Polymer and light-emitting polymer element using the same

A technology of polymer compounds and luminescent materials, which is applied in the field of polymer light-emitting elements, and can solve problems such as long emission wavelengths and insufficient characteristics

Inactive Publication Date: 2011-09-21
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, when the above-mentioned polymer compound is used in a polymer light-emitting device (polymer LED), there are problems in that the emission wavelength is long, the chromaticity when used as a blue light-emitting material, and the luminescence as blue, green, red, white, etc. Component characteristics such as lifespan during use of materials may not be sufficient

Method used

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  • Polymer and light-emitting polymer element using the same
  • Polymer and light-emitting polymer element using the same
  • Polymer and light-emitting polymer element using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0423] Synthesis of Compound B and Compound B-1

[0424] (Synthesis of Compound A)

[0425]

[0426] Install a reflux tube on the three-necked flask. Under a nitrogen atmosphere, 10.0 g of phenoxazine, 15.2 g of 1-bromo-4-tert-butyl 2,6-dimethylbenzene, 21.9 g of sodium tert-butoxide, and 345 ml of toluene were added and stirred, and then tridibenzylidene was added. 0.25 g of acetone dipalladium, and 0.13 g of tert-butylphosphine tetrafluoroborate. Stir at reflux for 9 hours and cool to room temperature. The reaction solution was filtered through a glass filter precoated with alumina, the resulting solution was washed with 3.5% hydrochloric acid, and the toluene solution was concentrated. To the obtained solid, 5 ml of toluene and 50 ml of isopropanol were added, heated, stirred for 1 hour, and then cooled to room temperature. The generated precipitate was filtered and washed with isopropanol to obtain 8.3 g of Compound A as a pale yellow solid.

[0427] 1 H-NMR (CDC...

Synthetic example 1

[0439] Synthesis of Compound D

[0440] (Synthesis of Compound C)

[0441]

[0442]Install a mechanical stirrer and a condenser on a 3L four-neck round bottom flask. The inside of the reaction vessel was replaced with nitrogen, 1.10 g of palladium(II) acetate, 1.51 g of tris(o-tolyl)phosphine, and 368 ml of toluene were added, and the mixture was stirred at room temperature for 30 minutes. 143 g of phenoxazine, 97.1 g of sodium tert-amyloxide, and 800 ml of toluene were added and stirred, 133.4 ml of 1-bromo-4-butylbenzene was dissolved in 60 ml of toluene, and added dropwise to the reaction vessel using a dropping funnel. Stir at 105°C for 5 hours, then cool to room temperature. Filtration was performed through a glass filter pre-coated with 2 cm of alumina, and the resulting solution was neutralized with 3.5% hydrochloric acid. The toluene solution was concentrated, 30 ml of toluene was added, and the mixture was stirred at 75° C. for 30 minutes, and then 700 ml of is...

Synthetic example 2

[0450] Synthesis of Compound F

[0451] (Synthesis of Compound E)

[0452]

[0453] Install a mechanical stirrer and a condenser on a 3L three-necked round-bottomed flask for nitrogen replacement. Then, 86.5 g of 2,7-dibromo-9-fluorenone and 500 g of phenol dissolved by heating in a furnace were added. The temperature was raised to 105°C while stirring, and cooled to 65°C when 2,7-dibromo-9-fluorenone was completely dissolved. 1.98 g of 3-mercaptopropane-1-sulfonic acid was weighed in a spherical box, and it was slowly added while being careful not to raise the temperature in the reaction system. After adding the catalyst, the mixture was stirred at 65° C. for 21 hours, 722 ml of ethanol was added, and heated to dissolve. It was then cooled to 45°C, poured into 7.6L of ion-exchanged water heated to 65°C, and then stirred for 2 hours. The precipitated orange precipitate was filtered, washed with water, and left to dry overnight. The obtained orange solid was transferre...

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Abstract

Disclosed is a polymer compound containing a residue of a compound represented by the following formula (1). In the formula, ring C<1>, ring C<2> and ring C<3> independently represent an aromatic hydrocarbon ring or a heterocyclic ring; A<1> represents a divalent group containing one ore more atoms selected from a boron atom, carbon atom, nitrogen atom, oxygen atom, phosphorus atom, sulfur atom and selenium atom; R<1> represents an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, alkenyl group, alkynyl group, disubstituted amino group, trisubstituted silyl group, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, substituted carboxyl group, heteroaryloxy group or heteroarylthio group, or alternatively forms a ring together with an atom adjacent to the atom of the ring C<3> to which R<1> is bonded.

Description

technical field [0001] The present invention relates to a polymer compound, a method for producing the polymer compound, a compound used as a raw material for synthesizing the polymer compound, a solution containing the polymer compound, a film containing the polymer compound, and a polymer compound containing the polymer compound. Molecular light emitting elements. Background technique [0002] Various studies have been conducted on high-molecular-weight light-emitting materials and charge-transporting materials that are soluble in solvents and capable of forming organic layers in light-emitting elements by coating methods. A polymer compound with oxazine as a repeating unit (Patent Document 1: JP-A-2003-165829) and a blue electroluminescent polymer with a phenoxazine unit introduced into the main chain (Patent Document 2: JP-A-2004-137456). [0003] However, when the above-mentioned polymer compound is used in a polymer light-emitting device (polymer LED), there are probl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D265/38C07D279/22C09K11/06H01L51/50
CPCH01L51/0035H01L51/5012C07D279/22C09K2211/1425C09K2211/1475C09K2211/1458H01L51/5048C08G73/026C09K2211/1416C08G61/02C09K2211/185C07D265/38H05B33/14C09K11/06C09K2211/1466C09K2211/1483C09K2211/145C09K2211/1433C09K2211/182C08G61/12C08G61/122C09K2211/1491H10K85/111H10K50/14H10K50/11H10K50/00H10K85/631
Inventor 小林谕小林重也
Owner SUMITOMO CHEM CO LTD
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