CN115093363A - Organic blue light micromolecules and preparation and application thereof - Google Patents
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Abstract
The invention discloses organic blue light micromolecules and preparation and application thereof, wherein benzophenone is used as an electron acceptor, carbazole is used as an electron donor, and an electron-withdrawing group trifluoromethyl is introduced and modified at different positions to form a strong D-A structure. The carbazole with high rigidity can increase the steric hindrance of the benzophenone, the molecular structure generates certain distortion, after the electron-withdrawing group trifluoromethyl is introduced, the electron-withdrawing capability of the benzophenone group is further effectively enhanced, the space charge transfer capability is enhanced, the red shift of the molecule is weakened, the emission of the molecule is ensured to be positioned in a blue light region, the deep blue luminescence can be realized, and a new thought is provided for the research and development of the TADF blue luminescent material.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent material synthesis, in particular to an organic blue light micromolecule and preparation and application thereof.
Background
With the advancement of technology, the development of electronic technology products is rapid, and especially in terms of display screens, the transition from ubiquitous to small to large size, from monochrome to multi-color screens, and from liquid crystal displays to OLEDs is experienced. Among them, the OLED is favored by its excellent properties such as high brightness, fast response, high definition, high light emitting efficiency, and good flexibility. OLEDs have three mechanisms of light emission: OLEDs based on fluorescence emission (first generation), OLEDs based on phosphorescence emission (second generation) and OLEDs based on Thermally Activated Delayed Fluorescence (TADF) (third generation).
The traditional phosphorescent material mostly adopts metal complexes, but the metal complexes are expensive and have larger pollution because of the coordination of noble metals, and on the other hand, the metal complex phosphorescent material with longer service life (microsecond level) may cause dominant Triplet-Triplet annihilation (TTA) under high current, which limits the development of the phosphorescent material. The third generation of the OLED based on the TADF material breaks through the IQE limit of the first generation of fluorescent OLED, can realize the preparation of the OLED by using a pure organic material, overcomes the defects of the second generation of phosphorescent OLED, and becomes a research hotspot. The research on new high-performance TADF materials has been one of the exploration directions of numerous researchers, but the operational stability of OLEDs based on TADF materials is still in the optimization so far.
To obtain a full color display or a white OLED, a combination of the three primary colors red, green and blue (RGB) is essential. Currently, high emissivity and stable blue light emitters are actively being researched. TADF blue emitting materials are considered as strong candidates to solve the problems of color purity, quantum efficiency, and long-term device stability. Based on the enthusiasm of the scientific community for researching the blue luminescent material, the research field develops very rapidly.
The influence of device processing technology and functional materials is eliminated, and the development of a new blue light material is the most effective and direct method for improving the luminous capacity of the device. The benzophenone group is an excellent basic unit which has a plurality of modifiable chemical reaction sites and can be used for researching high-efficiency blue-light materials. In addition, the introduction of a rigid carbazole group further increases the steric hindrance of the molecule, which further contributes to light emission.
Chinese patent CN 111574431 a discloses a multifunctional organic light emitting material based on carbazole and benzophenone derivatives, which is based on carbazole derivative groups with electron donating ability, and is modified at different substitution positions by utilizing carbonyl groups of benzophenone, so that molecules can form distorted D-a type compounds, and the ratio of n-orbitals to pi-orbitals and the accumulation structure of aggregation states are changed to adjust the photophysical properties and other properties, but in the material, only the fluorescence peak of individual compound molecules is located in the blue light region, and with the change of melting state, the maximum emission peak of the material appears red shift, the emission color changes from blue to green, and it is difficult to realize stable strong blue light emission.
Therefore, it is necessary to further design the molecular structure of the compound to obtain high-performance organic blue-light small molecules, so as to improve the luminescent quantum efficiency and film forming capability of the material, and provide a new idea for the development of TADF blue luminescent materials.
Disclosure of Invention
The invention aims to solve the problems in the prior art, and provides an organic blue light small molecule which is modified at different positions on benzophenone by introducing electron-withdrawing group trifluoromethyl to form a stronger D-A structure, and the obtained small molecule compound can realize strong blue light emission in different solvents.
