JP2008244471A - Material for organic electronics, thin-film employing the material, organic electronics element and organic electroluminescence element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a material for organic electronics which can be multilayered easily and can form a thin film of favorable quality, and to provide a thin film employing the material, an organic electronics element and an organic EL element. <P>SOLUTION: There are provided material for organic electronics containing a compound having one or more polymelizable substituents and two or more carbazole groups, and a thin film employing the material, an organic electronics element and an organic EL element. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a material for organic electronics, and a thin film, an organic electronics element and an organic electroluminescence element (hereinafter sometimes referred to as an organic EL element) using the same.

  Organic electronics elements are elements that perform electrical operations using organic substances, and are expected to exhibit features such as energy saving, low cost, and flexibility, and are attracting attention as a technology that can replace conventional inorganic semiconductors based on silicon. ing.

  Among organic electronics elements, organic EL elements are attracting attention as applications for large-area solid-state light sources as an alternative to incandescent lamps and gas-filled lamps, for example. It is also attracting attention as the most powerful self-luminous display that can replace the liquid crystal display (LCD) in the flat panel display (FPD) field, and its commercialization is progressing.

  The organic EL element has a configuration in which a thin film of an organic compound is sandwiched between a cathode and an anode, and the method of forming the thin film is roughly classified into a vapor deposition method and a coating method. The vapor deposition method is a method of forming a thin film on a substrate in a vacuum mainly using a low molecular compound, and commercialization has preceded. On the other hand, the coating method is a method of forming a thin film on a substrate using a solution, such as ink jet or printing, and the use efficiency of the material is high, and it is suitable for large area and high definition. This is an indispensable technique for EL displays. However, organic EL devices using either method still have great problems, despite their intensive research, low light emission efficiency and short device life. As one means for solving this problem, organic EL elements are multilayered by vapor deposition.

  FIG. 1 shows an example of a multilayered organic EL element. In FIG. 1, the layer responsible for light emission is referred to as a light emitting layer 1, and the layer in contact with the anode 2 is referred to as a hole injection layer 3 and the layer in contact with the cathode 4 is referred to as an electron injection layer 5. Further, when a different layer exists between the light emitting layer 1 and the hole injection layer 3, it is described as a hole transport layer 6, and when a different layer exists between the light emitting layer 1 and the electron injection layer 5, the electron transport It is described as layer 7. In FIG. 1, 8 is a substrate.

  Here, when forming a film by a vapor deposition method, multilayering can be easily achieved by performing vapor deposition while sequentially changing the compound to be used. On the other hand, in the case of film formation and multilayering by a coating method, a method is required in which the formed layer does not change when a new layer is formed. Therefore, many organic EL devices by the coating method use a hole injection layer made of polythiophene: polystyrene sulfonic acid (PEDOT: PSS) which is formed using an aqueous dispersion, and an aromatic organic solvent such as toluene. It has a two-layer structure of a light emitting layer for film formation. In this case, since the PEDOT: PSS layer is not dissolved in toluene, a two-layer structure can be produced.

  The reason why it is difficult to further increase the number of layers in the organic EL device by the coating method is that the lower layer dissolves when lamination is performed with a similar solvent. In order to cope with this problem, a technique is known in which a low molecular compound having a polymerizable substituent is applied and then the solubility is changed by polymerization to form a multilayer structure (for example, Non-Patent Document 1, Patent Document 1). However, low-molecular compounds tend to be crystallized, and there is a problem that it is difficult to form a high-quality thin film.

  In other words, in order to solve the problems of the current organic EL elements, a high-quality thin film (organic layer) is formed by a coating method that can be easily formed even in a large area, and the functions of each layer are separated by multilayering. is important.

  By the way, in recent years, phosphorescent organic EL elements have been actively developed in order to increase the efficiency of organic EL elements. In this phosphorescent organic EL element, not only singlet state energy but also triplet state energy can be used, and the internal quantum yield can be increased to 100% in principle.

  Further, in a phosphorescent organic EL element, phosphorescence is extracted by doping a host material with a metal complex light emitting material containing a heavy metal such as platinum or iridium as a phosphorescent dopant (for example, Non-Patent Document 2, Non-Patent Document 2). Reference 3 and Non-Patent Document 4). The emission of this phosphorescent dopant has a dependence on the host material. The basic performance required for the host material includes a hole transport property and an electron transport property, and the host material has a high triplet state energy level. Generally, CBP (4,4′-Bis A carbazole derivative such as (Carbazol-9-yl) -biphenyl) is preferably used (for example, see Patent Document 2). However, charge transport materials such as CBP are easily crystallized, and film formation by a coating method is difficult. On the other hand, polyfluorene derivatives, polyparaphenylene vinylene (PPV) derivatives, and the like are widely used in organic EL elements by the coating method, but these have a low triplet state energy level and are host materials for phosphorescent organic EL elements. As it was insufficient.

JP 2006-279007 A JP 2003-068466 A Kengo Hirose, Daisuke Kumaki, Nobuaki Koike, Satoshi Kuriyama, Seiichiro Ikehata, Shizushi Tokito, 53rd Joint Physics Conference on Applied Physics, 26p-ZK-4 (2006) M.M. A. Baldo et al. , Nature, vol. 395, p. 151 (1998) M.M. A. Baldo et al. , Applied Physics Letters, vol. 75, p. 4 (1999) M.M. A. Baldo et al. , Nature, vol. 403, p. 750 (2000)

In view of the above problems, an object of the present invention is to provide a material for organic electronics that can be easily multilayered and can form a high-quality thin film.
Another object of the present invention is to provide an organic electronics element and an organic EL element which are more efficient and have a longer life than those of the conventional materials using the organic electronics material of the present invention.

