Fluorene Derivatives with Oxirane Rings for Room-Temperature Polymerization

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Solution Overview

Problem

Current liquid crystal compounds face challenges in being polymerized at room temperature, maintaining orientation in air, having a broad temperature range, chemical stability, and miscibility with other compounds, while also ensuring optical anisotropy and adhesion properties.

Innovation Solution

Development of fluorene derivatives with oxirane or oxetane rings, specifically formulated compounds represented by certain chemical formulae that can be polymerized at room temperature, exhibit optical anisotropy, and possess improved adhesion and miscibility, along with a broad temperature range and chemical stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If liquid crystal compounds are polymerized at room temperature, then polymerizability is improved, but maintaining orientation and adhesion becomes difficult

Engineering Contradiction:
ImprovepolymerizabilityVSAvoidorientation maintenance
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the liquid crystal compound by introducing specific fluorine-containing groups and controlling molecular geometry, enabling polymerization at room temperature while maintaining orientation and adhesion properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite structure within the molecule by combining fluorene backbone with oxirane or oxetane rings, achieving multiple functions including polymerizability, orientation maintenance, and adhesion in a single compound

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If liquid crystal compounds are polymerized in air, then ease of operation is improved, but chemical stability deteriorates

Engineering Contradiction:
Improvepolymerization conditionVSAvoidchemical stability
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent uses air as the polymerization atmosphere without requiring inert gas protection, simplifying the process while the fluorine-containing structure provides inherent chemical stability to the polymerized product

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Adaptability or versatility

If liquid crystal compounds have broad temperature range, then adaptability is improved, but manufacturing precision becomes difficult

Engineering Contradiction:
Improvetemperature rangeVSAvoidphase transition control
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent adjusts the molecular structure parameters by varying fluorine substitution patterns and alkyl chain lengths to precisely control phase transition temperatures while maintaining a broad operational temperature range

Inventive Principle:
Principle #35Parameter changes

4Strength

If liquid crystal compounds have improved adhesion, then strength is improved, but miscibility with other compounds deteriorates

Engineering Contradiction:
ImproveadhesionVSAvoidmiscibility
Core Design Contradiction:
StrengthVSAdaptability or versatility

Solution Approach 1:

The patent introduces fluorine-containing groups at specific positions on the fluorene backbone to enhance adhesion locally, while the overall molecular structure maintains compatibility with common liquid crystal compounds

Inventive Principle:
Principle #3Local quality

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The compounds and derived polymers demonstrate enhanced polymerizability, optical anisotropy, and stability, maintaining orientation and adhesion, while offering a broad temperature range and improved miscibility, leading to superior performance in liquid crystal applications.

Implementation Method 1

it is readily polymerized by irradiation with UV rays

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Implementation Method 2

a polymer having an optical anisotropy is obtained by polymerizing the compound. This is because orientation of molecules in the liquid crystals is fixed by polymerization

Methodology Applied
Scientific EffectOptical anisotropy: Anisotropy

Data Source

PatentUS7381350B2Fluorene derivatives and polymers thereof
Publication Date: 2008.06.03 JIANGSU HECHENG DISPLAY TECH CO LTD
  • US7381350B2 patent drawing
  • US7381350B2 patent drawing
  • US7381350B2 patent drawing

AI summary

The compound (1) or (2), a composition containing the compound and a polymer obtained by polymerizing the composition.R1 is fluorine, cyano, alkyl, and so forth; R2 is hydrogen, alkyl, and so forth; R3 and R4 are independently hydrogen, fluorine, alkyl, and so forth; A is 1,4-cyclohexylene, 1,4-phenylene, and so forth; X is a single bond, —COO—, —OCO—, and so forth; P is alkylene and so forth; m and n are independently 0, 1 or 2.