Quantum dot-containing material, preparation method thereof, and optical component and device comprising the same
By using quantum dot-containing materials in optical components, and using the characteristics of quantum dots and matrix materials to achieve multiple reflection and absorption of light, the problem of insufficient light conversion efficiency of existing optical components is solved, and the light conversion efficiency is significantly improved.
Patent Information
- Application Number
- CN202010657752.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-07-06
- Filing Date
- 2020-07-09
- Publication Date
- 2025-02-21
- Estimated Expiration
- 2040-07-09
AI Technical Summary
The existing optical components have shortcomings in light conversion efficiency, making it difficult to achieve excellent color conversion performance.
A quantum dot-containing material is used, which consists of quantum dots, a first matrix material and a second matrix material, which is dispersed in the first matrix material, and the quantum dot-containing composite is dispersed in the second matrix material, and passes through a specific The refractive index relationship realizes multiple reflections and absorption of light.
The light conversion efficiency is significantly improved, and the poor particle dispersion and quality problems caused by the use of scattering agents in traditional methods are avoided, thereby achieving higher quality optical components and equipment.
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Figure CN112210179B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0084547 filed on Jul. 12, 2019, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2020-0082962 filed on Jul. 6, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0002] The present disclosure relates to quantum-dot materials, methods for preparing the quantum-dot materials, and optical components and devices including the quantum-dot materials. Background Art
[0003] Among optical members, quantum dots can be used as materials capable of performing various optical functions (eg, light conversion functions). Quantum dots, which are nano-scale semiconductor nanocrystals, can have different energy gaps depending on the size and composition of the nanocrystals, and thus can emit light with various emission wavelengths.
[0004] The optical member including quantum dots may have a thin film form, for example, a thin film form patterned according to sub-pixels. Such an optical member may also be used as a color conversion member of a device having various light sources.
[0005] In order to realize high quality devices, there remains a need to develop color conversion components that can provide excellent light conversion efficiency. Summary of the invention
[0006] One or more aspects of the embodiments of the present disclosure relate to quantum dot materials capable of providing excellent (or suitable) light conversion efficiency, methods for preparing quantum dot materials, and optical components and devices including quantum dot materials and thus having excellent (or suitable) light conversion efficiency.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0008] An embodiment of the present disclosure provides a quantum dot-containing material, the quantum dot-containing material comprising:
[0009] A quantum dot composite comprising quantum dots and a first host material; and
[0010] The second matrix material,
[0011] Wherein, the quantum dots are dispersed in the first matrix material,
[0012] The quantum dot complex is dispersed in a second matrix material, and
[0013] The refractive index of the first matrix material is greater than the refractive index of the second matrix material.
[0014] The quantum dot-containing material may be in the form of a film, that is, the quantum dot-containing material may be a quantum dot-containing film.
[0015] Another embodiment of the present disclosure provides a method for preparing a quantum dot-containing material, the method comprising:
[0016] preparing a first composition comprising quantum dots, a first monomer, a polymerization initiator, and a solvent;
[0017] The second composition is prepared by converting the first monomer in the first composition into at least a portion of the first matrix material, the second composition comprising a quantum dot complex and a solvent, the quantum dot complex comprising quantum dots and the first matrix material in which the quantum dots are dispersed;
[0018] obtaining a quantum dot-containing complex by removing the solvent from the second composition;
[0019] preparing a third composition comprising a quantum dot complex, a second monomer, a polymerization initiator, and a solvent; and
[0020] The quantum dot-containing material is prepared by converting the second monomer in the third composition into at least a portion of the second matrix material, wherein the quantum dot-containing material includes a quantum dot-containing composite and a second matrix material in which the quantum dot-containing composite is dispersed.
[0021] The refractive index of the first matrix material is greater than the refractive index of the second matrix material.
[0022] Another embodiment of the present disclosure provides an optical member including a quantum dot-containing material.
[0023] The optical member may be a color conversion member.
[0024] Another embodiment of the present disclosure provides a device including a quantum dot-containing material.
[0025] The device may further include a light source, and the quantum dot-containing material may be arranged in a path of light emitted from the light source.
[0026] The light source may be an organic light emitting device (OLED) or a light emitting diode (LED).
[0027] The light source may emit blue light. BRIEF DESCRIPTION OF THE DRAWINGS
[0028] These and / or other aspects will become apparent and more easily understood through the following description of embodiments in conjunction with the accompanying drawings. Figure 1 is a schematic diagram of a quantum dot-containing material according to an embodiment. DETAILED DESCRIPTION
[0029] Now will refer to embodiment in more detail, the example of embodiment is shown in the accompanying drawings, wherein the same reference numerals refer to the same element from time to time. In this regard, the present embodiment can have different forms, and should not be construed as being limited to the description set forth herein. Therefore, the embodiment is described below only by reference to the accompanying drawings to explain the aspects of this specification. As used herein, the term "and / or" includes any combination and all combinations of one or more of the relevant listed items. When such as "at least one (kind / person) in ... ", "one (kind / person) in ... " and "selected from ... " are expressed after (before) a column of elements (elements), what is modified is the element (element) of the entire column, rather than modifying the individual element (element) in the column. In addition, when describing embodiments of the present invention, the use of "can" refers to "one or more embodiments of the present invention".
[0030] exist Figure 1 In the embodiment, the quantum-dot-containing material 1 may include a quantum-dot-containing composite 110 and a second matrix material 130. The quantum-dot-containing material 1 may include a plurality of quantum-dot-containing composites 110.
[0031] The second matrix material 130 refers to a material other than the quantum-dot-containing composite 110 in the quantum-dot-containing material 1, and may be a mixture of two or more different materials.
[0032] The quantum dot composite 110 may be dispersed in the second matrix material 130 .
[0033] The quantum dot composite 110 may include quantum dots 111 and a first host material 113. The quantum dot composite 110 may include a plurality of quantum dots 111.
[0034] The first host material 113 refers to a material other than the quantum dots 111 contained in the quantum dot composite 110 , and may be a mixture of two or more different materials.
[0035] The quantum dots 111 may be dispersed in the first matrix material 113 .
[0036] The quantum dot 111 may be a quantum dot particle capable of emitting light by light stimulation. For example, the quantum dot 111 may include: a II-VI semiconductor compound; a III-VI semiconductor compound; a III-V semiconductor compound; a IV-VI semiconductor compound; a IV element or a compound including the same; an I-III-VI semiconductor compound; or any combination thereof.
[0037] II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS and / or MgSe, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS e, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS and / or MgZnSe, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe, etc.; or any combination thereof.
[0038] III-VI semiconductor compounds may include: binary compounds such as In 2 S 3 and / or In 2 Se 3 etc.; ternary compounds such as InGaS 3 and / or InGaSe 3 etc.; or any combination thereof.
[0039] The III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs and / or InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs and / or InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and / or InAlPSb, etc.; or any combination thereof. The III-V semiconductor compounds may also include Group II metals (e.g., the III-V semiconductor compounds may include InZnP, etc.).
[0040] Group IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; and quaternary compounds such as SnPbSSe, SnPbSeTe and / or SnPbSTe; or any combination thereof.
[0041] The Group IV element or a compound including the same may include: Si and / or Ge; a binary compound such as SiC and / or SiGe, etc.; or any combination thereof.
[0042] I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and / or AgAlO 2 etc.; or any combination thereof.
[0043] The quantum dot 111 may have a single (e.g., uniform) structure in which its components and composition are uniform, or a composite structure such as a core-shell structure and / or a gradient structure, etc. In the core-shell structure, the shell may be a single layer in which its components and composition are uniform, or a multilayer having two or more layers having different components and / or compositions.
