CN110551054B - Maleimide derivative, and preparation method and application thereof - Google Patents

Maleimide derivative, and preparation method and application thereof Download PDF

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CN110551054B
CN110551054B CN201810536319.4A CN201810536319A CN110551054B CN 110551054 B CN110551054 B CN 110551054B CN 201810536319 A CN201810536319 A CN 201810536319A CN 110551054 B CN110551054 B CN 110551054B
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maleimide
phenanthroline
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maleimide derivative
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王鹰
王瑞芳
汪鹏飞
刘彦伟
魏晓芳
刘建君
李志毅
胡晓晓
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Technical Institute of Physics and Chemistry of CAS
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Abstract

The invention discloses a maleimide derivative, a preparation method and application thereof. The structural general formula of the maleimide derivative is shown as formula I:
Figure DDA0001678253220000011
wherein R is1And R2Each independently selected from at least one of an arylamine group of 6 to 30 carbon atoms, an aryl group of 6 to 30 carbon atoms, a substituted heteroaromatic group of 5 to 50 ring atoms; r3At least one selected from the group consisting of a hydrogen atom, an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 30 carbon atoms, a substituted aryl group of 6 to 30 carbon atoms, and a substituted aromatic heterocyclic group of 5 to 50 ring atoms. The maleimide derivative of the invention introduces a plurality of electron-rich groups, and can effectively separate the highest occupied orbital level and the lowest vacancy thereof through group modification of different electron donating abilitiesAnd the energy level of the orbit not only reduces the energy level difference between the singlet state and the triplet state, but also realizes the light emission of different colors.

Description

Maleimide derivative, and preparation method and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display. More particularly, relates to a maleimide derivative, a preparation method and application thereof.
Background
Organic electroluminescence refers to a phenomenon that an Organic material emits Light under the excitation action of current or electric field, and a device made of Organic small molecules or macromolecules as an electroluminescent material is generally called an Organic Light-Emitting device (Organic Light-Emitting Devices), which is abbreviated as OLEDs. Compared with the traditional inorganic electroluminescent devices, OLEDs have the advantages of wide material selection range, capability of realizing full-color display, low driving voltage (3-10V), high luminous brightness and luminous efficiency, wide viewing angle, high response speed (1 us), capability of realizing flexible display and the like.
Currently, a Thermally Activated Delayed Fluorescence (TADF) material as a third-generation organic electroluminescent material theoretically can realize 100% of exciton utilization rate, and has the advantages of material diversity, good stability, low cost and the like, so that people pay attention to the TADF material. The D-A type TADF molecule based on the design principle of Intramolecular Charge Transfer (ICT) can simultaneously realize smaller Delta ESTTo ensure T1State to S1Effective reverse gap crossing of states and higher fluorescence quantum efficiency to obtain high performance devices.
The aromatic imide acceptor is an electron transport material of polycyclic aromatic hydrocarbon with excellent thermal stability and oxidation resistance, and has strong electron affinity and higher electron mobility. Among them, maleimide derivatives were extracted from natural substances at the earliest time, and have received wide attention from researchers because of their biological activities. In addition, the maleimide derivative also has the advantages of high fluorescence intensity, good chemical stability and the like, so the maleimide derivative has good application prospect in the aspect of organic photoelectric materials.
The maleimide is easy to derive, is a strong electron-withdrawing group and also has three reaction sites capable of being functionalized, so that the maleimide derivative with substituents introducing different electron-donating abilities is provided, the optical band gap can be effectively adjusted, and the light emission of different colors is realized.
Disclosure of Invention
The first purpose of the invention is to provide a maleimide derivative which can realize different colors of luminescence by selecting donor groups with different electron donating abilities.
The second object of the present invention is to provide a process for producing the maleimide derivative.
The third purpose of the invention is to provide an application of the maleimide derivative.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a maleimide derivative, which has a structural general formula shown in formula I:
Figure BDA0001678253200000021
wherein R is1And R2Each independently selected from at least one of an arylamine group of 6 to 30 carbon atoms, an aryl group of 6 to 30 carbon atoms, a substituted heteroaromatic group of 5 to 50 ring atoms; r3Selected from hydrogen atoms, alkyl groups of 1 to 20 carbon atoms, aryl groups of 6 to 30 carbon atoms, substituted aromatic heterocyclic groups of 5 to 50 ring atomsAt least one of the clusters.
Further, the arylamine group having 6 to 30 carbon atoms is at least one selected from the group consisting of a diphenylamine group, a triphenylamine group, a methylphenylamine group, an ethylphenylamine group, a propylphenylamino group, an isopropylphenylamino group, an ethoxyphenylamino group, a propoxyphenylamine group, a fluorophenylamine group, a chlorophenylamine group, a bromophenylamino group, an iodophenylamino group, a dimethylphenylamino group, a diethylphenylamino group, a dipropylphenylamine group, a diisopropylphenylamino group, a dimethoxyphenylamino group, a diethoxyphenylamine group, a dipropoxyphenylamine group, a difluorophenylamino group, a dichlorophenylamino group, a dibromophenylamino group, and a diiodophenylamino group, and a substituent of the phenyl group may be ortho-para-position.
