TW386100B - Organosilicon-modified charge transporting compound and curable composition containing the compound and having charge transporting ability - Google Patents

Description

V. Description of the invention (2) Gas type polymers, such as polytetrafluoroethylene and fluorinated carbon powder, have typical low surface energy. The surface protective layer containing gold compounds and other materials has high hardness, but due to its high surface Energy, which makes cleaning difficult • Silicone resins are advantageous in terms of their low surface energy, but due to their low compatibility with other resins they cause difficulties in coagulating easily in the system, causing light Scattering * and its possible exudation and separation on the surface, leading to instability * Fluoropolymers are resins with low surface energy, but are usually insoluble in solvents and have low dispersibility, so it is difficult to separate such resins When it is made into a smooth surface, light scattering occurs due to its low refractive index, so there is a problem of transparency degradation. In addition, fluorinated fluorene polymers are usually soft and have a problem of scratching the surface. These resins also have the disadvantage of being easily charged with static electricity when used alone due to their resistance. 4. 'Invention Summary Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) An object of the present invention is to provide a silicone-modified charge-transporting compound capable of solving the above-mentioned problems and a curable composition containing the same, which can form a uniform surface layer with charge-transporting properties without Exudation or light scattering, while forming a surface layer with low surface energy and mechanical and electrical durability. First, the present invention relates to a silicone-modified charge transfer compound A- 化合物 represented by the following formula (I) · ΕΗ2 · ^-Si -fQ) β) ι (工) (Η2) 3- This paper size is applicable to China National Standards (CNS) Α4 specifications (210 X 297 mm) -5-Staff Consumption of Central Standards Bureau, Ministry of Economic Affairs Printed by the cooperative A7 B7 V. Description of the invention (1) Invention back I Inventory of jaw · The invention relates to charge-transporting compounds and curable compositions with charge-transporting properties. In particular, the present invention relates to a charge-transporting compound and a curable composition having charge-transporting properties, and the compound and composition have excellent durability, such as abrasion resistance due to its high surface hardness, Due to its low surface energy, it has excellent rust resistance and smoothness, as well as antistatic properties. Related prior art_ The surfaces of plastics and soft metals (such as aluminum) are easily scratched and soiled by mechanical and electrical effects. In severe cases, they can be used acoustically due to friction. In detail, plastic lenses, CRT surfaces, car bodies, etc. have difficulties in use after repeated damage caused by abrasion or rubber adhesion. In order to meet the various properties and characteristics required for such surfaces, various attempts have been made to provide a variety of surface protective layers mainly composed of resin. For example, metal oxide particles have been proposed to be added to the surface protective layer as conductive Particles to control their abrasion resistance and electrical resistance. Studies have also been made to add various substances to improve surface properties. For example, it has been reported that silicones with inherently low surface energy are used as additives. For example, silicone oil, polydimethylsiloxane, silicone resin powder, cross-linking. Silicone resin, poly (carbonate-silicon) block copolymer, silicone-modified polyurethane and silicone-modified polyester. This paper size is applicable to Chinese National Standard (CNS) A4 specification (2 丨 0X297mm) 1T, word (Please read the precautions on the back before filling this page)

4 A7 B7

H7.12.30 · Revision Year 0 · Master's Supplement I V. Description of Invention (4) (I) A ~ H-CH2-) ir-Si-fQ) li) 1

I (Rj) 3 ^ where A represents a charge transfer group, Q represents a hydrolysable group or a hydroxyl group, and R 2 represents a monovalent radical having 1 to 15 carbon atoms or a halogen-substituted monofluorene hydrocarbon group, which is 1 to 1 8 (Notes on the back of the poem before reading the page, then fill in this page) Yes 1-3, and 芡 Yes, 1-5 β In the formula (I), the hydrolyzable group shown by Q may include methoxy and ethoxy Methyl, methyl ethyl ketoxime, diethylamino, acetate, propyleneoxy, propoxy, butoxy and methoxyethyl, and more preferably a group represented by 0 R 1, where R 1 Is a hydrolyzable hydrazone or alkoxyalkoxy group, and is an alkyl or alkoxyalkyl group having 1 to 6 carbon atoms, including methyl, ethyl, propyl, butyl, pentyl, hexyl and Methoxyethyl · Q is preferably an alkoxy group represented by OR 1 * In general, the condensation reaction of the organic silicon compound itself is more difficult to occur when the number m of the hydrolytic groups bonded to the silicon atom is 1. , So the polymerization reaction is suppressed. • When m is 2 ^ 3, the condensation reaction and possible high cross-linking reaction can occur quickly, so * Although properties such as the hardness of the cured product are expected to be improved, the resulting The solubility of the polymer in the silicon type thermosetting resin and its reactivity may change. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. R 2 is a group directly bonded to the silicon atom. It is shown to be 1 to 15 carbons. Atomic monovalent hydrocarbon groups, including methyl, ethyl, propyl, butyl, and pentyl, which may additionally include alkenyl groups such as vinyl and allyl groups, and aryl groups such as phenyl and tolyl groups, which may additionally Monovalent hydrocarbon groups containing monohalo substitutions, such as fluorocarbons, such as trifluoropropyl, heptafluoropentyl, and nonafluorohexyl · η is 1 to 18, and the alkylene group need not be a straight bond • If η is 1 9 or more , The charge transfer group A can leave quickly, resulting in a decrease in hardness. • The size of the straight paper applies to the Chinese national standard (CNS > A4 size (210X297 mm) -7-

V. Description of the invention (2) Gas type polymers, such as polytetrafluoroethylene and fluorinated carbon powder, have typical low surface energy. The surface protective layer containing gold compounds and other materials has high hardness, but due to its high surface Energy, which makes cleaning difficult • Silicone resins are advantageous in terms of their low surface energy, but due to their low compatibility with other resins they cause difficulties in coagulating easily in the system, causing light Scattering * and its possible exudation and separation on the surface, leading to instability * Fluoropolymers are resins with low surface energy, but are usually insoluble in solvents and have low dispersibility, so it is difficult to separate such resins When it is made into a smooth surface, light scattering occurs due to its low refractive index, so there is a problem of transparency degradation. In addition, fluorinated fluorene polymers are usually soft and have a problem of scratching the surface. These resins also have the disadvantage of being easily charged with static electricity when used alone due to their resistance. 4. 'Invention Summary Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) An object of the present invention is to provide a silicone-modified charge-transporting compound capable of solving the above-mentioned problems and a curable composition containing the same, which can form a uniform surface layer with charge-transporting properties without Exudation or light scattering, while forming a surface layer with low surface energy and mechanical and electrical durability. First, the present invention relates to a silicone-modified charge transfer compound A- 化合物 represented by the following formula (I) · ΕΗ2 · ^-Si -fQ) β) ι (工) (Η2) 3- This paper size applies to China National Standards (CNS) Α4 specification (210 X 297 mm) -5-

A7 B7 V. Description of the invention (>) Hydrogenated charge transfer group A compound can be synthesized by the following method

To 20 ml of nitrobenzene was added 10.0 g of 2-amino-9,9-dimethylfluorene, 36.1 g (165.6 millimoles) of p-iodomethyl, 2 2. 9 grams (16.57 mmol) of anhydrous potassium carbonate and 7.0 grams of copper powder, followed by stirring and heating under reflux for 8 hours, after cooling the reaction mixture, suction filtration, and evaporating the resulting filtrate at a low level, The residue was purified by silica gel column chromatography to obtain 15.6 g of the title compound, m. P.: 14 1. 0 0C to 14 1 · 5 ° C * H3c- ^ g ^ (0: <〇; MA response: {Please read the notes on the back before filling out this page) The paper size of the printed paper is applicable to the Chinese National Standard (CNS) A4 (210X297 mm) 39 A7 B7 V. Description of the invention (3) where A represents a charge transfer group, Q represents a hydrolysable group or a hydroxyl group, R2 represents a monovalent hydrocarbon group having 1 to 15 carbon atoms or a halogen-substituted monovalent hydrocarbon group, and η is 1 to 18 , M is 1-3, and 芡 is 1-5. The second system of the present invention is a curable composition having charge transfer properties, which includes:-a curable resin, mainly composed of It is composed of an organosilicon polymer, in which a monovalent hydrocarbon group is bonded to a silicon atom and the ratio of the silicon atom and the hydrocarbon group is 0.5 to 15; and the organosilicon modified charge transfer compound represented by the above formula (I). The schematic diagram is shown in Figure 1. Figure 1 shows the H-NMR spectrum of 4- (2- (triethoxysilyl) ethyl] triphenylamine in Example 1. Figure 2 shows 4- in Example 4— [N, N -Bis (3,4-xylyl) amino]-[2- (triethoxysilyl) ethyl] benzene-NMR spectrum "Figure 3 shows Example 4 of 4-[Ν, Ν C-NMR spectrum of —bis (3,4-xylyl) amino]-[2- (triethoxysilyl) ethyl] benzene. A preferred system is described in the present invention. The charge transfer compound has the structure shown by the following formula (I). The paper size is applicable to China National Standard (CNS) 8-4 specifications (210 × 297 mm) (please read the precautions on the back before filling this page). Printed by the Consumer Cooperative of the Bureau of Standards. Λ -6-V. Element description of the invention C ηΗ 1βΝ 0 sp: c («) Η (») Ν (») Calculated value: 48.36 5.9 0 5. 13 Experimental value: 48.39 5.92 5. 40 (Please read the notes on the back before filling in this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs at room temperature 1.5 ml. 0 grams (about 90 millimoles) of oily sodium hydride (about 60%). After the addition is complete, the mixture is heated in an oil bath to bring the internal temperature to about 70 ° C, and stirred at the same temperature for 1 hour, then The reaction solution was cooled to room temperature, and 25.1 g (92 mmol) of diethyl-4 mononitrobenzylphosphonate and 10.0 g (48.6 mmol) of 5H-diphenyl M were added dropwise. [A, d] A solution of cycloheptene-5 ketone in 50 ml of dimethylasoterol. The resulting mixture was stirred at the same temperature for 15 minutes, and then heated and stirred in an oil bath for 2 hours while maintaining the internal temperature at 70 ° -80 ° C. After the reaction is completed, the reaction mixture is cooled to room temperature, and poured into 1 liter of saturated brine and then extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate, and the solvent is removed at low temperature. Methanol was added to the obtained residue, and the precipitated crystals were collected by filtration, and the crystals were reconstituted in a methanol / acetone mixed solvent. Crystal to obtain 10.94 g of 5- (4-nitrobenzylidene) -5H-dibenzo [a, d] cycloheptene • yield: 69.3%: m.p: 151. 5-152. 5 ° C · This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) ~ A7 B7

H7.12.30 · Revision Year 0 · Master's Supplement I V. Description of Invention (4) (I) A ~ H-CH2-) ir-Si-fQ) li) 1

