Bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, preparation method thereof and application thereof as electroluminescent device

A technology of phenanthroimidazole and compounds, which is applied in the field of organic light-emitting materials and optoelectronic devices, can solve the problems of unbalanced carrier transport and insufficient purity of luminous color, achieve carrier injection and transport balance, and improve fluorescence quantum Efficiency, the effect of achieving high fluorescence quantum efficiency

Inactive Publication Date: 2020-04-21

GUANGDONG UNIV OF TECH

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AI-Extracted Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the disadvantages of unbalanced carrier transport and insufficient luminous color purity in the prior art, and provide a...

Abstract

The invention discloses a bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound, a preparation method thereof and application of the compound serving as an electroluminescent device. Thecompound has a molecular structure shown as a formula (I) shown in the specification. The preparation method comprises the following steps: carrying out a one-pot reaction on 4-bromobenzaldehyde, p-bromoaniline and 9,10-phenanthrenequinone to prepare 4,4-bisbromo-phenanthroimidazole; adding N-phenyl-3-carbazole boric acid, and carrying out a Suzuki reaction under the action of a catalyst tetrakis(triphenylphosphine) palladium, so as to obtain the bis(N-phenyl)-3-carbazole substituted phenanthroimidazole compound. The preparation method is simple and convenient, and large-scale batch preparation can be realized; the compound shown in the formula (I) has good carrier transport capacity, high fluorescence quantum yield in an aggregation state and high blue light color purity, and can be widely applied to organic light-emitting devices, especially stable and efficient dark blue organic light-emitting devices as a light-emitting material.

Application Domain

Organic chemistrySolid-state devices +3

Technology Topic

BromobenzeneBoronic acid +14

Image

Examples

Experimental program(2)

Example Embodiment

[0053] Example 1

[0054] The molecular structure of the phenanthroimidazole compound substituted by bis-N-phenyl-3-carbazole is shown in formula (I).

[0055] The preparation method of phenanthroimidazole compound substituted by bis-N-phenyl-3-carbazole includes the following steps:

[0056] S1. 4-bromobenzaldehyde (1.86g, 10mmol), p-bromoaniline (1.70g, 10mmol), 9,10-phenanthrenequinone (2.08g, 10mmol), ammonium acetate (4.62g, 60mmol) were added to 100mL of A two-neck flask was added with 60 mL of glacial acetic acid to obtain a dark brown suspension. After the mixture was stirred at 120°C for 2 hours, the color of the solution changed from dark brown to black, and the reaction mixture was stirred overnight (12 hours) at normal temperature. The crude product was separated by washing with methanol and filtered, and then dried under vacuum. Use silica gel powder as stationary phase, petroleum ether and dichloromethane as eluent (petroleum ether: CH 2 Cl 2 , 1:2) Purify the product to obtain bisbromophenanthrimidazole white powder with a yield of 82%.

[0057] The reaction equation is as follows:

[0058]

[0059] S2. Dibromophenanthrimidazole (1.58g, 3mmol) and N-phenyl-3-carbazole boronic acid (1.72g, 6mmol), tetrakistriphenylphosphine palladium (0.16g, 0.14mmol), add 100ml of two In the neck flask, the flask was evacuated under vacuum and replaced with dry nitrogen three times, and then 60mL THF and 8mL saturated K were added. 2 CO 3 Aqueous solution. The mixture was heated under reflux and stirred for 48 hours at 90°C. It was extracted with saturated brine and dichloromethane. Distill under reduced pressure to obtain a black solid, use silica gel powder as a stationary phase, petroleum ether/dichloromethane as eluent, and obtain 1.0 g of bis-N-phenyl-3-carbazole-modified phenanthrene by column chromatography Imidazole yellow powder (40% yield).