Further, the aryl group having 6 to 30 carbon atoms is selected from at least one of phenyl, perylenyl, pyrenyl, fluorenyl, spirobifluorenyl, diphenyl, triphenyl, tetracenyl and 9, 9' -spirobifluorenyl.
Further, the substituted aryl group having 6 to 30 carbon atoms is selected from at least one of o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, o-cumyl group, m-cumyl group, p-cumyl group, trimethylphenyl group and 9, 9' -dimethylfluorenyl group.
Further, the heterocyclic aryl group of 5 to 50 carbon atoms is selected from the group consisting of 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, p-benzofuryl, 7-benzofuranyl, dibenzofuran-2-yl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalyl, 5-quinoxalyl, 6-quinoxalyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, N-phenylcarbazolyl, 1-phenazine group, 2-phenazine group, 3-phenazine group, 4-phenazine group, 6-phenazine group, 7-phenazine group, 8-phenazine group, 9-phenazine group, 10-phenazine group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9, 10-dimethylazinyl group, 1, 7-phenaline-2-yl group, 1, 7-phenaline-3-yl group, 1, 7-phenaline-4-yl group, 1, 7-phenaline-5-yl group, 1, 7-phenaline-6-yl group, 1, 7-phenaline-8-yl group, 1-phenaline-3-yl group, 1, 7-phenaline-4-yl group, 1, 7-phenaline-5-yl group, 1, 7-phenaline-6-yl group, 1, 7-phenaline-8-yl group, 1, 7-phenanthroline-9-yl group, 1, 7-phenanthroline-10-yl group, 1, 8-phenanthroline-2-yl group, 1, 8-phenanthroline-3-yl group, 1, 8-phenanthroline-4-yl group, 1, 8-phenanthroline-5-yl group, 1, 8-phenanthroline-6-yl group, 1, 8-phenanthroline-7-yl group, 1, 8-phenanthroline-9-yl group, 1, 8-phenanthroline-10-yl group, 1, 9-phenanthroline-2-yl group, 1, 9-phenanthroline-3-yl group, 1, 9-phenanthroline-4-yl group, 1, 9-phenanthroline-5-yl group, 1, 9-phenanthroline-6-yl group, 1, 9-phenanthroline-7-yl group, 1, 9-phenanthroline-8-yl group, 1, 9-phenanthroline-10-yl group, 1, 10-phenanthroline-2-yl group, 1, 10-phenanthroline-3-yl group, 1, 10-phenanthroline-4-yl group, 1, 10-phenanthroline-5-yl group, 2, 9-phenanthroline-1-yl group, 2, 9-phenanthroline-3-yl group, 2, 9-phenanthroline-4-yl group, 2, 9-phenanthroline-5-yl group, 2, 9-phenanthroline-6-yl group, 2, 9-phenanthroline-7-yl group, 2, 9-phenanthroline-8-yl group, 2, 9-phenanthroline-10-yl group, 2, 2, 8-phenanthroline-1-yl, 2, 8-phenanthroline-3-yl, 2, 8-phenanthroline-4-yl, 2, 8-phenanthroline-5-yl, 2, 8-phenanthroline-6-yl, 2, 8-phenanthroline-7-yl, 2, 8-phenanthroline-9-yl, 2, 8-phenanthroline-10-yl, 2, 7-phenanthroline-1-yl, 2, 7-phenanthroline-3-yl, 2, 7-phenanthroline-4-yl, 2, 7-phenanthroline-5-yl, 2, 7-phenanthroline-6-yl, 2, 7-phenanthroline-8-yl, 2, 7-phenanthroline-9-yl, 2, 7-phenanthroline-10-yl, 1-phenothiazinyl, 2-phenazinyl, phenothiazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, phenoxazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, dibenzothiophen-2-yl.
Further, the alkyl group having 1 to 20 carbon atoms is selected from at least one of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, and 2-methylpentyl group.
The invention further provides a preparation method of the maleimide derivative, which comprises the following steps:
1) synthesis of 2, 3-dibromo N-R3-a maleimide;
2) 2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Suzuki reaction of substituted pinacol borate or reaction with R-bearing boronic acid pinacol ester1And/or R2And carrying out Ullmann reaction on the nitrogen-containing heterocyclic compound of the substituent group to obtain the maleimide derivative.
Wherein said has R1And/or R2The structural formula of the substituent pinacol borate is as follows:
Figure BDA0001678253200000041
further, the Suzuki reaction is 2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Adding the pinacol borate of the substituent group into a mixed solution of palladium tetratriphenylphosphine and potassium carbonate as catalysts and toluene and water as solvents, refluxing under the protection of nitrogen, removing the solvents, extracting, and evaporating to dryness. Preferably, the refluxing time is 3-5 h; the reaction is incomplete when the time is too short, and energy is wasted when the time is too long.
