CN114213444A - Tetraphenylsilane derivative and preparation method thereof - Google Patents
Tetraphenylsilane derivative and preparation method thereof Download PDFInfo
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- CN114213444A CN114213444A CN202111508137.4A CN202111508137A CN114213444A CN 114213444 A CN114213444 A CN 114213444A CN 202111508137 A CN202111508137 A CN 202111508137A CN 114213444 A CN114213444 A CN 114213444A
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- tetraphenylsilane
- derivative
- aryl
- dropwise adding
- butyl lithium
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- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical class C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- -1 nitro, carboxyl Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- 150000001491 aromatic compounds Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 238000000967 suction filtration Methods 0.000 claims description 23
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 13
- 150000001502 aryl halides Chemical class 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 5
- 238000010791 quenching Methods 0.000 claims description 5
- 230000000171 quenching effect Effects 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical group BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 claims description 4
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 claims description 3
- JMLWXCJXOYDXRN-UHFFFAOYSA-N 1-chloro-3-iodobenzene Chemical compound ClC1=CC=CC(I)=C1 JMLWXCJXOYDXRN-UHFFFAOYSA-N 0.000 claims description 3
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 claims description 3
- BPRGLVVFWRNXEP-UHFFFAOYSA-N 2,6-dibromoanthracene Chemical compound C1=C(Br)C=CC2=CC3=CC(Br)=CC=C3C=C21 BPRGLVVFWRNXEP-UHFFFAOYSA-N 0.000 claims description 3
- RWQLKZHFRDFSFA-UHFFFAOYSA-N 2-bromo-1-iodo-4-phenylbenzene Chemical group C1=C(I)C(Br)=CC(C=2C=CC=CC=2)=C1 RWQLKZHFRDFSFA-UHFFFAOYSA-N 0.000 claims description 3
- PYXBCVWIECUMDW-UHFFFAOYSA-N 2-bromoanthracene Chemical compound C1=CC=CC2=CC3=CC(Br)=CC=C3C=C21 PYXBCVWIECUMDW-UHFFFAOYSA-N 0.000 claims description 3
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 claims description 3
- SQTPFYJEKHTINP-UHFFFAOYSA-N 2-bromophenanthrene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3C=CC2=C1 SQTPFYJEKHTINP-UHFFFAOYSA-N 0.000 claims description 3
- BNGNNFQSUWVWCW-UHFFFAOYSA-N 3-bromophenanthrene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3C=CC2=C1 BNGNNFQSUWVWCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- UDZSLJULKCKKPX-UHFFFAOYSA-N (4-bromophenyl)-triphenylsilane Chemical compound C1=CC(Br)=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UDZSLJULKCKKPX-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000009991 scouring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NYSAPLQZKHQBSO-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-phenylbenzene Chemical group BrC1=C(Br)C(Br)=CC(C=2C=CC=CC=2)=C1Br NYSAPLQZKHQBSO-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010887 waste solvent Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
The application belongs to the technical field of organic chemical synthesis, and particularly relates to a tetraphenylsilane derivative and a preparation method thereof. The existing tetraphenyl silane and derivatives thereof have complex reaction, low yield and complex post-treatment. The application provides a tetraphenylsilane derivative having the general formula:
wherein R1 is hydrogen, alkyl, halogen, amino, cyano, nitro, carboxyl, aromatic compound and its derivative or condensed ring. The reaction is simple and easy to operate, the reaction is safe, the yield is high, the post-treatment is simple, the waste water is less, and the method is more environment-friendly.
Description
Technical Field
The application belongs to the technical field of organic chemical synthesis, and particularly relates to a tetraphenylsilane derivative and a preparation method thereof.
