CN111875635A - Organic compound, electronic device and corresponding preparation method - Google Patents

Organic compound, electronic device and corresponding preparation method Download PDF

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CN111875635A
CN111875635A CN201910822621.0A CN201910822621A CN111875635A CN 111875635 A CN111875635 A CN 111875635A CN 201910822621 A CN201910822621 A CN 201910822621A CN 111875635 A CN111875635 A CN 111875635A
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郑江波
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Guangdong Juhua Printing Display Technology Co Ltd
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Abstract

The invention relates to an organic compound, an electronic device and a corresponding preparation method. The structural formula of the organic compound is as follows:
Figure DDA0002187999870000011
the organic compound takes an aromatic ring group or an aromatic heterocyclic group as a core, takes a phosphorus-oxygen bond as arm connection, and takes a vinyl group as a terminal to construct a crosslinkable material, wherein the phosphorus-oxygen bond has a strong electron-withdrawing induction effect, can polarize molecules, improves the electronegativity of the molecules, and sigmaC‑PThe bond can effectively shield the electrons in the moleculeThe interaction has influence on the molecular triplet state energy level, so that the triplet state energy level of the compound is high, the diffusion of excitons can be effectively blocked, the electron transport capacity is high, and the electron transport can be effectively promoted. The compound is a small molecule which can be dissolved by a conventional solvent at normal temperature, and can form a crosslinking compound which is insoluble in the conventional solvent by a thermal crosslinking mode after film formation, and is not easily dissolved by a functional layer solvent of a next layer. The material is suitable for forming a film by using a solution to obtain an electronic device with large area and low cost.

Description

Organic compound, electronic device and corresponding preparation method
Technical Field
The invention relates to the technical field of carrier transmission materials, in particular to an organic compound, an electronic device and corresponding preparation methods.
Background
An Organic Light Emitting Diode (OLED) device is a device that emits light by stacking a carrier injection layer, a carrier transport layer, and a light emitting layer. The solution method for processing and preparing the OLED device, particularly the large-size OLED device, has the advantages of low cost, large-area preparation and the like, so that attention of many manufacturers is paid. However, conventional solution processing methods can easily cause intermixing between functional layers, which can affect device performance. Therefore, how to solve the problem of mixing of multiple functional layers in the manufacturing process without affecting the performance of the device is a problem that needs to be solved in the device manufacturing. The traditional solution includes an orthogonal solvent system, etc., and because the commonly used organic small molecule materials have good solubility in organic solvents, it is difficult to ensure that the solvent used in the next layer does not dissolve the material deposited in the previous layer. However, the functional cross-linked material has different characteristics, and is soluble in a solvent before cross-linking, while the polymer formed after cross-linking is not soluble in a conventional solvent. Therefore, the cross-linked functional layer is not easy to form mutual solution or mixture with the next functional layer. Therefore, the development of a suitable crosslinkable functional layer material is necessary for the solution processing to prepare OLED devices. However, the conventional crosslinkable functional layer material has low carrier transport efficiency, and particularly, the crosslinkable electron transport material is less, which limits the improvement of device performance.
Disclosure of Invention
Based on this, it is necessary to provide a crosslinkable organic compound having high carrier transport efficiency which can be used as, but not limited to, an electron transport material, and a method for preparing the same.
The technical scheme of the invention for solving the technical problems is as follows.
An organic compound having the formula:
Figure BDA0002187999850000011
wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
plural R2Each independently selected from the group consisting of empty, withAn aromatic ring group with an alkyl chain, an aromatic ring group without an alkyl chain, an aromatic ring group with an alkoxy chain, an aromatic ring group without an alkoxy chain, or an aromatic ring group without an alkoxy chain.
A method for preparing an organic compound, comprising the steps of:
in the compound
Figure BDA0002187999850000021
Introduction of group(s) thereon
Figure BDA0002187999850000022
Formation of the target Compound
Figure BDA0002187999850000023
Wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
plural R2Each independently selected from a vacancy, an aromatic ring group with an alkyl chain, an aromatic ring group without an alkyl chain, an aromatic ring group with an alkoxy chain, an aromatic ring group without an alkoxy chain, or an aromatic ring group without an alkoxy chain.
In addition, it is necessary to provide an electronic device containing the organic compound and a method for preparing the same.
An electronic device comprising a crosslinked compound formed by crosslinking reaction of the above organic compound.