〔式中、Ｅ_１〜Ｅ_５９は、重合可能な置換基を含む基又は置換基Ｒ［Ｒは、それぞれ独立に−Ｒ^１、−ＯＲ^２、−ＳＲ^３、−ＯＣＯＲ^４、−ＣＯＯＲ^５、−ＳｉＲ^６Ｒ^７Ｒ^８、又は下記一般式（４ａ）〜（６ａ）

（ただし、Ｒ^１〜Ｒ^１１は、それぞれ独立に、水素原子、炭素数１〜２２個の直鎖、環状若しくは分岐アルキル基、又は炭素数２〜３０個のアリール基若しくはヘテロアリール基を表し、ａ、ｂ、及びｃは、１以上の整数を表す。）を表す。］を表し、Ｅ_１〜Ｅ_１７のうち、１つ以上が重合可能な置換基を含む基であり、それ以外は前記置換基Ｒであり、Ｅ_１８〜Ｅ_３５のうち、１つ以上が重合可能な置換基を含む基であり、それ以外は前記置換基Ｒであり、Ｅ_３６〜Ｅ_５９のうち、１つ以上が重合可能な置換基を含む基であり、それ以外は前記置換基Ｒであり、Ｘ_１〜Ｘ_４は、前記置換基Ｒのうち、水素原子を２つ以上有する基から、さらに水素原子を２つ除いた基を表す。〕
前記化合物が有する前記重合可能な置換基は、オキセタン基であることが好ましい。また、前記化合物の分子量は、３０００以下であることが好ましい。
本発明の有機エレクトロニクス用材料は、さらにイリジウム錯体又は白金錯体を含有していてもよく、また、さらに重合開始剤を含有していてもよい。
また、本発明は、上記有機エレクトロニクス用材料を含む溶液を用いて形成された薄膜に関する。
さらに、本発明は、上記有機エレクトロニクス用材料を用いて作製された有機エレクトロニクス素子、または、上記有機エレクトロニクス用材料を用いて作製された有機エレクトロルミネセンス素子に関する。
本発明の有機エレクトロルミネセンス素子の態様として、例えば、少なくとも陽極、発光層及び陰極が積層されてなる有機エレクトロルミネセンス素子であって、前記発光層が上記有機エレクトロニクス用材料により形成された層である有機エレクトロルミネセンス素子；少なくとも陽極、正孔輸送層、発光層及び陰極が積層されてなる有機エレクトロルミネセンス素子であって、前記正孔輸送層が上記有機エレクトロニクス用材料により形成された層である有機エレクトロルミネセンス素子；少なくとも陽極、正孔注入層、発光層及び陰極が積層されてなる有機エレクトロルミネセンス素子であって、前記正孔注入層が上記有機エレクトロニクス用材料により形成された層である有機エレクトロルミネセンス素子などがある。 As a result of intensive studies, the inventors of the present invention can form a thin film stably and easily using a material containing a compound having both one or more polymerizable substituents and two or more carbazole groups. It has been found that the solubility is changed by the polymerization reaction, and further, this material has been found to be useful as a material for organic electronics, and the present invention has been completed.
That is, the present invention relates to an organic electronic material containing a compound having one or more polymerizable substituents and two or more carbazole groups in the molecule.
Specific examples of the compound include compounds having a structure represented by any of the following general formulas (1a) to (3a).

[Wherein, E _{1 to} E ₅₉ are a group containing a polymerizable substituent or a substituent R [wherein R is independently —R ¹ , —OR ² , —SR ³ , —OCOR ⁴ , —COOR ⁵ , —SiR ⁶ R ⁷ R ⁸ , or the following general formulas (4a) to (6a)

(However, R ^{1 to} R ¹¹ each independently represents a hydrogen atom, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms, or an aryl group or heteroaryl group having 2 to 30 carbon atoms, a, b, and c represent an integer of 1 or more. And one or more of E _{1 to} E ₁₇ is a group containing a polymerizable substituent, the other is the substituent R, and one or more of E _{18 to} E ₃₅ are polymerized. A group containing a possible substituent, the others being the substituent R, and one or more of E _{36 to} E _{59 being} a group containing a polymerizable substituent, and the others being the substituent R And X _{1 to} X ₄ represent a group obtained by removing two hydrogen atoms from a group having two or more hydrogen atoms in the substituent R. ]
The polymerizable substituent that the compound has is preferably an oxetane group. The molecular weight of the compound is preferably 3000 or less.
The material for organic electronics of the present invention may further contain an iridium complex or a platinum complex, and may further contain a polymerization initiator.
Moreover, this invention relates to the thin film formed using the solution containing the said material for organic electronics.
Furthermore, this invention relates to the organic electronics element produced using the said organic electronics material, or the organic electronics element produced using the said organic electronics material.
As an aspect of the organic electroluminescent device of the present invention, for example, an organic electroluminescent device in which at least an anode, a light emitting layer and a cathode are laminated, wherein the light emitting layer is a layer formed of the organic electronics material. An organic electroluminescence device; an organic electroluminescence device in which at least an anode, a hole transport layer, a light emitting layer, and a cathode are laminated, wherein the hole transport layer is a layer formed of the organic electronics material. An organic electroluminescent element; an organic electroluminescent element in which at least an anode, a hole injection layer, a light emitting layer, and a cathode are laminated, wherein the hole injection layer is a layer formed of the organic electronics material. There are certain organic electroluminescent elements.

  The material for organic electronics of the present invention can form a thin film stably and easily, and the solubility is changed by a polymerization reaction, so that the thin film layer can be easily multi-layered. In particular, it is an extremely useful material for improving the light emission efficiency, light emission lifetime, and productivity of an organic EL device that forms a thin film by a coating method.

  The organic electronic material of the present invention is characterized by containing a compound having both one or more polymerizable substituents and two or more carbazole groups.

  Here, the “polymerizable substituent” means a substituent capable of forming a bond between two or more molecules by causing a polymerization reaction. For example, a group having a carbon-carbon multiple bond ( For example, vinyl group, acetylene group, butenyl group, acryloyl group, acryloyloxy group, acrylamide group, methacryloyl group, methacryloyloxy group, methacrylamide group, arene group, allyl group, vinyloxy group, vinylamino group, furyl group, pyrrole group , A thiophene group, a silole group, etc.), a group having a small ring (eg, cyclopropyl group, cyclobutyl group, epoxy group, oxetane group, diketene group, episulfide group, etc.), lactone group, lactam group or Examples thereof include a group containing a siloxane derivative.

  In addition to the above groups, a combination of groups capable of forming an ester bond or an amide bond can be used as a polymerizable substituent. For example, a combination of an ester group and an amino group, an ester group and a hydroxyl group, or the like. As the polymerizable substituent, an oxetane group, an epoxy group, a vinyl group, an acryloyloxy group, and a methacryloyloxy group are particularly preferable from the viewpoint of reactivity, and an oxetane group is most preferable. The use of an oxetane group is most preferable because a thin film can be formed stably and easily.

