KR20210027698A - Photosensitive resin composition, photosensitive resin layer using same, color filter and display device - Google Patents
Photosensitive resin composition, photosensitive resin layer using same, color filter and display device Download PDFInfo
- Publication number
- KR20210027698A KR20210027698A KR1020190108280A KR20190108280A KR20210027698A KR 20210027698 A KR20210027698 A KR 20210027698A KR 1020190108280 A KR1020190108280 A KR 1020190108280A KR 20190108280 A KR20190108280 A KR 20190108280A KR 20210027698 A KR20210027698 A KR 20210027698A
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- KR
- South Korea
- Prior art keywords
- formula
- photosensitive resin
- resin composition
- group
- binder resin
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 144
- 239000011347 resin Substances 0.000 title claims abstract description 144
- 239000011342 resin composition Substances 0.000 title claims abstract description 92
- 239000011230 binding agent Substances 0.000 claims abstract description 93
- 239000002096 quantum dot Substances 0.000 claims abstract description 71
- 239000004593 Epoxy Substances 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000000126 substance Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 239000000654 additive Substances 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 19
- 229920005822 acrylic binder Polymers 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
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- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 239000012965 benzophenone Substances 0.000 description 4
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
본 기재는 감광성 수지 조성물, 이를 이용하여 제조된 감광성 수지막, 상기 감광성 수지막을 포함하는 컬러필터 및 상기 컬러필터를 포함하는 디스플레이 장치에 관한 것이다.The present disclosure relates to a photosensitive resin composition, a photosensitive resin film prepared using the same, a color filter including the photosensitive resin film, and a display device including the color filter.
일반적으로 디스플레이에 적용하는 컬러필터는 감광성 레지스트 조성을 사용하여 포토마스크를 적용한 노광공정을 통해 원하는 패턴을 형성하고, 현상 공정을 통해 비노광부를 용해시켜 제거하는 패터닝 공정을 통해 컬러필터를 형성한다. 컬러필터용 소재는 알칼리 가용성이며 높은 감도, 기판에 대한 부착력, 내화학성, 내열성 등이 요구된다. 그런데 통상적으로 노광 공정만으로 경화반응이 충분하지 못하기 때문에 요구되는 특성들을 얻기 위해서는 200℃이상의 고온에서 일정시간 열경화 시켜주는 단계가 필요하다. 따라서 전자종이, OLED 등 저온 공정이 필요한 응용에는 한계가 있다.In general, a color filter applied to a display forms a desired pattern through an exposure process in which a photomask is applied using a photosensitive resist composition, and a color filter is formed through a patterning process in which an unexposed part is dissolved and removed through a development process. The color filter material is alkali-soluble and requires high sensitivity, adhesion to the substrate, chemical resistance, and heat resistance. However, since the curing reaction is not usually sufficient only by the exposure process, a step of thermally curing at a high temperature of 200°C or higher for a certain period of time is required in order to obtain the required properties. Therefore, there is a limit to applications requiring low-temperature processes such as e-paper and OLED.
한편, 전자종이, OLED 등 비교적 저온 공정 적용이 필요한 컬러 필터용 감광성 수지 조성물을 개발하기 위해, 조성물 내에 추가적인 화합물, 예컨대 에폭시드 및 과산화물 등을 첨가하여 부족한 경화특성을 보완하려는 노력이 있었으나, 경화도가 충분하지 않아, 신뢰성이 낮다는 문제점이 있다. On the other hand, in order to develop a photosensitive resin composition for color filters requiring relatively low-temperature process application such as electronic paper and OLED, efforts have been made to supplement the insufficient curing characteristics by adding additional compounds, such as epoxides and peroxides, in the composition. It is not enough, there is a problem that the reliability is low.
상기 문제점은 안료 또는 염료 등의 색재료가 광중합 개시제와 광에너지를 경쟁적으로 흡수하기 때문에 나타나는 현상이며, 또한 안료 및 염료가 생성된 라디칼을 제거하는 작용을 하기 때문에 충분한 개시효율을 얻기 어렵고, 따라서 광중합성 단량체의 경화율이 색재료를 사용하지 않은 경우보다 감소하게 되게 되는 것이다.The above problem is a phenomenon that occurs because color materials such as pigments or dyes absorb light energy competitively with the photopolymerization initiator, and it is difficult to obtain sufficient initiation efficiency because the pigments and dyes act to remove the generated radicals. The curing rate of the synthetic monomer decreases compared to the case where no color material is used.
따라서, 기존의 염료 혹은 안료 등의 색재료 대신 다른 물질을 사용함으로써 내화학성, 내열성 등의 신뢰성을 현저히 향상시킬 수 있는, 감광성 수지 조성물을 개발하려는 노력이 계속되고 있다.Accordingly, efforts to develop a photosensitive resin composition that can significantly improve reliability such as chemical resistance and heat resistance by using other materials instead of color materials such as conventional dyes or pigments have been continued.
일 구현예는 패턴성과 저장안정성이 우수하고, 열공정 이후 양자점의 광변환 유지율 저하를 최소화할 수 있는 양자점 함유 감광성 수지 조성물을 제공하기 위한 것이다.One embodiment is to provide a photosensitive resin composition containing a quantum dot, which has excellent pattern properties and storage stability, and can minimize a decrease in the photo-conversion retention rate of the quantum dot after a thermal process.
다른 일 구현예는 상기 감광성 수지 조성물을 이용하여 제조된 감광성 수지막을 제공하기 위한 것이다.Another embodiment is to provide a photosensitive resin film prepared by using the photosensitive resin composition.
또 다른 일 구현예는 상기 감광성 수지막을 포함하는 컬러필터를 제공하기 위한 것이다.Another embodiment is to provide a color filter including the photosensitive resin film.
또 다른 일 구현예는 상기 컬러필터를 포함하는 디스플레이 장치를 제공하기 위한 것이다.Another embodiment is to provide a display device including the color filter.
일 구현예는 (A) 양자점; (B) 바인더 수지; (C) 광중합성 단량체; (D) 광중합 개시제; 및 (E) 용매를 포함하고, 상기 (B) 바인더 수지는 (B-1) 하기 화학식 1로 표시되는 구조단위를 포함하는 카도계 바인더 수지 및 (B-2) 아크릴계 바인더 수지 및 에폭시계 바인더 수지로 이루어진 군에서 선택된 적어도 하나 이상의 바인더 수지를 포함하는 감광성 수지 조성물을 제공한다. One embodiment is (A) quantum dots; (B) binder resin; (C) photopolymerizable monomer; (D) photoinitiator; And (E) a solvent, wherein the (B) binder resin is (B-1) a cardo-based binder resin including a structural unit represented by the following formula (1), and (B-2) an acrylic-based binder resin and an epoxy-based binder resin. It provides a photosensitive resin composition comprising at least one binder resin selected from the group consisting of.
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R11 및 R12은 각각 독립적으로 하기 화학식 2로 표시되고,R 11 and R 12 are each independently represented by the following formula (2),
[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,
L1은 치환 또는 비치환된 C1 내지 C10 알킬렌기이고,L 1 is a substituted or unsubstituted C1 to C10 alkylene group,
L2는 산소 원자 또는 황 원자이고,L 2 is an oxygen atom or a sulfur atom,
R1은 "C1 내지 C10 알킬티오기로 치환된 C1 내지 C10 알킬기" 또는 "C1 내지 C10 알킬티오기로 치환된 C6 내지 C20 아릴기"이고,R 1 is “a C1 to C10 alkyl group substituted with a C1 to C10 alkylthio group” or “C6 to C20 aryl group substituted with a C1 to C10 alkylthio group”,
R13 및 R14는 각각 독립적으로 수소 원자, 할로겐 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기이고, R 13 and R 14 are each independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,
Z1은 단일결합, O, CO, SO2, CR17R18, SiR19R20(여기서, R17 내지 R20은 각각 독립적으로 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기임) 또는 하기 화학식 1-1 내지 화학식 1-11로 표시되는 연결기 중 어느 하나이고,Z 1 is a single bond, O, CO, SO 2 , CR 17 R 18 , SiR 19 R 20 (wherein R 17 to R 20 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or the following It is any one of the linking groups represented by Formula 1-1 to Formula 1-11,
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
(상기 화학식 1-5에서,(In Formula 1-5,
Ra는 수소 원자, 에틸기, C2H4Cl, C2H4OH, CH2CH=CH2 또는 페닐기이다.)R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH=CH 2 or a phenyl group.)
[화학식 1-6][Formula 1-6]
[화학식 1-7][Formula 1-7]
[화학식 1-8][Formula 1-8]
[화학식 1-9][Formula 1-9]
[화학식 1-10][Formula 1-10]
[화학식 1-11][Formula 1-11]
Z2는 산무수물 잔기이고,Z 2 is an acid anhydride residue,
t1 및 t2는 각각 독립적으로 0 내지 4의 정수이다.t1 and t2 are each independently an integer of 0 to 4.
상기 Z2는 하기 화학식 3 내지 화학식 5로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.Z 2 may be represented by any one selected from the group consisting of the following Chemical Formulas 3 to 5.
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
상기 화학식 3에서,In Chemical Formula 3,
L3은 단일결합, 산소 원자, 황 원자, *-C(=O)-* 또는 *-CR2R3-* (상기 R2 및 R3은 각각 독립적으로 할로겐원자로 치환 또는 비치환된 C1 내지 C10 알킬기)이다.L 3 is a single bond, an oxygen atom, a sulfur atom, *-C(=O)-* or *-CR 2 R 3 -* (wherein R 2 and R 3 are each independently substituted or unsubstituted with a halogen atom C1 to C10 alkyl group).
상기 카도계 바인더 수지는 2,000 g/mol 내지 20,000 g/mol의 중량평균분자량을 가질 수 있다.The cardo-based binder resin may have a weight average molecular weight of 2,000 g/mol to 20,000 g/mol.
상기 ‘카도계 바인더 수지’와 ‘아크릴계 바인더 수지 및 에폭시계 바인더 수지로 이루어진 군에서 선택된 적어도 하나 이상의 바인더 수지’는 2:1 내지 7:1의 중량비로 포함될 수 있다.The'cardo-based binder resin' and'at least one binder resin selected from the group consisting of an acrylic-based binder resin and an epoxy-based binder resin' may be included in a weight ratio of 2:1 to 7:1.
상기 아크릴계 바인더 수지는 이중결합 당량이 150 g/mol 내지 400 g/mol 일 수 있다.The acrylic binder resin may have a double bond equivalent of 150 g/mol to 400 g/mol.
상기 에폭시계 바인더 수지는 에폭시 당량이 100 g/eq 내지 200 g/eq 일 수 있다.The epoxy-based binder resin may have an epoxy equivalent of 100 g/eq to 200 g/eq.
상기 에폭시계 바인더 수지는 하기 화학식 6으로 표시될 수 있다.The epoxy-based binder resin may be represented by the following formula (6).
[화학식 6][Formula 6]
상기 화학식 6에서,In Chemical Formula 6,
R4는 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 4 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
n1 내지 n3은 각각 독립적으로 1 내지 20의 정수이다.n1 to n3 are each independently an integer of 1 to 20.
상기 감광성 수지 조성물은 (F) 확산제를 상기 감광성 수지 조성물 총량에 대해 0.5 중량% 내지 10 중량% 더 포함할 수 있다.The photosensitive resin composition may further include (F) a diffusing agent in 0.5% to 10% by weight based on the total amount of the photosensitive resin composition.
상기 확산제는 황산바륨, 탄산칼슘, 이산화티타늄, 지르코니아 또는 이들의 조합을 포함할 수 있다.The diffusion agent may include barium sulfate, calcium carbonate, titanium dioxide, zirconia, or a combination thereof.
상기 감광성 수지 조성물은 티올계 첨가제를 더 포함할 수 있다.The photosensitive resin composition may further include a thiol-based additive.
상기 티올계 첨가제는 말단에 하기 화학식 7로 표시되는 관능기를 적어도 2개 이상 포함할 수 있다.The thiol-based additive may include at least two or more functional groups represented by the following formula (7) at the terminal.
[화학식 7][Formula 7]
상기 화학식 7에서,In Chemical Formula 7,
L7 및 L8은 각각 독립적으로 단일결합, 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 치환 또는 비치환된 C2 내지 C20 헤테로아릴렌기이다.L 7 and L 8 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted It is a C2 to C20 heteroarylene group.
상기 양자점은 360 nm 내지 780nm의 광을 흡수해, 500nm 내지 700nm에서 형광을 방출하는 양자점일 수 있다.The quantum dots may be quantum dots that absorb light of 360 nm to 780 nm and emit fluorescence at 500 nm to 700 nm.
상기 감광성 수지 조성물은, 상기 감광성 수지 조성물 총량에 대해, 상기 (A) 양자점 1 중량% 내지 50 중량%; 상기 (B) 바인더 수지 1 중량% 내지 10 중량%; 상기 (C) 광중합성 단량체 1 중량% 내지 10 중량%; 상기 (D) 광중합 개시제 0.01 중량% 내지 5 중량%; 및 상기 (E) 용매 잔부량을 포함할 수 있다.The photosensitive resin composition, based on the total amount of the photosensitive resin composition, the (A) quantum dots 1% by weight to 50% by weight; (B) 1% to 10% by weight of the binder resin; (C) 1% to 10% by weight of the photopolymerizable monomer; (D) 0.01% to 5% by weight of the photopolymerization initiator; And the residual amount of the (E) solvent.
상기 감광성 수지 조성물은 말론산; 3-아미노-1,2-프로판디올; 실란계 커플링제; 레벨링제; 불소계 계면활성제; 또는 이들의 조합을 더 포함할 수 있다.The photosensitive resin composition is malonic acid; 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine-based surfactant; Or it may further include a combination of these.
다른 일 구현예는 상기 감광성 수지 조성물을 이용하여 제조된 감광성 수지막을 제공한다.Another embodiment provides a photosensitive resin film prepared by using the photosensitive resin composition.
또 다른 일 구현예는 상기 감광성 수지막을 포함하는 컬러필터를 제공한다.Another embodiment provides a color filter including the photosensitive resin film.
또 다른 일 구현예는 상기 컬러필터를 포함하는 디스플레이 장치를 제공한다.Another embodiment provides a display device including the color filter.
기타 본 발명의 측면들의 구체적인 사항은 이하의 상세한 설명에 포함되어 있다.Other specifics of aspects of the present invention are included in the detailed description below.
열공정을 포함하는 컬러필터 제조 공정을 거친 후에도, 양자점의 광변환 유지율 저하를 최소화하면서, 동시에 저장안정성 및 패턴성이 우수한 감광성 수지 조성물을 제공할 수 있다.Even after passing through the color filter manufacturing process including the thermal process, it is possible to provide a photosensitive resin composition having excellent storage stability and pattern property while minimizing the decrease in the photo-conversion retention rate of the quantum dot.
도 1은 실시예 1에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 단면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X20000)이다.
도 2는 실시예 2에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 단면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X20000)이다.
도 3은 실시예 3에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 단면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X20000)이다.
도 4는 비교예 1에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 단면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X20000)이다.
도 5는 비교예 2에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 단면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X20000)이다.
도 6은 실시예 1에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 표면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X15000)이다.
도 7은 실시예 2에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 표면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X15000)이다.
도 8은 실시예 3에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 표면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X15000)이다.
도 9는 비교예 1에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 표면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X15000)이다.
도 10은 비교예 2에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막의 패턴 표면의 집속이온빔(FIM) 주사전자현미경(SEM) 사진(X15000)이다.1 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X20000) of a pattern cross section of a photosensitive resin film prepared using the photosensitive resin composition according to Example 1. FIG.
FIG. 2 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X20000) of a pattern cross section of a photosensitive resin film prepared using the photosensitive resin composition according to Example 2. FIG.
3 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X20000) of a pattern cross section of a photosensitive resin film prepared using the photosensitive resin composition according to Example 3. FIG.