Background
The molecular formula of the tetraphenylsilane derivative is C24H19SiR, and the tetraphenylsilane derivative is insoluble in water. The tetraphenylsilane derivatives have various applications due to their special structures. Different active groups are introduced into the 2.3.4.5.6 position of one benzene ring in the structure, so that the organic electroluminescent material has different applications and more excellent performance in different fields, particularly, silicon atoms can be introduced into the organic electroluminescent material in the aspect of organic electroluminescence, and the organic electroluminescent material has outstanding effects on the service life, the chromaticity and the oxidation resistance of the luminescent material. In recent years, scientists continuously research and develop organic electroluminescence to luminescent materials, the large conjugated structure has excellent luminescent performance or luminescence promoting performance, the requirement on the purity of intermediate materials is higher and higher, and the intermediate materials of the OLED organic luminescent materials are more and more required along with continuous breakthrough and marketization of the OLED organic luminescent materials, so continuous innovation and continuous optimization and improvement of the process are required.
The existing tetraphenyl silane derivative has complex reaction, low yield and complex post-treatment.
Disclosure of Invention
1. Technical problem to be solved
Based on the problems of complex reaction, low yield and complex post-treatment of the existing tetraphenylsilane derivatives, the application provides a tetraphenylsilane derivative and a preparation method thereof.
2. Technical scheme
In order to achieve the above objects, the present application provides a tetraphenylsilane derivative having the general formula:
wherein R is hydrogen, alkyl, halogen, cyano, nitro, aromatic compounds and derivatives or condensed rings thereof.
Another embodiment provided by the present application is: the alkyl is C1-C40, the aryl is benzene, toluene, biphenyl or other aryl derivatives, and the condensed ring is naphthyl, phenanthrene or anthracene.
Another embodiment provided by the present application is: the alkyl is C1-C5, the aryl is a benzene ring or toluene, and the condensed ring is naphthyl.
Another embodiment provided by the present application is: selected from the following specific structural formulas:
the application also provides a preparation method of the tetraphenylsilane derivative, wherein aryl halide is used as a raw material to perform lithium halide exchange under the action of butyl lithium to form an aryl lithium reagent, and the aryl lithium reagent and triphenylchlorosilane undergo nucleophilic substitution reaction to obtain the tetraphenylsilane derivative.
Another embodiment provided by the present application is: the method comprises the following steps:
adding a solvent into a reaction container under the protection of inert gas, stirring, adding an aryl halide, cooling to-90 to-78 ℃ after dissolving, then dropwise adding butyl lithium, keeping the temperature at-90 to-78 ℃ for 0.5 to 3 hours after dropwise adding, dropwise adding a triphenylchlorosilane solution at-90 to-78 ℃, heating to room temperature after dropwise adding, pouring into water for quenching, carrying out suction filtration to obtain a crude solid, and boiling and washing the crude product with toluene to obtain a tetraphenylsilane derivative W1.
Another embodiment provided by the present application is: the solvent is tetrahydrofuran or diethyl ether.
Another embodiment provided by the present application is: the butyl lithium is n-butyl lithium, sec-butyl lithium or tert-butyl lithium.
Another embodiment provided by the present application is: the aryl halide is m-dibromobenzene, p-chloroiodobenzene, m-chloroiodobenzene, 3-bromo-4-iodobiphenyl, 2-bromophenanthrene, 3-bromophenanthrene, 1-bromonaphthalene, 2-bromonaphthalene, 4-bromotoluene, 2-bromoanthracene or 2, 6-dibromoanthracene.
The application also provides an application of the tetraphenylsilane derivative, and the tetraphenylsilane derivative is applied to an organic electro-luminescent material, a high molecular material or an organic flexible material.
3. Advantageous effects
Compared with the prior art, the tetraphenyl silane derivative and the preparation method thereof have the beneficial effects that:
the preparation method of the tetraphenyl silane derivative has the advantages that raw materials are cheap and easy to obtain, the synthetic operation process is simple and easy to operate, corresponding energy consumption is less compared with other schemes, post-treatment is simpler, water washing can be carried out to obtain a product, a high-purity product can be obtained after simple and convenient post-treatment, the cost is high, the cost is lower compared with other methods, no waste solvent is generated, generated waste water is less, the atom utilization rate is high, and the method is more environment-friendly.
Drawings
FIG. 1 is a schematic diagram of the synthetic route to tetraphenylsilane derivatives of the present application.