Further, as the above compound having both one or more polymerizable substituents and two or more carbazole groups, for example, a monomer having two or more carbazole groups is preferable. What has the structure represented by 1a), (2a), or (3a) is mentioned.

In the general formulas (1a) to (3a), the substituents E _{1 to} E ₅₉ represent a group containing a polymerizable substituent or a substituent R (substituent R will be described later). The substituents E _{1 to} E ₅₉ may be the same or different.

The “group containing a polymerizable substituent” is a substituent having the polymerizable substituent described above, for example, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a carbazole group, or a combination thereof. A group in which one or more of the aforementioned polymerizable substituents, preferably an oxetane group, is bonded to the above-described group. Examples of the group containing an oxetane group include the following structural formulas (7a) to (12a).

In the general formula (1a), one or more of the substituents E _{1 to} E ₁₇ is a group containing a polymerizable substituent, and preferably two or more are groups containing a polymerizable substituent. And most preferably two or four are groups containing polymerizable substituents. Similarly, in the general formula (2a), among the substituents E _{18 to} E ₃₅ , one or more are groups containing a polymerizable substituent, and preferably two or more are groups containing a polymerizable substituent. And most preferably 2 or 4 are groups containing polymerizable substituents. In the general formula (3a), among the substituents E _{36 to} E ₅₉ , one or more are groups containing a polymerizable substituent, and preferably two or more are groups containing a polymerizable substituent. And most preferably two or three are groups containing polymerizable substituents.

（ただし、Ｒ^１〜Ｒ^１１は、それぞれ独立に、水素原子、炭素数１〜２２個の直鎖、環状若しくは分岐アルキル基、又は炭素数２〜３０個のアリール基若しくはヘテロアリール基を表し、ａ、ｂ、及びｃは、それぞれ独立に、１以上の整数、好ましくは１〜４の整数を表す。）で表される置換基を挙げることができ、それぞれは同一であっても異なっていてもよい。置換基Ｒとしては、重合反応性及び耐熱性の点から、未置換のもの、すなわち水素原子であるか又は−Ｒ^１で表されるアルキル基、アリール基、ヘテロアリール基が直接置換したもの、−ＯＲ^２で表される水酸基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基が好ましい。 In addition, among the substituents E _{1 to} E _{59 in} the general formulas (1a) to (3a), except for a group containing the polymerizable substituent, the substituent R is not particularly limited. , for ^{example, -R 1, -OR 2, -SR} 3, -OCOR 4, -COOR 5, -SiR 6 R 7 R 8, or the following general formula is a polyether (4a) ~ (6a)

(However, R ^{1 to} R ¹¹ each independently represents a hydrogen atom, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms, or an aryl group or heteroaryl group having 2 to 30 carbon atoms, a, b, and c each independently represents an integer of 1 or more, preferably an integer of 1 to 4, and each may be the same or different. Also good. As the substituent R, from the viewpoint of polymerization reactivity and heat resistance, an unsubstituted one, that is, a hydrogen atom or an alkyl group, an aryl group, or a heteroaryl group directly represented by -R ¹ , A hydroxyl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group represented by —OR ² is preferable.

In the general formulas (1a) to (3a), X _{1 to} X ₄ are each independently a group having two or more hydrogen atoms in the substituent R (preferably —R ¹ ). A group obtained by removing two hydrogen atoms. In _the case E of binding to X 1 to X ₄ is a hydrogen _atom, X 1 to X ₄ are each independently, said the substituents R (preferably -R ^1), 1 or more hydrogen atoms It represents a group in which one hydrogen atom is further removed from the group having it. Such a group is preferably a group containing a benzene ring, and examples thereof include the following structural formulas (13a) to (15a). X _{1 to} X ₄ may have a substituent. Examples of the substituent include a halogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, an alkoxy group, a trifluoromethyl group, and the like. Can be mentioned.

  Further, the compound used in the present invention preferably has a molecular weight of 3,000 or less, more preferably 400 or more and 2500 or less, and particularly preferably 450 or more and 2000 or less. When this molecular weight exceeds 3,000, the change in solubility during film formation is small, and lamination tends to be difficult.

When the organic electronics material of the present invention is used for the light emitting layer of a phosphorescent organic EL device, a metal complex containing a central metal such as Ir or Pt can be added in addition to the above compound. Although it does not specifically limit as a metal complex, As Ir complex, Ir (ppy) ₃ (Tris (2-phenyl pyridine) iridium) (For example, MA Baldo et al., Applied Physics) which performs green light emission is mentioned, for example. Letters, vol. 75, p. 4 (1999)) or emitting red light (btp ₂ ) Ir (acac) (bis (2- (2′-benzo [4,5-α] thienyl) pyridinate-N, C ³ ) iridium (acetyl-acetonate)) (see, for example, Adachi et al., Appl. Phys. Lett., 78 no. 11, 2001, 1622), Ir (piq) ₃ (tris (1-phenylisoquinoline) iridium) Etc. Examples of the Pt complex include 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-forminplatinum (PtOEP) that emits red light. The phosphorescent material can be a small molecule or a dendrite species, such as an iridium nucleus dendrimer. Moreover, these derivatives can also be used conveniently.

  The compounding ratio of the metal complex is preferably in the range of 0.1% by weight to 20% by weight, more preferably in the range of 0.5% by weight to 15% by weight with respect to the above compound, and 1% by weight. Most preferably, it is in the range of -10 wt%. When the blending ratio of the metal complex is less than 0.1% by weight, the color purity is lowered, and when it exceeds 20% by weight, the driving voltage tends to increase.

  In addition to the above compounds, a polymerization initiator can be further blended in the organic electronics material of the present invention. The polymerization initiator is not particularly limited as long as it exhibits the ability to polymerize a polymerizable substituent by application of heat, light, microwave, radiation, electron beam, and the like. It is preferably one that initiates polymerization by heating, and more preferably one that initiates polymerization by light irradiation (hereinafter referred to as a photoinitiator).

