WO2013187749A1 - Method for producing a novel luminescent polymer material - Google Patents

Method for producing a novel luminescent polymer material Download PDF

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WO2013187749A1
WO2013187749A1 PCT/LV2012/000021 LV2012000021W WO2013187749A1 WO 2013187749 A1 WO2013187749 A1 WO 2013187749A1 LV 2012000021 W LV2012000021 W LV 2012000021W WO 2013187749 A1 WO2013187749 A1 WO 2013187749A1
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copolymer
luminescent
producing
devices
materials
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Георгийс КИРИЛОВС
Андрейс БУЛАНОВС
Ирена ИВАНОВА
Елена КИРИЛОВА
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Даугавпилсский Университет
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/12—N-Vinylcarbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • This method relates to the field of materials science and spectroscopy. It can be used to develop new luminescent materials using a luminescent polymer based on polyvinylcarbazole, which is characterized by intense luminescence in the red spectrum. The resulting copolymer can be used to develop new luminescent materials, in electrophotography, for the production of displays, light sources, sensors, diode lasers, as well as in other areas in which it is necessary to ensure luminescence by converting electrical energy into light.
  • Phosphors are part of fluorescent inks, which, thanks to luminescent and reflective compounds, are very bright. Phosphors are used for dyeing plastics, fabrics, paper, natural and synthetic fibers, as well as for various coatings.
  • luminescent polymers One of the modern areas of application of luminescent polymers is the design of various electroluminescent devices (diodes, monitors, etc.), since currently in the world the production of OLED-containing light sources, displays and other devices is rapidly developing. Due to their significant advantages - economy, elasticity, high intensity and color brightness, the need for these technologies is constantly growing.
  • Polyvinylcarbazole polymers are known and widely used, which have good electrical conductivity and green luminescence in comparison with many other polymeric materials. As is known from the literature, by copolymerizing ⁇ -vinylcarbazole with organic phosphors containing polymerizable fragments, materials with modified mechanical and optical properties can be obtained. The scientific literature describes copolymers with derivatives of naphthalic acid, fluorene, styrene, thiophene, triphenylmethane and phenalene.
  • benzanthrone derivatives are used - organic derivatives that relate to anthrone dyes, many of which are characterized by intense fluorescence in a wide spectral range. Due to the high photostability and bright luminescence of anthrone dyes, 3- ⁇ -allylaminobenzantrone, a derivative of an anthron with a polymerized fragment, was synthesized and used in the work as the starting compound for the preparation of copolymers.
  • the copolymer production method is realized by copolymerizing ⁇ -vinylcarbazole and 3-1-allyl-aminobenzantrone in various ratios (from 0.5 to 8% of the mass fraction of the second component) as a catalyst using 4,4'-azobis (4-cyanvalerianic acid).
  • the production method is implemented as follows:
  • the luminescence spectra of the obtained samples were taken.
  • the obtained spectral data showed that the luminescence parameters of the developed polymer materials depend on the content of 3- ⁇ -allylaminobenzantrone in the sample: the lower the concentration of 3-M-allylaminobenzantrone, the wider the luminescence band of this material and the emitted light closer to white, which can be explained by overlapping luminescence bands polyvinylcarbazole and the resulting copolymer.
  • a shift of the luminescence band from 595 nm (0.5%) to 650 nm (8%) is observed.
  • This feature of the obtained material can be considered as its advantage, since this makes it possible to adjust the optical properties of the copolymer depending on operational requirements.
  • Fig. 1 Luminescence of the obtained polymer materials in ultraviolet for samples with a content of 3M-allylaminobenzantrone 0.5% (left) and 3% (right).
  • Fig. 2 Luminescence spectra of the obtained polymer materials with a content of 3-M-allylaminobenzantrone 0.5%; one%; 3% and 8%, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

A method for producing a novel luminescent polymer material has been developed, said method comprising copolymerizing two monomers (vinyl-carbazole and a benzathrone derivative), thereby producing an electrically conductive copolymer which is intensively luminescent in the red part of the spectrum from 595 nm to 650 nm, depending on the allyl-component content. This characteristic of the material produced can be considered an advantage thereof, since this provides the possibility of adjusting the optical properties of the copolymer depending on operational requirements. Said method relates to the field of materials technology and spectroscopy. Said method can be used for developing novel luminescent materials using a luminescent polymer produced on the basis of polyvinyl-carbazole, the presence of which ensures electrical conductivity. The copolymer produced can be used for developing novel flexible luminous materials, which can be used in electrophotography, for producing displays, light sources, sensors, diode lasers, and also in other fields requiring the provision of intensive red or orange luminescence, thereby converting electrical energy into light. For example, said copolymer is used in the construction of various electro-luminescent devices (OLEDs, monitors, etc.), since the production of OLED-containing light sources, displays and other devices is currently being intensively developed worldwide. Owing to the significant advantages of said devices - economy, flexibility, high degree of colour intensity and clarity, demand for said devices in these technologies continuously increases.