I (Rj) 3 ^ where A represents a charge transfer group, Q represents a hydrolysable group or a hydroxyl group, and R 2 represents a monovalent radical having 1 to 15 carbon atoms or a halogen-substituted monofluorene hydrocarbon group, which is 1 to 1 8 (Notes on the back of the poem before reading the page, then fill in this page) Yes 1-3, and 芡 Yes, 1-5 β In the formula (I), the hydrolyzable group shown by Q may include methoxy and ethoxy Methyl, methyl ethyl ketoxime, diethylamino, acetate, propyleneoxy, propoxy, butoxy and methoxyethyl, and more preferably a group represented by 0 R 1, where R 1 Is a hydrolyzable hydrazone or alkoxyalkoxy group, and is an alkyl or alkoxyalkyl group having 1 to 6 carbon atoms, including methyl, ethyl, propyl, butyl, pentyl, hexyl and Methoxyethyl · Q is preferably an alkoxy group represented by OR 1 * In general, the condensation reaction of the organic silicon compound itself is more difficult to occur when the number m of the hydrolytic groups bonded to the silicon atom is 1. , So the polymerization reaction is suppressed. • When m is 2 ^ 3, the condensation reaction and possible high cross-linking reaction can occur quickly, so * Although properties such as the hardness of the cured product are expected to be improved, the resulting The solubility of the polymer in the silicon type thermosetting resin and its reactivity may change. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. R 2 is a group directly bonded to the silicon atom. It is shown to be 1 to 15 carbons. Atomic monovalent hydrocarbon groups, including methyl, ethyl, propyl, butyl, and pentyl, which may additionally include alkenyl groups such as vinyl and allyl groups, and aryl groups such as phenyl and tolyl groups, which may additionally Monovalent hydrocarbon groups containing monohalo substitutions, such as fluorocarbons, such as trifluoropropyl, heptafluoropentyl, and nonafluorohexyl · η is 1 to 18, and the alkylene group need not be a straight bond • If η is 1 9 or more , The charge transfer group A can leave quickly, resulting in reduced hardness. • The size of the straight paper is applicable to the Chinese national standard (CNS > A4 size (210X297 mm) -7-A7 '> fl e B7___ Weng :, V. Invention Explanation (1) Hydrocarbyl groups, such as trifluoropropyl, heptapentyl, and nonafluorohexyl; chlorohydrocarbon groups * such as chloromethyl and chloroethyl. R β is not necessarily a single category, and depends on the nature of the improvement ( Such as resin properties) and the solubility of the resin in solvents It is well known in the art that when a system has both methyl and phenyl groups, it usually has more affinity for organic compounds than a system with only methyl groups. • When a fluorohydrocarbon group is introduced into an organopolysiloxane, the fluorine atom is The polymer reduces the surface tension, so that properties such as water repellency and oil repellency are changed. At the same time, when a low surface tension is required in the present invention, the silicon unit bonded to the fluorohydrocarbon group can be introduced by copolymerization. In (III), the OR 7 group bonded to the silicon atom represents a hydroxyl group or a hydrolyzable condensation group, and R 7 is selected from a hydrogen atom and a lower alkyl group, such as methyl, ethyl, propyl, and butyl. 0 R 7 is most reactive when R 7 is hydrogen / R 7 is less reactive when the number of carbon atoms in the alkyl group is increased * and R 7 may be appropriately selected depending on the reaction system used • Hydrolyzable The number of condensed groups is represented by m. As long as m is 0.01 or higher, this group is printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page). Resin cross-linking. It is well known that the hardness of a resin is controlled by the crosslink density. This is also the case in the present invention. The hardness of a resin can be controlled by the number of hydrolytically condensable groups bonded to the silicon atom as described above. * However, if the The number of condensed groups is too large, and unreacted groups may remain in the system, so that they may be hydrolyzed in the environment of use, which has an adverse effect on surface properties. Ιη is preferably 0_. 0 1 — 1.5. One of the common characteristics is that the organic silicon polymer has a non-paper size for organic compounds. The Chinese National Standard (CNS) A4 specification (210X297 mm) is applicable. 62 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. (5) The charge-transporting group bonded to the silicon atom, because of problems such as steric hindrance, endangers stability and physical properties. Β η is more preferably 2-8, and 1-5. If β is 6 or more, it is cured. Unreacted groups will increase during the reaction, resulting in reduced electrical properties. In the present invention, the charge transfer ability means the ability to transfer a charge and it is preferable that the ionization potential is 6. 2ev or less. That is, the hydrogenated combination of the organosilicon-modified charge-transporting compound represented by the formula (I) and the charge-transporting group A preferably has an ionization potential of 6.2 ev or less, particularly 4. 5-6.2 e. If the ionization potential is higher than 6.2ev, charge injection becomes difficult, and the compound is liable to be charged. If the ionization potential is lower than 4.5 ev, the compound is easily oxidized and causes decay. The ionization potential was measured by atmospheric pressure photoelectron analysis using a surface analyzer AC-1 (manufactured by Riken Keiki K.K). When the electron-transporting group A in the above formula (I) appears with its hydrogenated compound (charge-transport property) formation formula, it may include an oxo derivative, an oxazole derivative, an imidazole derivative, and a triarylamine derivative. 'For example triphenylamine, 9 mono (p-diethylaminostyryl) M, 1,1 di (4-dibenzylaminophenyl) propane, styryl M' styrylpyrazoline, phenylhydrazone Class, α-phenylstilbene derivatives, 'blazole derivatives', triazole derivatives, phenazine derivatives, acridine derivatives, benzofuran derivatives, benzimidazole derivatives, phenphene derivatives and N-phenylcarboxamide derivative. The charge transfer group A is preferably a group represented by the following formula (I I): This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) (Please read the precautions on the back before filling this page)

-8-Alpha correction "year, month, and day supplement; V. Description of the invention (π) Very poor affinity and solubility * For example, antioxidants commonly used in general organic resins, ultraviolet light absorbers, etc. cannot be dissolved in dimethyl polysilicon Oxygen is condensed in it. • Traditional charge transfer compounds are no exception. They are difficult to dissolve at effective charge transfer concentrations. • The charge transfer compound represented by formula (I) and the above-mentioned organosilicon polymers, especially organic polymers. Siloxane has excellent compatibility and can significantly improve mechanical properties. The above-mentioned curable resin can also be crosslinked by adding a crosslinking agent during curing. The above-mentioned curable resin may also contain a crosslinking agent * a silane compound represented by the following formula (I v), which makes it easy to control the physical properties such as the hardness and strength of the surface protective layer obtained by curing the curable composition. R 8e S i X (IV) * i. Where R8 represents a straight or branched alkyl or alkenyl group having 1 to 18 carbon atoms, or a phenyl group; X represents a hydrolyzable group: and a Shows the Morbi of Si · Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs ^ (please read "Notes on the back ^ before filling this page") In formula (IV), the group shown by R 8 may include a Group, ethyl, propyl, butyl, pentyl, hexyl, vinyl, allyl, phenyl and tolyl. The hydrolyzable group shown by X may contain a hydrogen atom, methoxy, ethoxy, methyl ethyl ketone Fatty, diethylamino, ethoxy, propyleneoxy, propoxy, and butoxy beta For the above-mentioned resins, the addition of catalyst is not necessary, but when considering the curing time and curing temperature For other factors, if this paper size is used, the Chinese National Standard (CNS) Α4 specification (210X297 mm1)

Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (6) i R3 -N- R4 .C b where R3, R 4 and R 5 are each an organic group, at least one of which is an aromatic hydrocarbon Ring or heterocyclic group, and 'R 3, R 4 and R 5 may be the same or different. Therefore, a hydrogen atom is removed from any of R3, R4 and R5 to form a charge transfer group. Preferred examples of the structure represented by R 3, R 4 and R 5 are shown below. In the following structural formulas, Ph represents phenyl, Me represents methyl, E t represents ethyl, Bu represents butyl, and Pr represents propyl. "This paper size applies to China National Standard (CNS) A4 (210X297 mm) (please (Read the notes on the back before filling out this page)

-9-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs ^ η: 'λ η

V. Description of the invention (4 buckets) g methyl = f Zhuang | Wuzheng 丨 supplement v methyl ethyl ketone oxime) silane and 0.2 g dibutyltin diacetate to form a ~ uniform solution · Reference Example 3 Stomach & amp Preparation of a curing resin solution consisting of ^ -based phenyl polysiloxane resin: & 1 g of toluene was dissolved in 2 g of methyl phenyl polysiloxane (containing 1% by weight salicyl alcohol group, and Contains 40 mole% phenylsiloxane units and 20 gastric diphenylsiloxane units, 20 mole% methylsilazane monofluorene and 20 mole% dimethylsilane units) in 0.2 g of dibutyltin diacetate was added to the obtained solution to form a homogeneous solution. Reference Example 4 Preparation of a curing resin solution mainly composed of i-ketone resin: 11 g of toluene was added to 10 g of toluene. Nonafluorohexyl-polysiloxane resin (containing 1% by weight silyl acid groups, and contains 50 mole% methylsiloxane units, 10 mole% dimethylsiloxane units and 100 moles % 3, 4, 4, 5, 5, 6, 6, 6, 6-nonafluorohexylsiloxane units), 0.2 g of dibutyltin diacetate was added to the resulting solution to form A homogeneous solution--Examples of organosilicon-modified charge-transport compounds-Example 4-A combination of [2- — (triethoxysilyl) ethyl] triphenylamine The paper dimensions are applicable to China National Standards (CNS > A4 size (210 X 297 mm) (please read the precautions on the back before filling this page)

61 V. Description of the invention (7) A7 B7 n = 1 3 _ CnH2n + i η = 1 to 18

ocnH2n + l) m n = l to _4, m = l to 3 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

(Please read the notes on the back before filling this page)

This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297mm) -10-A7 B7 V. Description of the invention (less) Enter 20 ml 4.9.9 g 4 ~ [N, N > 2 (3 , 4-xylyl) amino] styrene in toluene solution * After the addition was completed, the mixture was stirred at 70 ° C for 3 hours, and then the solvent was removed under low pressure to obtain an oily pale yellow 4 _ [N, N -Bis (3,4-xylyl) amino]-[2- (triethoxysilyl) ethyl] benzene, 13.4 g (yield: 90.1%) · Η of the compound-NMR spectrum (APC 3 0 0, manufactured by Burker Co.) shown in Figure 2 «* Compound CN MR spectrum (APC 3 0 0, manufactured by Bruker Co.) is shown in Figure 3. The ionization potential of the β compound was analyzed by atmospheric photoelectricity (using surface Analyzer AC — 1, manufactured by Riken Keiki; Ki) is 5. 2 6 e ν ο Example 5 4-[N, N-bis (3,4-xylyl) amino]-[2-(triethyl Synthesis of oxysilyl) ethyl] amines in the Ministry of Relief and Relief, β-τ · " ^ ΑΠ 竹 杉 印 y (" Read the precautions before filling in this page) 1 4 1 [N, N —Hydrosulfidation reaction of bis (3,4-xylyl) amino] styrene Into a three-necked flask, 40 ml of toluene, 6.0 g (37 mmol) of triethoxysilane and 〇 · 34 millimoles of dichloro (h-cyclooctane 1 '5-diene) complex platinum (0), at room temperature and with stirring, add 20 ml of 9.9 g 4- [N, N-di After the addition of (3,4-xylyl) amino] styrene in toluene, the mixture was stirred at 701 for 3 hours, and then the solvent was removed under low pressure to obtain an oily paper. Standard? F (CNS) Λ4 specification (210X297 mm) V. Description of the invention (8) ^ §Η§τ ^ ηΗ2η + 1) m A7 B7 η to 4, m. ¾ 3-< g)-^ gf ^ CnH2n + i) mn = 1 to: 4, m = 1 to 3

(cnH2n + l) n 1 to 4, m = 〇 to 3 m

n To printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

n CH incense

CH to .6 x- = (ci, F, Br) (Please read the notes on the back before filling this page)