The photoinitiator is not particularly limited as long as it exhibits the ability to polymerize a polymerizable substituent by irradiation with light of 200 nm to 800 nm. For example, when the polymerizable substituent is an oxetane group. In view of reactivity, iodonium salts, sulfonium salts, and ferrocene derivatives are preferable, and the following compounds (16a) to (19a) are exemplified.

  The photoinitiator may be used in combination with a photosensitizer in order to improve photosensitivity. Examples of the photosensitizer include anthracene derivatives and thioxanthone derivatives.

  The blending ratio of the polymerization initiator is preferably in the range of 0.1% by weight to 10% by weight, and in the range of 0.2% by weight to 8% by weight with respect to the total weight of the organic electronics material. It is more preferable that the range is 0.5 to 5% by weight. When the blending ratio of the polymerization initiator is less than 0.1% by weight, stacking tends to be difficult, and when it exceeds 10% by weight, device characteristics tend to deteriorate.

  In addition to the above compounds, carbon materials such as carbon nanotubes and fullerenes can be further blended with the organic electronics material of the present invention in order to adjust electrical characteristics.

  In order to form various layers (thin films) used for an organic electronics element or the like using the organic electronics material of the present invention, for example, a solution containing the organic electronics material of the present invention is used, for example, an inkjet method, a cast After coating on a desired substrate by a known method such as a printing method, dipping method, letterpress printing, intaglio printing, offset printing, flat plate printing, letterpress reverse printing, screen printing, gravure printing, etc. It can be carried out by advancing the polymerization reaction of the above compound by light irradiation, heat treatment or the like, and changing (curing) the solubility of the coating layer. By repeating such an operation, it becomes possible to increase the number of organic electronics elements and organic EL elements using a coating method.

  The coating method as described above can be usually carried out at a temperature range of -20 to + 300 ° C, preferably 10 to 100 ° C, particularly preferably 15 to 50 ° C. Although there is no particular limitation, for example, chloroform, methylene chloride, dichloroethane, tetrahydrofuran, toluene, xylene, mesitylene, anisole, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, ethyl cellosolve acetate and the like can be mentioned.

  In addition, a light source such as a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a xenon lamp, a fluorescent lamp, a light emitting diode, or sunlight can be used for the light irradiation.

  Moreover, the said heat processing can be performed on a hotplate or in oven, and can be implemented at the temperature range of 0- + 300 degreeC, Preferably it is 20-250 degreeC, Most preferably, it is 80-200 degreeC.

  The material for organic electronics of the present invention can be used alone or in combination with other materials as a functional material of an organic electronics element. In addition, the organic electronics material of the present invention may be used alone or in combination with other materials to form a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron of an organic EL element. It can be used as a transport layer and an electron injection layer.

  The organic electronics element and the organic EL element of the present invention are not particularly limited as long as the organic electronics element and the organic EL element of the present invention have a layer formed using the organic electronics material of the present invention. The general structure of the organic EL is disclosed in, for example, US Pat. No. 4,539,507, US Pat. No. 5,151,629, and the like. The polymer-containing organic EL device is disclosed in, for example, International Publication No. 90/13148, European Patent Application Publication No. 04383861, and the like. These usually include an electroluminescent layer (light-emitting layer) between a cathode (cathode) and an anode (anode) in which at least one of the electrodes is transparent. Furthermore, one or more electron injection layers and / or electron transport layers are inserted between the electroluminescent layer (light emitting layer) and the cathode, one or more hole injection layers and / or hole transport In some cases, a layer is inserted between the electroluminescent layer (light emitting layer) and the anode.

  The cathode material is preferably a metal or metal alloy such as Li, Ca, Mg, Al, In, Cs, Ba, Mg / Ag, LiF, and CsF. As an anode material, a metal (for example, Au) or other material having metal conductivity, for example, an oxide (for example, ITO: indium oxide / tin oxide) on a transparent substrate (for example, glass or transparent polymer). It can also be used.

  As described above, the material for organic electronics of the present invention can be used as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like of an organic electronics element. Are preferably used as a hole injection layer, a hole transport layer, and a light emitting layer, more preferably used as a hole transport layer and a light emitting layer, and most preferably used as a light emitting layer.

  Moreover, there is no restriction | limiting in particular about the film thickness of these layers, However, It is preferable that it is 5-100 nm, It is more preferable that it is 10-80 nm, It is further more preferable that it is 20-60 nm.

  The organic electronic material of the present invention can form a high-quality thin film. Here, a good quality thin film is a thin film that is difficult to progress in crystallization. The ease of progress of crystallization can be measured, for example, by the ratio of the area that becomes cloudy when a thin film made of an organic electronics material is heated in nitrogen at 100 ° C. for 10 minutes. The ratio of the cloudy area is preferably 50% or less, more preferably 30% or less, and most preferably 10% or less.

  Since the solubility of the organic electronic material of the present invention is changed by the polymerization reaction of the compound described above, not only is it easy to stack thin films made of the material, but it is also possible to improve the thermal stability of the thin film. is there. For example, when a dopant such as an iridium complex is introduced, aggregation can be suppressed and thermal stability and luminous efficiency can be improved.

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

丸底フラスコに、３−エチル−３−ヒドロキシメチルオキセタン（５０ｍｍｏｌ）、４−ブロモベンジルブロミド（５０ｍｍｏｌ）、ｎ−ヘキサン（２００ｍＬ）、テトラブチルアンモニウムブロミド（２．５ｍｍｏｌ）及び５０重量％水酸化ナトリウム水溶液（３６ｇ）を加え、窒素下、７０℃で６時間加熱撹拌した。室温（２５℃）まで冷却後、水２００ｍＬを加え、ｎ−ヘキサンで抽出した。溶媒留去後、シリカゲルカラムクロマトグラフィーと減圧蒸留によって精製し、オキセタン化合物Ａを無色油状物として９．５１ｇ得た（収率６７重量％）。
^１Ｈ−ＮＭＲ（３００ＭＨｚ，ＣＤＣｌ_３，δｐｐｍ）；０．８６（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ），１．７６（ｔ，Ｊ＝７．５Ｈｚ，２Ｈ），３．５７（ｓ，２Ｈ），４．３９（ｄ，Ｊ＝５．７Ｈｚ，２Ｈ），４．４５（ｄ，Ｊ＝５．７Ｈｚ，２Ｈ），４．５１（ｓ，２Ｈ），７．２２（ｄ，Ｊ＝８．４Ｈｚ，２Ｈ），７．４７（ｄ，Ｊ＝８．４Ｈｚ，２Ｈ）

