CN101139319A - Substituted quinoline trimer indene derivative and method for making same - Google Patents
Substituted quinoline trimer indene derivative and method for making same Download PDFInfo
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Abstract
The present invention belongs to the technological field of the organic electroluminescent material, specifically relating to the substituted quinoline tripolyphosphate indene derivative and the preparation. In the present invention, the tripolyphosphate indene is used as the raw material; the secondary base is introduced on the fifth, tenth and fifteenth levels to increase the solubility; then the material is acylated with the friedel gram; the acetyl can be introduced on the second, seventh and twelfth levels; the different dosages of the acylating reagent is adjusted to get the single-acylated, double-acylated and wholly acylated tripolyphosphate indene. The intermediates are respectively concentrated with the substituted 2-amido dibenzophenone through the Furuidelande with the acid catalyst to prepare a series of phenyl substituted single-quinoline, double-quinoline, tri-quinoline tripolyphosphate indene derivative. The molecule of the compounds has the good fluorescent characteristics and provides a novel way for the novel electroluminescent material.
Description
Technical field
The present invention relates to the electroluminescent organic material technical field, particularly class substituted quinoline trimer indene derivative and preparation method thereof.
Background technology
Traditional photoelectric functional material mainly is metal, metalloid and some oxide compounds, and how organic compound does not possess unbound electron owing to its constructional feature, thereby has no chance with functions such as light, electricity, magnetic for a long time.Flourish along with the optoelectronic information industry constantly proposed new higher level requirement to material, and over nearly two, 30 years, people have also showed keen interest to the photoelectric properties of organic compound.Since the seventies, people have successively found organic conductor, organic superconductor, Organic Ferromagnet, organic non linear optical material etc., explore at theory research and material and have showed brilliant prospect aspect two.
Organic electroluminescent also is Organic Light Emitting Diode (OLED), is one of the flat pannel display field to study focus ([1] Tang, C.W greatly in the world in recent years; Van Slyke S.A.Appl.Phys.Lett.1987,51,91; [2] Muller C.D., Falcou A., Reckefuss N.et al.Nature, 2003,421,829.), advantage such as have panelized, active illuminating, brightness height, high-contrast, response speed is fast, driving voltage is low and be considered to a kind of new technology ([3] Teng Feng, Hou Yanbing, the seal Shou Gen etc. of following most possible replacement liquid crystal display, electroluminescent organic material and use in May, 2006, Chemical Industry Press).The application of technique of display in the modern life also more and more widely, as mobile phone screen, instrument display screen, computer terminal indicating meter, televisor and outdoor large screen display screen etc.Therefore, no matter still from a business perspective from scientific and technological angle, the novel high-performance technique of display all can become the research focus in technique of display field in the world, therefore cause the very big concern of people, explore and study the heat subject that novel luminous organic material has just become research field electroluminescent organic material and electroluminescent device.
Three polyindenes are highly symmetric condensed-nuclei aromaticss, have been proved to be one of idealized compound for preparing liquid crystal material, fullerene derivate and C3 type asymmetry catalysis material etc.If three polyindenes can be carried out suitable chemically modified, and construct novel organic conjugate functional materials, will produce unique optics and photoelectron behavior as structural motif.
Biological organic organic solid and the macromolecular material research department that leads with doctor Pei Jian of key lab of the molecular engineering the Ministry of Education of Chemical and Molecular Engineering College of Beijing Univ., first three polyindene structures are introduced the organic photoelectrical material field, they utilize three polyindenes as structural motif, have successfully prepared a trimer indene derivative that a series of starlike oligo-thiophenes replace and a class novel conjugated dendritic macromole ([4] J.Pei, the J-L Wang based on three polyindene structures, X-Y.Cao, X-H Zhou, W-B.Zhang, J.Am Chem.Soc.2003,125, p9944-9945.[5] X.Y Cao, W.-B.Zhang, J.-L.Wang, X.H Zhou, J.Pei, J.Am.Chem.Soc.2003,12340-12341.[6] S.-C.Yuan, H.-B.Chen, Y.Zhang, J.Pei, Org.Lett.2006,8,5701-5704.).This achievement broken through traditional with simple molecules such as benzene, fluorenes, thiophene phenylenevinylenes as the limitation of constructing primitive, provide a kind of brand-new thinking for constructing novel organic conjugate functional materials.
