CN109851618A - A kind of N heterocycle Benzophenone analog derivative and its preparation method and application containing hydrogenation phenthazine group - Google Patents
A kind of N heterocycle Benzophenone analog derivative and its preparation method and application containing hydrogenation phenthazine group Download PDFInfo
- Publication number
- CN109851618A CN109851618A CN201910223531.XA CN201910223531A CN109851618A CN 109851618 A CN109851618 A CN 109851618A CN 201910223531 A CN201910223531 A CN 201910223531A CN 109851618 A CN109851618 A CN 109851618A
- Authority
- CN
- China
- Prior art keywords
- heterocycle
- analog derivative
- preparation
- benzophenone analog
- benzophenone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a kind of N heterocycle Benzophenone analog derivative and its preparation method and application containing hydrogenation phenthazine group, the N heterocycle Benzophenone analog derivative has the chemical structure as shown in formula (I)；N heterocycle Benzophenone analog derivative provided by the invention has unique AIE effect, high luminous intensity, good thermal stability and good dissolubility, can be used as that a kind of performance is good, cost is relatively low, the novel soluble light emitting molecule of space structure high distortion.The N heterocycle Benzophenone analog derivative is preparing the application aspects such as luminescent material, luminescent device or intellectual material with significant economic value, has a good application prospect in full-color display and solid-state lighting field.
Description
Technical field
The present invention relates to luminous organic material fields, more particularly, to a kind of N heterocycle containing hydrogenation phenthazine group
Benzophenone analog derivative and its preparation method and application.
Background technique
With the high-tech rise such as big screen intelligent mobile phone, tablet computer, wearable device, Organic Light Emitting Diode
(Organic Light-Emitting Diodes, abbreviation OLED) self-luminous, visual angle be wide, the low in energy consumption, response time because having
Fastly, thickness is thin, the advantages that flexible can be achieved, and is considered as a new generation of great development prospect in the FPD market of diversification
It shows product, is known as " dreamlike display ".Organic Light Emitting Diode (OLED) technology compared to traditional LED technology, due to
Table in terms of realizing that large-area high-quality is shown with illumination, ultrahigh resolution, super fast response speed and flexible electronic
The significant advantage revealed has huge application potential in fields such as FPD, smart phone and solid luminescences, attracts
The extensive concern of Global Academy and industry.
But currently, existing luminescent material that there are luminous intensities is not high, thermal stability is insufficient and dissolubility is bad
Problem.In addition, Chinese patent CN105111202A, CN108178758A are disclosed containing 2- phenylimidazole simultaneously [1,2-a] pyridine
The derivative of group, but it is not related to luminescent properties.
Summary of the invention
The present invention is to overcome that luminous intensity described in the above-mentioned prior art is not high, thermal stability is insufficient and dissolubility is bad
Defect, provide a kind of N heterocycle Benzophenone analog derivative containing hydrogenation phenthazine group, the N heterocycle Benzophenone class provided spreads out
Biology can be used as luminous organic material, have unique AIE effect, high luminous intensity, good thermal stability and good
Dissolubility.
Another object of the present invention is to provide the preparation methods of above-mentioned N heterocycle Benzophenone analog derivative.
A further purpose of the present invention is to provide above-mentioned N heterocycle Benzophenone analog derivative in luminescent material or intellectual material
In application.
In order to solve the above technical problems, the technical solution adopted by the present invention is that:
A kind of N heterocycle Benzophenone analog derivative containing hydrogenation phenthazine group has the knot of the chemistry as shown in formula (I)
Structure；
Wherein, hydrogenation phenthazine group alternatively referred to as contains N fragrance anthryl.
The present invention provides a kind of N heterocycle Benzophenone analog derivative, in the N heterocycle Benzophenone analog derivative, on the one hand by
The phenyl ring that bridging is introduced between the anthryl of fragrance containing N and carbonyl, forms big conjugate planes；On the other hand, since there are C ...
H ... pi accumulation, this is conducive to shining for molecule, obtains high fluorescence quantum yield.Spread out further, since this contains N heterocycle Benzophenone class
The phenomenon that biological energy source generates aggregation-induced emission (AIE) effect, can effectively inhibit exciton annihilation keeps molecule poly- in high concentration
Collect under state than there is stronger fluorescent emission under low concentration, to have high luminous intensity.
