JPH09188764A - Production of polysiloxane hole transporting material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the above material useful for electrophotographic devices, etc., by binding a hole transporting group to a silicon atom in a polysiloxane resin. SOLUTION: (A) One or more kinds of silicon compounds selected from among the formula R3 SiZ (R is a monovalent hydrocarbon group; Z is a hydrolyzable group), the formula R2 SiZ2 , the formula R1 SiZ3 and the formula SiZ and/or its partial hydrolysis condensation product is subjected to co-hydrolytic condensation with (B) a hole transporting organosilicon compound of the formula A-[R<1> SiR<2> 3-n Qn ]p [A is an aromatic substituted tertiary amine having plural aromatic groups and is an organic group derived from a hole transporting compound having 4.5-6.2eV ionized potential; R<1> is a 1-18C alkylene; R<2> is a 1-15C monovalent hydrocarbon; Q is a hydrolyzable group; (n) is an integer of 1-3; (p) is an integer of 1-3] in an organic solvent. Furthermore, the component A is a compound capable of providing a polysiloxane resin having 0.5-1.5 ratio of a monovalent hydrocarbon group to silicon atom by hydrolytic condensation.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a polysiloxane-based hole-transporting material for use in an electrophotographic device or the like in which a hole-transporting group is bonded to a silicon atom in polysiloxane.

[0002]

2. Description of the Related Art An electrophotographic photosensitive member is required not only to have electrical characteristics and optical characteristics according to an electrophotographic process, but also to have durability in a charging process and durability in a toner removing process after a developing / transferring process. Chemical and mechanical durability such as abrasion resistance is required. In recent years, electrophotographic photoreceptors using organic compounds have become mainstream from the viewpoints of pollution-free and high productivity. The organic photoconductor is one in which an organic compound having a hole transporting ability is dispersed or dissolved in a resin such as an acrylic resin, a polycarbonate resin, a polyester resin, or a polyurethane resin, which is coated on the charge generation layer,
Alternatively, it is configured by a method of applying a resin in which the charge generating substance is dispersed as described above.

In the electrophotographic process, the charge transport layer is required to have electrical and mechanical characteristics in addition to simply transporting the charges generated in the charge generation layer to the surface of the photoreceptor. In addition to corona chargeability and characteristics associated with deterioration, toner development, transferability and cleaning characteristics, many characteristics related to production processes such as film formation are required, and current organic photoreceptors are not always satisfied. Do not mean.
In order to improve these drawbacks, silicone resins have attracted attention because of their high stability against corona discharge and low surface energy, and the following studies have been conducted. Addition of silicone oil (JP-A-61-129595)
4), an attempt to improve the surface characteristics of the photoconductor by adding polydimethylsiloxane, silicone resin powder, etc. (JP-A-4-324454), addition of a crosslinked silicone resin, block copolymerization with polycarbonate, silicone Modified polyurethane, silicone modified polyester, and the like have been investigated as photosensitive material surface protecting materials for photosensitive materials.

[0004]

Since the polysiloxane resin does not exhibit sufficient compatibility with other resins, if it is simply blended with another resin, phase separation occurs, or bleeding on the surface of the blended resin results in poor properties. Change. Although block copolymers have been used in an attempt to improve this, block copolymers consisting of resins that are essentially incompatible, as is known in polymer chemistry, form phase separated structures. In this case also, light scattering will occur.

Further, since the polysiloxane resin is essentially electrically neutral and inactive, the polysiloxane resin alone has no hole transporting ability. Therefore, a hole transporting material is added for functionalization. There is a need. However, the polysiloxane resin is a resin in which it is difficult to uniformly disperse a large amount of general low molecular weight organic molecules in a uniform manner. An object of the present invention is to provide a method for producing a polysiloxane resin having a hole-transporting ability, which is obtained by uniformly bonding a hole-transporting group imparting a hole-transporting function to a silicon atom in the polysiloxane resin. It is in.