Further, the Ullmann reaction is 2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Adding a catalyst PEPSI-Ipr, alkali sodium tert-butoxide and solvent anhydrous toluene into the nitrogen-containing heterocyclic compound of the substituent group, refluxing under the protection of nitrogen, removing the solvent, extracting, and evaporating to dryness to obtain the compound. Preferably, refluxing for 16-24 h; the reaction is incomplete when the time is too short, and energy is wasted when the time is too long.
The invention further provides application of the maleimide derivative in preparation of organic electroluminescent devices and organic solar cells.
Further, the organic electroluminescent device is an organic electroluminescent device based on thermally activated delayed fluorescence.
In a specific embodiment of the present invention, the organic electroluminescent device has a structure that: substrate-anode-hole transport layer-organic light emitting layer-electron transport layer-cathode;
the organic light-emitting layer is a maleimide derivative shown in a formula I or a mixture of the maleimide derivative shown in the formula I and 3, 5 DCzPPY; the substrate is one of glass, polyester and polyimide compounds; the anode is one of indium tin oxide, zinc oxide, tin zinc oxide, gold, silver, copper, polythiophene/sodium polyvinyl benzene sulfonate and polyaniline; the hole transport layer is made of triarylamine materials; the electron transport layer is a nitrogen heterocyclic material; the cathode is an electrode layer formed by lithium, magnesium, calcium, strontium, aluminum or indium, or an alloy of one of the above and copper, gold or silver, or the above metal or alloy and metal fluoride alternately.
The invention has the following beneficial effects:
1. the maleimide derivative has certain electron transmission capacity by introducing a plurality of electron-rich groups, and can effectively separate the highest occupied orbital (HOMO) energy level and the lowest unoccupied orbital (LUMO) energy level of the maleimide derivative by modifying groups with different electron-donating capacities, thereby not only reducing the energy level difference between the singlet state and the triplet state, but also realizing the luminescence of different colors.
2. The maleimide derivative of the invention introduces large substituent groups, improves the film forming property and chemical stability, and enables the prepared organic electroluminescent device to have higher stability, high device efficiency and low turn-on voltage.
3. The solid film prepared from the maleimide derivative has a wider absorption spectrum, and the maximum absorption wavelength of part of materials is even prolonged to a near infrared region, so that the prepared organic solar cell has better performance.
4. The maleimide derivative of the invention adopts a simple and convenient synthetic method and is easy to operate, and the obtained maleimide derivative has good performance.
5. The organic electroluminescent device based on thermally activated delayed fluorescence prepared by using the maleimide derivative as the guest luminescent material has the superior performances of high brightness and high efficiency.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1a shows an absorption spectrum of an N-phenylmaleimide derivative of example 9 of the present invention.
FIG. 1b shows an absorption spectrum at room temperature and a 77K fluorescence spectrum and phosphorescence spectrum of an N-phenylmaleimide derivative of example 9 of the present invention.
FIG. 2a shows an absorption spectrum of a maleimide derivative of example 20 of the present invention.
FIG. 2b shows an absorption spectrum at room temperature and a 77K fluorescence spectrum and phosphorescence spectrum of the N-phenylmaleimide derivative of example 20 of the present invention.
Fig. 3 shows a schematic structural diagram of an organic electroluminescent device based on thermally activated delayed fluorescence prepared by using the maleimide derivative of the present invention as a guest material.
Fig. 4a shows the EL of organic electroluminescent devices based on example 9 of the invention with a doping ratio of 0.8% based on Comp-7 and 3, 5DCzPPY at different luminances.
Fig. 4b shows the L-V curves at different brightnesses for organic electroluminescent devices based on Comp-7 and 3, 5DCzPPY with a doping ratio of 0.8% according to example 9 of the present invention.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
On one hand, the invention provides a maleimide derivative, the structural general formula of which is shown as formula I:
Figure BDA0001678253200000061
wherein R is1And R2Each independently selected from at least one of an arylamine group of 6 to 30 carbon atoms, an aryl group of 6 to 30 carbon atoms, a substituted heteroaromatic group of 5 to 50 ring atoms; r3At least one selected from the group consisting of a hydrogen atom, an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 30 carbon atoms, a substituted aryl group of 6 to 30 carbon atoms, and a substituted aromatic heterocyclic group of 5 to 50 ring atoms.
The maleimide derivative has certain electron transmission capacity by introducing a plurality of electron-rich groups, and can effectively separate the highest occupied orbital (HOMO) energy level and the lowest unoccupied orbital (LUMO) energy level of the maleimide derivative by modifying groups with different electron-donating capacities, thereby not only reducing the energy level difference between the singlet state and the triplet state, but also realizing the luminescence of different colors.
