CN114685351A - OLED main body material based on triptycene framework and preparation method and application thereof - Google Patents

OLED main body material based on triptycene framework and preparation method and application thereof Download PDF

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CN114685351A
CN114685351A CN202210322954.9A CN202210322954A CN114685351A CN 114685351 A CN114685351 A CN 114685351A CN 202210322954 A CN202210322954 A CN 202210322954A CN 114685351 A CN114685351 A CN 114685351A
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陈传峰
谭珂珂
李猛
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Institute of Chemistry CAS
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Abstract

The invention discloses an OLED (organic light emitting diode) main body material based on a triptycene framework as well as a preparation method and application thereof, and belongs to the field of organic electroluminescent materials and devices. The structure of the compound of the invention is shown as formula 1

Description

OLED main body material based on triptycene framework and preparation method and application thereof
Technical Field
The invention relates to the field of organic electroluminescent materials and devices, in particular to an OLED (organic light emitting diode) main body material based on a triptycene framework as well as a preparation method and application thereof.
Background
Organic Light Emitting Diodes (OLEDs), as a new generation display technology, have the advantages of low cost, low power consumption, flexibility, rich colors, wide viewing angles, etc., as compared to conventional displays, and are increasingly used in the fields of solid state lighting, flat panel display, etc. With the development of research, the light emitting materials have been also expanded to the third generation, the first generation OLED material is a conventional fluorescent molecule, the second generation is a phosphorescent OLED material, and the third generation Thermal Activated Delayed Fluorescence (TADF) material, wherein the phosphorescent OLED material and the thermal activated delayed fluorescence material can effectively utilize 75% of triplet excitons so as to obtain high External Quantum Efficiency (EQE), but the stability and lifetime of the device limit the practical application thereof. Fluorescence quenching is one of the important factors influencing the performance of an OLED device, and people can uniformly disperse guest molecules in a host material by selecting a proper host material and utilizing host-guest doping to enhance the performance of the OLED device, so that the host material can reduce the concentration fluorescence quenching on one hand, and can transfer the energy of the host material to the guest material through energy transfer on the other hand, thereby improving the performance of the OLED device.
Currently, a number of new OLED emissive layer guest materials have been developed, in contrast to the relatively late studies of host materials for OLED devices. The triptycene is a molecule with a non-planar structure, has a larger framework and a larger cavity, is beneficial to uniform dispersion of small molecular materials, and inhibits the aggregation quenching effect of the small molecular materials, thereby improving the efficiency of an OLED device.
Disclosure of Invention
The invention provides an OLED (organic light emitting diode) main body material based on a triptycene framework, and a preparation method and application thereof.
The present invention first provides a compound represented by formula 1:
Figure BDA0003572445430000021
wherein, in formula 1, Ar represents one or more aromatic rings or aromatic condensed rings.
Specifically, the Ar is selected from any one of the following groups: benzene, biphenyl, terphenyl, naphthalene, pyridine, naphthyridine, phenanthridine, quinoline, isoquinoline, pyrimidine, diphenyl sulfone, dibenzo [ f, h ] quinoxaline and derivatives thereof;
the structure of Ar is as follows:
Figure BDA0003572445430000022
wherein the connection position of Ar and the formula 1 can be any position in the Ar cyclic structure.
The compound may specifically be any one of the following:
Figure BDA0003572445430000023
Figure BDA0003572445430000031
the invention also provides a preparation method of the compound shown in the formula 1, which comprises the following steps:
1) will be formula A1A compound of the formula A2Reacting the compound under the catalysis of palladium to obtain a compound shown as a formula B;
Figure BDA0003572445430000041
2) reacting the compound shown in the formula B under the catalysis of palladium to obtain a compound shown in a formula C;
Figure BDA0003572445430000042
3) and (3) reacting the compound shown in the formula C with an aromatic ring or aromatic condensed ring compound to obtain the compound shown in the formula 1.