Also, since the relative molecular weight of the N heterocycle Benzophenone analog derivative is larger, heterocycle structure containing N and the anthracene of fragrance containing N
There is conjugation situation in based structures, so that the N heterocycle Benzophenone analog derivative of preparation has the advantages that good thermal stability.Separately
Outside, above-mentioned N heterocycle Benzophenone analog derivative also has good dissolubility.
Therefore, N heterocycle Benzophenone analog derivative provided by the invention can be used as luminescent material or intellectual material, full-color
It is had a good application prospect in display and solid-state lighting field.
Meanwhile the present invention realizes the controllable preparation of the above-mentioned Benzophenone of heterocycle containing N analog derivative.
The present invention also protects the preparation method of above-mentioned N heterocycle Benzophenone analog derivative, the preparation method is that, by (4- bromine
Phenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone 10- hydrogen-phenthazine is by nucleophilic substitution post-treated
To formula (I) compound.
Preferably, (4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone rubs with 10- hydrogen-phenthazine
You are than being 1: (1~1.2).(2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone and 10- it is highly preferred that (4- bromophenyl)
Hydrogen-phenthazine molar ratio is 1: 1.1.
Preferably, the nucleophilic substitution carries out in the presence of palladium catalyst, alkali and solvent.
Preferably, the palladium catalyst is palladium acetate.
Preferably, the alkali is potassium tert-butoxide.
Preferably, the solvent is toluene.
Preferably, the nucleophilic substitution carries out in inert atmosphere.Preferably, the inert atmosphere is nitrogen atmosphere
It encloses, argon atmosphere or helium atmosphere.
Preferably, the condition of the nucleophilic substitution is at a temperature of 128~130 DEG C, to be stirred to react 12~15h.More
Preferably, the condition of the nucleophilic substitution is at a temperature of 130 DEG C, to be stirred to react 15h.
Preferably, the post-processing is cooling, distillation, extracts, dry, concentration, separation.Cooling collect obtains yellow muddiness
Turbid solution is evaporated under reduced pressure and removes toluene by liquid, and remaining solid is extracted with dichloromethane three times, merges gained organic phase three times, uses
Anhydrous magnesium sulfate is dry, then is evaporated under reduced pressure organic phase and obtains crude product；Finally use ethyl acetate and petroleum ether as eluant, eluent into
Row silica gel column layer is separated by decantation to ((4- (10H- phenthazine -10- base) phenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) first
Ketone.
The present invention also protects application of the above-mentioned N heterocycle Benzophenone analog derivative in luminescent material or intellectual material.
Above-mentioned N heterocycle Benzophenone analog derivative prepare in luminescent device application also protection scope of the present invention it
It is interior.
(the 4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone can be joined by those skilled in the art
Prior art preparation is examined to obtain.
Specifically, described (4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone is by (E) -1- (4- bromine
Phenyl) -3- phenyl propyl- 2- alkene -1- ketone and 2-aminopyridine carry out Michael cyclization reaction after processing in the presence of elemental iodine
It obtains.
Preferably, described (E) -1- (4- the bromophenyl) -3- phenyl propyl- 2- alkene -1- ketone, 2-aminopyridine and elemental iodine rub
You are than being (1~1.1): (2~2.2): (0.23~0.25).It is highly preferred that (E) -1- described in step S1. (4- bromophenyl) -
The molar ratio of 3- phenyl propyl- 2- alkene -1- ketone, 2-aminopyridine and elemental iodine is 1: 2: 0.23.
Preferably, the solvent of the Michael cyclization reaction is dichloroethanes.
Preferably, the condition of the Michael cyclization reaction is to carry out heating stirring under air.Because dichloroethanes
Boiling point is relatively low, so reaction must carry out in tube sealing.
Preferably, it is preferable that the temperature of the heating stirring is 115~120 DEG C, and the time is 10~13h.It is highly preferred that
The temperature of the heating stirring is 118~120 DEG C, and the time is 10~12h.It is further preferred that heating described in step S1. is stirred
The temperature mixed is 120 DEG C, time 12h.
Preferably, the processing is cooling, transfer, concentration, separation.After solution after reaction is cooled to room temperature, with two
Chloromethanes washs tube sealing transfer solution in eggplant-shape bottle；Organic phase is concentrated under reduced pressure again and obtains crude product；Finally with ethyl acetate with
Petroleum ether carries out silica gel column layer as eluant, eluent and is separated by decantation to (4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl)
Ketone.
