2,6-Naphthyl Liquid-Crystalline Compounds for Wide Phase Width

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Solution Overview

Problem

Existing liquid-crystalline materials often have a temperature range for the liquid-crystalline phase that is outside the desired application temperature or is too narrow, limiting their usability, and there is a need for compounds with high birefringent properties and a broader phase width for processing.

Innovation Solution

Development of compounds with specific chemical structures, including 2,6-naphthyl radicals and reactive groups, that can form polymerizable liquid-crystalline compositions capable of forming nematic, chiral nematic, or cholesteric phases with enhanced optical properties and a wider temperature range.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If existing liquid-crystalline materials are used, then they can provide liquid-crystalline phases, but the temperature range is outside the desired application temperature or too narrow

Engineering Contradiction:
Improvetemperature range of liquid-crystalline phaseVSAvoidusability in desired application temperature
Core Design Contradiction:
TemperatureVSAdaptability or versatility

Solution Approach 1:

The patent modifies the molecular structure parameters of liquid-crystalline compounds by introducing 2,6-naphthyl radicals and various spacer groups (A1, A2) with different carbon chain lengths and compositions. These structural parameter changes systematically adjust the liquid-crystalline phase temperature range to fall within the desired application temperature window of -50°C to +50°C, resolving the contradiction between inherent material temperature ranges and application requirements

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures combining 2,6-naphthyl radicals with diverse spacer groups and terminal groups (Z1, Z2). This composite approach allows tuning of both the temperature range and optical properties simultaneously, enabling the liquid-crystalline phase to exist within the desired temperature range while maintaining high birefringence for optical applications

Inventive Principle:
Principle #40Composite materials

2Duration of action of moving object

If existing liquid-crystalline materials are used, then they can form liquid-crystalline phases, but the phase width is too narrow for processing

Engineering Contradiction:
Improvephase widthVSAvoidprocessing capability
Core Design Contradiction:
Duration of action of moving objectVSEase of manufacture

Solution Approach 1:

The patent extends the liquid-crystalline phase width by optimizing molecular parameters including the introduction of rigid 2,6-naphthyl cores combined with flexible spacers of varying lengths (A1, A2). This parameter optimization broadens the temperature interval over which the liquid-crystalline phase stabilizes, providing sufficient processing window for manufacturing operations while maintaining phase stability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces polymerizable functional groups (Z1, Z2) that enable dynamic transition from liquid-crystalline state to crosslinked gel state. This dynamic capability allows the material to be processed during the liquid-crystalline phase and then fixed in the desired configuration through polymerization, significantly enhancing ease of manufacture

Inventive Principle:
Principle #15Dynamics

3Stability of the object's composition

If liquid-crystalline ordered structures are fixed in the solid state through polymerization, then stability is improved, but the compounds require polymerizable groups adding structural complexity

Engineering Contradiction:
Improvestability of liquid-crystalline ordered structuresVSAvoidmolecular structure complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The patent segments the molecular structure into distinct functional modules: 2,6-naphthyl radical core, spacer groups (A1, A2), and terminal polymerizable groups (Z1, Z2). This segmentation allows independent optimization of each module's function while maintaining overall structural stability, reducing the complexity burden by making the structure modular and systematic

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent designs terminal groups (Z1, Z2) that serve multiple functions: they provide polymerizability for crosslinking, maintain liquid-crystalline ordering, and can be selected from various chemical families (acrylates, vinyl, epoxides). This multi-functionality reduces overall molecular complexity by using versatile functional groups that accomplish multiple objectives simultaneously

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 new compounds provide liquid-crystalline compositions with high birefringence and a broader phase width, enabling their use in various optical and electrooptical applications by fixing ordered structures in the solid state through polymerization, thus overcoming the limitations of existing materials.

Implementation Method 1

On heating, numerous compounds are not converted from the crystalline state with defined short-range and long-range order of the molecules directly into the liquid, unordered state, but rather pass through a liquid-crystalline phase in which the molecules are mobile but the molecular axes form an ordered structure

Methodology Applied
Scientific EffectLiquid crystalline phase formation: Liquid Crystals

Implementation Method 2

maximum refraction of the liquid-crystalline materials is often desired. Under this aspect, especially liquid-crystalline materials which comprise 2,6-naphthyl radicals appear to possess high potential

Methodology Applied
Scientific EffectBirefringence: Birefringence

Implementation Method 3

there is the possibility of polymerization into polymeric networks or, in the case that the liquid-crystalline compounds comprise polymerizable groups, of polymerizing the liquid-crystalline compounds themselves

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Data Source

PatentUS7670505B2Compounds comprising 2,6-naphthyl groups
Publication Date: 2010.03.02 BASF SE
  • US7670505B2 patent drawing
  • US7670505B2 patent drawing
  • US7670505B2 patent drawing

AI summary

Compounds of the general formula I(variables defined herein) and processes for making compounds including 2,6 -naphthyl radicals are provided. Polymerizable or nonpolymerizable liquid-crystalline compositions including one or more compounds including 2,6 -naphthyl radicals, and products and processes employing such compositions, are also provided.