In the above preparation method, step 1), the reaction is carried out in Pd (OAc)24, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (xanthphos) and sodium tert-butoxideA row;
the Pd (OAc)2And the formula A1The molar ratio of the compounds is 0.05-0.2: 1; specifically, the ratio can be 0.1: 1;
the 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene and the compound of formula A1The molar ratio of the compounds is 0.1-0.4: 1; specifically, the ratio can be 0.2: 1;
the sodium tert-butoxide is of the formula A1The molar ratio of the compounds is 1-3: 1; specifically 3: 1;
the formula A1Compounds and said A2The molar ratio of the compounds is 1: 3-10; specifically 1: 3;
the reaction of step 1) is carried out in a solvent; specifically, the solvent is at least one of toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide and dimethylformamide;
in the step 1), the reaction temperature is 70-120 ℃, and can be 120 ℃; the reaction time is 3-6 hours; specifically, the time can be 4 hours;
in the step 1), after the reaction, the system is cooled to room temperature and is extracted by water and dichloromethane, and an extracted organic phase is dried by anhydrous sodium sulfate, filtered and distilled to remove the organic phase to obtain a crude product.
The step 1) also comprises a step of purifying the crude product; specifically, the purification method adopts at least one of recrystallization, column chromatography and sublimation; more specifically, column chromatography (petroleum ether: dichloromethane volume ratio 4:1) is adopted for purification.
In the above preparation method, step 2), the reaction is carried out in Pd (OAc)2The tri-tert-butylphosphonium tetrafluoroborate and the potassium carbonate;
the Pd (OAc)2The molar ratio of the compound to the compound shown in the formula B is 0.05-0.2: 1; specifically, the ratio can be 0.1: 1;
the molar ratio of the tri-tert-butylphosphonium tetrafluoroborate to the compound shown in the formula B is 0.1-0.4: 1; specifically, the ratio can be 0.2: 1;
the molar ratio of the potassium carbonate to the compound shown in the formula B is 1-3: 1; specifically 3: 1;
the reaction in step 2) is carried out in a solvent; specifically, the solvent is at least one of toluene, dimethylformamide and dimethylacetamide;
in the step 2), the reaction temperature is 100-140 ℃, and can be 120 ℃; the reaction time is 10-16 hours, specifically 12 hours;
in the step 2), after the reaction, the system is cooled to room temperature and is extracted by water and ethyl acetate, and the extracted organic phase is dried by anhydrous sodium sulfate, filtered and distilled to remove the organic liquid phase to obtain a crude product.
The step 2) also comprises a step of purifying the crude product; specifically, the purification method adopts at least one of recrystallization, column chromatography and sublimation; more specifically, the purification can be performed by column chromatography (petroleum ether: dichloromethane volume ratio 3: 1).
In the preparation method, in the step 3), the reaction temperature is 100-150 ℃, and specifically can be 120 ℃; the reaction time is 12-48 hours, specifically 24 hours;
the aromatic ring or aromatic condensed ring compound is dibromo biphenyl, m-dibromo benzene, dibromo terphenyl, 1-bromo-3- (4-bromophenyl) benzene, dibromo naphthalene, dibromo isoquinoline, 6, 11-dibromo dibenzo [ f, h ] quinoxaline, dibromo pyrimidine, dibromo phenanthridine, dibromo diphenyl sulfone, difluoropyridine, dibromo quinazoline or dichloro-1, 8-naphthyridine;
the molar ratio of the compound shown in the formula C to the aromatic ring or aromatic condensed ring compound is 2.5-4: 1; specifically 3: 1;
in the step 3), the reaction is carried out under any one of the following conditions a) to c):
a) in sodium tert-butoxide, Pd (OAc)2And tri-tert-butylphosphonium tetrafluoroborate;
specifically, the molar ratio of the compound shown in the formula C to sodium tert-butoxide is 1: 1-3; specifically 1: 3;
the compound shown as the formula C is reacted with Pd (OAc)2May be in a molar ratio of1: 0.05-0.2; specifically 1:0.1 or 1: 0.05;
the molar ratio of the compound shown in the formula C to the tri-tert-butylphosphonium tetrafluoroborate can be 1: 0.1-0.4; specifically 1: 0.2;
b) in the presence of potassium carbonate, copper and 18-crown-6;
specifically, the molar ratio of the compound shown in the formula C to potassium carbonate is 1: 1-3; specifically 1: 3;
the molar ratio of the compound shown in the formula C to copper can be 1: 2-7; specifically 1: 2;
the molar ratio of the compound shown in the formula C to the 18-crown-6 can be 1: 0.2-0.8; specifically 1: 0.2;
c) in the presence of sodium tert-butoxide;
specifically, the molar ratio of the compound shown in the formula C to sodium tert-butoxide can be 1: 1-3, specifically 1: 3;
the reaction in step 3) is also carried out in a solvent; specifically, the solvent is at least one of toluene, dimethylformamide and dimethylacetamide;
in the step 3), after the reaction, the system is cooled to room temperature and is extracted by water and ethyl acetate, and the extracted organic phase is dried by anhydrous sodium sulfate, filtered and distilled to remove the organic liquid phase to obtain a crude product.