[0044] For example, in the core-shell structure, each of the material for forming the core and the material for forming the shell may be selected from the above-mentioned semiconductor compounds.
[0045] In one or more embodiments, the quantum dots 111 may include Group III-V semiconductor compounds.
[0046] In one or more embodiments, the quantum dot 111 may include In.
[0047] In one or more embodiments, the quantum dot 111 may include In and P.
[0048] In one or more embodiments, the quantum dots 111 may include group III-V semiconductor compounds and group II-VI semiconductor compounds.
[0049] In one or more embodiments, the quantum dot 111 may have a core-shell structure, wherein the core may include a III-V semiconductor compound, and the shell may include a II-VI semiconductor compound.
[0050] In one or more embodiments, the quantum dot 111 may have a core-shell structure. The core may include GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or their In any combination, the shell can include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or any combination thereof.
[0051] In one or more embodiments, the quantum dot 111 may have a core-shell structure. The core may include CdSe, CdS, ZnS, ZnSe, CdTe, CdSeTe, CdZnS, PbSe, AgInZnS, ZnO, InN, InP, InAs, InSb, InGaP, or any combination thereof, and the shell may include CdSe, ZnSe, ZnS, ZnSeS, ZnTe, CdTe, PbS, TiO, SrSe, HgSe, or any combination thereof.
[0052] In one or more embodiments, the quantum dot 111 may have a core-shell structure including InP / ZnS or InP / ZnSeS.
[0053] The quantum dots 111 may be synthesized according to one or more suitable methods, such as a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, and / or a molecular beam epitaxy (MBE) process.
[0054] The average particle diameter of the quantum dots 111 may be 1 nm to 20 nm, for example, 1 nm to 15 nm, and for example, 1 nm to 10 nm.
[0055] When the quantum dot 111 has a core-shell structure, a ratio of a radius of the core to a thickness of the shell may be 2:8 to 8:2, for example 3:7 to 7:3, and for example 4:6 to 6:4.
[0056] The number of quantum dots 111 in the quantum dot composite 110 may be 50 to 2,000, for example, 100 to 1,000. The number of quantum dots 111 in the quantum dot composite 110 may be measured using a scanning electron microscope (SEM) or a transmission electron microscope (TEM).
[0057] The content (e.g., amount) of the quantum dots 111 in the quantum dot composite 110 may be about 0.01 parts by weight to about 10 parts by weight, for example, about 0.1 parts by weight to about 2 parts by weight, based on 100 parts by weight of the quantum dot composite 110. When the content of the quantum dots 111 in the quantum dot composite 110 is within the above range, the quantum dot material 1 may have excellent (or suitable) light conversion efficiency.
[0058] The refractive index of the first matrix material 113 may be greater than the refractive index of the second matrix material 130. Therefore, light incident on the quantum dot material 1 may be multiple-reflected in the quantum dot composite 110. In this regard, the light absorption of the quantum dots 111 in the quantum dot composite 110 may be increased, thereby increasing the light conversion efficiency of the quantum dot material 1. Therefore, a separate scattering agent (e.g., an oxide-based scattering agent such as TiO2) may not be used. 2 etc.) to induce multiple reflections and / or scattering of light incident on the quantum dot-containing material 1. Therefore, the problem of poor quality of the quantum dot-containing material 1 due to poor particle dispersion caused by the difference between the average particle size of the quantum dots 111 and the average particle size of the conventional scattering agent can be substantially prevented.
[0059] In the specification, the term "refractive index" as used herein refers to an absolute refractive index relative to the D line of sodium (Na) (λ = 589nm, yellow). For example, the refractive index can be an absolute refractive index measured based on a wavelength of 589nm using a refractometer (e.g., ellipsometer, M-2000, JA Woollam) at a temperature of 25°C and a relative humidity of 50%, for example, using a Cauchy equation (e.g., Cauchy Film Model).
[0060] The refractive index of each of the first matrix material 113 and the second matrix material 130 can be evaluated using a refractometer (e.g., an ellipsometer, M-2000, JA Woollam) as follows: the refractive index of each of the first matrix material 113 and the second matrix material 130 containing the quantum dots 111 therein can be measured; or the refractive index of each of a film or particle consisting only of the first matrix material 113 without the quantum dots 111 and a film or particle consisting of the second matrix material 130 without the quantum dots 111 can be measured.
[0061] The refractive index of the first matrix material 113 may be 1.55 to 2.00, for example, 1.55 to 1.85, and in one or more embodiments, may be 1.580 to 1.802. The refractive index of the second matrix material 130 may be 1.30 to 1.55, for example, 1.40 to 1.50, and in one or more embodiments, may be 1.490. In one or more embodiments, the difference between the refractive index of the first matrix material 113 and the refractive index of the second matrix material 130 may be 0.05 to 0.60, for example, 0.06 to 0.45, and in one or more embodiments, 0.090 to 0.312. By satisfying the above range, multiple reflections of light incident on the quantum dot material 1 can be effectively induced, thereby improving the light absorption rate of the quantum dots 111 of the quantum dot composite 110. Therefore, the light conversion efficiency of the quantum dot material 1 can also be improved.
[0062] Each of the first host material 113 and the second host material 130 may include a material capable of providing the above-mentioned refractive index.
[0063] The first host material 113 may include a first polymer serving as a medium in which the quantum dots 111 are dispersed.
[0064] The first polymer may be a polymer obtained by polymerizing a first monomer as described herein (eg, by polymerizing a first monomer solution as described herein).
[0065] For example, the first monomer may include a water-soluble vinyl-based monomer, a water-soluble acrylic-based monomer, a water-soluble acrylamide-based monomer, or any combination thereof. The first monomer may be understood by referring to the description thereof provided below.
[0066] The content (e.g., amount) of the first polymer may be about 70 parts by weight to about 100 parts by weight, for example, about 80 parts by weight to about 100 parts by weight, based on 100 parts by weight of the first matrix material 113. When the content of the first polymer is within the above range, the first matrix material 113 may have excellent (or suitable) rigidity, and the quantum dots 111 may be relatively uniformly dispersed in the first matrix material 113.
[0067] In addition to the first polymer, the first matrix material 113 may also include a polymerization initiator. The polymerization initiator may be any material capable of initiating polymerization of the first monomer as described herein. For example, the polymerization initiator may be any polymerization initiator used in solution polymerization.
[0068] In one or more embodiments, the polymerization initiator may include potassium persulfate (KPS).
[0069] In one or more embodiments, the first matrix material 113 may further include a dispersant, etc., in order to improve the dispersion of the quantum dots 111. The dispersant may be the same as described herein.
[0070] The second matrix material 130 may include a second polymer serving as a medium in which the quantum dot composite 110 is dispersed.
[0071] The second polymer may be a polymer obtained by polymerizing the second monomer (eg, by photopolymerizing the second monomer).
[0072] For example, the second monomer may include an acrylic monomer.The second monomer may be understood by referring to the description thereof provided below.
[0073] The content (e.g., amount) of the second polymer may be about 10 parts by weight to about 90 parts by weight, for example, about 20 parts by weight to about 80 parts by weight, based on 100 parts by weight of the second matrix material 130. When the amount of the second polymer is within the above range, the second matrix material 130 may have excellent (or suitable) rigidity, and the quantum dot composite 110 may be relatively uniformly dispersed in the second matrix material 130.
[0074] In addition to the second polymer, the second matrix material 130 may also include a polymerization initiator. The polymerization initiator may be any material capable of initiating polymerization of the second monomer. For example, the polymerization initiator may be any suitable photopolymerization initiator used in photopolymerization. The photopolymerization initiator may be understood by referring to the description thereof provided below.