[0060] The reaction equation is as follows:

[0061]

[0062] The NMR spectrum of the compound is as figure 1 Shown. figure 1 The molecular hydrogen spectrum tested by Bruker's 400MHz superconducting nuclear magnetic resonance instrument. The solvent is deuterated DMSO. From figure 1 It can be seen that its characteristic wave number (ppm) is 1H NMR (400MHz, DMSO-d6) δ8.96 (d, J = 8.5Hz, 1H), 8.94-8.86 (m, 2H), 8.77 (d, J = 7.9Hz, 1H), 8.66 (d, J = 1.5 Hz, 1H), 8.42 (d, J = 7.7 Hz, 1H), 8.34 (d, J = 7.7 Hz, 1H), 8.20 (d, J = 8.4 Hz, 2H) ,7.99(d,J=8.6Hz,1H),7.93-7.84(m,4H),7.84-7.78(m,3H),7.76-7.66(m,8H),7.64(d,J=7.1Hz,2H ), 7.61–7.51(m,5H), 7.51–7.32(m,10H), 7.29(t,J=7.0Hz,1H), the peak energy corresponds to the hydrogen atoms of phenanthrimidazole and carbazole one to one, and the number is reasonable . It shows that the bis-N-phenyl-3-carbazole-substituted phenanthrimidazole compound has a single structure.

[0063] figure 2 It is a mass spectrum of bis-N-phenyl-3-carbazole modified phenanthrimidazole, and its fragment peak is consistent with the molecular weight of the bis-N-phenyl-3-carbazole modified phenanthrimidazole compound, and there is no miscellaneous peak, indicating Its molecular weight is determined and its purity is high.

Example Embodiment

[0064] Example 2 Performance Test

[0065] The bis-N-phenyl-3-carbazole-modified phenanthroimidazole prepared in Example 1 was used as the test object to test its photophysical properties and other luminescence properties. The test results are as follows Figure 3 to Figure 8 Shown.

[0066] image 3 It is the normalized absorption spectrum of molecule M1 under tetrahydrofuran measured by Shimadzu UV-2700 ultraviolet-visible spectrophotometer. The results show that the molecule exhibits the maximum absorption intensity at 250nm, which is attributed to the π-π* transition of the benzene ring.

[0067] Figure 4 It is the fluorescence emission spectrum of the obtained molecule M1 tested by Edinburgh FLS980 at an excitation wavelength of 350nm. The results show that the molecule emits fluorescence efficiently in tetrahydrofuran solution, and its fluorescence peak is between 390-440nm, showing a deep blue fluorescence emission.

[0068] Figure 5 It is the normalized absorption spectrum of molecular M1 film measured by Shimadzu UV-2700 ultraviolet-visible spectrophotometer.

[0069] Image 6 It is the fluorescence emission spectrum of the obtained molecular M1 film tested by the Edinburgh FL980 transient steady-state fluorescence phosphorescence spectrometer at an excitation wavelength of 350nm.

[0070] Such as Figure 5 with Image 6 As shown, where 2-Cz-PPI is a phenanthroimidazole substituted with bis-N-phenyl-3-carbazole, the absorption intensity and emission intensity are read by the normalization method. Its maximum absorption and emission wavelength is 300nm/430nm, and its absolute fluorescence quantum yield in the film can reach nearly 30%, indicating that it can also emit fluorescence efficiently in the aggregate state, and its emission peak is still at 430nm in the aggregate state Around this time, it has shown great potential in the application of high-efficiency dark blue organic electroluminescent devices.

[0071] Figure 7 It was tested by Photo Research PR745 spectral scanner to obtain the electroluminescence spectrum of the bis-N-phenyl-3-carbazole substituted phenanthroimidazole compound prepared in Example 1 as the light-emitting layer device. Such as Figure 7 As shown, the maximum emission wavelength is 434nm and the half-peak width is only 68nm, which indicates that the color purity is relatively high. The CIE color coordinate is (0.16, 0.10), which has reached the international standard dark blue emission.

[0072] Figure 8 The electroluminescence current density-voltage-luminance spectrum of the phenanthroimidazole compound substituted with the bis-N-phenyl-3-carbazole prepared in Example 1 as a light-emitting layer device was tested by the Photo Research PR745 spectral scanner. The device has a starting voltage of 5V and a maximum brightness of 1400cd/m 2 , The current efficiency is 1.20cd/A. It shows that the organic electroluminescent device has good photoelectric properties and carrier transport ability.

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