The technical scheme disclosed by the invention is as follows: the organic blue light micromolecule has the following structural general formula:
wherein L is carbazole, 3-bromocarbazole or 3, 6-dibromocarbazole.
Specifically, the structural formula of the organic blue light micromolecule is any one of the following:
further, the organic blue light small molecule can be dissolved in dichloromethane, toluene, tetrahydrofuran and N, N' -dimethylformamide and has solution processability.
Further, the vibrational absorption bands of the compounds M1-M12 in dichloromethane, tetrahydrofuran, toluene and N, N' -dimethylformamide solutions were at 270-300nm and 310-350 nm.
Further, the emission wavelength range of the compounds M1-M12 is 420-480nm, which belongs to the blue light region.
The organic blue light small molecule can be applied to the field of OLED based on TADF materials, and shows deep blue light emitting characteristics in solvents with different polarities.
The invention has the beneficial effects that:
1. the organic blue light micromolecule disclosed by the application takes benzophenone as an electron acceptor and carbazole as an electron donor, and modification is carried out at different positions by introducing electron-withdrawing group trifluoromethyl, so that a strong D-A structure is formed. The carbazole with high rigidity can increase the steric hindrance of the benzophenone, the molecular structure generates certain distortion, meanwhile, after an electron-withdrawing group trifluoromethyl is introduced into different positions, the electron-withdrawing capability of the benzophenone group is further effectively enhanced, the space charge transfer capability is enhanced, the red shift of the molecule is weakened, the emission of the molecule is ensured to be positioned in a blue light region, deep blue luminescence can be realized in part of organic solvents, and a new thought is provided for the research and development of a TADF blue luminescent material;
2. the organic blue light micromolecule disclosed by the application improves the proportion of the interaction force of hydrogen bonds by introducing the electron-withdrawing group trifluoromethyl, particularly the introduction of the trifluoromethyl on the third position is more beneficial to enhancing the interaction force of the hydrogen bonds, and the factors can enhance space charge transfer, promote spin-orbit coupling, weaken the emission red shift of the molecule and be more beneficial to blue light emission;
3. the organic luminescent material is prepared by adopting cheap and easily-obtained raw materials and simple synthesis steps, a series of organic luminescent materials with excellent luminescent performance are synthesized, and the luminescent wavelength of molecules can be adjusted and the luminescent performance of the materials can be improved by changing the position of an electron-withdrawing group.
Drawings
FIG. 1 shows M3 in CDCl prepared in example 1 3 Hydrogen spectrum of (1);
FIG. 2 is a MALDI-TOF plot of M3 prepared in example 1;
FIG. 3 shows M7 in CDCl prepared in example 2 3 Hydrogen spectrum of (1);
FIG. 4 is a MALDI-TOF plot of M7 prepared in example 2;
FIG. 5 shows M9 in CDCl prepared in example 3 3 Hydrogen spectrum of (1);
FIG. 6 is a MALDI-TOF plot of M9 prepared in example 3;
FIG. 7 is a normalized UV absorption and PL spectrum of Compound M3 in different solvents;
FIG. 8 is a normalized UV absorption and PL spectrum of Compound M7 in different solvents;
FIG. 9 is a normalized UV absorption and PL spectrum of Compound M9 in different solvents;
FIG. 10 is a normalized CIE chromaticity coordinates of compounds M3, M7, and M9 in different solvents;
FIG. 11 is a diagram of the single crystal structure and two-dimensional stacking of Compound M3;
FIG. 12 is a diagram of the single crystal structure and two-dimensional stacking of Compound M7;
FIG. 13 is a diagram of the single crystal structure and two-dimensional stacking of Compound M9;
FIG. 14 is the composition of Hirshfeld surface forces for each component in single crystals of compounds M3, M7, M9 and O-2 BrCzBP.
Detailed Description
The following examples further illustrate the present invention but are not to be construed as limiting the invention. Modifications and substitutions to methods, procedures, or conditions of the invention may be made without departing from the spirit of the invention.
Example 1: preparation of M3
The molecular structure of M3 is as follows
The preparation process of M3 is as follows: 3, 6-dibromocarbazole (0.99g, 3.05mmol) and cesium carbonate (2.94g, 9mmol) are weighed into a clean two-necked flask, evacuated under nitrogen and bubbled three times, DMF (40mL, water and oxygen removed) is added, 2-fluoro-3 (trifluoromethyl) benzophenone liquid (0.78g, 2.9mmol) is added, the mixture is condensed and refluxed at 150 ℃ for 12h, after the reaction is cooled, dichloromethane and water are used for extraction, the organic phase is dried over anhydrous sodium sulfate, concentrated and spun, the crude product is separated by silica gel column chromatography (eluent is petroleum ether: ethyl acetate ═ 3:1, V: V), and the crude product is dried under vacuum to obtain 0.84g of white powder product (yield: 51%).
1 H NMR(400MHz,Chloroform-d)δ8.11(dd,J＝7.4,2.1Hz,1H),7.96(d,J＝1.9Hz,2H),7.91-7.81(m,2H),7.39(dd,J＝8.7,1.9Hz,2H),7.34-7.26(m,1H),7.23-7.17(m,2H),7.07(t,J＝7.7Hz,2H),6.82(d,J＝8.7Hz,2H). 13 C NMR(100MHz,CDCl 3 ) δ 192.99,141.69,140.15,134.39,132.48,132.36,128.83,128.74,128.69,128.14,127.70,126.90,122.78,121.88,112.38,111.19.MALDI-TOF, m/z: 573.21, Experimental value: 572.69.
example 2: preparation of M7
The molecular structure of M7 is as follows
The preparation process of M7 is as follows: carbazole (0.683g, 4.08mmol), cesium carbonate (3.905g, 12mmol) were weighed into a clean two-necked flask, evacuated under nitrogen bubbling for 3 times, DMF (40mL, water and oxygen removal) was added, 2-fluoro-5 (trifluoromethyl) benzophenone liquid (1.061g, 3.96mmol) was added, condensed under reflux at 150 ℃ for 12h, after cooling the reaction, extracted with dichloromethane and water several times, the organic phase was dried over anhydrous sodium sulfate, concentrated and spun, the crude product was separated by silica gel column chromatography (eluent petroleum ether: ethyl acetate ═ 3:1, V: V), and dried under vacuum to give 0.954g of white crystalline product (yield: 58%).
1 H NMR(400MHz,DMSO-d 6 )δ8.27(dd,J＝8.3,2.2Hz,1H),8.19(d,J＝2.2Hz,1H),7.98(d,J＝7.2Hz,3H),7.35(td,J＝7.5,6.9,1.2Hz,2H),7.25(d,J＝8.2Hz,2H),7.21–7.17(m,5H),6.93(t,J＝7.7Hz,2H). 13 C NMR(100MHz,CDCl 3 ) δ 194.25,139.40,138.35,136.79,134.67,131.33,128.36,128.31,128.28,127.66,127.63,126.65,126.00,124.98,122.44,119.53,119.03,108.66 MALDI-TOF, m/z: theoretical values are as follows: 415.42, Experimental value: 414.797.
example 3: preparation of M9
The molecular structure of M9 is as follows
The preparation process of M9 is as follows: respectively weighing 3, 6-dibromocarbazole (0.987g, 3mmol) and cesium carbonate (2.94g, 9mmol), adding into a clean two-necked bottle, vacuumizing and blowing nitrogen for three times, adding DMF (50ml, removing water and oxygen), adding 2-fluoro-5 (trifluoromethyl) benzophenone liquid (0.74g, 2.76mmol), condensing and refluxing at 150 ℃ for 12h, after reaction cooling, extracting with dichloromethane and water for multiple times, drying with sodium sulfate anhydrous, concentrating and spin-drying, separating the crude product by silica gel column chromatography, wherein an eluent is dichloromethane: petroleum ether 2:1(V: V), and dried in vacuo to give 1.03g of the product as white crystals (yield: 65%).
1 H NMR(400MHz,Chloroform-d)δ8.14(d,J＝2.1Hz,1H),8.06(dd,J＝8.2,2.2Hz,1H),7.90(d,J＝1.9Hz,2H),7.73(d,J＝8.2Hz,1H),7.47(dd,J＝8.7,1.9Hz,2H),7.16-7.02(m,5H),6.84(dd,J＝8.3,7.3Hz,2H). 13 C NMR(101MHz,CDCl 3 ) δ 193.70,138.46,137.25,137.05,134.45,131.97,128.48,128.45,128.42,128.29,127.63,127.59,126.83,126.43,122.97,122.07,112.75,110.40.MALDI-TOF, m/z: theoretical values are as follows: 573.21, Experimental value: 572.722.
the synthetic routes for M3, M7, and M9 prepared in examples 1-3 are as follows:
the molecular structures of M3, M7 and M9 are confirmed by mass spectrometry (MALDI-TOF), nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the related spectra are shown in figures 1-6.
The preparation methods of M1, M2, M4, M5, M6, M8, M10, M11, and M12 are similar to the preparation methods of M3, M7, and M9 disclosed above, so that the details are not repeated herein, and the corresponding structures are also subjected to characterization confirmation, so that the preparation can be successfully confirmed.
Photophysical property detection
Through experimental research, the 12 compounds M1-M12 prepared in the embodiment have good solubility in common organic solvents such as toluene, dichloromethane, tetrahydrofuran, N' -dimethylformamide and the like, and the compounds have good solution-processable properties.
The photophysical properties of the compounds were studied by uv-vis absorption spectroscopy and photoluminescence spectroscopy. Three substances M3, M7 and M9 are specifically selected as representatives to analyze specific performance parameters. FIGS. 7-10 show the UV absorption and PL spectra and CIE chromaticity coordinates of normalized compounds M3, M7, and M9, respectively, in different solvents;
as shown, M9 and M3 exhibited similar uv absorption spectra in Toluene (TOL), Dichloromethane (DCM), Tetrahydrofuran (THF) and N, N '-Dimethylformamide (DMF) (the polarity magnitudes of these four solvents are toluene < dichloromethane < tetrahydrofuran < N, N' -dimethylformamide), with the major absorption bands centered at 280-300nm, again due to local pi-pi transition within the molecule. Compared with the TOL solvent with the minimum polarity, the maximum emission peak of M9 appears obvious red shift along with the increase of the polarity of the solvent, the maximum emission peaks in TOL, DCM, THF and DMF are respectively positioned at 437nm, 490nm, 466nm and 504nm, blue light emission is realized in toluene and tetrahydrofuran, and the maximum emission peak is positioned in a deep blue region in TOL (the maximum emission peak interval is generally considered to be deep blue light emission in the range of 410-440nm in the field), and the CIE coordinates of the maximum emission peak are (0.16, 0.14).
Looking again at the emission of M3, the emission peak of M3 appears as a distinct blue shift in both the more polar THF and DMF solvents and a distinct red shift in the less polar DCM solvent, compared to the emission peak of M dissolved in the least polar TOL solution, and the emission wavelengths of M3 in TOL, DCM, THF, and DMF lie at 444nm, 480nm, 397nm, and 420nm, respectively, except that blue emission is exhibited in THF, and deep blue emission is exhibited in both TOL and DMF. CIE coordinates in toluene were (0.16,0.17) and in DMF were (0.15, 0.09).
The absorption peak of M7 is at 285-300nm, and has stronger absorption peaks at 330-350nm in DCM and TOL solvent, the maximum emission peaks of M7 in TOL and THF are 437nm and 466nm, both in blue region, and the emission spectrum shows dark blue luminescence with CIE color coordinates of (0.16,0.14) in toluene. Compared with a compound without an electron-withdrawing group, due to the introduction of the electron-withdrawing group trifluoromethyl, the D-A structure is further strengthened, the charge transfer in molecules is enhanced, and the red shift emitted by the molecules is weakened, so that the compound can emit deep blue light.
