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WO2015108360A1 - Polymère de dicétopyrrolopyrrole asymétrique contenant un hétérocycle-vinylène-hétérocyclique, dispositif électronique organique l'utilisant, et monomère pour le préparer - Google Patents

Polymère de dicétopyrrolopyrrole asymétrique contenant un hétérocycle-vinylène-hétérocyclique, dispositif électronique organique l'utilisant, et monomère pour le préparer Download PDF

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WO2015108360A1
WO2015108360A1 PCT/KR2015/000459 KR2015000459W WO2015108360A1 WO 2015108360 A1 WO2015108360 A1 WO 2015108360A1 KR 2015000459 W KR2015000459 W KR 2015000459W WO 2015108360 A1 WO2015108360 A1 WO 2015108360A1
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heterocyclic
vinylene
asymmetric
organic
diketopyrrolopyrrole
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김윤희
권순기
백장열
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Gyeongsang National University GNU
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Definitions

  • the present invention relates to an asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer, an organic semiconductor compound for an organic electronic device, a use thereof, and a monomer for preparing the same.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention is a novel organic semiconductor compound having a high pi electron overlap, and the organic electronic device employing the same has excellent charge mobility and flashing ratio.
  • OFTs organic thin film transistors
  • the organic thin film transistor using the organic semiconductor has the advantages of simpler manufacturing process and lower cost production compared to the organic thin film transistor using amorphous silicon and polysilicon, and is compatible with the plastic substrates for implementing the flexible display. Due to this superior advantage, many researches are being made recently.
  • the use of a polymer organic semiconductor has the advantage that the manufacturing cost can be reduced compared to the low molecular organic semiconductor compound because of the advantage that the thin film can be easily formed by the solution process.
  • Representative semiconductor compounds for polymer-based organic thin film transistors developed to date include P3HT [poly (3-hexylthiophene)] and F8T2 [poly (9,9-dioctylfluorene-co-bithiophene)].
  • P3HT poly (3-hexylthiophene)
  • F8T2 poly (9,9-dioctylfluorene-co-bithiophene
  • an organic thin film transistor is formed of a substrate / gate / insulation layer / electrode layer (source, drain) / derivative conductor layer, and a gate electrode is formed on the substrate.
  • An insulating layer is formed on the gate electrode, and an organic semiconductor layer, and a source and a drain electrode are sequentially formed on the gate electrode.
  • the driving principle of the organic thin film transistor having the above structure will be described below with an example of a p-type semiconductor. First, when a current is applied by applying a voltage between the source and the drain, a current proportional to the voltage flows under a low voltage. When a positive voltage is applied to the gate, holes that are positive charges are all pushed up to the top of the semiconductor layer by the electric field by the applied voltage.
  • the portion close to the insulating layer will have a depletion layer without conduction charge, and in such a situation, a low amount of current will flow due to the reduced number of conducting charge carriers even when a voltage is applied between the source and the drain.
  • a negative voltage is applied to the gate
  • an accumulation layer in which positive charges are induced near the insulating layer is formed by the effect of the electric field caused by the applied voltage.
  • the current flowing between the source and the drain can be controlled by alternately applying a positive voltage and a negative voltage to the gate while a voltage is applied between the source and the drain.
  • the organic thin film transistors which are constructed on the principle described above, include electrodes (source and drain), substrates and gate electrodes requiring high thermal stability, insulators having high dielectric properties and dielectric constants, and semiconductors that transfer charges well.
  • the core material is organic semiconductor.
  • Organic semiconductors can be classified into low molecular organic semiconductors and high molecular organic semiconductors according to molecular weight, and are classified into n-type organic semiconductors or p-type organic semiconductors according to whether electrons or holes are transferred. In general, when a low molecular weight organic semiconductor is used in forming an organic semiconductor layer, the low molecular weight organic semiconductor is easy to purify and almost removes impurities, so the charge transfer characteristics are excellent.
  • Korean Patent Publication No. 2011-0091711 and Korean Patent Publication No. 2009-0024832 disclose polymers in which an S-containing heteroaromatic ring is directly bonded to a diketopyrrolopyrrole group.
  • a polymer semiconductor material exhibiting sufficient pi electron overlap since it still does not show sufficient pi electron expansion.
  • the present invention provides an asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer.