Compared with prior art, the beneficial effects of the present invention are:
It is provided by the invention containing hydrogenation phenthazine group N heterocycle Benzophenone analog derivative have unique AIE effect,
High luminous intensity, good thermal stability and good dissolubility, can be used as that a kind of performance is good, cost is relatively low, space structure
The novel soluble light emitting molecule of high distortion.The N heterocycle Benzophenone analog derivative is preparing luminescent material, luminescent device or intelligence
The application aspects such as energy material have significant economic value, before having good application in full-color display and solid-state lighting field
Scape.
Detailed description of the invention
PDI-POZ is the abbreviation of formula (I) compound.
Fig. 1 is the hydrogen spectrogram of N heterocycle Benzophenone analog derivative made from embodiment 1.
Fig. 2 is the mass spectrogram of N heterocycle Benzophenone analog derivative made from embodiment 1.
Fig. 3 is the ultraviolet-visible absorption spectroscopy figure of N heterocycle Benzophenone analog derivative made from embodiment 1.
Fig. 4 is the AIE spectrum in the solution of different moisture content of N heterocycle Benzophenone analog derivative made from embodiment 1
Figure.
Fig. 5 is the solvation effect figure of N heterocycle Benzophenone analog derivative made from embodiment 1.
Fig. 6 is the cyclic voltammogram of N heterocycle Benzophenone analog derivative made from embodiment 1.
Fig. 7 is the thermogravimetric analysis figure (TGA) of N heterocycle Benzophenone analog derivative made from embodiment 1.
Fig. 8 is the differential scanning calorimetry figure (DSC) of N heterocycle Benzophenone analog derivative made from embodiment 1
Specific embodiment
The present invention is further illustrated With reference to embodiment.
Raw material in embodiment can be by being commercially available；
Unless stated otherwise, the present invention uses reagent, method and apparatus for the art conventional reagent, method and are set
It is standby.
Embodiment 1
A kind of N heterocycle Benzophenone analog derivative containing hydrogenation phenthazine group, i.e. formula (I) compound, by following methods
It is prepared:
(1) preparation of (4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone:
Weigh (E) -1- (4- bromophenyl) -3- phenyl propyl- 2- alkene -1- ketone 43mg, 2-aminopyridine 30mg elemental iodine 60mg
With 2mL dichloroethanes in 10mL tube sealing, Michael cyclization reaction is carried out under the conditions of 120 DEG C of temperature, (4- bromine is obtained after processing
Phenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone；
(2) preparation of formula (I) compound:
Weigh (4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone 180mg, 10- hydrogen-phenthazine
115mg, potassium tert-butoxide 80mg, tri-tert-butylphosphine 4mg, for the toluene of palladium acetate 5.5mg and 5mL in tube sealing, device is taken out in stirring
Middle air is simultaneously filled with nitrogen protection, and after having reacted, crude product is passed through by the heating stirring back flow reaction 15h under 130 DEG C of nitrogen protections
Supercooling, distillation, extraction, drying, concentration, separation.Cooling collect obtains yellow turbid solution, and turbid solution is evaporated under reduced pressure and removes first
Benzene, remaining solid are extracted with dichloromethane three times, merge gained organic phase three times, dry with anhydrous magnesium sulfate, then are evaporated under reduced pressure
Organic phase obtains crude product；It finally uses ethyl acetate to carry out silica gel column chromatography as eluant, eluent with petroleum ether to separate.What is obtained is pure
Reaction mixture is evaporated under reduced pressure and obtains after being dried in vacuo 190g yellow solid, as formula (I) compound, purity 99%, yield
80%.
Characterization and performance test
Characterization and performance test are carried out to the N heterocycle Benzophenone analog derivative that embodiment 1 obtains.
(1) nuclear magnetic resonance: Brooker 400MHz NMR spectrometer with superconducting magnet.
Using the MRI scan N heterocycle Benzophenone analog derivative hydrogen signal and its hydrogen signal is referred to
Recognize, the result of embodiment 1 is as shown in Figure 1.
From fig. 1, it can be seen that the δ (ppm) of the N heterocycle Benzophenone analog derivative is 8.22,8.19,8.17,8.17,7.77,
7.75,7.58,7.57,7.56,7.54,7.52,7.51,7.50,7.44,7.42,7.36,7.35,7.34,7.26,7.24,
7.22,7.20,7.13,7.11,7.09,7.04,7,03,7.01,6.85.
(2) mass spectrum: LC-MS instrument LCMS-2020.It N heterocycle Benzophenone analog derivative is dissolved in acetonitrile is made into concentration and be
The solution of 1mg/mL is tested.
