JP2006237442A - Composition for conductive material, conductive material, conductive layer, electronic device and electronic apparatus - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a conductive material excellent in carrier transportability, a conductive layer principally comprising such a conductive material, and a highly reliable electronic device and electronic apparatus. <P>SOLUTION: A composition for the conductive material contains a compound represented by general formula (1), and an acryl based crosslinking agent. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a composition for a conductive material, a conductive material, a conductive layer, an electronic device, and an electronic apparatus.

Electroluminescent elements using organic materials (hereinafter simply referred to as “organic EL elements”) are promising for use as solid light-emitting, inexpensive, large-area full-color display elements (light-emitting elements), and many developments have been made. It has been broken.
In general, an organic EL device has a light emitting layer between a cathode and an anode. When an electric field is applied between the cathode and the anode, electrons are injected into the light emitting layer from the cathode side, and holes are formed from the anode side. Is injected.

Then, the injected electrons and holes are recombined in the light emitting layer, and the light emitting layer emits light by releasing the excitation energy when the energy level returns from the conduction band to the valence band as light energy.
In such an organic EL element, in order to increase the efficiency of the organic EL element, that is, to obtain high light emission, an organic layer composed of organic materials having different electron or hole carrier transport properties, and a light emitting layer, It has been found that an element structure laminated between the cathode and / or the anode is effective.

  Therefore, it is necessary to laminate a light emitting layer and an organic layer (hereinafter collectively referred to as “organic layer”) having different carrier transport properties on the electrode. In the manufacturing method using the conventional coating method, When laminating layers, phase dissolution occurs between adjacent organic layers, resulting in a decrease in characteristics such as emission efficiency, color purity or color accuracy of the organic EL element. was there.

Therefore, in the case of stacking organic layers, the organic material is limited to stacking by using a combination of organic materials having different solubility.
As a method for solving such problems, a method for improving the durability of the lower layer, that is, the solvent resistance by polymerizing organic materials constituting the lower organic layer has been disclosed (for example, patents) Reference 1).

Also disclosed is a method for improving the solvent resistance of the lower layer by adding a curable resin to the organic material constituting the lower organic layer and curing it together with the curable resin (for example, patents). Reference 2).
However, even when these methods are used, the actual situation is that the improvement of the characteristics of the organic EL element has not been obtained as expected.
Such a problem also occurs in a thin film transistor using an organic material.

Japanese Patent Laid-Open No. 9-255774 JP 2000-208254 A

  An object of the present invention is to provide a conductive material composition capable of forming a conductive layer having excellent carrier transporting ability, a conductive material having excellent carrier transporting ability obtained by using such a conductive material composition, An object of the present invention is to provide a conductive layer mainly composed of such a conductive material, a highly reliable electronic device, and an electronic apparatus.

［式中、２つのＲ^１は、それぞれ独立して、炭素数２〜８の直鎖アルキル基を表し、同一であっても、異なっていてもよく、４つのＲ^２は、それぞれ独立して、水素原子、メチル基またはエチル基を表し、同一であっても、異なっていてもよく、２つのＸは、それぞれ独立して、下記一般式（２）で表される置換基を表し、同一であっても、異なっていてもよく、Ｙは、置換もしくは無置換の複素環を少なくとも１つ含む基を表す。］

［式中、ｎは、２〜８の整数を表し、Ｚは、水素原子またはメチル基を表す。］
これにより、キャリア輸送能の優れた導電層を形成することができる導電性材料用組成物とすることができる。 Such an object is achieved by the present invention described below.
The composition for conductive materials of the present invention contains a compound represented by the following general formula (1) and an acrylic crosslinking agent.

[Wherein, two R ^{1 s} each independently represent a straight-chain alkyl group having 2 to 8 carbon atoms, and may be the same or different, and four R ^{2 s} each independently Represents a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and two X's each independently represent a substituent represented by the following general formula (2); Or Y may be different, and Y represents a group containing at least one substituted or unsubstituted heterocycle. ]

[Wherein, n represents an integer of 2 to 8, and Z represents a hydrogen atom or a methyl group. ]
Thereby, it can be set as the composition for conductive materials which can form the conductive layer excellent in carrier transport ability.

In the composition for conductive material of the present invention, it is preferable that the acrylic crosslinking agent has a polyester (meth) acrylate crosslinking agent as a main component.
Thereby, the polymer (conductive material) obtained by polymerizing the substituent X between the compounds represented by the general formula (1) directly or via a polyester (meth) acrylate-based crosslinking agent. In the inside, the ratio of the substituent X and the ratio of the polyester (meth) acrylate crosslinking agent become uniform. As a result, the conductive layer formed of this polymer can have uniform film characteristics.

In the composition for conductive material of the present invention, the polyester (meth) acrylate-based crosslinking agent preferably has at least two (meth) acryloyl groups.
Thus, the two substituents X can be more reliably connected via the polyester (meth) acrylate-based crosslinking agent, and when the polymer is formed, the two substituents X are represented by the general formula (1). Among the main skeletons other than the substituent X of the compound, adjacent ones can be kept at a more appropriate distance.

［式中、ｎは、４５００以下の整数を表し、２つのＡは、それぞれ独立して、水素原子またはメチル基を表し、同一であっても、異なっていてもよい。］
かかる化合物を用いることにより、置換基Ｘを、直接、またはポリエステル（メタ）アクリレート系架橋剤を介して、重合反応させて得られた高分子は、キャリア輸送能がより優れたものとなる。 In the composition for conductive material of the present invention, it is preferable that the polyester (meth) acrylate-based cross-linking agent contains a compound represented by the following general formula (3) as a main component.

[Wherein n represents an integer of 4500 or less, and two A's each independently represent a hydrogen atom or a methyl group, and may be the same or different. ]
By using such a compound, the polymer obtained by subjecting the substituent X to a polymerization reaction directly or via a polyester (meth) acrylate-based crosslinking agent has a higher carrier transport ability.

In the composition for conductive material of the present invention, the two substituents X are preferably the same.
Thereby, in polymer | macromolecule, the separation distance of main frame | skeleton can be made into a magnitude | size beyond a fixed level. As a result, it is possible to suitably prevent the interaction between the main skeletons in the polymer. Thereby, the carrier transport ability of the polymer can be improved.

In the composition for a conductive material of the present invention, the substituent X is preferably bonded to any of the 3-position, 4-position or 5-position of the benzene ring.
Thereby, in the polymer, the main skeletons can be more reliably separated at an appropriate distance.
In the composition for conductive material of the present invention, the two substituents R ¹ are preferably the same.
Thereby, in the conductive layer to be formed, the distance between adjacent polymers can be maintained at a substantially constant interval. As a result, the polymer density in the conductive layer becomes constant.

In the composition for a conductive material of the present invention, the substituent R ¹ is preferably bonded to the 4-position of the benzene ring.
Thereby, in the conductive layer to be formed, it is possible to more reliably prevent adjacent polymers from being too close to each other.
In the composition for a conductive material of the present invention, the heterocyclic ring preferably contains at least one heteroatom selected from nitrogen, oxygen, sulfur, selenium and tellurium.
As a result, the energy level of the valence band and the conduction band of the polymer, the size of the band gap (forbidden band width), etc. can be changed more easily, and the characteristics of the carrier transport ability of the polymer can be changed reliably. Can do.

In the composition for a conductive material of the present invention, the heterocyclic ring is preferably aromatic.
Thereby, it is possible to suitably prevent the deviation of the electron density in the conjugated chemical structure of the main skeleton, that is, the localization of π electrons, and to prevent the carrier transport ability of the polymer from being lowered.
In the composition for conductive material of the present invention, the group Y preferably contains 1 to 5 heterocycles.
If such a number of heterocyclic rings are present in the group Y, the energy level of the valence band and the conduction band of the polymer, the size of the band gap (forbidden band width), and the like can be sufficiently changed.

In the composition for conductive material of the present invention, it is preferable that the group Y includes at least one substituted or unsubstituted aromatic hydrocarbon ring in addition to the heterocyclic ring.
By selecting a group Y containing a heterocyclic ring and an aromatic hydrocarbon ring, the target carrier transporting property can be reliably imparted to the polymer.
In the composition for conductive material of the present invention, the group Y is between the aromatic hydrocarbon ring directly bonded to each N in the general formula (1) and the aromatic hydrocarbon ring. It is preferable that at least one said heterocyclic ring which exists is included.
Thereby, it is possible to surely prevent the electron density in the polymer from being biased, and the carrier transport ability of the polymer becomes uniform.

［式中、２つのＲ^１は、それぞれ独立して、炭素数２〜８の直鎖アルキル基を表し、同一であっても、異なっていてもよく、４つのＲ^２は、それぞれ独立して、水素原子、メチル基またはエチル基を表し、同一であっても、異なっていてもよく、２つのＸは、それぞれ独立して、下記一般式（２）で表される置換基を表し、同一であっても、異なっていてもよく、Ｙは、置換もしくは無置換の複素環を少なくとも１つ含む基を表す。］

［式中、ｎは、２〜８の整数を表し、Ｚは、水素原子またはメチル基を表す。］
これにより、優れたキャリア輸送能を有する導電性材料（高分子）とすることができる。 In the composition for conductive material of the present invention, the total number of carbon atoms of the group Y is preferably 2 to 75.
Thereby, the solubility with respect to the solvent of the compound represented by the said General formula (1) becomes high, and when adjusting the composition for electroconductive materials, there exists an advantage that the selection range of a solvent spreads.
The conductive material of the present invention is obtained by polymerizing a substituent X between compounds represented by the following general formula (1) directly or via the acrylic crosslinking agent.

[Wherein, two R ^{1 s} each independently represent a straight-chain alkyl group having 2 to 8 carbon atoms, and may be the same or different, and four R ^{2 s} each independently Represents a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and two X's each independently represent a substituent represented by the following general formula (2); Or Y may be different, and Y represents a group containing at least one substituted or unsubstituted heterocycle. ]

[Wherein, n represents an integer of 2 to 8, and Z represents a hydrogen atom or a methyl group. ]
Thereby, it can be set as the electroconductive material (polymer) which has the outstanding carrier transport ability.

In the conductive material of the present invention, it is preferable that the acrylic crosslinking agent is mainly composed of a polyester (meth) acrylate crosslinking agent.
Thereby, in the conductive material, the ratio of the substituent X and the ratio of the polyester (meth) acrylate-based crosslinking agent become uniform. As a result, the conductive layer formed of this polymer can have uniform film characteristics.

In the conductive material of the present invention, the polyester (meth) acrylate-based crosslinking agent preferably has at least two (meth) acryloyl groups.
Accordingly, in the conductive material, the two substituents X can be more reliably connected via the polyester (meth) acrylate-based crosslinking agent, and the adjacent main skeletons are kept at a more appropriate distance. be able to.

［式中、ｎは、４５００以下の整数を表し、２つのＡは、それぞれ独立して、水素原子またはメチル基を表し、同一であっても、異なっていてもよい。］
かかる化合物を用いて形成された導電性材料は、キャリア輸送能がより優れたものとなる。 In the conductive material of the present invention, it is preferable that the polyester (meth) acrylate-based cross-linking agent contains a compound represented by the following general formula (3) as a main component.

[Wherein n represents an integer of 4500 or less, and two A's each independently represent a hydrogen atom or a methyl group, and may be the same or different. ]
A conductive material formed using such a compound has a better carrier transport capability.

In the conductive material of the present invention, the two substituents X are preferably the same.
Thereby, in the conductive material, the distance between the main skeletons can be set to a certain level or more. As a result, it is possible to suitably prevent the interaction between the main skeletons in the conductive material. Thereby, the carrier transport capability of the conductive material can be improved.

In the conductive material of the present invention, the substituent X is preferably bonded to any of the 3-position, 4-position or 5-position of the benzene ring.
As a result, the main skeletons can be more reliably separated at an appropriate distance.
In the conductive material of the present invention, the two substituents R ¹ are preferably the same.
Thereby, in the conductive layer to be formed, the distance between adjacent polymers (conductive materials) can be maintained at a substantially constant interval. As a result, the density of the conductive material in the conductive layer becomes constant.

In the conductive material of the present invention, the substituent R ¹ is preferably bonded to the 4-position of the benzene ring.
Thereby, in the conductive layer to be formed, it is possible to more reliably prevent adjacent polymers from being too close to each other.
In the conductive material of the present invention, the heterocyclic ring preferably contains at least one heteroatom selected from nitrogen, oxygen, sulfur, selenium and tellurium.
As a result, the valence band of the conductive material, the energy level of the conductive band, the size of the band gap (forbidden band width), etc. can be changed more easily, and the characteristics of the carrier transport ability of the conductive material can be changed reliably. Can be made.

In the conductive material of the present invention, the heterocyclic ring is preferably aromatic.
Thereby, it is possible to suitably prevent the uneven electron density in the conjugated chemical structure of the main skeleton, that is, the localization of π electrons, and to prevent the carrier transport ability of the conductive material from being lowered.
In the conductive material of the present invention, the group Y preferably contains 1 to 5 heterocycles.
If such a number of heterocyclic rings are present in the group Y, the energy level of the conductive material, the energy level of the conduction band, the size of the band gap (forbidden band width), and the like can be sufficiently changed.