５０ｍＬ丸底フラスコに、上記で得たオキセタン化合物Ａ２．９９ｇ（１０ｍｍｏｌ）、ビス（ピナコラト）ジボラン３．８１ｇ（１５ｍｍｏｌ）、Ｐｄ（ｄｐｐｆ）０．２４ｇ（０．３ｍｍｏｌ）及び酢酸カリウム４．９１ｇ（５０ｍｍｏｌ）を入れ、窒素置換した。ここにＤＭＦ２０ｍＬを加え、窒素気流下で９５℃、９時間加熱撹拌した。室温まで冷却後、水を加え、酢酸エチルで抽出した。溶媒を留去後、シリカゲルカラムクロマトグラフィーを用いて精製を行い、ほぼ純粋なオキセタン化合物Ｂを１．９９ｇ得た（収率６０％）。
^１Ｈ−ＮＭＲ（３００ＭＨｚ，ＣＤＣｌ_３，δｐｐｍ）；０．８６（ｔ，Ｊ＝７．５Ｈｚ，２Ｈ），１．３５（ｓ，１２Ｈ），１．７８（ｑ，Ｊ＝７．５Ｈｚ，２Ｈ）， ３．５６（ｓ，２Ｈ），４．３９（ｄ，Ｊ＝５．７Ｈｚ，２Ｈ），４．４６（ｄ，Ｊ＝５．７Ｈｚ，２Ｈ），４．５９（ｓ，２Ｈ），７．３５（ｄ，Ｊ＝８．４Ｈｚ，２Ｈ），７．８１（ｄ，Ｊ＝８．４Ｈｚ，２Ｈ）

１Ｌ丸底フラスコに、ＣＢＰ（３．５６ｇ，７．３５ｍｍｏｌ）、塩化メチレン（５００ｍＬ）を入れた。ここに、臭素（６．２２ｇ，３８．９ｍｍｏｌ）の塩化メチレン（５０ｍｌ）溶液を滴下した。室温で１０時間撹拌した後、加熱還流しながら１０時間反応させた。室温まで冷却後、不溶物をろ別し、ヘキサンで洗浄した。真空乾燥後、ほぼ純粋なＢｒ４−ＣＢＰを得た。ついで、丸底フラスコに、上記で得たＢｒ４−ＣＢＰ（１．７４ｇ、１ｍｍｏｌ）、オキセタン化合物Ｂ（１．５９ｇ、５ｍｍｏｌ）、トルエン（３０ｍＬ）、Ａｌｉｑｕａｔ３３６（０．２ｇ）、炭酸カリウム（２Ｍ、１２ｍＬ）及びテトラキス（トリフェニルホスフィン）パラジウム（０．１ｇ）を入れ、窒素気流下、マイクロウェーブを照射して９０℃で５時間加熱撹拌した。室温まで冷却後、水を加え、塩化メチレンを用いて抽出した。水洗後、溶媒留去し、シリカゲルカラムクロマトグラフィーによって精製し、ＯＸＴ４−ＣＢＰ ５１８ｍｇを得た（収率４０％）。 <Synthesis Example of Carbazole Derivative Having Polymerizable Substituent>
(Synthesis Example 1)

In a round bottom flask, 3-ethyl-3-hydroxymethyloxetane (50 mmol), 4-bromobenzyl bromide (50 mmol), n-hexane (200 mL), tetrabutylammonium bromide (2.5 mmol) and 50 wt% sodium hydroxide An aqueous solution (36 g) was added, and the mixture was heated with stirring at 70 ° C. for 6 hours under nitrogen. After cooling to room temperature (25 ° C.), 200 mL of water was added and extracted with n-hexane. After the solvent was distilled off, the residue was purified by silica gel column chromatography and distillation under reduced pressure to obtain 9.51 g of oxetane compound A as a colorless oil (yield: 67% by weight).
¹ H-NMR (300 MHz, CDCl ₃ , δ ppm); 0.86 (t, J = 7.5 Hz, 3H), 1.76 (t, J = 7.5 Hz, 2H), 3.57 (s, 2H) ), 4.39 (d, J = 5.7 Hz, 2H), 4.45 (d, J = 5.7 Hz, 2H), 4.51 (s, 2H), 7.22 (d, J = 8) .4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H)

In a 50 mL round bottom flask, 2.99 g (10 mmol) of the oxetane compound A obtained above, 3.81 g (15 mmol) of bis (pinacolato) diborane, 0.24 g (0.3 mmol) of Pd (dppf) and 4.91 g of potassium acetate ( 50 mmol) and nitrogen substitution was performed. DMF20mL was added here and it heat-stirred at 95 degreeC for 9 hours under nitrogen stream. After cooling to room temperature, water was added and extracted with ethyl acetate. After distilling off the solvent, purification was performed using silica gel column chromatography to obtain 1.99 g of an almost pure oxetane compound B (yield 60%).
¹ H-NMR (300 MHz, CDCl ₃ , δ ppm); 0.86 (t, J = 7.5 Hz, 2H), 1.35 (s, 12H), 1.78 (q, J = 7.5 Hz, 2H) ), 3.56 (s, 2H), 4.39 (d, J = 5.7 Hz, 2H), 4.46 (d, J = 5.7 Hz, 2H), 4.59 (s, 2H), 7.35 (d, J = 8.4 Hz, 2H), 7.81 (d, J = 8.4 Hz, 2H)

A 1 L round bottom flask was charged with CBP (3.56 g, 7.35 mmol) and methylene chloride (500 mL). A solution of bromine (6.22 g, 38.9 mmol) in methylene chloride (50 ml) was added dropwise thereto. After stirring at room temperature for 10 hours, the reaction was carried out for 10 hours while heating under reflux. After cooling to room temperature, the insoluble material was filtered off and washed with hexane. After vacuum drying, almost pure Br4-CBP was obtained. Subsequently, Br4-CBP (1.74 g, 1 mmol) obtained above, oxetane compound B (1.59 g, 5 mmol), toluene (30 mL), Aliquat 336 (0.2 g), potassium carbonate (2M, 12 mL) and tetrakis (triphenylphosphine) palladium (0.1 g) were added, and the mixture was heated and stirred at 90 ° C. for 5 hours while being irradiated with microwaves under a nitrogen stream. After cooling to room temperature, water was added and extracted with methylene chloride. After washing with water, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 518 mg of OXT4-CBP (yield 40%).

