Triphenylphosphine oxide unit bridged bipolar host material and application thereof

A technology of triphenylphosphine oxide and host materials, which is applied in the fields of compounds of group 5/15 elements of the periodic table, electrical components, and electric solid-state devices. Limited solubility and other issues, to achieve strong electron transport capabilities, improve hole transport capabilities, and enhance rigidity

Inactive Publication Date: 2016-03-23
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron affinity of fluorene is small, and the solubility of polyfluorene is limited. The 9-position carbon atom of fluorene is relatively easy to oxidize to become a carbonyl group, and the carbonyl group is easy to form a "trap" for the excitons generated by electron-hole recombination. A certain "quenching" effect will eventually reduce the luminous efficiency of the device

Method used

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  • Triphenylphosphine oxide unit bridged bipolar host material and application thereof
  • Triphenylphosphine oxide unit bridged bipolar host material and application thereof
  • Triphenylphosphine oxide unit bridged bipolar host material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of SFOPO-Cz

[0033] Synthesis of 2-bromospiro[fluorene-9,9'-oxanthene]

[0034] Methanesulfonic acid (2.14 mL, 24.4 mmol), 2-bromo-9-fluorenone (6 g, 24.63 mmol) and phenol (23.15 g, 246.3 mmol) were added into a two-necked flask. After pumping 3 times in N 2 In the atmosphere, react at a temperature of 150°C for 8h. The reaction substrate was quenched with water, extracted three times with dichloromethane and then washed with MgSO 4 dry. TLC analysis yielded 6.1 g (60%) of pure product. 1 H-NMR (400MHz), CDCl 3 ,δ:δ7.78(s,1H),δ7.66(s,1H),δ7.50(s,1H),δ7.38(m,1H),δ7.3-7.15(m,7H), δ6.79(m,2H), δ6.40(s,2H).

[0035] Synthesis of Bis(4-bromobenzene)(phenyl)phosphine oxide

[0036] First at N 2 Under atmosphere, 1,4-dibromobenzene (4.72 g, 20 mmol) was dissolved in 140 ml of dehydrated tetrahydrofuran solvent in a two-necked flask. At a temperature of -78°C, 1.6 mol / L n-butyllithium (11.865 mL, 19 mmol) was added dropwise. After reacti...

Embodiment 2

[0051] Example 2: Electrophosphorescent device with SFOPO-Cz as host material

[0052] We used SFOPO-Cz as the host material, and the guest material Ir(ppy) 3 ,Ir(pq) 2 (acac) doping prepared electroluminescent red and green light devices, the device structure is: ITO / MoO 3 / CBP / EML / TPBi / LiF / Al, the specific steps for preparing electroluminescent devices:

[0053] (1) The ITO electrode glass plate is ultrasonically treated with a cleaning agent, then rinsed in deionized water, then ultrasonically treated with acetone-ethanol (1:3) mixed solvent to remove oil, and baked in a clean environment until the water is completely removed. Irradiate with a UV light cleaner for 10 minutes;

[0054] (2) evaporate the CBP layer on the above-mentioned ITO glass plate as the hole injection layer, the evaporation rate is 0.1nm / s, and the evaporation thickness is 45nm;

[0055] (3) Place the above-mentioned ITO glass covered with the CBP layer in a vacuum chamber and vacuumize.

[0056] (...

Embodiment 3

[0060] Example 3: Application of organic electroluminescent materials in the preparation of electroluminescent devices

[0061] The compounds of the present invention can be used as electroluminescent materials to prepare electroluminescent devices, especially for active layers of electroluminescent devices. The so-called active layer is an organic thin film layer that can emit light or have charge injection and transport properties under a certain driving voltage. The active layer can be a hole transport layer, an organic light-emitting layer, or an electron transport layer. Electroluminescent devices have one or more active layers. The compound of the present invention can be used as an electroluminescent material, preferably mixed with other dyes as a light-emitting layer.

[0062] The basic structure of organic electroluminescence is: substrate / anode / hole injection layer / hole transport layer / hole blocking layer / organic light-emitting layer / electron transport layer / electr...

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Abstract

The present invention discloses a triphenylphosphine oxide unit bridged bipolar host material and an application thereof. Firstly, a spiro-[fluorene-9,9'-xanthene] structure is prepared by a cyclization reaction between 2-bromo-fluorenone and phenol, by two steps of Suzuki reaction, carbazole and spiro-[fluorene-9,9'-xanthene] is introduced on a triphenylphosphine oxide structure to obtain a target product SFOPO-Cz. According to the material disclosed by the present invention, the material has the spiro-[fluorene-9,9'-xanthene] group; properties of fluorene of wide energy gap and high luminous efficiency can be fully used; meanwhile, the carbazole group having good hole transporting property is adopted as a hole transport unit; the triphenylphosphine oxide group having strong electron transporting ability is adopted as an electron transport unit; so that implementation of carrier transporting balance is facilitated. A device which is designed and prepared by the material has the advantages of high efficiency, high stability and relatively small efficiency roll-off, and has excellent potential for being a new generation of an electroluminescent phosphor host material.

Description

technical field [0001] The invention relates to bipolar host materials bridged by triphenylphosphine oxygen units and applications thereof. Background technique [0002] The phenomenon of organic electroluminescence has been developed for nearly 50 years. It has many advantages and is expected to be the next generation display technology. As we all know, the basis and key to the further development and large-scale commercialization of organic electroluminescent devices (OLEDs) are organic light-emitting materials, especially high-performance, low-cost three-color organic light-emitting materials. At present, the research on red and green organic light-emitting materials has become mature and basically meets the needs of commercialization. However, the research progress of blue light materials that require wide energy system, high stability and high performance is not satisfactory. Due to the low luminous efficiency and short service life of blue light materials, the effec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558H01L51/54
CPCC07F9/65586H10K85/6574
Inventor 姜鸿基张庆维
Owner NANJING UNIV OF POSTS & TELECOMM
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