CN110746462A - Efficient synthesis method of dendritic cyclotriphosphazene compound - Google Patents
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- -1 cyclotriphosphazene compound Chemical class 0.000 title claims description 7
- 238000001308 synthesis method Methods 0.000 title abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 8
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004305 biphenyl Substances 0.000 claims abstract description 7
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- VHHDLIWHHXBLBK-UHFFFAOYSA-N anthracen-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=C(C=CC=C3)C3=CC2=C1 VHHDLIWHHXBLBK-UHFFFAOYSA-N 0.000 claims description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XUNKEUNEDNWXFV-UHFFFAOYSA-N 1-(2-phenylphenyl)anthracene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 XUNKEUNEDNWXFV-UHFFFAOYSA-N 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 claims description 2
- 239000003049 inorganic solvent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 125000005577 anthracene group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- LOZAIRWAADCOHQ-UHFFFAOYSA-N triphosphazene Chemical compound PNP=NP LOZAIRWAADCOHQ-UHFFFAOYSA-N 0.000 claims 1
- 238000007039 two-step reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical compound N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004327 boric acid Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 3
- QARVLSVVCXYDNA-IDEBNGHGSA-N bromobenzene Chemical group Br[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 QARVLSVVCXYDNA-IDEBNGHGSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 230000004580 weight loss Effects 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the field of new chemical materials, and aims to provide a dendritic organic blue-light material and a high-efficiency synthesis method thereof. The organic molecules with dendritic structures are used as photoelectric conversion materials, have the characteristics of high photoelectric conversion efficiency, easiness in processing and forming and the like, but are difficult to prepare and low in synthesis yield. The invention discloses a high-efficiency synthesis method of an organic blue light material which takes cyclotriphosphazene as a core and is connected with a luminescent group anthracene through biphenyl. In the synthesis method, 9-anthracene boric acid and 4-bromo-4' -hydroxybiphenyl are connected to generate an arm monomer through Suzuki coupling reaction; and then an arm monomer is connected with hexachlorocyclotriphosphazene through nucleophilic substitution reaction to generate a dendritic target product. The synthesis method has the characteristics of simple synthesis route, mild conditions, short reaction time, complete reaction and high yield of the 6-arm dendritic target product.
Description
Technical Field
The invention belongs to the field of new chemical materials, and aims to provide a dendritic organic blue-light material and a high-efficiency synthesis method thereof.
Background
Dendrimers are highly branched and structurally precise molecules whose main structure comprises three parts, an inner core, branching units and peripheral groups. The organic molecules with the dendritic structures are used as photoelectric conversion materials and have the characteristics of high photoelectric conversion efficiency and easy dissolution and processing forming. The dendrimer which takes cyclotriphosphazene as a core and is connected with the luminescent group through biphenyl also has excellent high temperature resistance and is particularly suitable for connecting the blue-emitting group. At present, for the compounds, the synthesis method generally starts from hexachlorocyclotriphosphazene, a branching unit is connected through nucleophilic substitution reaction in the first step, and a peripheral luminescent group is connected through coupling reaction in the second step. However, for the synthetic route, in the second step of reaction, because the number of branching units is more (6), the steric hindrance is very large, the difficulty of directly coupling the bromobenzene unit with the boric acid structure on the luminescent group is very large, the reaction is incomplete, and the yield of the 6-arm dendritic target product is very low. In order to promote the reaction, a method of activating end groups is adopted, a first step is to connect a branching unit through nucleophilic substitution reaction, a second step is to convert a bromobenzene end group into a boron ester structure through activating the end groups, and also in order to meet the reaction requirement, a part of a luminescent group is also converted into the bromobenzene structure, and a third step is to connect the two parts through coupling reaction. The synthesis yield is low due to the addition of one step reaction.