Description

Описание  Description
Метод получения нового люминесцентного полимерного материала The method of obtaining a new luminescent polymer material
Данный метод относится к области материаловедения и спектроскопии. Он может быть применен для разработки новых люминесцентных материалов, используя люминесцентный полимер на основе поливинилкарбазола, для которого характерна интенсивная люминесценция в красной области спектра. Полученный сополимер может быть использован для разработки новых люминесцентных материалов, в электрофотографии, для производства дисплеев, источников света, сенсоров, диодных лазеров, а также в других областях, в которых необходимо обеспечить люминесценцию, преобразуя электрическую энергию в свет. This method relates to the field of materials science and spectroscopy. It can be used to develop new luminescent materials using a luminescent polymer based on polyvinylcarbazole, which is characterized by intense luminescence in the red spectrum. The resulting copolymer can be used to develop new luminescent materials, in electrophotography, for the production of displays, light sources, sensors, diode lasers, as well as in other areas in which it is necessary to ensure luminescence by converting electrical energy into light.
В настоящее время известны много химических соединений (люминофоры), которые могут люминесцировать под действием ультрафиолетового излучения. Люминофоры входят в состав флуоресцентныз красок, которые благодаря люминесцирующим и светоотражающим соединениям, очень яркие. Люминофоры используют для крашения пластмасс, тканей, бумаги, природных и синтетических волокон, а также для различных покрытий.  Currently, there are many chemical compounds (phosphors) that can luminesce under the influence of ultraviolet radiation. Phosphors are part of fluorescent inks, which, thanks to luminescent and reflective compounds, are very bright. Phosphors are used for dyeing plastics, fabrics, paper, natural and synthetic fibers, as well as for various coatings.
Одно из современных направлений применения люминесцирующих полимеров является конструирование различных элекролюминесцирующих устройств (диодов, мониторов и др.), так как в настоящее время в мире интенсивно развивается производство OLED- содержащих источников света, дисплеев и других устройств. Благодаря их значительным преимуществам - экономичности, эластичности, высокой интенсивности и яркости цвета, непрерывно растет потребность в данных технологиях.  One of the modern areas of application of luminescent polymers is the design of various electroluminescent devices (diodes, monitors, etc.), since currently in the world the production of OLED-containing light sources, displays and other devices is rapidly developing. Due to their significant advantages - economy, elasticity, high intensity and color brightness, the need for these technologies is constantly growing.
Особый интерес привлекают материалы, имеющие красную люминесценцию, так как количество таких соединений ограничено по сравнению с синими, зелеными и желтыми люминофорами. Также велик спрос на композитные и полимерные материалы с люминес- ценцией белого света.  Of particular interest are materials having red luminescence, since the number of such compounds is limited in comparison with blue, green, and yellow phosphors. There is also a great demand for composite and polymeric materials with white light luminescence.
Известны и широко используются поиливинилкарбазольные полимеры, которые обладают хорошей по сравнению со многими другими полимерными материалами электропроводностью и зеленой люминесценцией. Как известно из литературы, при сополимеризации Ν-винилкарбазола с содержащими полимеризующиеся фрагменты органическими люминофорами можно получить материалы с модифицированными механическими и оптическими свойствами. В научной литературе описаны сополимеры с производными нафталевой кислоты, флуорена, стирола, тиофена, трифенилметана и феналена.  Polyvinylcarbazole polymers are known and widely used, which have good electrical conductivity and green luminescence in comparison with many other polymeric materials. As is known from the literature, by copolymerizing Ν-vinylcarbazole with organic phosphors containing polymerizable fragments, materials with modified mechanical and optical properties can be obtained. The scientific literature describes copolymers with derivatives of naphthalic acid, fluorene, styrene, thiophene, triphenylmethane and phenalene.