The trimer indene derivative that the starlike oligo-thiophenes of this study group's synthetic replaces is along with the progressively growth of thiophene arm, the ultraviolet of compound and absorption spectrum be red shift thereupon all, not only good restraining the p synergistic effect between the aromatic ring plane, improve simultaneously institute's synthetic material well at solid-state pattern down, had the very optical property of excellence.This type of material is quite optimistic as the prospect of organic electroluminescent diode apparatus and organic solar batteries.
Summary of the invention
The object of the present invention is to provide class substituted quinoline trimer indene derivative and preparation method thereof, this organic compound structure is simple, can be used as electroluminescent organic material, and the preparation method is very simple.
The object of the present invention is achieved like this:
One class substituted quinoline trimer indene derivative, characteristics are on ethylating three polyindenes, have introduced the quinoline group that replaces.
On described three polyindenes, introduce quinoline group, the quinoline group of two replacements or the quinoline group of three replacements of a replacement, be respectively the single substituted quinoline trimer indene, 2 of 2-, the two substituted quinoline trimer indenes or 2,7 of 7-, 12-three substituted quinoline trimer indenes, its chemical structural formula is as follows:
Wherein: substituent X is H, F or Br.
The method for preparing above-mentioned substituted quinoline trimer indene derivative is: with three polyindenes is raw material, introduces ethyl at its 5,10,15 earlier, then through Fu Ke (Friedel-Crafts) acylations, 2,7, introduces ethanoyl for 12; These intermediates respectively with the 2-aminobenzophenone that replaces under acid catalysis through blue moral (Friedlander) condensation of Fred, single quinoline that the preparation phenyl replaces, two quinoline, three quinoline trimer indene derivatives.
Above-mentioned described method can obtain single acidylate through acylations, two acidylates, and three polyindenes of full acidylate, its structural formula is as follows:
In the aforesaid method, ethylating three polyindenes and acylting agent molar ratio are 1: 1.2 o'clock, and three polyindenes of single acidylate are main; Molar ratio is 1: during 1.9-2.5, three polyindenes of two acidylates are main; Molar ratio is 1: during 3-4, three polyindenes of full acidylate are main.
Three polyindenes of described single acidylate and the reaction of the 2-aminobenzophenone of replacement obtain three polyindenes (4d-4f) that single quinoline replaces; Three polyindenes of two acidylates and the reaction of 2-aminobenzophenone obtain three polyindenes (5d-5f) that two quinoline replace; Three polyindenes of full acidylate and the reaction of 2-aminobenzophenone obtain three polyindenes (6d-6f) that three quinoline replace.
Acylting agent of the present invention is Acetyl Chloride 98Min. or diacetyl oxide.
The present invention introduces the quinoline group that a phenyl replaces respectively complete 2,7,12 of ethylizing three polyindenes, two quinoline groups that phenyl replaces, three quinoline groups that phenyl replaces, ultraviolet and fluorometric investigation show that it has excellent photoelectric performance, are expected to become novel organic conjugate functional materials.
Description of drawings
Accompanying drawing is a schema of the present invention
Embodiment
The invention is further illustrated by the following examples
Adopt reagent: n-Butyl Lithium, tert-butyl lithium and lithium methide analytical pure [the chemical company limited of A Faaisha (Tianjin)] are produced; Bromic ether chemical pure [Chemical Reagent Co., Ltd., Sinopharm Group] is produced; Diacetyl oxide chemical pure [Chemical Reagent Co., Ltd., Sinopharm Group] is produced; Aluminum chloride analytical pure [Meixing Chemical Co., Ltd., Shanghai] is produced; 2-aminobenzophenone, 2-amino-4 '-fluorine benzophenone, 2-amino-4 '-bromo-benzophenone chemical pure [source, sky, Jintan, Jiangsu medicine company chemistry institute] are produced.
