CN108191847A - It is a kind of asymmetric to the organic red fluorescent small molecule material of receptor type and its application in organic electroluminescence device - Google Patents
It is a kind of asymmetric to the organic red fluorescent small molecule material of receptor type and its application in organic electroluminescence device Download PDFInfo
- Publication number
- CN108191847A CN108191847A CN201810013495.XA CN201810013495A CN108191847A CN 108191847 A CN108191847 A CN 108191847A CN 201810013495 A CN201810013495 A CN 201810013495A CN 108191847 A CN108191847 A CN 108191847A
- Authority
- CN
- China
- Prior art keywords
- organic
- small molecule
- red fluorescent
- fluorescent small
- receptor type
- 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.)
- Granted
Links
- 0 CN=C(C1=*)C(Br)=C(C=CC=C2)C2=C1Br Chemical compound CN=C(C1=*)C(Br)=C(C=CC=C2)C2=C1Br 0.000 description 2
- WJEHUFFIYYOQJL-UHFFFAOYSA-N Brc(c1n[s]nc11)c(cccc2)c2c1-c1ccccc1 Chemical compound Brc(c1n[s]nc11)c(cccc2)c2c1-c1ccccc1 WJEHUFFIYYOQJL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
-
- 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
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
A kind of asymmetry belongs to electroluminescent organic material technical field to receptor type organic red light fluorescent small molecule material and its application in organic electroluminescence device is prepared.The present invention will be connected to receptor by linear conjugate mode using Suzuki coupling reactions, can realize high efficiency red emission, when preparing feux rouges doping device, by using different parents and optimized doping concentration, reached preferable device effect；In addition, the molecular structure for tending to plane can be buried in oblivion by triplet state-triplet state utilizes Triplet exciton.Gained compound of the invention has very high fluorescence quantum yield, and undoped red device maximum external quantum efficiency is 6.66%, is 100 and 1000cd m in brightness‑2When external quantum efficiency be respectively 6.51% and 5.11%, efficiency roll-off is small.Cut-in voltage is low, is 2.6V, and device synthesis performance is in a leading position level in organic red luminescent material, is hopeful to realize commercial applications.
Description
Technical field
The invention belongs to electroluminescent organic material technical fields, and in particular to a kind of asymmetric to receptor type organic red light
Fluorescent small molecule material and its application in organic electroluminescence device is prepared.
Background technology
Organic electroluminescent LED (OLEDs) is rollable, bright in luster with low energy consumption, wide viewing angle, low cost, flexibility
The advantages that, promise to be next-generation display and illuminating device.At present, the display screen based on OLEDs technologies have been supplied in mobile phone,
On TV and computer.But the material and device process technology of current OLEDs are still immature.Material is the technology core of OLEDs
The heart.The material applied in display screen is had been commercialized at present, the overwhelming majority is centered on precious metal iridium (Ir) or platinum (Pt)
Metal complex phosphor material.But Ir and Pt are scarce resources, and it is expensive, being produced into for OLEDs will necessarily be increased
This.Secondly, Ir and Pt is the precious resources that China has strategic importance, is not suitable for the utilization of long term commercial.In addition,
The metalcomplex sythesis of Ir and Pt is difficult, and main ligand and assistant ligand selection are limited, are difficult to realize the diversification of molecular structure.
Organic red fluorescent small molecule is without precious metal, mainly by elements groups such as C, H, O, N, P, S of nature content very abundant
Into synthesis cost is more cheap.Molecular structure Modulatory character is strong, can synthesize a variety of differences by abundant methodology of organic synthesis
The molecule of structure, material structure are ever-changing.Therefore, organic red fluorescent small molecule has abundanter photophysical property,
It can realize abundanter color displays.But constrained by spin statistics, in OLEDs devices, singlet and triplet state swash
Sub- generation ratio is 1：3, that is, singlet exciton production rate is only 25%.For organic red fluorescent small molecule, only singly
Line state can shine, and account for the exciton generation most of triplet state of ratio and be dissipated in the form of nonradiative transition, cause huge
Waste.Metal complex phosphor material can realize that 100% exciton utilizes, this is metal complex phosphor material relative to organic
The main advantage of red fluorescence small molecule fluorescent material.Meet actual displayed or illumination needed for brightness generally require it is larger
Current density.But triplet excitons radiation transistion rate is slow, lasts a long time.Under big current density, triplet excitons
Having little time rapidly to return to ground state in the form of radiation transistion, this can cause a large amount of accumulations of triplet excitons, easily be quenched,
For example singlet-triplet state is quenched, and triplet state-triplet state is quenched, and triplet state-charge is quenched etc., this leads to metal combination
Object phosphor material often will appear serious efficiency roll-off in high brightness.Therefore, exploitation breaks through the organic red of exciton statistics
Fluorescent small molecule material realizes high efficiency under high brightness, and to pushing OLEDs, further commercialization is of great significance.