В производстве флуоресцентных красок и пигментов используются производные бензантрона - органические производные, которые относятся к антроновым красителям, многим из которых присуща интенсивная флуоресценция в широком спектральном диапазоне. В связи с высокой фотостабильностью и яркой люминесценцией антроновых красителей З- -аллиламинобензантрон, производное антрона с полимеризуемым фрагментом, был синтезирован и спользован в работе как исходное соединение для получения сополимеров.  In the production of fluorescent paints and pigments, benzanthrone derivatives are used - organic derivatives that relate to anthrone dyes, many of which are characterized by intense fluorescence in a wide spectral range. Due to the high photostability and bright luminescence of anthrone dyes, 3-β-allylaminobenzantrone, a derivative of an anthron with a polymerized fragment, was synthesized and used in the work as the starting compound for the preparation of copolymers.
Способ получения сополимера реализуют, сополимеризуя Ν-винилкарбазол и 3-1 -аллил- аминобензантрон в различных соотношениях (от 0,5 до 8 % массовой доли второго компонента) как катализатор используя 4,4'-азобис(4-цианвалерьяновую кислоту).  The copolymer production method is realized by copolymerizing Ν-vinylcarbazole and 3-1-allyl-aminobenzantrone in various ratios (from 0.5 to 8% of the mass fraction of the second component) as a catalyst using 4,4'-azobis (4-cyanvalerianic acid).
Метод получения реализуют следующим образом: The production method is implemented as follows:
1. 1. Синтез З-И-аллиламинобензантрона.  1. 1. Synthesis of Z-I-allylaminobenzantrone.
В 100 мл круглодонную колбу помещают 0,25 г (1ммоль) 3-аминобензантрона, 30 мл толуола, 5 мл триэтиламина и 061 мл аллилбромида. Реакционную смесь кипятят с обратным холодильником, контролируя ход реакции с помощью тонкослойной хроматографии в системе бензол'.ацетонитрил 3:1, до тех пор пока в реакционной смеси остаётся исходный 3-аминобензантрон. Затем охлаждают, выпавший осадок фильтруют, сушат и перекристаллизовывают из хлороформа. 0.25 g (1 mmol) of 3-aminobenzantrone, 30 ml of toluene, 5 ml of triethylamine and 061 ml of allyl bromide are placed in a 100 ml round bottom flask. The reaction mixture is boiled with reflux condenser, controlling the course of the reaction using thin-layer chromatography in a benzene'.acetonitrile 3: 1 system, until the initial 3-aminobenzantrone remains in the reaction mixture. Then it is cooled, the precipitated precipitate is filtered, dried and recrystallized from chloroform.
2. Получение сополимера с массовой долей 0,5%.  2. Obtaining a copolymer with a mass fraction of 0.5%.
В 50 мл круглодонную колбу помещают 9,95 г Ν-винилкарбазола, 0,05 г З-М-аллил- аминобензантрона и 0,1 мг 4,4'-азобис(4-цианвалерьяновую кислоты), хорошо пере- мешивают. Полученную смесь греют 10-12 часов при температуре 80-90°С.  9.95 g of он-vinylcarbazole, 0.05 g of 3-M-allyl-aminobenzantrone and 0.1 mg of 4,4'-azobis (4-cyano-valeric acid) are mixed well in a 50 ml round bottom flask. The resulting mixture is heated for 10-12 hours at a temperature of 80-90 ° C.
3. Получение сополимера с массовой долей 1%.  3. Obtaining a copolymer with a mass fraction of 1%.
В 50 мл круглодонную колбу помещают 9,90 г Ν-винилкарбазола, 0,10 г З-Ы-аллил- аминобензантрона и 0,1 мг 4,4'-азобис(4-цианвалерьяновую кислоты), хорошо пере- мешивают. Полученную смесь греют 10-12 часов при температуре 80-90°С.  9.90 g of α-vinylcarbazole, 0.10 g of 3-Y-allyl-aminobenzantrone and 0.1 mg of 4,4'-azobis (4-cyanvalerianic acid) are mixed well in a 50 ml round bottom flask. The resulting mixture is heated for 10-12 hours at a temperature of 80-90 ° C.
4. Получение сополимера с массовой долей 3%.  4. Obtaining a copolymer with a mass fraction of 3%.
В 50 мл круглодонную колбу помещают 9,70 г Ν-винилкарбазола, 0,30 г З-Т -аллил- аминобензантрона и 0,1 мг 4,4'-азобис(4-цианвалерьяновую кислоты), хорошо перемешивают. Полученную смесь греют 10-12 эчасов при температуре.80-90°С.  9.70 g of он-vinylcarbazole, 0.30 g of 3-T-allyl-aminobenzantrone and 0.1 mg of 4,4'-azobis (4-cyano-valeric acid) are mixed well in a 50 ml round bottom flask. The resulting mixture is heated for 10-12 hours at a temperature of 80-90 ° C.