Specifically, the arylamine group having 6 to 30 carbon atoms is at least one selected from the group consisting of a diphenylamine group, a triphenylamine group, a methylphenylamine group, an ethylphenylamine group, a propylphenylamino group, an isopropylphenylamino group, an ethoxyphenylamino group, a propoxyphenylamine group, a fluorophenylamine group, a chlorophenylamine group, a bromophenylamino group, an iodophenylamino group, a dimethylphenylamino group, a diethylphenylamino group, a dipropylphenylamine group, a diisopropylphenylamino group, a dimethoxyphenylamino group, a diethoxyphenylamine group, a dipropoxyphenylamine group, a difluorophenylamino group, a dichlorophenylamino group, a dibromophenylamino group and a diiodophenylamino group, and the substituent of the phenyl group may be ortho-para-position.
Specifically, the aryl group having 6 to 30 carbon atoms is selected from at least one of phenyl, perylenyl, pyrenyl, fluorenyl, spirobifluorenyl, diphenyl, triphenyl, tetracenyl and 9, 9' -spirobifluorenyl.
Specifically, the substituted aryl group having 6 to 30 carbon atoms is selected from at least one of o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, o-cumyl group, m-cumyl group, p-cumyl group, trimethylphenyl group and 9, 9' -dimethylfluorenyl group.
Specifically, the heterocyclic aryl group of 5 to 50 carbon atoms is selected from the group consisting of 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, p-benzofuryl, 7-benzofuranyl, dibenzofuran-2-yl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalyl, 5-quinoxalyl, 6-quinoxalyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, N-phenylcarbazolyl, 1-phenazine group, 2-phenazine group, 3-phenazine group, 4-phenazine group, 6-phenazine group, 7-phenazine group, 8-phenazine group, 9-phenazine group, 10-phenazine group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9, 10 dimethyl-acridinyl group, 1, 7-phenaline-2-yl group, 1, 7-phenaline-3-yl group, 1, 7-phenaline-4-yl group, 1, 7-phenaline-5-yl group, 1, 7-phenaline-6-yl group, 1, 7-phenaline-8-yl group, 1-phenaline-3-yl group, 1, 7-phenaline-4-yl group, 1, 7-phenaline-5-yl group, 1, 7-phenaline-6-yl group, 1, 7-phenaline-8-yl group, 1, 7-phenanthroline-9-yl group, 1, 7-phenanthroline-10-yl group, 1, 8-phenanthroline-2-yl group, 1, 8-phenanthroline-3-yl group, 1, 8-phenanthroline-4-yl group, 1, 8-phenanthroline-5-yl group, 1, 8-phenanthroline-6-yl group, 1, 8-phenanthroline-7-yl group, 1, 8-phenanthroline-9-yl group, 1, 8-phenanthroline-10-yl group, 1, 9-phenanthroline-2-yl group, 1, 9-phenanthroline-3-yl group, 1, 9-phenanthroline-4-yl group, 1, 9-phenanthroline-5-yl group, 1, 9-phenanthroline-6-yl group, 1, 9-phenanthroline-7-yl group, 1, 9-phenanthroline-8-yl group, 1, 9-phenanthroline-10-yl group, 1, 10-phenanthroline-2-yl group, 1, 10-phenanthroline-3-yl group, 1, 10-phenanthroline-4-yl group, 1, 10-phenanthroline-5-yl group, 2, 9-phenanthroline-1-yl group, 2, 9-phenanthroline-3-yl group, 2, 9-phenanthroline-4-yl group, 2, 9-phenanthroline-5-yl group, 2, 9-phenanthroline-6-yl group, 2, 9-phenanthroline-7-yl group, 2, 9-phenanthroline-8-yl group, 2, 9-phenanthroline-10-yl group, 2, 2, 8-phenanthroline-1-yl, 2, 8-phenanthroline-3-yl, 2, 8-phenanthroline-4-yl, 2, 8-phenanthroline-5-yl, 2, 8-phenanthroline-6-yl, 2, 8-phenanthroline-7-yl, 2, 8-phenanthroline-9-yl, 2, 8-phenanthroline-10-yl, 2, 7-phenanthroline-1-yl, 2, 7-phenanthroline-3-yl, 2, 7-phenanthroline-4-yl, 2, 7-phenanthroline-5-yl, 2, 7-phenanthroline-6-yl, 2, 7-phenanthroline-8-yl, 2, 7-phenanthroline-9-yl, 2, 7-phenanthroline-10-yl, 1-phenothiazinyl, 2-phenazinyl, phenothiazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, phenoxazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, dibenzothiophen-2-yl.
Specifically, the alkyl group having 1 to 20 carbon atoms is at least one selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group and a 2-methylpentyl group.
The invention adjusts the physical properties of solubility of the substance by introducing alkyl, and adjusts the photophysical properties of the substance such as luminous color, luminous efficiency, intramolecular charge transfer and the like by introducing aryl, substituted aryl, arylamine and heterocyclic aryl through the strength of electron donating ability.
In a second aspect, the present invention provides a method for preparing the maleimide derivative, comprising the following steps:
1) synthesis of 2, 3-dibromo N-R3-a maleimide;
2) 2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Suzuki reaction of substituted pinacol borates or reaction with substituted pinacol estersHas R1And/or R2And carrying out Ullmann reaction on the nitrogen-containing heterocyclic compound of the substituent group to obtain the maleimide derivative.
Wherein said has R1And/or R2The structural formula of the substituent pinacol borate is as follows:
Figure BDA0001678253200000081
the maleimide derivative of the invention adopts a simple and convenient synthetic method and is easy to operate, and the obtained maleimide derivative has good performance.
Specifically, the 2, 3-dibromo-N-R3Maleimide against R3The various substituents are prepared according to conventional methods in the prior art.
Specifically, the Suzuki reaction is 2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Adding the pinacol borate of the substituent group into a mixed solution of palladium tetratriphenylphosphine and potassium carbonate as catalysts and toluene and water as solvents, refluxing under the protection of nitrogen, removing the solvents, extracting, and evaporating to dryness. Preferably, the refluxing time is 3-5 h; the reaction is incomplete when the time is too short, and energy is wasted when the time is too long.
Specifically, the Ullmann reaction is 2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Adding a catalyst PEPSI-Ipr, alkali sodium tert-butoxide and solvent anhydrous toluene into the nitrogen-containing heterocyclic compound of the substituent group, refluxing under the protection of nitrogen, removing the solvent, extracting, and evaporating to dryness to obtain the compound. Preferably, refluxing for 16-24 h; the reaction is incomplete when the time is too short, and energy is wasted when the time is too long.
In a third aspect, the invention provides the application of the maleimide derivative in the preparation of organic electroluminescent devices and organic solar cells.
The maleimide derivative of the invention introduces large substituent groups, improves the film forming property and chemical stability, and enables the prepared organic electroluminescent device to have higher stability, high device efficiency and low turn-on voltage.
The solid film prepared from the maleimide derivative has a wider absorption spectrum, and the maximum absorption wavelength of part of materials is even prolonged to a near infrared region, so that the prepared organic solar cell has better performance.
Specifically, the organic electroluminescent device is an organic electroluminescent device based on thermally activated delayed fluorescence.
Specifically, the organic light-emitting layer of the organic electroluminescent device is a maleimide derivative shown in formula I or a mixture of the maleimide derivative shown in formula I and 3, 5 DCzPPY.
In a specific embodiment of the present invention, the organic electroluminescent device has a structure that: substrate-anode-hole transport layer-organic light emitting layer-electron transport layer-cathode;
wherein, the organic light-emitting layer of the organic electroluminescent device is a maleimide derivative shown as a formula I or a mixture of the maleimide derivative shown as the formula I and 3, 5 DCzPPY; the substrate is one of glass, polyester and polyimide compounds; the anode is one of indium tin oxide, zinc oxide, tin zinc oxide, gold, silver, copper, polythiophene/sodium polyvinyl benzene sulfonate and polyaniline; the hole transport layer is made of triarylamine materials; the electron transport layer is a nitrogen heterocyclic material; the cathode is an electrode layer formed by lithium, magnesium, calcium, strontium, aluminum or indium, or an alloy of one of the above and copper, gold or silver, or the above metal or alloy and metal fluoride alternately.
The present invention will be further described below by way of specific examples.
In the present invention, the raw materials and equipment used are commercially available or commonly used in the art, unless otherwise specified. The methods in the following examples are conventional in the art unless otherwise specified.
Example 1
Synthesis of 2, 3-dibromo-N-phenyl-maleimide: dissolving 600mg of 2, 3-dibromomaleic anhydride and 0.5mL of aniline in 3mL of glacial acetic acid, refluxing and stirring at 120 ℃ for 10min, cooling to room temperature, adding distilled water to precipitate, performing suction filtration to obtain a precipitate, drying in a vacuum drying oven overnight, and performing column chromatography to obtain 421mg of a product.
Figure BDA0001678253200000091
Example 2
Synthesis of 2, 3-dibromo-N-isobutane-maleimide: dissolving 200mg of sodium hydride in 10mL of N, N-dimethylformamide in an ice water bath, dissolving 600mg of 2, 3-dibromomaleimide in 10mL of N, N-dimethylformamide, dropwise adding the solution into the sodium hydride, stirring for 30min, adding 1-bromo-2-methylpropane, heating to 60 ℃, continuing to react for 1h, cooling, quenching with saturated ammonium chloride, extracting with ethyl acetate, drying with anhydrous sodium sulfate, concentrating, and carrying out column chromatography to obtain 403mg of a product.