A method for preparing electronic device includes depositing functional material solution containing above organic compound on a substrate, drying to remove solvent, heating to make organic compound with vinyl end generate cross-linking reaction to form a functional layer.
The organic compound takes an aromatic ring group or an aromatic heterocyclic group as a core and takes a phosphorus-oxygen bond as an arm connectionThe crosslinkable material is constructed by taking vinyl as the tail end, wherein phosphorus-oxygen bonds have strong electron-withdrawing induction effect, can polarize molecules, improve electronegativity of the molecules, and sigmaC-PThe bond can effectively shield the influence of the electronic interaction in the molecule on the triplet state energy level of the molecule, so that the triplet state energy level of the material is high, the diffusion of excitons can be effectively blocked, the electron transport capacity is high, and the electron transport can be effectively promoted. The organic compound is a small molecule which can be dissolved by a conventional solvent at normal temperature, and can form a crosslinking compound which is insoluble in the conventional solvent by a thermal crosslinking mode after film formation, and is not easily dissolved by a functional layer solvent of a next layer. Therefore, the organic compound can be used as an electron transport material, has high carrier efficiency, is not easily dissolved by an organic solvent after being solidified, and is beneficial to ensuring the performance of a product.
The organic compound is suitable for forming a film by using a solution to obtain an electronic device with a large area and low cost.
Drawings
Fig. 1 is a schematic structural diagram of an organic light emitting diode provided in the present invention.
Detailed Description
To facilitate an understanding of the invention, the invention will now be described more fully with reference to the accompanying drawings. Preferred embodiments of the present invention are shown in the drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The invention provides an organic compound, which has the following structural formula:
Figure BDA0002187999850000031
wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
plural R2Each independently selected from a vacancy, an aromatic ring group with an alkyl chain, an aromatic ring group without an alkyl chain, an aromatic ring group with an alkoxy chain, an aromatic ring group without an alkoxy chain, or an aromatic ring group without an alkoxy chain.
In one embodiment, Ar1The aromatic heterocyclic group is selected from phenyl, a fused ring aromatic group or an aromatic heterocyclic group containing nitrogen atoms on the ring, and can be selected from but not limited to one of the following groups:
Figure BDA0002187999850000032
in one embodiment, R1The group selected from phenyl, a fused ring aromatic group, a biphenyl group, an aromatic heterocyclic group containing a nitrogen atom in the ring, a group formed by connecting an aromatic heterocyclic group containing a nitrogen atom in the ring and an aromatic heterocyclic group, or a group formed by connecting an aromatic heterocyclic group containing a nitrogen atom in the ring and an aromatic ring group may be, for example, one selected from, but not limited to:
Figure BDA0002187999850000033
in one embodiment, R2The group is selected from a vacancy, a biphenyl group, a group in which the biphenyl group is connected with a benzene ring through an alkyl chain or an alkoxy chain of C1-C8, a group in which the biphenyl group is connected with the biphenyl group through an alkyl chain or an alkoxy chain of C1-C8, or a group in which two benzene rings are connected through an alkyl chain or an alkoxy chain of C1-C8, and can be selected from, but not limited to, one of the following groups:
Figure BDA0002187999850000041
wherein n ranges from 1 to 8.
In one embodiment, Ar1Is an aromatic heterocyclic group, e.g. s-triazine group, R1Selected from aromatic or heteroaromatic groups, or Ar1Is an aromatic ring radical, R1Is an aromatic heterocyclic group.
In one embodiment, the organic compound is selected from the group consisting of compounds represented by the following structural formulas M1-M18:
Figure BDA0002187999850000042
Figure BDA0002187999850000051
Figure BDA0002187999850000061
in one embodiment, the organic compound is selected from one of the compounds represented by the following structural formula:
Figure BDA0002187999850000071
core Ar in the molecule of the organic compound1Can be a strong electron-withdrawing unit (for example, a1, 3, 5-triazine structural unit (also referred to as s-triazine) linked to a phosphorus oxy group through an aromatic ring group or an aromatic heterocyclic group, a vinyl double bond introduced at the end of the aryl group linked to the phosphorus oxy group as an active end for thermal crosslinkingC-PThe bond can effectively shield the influence of the electronic interaction in the molecule on the triplet state energy level of the molecule; therefore, the introduction of phosphorus-oxygen bonds is a material favorable for constructing electron transport layers with high triplet energy levels. Aromatic heterocyclic groups such as s-triazine are also strong electronic units, and the organic compounds obtained by such structures are useful as electron donorsThe sub-transmission capacity is strong. If the middle core Ar1Being a pure aromatic ring group such as a benzene ring unit, or a condensed ring unit phenanthrene, an aromatic heterocyclic group (e.g., a pyridine group) having a strong electron-withdrawing group attached between the aromatic ring group as a core and a phosphorus-oxygen bond can also contribute to an improvement in the electron transport ability thereof. Thus, the organic compound can be widely used in, but not limited to, electron transport materials.