Disclosure of Invention
The invention discloses a high-efficiency synthesis method of a dendritic cyclotriphosphazene compound. Research on a target compound synthesis method which takes cyclotriphosphazene as a core and is connected with luminescent group anthracene through biphenyl shows that the synthesis route reported in the literature is reversed, and the Suzuki coupling reaction is firstly carried out on 9-anthraceneboronic acid and 4-bromo-4' -hydroxybiphenyl to generate an arm monomer, so that the generation of a steric hindrance effect is avoided; then, an arm is attacked by hexachlorocyclotriphosphazene through nucleophilic substitution reaction to generate a dendritic target product. The synthesis method has the characteristics of simple synthesis route, mild conditions, short reaction time, complete reaction and high yield of the 6-arm dendritic target product.
The invention is realized by the following measures: the general formula of the structure of the dendritic cyclotriphosphazene compound is shown in figure 1, and the synthesis method comprises 2 steps of reaction. The first step is that 9-anthracene boric acid reacts with 4-bromo-4 ' -hydroxybiphenyl to generate anthracene base-biphenyl ' arm ',
the second step is that the anthracene group-biphenyl 'arm' and hexachlorocyclotriphosphazene take nucleophilic substitution reaction to generate target compound,
in the first step of the reaction, the organic solvent used is a polar aprotic solvent, such as dioxane, tetrahydrofuran; the inorganic solvent is deionized water, and the adding proportion is 10-20: 1; the reaction temperature is 66-101 ℃.
In the first step, strong alkali and weak acid salt such as sodium carbonate and potassium carbonate are added.
In the first step, palladium complex compounds such as tetrakis (triphenylphosphine) palladium, 1' -bisdiphenylphosphinoferrocene palladium dichloride and tris (dibenzylideneacetone) dipalladium are used as catalysts.
In the first-step reaction, the molar ratio of the 4-bromo-4' -hydroxybiphenyl to the 9-anthraceneboronic acid is 1: 1.2-1.5.
In the second step, the solvent used is an anhydrous polar aprotic solvent, such as dioxane and tetrahydrofuran, and the reaction is carried out under reflux conditions.
In the second reaction step, the base used was cesium carbonate.
In the second step of reaction, the molar ratio of hexachlorocyclotriphosphazene to anthracenyl-biphenyl "arms" is 1: 7-9.
The method can effectively reduce the influence of the steric hindrance of the catalyst ligand and the reactant molecules in the coupling reaction, and has the advantages of simple route, mild condition, short reaction time and high yield of the 6-arm dendritic target product. The Suzuki coupling yield can reach 85 percent.
Drawings
FIG. 1 structural general formula of dendritic cyclotriphosphazene compound
FIG. 2 absorption and emission spectra of the compound hexa [9- (4' -oxydiphenyl) anthracene ] cyclotriphosphazene (solvent chloroform)
FIG. 3 shows the thermogravimetric curve of hexa [9- (4' -oxydiphenyl) anthracene ] cyclotriphosphazene at 20-800 deg.C
Detailed Description
For a better understanding of the present invention, the following examples are presented:
example 1
Synthesis of 9- (4-hydroxybiphenyl) anthracene, 1.120g of 9-anthraceneboronic acid, 1.000g of 4-bromo-4' -hydroxybiphenyl and 1.104g of potassium carbonate were sequentially added to a 100mL double-necked flask, and 0.462g of tetrakis (triphenylene) was rapidly added under an argon flow atmospherePhenylphosphine) palladium, 20mL of 1, 4-dioxane and 2mL of deionized water were added with further syringe and finally the flask was subjected to three evacuation/argon cycles. The reaction was stopped after 12 hours under reflux, the reaction solution was filtered, the filtrate was extracted with ethyl acetate and saturated brine, the organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was spin-dried to obtain a crude product. The crude product was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (2: 1). After spin-drying of the solvent 1.051g were obtained as a yellow solid, yield (82.9%).1H NMR(400MHz,DMSO-d6)δ9.63(s,1H),8.69(s,1H),8.16(d,J＝8.4Hz,2H), 7.84(d,J＝7.8Hz,2H),7.65(dd,J＝13.1,8.6Hz,4H),7.57–7.50(m,2H),7.44(dt,J＝8.9,3.5 Hz,4H),7.02–6.85(m,2H).
