.
The EL spectrum is shown in FIG.
Each is shown.
The effect of the doping concentration of the red phosphor element using the two BAlq as a host is shown in the following table.

It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. 2 shows a UV spectrum of a deposited film of 2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (B3PyPPM) obtained in Example 1. The UV spectrum of the vapor deposition film of 2-phenyl-4,6-bis [3,5-di (pyridin-4-yl) phenyl] pyrimidine (B4PyPPM) obtained in Example 2 is shown. The low temperature phosphorescence spectrum (T = 4.2K) of 2-phenyl-4,6-bis [3,5-di (pyridin-3-yl) phenyl] pyrimidine (B3PyPPM) obtained in Example 1 is shown. The energy diagram which the organic EL element of Example 3 and Reference Examples 4-5 has is shown. The current density-voltage characteristic which the organic EL element of Example 3 and Reference Examples 4-5 has is shown. The luminance-voltage characteristics of the organic EL elements of Example 3 and Reference Examples 4 to 5 are shown. The luminous efficiency-voltage characteristic which the organic EL element of Example 3 and Reference Examples 4-5 has is shown. The current efficiency-voltage characteristic which the organic EL element of Example 3 and Reference Examples 4-5 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Example 3 and Reference Examples 4-5 has is shown. The EL spectrum which the organic EL element of Example 3 and Reference Examples 4-5 has is shown. The energy diagram which the organic EL element of Example 4 and Reference Example 6 has is shown. The current density-voltage characteristic which the organic EL element of Example 4 and Reference Example 6 has is shown. The luminance-voltage characteristic which the organic EL element of Example 4 and Reference Example 6 has is shown. The luminous efficiency-voltage characteristic which the organic EL element of Example 4 and Reference Example 6 has is shown. The current efficiency-voltage characteristic which the organic EL element of Example 4 and Reference Example 6 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Example 4 and Reference Example 6 has is shown. The EL spectrum which the organic EL element of Example 4 and Reference Example 6 has is shown. The energy diagram which the organic EL element of Examples 5-7 has is shown. The current density-voltage characteristic which the organic EL element of Examples 5-7 has is shown. The luminance-voltage characteristic which the organic EL element of Examples 5-7 has is shown. The luminous efficiency-voltage characteristic which the organic EL element of Examples 5-7 has is shown. The current efficiency-voltage characteristic which the organic EL element of Examples 5-7 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Examples 5-7 has is shown. The EL spectrum which the organic EL element of Examples 5-7 has is shown. The current density-voltage characteristic which the organic EL element of Examples 8 and 9 has is shown. The luminance-voltage characteristics of the organic EL elements of Examples 8 and 9 are shown. The luminous efficiency-voltage characteristic which the organic EL element of Example 8, 9 has is shown. The current efficiency-voltage characteristic which the organic EL element of Example 8 and 9 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Example 8 and 9 has is shown. The EL spectrum which the organic EL element of Examples 8 and 9 has is shown. The energy diagram which the organic EL element of Examples 10-11 and the reference example 7 has is shown. The current density-voltage characteristic which the organic EL element of Examples 10-11 and Reference Example 7 has is shown. The luminance-voltage characteristics of the organic EL elements of Examples 10 to 11 and Reference Example 7 are shown. The luminous efficiency-voltage characteristic which the organic EL element of Examples 10-11 and Reference Example 7 has is shown. The current efficiency-voltage characteristic which the organic EL element of Examples 10-11 and Reference Example 7 has is shown. The quantum efficiency-luminance characteristic which the organic EL elements of Examples 10 to 11 and Reference Example 7 have is shown. The EL spectrum which the organic EL element of Examples 10-11 and the reference example 7 has is shown. The energy diagram which the organic EL element of Example 12 and Reference Example 8 has is shown. The current density-voltage characteristic which the organic EL element of Example 12 and Reference Example 8 has is shown. The luminance-voltage characteristic which the organic EL element of Example 12 and Reference Example 8 has is shown. The luminous efficiency-voltage characteristic which the organic EL element of Example 12 and Reference Example 8 has is shown. The current efficiency-voltage characteristic which the organic EL element of Example 12 and Reference Example 8 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Example 12 and Reference Example 8 has is shown. The EL spectrum which the organic EL element of Example 12 and Reference Example 8 has is shown. The energy diagram which the organic EL element of Example 13 and 14 has is shown. The current density-voltage characteristic which the organic EL element of Examples 13 and 14 has is shown. The luminance-voltage characteristic which the organic EL element of Example 13 and 14 has is shown. The luminous efficiency-voltage characteristic which the organic EL element of Examples 13 and 14 has is shown. The current efficiency-voltage characteristic which the organic EL element of Example 13 and 14 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Example 13 and 14 has is shown. The EL spectrum which the organic EL element of Examples 13 and 14 has is shown. The energy diagram which the organic EL element of Examples 15-17 has is shown. The current density-voltage characteristic which the organic EL element of Examples 15-17 has is shown. The luminance-voltage characteristic which the organic EL element of Examples 15-17 has is shown. The luminous efficiency-voltage characteristic which the organic EL element of Examples 15-17 has is shown. The current efficiency-voltage characteristic which the organic EL element of Examples 15-17 has is shown. The quantum efficiency-luminance characteristic which the organic EL element of Examples 15-17 has is shown. The EL spectrum which the organic EL element of Examples 15-17 has is shown.

Explanation of symbols

1 Substrate 2 Anode (ITO)
3 Light emitting layer 4 Cathode 5 Hole transport layer (hole transport layer)
6 Electron transport layer 7 Hole injection layer (hole injection layer)
8 Electron injection layer 9 Hole blocking layer (hole blocking layer)

Claims (3)

The following general formula (1)

(Where Q is

R ^{1 to} R ⁶ and R ^{10 to} R ¹¹ are groups selected from the group consisting of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, and a linear or branched group having 1 to 6 carbon atoms. Each independently selected from the group consisting of an alkoxy group and a linear or branched mono- or di-alkylamino group having 1 to 6 carbon atoms)
A di (pyridylphenyl) derivative represented by:   An electron transport material comprising the di (pyridylphenyl) derivative according to claim 1.   An organic electroluminescence device comprising the di (pyridylphenyl) derivative according to claim 1.

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