CN109438469B - Organic photoelectric material containing thiophene structure and application thereof - Google Patents
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Abstract
本发明涉及一种含有噻吩结构的有机光电材料及其应用，属于有机光电材料领域。该材料空间结构为扭曲非平面结构，有效避免了分子紧密积聚。实验结果表明，该材料具有高热稳定性和玻璃化温度，分别用作有机电致发光器件的发光材料，都能得到色纯度和效率非常高的电致发光。The invention relates to an organic optoelectronic material containing a thiophene structure and its application, belonging to the field of organic optoelectronic materials. The spatial structure of the material is a twisted non-planar structure, which effectively avoids the close accumulation of molecules. The experimental results show that the material has high thermal stability and glass transition temperature, and can be used as light-emitting materials for organic electroluminescent devices, respectively, and can obtain electroluminescence with very high color purity and efficiency.
Description
Technical Field
The invention relates to an organic photoelectric material containing a thiophene structure and application thereof, belonging to the technical field of organic photoelectric materials.
Background
The origin of organic electroluminescent devices (OLEDs) dates back to the sixties of the twentieth century, and Pope et al use anthracene single crystals to emit light with a direct current voltage applied thereto, but they do not attract much attention because of their high driving voltage (100V) and low luminance and efficiency. With the continuous improvement of the technology, C.W. Tang et al, Kodak, Inc. in 1987, used 8-hydroxyquinoline aluminum (AIq)3) The OLED device with double-layer sandwich structure is made of luminescent material by vacuum evaporation, the turn-on voltage is only a few volts, and the brightness can reach 1000cd/m2The mark OLED has taken an important step toward practical application, and becomes an important milestone in the field of organic electroluminescence.
Thiophene is one of the heteroatom-sulfur-containing compounds present in nature, and it is widely used as a basic skeleton of medicines, pesticides, and functional materials. For bithiophenes, in which a few thiophenes are fused, they have important applications in organic field devices, organic semiconductors, organic light-emitting diodes and photovoltaic cells. Because the bithiophene derivatives have special chirality and cross-conjugation property, the bithiophene derivatives have attracted great research interest and are widely researched as electronic materials. Although people have limited knowledge on the electronic behavior of the chiral and cross-conjugated materials, the scientific significance and the application prospect of the cross-conjugated materials are quite clear, and a new generation of organic electronic materials which cannot be compared with the current inorganic electronic materials are possibly developed.
At present, the problems of low luminous efficiency, short service life and the like of the device when the maximum obstacle of the comprehensive and practical OLED technology is blocked are solved. Research shows that the electron mobility of the electron transport material is far lower than the hole mobility of the hole transport material, so that the positive and negative carrier transport is unbalanced, which is one of the main reasons for limiting the luminous efficiency and the service life of the OLED, and therefore, the design of the material with the bipolar property has important significance. Theoretically, the performance of the electroluminescent device using the appropriate luminescent material with high-efficiency bipolar characteristics can be greatly improved compared with the performance of the common unipolar transmission luminescent material. However, most of the existing luminescent materials are unipolar transmission, for example, most of the carbazole derivatives which are most widely used are mainly hole transmission, the carrier transmission line of the organic silicon derivative luminescent materials is not high for holes and electrons, and the phenanthroline and triazine luminescent materials are mainly electron transmission.
In the patent, a nitrogen-containing structural group unit with hole transmission performance is connected with a thiophene structural group with electron transmission performance to prepare a compound with bipolar carrier transmission performance. The compounds are used for preparing devices with different structures, the devices can be used as OLED light-emitting main materials, and the prepared electroluminescent devices prove that the materials have great application potential.
Disclosure of Invention
The invention aims to solve the technical problem of providing an organic photoelectric material containing a thiophene structure and application thereof, and devices prepared by using the compound as a main material of a light-emitting layer have better performance and effect. In addition, the compound has higher glass transition temperature and molecular thermal stability, is easy to form a good amorphous film, has strong fluorescence in both solution and solid, and has high fluorescence quantum efficiency.
The technical scheme for solving the technical problems is as follows: an organic photoelectric material containing a thiophene structure has the following structural formula:
wherein R is a substituted or unsubstituted carbazole derivative or a nitrogen-containing aryl compound.
R is one of the substituents of the following structural formula:
the invention has the beneficial effects that:
the invention synthesizes a series of organic photoelectric materials containing thiophene structural groups, wherein nitrogen-containing structural group units with hole transmission performance and thiophene structural groups with electron transmission performance are connected to prepare compounds with bipolar carrier transmission performance, and the advantages of the compounds and the compounds are combined. The bipolar transmission material is formed by adjusting the molecular structures of different parts of molecules to ensure that the molecules have both hole and electron transmission properties. The spatial structure of the material is a twisted non-planar structure, so that the tight accumulation of molecules is effectively avoided. Experimental results show that the material has high thermal stability and glass transition temperature, and can be respectively used as a luminescent material of an organic electroluminescent device to obtain electroluminescence with very high color purity and efficiency.