The step 3) also comprises a step of purifying the crude product; specifically, the purification method adopts at least one of recrystallization, column chromatography and sublimation; specifically, the purification can be performed by column chromatography (petroleum ether: dichloromethane volume ratio 5: 1).
In the above preparation method, the steps 1) to 3) are carried out in an inert atmosphere; specifically, the method is carried out under the protection of nitrogen.
The application of the compound shown in the formula 1 in the preparation of the organic light-emitting diode device also belongs to the protection scope of the invention.
Specifically, the host material of the light-emitting layer of the organic light-emitting diode device comprises the compound.
The invention finally provides an organic light-emitting diode device, wherein the host material of the light-emitting layer of the organic light-emitting diode device comprises the compound.
The organic light-emitting diode device sequentially comprises an anode, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode from bottom to top.
The room temperature is well known to those skilled in the art, and is generally 15-35 ℃.
The invention has the following advantages:
(1) the synthesis method of the triptycene skeleton-based OLED main body material is simple, the product yield is high, and the triptycene skeleton-based OLED main body material can be prepared in a large scale;
(2) the OLED main body material based on the triptycene framework has a wide application range, and can be suitable for most common yellow light and green light materials;
(3) the organic film formed by the OLED main body material based on the triptycene skeleton has high surface smoothness, oxidation and reduction resistance and high luminous efficiency, and can be used as a luminous layer of an organic light-emitting diode;
(4) the organic light-emitting diode using the organic thin film layer formed by the OLED main body material based on the triptycene framework as the light-emitting layer has the advantages of high efficiency, low driving voltage, long service life and low-efficiency roll-off.
Drawings
Fig. 1 is a schematic structural diagram of an organic light emitting diode prepared according to the present invention.
Detailed Description
The present invention is described in further detail below with reference to specific embodiments, which are given for the purpose of illustration only and are not intended to limit the scope of the invention.
The experimental procedures in the following examples are conventional unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The title reported in 2018 by Timothy m. swager, Stephen l. buchwald et al for 2-amino-triptycene in the following examples is: the literature synthesis of Molecular Design of Deep Blue Thermally Activated Delayed Fluorescence Materials applied to a biocompatible Triptycene Scaffold and digital Angle Tuning (chem. Mater.2018,30,1462-1466) can be obtained from commercial sources.
The synthetic route is as follows:
Figure BDA0003572445430000071
the following examples used 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (xanthphos) and tri-tert-butylphosphonium tetrafluoroborate, respectively, and were purchased from Beijing Yinaoka technologies, Inc.: a66803, a 90323.
Example 1 preparation of Compound of formula D
Figure BDA0003572445430000081
The method comprises the following specific steps:
(1) 5.00g (18.6mmol) of 2-amino-triptycene, 10.66g (55.69mmol) of o-bromochlorobenzene, 5.35g (55.69mmol) of sodium tert-butoxide, 0.417g (1.86mmol) of palladium acetate, 3.58g (3.72mmol) of 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (xanthphos) and 150mL of toluene were added in this order to a 500mL two-necked round-bottomed flask under nitrogen, and the mixture was refluxed at 120 ℃ for 4 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of dichloromethane into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product B. The crude product was purified by column chromatography (petroleum ether: dichloromethane vol: 4:1) to yield 6.21g of a white powder. The white powder was B, with a yield of 88%.
The structure confirmation data for B are as follows:1H NMR(300MHz,Chloroform-d)δ7.37(dt,J＝6.3,2.2Hz,4H),7.30(dd,J＝7.9,1.4Hz,2H),7.23(d,J＝2.2Hz,1H),7.11(ddd,J＝16.9,7.6,1.6Hz,2H),7.04–6.96(m,4H),6.80–6.70(m,2H),5.37(d,J＝11.0Hz,2H).