丸底フラスコに、３−ブロモカルバゾール（１２ｍｍｏｌ）、４，４’−ジヨードビフェニル（３．９ｍｍｏｌ）、銅（１６ｍｍｏｌ）、炭酸カリウム（１８ｍｍｏｌ）、ｏ−ジクロロベンゼン（８０ｍＬ）を入れ、１８０℃で７２時間撹拌した。冷却後ろ過し、溶媒留去した。シリカゲルカラムクロマトグラフィーと再結晶によって精製し、ＣＺ１を０．７７ｇ得た。
^１Ｈ−ＮＭＲ（３００ＭＨｚ，ＣＤＣｌ_３，δｐｐｍ）；７．３２−７．３９（ｍ，４Ｈ），７．４７−７．５５（ｍ，６Ｈ），７．６９（ｍ，４Ｈ），７．９３（ｍ，４Ｈ），８．１２（ｍ，２Ｈ），８．２８（ｍ，２Ｈ）

５０ｍＬフラスコにＣＺ１（０．７ｍｍｏｌ）、オキセタン化合物Ｂ（１．７５ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．０１４ｍｍｏｌ）、トルエン（１０ｍＬ）、Ａｌｉｑｕａｔ３３６（３０％トルエン溶液、０．６ｍＬ）、２Ｍ炭酸カリウム水溶液（４．２ｍＬ）を入れ、窒素下、９５℃で１８時間加熱撹拌した。反応終了後トルエンで抽出し、溶媒留去後、シリカゲルカラムクロマトグラフィーで精製し、無色粉末としてＣＺ１−ＯＸＴ（０．３ｇ）を得た。図２に、ＣＺ１−ＯＸＴの^１Ｈ−ＮＭＲスペクトルを示す。
^１Ｈ−ＮＭＲ（３００ＭＨｚ，ＣＤＣｌ_３，δｐｐｍ）；０．９３（ｔ，Ｊ＝７．５Ｈｚ，６Ｈ），１．８２（ｑ，Ｊ＝７．５Ｈｚ，４Ｈ）， ３．６５（ｓ，４Ｈ），４．４３（ｄ，Ｊ＝６．０Ｈｚ，４Ｈ），４．５２（ｄ，Ｊ＝６．０Ｈｚ，４Ｈ），４．６５（ｓ，４Ｈ），７．３４（ｍ，２Ｈ），７．３８−７．５９（ｍ，１０Ｈ），７．７０−７．７６（ｍ，１０Ｈ），７．９３（ｍ，４Ｈ），８．２３（ｍ，２Ｈ），８．４０（ｍ，２Ｈ） (Synthesis Example 2)

In a round bottom flask, 3-bromocarbazole (12 mmol), 4,4′-diiodobiphenyl (3.9 mmol), copper (16 mmol), potassium carbonate (18 mmol), o-dichlorobenzene (80 mL) were placed, and 180 ° C. For 72 hours. After cooling, the mixture was filtered and the solvent was distilled off. Purification by silica gel column chromatography and recrystallization gave 0.77 g of CZ1.
¹ H-NMR (300 MHz, CDCl ₃ , δ ppm); 7.32-7.39 (m, 4H), 7.47-7.55 (m, 6H), 7.69 (m, 4H), 7. 93 (m, 4H), 8.12 (m, 2H), 8.28 (m, 2H)

In a 50 mL flask, CZ1 (0.7 mmol), oxetane compound B (1.75 mmol), Pd (PPh ₃ ) ₄ (0.014 mmol), toluene (10 mL), Aliquat 336 (30% toluene solution, 0.6 mL), 2M carbonic acid A potassium aqueous solution (4.2 mL) was added, and the mixture was heated and stirred at 95 ° C. for 18 hours under nitrogen. After completion of the reaction, the mixture was extracted with toluene, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain CZ1-OXT (0.3 g) as a colorless powder. FIG. 2 shows the ¹ H-NMR spectrum of CZ1-OXT.
¹ H-NMR (300 MHz, CDCl ₃ , δ ppm); 0.93 (t, J = 7.5 Hz, 6H), 1.82 (q, J = 7.5 Hz, 4H), 3.65 (s, 4H) ), 4.43 (d, J = 6.0 Hz, 4H), 4.52 (d, J = 6.0 Hz, 4H), 4.65 (s, 4H), 7.34 (m, 2H), 7.38-7.59 (m, 10H), 7.70-7.76 (m, 10H), 7.93 (m, 4H), 8.23 (m, 2H), 8.40 (m, 2H)

合成例２と同様の方法で、４，４’−ジヨードビフェニルの代わりに２，２’−ジメチル−４，４’−ジヨードビフェニルを用いてＣＺ２を合成し、さらにオキセタン化合物Ｂと反応させてＣＺ２−ＯＸＴを合成した。図３に、ＣＺ２−ＯＸＴの^１Ｈ−ＮＭＲスペクトルを示す。
^１Ｈ−ＮＭＲ（３００ＭＨｚ，ＴＨＦ−ｄ_８，δｐｐｍ）；０．９０（ｔ，Ｊ＝７．５Ｈｚ，６Ｈ），１．７９（ｑ，Ｊ＝７．５Ｈｚ，４Ｈ）， ２．５６（ｓ，６Ｈ），３．６３（ｓ，４Ｈ），４．２８（ｄ，Ｊ＝６．０Ｈｚ，４Ｈ），４．３８（ｄ，Ｊ＝６．０Ｈｚ，４Ｈ），４．６０（ｓ，４Ｈ），７．２６（ｍ，２Ｈ），７．３９−７．７５（ｍ，２２Ｈ），８．２２（ｍ，２Ｈ），８．４４（ｍ，２Ｈ） (Synthesis Example 3)

