CN107739608A - A kind of high temperature resistant blue fluorescent material and preparation method thereof - Google Patents
A kind of high temperature resistant blue fluorescent material and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to technical field of organic luminescence materials, more particularly to a kind of high temperature resistant blue fluorescent material and preparation method thereof, the high temperature resistant blue fluorescent material is organic material 4 ' (base of 8 (4 (base of 9H carbazoles 9) phenyl) naphthalene 1) [1,1 ' biphenyl] 4 formonitrile HCNs, molecular formula C41H21N2, using 4 cyanobiphenyls as electron acceptor, 4 (base of 9H carbazoles 9) phenyl boric acids are electron donor, and carrying out chemical reaction under tetrakis triphenylphosphine palladium catalysis is prepared.There is certain dihedral angle between 4 cyanobiphenyls and N phenyl carbazoles in high temperature resistant blue fluorescent material prepared by the present invention, HOMO and LUMO is enabled to realize that conjugation blocks, in the case where 280nm light excites, its maximum emission peak is in 440nm, for dark blue coloured light, the fluorescent material that simultaneously prepared by the present invention has good heat endurance, and its decomposition temperature is 409 DEG C.High temperature resistant blue fluorescent material obtained by the present invention has good heat endurance and blue fluorescent emissions performance, has potential application prospect as fluorescent material.
Description
【Technical field】
The present invention relates to technical field of organic luminescence materials, and in particular to a kind of high temperature resistant blue fluorescent material and its preparation
Method.
【Background technology】
Organic Light Emitting Diode (OLED) has great application potential in FPD and general illumination, therefore causes
Greatly concern.In order to realize that OLED white light is shown, the development of three primary colors fluorescent material is most important, compared to green glow and red
Luminescent material, the development of blue fluorescent material are but made slow progress.In recent years, thermic delayed fluorescence (TADF) material is by quantum in the inner
The advantages that efficiency high, stability are good, cost is cheap, become the important means that scientists expand blue fluorescent material.
In order to design effective blue TADF materials, material molecule should meet following three key requests simultaneously：(1) it is single
Energy level difference Δ EST between weight state and triplet is sufficiently small, can so accelerate to wear between the inverse system from triplet to singlet state
More process；(2) there is high luminescence S1 and stable T1 to provide the radiant light of pure blue；(3) have it is at a relatively high from T1 to
Speed is passed through between S1 inverse system to obtain a higher luminous efficiency.In principle, when minimum singlet state and minimum triplet it
Between energy difference it is less when, can also occur to pass through between inverse system in the pure aromatic organic compounds without heavy metal
[14].As shown by data, Δ EST can be directly proportional to electron exchange, and electron exchange can be with the occupied molecular orbit of highest (HOMO)
It is overlapping directly proportional between lowest unoccupied molecular orbital (LUMO), so overlapping between less HOMO and LUMO can subtract
Small Δ EST.These three require the selection for limiting electron donor (D) and acceptor (A) so that realize one using blue TADF as base
The high-quantum efficiency OLEDs of plinth becomes problem.
Because blue fluorescent material has wider native band gap, unbalanced carrier transport ability, and be difficult to
Other functional layers match in OLEDs.Although the exploitation of OLEDs materials has been concentrated on the blue glimmering of high efficiency and long-life
In design, synthesis and the application of luminescent material, but the efficiency of blue fluorescent material and heat endurance still are below red and green
Material.
【The content of the invention】
The goal of the invention of the present invention is：For blue-light fluorescent material heat endurance it is poor the problem of, there is provided a kind of high fever
Blue fluorescent material of stability and preparation method thereof.
