CN105712950B - Amides compound and its preparation method and application based on benzothiazole - Google Patents
Amides compound and its preparation method and application based on benzothiazole Download PDFInfo
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- CN105712950B CN105712950B CN201610056123.6A CN201610056123A CN105712950B CN 105712950 B CN105712950 B CN 105712950B CN 201610056123 A CN201610056123 A CN 201610056123A CN 105712950 B CN105712950 B CN 105712950B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Abstract
The present invention relates to a kind of amides compound and preparation method thereof based on benzothiazole.The structure of the compound is as shown in logical formula (I), wherein R is-H or-OH；N is the integer of 1-4；R1It is identical or different, it is independent to be selected from H, C1‑6Alkyl, C1‑6Alkoxy, halogen ,-NR3R4, aryl, heteroaryl；R2For C1‑18Alkyl, aryl, heteroaryl；R3、R4It is identical or different, it is independently H, C1‑6Alkyl, aryl.The invention further relates to application of the compound in terms of organic optical function material.The compound can issue the fluorescence of stronger blue, green or yellow, shining for different colours can be obtained and configuring different ratios, and can be superimposed generation white light.Therefore compound of the present invention is mixed or is adulterated, white light emitting material can be prepared, can apply in the solid luminescents material such as white organic light emitting diode.
Description
Technical field
The present invention relates to benzothiazole analog derivatives, more particularly to the amides compound based on benzothiazole, and should
The preparation method of class compound and its application in terms of small organic molecule luminescent material.
Background technique
Excited state intramolecular proton transfer (ESIPT) phenomenon is widely present in nature, be biology, in chemical process most
One of basic and most important proton translocation mode.Compared with other organic luminescent compounds, ESIPT compound has uniqueness
E-E*-K*-K-E four-level transition behavior to have biggish Stokes shift and higher luminous efficiency be a kind of
Typically due to interaction of hydrogen bond and with aggregation-induced emission enhancement (AIEE) property compound, in high concentration or aggregation
Luminous efficiency when state is significantly larger than its luminous efficiency in the weak solution of low concentration.ESIPT compound has special light
Physical process and photophysical property are a kind of New Solid (state of aggregation) luminous organic materials with excellent properties, pesticide,
The numerous areas such as medicine, biology and optical function material, which suffer from, to be widely applied.
The organic solid-state luminescent material of high brightness has good application prospect in electroluminescent field, especially organic white
Application in light-emitting diode.ESIPT compound with AIEE property can well solve aggregation fluorescent quenching (ACQ)
The problem of, therefore ESIPT compound is applied in Organic white light luminescence material be a meaningful research direction.White light
Luminescent material can be divided mainly into two class of unimolecule white light emitting material and polymolecular white light emitting material.It is found that it can by colorimetry
White light is obtained by the superposition of red, green, blue three primary colours.As long as the line segment that the chromaticity coordinates of three kinds of light is linked to be two-by-two surrounded three
Angular includes white point, then these three light can generate white light by reasonably superposition.If it is the chromaticity coordinates institute of two kinds of light
The line segment being linked to be crosses white point, then both light also can produce white light by being reasonably superimposed.
Summary of the invention
The purpose of the present invention is to provide the amides compounds based on benzothiazole.
Another object of the present invention is to provide the preparation methods of the amides compound based on benzothiazole.
A further object of the present invention is to provide the amides compounds based on benzothiazole to be used to prepare small organic molecule
Purposes in terms of luminescent material.
The object of the invention is achieved by following technical solution:
A kind of amides compound based on benzothiazole, structure are shown in logical formula (I):
Wherein,
R is-H or-OH；N is the integer of 1-4；
R1It is identical or different, it is independent to be selected from H, C1-6Alkyl, C1-6Alkoxy, halogen ,-NR3R4, aryl, heteroaryl；
R2For C1-18Alkyl, aryl, heteroaryl；
R3、R4It is identical or different, it is independently H, C1-6Alkyl, aryl.
The alkyl is linear or branched alkyl group, for example, methyl, ethyl, propyl, butyl, isobutyl group, tert-butyl etc..
The aryl refers to monocycle or polycyclic aromatic group with 6-20 carbon atom, and representative aryl includes: benzene
Base, naphthalene, anthryl, pyrenyl etc..
The heteroaryl refers to 1-20 carbon atom, 1-4 selected from the heteroatomic monocycle of N, S, O or polycyclic hetero-aromatic
Group, representative heteroaryl include: pyrrole radicals, pyridyl group, pyrimidine radicals, imidazole radicals, thiazolyl, indyl, azepine naphthalene etc..
Preferably, in the logical formula (I) compound, amide groups and group R are at contraposition or meta position.
Preferably, R is-H and is in meta position with amide group；Or R is-OH and is in meta position with amide group；Or R
Contraposition is in for-OH and with amide group.
Preferably, n is 1 or 2.