In the same manner as in Synthesis Example 2, CZ2 was synthesized using 2,2′-dimethyl-4,4′-diiodobiphenyl instead of 4,4′-diiodobiphenyl, and further reacted with oxetane compound B. Thus, CZ2-OXT was synthesized. FIG. 3 shows the ¹ H-NMR spectrum of CZ2-OXT.
¹ H-NMR (300 MHz, THF-d ₈ , δ ppm); 0.90 (t, J = 7.5 Hz, 6H), 1.79 (q, J = 7.5 Hz, 4H), 2.56 (s 6H), 3.63 (s, 4H), 4.28 (d, J = 6.0 Hz, 4H), 4.38 (d, J = 6.0 Hz, 4H), 4.60 (s, 4H). ), 7.26 (m, 2H), 7.39-7.75 (m, 22H), 8.22 (m, 2H), 8.44 (m, 2H)

合成例２と同様の方法で、４，４’−ジヨードビフェニルの代わりに３，５−ジヨードトルエンを用いてＣＺ３合成し、さらにオキセタン化合物Ｂと反応させてＣＺ３−ＯＸＴを合成した。図４は、ＣＺ３−ＯＸＴの^１Ｈ−ＮＭＲスペクトルである。
^１Ｈ−ＮＭＲ（３００ＭＨｚ，ＣＤＣｌ_３，δｐｐｍ）；０．９０（ｔ，Ｊ＝７．５Ｈｚ，６Ｈ），１．８１（ｑ，Ｊ＝７．５Ｈｚ，４Ｈ）， ２．６３（ｓ，３Ｈ），３．６３（ｓ，４Ｈ），４．４２（ｄ，Ｊ＝６．０Ｈｚ，４Ｈ），４．５０（ｄ，Ｊ＝６．０Ｈｚ，４Ｈ），４．６４（ｓ，４Ｈ），７．３１−７．７３（ｍ，２１Ｈ），８．２２（ｍ，２Ｈ），８．３７（ｍ，２Ｈ） (Synthesis Example 4)

In the same manner as in Synthesis Example 2, CZ3 was synthesized using 3,5-diiodotoluene instead of 4,4′-diiodobiphenyl, and further reacted with oxetane compound B to synthesize CZ3-OXT. FIG. 4 is a ¹ H-NMR spectrum of CZ3-OXT.
¹ H-NMR (300 MHz, CDCl ₃ , δ ppm); 0.90 (t, J = 7.5 Hz, 6H), 1.81 (q, J = 7.5 Hz, 4H), 2.63 (s, 3H ), 3.63 (s, 4H), 4.42 (d, J = 6.0 Hz, 4H), 4.50 (d, J = 6.0 Hz, 4H), 4.64 (s, 4H), 7.31-7.73 (m, 21H), 8.22 (m, 2H), 8.37 (m, 2H)

<Production of organic EL element>
Example 1 Application Example as Light-Emitting Layer
PEDOT: PSS dispersion (Stark Vitech, CH8000 LVW233) was spin-coated at 4000 min ⁻¹ on a glass substrate patterned with ITO to a width of 1.6 mm, and 200 ° C./10 minutes in air on a hot plate. A hole injection layer (40 nm) was formed by heating and drying. The subsequent steps were performed in a dry nitrogen environment.
Next, a coating solution in which OXT4-CBP (20 mg), tris (2- (4-tolyl) pyridine) iridium (0.6 mg) and anisole (1 ml) obtained above were mixed on the hole injection layer was added for 2000 min. After spin coating at ⁻¹ , the mixture was dried by heating at 80 ° C. for 15 minutes on a hot plate to form a light emitting layer (80 nm).
Furthermore, the obtained glass substrate was moved into a vacuum evaporation machine, and electrodes were formed on the light emitting layer in the order of Ba (film thickness: 3 nm) and Al (film thickness: 100 nm). After electrode formation, the substrate is moved into a dry nitrogen environment without opening to the atmosphere, and the sealing glass and ITO substrate in which 0.4 mm of counterbore is added to 0.7 mm non-alkali glass are coated with a photocurable epoxy resin. The organic EL element was produced by sealing by using and bonding. The subsequent steps were performed in the atmosphere at room temperature (25 ° C.).
When a voltage was applied using ITO as an anode and Al as a cathode of this organic EL element, uniform green light emission was observed at about 8V.

(Comparative Example 1)
An EL device was produced in the same manner as in Example 1 except that CBP was used instead of OX4-CBP. However, many dark spots were generated, and uniform light emission could not be obtained.

で表される光開始剤（０．１３ｍｇ）、トルエン（０．７５ｍｌ）を混合した塗布溶液を、３０００ｒｐｍでスピンコートした後、メタルハライドランプを用いて光照射（３Ｊ／ｃｍ^２）し、ホットプレート上で１８０℃、６０分間加熱して硬化させ、正孔輸送層（２０ｎｍ）を形成した。
次いで、得られたガラス基板を真空蒸着機中に移し、ＣＢＰとＩｒ（ｐｉｑ）_３の共蒸着膜（４０ｎｍ）、ＢＡｌｑ（５ｎｍ）、Ａｌｑ_３（３０ｎｍ）、ＬｉＦ（０．５ｎｍ）、Ａｌ（１００ｎｍ）の順に蒸着し、窒素環境中で封止を行った。
この有機ＥＬ素子のＩＴＯを陽極、Ａｌを陰極として電圧を印加したところ、約６Ｖで赤色発光が観測され、輝度１０００ｃｄ／ｍ^２における電流効率は６．０ｃｄ／Ａであった。
また、寿命特性として、０．７ｍＡの定電流を印加しながらトプコン社製ＢＭ−７で輝度を測定し、輝度が初期輝度から半減する時間を測定したところ、５０時間であった。 Example 2 Application Example as Hole Transport Layer
In the same manner as in Example 1, a hole injection layer (40 nm) was formed using a PEDOT: PSS dispersion. The subsequent steps were performed in a dry nitrogen environment.
Next, CZ1-OXT (3.1 mg) obtained above on the hole injection layer, the following chemical formula

A coating solution in which a photoinitiator represented by the formula (0.13 mg) and toluene (0.75 ml) are mixed is spin-coated at 3000 rpm, and then irradiated with light using a metal halide lamp (3 J / cm ² ) to form a hot plate. The above was heated and cured at 180 ° C. for 60 minutes to form a hole transport layer (20 nm).
Next, the obtained glass substrate was transferred into a vacuum deposition machine, and a co-deposited film of CBP and Ir (piq) ₃ (40 nm), BAlq (5 nm), Alq ₃ (30 nm), LiF (0.5 nm), Al ( 100 nm) in order and sealed in a nitrogen environment.
When voltage was applied with ITO as the anode and Al as the cathode of this organic EL element, red light emission was observed at about 6 V, and the current efficiency at a luminance of 1000 cd / m ² was 6.0 cd / A.
Further, as a lifetime characteristic, the luminance was measured with Topcon BM-7 while applying a constant current of 0.7 mA, and the time for the luminance to be halved from the initial luminance was 50 hours.

