Coumarinyl Oxime Derivatives for Photoresist Sensitivity

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current photoresist compositions for display applications, such as LCD and OLED devices, face challenges in achieving high sensitivity and transparency due to limitations in photosensitivity and transmittance, particularly in the radiation-sensitive resin compositions used for forming insulation layers, color filters, and microlenses.

Innovation Solution

Incorporating oxime derivatives with a coumarinyl chromophore containing a strong electron-withdrawing group, such as a perfluoroalkyl or perfluoroaryl group, to enhance photo sensitivity and transparency, specifically in the form of compounds like those described in formula (I), which act as latent acids in chemically amplified photoresist compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional photoresist compositions are used, then manufacturing process is simple, but photo sensitivity and transparency are insufficient

Engineering Contradiction:
Improvephoto sensitivityVSAvoidcomposition complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the molecular structure of photoacid generator compounds by introducing specific substituents (perfluoroalkyl groups at positions 3 and 5, coumarinyl chromophore) to change the chemical parameters of the photoresist composition. This structural modification enhances photo sensitivity and transparency without fundamentally changing the composition architecture

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite photoacid generator molecule combining multiple functional groups: coumarinyl chromophore for light absorption, oxime sulfonate for photoacid generation, and perfluoroalkyl groups for enhanced properties. This composite structure achieves superior photo sensitivity and transparency compared to conventional single-function compounds

Inventive Principle:
Principle #40Composite materials

2Productivity

If radiation-sensitive resin composition is used for forming insulation layers, then patterning efficiency is improved, but transmittance is reduced

Engineering Contradiction:
Improvepatterning efficiencyVSAvoidtransmittance
Core Design Contradiction:
ProductivityVSIllumination intensity

Solution Approach 1:

The patent optimizes the molecular parameters of the photoacid generator to achieve high photo sensitivity at low concentrations (0.1-10 wt%), thereby maintaining high transmittance while ensuring sufficient patterning efficiency. The specific molecular structure enables effective photoacid generation with minimal absorption of exposure light

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If photoresist composition with high sensitivity is used, then resolution is improved, but transparency is reduced

Engineering Contradiction:
ImproveresolutionVSAvoidtransparency
Core Design Contradiction:
Manufacturing precisionVSIllumination intensity

Solution Approach 1:

The invention fine-tunes the molecular parameters of the photoacid generator compound, specifically the substitution pattern on the coumarinyl ring and the nature of electron-withdrawing groups, to achieve optimal balance between photo sensitivity (affecting resolution) and light absorption characteristics (affecting transparency). The patent identifies specific structural parameters that maximize resolution while minimizing light absorption

Inventive Principle:
Principle #35Parameter changes

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 introduction of these oxime derivatives significantly increases photo sensitivity and transparency, enabling the development of chemically amplified photoresist compositions with improved resolution and image quality, suitable for high-resolution patterns in display devices.

Implementation Method 1

photo exposure to the photoresist are known for the application as photo acid generator

Methodology Applied
Scientific EffectPhotochemical reaction: Photophoresis

Implementation Method 2

Incorporating oxime derivatives with a coumarinyl chromophore containing a strong electron-withdrawing group

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentEP3253735B1Latent acids and their use
Publication Date: 2021.03.31 BASF SE
  • EP3253735B1 patent drawing
  • EP3253735B1 patent drawing
  • EP3253735B1 patent drawing

AI summary

Compounds of the formula (I) and (IA) wherein X is -O(CO)-; R1 is C1-C12haloalkyl or C6-C10haloaryl; R2 is located in position 7 of the coumarinyl ring and is OR8; R2a, R2b and R2C independently of each other are hydrogen; R3 is C1-C8haloalkyl or C1-C8haloalkyl; R4 is hydrogen; and R8 is C1-C6alkyI; are suitable as photosensitive acid donors in the preparation of photoresist compositions such as used for example in the preparation of spacers, insulating layers, interlayer dielectric films, insulation layers, planarization layers, protecting layers, overcoat layers, banks for electroluminescence displays and liquid crystal displays (LCD).