CN110713486A - Pyrimidine derivative with self-assembly characteristic, preparation method and application thereof - Google Patents
Pyrimidine derivative with self-assembly characteristic, preparation method and application thereof Download PDFInfo
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Abstract
The pyrimidine derivative with the self-assembly characteristic has high fluorescence quantum yield and the property of thermal activation delayed fluorescence, so that the pyrimidine derivative can be used as a material of an organic electroluminescent device, and particularly can be used as a high-efficiency orange-red non-doped fluorescent agent. The organic electroluminescent device formed by the non-doped fluorescent agent has the characteristics of low driving voltage, low efficiency roll-off, high efficiency and the like. Therefore, the pyrimidine derivative of the present invention can be used as a component of an organic electroluminescent device which can be driven at a low voltage, has high efficiency and low roll-off efficiency.
Description
Technical Field
The invention relates to a pyrimidine derivative with self-assembly characteristics, a preparation method and application, and belongs to the technical field of organic chemistry.
Background
Organic electroluminescent devices (OLEDs) have a great application prospect in the fields of display and white light illumination because of their characteristics of all solid state, self-luminescence, wide viewing angle, low energy consumption, low driving voltage, and the like. However, under the condition of electro-excitation, the generation ratio of singlet/triplet excitons is 1:3, so that the conventional fluorescent material can only achieve 25% of internal quantum yield (IQE). Although phosphorescent materials can theoretically achieve IQE close to 100%, the use of noble metals is a disadvantage that it cannot avoid. Thermal activated delayed-mechanism fluorescent materials (TADFs) have been the focus of research because they can up-convert 75% of triplet excitons to singlet excitons at room temperature to obtain theoretically 100% of IQE.
Most of the TADF materials adopt a host-guest doping system to improve the performance of OLEDs, which is to reduce exciton quenching and efficiency roll-off caused by high-concentration triplet excitons. However, the doping system not only increases the complexity of the device, but also presents challenges to precisely controlling the doping ratio. Therefore, undoped devices based on TADF materials are the most desirable target. Among them, the orange and red TADF material is an important component of white light illumination, but due to the influence of non-radiative transition, the high-efficiency orange and red TADF material which can be used for non-doped OLED is a difficult point of research.
Disclosure of Invention
In order to solve the defects and shortcomings in the prior art, the invention provides the pyrimidine derivative which can be used as a non-doped light-emitting layer of an organic electroluminescent device, can be driven by low voltage and can endow the organic electroluminescent device with high efficiency and low efficiency roll-off, and the preparation method thereof.
In order to solve the above technical problems, the present invention provides a pyrimidine derivative having a self-assembly property. The pyrimidine derivative is represented by the following general formula (1).
[ chemical formula 1 ]
In the formula (1), Ar1，Ar2At least one substituent containing an electron-deficient pyridine, R isAn electron rich aromatic amine substituent containing at least one nitrogen, and the amine nitrogen and the pyrimidine group are directly linked through a benzene ring.
Further, Ar1，Ar2Respectively phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidinyl, 3, 5-pyrimidinyl, 2, 3-pyridazinyl or 2, 5-pyrazinyl, wherein 3-pyridyl or 3, 5-pyrimidinyl is a preferred group.
In addition, the invention also provides a preparation method of the pyrimidine derivative shown in the general formula (1), and according to the situation, in the presence of the first alkali solution and the palladium catalyst, the pyrimidine derivative shown in the formula (3) and the electron-rich aromatic substituent containing at least one nitrogen are subjected to coupling reaction.
Further, the first alkaline solution is potassium tert-butoxide, sodium tert-butoxide or sodium ethoxide; the palladium catalyst is palladium salt or a palladium complex, the palladium salt is one of palladium chloride, palladium acetate, palladium trifluoroacetate or palladium nitrate, and a ligand of the palladium complex is tri-tert-butylphosphine, acetylacetone or dichloro (bistriphenylphosphine); the molar ratio of the palladium catalyst to the compound represented by the formula (3) is 1: 10-50 parts of; the molar ratio of the compound shown in the formula (3) to the compound shown in the formula (2) is 1-5: 1; the solvent used in the reaction is toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide or dimethylformamide.