4 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X20000) of a pattern cross section of a photosensitive resin film prepared using the photosensitive resin composition according to Comparative Example 1. FIG.
5 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X20000) of a pattern cross section of a photosensitive resin film prepared using the photosensitive resin composition according to Comparative Example 2. FIG.
6 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X15000) of a pattern surface of a photosensitive resin film prepared using the photosensitive resin composition according to Example 1. FIG.
7 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X15000) of a pattern surface of a photosensitive resin film prepared using the photosensitive resin composition according to Example 2. FIG.
8 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X15000) of a pattern surface of a photosensitive resin film prepared using the photosensitive resin composition according to Example 3. FIG.
9 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X15000) of a pattern surface of a photosensitive resin film prepared using the photosensitive resin composition according to Comparative Example 1. FIG.
10 is a focused ion beam (FIM) scanning electron microscope (SEM) photograph (X15000) of a pattern surface of a photosensitive resin film prepared using the photosensitive resin composition according to Comparative Example 2. FIG.
이하, 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다. Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereby, and the present invention is only defined by the scope of the claims to be described later.
본 명세서에서 특별한 언급이 없는 한, "알킬기"란 C1 내지 C20 알킬기를 의미하고, "알케닐기"란 C2 내지 C20 알케닐기를 의미하고, "사이클로알케닐기"란 C3 내지 C20 사이클로알케닐기를 의미하고, "헤테로사이클로알케닐기"란 C3 내지 C20 헤테로사이클로알케닐기를 의미하고, "아릴기"란 C6 내지 C20 아릴기를 의미하고, "아릴알킬기"란 C6 내지 C20 아릴알킬기를 의미하며, "알킬렌기"란 C1 내지 C20 알킬렌기를 의미하고, "아릴렌기"란 C6 내지 C20 아릴렌기를 의미하고, "알킬아릴렌기"란 C6 내지 C20 알킬아릴렌기를 의미하고, "헤테로아릴렌기"란 C3 내지 C20 헤테로아릴렌기를 의미하고,"알콕실렌기"란 C1 내지 C20 알콕실렌기를 의미한다.Unless otherwise specified in the specification, "alkyl group" refers to a C1 to C20 alkyl group, "alkenyl group" refers to a C2 to C20 alkenyl group , and "cycloalkenyl group" refers to a C3 to C20 cycloalkenyl group , and , "Heterocycloalkenyl group" refers to a C3 to C20 heterocycloalkenyl group, "aryl group" refers to a C6 to C20 aryl group, and "arylalkyl group" refers to a C6 to C20 arylalkyl group, and "alkylene group" Refers to a C1 to C20 alkylene group, "arylene group" refers to a C6 to C20 arylene group, "alkylarylene group" refers to a C6 to C20 alkylarylene group, and "heteroarylene group" refers to a C3 to C20 hetero It means an arylene group, and the "alkoxyl group" means a C1 to C20 alkoxyl group.
본 명세서에서 특별한 언급이 없는 한, "치환"이란 적어도 하나의 수소 원자가 할로겐 원자(F, Cl, Br, I), 히드록시기, C1 내지 C20 알콕시기, 니트로기, 시아노기, 아민기, 이미노기, 아지도기, 아미디노기, 히드라지노기, 히드라조노기, 카르보닐기, 카르바밀기, 티올기, 에스테르기, 에테르기, 카르복실기 또는 그것의 염, 술폰산기 또는 그것의 염, 인산이나 그것의 염, C1 내지 C20 알킬기, C2 내지 C20 알케닐기, C2 내지 C20 알키닐기, C6 내지 C20 아릴기, C3 내지 C20 사이클로알킬기, C3 내지 C20 사이클로알케닐기, C3 내지 C20 사이클로알키닐기, C2 내지 C20 헤테로사이클로알킬기, C2 내지 C20 헤테로사이클로알케닐기, C2 내지 C20 헤테로사이클로알키닐기, C3 내지 C20 헤테로아릴기 또는 이들의 조합의 치환기로 치환된 것을 의미한다.Unless otherwise specified in the specification, "substituted" means that at least one hydrogen atom is a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, Azido group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, ether group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, C1 To C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C6 to C20 aryl group, C3 to C20 cycloalkyl group, C3 to C20 cycloalkenyl group, C3 to C20 cycloalkynyl group, C2 to C20 heterocycloalkyl group, C2 To C20 heterocycloalkenyl group, C2 to C20 heterocycloalkynyl group, C3 to C20 heteroaryl group, or a combination thereof.
또한 본 명세서에서 특별한 언급이 없는 한, "헤테로"란, 화학식 내에 N, O, S 및 P 중 적어도 하나의 헤테로 원자가 적어도 하나 포함된 것을 의미한다.In addition, unless otherwise specified in the specification, "hetero" means that at least one hetero atom of at least one of N, O, S, and P is included in the formula.
또한 본 명세서에서 특별한 언급이 없는 한, "(메타)아크릴레이트"는 "아크릴레이트"와 "메타크릴레이트" 둘 다 가능함을 의미하며, "(메타)아크릴산"은 "아크릴산"과 "메타크릴산" 둘 다 가능함을 의미한다. In addition, unless otherwise specified in the specification, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" refers to "acrylic acid" and "methacrylic acid. "It means both are possible.
본 명세서에서 특별한 언급이 없는 한, "조합"이란 혼합 또는 공중합을 의미한다.Unless otherwise specified in the specification, "combination" means mixing or copolymerization.
본 명세서 내 화학식에서 별도의 정의가 없는 한, 화학결합이 그려져야 하는 위치에 화학결합이 그려져있지 않은 경우는 상기 위치에 수소 원자가 결합되어 있음을 의미한다.Unless otherwise defined in the chemical formula in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded at the position.
또한 본 명세서에서 특별한 언급이 없는 한, "*"는 동일하거나 상이한 원자 또는 화학식과 연결되는 부분을 의미한다.In addition, unless otherwise specified in the specification, "*" means a moiety connected with the same or different atoms or chemical formulas.
일 구현예에 따른 감광성 수지 조성물은 (A) 양자점; (B) 바인더 수지; (C) 광중합성 단량체; (D) 광중합 개시제; 및 (E) 용매를 포함하며, 상기 (B) 바인더 수지는 (B-1) 하기 화학식 1로 표시되는 구조단위를 포함하는 카도계 바인더 수지 및 (B-2) 아크릴계 바인더 수지 및 에폭시계 바인더 수지로 이루어진 군에서 선택된 적어도 하나 이상의 바인더 수지를 포함한다. Photosensitive resin composition according to one embodiment (A) quantum dots; (B) binder resin; (C) photopolymerizable monomer; (D) photoinitiator; And (E) a solvent, wherein the (B) binder resin is (B-1) a cardo-based binder resin and (B-2) an acrylic-based binder resin and an epoxy-based binder resin including a structural unit represented by the following formula (1). It includes at least one or more binder resins selected from the group consisting of.
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R11 및 R12은 각각 독립적으로 하기 화학식 2로 표시되고,R 11 and R 12 are each independently represented by the following formula (2),
[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,
L1은 치환 또는 비치환된 C1 내지 C10 알킬렌기이고,L 1 is a substituted or unsubstituted C1 to C10 alkylene group,
L2는 산소 원자 또는 황 원자이고,L 2 is an oxygen atom or a sulfur atom,
R1은 "C1 내지 C10 알킬티오기로 치환된 C1 내지 C10 알킬기" 또는 "C1 내지 C10 알킬티오기로 치환된 C6 내지 C20 아릴기"이고,R 1 is “a C1 to C10 alkyl group substituted with a C1 to C10 alkylthio group” or “C6 to C20 aryl group substituted with a C1 to C10 alkylthio group”,
R13 및 R14는 각각 독립적으로 수소 원자, 할로겐 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기이고, R 13 and R 14 are each independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,
Z1은 단일결합, O, CO, SO2, CR17R18, SiR19R20(여기서, R17 내지 R20은 각각 독립적으로 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기임) 또는 하기 화학식 1-1 내지 화학식 1-11로 표시되는 연결기 중 어느 하나이고,Z 1 is a single bond, O, CO, SO 2 , CR 17 R 18 , SiR 19 R 20 (wherein R 17 to R 20 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or the following It is any one of the linking groups represented by Formula 1-1 to Formula 1-11,
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
(상기 화학식 1-5에서,(In Formula 1-5,
Ra는 수소 원자, 에틸기, C2H4Cl, C2H4OH, CH2CH=CH2 또는 페닐기이다.)R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH=CH 2 or a phenyl group.)
[화학식 1-6][Formula 1-6]
[화학식 1-7][Formula 1-7]
[화학식 1-8][Formula 1-8]
[화학식 1-9][Formula 1-9]
[화학식 1-10][Formula 1-10]
[화학식 1-11][Formula 1-11]
Z2는 산무수물 잔기이고,Z 2 is an acid anhydride residue,
t1 및 t2는 각각 독립적으로 0 내지 4의 정수이다.t1 and t2 are each independently an integer of 0 to 4.
일 구현예에 따른 감광성 수지 조성물은 바인더 수지로, 상기 화학식 1로 표시되는 구조단위를 포함하는 카도계 바인더 수지와 함께, 아크릴계 바인더 수지 및/또는 에폭시계 바인더 수지를 더 포함함으로써, 컬러펄티 제조 시 열 공정에서의 광변환율 저하를 최소화할 수 있을뿐만 아니라, 종래 바인더 수지를 적용한 감광성 수지 조성물과 비교하여, 감광성 수지막을 제조했을 때, 상기 수지막의 표면의 거칠기 및 단면의 암점(dark spot)을 최소화하여 패턴성을 향상시키고, 저장안정성 또한 개선시킬 수 있다. The photosensitive resin composition according to the embodiment is a binder resin, and further includes an acrylic binder resin and/or an epoxy binder resin together with a cardo-based binder resin including the structural unit represented by Formula 1 In addition to minimizing the decrease in the light conversion rate in the thermal process, when the photosensitive resin film is manufactured, compared to the photosensitive resin composition to which the conventional binder resin is applied, the roughness of the surface of the resin film and the dark spot of the cross-section are minimized. By doing so, it is possible to improve patternability and improve storage stability.
구체적으로, 본 발명은 최근 디스플레이 분야의 새로운 기술 트렌드로 자리잡고 있는, 디스플레이 장치에 적용되는 컬러필터용 양자점 함유 감광성 수지 조성물에 관한 것이다. Specifically, the present invention relates to a photosensitive resin composition containing quantum dots for a color filter applied to a display device, which has become a new technology trend in the recent display field.
양자점 디스플레이에 적용되는 양자점 함유 감광성 수지 조성물은 기존 조성물과 같이 광중합성 단량체, 바인더 수지, 광중합 개시제, 용매 등으로 기본 구성물을 이루며, 색재료로서 안료나 염료 대신 양자점과 광확산제를 사용하며, 양자점은 감광성 수지막 형성 후 입사되는 청색광을 적색광 및 녹색광으로 변환시키는 기능을 갖는다.Quantum dot-containing photosensitive resin composition applied to a quantum dot display constitutes a basic composition of a photopolymerizable monomer, a binder resin, a photopolymerization initiator, a solvent, etc., as in the existing composition, and uses a quantum dot and a light diffusing agent instead of a pigment or dye as a color material. Silver has a function of converting blue light incident after formation of the photosensitive resin film into red light and green light.
CdSe, InP 등으로 대표되는 양자점은 발광효율(Quantum Yield) 측면에서 빠르게 발전하여, 현재에는 발광효율이 100%에 가까운 합성법들이 소개되고 있으며, 현재 양자점 시트를 적용한 QD SUHD TV가 상품화까지 되었고, 다음 버전으로 양자점을 기존 LED TV의 컬러필터층에 포함시켜 더욱 높은 색재현율의 표현을 가능케하려는 기술에 대한 개발이 계속되고 있다. 그런데, 이러한 양자점 함유 감광성 수지 조성물이 적용된 TV의 핵심은 상기 조성물이 열공정-노광-현상-수세-증착 및 추가 열공정 등에서 양자점의 광 효율을 얼마나 잘 유지하느냐, 그리고 상기 조성물이 얼마나 패턴성을 잘 구현하느냐이며, 이 2가지가 제품개발의 key technology가 된다. Quantum dots represented by CdSe, InP, etc. have rapidly developed in terms of Quantum Yield, and now, synthesis methods with luminous efficiency close to 100% are being introduced, and QD SUHD TVs using quantum dot sheets have been commercialized. As a version, development of a technology to enable the expression of higher color gamut by including quantum dots in the color filter layer of the existing LED TV is continuing. However, the core of the TV to which such a photosensitive resin composition containing quantum dots is applied is how well the composition maintains the optical efficiency of the quantum dots in thermal process-exposure-development-washing-deposition and additional thermal processes, and how patterning the composition is. It is well implemented, and these two become key technologies for product development.
이러한 맥락에서 단계별 패터닝 프로세스에서 일정 수준의 발광효율, 열 안정성 및 물리적 모폴로지(morphology) 특성을 유지시킬 수 있는 조성물이 요구되고 있으나, 아직까지 요구되고 있는 수준의 조성물은 개발되지 않고 있다.In this context, a composition capable of maintaining a certain level of luminous efficiency, thermal stability, and physical morphology characteristics in a step-by-step patterning process is required, but a composition at the required level has not been developed.
본 발명자들은 오랜 연구 끝에, 바인더 수지의 조성을 변화시킴으로써, 시장에서 요구되는 수준, 즉 열공정 등을 거친 후에도 양자점이 우수한 광변환 효율을 유지하며 동시에 패턴성과 저장안정성까지 개선시킬 수 있는 확인하였으며, 본 발명은 상기와 같은 수준을 구현할 수 있는 양자점 함유 감광성 수지 조성물에 대한 것이다.After a long study, the inventors have confirmed that by changing the composition of the binder resin, the quantum dots can maintain excellent photo-conversion efficiency even after going through a level required in the market, that is, thermal process, and at the same time improve pattern and storage stability. The present invention relates to a photosensitive resin composition containing quantum dots that can achieve the same level as described above.
이하에서 각 성분에 대하여 구체적으로 설명한다.Hereinafter, each component will be described in detail.
(A) 양자점(A) quantum dots
상기 양자점은 360nm 내지 780nm의 파장영역, 예컨대 400nm 내지 780nm의 파장영역의 광을 흡수하여, 500nm 내지 700nm의 파장영역, 예컨대 500nm 내지 580nm에서 형광을 방출하거나, 600nm 내지 680nm에서 형광을 방출할 수 있다. 즉, 상기 광변환 물질은 500nm 내지 680nm에서 최대형광 발광파장(fluorescence λem)을 가질 수 있다.The quantum dots may absorb light in a wavelength region of 360 nm to 780 nm, such as 400 nm to 780 nm, and emit fluorescence in a wavelength region of 500 nm to 700 nm, such as 500 nm to 580 nm, or may emit fluorescence in a wavelength region of 600 nm to 680 nm. . That is, the photoconversion material may have a maximum fluorescence emission wavelength (fluorescence λ em ) at 500 nm to 680 nm.
상기 양자점은 각각 독립적으로 20nm 내지 100nm, 예컨대 20nm 내지 50nm의 반치폭(Full width at half maximum; FWHM)을 가질 수 있다. 상기 양자점이 상기 범위의 반치폭을 가질 경우, 색순도가 높음에 따라, 컬러필터 내 색재료로 사용 시 색재현율이 높아지는 효과가 있다.Each of the quantum dots may independently have a full width at half maximum (FWHM) of 20 nm to 100 nm, for example, 20 nm to 50 nm. When the quantum dots have a half width of the above range, as the color purity is high, when used as a color material in a color filter, there is an effect of increasing the color reproducibility.
상기 양자점은 각각 독립적으로 유기물이거나 무기물 또는 유기물과 무기물의 하이브리드(혼성물)일 수 있다.The quantum dots may each independently be an organic material, an inorganic material, or a hybrid (mixture) of an organic material and an inorganic material.