The invention further provides a preparation method of the organic compound, which comprises the following steps:
in the compound
Figure BDA0002187999850000081
Introduction of group(s) thereon
Figure BDA0002187999850000082
Formation of the target Compound
Figure BDA0002187999850000083
Wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
plural R2Each independently selected from a vacancy, an aromatic ring group with an alkyl chain, an aromatic ring group without an alkyl chain, an aromatic ring group with an alkoxy chain, an aromatic ring group without an alkoxy chain, or an aromatic ring group without an alkoxy chain.
In the third step, R2In the form of a vacancy, in which radicals are introduced
Figure BDA0002187999850000084
When the compound is mixed
Figure BDA0002187999850000085
Reacting with tributylvinyltin; or R2Selected from aromatic or heteroaromatic groups with or without alkyl or alkoxy chains, in which groups are introduced
Figure BDA0002187999850000091
When the compound is mixed
Figure BDA0002187999850000092
And compounds
Figure BDA0002187999850000093
And (4) reacting. In one embodiment, the reaction is carried out under palladium-catalyzed conditions, for example, in Pd (PPh)3)4Or Pd2(dba)3The reaction is carried out under catalysis.
In one particular example, the compound
Figure BDA0002187999850000094
Can be prepared by but not limited to the following steps:
the method comprises the following steps: the compound
Figure BDA0002187999850000095
Reacting with diphenylphosphine or its derivative (such as diphenylphosphine chloride, etc.), introducing phosphorus-oxygen bond and phenyl group, and preparing compound
Figure BDA0002187999850000096
Wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
step two: will be provided with
Figure BDA0002187999850000097
With Br2Reacting to form a compound
Figure BDA0002187999850000098
The organic compound takes an aromatic ring group or an aromatic heterocyclic group as a core, takes a phosphorus-oxygen bond as arm connection, and takes a vinyl group as a terminal to construct a crosslinkable material, wherein the phosphorus-oxygen bond has a strong electron-withdrawing induction effect, can polarize molecules, improves the electronegativity of the molecules, and sigmaC-PThe bond can effectively shield the molecule from the electronic interactionThe organic compound has a high triplet level due to the influence of the triplet level, and thus can effectively block the diffusion of excitons, and has a high electron transport ability, which can effectively promote the transport of electrons. The organic compound is a small molecule which can be dissolved by a conventional solvent at normal temperature, and can form a crosslinking compound which is insoluble in the conventional solvent by a thermal crosslinking mode after film formation, and is not easily dissolved by a functional layer solvent of a next layer.
The organic compound is suitable for forming a film by using a solution to obtain an electronic device with a large area and low cost.
For example, the present invention also provides an electronic device containing a crosslinking compound formed by a crosslinking reaction of the above organic compound.
The electronic device may be, but is not limited to, an organic light emitting diode, a quantum dot light emitting diode, an organic thin film photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, or an organic plasmon emitting diode.
The invention further provides a preparation method of the electronic device, which comprises the steps of depositing the functional material solution containing the organic compound on a substrate, drying to remove the solvent, and heating to enable the organic compound with vinyl at the tail end to carry out a crosslinking reaction to form a functional layer.
The substrate can be a substrate, an electrode layer on the substrate, or other functional layers on the electrode layer.
In one embodiment, the drying is carried out by baking at 80-150 deg.C, such as 120 deg.C, for 1-10 min, such as 10min, to remove the solvent.
In one embodiment, the crosslinking reaction is carried out at 200 ℃ to 300 ℃, for example 230 ℃, for 30min to 60 min.
The deposition may be performed by printing or coating, and may be, but is not limited to, ink jet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roll printing, twist roll printing, plate printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, or slot die coating.
The following provides some specific methods for preparing organic compounds, and organic electroluminescent devices are manufactured by using the organic compounds as electron transport layer materials. It is to be understood that the present disclosure is not intended to be limited to any one of the methods recited herein. One skilled in the art can readily modify the methods described or utilize different methods to prepare one or more of the disclosed compounds. The following methods are exemplary only, and are not intended to limit the scope of the present disclosure.
The general synthetic route of the compound M1-M9 disclosed in the invention is shown as follows:
Figure BDA0002187999850000101
synthesis steps a1 to a 2:
a solution of bromobenzonitrile (25mmol) in anhydrous chloroform was added dropwise to a solution of trifluoromethanesulfonic acid (50mmol) in toluene (toluene) under a nitrogen atmosphere, reacted under ice-bath conditions, gradually warmed to room temperature and stirred for 24 h. And after the reaction is finished, adding water to stop the reaction, stirring for two hours, filtering to obtain filter residue, washing the filter residue with water, washing with cold chloroform, and airing in the air to obtain the crude product A2. The reaction yield of the o-bromobenzonitrile, the yield of the m-bromobenzonitrile and the yield of the p-bromobenzonitrile are respectively 60%, 60% and 70%.
Synthesis steps a2 to A3:
under a nitrogen atmosphere, the raw materials A2(5mmol), NaOAc (16mmol), Pd (OAc)2(0.15mmol) and diphenylphosphine (16mmol) were dissolved in dimethylformamide DMF (25ml) as a solvent, the mixture was heated to 130 ℃ and stirred for 24 hours, then cooled to room temperature, and water was added to terminate the reaction. Extracting with dichloromethane for several times, combining organic layers, and adding anhydrous Na2SO4Drying to remove water, and removing the solvent to obtain a crude intermediate of the phosphorus product. Then the intermediate is dissolved in dichloromethane solution, and H is added dropwise under ice bath condition2O2(30%, 12ml) and reacted at this temperature for 2 h. And after the reaction is finished, extracting and separating by using dichloromethane, drying, separating and purifying by using a silica gel chromatographic column, removing the solvent by using normal hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying in vacuum at room temperature for 12 hours, weighing, and controlling the yield to be about 65%.
Synthesis steps A3 to a 4:
under nitrogen atmosphere, a solution of liquid bromine (35mmol) in dichloromethane was dropwise added to a solution of A3(10mmol) in dichloromethane, the reaction was carried out under ice bath conditions, the reaction was gradually allowed to warm to room temperature, and the reaction was stirred for 24 hours. And after the reaction is finished, extracting and separating by using dichloromethane, drying, separating and purifying by using a silica gel chromatographic column, removing the solvent by using normal hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying in vacuum at room temperature for 12 hours, weighing, and controlling the yield to be about 30%.
Synthesis steps a4 to a 5:
Figure BDA0002187999850000111
under a nitrogen atmosphere, a raw material A4(5mmol) and tributylvinyltin were added
Figure BDA0002187999850000112
(16mmol) with palladium tetratriphenylphosphine Pd (PPh) as catalyst3)4(0.15mmol) was dissolved in dimethylformamide DMF (45ml), the mixture was heated to 130 ℃ and stirred for 24h, then cooled to room temperature and quenched by the addition of water. And after the reaction is finished, extracting and separating by using dichloromethane, drying, separating and purifying by using a silica gel chromatographic column, removing the solvent by using n-hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying for 12 hours in vacuum at room temperature, and weighing.
Compounds M1, M2, M3 were synthesized by the general procedure A3 to a 4:
Figure BDA0002187999850000113
the results are as follows:
of compound M1Yield 62%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):7.97(d,12H),7.75(m,12H),7.53(m,15H),6.72(m,3H),5.76(m,3H),5.25(d,3H)。
yield of compound M2 was 70%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):8.53(d,3H),8.13(s,3H),7.87(m,3H),7.77(m,3H),7.72(m,3H),7.54(m,6H),7.51(m,9H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
yield of compound M3 was 70%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):7.97(m,6H),7.87(m,3H),7.77(m,9H),7.72(m,6H),7.61(m,3H),7.54(m,6H),7.51(m,9H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
synthesis steps a4 to a 6:
Figure BDA0002187999850000121
under a nitrogen atmosphere, a raw material A4(5mmol) and a boric acid compound were added
Figure BDA0002187999850000122
(26mmol) and Pd as a catalyst2(dba)3(0.45mmol) with PCy3(0.90mmol) was dissolved in 1, 4-dioxane (200ml), an aqueous solution of potassium hydrogenphosphate (2.4M,12.5ml) was added to the solution, the mixture was heated to 100 ℃ and stirred under reflux for overnight reaction for 24 hours, and then the mixture was cooled to room temperature. After the reaction, the mixture was extracted with dichloromethane and dried. Separating and purifying with silica gel chromatographic column, eluting with dichloromethane/ethyl acetate, removing solvent by rotary evaporation, collecting product, vacuum drying at room temperature for 12 hr, and weighing.
