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9,9'- connected host material based on 4,4'-difluorene structure and application thereof

A technology of host materials and doping materials, which is applied in the field of host materials connected at 9,9'-position, can solve the problems of decreased energy transmission efficiency, low triplet state, and high device startup voltage, and achieves high-efficiency electroluminescence performance, high The effect of stability

Active Publication Date: 2015-02-04
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

In 2009, Jiang Zuoquan et al reported (Jiang, Z.; Xu, X.; Zhang, Z.; Yang, C.; Liu, Z.; Tao, Y.; Qin, J.; Ma, D.J. Mater.Chem. 2009,19,7661.) The host material based on part of the ortho-linked doublet spirofluorene, but due to its relatively low triplet state (E T =2.55eV), so it can only be used as the main body of green light, and then Fan Cong et al reported (Fan, C.; Chen, Y.; Gan, P.; Yang, C.; Zhong, C.; Qin, J .;Ma,D.Org.Lett.2010,12,5648.) Sky-blue host material based on 4,4'-dibromo-9,9'-spirofluorene, but due to HOMO (HOMO=-6.08eV) value If it is too low, the front track of the light-emitting layer does not match the adjacent layer, resulting in a high start-up voltage (4.5V) and a relatively low external quantum efficiency. The best external quantum efficiency is only 11.6%.
[0008] In order to prevent the energy feedback from the FIrpic excitons (triplet state energy level is 2.65eV) to the triplet state energy level of the host material, the triplet state energy level of the host material based on the FIrpic blue light device is generally higher than 2.75eV, and most of the host material While maintaining a high triplet state, the material also makes the HOMO value very low, which will lead to a decrease in energy transmission efficiency due to the low HOMO energy level, thereby reducing the efficiency of the device

Method used

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  • 9,9'- connected host material based on 4,4'-difluorene structure and application thereof
  • 9,9'- connected host material based on 4,4'-difluorene structure and application thereof
  • 9,9'- connected host material based on 4,4'-difluorene structure and application thereof

Examples

Experimental program
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Effect test

Embodiment 110

[0024] Example 11 Synthesis of 110-phenyl-10 hydrogen-spiro[acridine-9,9'-fluorene]-4-ylboronic acid pinacol borate (abbreviated as intermediate 1)

[0025] Synthesis of intermediate (A)

[0026]

[0027] Under the protection of Ar gas, add o-bromotriphenylamine (1.6g; 5mmol) and 60ml of anhydrous and oxygen-free tetrahydrofuran into a 200ml Chirank bottle, cool to -78°C at low temperature, and add 3ml of n-butyllithium (2M; 6mmol) dropwise. ), after reacting at low temperature for 1 hour, dropwise added 4-bromo-9-fluorenone (1.2 g; 5 mmol) dissolved in anhydrous and oxygen-free tetrahydrofuran under the protection of Ar gas, and continued the reaction at low temperature for 1 hour, then took it out and stirred overnight at room temperature. The reaction was then quenched with saturated ammonium chloride solution and dried over anhydrous sodium sulfate. After the solvent was evaporated by a rotary evaporator, the remaining solid was dissolved in acetic acid, refluxed at 12...

Embodiment 24

[0030] Example 2 Synthesis of 4'-bromo-5-phenylspiro[phosphine-10,9'fluorene] 5-oxide (abbreviated as intermediate product B) Synthesis of o-bromotriphenylphosphine oxygen

[0031]

[0032]Under the protection of Ar gas, o-dibromobenzene (1.2 g; 5 mmol) and 40 ml of dehydrated and deoxygenated tetrahydrofuran were added to a 200 ml Chirac flask, and cooled to 0° C. in an ice bath. Add 4ml of Grignard reagent (1.8M; 7.2mmol) dropwise and react at low temperature for 1h, then add diphenylphosphorus chloride (0.7ml; 6mmol) dropwise, keep it at 0°C for 1h, then take it out to react overnight at room temperature. Saturated ammonium chloride solution was quenched, and after the solvent was evaporated by a rotary evaporator, the product was separated and purified by column chromatography to obtain 0.8 g (58%) of the product o-bromotriphenylphosphine oxide.

[0033]

[0034] Using o-bromotriphenylphosphine oxide instead of o-bromotriphenylamine, using the same synthesis conditio...

Embodiment 3

[0035] Synthesis of Example 34-(4-pinacol borate ester-9 hydrogen-fluoren-9-yl)-nitrogen, nitrogen-diphenylaniline (intermediate 2 for short)

[0036]

[0037] Synthesis of Intermediate C

[0038]

[0039] Under the protection of nitrogen, put 4-bromo-triphenylamine (1.6g; 5mmol) into a 200ml Chirank bottle, then add 40ml of ether, put it into a low-temperature reactor and cool it to -78°C, and add n-butyllithium dropwise 3ml (2M; 6mmol), after low temperature reaction for 1h, slowly drop 4-bromo-9-fluorenone (1.3g; 5mmol) which has been dissolved in anhydrous oxygen-free ether into the Schrank bottle, and react for 1h take out. Slowly return to room temperature, pass dry ammonia gas (200ml) into the reaction bottle, remove the gas device, add 200mg of lithium wire, react for 0.5h, open the bottle mouth to volatilize the ammonia gas. The remaining solvent was quenched with saturated ammonium chloride, extracted with ethyl acetate, evaporated to dryness with a rotary ev...

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Abstract

A 9,9'- connected host material based on a 4,4'-difluorene structure and an application thereof. The invention discloses a host material which has high triplet state and HOMO energy level and has excellent performance. According to the host material, 4,4'- connected difluorene structure is used as a molecular skeleton, and a substituent group is connected at 9,9'- site. Diphenylamine element Dn with hole transport performance can be connected, and An element with electron-transport performance also can be connected, wherein the An element contains an oxygen-phosphorus element and a sulfur-oxygen element; and in addition to the oxygen-phosphorus element and the sulfur-oxygen element, a special spiral structure also can be formed. A synthetic method of the host material is simple and practicable, and the host material is suitable for wide application. An organic electroluminescence blue phosphorescent luminescent device made of the host material has high efficiency, high brightness, low extinction efficiency and electroluminescence performance of low starting voltage, and can widely be applied in the field of organic electroluminescence.

Description

technical field [0001] The present invention relates to a class of 9,9'-position-connected host materials based on 4,4'-bifluorene structure and applications thereof, [0002] It belongs to the field of luminescent materials. Background technique [0003] Since 1987, C.W.Tang et al. of Kodak reported for the first time that Alq was prepared by vacuum evaporation method. 3 Since the double-layer device structure of light-emitting materials, organic electroluminescence has received great attention. Organic electroluminescence can be divided into fluorescence and phosphorescence electroluminescence, and electroluminescence of phosphorescent materials can utilize the energy of all excitons, which has greater advantages. [0004] Most of the current phosphorescent electroluminescent devices adopt the host-guest structure, that is, the phosphorescent emitting substance is doped in the host substance at a certain concentration, so as to avoid concentration quenching and triplet-t...

Claims

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Application Information

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IPC IPC(8): C07D221/20C07F9/6568C07D209/86C07F9/572C07F9/53C07D249/08C07C317/32C07D213/38C07C211/54H01L51/54
CPCC07C211/54C07C317/32C07D209/86C07D213/38C07D221/20C07D249/08C07F9/5325C07F9/572C07F9/65685C07C2603/18H10K85/624H10K85/631H10K85/626H10K85/654H10K85/657H10K85/6572
Inventor 杨楚罗刘腾霄樊聪
Owner WUHAN UNIV
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