Fig. 2 is the mass spectrogram for the N heterocycle Benzophenone analog derivative that embodiment 1 is prepared, from the figure, it can be seen that Fig. 2
Middle relative molecular mass is 495.28, consistent with the synthesized relative molecular mass of N heterocycle Benzophenone analog derivative.
(3) ultraviolet-visible absorption spectroscopy: Shimadzu ultra-violet and visible spectrophotometer UV-2700.N heterocycle Benzophenone class is spread out
Biology, which is dissolved in THF, is made into 1 × 10-3The mother liquor of mol/L when test, is diluted to 1 × 10-5mol/L。
Fig. 3 is the N heterocycle Benzophenone analog derivative that is prepared of embodiment 11 × 10-5In the tetrahydrofuran of mol/L
Ultraviolet-visible absorption spectroscopy figure.As can be seen from Figure 3, the major absorbance peak position of the N heterocycle Benzophenone analog derivative is 347nm.
(5) AIE spectrum: FLS980 luminoscope.
The concentration for keeping N heterocycle Benzophenone analog derivative in test solution is 1 × 10-5Mol/L is adjusted four in test solution
The ratio of hydrogen furans and water.First N heterocycle Benzophenone analog derivative is dissolved in tetrahydrofuran and is made into 1 × 10-3The mother liquor of mol/L,
Maintaining test overall solution volume is 3mL.Such as: when water content is 90%, the amount that each ingredient is added is mother liquor: water: tetrahydrofuran
=30uL: 2700uL: 270uL.
Fig. 4 is AIE spectrum of the N heterocycle Benzophenone analog derivative that is prepared of embodiment 1 in the solution of various concentration
Figure.Fluorescence of the N heterocycle Benzophenone analog derivative in tetrahydrofuran-aqueous solution that water content is 1%~99% is tested respectively
Spectrum；In figure, arrow instruction direction is that the water content of solution corresponding to 11 fluorescence figure lines successively increases direction.By in Fig. 4
As can be seen that the launch wavelength of N heterocycle Benzophenone analog derivative is 572nm；When water content is lower than 95%, N heterocycle Benzophenone
There is apparent red shift in the glimmering launch wavelength of analog derivative in the solution；And after water content is more than 95%, corresponding fluorescence intensity
It is greatly enhanced, it is known that there are apparent AIE phenomenons for N heterocycle Benzophenone analog derivative.
(6) solvation effect: FLS980 luminoscope
Fig. 5 is the N heterocycle Benzophenone analog derivative that is prepared of embodiment 1 corresponding normalized light in different solvents
Spectrogram, it can be seen that with the enhancing of solvent polarity, spectrum shows apparent solvatochromic effect, this is because point
ICT effect in son, i.e., caused by charge-transfer excitation state.
(7) cyclic voltammetric: electrochemical workstation PGSTAT302.
Fig. 6 is the cyclic voltammogram for the N heterocycle Benzophenone analog derivative that embodiment 1 is prepared.By N heterocycle Benzophenone class
Derivative is dissolved in the solution that 1mg/mL is made into acetonitrile, measures N heterocycle benzene first by cyclic voltammetry under electrochemical workstation
The reduction potential of ketones derivant is E=0.6746V.
(8) thermogravimetric analysis: high temperature synchronous solving STA409PC, heating rate: 10K/min；Temperature range: room temperature~
800℃；Gas shield: nitrogen；
Under nitrogen protection, thermogravimetric analysis has been carried out to N heterocycle Benzophenone analog derivative.
As can be known from Fig. 7,5% weightless temperature of N heterocycle Benzophenone analog derivative is 404.03 DEG C, illustrates N heterocycle benzene first
Ketones derivant has good thermal stability, the potentiality with the good OLED of processability.
(9) differential scanning calorimetry: low temperature differential scanning calorimeter DSC3 1707908S, temperature range: -90~500
℃；Lifting/lowering temperature speed: 0.001~300 DEG C/min；Gas shield: nitrogen；
Under nitrogen protection, the analysis of differential scanning calorimetry has been carried out to N heterocycle Benzophenone analog derivative.
As it can be observed in the picture that the glass transition temperature of N heterocycle Benzophenone analog derivative is 211.6 DEG C
Illustrate that N heterocycle Benzophenone analog derivative has good thermal stability, it is latent with the good OLED of processability
Power.
