CN113896675A - Organic luminescent material based on carbazole-triphenylamine derivative and preparation method thereof - Google Patents
Organic luminescent material based on carbazole-triphenylamine derivative and preparation method thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 39
- SHNBZFPUQOYBTJ-UHFFFAOYSA-N 9h-carbazole;n,n-diphenylaniline Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SHNBZFPUQOYBTJ-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- -1 boron ester compounds Chemical class 0.000 claims abstract description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004440 column chromatography Methods 0.000 claims abstract description 7
- CGNKSELPNJJTSM-UHFFFAOYSA-N phenylphosphonous acid Chemical compound OP(O)C1=CC=CC=C1 CGNKSELPNJJTSM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052796 boron Inorganic materials 0.000 claims abstract description 6
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 6
- 238000010276 construction Methods 0.000 claims abstract description 4
- 238000006052 Horner reaction Methods 0.000 claims abstract description 3
- 150000001716 carbazoles Chemical class 0.000 claims abstract description 3
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 238000005859 coupling reaction Methods 0.000 claims abstract description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims abstract description 3
- 238000001953 recrystallisation Methods 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 238000003828 vacuum filtration Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000006617 triphenylamine group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 4
- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
- 238000007385 chemical modification Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 150000001651 triphenylamine derivatives Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present case relates to an organic photoelectric material based on carbazole-triphenylamine derivatives and a preparation method thereof, the material is prepared by taking carbazole derivatives, triphenylamine derivatives, boron ester compounds and triethyl phenylphosphonite as construction units through intermolecular nucleophilic substitution reaction, palladium catalytic coupling reaction and twisting-horner reaction, and is purified through column chromatography or recrystallization, and the material molecules have the following structural general formula:
Description
Technical Field
The invention relates to the field of organic photoelectric functional materials and organic synthesis, in particular to an organic photoelectric material based on carbazole-triphenylamine derivatives and a preparation method thereof.
Background
The organic photoluminescence material is mainly some organic conjugated small molecules or macromolecules, and the organic conjugated small molecules have the characteristics of wide adjustable range of emission wavelength, easiness in modification, simplicity in preparation and the like. The conjugation degree and intramolecular charge distribution of the system can be changed by introducing electron-donating groups such as nitrogen-containing groups and aromatic rings and strong electron-withdrawing structures such as cyano-groups, carboxylic acids and halogens in the molecules, so that push-pull electron structure molecules are constructed, and the change of energy bands of electron pairs and pi conjugated systems is further pushed and pulled, so that the photoelectric properties of the compound can be changed. The organic luminescent molecule taking triphenylamine as a donor group has good film forming property and solubility, has the characteristics of good charge transmission capability, high oxidation potential and the like, and is therefore an alternative material of an organic photoelectric functional material; recently, carbazole and its derivatives have become star molecules for constructing long-life phosphorescent materials due to their unique light-emitting properties.
In recent years, research on organic luminescent materials is mainly focused on research on organic fluorescent materials, and the organic fluorescent materials generally have the problem of short luminescent life, so that the construction of the luminescent materials with long service life is the main object of the invention.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to construct and synthesize a push-pull type long-life luminescent material based on carbazole-triphenylamine derivatives.