In the conductive material of the present invention, the group Y preferably contains at least one substituted or unsubstituted aromatic hydrocarbon ring in addition to the heterocyclic ring.
By selecting the group Y containing a heterocyclic ring and an aromatic hydrocarbon ring, the target carrier transporting property can be reliably imparted to the conductive material.
In the conductive material of the present invention, the group Y is present at least between each of the aromatic hydrocarbon rings directly bonded to each N in the general formula (1) and these aromatic hydrocarbon rings. It is preferable that it contains one said heterocyclic ring.
Thereby, it is possible to surely prevent the electron density in the conductive material from being biased, and the carrier transporting ability of the conductive material becomes uniform.

In the conductive material of the present invention, the total number of carbon atoms of the group Y is preferably 2 to 75.
Thereby, since the planarity in the main skeleton is maintained, it is possible to reliably prevent the carrier transport ability in the conductive material from being lowered.
In the conductive material of the present invention, it is preferable that the compound and the acrylic crosslinking agent undergo a polymerization reaction by light irradiation.
According to the light irradiation, it is possible to relatively easily select a region and a degree to be polymerized.

The conductive layer of the present invention is formed using the composition for conductive material of the present invention.
Thereby, the conductive layer excellent in carrier transport ability can be formed.
The conductive layer of the present invention is characterized in that the conductive material of the present invention is a main material.
Thereby, the electroconductive layer excellent in carrier transport ability can be obtained.

The conductive layer of the present invention is preferably a hole transport layer.
Thereby, the hole transport layer excellent in hole transport ability can be formed.
In the conductive layer of the present invention, the hole transport layer preferably has an average thickness of 10 to 150 nm.
Thereby, a highly reliable organic electroluminescent element can be formed.

The conductive layer of the present invention is preferably an electron transport layer.
Thereby, an electron transport layer having excellent electron transport ability can be formed.
In the conductive layer of the present invention, the electron transport layer preferably has an average thickness of 1 to 100 nm.
Thereby, a highly reliable organic electroluminescent element can be formed.

The conductive layer of the present invention is preferably an organic semiconductor layer.
Thereby, the organic-semiconductor layer which shows the outstanding semiconductor characteristic can be formed.
In the conductive layer of the present invention, the average thickness of the organic semiconductor layer is preferably 0.1 to 1000 nm.
Thereby, a highly reliable organic thin film transistor can be formed.

The electronic device of the present invention includes the conductive layer of the present invention.
Thereby, an electronic device with high reliability can be obtained.
The electronic device of the present invention is characterized by including a laminate having the conductive layer of the present invention.
Thereby, an electronic device with high reliability can be obtained.
The electronic device of the present invention is preferably a light emitting element or a photoelectric conversion element.
Thereby, a highly reliable light emitting element and photoelectric conversion element are obtained.

In the electronic device of the present invention, the light emitting element is preferably an organic electroluminescence element.
Thereby, a highly reliable organic electroluminescent element is obtained.
The electronic device of the present invention is characterized by including a laminate having the conductive layer of the present invention.
Thereby, an electronic device with high reliability can be obtained.

The electronic device of the present invention is preferably a switching element.
Thereby, a highly reliable switching element is obtained.
In the electronic device of the present invention, the switching element is preferably an organic thin film transistor.
Thereby, a highly reliable organic thin-film transistor is obtained.
An electronic apparatus according to the present invention includes the electronic device according to the present invention.
As a result, a highly reliable electronic device can be obtained.

Hereinafter, the composition for conductive material, the conductive material, the conductive layer, the electronic device, and the electronic apparatus of the present invention will be described in detail based on preferred embodiments shown in the accompanying drawings.
<Conductive layer>
First, the conductive layer (the conductive layer of the present invention) composed of the conductive material of the present invention as a main material will be described.

  The conductive material of the present invention was obtained by subjecting a substituent X between compounds (heteroarylamine derivatives) represented by the following general formula (1) to a polymerization reaction directly or via an acrylic crosslinking agent. Polymer (polymer), that is, a main structure (heteroarylamine skeleton) other than the substituent X, the chemical structure formed by direct reaction of the substituent X and the substituent X, or a substituent by an acrylic crosslinking agent The main component is a polymer formed by linking by a chemical structure formed by crosslinking X and a substituent X (hereinafter, these chemical structures are collectively referred to as “linked structure”).

［式中、２つのＲ^１は、それぞれ独立して、炭素数２〜８の直鎖アルキル基を表し、同一であっても、異なっていてもよく、４つのＲ^２は、それぞれ独立して、水素原子、メチル基またはエチル基を表し、同一であっても、異なっていてもよく、２つのＸは、それぞれ独立して、下記一般式（２）で表される置換基を表し、同一であっても、異なっていてもよく、Ｙは、置換もしくは無置換の複素環を少なくとも１つ含む基を表す。］

[Wherein, two R ^{1 s} each independently represent a straight-chain alkyl group having 2 to 8 carbon atoms, and may be the same or different, and four R ^{2 s} each independently Represents a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and two X's each independently represent a substituent represented by the following general formula (2); Or Y may be different, and Y represents a group containing at least one substituted or unsubstituted heterocycle. ]

［式中、ｎは、２〜８の整数を表し、Ｚは、水素原子またはメチル基を表す。］

[Wherein, n represents an integer of 2 to 8, and Z represents a hydrogen atom or a methyl group. ]

Here, in such a polymer, the main skeleton is repeatedly bonded through a connecting structure, that is, the main skeleton is repeatedly present at a predetermined distance, Interaction between adjacent main skeletons is reduced.
The main skeleton has a conjugated chemical structure, and contributes to the smooth transport of carriers (holes or electrons) in the polymer due to its unique electron cloud spread.
For this reason, this polymer exhibits an excellent carrier transport ability, and a conductive layer mainly composed of such a polymer has an excellent carrier transport ability.
In such a polymer, if the distance between the main skeletons becomes too short, the interaction between adjacent main skeletons tends to increase, and if the distance between the main skeletons becomes too long, the main skeletons It is difficult to deliver carriers between the two, and the carrier transport ability of the polymer tends to decrease.

Taking these into consideration, the configuration of the linking structure is selected (determined), that is, the structure (configuration) of the substituent X and the acrylic crosslinking agent is set (determined).
In the connection structure, even when the substituents X are directly polymerized, the interaction between the main skeletons can be reduced. However, the substituent X and the substituent X are bonded via an acrylic crosslinking agent. When the polymerization reaction occurs, the distance between the main skeletons is maintained at an appropriate size, and the interaction between the main skeletons is further reduced. As a result, the polymer having such a connection structure exhibits an excellent carrier transport ability.

  Substituent X is preferably a linear carbon-carbon bond (alkylene group) in which n is 2 to 8, particularly 2 to 6, in general formula (2). This makes it possible to keep the distance between the main skeletons moderately, and in the polymer, the interaction between adjacent main skeletons can be reliably reduced, and more carriers can be transferred between the main skeletons. Since it is reliably performed, the carrier transport ability of the polymer is excellent.

  Further, the two substituents X preferably have substantially the same carbon number, and more preferably have the same carbon number. Thus, regardless of whether the linking structure is formed by directly bonding substituents X to each other or bonded via an acrylic crosslinking agent, the separation distance between main skeletons in the polymer is constant. The size can be made larger. As a result, it is possible to suitably prevent the interaction between the main skeletons in the polymer. Thereby, the carrier transport ability of the polymer can be improved.

  Further, as shown in the general formula (2), the substituent X has a (meth) acryloyl group (when the substituent Z is a hydrogen atom in the general formula (2), an acryloyl group at the terminal. And when the substituent Z is a methyl group, it represents a methacryloyl group. Here, since the (meth) acryloyl group has high reactivity and bond stability, the substituents X are relatively easily polymerized directly or via an acrylic cross-linking agent, resulting in a long chain length. A polymer can be formed.

Furthermore, a double bond (π bond) between an oxygen atom and a carbon atom exists in the linked structure generated by the polymerization reaction using the (meth) acryloyl group. Thus, even when the distance between the main skeletons is relatively long, the carriers can be reliably transferred between the main skeletons via the π bond.
In addition, since a linear carbon-carbon bond (alkylene group) exists between the π bond and the main skeleton, enhancement of the interaction between the main skeletons can be prevented.

For example, when a structure having many conjugated bonds among π bonds, such as a benzene ring, is present in a linked structure, adjacent main skeletons interact with each other through this structure, and the main skeleton The effect of separating them will be offset.
The substituent X may be bonded to any position from the 2-position to the 6-position of the benzene ring, but is particularly preferably bonded to any one of the 3-position, 4-position or 5-position. . Thereby, the effect of performing the coupling | bonding of adjacent main frame | skeletons via a connection structure can be exhibited more notably. That is, the adjacent main skeletons can be more reliably separated at an appropriate distance.

  In addition, the acrylic crosslinking agent is not particularly limited, but a (meth) acrylic acid crosslinking agent, a polyester (meth) acrylate crosslinking agent, a polyurethane (meth) acrylate crosslinking agent, an epoxy (meth) acrylate crosslinking agent, (Meth) acrylate crosslinkers such as amine (meth) acrylate crosslinkers and melamine (meth) acrylate crosslinkers can be used, and one or more of these can be used in combination. it can. Among these, as an acrylic type crosslinking agent, what has a polyester (meth) acrylate type crosslinking agent as a main component is preferable. Since the polyester (meth) acrylate-based crosslinking agent can be synthesized relatively easily with few steps, the cost can be reduced by using this as an acrylic crosslinking agent. Moreover, since this thing has high solubility, there also exists an advantage that the selection range of the solvent used when preparing the composition for electrically conductive materials of this invention spreads.

Further, since the (meth) acryloyl group has stable photopolymerization reaction characteristics, it reacts efficiently with the substituent X, and the unreacted substituent X and the polyester (meth) acrylate-based crosslinking agent remain. Can be suitably prevented. As a result, a polymer is formed in which the portion where the substituents X are directly bonded to each other and the portion bonded via the polyester (meth) acrylate-based cross-linking agent are biased (distributed). Thus, a conductive layer having uniform film characteristics can be formed.
Furthermore, since the polyester (meth) acrylate-based crosslinking agent has high transparency, high transparency can be imparted to the formed polymer. Therefore, it is particularly effective to apply the conductive material (polymer) of the present invention to an electronic device that requires transparency, for example, a hole transport layer provided in an organic EL element described later.

The polyester (meth) acrylate-based crosslinking agent is not particularly limited as long as it can link the substituent X and the substituent X through this, and has at least two (meth) acryloyl groups. Is preferred. As a result, the substituent X and the substituent X can be more reliably connected via the polyester (meth) acrylate-based crosslinking agent, and when the polymer is formed, the adjacent main skeletons are bonded to each other. A more appropriate distance can be maintained.
Examples of the polyester (meth) acrylate-based crosslinking agent having at least two (meth) acryloyl groups include one or more of the compounds represented by the following general formulas (3) to (5). Although it can be used in combination, it is particularly preferable to use a compound represented by the following general formula (3) as a main component.

［式中、ｎは、４５００以下の整数を表し、２つのＡは、それぞれ独立して、水素原子またはメチル基を表し、同一であっても、異なっていてもよい。］

[Wherein n represents an integer of 4500 or less, and two A's each independently represent a hydrogen atom or a methyl group, and may be the same or different. ]

［式中、ｎは、１〜３の整数を表し、２つのＲ^３は、それぞれ独立して、炭素数が１〜１０のアルキレン基を表し、同一であっても、異なっていてもよく、Ｒ^４は、炭素数が１〜１００のアルキレン基を表し、各Ａは、それぞれ独立して、水素原子またはメチル基を表し、同一であっても、異なっていてもよい。］

[Wherein, n represents an integer of 1 to 3, and two R ^{3 s} each independently represent an alkylene group having 1 to 10 carbon atoms, which may be the same or different, R ⁴ represents an alkylene group having 1 to 100 carbon atoms, and each A independently represents a hydrogen atom or a methyl group, and may be the same or different. ]

［式中、ｎは、０〜１５００の整数を表し、３つのＡは、それぞれ独立して、水素原子またはメチル基を表し、同一であっても、異なっていてもよい。］

[Wherein n represents an integer of 0 to 1500, and three A's each independently represent a hydrogen atom or a methyl group, and may be the same or different. ]

What is represented by the general formula (3) is a (meth) acryloyl group at both ends thereof (in the general formula (3), when the substituent A is a hydrogen atom, it represents an acryloyl group, and the substituent A When it is a methyl group, it represents a methacryloyl group.), And therefore, a polymerization reaction (bonding) with the substituent X can be carried out at both ends thereof.
In addition, since there is a portion composed of polyester between these (meth) acryloyl groups, the length of the portion composed of this polyester, that is, the portion composed of carbon-carbon bonds (alkylene) The length (chain length) of the linking structure can be adjusted by appropriately setting the length of the group). Thereby, main skeletons can be kept at an appropriate distance.
From these facts, the formed polymer has more excellent carrier transport ability.

