JP2005035980A - Quinone compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound that has excellent electron transport function that is useful for electrophotographic photoreceptor and in organic luminescence (EL) uses. <P>SOLUTION: The quinone compound has a structure represented by general formula (I) (wherein R<SP>1</SP>to R<SP>4</SP>are each H, an alkyl which may be substituted, an aryl which may be substituted and a heterocyclic ring which may be substituted; R<SP>5</SP>is an aryl which may be substituted and a heterocyclic ring which may be substituted; R<SP>6</SP>is a halogen, an alkyl which may be substituted, an alkoxy which may be substituted, an aryl which may be substituted and a heterocycles which may be substituted; X is a sulfur atom, an oxygen atom; n is an integer of 0 to 3 where, in the case where n is 2 or 8, R<SP>6</SP>s may be identical or different, mutually bond to form a ring or condensed ring structure and these substituents means halogen atoms, alkyls, alkoxyls, halogenated alkyls, nitro, aryls and heterocycles). <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a quinone compound, and more particularly to a novel quinone compound useful as an electron transport material in an electrophotographic photoreceptor (hereinafter also simply referred to as “photoreceptor”), an organic electroluminescence (EL) device, and the like.

  In recent years, as one of electronic devices using organic compounds, so-called organic photoconductors using organic photoconductive materials can be designed to have various characteristics of photoconductors with no pollution, low cost, and freedom of material selection. Many have been proposed and put to practical use.

  The photosensitive layer of the organic photoreceptor is mainly composed of a layer in which an organic photoconductive material is dispersed in a resin. A layer in which a charge generation material is dispersed in a resin (charge generation layer) and a charge transport material are dispersed in the resin. Many layers have been proposed, such as a layered structure in which a layer (charge transport layer) is laminated, or a single layer structure consisting of a single layer in which a charge generating material and a charge transport material are dispersed in a resin. Yes.

  Among them, as a photosensitive layer, a function-separated laminated type photoreceptor in which a charge transport layer is laminated on a charge generation layer has been widely put into practical use because of excellent photoreceptor characteristics and durability. Since the hole transport material is usually used as the charge transport material in the charge transport layer provided in the function-separated multilayer photoreceptor, this photoreceptor is used in an electrophotographic apparatus that operates in a negative charging process. . However, the negative corona discharge used in the negative charging process is unstable compared to that of the positive polarity and has a large amount of generated ozone. It is a problem. In order to solve these problems, an organic photoreceptor that can be used in a positive charging process is effective.

  By the way, in order to make a photoconductor excellent in durability as described above for a positive charging process and high sensitivity, it is necessary to use a substance having an excellent electron transport function. Many such substances and photoreceptors using the same have been proposed so far. For example, in Patent Document 1 to Patent Document 14, Non-Patent Document 1 to Non-Patent Document 4 and the like, many electron transport materials and electrophotographic photoreceptors using the same have been proposed and described, and have come to attract attention. ing. In addition, in a single-layer type photosensitive layer, for example, a photoreceptor using a combination of a hole transport material and an electron transport material as described in Patent Document 15 to Patent Document 19 has been noted as having high sensitivity. Some have been put to practical use.

  In addition, the present inventors have also proposed various photoreceptors containing a substance having an electron transport function with the aim of achieving a photoreceptor having superior characteristics (for example, described in Patent Documents 20 to 24). ).

  In addition, there is an organic EL as a light emitting device using an organic photoconductive substance, which is expected to be applied to a display recently. For this organic EL, many proposals for improving organic materials have been made. Some have been put to practical use.

