Color conversion composition, color conversion film including the same, backlight unit and display device
By using a color conversion composition composed of specific compounds, the problem of color gamut reduction and high cost in LED color display technology is solved, and the color conversion effect with high brightness and high efficiency is achieved.
Patent Information
- Application Number
- CN202080005880.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-02-28
- Filing Date
- 2020-02-17
- Publication Date
- 2025-01-07
- Estimated Expiration
- 2040-02-17
AI Technical Summary
The existing LED color display technology is difficult to control color, resulting in a decrease in color gamut. The use of cadmium series quantum dots has safety and stability problems, and the production cost is high.
Using a color conversion composition composed of specific compounds, chemical formula 1 and chemical formula 2, a compound of a maximum absorption wavelength in the range of 400 nm to 500 nm and a maximum emission wavelength in the range of 500 nm to 650 nm is used for color conversion films, enhancing green and Red brightness and blue light absorption.
The brightness and color gamut of the color conversion film are improved, the luminous efficiency is enhanced, the production cost is reduced, and the durability is excellent.
Smart Images

Figure CN112996880B_ABST
Abstract
Description
Technical Field
[0001] This specification claims priority to and the benefit of Korean Patent Application No. 10-2019-0023886 filed in the Korean Intellectual Property Office on February 28, 2019, the entire contents of which are incorporated herein by reference.
[0002] The present invention relates to a color conversion composition, and a color conversion film, a backlight unit, and a display device including the same. Background Art
[0003] Existing light emitting diodes (LEDs) are obtained by mixing green phosphors and red phosphors into blue LEDs or mixing yellow phosphors and blue-green phosphors into UV LEDs. However, using this method, it is difficult to control the color, and therefore, the color rendering is not good. Therefore, the color gamut decreases.
[0004] In order to overcome this color gamut decline and reduce production costs, a method of obtaining green and red by filming quantum dots and combining the dots with blue LEDs has recently been attempted. However, there are safety issues with cadmium series quantum dots, and other quantum dots have significantly reduced efficiency compared to cadmium series quantum dots. In addition, quantum dots have reduced stability to oxygen and water, and have the disadvantage of significantly reduced performance when aggregated. In addition, the unit cost of production is high because it is difficult to keep the size constant when producing quantum dots.
[0005] Existing compounds having a bodipy structure have a narrow light emission half-maximum full width and are suitable for obtaining high color reproduction and high efficiency when used as a color conversion film, but are insufficient in light absorption of a light source due to a narrow light absorption region. Therefore, in order to absorb blue light and efficiently convert the blue light into green and red, an auxiliary fluorescent substance that helps energy transfer by assisting light absorption of the bodipy structure is required. Summary of the invention
[0006] Technical issues
[0007] The present disclosure aims to provide a color conversion composition, and a color conversion film, a backlight unit, and a display device including the same.
[0008] Technical Solution
[0009] One embodiment of the present specification provides a color conversion composition including a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2, wherein the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 have a molar ratio of 1:1 to 5:1.
[0010] [Chemical formula 1]
[0011]
[0012] [Chemical formula 2]
[0013]
[0014] In Chemical Formulas 1 and 2,
[0015] X1 to X4 are the same as or different from each other and are each independently a halogen group; a cyano group; a hydroxyl group; -OR A ; -C(=O)OR B ;-OC(=O)R C ; substituted or unsubstituted alkyl; substituted or unsubstituted alkynyl; substituted or unsubstituted aryl; or substituted or unsubstituted aralkyl,
[0016] R1 to R 17 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; -OR D ; -C(=O)OR E ;-OC(=O)R F ;-R G OR H ;-SR I ; -S(=O)2OR J ; a substituted or unsubstituted amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted coumarin group, or adjacent groups are bonded to each other to form a ring, and
[0017] R A To R J are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted coumarin group; or a substituted or unsubstituted naphthalimide group.
[0018] Another embodiment of the present specification provides a color conversion composition including a compound having a maximum absorption wavelength within a wavelength range of 400 nm to 500 nm, and a compound having a maximum emission wavelength within a wavelength range of 500 nm to 650 nm.
[0019] Another embodiment of the present specification provides a color conversion film including: a resin matrix; and a color conversion composition dispersed in the resin matrix.
[0020] Another embodiment of the present specification provides a backlight unit including the color conversion film.
[0021] Another embodiment of the present specification provides a display device including the backlight unit.
[0022] Beneficial Effects
[0023] The color conversion composition according to one embodiment of the present specification can enhance green and red brightness and enhance blue light absorption rate by including the compound of Chemical Formula 1 as an auxiliary fluorescent substance and the compound of Chemical Formula 2, compared with when only the existing compound having a bodipy structure is used. Therefore, by using the color conversion composition described in the present specification as a fluorescent material for a color conversion film under a blue backlight, a color conversion film having excellent brightness and color gamut and excellent durability can be provided.
[0024] Particularly, when the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are included in a molar ratio of 1:1 to 5:1, the compound of Chemical Formula 2 has favorable luminous efficiency. BRIEF DESCRIPTION OF THE DRAWINGS
[0025] Figure 1 is a mimetic diagram illustrating the structure of a backlight unit according to an embodiment of the present specification.
[0026] Figure 2 A mimetic diagram showing the structure of a display device according to an embodiment of the present specification. DETAILED DESCRIPTION
[0027] Hereinafter, the present application will be described in more detail.
[0028] One embodiment of the present specification provides a color conversion composition including a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.
[0029] In the present specification, unless otherwise specified, a specific part “comprising” a specific constituent element means that the specific part can further include other constituent elements, and does not exclude other constituent elements.