[0075] In addition to the second polymer and the polymerization initiator, the second matrix material 130 may further include an alkali-soluble resin, a dispersant, an additive, or any combination thereof. The alkali-soluble resin, the dispersant, and the additive may be understood by referring to the description thereof provided below.
[0076] The quantum dot-containing composite 110 may be a spherical particle. For example, the quantum dot-containing composite 110 may be a spherical particle, and its surface may be smooth. When the quantum dot-containing composite 110 is a spherical particle, the quantum dot-containing composite 110 may be prepared by a separate process, and then, may be mixed with a mixture for forming the second matrix material 130 in a spherical form (i.e., a bead or powder form in which a solvent, etc. is removed). Therefore, in the quantum dot-containing material 1, the boundary between the quantum dot-containing composite 110 and the second matrix material 130 may be clearly distinguished.
[0077] As such, the "quantum dot-containing composite 110" and the "second matrix material 130" are clearly distinguished from the comparable "quantum dot-containing region" and "quantum dot-free region" induced by mixing a quantum dot-containing solution and a polymer solution and then partially phase-separating the quantum dot-containing solution and the polymer solution due to the polarity difference between the quantum dot-containing solution and the polymer solution. When the "quantum dot-containing region" and the "quantum dot-free region" are induced by phase separation, the boundary between the "quantum dot-containing region" and the "quantum dot-free region" may be unclear. In addition, the "quantum dot-containing region" may be irregular in appearance, have a rough surface, and have a very high uniformity coefficient. Therefore, the comparable quantum dot-containing material including the "quantum dot-containing region" and the "quantum dot-free region" induced by phase separation as described above may have poor light conversion efficiency.
[0078] The average particle size (D50) of the quantum dot composite 110 may be about 40 nm to 1,000 nm, for example, about 50 nm to about 1,000 nm or about 100 nm to about 500 nm, and in one or more embodiments, may be about 100 nm to about 200 nm. When the average particle size D50 of the quantum dot composite 110 is within the above range, the quantum dot composite 110 including a relatively large amount of quantum dots 111 may be dispersed in the second matrix material 130 with an excellent (or appropriate) degree of dispersion.
[0079] The uniformity coefficient (D60 / D10) of the quantum dot composite 110 may be about 1.0 to about 2.0, for example, about 1.4 to about 1.8. When the uniformity coefficient of the quantum dot composite 110 is within any of the above ranges, the average particle size D50 of the quantum dot composite 110 may cause a high degree of uniformity, and thus, the quantum dot composite 110 may be dispersed in the second matrix material 130 with an excellent (or appropriate) degree of dispersion.
[0080] The average particle size D50 may be measured by measuring a particle size distribution curve of the quantum dot composite 110 by using a particle size analyzer, and then by measuring a particle size corresponding to 50% in terms of passage mass percentage.
[0081] The uniformity coefficient D60 / D10 can be measured by evaluating the particle size distribution curve of the quantum dot composite 110 using a particle size analyzer, and then by evaluating the ratio of D60 (i.e., the particle size corresponding to 60% by mass percentage) to D10 (i.e., the particle size corresponding to 10% by mass percentage).
[0082] The quantum dot-containing material 1 may have an irregular shape that fills a set or predetermined space, or may have a film form. When the quantum dot-containing material 1 has a film form, the "quantum dot-containing material 1" may be referred to as a "quantum dot-containing film 1". Here, the film may have a thickness of about 0.1 μm to about 100 μm, for example, about 1 μm to about 10 μm.
[0083] Another embodiment of the present disclosure provides a method for preparing a quantum dot-containing material 1, the method comprising:
[0084] preparing a first composition including quantum dots 111, a first monomer, a polymerization initiator and a solvent;
[0085] The second composition is prepared by converting the first monomer in the first composition into at least a portion of the first matrix material 113, the second composition comprising a quantum dot complex 110 and a solvent, the quantum dot complex 110 comprising quantum dots 111 and the first matrix material 113 in which the quantum dots 111 are dispersed;
[0086] obtaining a quantum dot-containing composite 110 by removing the solvent from the second composition;
[0087] preparing a third composition including the quantum dot complex 110, a second monomer, a polymerization initiator, and a solvent; and
[0088] The quantum-dot-containing material 1 is prepared by converting the second monomer in the third composition into at least a portion of the second matrix material 130 , and the quantum-dot-containing material 1 includes the quantum-dot-containing composite 110 and the second matrix material 130 in which the quantum-dot-containing composite 110 is dispersed.
[0089] Here, the refractive index of the first host material 113 may be greater than the refractive index of the second host material 130 as described above.
[0090] Hereinafter, a method of preparing the quantum-dot-containing material 1 may be described in more detail below.
[0091] First, a first composition including quantum dots 111, a first monomer, a polymerization initiator, and a solvent is prepared.
[0092] The quantum dots 111 in the first composition are the same as described herein.
[0093] Based on 100 parts by weight of the first composition, the content (e.g., amount) of the quantum dots 111 can be about 0.1 parts by weight to about 10 parts by weight, for example, about 0.1 parts by weight to about 5 parts by weight. When the content of the quantum dots 111 is within the above range, a quantum dot material 1 having excellent (or suitable) light conversion efficiency can be prepared.
[0094] The first monomer in the first composition may be a monomer that is polymerizable by solution polymerization.
[0095] For example, the first monomer in the first composition may include a vinyl-based monomer, an acrylic-based monomer, an acrylamide-based monomer, or any combination thereof.
[0096] In one or more embodiments, the first monomer in the first composition may include a water-soluble vinyl-based monomer, a water-soluble acrylic-based monomer, a water-soluble acrylamide-based monomer, or any combination thereof.
[0097] In one or more embodiments, the first monomer may be a group represented by one of Formula 1-1 to Formula 1-3:
[0098]
[0099] In Formula 1-1 to Formula 1-3,
[0100] L 1 Can be a single bond, C(R 5 )(R 6 )、N(R 5 ), O or S,
[0101] a1 may be an integer from 1 to 10, and when a1 is 2 or more, two or more L 1 can be the same or different from each other,
[0102] R 1 To R 6 can be independently hydrogen, deuterium, C 1 -C 20 alkyl, phenyl or biphenyl, and
[0103] *Indicates the binding site with the adjacent atom.
[0104] In one or more embodiments, the first monomer may include a cyclic (e.g., ring-containing) vinyl monomer, a cyclic (e.g., ring-containing) acrylic monomer, a cyclic (e.g., ring-containing) acrylamide monomer, or any combination thereof. The cyclic vinyl monomer, the cyclic acrylic monomer, and the cyclic acrylamide monomer may each independently be a compound having: 1) at least one substituted or unsubstituted C 5 -C 60 A carbocyclic group, at least one substituted or unsubstituted C 1 -C 60 heterocyclic group or any combination thereof; and 2) vinyl group (for example, a group represented by Formula 1-1), acrylate group (for example, a group represented by Formula 1-2), acrylamide group (for example, a group represented by Formula 1-3) or any combination thereof.
[0105] For example, the cyclic vinyl monomers can be understood by referring to the following compounds 1 and 11, the cyclic acrylic monomers can be understood by referring to the following compounds 2 to 8, 10, and 101 to 107, and the cyclic acrylamide monomers can be understood by referring to the following compound 9.
[0106] In one or more embodiments, the first monomer may be a compound represented by Formula 1:
[0107] Formula 1
[0108] (A 1 ) n1 -L-(A 2 ) n2 .