Embodiment
The first step: 5,10, the preparation of 15-Hexaethyl three polyindenes 1
N
2Under the protection, three polyindenes (10mmol) of 3.42g are added among the THF of 100ml, are cooled to 0 ℃, slowly drip the n-Butyl Lithium (36mmol) of 12.6ml, dropwise the back and rise to room temperature naturally, continue to stir 0.5 hour.And then be cooled to 0 ℃ of bromic ether (45mmol) that is added dropwise to 4.9g, after the stirring at room 4 hours, under similarity condition, add butyllithium again with equivalent last time, stir after 1 hour, be added dropwise to the bromic ether (45mmol) of 4.9g again, after the stirring at room 12 hours, mixed solution is poured in the water of 70ml, CH
2Cl
2Extraction, removal of solvent under reduced pressure gets faint yellow solid, in ethanol, reflux filtered in 1 hour white powder solid 4.18g (compound 1), yield 82%, m.p.218-221 ℃;
1HNMR (500Mz, CDCl
3, ppm): δ 8.4 (1H, d, J=7.2Hz, Tr-H), 7.5 (1H, m, Tr-H), 7.4 (1H, m, Tr-H), 3.0 (2H, m ,-CH
2-), 2.2 (2H, m ,-CH
2-), 0.2 (6H, t, J=7.3Hz ,-CH
3).
Second step:
(1), the preparation of single acetyl three polyindene 2a
5.1g compound 1 add the anhydrous CH of 50ml
2Cl
2In, add the anhydrous AlCl of 2.8g immediately
3(0.021mol), mixed solution is chilled to 0 ℃, and the diacetyl oxide of 1.13g (0.01mol) dissolves into the CH of 5ml
2Cl
2In be added dropwise in the above-mentioned mixed solution, rise to stirring at room after dropwising and pour into after 2 hours in the trash ice that contains concentrated hydrochloric acid, behind the ethyl acetate extraction, use Na respectively
2CO
3Solution, saturated common salt washing, organic phase MgSO
4Drying is removed and to be desolvated, column chromatography separate pale yellow powder shape solid, yield 81%, m.p.209-212 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.38-8.36 (1H, d, J=8.0Hz, Tr-H), 8.29 (2H, t, J=6Hz, Tr-H), 8.00 (1H, s, Tr-H), 7.95-7.94 (1H, m, Tr-H), 2.99-2.90 (1H, m ,-CH
2-), 2.65 (3H, s ,-COCH
3), 2.17-2.09 (6H, m ,-CH
2-), 0.16-0.12 (18H, m ,-CH
3).
(2), the preparation of di-acetyl three polyindene 2b
The preparation method is with second step (1), and the consumption of diacetyl oxide increases to 2.47g (0.022mol), and other consumption is constant, yield 72%, m.p.304-306 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.45-8.35 (m, 3H, Tr-H), 8.08-8.02 (m, 4H, Tr-H), 7.47-7.41 (m, 3H, Tr-H), 3.07-2.95 (m, 6H ,-CH
2-), 2.71 (s, 6H ,-COCH
3), 2.28-2.17 (m, 6H ,-CH
2), 0.22-0.18 (m, 18H ,-CH
3).
(3), the preparation of full acetyl three polyindene 2c
The preparation method is with second step (1), and the consumption of diacetyl oxide increases to 3.94g (0.035mol), and other consumption is constant, yield 78%, m.p.226-229 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.45 (d, 1H, J=9Hz, Tr-H), 8.09 (s, 1H, Tr-H), 8.04 (d, 1H, J=8Hz, Tr-H), 3.03-2.97 (m, 2H ,-CH
2-), 2.72 (s, 3H ,-COCH
3), 2.30-2.25 (m, 2H ,-CH
2-), 0.22 (m, 6H ,-CH
3)
The 3rd step:
(1), the preparation of single substituted quinoline trimer indene 4d-4f