(2) a500 mL two-necked round-bottomed flask was charged with compound B, 5.00g (13.2mmol), potassium carbonate 5.47g (39.6mmol), palladium acetate 0.295g (1.32mmol), tri-tert-butylphosphonium tetrafluoroborate 0.766g (2.64mmol), and 150mL of toluene in this order under a nitrogen atmosphere, and refluxed at 120 ℃ for 12 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product C. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 3:1) to yield 3.5g of a yellow powder. The yellow powder was C in 78% yield.
The structure confirmation data for C are as follows:1H NMR(300MHz,Chloroform-d)δ8.03(s,1H),7.95(dt,J＝7.8,1.0Hz,1H),7.45–7.38(m,5H),7.33–7.30(m,2H),7.16(ddd,J＝8.1,6.0,2.2Hz,1H),7.03–6.94(m,4H),5.55(s,1H),5.49(s,1H).
(3) to a 500mL two-necked round-bottomed flask, under a nitrogen blanket, were added compound C, 1.00g (2.91mmol), 0.302g (0.97mmol) of 4, 4-dibromobiphenyl, 0.839g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate to extract, drying the extracted organic phase by using anhydrous sodium sulfate, filtering, and distilling to remove the organic liquid phase to obtain a crude product D. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was D, yield 63%.
D, the structural confirmation data are as follows, HRMS (MALDI TOF) m/z calcd for C84H72N2O4[M+H]+836.3191,found 836.3348.
Example 2 preparation of Compound of formula N
Figure BDA0003572445430000091
The method comprises the following specific steps:
(1) to a 250mL two-necked round-bottomed flask, under nitrogen, were added in this order compound C, 0.800g (2.33mmol), m-dibromobenzene 0.184g (0.776mmol), potassium carbonate 0.784g (6.99mmol), copper 0.296g (4.66mmol), 18-crown-60.123 g (0.466mmol), and 50mL of toluene, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product N. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to yield 1.0g of a white powder. The white powder was N, the yield was 58%.
The structure confirmation data for N is as follows: HRMS (MALDI TOF) m/z calcd for C58H36N2[M]+760.2878,found 760.3673.
Example 3 preparation of Compound of formula E
Figure BDA0003572445430000101
The method comprises the following specific steps:
(1) under nitrogen protection, to a 500mL two-necked round-bottomed flask, compound C, 1.00g (2.91mmol), 0.376g (0.97mmol) of 4, 4-dibromoterphenyl, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene were added in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product E. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 610g of a white powder. The white powder was E in 61% yield.
The structure confirmation data for E is as follows: HRMS (APCI) m/z calcd for C70H46N2[M+H]+914.3361,found 914.3348.
Example 4 preparation of Compound of formula F
Figure BDA0003572445430000111
The method comprises the following specific steps:
(1) to a 500mL two-necked round-bottomed flask, under a nitrogen blanket, were added 1.00g (2.91mmol), 0.302g (0.97mmol) of 1-bromo-3- (4-bromophenyl) benzene, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product F. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to yield 400g of a white powder. The white powder was F, with a yield of 40%.
The structure confirmation data for F is as follows: RMS (APCI) m/z calcd for C64H42N2[M+H]+838.3348,found 838.3673.
Example 5 preparation of Compound of formula G
Figure BDA0003572445430000112
The method comprises the following specific steps:
(1) to a 500mL two-necked round-bottomed flask, under a nitrogen blanket, were added 1.00g (2.91mmol), 0.277g (0.97mmol) of 2, 6-dibromonaphthalene, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product G. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was G in 63% yield.
The structure confirmation data for G is as follows: HRMS (APCI) m/z calcd for C62H40N2[M+H]+812.3191,found 812.3278.
Example 6 preparation of Compound of formula H
Figure BDA0003572445430000121
The method comprises the following specific steps:
(1) under nitrogen protection, to a 500mL two-necked round-bottomed flask, compound C, 1.00g (2.91mmol), 0.278g (0.97mmol) of 1, 4-dibromoisoquinoline, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphine tetrafluoroborate, and 50mL of toluene were added in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product H. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was H, yield 60%.
The structure confirmation data for H are as follows: HRMS (APCI) m/z calcd for C61H39N3[M+H]+813.3144,found 813.3278.
Example 7 preparation of a Compound of formula I
Figure BDA0003572445430000131
The method comprises the following specific steps:
(1) under nitrogen protection, 1.00g (2.91mmol), 0.193g (0.97mmol) of 2, 6-dichloro-1, 8-naphthyridine, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate and 50mL of toluene were added in this order to a 500mL two-necked round-bottomed flask, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product I. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was I, yield 63%.