[0109] In formula 1,
[0110] A 1 It may be a group represented by one of Formulae 2-1 to 2-9, a group derived from a hole transport material in an organic layer of an organic light-emitting device, a group derived from a light-emitting material in an organic layer of an organic light-emitting device, or a group derived from an electron transport material in an organic layer of an organic light-emitting device,
[0111] L can be a single bond, a double bond, O or S,
[0112] A 2 It may be a vinyl group (for example, a group represented by Formula 1-1), an acrylate group (for example, a group represented by Formula 1-2), or an acrylamide group (for example, a group represented by Formula 1-3), and
[0113] n1 and n2 may each independently be an integer from 1 to 10, wherein when n1 is 2 or greater, two or more A 1 may be the same as or different from each other, and when n2 is 2 or greater, two or more A 2 Can be the same or different from each other:
[0114]
[0115] In Formula 2-1 to Formula 2-9,
[0116] R 11 To R 14 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0117] * indicates the same as L or A in formula 1 2 The combination position.
[0118] In the present specification, the term "group derived from a hole transport material" as used herein means that any atom of the hole transport material is radicalized and becomes capable of chemically bonding to L or A in Formula 1. 2 In the present specification, the term "group derived from a light-emitting material" and the term "group derived from an electron transporting material" as used herein may also be interpreted in the same meaning.
[0119] Examples of each of the hole transport material in the “group derived from a hole transport material”, the light emitting material in the “group derived from a light emitting material”, and the electron transport material in the “group derived from an electron transport material” are as follows:
[0120] Examples of hole transport materials
[0121] The hole transport material may be a compound represented by Formula 201 or a compound represented by Formula 202:
[0122] Formula 201
[0123]
[0124] Formula 202
[0125]
[0126] In equation 201 and equation 202,
[0127] L 201 To L 204 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0128] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2-C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0129] xa1 to xa4 may each independently be 0, 1, 2 or 3 (e.g., 0, 1 or 2),
[0130] xa5 may be an integer from 1 to 10 (e.g., 1, 2, 3, or 4), and
[0131] R 201 To R 204 and Q 201 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0132] For example, in Equation 202, R 201 and R 202 can be optionally linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, R 203 and R 204The groups may alternatively be linked to each other via single bonds, dimethyl-methylene groups or diphenyl-methylene groups.
[0133] In one or more embodiments, the hole transport material may be one of the following compounds HT1 to HT44, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD or 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA):
[0134]
[0135]
[0136]
[0137]
[0138]
[0139] Examples of Emissive Materials
[0140] The light emitting material may be a compound represented by the following Formula 301:
[0141] Formula 301
[0142] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0143] In formula 301,
[0144] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0145] xb11 can be 1, 2 or 3,
[0146] L 301 It can be substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0147] xb1 can be 0, 1, 2, 3, 4, or 5.
[0148] R 301 It can be deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0149] xb21 can be 1, 2, 3, 4, or 5, and
[0150] Q 301 To Q 303 can be independently defined as the combination of Q 1 Same as described.
[0151] For example, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0152] In one or more embodiments, the light-emitting material may be one of the following compounds H1 to H36, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP) or 1,3,5-tri(carbazolyl-9-yl)benzene (TCP):
[0153]
[0154]
[0155]
[0156] Examples of Electron Transport Materials
[0157] The electron transport material may be a compound represented by Formula 601-1:
[0158] Formula 601-1
[0159]
[0160] In formula 601-1,
[0161] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and X 614 To X 616 At least one of may be N,
[0162] L 611 To L 613 can be independently selected from substituted or unsubstituted C 3 -C 10Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0163] xe611 to xe613 can each independently be an integer from 0 to 5,
[0164] R 611 To R 613 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),and
[0165] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl.
[0166] Q 601 To Q 603 can be independently defined as the combination of Q 1 Same as described.
[0167] For example, xe611 to xe613 in formula 601-1 can all independently be 0, 1 or 2.
[0168] In one or more embodiments, the electron transport material may be one of Compound ET1 to Compound ET36:
[0169]
[0170]
[0171] General Definition of Substituents
[0172] As used herein, the term "C 1 -C 60 The term “alkyl” may refer to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and / or tert-decyl, etc. As used herein, the term “C 2+” may refer to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and / or tert-decyl, etc. 1 -C 60 "Alkylene" may refer to 1 -C 60 An alkyl group is a divalent group having the same structure.
[0173] As used herein, the term "C 2 -C 60 "Alkenyl" may refer to 2 -C 60 One or more positions of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond (in the middle and / or at the terminal of the alkyl group), and non-limiting examples thereof include ethenyl, propenyl and / or butenyl, etc. 2 -C 60 "Alkenylene" may refer to 2 -C 60Alkenyl groups have divalent groups of the same structure.
[0174] As used herein, the term "C 2 -C 60 "Alkynyl" may refer to 2 -C 60 One or more positions of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond (in the middle and / or at the end of the alkyl group), and non-limiting examples thereof include ethynyl and / or propynyl, etc. 2 -C 60 "Alkynylidene" may refer to 2 -C 60 Alkynyl groups are divalent groups with the same structure.
[0175] As used herein, the term "C 1 -C 60 "Alkoxy" may refer to -OA 101 (Among them, A 101 C 1 -C 60 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include a methoxy group, an ethoxy group, and / or an isopropoxy group, and the like.
[0176] As used herein, the term "C 3 -C 10 The term "cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl and / or bicyclo[2.2.2]octyl, and the like. As used herein, the term "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept 3 -C 10 "Cycloalkylene" may refer to 3 -C 10 The cycloalkyl group has a divalent group of the same structure.
[0177] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" may refer to a monovalent monocyclic group having at least one heteroatom (eg, N, O, Si, P, S, or any combination thereof) as a ring-forming atom and 1 to 10 carbon atoms. 1 -C 10 Non-limiting examples of heterocycloalkyl include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl, etc. As used herein, the term "C 1 -C 10"Heterocycloalkylene" may refer to 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.
[0178] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" may refer to a monovalent monocyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond, and no aromaticity in its ring. 3 -C 10 Non-limiting examples of cycloalkenyl groups include cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. As used herein, the term "cycloalkenyl" 3 -C 10 "Cycloalkenylene" may refer to 3 -C 10 The cycloalkenyl group has a divalent group of the same structure.
[0179] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" may refer to a monovalent monocyclic group having at least one heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term "C 1 -C 10 "Heterocycloalkenylene" may refer to 1 -C 10 The heterocycloalkenyl group has a divalent group of the same structure.
[0180] As used herein, the term "C 6 -C 60 The term "aryl" may refer to a monovalent group having a monovalent carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The term "C" as used herein refers to a phenyl group, ... 6 -C 60 "Arylene" may refer to 6 -C 60 Aryl has a divalent group with the same structure. 6 -C60 Aryl and C 6 -C 60 When the arylene groups each independently include two or more rings, the respective rings may be condensed with each other.
[0181] As used herein, the term "C 1 -C 60 The term "heteroaryl" may refer to a monovalent group having a heterocyclic aromatic system having at least one heteroatom (eg, N, O, Si, P, S, or any combination thereof) as a ring-forming atom and 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and / or naphthyridinyl, and the like. As used herein, the term “C 1 -C 60 "Heteroarylene" may refer to 1 -C 60 Heteroaryl has a divalent group with the same structure. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group each independently includes two or more rings, the respective rings may be condensed with each other.
