A kind of bipolar host material and its preparation method and application

A host material and bipolar technology, which is applied in the field of bipolar host materials and preparation, can solve the problems of reduced lifetime, quenching, and reduced luminous efficiency of devices, so as to reduce the degree of conjugation, improve efficiency, and improve singlet energy. level effect

Active Publication Date: 2020-03-31
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Studies have shown that the transport rate of holes in most organic materials is usually much faster than that of electrons. Therefore, most of the holes injected from the anode can easily pass through the light-emitting layer to the electron transport layer and be quenched at the cathode. This is an important reason for the reduction of device luminous efficiency and lifespan

Method used

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  • A kind of bipolar host material and its preparation method and application
  • A kind of bipolar host material and its preparation method and application
  • A kind of bipolar host material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of compound CzCNPyCa-1

[0045] The specific implementation method is as follows:

[0046] Step 1, add 2-naphthol (14.71g, 100mmol), p-bromobenzaldehyde (18.5g, 100mmol), 4-(aminomethyl)pyridine (10.81g, 100mmol) into a 250mL reaction flask, pump nitrogen three times , turn on the heating stirrer and raise the temperature to 120°C. After 12 hours of reaction, cool down to 90°C, add 42mL of ethanol for ultrasonication, and filter with suction after cooling to obtain a yellow solid, which is purified by column chromatography (eluent is ethyl acetate:petroleum ether=5: 1) Obtain 30.15 g of light yellow powder (75% yield).

[0047]

[0048] Step 2, add compound a 1-(4-bromophenyl)-2-(pyridin-4-yl)-2,3-dihydro-1H-benzo[e]indole (1.1603g , 2.89mmol), NBS (1.0814g, 6.08mmol), evacuated nitrogen 3 times, added 6mL DMF as a solvent in the dark, turned on the stirrer and stirred overnight. After the reaction, it was extracted with ethyl acetate a...

Embodiment 2

[0061] Embodiment 2: the synthesis of compound CzCNPyCa-2

[0062] The specific implementation method is as follows:

[0063] The synthetic method of compound CzCNPyCa-2 is similar to the synthetic synthetic method of CzCNPyCa-1, and difference is, in embodiment 1 step 6, reactant 9-(2-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was replaced by 3-(9H-carbazol-9-yl)phenylboronic acid, the rest of the operation was the same, and finally yellow Solid powder CzCNPyCa-20.042g (29.8% yield).

[0064]

[0065] 1 H NMR (400MHz, CDCl3) δ8.62(s,11H),8.26(s,3H),8.26–8.17(m,18H),8.13(s,6H),8.20–7.85(m,36H),7.85– 7.65(m,40H),7.61(s,7H),7.59–7.42(m,35H),7.38–7.10(m,55H),4.27(t,J=41.2Hz,13H),1.09–1.04(m, 2H).

[0066] 13 C NMR(101MHz,CDCl3)δ149.72(s,25H),143.58(s,4H),141.29(s,3H),140.80(s,26H),140.12(s,3H),139.34(s,4H) ,137.88(s,5H),136.98(s,4H),136.52(s,3H),135.64(s,4H),133.89(s,3H),132.76(s,38H),132.37(s,27H), 130.04(s,14H),129.79(s,13H),129.35(s,11H),129....

Embodiment 3

[0067] Embodiment 3: the synthesis of compound CzCNPyCa-3

[0068] The specific implementation method is as follows:

[0069] The synthetic method of compound CzCNPyCa-3 is similar to the synthetic synthetic method of CzCNPyCa-1 in Example 1, and the difference is that in Example 1 step 6, the reactant 9-(2-(4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole is replaced by 4-(9H-carbazol-9-yl)phenylboronic acid, and the rest are the same , the final yellow solid powder CzCNPyCa-2 0.12 (yield 49.3%).

[0070]

[0071] 1 H NMR (400MHz, DMSO) δ8.63 (dd, J = 14.4, 3.6Hz, 15H), 8.40 (d, J = 8.5Hz, 6H), 8.29 (d, J = 7.7Hz, 19H), 8.10–7.92 (m,21H),7.92–7.75(m,30H),7.59(s,3H),7.59–7.22(m,89H),4.40(d,J=7.0Hz,12H),1.61–0.67(m,49H ).

[0072] 13C NMR(101MHz, CDCl3)δ149.87(s,21H),141.30(s,5H),140.86(d,J=13.2Hz,25H),140.04(s,4H),139.34(s,5H),136.95 (d,J=16.6Hz,10H),136.51(s,4H),135.85(s,4H),133.90(s,4H),132.78(d,J=7.5Hz,28H),132.39(s,20H) ,131.82(s,18H),130.05(s,1...

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Abstract

The invention provides a bipolar host material and its preparation method and application. The structural formula of the host material is wherein R1, R2, and R3 are the same or different, and are selected from H or carbazolyl. Its preparation method is to adopt 4'-(5-bromo-2-(pyridine-4-yl)-3H-benzo[e]indol-1-yl)-4-(9H-carbazole-9-yl) ‑[1,1'‑biphenyl]‑3‑carbonitrile reacted with phenylcarbazole derivatives under dark conditions. The compound uses benzindole as the core group, introduces electron-withdrawing pyridine groups, cyano groups, and electron-donating carbazole groups, which balances the injection of electrons and holes and the transport in the light-emitting layer. , and improve the efficiency of the corresponding device.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and in particular relates to a bipolar host material, a preparation method and an application. Background technique [0002] Organic light-emitting diodes (OLEDs), as a new type of flat-panel display and solid-state lighting device, have been widely used in recent has attracted people's attention for years. In 1997, Forrest and others from Princeton University in the United States first discovered the phenomenon of triplet electrophosphorescence, which broke through the limit of the internal quantum efficiency (IQE) of organic electroluminescent devices to 25%, and since then there has been an upsurge in the research and development of new phosphorescent materials. . However, the phosphorescence lifetime of heavy metals is relatively long, and it is easy to cause concentration quenching and triplet-triplet annihilation, so heavy metal atoms are usually doped with host materials. Due ...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C09K2211/1007C09K2211/1029H10K85/6572H10K50/00H10K50/11H10K2101/10H10K2102/00H10K2102/301
Inventor 李咏华刘加伟郭金飞苏艳荣琚飞飞黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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