The structure confirmation data for I are as follows: HRMS (APCI) m/z calcd for C60H38N4[M+H]+814.3096,found 814.4277.
Example 8 preparation of Compound of formula J
Figure BDA0003572445430000132
The method comprises the following specific steps:
(1) to a 500mL two-necked round-bottomed flask, under a nitrogen blanket, were added compound C in the order of 1.00g (2.91mmol), 0.229g (0.97mmol) of 2, 5-dibromopyrimidine, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product J. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was J, yield 63%.
The structure confirmation data for J are as follows: HRMS (APCI) m/z calcd for C56H34N4[M+H]+764.2940,found 764.3067.
Example 9 preparation of a Compound of formula K
Figure BDA0003572445430000141
The method comprises the following specific steps:
(1) to a 500mL two-necked round-bottomed flask, under a nitrogen blanket, were added 1.00g (2.91mmol), 0.326g (0.97mmol) of 3, 8-dibromophenanthridine, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product K. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was K, with a yield of 63%.
The structure confirmation data for K is as follows: HRMS (APCI) m/z calcd for C65H39N3[M+H]+861.3144,found 861.3367.
Example 10 preparation of Compound of formula L
Figure BDA0003572445430000151
The method comprises the following specific steps:
(1) in the air atmosphere, 0.800g (2.186mmol) of 2, 7-dibromo-9, 10-phenanthrenequinone, 0.350g (5.733mmol) of ethylenediamine and 50mL of acetic acid are sequentially added into a 500mL double-neck round-bottom flask, reflux is carried out at 120 ℃ for 10 hours, after a reaction system is cooled to room temperature, a reaction solution is poured into 200mL of cold water, reduced pressure suction filtration is carried out, and a solid is sequentially washed by water and ethanol, so that 0.690g of white powder is obtained. The white powder was the precursor compound for preparation L in 94% yield.
(2) To a 500mL two-necked round-bottomed flask, 1.00g (2.91mmol), 0.373g (0.97mmol) of the precursor compound, 0.838g (8.73mmol) of sodium tert-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate and 50mL of toluene were successively added under nitrogen atmosphere, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product L. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was L, yield 63%.
The structure validation data for L is as follows: HRMS (APCI) m/z calcd for C68H42N4[M+H]+914.3409,found 914.3482.
Example 11 preparation of a Compound of formula M
Figure BDA0003572445430000161
The method comprises the following specific steps:
(1) to a 500mL two-necked round-bottomed flask, 1.00g (2.91mmol), 0.364g (0.97mmol) of 4,4' -dibromodiphenylsulfone, 0.838g (8.73mmol) of sodium t-butoxide, 0.065g (0.291mmol) of palladium acetate, 0.168g (0.582mmol) of tri-t-butylphosphonium tetrafluoroborate, and 50mL of toluene were sequentially added under a nitrogen atmosphere, and refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product M. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was M, yield 63%.
The structure validation data for M are as follows: HRMS (APCI) m/z calcd for C64H42N2O2S[M+H]+902.2967,found 902.5376.
Example 12 preparation of Compound of formula O
Figure BDA0003572445430000162
The method comprises the following specific steps:
(1) to a 250mL two-necked round-bottomed flask, under nitrogen, were added, in this order, compound C, 0.100g (0.291mmol), 0.011g (0.0970mmol) of 2, 6-difluoropyridine, 0.083g (0.873mmol) of sodium tert-butoxide, and 10mL of toluene, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying the extracted organic phase by using anhydrous sodium sulfate, filtering, and distilling to remove the organic liquid phase to obtain a crude product O. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.0g of a white powder. The white powder was O, yield 58%.
The structure confirmation data for O is as follows: HRMS (APCI) m/z calcd for C57H35N3[M+H]+761.2831,found 761.5486.
Example 13 preparation of a Compound of formula P
Figure BDA0003572445430000171
The method comprises the following specific steps:
(1) to a 250mL two-necked round-bottomed flask, under nitrogen, were added 0.100g (0.291mmol), 0.028g (0.0970mmol) of 2, 4-dibromoquinazoline, 0.083g (0.873mmol) of sodium tert-butoxide, 10mL of toluene in that order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product P. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.0g of a white powder. The white powder was P, yield 58%.