The simplest structure of organic EL is a structure in which a light emitting layer containing a light emitting material that is an organic compound is sandwiched between electrodes, and by passing an electric current through the electrode, electrons and holes are injected from the electrode into the light emitting layer, Excitons are formed in the light emitting layer, and recombination occurs to generate light emission. In addition, for the purpose of efficiently injecting electrons and holes injected from the electrode into the light emitting layer, functional layers such as a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer are combined with the light emitting layer. Layered structures have also been proposed, and among these, an organic compound having an electron transport function is used for the electron transport layer and the electron injection layer (see Non-Patent Document 5 and the like).
JP-A-1-206349 JP-A-4-360148 JP-A-3-290666 JP-A-5-92936 JP-A-9-151157, JP-A-5-279582 JP-A-7-179775 Japanese Patent Laid-Open No. 10-73937 JP-A-4-338760 JP-A-1-230054 JP-A-8-278743 JP-A-9-190002 JP-A-9-190003 JP 2001-222122 A Japanese Patent Laid-Open No. 5-150481 JP-A-6-130688 JP-A-9-281728 JP-A-9-281729 JP-A-10-239874 JP 2000-75520 A JP 2000-199979 A JP 2000-143607 A JP 2001-142239 A JP 2002-278112 A The Journal of Electrophotographic Society Vol. 30, p266-273 (1991) Pan-Pacific Imaging Conference / Japan Hardcopy '98 July 15-17, 1998 JA HALL, Tokyo, Japan Proceedings p207-210 Japan Hardcopy '97 Proceedings July 9, 10 and 11, 1997 JA Hall (Otemachi, Tokyo) p21-24 Japan Hardcopy '92 Proceedings July 6, 7, and 1992 JA Hall (Otemachi, Tokyo) p173-176 Applied Physics Vol. 70, No. 12 (2001) p1419-1425 “Development Trends of Highly Efficient Organic EL Materials (Omori)”

  However, diphenoquinone compounds and stilbenequinone compounds, which are known as substances having an electron transport function, have not been sufficiently satisfactory in electrical characteristics such as sensitivity and residual potential for use in electrophotographic photoreceptors. Therefore, an electron transport material having better electrical characteristics has been desired. Further, in organic EL applications, there has been a demand for a high-performance electron transporting material that has higher luminance than before and can improve luminous efficiency.

  Therefore, an object of the present invention is to provide a compound having an excellent electron transport function useful for electrophotographic photoreceptors and organic EL applications.

（式（Ｉ）中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴は、同一または異なって、水素原子、置換基を有してもよい炭素数１〜１２のアルキル基、置換基を有してもよいアリール基または置換基を有してもよい複素環基を表し、Ｒ⁵は、置換基を有してもよいアリール基または置換基を有してもよい複素環基を表し、Ｒ⁶は、ハロゲン原子、置換基を有してもよい炭素数１〜６のアルキル基、置換基を有してもよい炭素数１〜６のアルコキシ基、置換基を有してもよいアリール基または置換基を有してもよい複素環基を表し、Ｘは、硫黄原子または酸素原子を表し、ｎは０〜３の整数を表し、ｎが２または３の場合には、少なくとも２つあるＲ⁶は同一であっても異なっていてもよく、互いに結合して置換基を有してもよい環または縮合環を形成していてもよく、置換基は、ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基、炭素数１〜６のハロゲン化アルキル基、ニトロ基、アリール基または複素環基を表す）で表される構造を有することを特徴とするものである。 In order to solve the above problems, the quinone compound of the present invention has the following general formula (I),

(In the formula (I), R ¹ , R ² , R ³ and R ⁴ are the same or different and each have a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and a substituent which may have a substituent. R ⁵ represents an optionally substituted aryl group or an optionally substituted heterocyclic group, R ⁵ represents an optionally substituted aryl group or an optionally substituted heterocyclic group, R ⁶ is a halogen atom, an optionally substituted alkyl group having 1 to 6 carbon atoms, an optionally substituted alkoxy group having 1 to 6 carbon atoms, and an optionally substituted aryl group. Or an optionally substituted heterocyclic group, X represents a sulfur atom or an oxygen atom, n represents an integer of 0 to 3, and when n is 2 or 3, there are at least two. R ⁶ may be the same or different and may form a good or fused ring which may have a bond to a substituent from each other And the substituent represents a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a nitro group, an aryl group, or a heterocyclic group). It has the structure represented.