This paper size applies the Chinese National Standard (CNS) A4 specification (210 X 297 mm) ~ 11- RTTETirtr year-day-day supplementary sample τ-ν ·,-? Ρ ', τ in the Ministry of Economic Affairs.ΐ- Print y A7 _ B7 V. Description of the invention (l |) Yellow 4 a [N, N —bis (3,4 xylyl) amino] a [2-(triethoxysilyl) .ethyl ] Benzene, 14.0 g (yield: 94.2%). The ionization potential of the compound was analyzed by atmospheric photoelectricity (using a surface analyzer AC-l'RikenKeikiK. K.) was 5.31ev Example 6 4 Synthesis of a [3- (triethoxysilyl) propyl] triphenylamine: A synthesis of 4-bromotriphenylamine in a 200 ml three-necked flask was put into 8. 0g (4 5mmol) ) N-bromosuccinimide and 10.0 g (41 mmol) of triphenylamine, followed by 150 ml of N, N-dimethylformamide, the mixture was stirred at room temperature overnight, and then removed N, N-dimethylformamide in the reaction, and the solid matter obtained by extraction with carbon tetrachloride, removing carbon tetrachloride, and recrystallizing it twice with ethanol to obtain a white solid, 4-bromotriphenylamine, 8 2 g (yield: 6 1. 0%). Synthesis of 4-1 N, N-diphenylamino allylbenzene In a 300 ml four-necked flask, 1.0 g (40 mmol) of magnesium metal was placed, and air was replaced with nitrogen * followed by addition of 100 3 ml of diethyl ether and start stirring. 30 ml of an ether solution containing 8.6 g (27 mmol) of 4-bromotriphenylamine dissolved in the mixture was slowly added dropwise to the stirring mixture. House Mark (CNS) Λ4 Specification (210X297 mm): (¾Read the precautions before writing this page)

V. Description of the invention (9) Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 — (〇) ~ ch2 ~ (〇) C η Η2η + ι

CH = CH X: Halogen (Cl, F, Br) n = " 〇 to .3 This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page )

-12-Printed by A7 B7, Consumer Cooperatives, Central Standards Bureau, Ministry of Economic Affairs 5. Description of the Invention (1 ()) The preferred examples of hydrogenated compounds of charge transfer group A are shown below. ) A4 size (210X297mm) (Please read the precautions on the back before filling this page)

-13-A7 B7 £ V. Description of the Invention (l |) 腙: CH a CHS C Η-C H = N-N CH3

C Η

〇ι _: Ν-< g > —CH = N_N \ ΌΤ CH (C 2 Η 5) 2

N CH = N-N

I oxidation potential ionization potential

: 0.57 V): 5.22 eV CHS Ο

C = CH-CH = N-N

I CHS 0 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (Oxidation potential _ ionization potential

0.84 V) 5.47 eV (Please read the notes on the back before filling this page)

This paper is again applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm)-(4. V. Description of the invention (P- A7 B7

CH = N-N CHS

I oxidation potential_position ionization potential

: 0.83 V): 5.47 eV (C 2 Η 5) 2 Ν 舍

OToT CH = N-N〇 ^,% (oxidation potential ionization ionization.

: 0.91 V).: 5.54 eV Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs. (Please read the precautions on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) M specifications (210X 297 mm) A7 B7 V. Description of invention (13) Printed by the staff consumer cooperative of the Central Bureau of Standards, Ministry of Economic Affairs

(Please read the precautions on the back before filling in this page) Φ. Ordering, 'This paper size applies to Chinese national standard (CNS> A4 specification (210X29? Mm) -16-V. Description of invention (M)

P h CH 2 A7 B7 oTo

• C Η = N — N

I

P h CH 2 P h (oxidation potential ionization potential

0.59 V) 5.24 eV E 1

Ionization potential

0.65 V) 5.30 eV P h: N · P h

C Η = N — N

(Oxidation potential ionization potential

0.65 V) 5.30 eV Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economy P h C Η 2 N.

/) C Η = N-N

P h CEL P h P h (oxidation potential ionization potential

: 0.67 V): 5.31 eV (Please read the precautions on the back before filling this page)

This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) -17-V. Description of Invention (I5)

P h CH 2 A7 B7

P li CH 2 ci P h CH = N-M <P h oxidation potential ionization potential

: 0.76 V): 5.40 eV

E

P h

CH = N-N

Ph (oxidation potential ionization potential

: 0.81 V) Lai: 5.45 eV

P h

CH = N-N P h oxidation potential ionization potential

: 0.83V): 5.47 eV Pyrazoline: Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

N -N

Oxazoles: (CH3) 2 N

N CC s H7), (Please read the notes on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -18-V. Description of invention (16) Oxazoles:

(CH,), N oxazoles:

A7 B7

N—N

N (CH 3 〇XsV-CH = CH— (g) _N (c 2fJ 5) 2 azoles: CH, 〇

Ν (〇2η5): (Please read the notes on the back before filling this page)

• 4T Order Azazine: Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs C = N-N = CH- &lt; g &gt; -N (C2H5):

N ~ (〇) — CH = N This paper size applies the Chinese National Standard (CNS) A4 specification (2 〖0X297mm） -19-A7 B7 V. Description of the invention (Π) Diphenylhydrazine &lt; §)- ch2 ch2- / 〇) &lt; g) -CH2 CH2- &lt; g &gt; Aniline:

General ch3 ch3 (Oxidation potential: 0.78 V): Ionization potential: 5.42 eV Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

H 3 C N; ^ Q / ~~ C H; i〇) ~~ C H: (oxidation potential ionization potential

: 0.81 V): 5.45 eV (Please read the precautions on the back before filling this page)

This paper size applies to China National Standard (CNS) A4 (210X297 mm) -20-Description Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

(Please read the notes on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm). -21-Printed by the Employees' Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs.

-. A7 B7 _ -v · V. Description of the invention (19) This paper size is applicable to the Chinese National Standard (CNS) A4 (210X297 mm) •-22-(Please read the precautions on the back before filling this page )

V. Description of the invention (20) A7 · B7 ·, ^ (〇1 1〇) N— &lt; 〇

N

C C H · C H: NEt2 —〇 ~~ (wV-NPh Printed by the Consumers' Cooperatives of the t'Central Standards Bureau of the Ministry of Economic Affairs

Me Me (Oxidation potential: 0.57 V) Ionization potential: 5.22 eV &quot; Ον -〇 / N y &lt; Q ^ ~ Me Νχ ^ —Me (Oxidation potential: 0.75 V) Ionization potential: 5.40 eV (Please read the note on the back first (Fill in this page again)

This paper size applies to Chinese National Standard (CNS) A4 specification (2ΙΟχ 297 mm) -23-• V. Five, invention description (21) A7 B-7

0.76 V)

(Oxygen.Ionization potential

: 0.86 V): 5.49 eV

Me

Me printed by the Consumer Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs (Oxidation potential, Ionization potential

: 0.76 V): 5.40 eV (Please read the precautions on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -24-A7 B7 V. Description of Invention (22)

(Oxidation potential ionization potential Me, ^ M e

0.79 V) 5.43 eV M e-

N

Me Me (Please read the notes on the back before filling this page) Oxidation potential Ionization potential N- C Oxidation potential Ionization potential

0.75 V) 5.40 eV

Me, e

0.77 V) 5.41 eV Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

(Oxidation potential ionization potential

0.80 V) 5.44 eV This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) -25-A7 B7 V. Description of the invention (23)

0.79 V) 5.43 eV

0.88 V) 5.51 eV _________ «lb._ | (Please read the notes on the back before filling this page) E t

1T (oxidation potential ionization potential

0.76 V) 5.40 eV Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

0.74 V) 5.38 eV This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -26-A7 B7 V. Description of the invention (24)

: 0.77 V): 5.41 eV

Me (Please read the precautions on the back before filling this page) (Oxidation potential Ionization potential

: 0.63 V): 5-28 eV

Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

N / 0 ~ (oxidation potential ionization potential

: 0.62 V): 5.27 eV

Me

: 0.58 V): 5.22 eV The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) -27-A7 B7 V. Description of the invention (25)

(Oxidation potential ionization potential

: 0.59 V): 5.23 eV

Me Me

(Please read the precautions on the arm surface before filling out this page) (&lt; Oxidation potential Ionization potential

: 0.80 V): 5.44 eV

Me

Me -〇 \ -Q7 E N-

E (oxidation potential. Ionization potential

: 0.78 V): 5.43 eV Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

η B u

: 0.78 V): 5.43 eV This paper is sized for China National Standard (CNS) A4 (21 OX297 mm)-28-A7 W1

-29-A7 B7 Duplicate printing of employee consumption cooperation with Central Bureau of Standards, Ministry of Economic Affairs

I 30-V. Description of Invention (28)

Me M e Μ A7 B7 N-O- isoP r (oxidation potential: ionization potential M e

0.83 V) 5.47 eV J-Q-hG M e (, oxidation potential ionization potential

0.83 V) 5.47 eV

Me ~ 0 \ 〇 / C H 2 (oxidation potential. Ionization potential

0.85 V) 5.48 eV M e Μ Ν- (oxidation potential ionization potential

0.74 V) 5.38 eV (Please read the notes on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm> -31-V. Description of invention (29)

Me Q \ Q \ 〇 / Ν- A7 B7

Ν ~ Ό—0M oxidation potential ® ionization potential

: 0.80 V): 5.44 eV 〇 M e c Oxidation potential: Ionization potential

0.83 V) 5.47 eV (Please read the notes on the back before filling this page) Order

Me

Me ~ 〇 \, 0 M e 0M e (oxidation potential ionization potential

0.84 V) 5.47 eV policy, printed by employee's consumer cooperation of Central Bureau of Standards, Ministry of Economic Affairs

Q ('oxidation potential: ionization potential

0.72 V) 5.36 eV This paper size is applicable to China National Standard (CNS) A4 (210X297 mm) -32-A7 B7

-33-A7 B7 V. Description of the Invention (31) CH.3 Printed by the Consumers' Cooperative of the Central Bureau of Economics and Industry

(Please read the precautions on the back before filling this page), 1T This paper size applies the Chinese National Standard (CNS) A4 specification (21OX297mm) -34-V. Description of the invention (32)

N— &lt; \ / &gt; — M e

N— &lt; \ /) — M e Me

N—- A7 B7 (: oxidation potential ionization potential

0.78 V) 5.43 eV -Qr (oxidation potential ionization potential

Me, / Me

(Please read the notes on the back before filling this page)

0.76 V) 5.40 eV Printed by the Central Government Bureau of Labor Standards Consumer Cooperatives (Oxidation potential Ionization potential

0-82 V) 5.46 eV

Ionization potential

0.82 V) 5.45 eV This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -35-V. Description of the invention (33) Q \

Me A7 B7 :.