상기 양자점은 각각 독립적으로 코어 및 상기 코어를 감싸는 쉘로 구성될 수 있으며, 상기 코어 및 쉘은 각각 독립적으로 II-IV족, III-V족 등으로 이루어진 코어, 코어/쉘, 코어/제1쉘/제2쉘, 합금, 합금/쉘 등의 구조를 가질 수 있으며, 이에 한정되는 것은 아니다.The quantum dots may each independently consist of a core and a shell surrounding the core, and the core and shell are each independently a core, a core/shell, a core/first shell/ It may have a structure such as a second shell, an alloy, and an alloy/shell, but is not limited thereto.
예컨대, 상기 코어는 CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, GaN, GaP, GaAs, InP, InAs 및 이들의 합금으로 이루어진 군으로부터 선택된 적어도 하나 이상의 물질을 포함할 수 있으나, 반드시 이에 한정되는 것은 아니다. 상기 코어를 둘러싼 쉘은 CdSe, ZnSe, ZnS, ZnTe, CdTe, PbS, TiO, SrSe, HgSe 및 이들의 합금으로 이루어진 군으로부터 선택된 적어도 하나 이상의 물질을 포함할 수 있으나, 반드시 이에 한정되는 것은 아니다. For example, the core may include at least one material selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, GaN, GaP, GaAs, InP, InAs, and alloys thereof. , Is not necessarily limited thereto. The shell surrounding the core may include at least one material selected from the group consisting of CdSe, ZnSe, ZnS, ZnTe, CdTe, PbS, TiO, SrSe, HgSe, and alloys thereof, but is not limited thereto.
일 구현예에서는, 최근 전 세계적으로 환경에 대한 관심이 크게 증가하고 유독성 물질에 대한 규제가 강화되고 있으므로, 카드뮴계 코어를 갖는 발광물질을 대신하여, 양자 효율(quantum yield)은 다소 낮지만 친환경적인 비카드뮴계 발광소재(InP/ZnS)를 사용하였으나, 반드시 이에 한정되는 것은 아니다.In one embodiment, since interest in the environment has recently increased greatly around the world and regulations on toxic substances have been strengthened, instead of a light emitting material having a cadmium-based core, the quantum yield is somewhat low, but environmentally friendly. Although a non-cadmium-based light emitting material (InP/ZnS) was used, it is not necessarily limited thereto.
상기 양자점의 구조는 특별하게 한정되지 않으나, 상기 코어/쉘 구조의 양자점의 경우, 쉘을 포함한 전체 양자점 각각의 크기(평균 입경)는 1nm 내지 15nm, 예컨대 5nm 내지 15nm 일 수 있다. The structure of the quantum dot is not particularly limited, but in the case of the quantum dot of the core/shell structure, the size (average particle diameter) of each of the entire quantum dots including the shell may be 1 nm to 15 nm, for example, 5 nm to 15 nm.
예컨대, 상기 양자점은 각각 독립적으로 적색 양자점, 녹색 양자점 또는 이들의 조합을 포함할 수 있다. 상기 적색 양자점은 각각 독립적으로 10nm 내지 15nm의 평균 입경을 가질 수 있다. 상기 녹색 양자점은 각각 독립적으로 5nm 내지 8nm의 평균 입경을 가질 수 있다.For example, the quantum dots may each independently include red quantum dots, green quantum dots, or a combination thereof. Each of the red quantum dots may independently have an average particle diameter of 10 nm to 15 nm. Each of the green quantum dots may independently have an average particle diameter of 5 nm to 8 nm.
한편, 상기 양자점의 분산안정성을 위해, 일 구현예에 따른 감광성 수지 조성물은 분산제를 더 포함할 수도 있다. 상기 분산제는 양자점과 같은 광변환 물질이 감광성 수지 조성물 내에서 균일하게 분산되도록 도와주며, 비이온성, 음이온성 또는 양이온성 분산제 모두를 사용할 수 있다. 구체적으로는 폴리알킬렌 글리콜 또는 이의 에스테르류, 폴리옥시 알킬렌, 다가 알코올 에스테르 알킬렌 옥사이드 부가물, 알코올 알킬렌 옥사이드 부가물, 술폰산 에스테르, 술폰산 염, 카르복시산 에스테르, 카르복시산 염, 알킬 아미드 알킬렌 옥사이드 부가물, 알킬 아민 등을 사용할 수 있으며, 이들은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. 상기 분산제는 양자점과 같은 광변환 물질의 고형분 대비 0.1 중량% 내지 100 중량%, 예컨대 10 중량% 내지 20 중량%로 사용될 수 있다.Meanwhile, for the dispersion stability of the quantum dots, the photosensitive resin composition according to an embodiment may further include a dispersant. The dispersant helps to uniformly disperse a photo-conversion material such as quantum dots in the photosensitive resin composition, and nonionic, anionic, or cationic dispersants may be used. Specifically, polyalkylene glycol or esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salt, alkyl amide alkylene oxide Adducts, alkyl amines, and the like may be used, and these may be used alone or in combination of two or more. The dispersant may be used in an amount of 0.1% to 100% by weight, such as 10% to 20% by weight, based on the solid content of a photo-conversion material such as a quantum dot.
상기 양자점은 일 구현예에 따른 감광성 수지 조성물 총량에 대해 1 중량% 내지 50 중량%, 예컨대 10 중량% 내지 50 중량%로 포함될 수 있다. 상기 양자점이 상기 범위 내로 포함될 경우, 광변환률이 우수하며 패턴 특성과 현상 특성을 저해하지 않아 우수한 공정성을 가질 수 있다. The quantum dots may be included in an amount of 1% to 50% by weight, such as 10% to 50% by weight, based on the total amount of the photosensitive resin composition according to an embodiment. When the quantum dots are included within the above range, the light conversion rate is excellent and the pattern characteristics and development characteristics are not impaired, so that excellent fairness may be obtained.
(B) 바인더 수지(B) binder resin
상기 바인더 수지는 상기 화학식 1로 표시되는 구조단위를 포함하는 카도계 바인더 수지와 아크릴계 바인더 수지 및/또는 에폭시계 바인더 수지를 더 포함한다.The binder resin further includes a cardo-based binder resin including a structural unit represented by Chemical Formula 1, an acrylic binder resin, and/or an epoxy-based binder resin.
구체적으로, 상기 화학식 2에서, L2의 산소 원자 또는 황 원자(보다 구체적으로는 황 원자) 및 R1의 티오기를 구성하는 황 원자가 전술한 양자점 표면에 리간드로 작용하여 바인딩하거나, 양자점을 패시베이션하여, 양자점의 분산 및 안정성이 개선되어, 궁극적으로 광변환율의 저하를 방지할 수 있다.Specifically, in Formula 2, an oxygen atom or a sulfur atom of L 2 (more specifically, a sulfur atom) and a sulfur atom constituting a thio group of R 1 act as a ligand to bind to the surface of the quantum dot, or passivate the quantum dot. , The dispersion and stability of the quantum dots are improved, and ultimately, a decrease in the light conversion rate can be prevented.
청색광 변환에 핵심적인 기능을 하는 양자점은 소수성 리간드(Hydrophobic ligand)로 둘러싸여 있어 소수성을 가지며, 이 때문에 양자점은 친수성인 감광성 수지 조성물에 투입 시 분산성이 떨어지는 문제가 필연적으로 발생할 수 밖에 없다. 이러한 분산성 문제를 해결하기 위해 양자점 표면의 리간드 치환을 비롯한 패시베이션 연구가 많이 진행되고 있으며, 특히 특정 화합물을 사용하여 리간드 교환 반응을 일으켜 양자점 표면을 표면개질시키는 기술에 대한 연구가 활발하게 진행되고 있다. 그러나, 이와 같이 리간드 교환된 양자점(표면개질된 양자점)은 감광성 수지 조성물의 패터닝 공정 중 열 공정에 의해 광변환 능력이 크게 저하되는 것은 마찬가지기에, 양자점의 표면개질만으로는 종래 문제점을 완전히 해결하기에는 많이 역부족이었다.Quantum dots, which play a key function in blue light conversion, have hydrophobicity because they are surrounded by a hydrophobic ligand, and therefore, when the quantum dots are introduced into a hydrophilic photosensitive resin composition, the problem of poor dispersibility inevitably occurs. In order to solve this dispersibility problem, a lot of researches on passivation including ligand substitution on the surface of quantum dots are being conducted, and in particular, research on a technology to surface-modify the surface of quantum dots by causing a ligand exchange reaction using a specific compound is actively progressing. . However, since the photosensitive resin composition's photosensitive resin composition patterning process significantly lowers its photoconversion ability, the quantum dot surface modification alone is not enough to completely solve the conventional problems. Was.
그러나, 일 구현예에 따르면, 별도의 리간드 교환 물질을 사용하지 않아 열 공정에 의한 양자점의광변환 능력을 크게 저하시키지 않으면서 동시에 양자점의 분산성과 열에 의한 광변환 효율을 더욱 향상시키기 위해 카도계 바인더 수지 내에 thiol 및/또는 sulfide(-SH 및/또는 -S-)를 도입함으로써, 상기 카도계 바인더 수지가 양자점 표면에 직접 리간드로 작용하여 바인딩(binding)하거나 양자점을 패시베이션(passivation)하여, 양자점의 분산 및 안정성에 긍정적 효과를 가져온다. 나아가 상기 카도계 바인더 수지와 함께 아크릴계 바인더 수지나 에폭시계 바인더 수지를 추가로 사용함으로써, 열 공정 후에도 전체 조성물이 안정된 상태로 유지되도록 함으로써, 양자점의 광변환 효율을 비롯한 모폴로지(Morphology) 특성의 균일화 효과, 즉 수지막의 표면 내 홀 발생 최소화 및 수지막의 단막 내 암점 최소화를 꾀할 수 있다.However, according to an embodiment, since a separate ligand exchange material is not used, cardo-based binders are used to further improve the dispersibility of the quantum dots and the photoconversion efficiency due to heat without significantly lowering the photoconversion ability of the quantum dots by the thermal process. By introducing thiol and/or sulfide (-SH and/or -S-) into the resin, the cardo-based binder resin directly acts as a ligand on the surface of the quantum dot to bind or passivation of the quantum dot. It has a positive effect on dispersion and stability. Furthermore, by additionally using an acrylic binder resin or an epoxy binder resin together with the cardo-based binder resin, the entire composition is maintained in a stable state even after the thermal process, thereby equalizing the morphology characteristics including the light conversion efficiency of quantum dots. That is, it is possible to minimize the occurrence of holes in the surface of the resin film and to minimize dark spots in the single film of the resin film.
예컨대, 상기 R1은 C1 내지 C5 알킬티오기로 치환된 C1 내지 C5 알킬기 또는 C1 내지 C5 알킬티오기로 치환된 C6 내지 C10 아릴기일 수 있다. 상기 R1이 알킬티오기인 경우, 에폭시기나 아크릴레이트기로 치환된 알킬기나 아릴기 등인 경우 대비 우수한 패턴성 및 저장안정성을 가질 수 있고, 열공정 이후의 광변환 유지율도 양호한 특성을 가질 수 있어 바람직하다.For example, R 1 may be a C1 to C5 alkyl group substituted with a C1 to C5 alkylthio group or a C6 to C10 aryl group substituted with a C1 to C5 alkylthio group. When R 1 is an alkylthio group, it is preferable because it can have excellent patterning properties and storage stability compared to the case of an alkyl group or an aryl group substituted with an epoxy group or an acrylate group, and the photoconversion retention rate after the thermal process can also have good properties. .
예컨대, 상기 Z2는 하기 화학식 3 내지 화학식 5로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.For example, Z 2 may be represented by any one selected from the group consisting of the following Chemical Formulas 3 to 5.
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
상기 화학식 3에서,In Chemical Formula 3,
L3은 단일결합, 산소 원자, 황 원자, *-C(=O)-* 또는 *-CR2R3-* (상기 R2 및 R3은 각각 독립적으로 할로겐원자로 치환 또는 비치환된 C1 내지 C10 알킬기)이다.L 3 is a single bond, an oxygen atom, a sulfur atom, *-C(=O)-* or *-CR 2 R 3 -* (wherein R 2 and R 3 are each independently substituted or unsubstituted with a halogen atom C1 to C10 alkyl group).
예컨대, 상기 화학식 3에서, L3은 황 원자일 수 있다.For example, in Formula 3, L 3 may be a sulfur atom.
상기 카도계 바인더 수지는 상기 화학식 1로 표시되는 구조단위를 2 이상 포함할 수 있다. The cardo-based binder resin may include two or more structural units represented by Chemical Formula 1.
상기 카도계 바인더 수지는 2,000 g/mol 내지 20,000 g/mol의 중량평균분자량, 예컨대 3,000 g/mol 내지 10,000 g/mol의 중량평균분자량을 가질 수 있다. 상기 카도계 바인더 수지의 중량평균 분자량이 상기 범위 내일 경우 컬러필터 제조 시 잔사 없이 패턴 형성이 잘되며, 현상 시 막두께의 손실이 없고, 양호한 패턴을 얻을 수 있다.The cardo-based binder resin may have a weight average molecular weight of 2,000 g/mol to 20,000 g/mol, for example, 3,000 g/mol to 10,000 g/mol. When the weight average molecular weight of the cardo-based binder resin is within the above range, pattern formation is well performed without residues during manufacturing of a color filter, there is no loss of film thickness during development, and a good pattern can be obtained.
상기 카도계 바인더 수지는 양 말단 중 적어도 하나에 하기 화학식 10으로 표시되는 관능기를 포함할 수 있다.The cardo-based binder resin may include a functional group represented by the following Formula 10 at at least one of both ends.
[화학식 10][Formula 10]
상기 화학식 10에서,In Chemical Formula 10,
Z3은 하기 화학식 10-1 내지 화학식 10-7로 표시될 수 있다.Z 3 may be represented by the following Chemical Formulas 10-1 to 10-7.
[화학식 10-1][Formula 10-1]
(상기 화학식 10-1에서, Rb 및 Rc는 각각 독립적으로, 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기, 에스테르기 또는 에테르기이다.)(In Formula 10-1, R b and R c are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group, or an ether group.)
[화학식 10-2][Formula 10-2]
[화학식 10-3][Formula 10-3]
[화학식 10-4][Formula 10-4]
[화학식 10-5][Formula 10-5]
(상기 화학식 10-5에서, Rd는 O, S, NH, 치환 또는 비치환된 C1 내지 C20 알킬렌기, C1 내지 C20 알킬아민기 또는 C2 내지 C20 알케닐아민기이다.)(In Formula 10-5, R d is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, a C1 to C20 alkylamine group, or a C2 to C20 alkenylamine group.)
[화학식 10-6][Formula 10-6]
[화학식 10-7][Formula 10-7]
일 구현예에 따른 감광성 수지 조성물은 아크릴계 바인더 수지를 더 포함할 수 있다.The photosensitive resin composition according to an embodiment may further include an acrylic binder resin.
상기 아크릴계 바인더 수지는 제1 에틸렌성 불포화 단량체및 이와 공중합 가능한 제2 에틸렌성 불포화 단량체의 공중합체로, 하나 이상의 아크릴계 반복단위를 포함하는 수지일 수 있다.The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin including one or more acrylic repeating units.
상기 제1 에틸렌성 불포화 단량체는 하나 이상의 카르복시기를 함유하는 에틸렌성 불포화 단량체이며, 이의 구체적인 예로는 아크릴산, 메타크릴산, 말레산, 이타콘산, 푸마르산, 또는 이들의 조합을 들 수 있다.The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxy group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
상기 제1 에틸렌성 불포화 단량체는 상기 아크릴계 바인더 수지 총량에 대하여5 중량%내지50중량%, 예컨대 10 중량%내지40 중량%로 포함될 수 있다.The first ethylenically unsaturated monomer may be included in an amount of 5% to 50% by weight, such as 10% to 40% by weight, based on the total amount of the acrylic binder resin.