Compounds M4, M5, M6 were synthesized by the general procedure a4 to a 7:
Figure BDA0002187999850000123
the results are as follows:
yield of compound M4 was 75%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):7.97(d,24H),7.77(m,9H),7.59(m,6H),7.53(m,6H),7.51(m,9H),6.72(d,3H),5.76(d,3H),5.25(d,3H)。
yield 80% of compound M5, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):8.53(d,3H),8.13(s,3H),7.97(d,12H),7.87(d,3H),7.87(m,3H),7.77(m,6H),7.74(m,3H),7.59(m,6H),7.53(m,6H),6.72(d,3H),5.76(d,3H),5.25(d,3H)。
yield 73% of compound M6, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):7.97(d,18H),7.77(m,6H),7.59(m,6H),7.53(m,6H),7.51(m,9H),6.72(d,3H),5.76(d,3H),5.25(d,3H)。
general synthetic procedures from a4 to A8:
Figure BDA0002187999850000131
under a nitrogen atmosphere, a raw material A4(5mmol) and a boric acid compound were added
Figure BDA0002187999850000132
(26mmol) and Pd as a catalyst2(dba)3(0.45mmol) with PCy3(0.90mmol) was dissolved in 1, 4-dioxane (200ml), an aqueous solution of potassium hydrogenphosphate (2.4M,12.5ml) was added to the solution, the mixture was heated to 100 ℃ and stirred under reflux for overnight reaction for 24 hours, and then the mixture was cooled to room temperature. After the reaction, the mixture was extracted with dichloromethane and dried. Separating and purifying with silica gel chromatographic column, eluting with dichloromethane/ethyl acetate, removing solvent by rotary evaporation, collecting product, vacuum drying at room temperature for 12 hr, and weighing.
Compounds M7, M8, M9 were synthesized by the general procedure a4 to a 8:
Figure BDA0002187999850000133
the results are as follows:
yield of compound M7 was 75%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):7.97(d,24H),7.77(m,6H),7.67(m,6H),7.61(m,6H),7.51(m,6H),7.23(d,6H),7.03(d,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H),5.14(s,6H)。
yield 80% of compound M8, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):8.53(d,3H),8.13(s,3H),7.97(d,12H),7.87(d,3H),7.87(m,3H),7.74(m,3H),7.67(m,6H),7.61(m,6H),7.23(m,6H),7.03(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H),5.14(s,6H)。
yield 73% of compound M9, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):7.97(d,18H),7.76(m,9H),7.67(m,6H),7.61(m,6H),7.51(m,9H),7.23(m,6H),7.03(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H),5.14(s,6H)。
secondly, the general synthetic route of the compound M10-M18 disclosed in the invention is as follows:
Figure BDA0002187999850000134
synthesis steps of B1 to B2:
under nitrogen atmosphere, at a low temperature of-78 ℃, n-butyllithium (2.5mol/l, 35mmol) is dropwise added into a THF solution of B1(10mmol), the reaction is stirred for 4h, then diphenyl phosphonium chloride (40mmol) is dropwise added, and the reaction is continued for 12 h. After the reaction, the mixture was extracted with dichloromethane and dried. Separating and purifying by using a silica gel chromatographic column, removing the solvent by using normal hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying in vacuum at room temperature for 12 hours, and weighing to obtain a reaction intermediate. Dissolving the intermediate in dichloromethane solution, and dropwise adding H under ice bath condition2O2(30%, 24ml) and reacted at this temperature for 2 h. And after the reaction is finished, extracting and separating by using dichloromethane, drying, separating and purifying by using a silica gel chromatographic column, removing the solvent by using n-hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying for 12 hours in vacuum at room temperature, and weighing.
