CN112266385B - Pyridoimidazo pyrrole compound and application thereof - Google Patents

Pyridoimidazo pyrrole compound and application thereof Download PDF

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CN112266385B
CN112266385B CN202011091847.7A CN202011091847A CN112266385B CN 112266385 B CN112266385 B CN 112266385B CN 202011091847 A CN202011091847 A CN 202011091847A CN 112266385 B CN112266385 B CN 112266385B
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nitrogen atom
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刘凯鹏
孙军
张宏科
杨丹丹
田密
何海晓
李江楠
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Xi'an Manareco New Materials Co ltd
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Abstract

The invention provides a pyrido-imidazo-pyrrole compound, belonging to the technical field of organic electroluminescent functional materials. The structural general formula is shown as formula (I) or formula (II): in formula (I) or formula (II), R1、R2、R3Each independently selected from hydrogen, C6-16 aryl, nitrogen atom electron donating group or nitrogen atom electron withdrawing group; and R is1、R2、R3At least one is an electron donating group containing a nitrogen atom. The compound provided by the invention has the advantages of relatively balanced carrier transmission performance, relatively high triplet state energy level, relatively high glass transition temperature, difficult crystallization, good thermal stability and film forming property, and can be used as a main material, a sensitizing material and a doping material to be applied to a light-emitting layer of an organic electroluminescent device, so that the light-emitting efficiency of the device is effectively improved, and the service life of the device is effectively prolonged. The structural general formula is shown as formula (I) or formula (II):

Description

Pyridoimidazo pyrrole compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent functional materials, and particularly relates to a pyrido-imidazo-pyrrole compound and application thereof.
Background
The basic structure of organic electroluminescent display (OLED) is a sandwich structure composed of a thin and transparent Indium Tin Oxide (ITO) with semiconductor property, which is connected to the anode, and another metal cathode. The entire structure layer includes a Hole Transport Layer (HTL), an Emission Layer (EL), and an Electron Transport Layer (ETL). When power is supplied to a suitable voltage, positive holes and negative charges combine in the light-emitting layer, producing light.
The OLED display technology has the advantages of self-luminescence, wide viewing angle, low energy consumption, high reaction speed and the like, and the technology enables a portable highly-foldable display screen to be possible, so that the OLED display technology is widely applied to the fields of mobile phones, digital video cameras, notebook computers, televisions, automobiles and the like. However, compared with the requirements of products in practical application, there is a certain gap in performance, especially, the luminous efficiency and the lifetime are still required to be further improved. The improvement is mainly carried out from two aspects: the optimization and innovation of the device structure, and the research and development of high-performance functional materials.
In order to fabricate a high-performance OLED light emitting device, researchers have proposed new light emitting mechanisms and functional materials in recent years. The qieyong project group at Qinghua university in 2014 proposed a second host thermal activation sensitized light-emitting mechanism, and TADF materials are used as host materials of OLED devices, so that the improvement of the device performance is realized by sensitizing traditional fluorescent/phosphorescent materials through the TADF materials. Almost at the same time, the Adachi topic group at kyushu university, japan also proposes a similar light emission mechanism. With the continuous research on this type of material, researchers are continuously designing new OLED functional materials, but no TADF host material with superior performance and capable of meeting the requirements of mass production is available at present. The focus of such TADF material design development is to balance the charge transport properties of the material and maintain high charge mobility and triplet energy levels.
According to the industrial application requirements of the current OLED device, in order to meet the photoelectric characteristic requirements of the device, an OLED functional material or a material combination with high performance needs to be selected, and the comprehensive characteristics of high efficiency, long service life and low voltage of the device can be realized. The development of the OLED materials at present is still significantly behind the requirements of panel manufacturing enterprises and the requirements of practical applications, and the development of organic functional materials with higher performance is more important and urgent in the presence of the current market demands.
Disclosure of Invention
In order to solve the problems, the invention provides a pyrido-imidazo-pyrrole compound which has the advantages of relatively balanced carrier transmission performance, relatively high triplet state energy level, relatively high glass transition temperature, difficult crystallization, good thermal stability and good film forming property, and aims to solve the problem that the current OLED functional material cannot meet the application in practical production.
The invention aims to provide a pyrido-imidazo-pyrrole compound, which has a structural general formula shown as a formula (I) or a formula (II):
Figure BDA0002722383290000021
in the formula (I) or the formula (II),
R1、R2、R3each independently selected from hydrogen, C6-16 aryl, nitrogen atom electron donating group or nitrogen atom electron withdrawing group; and R is1、R2、R3At least one is an electron donating group containing a nitrogen atom.
Compared with the prior art, the invention has the beneficial effects that:
1. the pyrido-imidazo-pyrrole compound provided by the invention has higher thermal stability, so that the pyrido-imidazo-pyrrole compound has better film-forming property, and the service life of the compound applied to an OLED device is prolonged;
2. the pyrido-imidazo-pyrrole compound provided by the invention also has balanced carrier transmission performance and higher triplet state energy level, can greatly improve the device performance when being used as a main material, and is a novel organic OLED functional material with a development prospect.
3. The pyrido-imidazo-pyrrole compound provided by the invention has smaller singlet state-triplet state energy level difference, and can be used as a TADF (TADF) main body material, a TADF sensitized material and a TADF luminescent material to be applied to OLED devices.
Detailed Description
The present invention is further illustrated by the following examples, but it should be understood that these examples are included merely for the purpose of facilitating an understanding of the core and practice of the invention, and are not intended to limit the scope of the invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
The invention provides a pyrido-imidazo pyrrole compound, which has a structural general formula shown as a formula (I) or a formula (II):
Figure BDA0002722383290000031
in the formula (I) or the formula (II),
R1、R2、R3each independently selected from hydrogen, C6-16 aryl, nitrogen atom electron donating group or nitrogen atom electron withdrawing group; and R is1、R2、R3At least one is an electron donating group containing a nitrogen atom.
The pyridoimidazopyrrole compounds of the present invention are shown below, specifically the following compounds:
Figure BDA0002722383290000041
Figure BDA0002722383290000051
Figure BDA0002722383290000061
Figure BDA0002722383290000071
Figure BDA0002722383290000081
Figure BDA0002722383290000091
in the following, we provide specific synthetic methods for preparing the above partial compounds and partial intermediates selected from the compounds, the synthetic steps of which are as follows:
the specific synthesis process of the intermediate of the compound with the structural general formula (I) is as follows:
Figure BDA0002722383290000092
adding the compound 1-1 into a mixed solution of concentrated sulfuric acid and concentrated nitric acid, heating to 100 ℃ for reacting for 2 hours, slowly pouring the reaction liquid into ice water under the condition of stirring, stirring to separate out a solid, and filtering. Washing the filter cake to neutrality, drying, and purifying by silica gel column to obtain compound 1-2.
Figure BDA0002722383290000093
Toluene was added to a three-necked flask, then 1mol of 1 to 2 compounds, 1.1mol of 1 to 3 compounds, 0.05mol of 2-dicyclohexyl-phosphorus-2, 4, 6-triisopropyl-biphenyl, 2.2mol of lithium tert-butoxide, 0.025mol of tris (dibenzylideneacetone) dipalladium was added under nitrogen atmosphere, and the mixture was heated to 110 ℃ for reflux reaction. And (3) cooling to room temperature after TLC monitoring that the raw materials completely react, washing the reaction solution to be neutral, drying the reaction solution by using anhydrous sodium sulfate, and purifying the reaction solution by using a silica gel column to obtain the compounds 1-4.
Figure BDA0002722383290000101
Adding tetrahydrofuran into a three-neck flask, then adding 1mol of compound 1-4, heating a reaction system to 60 ℃, slowly dropwise adding 2.2mol of acetic acid, heating to reflux reaction for 2h after dropwise adding, cooling to room temperature after TLC (thin layer chromatography) monitoring of complete reaction of raw materials, adding a saturated sodium carbonate solution into a reaction liquid to adjust the pH to 7, drying organic phase anhydrous sodium sulfate after liquid separation, purifying by a silica gel column, completely dissolving the obtained compound in dichloromethane, adding 1mol of BOC-anhydride, 2mol of triethylamine and 0.1mol of 4-dimethylaminopyridine, stirring at room temperature to react for 8h, washing to neutrality after TLC monitoring of complete reaction of raw materials, drying the organic phase with anhydrous sodium sulfate, and purifying by the silica gel column to obtain the compound 1-6.
Figure BDA0002722383290000102
Dissolving the compounds 1-6 in ethyl acetate solution of trifluoroacetic acid, stirring at normal temperature to react until the TLC monitors that the raw materials completely react, adding saturated sodium carbonate solution into the reaction solution to adjust the pH to 7, separating, drying organic phase anhydrous sodium sulfate, and purifying by silica gel column to obtain the compounds 1-7.
Similar to the synthetic route and method of intermediates with the same core structure and different substituents of intermediates 1-7, the substituents and yield of each intermediate are shown in the following table:
Figure BDA0002722383290000111
Figure BDA0002722383290000112
1mol of intermediate 1-7, 1.1mol of R in a three-necked flask3Bromide, 2mol of potassium carbonate, 0.1mol of 1, 10-phenanthroline completely dissolved in toluene, nitrogen is introduced to remove air in the system, 0.1mol of cuprous bromide is added, the reaction system is heated to 110 ℃, stirred and reacted for 8 hours, TLC (thin layer chromatography) detection is carried out on the raw materials, the raw materials are cooled to room temperature after completely reacting, the reaction solution is washed to be neutral, anhydrous sodium sulfate is dried and then silicon is addedPurifying with gel column to obtain intermediate 1-8.
Similar to the synthetic route and method of intermediates with the same core structure and different substituents of intermediates 1-8, the substituents and yields of each intermediate are shown in the following table:
Figure BDA0002722383290000121
the specific synthesis process of the intermediate of the compound with the structural general formula (II) is as follows:
Figure BDA0002722383290000131
adding the compound 2-1 into a mixed solution of concentrated sulfuric acid and concentrated nitric acid, heating to 100 ℃ for reacting for 2 hours, slowly pouring the reaction liquid into ice water under the condition of stirring, stirring to separate out a solid, and filtering. Washing the filter cake to be neutral, drying, and purifying by a silica gel column to obtain a compound 2-2.
Figure BDA0002722383290000132
Toluene was added to a three-necked flask, and then 1mol of 2-2 compounds, 1.1mol of 2-3 compounds, 0.05mol of 2-dicyclohexyl-phosphorus-2, 4, 6-triisopropyl-biphenyl, 2.2mol of lithium tert-butoxide, 0.025mol of tris (dibenzylideneacetone) dipalladium were added under nitrogen atmosphere, and the mixture was heated to 110 ℃ for reflux reaction. And (3) cooling to room temperature after TLC monitoring that the raw materials are completely reacted, washing the reaction solution to be neutral, drying the reaction solution by using anhydrous sodium sulfate, and purifying the reaction solution by using a silica gel column to obtain a compound 2-4.
Figure BDA0002722383290000133
Adding tetrahydrofuran into a three-neck flask, then adding 1mol of compound 2-4, heating a reaction system to 60 ℃, slowly dropwise adding 2.2mol of acetic acid, heating to reflux reaction for 2h after dropwise adding is finished, cooling to room temperature after TLC (thin layer chromatography) monitoring of the complete reaction of raw materials, adding a saturated sodium carbonate solution into a reaction liquid to adjust the pH to 7, drying organic phase anhydrous sodium sulfate after liquid separation, purifying by a silica gel column, completely dissolving the obtained compound in dichloromethane, adding 1mol of BOC-anhydride, 2mol of triethylamine and 0.1mol of 4-dimethylaminopyridine, stirring at room temperature to react for 8h, washing to be neutral after the TLC monitoring of the complete reaction of the raw materials, drying the organic phase with anhydrous sodium sulfate, and purifying by the silica gel column to obtain the compound 2-6.
Figure BDA0002722383290000141
Dissolving the compound 2-6 in ethyl acetate solution of trifluoroacetic acid, stirring at normal temperature to react until the TLC monitors that the raw materials completely react, adding saturated sodium carbonate solution into the reaction solution to adjust the pH to 7, separating, drying organic phase anhydrous sodium sulfate, and purifying by silica gel column to obtain the compound 2-7.
Similar to the synthetic route and method of the intermediates with the same core structure and different substituents of the intermediates 2-7, the substituents and the yield of each intermediate are shown in the following table:
Figure BDA0002722383290000142
Figure BDA0002722383290000143
1mol of intermediate 2-7, 1.1mol of R in a three-necked flask3Bromide, 2mol of potassium carbonate and 0.1mol of 1, 10-phenanthroline are completely dissolved in toluene, nitrogen is introduced to remove air in the system, 0.1mol of cuprous bromide is added, the reaction system is heated to 110 ℃ and stirred for reaction for 8 hours, TLC detects that raw materials are completely reacted and then cooled to room temperature, reaction liquid is washed to be neutral, and anhydrous sodium sulfate is dried and purified by a silica gel column to obtain an intermediate 2-8.
Similar to the synthetic route and method of the intermediates with the same core structure and different substituents of the intermediates 2-8, the substituents and the yield of each intermediate are shown in the following table:
Figure BDA0002722383290000151
synthesis of Compounds 1-1-12
Figure BDA0002722383290000161
10g of intermediate 6, 7.0g of donor 1, 7.1g of potassium carbonate, 0.5g of 1, 10-phenanthroline and 300ml of toluene are added into a 500ml three-necked flask, nitrogen is introduced to remove air in the system, 0.4g of cuprous bromide is added, the temperature is increased to 110 ℃, the mixture is stirred and reacted for 8 hours, TLC (thin layer chromatography) is used for detecting that the raw materials are completely reacted, the temperature is reduced to room temperature, the reaction solution is washed to be neutral, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 11.9g of compound 1-1-12, and the yield is 83.5%.
1H NMR(400MHz,CDCl3)δ8.48(d,J＝8.4Hz,1H),7.75(d,J＝6.4Hz,2H),7.62(d,J＝6.4Hz,2H),7.58(t,J＝6.4Hz,1H),7.50-7.55(m,9H),7.41(t,J＝6.4Hz,1H),7.37(d,J＝6.4Hz,4H),7.20-7.24(m,4H),7.08(d,J＝6.4Hz,2H),7.00(t,J＝6.4Hz,1H),6.86(t,J＝8.4Hz,1H)；
Synthesis of Compounds 2-2-26
Figure BDA0002722383290000162
10g of intermediate 21, 4.7g of donor 2, 7.1g of potassium carbonate, 0.5g of 1, 10-phenanthroline and 300ml of toluene are added into a 500ml three-necked flask, nitrogen is introduced to remove air in the system, 0.4g of cuprous bromide is added, the temperature is increased to 110 ℃, the mixture is stirred and reacted for 8 hours, TLC (thin layer chromatography) is used for detecting that the raw materials are completely reacted, the temperature is reduced to room temperature, the reaction solution is washed to be neutral, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 9.7g of compound 2-2-26, and the yield is 79.6%.
1H NMR(400MHz,CDCl3)δ8.71(s,1H),8.48(d,J＝8.4Hz,1H),8.46(d,J＝8.0Hz,1H),8.21(s,1H),8.19(d,J＝7.2Hz,2H),7.87(d,J＝8.0Hz,1H),7.68(t,J＝6.4Hz,1H),7.60(d,J＝6.4Hz,1H),7.58(d,J＝7.2Hz,2H),7.47-7.50(m,5H),7.18-7.21(m,4H),6.86(t,J＝8.4Hz,1H)；
Synthesis of Compounds 1-1-35
Figure BDA0002722383290000171
10g of the intermediate 10, 4.0g of the donor 1, 5.9g of potassium carbonate, 0.43g of 1, 10-phenanthroline and 300ml of toluene are added into a 500ml three-necked flask, nitrogen is introduced to remove air in the system, 0.31g of cuprous bromide is added, the temperature is increased to 110 ℃, the mixture is stirred and reacted for 8 hours, TLC (thin layer chromatography) is used for detecting that the raw materials are completely reacted, the temperature is reduced to room temperature, the reaction solution is washed to be neutral, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 9.0g of the compound 1-1-35, and the yield is 76.2%.
1H NMR(400MHz,CDCl3)δ8.48(d,J＝8.4Hz,1H),8.31(s,2H),8.19(d,J＝7.2Hz,2H),7.90(s,1H),7.75(d,J＝6.4Hz,2H),7.58-7.62(m,5H),7.49-7.52(m,7H),7.41(t,J＝6.4Hz,1H),7.18-7.21(m,4H),6.86(t,J＝8.4Hz,1H)；
Synthesis of Compound 1-2-6
Figure BDA0002722383290000172
10g of the intermediate 1, 15.2g of the donor 3, 8.2g of sodium tert-butoxide and 300ml of toluene are added into a 500ml three-necked bottle, nitrogen is introduced to remove air in the system, 96.2mg of palladium acetate and 0.11g of tris (phenyl) phosphine are added, the temperature is raised to 110 ℃, stirring is carried out for reaction for 8 hours, TLC detection is carried out to ensure that the raw materials are cooled to room temperature after complete reaction, the reaction solution is washed to be neutral by water, anhydrous sodium sulfate is dried and then purified by a silica gel column to obtain 10.9g of the compound 1-2-6, and the yield is 53.6%.
1H NMR(400MHz,CDCl3)δ8.48(d,J＝8.4Hz,1H),7.72(d,J＝7.2Hz,1H),7.67(s,1H),7.58-7.62(m,5H),7.46-7.51(m,7H),7.41(t,J＝6.4Hz,1H),7.38(t,J＝7.2Hz,1H),7.33(t,J＝7.2Hz,1H),7.20(m,2H),7.16(t,J＝7.2Hz,1H),6.86(t,J＝8.4Hz,1H)；
Synthesis of Compound 2-2-17
Figure BDA0002722383290000181
10g of the intermediate 13, 20.67 of the donor 4, 8.2g of sodium tert-butoxide and 300ml of toluene are added into a 500ml three-necked flask, nitrogen is introduced to remove air in the system, 96.2mg of palladium acetate and 0.11g of tris (phenyl) phosphine are added, the temperature is raised to 110 ℃, stirring is carried out for 8 hours, TLC detection is carried out to ensure that the raw materials are cooled to room temperature after complete reaction, the reaction liquid is washed to be neutral by water, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 11.7g of compound 1-2-17, and the yield is 46.3%.
1H NMR(400MHz,CDCl3)δ8.55(d,J＝7.2Hz,1H),8.48(d,J＝8.4Hz,1H),8.24(d,J＝7.2Hz,1H),7.94(d,J＝7.2Hz,1H),7.88(s,1H),7.74(d,J＝7.2Hz,1H),7.63(t,J＝6.4Hz,1H),7.57(d,J＝7.2Hz,1H),7.46-7.51(m,9H),7.41(t,J＝6.4Hz,1H),7.38(t,J＝7.2Hz,1H),7.33(t,J＝6.8Hz,1H),7.20(m,2H),7.16(t,J＝7.2Hz,1H),6.86(t,J＝8.4Hz,1H),1.69(s,6H)；
Synthesis of Compounds 1-2-26
Figure BDA0002722383290000182
10g of the intermediate 8, 15.1g of the donor 5, 8.2g of sodium tert-butoxide and 300ml of toluene are added into a 500ml three-necked bottle, nitrogen is introduced to remove air in the system, 96.2mg of palladium acetate and 0.11g of tris (phenyl) phosphine are added, the temperature is raised to 110 ℃, stirring is carried out for 8 hours, TLC detection is carried out to ensure that the raw materials are cooled to room temperature after complete reaction, the reaction solution is washed to be neutral by water, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 11.6g of the compound 1-2-26, and the yield is 57.2%.
1H NMR(400MHz,CDCl3)δ9.24(s,1H),8.70(d,J＝8.0Hz,1H),8.48(d,J＝8.4Hz,1H),8.42(d,J＝8.0Hz,1H),8.19(d,J＝7.2Hz,2H),7.57-7.63(m,5H),7.46-7.51(m,6H),7.20(m,2H),7.16(t,J＝7.2Hz,1H),6.86(t,J＝8.4Hz,1H)；
Synthesis of Compound 2-3-22
Figure BDA0002722383290000191
10g of the intermediate 19, 10.6g of the donor 6, 8.0g of potassium carbonate, 0.58g of 1, 10-phenanthroline and 300ml of toluene are added into a 500ml three-necked bottle, nitrogen is introduced to remove air in the system, 0.42g of cuprous bromide is added, the temperature is increased to 110 ℃, the mixture is stirred and reacted for 8 hours, TLC (thin layer chromatography) is used for detecting that the raw materials are completely reacted, the temperature is reduced to room temperature, the reaction solution is washed to be neutral, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 12.9g of the compound 2-3-22, and the yield is 69.2%.
1H NMR(400MHz,CDCl3)δ8.62(d,J＝8.4Hz,1H),8.19(d,J＝7.2Hz,3H),7.94(d,J＝7.2Hz,2H),7.72(d,J＝7.2Hz,1H),7.67(s,1H),7.58-7.63(m,5H),7.46-7.51(m,7H),7.35-7.41(m,4H),7.20(m,2H),7.16(t,J＝7.2Hz,2H),6.77(t,J＝8.4Hz,1H)；
Synthesis of Compounds 1-3-22
Figure BDA0002722383290000192
10g of intermediate 7, 12.0g of donor 7, 8.0g of potassium carbonate, 0.94g of tetrabutylammonium bromide, 200ml of toluene, 60ml of ethanol and 40ml of water are added into a 500ml three-necked flask, nitrogen is introduced to remove air in the system, 0.84g of tetrakis (triphenyl) phosphine is added, the temperature is increased to 80 ℃, the reaction is stirred for 8 hours, TLC detection is carried out on raw materials, the temperature is reduced to room temperature after complete reaction, reaction liquid is washed to be neutral, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 14.9g of compound 1-3-26, and the yield is 75.8%.
1H NMR(400MHz,CDCl3)δ8.67(d,J＝8.4Hz,1H),8.42(d,J＝7.6Hz,2H),8.19(d,J＝8.0Hz,1H),8.11(d,J＝8.0Hz,1H),8.10(d,J＝7.6Hz,2H),7.91-7.94(m,6H),7.88(d,J＝8.0Hz,1H),7.85(s,1H),7.67(t,J＝8.0Hz,1H),7.65(t,J＝8.0Hz,1H),7.62(t,J＝6.4Hz,2H),7.58(t,J＝6.4Hz,1H),7.50-7.52(m,4H),7.46(t,J＝6.4Hz,2H),7.41(t,J＝6.4Hz,1H),7.33(t,J＝8.0Hz,1H),7.20(s,1H),6.99(t,J＝8.4Hz,1H)；
Synthesis of Compound 2-3-29
Figure BDA0002722383290000201
10g of intermediate 23, 8.4g of donor 8, 8.0g of potassium carbonate, 0.94g of tetrabutylammonium bromide, 200ml of toluene, 60ml of ethanol and 40ml of water are added into a 500ml three-necked flask, nitrogen is introduced to remove air in the system, 0.84g of tetrakis (triphenyl) phosphine is added, the temperature is increased to 80 ℃, the reaction is stirred for 8 hours, TLC detection is carried out on raw materials, the temperature is reduced to room temperature after complete reaction, reaction liquid is washed to be neutral, anhydrous sodium sulfate is dried and then is purified by a silica gel column to obtain 11.5g of compound 2-3-29, and the yield is 71.6%.
1H NMR(400MHz,CDCl3)δ8.71(d,J＝8.0Hz,1H),8.67(d,J＝8.4Hz,2H),8.46(d,J＝8.0Hz,1H),8.21(s,1H),8.19(d,J＝7.2Hz,2H),7.87(d,J＝8.0Hz,1H),7.85(s,1H),7.68(t,J＝6.4Hz,1H),7.60(d,J＝6.4Hz,1H),7.58(d,J＝7.2Hz,2H),7.46-7.51(m,7H),7.41(t,J＝6.4Hz,1H),7.20(s,1H),7.16(t,J＝7.2Hz,2H),6.99(t,J＝8.4Hz,1H)；
The pyrido-imidazo-pyrrole compound provided by the invention can be used as a main material, a sensitizing material or a doping material of a light-emitting layer of an OLED device, and the performance parameters (including a thermal weight loss temperature Td, a Tg temperature, a HOMO energy level and a LUOMO energy level) of the partial compound and the CBP of the existing OLED material are measured, wherein:
the thermogravimetric temperature Td was a temperature at which 1% weight loss was observed in a nitrogen atmosphere, and was measured with a TGA-50H thermogravimetric analyzer (Shimadzu corporation, Japan) at a nitrogen flow rate of 20 ml/min;
the Tg temperature was measured on a DSC-60 differential scanning calorimeter (Shimadzu, Japan) with a nitrogen flow of 10 ml/min;
HOMO/LUOMO energy level is data obtained by simulation calculation in Gaussian 09 software, and the calculation method adopts a B3LYP hybridization functional, and the group is 6-31g (d);
ΔESTand calculating according to the fluorescence spectrum and the low-temperature phosphorescence spectrum of the compound.
The comparative results are shown in Table 1.
Table 1 comparison of performance parameters of the compounds provided in the examples and the existing OLED materials
Compound (I) Tg(℃) Td(℃) HOMO LUMO ΔEST(eV)
Compounds 1-1-12 148 398 -5.50 -2.36 0.22
Compounds 2-2-26 151 407 -5.54 -2.23 0.26
Compounds 1-1-35 149 401 -5.60 -2.17 0.23
Compound 1-2-6 142 409 -5.52 -2.41 0.18
Compound 2-2-17 166 412 -5.61 -2.77 0.14
Compounds 1-2-26 161 407 -5.65 -2.75 0.19
Compound 2-3-22 147 402 -5.42 -2.35 0.12
Compounds 1-3-26 160 405 -5.33 -2.67 0.15
Compound 2-3-29 154 400 -5.45 -2.65 0.18
TCzCN 153 401 -5.65 -1.94 0.21
CBP 62 353 -5.9 -2.6 /
As can be seen from Table 1, the pyrido-imidazo-pyrrole compound provided by the invention has higher thermal stability, so that the compound has better film-forming property, and the service life of the OLED device containing the material provided by the invention is prolonged; the derivative also has different HOMO energy levels, and can be applied to different functional layers.
In order to better evaluate the applicability of the compound provided by the invention as a host material, a sensitizing material and a doping material of a light-emitting layer in an OLED device, a device made of an existing material is used as a comparative example, a device made of the material provided by the invention is used as an example, the manufacturing process of the device in the example is completely the same as that in the comparative example, the same substrate material and electrode material are adopted, the film thickness of the electrode material is also consistent, and the difference is that some adjustment is carried out on part of materials used in the device.
The organic film is subjected to double-source co-evaporation through ANS evaporation equipment, an evaporation substrate is made of high-transparency quartz glass, the impurity doping concentration of an object material is 2%, and after evaporation, the organic film is packaged in a glove box (the glove box is in an argon environment, and the water content and the oxygen concentration are less than 1 ppm).
Example 1
Transparent substrate layer 1/ITO anode layer 2/hole transport layer 3(TAPC, thickness of 40 nm)/luminescent layer 4 (including host material CBP, sensitizing material compound 1-1-35, doping material TCzCN, mixed according to the mass ratio of 93:5:2, thickness of 30 nm)/electron transport layer 5(TPBi, thickness of 40 nm)/electron injection layer 6(LiF, thickness of 1 nm)/cathode reflection electrode layer Al.
The structure of part of materials used in the device is as follows:
Figure BDA0002722383290000221
the preparation process comprises the following steps:
the transparent substrate layer is a transparent substrate, such as a transparent PI film, glass, or the like.
And washing the ITO anode layer, sequentially carrying out alkali washing, ultrapure water washing and drying, and then carrying out ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO.
TAPC having a thickness of 40nm was deposited on the ITO anode layer by a vacuum deposition apparatus to form a hole transport layer 1.
And after the evaporation of the hole transport material is finished, manufacturing a light-emitting layer of the OLED light-emitting device, wherein a compound CBP is used as a main material, a compound TCzCN is used as a doping material, the doping proportion of the doping material is 2% by weight, and the thickness of the light-emitting layer is 30 nm.
After the light-emitting layer, an electron transport material TPBI was continuously vacuum-evaporated to form an electron transport layer having a thickness of 40 nm.
On the electron transport layer, a lithium fluoride layer having a film thickness of 1nm was produced as an electron injection layer by vacuum evaporation.
On the electron injection layer, an aluminum layer having a film thickness of 80nm was formed as a cathode electrode layer by vacuum evaporation.
After the OLED device is manufactured, the anode and the cathode are connected by a driving circuit, and the current efficiency, the luminous brightness and the service life of the device are measured.
Example 2
The same as example 1, except that: the luminescent layer 4 comprises a main material CBP, a sensitizing material compound 2-2-17 and a doping material TCzCN, the mass ratio of which is 93:5:2, and the thickness of which is 30 nm.
Example 3
The same as example 1, except that: the luminescent layer 4 comprises a main material CBP, a sensitizing material compound 2-3-22 and a doping material TCzCN, the mass ratio of which is 93:5:2, and the thickness of which is 30 nm.
Example 4
The same as example 1, except that: the luminescent layer 4 comprises a host material compound 1-1-12 and a doping material TCzCN, the mass ratio of which is 98:2, and the thickness of which is 30 nm.
Example 5
The same as example 1, except that: the luminescent layer 4 comprises a host material compound 1-2-6 and a doping material TCzCN, the mass ratio of which is 98:2, and the thickness of which is 30 nm.
Example 6
The same as example 1, except that: the luminescent layer 4 comprises 1-3-26 of a host material compound and a doping material TCzCN, the mass ratio of the host material compound to the doping material TCzCN is 98:2, and the thickness of the luminescent layer is 30 nm.
Example 7
The same as example 1, except that: the light-emitting layer 4 includes a host material CBP: 2-2-26 of doping material compound, wherein the mass ratio is as follows: 98:2 and a thickness of 30 nm.
Example 8
The same as example 1, except that: the light-emitting layer 4 comprises a main material CBP and doping material compounds 1-2-26 in a mass ratio of: 98:2 and a thickness of 30 nm.
Example 9
The same as example 1, except that: the light-emitting layer 4 comprises a main material CBP and a doping material compound 2-3-29, and the mass ratio is as follows: 98:2 and a thickness of 30 nm.
Comparative example 1
The same as example 1, except that: the light-emitting layer 4 comprises a host material CBP and a doping material TCzCN, which are arranged in a ratio of 98:2, and the thickness is 30 nm.
Examples 1 to 9 show that the synthesized compound of the present invention is used as a sensitizing material, a host material or a doping material of a light emitting layer of an OLED device, and compared with comparative example 1, the manufacturing processes of the devices of examples 1 to 9 are completely the same, the substrate material and the electrode material are also completely the same, the film thicknesses of the electrode materials are also kept the same, the device performance testing method is the same as comparative example 1, the obtained device structure is shown in table 2, and the device performance testing result is shown in table 3.
Table 2 device structures provided in examples 1-9 and comparative examples
Device with a metal layer Host material Sensitizing material Doping material Electron transport layer
Example 1 CBP Compounds 1-1-35 TCzCN TPBI
Example 2 CBP Compound 2-2-17 TCzCN TPBI
Example 3 CBP Compound 2-3-22 TCzCN TPBI
Example 4 Compounds 1-1-12 / TCzCN TPBI
Example 5 Compound 1-2-6 / TCzCN TPBI
Example 6 Compounds 1-3-26 / TCzCN TPBI
Example 7 CBP / Compounds 2-2-26 TPBI
Example 8 CBP / Compounds 1-2-26 TPBI
Examples9 CBP / Compound 2-3-29 TPBI
Comparative example 1 CBP / TCzCN TPBI
Table 3 results of performance testing of devices of examples 1-9 and comparative example
Grouping Efficiency (cd/A) LT90(hr)@5000nits
Example 1 18.6 23.6
Example 2 16.5 18.3
Example 3 19.2 23.7
Example 4 12.9 15.2
Example 5 13.2 13.6
Example 6 12.6 15.8
Example 7 11.7 16.3
Example 8 13.2 14.9
Example 9 12.2 14.3
Comparative example 1 7.3 8.2
As can be seen from the device performance data in Table 3, compared with a device using the existing material CBP as the Host material, the current efficiency and the service life of the device are greatly improved by using the material of the invention as the sensitizing material in device examples 1-3, using the material of the invention as the Host material in device examples 4-6, and using the material of the invention as the doping material in device examples 7-9;
in summary, compared with the existing materials, the compound material provided by the invention can greatly improve the device performance when being applied to OLED devices, especially sensitized materials, main body materials and doped materials of a light-emitting layer, and is a novel organic OLED functional material with a relatively promising development prospect.
The above examples are only some examples for facilitating understanding of the synthesis and application methods of the materials of the present invention, and are not intended to limit the present invention. It will be understood that the structure may be readily modified by the skilled person, and any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the scope of the present invention.

Claims (6)

1. A pyridoimidazopyrrole compound is characterized in that the structural general formula is shown as a formula (I) or a formula (II):
Figure FDA0003234598390000011
in the formula (I) or the formula (II),
R1、R2、R3each independently selected from hydrogen, C6-16 aryl, nitrogen atom electron donating group or nitrogen atom electron withdrawing group; and R is1、R2、R3At least one is an electron donating group containing a nitrogen atom;
the aryl of C6-16 is one of the following structural formulas:
Figure FDA0003234598390000012
the electron-withdrawing group containing nitrogen atoms is selected from one of the following structural formulas:
Figure FDA0003234598390000013
the electron-donating group containing nitrogen atom is selected from one of the following structural formulas:
Figure FDA0003234598390000014
Figure FDA0003234598390000021
2. the pyridoimidazopyrrole compound according to claim 1, which is specifically any one of the following compounds:
Figure FDA0003234598390000022
Figure FDA0003234598390000031
Figure FDA0003234598390000041
Figure FDA0003234598390000051
Figure FDA0003234598390000061
Figure FDA0003234598390000071
3. use of the pyridoimidazopyrrole compounds according to claim 1 in organic electroluminescent devices.
4. An organic electroluminescent device comprising a light-emitting layer, wherein the light-emitting layer comprises a host material and a dopant material, and at least one of the host material and the dopant material comprises the pyridoimidazopyrrole compound according to claim 1.
5. An organic electroluminescent device comprising a light-emitting layer, wherein a sensitizing material of the light-emitting layer comprises the pyridoimidazopyrrole compound according to claim 1.
6. Use of the organic electroluminescent device of claim 4 or 5 in an organic electroluminescent display device.
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