[ chemical formula 2 ]
In the formula (2), R1Is oxygen atom, sulfur atom, methylene, diphenylmethylene or dimethylmethylene, wherein oxygen atom or sulfur atom is a preferred group;
[ chemical formula 3 ]
In the formula (3), Ar1，Ar2Is at least one pyridine substituent containing an electron deficiency, and x is a leaving group;Ar1and Ar2Respectively phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidinyl, 3, 5-pyrimidinyl, 2, 3-pyridazinyl or 2, 5-pyrazinyl, wherein 3-pyridyl or 3, 5-pyrimidinyl is a preferred group; x is a chlorine atom, a bromine atom or an iodine atom.
The present invention also provides a process for producing a pyrimidine derivative represented by the general formula (3), wherein a compound represented by the formula (4) is subjected to a cycloreaction with a compound represented by the formula (5) in the presence of a second alkali solution.
Further, the second alkaline solution is potassium carbonate, sodium hydroxide, potassium hydroxide and cesium carbonate; the molar ratio of the second alkaline solution to the compound shown in the formula (4) is 1-10: 1; the molar ratio of the compound shown in the formula (4) to the compound shown in the formula (5) is 1: 1-2; the solvent used in the reaction is methanol, ethanol, toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide or dimethylformamide.
[ chemical formula 4 ]
In the formula (4), Ar1Is an aromatic compound, and x is a leaving group; preferably, Ar1Is phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidinyl, 3, 5-pyrimidinyl, 2, 3-pyridazinyl or 2, 5-pyrazinyl, wherein 3-pyridyl or 3, 5-pyrimidinyl is a preferred group; x is a chlorine atom, a bromine atom or an iodine atom.
[ chemical formula 5 ]
In the formula (5), Ar2Is an aromatic compound, such as phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidinyl, 3, 5-pyrimidinyl, 2, 3-pyridazinyl or 2, 5-pyrazinyl, with 3-pyridyl or 3, 5-pyrimidinyl being preferred groups.
The invention also provides application of the pyrimidine derivative with the self-assembly characteristic in an organic electroluminescent device.
The invention achieves the following beneficial technical effects: the pyrimidine derivative provided by the invention has high fluorescence quantum yield and the property of thermal activation delayed fluorescence, so that the pyrimidine derivative can be used as a material of an organic electroluminescent device, and especially can be used as a non-doped orange and red fluorescent agent. The organic electroluminescent device formed by the non-doped fluorescent agent has the characteristics of low driving voltage, low efficiency roll-off, high efficiency and the like. Therefore, the pyrimidine derivative of the present invention can be used as a component of an organic electroluminescent device which can be driven at a low voltage, has high efficiency and low roll-off efficiency.
Drawings
FIG. 1 is a schematic cross-sectional view showing the application of the pyrimidine derivative having self-assembly characteristics according to the present invention to an organic electroluminescent device.
Wherein, 1 a glass substrate; 2 a hole transport layer; 3 an electron blocking layer; 4 a light emitting layer; 5 an electron transport layer; 6 cathode layer.
Detailed Description
The invention is further described with reference to specific examples. The following examples are only for illustrating the technical solutions of the present invention more clearly, and the protection scope of the present invention is not limited thereby.
Example 1: synthesis of 4-phenyl- (2, 6-bis-3-pyridyl-1, 3-pyrimidyl) -phenoxazine
Synthesis of intermediate 1: adding a magnetic stirrer into a 100ml single-mouth eggplant-shaped bottle, sequentially adding 0.92g of p-bromobenzaldehyde, 0.60ml of 3-acetylpyridine and 40ml of methanol, stirring to completely dissolve the mixture, then adding 2ml of 10% NaOH aqueous solution, stirring at room temperature for 1 hour, filtering under reduced pressure, washing a filter cake with methanol and deionized water sequentially, and drying in vacuum to obtain a light green solid intermediate 1, wherein the yield is 1.31g, the yield is 90.1%, and the product is directly subjected to the next reaction without further purification.
Synthesis of intermediate 2: adding a magnetic stirrer into a 100ml single-mouth eggplant-shaped bottle, sequentially adding 11.4 g of an intermediate, 0.72g of pyridine-3-formamidine hydrochloride, 0.76g of potassium hydroxide and 50ml of ethanol, heating to reflux, reacting overnight, filtering under reduced pressure, sequentially washing a filter cake with ethanol and deionized water, and drying in vacuum to obtain a white solid intermediate 2, wherein the yield is 0.80g, the yield is 45.2%, and the product is directly subjected to the next reaction without further purification.