Figure BDA0001678253200000092
Example 3
Synthesis of N-phenylmaleimide derivative Comp-1
Weighing 350mg of 2, 3-dibromo-N-phenyl-maleimide and 300mg of pinacol phenylboronate into a 100mL double-mouth bottle, adding 50mg of tetratriphenylphosphine palladium, 15mL of 2M potassium carbonate aqueous solution and 20mL of toluene solvent, performing reflux reaction for 5h under the protection of nitrogen, removing the solvent under reduced pressure, extracting with dichloromethane and water, combining organic phases, evaporating the solvent under reduced pressure, and performing column chromatography to obtain the maleimide derivative Comp-1.
Figure BDA0001678253200000101
Example 4
Synthesis of N-phenylmaleimide derivative Comp-2
In the same manner as in example 3, spirobifluorene-3-boronic acid pinacol ester was used instead of phenylboronic acid pinacol ester to obtain N-phenylmaleimide derivative Comp-2.
Figure BDA0001678253200000102
Example 5
Synthesis of N-phenylmaleimide derivative Comp-3
In the same manner as in example 3, 9' -dimethylfluorenylboronic acid pinacol ester was used in place of phenylboronic acid pinacol ester to obtain N-phenylmaleimide derivative Comp-3.
Figure BDA0001678253200000111
Example 6
Synthesis of N-phenylmaleimide derivative Comp-4
In the same manner as in example 3, the pinacol ester phenylboronic acid was replaced with the pinacol ester 1-pyrenyl boronic acid to obtain the N-phenylmaleimide derivative Comp-4.
Figure BDA0001678253200000112
Example 7
Synthesis of N-phenylmaleimide derivative Comp-5
In the same manner as in example 3, the pinacol ester phenylboronic acid was replaced with 3-perylenepinacol ester borate to obtain N-phenylmaleimide derivative Comp-5.
Figure BDA0001678253200000113
Example 8
Synthesis of N-phenylmaleimide derivative Comp-6
In the same manner as in example 3, the pinacol ester phenylboronic acid was replaced with pinacol ester N-phenylcarbazole borate to obtain N-phenylmaleimide derivative Comp-6.
Figure BDA0001678253200000121
Example 9
Synthesis of N-phenylmaleimide derivative Comp-7
In the same manner as in example 3, triphenylamine pinacol ester was used in place of pinacol phenylboronate to obtain N-phenylmaleimide derivative Comp-7.
Figure BDA0001678253200000122
FIG. 1a is the absorption spectrum of the photophysical data of Comp-7 prepared by the present invention, the absorption band at 360nm of 250-; the wider and strong charge transfer absorption peak shows that the compound has stronger intramolecular charge transfer characteristic and is similar to the property of the reported intramolecular charge transfer compound; and moreover, the stronger intramolecular charge transfer state is beneficial to efficient energy transfer between the host and the guest, and provides a good foundation for subsequent device preparation. FIG. 1b is a diagram of the spectra of room temperature fluorescence and 77K fluorescence and phosphorescence of Comp-7, and the singlet state and triplet state energy levels of the compound can be calculated from the peak side bands of the 77K low temperature fluorescence and the low temperature phosphorescence respectively, so as to facilitate the subsequent device structure design and optimization.
Example 10
Synthesis of N-phenylmaleimide derivative Comp-8
2, 3-dibromo-N-p-tert-butylaniline was obtained by using p-tert-butylaniline instead of aniline in the same manner as in example 1, and pinacol ester was used as triphenylamine instead of pinacol ester phenylboronate in the same manner as in example 3 to obtain N-p-tert-butylphenyl maleimide derivative Comp-8.
Figure BDA0001678253200000131
Example 11
Synthesis of maleimide derivative Comp-9
Weighing 350mg of 2, 3-dibromo-N-phenyl-maleimide and 382mg of carbazole, adding the 2, 3-dibromo-N-phenyl-maleimide and 382mg of carbazole into a 100mL double-mouth bottle, adding 60mg of PEPSI-Ipr and 98mg of sodium tert-butoxide as catalysts and 10mL of anhydrous toluene solvent, performing reflux reaction for 24 hours under the protection of nitrogen, removing the solvent under reduced pressure, extracting with dichloromethane and water, combining organic phases, evaporating the solvent under reduced pressure, and performing column chromatography to obtain the maleimide derivative Comp-8.
Figure BDA0001678253200000132
Example 12
Synthesis of N-phenylmaleimide derivative Comp-10
In the same manner as in example 11, 9, 10-dimethylacridine was used in place of carbazole to give N-phenylmaleimide derivative Comp-10.
Figure BDA0001678253200000141
Example 13
Synthesis of N-phenylmaleimide derivative Comp-11
In the same manner as in example 11, instead of carbazole, phenothiazine was used to obtain N-phenylmaleimide derivative Comp-11.
Figure BDA0001678253200000142
Example 14
Synthesis of N-phenylmaleimide derivative Comp-12
In the same manner as in example 11, phenoxazine was used in place of carbazole to obtain N-phenylmaleimide derivative Comp-12.
Figure BDA0001678253200000143
Example 15
Synthesis of N-phenylmaleimide derivative Comp-13
In the same manner as in example 11, diphenylamine was used in place of carbazole to obtain N-phenylmaleimide derivative Comp-13.