  • the present invention provides an asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer which is an organic semiconductor compound having high solubility and viscosity due to high molecular weight and easy spin coating at room temperature to enable a solution process. to provide.
  • the present invention also provides an asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer which is an organic semiconductor compound having a high charge mobility applied to an organic electronic device.
  • the present invention also provides an organic thin film transistor comprising the novel asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention in an organic semiconductor layer.
  • the present invention relates to an organic semiconductor compound for organic electronic device such as an organic thin film transistor (OTFT) and its use. More specifically, the present invention includes an electron acceptor compound, a diketopyrrolopyro derivative, between two thiophenes, an electron donor compound, and another electron donor compound, thiophene-vinylene, in the electron donor compound thiophene.
  • OFT organic thin film transistor
  • Asymmetric heterocycles such as selenophene, selenophene-vinylene-thiophene, thiophene-vinylene-furan, furan-vinylene-thiophene, selenophene-vinylene-furan or furan-vinylene-selenophene
  • a diketopyrrolopyrrole polymer using an asymmetric heterocyclic-vinylene-heterocyclic derivative which is a p-type polymer organic semiconductor compound used as an active layer material of an organic thin film transistor in which a vinylene-heterocycle is bonded to a randomly polymerized organic thin film transistor and It relates to an organic electronic device using the same.
  • novel asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention is represented by the following formula (1).
  • X and Y are each independently S, Se or O, provided that X and Y are not identical to each other;
  • R 1 and R 2 are each independently hydrogen or a (C 1 -C 50) alkyl group, and the alkyl of R 1 and R 2 is each (C 1 -C 30) alkyl, (C 2 -C 30) alkenyl, (C 2 -C 30) alky May be further substituted with one or more substituents selected from nil, (C1-C30) alkoxy, amino, hydroxy, halogen, cyano, nitro, trifluoromethyl and tri (C1-C30) alkylsilyl;
  • n and n are each independently an integer of 0 to 1000 and m and n are not zero at the same time.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer represented by the formula (1) of the present invention is a polymer comprising a unit of formula (A) and a unit of formula (B), a block copolymer, Random copolymers, alternating copolymers, tapered copolymers, and the like.
  • X and Y are each independently S, Se or O, provided that X and Y are not identical to each other;
  • R 1 and R 2 are each independently hydrogen or a (C 1 -C 50) alkyl group.
  • the alkyl of R 1 and R 2 is (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, amino, hydroxy, halogen, cyano , Nitro, trifluoromethyl and tri (C1-C30) alkylsilyl may be further substituted;
  • m and n are each independently an integer of 0 to 1000 and m and n are 0 no.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer represented by the formula (1) of the present invention is coplanarity of the main chain by introducing a vinylene group (V) into the diketopyrrolopyrrole derivative
  • V vinylene group
  • the organic electronic device containing the same exhibits high mobility by increasing the molecular weight and increasing the conjugated structure, thereby enhancing the electron density and increasing the intermolecular interaction.
  • substituents R 1 and R 2 of the diketopyrrolopyrrole derivatives It has a higher solubility by having a phosphorus structure. That is, a has a structure in which a of R 1 and R 2 has an integer of 1 to 10, more preferably a has a branched alkyl at the terminal, with an integer of 1 to 7, resulting in as much as 10 compared to alkyl having no branched chain at the terminal. It has more than twice the charge mobility and at the same time has a high solubility, which is more advantageous for the solution process, so that a large area organic electronic device can be manufactured in a simple and inexpensive process.
  • R 1 and R 2 are each independently And a is an integer from 1 to 10, and R 11 and R 12 may each independently be (C 10 -C 30) alkyl.
  • Asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer according to an embodiment of the present invention is more specifically in terms of high solubility and excellent charge mobility and flashing ratio and is preferably the following compound It may be, but is not limited thereto.
  • m and n are each independently an integer of 0 to 1000 and m and n are not 0 at the same time.
  • R 1 and R 2 in the general formula (1) is a carbon number of 24 or more, while the linear carbon number of alkyl
  • the structure having a branched alkyl at the terminal of 1 to 7 has a high solubility, there is no decrease in charge mobility or flashing ratio, so that the organic electronic device containing the same has a very significant effect having high efficiency.
  • Compounds can be prepared.