상기 제2 에틸렌성 불포화 단량체는 스티렌, α-메틸스티렌, 비닐톨루엔, 비닐벤질메틸에테르 등의 방향족 비닐 화합물; 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 2-히드록시에틸(메타)아크릴레이트, 2-히드록시 부틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 사이클로헥실(메타)아크릴레이트, 페닐(메타)아크릴레이트 등의 불포화 카르복시산 에스테르 화합물; 2-아미노에틸(메타)아크릴레이트, 2-디메틸아미노에틸(메타)아크릴레이트 등의 불포화 카르복시산 아미노 알킬 에스테르 화합물; 초산비닐, 안식향산 비닐 등의 카르복시산 비닐 에스테르 화합물; 글리시딜(메타)아크릴레이트 등의 불포화 카르복시산 글리시딜 에스테르 화합물; (메타)아크릴로니트릴 등의 시안화 비닐 화합물; (메타)아크릴아미드 등의 불포화 아미드 화합물; 등을 들 수 있으며, 이들을 단독으로 또는 둘 이상 혼합하여 사용할 수 있다.The second ethylenically unsaturated monomer may include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzylmethylether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth)acrylate and phenyl (meth)acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds such as (meth)acrylonitrile; Unsaturated amide compounds such as (meth)acrylamide; And the like, and these may be used alone or in combination of two or more.
상기 아크릴계 바인더 수지의 구체적인 예로는 폴리벤질메타크릴레이트, (메타)아크릴산/벤질메타크릴레이트 공중합체, (메타)아크릴산/벤질메타크릴레이트/스티렌 공중합체, (메타)아크릴산/벤질메타크릴레이트/2-히드록시에틸메타크릴레이트 공중합체, (메타)아크릴산/벤질메타크릴레이트/스티렌/2-히드록시에틸메타크릴레이트 공중합체 등을 들 수 있으나, 이에 한정되는 것은 아니며, 이들을 단독 또는 2종 이상을 배합하여 사용할 수도 있다. Specific examples of the acrylic binder resin include polybenzyl methacrylate, (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/benzyl methacrylate/ 2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc. may be mentioned, but are not limited thereto, and these The above can also be used in combination.
상기 아크릴계 바인더 수지의 중량평균 분자량은 5,000 g/mol 내지 20,000g/mol 일 수 있다. 상기 아크릴계 바인더 수지의 중량평균 분자량이 상기 범위 내일 경우, 기판과의 밀착성이 우수하고 물리적, 화학적 물성이 좋으며, 점도가 적절하다.The weight average molecular weight of the acrylic binder resin may be 5,000 g/mol to 20,000 g/mol. When the weight average molecular weight of the acrylic binder resin is within the above range, adhesion to the substrate is excellent, physical and chemical properties are good, and viscosity is appropriate.
상기 아크릴계 바인더 수지의 산가는 80 mgKOH/g 내지 130 mgKOH/g 일 수 있다. 상기 아크릴계 바인더 수지의 산가가 상기 범위 내일 경우 픽셀 패턴의 해상도가 우수하다.The acid value of the acrylic binder resin may be 80 mgKOH/g to 130 mgKOH/g. When the acid value of the acrylic binder resin is within the above range, the resolution of the pixel pattern is excellent.
상기 아크릴계 바인더 수지는 이중결합 당량이 150 g/mol 내지 400 g/mol 일 수 있다. 상기 아크릴계 바인더 수지의 이중결합 당량이 상기 범위 이내일 경우 열 공정 이후 광흡수율 저하 현상을 효과적으로 방지할 수 있다.The acrylic binder resin may have a double bond equivalent of 150 g/mol to 400 g/mol. When the double bond equivalent of the acrylic binder resin is within the above range, a decrease in light absorption rate after the thermal process can be effectively prevented.
일 구현예에 따른 감광성 수지 조성물은 에폭시계 바인더 수지를 더 포함할 수 있다.The photosensitive resin composition according to an embodiment may further include an epoxy-based binder resin.
예컨대, 상기 예폭시계 바인더 수지로 노볼락형 에폭시계 화합물, 비스페놀 A형 에폭시계 화합물, 크레졸 노볼락형 에폭시계 화합물, 비페닐형 에폭시계 화합물 등을 들 수 있으나, 반드시 이에 한정되는 것은 아니다.For example, a novolak type epoxy compound, a bisphenol A type epoxy compound, a cresol novolak type epoxy compound, a biphenyl type epoxy compound, and the like may be mentioned as the amplified clock binder resin, but the present invention is not limited thereto.
상기 에폭시계 바인더 수지는 에폭시 당량이 100 g/eq 내지 190 g/eq 일 수 있다. 상기 범위의 에폭시 당량을 가지는 에폭시계 바인더 수지를 사용할 경우, 패턴성 개선 및 열공정 이후의 광변환 유지율 저하를 최소화하는데 큰 도움을 줄 수 있다.The epoxy-based binder resin may have an epoxy equivalent of 100 g/eq to 190 g/eq. In the case of using an epoxy-based binder resin having an epoxy equivalent in the above range, it can be of great help in improving pattern properties and minimizing a decrease in photo-conversion retention rate after a thermal process.
예컨대, 상기 에폭시계 바인더 수지는 하기 화학식 6으로 표시될 수 있다.For example, the epoxy-based binder resin may be represented by Formula 6 below.
[화학식 6][Formula 6]
상기 화학식 6에서,In Chemical Formula 6,
R4는 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 4 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
n1 내지 n3은 각각 독립적으로 1 내지 20의 정수이다.n1 to n3 are each independently an integer of 1 to 20.
예컨대, 상기 화학식 6에서, n1 내지 n3은 각각 독립적으로 1 내지 13의 정수이고, 상기 n1+n2+n3은 15의 정수일 수 있다.For example, in Formula 6, n1 to n3 may each independently be an integer of 1 to 13, and n1+n2+n3 may be an integer of 15.
상기 ‘카도계 바인더 수지’와 ‘아크릴계 바인더 수지 및 에폭시계 바인더 수지로 이루어진 군에서 선택된 적어도 하나 이상의 바인더 수지’는 2:1 내지 7:1의 중량비로 포함될 수 있다. 예컨대, 상기 카도계 바인더 수지 및 아크릴계 바인더 수지는 2:1 내지 7:1의 중량비로 포함될 수 있고, 상기 카도계 바인더 수지 및 에폭시계 바인더 수지는 2:1 내지 7:1의 중량비로 포함될 수 있고, 상기 '카도계 바인더 수지' 및 '아크릴계 바인더 수지 및 에폭시계 바인더 수지'는 2:1 내지 7:1의 중량비로 포함될 수 있다. 상기 바인더 수지 간 중량비가 상기 범위를 만족할 경우, 우수한 패턴성, 우수한 저장안정성 및 열공정 이후의 광변환 유지율 저하 방지 등의 효과를 동시에 달성할 수 있다. The'cardo-based binder resin' and'at least one binder resin selected from the group consisting of an acrylic-based binder resin and an epoxy-based binder resin' may be included in a weight ratio of 2:1 to 7:1. For example, the cardo-based binder resin and the acrylic-based binder resin may be included in a weight ratio of 2:1 to 7:1, and the cardo-based binder resin and the epoxy-based binder resin may be included in a weight ratio of 2:1 to 7:1, , The'cardo-based binder resin' and'acrylic-based binder resin and epoxy-based binder resin' may be included in a weight ratio of 2:1 to 7:1. When the weight ratio between the binder resins satisfies the above range, effects such as excellent patterning properties, excellent storage stability, and prevention of reduction of the photoconversion retention rate after the thermal process can be simultaneously achieved.
상기 바인더 수지는 감광성 수지 조성물 총량에 대하여 1 중량% 내지 10 중량%, 예컨대 1 중량% 내지 5 중량%로 포함될 수 있다. 바인더 수지가 상기 범위 내로 포함되는 경우 우수한 감도, 현상성, 해상도 및 패턴의 직진성을 얻을 수 있다.The binder resin may be included in an amount of 1% to 10% by weight, such as 1% to 5% by weight, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent sensitivity, developability, resolution, and straightness of the pattern can be obtained.
(C) 광중합성 단량체(C) photopolymerizable monomer
상기 광중합성 단량체는, 적어도 1개의 에틸렌성 불포화 이중결합을 가지는 (메타)아크릴산의 일관능 또는 다관능 에스테르가 사용될 수 있다.As the photopolymerizable monomer, a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond may be used.
상기 광중합성 단량체는 상기 에틸렌성 불포화 이중결합을 가짐으로써, 패턴 형성 공정에서 노광시 충분한 중합을 일으킴으로써 내열성, 내광성 및 내화학성이 우수한 패턴을 형성할 수 있다.Since the photopolymerizable monomer has the ethylenically unsaturated double bond, it is possible to form a pattern having excellent heat resistance, light resistance, and chemical resistance by causing sufficient polymerization during exposure in the pattern formation process.
상기 광중합성 단량체의 구체적인 예로는, 에틸렌 글리콜 디(메타)아크릴레이트, 디에틸렌 글리콜 디(메타)아크릴레이트, 트리에틸렌 글리콜 디(메타)아크릴레이트, 프로필렌 글리콜 디(메타)아크릴레이트, 네오펜틸 글리콜 디(메타)아크릴레이트, 1,4-부탄디올 디(메타)아크릴레이트, 1,6-헥산디올 디(메타)아크릴레이트, 비스페놀A 디(메타)아크릴레이트, 펜타에리트리톨 디(메타)아크릴레이트, 펜타에리트리톨 트리(메타)아크릴레이트, 펜타에리트리톨 테트라(메타)아크릴레이트, 펜타에리트리톨 헥사(메타)아크릴레이트, 디펜타에리트리톨 디(메타)아크릴레이트, 디펜타에리트리톨 트리(메타)아크릴레이트, 디펜타에리트리톨 펜타(메타)아크릴레이트, 디펜타에리트리톨 헥사(메타)아크릴레이트, 비스페놀A 에폭시(메타)아크릴레이트, 에틸렌 글리콜 모노메틸에테르 (메타)아크릴레이트, 트리메틸올 프로판 트리(메타)아크릴레이트, 트리스(메타)아크릴로일옥시에틸 포스페이트, 노볼락에폭시 (메타)아크릴레이트 등을 들 수 있다. Specific examples of the photopolymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol Di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate , Pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth) Acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, trimethylol propane tri( Meth)acrylate, tris(meth)acryloyloxyethyl phosphate, novolac epoxy (meth)acrylate, and the like.
상기 광중합성 단량체의 시판되는 제품을 예로 들면 다음과 같다. 상기 (메타)아크릴산의 일관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-101®, 동 M-111®, 동 M-114® 등; 니혼 가야꾸(주)社의 KAYARAD TC-110S®, 동 TC-120S® 등; 오사카 유끼 가가꾸 고교(주)社의 V-158®, V-2311® 등을 들 수 있다. 상기 (메타)아크릴산의 이관능 에스테르의 예로는, 도아 고세이 가가꾸고교(주)社의 아로닉스 M-210®, 동 M-240®, 동 M-6200® 등; 니혼 가야꾸(주)社의 KAYARAD HDDA®, 동 HX-220®, 동 R-604® 등; 오사카 유끼 가가꾸 고교(주)社의 V-260®, V-312®, V-335 HP® 등을 들 수 있다. 상기 (메타)아크릴산의 삼관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-309®, 동 M-400®, 동 M-405®, 동 M-450®, 동 M-7100®, 동 M-8030®, 동 M-8060® 등; 니혼 가야꾸(주)社의 KAYARAD TMPTA®, 동 DPCA-20®, 동-30®, 동-60®, 동-120® 등; 오사카 유끼 가야꾸 고교(주)社의 V-295®, 동-300®, 동-360®, 동-GPT®, 동-3PA®, 동-400® 등을 들 수 있다. 상기 제품을 단독 사용 또는 2종 이상 함께 사용할 수 있다.For example, commercially available products of the photopolymerizable monomer are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ®, the same M-111 ®, the same M-114 ®; KAYARAD TC-110S ® of Nihon Kayaku Co., Ltd., TC-120S ®, etc.; Osaka yukki the like Kagaku Kogyo (main)社of V-158 ®, V-2311 ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei cultivating the T (weeks)社of Aronix M-210 ®, copper or the like M-240 ®, the same M-6200 ®; KAYARAD HDDA ® , HX-220 ® , R-604 ® of Nihon Kayaku Co., Ltd.; Osaka Yuki Kagaku High School Co., Ltd.'s V-260 ® , V-312 ® , and V-335 HP ® are listed. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ®, the same M-400 ®, the same M-405 ®, the same M-450 ®, Dong M ® -7100, Dong M-8030 ®, same M-8060 ®, and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ®, copper DPCA-20 ®, ® copper -30, -60 ® copper, copper ® -120 and the like; Osaka Yuki Kayaku High School Co., Ltd.'s V-295 ® , East-300 ® , East-360 ® , East-GPT ® , East-3PA ® , and East-400 ® are listed. The above products can be used alone or in combination of two or more.
상기 광중합성 단량체는 보다 우수한 현상성을 부여하기 위하여 산무수물로 처리하여 사용할 수도 있다.The photopolymerizable monomer may be used after treatment with an acid anhydride in order to impart better developability.
상기 광중합성 단량체는 감광성 수지 조성물 총량에 대하여 1 중량% 내지 10 중량%, 예컨대 1 중량% 내지 5 중량%로 포함될 수 있다. 광중합성 단량체가 상기 범위 내로 포함될 경우, 패턴 형성 공정에서 노광 시 경화가 충분히 일어나 신뢰성이 우수하며, 패턴의 내열성, 내광성, 내화학성, 해상도 및 밀착성 또한 우수하다.The photopolymerizable monomer may be included in an amount of 1% to 10% by weight, such as 1% to 5% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included within the above range, curing occurs sufficiently during exposure in the pattern formation process, resulting in excellent reliability, and excellent heat resistance, light resistance, chemical resistance, resolution and adhesion of the pattern.
(D) 광중합 개시제(D) photopolymerization initiator
상기 광중합 개시제는 감광성 수지 조성물에 일반적으로 사용되는 개시제로서, 예를 들어 아세토페논계 화합물, 벤조페논계 화합물, 티오크산톤계 화합물, 벤조인계 화합물, 트리아진계 화합물, 옥심계 화합물 등을 사용할 수 있다.The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, and for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, and the like can be used. .
상기 아세토페논계의 화합물의 예로는, 2,2'-디에톡시 아세토페논, 2,2'-디부톡시 아세토페논, 2-히드록시-2-메틸프로피오페논, p-t-부틸트리클로로 아세토페논, p-t-부틸디클로로 아세토페논, 4-클로로 아세토페논, 2,2'-디클로로-4-페녹시 아세토페논, 2-메틸-1-(4-(메틸티오)페닐)-2-모폴리노프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-모폴리노페닐)-부탄-1-온 등을 들 수 있다.Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and the like.
상기 벤조페논계 화합물의 예로는, 벤조페논, 벤조일 안식향산, 벤조일 안식향산 메틸, 4-페닐 벤조페논, 히드록시벤조페논, 아크릴화 벤조페논, 4,4'-비스(디메틸 아미노)벤조페논, 4,4'-비스(디에틸아미노)벤조페논,4,4'-디메틸아미노벤조페논,4,4'-디클로로벤조페논, 3,3'-디메틸-2-메톡시벤조페논 등을 들 수 있다.Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethyl amino) benzophenone, 4,4 '-Bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.
상기 티오크산톤계 화합물의 예로는, 티오크산톤, 2-메틸티오크산톤, 이소프로필 티오크산톤, 2,4-디에틸 티오크산톤, 2,4-디이소프로필 티오크산톤, 2-클로로티오크산톤 등을 들 수 있다.Examples of the thioxanthone compound include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- And chlorothioxanthone.