Feux rouges is essential in total colouring.Although the performance of the red phosphorescence material based on Ir and Pt is good
Meet commercialization requirement, but the noble metals such as Ir and Pt are expensive, be not suitable for long period of development.And organic fluorescence materials cost is honest and clean
Valency, but red fluorescence material efficiency is also than relatively low at present.So exploitation commercial presenceization can practical application high efficiency it is red
Fluorescent material is extremely important.Using asymmetry to acceptor molecule design concept, design synthesis have D (donor)-A (receptor)-
A ' (receptor) or D (donor)-A (receptor)-D ' (donor) type molecule, can realize the diversification of material structure.Meanwhile it compares
It is asymmetric that abundanter photochromic and excitation is advantageously implemented to receptor type molecular design method in traditional D-A type molecules
State property matter.In addition, the asymmetric MOLECULE DESIGN to receptor type material is conducive to introduce function difference simultaneously in same intramolecular
Group, realize that molecule has multiple functions, be conducive to improve the photoelectric properties of material.By introducing have triplet state-
Show state bury in oblivion (TTA) property to receptor unit, connected by way of linear conjugate, not only contribute to realize efficient
Red emission can also obtain high efficiency under high illumination by TTA mechanism using triplet state.
Invention content
To solve the problems, such as that organic red fluorescent small molecule devices are less efficient in OLEDs, develop height without precious metal
The organic red fluorescent small molecule material of efficiency, the present invention give acceptor molecule design from asymmetry, it is intended to prepare a kind of height
The asymmetry of efficiency and passes through optimised devices structure to the organic red light fluorescent small molecule material of acceptor type, by it using existing
In OLEDs devices.
The purpose of the present invention is to provide a kind of asymmetric organic red fluorescent small molecule materials of high efficiency for giving receptor type.
Another object of the present invention is to provide above-mentioned a kind of asymmetric organic red fluorescent small molecule material to receptor type
Expect the application in organic electroluminescence device is prepared.
A kind of asymmetric organic red fluorescent small molecule material for giving receptor type of the present invention, molecular structure are as follows
It is shown：
Wherein Ar represents following aromatic group：
Specifically, a kind of asymmetric organic red fluorescent small molecule material for giving receptor type of the present invention, molecule
Structure is as follows：
Above-mentioned organic red fluorescent small molecule is mainly prepared by one pot reaction, Ullmann couplings and Suzuki couplings
It obtains.
Above-mentioned a kind of asymmetry is to the organic red fluorescent small molecule material of receptor type in organic electroluminescence device is prepared
It can be applied.Prepared organic electroluminescence device is by glass substrate, ito anode, hole transmission layer, luminescent layer, electricity
Sub- transport layer and cathode composition；Luminescent layer is undoped luminescent layer, is at least given containing a kind of a kind of asymmetry of the present invention
The organic red fluorescent small molecule material of receptor type；Or luminescent layer is doping luminescent layer, by least one one kind of the present invention
Asymmetry is material doped to being prepared in fertile material to the organic red fluorescent small molecule of receptor type.Fertile material for CBP,
MADN or PIAnCN, doping concentration of the organic red fluorescent small molecule material in fertile material are 10%~50%.
The principle of the present invention is：A kind of asymmetric organic red fluorescent small molecule material for giving receptor type, by linearly common
Yoke mode connects, and can realize high efficiency red emission.The group such as benzo thiophene of triplet state can be utilized by TTA mechanism by introducing
Azoles, aphthothiazoles and phenanthro- imidazoles etc. can be in electroluminescent devices effectively using triplet excitons, and breaking through tradition has
The bottleneck of 25% exciton utilization rate of machine red fluorescence small molecule.
TTA mechanism is based on two triplet state collision one singlets of generation, in certain triplet state concentration range, three lines
State concentration is higher, and TTA is more effective, therefore can remain to keep high device efficiency in high brightness, overcomes metal complex phosphorescence
Material and thermal activation delayed fluorescence (TADF) material under high illumination serious efficiency roll-off the problem of.In addition, pass through device junction
The optimization of structure does parent using the blue light material MADN or PIAnCN of TTA types, effectively can utilize triplet state by TTA mechanism,
High device efficiency is realized under high illumination.
The organic red fluorescent small molecule luminescent material and organic electroluminescence device of the present invention has the following advantages that and has
Beneficial effect：
(1) organic red fluorescent small molecule structure of the invention is single determines, synthesis is simple, purification facility, convenient for research
Structure and theory is conducive to industrial amplification production.
(2) organic red fluorescent small molecule of the invention has good thermal stability, and evaporated film is smooth uniform, without apparent
Phase separation, suitable for the OLEDs devices based on evaporation coating technique.
(3) organic red fluorescent small molecule of the invention has higher HOMO energy levels and relatively low lumo energy, favorably
In the injection and transmission of carrier balance.