In order to achieve the purpose, the invention provides the following technical scheme:
the organic photoelectric material based on the carbazole-triphenylamine derivative is prepared by taking a carbazole derivative, a triphenylamine derivative, a boron ester compound and a triethyl phenylphosphonite derivative as a construction unit through intermolecular nucleophilic substitution reaction, palladium catalytic coupling reaction and cutting-horner reaction, and is purified through column chromatography or recrystallization, wherein the material molecule has the following structural general formula:
wherein the content of the first and second substances,
the invention further provides a preparation method of the carbazole-triphenylamine derivative organic photoelectric material, which comprises the following steps:
the first step,
Under the protection of nitrogen, adding a carbazole compound into a reaction bottle, adding 4,4 '-diiodo-4' -bromotriphenylamine or 4,4 '-diiodo-4' -aldehyde triphenylamine, taking potassium iodide/potassium carbonate as a catalyst, taking dimethyl acetamide as a solvent, and reacting in an oil bath kettle at the temperature of 160-165 ℃ for 48 hours to obtain a carbazole-triphenylamine bromide compound or carbazole-triphenylamine aldehyde compound;
step two,
Under the protection of nitrogen, dissolving a carbazole-triphenylamine aldehyde compound, a triethyl phenylphosphonite derivative and sodium hydride in DMF, slowly heating to 85-100 ℃ for reaction for 24 hours, and separating and purifying after the reaction is finished to obtain a target compound shown in formula 1);
under the protection of nitrogen, adding carbazole-triphenylamine bromine compound, boron ester compound, potassium carbonate and tetratriphenylphosphine palladium into a reaction bottle, adding DMSO to dissolve the carbazole-triphenylamine bromine compound, reacting at 85-100 ℃ for 24 hours, and after the reaction is finished, separating and purifying to obtain the target compound shown in formula 2).
Preferably, the separation and purification steps in the first step are as follows: after the reaction is finished, cooling to room temperature, pouring the reaction liquid into water, precipitating a large amount of solid after acidification, performing vacuum filtration, and recrystallizing in ethanol.
Preferably, the separation and purification steps in the second step are as follows: after the reaction is finished, pouring into ice water, adjusting the pH value to be weakly acidic, separating out solid, decompressing, filtering, drying, and performing column chromatography by using dichloromethane/petroleum ether.
Preferably, the triethyl phenylphosphonite derivative is
The boron esterThe compound is
The preparation process of the present invention can be represented by the following general formula:
1) synthesizing a compound represented by the formula 1):
2) synthesizing a compound represented by the formula 2):
the invention has the beneficial effects that: the invention selects carbazole with phosphorescence as a modification group, prepares the phosphorescent material with higher fluorescence quantum yield and longer luminescence life through chemical modification, and compared with the prior art, the material has longer luminescence life and good light stability. In addition, the material has the advantages of short synthetic route, mild reaction conditions, low requirements on instruments and equipment, market-oriented main sources of reaction raw materials, low price, wide sources and high yield of prepared materials, and provides reference for the research of enriching and developing phosphorescent materials.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments, and it should be understood that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In addition, the technical features involved in the different embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Example 1:
step 1:
under the protection of nitrogen, 8.5g (51mmol) of carbazolomide, 13.3g (25mmol) of 4,4 '-diiodo-4' -bromotriphenylamine, 4.8g of potassium iodide and 5g of phenanthroline (10g) potassium carbonate are added into a 100mL two-port bottle and dissolved in 100mL DMAC and reacted for 48 hours at the temperature of 160-165 ℃ in an oil bath kettle. Detecting the reaction process by a thin-layer chromatography plate, cooling to room temperature after the reaction is finished, pouring the reaction liquid into 80ml of water, carrying out vacuum filtration, and recrystallizing with ethanol to obtain a compound KZ-BR, 14.6g, yield: 88 percent. δ 8.16(d, J ═ 7.7Hz,4H),7.78(d, J ═ 8.64Hz,2H),7.60(d, J ═ 8.67Hz,4H),7.51-7.40(m,12H),7.32-7.26(m, 6H).
Step 2
Under the protection of nitrogen, dissolving a compound KZ-BR (8.0g, 12.2mmol), a 3, 5-trifluoromethyl boron ester compound (4.2g, 13mmol), tetratriphenylphosphine palladium (0.012g) and potassium carbonate (1.7g, 13mmol) in 100ml DMSO, bubbling nitrogen for 15-30min, slowly heating to 85-100 ℃, keeping the temperature for 24 hours, detecting and tracking the reaction process by chromatography, pouring the reaction solution into 30ml ice water after the reaction is finished, adjusting the pH value to weak acidity by hydrochloric acid to separate out a large amount of green solids, performing reduced pressure extraction, and performing column chromatography by using dichloromethane/petroleum ether as a mobile phase to obtain a light yellow solid KZ-SF 8.2g, wherein the yield is as follows: 82 percent.1H NMR(300MHz,CDCl3)δ8.33-8.24(s,3H),8.20(d,J＝7.7Hz,4H),7.88(d,J＝8.64Hz,2H),7.62(d,J＝8.67Hz,4H),7.54-7.43(m,12H),7.34-7.28(m,6H)。
Example 2
Step 1
KZ-CHO was prepared in 86% yield by replacing 4,4 '-diiodo-4' -bromotriphenylamine with 4,4 '-diiodo-4' -aldehyde triphenylamine in step 1 of example 1,1H NMR(300MHz,CDCl3)δ:9.93(s,1H),8.16(s,4H),7.86(d,J＝8.5Hz,2H),7.62(d,J＝8.49Hz,4H),7.54–7.45(m,12H),7.31(d,J＝8.19Hz,2H),1.50(s,36H)。
step 2
Synthesis of KZ-SFL, under nitrogen protection, compounds KZ-CHO (6.5g, 7.8mmol), 3, 5-trifluoromethylphenylphosphinite (2.7g, 8mmol), NaH (1.2g, 20mmol), dissolved in 100ml DMF, nitrogen bubbling for 30min, then slowly raising temperature to 85-100 ℃ and keeping warm for 24 hours, chromatographic detection and following the reaction progress, pouring the reaction solution into 30ml ice water, adjusting pH to weak acidity with hydrochloric acid, then precipitating a large amount of solid, vacuum pumping, column chromatography with dichloromethane/petroleum ether as mobile phase to obtain a pale yellow solid KZ-SFL 6.9g, yield 85%, delta: 8.18(s,4H),7.88(d, J ═ 8.5Hz,2H),7.64(d, J ═ 8.49Hz,4H), 7.59-7.56 (s,3H),7.56-7.46(m,12H),7.32(d, 8.19H), 19.19 ═ 8H, 19 Hz), 6.59-6.56(d, J ═ 9Hz,2H),1.54(s, 36H).
Example 3
Step 1
Synthetic yield of KZ-BR: 88 percent. δ 8.16(d, J ═ 7.7Hz,4H),7.78(d, J ═ 8.64Hz,2H),7.60(d, J ═ 8.67Hz,4H),7.51-7.40(m,12H),7.32-7.26(m, 6H).
Step 2
Synthetic yield of KZ-COH: 80 percent.1H NMR(300MHz,CDCl3)δ11.20(s,2H),8.34-8.24(s,3H),8.22-7.98(d,J＝7.7Hz,4H),7.88-7.82(d,J＝8.64Hz,2H),7.66(d,J＝8.67Hz,4H),7.56-7.44(m,12H),7.35-7.30(m,6H)。
Example 4
Step 1
The synthesis of KZ-CHO, the yield is 86 percent,1H NMR(300MHz,CDCl3)δ:9.93(s,1H),8.16(s,4H),7.86(d,J＝8.5Hz,2H),7.62(d,J＝8.49Hz,4H),7.54–7.45(m,12H),7.31(d,J＝8.19Hz,2H),1.50(s,36H)。
step 2
Synthesis of SKZ-B in 86% yield, δ 8.18(s,4H),7.88(d, J ═ 8.5Hz,2H),7.74-7.68(d, J ═ 9.0Hz,4H),7.64(d, J ═ 8.49Hz,4H),7.56-7.46(m,12H),7.34(d, J ═ 8.2Hz,2H),6.59-6.56(d, J ═ 9Hz,2H),1.56(s, 36H).
And (3) testing fluorescence and ultraviolet spectrums of the material: configuring a molecule to 10-5～10-6The THF solution with mol/L concentration is used for measuring the absorption spectrum and the emission spectrum of the material by an ultraviolet absorption spectrometer and a fluorescence spectrometer respectively, and the fluorescence quantum yield is calculated, wherein the following table 1 is the spectrum data of corresponding molecules.
TABLE 1
| Compound (I) | Maximum absorption lambdaWavelength nm | Maximum transmission lambdaWavelength nm | Yield of fluorescence quantum | Phosphorescent lifetime(s) |
| KZ-SF | 456 | 520 | 0.78 | 1.2 |
| KZ-SFL | 456 | 510 | 0.84 | 2.0 |
| KZ-COH | 450 | 524 | 0.78 | 2.1 |
| SKZ-B | 450 | 532 | 0.84 | 2.2 |
By combining the embodiments 1-4, the reaction conditions of the invention are mild, the reaction is efficient, the operation is simple and convenient, the applicability is wide, and a new reference is provided for enriching and developing the phosphorescent material.
While embodiments of the invention have been disclosed above, it is not limited to the applications listed in the description and the embodiments, which are fully applicable in all kinds of fields of application of the invention, and further modifications may readily be effected by those skilled in the art, so that the invention is not limited to the specific details without departing from the general concept defined by the claims and the scope of equivalents.
Claims (6)
1. The organic photoelectric material based on the carbazole-triphenylamine derivative is characterized in that the material is prepared by taking a carbazole derivative, a triphenylamine derivative, a boron ester compound and a triethyl phenylphosphonite derivative as construction units through intermolecular nucleophilic substitution reaction, palladium catalytic coupling reaction and twisting-horner reaction, and is purified through column chromatography or recrystallization, wherein the material molecule has the following structural general formula:
wherein R is1＝H，
2. The method for preparing the carbazole-triphenylamine derivative organic photoelectric material according to claim 1, comprising the steps of:
the first step,
Under the protection of nitrogen, adding a carbazole compound into a reaction bottle, adding 4,4 '-diiodo-4' -bromotriphenylamine or 4,4 '-diiodo-4' -aldehyde triphenylamine, taking potassium iodide/potassium carbonate as a catalyst, taking dimethyl acetamide as a solvent, and reacting in an oil bath kettle at the temperature of 160-165 ℃ for 48 hours to obtain a carbazole-triphenylamine bromide compound or carbazole-triphenylamine aldehyde compound;
step two,
Under the protection of nitrogen, dissolving a carbazole-triphenylamine aldehyde compound, a triethyl phenylphosphonite derivative and sodium hydride in DMF, slowly heating to 85-100 ℃ for reaction for 24 hours, and separating and purifying after the reaction is finished to obtain a target compound shown in formula 1);
under the protection of nitrogen, adding carbazole-triphenylamine bromine compound, boron ester compound, potassium carbonate and tetratriphenylphosphine palladium into a reaction bottle, adding DMSO to dissolve the carbazole-triphenylamine bromine compound, reacting at 85-100 ℃ for 24 hours, and after the reaction is finished, separating and purifying to obtain the target compound shown in formula 2).
3. The method for preparing the carbazole-triphenylamine derivative organic photoelectric material according to claim 2, wherein the step of separating and purifying in the first step is: after the reaction is finished, cooling to room temperature, pouring the reaction liquid into water, precipitating a large amount of solid after acidification, performing vacuum filtration, and recrystallizing in ethanol.
4. The method for preparing the carbazole-triphenylamine derivative organic photoelectric material according to claim 2, wherein the step of separating and purifying in the second step comprises: after the reaction is finished, pouring into ice water, adjusting the pH value to be weakly acidic, separating out solid, decompressing, filtering, drying, and performing column chromatography by using dichloromethane/petroleum ether.
5. The method for producing the carbazole-triphenylamine derivative organic photoelectric material according to claim 2, wherein the triethyl phenylphosphonite derivative is
6. The method for preparing the carbazole-triphenylamine derivative organic photoelectric material of claim 2, wherein the borate compound is
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| CN114644619A (en) * | 2022-04-06 | 2022-06-21 | 扬州工业职业技术学院 | Organic photoelectric material based on carbazole-naphthalimide derivative and preparation method thereof |
Citations (5)
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