상기 벤조인계 화합물의 예로는, 벤조인, 벤조인 메틸 에테르, 벤조인 에틸 에테르, 벤조인 이소프로필 에테르, 벤조인 이소부틸 에테르, 벤질디메틸케탈 등을 들 수 있다.Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethylketal.
상기트리아진계화합물의예로는, 2,4,6-트리클로로-s-트리아진, 2-페닐-4,6-비스(트리클로로메틸)-s-트리아진, 2-(3',4'-디메톡시스티릴)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(4'-메톡시나프틸)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(p-메톡시페닐)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(p-톨릴)-4,6-비스(트리클로로 메틸)-s-트리아진, 2-비페닐-4,6-비스(트리클로로 메틸)-s-트리아진, 비스(트리클로로메틸)-6-스티릴-s-트리아진, 2-(나프토-1-일)-4,6-비스(트리클로로메틸)-s-트리아진,2-(4-메톡시나프토-1-일)-4,6-비스(트리클로로메틸)-s-트리아진, 2-4-비스(트리클로로메틸)-6-피페로닐-s-트리아진, 2-4-비스(트리클로로메틸)-6-(4-메톡시스티릴)-s-트리아진 등을 들 수 있다.Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4 '-Dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-tri Azine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-tri Azine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl) -4,6-bis(trichloromethyl)-s-triazine,2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2- 4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like. have.
상기 옥심계 화합물의 예로는 O-아실옥심계 화합물, 2-(O-벤조일옥심)-1-[4-(페닐티오)페닐]-1,2-옥탄디온, 1-(O-아세틸옥심)-1-[9-에틸-6-(2-메틸벤조일)-9H-카르바졸-3-일]에탄온, O-에톡시카르보닐-α-옥시아미노-1-페닐프로판-1-온 등을 사용할 수 있다. 상기 O-아실옥심계 화합물의 구체적인 예로는, 1,2-옥탄디온, 2-디메틸아미노-2-(4-메틸벤질)-1-(4-모르폴린-4-일-페닐)-부탄-1-온, 1-(4-페닐술파닐페닐)-부탄-1,2-디온-2-옥심-O-벤조에이트, 1-(4-페닐술파닐페닐)-옥탄-1,2-디온-2-옥심-O-벤조에이트, 1-(4-페닐술파닐페닐)-옥탄-1-온옥심-O-아세테이트 및 1-(4-페닐술파닐페닐)-부탄-1-온옥심-O-아세테이트 등을 들 수 있다. Examples of the oxime-based compound include O-acyloxime-based compounds, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyloxime) -1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one, etc. Can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane- 1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione -2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime- O-acetate, etc. are mentioned.
상기 광중합 개시제는 상기 화합물 이외에도 카바졸계 화합물, 디케톤류 화합물, 술포늄 보레이트계 화합물, 디아조계 화합물, 이미다졸계 화합물, 비이미다졸계 화합물 등을 사용할 수 있다.In addition to the above compounds, the photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a biimidazole compound.
상기 광중합 개시제는 빛을 흡수하여 들뜬 상태가 된 후 그 에너지를 전달함으로써 화학반응을 일으키는 광 증감제와 함께 사용될 수도 있다.The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light and becoming excited and then transferring the energy.
상기 광 증감제의 예로는, 테트라에틸렌글리콜 비스-3-머캡토 프로피오네이트, 펜타에리트리톨 테트라키스-3-머캡토 프로피오네이트, 디펜타에리트리톨 테트라키스-3-머캡토 프로피오네이트 등을 들 수 있다. Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, etc. Can be mentioned.
상기 광중합 개시제는 감광성 수지 조성물 총량에 대하여 0.01 중량% 내지 5 중량%, 예컨대 0.1 중량% 내지 1 중량%로 포함될 수 있다. 광중합 개시제가 상기 범위 내로 포함될 경우, 패턴 형성 공정에서 노광시 경화가 충분히 일어나 우수한 신뢰성을 얻을 수 있으며, 패턴의 내열성, 내광성,내화학성, 해상도 및 밀착성이 우수하며, 미반응 개시제로 인한 투과율의 저하를 막을 수 있다.The photopolymerization initiator may be included in an amount of 0.01% to 5% by weight, such as 0.1% to 1% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, curing occurs sufficiently during exposure in the pattern formation process to obtain excellent reliability, excellent heat resistance, light resistance, chemical resistance, resolution and adhesion of the pattern, and decrease in transmittance due to unreacted initiator Can be prevented.
(E) 용매(E) solvent
상기 용매는 상기 양자점, 상기 바인더 수지, 상기 광중합성 단량체, 상기 광중합 개시제 및 기타 첨가제와 상용성을 가지되, 반응하지 않는 물질들이 사용될 수 있다.The solvent has compatibility with the quantum dots, the binder resin, the photopolymerizable monomer, the photopolymerization initiator, and other additives, but materials that do not react may be used.
상기 양자점, 상기 바인더 수지, 상기 광중합성 단량체, 상기 광중합 개시제 및 기타 첨가제와 상용성을 가지는 용매의 예로는, 메탄올, 에탄올 등의 알코올류; 디클로로에틸 에테르, n-부틸 에테르, 디이소아밀 에테르, 메틸페닐 에테르, 테트라히드로퓨란 등의 에테르류; 에틸렌 글리콜 모노메틸에테르, 에틸렌 글리콜 모노에틸에테르 등의 글리콜 에테르류; 메틸 셀로솔브 아세테이트, 에틸 셀로솔브 아세테이트, 디에틸 셀로솔브 아세테이트 등의 셀로솔브 아세테이트류; 메틸에틸 카르비톨, 디에틸 카르비톨, 디에틸렌 글리콜 모노메틸에테르, 디에틸렌 글리콜 모노에틸에테르, 디에틸렌 글리콜 디메틸에테르, 디에틸렌 글리콜 메틸에틸에테르, 디에틸렌 글리콜 디에틸에테르 등의 카르비톨류; 프로필렌 글리콜 메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류; 톨루엔, 크실렌 등의 방향족 탄화 수소류; 메틸에틸케톤, 사이클로헥사논, 4-히드록시-4-메틸-2-펜타논, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 메틸-n-아밀케톤,2-헵타논 등의 케톤류; 초산 에틸, 초산-n-부틸, 초산 이소부틸 등의 포화 지방족 모노카르복실산 알킬 에스테르류; 젖산 메틸, 젖산 에틸 등의 젖산 에스테르류; 옥시 초산 메틸, 옥시 초산 에틸, 옥시 초산 부틸 등의 옥시 초산 알킬 에스테르류; 메톡시 초산 메틸, 메톡시 초산 에틸, 메톡시 초산 부틸, 에톡시 초산 메틸, 에톡시 초산 에틸 등의 알콕시 초산 알킬 에스테르류; 3-옥시 프로피온산 메틸, 3-옥시 프로피온산 에틸 등의 3-옥시 프로피온산 알킬에스테르류; 3-메톡시 프로피온산 메틸, 3-메톡시 프로피온산 에틸, 3-에톡시 프로피온산 에틸,3-에톡시 프로피온산 메틸 등의 3-알콕시 프로피온산 알킬 에스테르류; 2-옥시 프로피온산 메틸, 2-옥시 프로피온산 에틸, 2-옥시 프로피온산 프로필 등의 2-옥시 프로피온산 알킬 에스테르류; 2-메톡시 프로피온산 메틸, 2-메톡시 프로피온산 에틸, 2-에톡시 프로피온산 에틸, 2-에톡시 프로피온산 메틸 등의 2-알콕시 프로피온산 알킬 에스테르류; 2-옥시-2-메틸 프로피온산 메틸, 2-옥시-2-메틸 프로피온산 에틸 등의 2-옥시-2-메틸 프로피온산 에스테르류, 2-메톡시-2-메틸 프로피온산 메틸, 2-에톡시-2-메틸 프로피온산 에틸 등의 2-알콕시-2-메틸 프로피온산 알킬류의 모노옥시 모노카르복실산 알킬 에스테르류; 2-히드록시 프로피온산 에틸, 2-히드록시-2-메틸 프로피온산 에틸, 히드록시 초산 에틸, 2-히드록시-3-메틸 부탄산 메틸 등의 에스테르류; 피루빈산 에틸 등의 케톤산 에스테르류 등이 있으며, 또한, N-메틸포름아미드, N,N-디메틸포름아미드, N-메틸포름아닐라드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드, 벤질에틸에테르, 디헥실에테르, 아세틸아세톤, 이소포론, 카프론산, 카프릴산, 1-옥탄올, 1-노난올, 벤질알코올, 초산 벤질, 안식향산 에틸, 옥살산 디에틸, 말레인산 디에틸, γ부티로락톤, 탄산 에틸렌, 탄산 프로필렌, 페닐 셀로솔브 아세테이트 등의 고비점 용매를 들 수 있다.Examples of a solvent having compatibility with the quantum dots, the binder resin, the photopolymerizable monomer, the photopolymerization initiator, and other additives include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactate esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetate alkyl esters such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxypropionic acid alkyl esters such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-alkoxy propionic acid alkyl esters such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, and 3-ethoxy methyl propionate; 2-oxypropionic acid alkyl esters such as 2-oxy methyl propionate, 2-oxy ethyl propionate, and 2-oxy propionate propyl; 2-alkoxy propionic acid alkyl esters such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate, and 2-ethoxy methyl propionate; 2-oxy-2-methyl propionic acid esters such as 2-oxy-2-methyl methyl propionate and 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2- Monooxy monocarboxylic acid alkyl esters of alkyl 2-alkoxy-2-methyl propionate such as ethyl methyl propionate; Esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate, and 2-hydroxy-3-methyl methyl butanoate; Ketone acid esters such as ethyl pyruvate, and the like, and N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, N,N-dimethylacetamide , N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, capronic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid And high boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, ?butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.
이들 중 좋게는 상용성 및 반응성을 고려하여, 에틸렌 글리콜 모노에틸에테르 등의 글리콜 에테르류; 에틸 셀로솔브 아세테이트 등의 에틸렌 글리콜 알킬에테르 아세테이트류; 2-히드록시 프로피온산 에틸 등의 에스테르류; 디에틸렌 글리콜 모노메틸에테르 등의 카르비톨류; 프로필렌 글리콜 모노메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류가 사용될 수 있다.Among these, in consideration of compatibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate may be used.
상기 용매는 감광성 수지 조성물 총량에 대하여 잔부량, 예컨대 30 중량% 내지 80 중량%, 예컨대 40 중량% 내지 75 중량%로 포함될 수 있다. 용매가 상기 범위 내로 포함될 경우 감광성 수지 조성물이 적절한 점도를 가짐에 따라 컬러필터 제조 시 공정성이 우수하다.The solvent may be included in a balance, such as 30% to 80% by weight, such as 40% to 75% by weight, based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, the photosensitive resin composition has an appropriate viscosity, and thus processability is excellent in manufacturing a color filter.
(F) 확산제(F) diffusion agent
일 구현예에 따른 감광성 수지 조성물은 확산제를 더 포함할 수 있다.The photosensitive resin composition according to an embodiment may further include a diffusion agent.
예컨대, 상기 확산제는 황산바륨(BaSO4), 탄산칼슘(CaCO3), 이산화티타늄(TiO2), 지르코니아(ZrO2) 또는 이들의 조합을 포함할 수 있다.For example, the diffusion agent may include barium sulfate (BaSO 4 ), calcium carbonate (CaCO 3 ), titanium dioxide (TiO 2 ), zirconia (ZrO 2 ), or a combination thereof.
상기 확산제는 전술한 광변환 물질에 흡수되지 않은 광을 반사시키고, 상기 반사된 광을 광변환 물질이 다시 흡수할 수 있도록 한다. 즉, 상기 확산제는 광변환 물질에 흡수되는 광의 양을 증가시켜, 감광성 수지 조성물의 광변환 효율을 증가시킬 수 있다.The diffusing agent reflects light that has not been absorbed by the above-described photo-conversion material, and allows the light-conversion material to absorb the reflected light again. That is, the diffusion agent may increase the amount of light absorbed by the photo-conversion material, thereby increasing the photo-conversion efficiency of the photosensitive resin composition.
상기 확산제는 평균 입경(D50)이 150nm 내지 250nm 일 수 있으며, 구체적으로는 180 nm 내지 230 nm일 수 있다. 상기 확산제의 평균 입경이 상기 범위 내일 경우, 보다 우수한 광확산 효과를 가질 수 있으며, 광변환 효율을 증가시킬 수 있다.The diffusing agent may have an average particle diameter (D 50 ) of 150 nm to 250 nm, and specifically 180 nm to 230 nm. When the average particle diameter of the diffusion agent is within the above range, it may have a better light diffusion effect and increase light conversion efficiency.
상기 확산제는, 구체적으로 상기 확산제 고형분은 상기 감광성 수지 조성물 총량에 대해 0.1 중량% 내지 10 중량%, 예컨대 0.5 중량% 내지 8 중량%로 포함될 수 있다. 상기 확산제가 상기 감광성 수지 조성물 총량에 대해 0.5 중량% 미만으로 포함될 경우, 확산제를 사용함에 따른 광변환 효율 향상 효과를 기대하기가 어렵고, 10 중량%를 초과하여 포함할 경우에는 컬러필터의 패턴 특성이 저하되며, 광변환 효율 또한 저하될 수 있다.The diffusing agent, specifically, the solid content of the diffusing agent may be included in an amount of 0.1% to 10% by weight, such as 0.5% to 8% by weight, based on the total amount of the photosensitive resin composition. When the diffusing agent is included in an amount of less than 0.5% by weight based on the total amount of the photosensitive resin composition, it is difficult to expect the effect of improving the light conversion efficiency by using the diffusing agent, and when it is included in an amount exceeding 10% by weight, the pattern characteristics of the color filter This decreases, and the light conversion efficiency may also decrease.
(G) 기타 첨가제(G) other additives
상기 양자점의 안정성 및 분산성 향상을 위해, 일 구현예에 따른 감광성 수지 조성물은 티올(thiol)계 첨가제를 더 포함할 수 있다.In order to improve the stability and dispersibility of the quantum dots, the photosensitive resin composition according to an embodiment may further include a thiol-based additive.
상기 티올계 첨가제는 상기 양자점의 쉘 표면에 치환되어, 용매에 대한 양자점의 분산 안정성을 향상시켜, 양자점을 안정화시킬 수 있다.The thiol-based additive may be substituted on the shell surface of the quantum dot to improve dispersion stability of the quantum dot in a solvent, thereby stabilizing the quantum dot.
상기 티올계 첨가제는 그 구조에 따라 말단에 2개 내지 10개, 예컨대 2개 내지 4개의 티올기(-SH)를 가질 수 있다. The thiol-based additive may have 2 to 10, for example, 2 to 4 thiol groups (-SH) at the ends depending on its structure.
예컨대, 상기 티올계 첨가제는 말단에 하기 화학식 7로 표시되는 관능기를 적어도 2개 이상 포함할 수 있다.For example, the thiol-based additive may include at least two or more functional groups represented by the following formula (7) at the terminal.
[화학식 7][Formula 7]
상기 화학식 7에서,In Chemical Formula 7,
L7 및 L8은 각각 독립적으로 단일결합, 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 치환 또는 비치환된 C2 내지 C20 헤테로아릴렌기이다.L 7 and L 8 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted It is a C2 to C20 heteroarylene group.
예컨대, 상기 티올계 첨가제는 하기 화학식 8로 표시될 수 있다.For example, the thiol-based additive may be represented by the following formula (8).
[화학식 8][Formula 8]
상기 화학식 8에서,In Chemical Formula 8,
L7 및 L8은 각각 독립적으로 단일결합, 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 치환 또는 비치환된 C2 내지 C20 헤테로아릴렌기이고,L 7 and L 8 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted Is a C2 to C20 heteroarylene group,
u1 및 u2는 각각 독립적으로 0 또는 1의 정수이다.u1 and u2 are each independently an integer of 0 or 1.
예컨대, 상기 화학식 7 및 화학식 8에서, 상기 L1 및 L2는 각각 독립적으로 단일결합 또는 치환 또는 비치환된 C1 내지 C20 알킬렌기일 수 있다.For example, in Formulas 7 and 8, L 1 and L 2 may each independently be a single bond or a substituted or unsubstituted C1 to C20 alkylene group.
상기 티올계 첨가제의 구체적인 예로는 하기 화학식 8a로 표시되는 펜타에리트리톨테트라키스(3-머캅토프로피오네이트)(pentaerythritol tetrakis(3-mercaptopropionate)),하기 화학식 8b로 표시되는 트리메틸올프로판 트리스(3-머캅토프로피오네이트)(trimethylolpropane tris(3-mercaptopropionate)), 하기 화학식 8c로 표시되는 펜타에리트리톨 테트라키스(머캅토아세테이트)Pentaerythritol tetrakis(mercaptoacetate), 하기 화학식 8d로 표시되는 트리메틸올프로판 트리스(2-머캅토아세테이트)(trimethylolpropane tris(2-mercaptoacetate)), 하기 화학식 8e로 표시되는 글리콜 디-3-머캅토프로피오네이트(Glycol di-3-mercaptopropionate) 및 이들의 조합으로 이루어진 군에서 선택된 어느 하나를 들 수 있다.Specific examples of the thiol-based additive include pentaerythritol tetrakis (3-mercaptopropionate) represented by the following formula (8a), trimethylolpropane tris (3) represented by the following formula (8b). -Mercaptopropionate) (trimethylolpropane tris (3-mercaptopropionate)), pentaerythritol tetrakis (mercaptoacetate) represented by the following formula 8c, Pentaerythritol tetrakis (mercaptoacetate), trimethylolpropane tris represented by the following formula 8d ( 2-mercaptoacetate) (trimethylolpropane tris (2-mercaptoacetate)), glycol di-3-mercaptopropionate represented by the following Formula 8e (Glycol di-3-mercaptopropionate) and any selected from the group consisting of a combination thereof There is one.
[화학식 8a][Formula 8a]
[화학식 8b][Formula 8b]
[화학식 8c][Formula 8c]
[화학식 8d][Formula 8d]
[화학식 8e][Formula 8e]
상기 티올계 첨가제는 감광성 수지 조성물 총량에 대하여 0.1 중량% 내지 10 중량%, 예컨대 0.1 중량% 내지 5 중량%로 포함될 수 있다. 티올계 첨가제가 상기 범위 내로 포함될 경우, 양자점 등의 광변환 물질의 안정성을 향상시킬 수 있으며, 성분 내 티올기가 수지 또는 단량체의 아크릴기와 반응하여 공유결합을 형성함으로써 양자점과 같은 광변환 물질의 내열성 향상 효과도 가질 수 있다.The thiol-based additive may be included in an amount of 0.1% to 10% by weight, such as 0.1% to 5% by weight, based on the total amount of the photosensitive resin composition. When the thiol-based additive is included within the above range, the stability of photoconversion materials such as quantum dots can be improved, and the thiol group in the component reacts with the acrylic group of the resin or monomer to form a covalent bond, thereby improving the heat resistance of photoconversion materials such as quantum dots. It can also have an effect.
일 구현예에 따른 감광성 수지 조성물은 상기 티올계 첨가제 외에 말론산; 3-아미노-1,2-프로판디올; 실란계 커플링제; 레벨링제; 불소계 계면활성제; 또는 이들의 조합을 더 포함할 수 있다.The photosensitive resin composition according to an embodiment includes malonic acid in addition to the thiol-based additive; 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine-based surfactant; Or it may further include a combination of these.
예컨대, 감광성 수지 조성물은 기판과의 밀착성 등을 개선하기 위해 비닐기, 카르복실기, 메타크릴옥시기, 이소시아네이트기, 에폭시기 등의 반응성 치환기를 갖는 실란계 커플링제를 더 포함할 수 있다.For example, the photosensitive resin composition may further include a silane-based coupling agent having a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, or an epoxy group in order to improve adhesion to the substrate.
상기 실란계 커플링제의 예로는, 트리메톡시실릴 벤조산, γ메타크릴 옥시프로필 트리메톡시실란, 비닐 트리아세톡시실란, 비닐 트리메톡시실란, γ이소시아네이트 프로필 트리에톡시실란, γ글리시독시 프로필 트리메톡시실란, β-(3,4-에폭시사이클로헥실)에틸트리메톡시실란 등을 들 수 있으며, 이들을 단독 또는 2종 이상 혼합하여 사용할 수 있다. Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ isocyanate propyl triethoxysilane, γ glycidoxy propyl Trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more.
상기 실란계 커플링제는 상기 감광성 수지 조성물 100 중량부에 대하여 0.01 중량부내지 10 중량부로 포함될 수 있다. 실란계 커플링제가 상기 범위 내로 포함될 경우 밀착성, 저장성 등이 우수하다. The silane-based coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane-based coupling agent is included within the above range, adhesion and storage properties are excellent.
또한 상기 감광성 수지 조성물은 필요에 따라 코팅성 향상 및 결점 생성 방지 효과를 위해 계면 활성제, 예컨대 불소계 계면활성제를 더 포함할 수 있다. In addition, the photosensitive resin composition may further include a surfactant, such as a fluorine-based surfactant, to improve coating properties and prevent defects from being generated, if necessary.
상기 불소계 계면활성제로는, BM Chemie社의 BM-1000®, BM-1100® 등; 다이 닛폰 잉키 가가꾸 고교(주)社의 메카 팩 F 142D®, 동 F 172®, 동 F 173®, 동 F 183® 등; 스미토모 스리엠(주)社의 프로라드 FC-135®, 동 FC-170C®, 동 FC-430®, 동 FC-431® 등; 아사히 그라스(주)社의 사프론 S-112®, 동 S-113®, 동 S-131®, 동 S-141®, 동 S-145® 등; 도레이 실리콘(주)社의 SH-28PA®, 동-190®, 동-193®, SZ-6032®, SF-8428® 등; DIC(주)社의 F-482, F-484, F-478, F-554 등의 명칭으로 시판되고 있는 불소계 계면활성제를 사용할 수 있다.The fluorine is a surfactant, the BM Chemie社BM-1000 ®, BM-1100 ® , and the like; Mecha Pack F 142D ® , F 172 ® , F 173 ® , F 183 ®, etc. of Dai Nippon Inki Chemical High School Co., Ltd.; Sumitomo M. (Note)社Pro rod FC-135 ®, the same FC-170C ®, copper FC-430 ®, the same FC-431 ®, and the like; Asahi Grass Co., Saffron S-112 ® of社, such S-113 ®, the same S-131 ®, the same S-141 ®, the same S-145 ®, and the like; Toray silicone (Note)社SH-28PA ®, ® -190 copper, copper -193 ®, SZ-6032 ®, SF-8428 ® , and the like; It is possible to use a fluorine-based surfactant marketed under the names of DIC Corporation's F-482, F-484, F-478, F-554, and the like.
상기 불소계 계면활성제는 상기 감광성 수지 조성물 100 중량부에 대하여 0.001 중량부 내지 5 중량부로 사용될 수 있다. 상기 불소계 계면활성제가 상기 범위 내로 포함될 경우 코팅 균일성이 확보되고, 얼룩이 발생하지 않으며, 유리 기판에 대한 습윤성(wetting)이 우수하다.The fluorine-based surfactant may be used in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the fluorine-based surfactant is included within the above range, coating uniformity is ensured, stains do not occur, and wettability to a glass substrate is excellent.
또한 상기 감광성 수지 조성물은 물성을 저해하지 않는 범위 내에서 산화방지제, 안정제 등의 기타 첨가제가 일정량더 첨가될 수도 있다.In addition, a certain amount of other additives such as antioxidants and stabilizers may be further added to the photosensitive resin composition within a range that does not impair physical properties.
다른 일 구현예는 전술한 감광성 수지 조성물을 이용하여 제조된 감광성 수지막을 제공한다. Another embodiment provides a photosensitive resin film prepared by using the photosensitive resin composition described above.
상기 감광성 수지막의 제조 방법은 다음과 같다.The method of manufacturing the photosensitive resin film is as follows.
(1) 도포 및 도막 형성 단계(1) Application and film formation step
전술한 감광성 수지 조성물을 소정의 전처리를 한 기판 상에 스핀 또는 슬릿 코트법, 롤 코트법, 스크린 인쇄법, 어플리케이터법 등의 방법을 사용하여 원하는 두께, 예를 들어 1.2㎛ 내지 3.5㎛의 두께로 도포한 후, 70℃ 내지 90℃의 온도에서 1분 내지 10분 동안 가열하여 용매를 제거함으로써 도막을 형성한다. The above-described photosensitive resin composition is applied onto a substrate subjected to a predetermined pretreatment to a desired thickness, for example, 1.2 µm to 3.5 µm using a method such as spin or slit coating method, roll coating method, screen printing method, and applicator method. After application, the coating film is formed by heating at a temperature of 70° C. to 90° C. for 1 to 10 minutes to remove the solvent.
(2) 노광 단계(2) exposure step
상기 얻어진 도막에 필요한 패턴 형성을 위해 소정 형태의 마스크를 개재한 뒤, 200nm 내지 500nm의 활성선을 조사한다. 조사에 사용되는 광원으로는 저압 수은등, 고압 수은등, 초고압 수은등, 금속 할로겐화물 램프, 아르곤 가스 레이저 등을 사용할 수 있으며, 경우에 따라 X선, 전자선 등도 이용할 수 있다. In order to form a pattern required for the obtained coating film, a mask of a predetermined shape is interposed, and then active rays of 200 nm to 500 nm are irradiated. As a light source used for irradiation, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, an argon gas laser, etc. may be used, and in some cases, an X-ray, an electron beam, and the like may be used.
노광량은 상기 감광성 수지 조성물 각 성분의 종류, 배합량 및 건조 막 두께에 따라 다르지만, 예를 들어 고압 수은등을 사용할 경우 500 mJ/cm2 이하(365 nm 센서에 의함)이다.The exposure amount varies depending on the type, blending amount, and dry film thickness of each component of the photosensitive resin composition, but, for example, when a high-pressure mercury lamp is used, it is 500 mJ/cm 2 or less (by a 365 nm sensor).
(3) 현상 단계(3) development stage
상기 노광 단계에 이어, 알칼리성 수용액을 현상액으로 이용하여 불필요한 부분을 용해, 제거함으로써 노광 부분만을 잔존시켜 화상 패턴을 형성시킨다. Following the exposure step, an alkaline aqueous solution is used as a developer to dissolve and remove unnecessary portions, so that only the exposed portions remain to form an image pattern.
(4) 후처리 단계(4) Post-processing step
상기 현상에 의해 수득된 화상 패턴을 내열성, 내광성, 밀착성, 내크랙성, 내화학성, 고강도, 저장 안정성 등의 면에서 우수한 패턴을 얻기 위해, 다시 가열하거나 활성선 조사 등을 행하여 경화시킬 수 있다.In order to obtain an excellent pattern in terms of heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength, storage stability, and the like, the image pattern obtained by the above development may be cured by heating again or irradiating with actinic rays.
또 다른 일 구현예는 상기 감광성 수지막을 포함하는 컬러필터를 제공한다.Another embodiment provides a color filter including the photosensitive resin film.
또 다른 일 구현예는 상기 컬러필터를 포함하는 디스플레이 장치를 제공한다.Another embodiment provides a display device including the color filter.
이하, 본 발명의 바람직한 실시예를 기재한다. 다만, 하기의 실시예는 본 발명의 바람직한 일 실시예일뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only preferred examples of the present invention, and the present invention is not limited by the following examples.
(카도계 바인더 수지 제조)(Manufacture of cardo-based binder resin)
합성예 1-1Synthesis Example 1-1
반응기에 9,9'-비스(4-글리실록시페닐)플루오렌(Hear chem社) 138g, 4-(메틸싸이오)벤젠싸이올(TCI社) 54g, 벤질트리에틸암모늄클로라이드(대정화금社) 1.4g, 트리페닐포스핀(Aldrich社) 1g, 프로필글리콜메틸에틸아세테이트(Daicel Chemical社) 128g, 및 하이드로퀴논 0.5g을 넣고 120℃로 승온 후 12시간 유지하여, 하기 화학식 A-1로 표시되는 화합물을 합성하였다.In the reactor, 9,9'-bis(4-glysiloxyphenyl)fluorene (Hear chem) 138g, 4-(methylthio)benzenethiol (TCI) 54g, benzyltriethylammonium chloride (Daejunghwakeum) Company) 1.4g, triphenylphosphine (Aldrich) 1g, propylglycolmethylethyl acetate (Daicel Chemical) 128g, and hydroquinone 0.5g were added, the temperature was raised to 120°C, and then maintained for 12 hours. The indicated compound was synthesized.
[화학식 A-1][Formula A-1]
합성예 1-2Synthesis Example 1-2
반응기에 9,9'-비스(4-글리실록시페닐)플루오렌(Hear chem社) 138g, 2-(메틸설파닐)에탄-1-싸이올(TCI社) 54g, 벤질트리에틸암모늄클로라이드(대정화금社) 1.4g, 트리페닐포스핀(Aldrich社) 1g, 프로필글리콜메틸에틸아세테이트(Daicel Chemical社) 128g, 및 하이드로퀴논 0.5g을 넣고 120℃로 승온 후 12시간 유지하여, 하기 화학식 A-2로 표시되는 화합물을 합성하였다.In the reactor, 9,9'-bis(4-glysiloxyphenyl)fluorene (Hear chem) 138g, 2-(methylsulfanyl)ethane-1-thiol (TCI) 54g, benzyltriethylammonium chloride ( Daejeonghwa Geum) 1.4g, triphenylphosphine (Aldrich) 1g, propyl glycol methylethyl acetate (Daicel Chemical) 128g, and hydroquinone 0.5g were added and heated to 120°C and held for 12 hours, the following formula A A compound represented by -2 was synthesized.
[화학식 A-2][Formula A-2]
합성예 2-1Synthesis Example 2-1
반응기에 상기 화학식 A-1로 표시되는 화합물 60g, 3,3',4,4'-싸이오디프탈릭 무수물(American chemical 社) 16g, 5-노보렌-2,3-디카르복실릭 무수물(TCI社) 3.4g, 프로필글리콜메틸에틸아세테이트(Daicel Chemical社) 20g 및 N,N'-테트라메틸암모늄 클로라이드 0.1g을 넣고 120℃로 승온 후 2시간 유지하여, 하기 화학식 B-1로 표시되는 화합물(중량평균 분자량: 5,600 g/mol)을 합성하였다. In the reactor, the compound represented by Formula A-1 60g, 3,3',4,4'-thiodiphthalic anhydride (American chemical) 16g, 5-norborene-2,3-dicarboxylic anhydride ( TCI) 3.4g, propyl glycol methylethyl acetate (Daicel Chemical) 20g and N,N'-tetramethylammonium chloride 0.1g, heated to 120 ℃ and maintained for 2 hours, the compound represented by the following formula B-1 (Weight average molecular weight: 5,600 g/mol) was synthesized.
[화학식 B-1][Formula B-1]
합성예 2-2Synthesis Example 2-2
반응기에 상기 화학식 A-1로 표시되는 화합물 60g, 1,2,3,4-싸이클로부탄테트라카르복실릭디무수물 (TCI 社) 16g, 5-노보렌-2,3-디카르복실릭 무수물(TCI社) 3.4g, 프로필글리콜메틸에틸아세테이트(Daicel Chemical社) 20g 및 N,N'-테트라메틸암모늄 클로라이드 0.1g을 넣고 120℃로 승온 후 2시간 유지하여, 하기 화학식 B-2로 표시되는 화합물(중량평균 분자량: 4,300 g/mol)을 합성하였다.In the reactor, the compound represented by Formula A-1 60g, 1,2,3,4-cyclobutanetetracarboxylic dianhydride (TCI) 16g, 5-norborene-2,3-dicarboxylic anhydride (TCI Company) 3.4g, 20g of propyl glycol methylethyl acetate (Daicel Chemical), and 0.1g of N,N'-tetramethylammonium chloride were added, the temperature was raised to 120°C, and maintained for 2 hours, the compound represented by the following formula B-2 ( Weight average molecular weight: 4,300 g/mol) was synthesized.
[화학식 B-2][Formula B-2]
합성예 2-3Synthesis Example 2-3
반응기에 상기 화학식 A-2로 표시되는 화합물 60g, 3,3',4,4'-싸이오디프탈릭 무수물(American chemical 社) 16g, 5-노보렌-2,3-디카르복실릭 무수물(TCI社) 3.4g, 프로필글리콜메틸에틸아세테이트(Daicel Chemical社) 20g 및 N,N'-테트라메틸암모늄 클로라이드 0.1g을 넣고 120℃로 승온 후 2시간 유지하여, 하기 화학식 B-3으로 표시되는 화합물(중량평균 분자량: 5,400 g/mol)을 합성하였다. In the reactor, 60g of the compound represented by Formula A-2, 3,3',4,4'-thiodiphthalic anhydride (American chemical) 16g, 5-norborene-2,3-dicarboxylic anhydride ( TCI) 3.4g, propyl glycol methylethyl acetate (Daicel Chemical) 20g and N,N'-tetramethylammonium chloride 0.1g, heated to 120 ℃ and maintained for 2 hours, the compound represented by the following formula B-3 (Weight average molecular weight: 5,400 g/mol) was synthesized.
[화학식 B-3][Formula B-3]
합성예 2-4Synthesis Example 2-4
반응기에 상기 화학식 A-2로 표시되는 화합물 60g, 1,2,3,4-싸이클로부탄테트라카르복실릭디무수물 (TCI 社) 16g, 5-노보렌-2,3-디카르복실릭 무수물(TCI社) 3.4g, 프로필글리콜메틸에틸아세테이트(Daicel Chemical社) 20g 및 N,N'-테트라메틸암모늄 클로라이드 0.1g을 넣고 120℃로 승온 후 2시간 유지하여, 하기 화학식 B-4로 표시되는 화합물(중량평균 분자량: 4,200 g/mol)을 합성하였다.In the reactor, the compound represented by Formula A-2 is 60g, 1,2,3,4-cyclobutanetetracarboxylic dianhydride (TCI) 16g, 5-norborene-2,3-dicarboxylic anhydride (TCI Company) 3.4g, 20g of propyl glycol methylethyl acetate (Daicel Chemical) and 0.1g of N,N'-tetramethylammonium chloride were added, the temperature was raised to 120°C, and maintained for 2 hours, a compound represented by the following formula B-4 ( Weight average molecular weight: 4,200 g/mol) was synthesized.
[화학식 B-4][Formula B-4]
비교합성예 2-1Comparative Synthesis Example 2-1
상기 화학식 A-1로 표시되는 화합물 5g을 취하여 프탈릭 무수물 (Sisco-Chem社) 2g, 테트라하이드로프탈릭 무수물 (Merck社) 1.4g, 테트라클로로프탈릭 무수물 (National Chemicals社) 2.4g, 테트라브로모 프탈릭 무수물 (Lancaster社) 1.7g 및 에피클로로히드린 (Merck社) 1g과 비스페놀A (Merck社) 0.5g을 아세톤 (Merck社) 50g과 함께 넣고 70℃로 승온 후 2시간 유지하여 카도계 수지에 에폭시기가 그라프트된 바인더 수지 (중량평균 분자량: 5,900g/mol)를 합성하였다. Taking 5 g of the compound represented by Formula A-1, 2 g of phthalic anhydride (Sisco-Chem), 1.4 g of tetrahydrophthalic anhydride (Merck), 2.4 g of tetrachlorophthalic anhydride (National Chemicals), tetrabro Add 1.7 g of mophthalic anhydride (Lancaster company), 1 g of epichlorohydrin (Merck company) and 0.5 g of bisphenol A (Merck company) together with 50 g of acetone (Merck company) and heat up to 70℃ and hold for 2 hours. A binder resin (weight average molecular weight: 5,900 g/mol) having an epoxy group grafted onto the resin was synthesized.
비교합성예 2-2Comparative Synthesis Example 2-2
상기 화학식 A-1로 표시되는 화합물 5g을 취하여 프탈릭 무수물 (Sisco-Chem社) 2g, 테트라하이드로프탈릭 무수물 (Merck社) 1.4g, 테트라클로로프탈릭 무수물 (National Chemicals社) 2.4g, 아크릴산 (Merck社) 0.2g 및 에틸아크릴레이트 (Merck社) 0.8g을 아세톤 (Merck社) 40g에 테트라하이드로퓨란 (Merck社) 10g과 함께 넣고 70℃로 승온 후 2시간 유지하여 카도계 수지에 아크릴레이트기가 그라프트된 바인더 수지 (중량평균 분자량: 5,600g/mol)를 합성하였다.Taking 5 g of the compound represented by Formula A-1, 2 g of phthalic anhydride (Sisco-Chem), 1.4 g of tetrahydrophthalic anhydride (Merck), 2.4 g of tetrachlorophthalic anhydride (National Chemicals), acrylic acid ( Merck company) 0.2g and ethyl acrylate (Merck company) 0.8g in acetone (Merck company) 40g together with tetrahydrofuran (Merck company) 10g, heated to 70℃ and maintained for 2 hours The grafted binder resin (weight average molecular weight: 5,600 g/mol) was synthesized.
(감광성 수지 조성물 제조)(Production of photosensitive resin composition)
실시예 1 내지 실시예 16, 비교예 1 및 비교예 2Examples 1 to 16, Comparative Example 1 and Comparative Example 2
하기 언급된 구성성분들을 이용하여 하기 표 1 및 표 2에 나타낸 조성으로 각 실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에 따른 감광성 수지 조성물을 제조하였다.Using the components mentioned below, the photosensitive resin compositions according to Examples 1 to 16, Comparative Examples 1 and 2 were prepared in the compositions shown in Tables 1 and 2 below.
구체적으로, 용매에 광중합 개시제를 용해시킨 후, 2시간 동안 상온에서 충분히 교반하였다. 이어서, 광중합성 단량체와 바인더 수지를 투입하고, 다시 1시간 동안 상온에서 교반하였다. 이 후, 양자점 분산액을 상기 광중합 개시제 등이 용해된 용매와 섞은 후, 여기에 확산제, 티올계 첨가제 및 불소계 계면활성제를 첨가한 후, 1시간 동안 상온에서 교반하고, 상기 생성물을 3회 여과하여 불순물을 제거함으로써, 감광성 수지 조성물을 제조하였다.Specifically, after dissolving the photopolymerization initiator in the solvent, it was sufficiently stirred at room temperature for 2 hours. Then, the photopolymerizable monomer and the binder resin were added, and the mixture was stirred at room temperature for 1 hour. Thereafter, the quantum dot dispersion was mixed with a solvent in which the photopolymerization initiator and the like were dissolved, and a diffusing agent, a thiol-based additive, and a fluorine-based surfactant were added thereto, followed by stirring at room temperature for 1 hour, and the product was filtered three times. By removing impurities, a photosensitive resin composition was prepared.
(A) 양자점(A) quantum dots
InP/ZnS 양자점 분산액(고형분 30%, fluorescence λem=635nm, FWHM=40nm, Red QD, 한솔케미칼社)InP/ZnS quantum dot dispersion (solid content 30%, fluorescence λ em =635nm, FWHM=40nm, Red QD, Hansol Chemical)
(B) 바인더 수지(B) binder resin
(B-1) 카도계 바인더 수지(B-1) Cardo-based binder resin
(B-1-1) 합성예 2-1에서 제조된 카도계 바인더 수지(B-1-1) Cardo-based binder resin prepared in Synthesis Example 2-1
(B-1-2) 합성예 2-2에서 제조된 카도계 바인더 수지(B-1-2) Cardo-based binder resin prepared in Synthesis Example 2-2
(B-1-3) 합성예 2-3에서 제조된 카도계 바인더 수지(B-1-3) Cardo-based binder resin prepared in Synthesis Example 2-3
(B-1-4) 합성예 2-4에서 제조된 카도계 바인더 수지(B-1-4) Cardo-based binder resin prepared in Synthesis Example 2-4
(B-1-5) 비교합성예 2-1에서 제조된 카도계 바인더 수지(B-1-5) Cardo-based binder resin prepared in Comparative Synthesis Example 2-1
(B-1-6) 비교합성예 2-2에서 제조된 카도계 바인더 수지(B-1-6) Cardo-based binder resin prepared in Comparative Synthesis Example 2-2
(B-2-1) 아크릴계 바인더 수지(SP-RY16, Showa denko社)(B-2-1) Acrylic binder resin (SP-RY16, Showa denko company)
(B-2-2) 에폭시계 바인더 수지(EHPE3150, 다이셀화학공업社)(B-2-2) Epoxy binder resin (EHPE3150, Daicel Chemical Industries, Ltd.)
(C) 광중합성 단량체(C) photopolymerizable monomer
디펜타에리트리톨헥사아크릴레이트(일본화약社)Dipentaerythritol hexaacrylate (Japan Explosives Co., Ltd.)
(D) 광중합 개시제(D) photopolymerization initiator
IRG784 (BASF社)IRG784 (BASF company)
(E) 용매(E) solvent
프로필렌 글리콜 모노메틸에테르 아세테이트 (PGMEA) (Sigma-Aldrich社)Propylene glycol monomethyl ether acetate (PGMEA) (Sigma-Aldrich)
(F) 확산제(F) diffusion agent
이산화티탄 분산액 (TiO2고형분 20중량%, 평균입경: 200nm, 디토테크놀로지㈜)Titanium dioxide dispersion (TiO 2 solid content 20% by weight, average particle diameter: 200nm, Dito Technology Co., Ltd.)
(G) 기타 첨가제(G) other additives
(G-1) 티올계 첨가제 (글리콜 디-3-머캅토프로피오네이트, BRUNO BOCK社)(G-1) Thiol-based additive (glycol di-3-mercaptopropionate, BRUNO BOCK company)
(G-2) 불소계 계면활성제 (F-554 (10%), DIC社)(G-2) Fluorine-based surfactant (F-554 (10%), DIC company)
평가 1: 현상 후 패턴성 평가Evaluation 1: Evaluation of patterning after development
실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에 따른 감광성 수지 조성물을 유리 기판 위에 스핀 코팅기(Mikasa社, Opticoat MS-A150)를 사용하여 각각 3 ㎛ 두께로 코팅한 후, 열판(hot-plate)을 이용하여 80℃에서 120초 동안 소프트-베이킹(soft-baking)을 하고, 노광기(Ushio社, ghi broadband)를 이용하여 60mJ의 출력(power)으로 노광하였다. 이어서 현상기(SVS社, SSP-200)를 사용하여 0.2 중량%의 수산화 칼륨(KOH) 수용액으로 현상하였다. 이 후, 집속이온빔(FIB) 주사전자현미경(SEM)을 이용하여 2만배의 배율로 현상 후 남아있는 패턴의 단면을 측정하였으며, 1만5천배의 배율로 현상 후 남아있는 패턴의 표면을 측정하여, 그 결과를 하기 표 3, 표 4 및 도 1 내지 도 10에 나타내었다. (패턴 단면의 암점과 패턴 표면의 홀의 개수는 육안으로 측정하였다.)The photosensitive resin compositions according to Examples 1 to 16, Comparative Example 1 and Comparative Example 2 were coated on a glass substrate to a thickness of 3 μm using a spin coater (Mikasa Corporation, Opticoat MS-A150), respectively, and then a hot plate (hot -plate) at 80° C. for 120 seconds, and exposed with a power of 60mJ using an exposure machine (Ushio Corporation, ghi broadband). Subsequently, it was developed with a 0.2% by weight aqueous solution of potassium hydroxide (KOH) using a developer (SVS, SSP-200). Thereafter, the cross section of the pattern remaining after development was measured at a magnification of 20,000 times using a focused ion beam (FIB) scanning electron microscope (SEM), and the surface of the pattern remaining after development was measured at a magnification of 15,000 times. , The results are shown in Table 3, Table 4, and FIGS. 1 to 10 below. (The number of dark spots on the cross section of the pattern and the number of holes on the pattern surface were measured with the naked eye.)
* 패턴성 평가 기준* Pattern evaluation criteria
○: 육안으로 관찰되는 암점 개수가 없고., 홀 개수가 10개 미만○: There is no number of dark spots observed with the naked eye, and the number of holes is less than 10
△: 육안으로 관찰되는 암점 개수가 1개 이상 5개 미만이고, 홀 개수가 1개 이상 10개 미만△: The number of dark spots observed with the naked eye is 1 or more and less than 5, and the number of holes is 1 or more and less than 10
ⅹ: 육안으로 관찰되는 암점 개수가 5개 이상 또는 육안으로 관찰되는 홀 개수가 10개 이상Ⅹ: The number of dark spots observed with the naked eye is 5 or more or the number of holes observed with the naked eye is 10 or more
표 3 내지 표 4 및 도 1 내지 도 10으로부터, 실시예에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막은, 비교예에 따른 감광성 수지 조성물을 이용하여 제조된 감광성 수지막보다, 현상 후 패턴 특성이 우수한 것을 확인할 수 있다.From Tables 3 to 4 and FIGS. 1 to 10, the photosensitive resin film prepared by using the photosensitive resin composition according to the embodiment is more pattern characteristics after development than the photosensitive resin film prepared by using the photosensitive resin composition according to the comparative example. It can be confirmed that this is excellent.
평가 2: 저장안정성 평가Evaluation 2: Storage stability evaluation
실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에 따른 감광성 수지 조성물 각각에 대하여 점도계(Brookfield社 DV-Ⅱ, RV-2스핀들, 23rpm)를 사용하여 25℃에서 점도값을 측정하고, 15일 후 다시 점도값을 측정하였으며, 15일 후의 점도값이 15일 전의 점도값보다 0.5 cps 미만으로 상승하면 양호로 판정하고, 15일 후의 점도값이 15일 전의 점도값보다 0.5 cps 초과로 상승하면 불량으로 판정하여, 그 결과를 하기 표 5 및 표 6에 나타내었다. For each of the photosensitive resin compositions according to Examples 1 to 16, Comparative Example 1 and Comparative Example 2, viscosity values were measured at 25°C using a viscometer (Brookfield Corporation DV-II, RV-2 spindle, 23 rpm), After 15 days, the viscosity value was measured again, and if the viscosity value after 15 days rises to less than 0.5 cps than the viscosity value before 15 days, it is judged as good, and the viscosity value after 15 days rises to more than 0.5 cps than the viscosity value before 15 days. The lower surface was determined to be defective, and the results are shown in Tables 5 and 6 below.
