High-efficiency non-doped electro-induced long-wave red light arylamine diphenyl trans-butene dinitrile derivative

A technology of arylamine diphenyl and butenedinitrile, which is applied in the preparation of amino compounds, circuits, electrical components, etc.

Pending Publication Date: 2020-10-30
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Description
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  • High-efficiency non-doped electro-induced long-wave red light arylamine diphenyl trans-butene dinitrile derivative
  • High-efficiency non-doped electro-induced long-wave red light arylamine diphenyl trans-butene dinitrile derivative
  • High-efficiency non-doped electro-induced long-wave red light arylamine diphenyl trans-butene dinitrile derivative

Examples

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Embodiment 1

[0060] Example 1 Synthesis of two (4-(N-(4-biphenyl)-9,9-diethyl-2-fluorenamine) phenyl) trans-butenedinitrile (BPFAFN, 3b):

[0061] 1. Preparation of N-(4-biphenyl)-9,9-diethyl-2-fluorenamine (2b)

[0062] Under argon protection, 301mg (1mmol) 2-bromo-9,9-diethylfluorene, 203mg (1.2mmol) 4-benzidine, 134mg (1.4mmol) sodium tert-butyl alkoxide were successively added to a 100mL round bottom flask , 1.9 mg (0.01 mmol) Pd (OAc) 2 , 14.3mg (0.03mmol) organophosphine Xphos, dissolved in 25mL of toluene. Temperature was 110°C, reacted for 20 hours; after cooling, 80 mL of brine was added, extracted with ethyl acetate (2×80 mL, twice, 80 mL each time), after the organic phase was dried and concentrated, column chromatography (silica gel, dichloromethane / petroleum ether eluent) to obtain white solid N-(4-biphenyl)-9,9-diethyl-2-fluorenamine (2b) with a yield of 79.4%.

[0063] Product Confirmation:

[0064] 1 H NMR (400MHz, CDCl 3 )–δ(ppm):0.36-0.39(t,6H),1.92-2.02(m,4H),7.08-...

Embodiment 2

[0071] Example 2 Synthesis of two (4-(N-(2-spirobifluorenyl)-3,5-xylaniline) phenyl) trans-butenedinitriles (SFPAFN, 3a):

[0072] 1. Preparation of N-(3,5-xylyl)-2-spirobifluorenamine (2a)

[0073] Take 395mg (1mmol) of 2-bromo-spirobifluorene and 145mg (1.2mmol) of 3,5-xylidine, and the amount and method of other compounds are the same as step 1 of Example 1 to obtain a white solid (2a) with a yield of 62.4 %.

[0074] Product Confirmation:

[0075] 1 H NMR (400MHz, CDCl 3 )–δ(ppm):2.284(s,6H),6.718–6.737(d,2H),6.753–7.081(m,6H),7.132–7.172(m,2H),7.261–7.322(m,4H), 7.422–7.605(m,4H);

[0076] Elemental analysis (molecular formula C 33 h 25 N): Theoretical: C, 91.00; H, 5.79; N, 3.22. Test values: C, 90.88; H, 5.71; N, 3.18.

[0077] 2. Preparation of bis(4-(N-(2-spirobifluorenyl)-3,5-xylaniline) phenyl) transbutenedinitrile (SFPAFN, 3a)

[0078] Take 958mg (2.2mmol) N-(3,5-xylyl)-2-spirobifluorenamine (2a), and the amount and method of other compounds are the same ...

Embodiment 3

[0082] Example 3 Synthesis of two (4-(N,N-bis(4-biphenyl)amino)phenyl)trans-butenedinitrile (BBPAFN, 3c):

[0083] 1. Preparation of N,N-bis(1-biphenyl)amine (2c)

[0084] Take 233mg (1mmol) of 4-bromobiphenyl and 203mg (1.2mmol) of 4-aminobiphenyl, and the amounts and methods of other compounds are the same as step 1 of Example 1. An off-white solid (2c) was obtained in 67.8% yield.

[0085] Product Confirmation:

[0086] 1 H NMR (400MHz, CDCl 3 )–δ(ppm):7.192–7.273(d,4H),7.461–7.482(m,6H),7.523–7.544(m,4H),7.585–7.596(m,4H);

[0087] Elemental analysis (molecular formula C 24 h 19 N): Theoretical: C, 89.68; H, 5.96; N, 4.36. Test values: C, 89.56; H, 5.92; N, 4.28.

[0088] 2. Preparation of bis(4-(N,N-bis(4-biphenyl)amino)phenyl)trans-butenedinitrile (BBPAFN, 3c)

[0089] Take 706 mg (2.2 mmol) of N,N-bis(1-biphenyl)amine (2c), and the amount and method of other compounds are the same as Step 2 of Example 1 to obtain a red solid (3c), with a yield of 68.6%.

[009...

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Abstract

The invention relates to a high-efficiency non-doped electro-induced long-wave red light arylamine diphenyl trans-butene dinitrile derivative, and belongs to the technical field of luminescent materials; arylamine diphenyl is bis(4-(N-(2-spirobifluorenyl)-3,5-xylylamine)phenyl), bis(4-(N-(4-biphenyl)-9,9-diethyl-2-fluoreneamine)phenyl) or bis(4-(N,N-bis(4-biphenyl)amino)phenyl). According to the arylamine diphenyl trans-butene dinitrile derivative, large-volume and large-conjugate group is introduced, so the luminous efficiency of the material and devices is enhanced, and the light-emitting wavelength moves towards the long-waveband red light; meanwhile, the organic light-emitting color can be effectively adjusted by introducing different groups; in addition, by introducing the groups, theinterlayer interface potential barrier can be reduced, the design of red non-doped organic light-emitting devices is optimized, and the light-emitting efficiency of the devices is effectively improved.

Description

technical field [0001] The present invention relates to a trans-butenedinitrile derivative, in particular to an arylamine diphenyl trans-butenedinitrile derivative with high efficiency non-doped electro-induced long-wave red light, especially to fluorene, spirobifluorene- 2. Trans-butenedinitrile derivatives of biphenyl and other units, belonging to the technical field of luminescent materials. Background technique [0002] Among the RGB three-primary-color organic light-emitting materials for full-color display and anti-counterfeiting, there are few red light-emitting materials that can meet the practical requirements. [0003] The main reasons are as follows: 1. The energy level difference between the lowest excited state and the ground state of red luminescent materials is small, and the non-radiative inactivation of excited state molecules is easy to occur. Therefore, the fluorescence quantum yield of most materials is not high. 2. Most of the red luminescent materials ...

Claims

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Application Information

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IPC IPC(8): C07C255/43C07C253/30C07C211/61C07C211/54C07C209/10C09K11/06H01L51/50H01L51/54
CPCC07C255/43C07C253/30C07C211/61C07C211/54C07C209/10C09K11/06C07B2200/09C09K2211/1007C09K2211/1011H10K85/624H10K85/633H10K85/631H10K85/615H10K50/11
Inventor 张文官
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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