Synthesis of example 1: under the protection of argon, 0.78g of 4-bromophenyl terpyridine derivative (intermediate 2), 0.40g of phenoxazine, 15mg of palladium acetate and 0.5mL of 10% tri-tert-butylphosphine solution in toluene were added to a 100mL two-port reactor equipped with a reflux tube, and 60mL of toluene was added. The resulting solution was heated to 90 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and methylene chloride and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using methylene chloride and methanol. After drying, 500mg of an orange powder was obtained in 50.8% yield.
And (3) product characterization:1H NMR(600MHz,Chloroform-d)δ9.93(d,J＝1.9Hz,1H),9.48(d,J＝2.2Hz,1H),9.06(d,J＝7.9Hz,1H),8.81(ddd,J＝15.6,4.8,1.7Hz,2H),8.64(dt,J＝8.2,1.9Hz,1H),8.51(d,J＝8.4Hz,2H),8.16(s,1H),7.59(d,J＝8.4Hz,2H),7.56(dd,J＝7.8,4.8Hz,1H),6.73(dd,J＝7.9,1.5Hz,2H),6.68(td,J＝7.6,1.5Hz,2H),6.62(td,J＝7.7,1.6Hz,2H),6.03(dd,J＝8.0,1.5Hz,2H).13c NMR (151MHz, Chloroform-d) delta 164.57,163.62,163.09,162.72,158.60,151.91,148.86,148.46,143.98,142.14,136.98,136.56,134.91,133.88,133.71,132.51,131.64,130.08,123.94,123.27,121.72,115.66,113.27,111.24 molecular formula C33H22N4O([M]+):m/z 491.55.Found:m/z 491.20.
Example 2: synthesis of 4-phenyl- (2- (3-pyridyl) -6- (3, 5-pyrimidyl) -1, 3-pyrimidyl) -phenoxazine
Synthesis of intermediate 3: a magnetic stirrer is added into a 100ml single-mouth eggplant-shaped bottle, then 0.92g of p-bromobenzaldehyde is sequentially added,5-acetyl pyrimidine 0.67g and 40ml methanol, stirring to dissolve completely, adding 5ml 10% Na2CO3And (3) stirring the aqueous solution at room temperature for 1 hour, filtering under reduced pressure, washing a filter cake by using methanol and deionized water in sequence, and drying in vacuum to obtain a light yellow solid intermediate 3, wherein the yield is 1.0g, the yield is 69.0%, and the product is directly subjected to the next reaction without further purification.
Synthesis of intermediate 4: adding a magnetic stirrer into a 100ml single-mouth eggplant-shaped bottle, sequentially adding 31.4 g of an intermediate, 0.78g of pyridine-3-formamidine hydrochloride, 0.76g of potassium hydroxide and 50ml of ethanol, heating to reflux, reacting overnight, filtering under reduced pressure, sequentially washing a filter cake with ethanol and deionized water, and drying in vacuum to obtain a white solid intermediate 4, wherein the yield is 0.40g, the yield is 20.0%, and the product is directly subjected to the next reaction without further purification.
Synthesis of example 2: under the protection of argon, 0.78g of 4-bromophenyl pyrimidine derivative (intermediate 4), 0.40g of phenoxazine, 15mg of palladium acetate, 0.5mL of 10% toluene solution of tri-tert-butylphosphine, and 60mL of toluene were added to a 100mL two-port reactor equipped with a reflux tube. The resulting solution was heated to 90 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and methylene chloride and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using methylene chloride and methanol. After drying, 300mg of orange powder was obtained, yield 30.5%.
And (3) product characterization:1H NMR(600MHz,Chloroform-d)δ9.90(dd,J＝2.2,0.9Hz,1H),9.60(s,2H),9.42(s,1H),8.94(dt,J＝8.0,1.9Hz,1H),8.80(d,J＝4.8Hz,1H),8.52(d,J＝8.4Hz,2H),8.13(s,1H),7.60(d,J＝8.4Hz,2H),7.51(ddd,J＝8.0,4.8,0.9Hz,1H),6.73(dd,J＝7.9,1.6Hz,2H),6.69(td,J＝7.6,1.4Hz,2H),6.62(ddd,J＝8.0,7.3,1.6Hz,2H),6.03(dd,J＝8.0,1.4Hz,2H).13C NMR(151MHz,cdcl3) Delta 164.84,163.67,160.53,160.30,155.60,151.96,150.21,143.98,142.33,136.34,135.76,133.84,132.67,131.69,130.44,130.10,123.48,123.27,121.76,115.69,113.26,110.84, formula C31H20N6O([M]+):m/z492.54.Found:m/z 492.23.
Example 3: synthesis of 4-phenyl- (2, 6-bis (3, 5-pyrimidinyl) -1, 3-pyrimidinyl) -phenoxazine
Synthesis of intermediate 5: adding a magnetic stirrer into a 100ml single-mouth eggplant-shaped bottle, sequentially adding 31.4 g of an intermediate, 0.78g of pyrimidine-5-formamidine hydrochloride, 0.76g of potassium hydroxide and 50ml of ethanol, heating to reflux, reacting overnight, filtering under reduced pressure, sequentially washing a filter cake with ethanol and deionized water, and drying in vacuum to obtain the intermediate 5 which is a white solid, wherein the yield is 0.30g, the yield is 15.0%, and the product is directly subjected to the next reaction without further purification.
Synthesis of example 3: under the protection of argon, 0.78g of 4-bromophenyl pyrimidine derivative (intermediate 5), 0.40g of phenoxazine, 15mg of palladium acetate, 0.5mL of 10% toluene solution of tri-tert-butylphosphine, and 60mL of toluene were added to a 100mL two-port reactor equipped with a reflux tube. The resulting solution was heated to 90 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and methylene chloride and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using methylene chloride and methanol. After drying, 300mg of red powder was obtained with a yield of 30.5%. And (3) product characterization:1h NMR (600MHz, Chloroform-d) δ 9.93(s,2H),9.59(s,2H),9.41(d, J ═ 15.4Hz,2H),8.51(d, J ═ 8.4Hz,2H),8.18(s,1H),7.61(d, J ═ 8.4Hz,2H),6.73(dd, J ═ 7.9,1.5Hz,2H),6.69(td, J ═ 7.6,1.4Hz,2H),6.62(td, J ═ 7.7,1.6Hz,2H),6.03(dd, J ═ 8.0,1.4Hz,2H), formula C31H20N6O([M]+):m/z 492.54.Found:m/z 492.33.
Example 4: synthesis of 4-phenyl- (4- (2, 6-bipyrazinyl) pyridine) -phenothiazine
Synthesis of example 4: under the protection of argon, 0.78g of 4-bromophenyl terpyridine derivative (intermediate 2), 0.42g of phenothiazine, 15mg of palladium acetate, 0.5mL of a 10% toluene solution of tri-tert-butylphosphine, and 60mL of toluene were added to a 100mL two-port reactor equipped with a reflux tube. The resulting solution was heated to 90 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and methylene chloride and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using methylene chloride and methanol. After drying, 490mg of an orange powder was obtained in 48.6% yield.
And (3) product characterization:1h NMR (600MHz, Chloroform-d) δ 9.90(d, J ═ 1.9Hz,1H),9.49(d, J ═ 2.2Hz,1H),9.03(d, J ═ 7.9Hz,1H),8.80(ddd, J ═ 15.6,4.8,1.7Hz,2H),8.63(dt, J ═ 8.2,1.9Hz,1H),8.50(d, J ═ 8.4Hz,2H),8.17(s,1H),7.58(d, J ═ 8.4Hz,2H),7.56(dd, J ═ 7.8,4.8Hz,1H),6.75(dd, J ═ 7.9,1.5, 2H),6.63 (J ═ 6.5, 6.59, 6.6, 6.5, 8, 1H), td ═ 8.5, 1H, 6.5, 1H, 6.5, 1H32H21N5OS([M]+):m/z 507.15.Found:m/z507.20.
The invention also provides application of the pyrimidine derivative with self-assembly capability in an organic non-doped electroluminescent device.
Firstly, the products of the following example 1 are applied to the manufacture and performance evaluation of an organic electroluminescent device of orange fluorescent non-doped dye:
a glass plate with ITO transparent electrodes in stripe form patterned with a 2mm wide Indium Tin Oxide (ITO) film was used as a substrate. After the glass substrate was washed with isopropyl alcohol, surface treatment was performed by ozone ultraviolet rays. Vacuum deposition of each layer was performed on the cleaned substrate by vacuum deposition to produce a light-emitting area 9mm as shown in FIG. 1 in a cross-sectional view2The organic electroluminescent device of (1).