  • the organic semiconductor compound according to the present invention is not limited to the above production method, and may be prepared by a conventional organic chemical reaction in addition to the above production method.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer according to the present invention can be used as a material for forming an organic semiconductor layer of the organic electronic device, the present invention is an asymmetric heterocyclic-vinylene-heterocyclic An organic electronic device containing a system diketopyrrolopyrrole polymer is provided.
  • the organic electronic device of the present invention may be an organic thin film transistor, and specific examples of the method for manufacturing the organic thin film transistor of the present invention are as follows.
  • n-type silicon used for a conventional organic thin film transistor as a substrate.
  • This substrate contains the function of the gate electrode.
  • a glass substrate or a transparent plastic substrate having excellent surface smoothness, ease of handling, and waterproofness may be used as the substrate.
  • a gate electrode must be added on the substrate.
  • Substances which can be employed as the substrate include glass, polyethylenenaphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC), polyvinyl alcohol (PVP), polyacrylate (Polyacrylate). , Polyimide, polynorbornene and polyethersulfone (PES).
  • an insulator having a high dielectric constant As the gate insulating layer constituting the OTFT device, an insulator having a high dielectric constant, which is commonly used, may be used. Specifically, Ba 0.33 Sr 0.66 TiO 3 (BST), Al 2 O 3 , Ta 2 O 5 , La 2 O 5 , Ferroelectric insulator selected from the group consisting of Y 2 O 3 and TiO 2 , PdZr 0.33 Ti 0.66 O 3 (PZT), Bi 4 Ti 3 O 12 , BaMgF 4 , SrBi 2 (TaNb) 2 O 9 , Ba (ZrTi) O 3 Inorganic insulators selected from the group consisting of (BZT), BaTiO 3 , SrTiO 3 , Bi 4 Ti 3 O 12 , SiO 2 , SiN x and AlON, or polyimide, BCB (benzocyclobutene), parylene, Organic precursors such as polyacrylate, polyvinylalcohol, and
  • the structure of the organic thin film transistor of the present invention is not only top-contact of the substrate / gate electrode / insulation layer / oil-based conductor layer / source and drain electrode but also the substrate / gate electrode / insulation layer / source, drain electrode / organic It includes all forms of bottom-contact of the semiconductor layer.
  • HMDS (1,1,1,3,3,3-hexamethyldisilazane), octadecyltrichlorosilane (OTS) or octadecyltrichlorosilane (OTDS) may or may not be coated as a surface treatment between the source and drain electrodes and the organic semiconductor layer.
  • the organic semiconductor layer employing the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer according to the present invention is vacuum deposition, screen printing, printing, spin casting, spin coating, dipping or ink powder. It can be formed into a thin film through the method, in this case, the deposition of the organic semiconductor layer may be formed using a high temperature solution at 40 °C or more, the thickness is preferably about 500 kPa.
  • the gate electrode and the source and drain electrodes may be conductive materials, but may be formed from a group consisting of gold (Au), silver (Ag), aluminum (Al), nickel (Ni), chromium (Cr), and indium tin oxide (ITO). It is preferably formed of the selected material.
  • the present invention provides an asymmetric heterocyclic-vinylene-heterocyclic monomer represented by the following formula (2).
  • Z 1 and Z 2 are each independently hydrogen, halogen, B (OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl or SnR 11 R 12 R 13 ; R 11 to R 13 are each independently (C 1 -C 10) alkyl.
  • Asymmetric heterocyclic-vinylene-heterocyclic monomers according to an embodiment of the present invention may be specifically illustrated by the following structure, but is not limited thereto.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention contains a diketopyrrolopyrrole derivative, an electron acceptor compound, between two thiophenes, an electron donor compound, Thiophene-vinylene-selenophene, selenophene-vinylene-thiophene, thiophene-vinylene-furan, furan-vinylene-thiophene, selenophene-vinylene-furan or Units in which asymmetric heterocyclic-vinylene-heterocycles, such as furan-vinylene-selenophene, are bonded are randomly polymerized, and have a conjugated structure extended to the increased coplanarity of the main chain. Increasing the density increases the intermolecular interactions and shows excellent thermal stability.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention has a low HOMO value, that is, an electron density increases in the repeating unit, thereby having excellent charge mobility and oxidation stability. It can be very usefully used as the organic semiconductor layer of the transistor.