(4) undoped and doping feux rouges OLEDs devices prepared by organic red fluorescent small molecule of the invention are in high brightness
Under show higher device efficiency.
(5) organic red fluorescent small molecule of the invention will be connected by linear conjugate mode to receptor, can realize height
Efficiency red emission.In addition, the molecular structure for tending to plane can be buried in oblivion by triplet state-triplet state utilizes triplet excitons
It shines.
Description of the drawings
Fig. 1：It is P4Thermogravimetric curve；
Fig. 2：It is P4Differential calorimetry curve；
Fig. 3：It is P4The Absorption and emission spectra of undoped evaporated film；
Fig. 4：It is the solvation emission spectrum of P4；
Fig. 5：It is based on P4Undoped OLEDs devices external quantum efficiency curve；
Fig. 6：It is based on P4Electroluminescent spectrum of the undoped OLEDs devices under different voltages；
Fig. 7：It is using CBP as parent P4For object, the device external quantum efficiency curve under different levels of doping；
Fig. 8：It is using CBP as parent P4For object, the electroluminescent spectrum under different levels of doping；
Fig. 9：It is using MADN as parent P4For object, the device external quantum efficiency curve under different levels of doping；
Figure 10：It is using MADN as parent P4For object, the electroluminescent spectrum under different levels of doping；
Figure 11：It is using PIAnCN as parent P4For object, the device external quantum efficiency curve under different levels of doping；
Figure 12：It is using PIAnCN as parent P4For object, the electroluminescent spectrum under different levels of doping；
Figure 13：It is based on P2Undoped OLEDs devices external quantum efficiency curve；
Figure 14：It is based on P2Electroluminescent spectrum of the undoped OLEDs devices under different voltages；
Figure 15：It is using CBP as parent P2For object, the device external quantum efficiency curve under different levels of doping；
Figure 16：It is using CBP as parent P2For object, the electroluminescent spectrum under different levels of doping；
Figure 17：It is using MADN as parent P2For object, the device external quantum efficiency curve under different levels of doping；
Figure 18：It is using MADN as parent P2For object, the electroluminescent spectrum under different levels of doping；
Figure 19：It is using PIAnCN as parent P2For object, the device external quantum efficiency curve under different levels of doping；
Figure 20：It is using PIAnCN as parent P2For object, the electroluminescent spectrum under different levels of doping；
Specific embodiment
Embodiment 1
P1Preparation, including following preparation process：
M1Synthesis：M1It is prepared by one kettle way.In 250mL round-bottomed flasks, by 9,10- phenanthrenequione (20mmol, 4.16g),
4- bromobenzaldehydes (20mmol, 3.68g), aniline (100mmol, 9.5mL), ammonium acetate (80mmol, 6.16g) are dissolved in 150mL
In glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction, reaction system is poured into 100mL ice water,
There are a large amount of Precipitations in moment.It filters, obtained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：1, volume
Than) obtain white brown solid (8.05g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 448.67, theoretical
Be worth is 448.06.
M2Synthesis：M2It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 2.24g) joins boron
Sour pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- bis- (diphenylphosphino) ferrocene] two
Palladium bichloride (0.1mmol, 73mg) is dissolved in 60mL dioxane, is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction knot
Shu Hou is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume
Than) obtain white brown solid (1.48g, yield：60%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 497.03, reason
It is 496.23 by value.
M3Synthesis：M3It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,7- bis- bromo- 2,1,3- benzo thiophene
Diazole (5mmol, 1.46g), phenyl boric acid (5mmol, 610mg), tetra-triphenylphosphine palladium (0.1 mmol, 115mg) are dissolved in 40mL
The wet chemical of toluene and 20mL (2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction terminates
Afterwards, it is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=50：1, volume ratio)
Obtain blue-green solid (510mg, yield：35%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 289.95, theoretical value
It is 290.12.
P1Synthesis：P1It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48 g), M3
(5mmol, 1.45g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain bright green solid (2.03g, yield：
70%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 580.32, theoretical value
580.17.Elemental analysis (%) C39H24N4S:Theoretical value C 80.67, H 4.17, N 9.65；Test value C 80.65, H 4.18,
N 9.66。
Embodiment 2
The present embodiment P2Preparation, including following preparation process：
M4Synthesis：M4It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,7- bis- bromo- 2,1,3- benzo thiophene
Diazole (5mmol, 1.46g), 4- cyanophenylboronic acids (5mmol, 735mg), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in
The wet chemical of 40mL toluene and 20mL (2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction knot
Shu Hou is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=50：1, volume
Than) obtain yellow-orange solid (630mg, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 315.05, theoretical
Be worth is 314.95.
