CN116102492A - Blue light organic luminescent molecule with ortho-steric hindrance induced torsion structure - Google Patents

Blue light organic luminescent molecule with ortho-steric hindrance induced torsion structure Download PDF

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CN116102492A
CN116102492A CN202211270052.1A CN202211270052A CN116102492A CN 116102492 A CN116102492 A CN 116102492A CN 202211270052 A CN202211270052 A CN 202211270052A CN 116102492 A CN116102492 A CN 116102492A
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blue light
steric hindrance
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杨晓龙
孙源慧
周桂江
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Shaanxi Baoguangliuyuan Technology Co ltd
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

A blue light organic luminescent molecule with an ortho-steric hindrance induced torsion structure has a chemical general formula as shown in the specification:
Figure DDA0003894775930000011
in the above formula, the substituent R 1 And R is R 2 Any aromatic amine and its derivative group selected from substituted or unsubstituted carbazole, diphenylamine, acridine, phenothiazine, phenoxazine, indole, etc.; according to the blue light material disclosed by the invention, a large-volume substituent is introduced to the 2,2' position of bipyridine to form an ortho-position substitution structure, so that the large-volume substituent and a bipyridine core are promoted to be strongly distorted to form an ortho-position steric hindrance induced distortion structure, the length of a molecular conjugated system can be effectively limited, and the excellent blue light color purity of the molecular conjugated system is ensured; at the same time, the twisted structure canThe consumption of energy by intramolecular vibration can be restrained, and the non-radiative transition rate constant is reduced, so that the luminous efficiency of molecules is improved, and the outstanding luminous performance of the molecules is ensured; therefore, the method has great application prospect in the aspect of preparing high-performance electronic devices.

