CN103421012A - Method for preparing tricarbazole material from aryl indolone in one step - Google Patents
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- -1 aryl indolone Chemical compound 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000000463 material Substances 0.000 title claims abstract description 11
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 title abstract description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 85
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- 150000001716 carbazoles Chemical class 0.000 claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 238000010189 synthetic method Methods 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 238000002189 fluorescence spectrum Methods 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YHIWBVHIGCRVLE-UHFFFAOYSA-N 3-bromo-1h-indole Chemical compound C1=CC=C2C(Br)=CNC2=C1 YHIWBVHIGCRVLE-UHFFFAOYSA-N 0.000 description 4
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- XHEMYHPZFLHSDC-UHFFFAOYSA-N 1-ethyl-5-(4-methoxyphenyl)-3H-indol-2-one Chemical compound C(C)N1C(CC2=CC(=CC=C12)C1=CC=C(C=C1)OC)=O XHEMYHPZFLHSDC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical class Br* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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Abstract
The invention provides a method for preparing a tricarbazole material from aryl indolone in one step. The invention solves the defects of long steps of synthesizing the tricarbazole compound by the conventional method and single mode of introducing substituent groups into the tricarbazole compound. The obtained compound is expected to be applied to organic light emitting diodes.
Description
Technical field
The present invention relates to a kind of three and the preparation method of carbazoles material, be specifically related to a kind ofly using (hetero) aryl indole ketone as raw material, directly at POCl
3For condensation under the dewatering agent condition obtains three and the method for carbazoles material.
Technical background
Three and carbazole can be regarded as phenyl ring of three carbazole unit common center and of forming has 3 heavy symmetric molecules.Obviously, because lone-pair electron on nitrogen-atoms participate in the π system, three and carbazole there is very large conjugacy.So divide the period of the day from 11 p.m. to 1 a.m constructing organic photoelectric, three and carbazole can make a good pi-conjugated bridge, but again due to its electron rich character Zuo Yige center to body, make its existing possibility that becomes good luminescent material, there is again the potential quality that becomes outstanding hole mobile material, having broad application prospects aspect the function photoelectric material.But current difficulty on synthetic due to it, with and to introduce the substituent method of aryl class of its performance of improvement limited, very limited to its research.
The synthetic method of (1986) report is to do raw material with indoles and 3-bromo indole in early days, under acidic conditions after both couplings again with the 3-bromo indole coupling of a part, finally with trifluoroacetic acid oxydehydrogenation, obtain (Tetrahedron, 1986,42,5019).This method yield only has 23%, and reason is that side reaction is very many, and separation difficulty, so be not used widely.
The synthetic method of Fig. 1 early stage three carbazole
2000, Mount etc. synthesized 2,3,7,8,12,13-hexabromo three carbazole by simple method, and have obtained relatively high yield (59%).In acetonitrile, process indoles with the bromine of three equivalents under room temperature and just directly obtain three and the carbazole that six bromines replace, operate fairly simple (J.Mater.Chem, 2000,10,2043).
The synthetic method of Fig. 2 hexabromo three carbazole
2005, the people such as Hiyoshi with indolone with POCl
3In situation for halogenating agent, halo condensation obtain three and carbazole, and productive rate is not too high (40%), but operation is very easy, and 1 step reaction just can obtain three carbazoles (WO2005077956,2005) also.But he has only studied, indole ketone compound that some less groups (alkyl, hydroxyl, halogen etc.) replace is synthetic obtains three and carbazole, but these little groups are on three and the character impact of carbazole little.
Fig. 3 indolone synthetic three carbazole
Due to three and the carbazole stability of molecule very high, introduce containing the method for the aryl side chain of good photoelectric properties few, the method for current introducing aryl side chain mainly contains two kinds: one be three and carbazole have 3 hydrogen on nitrogen to be substituted, then carry out molecular modification; The 2nd, bromination three carbazole and other molecule generation linked reactions, thereby the substituting group that can introduce equally some excellent in performance to three also carbazole carry out molecular modification and obtain new high performance OLED material.
Introduce the synthetic route of three and carbazole of side chain on Fig. 4 N
Three and carbazole of Fig. 4 bromination synthetic three and carbazole route containing the aryl side chain
In sum, the method for above-mentioned introducing aryl side chain all has synthesis step longer, and introduces substituting group mode and the single shortcoming of location comparison, and this has limited the three also application of carbazole compound in electroluminescent organic material greatly.The present invention is dissolved in (hetero) aryl indole ketone in toluene, at POCl
3For the dewatering agent condition, next step synthetic makes three and carbazole compound, has shortened synthetic route, and relevant research has no bibliographical information, and possesses industrial prospect preferably.