Me, ^ M e N-

(Oxidation potential ionization potential

: 0.89 V): 5.52 eV 〇 / M e ι &gt; M eN— ~~ \ J) (oxidation potential ionization potential

0.81 V) 5.45 eV

('Oxidation potential ionization potential

0.84 V) 5.47 eV Printed by the Consumer Standards Cooperative of the Central Standards Bureau Μ

(Oxidation potential ionization potential

: 0.79 V): 5.43 eV (Please read the precautions on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) A4 specification (2 丨 OX297 mm) -36-A7 B7 V. Description of the invention (34) Triphenylmethanes: (C 2 H5)

N (C 2 H5) 2 R = H R = C 〇 0 C Η 3 Styryl, homostilbene:

H = C Hh @)-n (c 2 Η 〇r ^ CH = Sa n X〇 &gt; -〇CH / C = C Η — (Xj) — N v E t 〇 E t 9

, Ph h (Please read the notes on the back before filling out this page)

E t 〇 N ('oxidation potential: ionization potential

: 0.50 V): 5.15 eV 2 / &gt; —NPh2 (oxidation potential m ionization potential

: 0.54 V).: 5.19 eV The paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) -37-V. Description of the invention (35)

A7 BJ

Oxidation potential

0.76 V) 5.40 eV

Me

Me ~ 〇 \

Ν-Λ / &gt;-CH

Oxidation potential

0.81 V) 5.45 eV P h Ν · C Η ~ Q /

r-CH = CH-VS c Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

: 0.82 V): 5.46 eV CH3 CH,

0 C 2ή (Please read the precautions on the back before filling out this page)

This paper size applies to China National Standard (CNS) Α4 specification (210 × 297 mm) _ 38 _

A7 B7 V. Description of the invention (&gt;) Hydrogenated charge transfer group A compound can be synthesized by the following method

To 20 ml of nitrobenzene was added 10.0 g of 2-amino-9,9-dimethylfluorene, 36.1 g (165.6 millimoles) of p-iodomethyl, 2 2. 9 grams (16.57 mmol) of anhydrous potassium carbonate and 7.0 grams of copper powder, followed by stirring and heating under reflux for 8 hours, after cooling the reaction mixture, suction filtration, and evaporating the resulting filtrate at a low level, The residue was purified by silica gel column chromatography to obtain 15.6 g of the title compound, m. P.: 14 1. 0 0C to 14 1 · 5 ° C * H3c- ^ g ^ (0: &lt;〇; MA response: {Please read the notes on the back before filling out this page) Printed on the paper of the Consumer Cooperatives of the Central Government Bureau of the Ministry of Economic Affairs, the paper size applies to the Chinese National Standard (CNS) A4 (210X297 mm) 39

A7 BJ Economy. That. Printed by the Central Consumers ’Cooperatives (Please read the notes on the back before filling this page)

V. Description of the invention (37) (〇) -ch2 c (BC) Engineering. Nitriding reaction 0 P (〇C2H5) 3 {TEP}

II (〇)-CH2P (0C2H5) I) III. Wittig reaction-〇2N-^ 0)-\ CH2P (0C2H5) 2 (If IV. Reduction 7 reaction 〇2N — @ &gt; — CH il} V · Ulmann reaction

H2N — (d) — CH {IV}

P-iodotoluene {PIT} 〇 &lt; (〇) -ch2 P (OC 2 Hs) m 〇2N — ^)-CH2P (0C2H5) jm 02n- ^ 〇)-HU}

Fe / HCl H2N (〇) &gt; — CH (IV)

O-Dichlorobenzene {ODCB} /Cu./K2C03

H, C-&lt; 〇 \ &lt; 0:) n— &lt; 〇) —CH- &lt; 〇 / 〈〇: m This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -40- Printed by A7 B7 of the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (38) 154 ml (1.34 mol) benzyl chloride (d = 1.10) and 206 ml (1.2 mol) The mixture of triethyl phosphate (d = 0.996) was gradually stirred and heated in an oil bath. The oil bath was maintained at 160 ° _ 180 ° C and stirred at reflux for 20 hours. After the reaction was completed, the pressure was reduced at low pressure. The reaction · mixture was distilled to obtain 21.5 g of diethylmandelylphosphonate. Yield: 78.6%; bp = 134.6— 1 3 5 · 0 〇C (7 mm H g) »Then 'in a 200 ml three-necked bottle, put 55.0 ml (1.05 moles) of hair Nicotinic acid (d = 1.52, 94%), stirring to reduce the internal temperature to 10 to 5 ° C, and then gradually adding 61.6 g (〇.27 Mol ) The diethyl benzyl phosphonate obtained above, after the addition is complete, the reaction mixture is stirred at the same temperature for 30 minutes, and then 2 is poured into about 600 ml of ice water and about 300 ml of ethyl acetate Ester extraction, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was distilled under reduced pressure to obtain 61.3 g of diethyl phosphonic acid 4-nitronitrate. Yield: 83 1%: b. Ρ .: 199-2 0 1. 〇. . (3 m m. H g). This paper is again applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page)

-41-V. Description of the invention C ηΗ 1βΝ 0 sp: c («) Η (») Ν (») Calculated value: 48.36 5.9 0 5.13 Experimental value: 48.39 5.92 5. 40 (Please read the note on the back first Please fill in this page again) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs at room temperature, add 150 grams of Dimethyone I to 3.6 grams (about 90 millimoles) of oily sodium hydride (about 60%), after the addition is complete, the mixture is heated in an oil bath to make the internal temperature of about 70 ° C, and stirred at the same temperature for 1 hour, and then the reaction solution is cooled to room temperature, and 25.1 g (1.5 g) is added dropwise. 92 mmol) diethyl-4 mononitrobenzyl phosphonate and 10.0 g (48.6 mmol) 5H-diphenyl M [a, d] cyclohepten-5 ketone in 50 ml di For the solution of Jia Yashuo, the resulting mixture was stirred at the same temperature for 15 minutes, and then heated and stirred in an oil bath for 2 hours while maintaining the internal temperature at 70-80 ° C. After the reaction was completed, the reaction mixture was cooled to At room temperature, it was poured into 1 liter of saturated brine and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed at low temperature. Alcohol was added to the obtained residue, and the precipitated crystals were collected by filtration. The crystals were recrystallized from a methanol / acetone mixed solvent to obtain 10.94 g of 5- (4-nitrobenzylidene) -5H-diphenyl. And [a, d] cycloheptene • Yield: 69.3%: m.p: 151.5 5-152. 5 ° C · This paper size applies to Chinese National Standard (CNS) A4 (210 X 297 mm) ) ~ A7 B7 V. Description of the invention (40) Element analysis shows C22HieN 0 CC%) H (%) N (%) Calculated value: 81.21 4.65 4.3 0 Experimental value: 81.18 4.69 4. 31 (Please read the precautions on the back first Fill out this page again) To 150 ml of N, N-dimethylformamide, add 10.0 g (30.7 mmol) of the above 5- (4-nitrobenzylidene) — 5H —di Benzo [a, d] cycloheptene, 8. 0 g (143 mmol) of reduced iron powder and 2. 70 ml (30.6 mmol) of concentrated hydrochloric acid (d: 1-18, 35%), The resulting mixture was heated to an internal temperature of about 70 ° C, and then heated and stirred at this temperature for 3 hours. After the reaction was completed, the reaction mixture was cooled in an ice-water bath, and about 12.4 ml of a 10% aqueous sodium hydroxide solution was added, followed by Scramble Filter by suction, pour the resulting filtrate into about 1 liter of saturated brine and extract with ethyl acetate. Dry the organic layer over anhydrous sodium sulfate and remove the solvent at low temperature. Add methanol to the resulting residue and filter. The precipitated crystals were collected and recrystallized from methanol to obtain 8.4.1 g of 5- (4-aminobenzylidene) -5H-dibenzo [a'd] cycloheptene. Yield: 92.7%; m p.: 119-120. (:. This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm). Ordering economy, printed by the Ministry of Standards Bureau's Consumer Cooperatives-43 — A7 ________B7 V. Explanation of the invention (41) Element analysis C22H17N: CC %) H (%) N (%) Calculated value: 89. 46 5. 80 4. 74 Experimental value: 8 9.41 5.33 4.76 (Please read the precautions on the back before filling out this page) Staff Consumer Cooperatives, Central Bureau of Standards, Ministry of Economic Affairs Printed in 30 ml of o-dichlorobenzene and added 7.90 g (26.7 mmol) of 5 —. (4-aminobenzylidene) — 5.H —dibenzo [a D] Cyclopeptide, 22- 0 g (101 mmol) p-iodotoluene '11 .0 g (79-6 mmol) anhydrous sodium carbonate and 22 g of copper powder, the mixture is about 190 Stir under reflux in an oil bath at ° C for 7 hours. After the reaction is completed, suction filtration is performed, and then the filtrate is successively washed with a 3 5% sodium thiosulfate aqueous solution and saturated saline. The solvent was removed, and about 60 ml of acetone was added to the obtained residue. The crystals precipitated were collected by filtration, and the mixture was treated with acetic acid. The ethyl acetate / n-hexane mixture was recrystallized from the solvent to obtain 9.52 g of 5- [4-((bis-tolylamino) benzylidene) -5H-dibenzo [a'd] cycloheptene. Yield: 75.0%; m. Ρ .; 168 · 0—169. 0 0C. This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) -44-A7 B7 V. Description of the invention (42) Element analysis C3eH29N: CC%) H (%) N (%) Calculated value: 8 9.46 5.80 4.74 Experimental value: 89.41 5.83 4.7 6 The preferred examples of the organosilicon-modified charge-transport compounds of the present invention are as shown below. Triphenylamines:

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

B = ten eCAVSi-tQUi I (R2) 3-m where Q represents a hydrolyzable group or a hydroxyl group 'R2 represents a monovalent hydrocarbon group having 1 to 15 carbon atoms or a halogen-substituted monovalent hydrocarbon group, nSl ·-18' ^^ is 1-3 and i? Are 1 to 5. (Same applies hereinafter) This paper size applies Chinese National Standard (CNS) A4 specification (2 丨 〇 &lt; 297 mm) -45-A7 B7 V. Description of the invention (43)

Printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page)

This paper size applies to China National Standard (CNS) A4 (2IOX297 mm) -46-V. Description of Invention (44)

B τ / A7 B7 M e Μ ^ // ~ \\ /;

Me

Me Recognize Me M

B // (Please read the notes on the back before filling this page)

N

B

CH,) 3 ^ 2, order

C H 3 ^ 2 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs and Ministry of Economic Affairs This paper is sized to the Chinese National Standard (CNS) A4 (210X297 mm) -47-A7 B7 V. Description of the invention (4δ)

Ν eΜ eΜ

Β

Ν

(Please read the notes on the back before filling this page)

Order Μ

6Μe / Μ Ν

Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs This paper is sized to the Chinese National Standard (CNS) Α4 (21〇 × 29 &lt; 7 mm) ~ 48-Mingfa A7 BJ,

Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling this page)

This paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm), -49-V. Description of the invention (47) CH3 A7? 7,

CH

CH ':

(B

B

OJ V-: H == c ^ 〇 · Β Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs CH, 3 Η 3 C-~ (〇 ^ — (δ) — Ν

声 '^ &lt; 〇) —CH (Please read the notes on the back before filling this page)

The size of this paper applies to Chinese National Standard (CNS) A4 specification (210 × 297 mm) 50-A7 R7 V. Description of the invention (48)

C H3 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

This paper size applies to Chinese national standard (CNS> A4 specification (210X297mm) -51-V. Description of invention (49) A7 .B7

NE 12-&lt; Q) —Q &gt; ~ NPh 2 &quot; B

Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling this page)

This paper size is applicable to China National Standard (CNS) A4 specification (210X 297 mm), -52-A7 37 V. Description of invention (50)

Me, ._ Me

N— &lt;

B

Printed by the Ministry of Economic Affairs.t Central Standards Bureau's Consumer Cooperatives

This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -53-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A 7 __; _ V. Description of the invention (51)

Me Me (Please read the notes on the back before filling out this page) This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm)..--54-A7 B Factory-Staff of Central Bureau of Standards, Ministry of Economic Affairs Printed by Consumer Cooperatives V. Invention Description (52)

(Please read the notes on the back before filling this page)

The size of the paper is applicable to the Chinese National Standard (CNS) A4 (210X2.97 mm).--55-V. Description of the invention (53)

Me

Me

Me ~ 0 \ ~ q / A7 .37.

E t i ^ E

B

Me, ^ M e B N—-

Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) -56-A7 Economic Hit

-57-

A \ — / 5 5 / V

Ν ο-- · Μ Μ

Ν

MICIM

Μ Μ

Ν 2 Η c (Please read the notes on the back before filling in this page) 通 11 、 1Τ

Β C

Ν ό e Μ ο Economic and Central Bureau of Standards staff consumer cooperatives printed this paper size applicable to China National Standard (CNS) A4 specifications (210X 297 mm) -58-

This paper size applies to China National Standard (CNS) A4 (210X297 mm) -59-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (57) Silicone shown by the formula (I) above Modified charge-transporting compounds can be synthesized by known methods. For example, the preferred method is a compound having a vinyl group on the aromatic ring and a substituent in the presence of a platinum catalyst or an organic peroxide catalyst. Hydrosilylation reaction between hydrogenated silicon compounds. There is no particular limitation on the platinum catalyst used. Any platinum catalyst used in the synthesis of ketone rubbers for general hydrosilation reactions and addition molding can be used, including platinum chloride, chloroplatinic acid, platinum-hydrocarbon complexes and Platinum-phosphine complex. There is no particular limitation on the amount of platinum catalyst used, and the amount of catalyst used should be as low as possible, so that any residual catalyst does not have a bad effect on the properties of the product. When the compound of the present invention is formed from an aromatic ring When a compound having a vinyl group and a hydrogenated silicon compound having a substituent are synthesized through an addition reaction in the presence of a platinum catalyst, the reaction occurs at the α-or yS-position of the vinyl group, and usually produces a mixture. In the present invention, it is useful if the reaction is at the α-position or the 8-position. When the number of carbon atoms of the hydrocarbon group and the charge transfer group bonded to the silicon atom is small, it reacts with; the compound at the δ-position is more advantageous to avoid steric obstacles. The available organic peroxides are those with a half-life at room temperature or above, Particularly suitable are alkyl peroxides (such as lauryl peroxide) because they hardly pull out hydrogen atoms. For compounds without a vinyl group, a vinyl group can be introduced into an aromatic ring, for example, via a methylation reaction and a reduction reaction or a dehydration reaction, or directly via a Witlig reaction, so that it can be used as a starting material in the present invention. Next, the following description of the charge transfer properties of the present invention can be used. This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) — -60-(Please read the precautions on the back before filling this page)

A7 B7__ 5. Description of the invention (58) Curable resin contained in the chemical composition. The main component of the curable resin, the silicone polymer, examples are organic polysiloxanes, polysilylsiloxanes and polysilylsiloxanes, in which the unit price of silicon atoms is bonded The ratio of the number of hydrocarbon groups to the number of silicon atoms is 0.5 to 1.5. When the ratio is less than 1.0, the composition of the polymer is similar to that of glass, so that the weight loss due to heating is reduced and the resin product becomes harder. When the ratio is lower than 0.5, it is difficult to make a film. On the other hand, when the ratio is greater than 1.0, the polymer exhibits the opposite trend, for example, the organic polysiloxane is converted into a polydiorganopolysiloxane when the ratio is 2.0. Therefore, if the ratio is greater than 1.5, the polymer becomes too elastic, resulting in insufficient hardness. The organopolysiloxane preferably contains a structural unit represented by the following formula (I I I). 'R 6 „S i O C4-nm) / 2 (0 RT) π. (III) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this purchase), among which the indicator 1- 18 linear or branched alkyl or alkenyl groups, or aryl groups; R 7 shows that alkyl groups with 1 to 4 carbon atoms, j η is 0.5 to 1.5 on average; and m average Yes 0_ 01 — 1_ 5 »

Re's straight or branched alkyl group with 1 to 18 carbon atoms may contain methyl, ethyl, propyl, butyl, pentyl, hexyl, 2-ethylhexyl, dodecyl and octadecane Alkenyl may include 'for example vinyl and allyl; and aryl may include phenyl and tolyl. Re may additionally contain halogen-substituted, straight-chain or branched-chain saturated hydrocarbon groups with 1 to 1 to 8 carbon atoms, such as fluorine. This paper is sized to the Chinese National Standard (CNS) A4 specification (210X297 mm) &quot; '~~~ -61-A7 '&gt; fl e B7___ Weng :, V. Description of the invention (1) Hydrocarbon groups, such as trifluoropropyl, heptapentyl and nonafluorohexyl; chlorohydrocarbon groups * such as chloromethyl and chloroethyl · R β is not necessarily a single category and is selected based on the properties to be improved (such as the properties of the resin) and the solubility of the resin in a solvent. It is conventionally known in the art that when the system has both methyl and phenyl groups, it is usually More affinity for organic compounds than systems with only methyl groups. • When fluorohydrocarbon groups are introduced into organopolysiloxanes, the surface tension of fluorine atoms and other polymers decreases, which changes properties such as water repellency and oil repellency. Meanwhile, when a low surface tension is required in the present invention, a silicon unit bonded to a fluorohydrocarbon group may be introduced by copolymerization. In the above (III), the OR 7 group bonded to the silicon atom represents a hydroxyl group or a hydrolyzable condensation group, and R 7 is selected from a hydrogen atom and a lower alkyl group, such as methyl, ethyl, propyl, and butyl 0 R 7 is most reactive when R 7 is hydrogen / R 7 is less reactive when the number of carbon atoms in the alkyl group is increased * and R 7 may be appropriately selected depending on the reaction system used The number of hydrolytic condensation groups is represented by m. As long as m is 0.01 or higher, this group is printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) and can be used in the present invention The resin is being crosslinked. It is well known that the hardness of a resin is controlled by the crosslink density. This is also the case in the present invention. The hardness of a resin can be controlled by the number of hydrolytically condensable groups bonded to the silicon atom as described above. * However, if the The number of condensed groups is too large, and unreacted groups may remain in the system, so that they may be hydrolyzed in the environment of use, which has an adverse effect on surface properties. Ιη is preferably 0_. 0 1 — 1.5. One of the common characteristics is that the organic silicon polymer has a non-paper size for organic compounds. The Chinese National Standard (CNS) A4 specification (210X297 mm) is applicable. π) Poor affinity and solubility * For example, the antioxidants commonly used in general organic resins, ultraviolet light absorbers, etc. cannot be dissolved in dimethylpolysiloxane and will condense in them. • Traditional charge transfer compounds are no exception. Difficult to dissolve at effective charge transfer concentration • The charge transfer compound represented by formula (I) and the above-mentioned organosilicon polymers, especially organopolysiloxanes, have excellent compatibility and can significantly improve mechanical properties. The curable resin may be crosslinked by adding a crosslinking agent during curing. The above-mentioned curable resin may also contain a crosslinking agent * a silane compound represented by the following formula (I v), which makes it easy to control the physical properties such as the hardness and strength of the surface protective layer obtained by curing the curable composition. R 8e S i X (IV) * i. Where R8 represents a straight or branched alkyl or alkenyl group having 1 to 18 carbon atoms, or a phenyl group; X represents a hydrolyzable group: and a Shows the Morbi of Si · Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs ^ (please read "Notes on the back ^ before filling this page") In formula (IV), the group shown by R 8 may include a Group, ethyl, propyl, butyl, pentyl, hexyl, vinyl, allyl, phenyl and tolyl. The hydrolyzable group shown by X may contain a hydrogen atom, methoxy, ethoxy, methyl ethyl ketone Fatty, diethylamino, ethoxy, propyleneoxy, propoxy, and butoxy beta For the above-mentioned resins, the addition of catalyst is not necessary, but when considering the curing time and curing temperature For other factors, if this paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm1) printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs A7 ____B7___ 5. Description of the invention (61) catalyst, you can use the general tradition The catalyst used for curing the silicone polymer is suitable. It is selected from alkyl tin organic acid salts, such as dibutyl Tin diacetate, dibutyltin dilaurate, and dibutyltin octanoate, or organic stannates, such as n-butyl stannate. Examples of the silane compound represented by formula (IV) used as a crosslinking agent include formazan Trimethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, phenyltriethoxysilane, and silanes having an ethoxy group instead of an alkoxy group, such as methyl ethyl ketone, diethylamine Or isopropenyloxy. The cross-linking agent may be in the form of an oligomer (such as polyethylene silicate). The organosilicon polymer used in the present invention can be prepared by a known method, which includes Japanese Laid-Open Patent 2 6 — 2 6 9 6 and 2 8 — 6 2 9 7 and methods uncovered, and Chemistry and Technolozy of Silicones, Chapten 5, P 1 9 1 (Welter Noll, Academic

Press, Inc., 19 6 8)). For example, an organic alkoxysilane or an organic halosilane having an average number of monovalent organic groups bonded to a silicon atom of 0.5 to 1.5 is dissolved in an organic solvent, followed by hydrolysis and condensation in the presence of an acid or base to A polymerization reaction was performed, and then the solvent was removed. The silicone polymer used in the present invention is soluble in a solvent containing aromatic hydrocarbons such as toluene and xylene, aliphatic hydrocarbons such as cyclohexanone and hexane, halogen-containing hydrocarbons such as chloroform and chlorobenzene, and Alcohols, such as ethanol and butanol. The curable composition of the present invention comprises a curable resin, which is mainly composed of an organosilicon polymer and an organosilicon-modified charge-transporting compound. The curable composition can pass through, for example, two solvents that can dissolve simultaneously. The solvent size of this paper applies the Chinese National Standard (CNS) A4 specification (210X297 mm) (please read the precautions on the back first and fill in this page).

~ 64-A7 B7 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Silicone-modified charge-transporting compounds are preferably mixed in an amount of 20-200 parts by weight per 100 parts by weight of the solid-curing resin without solvent. The amount of silicone-modified charge-transporting compounds should not be low. At 20 parts by weight, the charge transfer properties become insufficient and the potential increases. If the amount is higher than 200 parts by weight, it is not suitable because the mechanical strength decreases and the surface energy increases. The amount of the organosilicon-modified charge-transporting compound is more preferably from 30 to 150 parts by weight per 100 parts by weight of the curable resin. In the curable composition of the present invention, the curable resin can be partially reacted with a silicone-modified charge-transporting compound to make it into the form of a solution or a dispersion so that it can be applied to a photosensitive film after curing. Curing conditions. The composition should be heated at 100 ° C to 200 ° C. If the heating temperature is lower than 100 ° C, the curing reaction will take a long time, which may cause unreacted hydrolysis groups to remain. If the heating temperature is higher than 200 ° C, the charge transfer group is susceptible to deterioration by oxidation, resulting in undesired results. More preferably, the composition is heated at a temperature of 1 2 0_1 6 0 / C to cure. The curable composition having charge transfer properties of the present invention can form a surface protective layer having charge transfer properties after curing. In the curable composition having charge transfer properties of the present invention, in addition to the above-mentioned compounds, additives may be used to improve mechanical properties and durability. Useful additives include antioxidants, UV absorbers, stabilizers, lubricants, and conductivity control agents. The curable composition with charge transfer properties of the present invention can be used (please read the precautions on the back before filling out this page) nr, language

This paper is again applicable to China National Standard (CNS) A4 (210X297 mm) -65-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (63) Surface protection with high hardness and low surface energy Floor. 5—50 # m。 When used at this time, the thickness of the surface protective layer is 0. 5—50 # m. If it is thinner than 0.5, sufficient protective effect cannot be obtained, and if it is thicker than 5 0 // m, the cost will increase. EXAMPLES The present invention will be further described in detail by the following examples. -Curable resin mainly composed of organopolysiloxane-Reference Example 1 Preparation of a curable resin solution composed mainly of methylpolysiloxane resin f ft '··· Prepare · Dissolve 10 g in 10 g of toluene Methylpolysiloxane (containing 1% by weight of silanol groups and containing 80 mol% methylsiloxane units and 20 mol% dimethylsiloxane units), 5 was added to the resulting solution 3 g of methyltrimethoxysilyl and 0.2 g of dibutyltin diacetate to form a homogeneous solution. Reference Example 2 Preparation of a curing resin solution mainly composed of methyl polysiloxane resin: 10 g of methyl polysiloxane (containing 1% by weight of silanol groups and 10% by weight) was dissolved in 10 g of toluene. 0 mole% methylsiloxane units and 20 mole% dimethylsiloxane units) * 11.5 was added to the resulting solution. This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) ) (Please read the notes on the back before filling out this page) Yin _ Order 66 Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs ^: 'λ η

V. Description of the invention (4 buckets) g methyl = f Zhuang | Wuzheng 丨 supplement v methyl ethyl ketone oxime) silane and 0.2 g dibutyltin diacetate to form a ~ uniform solution · Reference Example 3 Stomach & amp Preparation of a curing resin solution consisting of ^ -based phenyl polysiloxane resin: &amp; 1 g of toluene was dissolved in 2 g of methyl phenyl polysiloxane (containing 1% by weight salicyl alcohol group, and Contains 40 mole% phenylsiloxane units and 20 gastric diphenylsiloxane units, 20 mole% methylsilazane monofluorene and 20 mole% dimethylsilane units) in 0.2 g of dibutyltin diacetate was added to the obtained solution to form a homogeneous solution. Reference Example 4 Preparation of a curing resin solution mainly composed of i-ketone resin: 11 g of toluene was added to 10 g of toluene. Nonafluorohexyl-polysiloxane resin (containing 1% by weight silyl acid groups, and contains 50 mole% methylsiloxane units, 10 mole% dimethylsiloxane units and 100 moles % 3, 4, 4, 5, 5, 6, 6, 6, 6-nonafluorohexylsiloxane units), 0.2 g of dibutyltin diacetate was added to the resulting solution to form A homogeneous solution--Examples of organosilicon-modified charge-transport compounds-Example 4-A combination of [2- — (triethoxysilyl) ethyl] triphenylamine The paper dimensions are applicable to China National Standards (CNS &gt; A4 size (210 X 297 mm) (please read the precautions on the back before filling this page)

61 Printed by A7 _____B7___ of the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the Invention (65) Into a three-necked flask, 10 1.4 g of triphenylamine and 3 5.5 ml of DMF (dimethylformamide) ), With ice water cooling and stirring, add 84.4 milliliters of phosphonium chloride as appropriate, then raise the temperature to 95 ° C for 5 hours, and pour the resulting reaction solution into 4 warm water, It was stirred for 1 hour, and then the precipitate formed was collected by filtration, and washed with an ethanol / water (1: 1) mixture to obtain 9 1.5 g of 4- (N, N-diphenylamino) benzaldehyde (yield). : 81.0%). 8 克 Bromine synthesis of one 4-vinyltriphenylamine in a one-necked flask was placed in 14.6 grams of sodium hydride and 700 ml of 1.2-dimethoxyethane, and stirred at room temperature. After trimethyl iron was added, a drop of absolute ethanol was added, and the reaction was allowed to proceed at 70 ° C for 4 hours. Then, 100 g of 4- (N, N-diphenylamino) benzaldehyde was added, and the temperature was raised to 7 The reaction was allowed to proceed at 0 ° C for 5 hours. The obtained reaction solution was filtered, and the filtrate and the ether extract of the precipitate were mixed together and washed with water. Then, the ether solution was dried with calcium chloride, and the ether was removed to obtain a crude reaction product. After recrystallization from ether, needle-shaped pale yellow vinyltriphenylamine was obtained. 83.4 g (yield: 84.0%) of 9-4 vinyltriphenylamine was hydrosulfurized in a three-necked flask and placed in 40 ml. Toluene, 9.9 grams (60 millimolar) of triethoxysilane and 0.018 millimolar of platinum (0) tris (tetramethyl-divinyldisiloxane) in toluene. At room temperature and with stirring, 20 ml of a toluene solution containing 8.2 g of 4-vinyltriphenylamine was added dropwise. After the addition was completed, the mixture was at 70. (: Stir down for 3 hours. This paper is again applicable to Chinese national standards ([Called the 8-4 specification (210 &gt; &lt; 297mm): -68-(Please read the precautions on the back before filling in this page)

Printed A7 £ 7_ by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (66), and then the solvent was removed under low pressure to obtain an oily pale yellow 4 — [2- (triethoxysilyl) ethyl ] Triphenylamine, 12.1 g (yield: 91.7%). -H-NMR spectrum of the compound (APC300, Burker

Co.) is shown in Figure 1 / »The ionization potential of the compound was analyzed by atmospheric photoelectricity (using a surface analyzer AC — 1, R [ken Ke’iki; K. [manufactured]) is 5: 6 8 ev 〇 Example 2 4 Synthesis of [2- (methyldiethoxysilyl) ethyl] triphenylamine_ Hydrogenation reaction of 4-vinyltriphenylamine Into a three-necked flask was placed 40 ml of toluene, 8.1 G of methyldiethoxysilane and 0.018 mol of platinum (0) tris (tetramethyl-divinyldisilazane) in toluene, one by one at room temperature with stirring 20 ml of a toluene solution containing 8-2 g of vinyl triphenylamine was added dropwise. After the addition was completed, the mixture was stirred at 70 ° C for 3 hours, and then the solvent was removed under low pressure to obtain an oily pale yellow 4 — [2 — ( Methyldiethoxymethanyl) ethyl] triphenylamine, 11.2 g (yield: 9i. 4%). The ionization potential of the compound after atmospheric photoelectric analysis (using surface analyzer Ac_1, manufactured by Riken Keiki KK · K) is 5 · 6 6 ev ο This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) — '-69-(Please read the notes on the back before filling this page)

A7 B7 V. Explanation of the invention (67) Example 3 Synthesis of 4, 4 /, 4, 1, 313 [2- (triethoxysilyl). Ethyl] triphenylamine: Tris (4-methylamyl) Synthesis of Phenyl) amine In a three-necked flask, 50.7 g of triphenylamine and 53.3 ml of DMF were built-in. With cooling and stirring with ice water, 12 6. 6 ml of phosphonium chloride was added dropwise. After that, the temperature was raised to 95 ° C. The reaction was carried out for 5 hours. The obtained reaction solution was poured into 5 warm water and stirred for 1 hour. Then the precipitate formed was collected by filtration, and the mixture was filtered with Z ether / water (1: 1 ) Of the mixture was washed to obtain 65.3 g of tri- (4-methylfluorenylphenylamine) (yield: 9 5.9%). Synthesis of tris (4-vinylphenyl) amine In a three-necked flask, put 14.6 g of sodium hydride and 70 ml of 1.2-dimethoxyethane, and stir at room temperature to add 1 30.8g of trimethylbromide bromide, followed by the addition of a drop of absolute ethanol, allowed the reaction to proceed at 70 ° C for 4 hours, and then added 40.2g (4-methylamidophenyl) amine to the mixture. The reaction was allowed to proceed at 70 ° C. for 5 hours. The resulting reaction solution was filtered to remove the filter cake. The ether extract of the filter cake was mixed with the filtrate and washed with water, and then the ether was removed to obtain a reaction mixture. After recrystallization from ether twice, 38.4 g of needle-like pale yellow tris (4-vinylphenyl) amine was obtained (yield: 97.3%). —Hydrogenation of tris (4-vinylphenyl) amine Into a three-necked flask was placed 40 ml of toluene, 9.9 g (60 mmol) of triethoxysilane and 0.018 mmol The paper size of Mor in toluene is applicable to the Chinese National Standard (CNS) A4 specification (21 ×: 297 mm) (Please read the precautions on the back before filling this page) Printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs -70-A7 B7 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs _ V. Description of the invention (68) Diplatinum (〇) tris (tetramethyl-divinyldisiloxane), at room temperature and with stirring 20 ml of a toluene solution containing 3.3 g of tris (4-vinyl'ylphenyl) amine was added dropwise. After the addition was completed, the mixture was at 70. Stir for 3 hours at 0 ° C, then remove the solvent under reduced pressure to obtain an oily pale yellow 4,4 &gt; '4 &quot; -tri [2- (triethoxysilyl) ethyl] triphenylamine, 7.8 g (Yield: 80.6). The ionization potential of the compound was analyzed by atmospheric photoelectric analysis (using surface analyzer AC-1, manufactured by Riken Keiki K.K.) to be 5 ·· 6 5 ev 〇 Example 4 4-[N, N-2 (3, 4 1-2 Synthesis of tolyl) amino]-[2- (triethoxysilyl) ethyl] benzene: Synthesis of mono-N, N-bis (3,4-xylyl) aminobenzene 20 ml of nitro To benzene was added 38.5 g (166 mmol) of 4-iodine-o-xylene, 22.9 g (166 mmol) of anhydrous potassium carbonate and 7.0 g of copper powder, followed by stirring and heating to reflux for 8 hours. The reaction mixture was cooled and filtered to remove precipitates, and the filtrate (crude reaction product) was passed through a silica gel column to obtain 15.7 g of N, N-bis (3,4-xylyl) aminobenzene (yield: 69 %). —4 — [N, N—Di (3,4-xylyl) amino] benzaldehyde was synthesized in a three-necked flask with 12.6 g of N, N —di (3 ′ 4-xylyl) ) Aminobenzene and 35.5 ml of DMF, apply Chinese national standard (CNS> A4 specification (210X297 mm)) on ice paper scale (please read the precautions on the back before filling this page)

Order -71-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of Invention (69) Add 84_ 4 ml of Phosphonium Chloride as appropriate while cooling and stirring, and then increase the temperature I to 9 5 ° C The reaction was allowed to proceed for 5 hours. The resulting reaction solution was poured into 4 warm water and stirred for 1 hour, and then the precipitate formed was collected by filtration and washed with a mixture of ethanol / water (1: 1) to obtain 107. 6 g of 4- [N, N-bis (3,4-xylyl) amino] benzaldehyde (yield: 79.0%). Synthesis of 2 4 [[N, N —bis (3,4-xylyl) amino] styrene] In a one-necked flask was placed 12.1 g of sodium hydride and 5 8 0 ml of 1.2-dimethoxy Ethyl ethane was added with stirring at room temperature; 108.5 g of trimethylbromide bromide was added, and then a drop of anhydrous ethanol was added, and the reaction was allowed to proceed at 70 ° C for 4 hours, and then 100 g of 4-[N N-bis (3,4-xylyl) amino] benzaldehyde, the temperature was raised to 70 ° C to allow the reaction to proceed for 5 hours, the resulting reaction solution was filtered to collect the filter cake, and the filter cake was extracted with ether, and The extract was mixed with the filtrate and washed with water, and then the ether solution was dried with calcium chloride. The ether was removed to obtain a crude product, and the ether was recrystallized twice to obtain needle-like 4-[N, N-di (3, 4 1 xylyl) amino] styrene, 84.5 g (yield: 85.0%). —4 — [N, N —bis (3,4-xylyl) amine] Hydrogenation reaction of styrene In a three-necked flask, 40 ml of toluene, 60 g of triethoxysilane and 0.5 · 4 millimoles in toluene _ diplatin (0) tri (tetramethyl 1 1 &quot; ———.--Yl-divinyl disiloxane) at room temperature with stirring The paper size is added dropwise to the Chinese National Standard (CNS) 8-4 specifications (nO X297 mm) &quot; -72-(Please read the precautions on the back before filling this page)

