Blue fluorescence chiral organic dye molecule as well as preparation method and application thereof

A technology of chiral resolution and organic solvents, applied in the field of fluorescent materials, can solve the problems of low efficiency and few types of blue light materials

Active Publication Date: 2017-09-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since blue is one of the three primary colors of red, green and blue, blue light is necessary to obtain white light-emitting devices. However, compared with red and green light-emitting materials, ...

Method used

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  • Blue fluorescence chiral organic dye molecule as well as preparation method and application thereof
  • Blue fluorescence chiral organic dye molecule as well as preparation method and application thereof
  • Blue fluorescence chiral organic dye molecule as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment 1, compound shown in preparation formula (M)-1A and formula (P)-1A

[0088] according to figure 1 The compound shown in the synthetic route preparation formula (M)-1A and formula (P)-1A, concrete steps are as follows:

[0089] 1) Add 50g of 2,2'-diphenyl-7,7'-dimethoxy-3,4,3',4'-tetrahydro-1,1'-dimethoxy to a 1000ml round bottom flask Naphthalene (structural formula as shown in formula 2), 150g methyl butynedicarboxylate (structural formula as shown in formula 3) and 500ml xylene were heated to reflux for 10 hours, cooled, spin-dried reaction solution, separated and purified through chromatographic column to obtain 61.9 The compound shown in g addition product formula 4 has a yield of 95%; the structural verification data are as follows: 1 H NMR (500MHz, CDCl 3 ): δ7.10(tt,J=7.1,1.3Hz,2H),6.99(td,J=7.2,1.5Hz,2H),7.09(d,J=6.0Hz,4H),6.86 (s,2H) ,6.77(s,2H),6.14(d,J=7.6Hz,2H),3.89(s,6H),2.97(s,6H),2.69–2.61(m, 2H),2.75(td,J=15.4 ,3.9Hz,2H),2.65(t,J=15.0,4.2...

Embodiment 2

[0103] Embodiment 2, compound shown in preparation formula (M)-1B and formula (P)-1B

[0104] The preparation method is the same as in Example 1, only the phenylboronic acid in step 4) is replaced with 595 mg of 4-methylphenylboronic acid (the structural formula is shown in formula 9B), and the synthetic route is as follows Figure 7 As shown, 244 mg of the compound represented by (M)-1B and formula (P)-1B was obtained, and the yield was 74%. The structure verification data is as follows: 1 H NMR (500MHz, CDCl 3 )δ7.59(d,J=7.7Hz,4H), 7.27–7.24(m,4H),6.99(t,J=7.4Hz,2H),6.93(s,4H),6.85(d,J=6.3 Hz, 4H), 6.23(d, J=7.6Hz, 2H), 3.91(s, 6H), 2.71(s, 6H), 2.70–2.65(m, 2H), 2.48(dd, J=15.3, 4.0Hz , 2H),2.43(s,6H),2.22(dd,J=13.7,3.2Hz,2H),1.42(td,J=14.8,4.0Hz,2H).HRMS (APCI)MS:791.3367([M+ H] + ). For related spectra, see Figure 8 and Figure 9 . Verified that the structure is correct.

Embodiment 3

[0105] Embodiment 3, compound shown in preparation formula (M)-1C and formula (P)-1C

[0106] The preparation method is the same as in Example 1, only the phenylboronic acid in step 4) is replaced by 610 mg of 4-methoxyphenylboronic acid (structural formula shown in formula 9C), and the synthetic route is as follows Figure 10 As shown, 251 mg of the compound represented by (M)-1C and formula (P)-1C was obtained with a yield of 75%. The structure verification data is as follows: 1 H NMR (500MHz, CDCl 3 )δ7.64(s,2H),7.62(s,2H),7.02–6.98(m,6H),6.93(d,J=4.9Hz,4H),6.89–6.81(m,4H),6.23(d ,J=7.6 Hz,2H),3.91(s,6H),3.88(s,6H),2.71(s,6H),2.68(d,J=3.4Hz,2H),2.46(td,J=15.4, 4.0Hz, 2H), 2.22(dt, J=13.9, 3.1Hz, 2H), 1.42(td, J=14.7, 4.0Hz, 2H).HRMS(APCI) MS: 823.3265([M+H] + ). For related spectra, see Figure 11 and Figure 12 . Verified that the structure is correct.

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Abstract

The invention discloses a blue fluorescence chiral organic dye molecule as well as a preparation method and the application of the blue fluorescence chiral organic dye molecule. The chiral organic dye molecule comprises a left-handed (M) screw type optical activity enantiomer and a right-handed (P) screw type optical activity enantiomer, the structural formulas of the left-handed (M) screw type optical activity enantiomer and the right-handed (P) screw type optical activity enantiomer are shown in the formulas (M)-1 and (P)-1, Ar in the formula (M)-1 or (P)-1 is chosen from a phenyl group or a replaced phenyl group, and the replaced phenyl group is chosen from at least one of 4-methylphenyl, 4-methoxy phenyl, 4-fluoro-phenyl, and 4-cyano-phenyl. The chiral organic dye molecule forms a twisting structure in a way that an aromatic diester attracting an electron and a dinaphthalene derivative are connected by a 6-membered ring through methylene, moreover, the chiral organic dye molecule also has a certain spiroconjugated compound; after the extra aromatic substituent group is introduced, the fluorescence emission is promoted, the structure is more twisted, then the excitation wavelength and the emission wavelength are relatively short, taking Ar serving as the phenyl group for an example, the excitation wavelength in the tetrahydrofuran is 344 nm, the emission wavelength is 439 nm, and the Ar shows approximately pure blue color in a solution.

Description

technical field [0001] The invention belongs to the field of fluorescent materials, in particular to a chiral organic dye molecule with blue fluorescence and its preparation method and application. Background technique [0002] Blue organic light-emitting materials have high application value in the field of optoelectronic materials such as organic electroluminescent devices (OELD), while blue chiral organic dyes have important application value in the fields of circularly polarized OLED (CP-OLED) and 3D display. . Since blue is one of the three primary colors of red, green and blue, blue light is necessary to obtain white light-emitting devices. However, compared with red and green light-emitting materials, there are fewer types of blue light-emitting materials and low efficiency. Therefore, the search for efficient blue organic photoelectric materials has been It is a hotspot of research by many scientists. [0003] Currently in this field, representative blue fluorescen...

Claims

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Application Information

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IPC IPC(8): C07C67/347C07C69/76C07C253/30C07C255/57C09B57/00C09K11/06
Inventor 陈传峰何栋强李猛吕海燕
Owner INST OF CHEM CHINESE ACAD OF SCI
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