Detailed Description
Hereinafter, specific embodiments of the present application will be described in detail with reference to the accompanying drawings, and it will be apparent to those skilled in the art from this detailed description that the present application can be practiced. Features from different embodiments may be combined to yield new embodiments, or certain features may be substituted for certain embodiments to yield yet further preferred embodiments, without departing from the principles of the present application.
Equivalent means an amount equivalent to a specified or customary value; chemical terminology is used as a reference to mass ratios at which substances interact.
Referring to fig. 1, the present application provides a tetraphenylsilane derivative having the general formula:
wherein R is hydrogen, alkyl, halogen, cyano, nitro, aromatic compounds and derivatives or condensed rings thereof;
another embodiment provided by the present application is: the alkyl is C1-C40, the aryl is benzene, toluene, biphenyl or other aryl derivatives, and the condensed ring is naphthyl, phenanthrene or anthracene.
Another embodiment provided by the present application is: the alkyl is C1-C5, the aryl is a benzene ring or toluene, and the condensed ring is naphthyl.
Another embodiment provided by the present application is: selected from the following specific structural formulas:
the application also provides a preparation method of the tetraphenylsilane derivative, wherein aryl halide is used as a raw material to perform lithium halide exchange under the action of butyl lithium to form an aryl lithium reagent, and the aryl lithium reagent and triphenylchlorosilane undergo nucleophilic substitution reaction to obtain the tetraphenylsilane derivative.
The aryl halide is firstly subjected to the action of butyl lithium to pull out a molecule of halogen, and then is coupled with the triphenylchlorosilane to obtain the tetraphenylsilane derivative.
Further, the method comprises the steps of: adding a solvent into a reaction container under the protection of inert gas, stirring, adding an aryl halide, cooling to-90 to-78 ℃ after dissolving, then dropwise adding butyl lithium, keeping the temperature at-90 to-78 ℃ for 0.5 to 3 hours after dropwise adding, dropwise adding a triphenylchlorosilane solution at-90 to-78 ℃, heating to room temperature after dropwise adding, pouring into water for quenching, carrying out suction filtration to obtain a crude solid, and boiling and washing the crude product with toluene to obtain a tetraphenylsilane derivative W1.
Quenching the reaction with water at a first point can destroy butyllithium in the system and stop the reaction; the water at the second point can prevent the rapid temperature rise in the quenching process, so that the temperature rise of the reaction system is mild, and the danger of spraying materials is avoided; the third water treatment can convert the product generated in the reaction system from a dissolved state into a solid state for precipitation so as to achieve the effects of separation and purification.
The product is obtained after the product is filtered by a filter funnel, the solid crude product needs to be further purified, the solubility of the product in toluene is lower than that of impurities in toluene, namely, the product can be purified by boiling and washing the toluene.
The purification method commonly used in organic synthesis in scouring is a purification method for purifying a product by the difference in solubility between impurities and the product in a certain solvent, and generally scouring is a purification method used when the solubility of a product in a solvent is lower than that of impurities in toluene.
Further, the solvent is tetrahydrofuran or diethyl ether.
Further, the butyl lithium is n-butyl lithium, sec-butyl lithium or tert-butyl lithium.
Further, the aryl halide is m-dibromobenzene, p-chloroiodobenzene, m-chloroiodobenzene, 3-bromo-4-iodobiphenyl, 2-bromophenanthrene, 3-bromophenanthrene, 1-bromonaphthalene, 2-bromonaphthalene, 4-bromotoluene, 2-bromoanthracene or 2, 6-dibromoanthracene but is not limited to the aryl halide.
The application also provides an application of the tetraphenylsilane derivative, and the tetraphenylsilane derivative is applied to an organic electro-luminescent material, a high molecular material or an organic flexible material.