Description

Blue light organic luminescent molecule with ortho-steric hindrance induced torsion structure
Technical Field
The invention relates to the technical field of new materials, in particular to a blue light organic luminescent molecule with an ortho-position steric hindrance induced torsion structure.
Background
Blue light is one of the three primary colors, which is essential, whether in full color display or high color rendering index white light illumination. Currently, the organic electroluminescent technology is gradually applied to the fields of display and illumination, and along with the increasing demands of people on wide-color-gamut high-definition display and high-quality white light illumination, the demands of organic electroluminescent devices on high-efficiency high-color-purity blue light luminescent materials are also increasing. The research and development of the high-performance blue light luminescent material becomes a core key point in the field of organic electroluminescence, and has great value for further improving the display and illumination quality and promoting the development of new application scenes such as AR/VR and the like of the organic electroluminescence technology. However, the blue light organic luminescent molecular material still faces the bottleneck problems of low efficiency, poor color purity and the like, and serious limitation is caused to the further development of the organic electroluminescent technology.
Disclosure of Invention
Aiming at the problems in the development of the existing blue light organic luminescent molecular material, the invention discloses a blue light organic luminescent molecule with an ortho-steric hindrance induced torsion structure, which has the characteristics of good thermal stability, good color purity and high luminescent efficiency.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a blue light organic luminescent molecule with ortho steric hindrance induced torsion structure has a chemical general formula as follows:
Figure BDA0003894775910000021
in the above formula, the substituent R 1 And R is R 2 Any aromatic amine and its derivative group selected from substituted or unsubstituted carbazole, diphenylamine, acridine, phenothiazine, phenoxazine, indole, etc., including the following molecules:
Figure BDA0003894775910000022
the beneficial effects of the invention are as follows:
the molecule introduces a bulky substituent to the 2,2' position of bipyridine to form an ortho-position substitution structure, promotes the bulky substituent and bipyridine core to strongly twist to form an ortho-position steric hindrance induced twisting structure, and can effectively limit the length of a molecular conjugated system, thereby ensuring that the emitted blue light has high purity, and the y value of the chromaticity coordinate of a light-emitting spectrum is less than 0.1, and belongs to high-color-purity deep blue light. The twisted structure can inhibit the consumption of energy by intramolecular vibration and reduce the non-radiative transition rate constant, thereby being very beneficial to improving the luminous efficiency of molecules, and the absolute luminous quantum efficiency measured by an integrating sphere is up to 98 percent and is obviously higher than that of the conventional blue light material by less than 80 percent. The thermal stability test shows that the thermal decomposition temperature of the materials exceeds 588K, and the requirements of the electroluminescent device on thermal stability in preparation and long service life are completely met. The characterization test results prove that the organic blue light luminescent material disclosed by the invention has the advantages of high stability, excellent color purity, excellent luminescent quantum efficiency and the like. Therefore, the method has innovativeness in the aspect of material molecular structure design and remarkable progress in the aspect of material performance.
Drawings
Fig. 1 is a reaction scheme for preparing a blue organic luminescent molecule 1 having an ortho-steric hindrance induced twist structure.
Fig. 2 is a reaction scheme for preparing a blue organic luminescent molecule 4 having an ortho-steric hindrance induced twist structure.
Fig. 3 is a reaction scheme for preparing a blue organic luminescent molecule 7 having an ortho-steric hindrance induced twist structure.
FIG. 4 is a graph showing luminescence spectra of molecules 1,4, and 7.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
A blue light organic luminescent molecule with an ortho-steric hindrance induced torsion structure has a chemical general formula as shown in the specification:
Figure BDA0003894775910000041
wherein the substituent R 1 And R is R 2 Optionally selected from substituted or unsubstituted carbazole, diphenylamine and acridineAromatic amines such as phenothiazine, phenoxazine and indole, and derivative groups thereof.
The synthesis method of the blue light organic luminescent molecule with the ortho-steric hindrance induced torsion structure comprises the following steps:
the first step: bipyridine intermediates are prepared. Bromopyridine which is a raw material to be reacted and corresponding boric acid ester and Pd (PPh) 3 ) 4 Dissolved in the mixed solution of tetrahydrofuran and aqueous solution of potassium carbonate, heated to 110 ℃ in nitrogen atmosphere, and stirred for 12h. After cooling to room temperature, water was added to the reaction mixture and extracted with dichloromethane to obtain an organic layer. Finally, concentrating the organic layer to obtain a crude product, and separating by using a silica gel column chromatography or a thin layer chromatography to obtain the target bipyridine intermediate.