  In the general formula (3), n is preferably an integer of 1300 or less. By setting n within the above range, the distance between the main skeletons can be made particularly appropriate. Thereby, in the polymer, the interaction between the adjacent main skeletons can be more reliably reduced, and the delivery of carriers between the main skeletons can be more reliably performed. As a result, the formed polymer is further improved in carrier transport ability.

Next, the main skeleton that contributes to carrier transport in the polymer will be described.
By appropriately setting the chemical structure of the group (bonding group) Y in this main skeleton, the characteristics of the polymer carrier transport ability can be changed.
This is because, in the polymer, for example, the energy levels and band gaps of the valence band and the conduction band (the band gap (electron distribution state) of the main skeleton that contributes to carrier transport change. This is thought to be due to the change in the size of the forbidden band.

In the conductive material of the present invention, the group Y contains at least one substituted or unsubstituted heterocyclic ring. By selecting the type of the heterocyclic ring, the characteristics of the carrier transport ability in the polymer are relatively easy. Can be adjusted.
The heterocyclic ring may be selected so that the polymer can have a desired carrier transporting ability. In particular, a heterocyclic ring containing at least one heteroatom selected from nitrogen, oxygen, sulfur, selenium and tellurium is selected. It is preferable to do this. By selecting a heterocyclic ring containing this kind of heteroatom, it becomes easier to change the energy level of the valence band and conduction band of the polymer, the size of the band gap (forbidden band width), and the like. .

The heterocyclic ring may be either aromatic or non-aromatic, but is preferably aromatic. Thereby, it is possible to suitably prevent the deviation of the electron density in the conjugated chemical structure of the main skeleton, that is, the localization of π electrons, and to prevent the carrier transport ability of the polymer from being lowered.
The group Y preferably contains 1 to 5 heterocycles that are the same or different, and more preferably contains 1 to 3 heterocycles. If such a number of heterocyclic rings are present in the group Y, the energy level of the valence band and the conduction band of the polymer, the size of the band gap (forbidden band width), and the like can be sufficiently changed.

Furthermore, the group Y can also select what contains at least 1 aromatic-hydrocarbon ring other than a heterocyclic ring. By selecting a group Y containing a heterocyclic ring and an aromatic hydrocarbon ring, the target carrier transporting property can be reliably imparted to the polymer.
Such a group Y includes an aromatic hydrocarbon ring directly bonded to each N in the general formula (1) and at least one heterocyclic ring existing between these aromatic hydrocarbon rings. It is particularly preferable that the Thereby, it is possible to reliably prevent the occurrence of bias in the electron density in the polymer. As a result, the carrier transport ability of the polymer becomes uniform.

In addition, the total number of carbon atoms in the group Y is preferably 2 to 75, and more preferably 2 to 50. When the total number of carbon atoms of the group Y is too large, depending on the type of the substituent X, the solubility of the compound represented by the general formula (1) in the solvent tends to be reduced, and the composition for conductive material of the present invention. There is a possibility that the range of selection of the solvent when adjusting is narrowed.
In addition, by setting the total number of carbon atoms of the group Y within such a range, the planarity of the main skeleton is maintained, so that it is possible to reliably prevent the carrier transport ability of the polymer from being lowered.
In consideration of these, in the compound represented by the general formula (1), as the group Y, for example, those represented by the following chemical formulas (6) to (25) are particularly preferable structures.

［式中、２つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。］

[Wherein, two Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph) and are the same. Or different. ]

［式中、２つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。］

[Wherein, two Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph) and are the same. Or different. ]

［式中、２つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよく、４つのＱ^２は、それぞれ独立して、ＳまたはＯを表し、同一であっても、異なっていてもよい。］

[Wherein, two Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph) and are the same. Each of the four Q ^{2 s} independently represents S or O, and may be the same or different. ]

［式中、２つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよく、４つのＱ^２は、それぞれ独立して、ＳまたはＯを表し、同一であっても、異なっていてもよい。］

[Wherein, two Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph) and are the same. Each of the four Q ^{2 s} independently represents S or O, and may be the same or different. ]

［式中、２つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよく、４つのＱ^２は、それぞれ独立して、ＳまたはＯを表し、同一であっても、異なっていてもよい。］

[Wherein, two Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph) and are the same. Each of the four Q ^{2 s} independently represents S or O, and may be the same or different. ]

［式中、Ｑ^１は、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表す。］

[Wherein, Q ¹ represents NT ¹ , S, O, Se or Te (where T ¹ represents H, CH ₃ or Ph). ]

［式中、Ｑ^３は、Ｎ−Ｔ^３、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^３は、Ｈ、ＣＨ_３、Ｃ_２Ｈ_５またはＰｈを表す。）を表す。］

[Wherein Q ³ represents NT ³ , S, O, Se or Te (where T ³ represents H, CH ₃ , C ₂ H ₅ or Ph). ]

［式中、Ｑ^１は、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表す。］

[Wherein, Q ¹ represents NT ¹ , S, O, Se or Te (where T ¹ represents H, CH ₃ or Ph). ]

［式中、Ｑ^１は、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表す。］

[Wherein, Q ¹ represents NT ¹ , S, O, Se or Te (where T ¹ represents H, CH ₃ or Ph). ]

［式中、３つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。］

[Wherein, three Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph), and are the same. Or different. ]

［式中、３つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。］

[Wherein, three Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph), and are the same. Or different. ]

［式中、Ｑ^１は、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表す。］

[Wherein, Q ¹ represents NT ¹ , S, O, Se or Te (where T ¹ represents H, CH ₃ or Ph). ]

［式中、Ｑ^１は、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表す。］

[Wherein, Q ¹ represents NT ¹ , S, O, Se or Te (where T ¹ represents H, CH ₃ or Ph). ]

［式中、３つのＱ^１は、それぞれ独立して、Ｎ−Ｔ^１、Ｓ、Ｏ、ＳｅまたはＴｅ（ただし、Ｔ^１は、Ｈ、ＣＨ_３またはＰｈを表す。）を表し、同一であっても、異なっていてもよい。］

[Wherein, three Q ^{1 s} each independently represent NT ¹ , S, O, Se, or Te (where T ¹ represents H, CH _3, or Ph), and are the same. Or different. ]

In addition, the heterocyclic ring or aromatic hydrocarbon ring contained in the group Y may be introduced with a substituent that does not significantly impair the planarity of the main skeleton. Examples of such a substituent include an alkyl group and a halogen group having a relatively small number of carbon atoms.
In the compound represented by the general formula (1), the substituent R ¹ is a linear alkyl group having 2 to 8 carbon atoms, and particularly a linear alkyl group having 3 to 6 carbon atoms. Is preferred. As a result, the steric hindrance caused by the substituent R ¹ can prevent adjacent polymers from being too close to each other, and can keep these distances appropriately. As a result, in the formed conductive layer, the interaction between main skeletons of different polymers can be reliably reduced, and the carrier transport ability of the conductive layer can be improved.

The two substituents R ¹ preferably have substantially the same carbon number, and more preferably have the same carbon number. Thereby, in the conductive layer to be formed, the distance between adjacent polymers can be maintained at a substantially constant interval. As a result, the polymer density in the conductive layer becomes constant.
The substituent R ¹ may be bonded to any position from the 2nd to 6th positions of the benzene ring, but it is particularly preferable to bond to the 4th position. This makes it possible to conspicuously exhibit the effect of introducing a substituent R ^1. That is, it is possible to more reliably prevent adjacent polymers from being too close to each other.

The substituent R ² is a hydrogen atom, a methyl group or an ethyl group, and the substituent R ² may be selected according to the number of carbon atoms of the substituent R ¹ . For example, if a large number of carbon atoms of the substituents R ^1, as the substituent R ^2, a hydrogen atom is selected, when the number of carbon atoms of the substituents R ¹ is small, the substituent R ^2, a methyl group Alternatively, an ethyl group may be selected.
Since such a conductive layer is mainly composed of a polymer obtained by a polymerization reaction, it has excellent solvent resistance. As a result, when the upper layer is formed in contact with the conductive layer, it is possible to reliably prevent the conductive layer from swelling or dissolving by the solvent or dispersion medium contained in the material for forming the upper layer. it can.

  In addition, when an electronic device as will be described later is constructed using a laminate having such a conductive layer, the layer that comes into contact with the conductive layer because the conductive layer is composed mainly of a polymer. In the vicinity of the interface of the (contact layer), it is possible to reliably prevent the constituent material of the conductive layer and the constituent material of the contact layer from being mixed with time. As a result, it is possible to prevent the characteristics of the electronic device from deteriorating with time.

<Organic electroluminescence device>
Next, an embodiment in which the electronic device of the present invention is applied to an organic electroluminescence element (hereinafter simply referred to as “organic EL element”) which is a light emitting element will be described.
FIG. 1 is a longitudinal sectional view showing an example of an organic EL element.
An organic EL element 1 shown in FIG. 1 includes a transparent substrate 2, an anode 3 provided on the substrate 2, an organic EL layer 4 provided on the anode 3, and a cathode provided on the organic EL layer 4. 5 and a protective layer 6 provided so as to cover each of the layers 3, 4, and 5.

The substrate 2 serves as a support for the organic EL element 1, and each of the layers is formed on the substrate 2.
As a constituent material of the substrate 2, a material having translucency and good optical characteristics can be used.
Examples of such materials include various resin materials such as polyethylene terephthalate, polyethylene naphthalate, polypropylene, cycloolefin polymer, polyamide, polyethersulfone, polymethyl methacrylate, polycarbonate, and polyarylate, and various glass materials. And at least one of these can be used.

Although the thickness (average) of the board | substrate 2 is not specifically limited, It is preferable that it is about 0.1-30 mm, and it is more preferable that it is about 0.1-10 mm.
The anode 3 is an electrode that injects holes into the organic EL layer 4 (a hole transport layer 41 described later). The anode 3 is substantially transparent (colorless transparent, colored transparent, translucent) so that light emission from the organic EL layer 4 (light emitting layer 42 described later) can be visually recognized.

From such a viewpoint, as the constituent material (anode material) of the anode 3, it is preferable to use a material having a large work function, excellent conductivity, and translucency.
Examples of such an anode material include ITO (Indium Tin Oxide), SnO ₂ , Sb-containing SnO ₂ , oxides such as Al-containing ZnO, Au, Pt, Ag, Cu, or alloys containing these, and the like. At least one of these can be used.

  The thickness (average) of the anode 3 is not particularly limited, but is preferably about 10 to 200 nm, and more preferably about 50 to 150 nm. If the thickness of the anode 3 is too thin, the function as the anode 3 may not be sufficiently exhibited. On the other hand, if the anode 3 is too thick, the light transmittance may be remarkably lowered depending on the type of anode material. There is a risk that it will not be suitable for practical use.

As the anode material, for example, a conductive resin material such as polythiophene or polypyrrole can be used.
On the other hand, the cathode 5 is an electrode for injecting electrons into the organic EL layer 4 (an electron transport layer 43 described later).
As a constituent material (cathode material) of the cathode 5, it is preferable to use a material having a small work function.

Examples of such cathode materials include Li, Mg, Ca, Sr, La, Ce, Er, Eu, Sc, Y, Yb, Ag, Cu, Al, Cs, Rb, and alloys containing these, and the like. At least one of them can be used.
In particular, when an alloy is used as the cathode material, an alloy containing a stable metal element such as Ag, Al, or Cu, specifically, an alloy such as MgAg, AlLi, or CuLi is preferably used. By using such an alloy as the cathode material, the electron injection efficiency and stability of the cathode 5 can be improved.

The thickness (average) of the cathode 5 is preferably about 1 nm to 1 μm, and more preferably about 100 to 400 nm. If the thickness of the cathode 5 is too thin, the function as the cathode 5 may not be sufficiently exhibited. On the other hand, if the cathode 5 is too thick, the light emission efficiency of the organic EL element 1 may be reduced.
Between the anode 3 and the cathode 5, an organic EL layer 4 is provided. The organic EL layer 4 includes a hole transport layer 41, a light emitting layer 42, and an electron transport layer 43, which are formed on the anode 3 in this order.

The hole transport layer 41 has a function of transporting holes injected from the anode 3 to the light emitting layer 42, and the electron transport layer 43 has a function of transporting electrons injected from the cathode 5 to the light emitting layer 42. It is what has.
As the constituent materials of the hole transport layer 41 and the electron transport layer 43, the conductive material of the present invention can be used.

Here, in the case where both the hole transport layer 41 and the electron transport layer 43 are formed using the conductive material of the present invention as a main material, the hole transport capability and the electron transport capability of the conductive material are taken into consideration, What is necessary is just to select a constituent material.
That is, the hole transport layer 41 has a relatively high hole transport capability and a low electron transport capability with respect to the electron transport layer 43, in other words, the electron transport layer 43 has a lower capacity than the hole transport layer 41. These constituent materials may be selected so that the electron transport ability is relatively high and the hole transport ability is low.

