KR101675073B1 - Organic semiconductor polymer, and transistor and electronic device including the same - Google Patents

Abstract

An organic semiconductor polymer comprising a first repeating unit of pyrimido [5,4-d] pyrimidine and a second repeating unit comprising a heteroaromatic ring represented by the formula (1) And a transistor and an electronic device including the same.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic semiconductor polymer, and a transistor including the organic semiconductor polymer and an electronic device. BACKGROUND OF THE INVENTION < RTI ID = 0.0 &

The present invention relates to an organic semiconductor polymer and a transistor including the same and an electronic device.

With the development of the information society, it has been required to develop a new image display device which improves disadvantages such as a heavy weight and a large volume of a conventional CRT (Cathode Ray Tube), and accordingly, a liquid crystal display Various flat panel display devices such as a liquid crystal display (LCD), an organic light emitting diode (OLED), a plasma display panel (PDP), a surface-conduction electron-emitter display device .

Thin film transistors (TFTs) using amorphous silicon as a semiconductor layer as switching elements of flat panel display devices have been widely used.

Amorphous silicon thin film transistors are widely used because of their good uniformity, high electrical characteristics in the doped state, and excellent insulating properties in the undoped state.

However, conventionally, in order to deposit an amorphous silicon thin film transistor on a substrate, a process has to be carried out at a high temperature of about 300 ° C., and thus, a polymer substrate for implementing a flexible display Which is difficult to apply.

An organic thin film transistor (OTFT) using an organic semiconductor material has been proposed to solve this problem.

The organic thin film transistor generally includes a bottom contact (BC) type including a substrate, a gate electrode, an insulating layer, a source / drain electrode, and a channel region and having a channel region formed on the source and drain electrodes, And a top contact (TC) type in which a metal electrode is formed from the back by evaporation or the like.

Examples of the low molecular weight or oligomer organic semiconductor material filled in the channel region of the organic thin film transistor (OTFT) include melocyanine, phthalocyanine, perylene, pentacene, C60, thiophene oligomer, etc. These low molecular weight or oligomer organic semiconductor materials Is formed in the channel region as a thin film mainly by a vacuum process.

Organic semiconductor polymer materials are advantageous in terms of processability in that they can be processed at a low cost by area processing such as a printing technique.

An aspect of the present invention is to provide an organic semiconductor polymer having an excellent charge mobility and being capable of a solution process.

Another aspect of the present invention is to provide a transistor including the organic semiconductor polymer.

Another aspect of the present invention is to provide an electronic device comprising the organic semiconductor polymer.

According to an aspect of the present invention, there is provided a method for producing a compound represented by Formula 1, comprising reacting a first repeating unit of pyrimido [5,4-d] pyrimidine represented by the following Formula 1 with a second repeating unit of a second aromatic ring containing a heteroaromatic ring An organic semiconductor polymer containing repeating units is provided.

[Chemical Formula 1]

In Formula 1,

R ¹ and R ² are the same or different from each other and each represents hydrogen, halogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 A substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, NR ³ R ⁴ (wherein R ³ and R ⁴ are the same or different from each other, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, or selected from the group consisting of heteroaryl groups and combinations of the unsubstituted C2 to C30), and is selected from the group consisting of, or alternatively the one or non-adjacent two or more CH ₂ -O- group, , -S- _{, -SO 2 -, -CO-, -OCO-} , -COO-, -CH = CH-, -C≡C- , and -SiR ⁵ R ⁶ (wherein R ⁵ and R ⁶ are different from or equal to each other, hydrogen, A substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof)

Ar is a substituted or unsubstituted, substituted or unsubstituted C6 to C30 condensed polycyclic group containing a substituted or unsubstituted C4 to C14 heteroaromatic ring or a heteroaromatic ring, provided that Ar is a substituted or unsubstituted pyrimido [ 5,4-d] pyrimidine,

a and b represent molar ratios where a ranges from about 0.01 to about 0.99 and b ranges from about 0.01 to about 0.99.

The first repeating unit may be represented by the following formula (2).

(2)

In Formula 2,

R ¹⁰ to R ¹³ are the same or different and each is hydrogen or a substituted or unsubstituted C1 to C20 linear or branched alkyl group.

The second repeating unit may be represented by the following general formula (3).

(3)

In Formula 3,

R ²⁰ to R ²⁶ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof.

The second repeating unit may be a repeating unit represented by the following general formula (4) including thiophene.

[Chemical Formula 4]

In Formula 4,

R ³⁰ represents hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 Or a substituted or unsubstituted C 2 to C 30 heteroaryl group and combinations thereof, or alternatively two or more of the two or more CH ₂ groups which are not adjacent or are selected from the group consisting of -O-, -S _{-, -SO 2 -, -CO-,} -OCO-, -COO-, -C = C-, -C≡C- , and -SiR ³¹ R ³² (wherein R ³¹ and R ³² are different from or equal to each other, hydrogen , A substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof. May be substituted by taekdoem),

k is an integer of 1 or 2,

Ar ₁ is a substituted or unsubstituted C4 to C14 heteroaromatic ring (heteroaromatic ring), or a substituted or unsubstituted condensed polycyclic unsubstituted C6 to C30 ventilation, including heteroaromatic rings, provided that Ar ₁ is a substituted or unsubstituted Is not a substituted pyrimido [5,4-d] pyrimidine or a substituted or unsubstituted thiophene,

c and d represent molar ratios where c ranges from about 0.01 to about 0.99 and d ranges from about 0.01 to about 0.99.