  According to the present invention, a compound having excellent electron transportability can be obtained. By using this compound in an electronic device using an organic compound such as an electrophotographic photoreceptor or organic EL, electrical characteristics, luminous efficiency, etc. The characteristics can be improved.

Hereinafter, specific embodiments of the present invention will be described in detail.
The quinone compound of the present invention can be synthesized, for example, according to the following reaction formulas (1) and (2). That is, first, as shown in the following reaction formula (1), a compound represented by the structural formula (B) is synthesized from a compound represented by the structural formula (B ′). Next, as shown in the following reaction formula (2), the compound represented by the structural formula (A) and the compound represented by the structural formula (B) are reacted with an appropriate organometallic reagent (for example, magnesium). And then removing the protecting group (TMS: trimethylsilyl group) to synthesize a compound represented by the structural formula (C). Further, after dehydration condensation between this and the compound represented by the structural formula (D), the compound represented by the general formula (I) is synthesized by oxidizing with an appropriate catalyst (for example, lead dioxide (PbO ₂ )). can do.
In addition, “TBAF” in the following reaction formula (2) represents tetrabutylammonium fluoride.

は、ｔ−ブチル基を表す。 Specific examples of the compound represented by the general formula (I) are shown below, but the present invention is not limited to these compounds. In addition, the substituent in the following specific example

Represents a t-butyl group.

  The quinone compound of the present invention represented by the general formula (I) is useful as a so-called electron transport material because it has excellent electron transport properties, and in particular, a photosensitive layer material of an electrophotographic photoreceptor, and It can be suitably used as a functional layer material such as an electron transport layer of organic EL.

Hereinafter, the present invention will be described based on examples.
Synthesis Example 1: Synthesis of Compound of Specific Example (I-3) The compound of Specific Example (I-3) was synthesized according to the following reaction formulas (1-1) and (2-1).

(1) To a dichloromethane solution of 100 mmol (14.7 g) of 2-thenoyl chloride (the above structural formula (B′-1)) and 110 mmol (10.7 g) of N, O-dimethylhydroxyamine hydrochloride at room temperature in a nitrogen atmosphere Below, 230 mmol (18.2 g) of pyridine was added and stirred for 2 hours. Thereafter, the mixture was poured into hydrochloric acid, extracted with dichloromethane, and concentrated to give a crude product with a yield of 14.8 g (86.7%) in a yield of N-methoxy-N-methylthiophenecarboxamide (the above structural formula (B-1 )).

(2) Next, to a tetrahydrofuran (THF) solution of 30 mmol (5.1 g) of the compound represented by the structural formula (B-1), 78 mmol (1.9 g) of magnesium and 4-bromo-2,6-di A Grignard reagent prepared from a THF solution of -t-butyl-1- (trimethylsiloxy) benzene (A-1) 60 mmol (21.4 g) was added dropwise and stirred at room temperature for 3 hours. Thereafter, a small amount of 1N aqueous hydrochloric acid was added to terminate the reaction. Further, 60 mmol (60 ml) of 1.0 M tetrabutylammonium fluoride solution (TBAF) was added and stirred, then poured into hydrochloric acid water, extracted with dichloromethane, and concentrated to yield 6.5 g (68) as a crude product. 0.1%), a compound represented by the structural formula (C-1) was obtained.

(3) Further, 15 mmol (4.7 g) of the compound represented by the structural formula (C-1) and 30 mmol (5.4 g) of 4-chlorophenylhydrazine hydrochloride (the structural formula (D-1)) are dissolved in pyridine. And heated to reflux. The reaction mixture was poured into aqueous hydrochloric acid, extracted with dichloromethane and concentrated. Then, the crude product was obtained by refine | purifying with column chromatography.

(4) 20 mmol (4.8 g) of lead dioxide (PbO ₂ ) was added to the chloroform solution of the above crude product at room temperature and stirred. After filtering the residue, the solid content obtained by concentrating the reaction solution was recrystallized with hexane to obtain the compound represented by the structural formula (I-3). The yield was 3.4 g (yield 51.4%) and MS m / z 438 (M +). The overall yield was 30.3%. The IR spectrum of the compound of this specific example (I-3) is shown in FIG. 1, and the ¹ H-NMR spectrum is shown in FIG.