Preferably, R1It is identical or different, it is independent to be selected from H, C1-6Alkyl, C1-6Alkoxy, aryl.
Preferably, R2For C1-10Alkyl, aryl.
It is further preferred that the logical formula (I) compound can be following particular compound:
The present invention also provides a kind of methods for preparing above-mentioned logical formula (I) compound, comprising: by logical formula (II) compound with
R2COOH reacts to obtain logical formula (I) compound:
Wherein R, R1、R2, n it is as defined above.
According to the present invention, above-mentioned reaction carries out under solvent environment, and the solvent is preferably toluene solvant.Preferably, make
Promote the amidation process between amino and carboxyl with dehydrating agent (such as N, N '-carbonyl dimidazoles (CDI)).
According to the present invention, above-mentioned product is subjected to separating-purifying by recrystallization or silica gel column chromatography.
According to the present invention, above-mentioned logical formula (II) compound can be prepared via a method which:
Wherein R, R1, n defines as described above；
Logical formula (III) compound is reacted with logical formula (IV) compound, obtains logical formula (II) compound.Preferably,
Above-mentioned reaction carries out in polyphosphoric acids.It is preferred that above-mentioned reaction carries out under protection of argon gas.Specific synthetic route, which can refer to, originally grinds
Chinese patent CN102993194 (the application number: 201110143095.9) of Jiu Zu poplar Guoqiang etc..
Compound synthesis step of the present invention is few, and the reaction time is short, and purification is convenient, simple process.
Compound of the present invention can issue the fluorescence of stronger blue, green or yellow respectively, can pass through and configure
Different ratios is mixed to get shining for the different colours including white luminous, such as can be obtained CIE coordinate and be
The white light of (0.31,0.32).This kind of compound can be applied in small organic molecule luminescent material.
The present invention also provides the purposes of above-mentioned logical formula (I) compound, can be used in luminous organic material.Such as with
In Organic Light Emitting Diode.
According to the present invention, above-mentioned logical formula (I) compound can be used for preparing the luminous luminous organic material of different colours, example
Such as blue, green, yellow, white.
According to the present invention, above-mentioned different logical formula (I) compound is subjected to physical mixed or doping, available white light hair
Luminescent material.
A kind of luminous organic material, including logical formula (I) compound of the present invention.
According to the present invention, the luminous organic material includes two or more logical formula (I) chemical combination of the present invention
Object.
Preferably, the luminous organic material contains following three kinds of compounds:
Detailed description of the invention
Fig. 1 is the normalized fluorescence emission spectra of compound P1s, P2s, P3s solid (λ em=prepared by embodiment 2~4
340nm)。
Fig. 2 is that P1s, P2s, P3s prepared by embodiment 5~7 is entrained in the film in polymethyl methacrylate in 365nm
Photo under ultraviolet lamp.
Fig. 3 is that P1s, P2s, P3s prepared by embodiment 5~7 is entrained in shining for the film in polymethyl methacrylate
Coordinate corresponding to color on 1931 color space chromatic diagram (CIE diagram) of CIE.
Specific embodiment
The present invention is described in detail by following embodiments.But skilled in the art realises that following embodiments are not
Limiting the scope of the invention.Any improvements and changes made on the basis of the present invention, all in protection model of the invention
Within enclosing.
Embodiment 1: the preparation of the aminated compounds of benzothiazole
Prepare 4- (benzothiazole -2- base) aniline (P1), 5- amino -2- (benzothiazole -2- base) phenol (P2), 4- ammonia
Base -2- (benzothiazole -2- base) phenol (P3)
According to the Chinese patent CN102993194 (application number: institute in 201110143095.9) of poplar Guoqiang, this study group etc.
The method stated synthesizes to obtain.
Embodiment 2~4: the preparation of the amides compound of benzothiazole
Embodiment 2
Prepare N- [4- (benzothiazole) phenyl] caprylamide (P1s), molecular structural formula are as follows:
The N of 2.43g (0.015mol) is weighed, N '-carbonyl dimidazoles (CDI) are added in the there-necked flask of 100mL, add
Reaction half an hour is stirred at room temperature, then in the caprylic acid of the dry toluene and 2.16g (0.015mol) of 50mL under protection of argon gas
Heating makes system stop heating after reflux in toluene reacts five hours, and 2.26g (0.01mol) is added after being cooled to room temperature
4- (benzothiazole -2- base) aniline, be stirred at room temperature reaction half an hour after, temperature rising reflux, reaction overnight.Stop adding
Heat filters after being cooled to room temperature, and obtained solid is recrystallized in toluene, and white solid, yield 47.2% can be obtained.1H
NMR(400MHz,DMSO)δ10.18(s,1H),8.12(d,1H),8.02(t,3H),7.79(d,2H),7.52(t,1H),7.43
(t, 1H), 2.34 (t, 2H), 1.60 (t, 2H), 1.28 (t, 8H), 0.86 (t, 3H), EI-MS, m/z:352. molecular formula are
C21H24N2OS, Elemental Analysis theory: C 71.55, H 6.86, N 7.95；Measured value: C 71.37, H 6.70, N 8.09.