Synthesis steps of B2 to B3:
under nitrogen atmosphere, a solution of liquid bromine (35mmol) in dichloromethane was dropwise added to a solution of B2(10mmol) in dichloromethane, the reaction was carried out under ice bath conditions, the reaction was gradually allowed to warm to room temperature, and the reaction was stirred for 24 hours. And after the reaction is finished, extracting and separating by using dichloromethane, drying, separating and purifying by using a silica gel chromatographic column, removing the solvent by using normal hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying in vacuum at room temperature for 12 hours, weighing, and controlling the yield to be about 35%.
Synthesis steps of B3 to B4:
Figure BDA0002187999850000141
under a nitrogen atmosphere, the raw material B3(5mmol) and tributylvinyltin were added
Figure BDA0002187999850000142
(16mmol) with palladium tetratriphenylphosphine Pd (PPh) as catalyst3)4(0.15mmol) was dissolved in dimethylformamide DMF (45ml), the mixture was heated to 130 ℃ and stirred for 24 hours, then cooled to room temperature and quenched by the addition of water. And after the reaction is finished, extracting and separating by using dichloromethane, drying, separating and purifying by using a silica gel chromatographic column, removing the solvent by using n-hexane/dichloromethane as an eluent through rotary evaporation, collecting a product, finally drying for 12 hours in vacuum at room temperature, and weighing.
Compounds M10, M11, M12 were synthesized by the general procedure of B3 to B4:
Figure BDA0002187999850000143
the results are as follows:
yield of material M10 71%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):9.49(s,3H),9.22(s,3H),8.62(s,3H),8.04(s,3H),7.75(m,12H),7.53(m,15H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
yield of material M11 was 70%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):9.13(s,3H),8.29(d,3H),8.10(d,3H),8.04(s,3H),7.75(m,12H),7.53(m,15H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
yield of material M12 was 72%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):9.44(s,3H),8.64(d,3H),8.10(d,6H),8.04(s,3H),7.75(m,12H),7.53(m,15H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
synthesis steps of B3 to B5:
Figure BDA0002187999850000151
under a nitrogen atmosphere, a raw material B3(5mmol) and a boric acid compound were added
Figure BDA0002187999850000152
(26mmol) and Pd as a catalyst2(dba)3(0.45mmol) with PCy3(0.90mmol) was dissolved in 1, 4-dioxane (200ml), an aqueous solution of potassium hydrogenphosphate (2.4M,12.5ml) was added to the solution, the mixture was heated to 100 ℃ and stirred under reflux for overnight reaction for 24 hours, and then the mixture was cooled to room temperature. After the reaction, the mixture was extracted with dichloromethane and dried. Separating and purifying with silica gel chromatographic column, eluting with dichloromethane/ethyl acetate, removing solvent by rotary evaporation, collecting product, vacuum drying at room temperature for 12 hr, and weighing.
Compounds M13, M14, M15 were synthesized by the general procedure of B3 to B5:
Figure BDA0002187999850000153
the results are as follows:
yield 78% of compound M13, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):9.49(s,3H),9.22(s,3H),8.62(s,3H),8.04(s,3H),7.97(m,12H),7.77(m,6H),7.59(m,6H),7.53(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
yield of compound M14 was 75%, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):9.13(s,3H),8.29(d,3H),8.10(d,3H),8.04(s,3H),7.97(m,12H),7.77(m,6H),7.59(m,6H),7.52(m,15H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
yield 73% of compound M15, assay data:1H NMR(500MHz,CDCl3),(TMS,ppm):9.44(s,3H),8.64(d,3H),8.10(d,3H),8.04(s,3H),7.97(d,12H),7.77(m,6H),7.59(m,6H),7.53(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
synthesis steps of B3 to B6:
Figure BDA0002187999850000161
under a nitrogen atmosphere, a raw material B3(5mmol) and a boric acid compound were added
Figure BDA0002187999850000162
(26mmol) and Pd as a catalyst2(dba)3(0.45mmol) with PCy3(0.90mmol) was dissolved in 1, 4-dioxane (200ml), an aqueous solution of potassium hydrogenphosphate (2.4M,12.5ml) was added to the solution, the mixture was heated to 100 ℃ and stirred under reflux for overnight reaction for 24 hours, and then the mixture was cooled to room temperature. After the reaction, the mixture was extracted with dichloromethane and dried. Separating and purifying with silica gel chromatographic column, eluting with dichloromethane/ethyl acetate, removing solvent by rotary evaporation, collecting product, vacuum drying at room temperature for 12 hr, and weighing.