(Comparative Example 2)
An organic EL device was produced in the same manner as in Example 2 except that the hole transport layer containing CZ1-OXT was not formed. When a voltage was applied to this organic EL element, red light emission was observed at about 6 V, the current efficiency at a luminance of 1000 cd / m ² was 4.0 cd / A, and in Example 2, 1.5 times that of Comparative Example 2. Efficiency was obtained. Further, when the lifetime characteristics were measured, the luminance was reduced by half in 5 hours, and in Example 1, a lifetime that was 10 times that of Comparative Example 2 was obtained.

Example 3 Application Example as Hole Transport Layer and Light-Emitting Layer
In the same manner as in Example 1, a hole injection layer (40 nm) was formed using a PEDOT: PSS dispersion, and subsequently, a hole transport layer containing CZ1-OXT was formed in the same manner as in Example 2.
Further, a coating solution in which CZ1-OXT (10 mg), Ir (piq) ₃ (0.5 mg) and anisole (0.7 ml) were mixed was spin-coated at 2000 rpm, and then heated on a hot plate at 80 ° C. for 5 minutes. And dried to form a light emitting layer (40 nm). The hole transport layer and the light emitting layer could be formed without crossing each other.
Next, the obtained glass substrate was transferred into a vacuum deposition machine, and BAlq (5 nm), Alq ₃ (30 nm), LiF (0.5 nm), and Al (100 nm) were deposited in this order, and sealed in a nitrogen environment. It was.
When voltage was applied using ITO as the anode and Al as the cathode of this organic EL element, red light emission was observed at about 6 V, and the current efficiency at a luminance of 1000 cd / m ² was 5.5 cd / A.

<Evaluation of progress of crystallization>
Example 4
A toluene solution (concentration: 0.8% by weight) of CZ1-OXT is spin-coated (3000 rpm) on a quartz substrate (29 mm × 22 mm), dried by heating at 80 ° C. for 5 minutes on a hot plate, and a film thickness of 40 nm. A thin film was prepared. The thin film was heated in nitrogen at 100 ° C. for 10 minutes, and the ratio of the area that became cloudy was determined with an optical microscope.

(Comparative Example 3)
Using a CBP toluene solution (concentration: 0.8 wt%), a thin film having a thickness of 40 nm was prepared in the same manner as in Example 4, and heated in nitrogen at 100 ° C. for 10 minutes. The ratio of the cloudy area was 64%, and Example 4 was 1/10 or less of Comparative Example 3.

It is the schematic which shows an example of the multilayered organic EL element. It is a ¹ H-NMR spectrum of CZ1-OXT. It is a ¹ H-NMR spectrum of CZ2-OXT. It is a ¹ H-NMR spectrum of CZ3-OXT.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Light emitting layer 2 Anode 3 Hole injection layer 4 Cathode 5 Electron injection layer 6 Hole transport layer 7 Electron transport layer 8 Substrate

Claims (12)

  An organic electronic material containing a compound having one or more polymerizable substituents and two or more carbazole groups in a molecule. The material for organic electronics according to claim 1, wherein the compound has a structure represented by any one of the following general formulas (1a) to (3a).

[Wherein, E _{1 to} E ₅₉ are a group containing a polymerizable substituent or a substituent R [wherein R is independently —R ¹ , —OR ² , —SR ³ , —OCOR ⁴ , —COOR ⁵ , —SiR ⁶ R ⁷ R ⁸ , or the following general formulas (4a) to (6a)

(However, R ^{1 to} R ¹¹ each independently represents a hydrogen atom, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms, or an aryl group or heteroaryl group having 2 to 30 carbon atoms, a, b, and c represent an integer of 1 or more. And one or more of E _{1 to} E ₁₇ is a group containing a polymerizable substituent, the other is the substituent R, and one or more of E _{18 to} E ₃₅ are polymerized. A group containing a possible substituent, the others being the substituent R, and one or more of E _{36 to} E _{59 being} a group containing a polymerizable substituent, and the others being the substituent R And X _{1 to} X ₄ represent a group obtained by removing two hydrogen atoms from a group having two or more hydrogen atoms in the substituent R. ]   The organic electronic material according to claim 1 or 2, wherein the polymerizable substituent is an oxetane group.   The molecular weight of the said compound is 3000 or less, The material for organic electronics in any one of Claims 1-3.   Furthermore, the material for organic electronics in any one of Claims 1-4 containing an iridium complex or a platinum complex.   Furthermore, the material for organic electronics in any one of Claims 1-5 containing a polymerization initiator.   The thin film formed using the solution containing the material for organic electronics in any one of Claims 1-6.   The organic electronics element produced using the organic electronics material in any one of Claims 1-6.   The organic electroluminescent element produced using the material for organic electronics in any one of Claims 1-6.   An organic electroluminescence device comprising at least an anode, a light emitting layer, and a cathode, wherein the light emitting layer is a layer formed of the organic electronics material according to claim 1. Sense element.   It is an organic electroluminescent element formed by laminating at least an anode, a hole transport layer, a light emitting layer, and a cathode, and the hole transport layer is formed of the organic electronics material according to any one of claims 1 to 6. An organic electroluminescence device which is a layer.   It is an organic electroluminescent element formed by laminating at least an anode, a hole injection layer, a light emitting layer, and a cathode, and the hole injection layer is formed of the organic electronics material according to any one of claims 1 to 6. An organic electroluminescence device which is a layer.

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