The structure confirmation data for P is as follows: HRMS (APCI) m/z calcd for C60H36N4[M+H]+812.2940,found 812.4606.
Example 14 preparation of Compound of formula Q
Figure BDA0003572445430000172
The method comprises the following specific steps:
(1) under nitrogen protection, compound C, 0.100g (0.291mmol), 0.019g (0.0970mmol) of 2, 7-dichloro-1, 8-naphthyridine, 0.083g (0.873mmol) of sodium tert-butoxide, 10mL of toluene were added in this order to a 250mL two-necked round-bottomed flask and refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic phase to obtain a crude product Q. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.0g of a white powder. The white powder was Q, and the yield was 58%.
The structure confirmation data for Q is as follows: HRMS (APCI) m/z calcd for C60H36N4[M+H]+812.2940,found 812.4606.
Example 15 preparation of a Compound of formula R
Figure BDA0003572445430000181
The method comprises the following specific steps:
(1) to a 500mL two-necked round-bottomed flask, under nitrogen protection, were added compound C, 1.00g (2.91mmol), 0.276g (0.97mmol) of 2, 7-dibromonaphthalene, 0.083g (0.873mmol) of sodium tert-butoxide, 0.033g (0.146mmol) of palladium acetate, 0.168g (0.582mmol) of tri-tert-butylphosphonium tetrafluoroborate, and 50mL of toluene in this order, and the mixture was refluxed at 120 ℃ for 24 hours. And after the reaction system is cooled to room temperature, adding 300mL of water and 300mL of ethyl acetate into the reaction system for extraction, drying and filtering an extracted organic phase by using anhydrous sodium sulfate, and then distilling to remove the organic liquid phase to obtain a crude product R. The crude product was purified by column chromatography (petroleum ether: dichloromethane volume ratio 5:1) to give 1.5g of a white powder. The white powder was R, yield 63%.
The structure confirmation data for R are as follows: HRMS (APCI) m/z calcd for C62H40N2[M+H]+812.3191,found 812.3278.
Example 16
The organic light emitting diode device using the triptycene skeleton-based host material D prepared in embodiment 1 of the present invention as a light emitting layer was manufactured and performance evaluated. Fig. 1 is a schematic structural diagram of an organic light emitting diode.
The manufacturing method of the organic light-emitting diode device with the main fluorescent material D based on the triptycene framework as the light-emitting layer comprises the following steps:
1) pretreatment of the glass substrate: selecting strips with a diameter of 3X 3mm2A glass substrate having an Indium Tin Oxide (ITO) film pattern as a transparent electrode; and cleaning the glass substrate with purified water, putting the glass substrate into ethanol for ultrasonic treatment, and treating the glass substrate with a plasma cleaning machine to obtain the pretreated glass substrate.
2) Vacuum evaporation: vacuum deposition of the subsequent layers was performed on the pretreated glass substrate by a vacuum deposition method. First, a glass substrate was placed in a vacuum deposition chamber, and the pressure was reduced to 6X 10-4Pa below; and then, carrying out vacuum evaporation on the organic compound subjected to resistance heating from the light-emitting layer at a film forming rate of 1-1.5 nm/s, and sequentially evaporating a hole transport layer, the light-emitting layer, an electron transport layer, an electron injection layer and a cathode. Wherein, the glass substrate with the ITO transparent electrode is used as an anode; NPB with the film thickness of 40nm is used as a hole transport layer; a material with a film thickness of 15nm and based on a triptycene skeleton is taken as a main material and is doped with PXZ-TRZ to be taken as a luminescent layer, and the doping proportion of PXZ-TRZ is 5 wt%; TPBi with the film thickness of 60nm is used as an electron transport layer; lithium fluoride with the film thickness of 0.8nm is used as an electron injection layer; aluminum having a film thickness of 80nm was provided with a metal mask so as to be orthogonal to the ITO stripes to form cathodes, thereby obtaining organic light-emitting diodes. The film thickness was measured by a stylus-type film thickness measuring instrument.
The hole transport layer materials NPB (N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine), the electron transport layer material TPBi (1,3, 5-tri (1-phenyl-1H-benzimidazole-2-yl) benzene), the luminescent layer material PXZ-TRZ (10- (4- (4, 6-diphenyl l-1,3, 5-triazine-2-yl) phenyl) -10H-phenoxazine), the electron injection layer material lithium fluoride and the cathode material aluminum are purchased from SianBaote photoelectric material science and technology limited company.