Synthesis Example 2: Synthesis of Compound of Specific Example (I-83) The compound of Specific Example (I-83) was synthesized according to the following reaction formulas (1-2) and (2-2).

As shown in the above reaction formula, 2-thenoyl chloride (the structural formula (B′-1)) of Synthesis Example 1 was replaced with 2-furoyl chloride (the structural formula (B′-2)). Was performed in the same manner as in Synthesis Example 1, to obtain a compound represented by the structural formula (I-83). The yield was 3.1 g (overall yield 32.5%) and MS m / z 422 (M +). The IR spectrum of the compound of this specific example (I-83) is shown in FIG. 3, and the ¹ H-NMR spectrum is shown in FIG.

Synthesis Example 3 Synthesis of Compound of Specific Example (I-163) The compound of Specific Example (I-163) was synthesized according to the following reaction formulas (1-3) and (2-3).

As shown in the above reaction formula, 2-thenoyl chloride of the synthesis example 1 (the structural formula (B′-1)) is converted to benzo [b] thiophene-2-carboxylic acid chloride (the structural formula (B′- The same operation as in Synthesis Example 1 was carried out, except for replacing 3)), to obtain the compound represented by the structural formula (I-163). The yield was 5.0 g (total yield 41.2%) and MS m / z 488 (M +). The IR spectrum of the compound of this specific example (I-163) is shown in FIG. 5, and the ¹ H-NMR spectrum is shown in FIG.

Synthesis Example 4: Synthesis of Compound of Specific Example (I-217) The compound of Specific Example (I-217) was synthesized according to the following reaction formulas (1-4) and (2-4).

As shown in the above reaction formula, 2-thenoyl chloride of the synthesis example 1 (the structural formula (B′-1)) is converted to 3-chlorobenzo [b] thiophene-2-carboxylic acid chloride (the structural formula (B The compound represented by the structural formula (I-217) was obtained in the same manner as in Synthesis Example 1 except that it was replaced with '-4)). The yield was 4.6 g (total yield 26.3%) and MS m / z 522 (M +). The IR spectrum of the compound of this specific example (I-217) is shown in FIG. 7, and the ¹ H-NMR spectrum is shown in FIG.

Synthesis Example 5: Synthesis of Compound of Specific Example (I-243) The compound of Specific Example (I-243) was synthesized according to the following reaction formulas (1-5) and (2-5).

As shown in the above reaction formula, 2-thenoyl chloride of the synthesis example 1 (the structural formula (B′-1)) is converted to benzo [b] furan-2-carboxylic acid chloride (the structural formula (B′- The compound represented by the structural formula (I-243) was obtained in the same manner as in Synthesis Example 1 except that the procedure was changed to 5)). The yield was 4.8 g (total yield 32.8%) and MS m / z 472 (M +). FIG. 9 shows the IR spectrum of the compound of this specific example (I-243), and FIG. 10 shows the ¹ H-NMR spectrum.

Synthesis Example 6: Synthesis of Compound of Specific Example (I-403) The compound of Specific Example (I-403) was synthesized according to the following reaction formulas (1-6) and (2-6).

As shown in the above reaction formula, 2-thenoyl chloride of the synthesis example 1 (the structural formula (B′-1)) is converted to 3,4-ethylenedioxythiophene-2-carboxylic acid chloride (the above structural formula ( A compound represented by the structural formula (I-403) was obtained in the same manner as in Synthesis Example 1 except for replacing B′-6)). The yield was 2.8 g (total yield 38.9%) and MS m / z 496 (M +). FIG. 11 shows the IR spectrum of the compound of this specific example (I-403), and FIG. 12 shows the ¹ H-NMR spectrum.