[0030] In this specification, a member being placed “on” another member includes not only a case where one member is in contact with another member but also a case where another member exists between the two members.
[0031] In this manual, It refers to the position at which a substituent is bonded.
[0032] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to an atom substituted by a corresponding substituent, a substituent that is spatially located closest to a corresponding substituent, or a substituent that replaces an atom substituted by a corresponding substituent. For example, two substituents that replace ortho positions in a benzene ring and two substituents that replace the same carbon in an aliphatic ring may be interpreted as groups that are "adjacent" to each other.
[0033] In the present specification, adjacent groups bond to each other to form a ring means that, as described above, adjacent groups bond to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle, and adjacent groups bond to each other to form a monocyclic or polycyclic ring, aliphatic, aromatic or a condensed form thereof, and the form is not limited thereto.
[0034] In the present specification, bonding with an adjacent group to form a ring means bonding with the adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a combination thereof.
[0035] In the present specification, the aliphatic hydrocarbon ring means, as a non-aromatic ring, a ring formed only of carbon atoms and hydrogen atoms.
[0036] In the present specification, examples of the aromatic hydrocarbon ring may include a phenyl group, a naphthyl group, an anthracenyl group, and the like, but are not limited thereto.
[0037] In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more hetero atoms.
[0038] In the present specification, an aromatic heterocycle means an aromatic ring containing one or more heteroatoms.
[0039] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.
[0040] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.
[0041] In the present specification, the term "substituted or unsubstituted" means substituted with one, two or more substituents selected from the following: deuterium; a halogen group; a cyano group; a nitro group; a -C(=O)R; a -C(=O)OR'; a -OC(=O)R", an imide group; an amide group; a hydroxyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted coumarin group; or Or it is substituted by a substituent in which two or more of the substituents exemplified above are linked to each other, or it has no substituent, and R, R' and R" are substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; or substituted or unsubstituted coumarinyl.
[0042] In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.
[0043] In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30.
[0044] In the present specification, in the amide group, nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
[0045] In the present specification, the amine group can be selected from: -NH2; monoalkylamine; dialkylamine; N-alkylamine; monoarylamine; diarylamine; N-arylheteroarylamine; N-alkylheteroarylamine; monoheteroarylamine and diheteroarylamine, and although there is no particular limitation, the number of carbon atoms is preferably 1 to 30.
[0046] In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
[0047] In the present specification, the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.
[0048] In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.
[0049] In the present specification, the alkyl group in the alkylamine group, the N-alkylarylamine group, the alkylthio group, the alkylsulfonyl group and the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above.
[0050] In the present specification, specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but are not limited thereto.
[0051] In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
[0052] In the present specification, the cycloalkyl group is not particularly limited but preferably has 3 to 30 carbon atoms, and specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
[0053] In this specification, haloalkyl represents an alkyl group in which the hydrogen atoms of the alkyl group are substituted by the same or different halogen groups. The haloalkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 10. Specific examples thereof may include -CH2Cl, -CF3, -CH2CF3, -CF2CF3, etc., but are not limited thereto.
[0054] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30.
[0055] In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. In the present specification, the alkynyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples thereof may include alkynyl groups such as ethynyl, propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl, and the like, but are not limited thereto.
[0056] In the present specification, the aryl group is not particularly limited but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
[0057] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
[0058] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group may include naphthyl, anthracenyl, phenanthrenyl, triphenyl, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.
[0059] In the present specification, the aryl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
[0060] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
[0061] When the fluorenyl group is substituted, it may include etc., however, the structure is not limited thereto.
[0062] In the present specification, the aryl in aryloxy and arylthio is the same as the example of aryl described above. Specific examples of aryloxy can include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthraceneoxy, 2-anthraceneoxy, 9-anthraceneoxy, 1-phenanthrenoxy, 3-phenanthrenoxy, 9-phenanthrenoxy, etc., and specific examples of arylthio can include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., however, aryloxy and arylthio are not limited thereto.
[0063] In the present specification, a heteroaryl group is a group containing one or more non-carbon atoms (i.e., heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, thiazolyl, isothiophene Azolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl and the like, but not limited thereto.
[0064] In the present specification, in the coumarin group, the carbon of the coumarin group may be substituted by: a halogen group; a nitrile group; a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms; an amine group; a linear or branched alkoxy group having 1 to 25 carbon atoms; or an aryl group having 6 to 30 carbon atoms.
[0065] In one embodiment of the present specification, the compound represented by Chemical Formula 1 is an aza-bodipy-based compound, and the compound represented by Chemical Formula 2 is a bodipy-based compound. When a color conversion film is prepared using a color conversion composition including both an aza-bodipy-based compound and a bodipy-based compound, a color conversion film having excellent brightness and color gamut and excellent durability can be provided.
[0066] In one embodiment of the present specification, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 have a molar ratio of 1:1 to 5:1. When the compound of Chemical Formula 1 and the compound of Chemical Formula 2 within the above molar ratio range are included, the compound of Chemical Formula 2 has excellent luminous efficiency. Specifically, based on the molar ratio of 1:1, more compounds of Chemical Formula 2 are included, and the amount of blue light absorption is rapidly reduced. In addition, when the amount of the compound of Chemical Formula 1 included is within 5 times the molar number of the compound of Chemical Formula 2, the ratio of blue light absorption and the brightness increase rate are high, and therefore, considering the amount of dye used, the efficiency is excellent.
[0067] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum absorption wavelength within a wavelength range of 400 nm to 500 nm. Energy transfer to bodipy may occur by effectively absorbing blue light OLED.
[0068] In one embodiment of the present specification, the compound represented by Chemical Formula 2 has a maximum emission wavelength within a wavelength range of 500 nm to 650 nm. By using a compound having a maximum emission within a target wavelength range, brightness and color gamut may be enhanced.