When the other 9 similar compounds are studied, the other 9 compounds can also show dark blue luminescence characteristics in toluene.
Analysis of crystal structure
The crystal structures of 12 compounds M1-M12 were characterized by a single crystal diffractometer. The crystal structure characteristics of the compounds are specifically analyzed by taking three substances of M3, M7 and M9 as representatives.
M9 has strong intramolecular pi-x interaction with distance of
This is because the carbazole group has a small dihedral angle (33.13 °) with the benzophenone group, and the M9 adjacent molecules also have a strong C-H … O interaction at a distance of
Meanwhile, the molecules have stronger C-H … pi interaction (respectively
And
)。
compared with M9 containing two bromine atoms, the product does not contain bromineThe dihedral angle between carbazole and benzophenone of atomic M7 becomes smaller (25.99), and the molecular structure alone shows that the radius of bromine atom is larger, and the introduction of bromine atom steric hindrance increases to change the dihedral angle, so that M7 containing no bromine atom has a smaller dihedral angle. And M7 became more strongly intramolecular pi-x interactions than bromine atom-containing M9
In addition, there are many different interactions between molecules, such as C-H … π interaction
C-H … O interaction
The greater dihedral angle (78 °) between the carbazole group and the benzophenone group of M3 compared to M9 is likely due to a further increase in steric hindrance caused by the introduced trifluoromethyl group in position 3, resulting in an increase in dihedral angle, which directly leads to a reduction in its intramolecular pi-pi x interaction. M3 there are many different kinds of intermolecular interactions, e.g., C … O interaction
C-H … O interaction (respectively
) C-H … F interaction
And intermolecular pi-interaction
Wherein C-H … F interact
The molecular structure is strongest, and shows that the introduction of trifluoromethyl at the 3 rd position enhances the interaction of hydrogen bonds, is favorable for enhancing space charge transfer, promotes spin-orbit coupling, weakens the red shift of the emission of the molecule, and is further favorable for the blue light emission of the molecule.
In addition, after analysis of Hirshfeld surface acting force of each component in M3, M7, M9 and O-2BrCzBP single crystals, it is found that the ratio of hydrogen bond interaction acting force is improved by introducing electron-withdrawing group trifluoromethyl, but the M7 does not contain Br atoms, so that the H … F ratio is relatively higher, and the improvement of the ratio of the hydrogen bond interaction acting force enhances space charge transfer and is beneficial to blue light emission.
The structural formula of O-2BrCzBP is as follows
The foregoing illustrates and describes the principles, general features, and advantages of the present invention. However, the above description is only an example of the present invention, the technical features of the present invention are not limited thereto, and any other embodiments that can be derived by those skilled in the art without departing from the technical scope of the present invention should be covered by the claims of the present invention.
Claims (6)
1. The organic blue light micromolecule is characterized in that the micromolecule has the following structural general formula:
wherein L is carbazole, 3-bromocarbazole or 3, 6-dibromocarbazole.
2. The organic blue-light small molecule of claim 1, wherein the organic blue-light small molecule has a structural formula of any one of the following:
3. the class of organic blue-light small molecules of claim 2, wherein said organic blue-light small molecules are soluble in dichloromethane, toluene, tetrahydrofuran, and N, N' -dimethylformamide.
4. The organic blue-light small molecule as claimed in claim 1, wherein the vibrational absorption bands of the compound M1-M12 in dichloromethane, tetrahydrofuran, toluene and N, N' -dimethylformamide are at 270-300nm and 310-350 nm.
5. The organic blue-light small molecule as claimed in claim 1, wherein the emission wavelength range of the compounds M1-M12 is 420-480nm, and belongs to the blue light region.
6. The application of the organic blue light small molecules as claimed in any one of claims 1 to 5 in the field of TADF material-based OLEDs, wherein the organic blue light small molecules exhibit deep blue light emission characteristics in solvents with different polarities.
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