Figure BDA0001678253200000144
Example 16
Synthesis of N-phenylmaleimide derivative Comp-14
In the same manner as in example 11, diphenylamine was used in place of carbazole, and triphenylamine was used in place of aniline, to obtain N-phenylmaleimide derivative Comp-14.
Figure BDA0001678253200000151
Example 17
Synthesis of maleimide derivative Comp-15
In the same manner as in example 3, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide to obtain maleimide derivative Comp-15.
Figure BDA0001678253200000152
Example 18
Synthesis of maleimide derivative Comp-16
In the same manner as in example 3, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and spirobifluorene-3-boronic acid pinacol ester was used in place of phenylboronic acid pinacol ester, to obtain maleimide derivative Comp-16.
Figure BDA0001678253200000153
Example 19
Synthesis of maleimide derivative Comp-17
In the same manner as in example 3, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and N-phenylcarbazole pinacol borate was used in place of pinacol phenylborate, whereby maleimide derivative Comp-17 was obtained.
Figure BDA0001678253200000161
Example 20
Synthesis of maleimide derivative Comp-18
In the same manner as in example 3, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and triphenylamine pinacol borate was used in place of pinacol phenylborate, whereby maleimide derivative Comp-18 was obtained.
Figure BDA0001678253200000162
FIG. 2a is the absorption spectrum of the photophysical data of Comp-18 prepared by the present invention, the absorption band at 285-360nm is the local state of the molecule, which is caused by pi-pi transition and n-pi transition, the absorption band at 400-600nm is caused by the charge transfer transition of the molecule; the wider and strong charge transfer absorption peak shows that the compound has stronger intramolecular charge transfer characteristic and is similar to the property of the reported intramolecular charge transfer compound; and moreover, the stronger intramolecular charge transfer state is beneficial to efficient energy transfer between the host and the guest, and provides a good foundation for subsequent device preparation. FIG. 2b is a diagram of the spectra of room temperature fluorescence and 77K fluorescence and phosphorescence of Comp-18, and the singlet state and triplet state energy levels of the compound can be calculated from the peak side bands of the 77K low temperature fluorescence and the low temperature phosphorescence, respectively, so as to facilitate the subsequent device structure design and optimization.
Example 21
Synthesis of N-isobutane maleimide derivative Comp-19
In the same manner as in example 20, 2, 3-dibromo-N-phenyl-maleimide was replaced with 2, 3-dibromo-N-isobutane-maleimide to obtain maleimide-based derivative Comp-19.
Figure BDA0001678253200000171
Example 22
Synthesis of maleimide derivative Comp-20
In the same manner as in example 11, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide to obtain maleimide-based derivative Comp-20.
Figure BDA0001678253200000172
Example 23
Synthesis of maleimide derivative Comp-21
In the same manner as in example 11, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and 9, 10-dimethylacridine was used in place of carbazole, whereby maleimide-based derivative Comp-21 was obtained.
Figure BDA0001678253200000173
Example 24
Synthesis of N-phenylmaleimide derivative Comp-22
In the same manner as in example 11, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and phenothiazine was used in place of carbazole, to obtain the maleimide-based derivative Comp-22.
Figure BDA0001678253200000181
Example 25
Synthesis of N-phenylmaleimide derivative Comp-23
In the same manner as in example 11, 2, 3-dibromo-N-N-pentyl-maleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and phenoxazine was used in place of carbazole to obtain the maleimide derivative Comp-23.
Figure BDA0001678253200000182
Example 26
Synthesis of N-phenylmaleimide derivative Comp-24
In the same manner as in example 10, 2, 3-dibromomaleimide was used in place of 2, 3-dibromo-N-phenyl-maleimide and diphenylamine was used in place of carbazole, to obtain the maleimide derivative Comp-24.
Figure BDA0001678253200000183
Example 27
Synthesis of maleimide derivative Comp-25
Weighing 350mg of 2, 3-dibromo-N-phenyl-maleimide and 150mg of phenylboronic acid, adding the mixture into a 100mL double-neck bottle, adding 25mg of tetrakis (triphenylphosphine) palladium, 8mL of 2M potassium carbonate aqueous solution and 10mL of toluene solvent, carrying out reflux reaction for 5h under the protection of nitrogen, removing the solvent under reduced pressure, extracting with dichloromethane and water, combining organic phases, evaporating the solvent under reduced pressure, and carrying out column chromatography to obtain the maleimide derivative Comp-25.
Figure BDA0001678253200000191
Example 28
Synthesis of maleimide derivative Comp-26
328mg of 2, 3-dibromo-N-phenyl-maleimide and 220mg of phenylboronic acid are weighed and added into a 100mL double-neck flask, 25mg of tetrakis (triphenylphosphine) palladium, 8mL of 2M potassium carbonate aqueous solution and 10mL of toluene solvent are added, reflux reaction is carried out for 5 hours under the protection of nitrogen, the solvent is removed under reduced pressure, dichloromethane and water are used for extraction, organic phases are combined, the solvent is evaporated to dryness under reduced pressure, and column chromatography is carried out to obtain the maleimide derivative Comp-26.