First, the glass substrate is introduced into a vacuum evaporation tank and reduced in pressure to 1X 10-4Pa. Then, on the glass substrate shown in fig. 1, a hole transport layer 2, an electron blocking layer 3, a light emitting layer 4, and an electron transport layer 5 are formed in this order as organic compound layers, and then a cathode layer 6 is formed. 4,4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline vacuum-evaporated in a film thickness of 40nm](TAPC) as hole transport layer2, 4' -tris (carbazol-9-yl) triphenylamine (TCTA) vacuum-deposited with a thickness of 10nm as an electron blocking layer 3, the compound synthesized in example 1 was vacuum-deposited with a thickness of 20nm as a light emitting layer 4, and 3,3' - [5' - [3- (3-pyridyl) phenyl ] vacuum-deposited with a thickness of 45nm as a light emitting layer 4][1,1':3', 1' -terphenyl]-3,3 "-diyl]Bipyridine (TmPyPb) was used as the electron transport layer 5. Wherein each organic material is formed into a film by means of resistance heating. Heating the compound to vacuum-evaporate at a film forming rate of 0.3-0.5 nm. Finally, a metal mask is disposed so as to be orthogonal to the ITO stripes, thereby forming a film cathode 6. The cathode layer 6 has a two-layer structure formed by vacuum-depositing lithium fluoride and aluminum in film thicknesses of 1nm and 100nm, respectively. Each film thickness was measured by a stylus type film thickness measuring instrument (DEKTAK). Further, the device was sealed in a nitrogen atmosphere glove box containing water and oxygen at a concentration of 1ppm or less. The sealing was carried out by using a vitreous sealing cap and the above film-forming substrate epoxy ultraviolet curable resin (manufactured by Nagase ChemteX Corporation).
The prepared organic electroluminescent device was subjected to direct current application, evaluated for light emission performance using a Spectrascan PR650 luminance meter, and measured for current-voltage characteristics using a computer-controlled Keithley 2400 digital source meter. As the light emission characteristics, CIE color coordinate values and maximum luminance (cd/m) were measured under the change of applied DC voltage2) External quantum efficiency (%), power efficiency (lm/W). The measured values of the fabricated devices were (0.50,0.49), 35640cd/m218.8% and 53.5 lm/W.
Secondly, the product of the embodiment 2 is applied to the manufacture and performance evaluation of the organic electroluminescent device of the red fluorescent non-doped dye:
the prepared organic electroluminescent device was subjected to direct current application, evaluated for light emission performance using a Spectrascan PR650 luminance meter, and measured for current-voltage characteristics using a computer-controlled Keithley 2400 digital source meter. As the light emission characteristics, CIE color coordinate values and maximum luminance (cd/m) were measured under the change of applied DC voltage2) External quantum efficiency (%), power efficiency (lm/W). The measured values of the fabricated devices were (0.56,0.44), 24750cd/m211.3% and 22.1 lm/W.
In conclusion, the pyrimidine derivative with self-assembly capability provided by the invention is applied to an organic electroluminescent device, and can effectively simplify the structure of the device, reduce power consumption and improve luminous efficiency. The pyrimidine derivative having self-assembly ability according to the present invention can be applied to various organic electroluminescent devices such as fluorescent light-emitting materials and phosphorescent light-emitting materials, and can be applied to applications such as flat panel displays and lighting applications where both low power consumption and high efficiency are achieved.
The present invention has been disclosed in terms of the preferred embodiment, but is not intended to be limited to the embodiment, and all technical solutions obtained by substituting or converting equivalents thereof fall within the scope of the present invention.
Claims (9)
1. A pyrimidine derivative having a self-assembly property, having a structural formula represented by formula (1):
in the formula (1), Ar1，Ar2Is at least one electron deficient pyridine substituent, R comprises at least one electron rich aromatic amine substituent of nitrogen, and the amine nitrogen and the pyrimidine group are directly connected through a benzene ring.
2. A pyrimidine derivative according to claim 1, wherein:
Ar1and Ar2Respectively phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyridazinyl and 2, 5-pyrazinyl.