(8) dissolubility
It is obtained by testing test, N heterocycle Benzophenone analog derivative made from embodiment 1 can be dissolved in acetone, acetic acid second
Ester, tetrahydrofuran, in dichloromethane solvent.In table 1, "+" expression can be dissolved in corresponding solvent, and "+" number is got over multilist and shown
Solubility is bigger in corresponding solvent.
The dissolubility of N heterocycle Benzophenone analog derivative made from 1 embodiment 1 of table
| Solvent | Acetone | Ethyl acetate | Tetrahydrofuran | Methylene chloride |
| Dissolubility | +++ | +++ | ++ | ++ |
In conclusion N heterocycle Benzophenone analog derivative provided by the invention has unique AIE effect, high strong light
Degree, good thermal stability and good dissolubility, can be used as that a kind of performance is good, cost is relatively low, space structure high distortion
Novel soluble light emitting molecule.The N heterocycle Benzophenone analog derivative is answered preparing luminescent material, luminescent device or intellectual material etc.
There is significant economic value with aspect, had a good application prospect in full-color display and solid-state lighting field.
Meanwhile the present invention realizes the controllable preparation of N heterocycle Benzophenone analog derivative；Preparation cost is cheap, raw material sources
Extensively, it can be achieved that large-scale production, has wide Commercial Prospect.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention.For those of ordinary skill in the art, may be used also on the basis of the above description
To make other variations or changes in different ways.There is no necessity and possibility to exhaust all the enbodiments.It is all this
Made any modifications, equivalent replacements, and improvements etc., should be included in the claims in the present invention within the spirit and principle of invention
Protection scope within.
Claims (10)
1. a kind of N heterocycle Benzophenone analog derivative containing hydrogenation phenthazine group, which is characterized in that have as shown in formula (I)
Chemical structure；
2. the preparation method of N heterocycle Benzophenone analog derivative described in claim 1, which is characterized in that by (4- bromophenyl) (2-
Phenylimidazole simultaneously [1,2-a] pyridin-3-yl) ketone and 10- hydrogen-phenthazine by the way that nucleophilic substitution is post-treated obtain formula
(I) compound.
3. preparation method according to claim 2, which is characterized in that (4- bromophenyl) (2- phenylimidazole simultaneously [1,2-a] pyrrole
Pyridine -3- base) ketone and 10- hydrogen-phenthazine molar ratio be 1: (1~1.2).
4. preparation method according to claim 2, which is characterized in that the nucleophilic substitution palladium catalyst, alkali and
It is carried out in the presence of solvent.
5. the preparation method according to claim 4, which is characterized in that the palladium catalyst is palladium acetate.
6. the preparation method according to claim 4, which is characterized in that the alkali is potassium tert-butoxide.
7. the preparation method according to claim 4, which is characterized in that the nucleophilic substitution in inert atmosphere into
Row.
8. the preparation method according to claim 4, which is characterized in that the condition of the nucleophilic substitution is, 128~
At a temperature of 130 DEG C, it is stirred to react 12~15h.
9. preparation method according to claim 8, which is characterized in that the nucleophilic substitution stirs at a temperature of 130 DEG C
Mix reaction 15h.
