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S,S-dioxo-dibenzothiophene monomer containing polar substituent groups, water/alcohol soluble polymers thereof, and application thereof

A technology of dibenzothiophene and polar substituents is applied in the application field of cathode interface modification layer in light-emitting diodes and photovoltaic cell devices, and can solve uninvolved and other problems

Active Publication Date: 2013-07-31
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, none of the above-mentioned reports involve the application of water / alcohol-soluble polymers based on polar group S,S-dioxy-dibenzothiophene units as cathode interface modification layers in light-emitting diodes and solar photovoltaic cell devices. Related Information

Method used

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  • S,S-dioxo-dibenzothiophene monomer containing polar substituent groups, water/alcohol soluble polymers thereof, and application thereof
  • S,S-dioxo-dibenzothiophene monomer containing polar substituent groups, water/alcohol soluble polymers thereof, and application thereof
  • S,S-dioxo-dibenzothiophene monomer containing polar substituent groups, water/alcohol soluble polymers thereof, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: 2,8-Dihydroxy-dibenzothiophene

[0068] Weigh thiofluorene (20 g, 108.7 mmol) and dissolve it in chloroform, add 0.31 g (54 mmol) of reduced iron powder, avoid light, add liquid bromine (14 ml, 271.8 mmol), reacted at room temperature for 20 hours. Then neutralize with saturated sodium bisulfite aqueous solution to remove unreacted liquid bromine, pour the reaction system into water, extract with dichloromethane, wash with saturated brine and distilled water, and dry over anhydrous magnesium sulfate. Spin dry and recrystallize with chloroform. 2,8-Dibromo-dibenzothiophene was obtained as white crystals. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 8.24 (m, 2H), 7.71 (m, 2H), 7.58 (m, 2H). 13 CNMR (75MHz, CDCl3) δ (ppm): 138.99, 136.55, 130.68, 125.08, 124.58, 119.01. ESI-MS: m / z 342 (M+). Elemental analysis calculated value [C 12 h 6 Br 2 S] (%): C, 42.14; H, 1.77; S, 9.37; Found: C, 42.16; H, 1.83; S, 9.31. 2,8-Dibromo-S,S-dioxo-dibenzothiophene (3.42 g, 10 m...

Embodiment 2

[0070] Example 2: 3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborinane)-2,8-dioctyloxy-S,S-diox -Dibenzothiophene

[0071]Dissolve 2,8-dihydroxy-dibenzothiophene (10.8 g, 50 mmol) in N,N-dimethylacetamide, add potassium carbonate (20.7 g, 150 mmol), heat to reflux, and Stir for 2 hours under the protection of argon, add 1-bromooctane, and react for 24 hours. Then the system was lowered to room temperature, potassium carbonate was removed by filtration, the filtrate was poured into ice water, extracted with dichloromethane, washed with saturated brine and distilled water, and dried over anhydrous magnesium sulfate. Spin to dryness, and distill off N,N-dimethylacetamide under reduced pressure. The residue was purified by column separation (petroleum ether: ethyl acetate = 10:1 as eluent). 1 H NMR (300MHz, CDCl 3 )δ(ppm):8.22(d,2H),8.16(s,2H),7.06(d,2H),4.08(m,4H),1.73(m,4H),1.42(m,4H),1.29( m,8H), 1.25(m,8H), 0.88(t,6H). 13 C NMR (75MHz, CDCl 3 )δ (ppm): 158.54, 133.69, 132.52...

Embodiment 3

[0073] Example 3: 3,7-dibromo-2,8-bis(6-bromo-hexyloxy)-S,S-dioxo-dibenzothiophene and 3,7-bis(4,4,5, 5-Tetramethyl-1,3,2-dioxaborolane)-2,8-bis(6-bromo-hexyloxy)-S,S-dioxo-dibenzothiophene

[0074] Under the protection of an inert atmosphere, the prepared 2,8-dihydroxy-dibenzothiophene (10.8 g, 50 mmol) was dissolved in N,N-dimethylacetamide, and potassium carbonate (20.7 g, 150 mmol), heated to reflux, stirred for 2 hours under argon protection, added 1,6-dibromohexane, and reacted for 24 hours. Then the system was lowered to room temperature, potassium carbonate was removed by filtration, the filtrate was poured into ice water, extracted with dichloromethane, washed with saturated brine and distilled water, and dried over anhydrous magnesium sulfate. Spin to dryness, and distill off N,N-dimethylacetamide under reduced pressure. The residue was purified by column separation (petroleum ether: ethyl acetate = 10:1 as eluent) to obtain 2,8-bis(6-bromo-hexyloxy)dibenzothiophen...

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Abstract

The invention discloses a S,S-dioxo-dibenzothiophene monomer containing polar substituent groups, water / alcohol soluble polymers thereof, and an application thereof The water / alcohol soluble linear polymers of the S,S-dioxo-dibenzothiophene monomer containing the polar substituent groups and hyperbranched polymers can be used as a cathode interface modification layer of high work function metals, such as aluminium and gold, and thus applied in light-emitting diodes and photovoltaic cell devices. Compared with present polymers (PFN) used for cathode interface layers, the S,S-dioxo-dibenzothiophene unit polymers containing the polar groups has relatively low highest occupied molecular orbital (HOMO) energy level and can simultaneously play effects of electron injection and hole blocking. The polymer can be dissolved in methanol, N,N-dimethyl formamide (DMF), dimethyl sulfoxide (DMSO), water and other polar solvents, and thus phenomena of interface mixing do not occur between an electron transport layer and an active layer during constructing multilayer devices.

Description

technical field [0001] The present invention relates to polymers based on polar group S, S-dioxy-dibenzothiophene units; the invention also relates to polymers based on polar group S, S-dioxy-dibenzothiophene units Application of water / alcohol-soluble cathode interface modification layer in light-emitting diodes and photovoltaic cell devices. Background technique [0002] For organic electroluminescent devices (Organic Light-emitting diodes, OLEDs), in order to achieve better device effects, a multi-layer thin film stack structure is often used, a hole transport layer is added between the anode and the light-emitting layer, and a hole transport layer is added between the cathode Adding an electron transport layer between the light-emitting layer, such as some alcohol / water-soluble polyelectrolytes with polyfluorene as the main chain and their neutral precursors, can effectively improve the transition from high work function metals (such as Al, Ag, Au) electron injection int...

Claims

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Application Information

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IPC IPC(8): C07D333/76C07F9/6553C08G61/12H01L51/54H01L51/46
CPCY02E10/549
Inventor 杨伟应磊肖慧萍余磊何瑞锋曹镛
Owner SOUTH CHINA UNIV OF TECH
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