[0182] The term "C 6 -C 60 "Aryloxy" may refer to -OA 102 (Among them, A 102 C 6 -C 60 The term "C 6 -C 60 "Arylthio" may refer to -SA 103 (Among them, A 103 C 6 -C 60 A monovalent group represented by an aryl group.
[0183] As used herein, the term "monovalent non-aromatic condensed polycyclic radical" may refer to a monovalent group having two or more rings condensed to each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic condensed polycyclic radicals include indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. As used herein, the term "divalent non-aromatic condensed polycyclic radical" may refer to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic radical.
[0184] The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may refer to a monovalent group having two or more rings condensed to each other, heteroatoms (e.g., N, O, Si, P, S, or any combination thereof) as ring-forming atoms, carbon atoms (e.g., 1 to 60 carbon atoms) as remaining ring-forming atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0185] As used herein, the term "C 5 -C 60 The term "carbocyclic group" may refer to a monocyclic group or a polycyclic group having only 5 to 60 carbon atoms as ring atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a compound such as benzene, a monovalent group such as phenyl, or a divalent group such as phenylene. 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group can be variously modified to be a trivalent group or a tetravalent group.
[0186] C 5 -C 60Non-limiting examples of carbocyclic groups include cyclopentadienyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The invention also includes phenyl, benzophenanthryl, phenanthrenyl, heptaphenyl, tetraphenyl, peryl, hexenyl, pentacene, rubinyl, camphenyl, ovaphenyl, indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc.
[0187] As used herein, the term "C 1 -C 60 The term "heterocyclic group" may refer to a monocyclic group or a polycyclic group having 1 to 60 carbon atoms and heteroatoms (eg, N, O, Si, P, S, or any combination thereof) as ring-forming atoms. 1 -C 60 Non-limiting examples of the heterocyclic group include an aromatic heterocyclic group or a non-aromatic heterocyclic group. 1 -C 60 The heterocyclic group can be a compound such as pyridine, a monovalent group such as pyridyl, or a divalent group such as pyridylene. 1 -C 60 The number of substituents of the heterocyclic group, C 1 -C 60 The heterocyclic group can be variously modified to be a trivalent group or a tetravalent group.
[0188] C 1 -C 60Non-limiting examples of heterocyclic groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolsyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolsyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiolsyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazole yl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenecarbazolyl, benzothiorrolocarbazolyl, benzoindolecarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophene, benzonaphthothiorryl, benzofuranodibenzofuranyl, benzofuranodibenzothiophene and / or benzothiophenedibenzothiophene, etc.
[0189] Substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 20 Alkylene, substituted C 2 -C 20 Alkenylene, substituted C 1 -C 60 Alkylene, substituted C 2 -C 60 Alkenylene, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
[0190] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0191] are unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11)、-P(=O)(Q 11 )(Q 12 ) or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;
[0192] are unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group;
[0193] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 );or
[0194] Any combination of them.
[0195] In this manual, Q 1 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group or a terphenyl group.
[0196] In one or more embodiments, the first monomer in the first composition may be one of the following compounds 1 to 11 and compounds 101 to 107 or any combination thereof:
[0197]
[0198]
[0199]
[0200] The content (e.g., amount) of the first monomer may be about 5 parts by volume to about 20 parts by volume based on 100 parts by volume of the first composition. When the content of the first monomer is within the above range, a quantum dot composite 110 in which quantum dots 111 are uniformly (or substantially uniformly) dispersed may be prepared.
[0201] In the first composition, the polymerization initiator may be any polymerization initiator capable of initiating polymerization of the first monomer. For example, the polymerization initiator may be a water-soluble polymerization initiator suitable for solution polymerization.
[0202] In one or more embodiments, the polymerization initiator in the first composition may be KPS.
[0203] In the first composition, the solvent may be any solvent that can be appropriately mixed with the first monomer, etc. For example, the solvent in the first composition may be water.
[0204] The content (e.g., amount) of the solvent may be about 70 parts by volume to about 99 parts by volume based on 100 parts by volume of the first composition. When the content of the solvent is within the above range, a quantum dot composite 110 in which quantum dots 111 are dispersed in the first matrix material 113 with a uniform (or substantially uniform) dispersion degree may be prepared.
[0205] Next, the first monomer in the first composition can be converted into at least a portion of the first matrix material 113, so that a second composition including a solvent and a quantum dot complex 110 can be prepared, in which the quantum dots 111 are dispersed in the first matrix material 113. The step of "converting the first monomer into at least a portion of the first matrix material 113" can be understood as a step of "forming a first polymer by polymerization of the first monomer".
[0206] In one or more embodiments, the solvent in the first composition may be water, and the first monomer in the first composition may include a water-soluble vinyl monomer, a water-soluble acrylic monomer, a water-soluble acrylamide monomer, or any combination thereof. The first composition may also include a water-soluble polymerization initiator, and the preparation of the second composition may be performed by using solution polymerization.
[0207] For example, the preparation of the second composition may include stirring the first composition at a temperature of about 50° C. to about 150° C. and a speed of about 300 rpm to about 800 rpm. When the conditions as described above are met, the first monomer may be effectively converted into at least a portion of the first matrix material 113, and the quantum dot composite 110 may have a spherical particle form.
[0208] Thereafter, by removing the solvent from the second composition, the quantum dot-containing complex 110 may be obtained. The obtaining of the quantum dot-containing complex 110 may be performed by using lyophilization (or freeze drying).
[0209] Then, a third composition including the quantum dot complex 110, a second monomer, a polymerization initiator, and a solvent may be prepared.
[0210] Based on 100 parts by weight of the third composition, the content (e.g., amount) of the quantum dot composite 110 may be about 5 parts by weight to about 25 parts by weight, for example, about 10 parts by weight to about 20 parts by weight. When the content of the quantum dot composite 110 is within any of the above ranges, a quantum dot material 1 having excellent (or appropriate) light conversion efficiency may be prepared while maintaining an excellent (or appropriate) degree of dispersion of the quantum dot composite 110 in the third composition.
[0211] The second monomer in the third composition may be a photopolymerizable monomer. For example, the second monomer may be an acrylic monomer.
[0212] Non-limiting examples of acrylic monomers include monofunctional (meth)acrylate monomers such as 2-ethylphenoxy (meth)acrylate, 2-ethylthiophene (meth)acrylate, phenyl (meth)acrylate, diphenyl methyl (meth)acrylate, benzyl (meth)acrylate, 2-phenylethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 2-(2-methylphenyl)ethyl (meth)acrylate, 2-(3-methylphenyl)ethyl (meth)acrylate, 2-(4-methylphenyl)ethyl (meth)acrylate, 2-(4-propylphenyl)ethyl (meth)acrylate, 2-(1-methylethyl)acrylate, 2-(2-methylphenyl)ethyl (meth)acrylate, 2-(3-methylphenyl)ethyl (meth)acrylate, 2-(4-propylphenyl)ethyl (meth)acrylate, 2-(1-methylethyl)acrylate, 2-(2-methylphenyl)ethyl (meth)acrylate, 2-(3-methylphenyl)ethyl (meth)acrylate, 2-(4-propylphenyl)ethyl (meth)acrylate, 2-(1-methylphenyl)ethyl (meth ...1-methylphenyl)ethyl ethyl (meth)acrylate, 2-(4-methoxyphenyl)ethyl (meth)acrylate, 2-(4-cyclohexylphenyl)ethyl (meth)acrylate, 2-(2-chlorophenyl)ethyl (meth)acrylate, 2-(3-chlorophenyl)ethyl (meth)acrylate, 2-(4-chlorophenyl)ethyl (meth)acrylate, 2-(4-bromophenyl)ethyl (meth)acrylate, 2-(3-phenylphenyl)ethyl (meth)acrylate, 2-(4-benzylphenyl)ethyl (meth)acrylate and / or o-phenylphenoxyethyl acrylate; difunctional (meth)acrylate monomers such as dicyclopentenyl di(meth)acrylate, caprolactone-modified dicyclopentenyl di(meth)acrylate, allylated cyclohexyl di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, dimethylol dicyclopentane di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, bisfluorene di(meth)acrylate, bisphenol-modified fluorene di(meth)acrylate, phenyl-modified polyurethane di(meth)acrylate and / or bisfluorene-modified polyurethane di(meth)acrylate, etc.; trifunctional (meth)acrylate monomers such as trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, tri(2-hydroxyethyl)isocyanurate tri(meth)acrylate, tris ... Glycerol (meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate and / or ditrimethylolpropane tri(meth)acrylate, etc.; tetrafunctional (meth)acrylate monomers, such as pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate and / or dipentaerythritol tetra(meth)acrylate, etc.; pentafunctional (meth)acrylate monomers, such as dipentaerythritol penta(meth)acrylate and / or ditrimethylolpropane penta(meth)acrylate, etc.; hexafunctional (meth)acrylate monomers, such as dipentaerythritol hexa(meth)acrylate and / or ditrimethylolpropane hexa(meth)acrylate, etc.; or any combination thereof.