10. application of the N heterocycle Benzophenone analog derivative described in claim 1 in luminescent material or intellectual material.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910223531.XA CN109851618A (en) | 2019-03-22 | 2019-03-22 | A kind of N heterocycle Benzophenone analog derivative and its preparation method and application containing hydrogenation phenthazine group |
| CN201910532978.5A CN110117283B (en) | 2019-03-22 | 2019-06-19 | N heterocyclic benzophenone derivative containing hydrogenated phenothiazine group and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910223531.XA CN109851618A (en) | 2019-03-22 | 2019-03-22 | A kind of N heterocycle Benzophenone analog derivative and its preparation method and application containing hydrogenation phenthazine group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109851618A true CN109851618A (en) | 2019-06-07 |
Family
ID=66901643
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910223531.XA Withdrawn CN109851618A (en) | 2019-03-22 | 2019-03-22 | A kind of N heterocycle Benzophenone analog derivative and its preparation method and application containing hydrogenation phenthazine group |
| CN201910532978.5A Active CN110117283B (en) | 2019-03-22 | 2019-06-19 | N heterocyclic benzophenone derivative containing hydrogenated phenothiazine group and preparation method thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910532978.5A Active CN110117283B (en) | 2019-03-22 | 2019-06-19 | N heterocyclic benzophenone derivative containing hydrogenated phenothiazine group and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN109851618A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113292552A (en) * | 2021-06-22 | 2021-08-24 | 广东工业大学 | Benzo five-membered ring aza derivative containing benzophenone group and preparation method and application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111875602B (en) * | 2020-07-15 | 2022-10-21 | 广东工业大学 | Cyano-modified pyridino-imidazole derivative and preparation method and application thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040072004A (en) * | 2003-02-07 | 2004-08-16 | 삼성에스디아이 주식회사 | Emitting compound for electroluminescence device and device using thereof |
| KR20110049244A (en) * | 2009-11-04 | 2011-05-12 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN105567217B (en) * | 2015-12-15 | 2017-12-01 | 华南理工大学 | A kind of more stimuli responsive organic molecule luminescent materials and preparation and application |
-
2019
- 2019-03-22 CN CN201910223531.XA patent/CN109851618A/en not_active Withdrawn
- 2019-06-19 CN CN201910532978.5A patent/CN110117283B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113292552A (en) * | 2021-06-22 | 2021-08-24 | 广东工业大学 | Benzo five-membered ring aza derivative containing benzophenone group and preparation method and application thereof |
| CN113292552B (en) * | 2021-06-22 | 2022-02-08 | 广东工业大学 | Benzo five-membered ring aza derivative containing benzophenone group and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110117283B (en) | 2021-06-15 |
| CN110117283A (en) | 2019-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110283169A (en) | A kind of N heterocycle Benzophenone analog derivative and preparation method thereof containing substituted hydrogenated acridine group | |
| CN109824659A (en) | A kind of organic compound and its application based on heteroaryl amine structure | |
| CN109761967A (en) | A kind of organic compound based on heteroaryl amine structure and its application on OLED | |
| CN108084150B (en) | Organic supramolecular white light emitting material and preparation method thereof and OLED device | |
| CN106467486A (en) | A kind of organic compound containing dimethylanthracene and its application | |
| CN109912578A (en) | A kind of compound of the structure containing spiro fluorene and its application on organic electroluminescence device | |
| CN110117283A (en) | A kind of N heterocycle Benzophenone analog derivative and preparation method thereof containing hydrogenation phenthazine group | |
| CN108203417A (en) | Organic compound and organic electroluminescence device based on fluorenes | |
| CN110128349A (en) | A kind of nitrogenous heterocyclic polycyclic aromatic hydrocarbon derivative and its application and organic electroluminescence device | |
| CN110467609A (en) | Gathering induced luminescence material and the preparation method and application thereof a kind of while that there is circular polarised luminescence and the transmitting of hot activation delayed fluorescence | |
| CN110183475A (en) | Double boron oxa- pyrene compounds and its application based on donor-receiver | |
| CN107868083A (en) | A kind of organic compound of fluorenes of 9,9 ' spiral shell two for core and its application on organic electroluminescence device | |
| CN106220514A (en) | A kind of Spirobifluorene compound containing the tert-butyl group and preparation thereof and application | |
| CN108822020A (en) | A kind of benzidine derivative and its organic electroluminescence device | |
| CN107868049A (en) | Organic compound and organic electroluminescence device using the fluorenes of 9,9 ' spiral shell two as core | |
| CN106432051B (en) | A kind of carbazole analog derivative and its preparation method and application | |
| CN106188026B (en) | A kind of unsymmetric structure electroluminescent organic material and its application | |
| CN112645949A (en) | Aromatic amine derivative containing benzophenone group and preparation method and application thereof | |
| CN109400519B (en) | A kind of tetraphenyl ethylene-benzophenone-carbazole derivates, crystal and the preparation method and application thereof | |
| CN110183476A (en) | Double boron oxa- dibenzo [A, J] anthracene derivants and its application | |
| CN110128329A (en) | Nitrogenous heterocyclic aromatic amino-derivative and its application and organic electroluminescence device | |
| CN114835663A (en) | Naphtho heteroaryl compound, organic electroluminescent device and display device | |
| CN113501817A (en) | Quinolinone derivative containing arylamine group and preparation and application thereof | |
| CN109535125A (en) | It is a kind of using dibenzo hexatomic ring as the compound of core and its application on OLED | |
| CN103304470A (en) | Organic semiconductor material containing naphthalene, preparation method thereof and organic light-emitting device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20190607 |
|
| WW01 | Invention patent application withdrawn after publication |