For example, as the conductive material used for the hole transport layer 41, when the chemical structure of the group Y is selected from the chemical formula (23) or (25), as the conductive material constituting the electron transport layer 43, The chemical structure of the group Y is preferably selected from the chemical formula (12) or (24), and the chemical structure (22) can also be selected. When the above-described materials are used as the conductive material constituting the electron transport layer 43, the chemical structure of the group Y is represented by the chemical formula (7) or ( 21) can also be selected.
Further, the hole transport layer 41 preferably has a volume resistivity of 10 Ω · cm or more, more preferably 10 ² Ω · cm or more. Thereby, the organic EL element 1 with higher luminous efficiency can be obtained.

  The thickness (average) of the hole transport layer 41 is not particularly limited, but is preferably about 10 to 150 nm, and more preferably about 50 to 100 nm. If the thickness of the hole transport layer 41 is too thin, pinholes may be generated. On the other hand, if the hole transport layer 41 is too thick, the transmittance of the hole transport layer 41 may be deteriorated, resulting in an organic EL element. There is a possibility that the chromaticity (hue) of the emission color of 1 will change.

Furthermore, the thickness (average) of the electron transport layer 43 is not particularly limited, but is preferably about 1 to 100 nm, and more preferably about 20 to 50 nm. If the thickness of the electron transport layer 43 is too thin, pinholes may occur and short circuit may occur, while if the electron transport layer 43 is too thick, the resistance value may increase.
In addition, the conductive material of the present invention is particularly useful when such a relatively thin hole transport layer 41 and electron transport layer 43 are formed.

  When the anode 3 and the cathode 5 are energized (voltage is applied), holes move in the hole transport layer 41 and electrons move in the electron transport layer 43. The electrons recombine. In the light emitting layer 42, excitons (excitons) are generated by the energy released upon this recombination, and energy (fluorescence or phosphorescence) is emitted (emitted) when the excitons return to the ground state.

As a constituent material (light emitting material) of the light emitting layer 42, holes can be injected from the anode 3 side when electrons are applied, and electrons can be injected from the cathode 5 side, thereby providing a field where holes and electrons recombine. Any thing can be used as long as it is possible.
Such luminescent materials include various low-molecular luminescent materials and various high-molecular luminescent materials as described below, and at least one of them can be used.

  In addition, since the dense light emitting layer 42 is obtained by using a low molecular light emitting material, the light emission efficiency of the light emitting layer 42 is improved. Moreover, since the polymer light-emitting material can be dissolved in a solvent relatively easily, the light-emitting layer 42 can be easily formed by various coating methods such as an ink jet printing method. Furthermore, by using a combination of a low-molecular light-emitting material and a high-molecular light-emitting material, the light-emitting layer has the effect of using a low-molecular light-emitting material and a high-molecular light-emitting material. 42 can be easily formed by various coating methods such as an ink jet printing method.

Examples of low-molecular light emitting materials include benzene compounds such as distyrylbenzene (DSB) and diaminodistyrylbenzene (DADSB), naphthalene compounds such as naphthalene and nile red, phenanthrene compounds such as phenanthrene, Chrysene, chrysene compounds such as 6-nitrochrysene, perylene, N, N′-bis (2,5-di-t-butylphenyl) -3,4,9,10-perylene-di-carboximide (BPPC) Perylene compounds such as coronene, anthracene compounds such as anthracene and bisstyrylanthracene, pyrene compounds such as pyrene, 4- (di-cyanomethylene) -2-methyl-6 Such as-(para-dimethylaminostyryl) -4H-pyran (DCM) Pyran compounds, acridine compounds such as acridine, stilbene compounds such as stilbene, thiophene compounds such as 2,5-dibenzoxazole thiophene, benzoxazole compounds such as benzoxazole, benzos such as benzimidazole Imidazole compounds, benzothiazole compounds such as 2,2 ′-(para-phenylenedivinylene) -bisbenzothiazole, bistyryl (1,4-diphenyl-1,3-butadiene), butadienes such as tetraphenylbutadiene Compounds, naphthalimide compounds such as naphthalimide, coumarin compounds such as coumarin, perinone compounds such as perinone, oxadiazole compounds such as oxadiazole, aldazine compounds, 1, 2, 3 , 4, Cyclopentadiene compounds such as 5-pentaphenyl-1,3-cyclopentadiene (PPCP), quinacridone compounds such as quinacridone and quinacridone red, pyridine compounds such as pyrrolopyridine and thiadiazolopyridine, 2,2 Spiro compounds such as', 7,7'-tetraphenyl-9,9'-spirobifluorene, phthalocyanine (H ₂ Pc), metal or non-metal phthalocyanine compounds such as copper phthalocyanine, florene such as fluorene Compounds, (8-hydroxyquinoline) aluminum (Alq ₃ ), tris (4-methyl-8quinolinolate) aluminum (III) (Almq ₃ ), (8-hydroxyquinoline) zinc (Znq ₂ ), (1,10- Phenanthroline) -tris- (4,4,4-trif Oro-1- (2-thienyl) - butane-1,3-Jioneto) europium _{(III) (Eu (TTA)} 3 (phen)), factory scan (2-phenylpyridine) iridium (Ir _(ppy) 3), Various metal complexes such as (2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphine) platinum (II) can be mentioned.

  Examples of the polymer light-emitting material include polyacetylene compounds such as trans-type polyacetylene, cis-type polyacetylene, poly (di-phenylacetylene) (PDPA), poly (alkyl, phenylacetylene) (PAPA), and poly (para-para-). Fenvinylene) (PPV), poly (2,5-dialkoxy-para-phenylenevinylene) (RO-PPV), cyano-substituted-poly (para-phenvinylene) (CN-PPV), poly (2-dimethyloctyl) Polyparaphenylene vinylene compounds such as silyl-para-phenylene vinylene (DMOS-PPV), poly (2-methoxy, 5- (2′-ethylhexoxy) -para-phenylene vinylene) (MEH-PPV), poly ( 3-alkylthiophene) (PAT), poly (oxypropylene) Polythiophene compounds such as riol (POPT), poly (9,9-dialkylfluorene) (PDAF), α, ω-bis [N, N′-di (methylphenyl) aminophenyl] -poly [9,9- Bis (2-ethylhexyl) fluorene-2,7-diyl] (PF2 / 6am4), poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) Polyfluorene compounds such as poly (para-phenylene) (PPP), polyparaphenylene compounds such as poly (1,5-dialkoxy-para-phenylene) (RO-PPP), poly (N-vinyl) Polycarbazole compounds such as carbazole (PVK), poly (methylphenylsilane) (PMPS), poly (naphthylphenylsilane) PnPs), polysilane-based compounds such as poly (biphenylyl phenyl silane) (pBPS), and the like.

Further, depending on the combination of constituent materials used for the hole transport layer 41 and the electron transport layer 43, the conductive material of the present invention can be used as the light emitting material.
For example, as a constituent material of the hole transport layer 41, poly (thiophene / styrenesulfonic acid) such as poly (3,4-ethylenedioxythiophene / styrenesulfonic acid), N, N′-bis (1-naphthyl) An arylamine compound such as —N, N′-diphenyl-benzidine (α-NPD) is used, and the electron transport layer 43 is made of a material such as 3,4,5-triphenyl-1,2,4-triazole. Triazole compounds, oxadiazole compounds such as 2- (4-t-butylphenyl) -5- (biphenyl-4-yl) -1,3,5-oxadiazole (PBD), etc. For the conductive material constituting the light emitting layer 42, those having the chemical structure of the group Y such as the chemical formulas (17) and (19) can be used.

The thickness (average) of the light emitting layer 42 is not particularly limited, but is preferably about 10 to 150 nm, and more preferably about 50 to 100 nm. By setting the thickness of the light emitting layer in the above range, recombination of holes and electrons is efficiently performed, and the light emission efficiency of the light emitting layer 42 can be further improved.
The organic EL element 1 may be such that any one of the hole transport layer 41, the light emitting layer 42, and the electron transport layer 43 is composed of the conductive material of the present invention. All may be composed of the conductive material of the present invention.

In addition, the light emitting layer 42 is provided separately from the hole transport layer 41 and the electron transport layer 43, but a hole transportable light emitting layer that serves as the hole transport layer 41 and the light emitting layer 42, or an electron transport layer An electron-transporting light-emitting layer that also serves as the light-emitting layer 43 and the light-emitting layer 42 can be used. In this case, the vicinity of the interface between the hole-transporting light-emitting layer and the electron-transporting layer 43 and the vicinity of the interface between the electron-transporting light-emitting layer and the hole-transporting layer 41 function as the light-emitting layer 42, respectively.
Furthermore, when a hole transporting light emitting layer is used, holes injected from the anode into the hole transporting light emitting layer are confined by the electron transport layer, and when an electron transporting light emitting layer is used, Since electrons injected from the cathode into the electron-transporting light-emitting layer are confined in the electron-transporting light-emitting layer, both have the advantage that the recombination efficiency between holes and electrons can be improved.

  An arbitrary target layer may be provided between the layers 3, 4, and 5. For example, a hole injection layer that improves the efficiency of hole injection from the anode 3 can be provided between the hole transport layer 41 and the anode 3. Further, an electron injection layer or the like for improving the efficiency of electron injection from the cathode 5 can be provided between the electron transport layer 43 and the cathode 5. Thus, when providing a positive hole injection layer and an electron injection layer in the organic EL element 1, the conductive material of this invention can be used as a constituent material of this positive hole injection layer and an electron injection layer.

As the constituent material of the hole injection layer, in addition to the conductive material of the present invention, for example, copper phthalocyanine or 4,4 ′, 4 ″ -tris (N, N-phenyl-3-methylphenylamino) tris Phenylamine (M-MTDATA) can also be used.
The protective layer 6 is provided so as to cover the layers 3, 4, and 5 constituting the organic EL element 1. The protective layer 6 has a function of hermetically sealing the layers 3, 4, and 5 constituting the organic EL element 1 and blocking oxygen and moisture. By providing the protective layer 6, it is possible to obtain the effects of improving the reliability of the organic EL element 1 and preventing deterioration and deterioration.

Examples of the constituent material of the protective layer 6 include Al, Au, Cr, Nb, Ta, Ti, alloys containing these, silicon oxide, various resin materials, and the like. In addition, when using the material which has electroconductivity as a constituent material of the protective layer 6, in order to prevent a short circuit, between the protective layer 6 and each layer 3, 4, 5 as needed, an insulating film Is preferably provided.
The organic EL element 1 can be used, for example, for a display, but can also be used as a light source or the like, and can be used for various optical applications.
Further, when the organic EL element 1 is applied to a display, the driving method is not particularly limited, and either an active matrix method or a passive matrix method may be used.
Such an organic EL element 1 can be manufactured as follows, for example.

[A1] Anode Formation Step First, the substrate 2 is prepared, and the anode 3 is formed on the substrate 2.
The anode 3 is, for example, a chemical vapor deposition method (CVD) such as plasma CVD, thermal CVD, or laser CVD, a dry plating method such as vacuum deposition, sputtering, or ion plating, or a wet method such as electrolytic plating, immersion plating, or electroless plating. It can be formed by using a plating method, a thermal spraying method, a sol-gel method, a MOD method, a metal foil bonding, or the like.

[A2] Hole transport layer forming step [A2-1] First, a composition for a conductive material (hole transport material) containing the compound represented by the general formula (1) and an acrylic crosslinking agent is used as an anode. 3 is applied (supplied).
The compounding ratio of the compound represented by the general formula (1) and the acrylic crosslinking agent in the composition for conductive material is preferably 1: 9 to 9: 1 in terms of molar ratio. More preferably, it is 4-4: 1. If the blending ratio of the acrylic crosslinking agent is too small, the main skeletons may not be kept at a more appropriate distance in the polymer to be produced, and there is a possibility that the main skeletons may interact with each other. When there are too many compounding ratios of an agent, the mixing ratio of the compound which can be represented by the said General formula (1) will decrease relatively. That is, in the polymer to be produced, the abundance ratio of the main skeleton is reduced, so that the hole transport ability may be lowered.

  For this coating, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, Various coating methods such as an offset printing method and an ink jet printing method can be used. According to such a coating method, the hole transport material can be supplied onto the anode 3 relatively easily.