The Ar1 may be a repeating unit represented by the formula (3).

The organic polymer containing the repeating unit represented by the formula (1) may be an organic polymer containing repeating units represented by the following formula (5) or (6).

[Chemical Formula 5]

In Formula 5,

R ¹⁰ to R ¹³ are the same or different and each is hydrogen or a substituted or unsubstituted C1 to C20 linear or branched alkyl group,

R ³³ and R ³⁴ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C 1 to C 20 linear or branched alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or non-substituted is selected from the group consisting of unsubstituted C6 to C30 aryl group, a substituted or unsubstituted heteroaryl group unsubstituted C2 to C30 and combinations thereof, or optionally more than one or non-adjacent CH ₂ groups are _{-O-, -S-, -SO 2 -,} -CO-, -OCO-, -COO-, -C = C-, -C≡C- , and -SiR ³¹ R ³² (wherein R ³¹ and R ³² are the same or different and are selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, An unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Sum may be substituted by selected from the group) consisting of,

a, c and d represent molar ratios, wherein a is in the range of 0.01 to 0.99 and c + d is in the range of 0.01 to 0.99.

[Chemical Formula 6]

In Formula 6,

R < ¹¹ > and R < ¹³ > are the same as or different from each other,

R ³⁴ , a, c and d are as defined in the above formula (5).

The organic semiconductor polymer may include a terminal functional group represented by any one of the following formulas (7) to (10).

(7)

In Formula 7,

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 5;

[Chemical Formula 8]

In Formula 8,

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 6;

[Chemical Formula 9]

In the above formula (9)

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 3;

[Chemical formula 10]

In Formula 10,

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 3;

According to another aspect of the present invention, there is provided a transistor including the organic semiconductor polymer.

The transistor comprising: a gate electrode located on a substrate; A source electrode and a drain electrode which are positioned opposite to each other to define a channel region; An insulating layer electrically isolating the source electrode and the drain electrode from the gate electrode; And an active layer including the organic semiconductor polymer formed in the channel region.

According to another aspect of the present invention, there is provided an electronic device including the organic semiconductor polymer.

Other details of the embodiments of the present invention are included in the following detailed description.

Since the organic semiconductor polymer has excellent charge mobility, it can be applied to transistors, solar cells, memory devices, organic light emitting devices (OLED), optical sensors, and laser devices. In addition, since it is possible to form a thin film by a solution process, it is advantageous to manufacture a large-sized device, and the manufacturing cost of the device can be reduced.

1 is a schematic cross-sectional view of a transistor according to an embodiment of the present invention.
2 is a schematic cross-sectional view of a transistor according to another embodiment of the present invention.
3 is a ¹ H NMR spectrum of the compound of Formula 11 prepared according to Example 1 of the present invention.
4 is a graph showing on-state current transfer characteristics of an organic thin film transistor (OTFT) device manufactured according to Example 3 in air.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

When a part of a layer, film, substrate, or the like is referred to as being "on" another component, it includes not only the case where it is "directly on" another component, but also the case where there is another component in between. Conversely, when a part is "directly over" another part, it means that there is no other part in the middle.

Unless otherwise defined herein, "heteroaromatic ring" means a C2 to C30 heteroaryl group, a C3 to C30 heterocycloalkenyl group or a C3 to C30 heterocycloalkynyl group. "Conjugated polycyclic" is selected from the group consisting of a C3 to C30 cycloalkyl group, a C3 to C30 cycloalkenyl group, a C2 to C30 heterocycloalkyl group, a C2 to C30 heteroaryl group, and a C3 to C30 heterocycloalkenyl group Quot; means a fused ring that is linked to at least one ring and the heteroaromatic ring.

Refers to a compound containing a heteroatom selected from the group consisting of N, O, S, Si and P, wherein one to four heteroatoms may be contained in one ring.

As used herein, the term "substitution" means that the hydrogen in the compound or compound is a fluoro group, a C1 to C30 linear or branched alkyl group, a C3 to C30 cycloalkyl group, a C1 to C20 fluoroalkyl group, a C1 to C20 perfluoroalkyl group (C _n F _{2n + 1} ), a C1 to C30 linear or branched alkoxy group, a C3 to C30 cycloalkoxy group, a C2 to C30 linear or branched alkoxyalkyl group, a C4 to C30 cycloalkoxyalkyl group, and combinations thereof ≪ / RTI > is substituted by a functional group selected from the group consisting of < RTI ID = 0.0 >

According to an embodiment of the present invention, there is provided a method for preparing a compound of formula (I), which comprises a first repeating unit of pyrimido [5,4-d] pyrimidine and a second repeating unit comprising a heteroaromatic ring , And an organic semiconductor polymer represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ and R ² are the same or different from each other and each represents hydrogen, halogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 A substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, NR ³ R ⁴ (wherein R ³ and R ⁴ are the same or different from each other, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, or selected from the group consisting of heteroaryl groups and combinations of the unsubstituted C2 to C30), and is selected from the group consisting of, or alternatively the one or non-adjacent two or more CH ₂ -O- group, , -S- _{, -SO 2 -, -CO-, -OCO-} , -COO-, -C = C-, -C≡C- and -SiR ⁵ R ⁶ (wherein R ⁵ and R ⁶ are different from or equal to each other, hydrogen, A substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof)

Ar is a substituted or unsubstituted, substituted or unsubstituted C6 to C30 condensed polycyclic group containing a substituted or unsubstituted C4 to C14 heteroaromatic ring or a heteroaromatic ring, provided that Ar is a substituted or unsubstituted pyrimido [ 5,4-d] pyrimidine,

a and b represent molar ratios where a ranges from about 0.01 to about 0.99 and b ranges from about 0.01 to about 0.99. Within the above range, the physical properties of the polymer can be improved.

The organic semiconductor polymer of Formula 1 may have a number average molecular weight (Mn) of about 5,000 to about 200,000 and a number average molecular weight (Mn) of about 10,000 to about 50,000.

In Formula 1, the first repeating unit and the second repeating unit may be alternately arranged or randomly arranged.

The first repeating unit may be a repeating unit represented by the following formula (2).

(2)

In the above formula (2).

R ¹⁰ to R ¹³ are the same or different and each is hydrogen or a substituted or unsubstituted C1 to C20 linear or branched alkyl group.

Examples of the repeating unit of the above formula (2) include the following formulas (2-1) to (2-3).

[Formula 2-1] [Formula 2-2] [Formula 2-3]

The second repeating unit may be represented by the following general formula (3).

(3)

In Formula 3,

R ²⁰ to R ²⁶ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof.

The second repeating unit may be a repeating unit represented by the following formula (4) containing thiophene.

[Chemical Formula 4]

In Formula 4,

R ₃₀ represents hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 Or a substituted or unsubstituted C 2 to C 30 heteroaryl group and combinations thereof, or alternatively two or more of the two or more CH ₂ groups which are not adjacent or are selected from the group consisting of -O-, -S _{-, -SO 2 -, -CO-,} -OCO-, -COO-, -C = C-, -C≡C- , and -SiR ³¹ R ³² (wherein R ³¹ and R ³² are different from or equal to each other, hydrogen , A substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof. May be substituted by taekdoem),

k is an integer of 1 or 2,

Ar ₁ is a substituted or unsubstituted C4 to C14 heteroaromatic ring (heteroaromatic ring), or a substituted or unsubstituted condensed polycyclic unsubstituted C6 to C30 ventilation, including heteroaromatic rings, provided that Ar ₁ is a substituted or unsubstituted Is not a substituted pyrimido [5,4-d] pyrimidine or a substituted or unsubstituted thiophene,

c and d represent molar ratios where c ranges from about 0.01 to about 0.99 and d ranges from about 0.01 to about 0.99. Within the above range, the physical properties of the polymer can be improved.

In the formula (4), when k is 2, R ³⁰ may be the same or different from each other.

The thiophene repeating unit and the Ar ₁ repeating unit in the above formula (4) may be alternately arranged or randomly arranged.

The Ar1 may be a repeating unit represented by the formula (3).

When the second repeating unit of Formula 1 is the repeating unit of Formula 4, the charge mobility can be improved by improving the coplanarity and the blocking current can be lowered by controlling the energy level.

The organic polymer containing the repeating unit represented by the formula (1) may be an organic polymer containing repeating units represented by the following formula (5) or (6).

[Chemical Formula 5]

In Formula 5,

R ¹⁰ to R ¹³ are the same or different and each is hydrogen or a substituted or unsubstituted C1 to C20 linear or branched alkyl group,

R ³³ and R ³⁴ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C 1 to C 20 linear or branched alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or non-substituted is selected from the group consisting of unsubstituted C6 to C30 aryl group, a substituted or unsubstituted heteroaryl group unsubstituted C2 to C30 and combinations thereof, or optionally more than one or non-adjacent CH ₂ groups are _{-O-, -S-, -SO 2 -,} -CO-, -OCO-, -COO-, -C = C-, -C≡C- , and -SiR ³¹ R ³² (wherein R ³¹ and R ³² are the same or different and are selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, An unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Sum may be substituted by selected from the group) consisting of,

a, c and d represent molar ratios, wherein a is in the range of 0.01 to 0.99 and c + d is in the range of 0.01 to 0.99.

The pyrimido [5,4-d] pyrimidine repeating unit, the thiophene repeating unit and the Ar ₁ repeating unit in Formula 5 may be alternately arranged or randomly arranged.

[Chemical Formula 6]

In Formula 6,

R < ¹¹ > and R < ¹³ > are the same as or different from each other,

R ³⁴ , a, c and d are as defined in the above formula (5).

The pyrimido [5,4-d] pyrimidine repeating unit, the thiophene repeating unit and the Ar ₁ repeating unit in Formula 5 may be alternately arranged or randomly arranged.

The organic semiconductor polymer may include a terminal functional group represented by any one of the following formulas (7) to (10).

(7)

In Formula 7,

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 5;

[Chemical Formula 8]

In Formula 8,

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 6;

[Chemical Formula 9]

In the above formula (9)

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 3;

[Chemical formula 10]

In Formula 10,

R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 3;

 Preferable examples of the formula (5) include, but are not limited to, the following formulas (11) to (16). A, b and c in the following formulas (11) to (15) are the same as a, c and d in formula (5), and a and b in formula (16) are the same as those in formula (1).