With single acetyl three polyindene 2a (5.52g, 0.01mol) and 2-aminobenzophenone derivative 0.01mol join in the flask that 30mL acetate is housed, be added dropwise to the 0.1mL vitriol oil, back flow reaction 20 hours is poured reactant in the 40mL aqueous solution of the 15mL strong aqua for preparing in advance, and yellow mercury oxide is arranged, filter, solid washes with water, head product, column chromatography separate faint yellow solid.4d: productive rate 56%, m.p.176-178 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.54 (d, 1H, J=8Hz) 8.41-8.37 (m, 2H), 8.33-8.25 (m, 3H), 7.97 (s, 1H), 7.94 (d, 1H, J=8Hz), 7.79-7.76 (m, 1H), 7.65-7.56 (m, 5H), 7.52-7.40 (m, 7H), 3.08 (m, 6H ,-CH
2-), 2.20 (m, 2H ,-CH
2-), 2.18 (m, 4H ,-CH
2-), 0.30-0.22 (m, 18H ,-CH
3) .4e: yield, 50%; M.p.281-283 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.53 (d, 1H, J=9Hz), 8.38 (t, 2H, J=8Hz), 8.32-8.24 (m, 3H), 7.92 (s, 1H), 7.88 (d, 1H, J=8Hz), 7.79-7.76 (m, 1H), and 7.63-7.60 (m, 2H), 7.53-7.47 (m, 3H), and 7.43-7.40 (m, 4H), 7.31-7.26 (m, 2H), 3.09-3.02 (m, 6H ,-CH
2-), 2.30 (m, 2H ,-CH
2-), 2.23-2.17 (m, 4H ,-CH
2-), 0.29-0.21 (m, 18H ,-CH
3) .4f: yield, 59%; M.p.291-294 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.52 (d, 1H, J=9Hz), 8.38 (t, 2H, J=8Hz), 8.32-8.24 (m, 3H), 7.91 (s, 1H), 7.87 (d, 1H, J=9Hz), 7.79-7.73 (m, 3H), 7.52-7.47 (m, 5H), 7.43-7.39 (m, 4H), 3.05 (m, 6H ,-CH
2-), 2.30 (m, 2H ,-CH
2-), 2.18 (m, 4H ,-CH
2-), 0.29-0.21 (m, 18H ,-CH
3).
(2), the preparation of two substituted quinoline trimer indene 5d-5f
With di-acetyl three polyindene 2b (5.94g, 0.01mol) and 2-aminobenzophenone derivative 0.022mol join in the flask that 30mL acetate is housed, be added dropwise to the 0.1mL vitriol oil, back flow reaction 20 hours is poured reactant in the 40mL aqueous solution of the 15mL strong aqua for preparing in advance, and yellow mercury oxide is arranged, filter, solid washes with water, head product, column chromatography separate faint yellow solid.5d: yield 51%; M.p.242 ℃ (124 ℃ time begin that bubble is arranged).
1H NMR (500Mz, CDCl
3, ppm): δ 8.56 (m, 2H), 8.42 (d, 1H, J=8Hz), 8.54 (m, 4H), 8.27 (d, 2H, J=7Hz), 7.98 (s, 2H), 7.94 (d, 2H, J=8Hz), 7.78 (t, 2H, J=8Hz), 7.66-7.56 (m, 10H), 7.51 (m, 3H), 7.43 (m, 2H), 3.31 (m, 6H ,-CH
2-), 2.37-2.33 (m, 4H ,-CH
2-), 2.23 (m, 2H ,-CH
2-), 0.35-0.25 (m, 18H ,-CH
3) .5e: yield 46%, m.p.223 ℃ (177 ℃ time begin that bubble is arranged).
1H NMR (500Mz, CDCl
3, ppm): δ 8.55 (t, 2H, J=9Hz), 8.40 (d, 1H, J=8Hz), 8.33-8.26 (m, 6H), 7.93 (s, 2H), 7.88 (d, 2H, J=8Hz), 7.77 (t, 2H, J=8Hz), 7.62-7.60 (m, 4H), 7.53-7.49 (m, 3H), and 7.45-7.39 (m, 2H), 7.29 (m, 4H), 3.13-3.07 (m, 6H ,-CH
2-), 2.36-2.32 (m, 4H ,-CH
2-), 2.22 (m, 2H), 0.32-0.24 (m, 16H ,-CH
3) .5f: 323-325 ℃ of yield 54%.m.p.
1H NMR (500Mz, CDCl
3, ppm): δ 8.55 (t, 2H, J=9Hz), 8.41 (d, 1H, J=8Hz), 8.32-8.30 (m, 4H), 8.26 (d, 2H, J=6Hz), 7.93 (s, 2H), 7.79-7.73 (m, 5H), 7.50-7.49 (m, 8H), 7.45-7.41 (m, 2H), 3.11 (m, 6H ,-CH
2-), 2.34 (m, 4H ,-CH
2-), 2.22 (m, 2H ,-CH
2-), 0.32-0.24 (m, 16H ,-CH
3).
