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Communication

Novel Yellow Aromatic Imine Derivative Incorporating Oxazolone Moiety for Color Resist Applications

by
Sunwoo Park
,
Sangwook Park
,
Seyoung Oh
,
Yeongjae Heo
,
Hayoon Lee
and
Jongwook Park
*
Integrated Engineering, Department of Chemical Engineering, Kyung Hee University, Youngin 17104, Republic of Korea
*
Author to whom correspondence should be addressed.
Appl. Sci. 2024, 14(11), 4362; https://doi.org/10.3390/app14114362
Submission received: 4 May 2024 / Revised: 14 May 2024 / Accepted: 20 May 2024 / Published: 21 May 2024
Browse Figures
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Abstract

:
A novel aromatic imine derivative, 2′-(1,4-phenylene)bis[4-[(4-methoxyphenyl)methylene]-5(4H)-oxazolone] (PBMBO), was designed and synthesized as a yellow colorant additive for green color filters used in image sensors. The optical and thermal properties of the newly developed material were evaluated both in solution and within color filter film conditions. PBMBO demonstrated a molar extinction coefficient of 2.24 × 104 L/mol·cm in solution, surpassing that of the commercially employed yellow colorant MBIQO by a factor of 1.82. Color resist (CR) films incorporating PBMBO exhibited outstanding optical characteristics, displaying 0.03% transmittance at 435 nm, 99.3% transmittance at 530 nm, and a sharp slope within the 400 to 550 nm range. The decomposition temperature of PBMBO was 303 °C, indicating relatively superior thermal stability compared to MBIQO. Consequently, PBMBO emerges as a highly promising candidate for a yellow colorant additive in imaging sensor color filters, owing to its exceptional optical and thermal stability. Its potential applications are anticipated to extend across various fields of organic semiconductors.

1. Introduction

The core technologies of the fourth industrial revolution, such as artificial intelligence and the internet of things, rely significantly on the essential utilization of color filter organic materials. These materials are based on semiconductor materials found in liquid crystal displays and charge-coupled devices. There is a growing demand for related technologies due to the significance of visual information. Color filters play a crucial role in impacting the performance of organic semiconductor technologies, particularly in image sensors and displays. In image sensors, color filters play a crucial role by selectively transmitting particular colors from the full spectrum of incident light. This process effectively converts optical images into electrical signals [1,2,3,4,5,6]. As smartphones and digital cameras require higher resolution, sharper images, and greater sensitivity, the size of image sensor pixels is steadily diminishing [7,8]. This reduction in pixel size results in a decrease in the quantity of the colorant used, thus requiring colorants of finer dimensions. In these smaller pixel sizes, it becomes crucial to have optimized absorption and transmission properties to produce top-notch images using compact color filters. Hence, there is a need for colorants with a high molar extinction coefficient capable of efficiently absorbing light at specific wavelengths to ensure clear imaging [9,10,11,12]. Moreover, it is essential to explore materials with superior thermal and chemical stability to reliably prepare and utilize components in small-sized pixels [13,14]. This reliability is crucial for ensuring stable components within these smaller pixels. These requisites apply across all primary colors: red, green, and blue. Particularly, yellow colorants, used to enhance optical properties, are applied to green colors, which are difficult to satisfy optically, as additives [15,16]. When used in conjunction with green in RGB color filters, the yellow color filter can block unnecessary transmission below 500 nm, which corresponds to the blue range present in green. This correction compensates for overlapping transmission spectra. Green color filters, thus corrected, can exhibit a narrow full width at half maximum and achieve high color purity, enabling the realization of excellent optical characteristics. Essential optical properties for yellow colorants include a low transmittance of 5% or less at 435 nm in the film state and a high transmittance of over 90% at 530 nm [17]. In this study, we designed and synthesized a novel yellow dye based on dimeric derivatives of oxazolone, belonging to the aromatic imine category, to investigate its potential as an additive green colorant. Incorporating a yellow additive into green colorant mixtures is crucial due to the inherent difficulty of green colorants in fully absorbing blue light. The synthesized aromatic imine derivatives were extensively studied to enhance their optical and thermal stability and to evaluate their potential as materials for yellow color filters.