P2Synthesis：P2It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48 g), M4
(5mmol, 1.57g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain orange/yellow solid (1.97g, yield：
65%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 605.42, theoretical value
605.17.Elemental analysis (%) C40H23N5S:Theoretical value C 79.32, H 3.83, N 11.56；Test value C 79.33, H 3.82,
N 11.58。
Embodiment 3
The present embodiment P3Preparation, including following preparation process：
M5Synthesis：M5It is coupled and prepared by Ullmann.In 100mL round-bottomed flasks, by carbazole (10mmol, 1.67g),
Isosorbide-5-Nitrae dibromobenzene (10mmol, 2.34g), potassium phosphate (20mmol, 4.24g), cuprous iodide (0.2mmol, 38mg), anti-form-1,2-
Cyclohexanediamine (0.4mmol, 0.05mL) is dissolved in 40mL toluene, is stirred at reflux 24 hours for 110 DEG C under nitrogen protection.Reaction
After, it is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=8：1, volume
Than) obtain white solid (1.61g, yield：50%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 321.33, theoretical value
It is 321.02.
M6Synthesis：M6It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M5(5mmol, 1.61g) joins boron
Sour pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- bis- (diphenylphosphino) ferrocene] two
Palladium bichloride (0.1mmol, 73mg) is dissolved in 60mL dioxane, is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction knot
Shu Hou is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=4：1, volume
Than) obtain white solid (1.29 g, yield：70%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 369.24, theoretical
Be worth is 369.19.
M7Synthesis：M7It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,7- bis- bromo- 2,1,3- benzo thiophene
Diazole (5mmol, 1.46g), M6(5mmol, 1.85g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene
With wet chemical (the 2.0mol L of 20mL-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it uses
Dichloromethane extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=6：1, volume ratio) obtain it is green
Color solid (910mg, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 455.13, theoretical value 455.01.
P3Synthesis：P3It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48 g), M7
(5mmol, 2.27g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain greenish yellow solid (2.79g, yield：
75%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 745.51, theoretical value
745.23.Elemental analysis (%) C51H31N5S:Theoretical value C 82.12, H 4.19, N 9.39；Test value C 82.13, H 4.20,
N 9.38。
Embodiment 4
The present embodiment P4Preparation, including following preparation process：
M8Synthesis：M8It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,7- bis- bromo- 2,1,3- benzo thiophene
Diazole (5mmol, 1.46g), 4- boric acid triphenylamine (5mmol, 1.45g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in
The wet chemical of 40mL toluene and 20mL (2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction
After, it is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=6：1, volume
Than) obtain Orange red solid (914mg, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 457.24, theoretical
Be worth is 457.02.
P4Synthesis：P4It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48 g), M8
(5mmol, 2.28g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain red solid (2.80g, yield：
75%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 747.33, theoretical value
747.25.Elemental analysis (%) C51H33N5S:Theoretical value C 81.90, H 4.45, N 9.36；Test value C 81.92, H 4.44,
N 9.37。
Embodiment 5
The present embodiment P5Preparation, including following preparation process：
P5Synthesis：P5It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(10mmol, 4.96 g), and 4,7-
Two bromo- 2,1,3- diazosulfide (5mmol, 1.46g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) is dissolved in 40mL toluene
With wet chemical (the 2.0mol L of 20mL-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it uses
Dichloromethane extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain Huang
Green solid (2.80g, yield：65%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test
It is 872.65 to be worth, theoretical value 872.27.Elemental analysis (%) C60H36N6S:Theoretical value C 82.55, H 4.16, N 9.63；It surveys
Examination value C 82.54, H 4.16, N 9.65.
Embodiment 6
The present embodiment P6Preparation, including following preparation process：
M9Synthesis：M9It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,9- dibromo naphtho- thiadiazoles
(5mmol, 1.71g), phenyl boric acid (5mmol, 610mg), tetra-triphenylphosphine palladium (0.1 mmol, 115mg) are dissolved in 40mL toluene
With wet chemical (the 2.0mol L of 20mL-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it uses
Dichloromethane extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=8：1, volume ratio) obtain orange
Red solid (595mg, yield：35%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 340.09, theoretical value
339.97。
P6Synthesis：P6It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48g), M9
(5mmol, 1.70g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain Orange red solid (2.36g, yield：
75%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 630.42, theoretical value
630.19.Elemental analysis (%) C43H26N4S:Theoretical value C 81.88, H 4.15, N 8.88；Test value C 81.87, H 4.16,
N 8.86。
Embodiment 7
The present embodiment P7Preparation, including following preparation process：
M10Synthesis：M10It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,9- dibromo naphtho- thiadiazoles
(5mmol, 1.71g), 4- cyanophenylboronic acids (5mmol, 735mg), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL
The wet chemical of toluene and 20mL (2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction terminates
Afterwards, it is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=8：1, volume ratio)
Obtain Orange red solid (730mg, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 365.11, theoretical value
It is 364.96.