(1) Adding a solvent into a 1000mL reaction container under the protection of inert gas, stirring, adding an aryl halide, cooling to-90 to-78 ℃ after dissolving, then dropwise adding butyl lithium at-90 to-78 ℃, keeping the temperature at-90 to-78 ℃ for 0.5 to 3 hours after completing dropwise adding, dropwise adding a triphenylchlorosilane solution at-90 to-78 ℃, heating to room temperature after completing dropwise adding, pouring into water, carrying out suction filtration to obtain a crude solid, and boiling and washing the crude product with toluene to obtain the tetraphenylsilane derivative.
The following examples are intended to illustrate the present application but are not intended to limit the scope of the present application. The basic raw materials used in this application are all conventional commercial products.
Example 1:
adding 400ml of tetrahydrofuran and 50g of tetrabromobiphenyl into a 1000ml reactor under the full protection of nitrogen, cooling to-78 ℃ after full dissolution, then dropwise adding 81.5ml of n-butyllithium (n-butyllithium is an n-hexane solution of 2.5 mol/L), preserving heat for 0.5 hour at-78 ℃ after dropwise adding, dropwise adding a tetrahydrofuran solution of triphenylchlorosilane (66.4g of triphenylchlorosilane is dissolved by 200ml of tetrahydrofuran) at-78 ℃, naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, obtaining 96g of crude solid by a suction filtration funnel, boiling and washing the crude solid by 192ml of toluene at 80 ℃ for 1 hour, cooling to 30 ℃, and carrying out suction filtration to obtain 75.2g of refined 4-biphenyltriphenylsilane, wherein HPLC (high performance liquid chromatography) is 99.3%, and the yield is 85%.
Example 2:
adding 400ml of tetrahydrofuran and 50g of p-dibromobenzene into a 1000ml reactor under the full protection of nitrogen, cooling to-90 ℃ after full dissolution, then dropwise adding 80.5ml of n-butyllithium (n-butyllithium is 2.5mol/L n-hexane solution) at-90 ℃, preserving heat for 1 hour at-90 ℃ after dropwise adding, dropwise adding a tetrahydrofuran solution of triphenylchlorosilane (65.6g of triphenylchlorosilane is dissolved by 200ml of tetrahydrofuran), naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, performing suction filtration by using a suction filtration funnel to obtain 88g of crude solid, boiling and washing the crude solid by using 176ml of toluene at 80 ℃ for 1 hour, cooling to 25 ℃, and performing suction filtration to obtain 80.2g of refined 4-bromotetraphenylsilane, wherein the HPLC (high performance liquid chromatography) is 99.5%, and the yield is 90%.
Example 3:
adding 400ml of diethyl ether and 50g of m-dibromobenzene into a 1000ml reactor under the full protection of nitrogen, cooling to-85 ℃ after full dissolution, then dropwise adding 80.5ml of n-butyllithium (n-butyllithium is 2.5mol/L n-hexane solution) at-85 ℃, preserving heat for 3 hours at-85 ℃ after dropwise adding, dropwise adding ethyl ether solution of triphenylchlorosilane (65.6g of triphenylchlorosilane is dissolved by 200ml of diethyl ether) at-85 ℃, naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, performing suction filtration by using a suction filtration funnel to obtain 85g of crude solid, boiling and washing the crude solid by using 176ml of toluene at 80 ℃ for 1 hour, cooling to 25 ℃ and performing suction filtration to obtain 67.7g of refined 4-bromotetraphenylsilane, wherein HPLC (high performance liquid chromatography) is 99.1%, and the yield is 76%.
Example 4:
adding 400ml of tetrahydrofuran and 50g of o-dibromobenzene into a 1000ml reactor under the full protection of nitrogen, cooling to-90 ℃ after full dissolution, then dropwise adding 80.5ml of sec-butyllithium (the sec-butyllithium is 2.5mol/L of n-hexane solution) at-90 ℃, preserving heat for 1 hour at-90 ℃ after dropwise adding, dropwise adding a tetrahydrofuran solution of triphenylchlorosilane (65.6g of triphenylchlorosilane is dissolved by 200ml of tetrahydrofuran), naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, performing suction filtration by using a suction filtration funnel to obtain 77g of crude solid, boiling and washing the crude solid by using 176ml of toluene at 80 ℃ for 1 hour, cooling to 25 ℃, and performing suction filtration to obtain 57.9g of refined 4-bromotetraphenylsilane, wherein the HPLC (high performance liquid chromatography) is 99.1%, and the yield is 65%.