(3), the preparation of three substituted quinoline trimer indene 6d-6f
With full acetyl three polyindene 2c (6.36g, 0.01mol) and 2-aminobenzophenone derivative 0.035mol join in the flask that 30mL acetate is housed, be added dropwise to the 0.1mL vitriol oil, back flow reaction 20 hours is poured reactant in the 40mL aqueous solution of the 15mL strong aqua for preparing in advance, and yellow mercury oxide is arranged, filter, solid washes with water, head product, column chromatography separate faint yellow solid.6d: yield 55%, m.p.290 ℃ (209 ℃ time begin that bubble is arranged).
1H NMR (500Mz, CDCl
3, ppm): δ 8.58 (d, 1H, J=9Hz), 8.36-8.29 (m, 3H), 7.98 (s, 1H), 7.34 (d, 1H, J=8Hz), 7.77 (t, 1H, J=8Hz), 7.65-7.54 (m, 5H), 7.51 (m, 1H), 3.15 (m, 2H ,-CH
2-), 2.37 (m, 2H ,-CH
2-), 0.32 (m, 6H ,-CH
3) .6e: yield 51%, m.p.270-272 ℃.
1HNMR (500Mz, CDCl
3, ppm): δ 8.57 (d, 1H, J=8Hz), 8.35-8.30 (m, 3H), 7.94 (s, 1H), 7.88 (d, 1H, J=8Hz), 7.77 (m, 1H), 7.62-7.60 (m, 2H), 7.53-7.49 (m, 1H), 7.29 (t, 2H, J=8.6Hz), 3.18-3.11 (m, 2H ,-CH
2-), 2.42-2.35 (m, 2H ,-CH
2-), 0.34-0.31 (m, 6H ,-CH
3) .6f: yield 60%, m.p.263-266 ℃.
1H NMR (500Mz, CDCl
3, ppm): δ 8.57 (d, 1H, J=8.3Hz), 8.34-8.29 (m, 3H), 7.93 (s, 1H), 7.87 (d, 1H, J=8.3Hz), 7.78 (m, 1H), 7.73 (d, 1H, J=8.2Hz), 7.52-7.50 (m, 3H), 3.17-3.10 (m, 2H ,-CH
2-), 2.42-2.35 (m, 2H ,-CH
2-), 0.35-0.32 (m, 6H ,-CH
3).
Claims (6)
1. a class substituted quinoline trimer indene derivative is characterized in that on ethylating three polyindenes, has introduced the quinoline group that replaces.
2. substituted quinoline trimer indene derivative according to claim 1, it is characterized in that on described three polyindenes, introducing quinoline group, the quinoline group of two replacements or the quinoline group of three replacements of a replacement, it is respectively the single substituted quinoline trimer indene, 2 of 2-, the two substituted quinoline trimer indenes or 2 of 7-, 7,12-three substituted quinoline trimer indenes, its chemical structural formula is as follows:
4d-4f 5d-5f 6d-6f
Wherein: substituent X is H, F or Br.
3. a method for preparing claim 1 or 2 described substituted quinoline trimer indene derivatives is characterized in that with three polyindenes be raw material, introduces ethyl at its 5,10,15 earlier, then through friedel-crafts acylation, 2,7, introduces ethanoyl for 12; These intermediates respectively with the 2-aminobenzophenone that replaces under acid catalysis through the blue moral condensation of Fred, single quinoline that the preparation phenyl replaces, two quinoline, three quinoline trimer indene derivatives.
4. preparation method according to claim 3 is characterized in that can obtaining single acidylate through acylations, two acidylates, and three polyindenes of full acidylate, its structural formula is as follows:
2a 2b 2c
5. preparation method according to claim 4 is characterized in that ethylating three polyindenes and acylting agent molar ratio are at 1: 1.2 o'clock, and three polyindenes of single acidylate are main; Molar ratio is 1: during 1.9-2.5, three polyindenes of two acidylates are main; Molar ratio is 1: during 3-4, three polyindenes of full acidylate are main.
6. preparation method according to claim 5 is characterized in that three polyindenes of single acidylate and the 2-aminobenzophenone reaction of replacement, obtains three polyindenes (4d-4f) that single quinoline replaces; Three polyindenes of two acidylates and the reaction of 2-aminobenzophenone obtain three polyindenes (5d-5f) that two quinoline replace; Three polyindenes of full acidylate and the reaction of 2-aminobenzophenone obtain three polyindenes (6d-6f) that three quinoline replace.
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| CN102807534A (en) * | 2011-05-31 | 2012-12-05 | 海洋王照明科技股份有限公司 | Organic semiconductor material and preparation method thereof |
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