  In addition, 2-thenoyl chloride (the structural formula (B′-1)), 2-furoyl chloride (the structural formula (B′-2)) and 4-chlorophenylhydrazine hydrochloride (the structural formula (D-1)). )) Can be purchased from Tokyo Chemical Industry Co., Ltd. In addition, benzo [b] thiophene-2-carboxylic acid chloride (the structural formula (B′-3)) and 3-chlorobenzo [b] thiophene-2-carboxylic acid chloride (the structural formula (B′-4)) are , And can be obtained from Lancaster Japan Co., Ltd. Furthermore, 4-bromo-2,6-di-tert-butyl-1- (trimethylsiloxy) benzene (formula (A-1)) is synthesized by, for example, a known method described in Patent Document 14 and the like. be able to.

Benzo [b] furan-2-carboxylic acid chloride (the above structural formula (B′-5)) was synthesized according to the following reaction formula (3).
Reaction formula (3)

  To 50 mmol (8.1 g) of benzo [b] furan-2-carboxylic acid, 75 mmol (8.9 g) of thionyl chloride was added, and 3 drops of N, N-dimethylformamide was added dropwise and heated to reflux. After 2 hours, excess thionyl chloride was distilled off to give 7.4 g (81.9%) of benzo [b] furan-2-carboxylic acid chloride as an oily substance (the above structural formula (B′-5)). )was gotten. Benzo [b] furan-2-carboxylic acid can be obtained from Sigma-Aldrich Japan Co., Ltd.

Furthermore, 3,4-ethylenedioxythiophene-2-carboxylic acid chloride (the structural formula (B′-6)) was synthesized according to the following reaction formula (4).
Reaction formula (4)

(1) A hexane solution of 3,4-ethylenedioxythiophene (200 mmol, 28.4 g) and N, N, N, N-tetramethylethylenediamine (220 mmol, 25.6 g) in an ice bath under a nitrogen atmosphere, n -BuLi 220 mmol (138 ml) was added dropwise, and then the mixture was heated to reflux at room temperature for 0.5 hour and further for 0.5 hour. The reaction solution was cooled, poured into dry ice and allowed to stand overnight. Thereafter, the mixture was extracted with chloroform and a 10% aqueous sodium hydroxide solution, and the resulting aqueous layer was acidified with hydrochloric acid to precipitate. By filtering this, 3,4-ethylenedioxythiophene-2-carboxylic acid was obtained as a crude product in a yield of 21.8 g (yield 58.5%).

(2) To 50 mmol (9.3 g) of 3,4-ethylenedioxythiophene-2-carboxylic acid obtained, 75 mmol (8.9 g) of thionyl chloride was added, and 3 drops of N, N-dimethylformamide was added dropwise and heated. Refluxed. After 2 hours, excess thionyl chloride was distilled off to give 3,4-ethylenedioxythiophene-2-carboxylic acid chloride (formula (B ′) as an oily substance in a yield of 7.9 g (77.2%). -6) was obtained.
3,4-ethylenedioxythiophene can be obtained from Sigma-Aldrich Japan Co., Ltd.

Photoconductor application example 1
A plate-shaped photoconductor was prepared for evaluating electrical characteristics, and a drum-shaped photoconductor was manufactured for evaluating printing. Hereinafter, “parts” represents parts by weight.
On the outer surface of an aluminum plate (3 cm × 10 cm, thickness 1 mm) and an aluminum tube (outer diameter 30 mmφ, length 247.5 mm, thickness 0.75 mm) The film was applied by a dip coating method and dried at 100 ° C. for 60 minutes to remove the solvent, thereby forming an undercoat layer having a thickness of 0.3 μm.

(Preparation of undercoat layer solution)
a1) Soluble nylon (Amilan CM8000: manufactured by Toray Industries, Inc.) 3 parts (30 g)
The undercoat layer material a1) was stirred and dissolved with 97 parts (970 g) of a mixed solvent of methanol / methylene chloride (5 vol./5 vol.) To prepare an undercoat layer solution.

  Next, on this undercoat layer, a single layer type photosensitive layer dispersion prepared as follows is applied by a dip coating method for a plate-like one, and by a ring coating method for a drum-like one. Each was coated and dried at 100 ° C. for 60 minutes to remove the solvent, and a single-layer type photosensitive layer having a thickness of 30 μm was formed to produce an electrophotographic photoreceptor.

で示されるスチリル化合物
（特開２００１−３１４９６９号公報中の（ＨＴ１−１０１）） ８部（４ｇ）
ｂ３）電子輸送物質：前記式（Ｉ−３）で示される化合物［合成実施例１］
５部（２．５ｇ）
ｂ４）酸化防止剤：３，５−ジ−ｔｅｒｔ−４−ヒドロキシトルエン（ＢＨＴ）
１部（０．５ｇ）
ｂ５）シリコーンオイル（ＫＦ−５０：信越化学工業（株）製）
０．０１部（０．００５ｇ）
ｂ６）バインダー樹脂：ビスフェノールＺ型ポリカーボネート樹脂
（パンライトＴＳ２０５０：帝人化成（株）製）
（特開２０００−３１４９６９号公報中の（ＢＤ１−１） ７部（３．５ｇ） (Preparation of single-layer photosensitive layer dispersion)
b1) Charge generation material: X-type metal-free phthalocyanine (see FIG. 2 in JP-A No. 2001-228637) 0.2 part (0.1 g)
b2) Hole transport material: Structural formula (HT1-101)

A styryl compound represented by the formula ((HT1-101) in JP-A-2001-314969) 8 parts (4 g)
b3) Electron transport material: compound represented by the formula (I-3) [Synthesis Example 1]
5 parts (2.5g)
b4) Antioxidant: 3,5-di-tert-4-hydroxytoluene (BHT)
1 part (0.5g)
b5) Silicone oil (KF-50: manufactured by Shin-Etsu Chemical Co., Ltd.)
0.01 part (0.005g)
b6) Binder resin: Bisphenol Z type polycarbonate resin (Panlite TS2050: manufactured by Teijin Chemicals Ltd.)
(7 parts (3.5 g) of (BD1-1) in JP 2000-314969 A

  The photosensitive layer materials b1) to b6) were put in a 100 ml plastic bottle together with 100 parts (50 g) of methylene chloride solvent and 50 g of stainless beads (3 mmφ), and the paint conditioner Model 5400 (USA: Red Devil) was used. A dispersion treatment was performed for 1 minute, and then the SUS balls were separated to prepare a single-layer photosensitive layer dispersion.

Photoconductor application example 2
Of the composition of the single-layer photosensitive layer dispersion used in the photoreceptor application example 1, 5 parts of the compound represented by the above formula (I-3) as an electron transporting substance is substituted with the above formula (I- 83) A photoconductor was prepared in the same manner as in Photoconductor Application Example 1 except that 5 parts of the compound shown in [Synthesis Example 2] were used.

Photoconductor Application Example 3
Of the composition of the single-layer photosensitive layer dispersion used in the photoreceptor application example 1, 5 parts of the compound represented by the above formula (I-3) as an electron transporting substance is substituted with the above formula (I- 163) A photoconductor was prepared by the same way as that of Photoconductor Application Example 1 except that 5 parts of the compound shown in [Synthesis Example 3] were used.

Photoconductor Application Example 4
Of the composition of the single-layer photosensitive layer dispersion used in the photoreceptor application example 1, 5 parts of the compound represented by the above formula (I-3) as an electron transporting substance is substituted with the above formula (I- 217) A photoconductor was prepared by the same way as that of Photoconductor Application Example 1 except that 5 parts of the compound shown in [Synthesis Example 4] were used.

Photoconductor Application Example 5
Of the composition of the single-layer photosensitive layer dispersion used in the photoreceptor application example 1, 5 parts of the compound represented by the above formula (I-3) as an electron transporting substance is substituted with the above formula (I- 243) A photoconductor was prepared in the same manner as in Photoconductor Application Example 1 except that 5 parts of the compound shown in [Synthesis Example 5] were used.

