Carborane derivative and preparation method and application thereof

A derivative and carborane technology, applied in the field of carborane derivatives and their preparation, can solve the problems of limiting the development of organic single-molecule white light devices, low luminous efficiency, and difficulty in realizing white light, and achieve excellent thermal stability, Efficient white light emission, effect of high thermal decomposition temperature

Active Publication Date: 2017-06-20
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the realization of white light requires precise control of the luminescent behavior of the excited state of the luminescent molecule, which is often difficult to achieve for broad-peak white light emission ((a) J.V.Caspar, T.J.Meyer, J.Phys.Chem., 1983, 87, 952; b) J. V. Caspar, E. M. Kober, B. P. Sullivan, T. J. Meyer, J. Am. Chem. Soc., 1982, 104, 630.)
On the other hand, due to the wide bandwidth and the aggregation quenching effect in the solid state, the luminous efficiency in the solid state is often not high ((a) J.Liang, B.Z.Tang, B.Liu, Chem.Soc.Rev., 2015,44 , 2798; b) J.Mei, Y.N.Hong, J.W.Y.Lam, A.J.Qin, Y.H.Tang, B.Z.Tang, Adv.Mater., 2014, 26, 5429; c) J.V.Caspar, T.J.Meyer, J.Phys.Chem., 1983, 87, 952; d) J.V. Caspar, E.M. Kober, B.P. Sullivan, T.J. Meyer, J.Am. Chem. Soc., 1982, 104, 630)
This severely limits the development of organic single-molecule white light devices

Method used

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  • Carborane derivative and preparation method and application thereof
  • Carborane derivative and preparation method and application thereof
  • Carborane derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] This embodiment designs following compound:

[0034]

[0035] The synthetic route is as follows:

[0036]

[0037] Compound 1-ph: Compound 9-4-ethynylphenanthrene (278.0mg, 1.0mmol), [B 10 h 12 ·(Et 2 S) 2 ] (450.0mg, 1.5mmol, 1.5 times equivalent), 50mL of toluene, stirred evenly in water under oxygen-free conditions, heated to 140°C, and reacted for 72 hours. After the reaction was cooled to room temperature, 20 mL of methanol was added, stirred at room temperature for 1 hour, and then the solvent was removed under reduced pressure. The residue was separated and purified by silica gel column chromatography (petroleum ether / dichloromethane=10:1, v / v), and dried in 258.0 mg of the target product was obtained as a white solid, with a yield of 65%. 1 H NMR (500MHz, CDCl 3 )δ8.79(d, J=8.2Hz, 1H), 8.73(d, J=8.3Hz, 1H), 7.88(d, J=7.7Hz, 1H), 7.81(d, J=8.2Hz, 1H) ,7.73–7.65(m,2H),7.67–7.59(m,4H),7.57–7.48(m,3H),4.05(s,1H,cage-H),3.20–1.70(m,10H). 11 B NMR (160MH...

Embodiment 2

[0043] Use the diffraction intensity data of the compound prepared in Example 1 to be collected on the CCD-Bruker Smart APEX II, use the SHELXTL-97 or SHELXTL-2014 program to analyze the structure, and use the Diamond software to draw a molecular thermodynamic ellipsoid with a probability of 30% (such as figure 1 shown). The results show that compounds 1-ph, 3-cl, 3-ph-me and 3-f have a large steric hindrance in the caged carborane in the crystal structure, which allows the molecules to effectively avoid the π... The π stacking ensures the high luminous efficiency of the compound in the solid state.

[0044] The emission spectrum of the compound prepared in Hitachi F-4600 Test Example 1 (wherein the absolute fluorescence quantum yield is measured by an integrating sphere, and the quantum yield is: 1-ph, 46%; 3-cl, 17%; 3- ph-me, 50%; 3-f, 67%). The result is as figure 2 As shown, compounds 1-ph, 3-cl, 3-ph-me and 3-f show bimodal emission (380-450, 450-700nm), and are whit...

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PUM

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Abstract

The invention belongs to the field of organic light-emitting materials, and particularly discloses a carborane derivative. The structural formula is as follows: (img file='DDA0001282150470000011.TIF' wi='435' he='543' /), R1 and R2 is H or a derivative of phenanthrene, and R1 and R2 are not H together. The carborane derivative disclosed by the invention has the following advantages: through charge transfer emission and/or localized state emission, the emission wavelength of the compound can be accurately regulated, so that a series of white light molecules are obtained; by introducing the carborane group, luminescence quenching caused by the aggregation of solid state molecules is prevented, the absolute luminescence quantum yield is high, and the carborane derivative has good properties, such as good thermal stability and easy sublimation, and has actual application value.

Description

technical field [0001] The invention belongs to the field of organic luminescent materials, and in particular relates to a carborane derivative and its preparation method and application. Background technique [0002] As people have more pursuits for lighting and display in daily life, organic white light emitting devices have attracted widespread attention (Y.Sun, N.C.Giebink, H.Kanno, B.W.Ma, M.E.Thompson, S.R.Forrest, Nature, 2006,440,908 ; b) S. Reineke, F. Lindner, G. Schwartz, N. Seidler, K. Walzer, B. Lüssem, K. Leo, Nature, 2009, 459, 234.). Since white light needs to cover all visible light regions, the usual design of white light devices is obtained by mixing multi-component luminescent materials, such as including three primary colors or complementary colors to achieve white light. Such a method inevitably encounters the following problems, such as spectral instability, poor color repeatability, and complicated device manufacturing process (L.Ying, C.Ho, H.B.Wu, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/50
CPCC09K11/06C07F5/027C09K2211/1096C09K2211/1007C09K2211/1011H10K50/11Y02B20/00
Inventor 燕红芦昌盛涂德双
Owner NANJING UNIV
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