The invention provides a preparation method of the organic photoelectric material containing the thiophene structural group, which is characterized by being realized according to the following synthetic route:
wherein R is preferably selected from one of the following groups:
in the steps, under the protection of nitrogen or inert gas, palladium acetate, palladium tetratriphenylphosphine and palladium dichlorotriphenylphosphine are used as catalysts, potassium carbonate, sodium hydroxide or potassium hydroxide is used for alkaline environment, and the reaction is carried out for 5-30 hours at the temperature of 40-100 ℃ for the nitrogenous aryl boric acid and the brominated thiophene-containing structural group.
The structure of the organic photoelectric material containing thiophene structural groups synthesized by the invention is as follows:
the invention also provides the application of the organic photoelectric material containing the thiophene structural group in an organic electroluminescent device;
the electroluminescent device of the present invention has various forms, but basically has a multilayer structure in which at least a hole transport layer, a light-emitting layer, and an electron transport layer are interposed between an anode and a cathode. Specific examples of the configuration of the element are (1) an anode/a hole transport layer/a light-emitting layer/an electron transport layer/a cathode; (2) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode; (2) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode, and the like. Wherein the luminescent layer of the fluorescent device and the host material of the phosphorescent device are the compounds shown in formula 1, and the doping material of the phosphorescent device is an iridium complex of a common ring metal ligand, such as Ir (piq) emitting red light2:(acac)。
The organic photoelectric material containing the thiophene structural group is applied to a blue light electroluminescent device, and can obtain the maximum current efficiency of 4.52cd/A and the maximum brightness of 10431cd/m2(ii) a In addition they may be referred to as Ir (piq)2(acac) the red device prepared by the host material has the electroluminescent peak value at 637nm, the maximum current efficiency of 12.2cd/A and the maximum brightness of 23321cd/m2This performance is far superior to CPB-based devices, which is one of the best device data for single emissive layer.
As shown in FIG. 1, the organic photoelectric material containing thiophene structural group synthesized by the invention is used as a luminescent layer applied to an organic electroluminescent device, and generally comprises an ITO conductive glass substrate 1 (anode) and a hole injection layer 2 (molybdenum trioxide MoO) which are sequentially stacked3) And a hole transport layer 3[ N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB)]And a light-emitting layer 4[ tris (8-hydroxyquinoline) aluminum (Alq)3) The compound containing thiophene structural group synthesized by the invention or the compound taking the compound as a main material and doped with phosphor photoligandCompound (I)]Hole-blocking layer 5[2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP)]And an electron transport layer 6[ the compound having a bipolar carrier transport property synthesized by the present invention or 1,3, 5-tris (1-naphthyl-1H-benzimidazol-2-yl) benzene (TPBI)]An electron injection layer 7(LiF) and a cathode layer 8 (Al).
All functional layers can adopt vacuum evaporation or solution film forming process. The molecular structural formulae of some of the organic compounds used in the device are shown below:
the functional layer of the organic electroluminescent device prepared by the organic photoelectric material containing thiophene structural group is not limited to the material, and can be replaced by other materials, for example, the hole transport layer can be replaced by N, N '-diphenyl-N, N' - (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), and the electron transport layer can be replaced by tris (8-hydroxyquinoline) aluminum (Alq)3) 2- (4 '-tert-butylphenyl) -5- (4' -biphenyl) -1,3, 4-oxadiazole (PBD),4, 7-diphenyl-1, 10-phenanthroline (BPhen). The molecular structural formula of these materials is as follows:
the invention has the beneficial effects that:
the organic photoelectric material containing thiophene structural groups, which is synthesized by the invention, is applied to an organic electroluminescent device to obtain high-efficiency electroluminescent performance, and has the following main advantages:
1. the novel material provided by the invention has a rigid carbon skeleton non-planar structure, effectively avoids intermolecular aggregation, and has high fluorescence quantum efficiency and color purity.
2. Has good thermal stability, high glass transition temperature and high decomposition temperature.
3. The material has good bipolar transmission performance, and has good hole and electron mobility by adjusting the molecular structure of different parts of the molecule.
4. The material has proper molecular energy level and is the main body material of the OLED luminescent material.
Drawings
FIG. 1 is a schematic diagram of an electroluminescent device according to the present invention;
FIG. 2 shows the electroluminescent curve of the device in example 1, wherein the compound 1 is used as the luminescent layer of the organic electroluminescent device;
FIG. 3 is an electroluminescence curve of a device in example 2 in which compound 2 is used as a light-emitting layer of an organic electroluminescence device;
FIG. 4 is an electroluminescence curve of a device in example 3, in which compound 3 is used as a host material of a light-emitting layer of an organic electroluminescence device;
FIG. 5 is an electroluminescence curve of a device in example 4, wherein the compound 4 is used as a main material of a light-emitting layer of an organic electroluminescence device;
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Examples of compound sample preparation:
example 1 synthesis of compound 1:
into a 100ml three-necked flask were charged 6.4g (22.0mmol) of (4- (9H-carbazol-9-yl) phenyl) boronic acid and 4.0g of 2- (2, 6-dibromo-4H-cyclopenta [1,2-b:5,4-b']Dithioen-4-yl) malononitrile (10.0mmol), 60mL of toluene were added, followed by 30.0mL of K2CO3The aqueous solution (1mol/L) was stirred with nitrogen for 1 hour to remove oxygen from the reaction flask. Then 12mg (0.1mmol) of palladium tetrakistriphenylphosphine was added, the mixture was refluxed with vigorous stirring, and the progress of the reaction was monitored by TLC. After 24 hours of reaction, 50mL of deionized water was added to the reaction solution, insoluble materials were removed by filtration, the aqueous phase and the organic phase were separated, the organic phase was concentrated by vacuum distillation to no fraction, column chromatography was performed, and the eluent was ethyl acetate/n-hexane (1:10, v/v). 5.63g of a white solid were obtained (yield 77.88%). The compound was identified using DEI-MS, formula C48H26N4S2Detection value [ M +1 ]]+723.63, calculate value 722.16.
