JP2007262151A - Charge-transporting organic polymer, method for preparing the same and organic device material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a charge-transporting organic polymer forming a highly stable film through a wet film-forming method and has a good charge-transporting property, a method for preparing the same, and an organic device material using the polymer. <P>SOLUTION: The charge-transporting organic polymer is obtained by reacting boron trihalide with a dihalide of a specific N-(substituted)phenylcarbazole lithiated by an alkyl lithium, is composed of at least two units of a specific repeating unit, is soluble in an organic solvent such as chloroform and forming a film through a wet film-forming method. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an organic charge transporting polymer suitable for a wet film-forming method and an organic electroluminescence device using the polymer (hereinafter, “electroluminescence” may be abbreviated as “EL”). The present invention relates to materials for organic devices such as light emitting devices and organic transistors.

  Organic devices are expected to expand into a wide range of basic elements and applications, such as organic light-emitting devices such as organic EL elements, organic transistors, and solar cells.

  An organic EL element using electroluminescence of an organic compound material is a self-luminous element that emits light by applying an electric field to a fluorescent organic compound, has a wide viewing angle, can be driven at a low voltage, and has high luminance. It has many advantages such as fewer constituent layers than a liquid crystal element, easy manufacturing, and reduced thickness, and has attracted attention as a next-generation display element.

  The organic EL element takes out the energy of an excited state generated by recombination of electrons and holes injected into the element as light emission, and the generated excited state has a singlet state of 25% and a triplet state. It is thought to be 75%. Since organic EL elements using fluorescence use only singlet energy, it is difficult for the internal quantum yield to remain at 25% in principle.

  At present, organic EL elements using phosphorescence are attracting attention. In an organic EL element using phosphorescence (also referred to as a phosphorescent organic EL element), not only singlet state energy but also triplet state energy can be used, and the internal quantum yield is 100 in principle. % Can be raised.

  A phosphorescent organic EL device takes out phosphorescence emission by doping a host material with a metal complex light emitting material containing a heavy metal such as platinum or iridium as a dopant emitting phosphorescence (see, for example, Non-Patent Document 1).

  The emission of the phosphorescent dopant depends on the host material, but the basic performance required for the host material is that it has a hole transporting property and an electron transporting property, and the reduction potential of the host material is higher than the reduction potential of the phosphorescent dopant. The energy level of the triplet state of the host material is lower than the reduction potential of the dopant. Generally, CBP (4,4′-bis (carbazol-9-yl) -biphenyl is a low molecular material. ) Is preferably used (see, for example, Patent Document 1).

  Phosphorescent devices using CBP as a host material are expected to have higher efficiency and longer life, but on the other hand, CBP crystallization and aggregation occur over time, resulting in deterioration of the device and significant effects on device life. There is a problem of giving. Further, the luminous efficiency is not yet able to withstand practical use, and further improvement is necessary. Furthermore, CBP has to be formed by a vapor deposition process, and there is a problem that a large vapor deposition apparatus is required and the cost is high, and further, it is difficult to increase the area of the base material. As a method that can be manufactured at a low cost and can produce a large area display as compared with a vacuum evaporation method, there is a wet film formation method such as application to a substrate using a solvent. However, even if an attempt is made to prepare a coating liquid by dissolving or dispersing a low-molecular material such as conventional CBP in a solvent, the solubility and dispersibility are poor, so a uniform and stable coating liquid cannot be obtained, and film formation is performed. Even if possible, it has been difficult to use conventional low molecular weight materials by the wet film formation method because the film stability is poor, such as crystallization and aggregation of the organic layer over time.

  On the other hand, Patent Document 2 contains an organic EL comprising a compound having both a boron atom substituted with at least one aromatic group and a nitrogen atom substituted with at least one aromatic group in the molecule. An element is disclosed. However, in Patent Document 2, film formation by a vacuum deposition method is preferable, and film stability by which a film formation by a wet film formation method or crystallization or aggregation of an organic layer does not occur has been studied. Absent.

M.A.Baldo et.al., Nature, vol.403, p.750-753 (2000) Japanese Patent Laid-Open No. 10-168443 JP 2001-93670 A

  The present invention has been made to solve the above-mentioned problems, and a first object of the present invention is to form a highly stable film by a wet film forming method, and to provide an organic material having good charge transportability. An object is to provide a charge transporting polymer and a method for producing the same.

  A second object of the present invention is to provide an organic device material capable of forming a layer having high film stability and charge transportability by a wet film forming method.

  The organic charge transporting polymer according to the present invention is represented by the following general formula (1).

（式（１）において、Ｒは、それぞれ独立に、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族基、ハロゲン原子、又は水素原子である。繰り返し単位中の３つのＲは、それぞれ同一であっても互いに異なっていても良い。また、繰り返し単位間で各Ｒは、全て同一であっても互いに異なっていても良い。ｎは、２以上の整数である。）

(In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. (It may be the same or different from each other, and each R may be the same or different from each other among the repeating units. N is an integer of 2 or more.)

  In addition, the present invention provides a repetition represented by the following formula (1), which comprises a step of reacting a halide represented by the following formula (2) with lithiated alkyllithium and boron trihalide. A method for producing an organic charge transporting polymer composed of units is also provided.

（式（２）において、Ｘは、ハロゲン原子を表す。Ｒは、それぞれ独立に、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族基、ハロゲン原子、又は水素原子である。）

(In Formula (2), X represents a halogen atom. R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom.)

（式（１）において、Ｒは、それぞれ独立に、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族基、ハロゲン原子、又は水素原子である。繰り返し単位中の３つのＲは、それぞれ同一であっても互いに異なっていても良い。また、繰り返し単位間で各Ｒは、全て同一であっても互いに異なっていても良い。ｎは、２以上の整数である。）

(In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. (It may be the same or different from each other, and each R may be the same or different from each other among the repeating units. N is an integer of 2 or more.)

  Furthermore, the present invention also provides an organic device material using the organic charge transporting polymer.

  The organic charge transporting polymer according to the present invention can form a highly stable film by a wet film forming method and has a good charge transporting property. According to the production method of the present invention, the polymer can be easily obtained. The organic charge transporting polymer according to the present invention is extremely useful as an organic device material capable of forming a layer having a high film stability and a charge transporting property by a wet film forming method.

Hereinafter, the organic electrotransport polymer of the present invention, the production method thereof, and the organic device material will be described in detail in order.
The organic charge transporting polymer according to the present invention is represented by the following general formula (1).

（式（１）において、Ｒは、それぞれ独立に、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族基、ハロゲン原子、又は水素原子である。繰り返し単位中の３つのＲは、それぞれ同一であっても互いに異なっていても良い。また、繰り返し単位間で各Ｒは、全て同一であっても互いに異なっていても良い。ｎは、２以上の整数である。）

(In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. (It may be the same or different from each other, and each R may be the same or different from each other among the repeating units. N is an integer of 2 or more.)

  The organic charge transporting compound according to the present invention has an electron transporting property due to the presence of a partial structure consisting of a boron atom that is fully substituted with an aromatic group, and has a hole transporting property due to the presence of a partial structure containing a carbazole group. Therefore, it is a bipolar molecule having an electron transporting property and a hole transporting property. Furthermore, the organic charge transporting compound according to the present invention has a hyperbranched structure, and by appropriately adjusting the substituent R, it has high solvent solubility and can be formed by a wet film forming method. In the case of film formation, crystallization and aggregation hardly occur and the film stability is high. As a result, the organic charge transporting compound of the present invention can be used as a charge transporting material excellent in hole transporting property and electron transporting property, which can form a highly stable film by a wet film forming method. is there.

  In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the unsubstituted alkyl group include a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, Examples include linear alkyl groups such as n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, and n-hexadecyl group. In addition, an i-propyl group, a sec-butyl group, in which one or more hydrogen atoms other than the terminal of these linear alkyl groups are substituted with an alkyl group such as a methyl group, an ethyl group, an n-propyl group, or an isopropyl group, A branched alkyl group such as a tert-butyl group can be exemplified. The carbon number of the alkyl group of R is not particularly limited.

  Examples of the substituted alkyl group include those in which one or more hydrogen atoms of the alkyl group exemplified above are substituted with a substituent that does not unduly hinder the effects of the present invention. For example, one or more hydrogen atoms of an alkyl group are substituted with a halogen atom or a substituted or unsubstituted aromatic group, trifluoromethyl group, cyano group, nitro group, alkoxy group, aryloxy group, alkylthio group, dialkylamino group, etc. Can be exemplified.

  The unsubstituted aromatic group may be an aromatic hydrocarbon group or a heterocyclic group. Of these, an aromatic hydrocarbon group is preferred. Examples of the unsubstituted aromatic group include a phenyl group, a naphthyl group, a diphenyl group, an anthryl group, a pyridyl group, a dipyridyl group, and a phenanthroyl group.

  Examples of the substituted aromatic group include those in which one or more hydrogen atoms of the aromatic groups exemplified above are substituted with a substituent that does not excessively hinder the intended effect of the present invention. For example, one in which one or more hydrogen atoms of an aromatic group are substituted with a halogen atom, a substituted or unsubstituted alkyl group, a trifluoromethyl group, a cyano group, a nitro group, or an alkoxy group can be exemplified.

  Further, the plurality of R present in the organic charge transporting polymer molecule according to the present invention may be the same or different from each other. That is, all three Rs present in the repeating unit may be the same or different from each other. Further, R may be the same or different from each other among the repeating units. From the viewpoint of synthesis, a polymer in which a plurality of Rs are all the same is preferable.

  By appropriately selecting R, the solubility of the organic charge transporting polymer according to the present invention in the solvent can be adjusted. For this reason, when the solvent which melt | dissolves the polymer of this invention is specified, R can be suitably selected so that it may melt | dissolve in the solvent with a desired density | concentration. In addition, all the polymers of this invention have high solubility with respect to the solvent used for wet film-forming methods, such as chloroform. Therefore, the polymer of the present invention can be easily and quickly formed into a thin film by a wet film formation method using a solvent such as a spin coating method, and there is no need to use a time-consuming and expensive vacuum deposition method or the like. Have advantages.

  The organic charge transporting polymer according to the present invention preferably has a weight average molecular weight of several thousand or more by GPC (polystyrene conversion) measurement. According to the present invention, it is relatively easy to molecularly design a polymer so as to have a desired charge transport property, and it is possible to provide an organic device material according to the purpose of use. For example, in an organic EL element, it can be used as a phosphorescent light-emitting host material or a fluorescent light-emitting material.

  The organic charge transporting polymer according to the present invention has a relatively high glass transition temperature and high thermal stability. The glass transition temperature varies depending on the combination of R in formula (1) and the average molecular weight. Since the glass transition temperature is high, when the organic charge transporting polymer of the present invention is applied to an organic device such as an EL element, the amount of heat generated when a driving voltage is applied can be suppressed.

  The method for producing an organic charge transporting polymer represented by the following general formula (1) according to the present invention includes a method in which a halide represented by the following formula (2) is lithiated with an alkyl lithium, and a trihalogenated compound. A step of reacting with boron.

（式（１）において、Ｒは、それぞれ独立に、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族基、ハロゲン原子、又は水素原子である。繰り返し単位中の３つのＲは、それぞれ同一であっても互いに異なっていても良い。また、繰り返し単位間で各Ｒは、全て同一であっても互いに異なっていても良い。ｎは、２以上の整数である。）

(In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. (It may be the same or different from each other, and each R may be the same or different from each other among the repeating units. N is an integer of 2 or more.)

（式（２）において、Ｘは、ハロゲン原子を表す。Ｒは、それぞれ独立に、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族基、ハロゲン原子、又は水素原子である。）

(In Formula (2), X represents a halogen atom. R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom.)

  According to the present invention, the number of steps necessary for the synthesis can be reduced by having the above steps, so that the synthesis can be performed in a shorter time and the cost is advantageous. According to the production method of the present invention, the polymer represented by the above formula (1) can be easily obtained.

  X represented by the general formula (2) is a halogen atom and is at least one selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Especially, it is preferable that X is a bromine atom or an iodine atom from a reactive point. As R, the same as described in the organic charge transporting polymer can be used. R represented by the general formula (2) corresponds to R of the polymer represented by the general formula (1) to be synthesized. When two or more different Rs are used as the halide represented by the above formula (2), three Rs in the repeating unit of the polymer represented by the general formula (1) or between the repeating units are used. Each of R may be the same as or different from each other.

The manufacturing method according to the present invention can be carried out, for example, as follows. First, the halide represented by the general formula (2) is dissolved in an inert solvent at room temperature under nitrogen. 1.6 to this solution
Add 2.7M concentrated alkyl lithium (eg, hexane solution) and lithiate at room temperature. The resulting solution is stirred for 2-10 hours at room temperature and then boron trihalide is added dropwise. A solution of 4-alkylphenyllithium in diethyl ether (1 equivalent to the halide represented by the formula (2)) is added dropwise to the resulting solution, and the mixture is stirred for 3 hours. Subsequently, a diethyl ether solution of 4-alkyl halogenated benzene (2 equivalents relative to the halide represented by the formula (2)) was added dropwise and stirred for 3 hours, followed by hydrolysis with distilled water added overnight. . The reaction time may be appropriately adjusted and is not particularly limited.
Here, it is preferable that the said alkyl lithium is 2.0 mol or more with respect to 1.0 mol of halides represented by the said General formula (2), Furthermore, 2.05-2.2 mol. Moreover, boron trihalide is 0.3-0.34 mol with respect to 1.0 mol of halide represented by the said General formula (2), Furthermore, it is 0.31-0.33 mol. preferable.
Examples of the alkyl lithium used for the reaction include n-butyl lithium, sec-butyl lithium, tert-butyl lithium and the like. Boron trihalide used in the reaction includes boron trifluoride / diethyl ether complex, boron trifluoride / acetic acid complex, boron trifluoride / dimethanol complex, boron trifluoride / methanol complex, boron tribromide, etc. Is mentioned. Examples of the inert solvent used in the reaction include dehydrated diethyl ether.

  After completion of the hydrolysis reaction, the organic layer is extracted with a solvent such as chloroform and water. Thereafter, the organic layer is preferably further washed with water. The obtained organic layer is dried with anhydrous magnesium sulfate or the like, and the solution obtained by filtration is concentrated using an evaporator or the like to obtain a residue. The obtained residue is dissolved in a small amount of chloroform and purified by reprecipitation with methanol. For example, the object is obtained by repeating this operation three times.

Since the organic charge transporting polymer according to the present invention has a good charge transporting property, it can be widely applied as an organic device material. For example, it is suitably used as a material for forming an organic layer of an organic light emitting device such as an organic EL element or an organic semiconductor layer in an organic transistor.
In addition, by design, it has both electron transporting and hole transporting properties in the molecule and luminescence, and the compound can be uniformly dispersed in the film. It is suitably used as a material for an EL element.

(Example 1: Production of organic charge transporting polymer according to the present invention)
According to the following scheme, an organic charge transporting polymer [1a] (wherein R ′ is a tert-butyl group) according to the present invention having a structural formula was prepared.

(1) Synthesis of Formula [2a] (wherein R ′ is a tert-butyl group) Formula [4a] (wherein R ′ is a tert-butyl group) is a literature (K.-T. Wong et al., Org). According to Lett. 2005, 7, 5361-5364).
Formula [4a] (6.007 g; 20.062 mmol) and N-iodosuccinimide (9.246 g; 41.096 mmol) were stirred in chloroform (75 ml) -acetic acid (50 ml) overnight at room temperature under nitrogen atmosphere. After that, chloroform was distilled off and then poured into 300 ml of water. The resulting precipitate was filtered and washed with a large amount of water. The precipitate was dissolved in chloroform and dried over anhydrous magnesium sulfate, and then unnecessary substances were filtered off. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent: chloroform), followed by recrystallization from dichloromethane-methanol to obtain the desired product (formula [2a] (wherein R ′ represents a tert-butyl group). )) Was obtained (10.408 g; 94.1%).

When ¹ HNMR and ¹³ CNMR of the obtained compound were measured, the following data was obtained.
¹ H NMR (400 MHz, CDCl 2 _C , TMS): δ (ppm) 1.42 (s, 9H, CH ₃ ), 7.17 (d, J = 8.8 Hz, 2H, arom.H), 7.39 (D, J = 8.4 Hz, 2H, arom.H), 7.60 (d, J = 8.8 Hz, 2H, arom.H), 7.65 (dd, J = 8.6 and 1.4 Hz) , 2H, arom.H), 8.38 (d, J = 2.0 Hz, 2H, arom.H).
¹³ C NMR (100.4 MHz, CDCl ₃ ): δ (ppm) 31.36, 34.84, 82.67, 112.09, 124.28, 126.37, 126.955, 129.23, 133. 84, 134.74, 140.18, 151.18.

(2) Synthesis of Formula [1a] (wherein R ′ is a tert-butyl group) Formula [2a] (5.000 g; 9.102 mmol) was stirred (suspended) in 15 ml of diethyl ether under a nitrogen atmosphere. Solution) Add 2.71 M butyllithium / hexane solution (6.8 ml) to the solution and lithiate. After stirring for 2 hours, the solution was ice-cooled, boron trifluoride / diethyl ether complex (0.76 ml) was added, and the mixture was stirred for 2 hours. Boron trifluoride-diethyl ether complex (0.76 ml) is further added twice every 2 hours. To this solution, 4-alkylphenyl lithium (1 equivalent to the formula [2a]) / diethyl ether (15 ml) is added dropwise and stirred for 3 hours. Subsequently, 4-alkyl halogenated benzene (2 equivalents relative to the formula [2a]) / diethyl ether (15 ml) is added dropwise and stirred for 3 hours, followed by hydrolysis with water (50 ml) added overnight. Chloroform (100 ml) and water (150 ml) are added to extract the organic layer. The organic layer is further washed twice with 200 ml of water. The organic layer is dried over anhydrous magnesium sulfate, and unnecessary substances are filtered, and then the organic solvent is concentrated. The obtained residue is dissolved in a small amount of chloroform and purified by reprecipitation with methanol. This operation was repeated three times to obtain a target polymer (formula [1a] (wherein R ′ is a tert-butyl group)).

When ¹ HNMR and GPC measurement of the obtained polymer was performed, the following data was obtained.
¹ H NMR (400 MHz, CDCl _C , TMS): δ (ppm) 1.36-1.46 (m, CH ₃ ), 7.22-8.19 (m, arom. H), 8.45-8 .73 (m, arom.H).
Mw = 7,388; Mn = 7,017; Mw / Mn = 1.053 (polystyrene standard in THF)

(Example 2: Production of organic charge transporting polymer according to the present invention)
According to the above scheme, the organic charge transporting polymer [1b] (wherein R ′ is an n-butyl group) of the present invention having the structural formula was prepared in the same manner as in Example 1.

(1) Synthesis of Formula [4b] (wherein R ′ is an n-butyl group) Carbazole [3] (10.122 g; 59.877 mmol) and 4-butyliodobenzene (15.606 g; 59.996 mmol), copper A powder (1.947 g; 30.636 mmol) and potassium carbonate (8.272 g; 59.853 mmol) were heated and stirred overnight at 140 ° C. under a nitrogen atmosphere in DMSO, and poured into 300 ml of water after cooling. The precipitate was filtered and washed with a large amount of water. These were dissolved in chloroform, dried over anhydrous magnesium sulfate, and unnecessary substances were removed by filtration. The residue obtained by concentrating the filtrate was reprecipitated with methanol to obtain the desired product [4b] (14.786 g; 82.5%).
¹ H NMR (400 MHz, CDCl _C , TMS): δ (ppm) 0.99 (t, J = 7.4 Hz, 3H, CH ₃ ), 1.395-1.49 (m, 2H, CH ₂ ), 1.66-1.74 (m, 2H, CH ₂ ), 2.73 (t, J = 8.0 Hz, 2H, ArCH ₂ ), 7.25-7.30 (m, 2H, arom. H) 7.38-7.40 (m, 6H, arom.H), 7.45 (d, J = 8.4 Hz, 2H, arom.H), 8.14 (d, J = 8.4 Hz, 2H) , Arom.H).
¹³ C NMR (100.4 MHz, CDCl ₃ ): δ (ppm) 13.99, 22.42, 33.60, 33.56, 109.80, 119.67, 120.21, 123.18, 125. 79, 126.90, 129.74, 135.08, 141.01, 142.30.
(2) Synthesis of Formula [2b] (wherein R ′ is an n-butyl group) Using Formula [4b] instead of Formula [4a] in Example 1, Formula [2b] (Wherein R ′ is an n-butyl group) was synthesized. The desired product (formula [2b] (wherein R ′ is an n-butyl group)) was obtained (yield 88.5%).

When ¹ HNMR and ¹³ CNMR of the obtained compound were measured, the following data was obtained.
¹ H NMR (400 MHz, CDCl _C , TMS): δ (ppm) 0.99 (t, J = 7.4 Hz, 3H, CH ₃ ), 1.39-1.48 (m, 2H, CH ₂ ), 1.66-1.73 (m, 2H, CH ₂ ), 2.73 (t, J = 8.0 Hz, 2H, ArCH ₂ ), 7.14 (d, J = 8.8 Hz, 2H, arom. H), 7.355 (d, J = 8.8 Hz, 2H, arom.H), 7.40 (d, J = 8.4 Hz, 2H, arom.H), 7.65 (dd, J = 8 .6 and 1.4 Hz, 2H, arom.H), 8.38 (d, J = 1.6 Hz, 2H, arom.H).
¹³ C NMR (100.4 MHz, CDCl ₃ ): δ (ppm) 13.98, 22.41, 33.55, 35.36, 82.66, 112.03, 124.265, 126.69, 129. 23, 129.97, 134.04, 134.75, 140.20, 143.10.

(2) Synthesis of Formula [1b] (wherein R ′ is an n-butyl group) In the same manner as in Example 1, using Formula [2b] obtained above instead of Formula [2a] in Example 1 The compound of formula [1b] (wherein R ′ is an n-butyl group) was synthesized. A target polymer (formula [1b] (wherein R ′ is an n-butyl group)) was obtained.

When ¹ HNMR and GPC measurement of the obtained polymer was performed, the following data was obtained.
¹ H NMR (400 MHz, CDCl _C , TMS): δ (ppm) 0.94-1.02 (m, CH ₃ ), 1.45 (m, CH ₂ ), 1.70-1.72 (m, _{CH 2), 2.74-2.77 (m,} CH 2), 7.18-7.965 (m, arom.H), 8.48-8.72 (m, arom.H).
Mw = 7,478; Mn = 7,020; Mw / Mn = 1.065 (polystyrene standard in THF)

Claims (3)

An organic charge transporting polymer composed of a repeating unit represented by the following formula (1).

(In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. (It may be the same or different from each other, and each R may be the same or different from each other among the repeating units. N is an integer of 2 or more.) An organic compound composed of a repeating unit represented by the following formula (1) having a step of reacting a lithiated halogenide represented by the following formula (2) with alkyllithium and boron trihalide. A method for producing a charge transporting polymer.

(In formula (2), X represents a halogen atom. R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom.)

(In the formula (1), each R is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, or a hydrogen atom. (It may be the same or different from each other, and each R may be the same or different from each other among the repeating units. N is an integer of 2 or more.)   An organic device material using the organic charge transporting polymer according to claim 1.