P7Synthesis：P7It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48 g), M10
(5mmol, 1.82g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain bright red solid (2.46g, yield：
75%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 655.37, theoretical value
655.18.Elemental analysis (%) C44H25N5S:Theoretical value C 80.59, H 3.84, N 10.68；Test value C 80.61, H 3.83,
N 10.67。
Embodiment 8
The present embodiment P8Preparation, including following preparation process：
M11Synthesis：M11It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,9- dibromo naphtho- thiadiazoles
(5mmol, 1.71g), M6(5mmol, 1.85g), tetra-triphenylphosphine palladium (0.1mmol, 115 mg) be dissolved in 40mL toluene and
Wet chemical (the 2.0mol L of 20mL-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, with two
Chloromethanes extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=6：1, volume ratio) obtain red
Solid (1.14g, yield：45%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 505.31, theoretical value 505.02.
P8Synthesis：P8It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48g), M11
(5mmol, 2.52g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain red solid (2.98g, yield：
75%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 795.47, theoretical value
795.25.Elemental analysis (%) C55H33N5S:Theoretical value C 82.99, H 4.18, N 8.80；Test value C 83.01, H 4.17,
N 8.81。
Embodiment 9
The present embodiment P9Preparation, including following preparation process：
M12Synthesis：M12It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by 4,9- dibromo naphtho- thiadiazoles
(5mmol, 1.71g), 4- boric acid triphenylamine (5mmol, 1.45g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in
The wet chemical of 40mL toluene and 20mL (2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.Reaction
After, it is extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=6：1, volume
Than) obtain dark red solid (1.01g, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 507.19, theoretical
Be worth is 507.04.
P9Synthesis：P9It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.48g), M12
(5mmol, 2.54g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and the wet chemical of 20mL
(2.0mol L-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, it is extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain dark red solid (2.79g, yield：
70%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 797.52, theoretical value
797.26.Elemental analysis (%) C55H35N5S:Theoretical value C 82.78, H 4.42, N 8.78；Test value C 82.77, H 4.43,
N 8.77。
Embodiment 10
The present embodiment P10Preparation, including following preparation process：
P10Synthesis：P10It is coupled and prepared by Suzuki.In 100mL round-bottomed flasks, by M2(10mmol, 4.96g), 4,
9- dibromo naphtho- thiadiazoles (5mmol, 1.71g), tetra-triphenylphosphine palladium (0.1mmol, 115 mg) be dissolved in 40mL toluene and
Wet chemical (the 2.0mol L of 20mL-1), it is stirred at reflux 24 hours for 90 DEG C under nitrogen protection.After reaction, with two
Chloromethanes extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain red
Solid (2.54g, yield：55%).Product further passes through sublimation purification.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is
922.53 theoretical value 922.29.Elemental analysis (%) C64H38N6S:Theoretical value C 83.27, H 4.15, N 9.10；Test value C
83.29,H 4.16,N 9.11。
Embodiment 11
A kind of undoped organic electroluminescence device, using molecular structure as P4Organic red fluorescent small molecule be luminescent layer
Material, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is with P4Undoped luminescent layer for luminescent material.
Device fabrication process is as follows：By transparent electro-conductive glass in deionized water：(volume ratio 1 in alcohol mixeding liquid：
1) impregnate 2 hours, then with dust-free paper wiped clean, be then cleaned by ultrasonic one time with deionized water, finally successively with isopropanol-
Acetone-toluene-acetone-isopropanol is cleaned by ultrasonic three times repeatedly.Before preparing device, with nitrogen by transparent electro-conductive glass
Substrate dries up, and half an hour is irradiated under ultraviolet and ozone, is subsequently placed in vapor deposition cavity, is evacuated to 5 × 10-4Pa, above-mentioned
The material needed for device is deposited on transparent electro-conductive glass substrate successively, obtains organic electroluminescence device.Wherein organic layer
Evaporation rate is 0.3A s-1, the evaporation rate of LiF is 0.1A s-1, the evaporation rate of Al is 2.0A s-1。
The present embodiment is with P4The external quantum efficiency curve of undoped organic electroluminescence device for emitting layer material and not
With electroluminescent spectrum under voltage, difference is as shown in Figure 5 and Figure 6.The photoelectric properties data of obtained device are as shown in table 1.
Table 1：The performance data of undoped feux rouges OLEDs devices prepared by embodiment 11
Embodiment 12
One kind is using molecular structure as P4Organic red fluorescent small molecule for light-emitting guest, using CBP as the doping type of parent
Organic electroluminescence device, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is using CBP as parent, P4Doping type luminescent layer for light-emitting guest.
Device fabrication process is similar to Example 11.Wherein, when preparing luminescent layer, by controlling the opposite of parent and object
Evaporation rate, be prepared for object doping ratio for 10%, 20%, 30% and 50% (mass concentration, unless otherwise specified, doping
Concentration refers both to mass concentration) luminescent layer, and therefrom the excellent optimum doping concentration that has selected for 50%.