EXAMPLE 2 Synthesis of Compound 2
Prepared by the synthetic method of compound 1 in example 1 using (4- (9, 9-dimethylacridin-10 (9H) -yl) phenyl) boronic acid as a starting material. The compound was identified using DEI-MS, formula C54H38N4S2Detection value [ M +1 ]]+807.75, calculate value 806.25.
EXAMPLE 3 Synthesis of Compound 3
Prepared by the synthetic method of compound 1 in example 1 starting from (4- (10H-phenoxazin-10-yl) phenyl) boronic acid. The compound was identified using DEI-MS, formula C48H26N4O2S2Detection value [ M +1 ]]+755.09, calculate value 754.15.
EXAMPLE 4 Synthesis of Compound 4
Prepared by the synthetic method of compound 1 in example 1 using (4- (10H-phenothiazin-10-yl) phenyl) boronic acid as a starting material. The compound was identified using DEI-MS, formula C48H26N4S4Detection value [ M +1 ]]+787.33, calculated: 786.10
The organic electroluminescent device can be manufactured according to the method in the field, and the specific method comprises the following steps: in high vacuum condition, sequentially evaporating MoO on cleaned conductive glass (indium tin oxide) substrate3Hole transport layer, light emitting layer, BCP, electron transport layer, LiF at 1nm and Al at 120 nm. The device shown in fig. 1 can be obtained by the method, and the method can be divided into the following functional layers according to the functional layers of the device: examples 1 and 2 of the light-emitting layer of the fluorescent device, examples 3 and 4 of the light-emitting layer of the phosphorescent device, examples 5 and 6 as the electron transport layer, and examples 7 and 8 as the hole transport layer.
Examples as light emitting layer of fluorescent device
Example 1
ITO/MoO3(10nm)/NPB (50 nm)/Compound 1(30nm)/BCP (10nm)/TPBI (30nm)/LiF(1m)/Al(120nm)。
Example 2
ITO/MoO3(10nm)/NPB (50 nm)/Compound 15(30nm)/BCP (10nm)/TPBI (30nm)/LiF (1m)/Al (120 nm).
Device embodiments as host materials for phosphorescent devices
Example 3
ITO/MoO3(10nm)/NPB (50 nm)/Compound 1: ir (piq)2:(acac)(6wt％，30nm) /BCP(10nm)/TPBI(30nm)/LiF(1m)/Al(120nm)。
Example 4
ITO/MoO3(10nm)/NPB (50 nm)/Compound 15: ir (piq)2:(acac)(6wt％，30nm) /BCP(10nm)/TPBI(30nm)/LiF(1m)/Al(120nm)。
The current-luminance-voltage characteristics of the device were obtained with a Keithley source measurement system (Keithley 236 source Measure Unit) with calibrated silicon photodiodes, the electroluminescence spectra were measured with a PR-705 spectrometer from photoreaarch corporation, usa, all in a room temperature atmosphere.
The device performance data is shown in the following table:
the devices 1 and 2 both emit blue light, and the highest current efficiencies obtained are 4.5cd/A and 3.5cd/A, which are outstanding in the blue fluorescent devices reported at present. The device 3 and the device 4 take the compound of the invention as a main body material, the prepared device emits red light, the highest current efficiency reaches 12.2cd/A, the maximum external quantum efficiency reaches 13.4 percent, and the device EL performance of a reference (adv. Mater, 2003,15,884) has obvious advantages in color efficiency, brightness and purity and strong operability.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
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| WO2018140578A1 (en) * | 2017-01-25 | 2018-08-02 | President And Fellows Of Harvard College | Non-fullerene solar panel acceptor compounds |
| CN108586289A (en) * | 2018-05-04 | 2018-09-28 | 西北大学 | The aryl anthracene phenanthrene class electroluminescent organic material and its preparation method and application of malononitrile substitution |
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| WO2018140578A1 (en) * | 2017-01-25 | 2018-08-02 | President And Fellows Of Harvard College | Non-fullerene solar panel acceptor compounds |
| CN108586289A (en) * | 2018-05-04 | 2018-09-28 | 西北大学 | The aryl anthracene phenanthrene class electroluminescent organic material and its preparation method and application of malononitrile substitution |
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