To achieve these goals, the technical solution adopted by the present invention is as follows：
A kind of high temperature resistant blue fluorescent material, 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 '-connection
Benzene] -4- formonitrile HCNs, molecular formula C41H21N2, its structural formula is：
The preparation method of the high temperature resistant blue fluorescent material, comprises the following steps：
S1. presoma I synthesis：Into the mixed solution of potassium carbonate and toluene, 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromo are added
Benzene, tetrakis triphenylphosphine palladium, then the heating reflux reaction 24-30 hours at 75-85 DEG C, through purification by liquid extraction, collect solid 4-
Bromo- 4 '-cyanobiphenyl, that is, obtain presoma I；
S2. presoma II synthesis：Into anhydrous Isosorbide-5-Nitrae-dioxane solution, presoma I, double (pinacol conjunctions) two are added
Double (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of boron, potassium acetate and 1,1'-, are heated to reflux at 88-95 DEG C
22-28 hours are reacted, through purification by liquid extraction, solid 4'- cyano group-[1,1'- biphenyl] -4- borates is collected, that is, obtains presoma II；
S3. presoma III synthesis：Into the mixed solution of Isosorbide-5-Nitrae-dioxane and potassium carbonate, presoma II, 1 are added,
8- dibromine naphthalenes, after standing 5-7 minutes, add tetrakis triphenylphosphine palladium, the back flow reaction 46-50 hours at 88-92 DEG C, through extraction
Purification, solid 4'- cyano group-[1,1'- biphenyl] -4- (8- bromonaphthalenes) is collected, that is, obtains presoma III；
S4. the synthesis of high temperature resistant blue fluorescent material：Into the mixed solution of Isosorbide-5-Nitrae-dioxane and potassium carbonate, 4- is added
(9H- carbazole -9- bases) phenyl boric acid and presoma III, tetrakis triphenylphosphine palladium is added after standing 8-10 minutes, at 78-82 DEG C
Be heated to reflux 24-26 hours, through purification by liquid extraction, collect solid 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,
1 '-biphenyl] -4- formonitrile HCNs, obtain high temperature resistant blue fluorescent material.
Further, in step S1, in molar ratio, the 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromobenzene, tetrakis triphenylphosphine palladium
Mol ratio be 40-42：45-47：0.2-0.3.
Further, in step S2, in molar ratio, the presoma I, double (pinacol conjunctions) two boron, potassium acetate and 1,1'-
The mol ratio of double (diphenylphosphine) ferrocene palladium chloride dichloromethane complex is 11-13：13-14：160-165：0.2-
0.3。
Further, in step S3, in molar ratio, the presoma II, 1,8- dibromine naphthalenes and tetrakis triphenylphosphine palladium
Mol ratio is 7-9：10-12：0.4-0.5.
Further, in step S4, in molar ratio, presoma III, 4- (9H- carbazole -9- bases) phenyl boric acid, four (three
Phenylphosphine) mol ratio of palladium is 10-12：9-10：0.5-0.6.
Wherein step S4 reaction equation is as follows：
In summary, by adopting the above-described technical solution, the beneficial effects of the invention are as follows：
The present invention is core using 1,8- dibromine naphthalenes, and design has synthesized a molecule, and two bromines of this molecule are respectively by 4-
Cyanobiphenyl, the substitution of N- phenyl carbazoles, so as to obtain 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 '-connection
Benzene] -4- formonitrile HCNs, wherein 4- cyanobiphenyls are as electron acceptor, due to the presence of naphthalene core so that electron donor and acceptor are by one
Big dihedral angle separates, and so as to realize that HOMO and lumo energy conjugation block, the molecule built typically has certain
Rigid structure, i.e., after molecule is excited, molecular configuration is held essentially constant, and is caused so as to effectively reduce by molecular vibration
Nonradiative decay.In addition, high temperature resistant blue fluorescent material prepared by the present invention, its decomposition temperature is (corresponding during material weightlessness 5%
Temperature) be 409 DEG C, there is good heat endurance, can by the way of sublimation purification and vacuum evaporation scale system
Standby device.Through fluorescence spectrometry, high temperature resistant blue fluorescent material prepared by the present invention maximum emission wavelength in dichloromethane
It is dark blue coloured light for 440nm.
【Brief description of the drawings】
Fig. 1 is the proton nmr spectra of the high temperature resistant blue fluorescent material.
Fig. 2 is the thermogravimetic analysis (TGA) curve of the high temperature resistant blue fluorescent material.
Fig. 3 is the fluorescence spectrum of the high temperature resistant blue fluorescent material in dichloromethane.
【Embodiment】
With reference to embodiment, the invention will be further described.
Embodiment 1
A kind of preparation method of blue-light fluorescent material, comprises the following steps：
S1. presoma I synthesis：In the mixed solution containing potassium carbonate and toluene, addition 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-
Dibromobenzene, tetrakis triphenylphosphine palladium, then heating reflux reaction 27 hours at 80 DEG C, through purification by liquid extraction, it is bromo- to collect solid 4-
4 '-cyanobiphenyl, that is, obtain presoma I；Wherein in molar ratio, the 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromobenzene, four (triphenyls
Phosphine) palladium mol ratio be 41：46：0.2.
S2. presoma II synthesis：Into anhydrous Isosorbide-5-Nitrae-dioxane solution, presoma I, double (pinacol conjunctions) two are added
Double (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of boron, potassium acetate and 1,1'-, the heating reflux reaction at 80 DEG C
25 hours, through purification by liquid extraction, solid 4'- cyano group-[1,1'- biphenyl] -4- borates are collected, that is, obtain presoma II；Wherein press
Mol ratio, double (diphenylphosphine) the ferrocene palladium chlorides two of the presoma I, double (pinacol conjunctions) two boron, potassium acetate and 1,1'-
The mol ratio of chloromethanes complex compound is 12：163：13-14：0.2.
S3. presoma III synthesis：Into the mixed solution containing Isosorbide-5-Nitrae-dioxane and potassium carbonate, presoma is added
II, 1,8- dibromine naphthalenes, after standing 6 minutes, tetrakis triphenylphosphine palladium is added, back flow reaction 48 hours at 80 DEG C, is carried through extraction
It is pure, solid 4'- cyano group-[1,1'- biphenyl] -4- (8- bromonaphthalenes) is collected, that is, obtains presoma III；Wherein, in molar ratio, it is described
Presoma II, 1,8- dibromine naphthalenes and tetrakis triphenylphosphine palladium mol ratio are 8：11：0.4.
S4. the synthesis of high temperature resistant blue fluorescent material：Into the mixed solution containing Isosorbide-5-Nitrae-dioxane and potassium carbonate, add
Enter presoma III and 4- (9H- carbazole -9- bases) phenyl boric acid, tetrakis triphenylphosphine palladium is added after standing 9 minutes, add at 80 DEG C
Heat backflow 25 hours, through purification by liquid extraction, collect solid 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 '-connection
Benzene] -4- formonitrile HCNs, obtain high temperature resistant blue fluorescent material；Wherein, in molar ratio, presoma III, 4- (9H- carbazoles -9-
Base) phenyl boric acid, tetrakis triphenylphosphine palladium mol ratio be 11：9：0.5.
Embodiment 2
A kind of preparation method of blue-light fluorescent material, comprises the following steps：
S1. presoma I synthesis：In the mixed solution containing potassium carbonate and toluene, addition 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-
Dibromobenzene, tetrakis triphenylphosphine palladium, then heating reflux reaction 24 hours at 75 DEG C, through purification by liquid extraction, it is bromo- to collect solid 4-
4 '-cyanobiphenyl, that is, obtain presoma I；Wherein in molar ratio, the 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromobenzene, four (triphenyls
Phosphine) palladium mol ratio be 40：45：0.2.
S2. presoma II synthesis：Into anhydrous Isosorbide-5-Nitrae-dioxane solution, presoma I, double (pinacol conjunctions) two are added
Double (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of boron, potassium acetate and 1,1'-, the heating reflux reaction at 88 DEG C
22 hours, through purification by liquid extraction, solid 4'- cyano group-[1,1'- biphenyl] -4- borates are collected, that is, obtain presoma II；Wherein press
Mol ratio, double (diphenylphosphine) the ferrocene palladium chlorides two of the presoma I, double (pinacol conjunctions) two boron, potassium acetate and 1,1'-
The mol ratio of chloromethanes complex compound is 11：160：13：0.2.
S3. presoma III synthesis：Into the mixed solution containing Isosorbide-5-Nitrae-dioxane and potassium carbonate, presoma is added
II, 1,8- dibromine naphthalenes, after standing 5 minutes, tetrakis triphenylphosphine palladium is added, back flow reaction 46 hours at 88 DEG C, is carried through extraction
It is pure, solid 4'- cyano group-[1,1'- biphenyl] -4- (8- bromonaphthalenes) is collected, that is, obtains presoma III；Wherein, in molar ratio, it is described
Presoma II, 1,8- dibromine naphthalenes and tetrakis triphenylphosphine palladium mol ratio are 7：10：0.4.
S4. the synthesis of high temperature resistant blue fluorescent material：Into the mixed solution containing Isosorbide-5-Nitrae-dioxane and potassium carbonate, add
Enter presoma III and 4- (9H- carbazole -9- bases) phenyl boric acid, tetrakis triphenylphosphine palladium is added after standing 8 minutes, add at 78 DEG C
Heat backflow 24 hours, through purification by liquid extraction, collect solid 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 '-connection
Benzene] -4- formonitrile HCNs, obtain high temperature resistant blue fluorescent material；Wherein, in molar ratio, presoma III, 4- (9H- carbazoles -9-
Base) phenyl boric acid, tetrakis triphenylphosphine palladium mol ratio be 10：9：0.5.