Summary of the invention
The object of the invention is to propose obtain three carbazole compounds also with (hetero) aryl indole ketone direct polycondensation, make three and the carbazole side chain abundanter, can introduce the mode that the aryl class substituting group of photoelectric properties excellence modified more diversified, can greatly promote three and the development of carbazole in electroluminescent organic material.
The synthetic method that the present invention adopts is for to be dissolved in (hetero) aryl indole ketone in toluene, and the indolone that concrete proportioning is 10mol adds the toluene of 10ml, then adds isopyknic POCl
3Back flow reaction 10-30h, obtain a series of three and carbazole compound, obtains the yield (30%-40% left and right) comparatively be satisfied with simultaneously, and reaction formula is:
R wherein
1Be selected from the alkyl of hydrogen, phenyl, C1-C12; R
2Be selected from substituted-phenyl, substituted biphenyl base, substituted diphenylamine ether, replace fluorenyl, substituted carbazole base, substituted thiophene base, substituted pyridinyl.Its structure is as follows:
R
3Alkyl, carbonatoms 7 to 12 aromatic bases for H, carbonatoms 1 to 12.
Wherein, typical compound 5,10,15-triethyl-3,8,13-triphenyl three carbazole, 5,10,15-triethyl-3,8,13-tri-tert phenyl three carbazole, 5,10,15-triethyl-3,8,13-trimethoxyphenyl three carbazole, 5,10,15-triethyl-3,8,13-, tri-fluorenyl three carbazoles, 5,10,15-triethyl-3,8,13-triphenylamine base three carbazole (
1a-
1e) productive rate between 28.6-40.5%, ultraviolet maximum absorption wavelength is between 311-345nm, maximum fluorescence emission spectrum (concrete spectral quality in Table 1) between 394.5-412.5nm, be the desirable blue light organic luminescent material of a class.
The accompanying drawing explanation
Fig. 1
1a-
1eUltraviolet-visible absorption spectroscopy in dichloromethane solution (c=1.0 * 10
-6MolL
-1)
Fig. 2
1a-
1eFluorescence emission spectrum in dichloromethane solution (c=1.0 * 10
-7MolL
-1)
Embodiment
Embodiment 1:5,10,15-triethyl-3,8,13-triphenyl three is synthesizing of carbazole (1a) also
N-ethyl-5-Phenylindole ketone (2.37g, 10.0mmol) is dissolved in toluene 10ml, is added in phosphorus oxychloride 10ml solution magnetic agitation, temperature control 100-110 ℃, reaction 16h.Then be cooled to room temperature, pour in frozen water, fully stir, use Na
2CO
3Be neutralized to neutrality, then use dichloromethane extraction 3 times, merge organic layer, drying, steaming desolventizes, and by column chromatography, obtains white solid powder 5,10,15-triethyl-3,8,13-triphenyl three carbazole (1a) 0.85g, yield 39%, 254.3 ℃ of fusing points, ultra-violet absorption spectrum is shown in accompanying drawing 1, fluorescence emission spectrum is shown in accompanying drawing 2.
Embodiment 2:5,10,15-triethyl-3,8,13-tri-tert phenyl three is synthesizing of carbazole (1b) also
N-ethyl-5-tert-butyl-phenyl indolone (2.93g, 10.0mmol) is dissolved in toluene 10ml, is added in phosphorus oxychloride 10ml solution magnetic agitation, temperature control 100-110 ℃, reaction 20h.Then be cooled to room temperature, pour in frozen water, fully stir, use Na
2CO
3Be neutralized to neutrality, then use dichloromethane extraction 3 times, merge organic layer, drying, steaming desolventizes, and by column chromatography, obtains white solid powder 5,10,15-triethyl-3,8,13-tri-tert phenyl three carbazole (1b) 1.11g, yield 40.5%, 254.8 ℃ of fusing points, ultra-violet absorption spectrum is shown in accompanying drawing 1, fluorescence emission spectrum is shown in accompanying drawing 2.
Embodiment 3:5,10,15-triethyl-3,8,13-trimethoxyphenyl three is synthesizing of carbazole (1c) also
N-ethyl-5-p-methoxy-phenyl indolone (2.67g, 10.0mmol) is dissolved in toluene 10ml, is added in phosphorus oxychloride 10ml solution magnetic agitation, temperature control 100-110 ℃, reaction 10h.Then be cooled to room temperature, pour in frozen water, fully stir, use Na
2CO
3Be neutralized to neutrality, then use dichloromethane extraction 3 times, merge organic layer, drying, steaming desolventizes, and by column chromatography, obtains faint yellow solid powder 5,10,15-triethyl-3,8,13-trimethoxyphenyl three carbazole (1c) 0.84g, yield 33.7%, 367.8 ℃ of fusing points, ultra-violet absorption spectrum is shown in accompanying drawing 1, fluorescence emission spectrum is shown in accompanying drawing 2.