A7 B7 V. Description of the invention (less) After adding 20 ml of 4.9.9 g of 4 ~ [N, N &gt; bis (3,4-xylyl) amino] styrene in toluene solution *, The mixture was stirred at 70 ° C for 3 hours, and then the solvent was removed under low pressure to obtain an oily pale yellow 4_ [N, N-bis (3,4-xylyl) amino group]-[2 — (three Ethoxysilyl) ethyl] benzene, 13.4 g (yield: 90.1%) · Compound Η-NMR spectrum (APC 300, manufactured by Burker Co.) is shown in Figure 2 «* Compound CN The MR spectrum (APC 300, manufactured by Bruker Co.) is shown in Fig. 3. The ionization potential of the β compound was analyzed by atmospheric photoelectricity (using a surface analyzer AC-1, manufactured by Riken Keiki; Ki) to be 5. 2 6 e ν ο Example 5 Synthesis of 4— [N, N —bis (3,4—xylyl) amino] — [2- (triethoxysilyl) ethyl] amine β-τ · &quot; ^ ΑΠ 竹 杉 印 y (&quot; Read the back notice first and then fill out this page) 1 4 1 [N, N —bis (3,4 xylyl) amino] styrene Hydrogen sulfide The flask was charged with 40 ml of toluene, 6.0 g (37 mmol) of triethoxysilane and 0.34 mmol of dichloro (h-cyclooctyl 1 '5-diene) complex platinum (0) 20 ml of a toluene solution containing 9.9 g of 4- [N, N-bis (3,4-xylyl) amino] styrene was added dropwise at room temperature with stirring. After the addition, the mixture was Stir for 3 hours at 701, and then remove the solvent under low pressure to obtain an oily paper. The paper size is applicable to the Chinese g family standard? F (CNS) Λ4 specification (210X297 mm). RTTETirtr -ν ·,-? ρ ', τ disappear in Hezhu. ΐ- 印 y A7 _ B7 V. Description of the invention (l |) Yellow 4 a [N, N —bis (3,4 xylyl) amino group 〕-[2-(triethoxysilyl) .ethyl] benzene, 14.0 g (yield: 94.2%). The ionization potential of the compound was analyzed by atmospheric photoelectricity (using surface analyzer AC -l 'RikenKeikiK. K.) is 5. 31ev Example 6 4 Synthesis of [3- (triethoxysilyl) propyl] triphenylamine: Synthesis of 4-bromotriphenylamine at 2 0 0 8.0 克 （4 5 mmol) N-bromosuccinimide and 10.0 g (41 mmol) of triphenylamine, followed by 150 ml of N, N-dimethylformamide, and the mixture was stirred at room temperature Overnight, then the N, N-dimethylformamide in the reaction was removed, and the solid matter obtained by extraction with carbon tetrachloride was removed. The carbon tetrachloride was removed and recrystallized twice with ethanol to obtain a white solid, 4-bromobromide. Triphenylamine, 8.2 g (yield: 61. 0%). Synthesis of 4-1 N, N-diphenylamino allylbenzene In a 300 ml four-necked flask, 1.0 g (40 mmol) of magnesium metal was placed, and air was replaced with nitrogen * followed by addition of 100 3 ml of diethyl ether and start stirring. 30 ml of an ether solution containing 8.6 g (27 mmol) of 4-bromotriphenylamine dissolved in the mixture was slowly added dropwise to the stirring mixture. House Mark (CNS) Λ4 Specification (210X297 mm): (¾Read the precautions before writing this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 ____B7 V. Description of the Invention (72) Then the remaining 4-bromotriphenylamine is added dropwise. After the addition was completed, reflux was performed for 1 hour to obtain a Grignand reagent solution, and the resulting reagent solution was cooled to room temperature, and then slowly added dropwise to 40 ml containing 2. under ice cooling. 1 g (27 mmol) of dipropyl chloride in ether. After the addition was completed, the reaction mixture was refluxed for 2 hours to ripen the reaction, and then 50 ml of water was added for hydrolysis while cooling with ice. Secondly, the ether layer was collected, rinsed once with a saturated aqueous sodium hydrogen carbonate solution, and rinsed with water two Then, it was dried over anhydrous sodium sulfate, and ether was removed after drying to obtain a white solid, 4-N, N-diphenylaminoallylbenzene, 4.9 g (yield: 63-3%). —4 N, N_diphenylaminoallylbenzene hydrosulfation reaction In a three-necked flask was placed 40 ml of toluene, 6.0 g (37 mmol) triethoxysilane and 0.54 7grams (3 4mmols) of platinum (0) tris (tetramethyldivinyldisilazane) in toluene, and 20ml of 9.7g (3 4mmol) was added dropwise at room temperature with stirring. Mol) 4-.N, N -diphenylaminoallylbenzene in toluene. After the addition was completed, the mixture was stirred at 70 ° C for 3 hours, and then the solvent was removed under reduced pressure to obtain -oily pale yellow 4- [3- (triethoxysilyl) propyl] triphenylamine, 10%. 7 g (yield: 70 · 1%) »The ionization potential of the compound was analyzed by atmospheric photoelectric analysis (using surface analyzer AC-1, manufactured by Riken Keiki K · K) as 5. 7 2 ev ο Example 7 This paper size Applicable to China National Standards (CNS) Α4 specifications (210 X 297 male: --75-(Please read the precautions on the back before filling this page)

Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (73) 4 — Synthesis of 4- (triethoxysilyl) butyl] triphenylamine: —4 — Synthesis of methyltriphenylamine To 30 ml of o-dichlorobenzene was added 4.5 grams (27 millimoles) of diphenylamine, 11.0 grams (51 millimoles) of p-iodotoluene, and 5.5 grams (40 millimoles) of anhydrous The reactant of sodium carbonate and 1.1 g of copper powder was refluxed for 7 hours by heating and stirring. After the reaction was completed, the reaction solution was filtered, and the filtrate was successively washed with a 35% sodium thiosulfate aqueous solution and saturated saline. The organic layer was dried over anhydrous sodium sulfate. Then, the solvent was removed, and the obtained crude reaction product was recrystallized from ethanol to obtain 5.7 g of 4-methyltriphenylamine (yield: 8 1.4%). Synthesis of 4-bromomethyltriphenylamine In a 300 ml three-necked flask was placed 6.9 g (39 mmol) of N-bromosuccinimide and 9.1 g (3.5 mmol) of 4-A 100 ml of carbon tetrachloride, and then the mixture was heated and stirred to reflux overnight. After the reaction was completed, the reaction solution was cooled, and then the reaction was filtered and the solvent was removed. The obtained reaction product was recrystallized from ethanol to obtain 4 monobromomethyltriphenylamine, 10.8 g (yield: 91.2%). _4 — N_, N —Diphenylaminophenyl-1, butadiene. Synthesis of 1.0 g (40 mmol) of magnesium metal in a 200 ml four-necked flask, replacing air with nitrogen, then Add 100 ml of diethyl ether and start stirring. Slowly add 20 ml of a solution of 9.1 g (27 mmol) of 4-bromomethyltriphenylamine in diethyl ether to the stirred mixture. After adding about 5 ml of solution, slowly begin to reflux, and then drop the size of this paper to apply Chinese National Standard (CNS) A4 size (210X297 cm) ~~~ '~' -76-111 I ~~~ Order (please first (Read the notes on the back and fill out this page)

nn m HI · Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (74) Add the remaining 4 _ bromotriphenylamine. After the addition was completed, reflux was continued for 1 hour to obtain a -Grignand reagent solution, and the obtained reagent solution was cooled to room temperature, and then slowly added dropwise to the solution under ice-cooling. (27 mmol) of allyl chloride in ether. After the addition was completed, the reaction mixture was refluxed for 2 hours to mature the reaction, and then 50 ml of water was added to hydrolyze while cooling with ice. Secondly, the ether layer was collected, rinsed once with a saturated aqueous sodium hydrogen carbonate solution, and rinsed once with water. Then, it was dried over anhydrous sodium sulfate, and ether was removed after drying to obtain a white solid, 4-N, N-diphenylaminophenyl-1-butene, 5,5 g (yield: 6 6.7%). —4 — N, N —diphenylaminophenyl— 1-butanhydrosulfide · (The reaction was placed in a three-necked flask with 40 ml of toluene, 9.9 g (60 mmol) of triethoxy 7 Silyl and 0.018 millimolar diplatinum (0) tris (tetramethyldivinyldisilazane) in toluene, and 20 ml of 16.7 ml was added dropwise at room temperature with stirring. Grams (54.7 millimoles) of 4-N, N-diphenylaminophenyl-1 monobutene in toluene solution. After the addition was complete, the mixture was stirred at 70 ° C for 3 hours, and the solvent was removed under reduced pressure. To obtain an oily pale yellow 4- [4- (triethoxysilyl) butyl] triphenylamine, 13.9 g (yield: 83.2%). The ionization potential of the compound was analyzed by atmospheric photoelectricity ( Use surface analyzer AC — 1, manufactured by Riken Keiki KK) is 5 6 9 ev This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page) Order Printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 _ B7 V. Description of Invention (75) Example 8 Add 4 to the resin solution of Reference Example 1 2- (triethoxysilyl) ethyl] triphenylamine (Example 1), the amount of which is 70% by weight of the resin solid matter, and mixed. The mixture is applied using a rod coater A glass plate was then allowed to dry at 140 ° C for 15 hours and observed under a microscope to obtain a uniform film. Comparative Example 1 30% by weight of the resin was added to the resin solution of Reference Example 1 The triphenylamine was then mixed and cured according to the method of Example 8 to form a thin film, the film was cloudy, and the triphenylamine deposition was determined by microscopic observation. Comparative Example 2 The steps of Comparative Example 1 were repeated to form a thin film, but the reference example 2 was used. Resin solution, the formed film is more transparent, but microscopic observation confirmed the deposition of triphenylamine crystals. Comparative Example 3 The procedure of Example 1 was repeated to obtain 4- [2- (trimethylsilyl) ethyl] triphenylamine, Only 6 g (60 mmol) of trimethylsilane was used in the hydrogenation reaction of 4-vinyltriphenylamine obtained in Example 1. Using this compound, a film was prepared according to the method of Comparative Example 1. The film was opaque. And observed 4 — [2 — (Trimethylsilyl) ethyl] triphenylamine separation》 This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) ': ~:--78-(Please read the precautions on the back before (Fill in this page)

Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (76) Example 9 4-(N -ethyl-N-phenylamino)-[2-(triethoxy'ylsilyl) Synthesis of ethyl] benzene: — Synthesis of 4- (N-ethyl-N-phenylamino) benzaldehyde In a three-necked flask, 82 g of diphenylethylamine and 35.5 ml of DMF were placed in ice. With water cooling and stirring, 84.4 milliliters of phosphonium chloride were added as appropriate, and then the temperature was raised to 95 ° C to allow the reaction to proceed for 5 hours. The resulting reaction solution was poured into 4 warm water and stirred for 1 hour. The precipitate formed was collected by filtration and rinsed with a mixture of ethanol / water (1: 1) to obtain 62 g of 4- (N-diphenylamino) benzaldehyde. Synthesis of 4- (N-ethyl-N-phenylamino) styrene In a three-necked flask, 14.6 g of sodium hydride and 700 ml of 1.2-dimethoxyethane were placed in a room. 13 0.8 g of trimethyl iron bromide was added under stirring, and then a drop of anhydrous ethanol was added, and the reaction was allowed to proceed at 70 ° C for 5 hours. The resulting reaction solution was filtered, and the filtrate and ether extract of the precipitate were deposited. Mix together and rinse with water, then dry the ether solution with calcium chloride, remove the ether to obtain a crude reaction product, and recrystallize with ether to obtain needle-like pale yellow crystals, 0.2 g. A 4_ (N-ethyl-N-phenylamino) styrene hydrosulfurization reaction In a three-necked flask, 40 ml of toluene, 9.9 g (60 mmol) of triethoxysilane and 0. 018 millimoles of two platinum (0) tris (tetramethyl-divinyldisilazane) in toluene, 20 ml of 7.6 g 4-ethylene was added dropwise at room temperature with stirring. The size of phenyl paper is applicable to Chinese National Standard (CNS) A4 (210X297 mm) (Please read the precautions on the back before filling this page)

-79-A7 B7 Consumption Cooperation Staff Printing

V. Description of the invention (77) 1 | (N-phenyl-N-ethyl) amine in toluene solution f After addition »Mixture 1 is stirred at 70 ° C for 3 hours and then the solvent is removed under low pressure.> Oil Shape 1 | Light yellow 4 — (N has ethyl — N — phenylamino) — C 2 — (diethyl 1 I oxymethylsilyl) ethyl) benzene 7 8 g 0 Please go. 1 1 read The ionization potential of the compound is analyzed by atmospheric photoelectricity (read 1 surface IAC — 1 by Riken Ke iki K. KK using a surface analyzer) is f). 3 0 Λ 7 »Note 1 | Italian | Ψ Item 1 News | Example 1 0 ii gen | Add 1 0 0 weight and curable solution of Reference Example 1 2 0 0 heavy page 1 | parts of toluene and 4 0 parts by weight of Example 9 4 — (N — B base- 1 IN —Phenylamino) —C 2 — (triethoxysilyl) ethyl] benzene 1 1 I Manufacture—Cureable composition 0 Apply composition to dip coating by dipping 1 — The coating formed on the substrate of 5 0 β m thick A was dried at 1 0 0 ° C for 1 1 and heat cured for 4 hours to form — 2 β m thick surface protective film 〇1 1 The plate formed was placed in Tabe Γ- S abrasion tester (Y as uda Seik i 1 K. K. manufacturing »5 0 0 g carrying X 2 wrapping tape # 2 0 0 0 purchase, X white Ta ji Photo Fi 1 m Co •, Ltd j 10 0] • ρ η 1) The wear depth measured with a 1 I measurement is better than 0 8 m. 0 1 1 1 Mill A. 9. The substrate and the corona discharge group are used to charge static electricity to 1 1 '7 0 0 V. The residual potential was measured after 5 seconds and found to be lower than 3 50 V. 〇1 1 Example 1 1 1 1 I added 1 0 0 parts by weight of the curable solution of Reference Example 1 9 2 0 0 1 part by weight of toluene And 4 0 parts by weight of Example 4 (NN 1 2 1 1 I) This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -80-Staff consumption cooperation of the Central Standards Bureau of the Ministry of Economic Affairs Preparation of A7 B7 V. Description of the invention (78) (3,4 xylyl) amino)-[2- (triethoxysilyl) ethyl] benzene to produce a curable composition. The composition was applied to a 50-thick Aβ substrate via dip coating, and the resulting coating was dried and thermally cured at 140 ° C for 4 hours to form -2 // m-thick surface protection film. The board was placed in a Tab.er's abrasion tester (manufactured by Yasuda Seiki KK; 50 g load x2; wrapping tape # 2000, purchased from Taj i Photo Film Co., Ltdj 1000rpm) to measure the depth of wear, and the result was as good as 0. 5 # m or less. Mill the A substrate and charge the static electricity to 700 V with a corona discharge group. After 5 seconds, the residual potential was measured and found to be lower than 50V. Comparative Example 4 A composition prepared by dipping coating 5 parts by weight of a polycarbonate resin (trade name: Z-200; purchased from Mitsubishi Gas Chemical Company, Ltd.) in 100 parts by weight of chlorobenzene was applied. Cover the substrate with a thickness of -50 μm, and the formed coating layer is dried at 120 ° C for 1 hour to form a 5em thick protective film. The obtained plate was placed in a Taber ^ s abrasion tester (manufactured by Yasuda Seiki KK; 500g load X2; wrapping tape # 2000; 1 0 0 0 r pm) to measure the wear depth, the result was worse than 4 "A and the substrate After grinding and using a corona discharge group to charge the static electricity to 700V, the residual potential measured after 5 seconds is below 500V, which shows that the paper size of the paper is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) (please read the back first) Please note this page, please fill out this page) -Order-81-Printed by the Consumers Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (79) The load is insufficient. Comparative Example 5 · A curable composition prepared by adding 200 parts by weight of toluene to 100 parts by weight of the curable resin solution of Reference Example 1 by dip coating was applied to -5 0 jum On a thick A 3? Substrate, the coating formed was dried at 140 ° C for 4 hours to form a 2 jam thick protective film. The obtained plate was placed in a Tabe〆s abrasion tester (manufactured by Yasuda Seiki K.K .; 500 g load x2; wrapping tape # 2000; 1000 rpm) to measure the depth of wear, and the result was as good as 0.5 from m or less. A The substrate was also ground and charged to 700V using a corona discharge group, but the residual potential was measured to be 450V after 5 seconds, indicating that the charge elimination force was insufficient. Example 1 2 Dipping coating was used to prepare 20 parts by weight of a polycarbonate resin (trade name: Z—200, purchased from Mitsubishi Gas Chemical Company, Ltd.) in 100 parts by weight of chlorobenzene. The composition is coated on a 50 μm thick A β substrate, and the coating formed is 120 °. (: Drying for 1 hour to form a 50 Am thick protective film. Then, by spray coating method, 55 parts by weight of the organosilicon modified triarylamine compound synthesized in Example 5 and 1,000 parts by weight are referenced. The curable resin of Example 3 was added to 100 parts by weight of toluene and dissolved to make the paper. The paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page)

-82-Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs

A7 ___B7 _ V. Description of the invention (80) The curable composition obtained in (80) is coated on a polycarbonate resin-coated plate as described above. The formed coating is dried and heat-cured at 120 ° C for 5 hours to obtain a -3 thick protective film. The protective film has a pencil hardness of 5 Η and a contact angle of 105 ° with water, even when immersed in water or minerals. Can be removed immediately after oil. The obtained plate was placed in a Taber &quot; * s abrasion tester (manufactured by Yasuda Seiki K.K .; 500g load x2; wrapping tape # 2000; 1000rpm) to measure the wear depth, and the result was as good as 0.5 ren m or less. Comparative Example 6 Dipping coating was used to pass 5 weight of triarylamine having the following structure and 5 weight parts of polycarbonate resin (trade name: Z — 2 0 0; purchased from Mitsubishi Gas Ch.emi.cal C.ompany, Ltd. ) The solution prepared by dissolving in 70. parts by weight of toluene was coated on a 1 mm thick stainless steel plate, so that after drying at 120 ° C for 1 hour, a -10 thickness coating was obtained. The contact angle of water is as small as 7 5 ° so dirt cannot be removed immediately. The resulting board was placed in a Taber es abrasion tester (manufactured by Yasuda Seiki KK; 500g load X2; wrapping tape # 2000, purchased from Fu ji Photo Film Co., Let ·; 1000 rpm) to measure wear Depth, with results up to 5am. H 3 9 c H

N Chinese paper standard is applicable to Chinese National Standard (CNS) A4 specification (210X297). (Please read the precautions on the back before filling this page)

83

Claims (1)

1.Appendix 1 (A) to the scope of patent application. A patent application of the following formula No. 851 13569 Chinese patent application scope amendments Revised in December 1987 [organic silicon modified charge transfer compound aH-CH2V S1- 4Q).)! (R2) 3- (I) Among them, A shows a structure of charge transfer group 圑 and has the following formula) R3 -N- R4 (II) 1111I —III11 lamp (please read the precautions on the back first) (Fill in this page) where R 4 and R 5 each printed as an organic group, and at least one of them shows an aromatic hydrocarbon or heterocyclic group, and R3, R 4 and R 5 May be the same or different, Q represents a member selected from the group consisting of: alkoxy groups having 1 to 6 carbon atoms * ketooxime groups having 1 to 2 carbon atoms, and fluorenyloxy groups having 1 to 4 carbon atoms A hydrolyzable group of the group, or a hydroxyl group; and R 2 represents a monovalent hydrocarbon group having 1 to 15 carbon atoms or a halogen-substituted monovalent hydrocarbon group, η is 1 to 18, m is 1 to 3, and 1 to 5 · 2. For example, the organic silicon-modified charge-transporting compound in item 1 of the patent application scope, wherein the hydrolyzable group is 1 to 6 carbons. Alkoxy group of the product 3. The charge-transporting compound modified by an organosilicon according to item 1 of the patent application range, wherein the ionization potential thereof is 4.5 ev to 6.2 ev 4. A curable composition having a transfer property of mint, It contains: This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 1.Appendix 1 (A) to the scope of patent application. A patent application of the following formula No. 851 13569 Chinese patent application scope amendments Revised in December 1987 [organic silicon modified charge transfer compound aH-CH2V S1- 4Q).)! (R2) 3- (I) Among them, A shows a structure of charge transfer group 圑 and has the following formula) R3 -N- R4 (II) 1111I —III11 lamp (please read the precautions on the back first) (Fill in this page) where R 4 and R 5 each printed as an organic group, and at least one of them shows an aromatic hydrocarbon or heterocyclic group, and R3, R 4 and R 5 May be the same or different, Q represents a member selected from the group consisting of: alkoxy groups having 1 to 6 carbon atoms * ketooxime groups having 1 to 2 carbon atoms, and fluorenyloxy groups having 1 to 4 carbon atoms A hydrolyzable group of the group, or a hydroxyl group; and R 2 represents a monovalent hydrocarbon group having 1 to 15 carbon atoms or a halogen-substituted monovalent hydrocarbon group, η is 1 to 18, m is 1 to 3, and 1 to 5 · 2. For example, the organic silicon-modified charge-transporting compound in item 1 of the patent application scope, wherein the hydrolyzable group is 1 to 6 carbons. Alkoxy group of the product 3. The charge-transporting compound modified by an organosilicon according to item 1 of the patent application range, wherein the ionization potential thereof is 4.5 ev to 6.2 ev 4. A curable composition having a transfer property of mint, It contains: This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297mm) A8 38S100?! D8 VI. Patent application scope A curing resin, which is mainly composed of silicone polymer The ratio of the monovalent hydrocarbon group to the silicon atom to the silicon atom is 0.5 5; and the organosilicon-modified charge transport compound represented by the following formula (I): 'A—HCH2- ^ ~ Si · — (0).) χ (Η2),-· where A shows a charge transfer group structure II (II) shown by R 3 -N- R 4 (I) (please fill in this page on the back of wt *), where R 3, R 4 and R 5 each represent an organic group, at least one of which represents an aromatic hydrocarbon group or a heterocyclic group, and R 3, R 4 and R 5 may be the same or different, and Q represents one selected from: having 1 to 6 A group consisting of an alkoxy group with 1 carbon atom, a ketoxime group with 1 to 2 carbon atoms, and an alkoxy group with 1 to 4 carbon atoms Or a hydroxyl group; and R 2 represents a monovalent hydrocarbon group having 1 to 15 carbon atoms or a halogen-substituted monovalent hydrocarbon group, η is 1 to 1 8 · ιη is 1 to 3, and JT is 1 to 5 · silicone The content of the modified charge-transporting compound is 20-200 parts by weight per 100 parts by weight of the organosilicon polymer of the curable resin. 5. The curable composition according to item 4 of the patent application. The hydrolyzable group is an alkoxy group having 1 to 6 carbon atoms. 6. The curable composition according to item 4 of the scope of patent application, wherein the organosilicon fluorene polymer has a structural unit represented by the following formula (III) The size of the organic paper is applicable to the China Solid State Standard (CNS) A4 (210X297 mm). Ordered by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs for printing 388100 A8 B8 C8 D8. The scope of patent application is polysiloxane. R6nS10Mn -«0/2 (〇R7) ·. (I 工 I) where Re shows a straight or branched alkyl or alkenyl group with 1 to 18 carbon atoms, or an aryl group; R 7 shows a 1 An alkyl group of 4 carbon atoms; η is on average 0.5 to 1. 5; and m is on average 0.01 to 1.5 * 7. If the patent application scope of the fourth item can be fixed A composition wherein the curable resin contains a silane compound represented by the following formula (IV), R 8eS i X (IV) wherein R 8 represents a straight or branched chain alkyl or olefin having 1 to 18 carbon atoms Group, or a phenyl group; X represents an alkoxy group having 1 to 6 carbon atoms, with ... a ketoxime group having 1 to 2 carbon atoms, an alkoxy group having 1 to 4 carbon atoms Or a hydrogen atom; and a Morse (Please read the note on the back first and then fill out this page) Printed on the paper by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. The paper size is applicable to the Chinese National Standard (CNS) A4 specification ( 210X297 mm)