  When the compound represented by the general formula (1) is dissolved in a solvent or dispersed in a dispersion medium, examples of the solvent or dispersion medium used include nitric acid, sulfuric acid, ammonia, hydrogen peroxide, water, carbon disulfide, and four. Inorganic solvents such as carbon chloride and ethylene carbonate, ketone solvents such as methyl ethyl ketone (MEK), acetone, diethyl ketone, methyl isobutyl ketone (MIBK), methyl isopropyl ketone (MIPK), cyclohexanone, methanol, ethanol, isopropanol, ethylene glycol , Alcohol solvents such as diethylene glycol (DEG) and glycerin, diethyl ether, diisopropyl ether, 1,2-dimethoxyethane (DME), 1,4-dioxane, tetrahydrofuran (THF), tetrahydropyran (THP), aniso , Ether solvents such as diethylene glycol dimethyl ether (diglyme), diethylene glycol ethyl ether (carbitol), cellosolve solvents such as methyl cellosolve, ethyl cellosolve, phenyl cellosolve, aliphatic hydrocarbon solvents such as hexane, pentane, heptane, cyclohexane , Aromatic hydrocarbon solvents such as toluene, xylene and benzene, aromatic heterocyclic compounds solvents such as pyridine, pyrazine, furan, pyrrole, thiophene and methylpyrrolidone, N, N-dimethylformamide (DMF), N, N Amide solvents such as dimethylacetamide (DMA), halogen compound solvents such as dichloromethane, chloroform, 1,2-dichloroethane, ester solvents such as ethyl acetate, methyl acetate, ethyl formate, dimethylsulfoxide Various organic solvents such as sulfur compound solvents such as DMSO, sulfolane, nitrile solvents such as acetonitrile, propionitrile, acrylonitrile, organic acid solvents such as formic acid, acetic acid, trichloroacetic acid, trifluoroacetic acid, or And mixed solvents containing these.

In addition, it is preferable to add a polymerization initiator to the composition for conductive materials. Thereby, in the next step [A2-2], when a predetermined treatment such as heating or light irradiation is performed, the polymerization reaction between the substituents X or via the acrylic crosslinking agent can be promoted. .
The polymerization initiator is not particularly limited, and examples thereof include photopolymerization initiators such as photo radical polymerization initiators and photo cationic polymerization initiators, thermal polymerization initiators and anaerobic polymerization initiators, among these, It is particularly preferable to use a photo radical polymerization initiator. Thereby, in the next step [A2-2], the polymerization reaction between the substituents X or via the acrylic crosslinking agent can be made to proceed relatively easily.

As the photoradical polymerization initiator, various photoradical polymerization initiators can be used. In addition, photo radical polymerization initiators such as thioxanthone can be used.
Furthermore, when using a photoinitiator as a polymerization initiator, you may add the sensitizer suitable for a photoinitiator to the composition for electroconductive materials.

[A2-2] Next, the hole transport material supplied onto the anode 3 is irradiated with light.
As a result, a polymer obtained by polymerizing the substituents X of the compound represented by the general formula (1) contained in the hole transport material directly or via an acrylic crosslinking agent (conductivity of the present invention). Material) can be obtained. As a result, a hole transport layer 41 mainly composed of the conductive material of the present invention is formed on the anode 3.

By configuring the hole transport layer 41 as the main material of the conductive material of the present invention, when the light emitting layer material is supplied in the next step [A3], the solvent or dispersion medium contained in the light emitting layer material It is possible to prevent the hole transport layer 41 from swelling and dissolving. As a result, phase dissolution of the hole transport layer 41 and the light emitting layer 42 can be reliably prevented.
Moreover, in the organic EL element 1 obtained by constituting the hole transport layer 41 with the conductive material (polymer) of the present invention as a main material, in the vicinity of the interface between the hole transport layer 41 and the light emitting layer 42. These constituent materials can be reliably prevented from being mixed with time.

The weight average molecular weight of the polymer is not particularly limited, but is preferably about 1,000 to 1,000,000, and more preferably about 10,000 to 300,000. Thereby, swelling and dissolution of the polymer can be suppressed or prevented more reliably.
In addition, the hole transport layer 41 has a low molecular weight (such as a compound represented by the general formula (1) or an acrylic cross-linking agent as long as the phase dissolution of the hole transport layer 41 and the light emitting layer 42 is prevented. Monomer or oligomer).

Examples of the light that irradiates the hole transport material include infrared rays, visible rays, ultraviolet rays, and X-rays, and one or more of these can be used in combination. Among these, it is particularly preferable to use ultraviolet rays. Thereby, it is possible to easily and reliably advance the polymerization reaction between the substituents X or via the acrylic crosslinking agent.
The wavelength of the ultraviolet rays to be irradiated is preferably about 100 to 420 nm, and more preferably about 150 to 400 nm.

The irradiation intensity of ultraviolet light is preferably in the range of about 1~600mW / cm ^2, more preferably about 1~300mW / cm ^2.
Furthermore, the irradiation time of ultraviolet rays is preferably about 60 to 600 seconds, and more preferably about 90 to 500 seconds.
By setting the ultraviolet wavelength, irradiation intensity, and irradiation time within such ranges, the progress of the polymerization reaction of the hole transport material supplied onto the anode 3 can be controlled relatively easily.

Note that the obtained hole transport layer 41 may be subjected to heat treatment, for example, in the air, in an inert atmosphere, or under reduced pressure (or vacuum), if necessary. Thereby, for example, the hole transport layer 41 can be dried (desolvent or dedispersion medium), solidified, and the like. The hole transport layer 41 may be dried regardless of heat treatment.
In addition to the light irradiation, examples of the predetermined treatment for the polymerization reaction between the substituents X or the acrylic crosslinking agent include heating and anaerobic treatment. Among these, as described above, Preferably, light irradiation is used. According to the light irradiation, it is possible to relatively easily select a region and a degree to be polymerized.

[A3] Light-Emitting Layer Formation Step Next, the light-emitting layer 42 is formed on the hole transport layer 41.
The light emitting layer 42 is formed, for example, by applying a light emitting layer material (light emitting layer forming material) obtained by dissolving the above light emitting material in a solvent or dispersing in a dispersion medium on the hole transport layer 41. Can do.
As the solvent or dispersion medium for dissolving or dispersing the light emitting material, the same solvent or dispersion medium used when forming the hole transport layer 41 can be used.
Further, as a method of applying the light emitting layer material on the hole transport layer 41, the same method as that used when forming the hole transport layer 41 can be used.

[A4] Electron Transport Layer Formation Step Next, the electron transport layer 43 is formed on the light emitting layer 42.
The electron transport layer 43 can be formed using the composition for conductive material of the present invention by the same method as described in the hole transport layer forming step [A2].
In addition, when the light emitting layer 42 is not comprised with polymers like the electroconductive material of this invention, the solvent or dispersion medium for melt | dissolving or disperse | distributing the composition for electroconductive materials used in order to form the electron carrying layer 43 For example, the light emitting layer 42 may be selected so that it does not swell and dissolve. Thereby, phase dissolution of the light emitting layer 42 and the electron transport layer 43 can be reliably prevented.

[A5] Cathode Formation Step Next, the cathode 5 is formed on the electron transport layer 43.
The cathode 5 can be formed using, for example, a vacuum deposition method, a sputtering method, a metal foil bonding, or the like.
[A6] Protective Layer Formation Step Next, the protective layer 6 is formed so as to cover the anode 3, the organic EL layer 4, and the cathode 5.
The protective layer 6 can be formed (provided), for example, by bonding a box-shaped protective cover made of the above-described material with various curable resins (adhesives).
As the curable resin, any of a thermosetting resin, a photocurable resin, a reactive curable resin, and an anaerobic curable resin can be used.
The organic EL element 1 is manufactured through the above processes.

<Organic thin film transistor>
Next, an embodiment in which the electronic device of the present invention is applied to an organic thin film transistor (hereinafter simply referred to as “organic TFT”) as a switching element will be described.
2A and 2B are diagrams showing the organic TFT 10, in which FIG. 2A is a longitudinal sectional view and FIG. 2B is a plan view. In the following description, the upper side in FIG. 2A is referred to as “upper” and the lower side is referred to as “lower”.

The organic TFT 10 shown in FIG. 2 is provided on the substrate 20, and includes a source electrode 30 and a drain electrode 40, an organic semiconductor layer (conductive layer of the present invention) 50, a gate insulating layer 60, and a gate electrode 70. These are stacked in this order from the substrate 20 side.
Specifically, in the organic TFT 10, the source electrode 30 and the drain electrode 40 are separately provided on the substrate 20, and the organic semiconductor layer 50 is provided so as to cover the electrodes 30 and 40. Further, a gate insulating layer 60 is provided on the organic semiconductor layer 50, and a gate electrode 70 is further provided thereon so as to overlap at least a region between the source electrode 30 and the drain electrode 40.

  In the organic TFT 10, a region between the source electrode 30 and the drain electrode 40 in the organic semiconductor layer 50 is a channel region 510 in which carriers move. Hereinafter, in this channel region 510, the length in the direction of carrier movement, that is, the distance between the source electrode 30 and the drain electrode 40 is the channel length L, and the length perpendicular to the channel length L direction is the channel width W. To tell.

Such an organic TFT 10 is an organic TFT having a configuration in which the source electrode 30 and the drain electrode 40 are provided on the substrate 20 side with respect to the gate electrode 70 via the gate insulating layer 60, that is, an organic TFT having a top gate structure. .
Hereinafter, each part which comprises organic TFT10 is demonstrated sequentially.
The substrate 20 supports each layer (each part) constituting the organic TFT 10. As the substrate 20, for example, a substrate similar to the substrate 2 described in the organic EL element 1 described above can be used, and a silicon substrate, a gallium arsenide substrate, or the like can be used.

On the substrate 20, a source electrode 30 and a drain electrode 40 are juxtaposed at a predetermined distance along the channel length L direction.
The constituent material of the source electrode 30 and the drain electrode 40 may be any material as long as it has conductivity. For example, Pd, Pt, Au, W, Ta, Mo, Al, Cr, Ti , Cu or metal materials such as alloys containing them, conductive oxide materials such as ITO, FTO, ATO, SnO ₂ , carbon materials such as carbon black, carbon nanotubes, fullerene, polyacetylene, polypyrrole, PEDOT (poly-ethylenedioxythiophene) And conductive polymer materials such as polythiophene, polyaniline, poly (p-phenylene), poly (p-phenylene vinylene), polyfluorene, polycarbazole, polysilane, or derivatives thereof. Polymer materials are usually chlorinated It is used in a state where it is doped with a polymer such as iron, iodine, strong acid, organic acid, polystyrene sulphonic acid, and imparted with conductivity. Further, one or more of these can be used in combination.

The thickness (average) of the source electrode 30 and the drain electrode 40 is not particularly limited, but is preferably about 30 to 300 nm, and more preferably about 50 to 200 nm.
The distance (separation distance) between the source electrode 30 and the drain electrode 40, that is, the channel length L is preferably about 2 to 30 μm, and more preferably about 2 to 20 μm.

The channel width W is preferably about 0.1 to 5 mm, and more preferably about 0.3 to 3 mm.
An organic semiconductor layer 50 is provided on the substrate 20 so as to cover the source electrode 30 and the drain electrode 40.
As the constituent material of the organic semiconductor layer 50, the conductive material of the present invention can be used.

As described above, the conductive material of the present invention can impart desired carrier transportability characteristics to the formed polymer by appropriately setting the chemical structure of the group Y.
Therefore, by appropriately setting the chemical structure of the group Y, it is possible to impart excellent semiconductor characteristics to the polymer. Therefore, it is particularly effective to use the conductive material of the present invention for the organic semiconductor layer 50.

As the conductive material constituting such an organic semiconductor layer 50, for example, those in which the chemical structure of the group Y has the chemical formulas (7), (8), (21), (22) and (25) are suitable. Selected.
The thickness (average) of the organic semiconductor layer 50 is preferably about 0.1 to 1000 nm, more preferably about 1 to 500 nm, and further preferably about 10 to 100 nm. Thereby, it can prevent that organic TFT10 enlarges (especially that thickness increases), maintaining the outstanding carrier transport capability.

  In addition, by using the organic semiconductor layer 50 that is composed mainly of a polymer such as the conductive material of the present invention, the resulting organic TFT 10 can be reduced in thickness and weight, and can be reduced. Excellent flexibility. Such an organic TFT 10 is suitable for application to a switching element of a flexible display including the above-described organic EL element.

Note that the organic semiconductor layer 50 is not limited to a structure provided so as to cover the source electrode 30 and the drain electrode 40, and is provided at least in a region (channel region 510) between the source electrode 30 and the drain electrode 40. It only has to be.
A gate insulating layer 60 is provided on the organic semiconductor layer 50.
The gate insulating layer 60 insulates the gate electrode 70 from the source electrode 30 and the drain electrode 40.
The gate insulating layer 60 is preferably mainly composed of an organic material (particularly an organic polymer material). The gate insulating layer 60 containing an organic polymer material as a main material can be easily formed and can improve the adhesion to the organic semiconductor layer 50.

  Examples of such organic polymer materials include polystyrene, polyimide, polyamideimide, polyvinylphenylene, polycarbonate (PC), acrylic resin such as polymethyl methacrylate (PMMA), and polytetrafluoroethylene (PTFE). Fluorine resin, phenolic resin such as polyvinylphenol or novolac resin, and olefinic resins such as polyethylene, polypropylene, polyisobutylene, polybutene, etc. are used, and one or more of these may be used in combination. it can.