Example 2
Hexa [ (9-hydroxydiphenyl) anthracene]Synthesis of Cyclotriphosphazene 1.038g of 9- (4-hydroxybiphenyl) anthracene obtained in example 1, 1.133g of cesium carbonate and 20mL of anhydrous THF were sequentially charged into a 100mL two-necked flask, and the flask was subjected to three cycles of evacuation and filling with argon. After heating and stirring, refluxing for 1h, a solution of 0.100g of hexachlorocyclotriphosphazene in 5mL of anhydrous THF was slowly added dropwise to the flask using a syringe. And continuing the reaction for 24 hours, stopping the reaction, filtering the reaction solution, extracting the filtrate by using chloroform and saturated saline solution, drying the organic layer by using anhydrous magnesium sulfate, filtering, and spin-drying the solvent in the filtrate to obtain a crude product. The crude product was purified by silica gel column chromatography eluting with chloroform/petroleum ether (1: 1). After spin-drying of the solvent 0.706g of a pale yellow solid was obtained, yield (85.3%).1H NMR(400MHz,Chloroform-d)δ8.40(s,6H),7.94(d,J＝8.5Hz,12H),7.80(d,J＝8.1Hz,12H),7.71(d,J＝8.6Hz,12H),7.64(d,J＝8.9Hz,12H),7.46(d,J＝8.2Hz,12H),7.27 (t,J＝9.2Hz,24H),7.26CDCl3(s,7H),7.14–7.04(m,12H).MALDI-TOF 2207.0(M+) The absorption and emission spectra of the target compound are shown in figure 2, and the thermal weight loss curve is shown in figure 3.
Claims (9)
1. A dendritic cyclotriphosphazene compound is characterized in that triphosphazene is taken as a core, an anthracene group is connected through biphenyl, and the structural general formula is
Wherein R is any possible substituent on the anthracene ring, including but not limited to an aromatic group or an alkyl group.
2. A method for preparing a dendritic cyclotriphosphazene compound according to claim 1, comprising a two-step reaction: in the first step of reaction, 9-anthraceneboronic acid reacts with 4-bromo-4 ' -hydroxybiphenyl to generate anthracenyl-biphenyl ' arms '; in the second step of reaction, anthracene base-biphenyl 'arm' reacts with hexachlorocyclotriphosphazene to generate target compound.
3. The process according to claim 2, wherein the organic solvent used in the first step is a polar aprotic solvent such as dioxane, tetrahydrofuran; the inorganic solvent is deionized water, and the adding proportion is 10-20: 1; the reaction temperature is 66-101 ℃.
4. The method of claim 2, wherein a strong alkali and weak acid salt such as sodium carbonate and potassium carbonate is added in the first reaction.
5. The process according to claim 2, wherein the first reaction step is carried out using a palladium complex compound as a catalyst, such as tetrakis (triphenylphosphine) palladium, 1' -bisdiphenylphosphinoferrocene palladium dichloride, tris (dibenzylideneacetone) dipalladium.
6. The production method according to claim 2, wherein the molar ratio of 4-bromo-4' -hydroxybiphenyl to 9-anthraceneboronic acid in the first reaction is 1:1.2 to 1.5.
7. The process according to claim 2, wherein the solvent used in the second step is an anhydrous polar aprotic solvent such as dioxane or tetrahydrofuran, and the reaction is carried out under reflux.
8. The method according to claim 2, wherein the base used in the second reaction step is cesium carbonate.
9. The method of claim 2, wherein the molar ratio of hexachlorocyclotriphosphazene to anthracenyl-biphenyl "arms" in the second reaction stage is 1:7 to 9.
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| CN113754886A (en) * | 2021-08-02 | 2021-12-07 | 株洲时代新材料科技股份有限公司 | Hyperbranched polyimide and preparation method thereof |
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| CN106398682A (en) * | 2016-03-21 | 2017-02-15 | 北京理工大学 | Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor |
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Cited By (2)
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| CN113754886A (en) * | 2021-08-02 | 2021-12-07 | 株洲时代新材料科技股份有限公司 | Hyperbranched polyimide and preparation method thereof |
| CN113754886B (en) * | 2021-08-02 | 2023-06-06 | 株洲时代新材料科技股份有限公司 | Hyperbranched polyimide and preparation method thereof |
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