(11)

[Chemical Formula 12]

[Chemical Formula 13]

 [Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

The organic semiconductor polymer represented by Formula 1 may be prepared according to the method of Stille et al (Angew. Chem. Int. Ed. Engl. 1986, Vol. 25, pp. 508-524), Suzuki et al (J. Am. Chem. , Vol. 111, pp. 314-321), McCullough et al (US 6,166,172, 1999) or Yamamoto et al. (Macromolecules 1992, Vol. 25, pp. 1214-1226). For example, in the case of an organic semiconductor polymer containing a repeating unit represented by the formula (5), the monomer may be reacted as shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In Scheme ₁ Ar 1, R ¹⁰ to ^{R 13, R 33, R 34} , a, c and d are the same as in formula 5, a ', c' and d 'are as in a, c and d the formula (5), respectively The same,

X, X ', Y, Y', Z and Z 'are each independently a reactive group selected from the group consisting of halogens such as Br, I and Cl, trialkyltin and borane groups , But is not limited thereto,

The trialkyltin may be represented by the following general formula (17), and the borane group may be represented by the following general formula (18) or (19).

[Chemical Formula 17]

In the formula (17), R ₃₁ to R ₃₃ are the same or different from each other and each independently represents hydrogen or a C 1 to C 7 alkyl group, and at least one of R ₃₁ to R ₃₃ is an alkyl group.

[Chemical Formula 18]

[Chemical Formula 19]

In the above formula (19), R ₃₄ to R ₃₇ are the same or different from each other and each independently represents hydrogen or a C 1 to C 7 alkyl group, and at least one of R ₃₄ to R ₃₇ is an alkyl group.

As the catalyst used in the reaction of Reaction Scheme 1, organometallic catalysts represented by the following Chemical Formulas 20-1 to 20-4 can be used.

[Chemical Formula 20-1]

Pd (L ₁ ) _x

[Chemical Formula 20-2]

Pd (L ₂ ) _{4- y} Cl _y

In Formulas (20-1) and (20-2), L ₁ and L ₂ are each independently selected from the group consisting of triphenylphosphine (PPh ₃ ), 1,4-bis (diphenylphosphine) phosphino) ferrocene (1,1'-bis (diphenylphosphino) ferrocene (dppf), acetate (OAc), triphenyl Ari new (AsPh _3), triphenyl phosphite, P (OPh) a ligand selected from the group consisting of ₃ x Is an integer of 2 to 4 and y is an integer of 1 to 3.

[Formula 20-3]

Ni (L ₃ ) _x

[Chemical Formula 20-4]

Ni (L ₄ ) _{3- y} Cl _y

L ₃ and L ₄ in the general formulas (20-3) and (20-4) are preferably 1,3-bis (diphenylphosphino) propane (dppp), 1,2-bis (diphenylphosphino) ethane A diphenylphosphinoalkane such as 4-diphenylphosphinobutane (dppb), and a cycloalkene such as bis (1,5-cyclooctadiene) (COD), and x is 2 or 3 And y is an integer of 1 or 2.

A specific example of the palladium catalyst is a palladium (0) catalyst of tetrakis (triphenylphosphine) palladium (0) compound (Pd (PPh ₃ ) ₄ ), and 1,4-bis (triphenylphosphine) palladium ) dichloride _{(PdCl 2 (PPh 3) 2} ), [1,4- bis (diphenoquinone skill phosphine) butane] palladium (II) dichloride _{(Pd (dppb) Cl 2)} , [1,1'- bis ( Palladium (II) catalysts such as diphenylphosphino) ferrocene] palladium (II) dichloride (Pd (dppf) Cl ₂ ) and palladium (II) acetate (Pd (OAc) 2).

Specific examples of the nickel catalyst include nickel (0) catalyst of bis (1,5-cyclooctadiene) nickel (0) compound (Ni (COD) ₂ ), 1,3- Nickel (II) catalysts such as chloride (Ni (dppp) Cl ₂ ) and 1,2-bis (diphenylphosphino) ethane nickel (II) chloride (Ni (dppe) Cl ₂ ).

For example, in the case of the tetrakis (triphenylphosphine) palladium (0) compound, the catalyst may be used in an amount of 0.2 to 15 mol% based on the monomer, and may be used in an amount of 2 to 10 mol %.

As the polymerization solvent, toluene, dimethylformaldehyde (DMF), tetrahydrofuran (THF), N-methylpyrrolidinone (NMP) and the like can be used.

The condensation reaction is carried out at 80 to 120 캜 in a nitrogen atmosphere for 6 to 48 hours.

The organic semiconductor polymer may be used in an active layer of a transistor. The transistor comprising: a gate electrode located on a substrate; A source electrode and a drain electrode which are positioned opposite to each other to define a channel region; An insulating layer electrically isolating the source electrode and the drain electrode from the gate electrode; And an active layer including the organic semiconductor polymer formed in the channel region.

The active layer may be formed by a solution process such as a screen printing process, a printing process, a spin coating process, a dipping process, an inkjet process, or the like, on a composition containing an organic semiconductor polymer. When the active layer is formed by the solution process as described above, the process cost can be reduced and it is useful in manufacturing a large-sized device.

1 and 2 are schematic cross-sectional views of a transistor according to an embodiment of the present invention. The transistor according to an embodiment of the present invention may be a thin film transistor. In case of a thin film transistor, the thickness of the thin film may be several nm to several 탆.

Referring to FIG. 1, a transistor 10 has a gate electrode 14 formed on a substrate 12, and an insulating layer 16 covering the gate electrode 14 is formed. A source electrode 17a and a drain electrode 17b defining a channel region are formed in the insulating layer 16 and an active layer 18 is formed in a channel region. The active layer 18 includes an organic semiconductor polymer do.

2, the transistor 20 includes a source electrode 27a and a drain electrode 27b defining a channel region on a substrate 22, an active layer 28 formed in a channel region, (28) includes an organic semiconductor polymer. An insulating layer 26 is formed while covering the source electrode 27a and the drain electrode 27b and the active layer 28 and a gate electrode 24 is formed thereon.

The substrate 12, 22 may be an inorganic material, an organic material, or a composite of an inorganic material and an organic material. The organic material may be, for example, polyethylene terephthalate (PEN), polyethylene terephthalate (PET), polycarbonate, polyvinyl alcohol, polyacrylate, polyimide, polynorbornene, polyethersulfone, PES), and the like, and examples of the inorganic material include glass and metal.

As the gate electrodes 14 and 24, the source electrodes 17a and 27a and the drain electrodes 17b and 27b, a commonly used metal may be used. Specifically, gold (Au), silver (Ag) (Al), nickel (Ni) indium tin oxide (ITO), and the like.

The insulating layer can be used with a large dielectric constant insulator which (16, 26) as is conventionally used, specifically _{Ba O .33 Sr O .66 TiO 3} (BST, Barium Strontium Titanate), Al 2 O 3, Ta _{2 O 5, La 2 O 5} , Y 2 O 3, and PbZr _O insulator series of TiO ₂ and ferroelectric _{.33 Ti O .66 O 3 (PZT} ), Bi 4 Ti 3 O 12, BaMgF 4, SrBi 2 (TaNb _{) 2 O 9, Ba (ZrTi} ) O 3 (BZT), BaTiO 3, SrTiO 3, Bi 4 Ti 3 O 12, SiO 2, SiN x, inorganic insulating material as polyimide (polyimide such as AlON), BCB (benzocyclobutane) An organic insulator such as parylene, polyacrylate, polyvinylalcohol or polyvinylphenol may be used, but the present invention is not limited thereto. Although not mentioned above, the inorganic insulator disclosed in U.S. Patent No. 5,946,551 and the organic insulator described in U.S. Patent No. 6,232,157 can also be used as the insulating layers 16 and 26.

The organic semiconductor polymer may be applied to a solar cell, a memory device, an organic light emitting diode (OLED), an optical sensor, a laser device, or the like.

Hereinafter, exemplary embodiments of the present invention will be described. However, the following examples are only illustrative examples of the present invention, and the present invention is not limited by the following examples.

Example

Synthesis Example 1 Synthesis of 2,4,6,8-tetrachloropyrimido [5,4-d] pyrimidine (2,4,6,8-tetrachloropyrimido [5,4-d] pyrimidine)

R. Pamukcu, et al. US 6,232,312: M. Murakami, et al. The synthesis method of US 3,687,950 was referred to for synthesis. ¹² C-NMR (CDCl ₃ , ppm): d 165.62 (4,8-C), 157.60 (2,6-C), 141.76 (4a, 8a-C).

Synthesis Example 2: 2,6-Dichloro-4,8-bis (N- octylamino) pyrimido [5,4-d] pyrimidine (2,6-dichloro -4,8-bis (N- octylamino) pyrimido [5,4-d] pyrimidine )

The chloroform solution of 2,4,6,8-tetrachloropyrimido [5,4-d] pyrimidine (0.65 g, 2.5 mmol) was lowered to -10 ° C as shown in Reaction Scheme 2, and octylamine 1.6 g, 12.3 mmol) in chloroform (15 mL) is slowly added at a temperature ranging from -10 ° C to room temperature (25 ° C). The reaction solution was reacted at 10 ° C or less for 30 minutes, and then chloroform was removed at room temperature under reduced pressure to obtain a white solid. (0.80 g, yield = 70.2%). ¹ H NMR (CDCl 3, ppm): d 6.86 (t, 2H, J = 5.37 Hz, NH), 3.57 (q, 4H, J = 6.25 Hz, (m, 20H, (CH2) 5), 0.88 (t, 6H, CH3). ¹³ C { ¹ H} NMR (CDCl 3, ppm): d 159.38 (4,8-C), 156.52 (2,6-C), 131.66 (4a, 8a-C), 41.20 (C2), 29.18 (C3), 29.16 (C4), 28.99 (C5), 26.84 (C6), 22.64 (C7), 14.05 (C8).

[Reaction Scheme 2]

Synthetic example  3: 2,6- Dichloro -4,8-bis (N- Dodecylamino ) Piramide [5,4-d] pyrimidine (2,6- dichloro -4,8-bis (N- dodecylamino ) 피리imli [5,4-d] 피리 미딘 ) Synthesis of

The chloroform solution of 2,4,6,8-tetrachloropyrimido [5,4-d] pyrimidine (0.65 g, 2.5 mmol) was lowered to -10 ° C as shown in Reaction Scheme 3, and then dodecylamine , 2.28 g, 12.3 mmol) in chloroform (15 mL) was added slowly at -10 [deg.] C to room temperature. The reaction solution was reacted at 10 ° C or less for 30 minutes, and then chloroform was removed at room temperature under reduced pressure to obtain a white solid. This white powder was purified by column using chloroform to obtain a white solid . Yield = 78%. ¹ H NMR (CDCl 3, ppm): d 6.89 (t, 2H, NH), 3.58 (q, 4H, N-CH 2) , 0.88 (t, 6H, CH3).

 [Reaction Scheme 3]

Synthetic example  4: 2,6- Dichloro -4,8-bis (N- Dodecylamino ) Piramide [5,4-d] pyrimidine (2,6- dichloro -4,8-bis (N- dodecylamino ) 피리imli [5,4-d] 피리 미딘 ) Synthesis of

The chloroform solution of 2,4,6,8-tetrachloropyrimido [5,4-d] pyrimidine (0.65 g, 2.5 mmol) was lowered to -10 ° C and methylhexylamine (1.42 g, 12.3 mmol ) In chloroform (15 mL) is slowly added at a temperature ranging from -10 ° C to room temperature. The reaction solution was reacted at 10 ° C or less for 30 minutes, and then chloroform was removed at room temperature under reduced pressure to obtain a white solid. This white powder was purified by column using chloroform to obtain a white solid. Yield = 86%. 1 H NMR (CDCl3, ppm): d 4.20 (broad, 6H, N-CH3), 3.41 (b, 4H, N-CH2) ), 0.89 (t, 6H, CH3).

[Reaction Scheme 4]

Synthetic example  5: 2,5- Bis (trimethylstannyl) te Synthesis of 2,5-bis (trimethylstannyl) thiophene (m = 1 in Reaction Scheme 5)

2,5-bis (trimethylstannyl) thiophene (m = 1 in Scheme 5 below) is prepared as described in B. L. Lee, et al. Synthesis method of US7030409 was synthesized by reference.

[Reaction Scheme 5]

18.4 mL, 30 mmol of n-butyllithium (n-BuLi in hexane, 1.63 mol) was added to a solution of 3.0 grams (12.4 mmol) of dibromothiophene in tetrahydrofuran (THF, 50 mL) (SnMe 3 Cl, 5 grams, 25 mmol) is added to the reaction system and the reaction is carried out at -50 ° C. for 4 to 5 hours. Thereafter, the organic layer obtained by separating with water and ether is dried with anhydrous sodium sulfate, and then the solvent is removed. White crystals can be obtained by recrystallization two times with ether. (Yield, 3.1 g, 60%). ¹ H-NMR (300 MHz, CDCl 3) d (ppm) 0.38 (CH 3, 18H), 7.38 (2H, Thiophene-H).

Synthetic example  6: 2,5- Bis (trimethylstannyl) bithiophene  Synthesis of (2,5-bis (trimethylstannyl) bithiophene) (m = 2 in Reaction Scheme 5)

2,5-bis (trimethylstannyl) thiophene (m = 2 in Scheme 5) is prepared as described in B. L. Lee, et al. Synthesis method of US7030409 was synthesized by reference.

18.4 mL of n-butyllithium (n-BuLi in hexane, 1.63 mol) and 30 mmol of n-butyllithium (50 mL) were added to a solution of 4.0 grams (12.4 mmol) of dibromobithiophene in THF (SnMe3Cl, 5 grams, 25 mmol) is added thereto, and the mixture is reacted at -50 ° C for 4 to 5 hours. Thereafter, the organic layer obtained by separating with water and ether is dried with a desiccant and then the solvent is removed. White crystals can be obtained by recrystallization two times with ether. (Yield, 3.9 g, 64%). ¹ H-NMR (300 MHz, CDCl 3) d (ppm) 0.38 (CH 3, 18H), 7.08 (d, 2H, Thiophene- ).

Synthetic example  7: 2- Bromo -3- Hexyl -5-trimethylstannylthiophene (2- Bromo -3- hexyl -5-trimethylstannylthiophene)

50 mmol of 2-bromo-3-hexylthiophene (d) obtained by reacting the same amount of enbromosuccinimide (hereinafter referred to as NBS) with 3-hexylthiophene in DMF at room temperature for 15 hours was reacted at -80 to -90 Was added to a solution of lithium diisopropylamine (hereinafter referred to as LDA, 2.0 M in mix of THF / Hexane) (57 mmol) in anhydrous THF (40 mL) at room temperature while stirring. After reacting at the same temperature for 20-30 minutes, add a THF solution of SnMe 3 Cl (50 mmol) and stir at -50 ° C for 1 hour. After the reaction, the mixture is extracted with ether and water, and the organic layer is concentrated, and the product of the colorless oil is obtained through distillation at a yield of 78%. ^{1 H-NMR (300 MHz,} CDCl 3) d (ppm) 0.34 (9H, CH 3), 0.88 (3H, CH 3), 1.31 (broad, 2nH, - (CH 2) n-), 1.56 (m, _{2H, -CH 2 -), 2.55} (t, 2H, Thiophene-CH 2 -), 6.84 (s, Thiophene-H).

[Reaction Scheme 6]

Example  One: Pyrimido [5,4-d] pyrimidine  Synthesis of polymer containing

Dichloro-4,8-bis (N-octylamino) pyrimido [5,4-d] pyrimidine (0.28 g, 0.62 mmol) obtained in Synthesis Example 2 and Synthesis Example 7 3-hexyl-5-trimethylstannylthiophene (0.41 g, 1.0 mmol) synthesized in Reference Example 5 and benzothiadiazole (0.04 g, 0.13 mmol) were added to anhydrous DMF, 2,5-bis (trimethylstannyl) thiophene (0.3 g, 0.75 mmol) obtained in Example 1 was also added. After completely dissolving the reaction mixture, Pd (PPh ₃ ) ₄ (7.0 mol%, 0.1 g) was added as a polymerization catalyst and the reaction was carried out at 90 ° C for 12 hours. After the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was filtered, washed twice with aqueous hydrochloric acid / chloroform, twice with aqueous ammonia solution / chloroform, twice with water / chloroform and then washed with methanol, acetone, The polymer was recovered by Soxhlet extraction using chloroform. Dried to obtain a red polymer (yield = 45%, number average molecular weight = 23,000, high temperature GPC, polystyrene standard). The ratio of the repeating units measured by NMR analysis (a: b: c in the following reaction formula 7) = ca. 0.36: 0.57: 0.07, and the ratio of hexylthiophene head-to-tail (HT) to head-to-head (HH) was 0.89: 0.11, .

The ¹ H NMR spectrum of the polymer of Formula 11 prepared in Example 1 is shown in FIG. _{^{1 H NMR (300MHz, CDCl 3}} , ppm) δ 0.9, 1.25, 1.45, 1.82, 2.60 (head-to-head, Th-CH 2), 2.81 (head-to-tail, Th-CH 2), 3.72 ( amine-CH ₂ ), 7.08 (broad, Th-H), 7.75 & 7.90.

[Reaction Scheme 7]

In the above Reaction Scheme 7, a: b: c is 0.36: 0.57: 0.07.

Example  2: Pyrimido [5,4-d] pyrimidine  Synthesis of polymer containing

Dichloro-4,8-bis (N-octylamino) pyrimido [5,4-d] pyrimidine (19.6 mg, 0.043 mmol) obtained in Synthetic Example 2 and Synthesis Example 7 (Trimethylstannyl) thiophene (74 mg, 0.15 mmol) and thiophene-thiazole tetramer derivative (DH Kim, et al., J. Am. Chem. Soc. (0.2 g, 0.17 mmol) were dissolved in anhydrous DMF while heating mildly. Then, Pd (PPh ₃ ) ₄ (a compound of palladium (0) %), And the mixture is reacted at 90 DEG C for 12 hours. After the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was filtered, washed twice with aqueous hydrochloric acid / chloroform, twice with aqueous ammonia solution / chloroform, twice with water / chloroform and then washed with methanol, acetone, The polymer was recovered by Soxhlet extraction using chloroform. Dried to obtain a red polymer (yield = 45%, number average molecular weight = 18,000, high temperature GPC, polystyrene standard). ¹ H NMR (300 MHz, CDCl 3)? 0.9, 1.25, 1.45, 1.82, 2.71, 2.29, 3.72 (amine-CH ₂ ), 7.05 (broad, Th-H), 7.11, 7.12 &

[Reaction Scheme 8]

Is a value determined by the molar ratio of the starting materials of a and b in Reaction Scheme 8 above.

Example  3: Fabrication of organic thin film transistor using polymer

First, chromium used as a gate electrode was deposited on the cleaned glass substrate by sputtering to a thickness of 1000 Å, and then SiO ₂ used as a gate insulating film was deposited to a thickness of 1000Å by CVD. And Au, which is used as a source-drain electrode, was deposited thereon to a thickness of 1200Å by sputtering. The substrate was washed with isopropyl alcohol for 10 minutes before the organic semiconductor material was deposited, dried and used. The sample was immersed in an octadecyldichlorosilane solution diluted with chloroform at a concentration of 10 mM for 30 seconds, washed with acetone, and dried. Then, the polymer of Formula 14 synthesized in Example 2 was dissolved in chlorobenzene at a concentration of 1.0 wt% Spin-coating method, and baked at 150 ° C for 1 hour in a nitrogen atmosphere to prepare an OTFT device.

Evaluation of electrical characteristics of organic thin film transistor

A bias voltage (V _DS = -40 V, V _DS = -1 V) was applied to the OTFT device manufactured according to the third embodiment using a Semiconductor Characterization System (4200-SCS) measuring device manufactured by KEITHLEY Co., state current transfer characteristics were measured in the atmosphere and the results are shown in Fig. The OTFT device exhibited a high current on / off ratio of 10 ⁶ and a high charge mobility of about 0.05 cm ² / Vs and exhibited a low off-state current of 10 ^-11 A or less. This indicates that the polymer used for the OTFT device is excellent in stability in air.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

10, 20: transistors 12, 22: substrate
16, 26: insulating layer 18, 28: active layer
14, 24: gate electrode 17a, 27a: source electrode
17b, 27b: drain electrode

Claims (11)

An organic semiconductor comprising a terminal repeating unit represented by any one of the following general formulas (7), (8) and (10) and comprising a first repeating unit of a pyrimidopyridine represented by the following general formula (1) and a second repeating unit containing a heteroaromatic ring: Polymers:
[Chemical Formula 1]

In Formula 1,
R ¹ and R ² are the same or different from each other and each represents hydrogen, halogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 A substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, NR ³ R ⁴ (wherein R ³ and R ⁴ are the same or different from each other, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, or selected from the group consisting of heteroaryl groups and combinations of the unsubstituted C2 to C30), and is selected from the group consisting of, or alternatively the one or non-adjacent two or more CH ₂ -O- group, , -S- _{, -SO 2 -, -CO-, -OCO-} , -COO-, -CH = CH-, -C≡C- , and -SiR ⁵ R ⁶ (wherein R ⁵ and R ⁶ are different from or equal to each other, hydrogen, A substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof)
Ar is a substituted or unsubstituted, substituted or unsubstituted C6 to C30 condensed polycyclic group containing a substituted or unsubstituted C4 to C14 heteroaromatic ring or a heteroaromatic ring, provided that Ar is a substituted or unsubstituted pyrimido [ 5,4-d] pyrimidine,
a and b represent mole ratios, a is in the range of 0.01 to 0.99, b is in the range of 0.01 to 0.99,
(7)

In Formula 7,
R is a fluoro group or a C1 to C20 perfluoroalkyl group, a is an integer of 1 to 5,
[Chemical Formula 8]

In Formula 8,
R is a fluoro group or a C1 to C20 perfluoroalkyl group, a is an integer of 1 to 6,
[Chemical formula 10]

In Formula 10,
R is a fluoro group or a C1 to C20 perfluoroalkyl group and a is an integer of 1 to 3;
The method according to claim 1,
Wherein the first repeating unit of the organic semiconductor polymer is represented by the following Chemical Formula 2:
(2)

In the above formula (2).
R ¹⁰ to R ¹³ are the same or different and each is hydrogen or a substituted or unsubstituted C1 to C20 linear or branched alkyl group.
The method according to claim 1,
Wherein the second repeating unit is any one of structures represented by Chemical Formula 3:
(3)

In Formula 3,
R ²⁰ to R ²⁶ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof.
The method according to claim 1,
Wherein the second repeating unit is a repeating unit of the following formula (4) containing thiophene:
[Chemical Formula 4]

In Formula 4,
R ³⁰ represents hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 Or a substituted or unsubstituted C 2 to C 30 heteroaryl group and combinations thereof, or alternatively two or more of the two or more CH ₂ groups which are not adjacent or are selected from the group consisting of -O-, -S _{-, -SO 2 -, -CO-,} -OCO-, -COO-, -CH = CH-, -C≡C- , and -SiR ³¹ R ³² (wherein R ³¹ and R ³² are different from or equal to each other, hydrogen , A substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof. Selected < / RTI >
k is an integer of 1 or 2,
Ar ₁ is a substituted or unsubstituted C4 to C14 heteroaromatic ring (heteroaromatic ring), or a substituted or unsubstituted condensed polycyclic unsubstituted C6 to C30 ventilation, including heteroaromatic rings, provided that Ar ₁ is a substituted or unsubstituted Is not a substituted pyrimido [5,4-d] pyrimidine or a substituted or unsubstituted thiophene,
c and d represent molar ratios, c is in the range of 0.01 to 0.99 and d is in the range of 0.01 to 0.99.
5. The method of claim 4,
Wherein Ar < 1 > is any one of structures represented by the following Chemical Formula 3:
(3)

In Formula 3,
R ²⁰ to R ²⁶ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, and combinations thereof.
The method according to claim 1,
Wherein the organic polymer comprising a repeating unit of Formula 1 comprises a repeating unit of Formula 5 and the organic functional polymer comprising a terminal functional group represented by Formula 7, Formula 8 or Formula 10:
[Chemical Formula 5]

In Formula 5,
R ¹⁰ to R ¹³ are the same or different and each is hydrogen or a substituted or unsubstituted C1 to C20 linear or branched alkyl group,
R ³³ and R ³⁴ are the same or different from each other and represent hydrogen, a substituted or unsubstituted C 1 to C 20 linear or branched alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or non-substituted is selected from the group consisting of unsubstituted C6 to C30 aryl group, a substituted or unsubstituted heteroaryl group unsubstituted C2 to C30 and combinations thereof, or optionally more than one or non-adjacent CH ₂ Wherein the group is selected from the group consisting of -O-, -S-, -SO ₂ -, -CO-, -OCO-, -COO-, -CH = CH-, -C≡C- and -SiR ³¹ R ³² where R ³¹ and R ³² are the same or different and are selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, An unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, , ≪ / RTI > and < RTI ID = 0.0 >
a, c and d represent molar ratios, wherein a is in the range of 0.01 to 0.99 and c + d is in the range of 0.01 to 0.99.
The method according to claim 6,
The organic polymer comprising the repeating unit represented by Formula 1 may include a repeating unit represented by Formula 6, and the organic functional polymer represented by Formula 7, Formula 8, or Formula 10,
[Chemical Formula 6]

In Formula 6,
R < ¹¹ > and R < ¹³ > are the same as or different from each other,
R ³⁴ , a, c and d are as defined in the above formula (5).
delete A transistor comprising an organic semiconductor polymer according to any one of claims 1 to 7.
10. The method of claim 9,
The transistor comprising: a gate electrode located on a substrate; A source electrode and a drain electrode which are positioned opposite to each other to define a channel region; An insulating layer electrically isolating the source electrode and the drain electrode from the gate electrode; And an active layer formed in the channel region,
Wherein the active layer comprises an organic semiconductor polymer.
An electronic device comprising an organic semiconductor polymer according to any one of claims 1 to 7.

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