Photoconductor Application Example 6
Of the composition of the single-layer photosensitive layer dispersion used in the photoreceptor application example 1, 5 parts of the compound represented by the above formula (I-3) as an electron transporting substance is substituted with the above formula (I- 403) A photoconductor was prepared in the same manner as in Photoconductor Application Example 1 except that 5 parts of the compound shown in [Synthesis Example 6] were used.

Evaluation of Photoconductor Application Examples 1 to 6 As an evaluation of electrical characteristics, evaluation was performed with an electrostatic copying paper testing apparatus EPA-8100 manufactured by Kawaguchi Electric Co., Ltd. using a plate-like photoconductor.
Under an environment of a temperature of 24 ° C. and a humidity of 50%, charging was performed so that the surface potential was about +700 V in a dark place, and the retention rate V _k5 of the surface potential after 5 seconds was obtained from the following equation.
Retention rate V _k5 (%) = (V ₅ / V ₀ ) × 100
V ₀ : Surface potential immediately after charging V ₅ : Surface potential after 5 seconds

Next, the surface potential is set to +600 V, and 1.0 μW / cm ² of monochromatic light obtained by splitting the light of the halogen lamp to 780 nm with a filter is exposed for 5 seconds, so that the surface potential is halved (+300 V). The exposure amount was determined as sensitivity E _1/2 (μJ / cm ² ), and the surface potential 5 seconds after exposure was determined as residual potential V _r (V).
These evaluation results are shown in Table 1 below.

  In addition, as an evaluation of durability by actual printing, a drum-shaped photoconductor was mounted on a laser printer HL-1850 manufactured by Brother Industries, Ltd., and a black solid image or a white solid image was obtained under an environment of a temperature of 25 ° C. and a humidity of 48%. Images and halftone images were printed. Subsequently, 5,000 images with a printing rate of about 5% were printed, and then a black solid image, a white solid image, and a halftone image were printed again, and the images after printing 5,000 sheets were evaluated.

  As a result, in the photoreceptors of the photoreceptor application examples 1 to 6, good images were obtained in both the initial image and the image after 5,000 sheets.

It is IR spectrum of the compound shown by Structural formula (I-3). ¹ is a ¹ H-NMR spectrum of a compound represented by Structural Formula (I-3). 3 is an IR spectrum of a compound represented by a structural formula (I-83). ¹ is a ¹ H-NMR spectrum of a compound represented by a structural formula (I-83). 3 is an IR spectrum of a compound represented by a structural formula (I-163). ¹ is a ¹ H-NMR spectrum of a compound represented by a structural formula (I-163). 3 is an IR spectrum of a compound represented by a structural formula (I-217). ¹ is a ¹ H-NMR spectrum of a compound represented by a structural formula (I-217). 3 is an IR spectrum of a compound represented by a structural formula (I-243). ¹ is a ¹ H-NMR spectrum of a compound represented by a structural formula (I-243). 3 is an IR spectrum of a compound represented by a structural formula (I-403). ¹ is a ¹ H-NMR spectrum of a compound represented by a structural formula (I-403).

Claims (1)

The following general formula (I),

(In the formula (I), R ¹ , R ² , R ³ and R ⁴ are the same or different and each have a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and a substituent which may have a substituent. R ⁵ represents an optionally substituted aryl group or an optionally substituted heterocyclic group, R ⁵ represents an optionally substituted aryl group or an optionally substituted heterocyclic group, R ⁶ is a halogen atom, an optionally substituted alkyl group having 1 to 6 carbon atoms, an optionally substituted alkoxy group having 1 to 6 carbon atoms, and an optionally substituted aryl group. Or an optionally substituted heterocyclic group, X represents a sulfur atom or an oxygen atom, n represents an integer of 0 to 3, and when n is 2 or 3, there are at least two. R ⁶ may be the same or different and may form a good or fused ring which may have a bond to a substituent from each other And the substituent represents a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a nitro group, an aryl group, or a heterocyclic group). A quinone compound having a structure represented by:

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