And a second step of: and preparing the target blue light organic luminescent molecular material. Dissolving the bipyridine intermediate obtained in the last step, aromatic amine or a derivative thereof and cesium carbonate in N, N-dimethylformamide, heating to 150 ℃ in nitrogen atmosphere, and reacting and stirring for 16h. After cooling to room temperature, the reaction mixture was dissolved in ethyl acetate. Water was added to the reaction mixture and extracted with ethyl acetate to obtain an organic layer. And finally concentrating the organic layer to obtain a crude product, and separating by using a silica gel column chromatography or a thin layer chromatography to obtain the target blue light organic luminescent molecular material.
Example 1
In this embodiment, the blue-light organic luminescent molecule with ortho-steric hindrance induced twisting structure
Figure BDA0003894775910000051
For example, referring to fig. 1, the synthetic route includes the following steps:
the first step: at N 2 Under atmosphere, 2-Fluoropyridine-3-boronic acid pinacol ester was reacted with 2-fluoro-3-bromopyridine (1 g,5.68 mmol), potassium carbonate solution (10 mL,20 mmol), pd (PPh) 3 ) 4 (0.33 g,0.29 mmol) was dissolved together in 25mL tetrahydrofuran, heated to 110℃and the reaction stirred for 12h. After the reaction was completed, the mixture was poured into 50mL of water, extracted three times with 30mL of methylene chloride, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The target was isolated by thin layer chromatography using ethyl acetate: petroleum ether (v: v=1:9) as developing solventBipyridine intermediate opy was 78% yield. The nuclear magnetic characterization data are: 1 H NMR(400MHz,CDCl 3 ,δ)8.30(dd,2H),7.95–7.88(m,2H),7.33(ddt,2H)。
and a second step of: at N 2 Opy (0.15 g,0.78 mmol), 3, 6-di-tert-butylcarbazole (0.55 g,1.97 mmol), cesium carbonate (3.18 g,9.76 mmol) were dissolved in 40mL of N, N-dimethylformamide under an atmosphere. The reaction was stirred for 16h with heating to 150℃under nitrogen. After cooling to room temperature, the reaction mixture was dissolved in ethyl acetate. Water was added to the reaction mixture and extracted with ethyl acetate to obtain an organic layer. Finally, the organic layer is concentrated to obtain a crude product, and the crude product is separated by thin layer chromatography to obtain the target blue-light organic luminescent molecule 1 with the yield of 78 percent. The nuclear magnetic characterization data are: 1 H NMR(400MHz,CDCl 3 ,δ)8.73(d,2H),8.45(s,2H),7.75(d,2H),7.55(d,4H),7.02(dd,4H),6.16(d,4H),1.43(s,36H)。
in the synthesis process, the carbazole moiety in the blue organic luminescent molecule 1 is replaced by aromatic amines such as diphenylamine, acridine and the like and derivative groups thereof, so that the blue organic luminescent molecules 2 and 3 can be obtained.
Figure BDA0003894775910000061
Example two
In this embodiment, the blue-light organic luminescent molecule with ortho-steric hindrance induced twisting structure
Figure BDA0003894775910000062
For example, referring to fig. 2, the synthetic route includes the following steps:
the first step: at N 2 Under atmosphere, 3-Fluoropyridine-4-boronic acid pinacol ester was reacted with 3-fluoro-4-bromopyridine (1 g,5.68 mmol), potassium carbonate solution (10 mL,20 mmol), pd (PPh) 3 ) 4 (0.33 g,0.29 mmol) was dissolved together in 25mL tetrahydrofuran, heated to 110℃and the reaction stirred for 12h. After the reaction was completed, the mixture was poured into 50mL of water, extracted three times with 30mL of methylene chloride, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. Ethyl acetate/petroleum ether (v: v=1:9) as developing agent through the thin layerThe target bipyridine intermediate mpy is obtained by separation through an analytical method, and the yield is 40%. The nuclear magnetic characterization data are: 1 H NMR(400MHz,CDCl 3 ,δ)8.64(s,2H),8.56(d,2H),7.44–7.34(m,2H)。
and a second step of: at N 2 Mpy (0.15 g,0.78 mmol), 3, 6-di-tert-butylcarbazole (0.55 g,1.97 mmol), cesium carbonate (3.18 g,9.76 mmol) were dissolved in 40mL of N, N-dimethylformamide under an atmosphere. The reaction was stirred for 16h with heating to 150℃under nitrogen. After cooling to room temperature, the reaction mixture was dissolved in ethyl acetate. Water was added to the reaction mixture and extracted with ethyl acetate to obtain an organic layer. Finally, the organic layer is concentrated to obtain a crude product, and the crude product is separated by thin layer chromatography to obtain the target blue-light organic luminescent molecule 4 with the yield of 89 percent. The nuclear magnetic characterization data are: 1 H NMR(400MHz,CDCl 3 ,δ)8.73(d,2H),8.45(s,2H),7.75(d,2H),7.55(d,4H),7.02(dd,4H),6.16(d,4H),1.43(s,36H)。
in the synthesis process, the carbazole moiety in the blue organic luminescent molecule 4 is replaced by aromatic amines such as diphenylamine, acridine and the like and derivative groups thereof, so that the blue organic luminescent molecules 5 and 6 can be obtained.
Figure BDA0003894775910000071
Example III
In this embodiment, the blue-light organic luminescent molecule with ortho-steric hindrance induced twisting structure
Figure BDA0003894775910000072
For example, referring to fig. 3, the synthetic route includes the following steps:
the first step: at N 2 Under atmosphere, 4-Fluoropyridine-3-boronic acid pinacol ester was reacted with 4-fluoro-3-bromopyridine (1 g,5.68 mmol), potassium carbonate solution (10 mL,20 mmol), pd (PPh) 3 ) 4 (0.33 g,0.29 mmol) was dissolved together in 25mL tetrahydrofuran, heated to 110℃and the reaction stirred for 12h. After the reaction was completed, the mixture was poured into 50mL of water, extracted three times with 30mL of methylene chloride, and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. Ethyl acetate: petroleum ether (v: v=2:3) was used as the developing solventThe target bipyridine intermediate ppy is obtained through thin layer chromatography separation, and the yield is 23%. The nuclear magnetic characterization data are: 1 H NMR(400MHz,CDCl 3 ,δ)8.67(q,J＝6.2,5.4Hz,4H),7.26–7.13(m,2H)。
and a second step of: at N 2 Ppy (0.15 g,0.78 mmol), 3, 6-di-tert-butylcarbazole (0.55 g,1.97 mmol), cesium carbonate (3.18 g,9.76 mmol) were dissolved in 40mL of N, N-dimethylformamide under an atmosphere. The reaction was stirred for 16h with heating to 150℃under nitrogen. After cooling to room temperature, the reaction mixture was dissolved in ethyl acetate. Water was added to the reaction mixture and extracted with ethyl acetate to obtain an organic layer. Finally, the organic layer is concentrated to obtain a crude product, and the crude product is separated by thin layer chromatography to obtain the target blue-light organic luminescent molecule 7 with the yield of 83 percent. The nuclear magnetic characterization data are: 1 H NMR(400MHz,CDCl 3 ,δ)9.25(s,2H),8.66(s,2H),7.38(s,6H),7.19(s,2H),6.95(s,6H),1.41(s,36H)。
in the synthesis process, the carbazole moiety in the blue organic luminescent molecule 7 is replaced by aromatic amine such as diphenylamine, acridine and the like and derivative groups thereof, so that the blue organic luminescent molecules 8 and 9 can be obtained.
Figure BDA0003894775910000081
After obtaining the related blue organic luminescent molecules, the luminescence spectrum was tested by using a fluorescence spectrometer, and the result is shown in fig. 4. The maximum emission wavelength of the luminescent molecules is less than 480nm, and the luminescent molecules show very excellent blue light color purity; the absolute quantum efficiency of the materials was tested with an integrating sphere, up to 94%,98% and 89%, respectively, indicating that these blue light emitting materials have very outstanding light emitting capabilities. At present, the reported absolute luminous quantum efficiency of the conventional blue light material is generally lower than 80%, and the absolute luminous quantum efficiency of the blue light material disclosed by the invention is more than 90%, belongs to deep blue light with high color purity, and has obvious progress. The reason is that the invention innovatively introduces the bulky substituent to the 2,2' position of the bipyridine to form an ortho-position substituent structure, so that the bulky substituent and the bipyridine core are promoted to be strongly distorted to form an ortho-position steric hindrance induced distortion structure, the length of a molecular conjugated system can be effectively limited, the excited state energy level of the material is improved, and the excellent color purity of the material is ensured; from luminescence property tests, the triplet energy level of the materials exceeds 2.8eV, is obviously higher than the triplet energy level of most blue light materials which is about 2.6eV, and is further higher than the triplet energy level of green light and red light materials. Meanwhile, the twisted structure can inhibit the consumption of energy by intramolecular vibration and reduce the non-radiative transition rate constant, thereby being very beneficial to improving the luminous efficiency of molecules and ensuring the outstanding luminous performance of the molecules. Therefore, the invention brings remarkable progress in the aspect of the molecular structure design of the material, and can be used as a luminescent material, a main material and a charge transport material for preparing high-performance electronic devices.
The above description of the embodiments of the invention has been presented in connection with the drawings but these descriptions should not be construed as limiting the scope of the invention, which is defined by the appended claims, and any changes based on the claims are intended to be covered by the invention.

Claims (2)

1. A blue light organic luminescent molecule with an ortho-steric hindrance induced torsion structure is characterized by having a chemical general formula as follows:
Figure FDA0003894775900000011
in the above formula, the substituent R 1 And R is R 2 Optionally substituted or unsubstituted carbazole, diphenylamine, acridine, phenothiazine, phenoxazine, indole and other aromatic amine and derivative groups thereof.
2. The blue-light organic luminescent molecule according to claim 1, wherein the blue-light organic luminescent molecule has an ortho-steric hindrance induced twist structure, comprising the following molecules:
Figure FDA0003894775900000012
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116804015A (en) * 2023-06-21 2023-09-26 季华恒烨(佛山)电子材料有限公司 Blue light material, preparation method thereof and organic electroluminescent device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116804015A (en) * 2023-06-21 2023-09-26 季华恒烨(佛山)电子材料有限公司 Blue light material, preparation method thereof and organic electroluminescent device
CN116804015B (en) * 2023-06-21 2023-12-29 季华恒烨(佛山)电子材料有限公司 Blue light material, preparation method thereof and organic electroluminescent device

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