Example 5:
adding 400ml of tetrahydrofuran and 50g of bromobenzene into a 1000ml reactor under the full protection of nitrogen, cooling to-90 ℃ after full dissolution, then dropwise adding 121ml of n-butyllithium (n-butyllithium is an n-hexane solution of 2.5 mol/L) at-90 ℃, preserving heat for 1 hour at-90 ℃ after dropwise adding, dropwise adding a tetrahydrofuran solution of triphenylchlorosilane (98.6g of triphenylchlorosilane is dissolved by 300ml of tetrahydrofuran) at-90 ℃, naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, obtaining 110g of crude solid by suction filtration through a suction filtration funnel, boiling and washing the crude solid by 220ml of toluene at 80 ℃ for 1 hour, cooling to 25 ℃ and obtaining 94.1g of fine 4-bromotetraphenylsilane, wherein HPLC (high performance liquid chromatography) is 99.4%, and the yield is 88%.
Example 6:
adding 400ml of tetrahydrofuran and 50g of p-bromotoluene into a 1000ml reactor under the full protection of nitrogen, cooling to-90 ℃ after full dissolution, then dropwise adding 111.1ml of n-butyllithium (n-butyllithium is 2.5mol/L n-hexane solution) at-90 ℃, preserving heat for 1 hour at-90 ℃ after dropwise adding, dropwise adding a tetrahydrofuran solution of triphenylchlorosilane (90.5g of triphenylchlorosilane is dissolved by 300ml of tetrahydrofuran) at-90 ℃, naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, performing suction filtration by using a suction filtration funnel to obtain 90g of crude solid, boiling and washing the crude solid by using 180ml of toluene at 80 ℃ for 1 hour, cooling to 25 ℃, and performing suction filtration to obtain 61.4g of refined 4-bromotetraphenylsilane, wherein HPLC (high performance liquid chromatography) is 99.1%, and the yield is 60%.
Example 7:
adding 400ml of diethyl ether and 50g of 2.6-dibromoanthracene into a 1000ml reactor under the full protection of nitrogen, cooling to-90 ℃ after full dissolution, then dropwise adding 56.5ml of tert-butyllithium (the tert-butyllithium is 2.5mol/L n-hexane solution) at-90 ℃, preserving heat for 1 hour at-90 ℃ after dropwise adding, dropwise adding an ether solution of triphenylchlorosilane (46g of triphenylchlorosilane is dissolved by 150ml of diethyl ether) at-90 ℃, naturally heating to room temperature after dropwise adding, pouring into 2000ml of water, stirring for 1 hour, performing suction filtration by using a suction filtration funnel to obtain 87g of crude solid, boiling and washing the crude solid by using 174ml of toluene at 80 ℃ for 1 hour, cooling to 25 ℃ and performing suction filtration to obtain 42.2g of 4-bromotetraphenylsilane, wherein HPLC (high performance liquid chromatography) is 99.6%, and the yield is 55%.
The above embodiment example 2 is the most preferred embodiment.
Although the present application has been described above with reference to specific embodiments, those skilled in the art will recognize that many changes may be made in the configuration and details of the present application within the principles and scope of the present application. The scope of protection of the application is determined by the appended claims, and all changes that come within the meaning and range of equivalency of the technical features are intended to be embraced therein.
Claims (10)
1. A tetraphenylsilane derivative characterized by: the general formula of the derivative is:
wherein R is hydrogen, alkyl, halogen, cyano, nitro, aromatic compounds and derivatives or condensed rings thereof.
2. The tetraphenylsilane derivative of claim 1, wherein: the alkyl is C1-C40, the aryl is benzene, toluene, biphenyl or other aryl derivatives, and the condensed ring is naphthyl, phenanthrene or anthracene.