  The thickness (average) of the gate insulating layer 60 is not particularly limited, but is preferably about 10 to 5000 nm, and more preferably about 100 to 1000 nm. By setting the thickness of the gate insulating layer 60 within the above range, the organic TFT 10 is increased in size while the source electrode 30 and the drain electrode 40 are reliably insulated from the gate electrode 70 (in particular, the thickness is increased). ) Can be prevented.

Note that the gate insulating layer 60 is not limited to a single-layer structure, and may have a multilayer structure.
A gate electrode 70 is provided on the gate insulating layer 60.
As the constituent material of the gate electrode 70, the same constituent materials as those of the source electrode 30 and the drain electrode 40 described above can be used.

The thickness (average) of the gate electrode 70 is not particularly limited, but is preferably about 0.1 to 5000 nm, more preferably about 1 to 5000 nm, and still more preferably about 10 to 5000 nm.
In the organic TFT 10 as described above, the amount of current flowing between the source electrode 30 and the drain electrode 40 is controlled by changing the voltage applied to the gate electrode 70.

That is, in the OFF state in which no voltage is applied to the gate electrode 70, even if a voltage is applied between the source electrode 30 and the drain electrode 40, almost no carriers are present in the organic semiconductor layer 50, so that a very small current Only flows. On the other hand, in the ON state in which a voltage is applied to the gate electrode 70, charges are induced in the portion of the organic semiconductor layer 50 facing the gate insulating layer 60, and a carrier flow path is formed in the channel region 510. When a voltage is applied between the source electrode 30 and the drain electrode 40 in this state, carriers (holes or electrons) flow through the channel region 510.
Such an organic TFT 10 can be manufactured as follows, for example.
3 to 4 are views (longitudinal sectional views) for explaining a method of manufacturing the organic TFT 10 shown in FIG. In the following description, the upper side in FIGS. 3 to 4 is referred to as “upper” and the lower side is referred to as “lower”.

[B1] Source and drain electrode formation step [B1-1] First, a substrate 20 as shown in FIG. 3A is prepared, and this substrate 20 is made of, for example, water (pure water or the like), an organic solvent, or the like. Washing alone or in combination.
Next, a photoresist is supplied onto the substrate 20 to form a film 80 ′ (see FIG. 3B).

The photoresist supplied onto the substrate 20 is a negative photoresist that is exposed to light (exposure) is cured, and a region other than the exposed region is dissolved and removed by development, and exposed. Any positive type photoresist in which the region is dissolved and removed by development may be used.
Negative photoresists include rosin-dichromate, polyvinyl alcohol (PVA) -bichromate, shellac-bichromate, casein-dichromate, PVA-diazo, acrylic photoresist, etc. And water-soluble photoresists such as oil-soluble photoresists such as polyvinyl cinnamate, cyclized rubber-azide, polyvinyl cinnamylidene acetate, and polycinnamic acid β-vinyloxyethyl ester.

Examples of positive photoresists include oil-soluble photoresists such as o-naphthoquinonediazide.
As a method for supplying the photoresist onto the substrate 20, any method may be used, but a coating method is preferably used.
As a coating method, the same method as described in the hole transport layer forming step [A2] of the method for producing the organic EL element 1 can be used.
Next, the film 80 ′ is exposed and developed through a photomask to form a resist layer 80 having an opening 820 in a region where the source electrode 30 and the drain electrode 40 are to be formed (see FIG. 3C). .

[B1-2] Next, as shown in FIG. 3D, in the opening 820 of the substrate 20 that has been subjected to the processing described above, depending on the source electrode 30 and the drain electrode 40 to be formed, A predetermined amount of the liquid material 90 containing these electrode constituent materials or precursors thereof is supplied.
In this liquid material 90, the solution or dispersion medium for dissolving or dispersing the constituent material of the source electrode 30 and the drain electrode 40 or the precursor thereof is the same as that described in the hole transport layer forming step [A2]. Things can be used.

  In addition, as a method for supplying the liquid material 90 into the opening 820, a coating method similar to that described above can be used, but among these, an inkjet method (droplet discharge method) is preferably used. . According to the ink jet method, the liquid material 90 can be discharged as a droplet from the nozzle of the droplet discharge head and reliably supplied into the opening 820. As a result, it is possible to reliably prevent the liquid material 90 from adhering to the resist layer 80.

[B1-3] Next, the solvent or the dispersion medium is removed from the liquid material 90 supplied to the opening 820 to form the source electrode 30 and the drain electrode 40.
The temperature at the time of removing the solvent or the dispersion medium (removal temperature) is not particularly limited and is slightly different depending on the type of the solvent or the dispersion medium, but is preferably about 20 to 200 ° C, and about 50 to 100 ° C. More preferably. Thereby, the solvent or dispersion medium contained in the liquid material 90 can be reliably removed.
In addition, you may make it heat the removal of this solvent or a dispersion medium under reduced pressure. Thereby, the solvent or the dispersion medium contained in the liquid material 90 can be removed more reliably.

[B1-4] Next, the resist layer 80 is removed from the substrate 20 to obtain the source electrode 30 and the drain electrode 40 formed on the substrate 20 (see FIG. 4F).
The removal method of the resist layer 80 may be appropriately selected according to the type of the resist layer 80. For example, ashing such as plasma treatment or ozone treatment, ultraviolet irradiation, Ne-He laser, Ar laser, CO ₂ laser, It can be carried out by irradiation with various lasers such as ruby laser, semiconductor laser, YAG laser, glass laser, YVO ₄ laser, excimer laser, contact with a solvent capable of dissolving or decomposing the resist layer 80 (for example, immersion).

[B2] Organic Semiconductor Layer Formation Step Next, as shown in FIG. 4 (h), the organic layer is formed on the substrate 20 on which the source electrode 30 and the drain electrode 40 are formed so as to cover the source electrode 30 and the drain electrode 40. A semiconductor layer 50 is formed.
At this time, a channel region 510 is formed between the source electrode 30 and the drain electrode 40 (region corresponding to the gate electrode 70).
This organic semiconductor layer 50 can be formed using the composition for conductive material of the present invention by the same method as described in the hole transport layer forming step [A2] of the method for producing the organic EL element 1. it can.

Here, the organic semiconductor layer 50 is composed mainly of the conductive material (polymer) of the present invention. Accordingly, in the next step [B3], when the gate insulating layer material is supplied onto the organic semiconductor layer 50, the polymer is preferably swollen and dissolved by the solvent or the dispersion medium contained in the gate insulating layer material. Can be suppressed or prevented. As a result, phase dissolution between the organic semiconductor layer 50 and the gate insulating layer 60 can be reliably prevented.
Moreover, in the organic TFT 10 obtained by configuring the organic semiconductor layer 50 using a polymer as a main material like the conductive material of the present invention, in the vicinity of the interface between the organic semiconductor layer 50 and the gate insulating layer 60, It is possible to reliably prevent the constituent materials from being mixed with each other over time.

[B3] Gate Insulating Layer Formation Step Next, as shown in FIG. 4I, a gate insulating layer 60 is formed on the organic semiconductor layer 50 by a coating method.
Specifically, the gate insulating layer 60 is formed by applying (supplying) a solution containing an insulating material or a precursor thereof onto the organic semiconductor layer 50 using the application method described above, and then applying the coating as necessary. The film can be formed by post-treatment (for example, heating, infrared irradiation, application of ultrasonic waves, etc.).

[B4] Gate Electrode Formation Step Next, as shown in FIG. 4J, the gate electrode 70 is formed on the gate insulating layer 60 by a coating method.
Specifically, the gate electrode 70 is applied (supplied) on the gate insulating layer 60 using a coating method with a solution containing an electrode material or a precursor thereof, and then applied to the coating film as necessary. The film can be formed by post-treatment (for example, heating, infrared irradiation, application of ultrasonic waves, etc.).

As the coating method, the same method as described above can be used, but it is particularly preferable to use the ink jet method. According to the inkjet method, a solution containing an electrode material or a precursor thereof can be patterned by discharging droplets from a nozzle of a droplet discharge head. As a result, the gate electrode 70 having a predetermined shape can be easily and reliably formed on the gate insulating layer 60.
Through the steps as described above, the organic TFT 10 is manufactured.

<Electronic equipment>
Moreover, the electronic devices of the present invention such as the organic EL element (light emitting element) 1 and the organic TFT (switching element) 10 as described above can be used in various electronic devices.
FIG. 5 is a perspective view showing a configuration of a mobile (or notebook) personal computer to which the electronic apparatus of the present invention is applied.

In this figure, a personal computer 1100 includes a main body 1104 provided with a keyboard 1102 and a display unit 1106 provided with a display. The display unit 1106 is rotatable with respect to the main body 1104 via a hinge structure. It is supported by.
In the personal computer 1100, for example, the display unit 1106 includes the organic EL element (light emitting element) 1 and the organic TFT (switching element) 10 described above.

FIG. 6 is a perspective view showing a configuration of a mobile phone (including PHS) to which the electronic apparatus of the present invention is applied.
In this figure, a cellular phone 1200 includes a plurality of operation buttons 1202, an earpiece 1204 and a mouthpiece 1206, and a display unit.
In the mobile phone 1200, for example, the display unit includes the organic EL element (light emitting element) 1 and the organic TFT (switching element) 10 described above.

FIG. 7 is a perspective view showing the configuration of a digital still camera to which the electronic apparatus of the present invention is applied. In this figure, connection with an external device is also simply shown.
Here, an ordinary camera sensitizes a silver halide photographic film with a light image of a subject, whereas a digital still camera 1300 photoelectrically converts a light image of a subject with an imaging device such as a CCD (Charge Coupled Device). An imaging signal (image signal) is generated.

A display unit is provided on the back of a case (body) 1302 in the digital still camera 1300, and is configured to display based on an imaging signal from the CCD, and functions as a finder that displays an object as an electronic image.
In the digital still camera 1300, for example, the display unit includes the organic EL element (light emitting element) 1 and the organic TFT (switching element) 10 described above.

A circuit board 1308 is installed inside the case. The circuit board 1308 is provided with a memory that can store (store) an imaging signal.
A light receiving unit 1304 including an optical lens (imaging optical system), a CCD, and the like is provided on the front side of the case 1302 (on the back side in the illustrated configuration).
When the photographer confirms the subject image displayed on the display unit and presses the shutter button 1306, the CCD image pickup signal at that time is transferred and stored in the memory of the circuit board 1308.

  In the digital still camera 1300, a video signal output terminal 1312 and an input / output terminal 1314 for data communication are provided on the side surface of the case 1302. As shown in the figure, a television monitor 1430 is connected to the video signal output terminal 1312 and a personal computer 1440 is connected to the input / output terminal 1314 for data communication as necessary. Further, the imaging signal stored in the memory of the circuit board 1308 is output to the television monitor 1430 or the personal computer 1440 by a predetermined operation.

  In addition to the personal computer (mobile personal computer) of FIG. 5, the mobile phone of FIG. 6, and the digital still camera of FIG. 7, the electronic apparatus of the present invention includes, for example, a television, a video camera, a viewfinder type, Monitor direct-view video tape recorder, laptop personal computer, car navigation system, pager, electronic notebook (including communication function), electronic dictionary, calculator, electronic game device, word processor, workstation, video phone, security TV Monitors, electronic binoculars, POS terminals, devices equipped with touch panels (for example, cash dispensers and automatic ticket vending machines for financial institutions), medical devices (for example, electronic thermometers, blood pressure monitors, blood glucose meters, electrocardiographs, ultrasound diagnostic devices, internal Endoscope display device), fish finder, various measuring instruments, Vessels such (e.g., gages for vehicles, aircraft, and ships), a flight simulator, various monitors, and a projection display such as a projector.

As mentioned above, although the composition for electroconductive materials of this invention, an electroconductive material, a conductive layer, an electronic device, and an electronic device were demonstrated based on embodiment of illustration, this invention is not limited to these.
For example, when the conductive layer is used as a hole transport layer, the electronic device of the present invention can be applied to an organic EL element which is an example of the above-described display element (light emitting element), for example, a light receiving element (photoelectric conversion). The present invention can be applied to a solar cell which is an example of an element.

Moreover, when using an electroconductive layer as an organic-semiconductor layer, the electronic device of this invention can be applied to the organic TFT which is an example of the switching element mentioned above, for example, can be applied to a semiconductor element etc.
Furthermore, the conductive layer of the present invention can be applied to, for example, wirings and electrodes in addition to being used as the above-described hole transport layer. In this case, the electronic device of the present invention can be applied to, for example, a wiring board.

Next, specific examples of the present invention will be described.
1. Synthesis of compounds First, compounds (A) to (S) as shown below were prepared.
<Compound (A)>
6- (p-aminophenyl) hexanol was treated with benzyl bromide and sodium hydride in anhydrous dimethylformamide to convert and protect the hydroxyl group to a benzyl ether group.

Next, 1 mol of the obtained compound was dissolved in 150 mL of acetic acid, and acetic anhydride was added dropwise at room temperature, followed by stirring. After completion of the reaction, the precipitated solid was filtered, washed with water and dried.
Next, 0.37 mol of the obtained substance, 0.66 mol of 1-bromo-4-hexylbenzene, 1.1 mol of potassium carbonate, copper powder and iodine were mixed and heated at 200 ° C. After allowing to cool, 130 mL of isoamyl alcohol, 50 mL of pure water, and 0.73 mol of potassium hydroxide were added and the mixture was stirred and dried.

Further, 130 mmol of the compound obtained there, 62 mmol of 2,5-bis (4-iodophenyl) -thiophene, 1.3 mmol of palladium acetate, 5.2 mmol of t-butylphosphine, 260 mmol of t-butoxynatrim, and 700 mL of xylene were mixed. , And stirred at 120 ° C.
Then, it stood to cool and crystallized.

The obtained compound was reduced with hydrogen gas under a Pd—C catalyst, converted from a benzyl ether group to a hydroxyl group, and deprotected.
Next, 100 mmol of the compound and 200 mmol of acryloyl chloride were added to the xylene solution, stirred while heating, then allowed to cool and crystallized to obtain a compound.
And mass spectrum (MS) method, ¹ H-nuclear magnetic resonance ( ¹ H-NMR) spectrum method, ¹³ C-nuclear magnetic resonance ( ¹³ C-NMR) spectrum method, and Fourier transform infrared absorption (FT-IR) It was confirmed by a spectral method that the obtained compound was the following compound (A).

<Compound (B)>
Compound (B) was obtained in the same manner as Compound (A) except that 1-bromo-3,5-dimethyl-4-hexylbenzene was used instead of 1-bromo-4-hexylbenzene.

<Compound (C)>
The above compound except that 2- (p-aminophenyl) ethanol was used instead of 6- (p-aminophenyl) hexanol and 1-bromo-4-ethylbenzene was used instead of 1-bromo-4-hexylbenzene. Compound (C) was obtained in the same manner as (A).

<Compound (D)>
Compound similar to the above compound (C) except that 2,5-bis (2-methyl-4-iodophenyl) -thiophene was used instead of 2,5-bis (4-iodophenyl) -thiophene (D) was obtained.

<Compound (E)>
Except that 8- (p-aminophenyl) octanol was used instead of 6- (p-aminophenyl) hexanol and 1-bromo-4-octylbenzene was used instead of 1-bromo-4-hexylbenzene. Compound (E) was obtained in the same manner as Compound (A).

<Compound (F)>
The compound (A) except that 1- (p-aminophenyl) methanol was used instead of 6- (p-aminophenyl) hexanol and 4-bromotoluene was used instead of 1-bromo-4-hexylbenzene. In the same manner as above, compound (F) was obtained.

<Compound (G)>
Except for using 5,5 ″ -bis (4-iodophenyl) -2,2 ′: 5 ′, 2 ″ -terthiophene instead of 2,5-bis (4-iodophenyl) -thiophene Compound (G) was obtained in the same manner as Compound (A).

<Compound (H)>
Compound (H) was prepared in the same manner as Compound (A) except that 3,5-diiodo-1,2,4-triazole was used instead of 2,5-bis (4-iodophenyl) -thiophene. Obtained.

<Compound (I)>
The same as the compound (A) except that 2,5- (4-iodophenyl) -1,3,4-oxadiazole was used instead of 2,5-bis (4-iodophenyl) -thiophene. Thus, compound (I) was obtained.

<Compound (J)>
Compound (A) is the same as compound (A) except that 3,3′-diiodo-1,1′-biisobenzothiophene is used instead of 2,5-bis (4-iodophenyl) -thiophene. J) was obtained.

<Compound (K)>
The above compound except that 2- (p-aminophenyl) ethanol was used instead of 6- (p-aminophenyl) hexanol and 1-bromo-4-ethylbenzene was used instead of 1-bromo-4-hexylbenzene. Compound (K) was obtained in the same manner as (J).

<Compound (L)>
Except that 8- (p-aminophenyl) octanol was used instead of 6- (p-aminophenyl) hexanol and 1-bromo-4-octylbenzene was used instead of 1-bromo-4-hexylbenzene. Compound (L) was obtained in the same manner as Compound (J).

<Compound (M)>
The compound (J) except that 1- (p-aminophenyl) methanol was used instead of 6- (p-aminophenyl) hexanol and 4-bromotoluene was used instead of 1-bromo-4-hexylbenzene. In the same manner as above, compound (M) was obtained.

<Compound (N)>
The above compound (A) was used except that 5,5′-diiodo-2,2′-bi (3,4-dioxyethyleneselenophene) was used in place of 2,5-bis (4-iodophenyl) -thiophene. ) To give compound (N).

<Compound (O)>
The above compound (A) except that 5,5 ″ -diiodo-2,2 ′: 5 ′, 2 ″ -terselenophene was used instead of 2,5-bis (4-iodophenyl) -thiophene In the same manner as above, compound (O) was obtained.

<Compound (P)>
5,5 ″ -diiodo-3,3 ′: 5 ′, 3 ″ -ter (4-phenyl-1,2,4-triazole) instead of 2,5-bis (4-iodophenyl) -thiophene Compound (P) was obtained in the same manner as Compound (A) except that was used.

<Compound (Q)>
1 mol of 1-amino-4-methylbenzene was dissolved in 150 mL of acetic acid, and acetic anhydride was added dropwise at room temperature, followed by stirring. After completion of the reaction, the precipitated solid was filtered, washed with water and dried.
Next, 0.37 mol of the obtained substance, 0.66 mol of 1-bromo-4-methylbenzene, 1.1 mol of potassium carbonate, copper powder and iodine were mixed and heated at 200 ° C. After allowing to cool, 130 mL of isoamyl alcohol, 50 mL of pure water, and 0.73 mol of potassium hydroxide were added and the mixture was stirred and dried.

Further, 130 mmol of the compound obtained there, 62 mmol of 2,5-bis (4-iodophenyl) -thiophene, 1.3 mmol of palladium acetate, 5.2 mmol of t-butylphosphine, 260 mmol of t-butoxynatrim, and 700 mL of xylene were mixed. , And stirred at 120 ° C.
Thereafter, the mixture was allowed to cool and crystallized to obtain a compound.
And mass spectrum (MS) method, ¹ H-nuclear magnetic resonance ( ¹ H-NMR) spectrum method, ¹³ C-nuclear magnetic resonance ( ¹³ C-NMR) spectrum method, and Fourier transform infrared absorption (FT-IR) It was confirmed by a spectral method that the obtained compound was the following compound (Q).

<Compound (R)>
As the following compound (R), poly (3,4-ethylenedioxythiophene / styrene sulfonic acid) (manufactured by Bayer, “Vitron P”) was prepared.

<Compound (S)>
Compound (S) was prepared in the same manner as Compound (Q) except that 3,5-diiodo-1,2,4-triazole was used in place of 2,5-bis (4-iodophenyl) -thiophene. Obtained.

2. Manufacture of Organic EL Element Five organic EL elements were manufactured in each of the following Examples, Reference Examples and Comparative Examples.
Example 1A
[Preparation of hole transport material]
Photopolymerization of the compound (A) as a heteroarylamine derivative and the polyester acrylate compound (n = 10-15, two A are hydrogen atoms) represented by the general formula (3) as an acrylic crosslinking agent are started. A radical polymerization initiator (“Irgacure 651” manufactured by Nagase Sangyo Co., Ltd.) was used as an agent, and these were dissolved in dichloroethane to prepare a hole transport material (composition for conductive material).
In addition, the mixing ratio of the compound (A) and the polyester acrylate compound (crosslinking agent) was 17: 2, and the ratio of the total weight of the compound (A) and the polyester acrylate compound to the weight of the radical polymerization initiator ( The weight ratio was 19: 1.
[Preparation of electron transport material]
An electron transport material (composition for conductive material) was obtained in the same manner as the hole transport material except that the compound (H) was used as the heteroarylamine derivative.

[Production of organic EL element]
-1A- First, an ITO electrode (anode) having an average thickness of 100 nm was formed on a transparent glass substrate having an average thickness of 0.5 mm by vacuum deposition.
-2A- Next, the hole transport material was applied onto the ITO electrode by a spin coating method and dried.
Thereafter, the compound (A) and the compound (A) were irradiated by irradiating ultraviolet rays having a wavelength of 185 nm and an irradiation intensity of ² mW / cm ^{2 in} the atmosphere using a filter for a mercury lamp (USHIO, “UM-452 model”) in the atmosphere. A hole transport layer having an average thickness of 50 nm was formed by a polymerization reaction with the polyester acrylate compound.

-3A- Next, on the hole transport layer, poly (9,9-dioctyl-2,7-divinylenefluorenyl-ortho-co (anthracene-9,10-diyl) (weight average molecular weight 200000) A 1.7 wt% xylene solution was applied by spin coating and then dried to form a light emitting layer having an average thickness of 50 nm.
-4A- Next, except that the electron transport material was used instead of the hole transport material on the light emitting layer, the same procedure as in Step 2A- Was subjected to a polymerization reaction to form an electron transport layer having an average thickness of 20 nm.
-5A- Next, an AlLi electrode (cathode) having an average thickness of 300 nm was formed on the electron transport layer by vacuum deposition.
-6A- Next, a protective cover made of polycarbonate was placed so as to cover each formed layer, and fixed and sealed with an ultraviolet curable resin to complete an organic EL element.

(Examples 2A to 17A)
Other than changing the heteroarylamine derivatives used for the hole transport material and the electron transport material, and the mixing ratio (molar ratio) of these heteroarylamine derivatives and the polyester acrylate compounds as shown in Table 1 (Table A). In the same manner as in Example 1A, after preparing the hole transport material and the electron transport material, an organic EL device was produced.

(Reference Example 1A)
An organic EL device was manufactured after preparing the hole transport material and the electron transport material in the same manner as in Example 1A except that the addition of the polyester acrylate compound was omitted.
(Reference Examples 2A to 13A)
Preparation of the hole transport material and the electron transport material in the same manner as in Reference Example 1A, except that the heteroarylamine derivatives used in the hole transport material and the electron transport material are those shown in Table 1 (Table B). Then, an organic EL element was manufactured.

(Comparative Example 1A)
[Preparation of hole transport material]
Compound (Q) was dissolved in dichloroethane to obtain a hole transport material.
[Production of organic EL element]
In the step-2A-, irradiation with ultraviolet rays from a mercury lamp is omitted, a hole transport layer is formed using the hole transport material, and in the step-4A-, the compound (S) is vacuum-deposited. An organic EL device was produced in the same manner as in Example 1A except that the electron transport layer was formed.

(Comparative Example 2A)
[Preparation of hole transport material]
A 2.0 wt% aqueous dispersion was prepared by dispersing the compound (R) in water to obtain a hole transport material.
In addition, as a compound (R), the thing with the ratio of 3, 4- ethylenedioxythiophene and styrenesulfonic acid 1:20 by weight ratio was used.
[Production of organic EL element]
An organic EL device was produced in the same manner as in Comparative Example 1A except that the hole transport material was used as the hole transport material.
(Comparative Examples 3A, 4A)
Preparation of the hole transport material and the electron transport material in the same manner as in Example 2A, except that the heteroarylamine derivatives used in the hole transport material and the electron transport material are those shown in Table 1 (Table B). Then, an organic EL element was manufactured.

3. Evaluation of organic EL device For each of the organic EL devices of each example, each reference example, and each comparative example, the light emission luminance (cd / m ² ) and the maximum light emission efficiency (lm / W) were measured, and the light emission luminance was initial. The time for half the value (half life) was measured.
Moreover, each measured value calculated | required the average value of five organic EL elements.

The measurement of light emission luminance was performed by applying a voltage of 6 V between the ITO electrode and the AlLi electrode.
And each measured value measured in Comparative Example 1A (luminescence brightness, maximum luminous efficiency, half life) as a reference value, each measured value measured in each example, each reference example and each comparative example, Evaluation was performed according to the following four-stage criteria.

A: The measurement value of Comparative Example 1A is 1.50 times or more. O: The measurement value of Comparative Example 1A is 1.25 times or more and less than 1.50 times. Δ: The measurement value of Comparative Example 1A. In contrast, 1.00 times or more and less than 1.25 times x: 0.75 times or more and less than 1.00 times the measured value of Comparative Example 1A. It shows in Table 1 (Table A) and Table 1 (Table B).

As shown in Table 1 (Table A) and Table 1 (Table B), organic EL elements of each example (organic EL including a hole transport layer and an electron transport layer mainly composed of the conductive material of the present invention) All of the devices were superior in terms of emission luminance, maximum emission efficiency, and half-life as compared with the organic EL devices of the respective comparative examples.
Thereby, it became clear that the interaction between main skeletons was suitably reduced in the organic EL element of the present invention. Moreover, it became clear that the phase dissolution of the hole transport layer and the light emitting layer was suitably prevented.

  Moreover, as for the organic EL element of each Example, all showed the tendency for the maximum luminous efficiency to be improved compared with the organic EL element of each reference example. In addition, such a tendency is such that it is formed of a particularly preferable hole transport material as in the case where the mixing ratio of the compound represented by the general formula (1) and the acrylic crosslinking agent is 1: 1. Remarkably recognized. This was a result suggesting that the separation distance of the main skeleton was maintained at a more appropriate distance by adding the acrylic crosslinking agent.

Further, by appropriately selecting the substituent X, in each example, the more the main skeleton separation distance is kept at an appropriate size, the better the emission luminance, the maximum emission efficiency, and the half-life A result indicating an extension of was obtained.
Further, in each example, the conductive materials constituting the hole transport layer and the electron transport layer are appropriately selected, that is, the group Y of the compound represented by the general formula (1) is appropriately selected. The more appropriate the combination of the hole transport layer and the electron transport layer, the better the emission luminance, the maximum emission efficiency, and the half-life extension.

  In addition, the examples except that a compound having a methacryloyl group as a functional group of the substituent X is used as the compound represented by the general formula (1) and a polyester methacrylate compound is used as a polyester (meth) acrylate-based crosslinking agent. A hole transport material and an electron transport material were prepared in the same manner as 1A to 17A and Reference Examples 1A to 13A, and organic EL devices were produced. These organic EL elements were evaluated in the same manner as in the above evaluation method, but the same results as described above were obtained.

4). Production of Organic TFT Five organic TFTs were produced in each of the following Examples, Reference Examples and Comparative Examples.
(Example 1B)
[Preparation of organic semiconductor materials]
An organic semiconductor material (composition for conductive material) was obtained in the same manner as the hole transport material of Example 1A except that the compound (J) was used as the heteroarylamine derivative.

[Manufacture of organic TFT]
-1B- First, a glass substrate having an average thickness of 1 mm was prepared and washed with water (cleaning liquid).
Next, a photoresist was applied on a glass substrate by a spin coating method, and then a pre-baking process was performed to form a film.
Next, the coating film was developed after being irradiated (exposed) with ultraviolet rays through a photomask. Thus, a resist layer having an opening in a region where the source electrode and the drain electrode are formed was formed.

-2B- Next, a gold colloid aqueous solution was supplied into the opening by an ink jet method. Thereafter, the glass substrate supplied with the aqueous gold colloid solution was dried by heating to obtain a source electrode and a drain electrode.
-3B- Next, after the resist layer was removed by oxygen plasma treatment, the glass substrate on which the source electrode and the drain electrode were formed was sequentially washed with water and methanol.

-4B- Next, the compound (J) and the polyester acrylate compound were subjected to a polymerization reaction in the same manner as in Step-2A- except that the organic semiconductor material was used instead of the hole transport material. An organic semiconductor layer having an average thickness of 50 nm was formed.
-5B- Next, a butyl acetate solution of polymethyl methacrylate (PMMA) was applied on the organic semiconductor layer by a spin coating method, and then dried to form a gate insulating layer having an average thickness of 500 nm.
-6B- Next, an aqueous dispersion of polyethylene dioxythiophene was applied to the region corresponding to the region between the source electrode and the drain electrode on the gate insulating layer by an ink jet method and then dried. Thereby, a gate electrode having an average thickness of 100 nm was formed.
The organic TFT was manufactured by the above process.

(Examples 2B-9B)
Except that the heteroarylamine derivative used for the organic semiconductor material and the mixing ratio (molar ratio) of the heteroarylamine derivative and the polyester acrylate compound were changed as shown in Table 2, respectively, in the same manner as in Example 1B. After preparing the organic semiconductor material, an organic TFT was manufactured.

(Reference Example 1B)
An organic TFT was manufactured after preparing an organic semiconductor material in the same manner as in Example 1B except that the addition of the polyester acrylate compound was omitted.
(Reference Examples 2B-7B)
An organic TFT was prepared after preparing an organic semiconductor material in the same manner as in Reference Example 1B, except that the heteroarylamine derivatives used in the organic semiconductor material were those shown in Table 2.

(Comparative Example 1B)
[Preparation of organic semiconductor materials]
Compound (Q) was dissolved in dichloroethane to obtain an organic semiconductor material.
[Production of organic TFT]
In the step-4B-, an organic TFT was manufactured in the same manner as in Example 1B except that the irradiation of ultraviolet rays by a mercury lamp was omitted and the organic semiconductor material was used.
(Comparative Examples 2B and 3B)
An organic TFT was manufactured after preparing an organic semiconductor material in the same manner as in Example 2B, except that the heteroarylamine derivatives used in the organic semiconductor material were those shown in Table 2.

5. Evaluation of Organic TFT The values of the OFF current and the ON current were measured for the organic TFTs produced in each Example, each Reference Example, and each Comparative Example.
Here, the OFF current is a value of a current that flows between the source electrode and the drain electrode when no gate voltage is applied, and the ON current is the value of the source electrode when the gate voltage is applied. It is the value of the current flowing between the drain electrode.

Therefore, the larger the ratio of the absolute value of the OFF current and the absolute value of the ON current (ON / OFF ratio), the more the organic TFT has better characteristics.
The OFF current was measured with the potential difference between the source electrode and the drain electrode as 30 V, and the ON current was measured with the potential difference between the source electrode and the drain electrode as 30 V and the absolute value of the gate voltage as 40 V.

And the value of ON / OFF ratio measured by each Example, each reference example, and each comparative example was each evaluated in accordance with the following four steps of criteria.
A: ON / OFF ratio value is 10 ⁴ or more B: ON / OFF ratio value is 10 ³ or more, less than 10 ⁴ Δ: ON / OFF ratio value is 10 ² or more, 10 ³ × less than: the value of the oN / OFF ratio is less than 10 ² these evaluation results, respectively, shown in Table 2 below.

As shown in Table 2, each of the organic TFTs of each example had a large ON / OFF ratio value and excellent characteristics as compared with the organic TFT of each comparative example.
Thereby, it became clear that the interaction between the main skeletons was suitably reduced. Moreover, it became clear that the phase dissolution of the organic semiconductor layer and the gate insulating layer was suitably prevented.

Moreover, the organic TFT of each Example showed the tendency for ON / OFF ratio to be improved compared with the organic TFT of each reference example. This was a result suggesting that the separation distance of the main skeleton was maintained at a more appropriate distance by adding the acrylic crosslinking agent.
Furthermore, by appropriately selecting the substituent X, in each example, the more the main skeleton separation distance is maintained, the larger the value of the ON / OFF ratio and the better the result. was gotten.

  In addition, the examples except that a compound having a methacryloyl group as a functional group of the substituent X is used as the compound represented by the general formula (1) and a polyester methacrylate compound is used as a polyester (meth) acrylate-based crosslinking agent. Organic semiconductor materials were prepared in the same manner as 1B to 9B and Reference Examples 1B to 7B, and organic TFTs were produced. These organic TFTs were evaluated in the same manner as in the above evaluation method, but the same results as described above were obtained.

It is the longitudinal cross-sectional view which showed an example of the organic EL element. It is a figure which shows embodiment of organic TFT, (a) is a longitudinal cross-sectional view, (b) is a top view. It is a figure (longitudinal sectional drawing) for demonstrating the manufacturing method of the organic TFT shown in FIG. It is a figure (longitudinal sectional drawing) for demonstrating the manufacturing method of the organic TFT shown in FIG. 1 is a perspective view showing a configuration of a mobile (or notebook) personal computer to which an electronic apparatus of the present invention is applied. It is a perspective view which shows the structure of the mobile telephone (PHS is also included) to which the electronic device of this invention is applied. It is a perspective view which shows the structure of the digital still camera to which the electronic device of this invention is applied.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 ... Organic EL element 2 ... Substrate 3 ... Anode 4 ... Organic EL layer 41 ... Hole transport layer 42 ... Light emitting layer 43 ... Electron transport layer 5 ... Cathode 6 ... Protective layer 10 ... Organic thin film transistor 20 ... Substrate 30 ... Source electrode 40 ... Drain electrode 50 ... Organic semiconductor layer 510 ... Channel region 60 ... Gate insulating layer 70 ... Gate electrode 80 ... Resist layer 80 '... Film 820 ... ... Opening 90 ... Liquid material 1100 ... Personal computer 1102 ... Keyboard 1104 ... Main body 1106 ... Display unit 1200 ... Mobile phone 1202 ... Operation buttons 1204 ... Earpiece 1206 ... Mouthpiece 1300 ... Digital still camera 1302 Case (body) 1304 Light receiving unit 1306 Shutter button 130 8 ... Circuit board 1312 ... Video signal output terminal 1314 ... Input / output terminal for data communication 1430 ... Television monitor 1440 ... Personal computer

Claims (32)

The composition for electroconductive materials characterized by containing the compound represented by following General formula (1), and an acrylic type crosslinking agent.

[Wherein, two R ^{1 s} each independently represent a straight-chain alkyl group having 2 to 8 carbon atoms, and may be the same or different, and four R ^{2 s} each independently Represents a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and two X's each independently represent a substituent represented by the following general formula (2); Or Y may be different, and Y represents a group containing at least one substituted or unsubstituted heterocycle. ]

[Wherein, n represents an integer of 2 to 8, and Z represents a hydrogen atom or a methyl group. ]   The composition for conductive materials according to claim 1, wherein the acrylic crosslinking agent contains a polyester (meth) acrylate crosslinking agent as a main component.   The composition for conductive materials according to claim 2, wherein the polyester (meth) acrylate-based crosslinking agent has at least two (meth) acryloyl groups. The composition for conductive materials according to claim 2 or 3, wherein the polyester (meth) acrylate-based crosslinking agent contains a compound represented by the following general formula (3) as a main component.

[Wherein n represents an integer of 4500 or less, and two A's each independently represent a hydrogen atom or a methyl group, and may be the same or different. ]   The said substituent X is the same, The composition for electroconductive materials in any one of Claim 1 thru | or 4.   The composition for a conductive material according to any one of claims 1 to 5, wherein the substituent X is bonded to any of the 3-position, 4-position, and 5-position of the benzene ring. Two of the substituents R ^1, the conductive material composition according to any one of claims 1 identical 6. The composition for a conductive material according to claim 1, wherein the substituent R ¹ is bonded to the 4-position of the benzene ring.   The composition for conductive materials according to any one of claims 1 to 8, wherein the heterocyclic ring contains at least one heteroatom selected from nitrogen, oxygen, sulfur, selenium, and tellurium.   The conductive material composition according to claim 1, wherein the heterocyclic ring is aromatic.   The composition for a conductive material according to claim 1, wherein the group Y includes 1 to 5 heterocycles.   The composition for a conductive material according to any one of claims 1 to 11, wherein the group Y includes at least one substituted or unsubstituted aromatic hydrocarbon ring in addition to the heterocyclic ring.   The group Y includes the aromatic hydrocarbon ring directly bonded to each N in the general formula (1), and at least one heterocyclic ring present between these aromatic hydrocarbon rings. The composition for conductive materials according to claim 12.   14. The composition for a conductive material according to claim 1, wherein the total number of carbon atoms of the group Y is 2 to 75. 15. A conductive material obtained by polymerizing a substituent X between compounds represented by the following general formula (1) directly or via the acrylic crosslinking agent.

[Wherein, two R ^{1 s} each independently represent a straight-chain alkyl group having 2 to 8 carbon atoms, and may be the same or different, and four R ^{2 s} each independently Represents a hydrogen atom, a methyl group or an ethyl group, which may be the same or different, and two X's each independently represent a substituent represented by the following general formula (2); Or Y may be different, and Y represents a group containing at least one substituted or unsubstituted heterocycle. ]

[Wherein, n represents an integer of 2 to 8, and Z represents a hydrogen atom or a methyl group. ]   The conductive material according to claim 15, wherein the compound and the acrylic crosslinking agent undergo a polymerization reaction by light irradiation.   A conductive layer formed using the composition for conductive material according to claim 1.   A conductive layer comprising the conductive material according to claim 15 or 16 as a main material.   The conductive layer according to claim 17 or 18, wherein the conductive layer is a hole transport layer.   The conductive layer according to claim 19, wherein the hole transport layer has an average thickness of 10 to 150 nm.   The conductive layer according to claim 17, wherein the conductive layer is an electron transport layer.   The conductive layer according to claim 21, wherein the electron transport layer has an average thickness of 1 to 100 nm.   The conductive layer according to claim 17, wherein the conductive layer is an organic semiconductor layer.   The conductive layer according to claim 23, wherein an average thickness of the organic semiconductor layer is 0.1 to 1000 nm.   An electronic device comprising the conductive layer according to claim 17.   An electronic device comprising the laminate having the conductive layer according to claim 19.   27. The electronic device according to claim 26, wherein the electronic device is a light emitting element or a photoelectric conversion element.   The electronic device according to claim 27, wherein the light emitting element is an organic electroluminescence element.   An electronic device comprising a laminate having the conductive layer according to claim 23 or 24.   30. The electronic device according to claim 29, wherein the electronic device is a switching element.   The electronic device according to claim 30, wherein the switching element is an organic thin film transistor. An electronic apparatus comprising the electronic device according to any one of claims 25 to 31.

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