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Fluorene polymer with crosslinkable group, crosslinked film and preparation method thereof

A technology of cross-linking groups and polymers, which is applied in the field of cross-linked films and their preparation, can solve the problems of complex preparation and low cross-linking degree, and achieve the effects of simple preparation, fast cross-linking speed and convenient preparation

Inactive Publication Date: 2011-04-13
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are mainly the following types of cross-linkable groups used: with oxetane as the cross-linking group, Muller et al. obtained a cross-linkable cross-linking group on TPD with an oxygen bridge to connect two oxetane end groups. Cross-linked polymer semiconductors, but the preparation is relatively complex
In previous reports, the position of the vinyl group as a crosslinking group is mostly at the end of the polymer chain segment, and the degree of crosslinking is not high.

Method used

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  • Fluorene polymer with crosslinkable group, crosslinked film and preparation method thereof
  • Fluorene polymer with crosslinkable group, crosslinked film and preparation method thereof
  • Fluorene polymer with crosslinkable group, crosslinked film and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: (synthesis of a homopolymer whose molar ratio of crosslinkable units is 50% fluorene)

[0049] Polymerization recipe:

[0050] Reactant II (2,7-dibromo-9,9-diallylfluorene) and reactant III (2,7-bis(4,4,5,5-tetramethyl-1,3,2- Dioxaborane-diyl)-9,9-dioctylfluorene) in a molar ratio of 1:1;

[0051] The molar ratio of catalyst and reactant III is 0.03:1;

[0052] The molar ratio of amine ligand to catalyst is 12:1;

[0053]The mol ratio of alkali and reactant III is 6:1;

[0054] Aggregation steps:

[0055] 0.321 g (0.5 mmol) of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene ( III), 0.202g (0.25mmol) 2,7-dibromo-9,9-diallyl fluorene (II), 0.0034g (0.015mmol) palladium catalyst Pd(OAc) 2 , 0.0202g (0.18mmol) ligand triethylenediamine, 0.0249g (0.18mmol) potassium carbonate, and 5ml toluene were added successively in a clean 100ml three-necked flask equipped with magnets, vacuumed and ventilated nitrogen, and the temperature was ...

Embodiment 2

[0056] Example two: (synthesis of a homopolymer whose molar ratio of crosslinkable units is 25% fluorene)

[0057] Polymerization recipe:

[0058] Reactant I (2,7-dibromo-9,9-dioctylfluorene), Reactant II (2,7-dibromo-9,9-diallylfluorene), Reactant III (2,7 - bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene) in a molar ratio of 1:1:2;

[0059] The molar ratio of catalyst and reactant III is 0.03:1;

[0060] The molar ratio of amine ligand to catalyst is 12:1;

[0061] The mol ratio of alkali and reactant III is 6:1;

[0062] Aggregation steps:

[0063] 0.321 g (0.5 mmol) of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene ( III), 0.137g (0.25mmol) 2,7-dibromo-9,9-dioctylfluorene (I), 0.101g (0.25mmol) 2,7-dibromo-9,9-diallylfluorene (II), 0.0034g (0.015mmol) palladium catalyst Pd(OAc) 2 , 0.0202g (0.18mmol) of ligand triethylenediamine, 0.415g (3mmol) of potassium carbonate, and 5ml of toluene were added successively in a c...

Embodiment 3

[0064] Example three: (synthesis of a homopolymer whose molar ratio of crosslinkable units is 20% fluorene)

[0065] Polymerization recipe:

[0066] Reactant I (2,7-dibromo-9,9-dioctylfluorene), Reactant II (2,7-dibromo-9,9-diallylfluorene), Reactant III (2,7 - bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene) in a molar ratio of 3:2:5

[0067] The molar ratio of catalyst to reactant III is 0.03:1

[0068] The molar ratio of amine ligand to catalyst is 12:1

[0069] The molar ratio of base to reactant III is 6:1

[0070] Aggregation steps:

[0071] 0.321 g (0.5 mmol) of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene ( III), 0.164g (0.30mmol) 2,7-dibromo-9,9-dioctylfluorene (I), 0.0808g (0.20mmol) 2,7-dibromo-9,9-diallylfluorene (II), 0.0034g (0.015mmol) palladium catalyst Pd(OAc) 2 , 0.0202g (0.18mmol) of ligand triethylenediamine, 0.415g (3mmol) of potassium carbonate, and 5ml of toluene were added successively in a clea...

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Abstract

The invention discloses a fluorene polymer with a crosslinkable group, a crosslinked film and a preparation method thereof, and relates to the field of preparation technology and application of organic semiconductor materials. The fluorene polymer has a molecular weight of 10,000 to 50,000; a C-9 position of fluorene contains allyl; and a molar ratio of a crosslinkable unit in the polymer can be adjusted. The preparation method for the crosslinked film is performed according to two conditions, namely, a crosslinkable polymer with allyl crosslinkable group can be crosslinked under the initiation of ultraviolet rays; and a polymer semiconductor without the crosslinkable group is mixed with the crosslinkable fluorene homopolymer serving as a crosslinking agent to be crosslinked through photo-initiation. The molar ratio of the crosslinkable unit in the prepared polymer can be adjusted. Compared with other crosslinkable luminous polymers, the fluorene polymer is simple in preparation and high in crosslinking speed, and has no influence on main luminous performance of the crosslinked luminous polymers.

Description

technical field [0001] The invention relates to the preparation technology and application field of organic semiconductor materials, and relates to the synthesis of crosslinkable fluorene homopolymers and copolymers with allyl groups in the C-9 position by Suzuki reaction (Suzuki coupling) and the crosslinked films prepared therefrom and its preparation method. Background technique [0002] Among all kinds of electroluminescent conjugated polymers, polyfluorene derivatives have some attractive features: the fluorene unit is a rigid coplanar biphenyl structure, and the C-9 position can easily introduce various substituent groups to Improve solubility and supramolecular structure without causing significant steric hindrance to affect the conjugation of the main chain; polyfluorene derivatives have good thermal stability, light stability and chemical stability; polyfluorene derivatives The photoluminescence (PL) and electroluminescence (EL) efficiencies are appropriate and can...

Claims

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Application Information

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IPC IPC(8): C08G61/02C08J3/24C08J5/18H01L51/54C09K11/06
Inventor 李坚孙明慧米衡
Owner CHANGZHOU UNIV
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