평가 3: 열 공정 이후 광흡수율 평가Evaluation 3: Evaluation of light absorption rate after thermal process
실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에 따른 감광성 수지 조성물을 유리 기판 위에 스핀 코팅기(Mikasa社, Opticoat MS-A150)를 사용하여 각각 3 ㎛ 두께로 코팅한 후, 열판(hot-plate)을 이용하여 80℃에서 120초 동안 소프트-베이킹(soft-baking)을 하고, 노광기(Ushio社, ghi broadband)를 이용하여 60mJ의 출력(power)으로 노광하였다. 이어서 현상기(SVS社, SSP-200)를 사용하여 0.2 중량%의 수산화 칼륨(KOH) 수용액으로 현상하였다. 이 후, convection oven에서 각각 180℃로 30분 동안 하드-베이킹(Hard-baking)을 진행하였다. 오츠카전자(OTSUKA)의 양자효율측정기 QE-2100 장비로 하드-베이킹 후의 시편의 광흡수율을 50℃의 오븐에서 측정하고, 15일 후 다시 광흡수율을 측정하였으며, 15일 전의 광흡수율과 15일 후의 광흡수율이 동일하면 매우 양호로 판정하고, 15일 후의 광흡수율이 15일 전의 광흡수율보다 2.0% 이하로 저하되면 양호로 판정하고, 15일 후의 광흡수율이 15일 전의 광흡수율보다 2.0% 초과로 저하하면 불량으로 판정하여, 그 결과를 하기 표 7 및 표 8에 나타내었다. The photosensitive resin compositions according to Examples 1 to 16, Comparative Example 1 and Comparative Example 2 were coated on a glass substrate to a thickness of 3 μm using a spin coater (Mikasa Corporation, Opticoat MS-A150), respectively, and then a hot plate (hot -plate) at 80° C. for 120 seconds, and exposed with a power of 60mJ using an exposure machine (Ushio Corporation, ghi broadband). Subsequently, it was developed with a 0.2% by weight aqueous solution of potassium hydroxide (KOH) using a developer (SVS, SSP-200). Thereafter, hard-baking was performed in a convection oven at 180° C. for 30 minutes. The light absorption rate of the specimen after hard-baking was measured in an oven at 50°C with the quantum efficiency meter QE-2100 of Otsuka Electronics, and the light absorption rate was measured again after 15 days. If the light absorption rate is the same, it is judged as very good, and if the light absorption rate after 15 days decreases to 2.0% or less than the light absorption rate before 15 days, it is judged as good, and the light absorption rate after 15 days is more than 2.0% than the light absorption rate before 15 days. If it decreases, it was judged as defective, and the results are shown in Tables 7 and 8 below.
평가 4: 양자점의 광변환 유지율 평가Evaluation 4: Evaluation of photoconversion retention rate of quantum dots
실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에서 제조된 감광성 수지 조성물을 각각 15ml씩 취해, 유리 기판 위에 스핀 코팅기(Mikasa社, Opticoat MS-A150)를 사용하여 약 10 ㎛ 두께로 코팅한 후, 열판(hot-plate)을 이용하여 100℃에서 3분 동안 소프트-베이킹(soft-baking)을 하고, 초기 청색 광변환율을 측정하였다.15 ml of each of the photosensitive resin compositions prepared in Examples 1 to 16, Comparative Examples 1 and 2 were taken, and coated on a glass substrate to a thickness of about 10 μm using a spin coater (Mikasa, Opticoat MS-A150). After that, soft-baking was performed at 100° C. for 3 minutes using a hot-plate, and the initial blue light conversion rate was measured.
노광기(Ushio社, ghi broadband)를 이용하여 100mJ/cm2의 출력(power)으로 UV를 조사한 후, convection oven에서 180℃로 30분 동안 하드-베이킹(Hard-baking)을 진행하고, 청색 광변환율을 측정하였다. After irradiating UV with a power of 100mJ/cm 2 using an exposure machine (Ushio, ghi broadband), hard-baking at 180℃ for 30 minutes in a convection oven, and blue light conversion rate Was measured.
소프트-베이킹 단계 및 하드-베이킹 단계에 대해, BLU로부터 입사되는 청색광의 적색으로의 광변환 유지율을 평가하여, 그 결과를 하기 표 9 및 표 10에 나타내었다. 여기서 청색 광변환 유지율 측정은 CAS 140 CT spectrometer 장비로 측정하였고, diffusing film이 덮인 blue BLU 위에 bare glass를 놓고 디텍터로 측정하여 먼저 reference를 잡은 다음, 같은 위치에서 실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에 따른 감광성 수지 조성물이 코팅된 단막을 올려 놓고, 청색광 흡수 피크의 감소량 대비 적색으로 변환된 피크의 증가량을 계산하여, 광변환 유지율(Red/blue)을 측정하였다. For the soft-baking step and the hard-baking step, the retention rate of light conversion of blue light incident from the BLU to red was evaluated, and the results are shown in Tables 9 and 10 below. Here, the measurement of the blue light conversion retention rate was measured with a CAS 140 CT spectrometer, and a bare glass was placed on the blue BLU covered with a diffusing film and measured with a detector. The single film coated with the photosensitive resin composition according to 1 and Comparative Example 2 was placed, and the increase in the peak converted to red compared to the decrease in the blue light absorption peak was calculated, and the photoconversion retention rate (Red/blue) was measured.
상기 표 9 및 표 10에서 보는 바와 같이, 실시예 1 내지 실시예 14의 경우, 실시예 15, 실시예 16, 비교예 1 및 비교예 2 대비해서, 열 공정 이후에도 광변환 유지율의 저하가 최소화됨을 확인할 수 있다.As shown in Tables 9 and 10, in the case of Examples 1 to 14, compared to Examples 15, 16, and Comparative Examples 1 and 2, the reduction in photoconversion retention even after the thermal process was minimized. I can confirm.
본 발명은 상기 실시예들에 한정되는 것이 아니라 서로 다른 다양한 형태로 제조될 수 있으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다른 구체적인 형태로 실시될 수 있다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야만 한다.The present invention is not limited to the above embodiments, but may be manufactured in a variety of different forms, and those of ordinary skill in the art to which the present invention pertains, other specific forms without changing the technical spirit or essential features of the present invention. It can be understood that Therefore, it should be understood that the embodiments described above are illustrative and non-limiting in all respects.
Claims (18)
(B) 바인더 수지;
(C) 광중합성 단량체;
(D) 광중합 개시제; 및
(E) 용매
를 포함하고,
상기 (B) 바인더 수지는
(B-1) 하기 화학식 1로 표시되는 구조단위를 포함하는 카도계 바인더 수지 및
(B-2) 아크릴계 바인더 수지 및 에폭시계 바인더 수지로 이루어진 군에서 선택된 적어도 하나 이상의 바인더 수지
를 포함하는 감광성 수지 조성물:
[화학식 1]
상기 화학식 1에서,
R11 및 R12은 각각 독립적으로 하기 화학식 2로 표시되고,
[화학식 2]
상기 화학식 2에서,
L1은 치환 또는 비치환된 C1 내지 C10 알킬렌기이고,
L2는 산소 원자 또는 황 원자이고,
R1은 "C1 내지 C10 알킬티오기로 치환된 C1 내지 C10 알킬기" 또는 "C1 내지 C10 알킬티오기로 치환된 C6 내지 C20 아릴기"이고,
R13 및 R14는 각각 독립적으로 수소 원자, 할로겐 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기이고,
Z1은 단일결합, O, CO, SO2, CR17R18, SiR19R20(여기서, R17 내지 R20은 각각 독립적으로 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기임) 또는 하기 화학식 1-1 내지 화학식 1-11로 표시되는 연결기 중 어느 하나이고,
[화학식 1-1]
[화학식 1-2]
[화학식 1-3]
[화학식 1-4]
[화학식 1-5]
(상기 화학식 1-5에서,
Ra는 수소 원자, 에틸기, C2H4Cl, C2H4OH, CH2CH=CH2 또는 페닐기이다.)
[화학식 1-6]
[화학식 1-7]
[화학식 1-8]
[화학식 1-9]
[화학식 1-10]
[화학식 1-11]
Z2는 산무수물 잔기이고,
t1 및 t2는 각각 독립적으로 0 내지 4의 정수이다.
(A) quantum dots;
(B) binder resin;
(C) photopolymerizable monomer;
(D) photoinitiator; And
(E) solvent
Including,
The (B) binder resin is
(B-1) a cardo-based binder resin containing a structural unit represented by the following formula (1), and
(B-2) at least one or more binder resins selected from the group consisting of acrylic binder resins and epoxy binder resins
Photosensitive resin composition comprising:
[Formula 1]
In Formula 1,
R 11 and R 12 are each independently represented by the following formula (2),
[Formula 2]
In Chemical Formula 2,
L 1 is a substituted or unsubstituted C1 to C10 alkylene group,
L 2 is an oxygen atom or a sulfur atom,
R 1 is “a C1 to C10 alkyl group substituted with a C1 to C10 alkylthio group” or “C6 to C20 aryl group substituted with a C1 to C10 alkylthio group”,
R 13 and R 14 are each independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,
Z 1 is a single bond, O, CO, SO 2 , CR 17 R 18 , SiR 19 R 20 (wherein R 17 to R 20 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or the following It is any one of the linking groups represented by Formula 1-1 to Formula 1-11,
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
(In Formula 1-5,
R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH=CH 2 or a phenyl group.)
[Formula 1-6]
[Formula 1-7]
[Formula 1-8]
[Formula 1-9]
[Formula 1-10]
[Formula 1-11]
Z 2 is an acid anhydride residue,
t1 and t2 are each independently an integer of 0 to 4.
상기 R1은 "C1 내지 C5 알킬티오기로 치환된 C1 내지 C5 알킬기" 또는 "C1 내지 C5 알킬티오기로 치환된 C6 내지 C10 아릴기"인 감광성 수지 조성물.
The method of claim 1,
The photosensitive resin composition of R 1 is “a C1 to C5 alkyl group substituted with a C1 to C5 alkylthio group” or “C6 to C10 aryl group substituted with a C1 to C5 alkylthio group”.
상기 Z2는 하기 화학식 3 내지 화학식 5로 이루어진 군에서 선택된 어느 하나로 표시되는 감광성 수지 조성물:
[화학식 3]
[화학식 4]
[화학식 5]
상기 화학식 3에서,
L3은 단일결합, 산소 원자, 황 원자, *-C(=O)-* 또는 *-CR2R3-* (상기 R2 및 R3은 각각 독립적으로 할로겐원자로 치환 또는 비치환된 C1 내지 C10 알킬기)이다.
The method of claim 1,
The Z 2 is a photosensitive resin composition represented by any one selected from the group consisting of the following Chemical Formulas 3 to 5:
[Formula 3]
[Formula 4]
[Formula 5]
In Chemical Formula 3,
L 3 is a single bond, an oxygen atom, a sulfur atom, *-C(=O)-* or *-CR 2 R 3 -* (wherein R 2 and R 3 are each independently substituted or unsubstituted with a halogen atom C1 to C10 alkyl group).
상기 카도계 바인더 수지는 2,000 g/mol 내지 20,000 g/mol의 중량평균분자량을 가지는 감광성 수지 조성물.
The method of claim 1,
The cardo-based binder resin is a photosensitive resin composition having a weight average molecular weight of 2,000 g/mol to 20,000 g/mol.
상기 '카도계 바인더 수지'와 '아크릴계 바인더 수지 및 에폭시계 바인더 수지로 이루어진 군에서 선택된 적어도 하나 이상의 바인더 수지'는 2:1 내지 7:1의 중량비로 포함되는 감광성 수지 조성물.
The method of claim 1,
The'cardo-based binder resin'and'at least one binder resin selected from the group consisting of an acrylic-based binder resin and an epoxy-based binder resin' are included in a weight ratio of 2:1 to 7:1.
상기 아크릴계 바인더 수지는 이중결합 당량이 150 g/mol 내지 400 g/mol인 감광성 수지 조성물.
The method of claim 1,
The acrylic binder resin is a photosensitive resin composition having a double bond equivalent of 150 g / mol to 400 g / mol.
상기 에폭시계 바인더 수지는 에폭시 당량이 100 g/eq 내지 200 g/eq인 감광성 수지 조성물.
The method of claim 1,
The epoxy-based binder resin is a photosensitive resin composition having an epoxy equivalent of 100 g / eq to 200 g / eq.
상기 에폭시계 바인더 수지는 하기 화학식 6으로 표시되는 감광성 수지 조성물:
[화학식 6]
상기 화학식 6에서,
R4는 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,
n1 내지 n3은 각각 독립적으로 1 내지 20의 정수이다.
The method of claim 1,
The epoxy-based binder resin is a photosensitive resin composition represented by the following formula (6):
[Formula 6]
In Chemical Formula 6,
R 4 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
n1 to n3 are each independently an integer of 1 to 20.
상기 감광성 수지 조성물은 (F) 확산제를 상기 감광성 수지 조성물 총량에 대해 0.5 중량% 내지 10 중량% 더 포함하는 감광성 수지 조성물.
The method of claim 1,
The photosensitive resin composition further comprises 0.5% to 10% by weight of a diffusing agent (F) based on the total amount of the photosensitive resin composition.
상기 확산제는 황산바륨, 탄산칼슘, 이산화티타늄, 지르코니아 또는 이들의 조합을 포함하는 감광성 수지 조성물.
The method of claim 9,
The diffusing agent photosensitive resin composition comprising barium sulfate, calcium carbonate, titanium dioxide, zirconia, or a combination thereof.
상기 감광성 수지 조성물은 티올계 첨가제를 더 포함하는 감광성 수지 조성물.
The method of claim 1,
The photosensitive resin composition further comprises a thiol-based additive.
상기 티올계 첨가제는 말단에 하기 화학식 7로 표시되는 관능기를 적어도 2개 이상 포함하는 감광성 수지 조성물:
[화학식 7]
상기 화학식 7에서,
L7 및 L8은 각각 독립적으로 단일결합, 치환 또는 비치환된 C1 내지 C20 알킬렌기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 치환 또는 비치환된 C2 내지 C20 헤테로아릴렌기이다.
The method of claim 11,
The thiol-based additive is a photosensitive resin composition comprising at least two or more functional groups represented by the following formula (7) at the terminal:
[Formula 7]
In Chemical Formula 7,
L 7 and L 8 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted It is a C2 to C20 heteroarylene group.
상기 양자점은 360 nm 내지 780nm의 광을 흡수해, 500nm 내지 700nm에서 형광을 방출하는 양자점인 감광성 수지 조성물.
The method of claim 1,
The quantum dot is a photosensitive resin composition that is a quantum dot that absorbs light of 360 nm to 780 nm and emits fluorescence at 500 nm to 700 nm.
상기 감광성 수지 조성물은, 상기 감광성 수지 조성물 총량에 대해,
상기 (A) 양자점 1 중량% 내지 50 중량%;
상기 (B) 바인더 수지 1 중량% 내지 10 중량%;
상기 (C) 광중합성 단량체 1 중량% 내지 10 중량%;
상기 (D) 광중합 개시제 0.01 중량% 내지 5 중량%; 및
상기 (E) 용매 잔부량
을 포함하는 감광성 수지 조성물.
The method of claim 1,
The photosensitive resin composition, relative to the total amount of the photosensitive resin composition,
(A) 1% to 50% by weight of quantum dots;
(B) 1 to 10% by weight of the binder resin;
(C) 1% to 10% by weight of the photopolymerizable monomer;
(D) 0.01% to 5% by weight of the photopolymerization initiator; And
The residual amount of the (E) solvent
Photosensitive resin composition comprising a.
상기 감광성 수지 조성물은 말론산; 3-아미노-1,2-프로판디올; 실란계 커플링제; 레벨링제; 불소계 계면활성제; 또는 이들의 조합을 더 포함하는 감광성 수지 조성물.
The method of claim 1,
The photosensitive resin composition is malonic acid; 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine-based surfactant; Or a photosensitive resin composition further comprising a combination thereof.
A photosensitive resin film manufactured using the photosensitive resin composition of any one of claims 1 to 15.
A color filter comprising the photosensitive resin film of claim 16.
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| KR20190086954A (en) * | 2018-01-15 | 2019-07-24 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using same and color filter |
| KR20190095070A (en) * | 2018-02-06 | 2019-08-14 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using same and color filter |
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| KR20120081557A (en) * | 2011-01-11 | 2012-07-19 | 도오꾜오까고오교 가부시끼가이샤 | Colored photosensitive resin composition for touch panel, touch panel and display device |
| KR20180025248A (en) * | 2016-08-30 | 2018-03-08 | 동우 화인켐 주식회사 | Self emission type photosensitive resin composition, color filter using thereof and image display device having the same |
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