Compounds M16, M17, M18 were synthesized by the general procedure of B3 to B6:
Figure BDA0002187999850000163
the results are as follows:
yield of compound M16 was 75%, as a result of detection1H NMR(500MHz,CDCl3),(TMS,ppm):9.49(s,3H),9.22(s,3H),8.62(s,3H),8.04(s,3H),7.97(m,12H),7.77(m,6H),7.67(m,6H),7.61(m,6H),7.59(m,6H),7.23(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H)。
77% yield of material M17, test result1H NMR(500MHz,CDCl3),(TMS,ppm):9.13(s,3H),8.29(d,3H),8.10(d,3H),8.04(s,3H),7.97(m,12H),7.77(m,6H),7.67(m,6H),7.61(m,6H),7.51(m,9H),7.23(m,6H),7.03(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H),5.14(d,6H)。
Yield of material M18 was 72%, test result1H NMR(500MHz,CDCl3),(TMS,ppm):9.44(s,3H),8.64(d,3H),8.10(d,3H),8.04(s,3H),7.97(m,12H),7.77(m,6H),7.67(m,6H),7.61(m,6H),7.51(m,9H),7.23(m,6H),7.03(m,6H),6.72(m,3H),5.76(d,3H),5.25(d,3H),5.14(d,6H)。
Three, organic light emitting diode device
As shown in fig. 1, the structure is: the organic light emitting device includes a substrate 11, a first electrode 12 formed on the substrate 11, an electron injection layer 13 formed on the first electrode 12, an electron transport layer 14 formed on the electron injection layer 13, a light emitting layer 15 formed on the electron transport layer 14, a hole transport layer 16 formed on the light emitting layer 15, a hole injection layer 17 formed on the hole transport layer 16, and a second electrode 18 on the hole injection layer 17. The electron transport layer 14 or the light-emitting layer 15 contains a crosslinked compound formed by a crosslinking reaction of the electron transport material. In addition, the organic light emitting diode device may further form a hole blocking layer between the light emitting layer 15 and the electron transport layer 14, and/or an electron blocking layer between the light emitting layer 15 and the hole transport layer 16.
Preparation example of a specific organic light emitting diode device:
firstly, the ITO substrate is cleaned according to the following sequence: 5% KOH solution is subjected to ultrasonic treatment for 15min, pure water is subjected to ultrasonic treatment for 15min, isopropanol is subjected to ultrasonic treatment for 15min, and the mixture is dried in an oven for 1 h; then transferring the ITO substrate to UV-ZONE equipment for surface treatment for 15min, and immediately transferring the ITO substrate to a glove box after the surface treatment;
spin-coating a layer of ZnO nanoparticles on a clean ITO substrate, and then baking for 15min at the temperature of 120 ℃ to form an electron injection layer (ZnO nano layer);
dissolving the electron transport material by using a solvent (such as o-dichlorobenzene or dimethyl sulfoxide), spinning a functional layer material solution containing the electron transport material on the ZnO nano layer, spinning the electron transport layer material, baking at 120 ℃ for 10min to remove residual solvent, and then crosslinking the phosphorus-oxygen-based derivative with the vinyl end at 230 ℃ for 30-60 min to form an electron transport layer;
after spin-coating the ink of the light-emitting layer, evaporating an electron blocking layer, a hole transport layer, a hole injection layer and an anode in a vacuum evaporation mode;
and finally, carrying out UV curing packaging, and heating and baking for 20min to prepare the device.
The specific organic matterStructure of light emitting diode device: ITO/ZnO (35nm)/crosslink-M (20nm)/mCP Ir (ppy)2acac,7 wt% (30nm)/TAPC (30nm)/NPB (10nm)/HAT-CN (10nm)/Al (120 nm). Wherein ZnO is used as electron injection layer, cross-linked electron transport material crosslink-M is used as electron transport layer, mCP is used as host material in luminescent layer, Ir (ppy)2acac is used as a guest material, TAPC is used as a hole transport layer and an electron blocking layer, NPB is used as a hole transport layer, HAT-CN is used as a hole injection layer material, and Al is used as an anode.
Example 1:
the compound M2 is used as a cross-linking host material (crosslink-M), and the organic light-emitting diode device 1 is prepared according to the preparation method of the organic light-emitting diode device.
Examples 2 to 6:
the organic light emitting diode devices 2 to 6 were prepared according to the above-described method for preparing organic light emitting diode devices, using the compounds M5, M8, M10, M13, and M16 as cross-linking host materials (crosslink-M), respectively.