3) Packaging the device: the prepared organic electroluminescent device was sealed in a nitrogen atmosphere glove box having a water oxygen concentration of 0.1ppm or less, and then the film-forming substrate was covered with a sealing cap made of glass with an epoxy type ultraviolet curable resin and sealed by curing under self-tapping.
(II) evaluation of Performance of organic light-emitting diode device having triptycene skeleton-based host Material D as light-emitting layer
Applying a direct current to the fabricated organic light emitting diode, and evaluating the light emitting performance by using a Spectrascan PR670 luminance meter; the current-voltage characteristics were measured using a computer controlled Keithley 2400 digital source meter. The light emitting properties of the organic light emitting diode were measured under the condition that the applied direct current voltage was changed.
The fabricated organic light-emitting diode device has CIE color coordinate values of (0.35, 0.59), External Quantum Efficiency (EQE) of 18.9%, current efficiency of 58.52cd/A, and power efficiency of 52.51 lm/W.
The organic light-emitting diode device is prepared by the method, except that the compound prepared in the embodiment 2-15 is used for replacing the material D. The results obtained are shown in Table 1 below.
TABLE 1 organic light emitting diode device Performance data Table prepared with the compounds of examples 1-15
Figure BDA0003572445430000191
Figure BDA0003572445430000201
The above examples of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. It will be apparent to those skilled in the art that various other modifications and variations can be made in the above-described embodiments, and it is not intended to be exhaustive or to limit the embodiments to the precise form disclosed. All obvious changes and modifications of the present invention shall fall within the scope of the present invention.

Claims (10)

1. A compound represented by formula 1:
Figure FDA0003572445420000011
wherein, in formula 1, Ar represents one or more aromatic rings or aromatic condensed rings.
2. The compound of claim 1, wherein: ar is selected from any one of the following groups: benzene, biphenyl, terphenyl, naphthalene, pyridine, naphthyridine, phenanthridine, quinoline, isoquinoline, pyrimidine, diphenyl sulfone, dibenzo [ f, h ] quinoxaline, and derivatives thereof.
3. The compound of claim 2, wherein: the compound is any one of the following compounds:
Figure FDA0003572445420000012
Figure FDA0003572445420000021
4. a process for the preparation of a compound according to any one of claims 1 to 3, comprising the steps of:
1) will be formula A1A compound of the formula A2Reacting the compound under the catalysis of palladium to obtain a compound shown as a formula B;
Figure FDA0003572445420000022
2) reacting the compound shown in the formula B under the catalysis of palladium to obtain a compound shown in a formula C;
Figure FDA0003572445420000031
3) and (3) reacting the compound shown in the formula C with an aromatic ring or aromatic condensed ring compound to obtain the compound shown in the formula 1.
5. The method of manufacturing according to claim 4, characterized in that: in step 1), the reaction is carried out in Pd (OAc)24, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (xanthphos) and sodium tert-butoxide;
the Pd (OAc)2And the formula A1The molar ratio of the compounds is 0.05-0.2: 1;
the 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene and the compound of formula A1The molar ratio of the compounds is 0.1-0.4: 1;
the sodium tert-butoxide is of the formula A1The molar ratio of the compounds is 1-3: 1;
the formula A1Compounds and said A2The molar ratio of the compounds is 1: 3-10;
the reaction of step 1) is carried out in a solvent; specifically, the solvent is at least one of toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide and dimethylformamide;
in the step 1), the reaction temperature is 70-120 ℃, and the reaction time is 3-6 hours;
the step 1) also comprises a purification step after the reaction; specifically, the purification method adopts at least one of recrystallization, column chromatography and sublimation.
6. The production method according to claim 4 or 5, characterized in that: in step 2), the reaction is carried out in Pd (OAc)2The tri-tert-butylphosphonium tetrafluoroborate and potassium carbonate;
the Pd (OAc)2The molar ratio of the compound to the compound shown in the formula B is 0.05-0.2: 1;
the molar ratio of the tri-tert-butylphosphonium tetrafluoroborate to the compound shown in the formula B is 0.1-0.4: 1;
the molar ratio of the potassium carbonate to the compound shown in the formula B is 1-3: 1;
the reaction in step 2) is carried out in a solvent; specifically, the solvent is at least one of toluene, dimethylformamide and dimethylacetamide;
in the step 2), the reaction temperature is 100-140 ℃, and the reaction time is 10-16 hours;
the step 2) also comprises a purification step after the reaction; specifically, the purification method adopts at least one of recrystallization, column chromatography and sublimation.