[0213] The second monomer may not include an epoxy-based monomer.
[0214] The second monomer may be included in an amount of about 10 to about 50 parts by weight based on 100 parts by weight of the third composition. When the second monomer is included in an amount within the above range, the second matrix material 130 may have high rigidity due to efficient formation of an exposed portion during exposure.
[0215] The polymerization initiator in the third composition may be any suitable polymerization initiator, such as any suitable photopolymerization initiator capable of initiating polymerization of the second monomer.
[0216] In terms of polymerization characteristics, initiation efficiency, absorption wavelength, availability and / or cost, etc., the photopolymerization initiator may be an acetone compound, a benzophenone compound, a triazine compound, a biimidazole compound, an oxime compound, a thioxanthone compound or any combination thereof.
[0217] Non-limiting examples of acetone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, benzyl dimethyl ketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropane-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methylthienyl)-2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propane-1-one and / or 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, and the like.
[0218] Non-limiting examples of benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3′,4,4′-tetrakis(tert-butylperoxycarbonyl)benzophenone and / or 2,4,6-trimethylbenzophenone.
[0219] Non-limiting examples of triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2 -(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine and / or 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.
[0220] Non-limiting examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole and / or biimidazole compounds in which the phenyl groups at the 4,4',5,5' positions are substituted with alkoxycarbonyl groups, and the like.
[0221] Nonlimiting examples of the oxime compound include o-ethoxycarbonyl-α-oxyimino-1-phenylpropane-1-one and the like.
[0222] Non-limiting examples of thioxanthone compounds include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and / or 1-chloro-4-propoxythioxanthone, and the like.
[0223] Non-limiting examples of commercially available photopolymerization initiators include: Irgacure-907, Irgacure 184, Irgacure 819, Irgacure 250, Darocur 1173, Irgacure OXE 01, and Irgacure OXE 02 (manufactured by BASF); WPI-113, WPI-116, WPI-169, WPI-170, WPI-124, WPAG-638, WPAG-469, WPAG-370, WPAG-367, and WPAG-336 (manufactured by Wako Pure Chemical Industries, Ltd.); B2380, B2381, C1390, D2238, D2248, D2253, I0591, T1608, T1609, T2041 and T2042 (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.); AT-6992, AT-6976 (manufactured by ACETO); CPI-100, CPI-100P, CPI-101A, CPI-200K and CPI-210S (manufactured by San-Apro Ltd.); SP-056, SP-066, SP-130, SP-140, SP-150, SP-170, SP-171 and SP-172 (manufactured by ADEKA CORPORATION); CD-1010, CD-1011 and CD-1012 (manufactured by Satomer Co., Ltd.); San Aid SI-60, SI-80, SI-100, SI-60L, SI-80L, SI-100L, SI-L145, SI-L150, SI-L160, SI-L110 and SI-L147 (manufactured by SANSHIN CHEMICAL INDUSTRY CO., LTD.); and PI2074 (manufactured by Rhodia Japan, Ltd.).
[0224] The content (e.g., amount) of the photopolymerization initiator may be about 0.1 parts by weight to about 10 parts by weight, for example, about 2 parts by weight to about 8 parts by weight, based on 100 parts by weight of the third composition. When the content of the photopolymerization initiator is within any of the above ranges, the second matrix material 130 may have high rigidity due to efficient formation of an exposed portion during exposure.
[0225] The solvent in the third composition may be selected from suitable solvents that can be mixed with the quantum dot complex 110, the second monomer and / or the polymerization initiator.
[0226] Non-limiting examples of the solvent in the third composition include: alkylene glycol alkyl ether solvents, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether and / or propylene glycol methyl ethyl ether, etc.; diethylene glycol dialkyl ether solvents, such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and / or diethylene glycol dibutyl ether, etc.; alkylene glycol alkyl ether acetate solvents, such as methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate and / or propylene glycol monopropyl ether acetate. etc.; alkoxyacetic acid alkyl ester solvents, such as methoxybutyl acetate and / or methoxypentyl acetate; aromatic hydrocarbon solvents, such as benzene, toluene, xylene and / or mesitylene; ketone solvents, such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and / or cyclohexanone; alcohol solvents, such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and / or glycerol; ester solvents, such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate and / or ethyl 3-phenylpropionate; cyclic ester solvents, such as γ-butyrolactone; or any combination thereof.
[0227] Based on 100 parts by weight of the third composition, the content (e.g., amount) of the solvent can be from about 20 parts by weight to about 70 parts by weight, for example, from about 30 parts by weight to about 60 parts by weight. When the content of the solvent is within any of the above ranges, the third composition can have excellent (or suitable) viscosity and can maintain high dispersibility of the solid in the third composition.
[0228] The third composition may further include an alkali-soluble resin, a dispersant, or any combination thereof in addition to the quantum dot complex 110 , the second monomer, the polymerization initiator, and the solvent.
[0229] The alkali-soluble resin can be used to: remove the non-exposed portion after exposure to the third composition by imparting alkali solubility to the non-exposed portion, thereby leaving the exposed portion; uniformly disperse the quantum-dot composite 110 of the third composition in the third composition; and / or protect the quantum-dot composite 110 during the preparation of the quantum-dot material 1.
[0230] The alkali-soluble resin may have an acid value of 50 to 200 (KOH mg / g). The term "acid value" as used herein may refer to a value measured in the amount (mg) of potassium hydroxide required to neutralize 1 g of a polymer, and is related to solubility. When the acid value of the alkali-soluble resin is within the above range, excellent (or suitable) development speed, excellent (or suitable) adhesion to a substrate, and storage stability of the third composition may be achieved.
[0231] The alkali-soluble resin may be a polymer derived from a carboxyl-containing unsaturated monomer, a copolymer with a monomer which is copolymerizable with the carboxyl-containing unsaturated monomer and has an unsaturated bond, or any combination thereof.