The prepared devices were tested for their luminescence properties by an IV-L test system using a machine model of F-star CS2000A instrument.
The performance of the organic light emitting diode device was examined as shown in table 1:
TABLE 1
Device numbering Maximum current efficiency (cd/A) (CIEx,CIEy)
1 75 (0.30,0.65)
2 80 (0.30,0.65)
3 65 (0.30,0.65)
4 53 (0.30,0.65)
5 62 (0.30,0.65)
6 68 (0.30,0.65)
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (13)

1. An organic compound having the formula:
Figure FDA0002187999840000011
wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
plural R2Each independently selected from a vacancy, an aromatic ring group with an alkyl chain, an aromatic ring group without an alkyl chain, an aromatic ring group with an alkoxy chain, an aromatic ring group without an alkoxy chain, or an aromatic ring group without an alkoxy chain.
2. The organic compound of claim 1, wherein Ar is Ar1Selected from phenyl, a fused ring aromatic group, or an aromatic heterocyclic group containing nitrogen atoms on the ring.
3. The organic compound of claim 1, wherein R is1Is selected from phenyl, condensed ring aromatic group, biphenyl group, aromatic heterocyclic group containing nitrogen atom on the ring, group formed by connecting aromatic heterocyclic group with nitrogen atom on the ring and aromatic heterocyclic group or group formed by connecting aromatic heterocyclic group with nitrogen atom on the ring and aromatic ring group.
4. The organic compound of claim 1, wherein R is2The compound is selected from a vacancy, a biphenyl group, a group formed by connecting a biphenyl group with a benzene ring through an alkyl chain or an alkoxy chain of C1-C8, a group formed by connecting a biphenyl group with a biphenyl group through an alkyl chain or an alkoxy chain of C1-C8 or a group formed by connecting two benzene rings through an alkyl chain or an alkoxy chain of C1-C8.
5. The organic compound of any one of claims 1-4, wherein Ar is Ar1Is an aromatic heterocyclic group, R1Selected from aromatic or heteroaromatic radicalsClustering; or
Ar1Is an aromatic ring radical, R1Is an aromatic heterocyclic group.
6. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of compounds of the following structural formulae M1-M18:
Figure FDA0002187999840000021
Figure FDA0002187999840000031
Figure FDA0002187999840000041
7. the organic compound of claim 6, wherein the organic compound is selected from one of the compounds represented by the following structural formulae:
Figure FDA0002187999840000042
Figure FDA0002187999840000051
8. a method for producing an organic compound, comprising the steps of:
in the compound
Figure FDA0002187999840000052
Introduction of group(s) thereon
Figure FDA0002187999840000053
Formation of the target Compound
Figure FDA0002187999840000061
Wherein Ar is1And a plurality of R1Each independently selected from an aromatic ring group or an aromatic heterocyclic group;
plural R2Each independently selected from a vacancy, an aromatic ring group with an alkyl chain, an aromatic ring group without an alkyl chain, an aromatic ring group with an alkoxy chain, an aromatic ring group without an alkoxy chain, or an aromatic ring group without an alkoxy chain.
9. The method of claim 8, wherein R is2In the form of a vacancy, in which radicals are introduced
Figure FDA0002187999840000062
When the compound is mixed
Figure FDA0002187999840000063
Reacting with tributylvinyltin; or
R2Selected from aromatic or heteroaromatic groups with or without alkyl or alkoxy chains, in which groups are introduced
Figure FDA0002187999840000064
When the compound is mixed
Figure FDA0002187999840000065
And compounds
Figure FDA0002187999840000066
And (4) reacting.
10. An electronic device comprising a crosslinked compound formed by crosslinking reaction of the organic compound according to any one of claims 1 to 7.
11. The electronic device of claim 10, wherein the electronic device is an organic light emitting diode, a quantum dot light emitting diode, an organic thin film photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, or an organic plasmon emitting diode.
12. A method for producing an electronic device, comprising depositing a functional material solution containing the organic compound according to any one of claims 1 to 7 on a substrate, drying to remove the solvent, and heating to cause a crosslinking reaction of the vinyl-terminated organic compound to form a functional layer.
13. The method for producing an electronic device according to claim 12, wherein the crosslinking reaction is a crosslinking reaction of the organic compound having a vinyl group at a terminal at 200 to 300 ℃ for 30 to 60 minutes.
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