  • the organic thin film transistor employing these devices improves the charge mobility and the flashing ratio, and when the organic thin film transistor is used, it is possible to make an electronic device having excellent efficiency and performance.
  • the organic thin film transistor can also be manufactured by a solution process such as vacuum deposition, spin coating, or printing, thereby reducing the manufacturing cost of an electronic device using the organic thin film transistor.
  • the asymmetric heterocyclic -vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention is a substituent substituted by N of the diketopyrrolopyrrole derivative, that is, to have a high solubility without affecting other electrical properties, that is,
  • the organic electronic device including the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention by introducing a substituent having a limited number of carbon atoms can be manufactured by a solution process such as vacuum deposition, spin coating or printing. Therefore, large area can be achieved by simple process and low cost.
  • FIG. 2 is a UV-vis absorption spectra of a solution phase and a film phase of a thiophene-vinylene-selenophene-based diketopyrrolopyrrole polymer (P-29-DPPTVSe) synthesized in Example 4;
  • Example 3 is a cyclic voltammetry diagram of the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-24-DPPTVSe) synthesized in Example 3,
  • Example 4 is a cyclic voltammetry diagram of the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-29-DPPTVSe) synthesized in Example 4,
  • DSC differential calorimetry
  • DSC differential calorimetry
  • Example 11 and 12 are prepared by the method of Example 5 using the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-24-DPPTVSe) synthesized in Example 3 and the device after 180 °C heat treatment
  • This diagram shows the characteristics of the transfer curve (Transfer curve, Output curve)
  • Example 13 and 14 show the device at room temperature fabricated by the method of Example 5 using the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-29-DPPTVSe) synthesized in Example 4.
  • This diagram shows the characteristics (Transfer curve, Output curve),
  • Example 15 and 16 are prepared by the method of Example 5 using the thiophene-vinylene-selenophene-based diketopyrrolopyrrole polymer (P-29-DPPTVSe) synthesized in Example 4 and the device after the 180 ° C heat treatment It is a figure which shows the characteristic (Transfer curve, Output curve) of.
  • N-bromosuccinimide (NBS) (3.13 g, 17.6 mmol) and DMF (50 mL) were added and dissolved in a 250 mL three-neck flask shielded with silver foil.
  • (E) -2- (2- (selenophen-2-yl) vinyl) thiophene ((E) -2- (2- (selenophen-2-yl) vinyl) thiophene) dissolved in DMF (30 mL) ( 2 g, 8.36 mmol) was added slowly dropwise. After stirring for 12 hours at room temperature, the reaction was terminated, 300 mL of water was added and extracted, dried over anhydrous MgSO 4 and the solvent was removed.
  • the polymer P-24-DPPTVSe can be polymerized through a Stille coupling reaction.
  • 3,6-bis (5-bromothiophen-2-yl) -2,5-bis (2-decyltetradecyl) pyrrolo [3,4-c] pyrrole-1,4 (2H, 5H) -da Ion (3,6-bis (5-bromothiophen-2-yl) -2,5-bis (2-decyltetradecyl) pyrrolo [3,4-c] pyrrole -1,4 (2H, 5H) -dione) (0.50 g, 0.44 mmol) and (E) -trimethyl (5- (2- (5- (trimethylstannyl) selenophen-2-yl) vinyl) thiophen-2-yl) stannan (Example 2, 0.249 g, 0.44 mmol) was dissolved in chlorobenzene (5 mL) and subjected to nitrogen
  • the polymer P-29-DPPTVSe can be polymerized through a Stille coupling reaction.
  • 3,6-bis (5-bromothiophen-2-yl) -2,5-bis (2-decylnonadecyl) pyrrolo [3,4-c] pyrrole-1,4 (2H, 5H)- Dione (3,6-bis (5-bromothiophen-2-yl) -2,5-bis (7-decylnonadecyl) pyrrolo [3,4-c] pyrrole-1,4 (2H, 5H) -dione) ( 0.50 g, 0.39 mmol) and (E) -trimethyl (5- (2- (5- (trimethylstannyl) selenophen-2-yl) vinyl) thiophen-2-yl) stannan (Example 2 , 0.220 g, 0.39 mmol) was dissolved in chlorobenzene (5 mL) and subjected to
  • the OTFT device was fabricated in a top-contact manner, using 100 nm n-doped silicon as a gate and SiO 2 as an insulator. Surface treatment was performed using a piranha cleaning solution (H 2 SO 4 : 2H 2 O 2 ) and then using the Adrich's ODTS (octadecyltrichlorosilane) surface was used after SAM (Self Assemble Monolayer) treatment. The organic semiconductor layer was coated with 0.2 wt% chloroform solution using a spin-coater for 1 minute at 2000 rpm. P-24-DPPTVSe and P-29-DPPTVSe synthesized in Examples 3 and 4 were used as organic semiconductor materials, respectively.