3. A process for preparing a pyrimidine derivative according to claim 1, wherein: carrying out coupling reaction on a compound with a structure shown in a formula (3) and a compound with a structure shown in a formula (2) in the presence of an alkaline solution I and a palladium catalyst to obtain a compound with a structure shown in a formula (1);
in the above formula (2), R1Is oxygen atom, sulfur atom, methylene, diphenylmethylene or dimethylmethylene;
in the above formula (3), Ar1And Ar2Respectively at least one pyridine substituent containing an electron deficiency, and x is a leaving group.
4. The production method according to claim 3, characterized in that: ar (Ar)1And Ar2Respectively phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidinyl, 3, 5-pyrimidinyl, 2, 3-pyridazinyl or 2, 5-pyrazinyl; x is a chlorine atom, a bromine atom or an iodine atom.
5. The production method according to claim 3, characterized in that: the first alkaline solution is potassium tert-butoxide, sodium tert-butoxide or sodium ethoxide; the palladium catalyst is palladium salt or a palladium complex, the palladium salt is palladium chloride, palladium acetate, palladium trifluoroacetate or palladium nitrate, and a ligand of the palladium complex is tri-tert-butylphosphine, acetylacetone or dichloro (bistriphenylphosphine); the molar ratio of the palladium catalyst to the compound represented by the formula (3) is 1: 10-50 parts of; the molar ratio of the compound shown in the formula (3) to the compound shown in the formula (2) is 1-5: 1; the solvent used in the reaction is toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide or dimethylformamide.
6. The production method according to claim 3, characterized in that: under the condition of an alkaline solution II, reacting a compound shown as a formula (4) with a compound shown as a formula (5) to obtain a compound shown as a formula (3);
in the formula (4), Ar1Is an aromatic compound, and x is a leaving group; in the formula (5), Ar2Is an aromatic compound.
7. The method of claim 6, wherein: the second alkaline solution is potassium carbonate, sodium hydroxide, potassium hydroxide or cesium carbonate; the molar ratio of the second alkaline solution to the compound shown in the formula (4) is 1-10: 1; the molar ratio of the compound shown in the formula (4) to the compound shown in the formula (5) is 1: 1-2; the solvent used in the reaction is ethanol, methanol, toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide or dimethylformamide.
8. The method of claim 6, wherein: ar (Ar)1And Ar2Respectively is phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyridazinyl and 2, 5-pyrazinyl; x is a chlorine atom, a bromine atom or an iodine atom.
9. Use of a pyrimidine derivative having self-assembly characteristics as set forth in claim 1 in an organic electroluminescent device.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113278018A (en) * | 2020-02-20 | 2021-08-20 | 苏州大学 | Pyridine-based thermally activated delayed fluorescent material and application thereof |
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| CN1701111A (en) * | 2002-03-22 | 2005-11-23 | 出光兴产株式会社 | Material for organic electroluminescent device and organic electroluminescent device using the same |
| WO2011013843A1 (en) * | 2009-07-31 | 2011-02-03 | Fujifilm Corporation | Organic electroluminescence device |
| US20120168730A1 (en) * | 2009-06-19 | 2012-07-05 | Doosan Corporation | Acridine derivative and organic electroluminescence device including the same |
| US20160028025A1 (en) * | 2013-03-18 | 2016-01-28 | Idemitsu Kosan Co., Ltd. | Light-emitting device |
| US20170148999A1 (en) * | 2014-05-02 | 2017-05-25 | Samsung Display Co., Ltd. | Organic light-emitting device |
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| CN1701111A (en) * | 2002-03-22 | 2005-11-23 | 出光兴产株式会社 | Material for organic electroluminescent device and organic electroluminescent device using the same |
| US20120168730A1 (en) * | 2009-06-19 | 2012-07-05 | Doosan Corporation | Acridine derivative and organic electroluminescence device including the same |
| WO2011013843A1 (en) * | 2009-07-31 | 2011-02-03 | Fujifilm Corporation | Organic electroluminescence device |
| US20160028025A1 (en) * | 2013-03-18 | 2016-01-28 | Idemitsu Kosan Co., Ltd. | Light-emitting device |
| US20170148999A1 (en) * | 2014-05-02 | 2017-05-25 | Samsung Display Co., Ltd. | Organic light-emitting device |
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| CN113278018A (en) * | 2020-02-20 | 2021-08-20 | 苏州大学 | Pyridine-based thermally activated delayed fluorescent material and application thereof |
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