The present embodiment is using CBP as parent, P4It is mixed for doping organic electroluminescence device of the object as luminescent layer in difference
The electroluminescent spectrum under external quantum efficiency curve and different levels of doping under miscellaneous concentration, respectively as shown in Fig. 7 and Fig. 8.Institute
The photoelectric properties data for obtaining device are as shown in table 2.
Table 2：Embodiment 12 is using CBP as the results of property of the doping type feux rouges OLEDs devices of parent
Embodiment 13
One kind is using molecular structure as P4Organic red fluorescent small molecule for light-emitting guest, using MADN as the doping type of parent
Organic electroluminescence device, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is using MADN as parent, P4Doping type luminescent layer for light-emitting guest.Device fabrication process is with implementing
Example 11 is similar.Wherein, when preparing luminescent layer, by controlling the opposite evaporation rate of parent and object, it is prepared for object doping ratio
Example is 10%, 20%, 30% and 50% luminescent layer, and therefrom the excellent optimum doping concentration that has selected is 20%.
The present embodiment is using MADN as parent, P4It is mixed for doping organic electroluminescence device of the object as luminescent layer in difference
The electroluminescent spectrum under external quantum efficiency curve and different levels of doping under miscellaneous concentration, respectively as shown in Figure 9 and Figure 10.
The photoelectric properties of obtained device are as shown in table 3.
Table 3：Embodiment 13 is using MADN as the results of property of the doping type feux rouges OLEDs devices of parent
Embodiment 14
One kind is using molecular structure as P4Organic red fluorescent small molecule for light-emitting guest, using PIAnCN as the doping of parent
Type organic electroluminescence device, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is using PIAnCN as parent, and P4 is the doping type luminescent layer device fabrication process and reality of light-emitting guest
It is similar to apply example 11.Wherein, when preparing luminescent layer, by controlling the opposite evaporation rate of parent and object, it is prepared for object doping
Ratio is 10%, 20%, 30% and 50% luminescent layer, and therefrom the excellent optimum doping concentration that has selected is 20%.
The present embodiment is using PIAnCN as parent, P4For object as luminescent layer doping organic electroluminescence device in difference
The electroluminescent spectrum under external quantum efficiency curve and different levels of doping under doping concentration, respectively such as Figure 11 and Figure 12 institutes
Show.The photoelectric properties of obtained device are as shown in table 4.
Table 4：Embodiment 14 is using PIAnCN as the results of property of the doping type feux rouges OLEDs devices of parent
Embodiment 15
A kind of undoped organic electroluminescence device, using molecular structure as P2Organic red fluorescent small molecule be luminescent layer
Material, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is with P2Undoped luminescent layer for luminescent material.Device fabrication process is similar to Example 11.
The present embodiment is with P2The external quantum efficiency curve of undoped organic electroluminescence device for emitting layer material and not
With electroluminescent spectrum under voltage, difference is as shown in Figure 13 and Figure 14.The photoelectric properties data of obtained device are as shown in table 5.
Table 5：The performance data of undoped feux rouges OLEDs devices prepared by embodiment 15
Embodiment 16
One kind is using molecular structure as P2Organic red fluorescent small molecule for light-emitting guest, using CBP as the doping type of parent
Organic electroluminescence device, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is using CBP as parent, P2Doping type luminescent layer for light-emitting guest.
Device fabrication process is similar to Example 11.Wherein, when preparing luminescent layer, by controlling the opposite of parent and object
Evaporation rate, is prepared for the luminescent layer that object doping ratio is 10%, 20%, 30% and 50%, and therefrom it is excellent have selected it is best
Doping concentration is 20%.
The present embodiment is using CBP as parent, P2It is mixed for doping organic electroluminescence device of the object as luminescent layer in difference
The electroluminescent spectrum under external quantum efficiency curve and different levels of doping under miscellaneous concentration, respectively as shown in Figure 15 and Figure 16.
The photoelectric properties data of obtained device are as shown in table 6.
Table 6：Embodiment 16 is using CBP as the results of property of the doping type feux rouges OLEDs devices of parent
Embodiment 17
One kind is using molecular structure as P2Organic red fluorescent small molecule for light-emitting guest, using MADN as the doping type of parent
Organic electroluminescence device, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is using MADN as parent, P2Doping type luminescent layer for light-emitting guest.Device fabrication process is with implementing
Example 11 is similar.Wherein, when preparing luminescent layer, by controlling the opposite evaporation rate of parent and object, it is prepared for object doping ratio
Example is 10%, 20%, 30% and 50% luminescent layer, and therefrom the excellent optimum doping concentration that has selected is 50%.
The present embodiment is using MADN as parent, P2It is mixed for doping organic electroluminescence device of the object as luminescent layer in difference
The electroluminescent spectrum under external quantum efficiency curve and different levels of doping under miscellaneous concentration, respectively as shown in Figure 17 and Figure 18.
The photoelectric properties of obtained device are as shown in table 7.