[0232] Non-limiting examples of carboxyl-containing unsaturated monomers include unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, unsaturated tricarboxylic acids or any combination thereof. Non-limiting examples of unsaturated monocarboxylic acids include acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid and / or cinnamic acid, etc. Non-limiting examples of unsaturated dicarboxylic acids include maleic acid, fumaric acid, itaconic acid, citraconic acid and / or mesaconic acid, etc. Non-limiting examples of unsaturated dicarboxylic acids include anhydrides (e.g., maleic anhydride, itaconic anhydride and / or citraconic anhydride, etc.). In addition, non-limiting examples of unsaturated dicarboxylic acids include mono (2- (meth) acryloyloxyalkyl) esters of unsaturated dicarboxylic acids, such as succinic acid mono (2-acryloyloxyethyl) ester, succinic acid mono (2-methacryloyloxyethyl) ester, phthalic acid mono (2-acryloyloxyethyl) ester and / or phthalic acid mono (2-methacryloyloxyethyl) ester, etc. The unsaturated dicarboxylic acid may include mono(meth)acrylate of a dicarboxylic acid polymer at both ends, and non-limiting examples thereof include ω-carboxy-polycaprolactone monoacrylate and / or ω-carboxy-polycaprolactone monomethacrylate, etc. The carboxyl group-containing monomer may be used alone or in mixture of two or more.
[0233] In one or more embodiments, the monomer copolymerizable with the carboxyl-containing unsaturated monomer may include an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated ether compound, a cyanide vinyl compound, an unsaturated amide compound, an unsaturated imide compound, an aliphatic conjugated diene compound, a macromonomer having a monoacryloyl group or a monomethacryloyl group at the end of the molecular chain, a bulky monomer, or any combination thereof.
[0234] Based on 100 parts by weight of the third composition, the content (e.g., amount) of the alkali-soluble resin may be from about 5 parts by weight to about 80 parts by weight, for example, from about 10 parts by weight to about 70 parts by weight. When the content of the alkali-soluble resin is within the above range, the reduction of the film of the pixel portion of the exposed portion during development can be prevented or reduced, so that the omission of the non-pixel portion can be protected (or the omission of the non-pixel portion can be protected).
[0235] The dispersant can be used to improve the deagglomeration effect (or "deagglomeration effect") of the quantum dot complex 110 in the third composition. For use as a dispersant, a resin-type (e.g., resin-containing) dispersant such as a phosphate dispersant, a polyurethane dispersant, and / or an acrylic dispersant can be used. In one or more embodiments, as a dispersant, commercially available products manufactured by BYK-Chemie company, such as DISPER BYK-103, DISPER BYK-110, DISPER BYK-111, DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2011, DISPER BYK-2070, DISPER BYK-2150, DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164 and / or DISPERBYK-166, may be used.
[0236] Based on 100 parts by weight of the third composition, the content (e.g., amount) of the dispersant may be from about 0.1 parts by weight to about 15 parts by weight, for example, from about 1 part by weight to about 10 parts by weight. When the content of the dispersant is within any of the above ranges, agglomeration of the quantum dot complex 110 in the third composition may be substantially prevented.
[0237] In one or more embodiments, the third composition may further include an adhesion promoter for increasing adhesion to a substrate, a surfactant for improving coating characteristics, an antioxidant, an ultraviolet absorber, or any combination thereof, as required.
[0238] Next, the second monomer in the third composition may be converted into at least a portion of the second matrix material 130 , so that the quantum-dot-containing material 1 in which the quantum-dot-containing complex 110 is dispersed in the second matrix material 130 may be prepared.
[0239] The step (or action) of “converting the second monomer into at least a portion of the second matrix material 130 ” may be understood as the step (or action) of “forming a second polymer by polymerizing the second monomer”.
[0240] The preparation of the quantum dot material 1 may be performed by using photopolymerization. Here, in order to prepare the quantum dot material 1 in the form of a thin film, the third composition may be provided on any suitable substrate, and then, exposure may be performed thereon to perform photopolymerization. The preparation of the quantum dot material 1 may further include baking the third composition before and / or after the exposure to remove at least a portion of the solvent from the third composition.
[0241] In one or more embodiments, the refractive index of the first monomer may be greater than the refractive index of the second monomer.
[0242] In one or more embodiments, the refractive index of the first monomer may be greater than the refractive index of the second monomer, wherein the refractive index of the first monomer may be about 1.55 to about 2.00, for example, about 1.55 to about 1.85, and the refractive index of the second monomer may be about 1.30 to about 1.55, for example, about 1.40 to about 1.50. In one or more embodiments, the difference between the refractive index of the first monomer and the refractive index of the second monomer may be about 0.05 to about 0.60, for example, about 0.06 to about 0.45. When using a first monomer and a second monomer both having a refractive index within any of the above ranges, it is easier to prepare a first host material and a second host material that satisfy the refractive index relationship described herein.
[0243] For example, the refractive indexes of Compounds 1 to 11 and Compounds 101 to 107 as examples of the first monomer and the refractive index of dipentaerythritol hexaacrylate (DPHA) as an example of the second monomer are summarized in the following Table 1. Here, it is confirmed that the refractive index of the first monomer is greater than that of the second monomer.
[0244] Table 1
[0245] Compound Refractive Index Compound 1 1.620 Compound 2 1.565 Compound 3 1.577 Compound 4 1.600 Compound 5 1.663 Compound 6 1.628 Compound 7 1.692 Compound 8 1.731 Compound 9 1.597 Compound 10 1.600 Compound 11 1.683 Compound 101 1.750 Compound 102 1.710 Compound 103 1.700 Compound 104 1.720 Compound 105 1.720 Compound 106 1.780 Compound 107 1.800 DPHA 1.488
[0246] Figure 1 The quantum dot-containing material 1 shown in FIG. 1 and prepared according to the above method can be used for various optical components.
[0247] Therefore, another embodiment of the present disclosure provides an optical member including the quantum-dot material 1. For example, both the quantum-dot material 1 and the optical member including the quantum-dot material 1 may have a thin film.
[0248] The optical member may be a color conversion member. When the color conversion member includes the quantum dot material 1 having excellent light conversion efficiency as described above, the color conversion member may also have excellent light conversion efficiency.
[0249] The color conversion member may include a substrate and a pattern layer formed on the substrate.
[0250] The substrate may be a substrate of the color conversion member or may refer to a region where the color conversion member is arranged in various devices (eg, a display device). The substrate may be made of glass, silicon (Si), silicon oxide (SiO x The polymer forming the substrate may be polyethersulfone (PES) and / or polycarbonate (PC).
[0251] The pattern layer may include a quantum dot material 1 in the form of a thin film. For example, the pattern layer may be a quantum dot material 1 in the form of a thin film. The pattern layer may be a layer formed by providing a third composition on a substrate, and then exposing the substrate in a set or predetermined pattern (for example, by performing photopolymerization on the second monomer in the third composition), developing and / or heat-treating.
[0252] The color conversion member including the substrate and the pattern layers may further include a partition wall or a black matrix formed between each pattern layer. In one or more embodiments, the color conversion member may further include a color filter for additionally improving light conversion efficiency.
[0253] The color conversion member may include a red pattern layer emitting red light, a green pattern layer emitting green light, a blue pattern layer emitting blue light, or any combination thereof. The red pattern layer, the green pattern layer, and / or the blue pattern layer may be realized by controlling the components, composition, and / or structure of the quantum dots 111 in the quantum dot material 1.
[0254] Another embodiment of the present disclosure provides a device including a quantum-dot material 1 (or an optical member including a quantum-dot material 1 ).
[0255] The apparatus may further include a light source, and the quantum dot-containing material 1 (or an optical member including the quantum dot-containing material 1) may be arranged in a path of light emitted from the light source.
[0256] The light source may emit blue light, red light, green light or white light. For example, the light source may emit blue light.
[0257] The light source may be an organic light emitting device (OLED) or a light emitting diode (LED).