Embodiment 3
A kind of preparation method of blue-light fluorescent material, comprises the following steps：
S1. presoma I synthesis：In the mixed solution containing potassium carbonate and toluene, addition 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-
Dibromobenzene, tetrakis triphenylphosphine palladium, then heating reflux reaction 30 hours at 85 DEG C, through purification by liquid extraction, it is bromo- to collect solid 4-
4 '-cyanobiphenyl, that is, obtain presoma I；Wherein in molar ratio, the 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromobenzene, four (triphenyls
Phosphine) palladium mol ratio be 42：47：0.3.
S2. presoma II synthesis：Into anhydrous Isosorbide-5-Nitrae-dioxane solution, presoma I, double (pinacol conjunctions) two are added
Double (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of boron, potassium acetate and 1,1'-, the heating reflux reaction at 95 DEG C
28 hours, through purification by liquid extraction, solid 4'- cyano group-[1,1'- biphenyl] -4- borates are collected, that is, obtain presoma II；Wherein press
Mol ratio, double (diphenylphosphine) the ferrocene palladium chlorides two of the presoma I, double (pinacol conjunctions) two boron, potassium acetate and 1,1'-
The mol ratio of chloromethanes complex compound is 13：165：13-14：0.3.
S3. presoma III synthesis：Into the mixed solution containing Isosorbide-5-Nitrae-dioxane and potassium carbonate, presoma is added
II, 1,8- dibromine naphthalenes, after standing 7 minutes, tetrakis triphenylphosphine palladium is added, back flow reaction 50 hours at 92 DEG C, is carried through extraction
It is pure, solid 4'- cyano group-[1,1'- biphenyl] -4- (8- bromonaphthalenes) is collected, that is, obtains presoma III；Wherein, in molar ratio, it is described
Presoma II, 1,8- dibromine naphthalenes and tetrakis triphenylphosphine palladium mol ratio are 9：12：0.5.
S4. the synthesis of high temperature resistant blue fluorescent material：Into the mixed solution containing Isosorbide-5-Nitrae-dioxane and potassium carbonate, add
Enter presoma III and 4- (9H- carbazole -9- bases) phenyl boric acid, tetrakis triphenylphosphine palladium is added after standing 10 minutes, add at 82 DEG C
Heat backflow 26 hours, through purification by liquid extraction, collect solid 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 '-connection
Benzene] -4- formonitrile HCNs, obtain high temperature resistant blue fluorescent material；Wherein, in molar ratio, presoma III, 4- (9H- carbazoles -9-
Base) phenyl boric acid, tetrakis triphenylphosphine palladium mol ratio be 12：10：0.6.
Embodiment 4
The proton nmr spectra of high temperature resistant blue fluorescent material is determined, hydrogen nuclear magnetic resonance spectrogram such as Fig. 1, is as a result 1H NMR
(400MHz, DMSO-d6) δ 8.14 (d, J=7.8Hz, 4H), 7.70 (q, J=8.1Hz, 2H), 7.61 (d, J=11.3Hz,
5H), 7.52 (d, J=7.5Hz, 3H), 7.28 (d, J=8.0Hz, 2H), 7.22 (d, J=7.9Hz, 2H), 7.17 (dd, J=
10.2,4.9Hz,4H),7.05(s,4H)。
Under nitrogen scope, with 10 DEG C/min heating rate, to high temperature resistant blue-fluorescence material in the range of 25-500 DEG C
Material carries out thermogravimetic analysis (TGA), thermogravimetric curve figure such as Fig. 2, from figure 2 it can be seen that high temperature resistant blue-fluorescence prepared by the present invention
Material has good heat endurance, and its decomposition temperature (corresponding temperature during material weightlessness 5%) is 409 DEG C.
By high temperature resistant blue fluorescent material with 10-5Mol/L is dissolved in dichloromethane solution, carries out fluorescence spectrometry,
The a length of 280nm of excitation light wave, fluorescence spectra such as Fig. 3, it can be seen that high temperature resistant blue fluorescent material prepared by the present invention exists
440nm has maximum emission peak, it is shown that good dark blue smooth fluorescent emission performance.
Described above is the detailed description for the present invention preferably possible embodiments, but embodiment is not limited to this hair
Bright patent claim, the equal change completed or modification change under the technical spirit suggested by all present invention, all should belong to
Cover the scope of the claims in the present invention.