Table 7：Embodiment 17 is using MADN as the results of property of the doping type feux rouges OLEDs devices of parent
Embodiment 18
One kind is using molecular structure as P2Organic red fluorescent small molecule for light-emitting guest, using PIAnCN as the doping of parent
Type organic electroluminescence device, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF( 1nm)/
Al(120nm).Wherein EML is using PIAnCN as parent, and P2 is the doping type luminescent layer device fabrication process and reality of light-emitting guest
It is similar to apply example 11.Wherein, when preparing luminescent layer, by controlling the opposite evaporation rate of parent and object, it is prepared for object doping
Ratio is 10%, 20%, 30% and 50% luminescent layer, and therefrom the excellent optimum doping concentration that has selected is 30%.
The present embodiment is using PIAnCN as parent, P2For object as luminescent layer doping organic electroluminescence device in difference
The electroluminescent spectrum under external quantum efficiency curve and different levels of doping under doping concentration, respectively such as Figure 19 and Figure 20 institutes
Show.The photoelectric properties of obtained device are as shown in table 8.
Table 8：Embodiment 18 is using PIAnCN as the results of property of the doping type feux rouges OLEDs devices of parent
The structural formula of material therefor is as follows in the organic electroluminescence device of embodiment 11-18, can be commercially available：
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (6)
- It is 1. a kind of asymmetric to the organic red fluorescent small molecule material of receptor type, it is characterised in that：Structural formula is as follows,Wherein, Ar groups are as follows,
- It is 2. as described in claim 1 a kind of asymmetric to the organic red fluorescent small molecule material of receptor type, it is characterised in that：Its Shown in structural formula is one of following,
- 3. one kind asymmetry described in claims 1 or 2 is preparing Organic Electricity to the organic red fluorescent small molecule material of receptor type Application in electroluminescence device.
- 4. a kind of asymmetry as claimed in claim 3 is preparing organic electroluminescence to the organic red fluorescent small molecule material of receptor type Application in luminescent device, it is characterised in that：Organic electroluminescence device is by glass substrate, ito anode, hole transmission layer, hair Photosphere, electron transfer layer and cathode composition；Luminescent layer is undoped luminescent layer, at least containing described in a kind of claims 1 or 2 It is a kind of asymmetric to the organic red fluorescent small molecule material of receptor type.
- 5. a kind of asymmetry as claimed in claim 3 is preparing organic electroluminescence to the organic red fluorescent small molecule material of receptor type Application in luminescent device, it is characterised in that：Organic electroluminescence device is by glass substrate, ito anode, hole transmission layer, hair Photosphere, electron transfer layer and cathode composition；Luminescent layer is doping luminescent layer, as one kind described at least one claims 1 or 2 Asymmetry is material doped to being prepared in fertile material to the organic red fluorescent small molecule of receptor type.
- 6. a kind of asymmetry as claimed in claim 5 is preparing organic electroluminescence to the organic red fluorescent small molecule material of receptor type Application in luminescent device, it is characterised in that：Fertile material be CBP, MADN or PIAnCN, organic red fluorescent small molecule material Quality doping concentration in fertile material is 10%~50%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810013495.XA CN108191847B (en) | 2018-01-08 | 2018-01-08 | Asymmetric donor-acceptor type organic red fluorescent small molecular material and application thereof in organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810013495.XA CN108191847B (en) | 2018-01-08 | 2018-01-08 | Asymmetric donor-acceptor type organic red fluorescent small molecular material and application thereof in organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108191847A true CN108191847A (en) | 2018-06-22 |
| CN108191847B CN108191847B (en) | 2021-01-05 |
Family
ID=62588061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810013495.XA Active CN108191847B (en) | 2018-01-08 | 2018-01-08 | Asymmetric donor-acceptor type organic red fluorescent small molecular material and application thereof in organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108191847B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113881020A (en) * | 2021-10-29 | 2022-01-04 | 云南电网有限责任公司电力科学研究院 | Electrochromic material with double triphenylamine structure and preparation method and application thereof |
| GB2609689A (en) * | 2021-08-06 | 2023-02-15 | Sumitomo Chemical Co | Compound |
| CN115895095A (en) * | 2022-11-11 | 2023-04-04 | 广东省大湾区华南理工大学聚集诱导发光高等研究院 | Aggregation-induced emission light conversion material and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007095753A1 (en) * | 2006-02-24 | 2007-08-30 | Merck Frosst Canada Ltd. | 2-(phenyl or heterocyclic) - 1h-phenanthro [9,10-d] imidazoles |
| CN104817540A (en) * | 2015-04-24 | 2015-08-05 | 华中科技大学 | Phenanimidazole derivative and application thereof |