Embodiment 4:5,10,15-triethyl-3,8,13-tri-fluorenyls three are synthesizing of carbazole (1d) also
N-ethyl-5-fluorenyl indolone (4.37g, 10.0mmol) is dissolved in toluene 10ml, is added in phosphorus oxychloride 10ml solution magnetic agitation, temperature control 100-110 ℃, reaction 30h.Then be cooled to room temperature, pour in frozen water, fully stir, use Na
2CO
3Be neutralized to neutrality, then use dichloromethane extraction 3 times, merge organic layer, drying, steaming desolventizes, and by column chromatography, obtains white solid powder 5,10,15-triethyl-3,8,13-tri-fluorenyl three carbazole (1d) 1.32g, yield 31.6%, 219.3 ℃ of fusing points, ultra-violet absorption spectrum is shown in accompanying drawing 1, fluorescence emission spectrum is shown in accompanying drawing 2.
Embodiment 5:5,10,15-triethyl-3,8,13-triphenylamine base three is synthesizing of carbazole (1e) also
N-ethyl-5-triphenylamine base indolone (4.04g, 10.0mmol) is dissolved in toluene 10ml, is added in phosphorus oxychloride 10ml solution magnetic agitation, temperature control 100-110 ℃, reaction 24h.Then be cooled to room temperature, pour in frozen water, fully stir, use Na
2CO
3Be neutralized to neutrality, then use dichloromethane extraction 3 times, merge organic layer, drying, steaming desolventizes, and by column chromatography, obtains faint yellow solid powder 5,10,15-triethyl-3,8,13-triphenylamine base three carbazole (1e) 1.10g, yield 28.6%, 372.6 ℃ of fusing points, ultra-violet absorption spectrum is shown in accompanying drawing 1, fluorescence emission spectrum is shown in accompanying drawing 2.
Table 1.
1a-
1eThe spectral quality list
Table?1.Spectra?properties?of?
1a-
1e
Although with preferred embodiment in detail the present invention has been described in detail, yet it is not intended to limit the present invention.Any those skilled in the art, without departing from the spirit and scope of the present invention, should make various modifications and change.Therefore protection scope of the present invention should be considered as appended claims limited range.
Claims (4)
1. one kind prepares three and the method for carbazoles material by (hetero) aryl indole ketone one step, it is characterized in that: (hetero) aryl indole ketone is dissolved in toluene, adds POCl
3Carry out condensation reaction.After reaction finishes, reaction solution is poured in frozen water after being cooled to room temperature, fully stirs, and uses Na
2CO
3Be neutralized to neutrality, then use dichloromethane extraction 3 times, merge organic layer, drying, steaming desolventizes, and by column chromatography, obtains three and carbazole compound, and reaction formula is as follows:
R wherein
1Be selected from the alkyl of hydrogen, phenyl, C1-C12; R
2Be selected from substituted-phenyl, substituted biphenyl base, substituted diphenylamine ether, replace fluorenyl, substituted carbazole base, substituted thiophene base, substituted pyridinyl, its structure is as follows:
R
3Alkyl, carbonatoms 7 to 12 aromatic bases for H, carbonatoms 1 to 12.
2. the synthetic method of a kind as claimed in claim 1 three and carbazole compound, is characterized in that: the (hetero) aryl indole ketone of 10mmol is dissolved to toluene and POCl with the toluene of 10mL
3Volume ratio be 1: 1.
3. the synthetic method of a kind as claimed in claim 1 three and carbazole compound, it is characterized in that: the reaction times is 10 to 30 hours.
4. the synthetic method of a kind as claimed in claim 1 three and carbazole compound, it is characterized in that: temperature of reaction is 100 ℃ to 110 ℃.
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| CN103739607A (en) * | 2014-01-22 | 2014-04-23 | 无锡方圆环球显示技术股份有限公司 | Tri-carbazole multi-arm structural red-light--emitting material and preparation method and application thereof |
| CN107445968A (en) * | 2017-06-14 | 2017-12-08 | 南京邮电大学 | A kind of two indoles and three and the more arm configuration conjugated molecular materials of carbazyl and preparation method and application |
| CN108794494A (en) * | 2018-06-18 | 2018-11-13 | 南京邮电大学 | One kind three and carbazole-aromatic amine derivant hole mobile material and the preparation method and application thereof |
| CN108948026A (en) * | 2018-06-15 | 2018-12-07 | 南京邮电大学 | One kind three and carbazole-phenyl hole mobile material and the preparation method and application thereof |
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