Claims (7)
1. a kind of high temperature resistant blue fluorescent material, it is characterised in that the high temperature resistant blue fluorescent material is 4 '-(8- (4- (9H-
Carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 '-biphenyl] -4- formonitrile HCNs, molecular formula C41H21N2。
A kind of 2. high temperature resistant blue fluorescent material according to claim 1, it is characterised in that the high temperature resistant blue-fluorescence
The structure of material is：
3. a kind of preparation method of blue-light fluorescent material, it is characterised in that comprise the following steps：
S1. presoma I synthesis：Into the mixed solution of potassium carbonate and toluene, add 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromobenzene,
Tetrakis triphenylphosphine palladium, then the heating reflux reaction 24-30 hours at 75-85 DEG C, through purification by liquid extraction, it is bromo- to collect solid 4-
4 '-cyanobiphenyl, that is, obtain presoma I；
S2. presoma II synthesis：Into anhydrous Isosorbide-5-Nitrae-dioxane solution, add presoma I, double (pinacol conjunctions) two boron,
Potassium acetate and double (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of 1,1'-, the heating reflux reaction at 88-95 DEG C
22-28 hours, through purification by liquid extraction, solid 4'- cyano group-[1,1'- biphenyl] -4- borates are collected, that is, obtain presoma II；
S3. presoma III synthesis：Into the mixed solution of Isosorbide-5-Nitrae-dioxane and potassium carbonate, presoma II, 1,8- bis- are added
Bromonaphthalene, after standing 5-7 minutes, tetrakis triphenylphosphine palladium is added, the back flow reaction 46-50 hours at 88-92 DEG C, is carried through extraction
It is pure, solid 4'- cyano group-[1,1'- biphenyl] -4- (8- bromonaphthalenes) is collected, that is, obtains presoma III；
S4. the synthesis of high temperature resistant blue fluorescent material：Into the mixed solution of Isosorbide-5-Nitrae-dioxane and potassium carbonate, 4- (9H- are added
Carbazole -9- bases) phenyl boric acid and presoma III, tetrakis triphenylphosphine palladium is added after standing 8-10 minutes, is heated at 78-82 DEG C
Flow back 24-26 hours, through purification by liquid extraction, collect solid 4 '-(8- (4- (9H- carbazole -9- bases) phenyl) naphthalene -1- bases)-[1,1 ' -
Biphenyl] -4- formonitrile HCNs, obtain high temperature resistant blue fluorescent material.
A kind of 4. preparation method of high temperature resistant blue fluorescent material according to claim 3, it is characterised in that step S1
In, in molar ratio, the 4- cyanophenylboronic acids, Isosorbide-5-Nitrae-dibromobenzene, the mol ratio of tetrakis triphenylphosphine palladium are 40-42：45-47：
0.2-0.3。
A kind of 5. preparation method of high temperature resistant blue fluorescent material according to claim 3, it is characterised in that step S2
In, in molar ratio, double (diphenylphosphine) the ferrocene dichloros of the presoma I, double (pinacol conjunctions) two boron, potassium acetate and 1,1'-
The mol ratio for changing palladium dichloromethane complex is 11-13：13-14：160-165：0.2-0.3.
A kind of 6. preparation method of high temperature resistant blue fluorescent material according to claim 3, it is characterised in that step S3
In, in molar ratio, the presoma II, 1,8- dibromine naphthalenes and tetrakis triphenylphosphine palladium mol ratio are 7-9：10-12：0.4-
0.5。
A kind of 7. preparation method of high temperature resistant blue fluorescent material according to claim 3, it is characterised in that step S4
In, in molar ratio, presoma III, 4- (9H- carbazole -9- bases) phenyl boric acid, the mol ratio of tetrakis triphenylphosphine palladium are 10-
12：9-10：0.5-0.6.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109761879A (en) * | 2019-01-10 | 2019-05-17 | 太原理工大学 | Organic blue fluorescent material and preparation method thereof, organic electroluminescence device |
| CN114516876A (en) * | 2022-03-22 | 2022-05-20 | 安徽科技学院 | Indole [3,2-b ] carbazole based blue fluorescent material and synthetic method thereof |
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| S. YU ET AL.，: ""Facile Synthesis of N-Aryl Pyrroles via Cu(II)-Mediated Cross Coupling of Electron Deficient Pyrroles and Arylboronic Acids"", 《J. ORG. CHEM.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109761879A (en) * | 2019-01-10 | 2019-05-17 | 太原理工大学 | Organic blue fluorescent material and preparation method thereof, organic electroluminescence device |
| CN114516876A (en) * | 2022-03-22 | 2022-05-20 | 安徽科技学院 | Indole [3,2-b ] carbazole based blue fluorescent material and synthetic method thereof |
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