| CN104987309A (en) * | 2015-04-28 | 2015-10-21 | 南京高光半导体材料有限公司 | Phenanthroimidazole symmetric derivative host material and electroluminescent device |
| CN106632063A (en) * | 2015-10-30 | 2017-05-10 | 香港科技大学深圳研究院 | Compound I and compound II based on phenanthroimidazole, and preparation method and applications thereof |
-
2018
- 2018-01-08 CN CN201810013495.XA patent/CN108191847B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007095753A1 (en) * | 2006-02-24 | 2007-08-30 | Merck Frosst Canada Ltd. | 2-(phenyl or heterocyclic) - 1h-phenanthro [9,10-d] imidazoles |
| CN104817540A (en) * | 2015-04-24 | 2015-08-05 | 华中科技大学 | Phenanimidazole derivative and application thereof |
| CN104987309A (en) * | 2015-04-28 | 2015-10-21 | 南京高光半导体材料有限公司 | Phenanthroimidazole symmetric derivative host material and electroluminescent device |
| CN106632063A (en) * | 2015-10-30 | 2017-05-10 | 香港科技大学深圳研究院 | Compound I and compound II based on phenanthroimidazole, and preparation method and applications thereof |
Non-Patent Citations (2)
| Title |
|---|
| JIAN ZHOU, ET AL.: "Tuning the AIE Activities and Emission Wavelengths of Tetraphenylethene-Containing Luminogens", 《CHEMISTRYSELECT》 * |
| XINHUA OUYANG, ET AL.: "Novel "Hot Exciton" Blue Fluorophores for High Performance Fluorescent/Phosphorescent Hybrid White Organic Light-Emitting Diodes with Superhigh Phosphorescent Dopant Concentration and Improved Efficiency Roll-Off", 《ACS APPLIED MATERIALS & INTERFACES》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2609689A (en) * | 2021-08-06 | 2023-02-15 | Sumitomo Chemical Co | Compound |
| CN113881020A (en) * | 2021-10-29 | 2022-01-04 | 云南电网有限责任公司电力科学研究院 | Electrochromic material with double triphenylamine structure and preparation method and application thereof |
| CN115895095A (en) * | 2022-11-11 | 2023-04-04 | 广东省大湾区华南理工大学聚集诱导发光高等研究院 | Aggregation-induced emission light conversion material and preparation method and application thereof |
| CN115895095B (en) * | 2022-11-11 | 2024-02-09 | 广东省大湾区华南理工大学聚集诱导发光高等研究院 | Aggregation-induced emission light conversion material and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108191847B (en) | 2021-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107879984B (en) | Organic blue light micromolecule based on triplet-triplet annihilation mechanism and application thereof | |
| CN106467526A (en) | A kind of organic compound containing xanthene and its application | |
| CN108264479A (en) | A kind of organic electroluminescence device | |
| CN108129386A (en) | Swash complex luminescent material and its application in organic electroluminescence device is prepared to receptor type intramolecular base based on break-in conjugated | |
| CN108383693A (en) | A kind of organic blue fluorescent material and its preparation method and application | |
| CN108774175A (en) | One kind containing fluorene compound and its organic luminescent device | |
| WO2020124771A1 (en) | Thermally activated delayed fluorescent compound, preparation method therefor and organic electroluminescent diode device thereof | |
| CN109503427B (en) | D-A type organic blue fluorescent material and preparation method and application thereof | |
| CN108191847A (en) | It is a kind of asymmetric to the organic red fluorescent small molecule material of receptor type and its application in organic electroluminescence device | |
| CN109970642A (en) | Bipolarity thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN107698613A (en) | A kind of thermal activation delayed fluorescence material and organic electroluminescence device based on aryl boron derivative | |
| CN109232376A (en) | A kind of fluorene derivative and its organic electroluminescence device | |
| CN106749050B (en) | It is a kind of using cyclic diketones as the hot activation delayed fluorescence OLED material of core and its application | |
| CN106800526B (en) | It is a kind of using cyclic diketones as the electroluminescent organic material of core and its application | |
| CN105237519A (en) | Mazarine electroluminescent compound, and preparation method and application thereof | |
| CN111574505B (en) | Compound with benzo [ c ] cinnoline as receptor and application thereof | |
| Zhu et al. | An efficient and stable blue-emission OLED based on the A-π-A configuration by “hot exciton” strategy | |
| CN108774177A (en) | One kind containing Benzofluorene compound and its organic luminescent device | |
| CN109678759A (en) | Organic blue fluorescent material of a kind of D-A type based on dianthracene and its preparation method and application | |
| CN111423340B (en) | Blue light organic small molecule based on triplet state-triplet state annihilation mechanism and application thereof | |
| CN108727275A (en) | A kind of benzo fluorene derivative and its organic luminescent device | |
| CN109535159B (en) | Red light thermal activation delay fluorescent material, preparation method thereof and organic light emitting diode device | |
| CN107068915B (en) | A kind of application of small molecule hole transport material in blue light organic emissive diode | |
| CN110144212A (en) | A kind of electroluminescent organic material of the structure containing acridine derivatives and its application | |
| CN108409722A (en) | A kind of dibenzo fluorene compound and its organic luminescent 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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |