CN113582908A - Near-ultraviolet organic electroluminescent material based on benzene cyano, preparation method thereof and application thereof in preparing OLED - Google Patents
Near-ultraviolet organic electroluminescent material based on benzene cyano, preparation method thereof and application thereof in preparing OLED Download PDFInfo
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Abstract
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a near ultraviolet organic electroluminescent material based on benzene cyano, a preparation method thereof and application thereof in preparing OLED. The near ultraviolet organic electroluminescent material based on the benzene cyano group takes the benzene cyano group as a core, different electron-donating groups are modified on a benzene ring, the obtained molecular structure is distorted, and the molecular distance is larger in an aggregation state, so that the near ultraviolet organic electroluminescent material has the characteristics of high-efficiency solid-state luminescence, high-electric excitation exciton utilization rate and bipolarity. Based on the near ultraviolet material, non-doped and doped organic electroluminescent devices with high efficiency and low roll-off efficiency can be prepared, have wide application prospect in the field of organic electroluminescence, and are expected to be widely applied in the fields of chemical and biological sensing, high-density information storage, excitation light sources, solid state display and the like.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a near ultraviolet organic electroluminescent material based on benzene cyano and application thereof in preparing an OLED (organic light emitting diode).
Background
An organic electroluminescent device, also called an Organic Light Emitting Diode (OLED), refers to a device based on an organic light emitting material, which converts electrical energy into optical energy, in which carriers are injected from both electrodes and are combined in a light emitting layer to cause light emission under the driving of an electric field by an organic semiconductor and the light emitting material. Compared with the traditional liquid crystal display technology, the OLED has the advantages of being ultra-thin, light and thin, high in response speed, high in resolution, low in power consumption, resistant to oscillation, low-temperature resistant, flexible and the like.
Many high performance red, green, blue and white OLED devices have been reported in recent years (adv.mater. 2014,26, 5429; angelw.chem.int.ed.2018, 57,9290; adv.funct.mater.2020,30,2000019; adv.funct.mater.2020,30,1908704; Chem Soc Rev 2021,50, 1030) and have achieved excellent results in the fields of display and lighting. However, high performance near-UV OLED devices with short wavelength emission have been reported (appl. Phys. Lett.2001,79, 1231-1233; adv. Mater.2020,32,2001248; Small,2020,16,1907569), mainly because short wavelength emitting organic molecules as their light emitting layers are difficult to design and synthesize. In addition, the near-ultraviolet organic materials reported at present have low luminous efficiency, the stability of OLED devices prepared from the near-ultraviolet organic materials is poor, and the efficiency roll-off of most near-ultraviolet OLED devices is extremely serious, so that the commercialization process of the near-ultraviolet OLED devices is greatly limited.
Therefore, the technical problem to be solved by those skilled in the art is how to provide a near-ultraviolet organic material with a small roll-off degree of efficiency, high stability and high luminous efficiency for a near-ultraviolet OLED device.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a near ultraviolet organic electroluminescent material based on a benzene cyano group.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a near ultraviolet organic electroluminescent material based on benzene cyan, which has one of the following structures:
wherein R is alkane containing 1-10 carbon atoms, Ar1 and Ar2 are the same or different electron donating groups, and n is an integer of 1-4.
Preferably, the electron-donating group is one of hydrogen or an aromatic ring derivative.
Preferably, the aromatic ring derivative electron donating group is one of phenyl, fluorenyl, diphenylamine phenyl, 1,3, 6, 8-tetramethyl carbazole phenyl, phenoxazine phenyl, phenothiazine phenyl, 9, 10-dihydro-9, 9-dimethyl acridine phenyl, 9, 10-dihydro-9, 9-diphenyl acridine phenyl, 10-H-spiro [ acridine-9, 9 '-fluorene ] phenyl, 10-H-spiro [ acridine-9, 9' -xanthene ] phenyl, diphenyl-2-naphthylamine and dinaphthylamine phenyl.
Preferably, the aromatic ring derivative electron-donating group is one of the structures shown in the following formulas a to v:
wherein R 'and R' can be the same or different hydrogen atoms or alkyl chains containing 1-10 carbon atoms, and n is an integer of 0-10.
The invention also aims to provide a preparation method of the near ultraviolet organic electroluminescent material based on the benzene cyano, which comprises the following steps:
taking 2-bromobenzonitrile substances and aromatic ring derivatives as raw materials, taking toluene, water and ethanol as mixed solvents under the condition of taking potassium carbonate and tetrakis (triphenylphosphine) palladium as catalysts, and heating for reaction to obtain the near-ultraviolet organic electroluminescent material based on the benzonitrile;
the 2-bromobenzonitrile comprises 2-bromo-6-phenoxybenzonitrile or 2-bromo-6- (3-bromophenoxy) benzonitrile or 2-bromo-6- (phenylthio) benzonitrile or 2-bromo-4, 6-bis (3-bromophenoxy) benzonitrile or 2-bromo-4, 6-bis ((3-bromophenyl) thio) benzonitrile or 2-bromo-6-methoxybenzonitrile or 2-bromo-4, 6-dimethoxybenzonitrile or 2-bromo-6- (methylthio) benzonitrile or 2-bromo-4, 6-bis (methylthio) benzonitrile; the aromatic ring derivative includes: (4- (carbazol-9-yl) phenyl) boronic acid, 3, 6-di-tert-butyl-9- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -carbazole or (4- (diphenylamino) phenyl) boronic acid.
Preferably, the molar ratio of the 2-bromobenzonitrile substance to the aromatic ring derivative is 1: 1.2-4.
Preferably, the volume ratio of the toluene to the water to the ethanol is 7-9: 1-2: 1;
the molar ratio of potassium carbonate to tetrakis (triphenylphosphine) palladium is 15-25: 0.5;
the amount of the catalyst and the raw material is 3-5: 1 in terms of molar ratio of potassium carbonate to 2-bromobenzonitrile;
the amount ratio of the solvent to the raw material is calculated by the volume molar ratio of the mixed solvent to the 2-bromobenzonitrile, and the volume molar ratio is 15-25 (L):1 (mol).
Preferably, the heating reaction temperature is 90-110 ℃, and the time is 10-24 h.
The third purpose of the invention is to provide the application of the near ultraviolet organic electroluminescent material based on the benzene cyano in the field of organic electroluminescence.
Preferably, the near-ultraviolet organic electroluminescent material based on the benzene cyano is used as an emitting layer of the OLED in a doped or undoped mode.
The invention takes benzene cyano as a core, electron-donating groups are connected to a benzene ring of the benzene cyano to construct a luminophor, and a certain amount of the luminophor is introduced into other sites of the benzene ring of the benzene cyano
And (4) primitive. The organic molecules obtained based on the design method have near ultraviolet wavelength emission, are integrally twisted, and have high solid-state light-emitting efficiency; based on the material, the material can be prepared with high efficiency and low roll-offDoped and undoped near ultraviolet OLED devices have wide application prospects in the field of organic electroluminescence, and are expected to be widely applied in the fields of chemical and biological sensing, high-density information storage, excitation light sources, solid state display and the like.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the invention synthesizes a new near ultraviolet organic electroluminescent material based on benzene cyan, and the material has high solid-state luminous efficiency and high exciton utilization rate.
(2) The near ultraviolet organic electroluminescent material based on the benzene cyano is simple in synthesis method, easy in obtaining of raw materials, high in yield, stable in structure of the obtained material and simple in storage.
(3) The near ultraviolet organic electroluminescent material based on the benzene cyano has excellent electroluminescent performance and can be widely applied to the fields of organic electroluminescence and the like.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the provided drawings without creative efforts.
FIG. 1 is a L-V-J graph of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 1.
FIG. 2 is a graph showing the efficiency of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 1 as a function of luminance.
FIG. 3 is a L-V-J graph of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 2.
FIG. 4 is a graph showing the efficiency of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 2 as a function of luminance.
FIG. 5 is a L-V-J graph of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 3.
FIG. 6 is a graph showing the efficiency of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 3 as a function of luminance.
FIG. 7 is a L-V-J graph of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 4.
FIG. 8 is a graph showing the efficiency of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 4 as a function of luminance.
FIG. 9 is a L-V-J graph of a doped OLED device fabricated based on the benzonitrile-based organic electroluminescent material obtained in example 6.
FIG. 10 is a graph showing the efficiency of a doped OLED device prepared based on the benzonitrile-based organic electroluminescent material obtained in example 6 as a function of luminance.
Detailed Description
The invention provides a near ultraviolet organic electroluminescent material based on benzene cyan, which has one of the following structures:
wherein R is alkane containing 1-10 carbon atoms, Ar1 and Ar2 are the same or different electron donating groups, and n is an integer of 1-4.
In the invention, the R is preferably C1-C8 alkane, and more preferably C4-C7 alkane; said n may in particular be 1, 2, 3 or 4.
In the present invention, the electron donating group is one of hydrogen or an aromatic ring derivative.
In the present invention, the aromatic ring derivative electron donating group is one of phenyl, fluorenyl, diphenylamine phenyl, 1,3, 6, 8-tetramethylcarbazole phenyl, carbazole phenyl, phenoxazine phenyl, phenothiazine phenyl, 9, 10-dihydro-9, 9-dimethylacridine phenyl, 9, 10-dihydro-9, 9-diphenylacridine phenyl, 10-H-spiro [ acridine-9, 9 '-fluorene ] phenyl, 10-H-spiro [ acridine-9, 9' -xanthene ] phenyl, diphenyl-2-naphthylamine, and dinaphthylamine phenyl.
In the invention, the electron donating group of the aromatic ring derivative is one of the structures shown in the following formulas a to v:
wherein R 'and R' can be the same or different hydrogen atoms or alkyl chains containing 1-10 carbon atoms, and n is an integer of 0-10; when R 'and R' are the same or different alkyl chains, the carbon number is preferably 2-9, and the carbon number is further preferably 3-6; said n may in particular be 1, 2, 3, 4 or 5.
The invention also provides a preparation method of the near ultraviolet organic electroluminescent material based on the benzene cyano, which comprises the following steps:
taking 2-bromobenzonitrile substances and aromatic ring derivatives as raw materials, taking toluene, water and ethanol as mixed solvents under the condition of taking potassium carbonate and tetrakis (triphenylphosphine) palladium as catalysts, and heating for reaction to obtain the near-ultraviolet organic electroluminescent material based on the benzonitrile;
in the present invention, the 2-bromobenzonitrile-type substance comprises 2-bromo-6-phenoxybenzonitrile or 2-bromo-6- (3-bromophenoxy) benzonitrile or 2-bromo-6- (phenylthio) benzonitrile or 2-bromo-4, 6-bis (3-bromophenoxy) benzonitrile or 2-bromo-4, 6-bis ((3-bromophenyl) thio) benzonitrile or 2-bromo-6-methoxybenzonitrile or 2-bromo-4, 6-dimethoxybenzonitrile or 2-bromo-6- (methylthio) benzonitrile or 2-bromo-4, 6-bis (methylthio) benzonitrile; the aromatic ring derivative includes: (4- (carbazol-9-yl) phenyl) boronic acid, 3, 6-di-tert-butyl-9- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -carbazole or (4- (diphenylamino) phenyl) boronic acid.
In the present invention, the molar ratio of the 2-bromobenzonitrile-based substance to the aromatic ring derivative is preferably 1:1.2 to 4, and more preferably 1: 3.
In the invention, the volume ratio of the toluene to the water to the ethanol is preferably 7-9: 1-2: 1, and more preferably 8:1: 1.
In the present invention, the molar ratio of potassium carbonate to tetrakis (triphenylphosphine) palladium is preferably 15 to 25:0.5, and more preferably 18 to 21: 0.5.
In the invention, the amount of the catalyst and the raw material is preferably 3-5: 1, and more preferably 4:1 in terms of the molar ratio of potassium carbonate to 2-bromobenzonitrile.
In the present invention, the amount ratio of the solvent to the raw material is preferably 15 to 25(L):1(mol), and more preferably 17 to 21(L): 1(mol), in terms of the volume molar ratio of the mixed solvent to the 2-bromobenzonitrile.
In the invention, the heating reaction temperature is preferably 90-110 ℃, and more preferably 95-105 ℃; the time is preferably 10 to 24 hours, and more preferably 15 to 18 hours.
The invention also provides an application method of the near ultraviolet organic electroluminescent material based on the benzene cyano in the field of organic electroluminescence.
In the present invention, the near-ultraviolet organic electroluminescent material based on the benzonitrile is used as a light emitting layer of the OLED in a doped or undoped manner.
The technical solutions provided by the present invention are described in detail below with reference to examples, but they should not be construed as limiting the scope of the present invention.
Example 1: preparation of near ultraviolet organic electroluminescent material (POPCN-CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-6-phenoxybenzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (10mmol), potassium carbonate (15mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction bottle, vacuumizing for three times, adding 75mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product POPCN-CP with yield of 94%. 1H NMR (500MHz, DMSO-d6) δ 8.29(d, J ═ 7.7Hz,2H), 7.97-7.93 (M,2H), 7.86-7.82 (M,2H), 7.79-7.75 (M,1H), 7.55-7.46 (M,7H), 7.35-7.30 (M,3H), 7.27-7.25 (M,2H),7.00(d, J ═ 8.4Hz,1H), 13C NMR (125MHz, DMSO-d6) δ 159.97,154.79,145.58,139.77,137.41,136.20,134.86,130.49,130.39,126.60, 126.29,125.10,124.36,122.84,120.52,120.24,119.63,116.13,115.35,109.58, 101.85 HRMS (C31H20N2O): M/z 437.1641[ M + H +, calcd 437.1648].
In the embodiment, the heating reaction temperature is 90 ℃ and the time is 10 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 7:1: 1.
Example 2: preparation of near ultraviolet organic electroluminescent material (POPCN-2CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-6- (3-bromophenoxy) benzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (15mmol), potassium carbonate (25mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction flask, vacuumizing for three times, adding 100mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product POPCN-2CP with yield of 97%. 1H NMR (500MHz, DMSO-d6) δ 8.30-8.26 (M,4H), 8.07-8.03 (M,2H), 7.99-7.95 (M,2H), 7.88-7.65 (M,8H), 7.54-7.42 (M,9H), 7.35-7.30 (M, 5H),7.15(d, J ═ 8.5Hz,1H), 13C NMR (125MHz, DMSO-d6) δ 159.97,155.53, 145.59,141.57,139.90,139.78,137.89,137.42,136.56,136.22,134.93,131.10, 130.51,128.47,126.96,126.62,126.29,126.21,124.48,123.47,122.84,122.73, 120.52,120.47,120.24,120.08,118.91,117.92,116.35,115.43,109.58,101.96 HRMS (C49H31N3O): M/z 700.2364[ M + Na +, calcd 700.2359].
In the embodiment, the heating reaction temperature is 95 ℃ and the time is 11 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 8:1.5: 1.
Example 3: preparation of a near-ultraviolet organic electroluminescent Material (POPCN-2TBCP) based on a benzonitrile group
The synthetic route is as follows:
adding 2-bromo-6- (3-bromophenoxy) benzonitrile (5mmol), 3, 6-di-tert-butyl-9- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -carbazole (20mmol), potassium carbonate (20mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction flask, vacuumizing for three times, adding 125mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product POPCN-2TBCP with yield of 36%. 1H NMR (500MHz, CD2Cl2) δ 8.19-8.16 (M,4H), 7.92-7.83 (M,4H), 7.78-7.72 (M,2H), 7.70-7.65 (M,2H), 7.65-7.57 (M,3H), 7.56-7.46 (M,7H),7.42(d, J ═ 8.6Hz,2H), 7.37-7.33 (M,1H), 7.24-7.21 (M,1H), 7.04-7.02 (M,1H),1.47(s,18H),1.46(s,18H), 13C NMR (125MHz, CD2Cl2) δ 161.22,156.22,146.90,143.63,143.47,143.11, 139.42,139.29,139.21,138.80,138.26,136.59,134.33,131.15,130.75,128.83, 127.27,126.87,124.60,124.18,124.13,123.89,123.76,119.38,119.00,116.74, 116.71,116.18,115.92,109.67,109.58,103.29,35.05,35.04,32.13 HRMS (C65H63N 3N O M/924.4866M + 8678, 36z ].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 4: preparation of a near-UV organic electroluminescent Material (POPCN-TBCP) based on a benzonitrile group
The synthetic route is as follows:
adding 2-bromo-6-phenoxybenzonitrile (5mmol), 3, 6-di-tert-butyl-9- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -carbazole (12.5mmol), potassium carbonate (20mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction flask, vacuumizing for three times, adding 100mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product POPCN-TBCP with yield of 77%. 1H NMR (500MHz, CD2Cl2) δ 8.18(d, J ═ 1.8Hz,2H), 7.87-7.83 (m,2H), 7.75-7.71 (m,2H), 7.59-7.56 (m,1H), 7.53-7.44 (m,6H), 7.34-7.25 (m,2H), 7.20-7.16 (m,2H), 6.91-6.89 (m,1H),1.47(s, 18H).
In the embodiment, the heating reaction temperature is 110 ℃ and the time is 24 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:1: 1.
Example 5: preparation of near ultraviolet organic electroluminescent material (POPCN-TPA) based on benzene cyano
The synthetic route is as follows:
2-bromo-6-phenoxybenzonitrile (5mmol), (4- (diphenylamino) phenyl) boronic acid (12.5mmol), potassium carbonate (20mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) were added to a reaction flask, and gas was purged three times, 100mL of a mixed solvent of toluene, water and ethanol was added, and the reaction was heated. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product POPCN-TPA with yield of 87%. 1H NMR (500MHz, DMSO-d6) delta 7.68-7.64 (m,1H), 7.56-7.45 (m,4H), 7.39-7.35 (m,4H), 7.33-7.26 (m,2H), 7.22-7.18 (m,2H), 7.16-7.10 (m,6H), 7.07-7.02 (m,2H), 6.91-6.86 (m,1H).
In the embodiment, the heating reaction temperature is 99 ℃ and the time is 18 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 7.5:1.6: 1.
Example 6: preparation of near ultraviolet organic electroluminescent material (POPCN-2TPA) based on benzene cyano
The synthetic route is as follows:
2-bromo-6- (3-bromophenoxy) benzonitrile (5mmol), (4- (diphenylamino) phenyl) boronic acid (12.5mmol), potassium carbonate (20mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) were added to a reaction flask, and gas was purged three times, 100mL of a mixed solvent of toluene, water and ethanol was added, and the reaction was heated. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product POPCN-2TPA with yield of 32%. 1H NMR (500MHz, DMSO-d6) δ 7.69-7.61 (m,3H), 7.58-7.51 (m,4H), 7.47-7.45 (m,1H), 7.39-7.30 (m,9H), 7.16-6.99 (m,17H),6.94(d, J ═ 8.4Hz,1H).
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 7: preparation of near ultraviolet organic electroluminescent material (PSPCN-CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-6- (phenylthio) benzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (12.5mmol), potassium carbonate (20mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction bottle, vacuumizing for three times, adding 100mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product PSPCN-CP with yield of 85%. HRMS (C31H20N2S) M/z 452.5750[ M + H +, calcd 452.5712].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 8: preparation of benzene cyano-based near ultraviolet organic electroluminescent material (2POPCN-3CP)
The synthetic route is as follows:
adding 2-bromo-4, 6-bis (3-bromophenoxy) benzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (15mmol), potassium carbonate (24mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction bottle, vacuumizing for three times, adding 100mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product 2POPCN-3CP with yield of 82%. HRMS (C73H46N4O2) M/z 1011.1970[ M + H +, calcd 1011.1910].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 9: preparation of benzene cyano-based near ultraviolet organic electroluminescent material (2PSPCN-3CP)
The synthetic route is as follows:
adding 2-bromo-4, 6-bis ((3-bromophenyl) thio) benzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (15mmol), potassium carbonate (23mmol) and tetrakis (triphenylphosphine) palladium (0.5mmol) into a reaction bottle, vacuumizing for three times, adding 100mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product 2PSPCN-3CP with yield of 82%. HRMS (C73H46N4S2) M/z 1043.3190[ M + H +, calcd 1043.3172].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 10: preparation of near ultraviolet organic electroluminescent material (MeOPCN-CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-6-methoxybenzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boric acid (6mmol), potassium carbonate (10mmol) and tetrakis (triphenylphosphine) palladium (0.25mmol) into a reaction bottle, vacuumizing for three times, adding 75mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product MeOPCN-CP with yield of 90%. HRMS (C26H18N2O) M/z 374.4430[ M + H +, calcd 374.4402].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 11: preparation of near ultraviolet organic electroluminescent material (2MeOPCN-CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-4, 6-dimethoxybenzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (7 mmol), potassium carbonate (11mmol) and tetrakis (triphenylphosphine) palladium (0.25mmol) into a reaction bottle, vacuumizing for three times, adding 80mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product 2MeOPCN-CP with yield of 87%. HRMS (C27H20N2O2) M/z 404.4690[ M + H +, calcd 404.4683].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 12: preparation of near ultraviolet organic electroluminescent material (MeSPCN-CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-6- (methylthio) benzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (9mmol), potassium carbonate (12mmol) and tetrakis (triphenylphosphine) palladium (0.25mmol) into a reaction bottle, vacuumizing for three times, adding 90mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product MeSPCN-CP with yield of 92%. HRMS (C26H18N2S) M/z 390.5040[ M + H +, calcd 390.5030].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 13: preparation of near ultraviolet organic electroluminescent material (2MeSPCN-CP) based on benzene cyano
The synthetic route is as follows:
adding 2-bromo-4, 6-bis (methylthio) benzonitrile (5mmol), (4- (carbazol-9-yl) phenyl) boronic acid (6mmol), potassium carbonate (10mmol) and tetrakis (triphenylphosphine) palladium (0.25mmol) into a reaction bottle, vacuumizing for three times, adding 75mL of a mixed solvent of toluene, water and ethanol, and heating for reaction. Extracting with dichloromethane and water, concentrating, making powder, and passing through column to obtain final product 2MeSPCN-CP with yield of 85%. HRMS (C27H20N2S2) M/z 436.5910[ M + H +, calcd 436.5895].
In the embodiment, the heating reaction temperature is 100 ℃ and the time is 17 h; the volume ratio of toluene, water and ethanol in the mixed solvent is 9:2: 1.
Example 14: performance of OLED device based on organic electroluminescent material (POPCN-CP) of benzene cyano
The doped device prepared by using the organic electroluminescent material POPCN-CP based on the benzonitrile prepared in the embodiment 1 as a luminescent material, and the performance test and characterization results of the device are shown in the figure 1-2.
The device structure is as follows:
ITO/HATCN/TAPC/TcTa/mCP/POPCN-CP:PPF/PPF/TmPyPB/LiF/Al
FIG. 1 is a L-V-J graph of an OLED device based on the material obtained in example 1, from which it can be seen that the maximum luminance of a POPCN-CP based doped device is high and the start-up voltage is low, 822cd/m2, 3.4V. FIG. 2 is a graph of external quantum efficiency as a function of luminance for a doped device based on the material obtained in example 1, from which it can be seen that the maximum external quantum efficiency of a POPCN-CP based doped device is 5.1% when the luminance is 100cd/m2The external quantum efficiency was maintained at 4.5%.
Example 15: performance of OLED device based on organic electroluminescent material (POPCN-2CP) of benzene cyano
The doped device prepared by using the organic electroluminescent material POPCN-2CP based on the benzonitrile prepared in the embodiment 2 as a luminescent material, and the performance test and characterization results of the device are shown in the figure 3-4.
The device structure is as follows:
ITO/HATCN/TAPC/TcTa/mCP/POPCN-2CP:PPF/PPF/TmPyPB/LiF/Al。
fig. 3 is a L-V-J graph of an OLED device based on the material obtained in example 2, from which it can be seen that the maximum luminance of a doped device based on POPCN-2CP is high and the start-up voltage is low, 1603cd/m2, 3.3V. FIG. 4 is a graph of external quantum efficiency as a function of luminance for a doped device based on the material obtained in example 2, from which it can be seen that the maximum external quantum efficiency of a POPCN-2 CP-based doped device is 5.6% when the luminance is 100cd/m2The external quantum efficiency was maintained at 5.0%.
Example 16: OLED device performance of organic electroluminescent materials (POPCN-2TBCP) based on benzene cyano
The doped device prepared by using the organic electroluminescent material POPCN-2TBCP based on the benzonitrile prepared in the embodiment 3 as a luminescent material, and the performance test and characterization results of the device are shown in FIGS. 5-6.
The device structure is as follows:
ITO/HATCN/TAPC/TcTa/mCP/POPCN-2TBCP:PPF/PPF/TmPyPB/LiF/Al。
FIG. 5 is a L-V-J graph of an OLED device based on the material obtained in example 3, from which it can be seen that the maximum luminance of a POPCN-2TBCP based doped device is high and the start-up voltage is low, 2675cd/m2, 3.2V. FIG. 6 is a graph of the external quantum efficiency of a doped device based on the material obtained in example 3 as a function of luminance, from which it can be seen that the maximum external quantum efficiency of a POPCN-2 TBCP-based doped device is 5.7% when the luminance is 100cd/m2The external quantum efficiency was maintained at 5.2%.
Example 17: OLED device performance of organic electroluminescent materials (POPCN-TBCP) based on benzene cyano
The doped device prepared by using the organic electroluminescent material POPCN-TBCP based on the benzonitrile prepared in the embodiment 4 as a luminescent material, and the performance test and characterization results of the device are shown in FIGS. 7-8.
The device structure is as follows:
ITO/HATCN/TAPC/TcTa/mCP/POPCN-TBCP:PPF/PPF/TmPyPB/LiF/Al。
FIG. 7 is a L-V-J graph of an OLED device based on the material obtained in example 4, and it can be seen that the maximum luminance of a POPCN-TBCP based doped device is high and the starting voltage is low, 1751cd/m2, 3.3V. FIG. 8 is a graph of the external quantum efficiency of a doped device based on the material obtained in example 4 as a function of luminance, from which it can be seen that the maximum external quantum efficiency of a POPCN-TBCP based doped device is 5.1% when the luminance is 100cd/m2The external quantum efficiency was maintained at 4.2%.
Example 18: performance of OLED device based on organic electroluminescent material (POPCN-2TPA) of benzene cyano
The doped device prepared by using the organic electroluminescent material POPCN-2TPA based on the benzonitrile prepared in the embodiment 6 as a luminescent material, and the performance test and characterization results of the device are shown in FIGS. 9-10.
The device structure is as follows:
ITO/HATCN/TAPC/TcTa/mCP/POPCN-2TPA:PPF/PPF/TmPyPB/LiF/Al。
fig. 9 is a L-V-J graph of an OLED device based on the material obtained in example 6, from which it can be seen that the maximum luminance of a doped device based on POPCN-2TPA is high and the start-up voltage is low, 11850cd/m2, 2.9V. FIG. 10 is a graph of the external quantum efficiency as a function of luminance for a doped device based on the material obtained in example 6, from which it can be seen that the maximum external quantum efficiency for a POPCN-2 TPA-based doped device is 7.4% when the luminance is 100cd/m2The external quantum efficiency was maintained at 7.1%.
The data show that the doped OLED device prepared by using the organic photoelectric material which takes the benzene cyano group as the core as the luminescent layer has high efficiency and smaller efficiency roll-off degree; the non-doped OLED device prepared based on the materials and having a simple structure has low starting voltage, high efficiency and smaller efficiency roll-off degree. In a word, the material has wide application prospect in the field of organic electroluminescence.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A near ultraviolet organic electroluminescent material based on benzene cyano is characterized by having one of the following structures:
wherein R is alkane containing 1-10 carbon atoms, Ar1 and Ar2 are the same or different electron donating groups, and n is an integer of 1-4.