  • Gold used as the source and drain was deposited to a thickness of 50 nm at 1 A / s.
  • the channel is 100 ⁇ m long and 1000 ⁇ m wide.
  • the measurement of OTFT characteristics was done using Keithley 2400 and 236 source / measure units.
  • the charge mobility was obtained from (S SD ) 1/2 and V G as variables from the saturation region current equation and obtained from the slope.
  • I SD is the source-drain current
  • ⁇ or ⁇ FET is the charge transfer
  • C 0 is the oxide capacitance
  • W is the channel width
  • L is the channel length
  • V G is the gate voltage
  • V T is the threshold voltage.
  • the cutoff leakage current I off is a current flowing in the off state, and is determined as the minimum current in the off state in the current ratio.
  • Table 1 describes the optical and electrochemical properties of the novel thiophene-vinylene-selenophene diketopyrrolopyrrole polymers synthesized in Examples 3 and 4 (P-24-DPPTVSe and P-29-DPPTVSe). It was.
  • the HOMO value is a value calculated using the result values measured in FIGS. 3 and 4.
  • the band gap was obtained from the UV absorption wavelength in the film state.
  • the thiophene-vinylene-selenophene-based diketopyrrolopyrrole polymer of the present invention has a low band gap and high charge mobility of the organic electronic device containing the same.
  • the decomposition temperature of the novel thiophene-vinylene-selenophene diketopyrrolopyrrole polymers synthesized in Examples 3 and 4 was determined by TGA. shows a result of measurement by (P-24-DPPTVSe of T d is 370 °C; T d of the P-29-DPPTVSe is 387 °C).
  • the organic semiconductor compound synthesized in the present invention is excellent in thermal stability and can be seen that the charge mobility is increased when annealing (annealing) it can be seen that the excellent organic electronic device material have.
  • Example 9 and 10 are manufactured by the method of Example 5 using the thiophene-vinylene-selenophene-based diketopyrrolopyrrole polymer (P-24-DPPTVSe) synthesized in Example 3, and then room temperature A diagram showing the transfer curve and the out-put curve of the device in Figure 2, which shows the organic electronic device characteristics of the polymer material.
  • Example 11 and 12 show the device of Example 5 using the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-24-DPPTVSe) synthesized in Example 3, and then 180 A diagram showing a transfer curve and an out-put curve of a device after heat treatment at °C, and a view showing the organic electronic device characteristics of the polymer material.
  • P-24-DPPTVSe thiophene-vinylene-selenophene diketopyrrolopyrrole polymer
  • Example 13 and 14 are manufactured by the method of Example 5 using the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-29-DPPTVSe) synthesized in Example 4, and then room temperature
  • P-29-DPPTVSe thiophene-vinylene-selenophene diketopyrrolopyrrole polymer
  • Example 15 and 16 show the device manufactured by the method of Example 5 using the thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-29-DPPTVSe) synthesized in Example 4, and then 180 A diagram showing a transfer curve and an out-put curve of a device after heat treatment at °C, and a view showing the organic electronic device characteristics of the polymer material.
  • P-29-DPPTVSe thiophene-vinylene-selenophene diketopyrrolopyrrole polymer
  • Example 5 Prepared in Example 5 using the novel thiophene-vinylene-selenophene diketopyrrolopyrrole polymer (P-24-DPPTVSe and P-29-DPPTVSe) synthesized in Examples 2 and 4 in Table 2 below The characteristics of the device were described.
  • the organic electronic device manufactured by the method of Example 5 and heat-treated at 180 ° C. is an asymmetric heterocyclic-vinylene such as the thiophene-vinylene-selenophene-based diketopyrrolopyrrole polymer of the present invention.