[0069] When the compound represented by Chemical Formula 2 is used alone, since the absorption of the blue light source is not significant, the color conversion in the green and red regions is low, however, when the compound of Chemical Formula 1 having high absorption in the blue light region is used therein, energy transfer occurs in the order of blue light, the compound of Chemical Formula 1, and the compound of Chemical Formula 2, and the fluorescence characteristics of the compound of Chemical Formula 2 are finally obtained.
[0070] A color conversion composition according to another embodiment of the present specification includes a compound having a maximum absorption wavelength within a wavelength range of 400 nm to 500 nm, and a compound having a maximum emission wavelength within a wavelength range of 500 nm to 650 nm.
[0071] The compound having a maximum absorption wavelength within a wavelength range of 400 nm to 500 nm may be represented by Chemical Formula 1, and the compound having a maximum emission wavelength within a wavelength range of 500 nm to 650 nm may be represented by Chemical Formula 2.
[0072] In one embodiment of the present specification, X1 to X4 are the same as or different from each other, and are each independently a halogen group; a cyano group; a hydroxyl group; -OR A ; -C(=O)OR B ;-OC(=O)R C ; substituted or unsubstituted alkyl; substituted or unsubstituted alkynyl; substituted or unsubstituted aryl; or substituted or unsubstituted aralkyl.
[0073] In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and are each independently a halogen group; a cyano group; -OR A ; -C(=O)OR B ;-OC(=O)R C ; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C1 to C20 alkynyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C6 to C30 heteroaryl.
[0074] In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and are each independently a halogen group; a cyano group; -OR A ; -C(=O)OR B ; substituted or unsubstituted methyl; substituted or unsubstituted ethynyl; substituted or unsubstituted phenyl; substituted or unsubstituted fluorenyl; or substituted or unsubstituted thienyl.
[0075] In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and are each independently a halogen group; a cyano group; -ORA ; -C(=O)OR B ; methyl; substituted or unsubstituted ethynyl; unsubstituted or substituted phenyl with a halogen group; substituted or unsubstituted fluorenyl; or thienyl.
[0076] In one embodiment of the present specification, X1 and X2 are each independently -OR A , and R A is a substituted or unsubstituted aryl group.
[0077] In one embodiment of the present specification, X1 and X2 are each independently -OR A , and R A is substituted or unsubstituted phenyl.
[0078] In one embodiment of the present specification, X1 and X2 are each independently -OR A , and R A is unsubstituted or nitro-substituted phenyl.
[0079] In one embodiment of the present specification, X1 and X2 are each independently -C(=O)OR B , and R B is a substituted or unsubstituted alkyl group.
[0080] In one embodiment of the present specification, X1 and X2 are each independently -C(=O)OR B , and R B is an alkyl group which is unsubstituted or substituted with a haloalkyl group.
[0081] In one embodiment of the present specification, X3 and X4 are the same as or different from each other, and are each independently a halogen group; a cyano group; a hydroxyl group; -OR A ; -C(=O)OR B ;-OC(=O)R C ; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C1 to C20 alkynyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C6 to C30 heteroaryl.
[0082] In one embodiment of the present specification, X3 and X4 are the same as or different from each other, and are each independently a halogen group; a cyano group; a hydroxyl group; -OR A ;-OC(=O)R C ; substituted or unsubstituted ethynyl; substituted or unsubstituted naphthyl; substituted or unsubstituted perylenyl.
[0083] In one embodiment of the present specification, X3 and X4 are the same as or different from each other, and are each independently a halogen group; a cyano group; a hydroxyl group; -OR A ;-OC(=O)R C ; substituted or unsubstituted ethynyl; naphthyl; or perylenyl.
[0084] In one embodiment of the present specification, X3 and X4 are each independently -OR A , and R A is a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
[0085] In one embodiment of the present specification, X3 and X4 are each independently -OR A , and R A is a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.
[0086] In one embodiment of the present specification, X3 and X4 are each independently -OR A , and R A is unsubstituted or substituted methyl by haloalkyl; or unsubstituted or substituted phenyl by nitro.
[0087] In one embodiment of the present specification, X3 and X4 are each independently -OC(=O)R C , and R C is a substituted or unsubstituted alkyl group.
[0088] In one embodiment of the present specification, X3 and X4 are each independently -OC(=O)R C , and R C is a substituted or unsubstituted methyl group.
[0089] In one embodiment of the present specification, X3 and X4 are each independently -OC(=O)R C , and R C is a methyl group which is unsubstituted or substituted by a halogen group.
[0090] In one embodiment of the present specification, R1 to R 17 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; -OR D ; -C(=O)OR E ;-OC(=O)R F ;-R G OR H ;-SR I ; -S(=O)2OR J; substituted or unsubstituted amino; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; or substituted or unsubstituted coumarinyl; or adjacent groups may be bonded to each other to form a ring.
[0091] In one embodiment of the present specification, R1 to R 10 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; -OR D ; -C(=O)OR E ;-SR I ; substituted or unsubstituted amine; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl, or adjacent groups may be bonded to each other to form a ring.
[0092] In one embodiment of the present specification, R1 to R 10 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; -OR D ; -C(=O)OR E ;-SR I ; a substituted or unsubstituted amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C1 to C20 alkenyl group; a substituted or unsubstituted C1 to C20 alkynyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, or adjacent groups may be bonded to each other to form a ring.
[0093] In one embodiment of the present specification, R1 to R 10 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a pyridyl group; a pyrrolyl group; a thienyl group; Azolyl; thiazolyl; -OR D ; -C(=O)OR E ;-SR I; an unsubstituted or substituted amino group with one or more substituents selected from an alkyl group and an aryl group; an unsubstituted or aryl substituted silyl group; an unsubstituted or halogen substituted alkyl group; an unsubstituted or substituted alkenyl group with one or more substituents selected from a cyano group and an aryl group; a substituted or unsubstituted ethynyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted indenyl group; a substituted or unsubstituted dihydroindenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzo substituted or unsubstituted benzofuranyl; substituted or unsubstituted indolyl; substituted or unsubstituted quinoxalinyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted carbazolyl, or adjacent groups may be bonded to each other to form a ring.
[0094] In one embodiment of the present specification, when R1 to R 10 Each is independently -C(=O)OR E When R E is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted coumarin group; or a substituted or unsubstituted naphthalimide group.
[0095] In one embodiment of the present specification, when R1 to R 10 Each independently is -SR I When R I is a substituted or unsubstituted alkyl group.
[0096] In one embodiment of the present specification, R 11 To R 16 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; -OR D ; -C(=O)OR E ;-R G OR H ;-SR I ; -S(=O)2OR J ; a substituted or unsubstituted amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted coumarin group, or adjacent groups may be bonded to each other to form a ring.
[0097] In one embodiment of the present specification, R 11 To R 16are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; -OR D ; -C(=O)OR E ;-R G OR H ;-SR I ; -S(=O)2OR J ; substituted or unsubstituted amino; substituted or unsubstituted silyl; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C1 to C20 alkenyl; substituted or unsubstituted C1 to C20 alkynyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; or substituted or unsubstituted coumarinyl, or adjacent groups may be bonded to each other to form a ring.
[0098] In one embodiment of the present specification, R 11 To R 16 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a pyrrolyl group; -OR D ; -C(=O)OR E ;-R G OR H ;-SR I ; -S(=O)2OR J ; substituted or unsubstituted amino; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted cyclohexyl; unsubstituted or aryl-substituted alkenyl; substituted or unsubstituted ethynyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted thienyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted carbazolyl; or substituted or unsubstituted coumarinyl, or adjacent groups may be bonded to each other to form a ring.
[0099] In one embodiment of the present specification, when R 11 To R 16 Each independently is -OR D When R D is a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
[0100] In one embodiment of the present specification, when R 11 To R 16 Each is independently -C(=O)OR E When R Eis a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted coumarin group; or a substituted or unsubstituted naphthalimide group.
[0101] In one embodiment of the present specification, when R 11 To R 16 Each is independently -OC(=O)R F When R F is a substituted or unsubstituted alkyl group.
[0102] In one embodiment of the present specification, when R 11 To R 16 Each independently is -R G OR H When R G and R H Each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
[0103] In one embodiment of the present specification, when R 11 To R 16 Each independently is -SR I When R I is a substituted or unsubstituted aryl group.
[0104] In one embodiment of the present specification, when R 11 To R 16 Each is independently -S(=O)2OR J When R J is a substituted or unsubstituted alkyl group.
[0105] In one embodiment of the present specification, R 17 is hydrogen; deuterium; halogen group; cyano group; -OR D ; -C(=O)OR E ;-SR I ; substituted or unsubstituted amino; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; or substituted or unsubstituted coumarinyl.
[0106] In one embodiment of the present specification, R 17 is hydrogen; deuterium; halogen group; cyano group; -OR D ; -C(=O)OR E ;-SR I; substituted or unsubstituted amino; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; or substituted or unsubstituted coumarin.
[0107] In one embodiment of the present specification, R 17 is hydrogen; deuterium; halogen group; cyano; pyrenyl; pyridyl; furanyl; thienyl; -OR D ; -C(=O)OR E ;-SR I ; substituted or unsubstituted amino; substituted or unsubstituted methyl; substituted or unsubstituted cyclohexyl; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; substituted or unsubstituted carbazolyl; or substituted or unsubstituted coumarinyl.
[0108] In one embodiment of the present specification, when R 17 For-OR D When R D is substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; or substituted or unsubstituted coumarinyl.
[0109] In one embodiment of the present specification, when R 17 For-OR D When R D is substituted or unsubstituted methyl; substituted or unsubstituted phenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted coumarinyl.
[0110] In one embodiment of the present specification, when R 17 -C(=O)OR E When R E is a substituted or unsubstituted alkyl group.
[0111] In one embodiment of the present specification, when R 17 For-SR I When R I is a substituted or unsubstituted alkyl group; or a substituted or unsubstituted coumarin group.
[0112] In one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by any one of the following compounds.
[0113]
[0114]
[0115]
[0116]
[0117]
[0118]
[0119] In one embodiment of the present specification, the compound represented by Chemical Formula 2 is represented by any one of the following compounds
[0120]
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132] In said compounds, Me is methyl and Ph is phenyl.
[0133] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in an amount of 0.1 to 10 parts by weight, specifically 0.1 to 5 parts by weight, and more specifically 0.1 to 3 parts by weight, based on 100 parts by weight of the color conversion composition.
[0134] When the content of the compound represented by Chemical Formula 1 satisfies the above range, energy absorbed by the blue light OLED may be efficiently transferred to the compound represented by Chemical Formula 2.
[0135] According to one embodiment of the present specification, the compound represented by Chemical Formula 2 may be included in an amount of 0.1 to 10 parts by weight, specifically 0.1 to 5 parts by weight, and more specifically 0.15 to 2.5 parts by weight, based on 100 parts by weight of the color conversion composition.
[0136] When the content of the compound represented by Chemical Formula 2 satisfies the above range, light having a maximum emission wavelength of 500 nm to 650 nm may be emitted with enhanced brightness by receiving energy absorbed by the compound represented by Chemical Formula 1.
[0137] According to one embodiment of the present specification, the color conversion composition may further include a resin matrix, a functional monomer, and a photoinitiator.
[0138] According to one embodiment of the present specification, the color conversion composition may further include a resin matrix.
[0139] The resin matrix material is preferably a thermoplastic polymer or a thermosetting polymer. Specifically, the following can be used as the resin matrix material: poly (meth) acrylic acid such as polymethyl methacrylate (PMMA), polycarbonate (PC), polystyrene (PS), polyarylene (PAR), polyurethane (PU), styrene-acrylonitrile (SAN), polyvinylidene fluoride (PVDF), modified polyvinylidene fluoride (modified-PVDF), etc.
[0140] The resin matrix may be included in an amount of 5 to 80 parts by weight, 10 to 70 parts by weight, or 15 to 50 parts by weight, based on 100 parts by weight of the color conversion composition.
[0141] In one embodiment of the present specification, as examples of functional monomers, one or more types selected from the following can be used: monofunctional monomers such as polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate and phenoxyethyl(methyl)acrylate; and multifunctional monomers such as polyethylene glycol (meth)acrylate, polypropylene glycol (meth)acrylate, trimethylolethane triacrylate, trimethylolpropane triacrylate, neopentyl glycol (meth)acrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, however, the functional monomers are not limited thereto.
[0142] In one embodiment of the present specification, the color conversion composition may include a multifunctional monomer. When the multifunctional monomer is included, more effective color conversion may be achieved and physical stability may be enhanced by combining with the compound of Chemical Formula 1 and the compound of Chemical Formula 2.
[0143] The functional monomer may be included in an amount of 1 to 70 parts by weight, 10 to 60 parts by weight, or 30 to 60 parts by weight, based on 100 parts by weight of the color conversion composition.
[0144] According to one embodiment of the present specification, the photoinitiator is not particularly limited as long as it is an initiator that generates free radicals by light to initiate crosslinking, and examples thereof may include one or more types selected from acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds.
[0145] The acetophenone compound can be selected from: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, but are not limited thereto.
[0146] The biimidazole compound can be selected from: 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, but is not limited thereto.
[0147] The triazine compound can be selected from: 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propanoate, ethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl- 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionamide, 2,4-bis(trichloromethyl)-6-p-methoxyphenylvinyl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s-triazine, 2-hydroxyphenyl-s-triazine and 2-trichloromethyl-4-amino-6-p-methoxyphenylvinyl-s-triazine, but are not limited thereto.
[0148] The oxime compound can be selected from: 1,2-octanedione-1-(4-phenylthio)phenyl-2-(o-benzoyl oxime) (Ciba-Geigy, CGI 124), ethyl ketone-1-(9-ethyl)-6-(2-methylbenzoyl-3-yl)-1-(O-acetyl oxime) (CGI242), N-1919 (Adeka) and OXE-02 ((E)-1-(((1-(9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl)ethylidene)amino)oxy)ethan-1-one, BASF), but is not limited thereto.
[0149] The photoinitiator may be included in an amount of 0.1 to 10 parts by weight, and preferably 1 to 5 parts by weight, based on 100 parts by weight of the color conversion composition.
[0150] According to one embodiment of the present specification, the color conversion film according to the above embodiment further comprises light diffusion particles. By dispersing the light diffusion particles in the color conversion film instead of the light diffusion film used in the art for improving brightness, higher brightness can be exhibited compared to using a separate light diffusion film, and the bonding process can also be omitted.
[0151] As light diffusing particles, particles with a high refractive index can be used with a resin matrix, and examples thereof may include TiO2, silica, borosilicate, alumina, sapphire, air or other gas-filled hollow beads or particles (e.g., air / gas-filled glass or polymer); polystyrene, polycarbonate, polymethyl methacrylate, acryl, methyl methacrylate, styrene, melamine resin, formaldehyde resin, or polymer particles containing melamine and formaldehyde resin, or any suitable combination thereof.
[0152] The particle diameter of the light diffusion particles may be in the range of 0.01 μm to 5 μm, for example, in the range of 0.3 μm to 1 μm. The content of the light diffusion particles may be determined as required, for example, in the range of about 1 to 30 parts by weight based on 100 parts by weight of the resin matrix.
[0153] In one embodiment of the present specification, the color conversion composition may further include one or more types of additives selected from a curing agent, a surfactant, an adhesion promoter, an adhesion aid, an ultraviolet absorber, and an anticoagulant, and the content of the additive is 0.1 to 10 parts by weight, and preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the color conversion composition.
[0154] In one embodiment of the present specification, the color conversion film may include the color conversion composition described above, or a cured material thereof. In one embodiment of the present specification, the color conversion film includes a cured material of the color conversion composition described above.
[0155] The color conversion film may further include an additional layer including a compound emitting light having a different wavelength from the above-mentioned color conversion composition.
[0156] The color conversion film according to the above embodiment may have a thickness of 2 μm to 200 μm. In particular, the color conversion film may exhibit high brightness even with a small thickness of 2 μm to 20 μm. This is due to the fact that the content of fluorescent material molecules contained in a unit volume is higher than that of quantum dots.
[0157] The color conversion film according to the above-described embodiment may have a substrate disposed on one surface. When preparing the color conversion film, the substrate may function as a support. The type of substrate is not particularly limited, and the material or thickness is not limited as long as it is transparent and can function as a support. Here, transparent means having a visible light transmittance of 70% or more. For example, a PET film may be used as the substrate.
[0158] The above-mentioned color conversion film may be prepared by coating a solution in which the color conversion composition is dissolved on a substrate and drying the resultant, or by extruding the color conversion composition and forming it into a film.
[0159] The color conversion composition is dissolved in the solution, and therefore, the color conversion composition is uniformly distributed in the solution. This is different from the quantum dot film preparation process which requires a separate dispersion process.
[0160] For the solution in which the color conversion composition is dissolved, the preparation method is not particularly limited as long as the color conversion composition is dissolved in the solution.
[0161] According to one example, a solution in which the color conversion composition is dissolved may be prepared by dissolving the above-mentioned color conversion composition in a solvent.
[0162] According to another example, a solution in which a color conversion composition is dissolved may be prepared by preparing a first solution by dissolving the color conversion composition in a solvent, preparing a second solution by dissolving a resin in a solvent, and mixing the first solution and the second solution. When the first solution and the second solution are mixed, they are preferably mixed uniformly. However, the method is not limited thereto, and a method in which the color conversion composition and the resin are simultaneously added and dissolved in a solvent, a method in which the color conversion composition is dissolved in a solvent and then the resin is added and dissolved, a method in which the resin is dissolved in a solvent and then the color conversion composition is added and dissolved, and the like may be used.
[0163] As the resin contained in the solution, the above-mentioned resin matrix material, a monomer curable to the resin matrix resin, or a mixture thereof can be used. For example, the monomer curable to the resin matrix resin includes a (meth) acrylic monomer, and can be formed into the resin matrix material by UV curing. When such a curable monomer is used, an initiator required for curing can be further added as needed.
[0164] The solvent is not particularly limited as long as it can be removed by drying thereafter while not adversely affecting the coating process.
[0165] Non-limiting examples of the solvent may include toluene, xylene, acetone, chloroform, various alcohol solvents, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), ethyl acetate (EA), butyl acetate, dimethylformamide (DMF), dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO), N-methylpyrrolidone (NMP), propylene glycol monomethyl ether acetate (PGEMA), etc., but are not limited thereto. In addition, the solvent may be used in one type or as a mixture of two or more.
[0166] In the solution in which the color conversion composition is dissolved, the solid content may be 10 wt % to 30 wt %, or 15 wt % to 25 wt %.
[0167] The process of coating the solution in which the color conversion composition is dissolved on the substrate may use a roll-to-roll process. For example, a process may be used in which a substrate is unwound from a roll on which the substrate is wound, a solution in which the color conversion composition is dissolved is coated on one surface of the substrate, the resultant is dried, and then the resultant is wound on a roll again. When the roll-to-roll process is used, the viscosity of the resin solution is preferably determined within a range capable of performing the process, and may be determined, for example, within a range of 200 cps to 2,000 cps.
[0168] As the coating method, various known methods may be used, for example, a die coater may be used, or various bar coating methods such as a comma coater and a reverse comma coater may be used.
[0169] After coating, a drying process is performed. The drying process may be performed under conditions required to remove the solvent. For example, by performing drying under conditions to sufficiently evaporate the solvent in an oven positioned close to a coater in the direction in which the substrate advances during the coating process, a color conversion film containing a fluorescent material containing a color conversion composition having a target thickness and concentration may be obtained on the substrate.
[0170] When a monomer curable into a resin matrix resin is used as the resin contained in the solution, curing such as UV curing may be performed before or simultaneously with drying.
[0171] When the color conversion composition is formed into a film by extrusion with a resin, an extrusion method known in the art can be used. For example, the color conversion film can be prepared by extruding the color conversion composition with a resin such as polycarbonate (PC), poly(meth)acryl, and styrene-acrylonitrile (SAN) resins.
[0172] According to one embodiment of the present specification, the color conversion film may have a protective film or a barrier film provided on at least one surface. As the protective film or the barrier film, those known in the art may be used.
[0173] One embodiment of the present specification provides a backlight unit including a color conversion film including the above-mentioned color conversion composition. In addition to including the color conversion film, the backlight unit may have a backlight unit configuration known in the art. Figure 1 A simulation diagram of a backlight unit structure according to an embodiment is shown. Figure 1 , a color conversion film including a color conversion composition is disposed on a surface of the light guide plate opposite to a surface facing the reflection plate. Figure 1A configuration including a light source and a reflection plate surrounding the light source is shown, however, the configuration is not limited to this structure and may be changed according to a backlight unit structure known in the art.
[0174] According to an embodiment of the present specification, the backlight unit includes a light source, and the light source may emit blue light.
[0175] In another embodiment, the backlight unit includes a light source, and light emitted from the light source may have an emission peak in a region of 430 nm to 470 nm.
[0176] In another embodiment, the backlight unit includes a light source, the light source may be a white light source, and light emitted from the white light source includes an emission peak in a region of 430 nm to 470 nm.
[0177] In another embodiment, the backlight unit includes a light source, the light source may be a blue light source, and light emitted from the blue light source includes an emission peak in a region of 430 nm to 470 nm.
[0178] In another embodiment, the backlight unit includes a light source, and the light source may be a blue light OLED.
[0179] The backlight unit according to one embodiment of the present specification uses blue light, and blue, red, and green light emissions may be obtained through a color conversion film including the compound of Chemical Formula 1 and the compound of Chemical Formula 2.
[0180] In addition, as the light source, a direct type and a side chain type can be used, and as required, a reflective plate or a reflective layer may not be included or may be replaced with other structures, and additional films such as a light diffusion film, a light collection film, and a brightness enhancement film may be provided as required. Preferably, a prism sheet, a multilayer reflective polarizing film, a light collection film, or a brightness enhancement film is further provided on the color conversion film.
[0181] In such Figure 1 In the configuration of the backlight unit in FIG. 1 , a scattering pattern may be provided on the upper or lower surface of the light guide plate as required. The light introduced into the light guide plate has an uneven light distribution due to repetition of an optical process such as reflection, total reflection, refraction, or transmission, and a scattering pattern may be used to induce the uneven light distribution into uniform brightness.
[0182] One embodiment of the present specification provides a display device including a backlight unit. The display device is not particularly limited as long as it includes a backlight unit. For example, the display device includes a display module and a backlight unit. Figure 2 However, the structure is not limited thereto, and additional films such as a light diffusion film, a light collection film, and a brightness enhancement film may be further provided between the display module and the backlight unit as required.
[0183] Hereinafter, this specification will be described in detail with reference to the embodiments. However, the embodiments according to this specification can be modified into a variety of other forms, and the scope of this specification should not be considered to be limited to the embodiments described below. The embodiments of this specification are provided to more fully describe this specification to those of ordinary skill in the art.
[0184] The compound according to one embodiment of the present application can be prepared using the preparation method to be described below.
[0185] For example, the compound of Chemical Formula 1 may have its core structure prepared as in the following Reaction Formula 1. Pyrrole is an intermediate of the compound of Chemical Formula 2 and may be prepared according to Reaction Formula 2. The substituents may be bonded using methods known in the art, and the type, position or number of the substituents may be varied according to techniques known in the art.
[0186] [Reaction 1]
[0187]
[0188] Under nitrogen, benz[c,d]indole-2(1H)-one (1 equivalent) and aminopyrimidine (1.5 equivalents) are introduced into a solvent and stirred while heating at 90°C. After the disappearance of benz[c,d]indole-2(1H)-one, the reaction material is cooled. After pouring water therein, the resultant is stirred for 30 minutes, then extracted with chloroform, and dried over anhydrous magnesium sulfate. The resultant is concentrated by vacuum distillation, then dissolved in toluene, and after adding TEA and BF3OET2 thereto while stirring, stirred at 120°C. After the reaction is completed, the resultant is cooled, extracted with CHCl3, dried over anhydrous magnesium sulfate, then concentrated by vacuum distillation, and purified by recrystallization or column.
[0189] [Reaction Scheme 2] General Synthesis of Pyrrole
[0190]
[0191] Under argon, aldehyde (1 equivalent) and azide (1.5 equivalent) are introduced into a solvent, and after a catalyst (about 2% to 5%) is introduced therein, the resultant is stirred while heating at 110°C. After the reaction is completed, the resultant is extracted with water and ethyl acetate and dried over anhydrous magnesium sulfate. The resultant is concentrated by vacuum distillation and then purified by column.
[0192] [Preparation Example 1] Preparation of Compound 1
[0193]
[0194] The preparation was performed in the same manner as in the method of Reaction Scheme 1, and Compound 1 was obtained in a yield of 38% by column purification.
[0195] C 40 H 16 BF 20 HR LC / MS / MS m / z calculated for N3 (M+): 929.1118, found: 929.1119.
[0196] [Preparation Example 2] Preparation of Compound 2
[0197]
[0198] The preparation was carried out in the same manner as in the method of Reaction Formula 1, and Compound 2 was obtained in a yield of 78% by column purification.
[0199] C 74 H 44 HR LC / MS / MS m / z calculated for BF8N3(M+): 1137.3501, found: 1137.3508.
[0200] [Preparation Example 3] Preparation of Compound 3
[0201]
[0202] The preparation was carried out in the same manner as in the method of Reaction Scheme 1, and Compound 3 was obtained in a yield of 55% by column purification.
[0203] C 33 H 13 BF 17 HR LC / MS / MS m / z calculated for N3 (M+): 785.0931; found: 785.0928.
[0204] [Preparation Example 4] Preparation of Compound 4
[0205]
[0206] The preparation was carried out in the same manner as in the method of Reaction Scheme 1, and Compound 4 was obtained in a yield of 58% by column purification.
[0207] C 33 H 13 BF 14 HR LC / MS / MS m / z calculated for N3(M+): 742.1010; found: 742.1011
[0208] [Preparation Example 5] Preparation of Compound 5
[0209]
[0210] The preparation was carried out in the same manner as in the method of Reaction Scheme 2, and Compound 5 was obtained in a yield of 62% by column purification.
[0211] C 65 H 53 HR LC / MS / MS m / z calculated for BF2N2O (M+): 926.4219; found: 926.4223.
[0212] [Preparation Example 6] Preparation of Compound 6
[0213]
[0214] The preparation was carried out in the same manner as in the method of Reaction Scheme 2, and Compound 6 was obtained in a yield of 78% by column purification.
[0215] C 21 H 19 HR LC / MS / MS m / z calculated for BN4 (M+): 338.1703; found: 338.1699.
[0216] The properties of the compounds 1 to 6 prepared in Preparation Examples 1 to 6 are shown in Table 1 below, and were measured by preparing the solution to 10 -5 After M.
[0217] [Table 1]
[0218]
[0219] Abs (maximum absorption wavelength) was measured using a MEGA-2100 device from SCINCO Co., Ltd., and the Abs intensity (absorbance in the 450 nm absorption region) was determined, and PL (maximum emission wavelength) was measured using an FS-2 device from SCINCO Co., Ltd., and the FWHM (full width at half maximum) of PL was determined. In addition, quantum efficiency was measured using a Quantaurus-QY device from Hamamatsu Photonics KK.
[0220] [Example 1]
[0221] A solution was prepared by mixing 0.5 parts by weight of the prepared compound 5 (in toluene solution, the maximum absorption wavelength was 590 nm, the maximum emission wavelength was 627 nm, and the half-maximum width was 39 nm), 1.0 parts by weight of the prepared compound 1 (in toluene solution, the maximum absorption wavelength was 458 nm, the maximum emission wavelength was 504 nm, and the half-maximum width was 63 nm), 33.9 parts by weight of an acrylic adhesive, 59.3 parts by weight of a multifunctional monomer (pentaerythritol triacrylate, Nippon Kayaku Co., Ltd.), 2.3 parts by weight of an adhesion promoter and surfactant (KBM 503, Shin-Etsu Chemical Co., Ltd.), and 3.0 parts by weight of a photoinitiator ( 477, BASF) was dissolved in propylene glycol monomethyl ether acetate (PGEMA) solvent to have a solid content of 21 wt%.
[0222] After the mixed solution was sufficiently stirred, the solution was coated on a glass substrate as a thin film and then dried to prepare a color conversion film.
[0223] The brightness spectrum of the prepared color conversion film was measured using a spectrophotometer (SR series from Topcon Technohouse). Specifically, the prepared color conversion film was laminated on one surface of a light guide plate of a backlight unit including an LED blue backlight (maximum emission wavelength 450 nm) and a light guide plate, and after laminating a prism sheet and a DBEF on the color conversion film, the initial value was set so that the brightness of the blue LED light based on the film was 600 nit.
[0224] [Example 2]
[0225] The experiment was conducted in the same manner as in Example 1, except that in Example 1, Compound 1 was used at 0.5 parts by weight.
[0226] [Example 3]
[0227] The experiment was conducted in the same manner as in Example 1, except that in Example 1, Compound 1 was used at 1.5 parts by weight.
[0228] [Example 4]
[0229] The experiment was performed in the same manner as in Example 1, except that Compound 2 (in toluene solution, maximum absorption wavelength 461 nm, maximum emission wavelength 509 nm, and full width at half maximum 60 nm) was used instead of Compound 1 in Example 1.
[0230] [Example 5]
[0231] The experiment was performed in the same manner as in Example 1, except that Compound 3 (maximum absorption wavelength 456 nm, maximum emission wavelength 504 nm, and full width at half maximum 68 nm in toluene solution) was used instead of Compound 1 in Example 1.
[0232] [Example 6]
[0233] The experiment was performed in the same manner as in Example 1, except that Compound 6 (maximum absorption wavelength 509 nm, maximum emission wavelength 520 nm, and full width at half maximum 23 nm in toluene solution) was used instead of Compound 5 in Example 1.
[0234] [Example 7]
[0235] The experiment was conducted in the same manner as in Example 6, except that Compound 3 (maximum absorption wavelength 456 nm, maximum emission wavelength 504 nm, and full width at half maximum 68 nm in toluene solution) was used instead of Compound 1 in Example 6.
[0236] [Comparative Example 1]
[0237] The experiment was conducted in the same manner as in Example 1, except that Compound 1 was not added and Compound 5 was used at 0.5 parts by weight in Example 1.
[0238] [Comparative Example 2]
[0239] The experiment was conducted in the same manner as in Example 6, except that in Example 6, Compound 1 was not added and Compound 6 was used at 0.5 parts by weight.
[0240] [Comparative Example 3]
[0241] The experiment was conducted in the same manner as in Example 1, except that Compound 5 was not added and Compound 1 was used at 1.0 part by weight in Example 1.
[0242] The measured properties of the color conversion films in Examples and Comparative Examples are described in Table 2 below.
[0243] [Table 2]
[0244]
[0245] In Table 2, Blue Light Source Absorption (%) indicates the extent to which the compound absorbs the LED blue backlight used (maximum emission wavelength 450 nm) as %, and Intensity (au) is a number representing the y value of the maximum peak in the 500 nm to 750 nm region in the brightness spectrum.
[0246] It has been determined that the prepared film containing both the compound of Chemical Formula 1 and the compound of Chemical Formula 2 closely follows the film prepared using only the compound of Chemical Formula 1 (Comparative Example 3) in terms of quantum efficiency and blue light source absorption, and closely follows the maximum emission wavelength and half-maximum full width characteristics of the film prepared using only the compound of Chemical Formula 2 (Comparative Examples 1 and 2). In addition, compared with the film prepared using only one compound alone, the film according to the present disclosure was measured to have a higher intensity, thereby showing more favorable efficiency.
Claims
1. A color conversion composition comprising: A compound represented by any one of the following compounds of Group 1; and A compound represented by any one of the following compounds of Group 2, wherein the molar ratio of the compound represented by any one of the compounds of Group 1 to the compound represented by any one of the compounds of Group 2 is 1:1 to 5:1: [Group 1] [Group 2] In the compound, Me is methyl; and Ph is phenyl. 2 . The color conversion composition according to claim 1 , wherein the compound represented by any one of the compounds of Group 1 has a maximum absorption wavelength in a wavelength region of 400 nm to 500 nm. 3 . The color conversion composition according to claim 1 , wherein the compound represented by any one of the compounds of Group 2 has a maximum emission wavelength in a wavelength region of 500 nm to 650 nm.
4. The color conversion composition according to claim 1, wherein based on a total of 100 parts by weight of the color conversion composition, The content of the compound represented by any one of the compounds of Group 1 is 0.1 parts by weight to 3 parts by weight; and The content of the compound represented by any one of the compounds of Group 2 is 0.15 parts by weight to 2.5 parts by weight.
5. The color conversion composition of claim 1, further comprising a resin matrix. 6 . A color conversion film comprising the color conversion composition according to claim 1 , or a cured material thereof.
7. A backlight unit comprising the color conversion film according to claim 6. The backlight unit according to claim 7 , comprising a light source, wherein the light source emits blue light.
9. A display device comprising the backlight unit according to claim 7.
Citation Information
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