3. The process for producing the tetraphenylsilane derivative according to claim 1, wherein: the alkyl is C1-C5, the aryl is a benzene ring or toluene, and the condensed ring is naphthyl.
4. The tetraphenylsilane derivative according to any one of claims 1 to 3, wherein: selected from the following specific structural formulas:
5. a method for preparing tetraphenylsilane derivatives, characterized in that: aryl halide is used as a raw material to perform lithium halide exchange under the action of butyl lithium to form an aryl lithium reagent, and the aryl lithium reagent and triphenylchlorosilane undergo nucleophilic substitution reaction to obtain the tetraphenylsilane derivative.
6. The process for producing a tetraphenylsilane derivative according to claim 5, wherein: the method comprises the following steps: adding a solvent into a reaction container under the protection of inert gas, stirring, adding an aryl halide, cooling to-90 to-78 ℃ after dissolving, then dropwise adding butyl lithium, keeping the temperature at-90 to-78 ℃ for 0.5 to 3 hours after dropwise adding, dropwise adding a triphenylchlorosilane solution at-90 to-78 ℃, heating to room temperature after dropwise adding, pouring into water for quenching, carrying out suction filtration to obtain a crude solid, and boiling and washing the crude product with toluene to obtain a tetraphenylsilane derivative W1.
7. The process for producing a tetraphenylsilane derivative according to claim 6, wherein: the solvent is tetrahydrofuran or diethyl ether.
8. The process for producing a tetraphenylsilane derivative according to claim 6, wherein: the butyl lithium is n-butyl lithium, sec-butyl lithium or tert-butyl lithium.
9. The process for producing a tetraphenylsilane derivative according to claim 6, wherein: the aryl halide is m-dibromobenzene, p-chloroiodobenzene, m-chloroiodobenzene, 3-bromo-4-iodobiphenyl, 2-bromophenanthrene, 3-bromophenanthrene, 1-bromonaphthalene, 2-bromonaphthalene, 4-bromotoluene, 2-bromoanthracene or 2, 6-dibromoanthracene.
10. The application of a tetraphenylsilane derivative is characterized in that: the tetraphenylsilane derivative as defined in claims 1 to 4 is applied to an organic electro-luminescent material, a polymer material or an organic flexible material.
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| CN101177431A (en) * | 2006-11-08 | 2008-05-14 | 三星Sdi株式会社 | Silanylamine-based compound, method of preparing the same and organic light emitting device including organic layer comprising the silanylamine-based compound |
| KR20090033741A (en) * | 2007-10-01 | 2009-04-06 | 동우 화인켐 주식회사 | Organosilane compounds, materials comprising the same for organic electroluminescent device, and organic electroluminescent device |
| WO2009148257A2 (en) * | 2008-06-03 | 2009-12-10 | 주식회사 두산 | Novel silicon-based compound, production method thereof, and organic light-emitting element employing the same |
| US20130293094A1 (en) * | 2012-05-04 | 2013-11-07 | Universal Display Corporation | Asymmetric Hosts With Triaryl Silane Side Chains |
| CN111675732A (en) * | 2019-03-11 | 2020-09-18 | 三星显示有限公司 | Heterocyclic compound and organic light-emitting device including the same |
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| CN101177431A (en) * | 2006-11-08 | 2008-05-14 | 三星Sdi株式会社 | Silanylamine-based compound, method of preparing the same and organic light emitting device including organic layer comprising the silanylamine-based compound |
| KR20090033741A (en) * | 2007-10-01 | 2009-04-06 | 동우 화인켐 주식회사 | Organosilane compounds, materials comprising the same for organic electroluminescent device, and organic electroluminescent device |
| WO2009148257A2 (en) * | 2008-06-03 | 2009-12-10 | 주식회사 두산 | Novel silicon-based compound, production method thereof, and organic light-emitting element employing the same |
| US20130293094A1 (en) * | 2012-05-04 | 2013-11-07 | Universal Display Corporation | Asymmetric Hosts With Triaryl Silane Side Chains |
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