  • Heterocyclic diketopyrrolopyrrole polymer contains a high charge mobility and a stable flashing ratio.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention comprises an electron acceptor compound, a diketopyrrolopyrrole derivative, between two thiophenes, an electron donor compound, and an electron donor compound, Thiophene-vinylene-selenophene, selenophene-vinylene-thiophene, thiophene-vinylene-furan, furan-vinylene-thiophene, selenophene-vinylene-furan or Units in which asymmetric heterocyclic-vinylene-heterocycles, such as furan-vinylene-selenophene, are bonded are randomly polymerized, and have a conjugated structure extended to the increased coplanarity of the main chain. Increasing the density increases the intermolecular interactions and shows excellent thermal stability.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention has a low HOMO value, that is, an electron density increases in the repeating unit, thereby having excellent charge mobility and oxidation stability. It can be very usefully used as the organic semiconductor layer of the transistor.
  • the organic thin film transistor employing these devices improves the charge mobility and the flashing ratio, and when the organic thin film transistor is used, it is possible to make an electronic device having excellent efficiency and performance.
  • the organic thin film transistor can also be manufactured by a solution process such as vacuum deposition, spin coating, or printing, thereby reducing the manufacturing cost of an electronic device using the organic thin film transistor.
  • the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention is a substituent substituted by N of the diketopyrrolopyrrole derivative, that is, to have high solubility without affecting other electrical properties, that is,
  • the organic electronic device including the asymmetric heterocyclic-vinylene-heterocyclic diketopyrrolopyrrole polymer of the present invention by introducing a substituent having a limited number of carbon atoms can be manufactured by a solution process such as vacuum deposition, spin coating or printing. Therefore, large area can be achieved by simple process and low cost.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

Cette invention concerne : un polymère de dicétopyrrolopyrrole asymétrique contenant un hétérocycle-vinylène-hétérocyclique qui est un composé semi-conducteur organique pour dispositif électronique organique ; son utilisation ; et un monomère pour le préparer. Le polymère de dicétopyrrolopyrrole asymétrique contenant un hétérocycle-vinylène-hétérocyclique selon la présente invention est un nouveau composé semi-conducteur organique ayant un empilement d'électrons π important, et un dispositif électronique organique l'utilisant peut obtenir une excellente mobilité de charges et un excellent rapport on/off.
PCT/KR2015/000459 2014-01-17 2015-01-16 Polymère de dicétopyrrolopyrrole asymétrique contenant un hétérocycle-vinylène-hétérocyclique, dispositif électronique organique l'utilisant, et monomère pour le préparer Ceased WO2015108360A1 (fr)

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KR10-2014-0005839 2014-01-17
KR1020150007430A KR101630173B1 (ko) 2014-01-17 2015-01-15 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체
KR10-2015-0007430 2015-01-15

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Citations (5)

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Publication number Priority date Publication date Assignee Title
KR20070021055A (ko) * 2005-08-16 2007-02-22 메르크 파텐트 게엠베하 티오펜 또는 셀레노펜 화합물의 중합 방법
KR20070112791A (ko) * 2005-03-11 2007-11-27 메르크 파텐트 게엠베하 티오펜 및 셀레노펜 함유 단량체, 올리고머 및 중합체
JP2009062537A (ja) * 2007-09-06 2009-03-26 Xerox Corp ジケトピロロピロール系ポリマーおよびその形成方法
KR20130069445A (ko) * 2011-12-15 2013-06-26 경상대학교산학협력단 신규한 다이케토피롤로피롤 중합체 및 이를 이용한 유기 전자 소자
KR20140062610A (ko) * 2012-11-13 2014-05-26 경상대학교산학협력단 신규한 나프탈렌 다이이미드를 포함하는 중합체 및 이를 이용한 유기 전자 소자

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070112791A (ko) * 2005-03-11 2007-11-27 메르크 파텐트 게엠베하 티오펜 및 셀레노펜 함유 단량체, 올리고머 및 중합체
KR20070021055A (ko) * 2005-08-16 2007-02-22 메르크 파텐트 게엠베하 티오펜 또는 셀레노펜 화합물의 중합 방법
JP2009062537A (ja) * 2007-09-06 2009-03-26 Xerox Corp ジケトピロロピロール系ポリマーおよびその形成方法
KR20130069445A (ko) * 2011-12-15 2013-06-26 경상대학교산학협력단 신규한 다이케토피롤로피롤 중합체 및 이를 이용한 유기 전자 소자
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