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Application of cross-linkable conjugated polymer materials in flip-chip organic optoelectronic devices

A technology of conjugated polymers and optoelectronic devices, which is applied in the direction of electrical solid devices, electrical components, semiconductor devices, etc., can solve the problems of insufficient processing methods, solvent erosion, and unsatisfactory charge transmission, etc., and achieve good thermal stability and electrochemical stability. Stability, simple device preparation process, and the effect of overcoming interfacial miscibility

Active Publication Date: 2011-11-30
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The flip-chip organic optoelectronic device needs to be combined with the solution processing technology to fully exert its low cost advantage compared with the inorganic semiconductor optoelectronic device, but the flip-chip organic optoelectronic device The solution processing method has deficiencies, especially the design of the electron injection / transport layer
The current flip-chip organic light-emitting devices and solar cell devices use zinc oxide or titanium oxide as electron injection / transport layer materials, and realize solution processing by sol / gel method, which requires heating at 200oC to 300oC to partially convert the precursor into metal oxide. material, such high-temperature heating is incompatible with large-scale solution processing
In addition, the charge transport at the interface between the metal oxide and the organic active layer is still not ideal. There are related patents that use organic substances to form a self-assembled monolayer on the metal oxide to improve its electron injection / transport performance ([US 2009 / 0188558-A1]) , but this undoubtedly increases the complexity of the process
Solution-processable organic materials have the advantage of simple processing compared with zinc oxide and titanium oxide, but they are not currently used as a separate electron transport / injection layer in flip-chip devices because they can still be dissolved in commonly used materials after film formation. Organic solvents, causing the next layer to be eroded or even completely eluted by solvents during processing, unable to perform its due function

Method used

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  • Application of cross-linkable conjugated polymer materials in flip-chip organic optoelectronic devices
  • Application of cross-linkable conjugated polymer materials in flip-chip organic optoelectronic devices
  • Application of cross-linkable conjugated polymer materials in flip-chip organic optoelectronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Crosslinkable conjugated polymer poly{2,7-[9,9'-bis(3-ethyl-3-(6-hexyl)methyl ether-oxetane)fluorene]-co-2 , Preparation of 7-[9,9'-bis(6-N,N-diethylamino-hexyl)fluorene]} (referred to as PFN-C)

[0050] The synthetic route is as follows:

[0051]

[0052] (1) Monomer 1 [2,7-dibromo-9,9'-bis(3-ethyl-3-(6-hexyl)methyl ether-oxetane)fluorene] was obtained according to the literature [ J. Polym. Sci. A Polym. Chem., 2007, 3, 388] prepared by the disclosed method, monomer 3 [2,7-bis(trimethylene borate)-9,9'-bis(6- N,N-Diethylamino-hexyl)fluorene] was prepared according to the method disclosed in "Advanced Materials" [Adv. Mater., 2011, 23, 1665].

[0053] (2) Poly{2,7-[9,9'-bis(3-ethyl-3-(6-hexyl)methyl ether-oxetane)fluorene]-co-2,7-[ Preparation of 9,9'-bis(6-N,N-diethylamino-hexyl)fluorene]} (referred to as PFN-C)

[0054] Monomer 2,7-bis(trimethylene borate)-9,9'-bis(6-N,N-diethylamino-hexyl)fluorene (728 mg, 1 mmol), monomer 2,7 -Dibromo-9,9'-bis(3-ethyl-3...

Embodiment 2

[0057] Poly{2,7-[9,9'-bis(3-ethyl-3-(6-hexyl)methyl ether-oxetane)fluorene]-co-2,7-[9,9 Preparation of '-bis(6-N,N-diethylamino-hexyl)fluorene]} (abbreviated as PFN-S)

[0058] The synthetic route is as follows:

[0059]

[0060] (1) Preparation of monomer 1 [2,7-dibromo-9,9’-bis(6-formylphenoxyhexyl)fluorene]

[0061] Add the raw material 2,7-dibromo-9,9'-(6-bromohexyl)fluorene (32.5g, 50mmol) into the reaction flask, add 300ml N,N-dimethylformamide (DMF) to dissolve the raw material , then add p-Hydroxybenzaldehyde (15.3g, 125mmol) and potassium carbonate 2g, and heat to reflux under argon protection for 12 hours. After cooling, the reaction solution is poured into ice water, extracted with dichloromethane and concentrated to the concentrate The column was carried out to obtain 29.2 g of the product with a yield of 80%.

[0062] The NMR data of the product are as follows: 1 H NMR (300 MHz, CDCl 3 ), δ (ppm): 9.86 (s, 2H), 7.82-7.78 (d, 4H), 7.77-7.51 (d, 2H), 7.50-...

Embodiment 3

[0070] Taking the polymer PFN-C as an example to illustrate that this type of polymer has anti-solvent elution properties after cross-linking treatment

[0071] Dissolve the polymer PFN-C synthesized in Example 1 in p-xylene, and then add photoacid [2-(4-methoxystyryl)-4,6-bis(tri Chloromethyl)-1,3,5-triazine], wherein the role of photoacid is to provide hydrogen ions under ultraviolet light irradiation, so that cationic ring-opening polymerization of oxetane occurs. The solution was filtered with a 0.45 micron filter membrane, and spin-coated on a common glass slide to form a film with a thickness of about 20 nanometers. The absorbance of PFN-C after film formation was measured with a UV tester (HP 8453 spectrophotometer) produced by Hewlett-Packard Company, corresponding to figure 1 Curve 1 in . Afterwards, the PFN-C film is irradiated with ultraviolet light with a wavelength of 365 nm for 1 minute, and then heated on a heating plate to cause ring-opening polymerization...

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Abstract

The invention provides an application of crosslinkable conjugated polymer materials in a flip organic photoelectric device. The conjugated polymer materials possess a conjugated main chain and functionalized side chain groups, wherein the functionalized side chain groups comprise a crosslinkable substituent group and a strong polar group possessing water alcohol solubility. Under the condition ofillumination or heating, the conjugated polymer materials can be processed to be insoluble and nonfusible interpenetrating polymer networks through using a strong polar solvent. When constructing a multilayer device, an interface miscibility phenomenon between layers can be overcome. The interpenetrating polymer networks can be regarded as materials of an electron injecting layer or an electron transmission layer to prepare a flip organic electroluminescent device or a flip organic solar cell device. The electron can be directly injected or extracted from a high work function transparency electrode. By using the crosslinkable conjugated polymer materials, processes of the flip organic electroluminescent device and the flip organic solar cell device can be simplified, and an object of preparing the efficient organic photoelectric device by using a low cost technology can be realized.

Description

Technical field [0001] The invention involves the application of co -pillar polymers and its application in the field of organic optoelectronics, and specially involves the application of cross -linking co -pyramid polymer materials in the inverted organic optoelectric components. Background technique [0002] ORGANIC LIGHT-EMITTING DIODES, OLED, [US 4539507], [WO 90 / 13148], [WO 99 / 21935] and Organic Solar Cells, OSC, [WO 94 / 0504555-A], [US 5331183-A], [WO 2002 / 101838-A]), due to the flexible material design, can use large-scale, low-cost solution processing process preparation devices and have a wide range of application prospects.The traditional organic glowing and solar battery components structures are transparent electrodes, cave injection / transmission layers, light -emitting layers or active layers, electronic injection / transmission layers and cathode in the process of processing order.Because the cathode needs to use unstable low -power function materials in the air, the t...

Claims

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Application Information

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IPC IPC(8): H01L51/54H01L51/52C08G61/02
Inventor 黄飞仲成美刘升建曹镛
Owner SOUTH CHINA UNIV OF TECH
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