[0006]

The present invention is a method for producing a polysiloxane hole transporting material, which comprises co-hydrolyzing and condensing the following first and second components in an organic solvent. First component: a silicon compound capable of giving a polysiloxane resin having a ratio of monovalent hydrocarbon groups to silicon atoms of 0.5 to 1.5 by hydrolysis condensation (provided that the silicon compound is 1 selected from and
It is a silicon compound of at least one species. R ₃ SiZ R ₂ SiZ ₂ R ₁ SiZ ₃ SiZ ₄ Here, R is a monovalent hydrocarbon group and Z is a hydrolyzable group. ) And / or a partial hydrolysis condensation product thereof. Second component: a hole-transporting organosilicon compound represented by the following formula (1) A- [R ¹ SiR ² _3-n Q _n ] _p (1) (where A has a plurality of aromatic groups) An aromatic substituted tertiary amine having an ionization potential of 4.5 to 6.
2 eV represents an organic group derived from a hole transporting compound, R ¹ is an alkylene group having 1 to 18 carbon atoms, and R ² is a monovalent hydrocarbon group having 1 to 15 carbon atoms which may have halogen. , Q is a hydrolyzable group, n is an integer of 1 to 3, p is 1 to
It is an integer of 3. The term “derived” means that it is generated by taking a hydrogen atom or another substituent of the aromatic ring contained in the hole transporting compound. )

As an example of the hydrolyzable group Q, a hydroxyl group,
Examples thereof include an alkoxy group, a methylethylketoxime group, a diethylamino group, an acetoxy group and a propenoxy group. Among these, a hydroxyl group and alkoxy having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, a butoxy group and a propoxy group are preferable. The above R ¹ is preferably an alkylene group having 1 to 6 atoms.

The silicon compound as the first component in the present invention is a silicon compound that can give a polysiloxane resin having a ratio of monovalent hydrocarbon groups to silicon atoms of 0.5 to 1.5 by hydrolysis and condensation. It refers to a compound and / or a partial hydrolysis-condensation product thereof. Here, the monovalent hydrocarbon group refers to a monovalent hydrocarbon group selected from the group consisting of an aliphatic hydrocarbon group and an aromatic hydrocarbon group. As the monovalent hydrocarbon group R directly bonded to a silicon atom,
A straight chain or branched saturated hydrocarbon group having 1 to 18 carbon atoms, for example, methyl, ethyl, propyl, butyl, amyl, hexyl, 2-ethylhexyl, dodecyl, octadecyl, etc., an alkenyl group, for example, vinyl, allyl, an aryl group, for example. Phenyl, tolyl, a halogenated hydrocarbon group, for example, a fluorohydrocarbon group represented by trifluoropropyl, heptafluoropentyl, nanofluorohexyl, etc., chloromethyl, chloroethyl, etc., which is a straight or branched chain having 1 to 18 carbon atoms. Regardless of this, a saturated hydrocarbon group halogen-substituted product can be mentioned. In addition, here, the hydrolyzable group Z
Is not particularly limited, and examples thereof include a hydroxyl group, an alkoxy group, a methylethylketoxime group, a diethylamino group, an acetoxy group, and a propenoxy group. Therefore, the silicon compound may be either an organic compound or an inorganic compound. However, Z is preferably an organic group. For the synthesis of the resin in the present invention, Japanese Patent Publication No. 26-26
96, the method described in JP-A-28-297 and "Chemistry and Technology".
ogy of Silicones ”, Walter
Noll, Academic Press, Inc.
(1968), the siloxane polymer synthesis method described in P191 can be applied. Although the solubility of the first silicon compound in a solvent is not necessarily good, it shows good solubility in aromatic hydrocarbons such as toluene and halogenated hydrocarbons such as chloroform, and therefore these are considered to be solvents commonly used. The use of mixed solvents is recommended. Water or an organic solvent is added to the obtained copolymerized polysiloxane and separated. After that, it is washed with water to be neutralized. The copolymerized polysiloxane produced in this manner contains 0.01 to 10% by weight of a silicon atom-bonded hydroxyl group and / or a hydrolyzable group. If it is too large, the storage stability deteriorates, and if it is too small, it affects the physical properties after film formation. It is preferably in the range of 0.1 to 4.0% by weight.

The polysiloxane-based hole transporting material produced by the production method of the present invention preferably has practically sufficient characteristics such as charge transportability, sensitivity and mechanical strength depending on the purpose. These properties are adjusted mainly by the amount of the units derived from the hole transporting organosilicon compound of the second component in the polysiloxane hole transporting material. The required amount varies somewhat depending on the purpose. Usually, the unit derived from the second component is 10 parts by weight to 2 parts by weight with respect to 100 parts by weight of the unit derived from the first component.
00 parts by weight is recommended, preferably 30 parts by weight to 150 parts by weight of the second component, more preferably 3 parts by weight of the second component.
0 to 100 parts by weight is recommended. When the amount of the units derived from the hole-transporting organosilicon compound as the second component decreases, the polysiloxane-based hole-transporting material has insufficient charge-transporting property and the sensitivity decreases. Further, when the amount of the same unit is excessive, the mechanical strength tends to be insufficient.

The second component, the hole-transporting organosilicon compound used in the present invention, is a silyl group having an electron-donating group having a hydrolyzable group represented by an alkoxysilyl group via a hydrocarbon group. It is one that is combined. In the case of direct bonding, the π electron of the aromatic ring of the aromatic group may cause a π-d interaction with the d electron of silicon to change the ionization potential. Avoiding this, the organic photoconductor design can be facilitated. This is because

One of the methods for producing the second component, a hole-transporting organosilicon compound, is an aromatic-substituted tertiary amine having a plurality of aromatic groups and has an ionization potential of 4.5 to 6.2 eV. In the hole-transporting compound, the unsaturated aliphatic hydrocarbon group is substituted on the aromatic group, and the unsaturated aliphatic hydrocarbon group further has a hydrogen atom and a hydrolyzable group as a substituent. A method of reacting a silicon compound (hereinafter referred to as a silicon hydride compound) can be mentioned.
According to this method, an unsaturated aliphatic hydrocarbon group substituted with the aromatic group (for example, a vinyl group substituted with an aromatic ring),
A silyl group (for example, an alkoxysilyl group) derived from the silicon hydride compound is introduced by the hydrosilylation reaction. The silicon hydride compound is preferably an organosilicon compound. As a method for introducing an unsaturated aliphatic hydrocarbon group such as a vinyl group into the aromatic group, a methyl group or a hydrogen atom substituted on the aromatic ring is formylated, and an aldehyde is dehydrated to introduce a vinyl group. be able to. After this, a hydrosilylation reaction can be used. As another method, there is a method in which a saturated hydrocarbon group substituted with an aromatic group, for example, a methyl group is bromomethylated to form a lithio complex, and this is reacted with a halogenated alkoxysilane. The ionization potential in the present invention is measured under atmospheric pressure by photoelectron spectroscopy (manufactured by Riken Keiki, using a surface analyzer AC-1).

Examples of the aromatic-substituted tertiary amine having an ionization potential of 4.5 to 6.2 eV used in the production method of the present invention include the following. In the formulas below, Me represents methyl and Et represents ethyl.

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[Chemical 6]

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Regarding the method for producing the hole transporting organosilicon compound as the second component, a typical example of the silyl group derived from the silicon hydride compound is an alkoxysilyl group, and the aromatic substitution is also performed. The unsaturated aliphatic hydrocarbon group substituted on the aromatic ring of the tertiary amine will be described in detail below taking the case of a vinyl group as an example. At which position in the aromatic ring of the aromatic-substituted tertiary amine the alkoxysilyl group is introduced is not particularly limited, and it is not always necessary that the alkoxysilyl group is bonded to all aromatic rings. It is determined in consideration of solubility in a polysiloxane resin described later. In this case, as a method for introducing the vinyl group into the aromatic ring bonded to nitrogen, the methyl group or hydrogen atom substituted on the aromatic ring as described above is formylated,
A vinyl group can be introduced by addition dehydration to an aldehyde. It can also be introduced by performing dehydrohalogenation between the hydrogen of the aromatic-substituted secondary amine and the halogenated aromatic compound substituted with the vinyl group.

In the present invention, the silicon hydride compound capable of reacting with the vinyl group bonded to the aromatic ring of the aromatic-substituted tertiary amine having an ionization potential of 4.5 to 6.2 eV is, for example, a molecule. Among them are hydrogenated organosilicon compounds having a hydrogen atom and an alkoxy group as essential substituents of a silicon atom, which are additionally bonded to a vinyl group by a hydrosilylation reaction. The hydrogen atom directly bonded to the silicon atom is an essential component for the hydrosilylation reaction to be added to the vinyl group, and the alkoxy group is the number of carbon atoms as R ³ when the alkoxy group is represented by OR ^3. From 1 to 6 methyl, ethyl, propyl, butyl, amyl, hexyl and other chain-like or branched alkyls with relatively low chain length, considering the stability and hydrolyzability during hydrosilation reaction, etc. Will be selected accordingly.

In this case, n in the general formula represents the number of silicon-substituted alkoxy groups, and when it is plural, hydrophilicity is generally increased, and when plural condensable groups are present, a crosslinking agent is used. Therefore, it must be set in consideration of not only the hydrophilicity but also the hardness of the resin due to crosslinking.

The organic group R ² directly bonded to a silicon atom other than the hydrogen atom and the alkoxy group is soluble in the resin, the reactivity during the hydrosilylation reaction, and the like, depending on the kind of the substituent on the silicon of the polysiloxane. Methyl, ethyl, propyl, butyl, amyl, hexyl, etc., alkenyl groups such as vinyl, allyl, etc. aryl groups such as phenyl, tolyl etc., halogenated hydrocarbon groups, etc. according to various purposes such as property adjustment of polysiloxane resin. For example, it can be appropriately selected from the group consisting of fluorohydrocarbon groups represented by trifluoropropyl, heptafluoropentyl, nanofluorohexyl and the like. When the substituent on the silicon of the polysiloxane is methyl, it can be easily imagined that the solubility is better when R ² is a methyl group.

The silicon compound as the first component is one that can be hydrolyzed and condensed to form a silicone resin, and various alkoxysilanes and the like are included in this category. There is no particular limitation as long as it can be hydrolyzed and condensed into a silicone resin, but organotrialkoxysilane is preferably selected. Organotrialkoxysilanes provide the silicone resin commonly referred to in the silicone industry as T-resin by hydrolytic condensation. The monovalent aliphatic or aromatic hydrocarbon group directly bonded to the silicon atom has 1 to 18 carbon atoms.
A linear or branched saturated hydrocarbon group such as methyl, ethyl, propyl, butyl, amyl, hexyl, 2-ethylhexyl, dodecyl, octadecyl, etc., an alkenyl group,
For example, vinyl, allyl, etc., aryl groups such as phenyl,
Tolyl, halogenated hydrocarbon groups such as trifluoropropyl, heptafluoropentyl, and fluorohydrocarbon groups represented by nanofluorohexyl, chloromethyl, chloroethyl, etc. In any case, a saturated hydrocarbon group halogen-substituted product can be used. In the present invention, as long as the ratio of the number of monovalent hydrocarbon groups to silicon atoms in the final product, polysiloxane, does not change within the range of 0.5 to 1.5, a plurality of hydrolyzable groups are included in one molecule. It is also possible to add a silicon compound having a as a third copolymerization component. For example, diorganodialkoxysilane, tetraorganodialkoxydisiloxane and the like, mechanical strength of the polysiloxane resin,
It is appropriately selected depending on the purpose of controlling physical properties such as film-forming property.

When the ratio of the number of monovalent organic groups to silicon atoms is smaller than the range of 0.5 to 1.5, the resin tends to become hard and brittle as the numerical value becomes smaller. If it gets bigger, the opposite is true. Therefore, the structure of the copolymer is optimized in consideration of the type of the alkyl group substituted on the silicon atom, the structure of the hole transporting organic silicon compound and the amount of the copolymerization.

The polysiloxane hole transport material according to the present invention can be dissolved in a suitable solvent and used for the production of an electrophotographic photoreceptor. Since the solvent used also serves for coating, it must be selected in consideration of the influence on other materials constituting the photoreceptor. The coating is performed on the equipment by a known coating method such as dipping, spray coating, spin coating and the like. Then, after heating at a temperature near the boiling point of the solvent to sufficiently remove the residual solvent, the coating film is formed by curing in the range of room temperature to 150 ° C. No white turbidity was observed in the coating film thus formed, and a transparent coating film having a thickness of several microns to several tens of microns was formed.

[0038]

【Example】

(Synthesis Example 1) (Synthesis of 4- [2- (triethoxysilyl) ethyl] triphenylamine) (Synthesis of 4- (N, N-diphenylamino) benzaldehyde) Triphenylamine 101.
4 g of DMF and 35.5 ml of DMF were added, phosphorus oxychloride 84.4 ml was added dropwise with stirring under ice water cooling, and the temperature was raised to 95 ° C.
And allowed to react for 5 hours. The reaction solution was poured into 4 L of warm water and stirred for 1 hour. Then, the precipitate was collected by filtration and washed with a mixed solution of ethanol / water (1: 1) to obtain 4- (N, N-diphenylamino) benzaldehyde. Yield 91.
5 g (81.0% yield).

(Synthesis of 4-vinyltriphenylamine)
Sodium hydride (14.6 g) and 1,2-dimethoxyethane (700 ml) were placed in a three-necked flask, and trimethylphosphonium bromide (130.8 g) was added with stirring at room temperature. Next, one drop of absolute ethanol was added, and the mixture was reacted at 70 ° C. for 4 hours. 4- (N, N-diphenylamino) benzaldehyde 100g was added to this, the temperature was raised to 70 degreeC, and it was made to react for 5 hours. The reaction solution was filtered, and the filtrate and the ether extract of the precipitate were combined and washed with water. Then, the ether solution was dehydrated with calcium chloride and then the ether was removed,
A reaction mixture was obtained. This was recrystallized from ethanol to obtain acicular, pale yellow vinyltriphenylamine.
Yield 83.4 g (84.0% yield).

(Hydrosilylation of 4-vinyltriphenylamine) Toluene 40 ml, triethoxysilane 9.9
0.018 mmol of a toluene solution of g (60 mmol) and tris (tetramethyldivinyldisiloxane) diplatinum (O)
Into a three-necked flask, 20 ml of a toluene solution of 8.2 g of 4-vinyltriphenylamine was added dropwise while stirring at room temperature. After completion of dropping, the mixture was stirred at 70 ° C. for 3 hours, and then the solvent was removed under reduced pressure to obtain pale yellow oily 4- [2- (triethoxysilyl) ethyl] triphenylamine. Yield 12.1 g (91.7% yield).

(Synthesis Example 2) (Synthesis of 4,4 ', 4 "-tris [2- (triethoxysilyl) ethyl] triphenylamine) (Synthesis of tri (4-formylphenyl) amine) Three-necked flask 50.7 g of triphenylamine and DMF5
3.3 ml was added, and 126.6 ml of phosphorus oxychloride was added dropwise while cooling with ice water. After the dropwise addition was completed, the mixed solution was reacted at 95 ° C. for 5 hours, poured into 5 L of warm water, and stirred for 1 hour. Then, the precipitate was collected by filtration, and ethanol / water (1:
It was washed with the mixed solution of 1) to obtain tri (4-formylphenyl) amine. Yield 65.3 g (yield 95.9
%).

(Synthesis of tri (4-vinylphenyl) amine) Sodium hydride (14.6 g) and 1,2-dimethoxyethane (700 ml) were placed in a three-neck flask, and trimethylphosphonium bromide (130.8) was stirred at room temperature.
g was added. Then add a drop of absolute ethanol and then 70
The reaction was performed at 4 ° C. for 4 hours. Tri (4-formylphenyl) amine 40.2 was added to the reaction mixture obtained as described above.
g was added, and the mixture was reacted at 70 ° C. for 5 hours, separated by filtration, and the filtered cake was extracted with ether, combined with the filtrate, and washed with water. Then, after dehydrating the ether solution with calcium chloride,
The ether was removed to give a reaction mixture. This was recrystallized twice with ethanol to obtain needle-shaped, pale yellow tri (4-vinylphenyl) amine. Yield 38.4 g (yield 97.
3%).

(Hydrosilylation of tri (4-vinylphenyl) amine) Toluene 40 ml, triethoxysilane 9.9 g (60 mmol) and tris (tetramethyldivinyldisiloxane) diplatinum (O) in toluene solution 0.01
8 mmol was placed in a three-necked flask, and 3.3 g (13 mmol) of tri (4-vinylphenyl) amine was stirred at room temperature.
20 ml of a toluene solution of was added dropwise. After dropping, 70 ° C
After stirring for 3 hours, the solvent was removed under reduced pressure to obtain pale yellow oily 4,4 ', 4 "-[2- (triethoxysilyl) ethyl] triphenylamine. Yield 7.8 g.
(Yield 80.6%).

(Example 1) Synthesis in a flask according to Synthesis Example 1
4- {2- (triethoxysilyl) ethyl} trif
7.9 g (18 mmol) of phenylamine, methyl trime
81 g of toxysilane, 20 of phenyltrimethoxysilane
g and tetrabutyl titanate 0.15 g
Then, a mixed solution of 20 g of methanol and 10 g of water was dropped.
Was. After the dropping was completed, the mixture was further mixed for 2 hours. Then,
The volatile solvent was removed under reduced pressure to give the formula: (QC_TwoH_FourSiO_3/2)_a(CH_ThreeSiO_3/2)_b(C₆
H_FiveSiO_3/2)_c− (O _1/2R)_d (However, Q is a para-diphenylamino-phenyl group.
R is a methyl group or an ethyl group, and a: b: c:
The ratio of d is approximately 0.2: 1: 1.9: 2. )so
The polysiloxane resin (S) shown was obtained. Polysiloki
Sun resin (S) 10 g, toluene 5 g and tetrahydrof
Add 5 g of orchid to dissolve it, and bar coat it on a glass plate.
Was applied and dried and cured at 140 ° C. for 15 hours.
When observed under a microscope, it was confirmed that a uniform film had been formed.
It turned out.

(Hole Transportability Test) (1) After washing an aluminum plate of 5 cm × 5 cm, the solution of Example 1 was cast, the solvent was removed and the product was dried. 140 this
The film was heated at 0 ° C. for 15 hours to be cured, and a film having a thickness of 12 μm was formed on an aluminum plate. 1kV on the surface of the film
It was charged with corona. On the other hand, DC power supply (T
R6120, manufactured by Advantest Corporation) 1kV
Injected positive charge. When the potential on the film surface was measured with a surface potential meter (TREK142000), the surface charge was neutralized and decreased to 600V. (2) A film was formed on the ITO glass by using the solution of Example 1 in the same manner as in the above (1). Further, gold was vapor-deposited on the film as a counter electrode. Irradiate a 337 nm N ₂ laser from the gold electrode side, and time-of-
The drift mobility of holes was measured by the Flight (TOF) method. The extrapolated mobility was 7 × 10 ⁻⁸ cm ² / Vs at room temperature.

Example 2 Toluene 40 was added to a flask.
g, 4- {2- (triethoxysilyl) ethyl} triphenylamine synthesized in Synthesis Example 1 (7.9 g (18 mmol)) and methylsilsesquioxane (a partial hydrolyzed condensate of methyltrimethoxysilane, 33 methoxy groups
The mixture was heated to reflux for 2 hours while mixing 60 g (containing wt%), 10 g of methanol, and 6 g of water. The volatile solvent is then removed under reduced pressure to give the formula: (QC ₂ H ₄ SiO _3/2 ) _x (CH ₃ SiO _3/2 ) _y (O
_1/2 R) _z (wherein Q is a para-diphenylamino-phenyl group, R is a methyl group or an ethyl group, and the ratio of x: y: z is approximately 0.2: 7: 2. .) To obtain a polysiloxane resin (T). 10 g of the polysiloxane resin (T) was dissolved in 10 g of toluene, and this was coated on a glass plate using a bar coat and dried at 140 ° C. for 15 hours. Observation under a microscope revealed that a uniform film had been formed.

Example 3 Toluene 40 was added to a flask.
g, 4- {2- (triethoxysilyl) synthesized in Synthesis Example 1
13 g of ethyl) triphenylamine and methylsilyl
Corn Resin Oligomer-Methylsiloxy Unit (MeS
iO_3/2): Dimethylsiloxy unit (Me_TwoSi
O_2/2): SiO_TwoThe unit ratio is 80: 15: 5
Containing 25 wt% of methoxy group] 45 g, methanol
Heating at 50 ° C for 2 hours while mixing 10g of water and 2g of water
And the formula: (QC_TwoH_FourSiO_3/2)_a(MeSiO_3/2)_b(Me_Two
SiO_2/2)_c(SiO _Two)_d(O_1/2R)_e (However, Q is a para-diphenylamino-phenyl group.
, Me is a methyl group, R is a methyl group or hydrogen source
Child, and the ratio of a: b: c: d: e is about 0.0.
The ratio is 6: 0.8: 0.15: 0.05: 0.3. )so
The polysiloxane resin (U) solution shown was obtained. policy
Add 10 g of the Roxaxane resin (U) solution to a glass plate using Barco
And was dried at 110 ° C. for 5 hours. microscope
As a result, it was confirmed that a uniform film was formed.
found.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Hideki Kobayashi 2-2 Chikusaigan, Ichihara-shi, Chiba Toray Dow Corning Silicone Co., Ltd. Research & Development Division (72) Toru Masatomi 2nd Chikusaigan, Ichihara-shi, Chiba 2 Toray Dow Corning Silicone Co., Ltd.

Claims (2)

[Claims] 1. A method for producing a polysiloxane-based hole transport material, comprising co-hydrolyzing and condensing the following first component and second component in an organic solvent. First component: a silicon compound capable of giving a polysiloxane resin having a ratio of monovalent hydrocarbon groups to silicon atoms of 0.5 to 1.5 by hydrolysis condensation (provided that the silicon compound is 1 selected from and
More than a seed. R ₃ SiZ R ₂ SiZ ₂ R ₁ SiZ ₃ SiZ ₄ Here, R is a monovalent hydrocarbon group and Z is a hydrolyzable group. ) And / or a partial hydrolysis condensation product thereof. Second component: a hole-transporting organosilicon compound represented by the following formula (1) A- [R ¹ SiR ² _3-n Q _n ] _p (1) (where A is a fragrance having a plurality of aromatic groups) Group III-substituted tertiary amines having an ionization potential of 4.5-6.
2 eV represents an organic group derived from a hole transporting compound, R ¹ is an alkylene group having 1 to 18 carbon atoms, and R ² is a monovalent hydrocarbon group having 1 to 15 carbon atoms which may have halogen. , Q is a hydrolyzable group, n is an integer of 1 to 3, p is 1 to
It is an integer of 3. ) 2. The polysiloxane according to claim 1, wherein the hydrolyzable group of the hole-transporting organosilicon compound represented by the general formula (1) is an alkoxy group in the method for producing a polysiloxane-based hole-transporting material. Method of manufacturing a hole transporting material.