2. The near ultraviolet organic electroluminescent material based on benzene cyano group as claimed in claim 1, characterized in that the electron donating group is one of hydrogen or aromatic ring derivatives.
3. The benzonitrile-based near ultraviolet organic electroluminescent material of claim 2, wherein the aromatic ring derivative electron donating group is one of phenyl, fluorenyl, diphenylaminophenyl, 1,3, 6, 8-tetramethylcarbazolylphenyl, carbazolylphenyl, phenoxazinylphenyl, phenothiazinylphenyl, 9, 10-dihydro-9, 9-dimethylacridinylphenyl, 9, 10-dihydro-9, 9-diphenylacridinylphenyl, 10-H-spiro [ acridine-9, 9 '-fluorene ] phenyl, 10-H-spiro [ acridine-9, 9' -xanthene ] phenyl, diphenyl-2-naphthylamine, dinaphthylamine phenyl.
4. The near ultraviolet organic electroluminescent material based on the benzene cyano group as claimed in any one of claims 1 to 4, characterized in that the electron donating group of the aromatic ring derivative is one of the following structures shown in formulas a to v:
wherein R 'and R' can be the same or different hydrogen atoms or alkyl chains containing 1-10 carbon atoms, and n is an integer of 0-10.
5. A preparation method of a near ultraviolet organic electroluminescent material based on a benzene cyano group is characterized by comprising the following steps:
taking 2-bromobenzonitrile substances and aromatic ring derivatives as raw materials, taking toluene, water and ethanol as mixed solvents under the condition of taking potassium carbonate and tetrakis (triphenylphosphine) palladium as catalysts, and heating for reaction to obtain the near-ultraviolet organic electroluminescent material based on the benzonitrile;
the 2-bromobenzonitrile comprises 2-bromo-6-phenoxybenzonitrile or 2-bromo-6- (3-bromophenoxy) benzonitrile or 2-bromo-6- (phenylthio) benzonitrile or 2-bromo-4, 6-bis (3-bromophenoxy) benzonitrile or 2-bromo-4, 6-bis ((3-bromophenyl) thio) benzonitrile or 2-bromo-6-methoxybenzonitrile or 2-bromo-4, 6-dimethoxybenzonitrile or 2-bromo-6- (methylthio) benzonitrile or 2-bromo-4, 6-bis (methylthio) benzonitrile; the aromatic ring derivative includes: (4- (carbazol-9-yl) phenyl) boronic acid, 3, 6-di-tert-butyl-9- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -carbazole or (4- (diphenylamino) phenyl) boronic acid.
6. The preparation method of the benzonitrile-based near-ultraviolet organic electroluminescent material as claimed in claim 5, wherein a molar ratio of the 2-bromobenzonitrile-based substances to the aromatic ring derivatives is 1: 1.2-4.
7. The preparation method of the benzonitrile-based near-ultraviolet organic electroluminescent material as claimed in claim 5, wherein the volume ratio of the toluene to the water to the ethanol is 7-9: 1-2: 1; the molar ratio of potassium carbonate to tetrakis (triphenylphosphine) palladium is 15-25: 0.5; the molar ratio of the potassium carbonate to the 2-bromobenzonitrile is 3-5: 1; the volume mol ratio of the mixed solvent to the 2-bromobenzonitrile substance is 15-25 (L):1 (mol).
8. The method for preparing a benzonitrile based near-ultraviolet organic electroluminescent material as in any of claims 5 to 7, wherein the heating reaction is performed at a temperature of 90 to 110 ℃ for 10 to 24 hours.
9. The application of the near-ultraviolet organic electroluminescent material based on the benzene cyano group in preparing OLED (organic light emitting diode) according to any one of claims 1 to 4.
10. The use according to claim 9, wherein the benzonitrile based near-ultraviolet organic electroluminescent material is used as a light-emitting layer of an OLED in a doped or undoped manner.
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