The compound issues stronger blue-fluorescence (see Fig. 1).Its luminous efficiency in ethyl acetate is 0.25.
Embodiment 3
Prepare N- [3- hydroxyl -4- (benzothiazole) phenyl] caprylamide (P2s), molecular structural formula are as follows:
4- (benzothiazole -2- base) aniline in embodiment 2 is changed to 5- amino -2- (benzothiazole -2- base) phenol,
Its step method obtains faint yellow solid, yield 69.0% with embodiment 2.1H NMR(400MHz,CDCl3)δ12.63(s,
1H),7.94(d,1H),7.88(d,1H),7.62(d,1H),7.49(t,1H),7.39(t,1H),7.27(d,1H),7.20(d,
2H), 2.38 (t, 2H), 1.74 (m, 2H), 1.36-1.29 (m, 8H), 0.88 (t, 3H) .EI-MS, m/z:368. molecular formula are
C21H24N2O2S, Elemental Analysis theory: C 68.45, H 6.56, N7.60；Measured value: C 68.19, H 6.61, N 7.43.
The compound issues stronger green fluorescence (see Fig. 1).
Embodiment 4
Prepare N- [3- (benzothiazole) -4- hydroxy phenyl] caprylamide (P3s), molecular structural formula are as follows:
Change 4- in embodiment 2 (benzothiazole -2- base) aniline into 4- amino -2- (benzothiazole -2- base) phenol, it is other
Synthetic method is the same as embodiment 2.The solid being obtained by filtration is washed three times with a small amount of methanol.It is with silica gel column chromatography that product is pure
Change, obtains faint yellow solid, yield 51.9%.1H NMR(400MHz,CDCl3)δ8.13(s,1H),7.99(d,1H),7.90
(d,1H),7.52-7.48(m,1H),7.43-7.39(m,1H),7.33-7.30(m,1H),7.15(s,1H),7.05(d,1H),
2.38 (t, 2H), 1.76 (t, 2H), 1.39-1.30 (m, 9H), 0.89 (t, 3H) .EI-MS, m/z:368. molecular formula are
C21H24N2O2S, Elemental Analysis theory: C 68.45, H 6.56, N 7.60；Measured value: C 68.10, H 6.54, N 7.40.
The compound issues stronger yellow fluorescence (see Fig. 1).
Embodiment 5~7: the system of the compound doped film in polymethyl methacrylate prepared in embodiment 2-4
It is standby
Embodiment 5
The polymethyl methacrylate (PMMA, molecular weight 15000) for weighing 0.3g, is dissolved in the methylene chloride of 6g, then plus
Enter N- [4- (benzothiazole) phenyl] caprylamide prepared in the embodiment 2 of 3mg, be sufficiently stirred, mixing mixes, and solution is shifted
Into culture dish, culture ware lid is covered, is put into draught cupboard, solvent is allowed slowly to volatilize completely, preparation obtains N- [4- (benzo thiophene
Azoles) phenyl] caprylamide is entrained in the film in PMMA.Wherein the mass ratio of compound and PMMA are 1:100.
The film is cut into small cube, blue light-emitting under the ultraviolet lamp of 365nm (see Fig. 2).
Embodiment 6
N- [4- (benzothiazole) phenyl] caprylamide in embodiment 5 is changed to N- [the 3- hydroxyl that embodiment 3 is prepared
Base -4- (benzothiazole) phenyl] caprylamide, other step methods are the same as embodiment 5.Preparation obtains N- [3- hydroxyl -4- (benzo thiophene
Azoles) phenyl] caprylamide is entrained in the film in PMMA.
The film is cut into small cube, in the ultraviolet lamp emitted green light of 365nm (see Fig. 2).
Embodiment 7
N- [4- (benzothiazole) phenyl] caprylamide in embodiment 5 is changed to the N- [3- being prepared in embodiment 4
(benzothiazole) -4- hydroxy phenyl] caprylamide, other step methods are the same as embodiment 5.Preparation obtains N- [3- (benzothiazole) -4-
Hydroxy phenyl] caprylamide is entrained in the film in PMMA.
The film is cut into small cube, Yellow light-emitting low temperature under the ultraviolet lamp of 365nm (see Fig. 2).
Shining for three kinds of films is detected with Fluorescence Spectrometer, converts 1931 color space chromatic diagram of CIE for light-emitting data
Coordinate points on (CIE diagram) (see Fig. 3).Three coordinate points are linked to be line segment and surround a triangle, it can be seen from the figure that this
Triangle includes white-light emitting region.Therefore, compound P1s, P2s, P3s is mixed or is adulterated according to suitable ratio, just
White light emitting material can be modulated.
Claims (1)
1. a kind of luminous organic material, wherein the luminous organic material contains following three kinds of compounds:
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