7. The production method according to any one of claims 4 to 6, characterized in that: in the step 3), the reaction temperature is 100-150 ℃, and the reaction time is 12-48 hours;
the aromatic or aromatic fused ring compound is dibromobiphenyl, m-dibromobenzene, dibromoterphenyl, 1-bromo-3- (4-bromophenyl) benzene, dibromonaphthalene, dibromo isoquinoline, 6, 11-dibromo dibenzo [ f, h ] quinoxaline, dibromo pyrimidine, dibromo phenanthridine, dibromo diphenyl sulfone, difluoropyridine, dibromo quinazoline or dichloro-1, 8-naphthyridine;
the molar ratio of the compound shown in the formula C to the aromatic ring or aromatic condensed ring compound is 2.5-4: 1;
in the step 3), the reaction is carried out under any one of the following conditions a) to c):
a) in sodium tert-butoxide, Pd (OAc)2And tri-tert-butylphosphonium tetrafluoroborate;
specifically, the molar ratio of the compound shown in the formula C to sodium tert-butoxide is 1: 1-3;
the compound shown as the formula C is reacted with Pd (OAc)2The molar ratio of (A) to (B) can be 1: 0.05-0.2;
the molar ratio of the compound shown in the formula C to the tri-tert-butylphosphonium tetrafluoroborate can be 1: 0.1-0.4;
b) in the presence of potassium carbonate, copper and 18-crown-6;
specifically, the molar ratio of the compound shown in the formula C to potassium carbonate is 1: 1-3;
the molar ratio of the compound shown in the formula C to copper can be 1: 2-7;
the molar ratio of the compound shown in the formula C to the 18-crown-6 can be 1: 0.2-0.8;
c) in the presence of sodium tert-butoxide;
specifically, the molar ratio of the compound shown in the formula C to sodium tert-butoxide can be 1: 1-3;
the reaction in step 3) is also carried out in a solvent; specifically, the solvent is at least one of toluene, dimethylformamide and dimethylacetamide;
the step 3) also comprises a purification step after the reaction; specifically, the purification method adopts at least one of recrystallization, column chromatography and sublimation.
8. Use of a compound according to any one of claims 1 to 3 for the preparation of an organic light emitting diode device.
9. Use according to claim 8, characterized in that: a host material for a light-emitting layer of the organic light-emitting diode device comprising the compound according to any one of claims 1 to 3.
10. An organic light emitting diode device, characterized in that: a host material of the light emitting layer includes the compound according to any one of claims 1 to 3.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011207792A (en) * 2010-03-29 2011-10-20 Fujifilm Corp Compound comprising triptycene structure
JP2012236786A (en) * 2011-05-11 2012-12-06 Konica Minolta Holdings Inc Ptycene-based compound, organic electroluminescent element and illuminating system
CN103420897A (en) * 2013-01-09 2013-12-04 烟台九目化学制品有限公司 Triptycene derivative and application thereof
US20180006225A1 (en) * 2014-12-29 2018-01-04 Dow Global Technologies Llc Compositions with Triarylamine Derivatives and Oled Device Containing the Same
CN111995562A (en) * 2020-09-14 2020-11-27 深圳大学 Triptycene D-A type thermal activation delayed fluorescent material, electronic device and application

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011207792A (en) * 2010-03-29 2011-10-20 Fujifilm Corp Compound comprising triptycene structure
JP2012236786A (en) * 2011-05-11 2012-12-06 Konica Minolta Holdings Inc Ptycene-based compound, organic electroluminescent element and illuminating system
CN103420897A (en) * 2013-01-09 2013-12-04 烟台九目化学制品有限公司 Triptycene derivative and application thereof
US20180006225A1 (en) * 2014-12-29 2018-01-04 Dow Global Technologies Llc Compositions with Triarylamine Derivatives and Oled Device Containing the Same
CN111995562A (en) * 2020-09-14 2020-11-27 深圳大学 Triptycene D-A type thermal activation delayed fluorescent material, electronic device and application

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
曹菁 等: "多蝶烯及其衍生物的合成与应用进展" *

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