2. Materials and Methods

2.1. Materials and Instrumentation

9-Methoxy-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (MBIQO) was purchased from Yedahm Chemical, Gimpo, Republic of Korea, with a purity of 98%. (E)-(4-(4-methoxybenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl) boronic acid was purchased from CK Chem, Suwon, Republic of Korea, with 98% purity. Other compounds used in this study were purchased from Sigma-Aldrich, Saint Louis, MO, USA, and Tokyo Chemical Industry (TCI), Tokyo, Japan; their purity was at least 98%, and they were used without further purification. 1H nuclear magnetic resonance (NMR) spectra were recorded on a JNM-ECZ400S/L1 (JEOL, Tokyo, Japan). Ultraviolet–visible (UV–Vis) optical absorption spectra were measured using a UV-1900i UV/Vis/NIR spectrometer (Shimadzu, Kyoto, Japan). The thermogravimetric analysis (TGA) was examined using an SDT Q600 (TA Instruments, Lukens Dr, New Castle, DE, USA), with the sample under an air condition. Samples were heated to 600 °C at a rate of 10 °C/min. Transmission electron microscopy (TEM) images were acquired using a JEM-2100F (JEOL, Tokyo, Japan). The particle size distribution was calculated using the ImageJ software (version 1.54i). ImageJ is a Java-based, multi-threaded, freely accessible, open-source, platform-agnostic, and public domain software designed for image processing and analysis.

2.2. Synthesis of 2,2′-(1,4-Phenylene)bis [4-[(4-Methoxyphenyl)methylene]-5(4H)-oxazolone] (PBMBO)

1,4-Dibromobenzene (0.3 g, 1.27 mmol), (E)-(4-(4-methoxybenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl) boronic acid (0.72 g, 2.92 mmol), palladium(II) acetate (Pd(OAc)2) (0.026 g, 0.09 mmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (0.07 g, 0.15 mmol) were added in a 30 mL solution of anhydrous toluene. Upon reaching a reaction temperature of 50 °C, tetraethylammonium hydroxide (Et4(NOH)) (20 wt%) (3 mL) was poured into the reaction mixture. The mixture was then heated to 100 °C under a nitrogen atmosphere for 5 h. Following the completion of the reaction, the mixture was extracted with dichloromethane and water. The organic layer was subsequently dried over anhydrous magnesium sulfate (MgSO4), filtered, and the solvent evaporated. The resulting residue was dissolved in dichloromethane, and ethanol was added. The resulting precipitate was filtered and washed with methanol. The precipitate was further purified with column chromatography using a dichloromethane:n-hexane (1:9) eluent, resulting in solid isolation. After column purification, the solid was reprecipitated using a mixture of dichloromethane and methanol, yielding a yellow solid (0.133 g, 22% yield). 1H NMR (400 MHz, THF-d8) δ 8.31 (s, 2H), 8.28 (dd, J = 8.7, 3.3 Hz, 4H), 8.26–8.13 (m, 2H), 7.26 (d, J = 9.6 Hz, 2H), 7.05–7.00 (m, 4H), 3.85 (d, J = 4.0 Hz, 6H).

2.3. Fabrication of Film and Color Filters

After drop-casting a solution of colorant at a concentration of 1 × 10−3 M onto the substrate in propylene glycol monomethyl ether acetate (PGMEA), a film containing a yellow colorant was fabricated by baking on a hotplate at 100 °C for 10 min. To evaluate the thermal and chemical stability of the image sensor, colorimetric measurements were carried out under specified conditions. Nano-sized colorant dispersion was prepared using a mixer (LQFS, London, UK) equipped with a 3 mm glass ball. A ratio of 100 balls to 1 colorant was used, and milling was conducted for 48 h to achieve nano-pigmentation [18,19]. To prepare the color resist solution, 11.25 g of colorant, which had undergone the nano-pigmentation process, is mixed with 7 g of an acrylic binder composed of methyl methacrylate, carboxylic acid groups, benzyl methacrylate groups, and 2 g of dispersant, along with 80 g of PGMEA solvent. The prepared solution was spin-coated onto a 2.5 cm × 2.5 cm transparent glass substrate using a MIDAS SPIN-1200D spin-coater. The coating speed started at 100 rpm for the initial 1 s and then increased to 1000 rpm, remaining constant for 10 s. After spin-coating, the colorant film was prebaked at 100 °C for 10 min and post-baked at 230 °C for 30 min. The thickness of all spin-coated color filter films was 2 μm.

3. Results and Discussion

The commercially utilized 9-methoxy-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (MBIQO), exhibiting yellow color characteristics, demonstrates excellent optical properties suitable for application as a color filter material for image sensors due to its aromatic imine group [20,21,22,23,24,25,26]. We conducted molecular design of a novel yellow colorant capable of enhancing absorption characteristics while retaining the aromatic imine group and functional groups present in MBIQO. The newly designed aromatic imine derivative, PBMBO, incorporates a benzene and (E)-4-(4-methoxybenzylidene)oxazol-5(4H)-one moiety. In synthetic compounds, a dimeric arrangement is prepared, where the structure contains an (E)-4-(4-methoxybenzylidene)oxazol-5(4H)-one framework comprising a phenyl core alongside an oxazolone and a methoxy group, connected on both ends. This dimerization is anticipated to enhance solvent interaction compared to conventional MBIQO, leading to increased solubility. Additionally, it is expected to improve absorbance through electron delocalization. The structural formula and synthesis pathway of the synthesized PBMBO are illustrated in Scheme 1 and Scheme 2. The synthesized compound was purified through a column and reprecipitation process, and its structure was confirmed via NMR spectroscopy (Figure S1).
The optical data in solution state of the newly synthesized yellow colorant, PBMBO, are presented in Figure 1 and Table 1. The measurements of absorbance and transmittance of PBMBO were conducted under conditions suitable for image sensor applications, utilizing a 1 × 10−4 M solution in PGMEA. The requirements for the molecular extinction coefficient of yellow colorants in image sensor applications are above 1.0 × 104 L/mol·cm, and the transmittance criteria are less than 5% at 435 nm and over 90% at 530 nm. The molecular extinction coefficient values were calculated using the Beer–Lambert law formula to evaluate the optical absorption properties of yellow colorants.
A = εcl
A: absorbance; ε: molecular extinction coefficient; c: molar concentration; l: optical path length
UV–Vis absorption spectroscopy is a method used to determine the range and intensity of wavelengths absorbed by a material in the 200–800 nm range. Absorption occurred in the 400–500 nm range for both synthesized materials, with maximum absorption wavelengths observed at 410 nm for MBIQO and 434 nm for PBMBO. While absorption intensity is typically expressed in the range of 0–1, the synthesized materials exhibited absorption intensities greater than 1 even at a low concentration of 1 × 10−4 M, owing to their extremely high molecular extinction coefficients and despite being dilute solutions. The molecular extinction coefficient values at the maximum absorption wavelengths of MBIQO and PBMBO were 1.23 × 104 and 2.24 × 104 L/mol·cm at 410 nm and 434 nm, respectively. Therefore, both MBIQO and PBMBO demonstrated molecular extinction coefficient values of over 1.0 × 104 L/mol·cm in PGMEA solvent, indicating their excellence as yellow colorant candidates. While both MBIQO and PBMBO exhibited absorption in the same range of 400–500 nm, PBMBO showed a significantly enhanced molecular extinction coefficient value, being 1.82 times higher than MBIQO. This increase in the molecular extinction coefficient value is interpreted as the result of the excellent absorption characteristics of the oxazolone moiety, which enhances the absorption properties when forming the colorant in a dimeric form [27,28,29,30]. Consequently, the transmittance spectra of both yellow colorants exceeded the requirements of image sensor applications. As indicated in Table 1, the transmittance of PBMBO was 0.58% and 95.9%, respectively, while MBIQO at 435 nm and 530 nm was 4.3% and 99.8%. Both materials satisfied the transmittance requirements. This showed enhanced transmittance characteristics for PBMBO in comparison to the commercial yellow colorant Y138, which exhibited transmittance values of 0.71% at 435 nm and 95.1% at 530 nm [31]. In the case of image sensor applications of yellow colorants, they are added to green colorants to enhance the optical properties of green colorants. Especially when applied to small-sized image sensor pixel ranges, several important characteristics are required to minimize color interference between pixels and achieve high color purity of the pixels. Firstly, excellent transmittance characteristics are required at 435 nm and 530 nm, as mentioned earlier. Secondly, the slope of the transmittance spectrum between wavelengths corresponding to long wavelengths with near 0% transmittance in the blue region and wavelengths corresponding to short wavelengths with near 100% transmittance in the green region is important, and the steeper the slope, the better the performance [32]. Examining the results corresponding to the slope of the transmittance spectrum in Figure 1b, PBMBO exhibited a steeper slope in the 425 nm and 550 nm regions compared to MBIQO, confirming superior optical properties.
The transmittance data of the synthesized materials in a film state are measured and presented in Figure 2 and Table 2. The film fabrication method of the yellow dye is described in the experimental section, and the transmittance values of MBIQO and PBMBO at 435 nm were 36.6% and 0.82%, respectively, while at 530 nm, they were 95.7% and 93.1%. At 435 nm, MBIQO did not meet the criterion of less than 5% transmittance, yielding unsatisfactory results; however, PBMBO exhibited excellent transmittance of less than 5%. At 530 nm, both materials exceeded the requirement of 90% transmittance. Additionally, the results regarding the slope between blue and green, as shown in Figure 2, indicated that PBMBO exhibited a very steep slope at 425 nm and 550 nm, demonstrating excellent performance. Therefore, PBMBO exhibited excellent optical properties suitable for commercialization in both solution and film states, and when applied as a yellow additive for image sensors, superior color purity can be expected.
To be used as a color filter material for image sensors, the solubility of the colorant in PGMEA solvent, commonly used in the display and image sensor industries, is checked. MBIQO and PBMBO exhibited solubilities in PGMEA solvent, as summarized in Table 3, with 0.15 wt% and 0.32 wt%, respectively. The solubility of PBMBO was enhanced by 2.1 times compared to MBIQO. Compared to the reported solubility of 0.1 wt% for the commercial material yellow colorant Y138, PBMBO exhibited a 3.2-fold improvement, while MBIQO showed a similar value [31]. For MBIQO, its relatively low solubility is attributed to its planar molecular structure, which results in poor solubility due to intermolecular packing. The improved solubility of PBMBO compared to MBIQO is interpreted as resulting from the increased number of functional groups capable of effectively interacting with the solvent and the rotatable molecular structure of the (E)-4-(4-methoxybenzylidene)oxazol-5(4H)-one moiety within the molecule. It is anticipated that utilizing PBMBO with high solubility will enable the uniform preparation of solutions and the preparation of dense films during film fabrication.
To investigate the thermal properties for commercialization, the decomposition temperature (Td) corresponding to a 5% weight loss was measured via TGA experiments on the synthesized materials. Figure 3 illustrates the relevant graph, and the Td values for MBIQO and PBMBO were found to be 288 °C and 303 °C, respectively. Both materials exceeded the process temperature of 200 °C, commonly used in color filter processes. The thermal characteristics of PBMBO are suitable for use in image sensor manufacturing processes. It is generally known that a higher molecular weight correlates with greater thermal stability. In the case of PBMBO, the substitution of aromatic imine groups on both sides of the phenyl group resulted in a dimeric structure, thereby increasing the molecular weight and interpreting the observed higher thermal stability.
To prepare color resist (CR) mixtures, a nano-pigmentation process is conducted following the synthesis of the colorant. The nano-pigmentation process is essential during the CR manufacturing process to minimize color interference due to the small size of image sensor pixels and to achieve high color purity. Subsequently, the prepared materials are mixed with monomers, photoinitiators, and solvents to obtain the final CR mixture. The synthesized PBMBO was also subjected to the nano-pigmentation process to assess its applicability in general display and semiconductor applications, and its properties were evaluated (Figure 4). Before the nano-pigmentation process, PBMBO formed long rods measuring 30 nm × 200 nm. After the nano-pigmentation process, analysis of particle size distribution obtained from TEM images revealed that the particles exhibited a spherical shape with an average size of 65 nm (Figure S2), representing a remarkable 55.2% size reduction compared to before the nano-pigmentation process. The smaller spherical particle sizes help reduce light scattering, especially in the blue wavelength region, which, in turn, improves the contrast ratio of the display devices. Higher transmittance and lower light scattering from color filters are desirable. This reduction in particle size is a crucial factor in obtaining excellent color purity and a high molar extinction coefficient during CR film fabrication. The ability to generate such small particles is attributed to inherent properties originating from the molecular structure, which is considered a crucial feature for producing high-performance CR particles.
The optical characteristics of the thin film after CR preparation are summarized in Figure 5 and Table 4. These optical properties were achieved by adding additives to a pure yellow colorant. The transmittance of MBIQO and PBMBO was 3.63% and 0.03% at 430 nm and 94.1% and 99.3% at 530 nm, respectively. The transmittance of both materials remained below 5% at 435 nm and exceeded 90% at 530 nm. The slope of the transmittance spectrum, which changes from 0% to 100%, was observed to characterize the color properties of the colorant. Examining the transmittance gradient near the band edge, a sharp slope was observed in the range of 475–525 nm for PBMBO, while MBIQO exhibited a relatively gentle slope in the range of 400–550 nm. This indicates that PBMBO possesses superior optical characteristics compared to MBIQO. The wavelength values corresponding to the high transmittance near the band edge in the range of 400–550 nm were 441 nm for MBIQO and 478 nm for PBMBO. Detailed analysis of the transmittance in the range of 400–550 nm revealed that PBMBO exhibited excellent transmittance of less than 1% in the range of 350–475 nm, indicating no interference from other colors. In contrast, MBIQO showed a transmittance of 3% in this range, indicating interference with other colors. The low transmittance of PBMBO in the visible light range is interpreted as being due to the use of oxazolone derivatives with excellent absorption properties among the aromatic imine groups. This high coefficient amplifies the absorption at wavelengths within that range, ultimately reducing the transmittance. The newly synthesized compound, PBMBO, showed a significant improvement in the transmittance of the color filter film through the nano-pigmentation process. For example, while the transmittance in the solution state was 0.58% at 435 nm, the transmittance in the film was improved to 0.03%. This indicates that in the solution state, the synthesized materials partially aggregate, resulting in less improvement in transmittance characteristics. The newly synthesized yellow colorant, PBMBO, successfully meets the stringent requirements for yellow in commercial image sensors. Particularly, PBMBO holds potential for future applications in organic semiconductor fields, such as commercial image sensor applications, due to its transmittance characteristics, thermal stability, and other factors.

4. Conclusions

The newly synthesized aromatic imine-based yellow colorant for image sensors, PBMBO, was successfully synthesized with optimized optical properties by incorporating various polar functional groups in a dimeric form. To assess its suitability as a colorant for image sensor color filters, the optical properties of PBMBO were evaluated. PBMBO exhibited a 2.1-fold higher solubility and a 1.82-fold higher molar extinction coefficient compared to MBIQO. The Td of PBMBO was 303 °C, exceeding the required temperature of 200 °C for color filter manufacturing processes. The particle size of PBMBO was observed to be an average of 65 nm through the nano-pigmentation process. In the transmittance spectrum of the color filter film prepared using a CR solution, PBMBO demonstrated satisfactory transmittance values, with 0.03% at 435 nm and 99.3% at 530 nm, meeting the transmittance requirements. Moreover, it exhibited a steep slope in the range of 400–550 nm, between blue and green, indicating excellent color purity. Therefore, the novel yellow colorant PBMBO holds promise for future applications not only in image sensors but also in various organic semiconductor fields.

Supplementary Materials

The following supporting information can be downloaded at https://www.mdpi.com/article/10.3390/app14114362/s1, Figure S1: 1H NMR spectrum of PBMBO. Figure S2. Particle size distribution diagram of PBMBO after the nano-pigmentation process.

Author Contributions

Conceptualization, S.P. (Sunwoo Park) and J.P.; methodology, S.P. (Sunwoo Park) and S.P. (Sangwook Park); validation H.L. and J.P.; formal analysis, S.P. (Sunwoo Park), S.P. (Sangwook Park), S.O. and Y.H.; investigation, S.P. (Sangwook Park), S.O. and Y.H.; resources, J.P.; writing—original draft preparation, S.P. (Sunwoo Park), H.L. and J.P.; writing—review and editing, S.P. (Sunwoo Park), H.L. and J.P.; visualization, S.P. (Sangwook Park), S.O. and Y.H.; supervision, J.P.; project administration, J.P.; funding acquisition, J.P. All authors have read and agreed to the published version of the manuscript.

Funding

This work was supported by the GRRC program of Gyeonggi Province [(GRRCKYUNGHEE2023-B01), Development of ultra-fine process materials based on the sub-nanometer class for the next-generation semiconductors].

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Data are contained within the article or Supplementary Materials.

Conflicts of Interest

The authors declare no conflicts of interest.

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Applsci 14 04362 sch001
Scheme 1. Chemical structures of MBIQO and PBMBO.
Scheme 1. Chemical structures of MBIQO and PBMBO.
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Scheme 2. Synthesis route of PBMBO.
Scheme 2. Synthesis route of PBMBO.
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Figure 1. UV–Vis optical spectra: (a) absorbance spectra and (b) transmittance spectra of MBIQO and PBMBO in 1 × 10−4 M PGMEA solution.
Figure 1. UV–Vis optical spectra: (a) absorbance spectra and (b) transmittance spectra of MBIQO and PBMBO in 1 × 10−4 M PGMEA solution.
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Figure 2. Transmittance spectra of MBIQO and PBMBO in a drop-casting film.
Figure 2. Transmittance spectra of MBIQO and PBMBO in a drop-casting film.
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Figure 3. Thermogravimetric analysis (TGA) curves of MBIQO and PBMBO.
Figure 3. Thermogravimetric analysis (TGA) curves of MBIQO and PBMBO.
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Figure 4. Transmission electron microscopy (TEM) images of PBMBO.
Figure 4. Transmission electron microscopy (TEM) images of PBMBO.
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Figure 5. Transmittance spectra of MBIQO and PBMBO on a CR film.
Figure 5. Transmittance spectra of MBIQO and PBMBO on a CR film.
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Table 1. Transmittance and molar extinction coefficient values of MBIQO and PBMBO in 1 × 10−4 M PGMEA solution.
Table 1. Transmittance and molar extinction coefficient values of MBIQO and PBMBO in 1 × 10−4 M PGMEA solution.
MBIQOPBMBO
Transmittance
[%]		435 nm4.300.58
530 nm99.8095.90
Molar extinction coefficient a
[L/mol·cm]		1.23 × 1042.24 × 104
a at maximum absorption wavelength.
Table 2. Transmittance values of MBIQO and PBMBO in a drop-casting film.
Table 2. Transmittance values of MBIQO and PBMBO in a drop-casting film.
MBIQOPBMBO
435 nm36.6%0.82%
530 nm95.7%93.1%
Table 3. Solubility of MBIQO and PBMBO in PGMEA solvent.
Table 3. Solubility of MBIQO and PBMBO in PGMEA solvent.
MBIQOPBMBO
Solubility0.150.32
Table 4. Transmittance values of MBIQO and PBMBO on a CR film.
Table 4. Transmittance values of MBIQO and PBMBO on a CR film.
MBIQOPBMBO
435 nm3.63%0.03%
530 nm94.1%99.3%
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MDPI and ACS Style

Park, S.; Park, S.; Oh, S.; Heo, Y.; Lee, H.; Park, J. Novel Yellow Aromatic Imine Derivative Incorporating Oxazolone Moiety for Color Resist Applications. Appl. Sci. 2024, 14, 4362. https://doi.org/10.3390/app14114362

AMA Style

Park S, Park S, Oh S, Heo Y, Lee H, Park J. Novel Yellow Aromatic Imine Derivative Incorporating Oxazolone Moiety for Color Resist Applications. Applied Sciences. 2024; 14(11):4362. https://doi.org/10.3390/app14114362

Chicago/Turabian Style

Park, Sunwoo, Sangwook Park, Seyoung Oh, Yeongjae Heo, Hayoon Lee, and Jongwook Park. 2024. "Novel Yellow Aromatic Imine Derivative Incorporating Oxazolone Moiety for Color Resist Applications" Applied Sciences 14, no. 11: 4362. https://doi.org/10.3390/app14114362

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