5. Получение сополимера с массовой долей 8%.  5. Obtaining a copolymer with a mass fraction of 8%.
В 50 мл круглодонную колбу помещают 9,20 г Ν-винилкарбазола, 0,80 г З-Ы-аллил- аминобензантрона и 0,1 мг 4,4'-азобис(4-цианвалерьяновую кислоты), хорошо перемешивают. Полученную смесь греют 10-12 Бчасов при температуре 80-90°С.  9.20 g of α-vinylcarbazole, 0.80 g of 3-Y-allyl-aminobenzantrone and 0.1 mg of 4,4'-azobis (4-cyano-valeric acid) are mixed well in a 50 ml round bottom flask. The resulting mixture is heated for 10-12 hours at a temperature of 80-90 ° C.
Структура полученного сополимера. The structure of the obtained copolymer.
Figure imgf000004_0001
Figure imgf000004_0001
Люминесцентные свойства полученных полимерных материалов. Luminescent properties of the obtained polymer materials.
Для описания спектральных свойств разработанных материалов были сняты спектры люминесценции полученных образцов. Полученные спектральные данные показали, что параметры люминесценции разработанных полимерных материалов зависят от содержания 3— Ν-аллиламинобензантрона в образце: чем меньше концентрация З-М-аллиламинобензантрона, тем шире полоса люминесценции данного материала и излучаемый свет ближе к белому, что можно объяснить перекрыванием полос люминесценции поливинилкарбазола и полученного сополимера. При увеличении содержания остатков аминобензантрона в синтезированном сополимере наблюдается сдвиг полосы люминесценции с 595 нм (0,5%) до 650 нм (8%). To describe the spectral properties of the developed materials, the luminescence spectra of the obtained samples were taken. The obtained spectral data showed that the luminescence parameters of the developed polymer materials depend on the content of 3-Ν-allylaminobenzantrone in the sample: the lower the concentration of 3-M-allylaminobenzantrone, the wider the luminescence band of this material and the emitted light closer to white, which can be explained by overlapping luminescence bands polyvinylcarbazole and the resulting copolymer. With an increase in the content of aminobenzantrone residues in the synthesized copolymer, a shift of the luminescence band from 595 nm (0.5%) to 650 nm (8%) is observed.
Данную особенность полученного материала можно рассматривать как его преимущество, так как это дает возможность регулировать оптические свойства сополимера в зависимости от эксплуатационных требований.  This feature of the obtained material can be considered as its advantage, since this makes it possible to adjust the optical properties of the copolymer depending on operational requirements.
Рисунки: Drawings:
Рис.1 Люминесценция полученных полимерных материалов в ультрафиолете для образцов с содержанием З-М-аллиламинобензантрона 0,5% (слева) и 3% (справа).  Fig. 1 Luminescence of the obtained polymer materials in ultraviolet for samples with a content of 3M-allylaminobenzantrone 0.5% (left) and 3% (right).
Рис.2 Спектры люменесценции полученных полимерных материалов с содержанием З-М- аллиламинобензантрона 0,5%; 1%; 3% и 8% соответственно. Fig. 2 Luminescence spectra of the obtained polymer materials with a content of 3-M-allylaminobenzantrone 0.5%; one%; 3% and 8%, respectively.

Claims

Формула изобретения Claim
1. Метод получения нового люминесцентного полимерного материала, котрый включает в себя проведение реакции сополимеризации Ν-винилкарбазола и 3-N- аллиламинобензантрона (массовы соотношения от 99,5:0,5 до 92:8) при температуре 80-90 С в течение 10-12 часов в присутствии радикального катализатора и который отличается от других светящихся подцействием ультрафиолетового излучения полимерных метериалов интенсивной люминесценцией, цвет которой (от желтой до красной) можно регулировать содержанием З-К-аллиламинобензантрона в данном мватериале. 1. The method of obtaining a new luminescent polymer material, which includes the copolymerization of Ν-vinylcarbazole and 3-N-allylaminobenzantrone (mass ratios from 99.5: 0.5 to 92: 8) at a temperature of 80-90 C for 10 -12 hours in the presence of a radical catalyst and which differs from other luminous ones by the ultraviolet radiation of polymer materials by intense luminescence, the color of which (from yellow to red) can be controlled by the content of 3-C-allylaminobenzantrone in this material.
PCT/LV2012/000021 2012-06-11 2012-12-13 Method for producing a novel luminescent polymer material WO2013187749A1 (en)

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