Figure BDA0001678253200000192
Example 29
An organic electroluminescent device was prepared using the derivative Comp-6 obtained in example 8;
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, irradiating for 10 minutes by using an ultraviolet light cleaning machine, and bombarding by using a low-energy cation beam to show;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, evaporating alpha-NPD (alpha-NPD) on the anode layer film by 20nm, and then evaporating TCTA (TCTA) as a hole transport layer, wherein the evaporated film is 20 nm; continuously evaporating 15nm MCP as an exciton blocking layer;
continuously evaporating a layer of Comp-6 doped 3, 5DCzPPY as an organic light emitting layer of the device on the exciton blocking layer, wherein the doping ratio of Comp-6 to 3, 5DCzPPY is 1.5%, and the total film thickness of the evaporation is 20 nm;
continuously evaporating a TMPYPB layer as an electron transmission layer of the device, wherein the total film thickness of the evaporation is 55 nm;
and finally, sequentially evaporating a LiF layer and Al on the electron transport layer to serve as a cathode layer of the device, wherein the thickness of the LiF layer is 1.0nm, and the thickness of the Al layer is 100 nm.
The device structure is Al (100nm)/LiF (1.0nm)/TMPYPB (55nm)/EML (15nm)/MCP (15nm)/TCTA (20 nm)/alpha-NPD (20nm)/ITO (100nm), as shown in FIG. 3;
the device performance index is as follows:
starting voltage: 3.3V;
maximum luminance: 10000cd/m2(9.6V)；
Luminous efficiency: 6.35 cd/A.
Example 30
Selecting the derivative Comp-7 obtained in example 9 to prepare an organic electroluminescent device;
an organic EL device was prepared and device properties were tested by following the same procedure as in example 27, except that Comp-9 was used instead of Comp-7, and the doping ratio of Comp-7 to 3, 5DCzPPY was 0.8%.
The device structure is Al (100nm)/LiF (1.0nm)/TMPYPB (55nm)/EML (20nm)/MCP (15nm)/TCTA (20 nm)/alpha-NPD (20nm)/ITO (100nm), as shown in FIG. 3;
the device performance index is as follows:
starting voltage: 3.3V;
maximum luminance: 6000cd/m2(9.6V)；
Luminous efficiency: 10.4 cd/A.
FIG. 4a shows the electroluminescence spectra at a certain brightness of the resulting organic electroluminescent devices based on a doping ratio of 0.8% for Comp-7 and 3, 5 DCzPPY; FIG. 4b shows the L-V curves of organic electroluminescent devices based on Comp-7 and 3, 5DCzPPY with a doping ratio of 0.8% at different luminances, the luminance gradually increases with increasing voltage, and the maximum luminance reaches 6000cd/m at 9.6V2。
Example 31
Preparing an organic electroluminescent device by using the derivative Com-18 obtained in the embodiment 20;
an organic EL device was prepared and device properties were tested by following the same procedures as in example 27, except that Com-18 was used instead of Com-6, and the doping ratio of Comp-18 to 3, 5DCzPPY was 0.6%.
The device structure is Al (100nm)/LiF (1.0nm)/TMPYPB (55nm)/EML (20nm)/MCP (15nm)/TCTA (20 nm)/alpha-NPD (20nm)/ITO (100nm), as shown in FIG. 3;
the device performance index is as follows:
starting voltage: 3.5V;
maximum luminance: 7000cd/m2(11.5V)；
Luminous efficiency: 6.39 cd/A.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (5)

1. The maleimide derivative is characterized in that the structural general formula of the maleimide derivative is shown as the formula I:
Figure 352337DEST_PATH_IMAGE001
the compound has a structure shown in a formula I,
wherein R is1And R2The same, and is selected from N-phenylcarbazolyl or triphenylamine; r3Selected from phenyl.
2. A process for producing the maleimide-based derivative according to claim 1, comprising the steps of:
synthesis of 2, 3-dibromo N-R3-a maleimide;
2, 3-dibromo N-R3Maleimide with a base having R1And/or R2Suzuki reaction of substituted pinacol borate or reaction with R-bearing boronic acid pinacol ester1And/or R2And carrying out Ullmann reaction on the nitrogen-containing heterocyclic compound of the substituent group to obtain the maleimide derivative.
3. Use of the maleimide derivative according to claim 1 for the preparation of organic electroluminescent devices and organic solar cells.
4. Use according to claim 3, wherein the organic electroluminescent device is an organic electroluminescent device based on thermally activated delayed fluorescence.
5. The use according to claim 3, wherein the organic light-emitting layer of the organic electroluminescent device is a maleimide derivative of formula I or a mixture of a maleimide derivative of formula I and 3, 5 DCzPPY.
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