[0258] Because light emitted from the light source can be photoconverted by the quantum dots 111 in the quantum dot material 1 while passing through the quantum dot material 1 as described above, light having a wavelength different from that of the light emitted from the light source can be emitted by the quantum dot material 1.
[0259] The device can be selected from various suitable display devices and / or lighting devices, etc.
[0260] Hereinafter, the quantum-dot-containing material 1 and a method of preparing the quantum-dot-containing material 1 will be described in more detail by way of examples and / or comparative examples.
[0261] Example
[0262] 1.1. Preparation of quantum dot-containing complex 1
[0263] 0.035g of polymerization initiator and 350mL of distilled water were mixed in a 500mL three-necked flask, and then 35mL of the first monomer and quantum dots (based on 100 parts by weight of the first monomer, the content is about 0.3 parts by weight) were added thereto. The resulting mixture was vigorously stirred at a speed of 500rpm at a temperature of 80°C under a nitrogen atmosphere, and then the reaction was allowed to proceed for 4 hours. After the reaction was completed, multiple washing processes were performed on it using distilled water and methanol (MeOH), and the resulting product was freeze-dried to prepare a monodisperse content quantum dot complex 1 (spherical particles). The polymerization initiator, the first monomer and the quantum dots used here are as follows:
[0264] Polymerization initiator: KPS (potassium persulfate)
[0265] First monomer: Compound 1
[0266] Quantum dots: InP / ZnS core-shell quantum dots (average particle size: 3nm to 8nm)
[0267] 1.2. Preparation of Quantum Dot-Containing Complexes 2 to 6
[0268] Quantum dot complexes 2 to 6 were each prepared in the same (or substantially the same) manner as in the preparation of quantum dot complex 1, except that compound 3, compound 4, compound 9, compound 101, and compound 107 were used instead of compound 1 as the first monomer:
[0269]
[0270] 1.3. Preparation of quantum dot-containing complex A
[0271] Quantum dot complex A was prepared in the same (or substantially the same) manner as in the preparation of quantum dot complex 1, except that a mixture of lauryl methacrylate and trimethylolpropane trimethacrylate mixed in a volume ratio of 8.25:1 was used instead of Compound 1 as the first monomer.
[0272] Evaluation Example 1 (Evaluation of average particle size and uniformity coefficient)
[0273] After evaluating the particle size distribution curve of each of the quantum dot composites 1 to 6 and the quantum dot composite A using a particle size analyzer (ELSZ-2000ZS manufactured by Otsuka Electronics), the average particle size (D50) and uniformity coefficient (D60 / D10) of each of the quantum dot composites 1 to 6 and the quantum dot composite A were evaluated, and the results are shown in Table 2.
[0274] Table 2
[0275] The number of the quantum dot complex Average particle size (D50) (nm) Uniformity coefficient (D60 / D10) 1 138 1.5 2 147 1.8 3 145 1.7 4 138 1.5 5 144 1.4 6 139 1.5 A 135 1.8
[0276] Referring to Table 2, it was confirmed that the quantum dot-containing composites 1 to 6 and the quantum dot-containing composite A all had relatively uniform particle size distributions.
[0277] 2.1. Preparation of Quantum Dot-Containing Composition 1
[0278] The quantum dot complex (15 wt %), the second monomer (30 wt %), the photopolymerization initiator (5 wt %), the dispersant (5 wt %), the first solvent (30 wt %) and the second solvent (15 wt %) shown below were mixed to prepare a quantum dot composition 1.
[0279] ·Containing quantum dot complex: containing quantum dot complex 1
[0280] Second monomer: dipentaerythritol hexaacrylate (DPHA) (Aldrich 407283)
[0281] Photopolymerization initiator: Irgacure-907 (BASF)
[0282] Dispersant: DISPER BYK-2011 (BYK-Chemie)
[0283] First solvent: 3-phenyl-ethyl propionate
[0284] Second solvent: propylene glycol monomethyl ether acetate
[0285] 2.2. Preparation of Quantum Dot Compositions 2 to 6
[0286] Quantum-dot compositions 2 to 6 are each prepared in the same (or substantially the same) manner as in the preparation of quantum-dot composition 1, except that quantum-dot composition 2 to 6 are respectively used instead of quantum-dot composition 1 as the quantum-dot composition.
[0287] 2.3. Preparation of Quantum Dot Composition A
[0288] Quantum-dot composition A was prepared in the same (or substantially the same) manner as in the preparation of quantum-dot composition 1, except that quantum-dot complex A was used instead of quantum-dot complex 1 as the quantum-dot complex and polyurethane acrylate (Dymax OP-4-20639) was used instead of DPHA as the second monomer.
[0289] 2.4. Preparation of Quantum Dot-Containing Composition B
[0290] Quantum-dot composition B was prepared in the same (or substantially the same) manner as in the preparation of quantum-dot composition 1, except that quantum-dot complex A was used instead of quantum-dot complex 1 as the quantum-dot complex and polyurethane acrylate (Dymax OP-4-26032) was used instead of DPHA as the second monomer.
[0291] 2.5. Preparation of Quantum Dot-Containing Composition C
[0292] In addition to the InP / ZnS core-shell quantum dots (10 wt%) and TiO 2 A quantum dot composition C was prepared in the same (or substantially the same) manner as in the preparation of the quantum dot composition 1, except that a mixture of particles (Degussa, average particle size D50: 5 wt %) was used as the quantum dot composite.
[0293] Evaluation Example 2 (Evaluation of dispersion stability)
[0294] Each of the quantum dot composition 1 to the quantum dot composition 6 and the quantum dot composition C was sampled and its dispersed particle size was evaluated using a particle size analyzer (ELSZ-2000ZS manufactured by Otsuka). Next, each of the sampled quantum dot composition 1 to the quantum dot composition 6 and the quantum dot composition C was stored at a temperature of 25° C. and a relative humidity of 20% for 30 days, and then, the dispersed particle size was evaluated using the same method as above. The results are shown in Table 3.
[0295] Table 3
[0296] Composition number of quantum dots Initial dispersion particle size (nm) Dispersion particle size after 30 days (nm) 1 142 153 2 153 151 3 150 149 4 146 156 5 152 154 6 147 161 C 846 2727
[0297] Referring to Table 3, it was confirmed that the quantum dot-containing compositions 1 to 6 had excellent dispersion stability.
[0298] Evaluation Example 3 (Evaluation of Discharge Stability)
[0299] After sampling each of the quantum dot composition 1 to the quantum dot composition 6 and the quantum dot composition C, the discharge stability of the inkjet head was evaluated by performing an evaluation of the impact accuracy thereon during 30 days of discharge using an inkjet printer, and the results are shown in Table 4. When the impact accuracy at the time of discharge for 30 days was ±5 μm in the x-axis direction and the y-axis direction, the discharge stability was evaluated as "excellent". When the impact accuracy at the time of discharge for 30 days was not ±5 μm in the x-axis direction and the y-axis direction, the discharge stability was evaluated as "poor".
[0300] Table 4
[0301]
[0302]
[0303] 3.1. Preparation of Quantum Dot-Containing Film 1
[0304] The quantum dot composition 1 was coated on a glass substrate using a spin coater and subjected to a pre-baking process at 100° C. for 1 minute using a hot plate. 2 After irradiating UV light (wavelength of 365 nm) with an exposure content of 1.5 μm, a post-baking process was performed in a thermal oven at a temperature of 180° C. for 30 minutes under a nitrogen atmosphere, thereby preparing a quantum dot film 1 having a thickness of 3 μm.
[0305] 3.2. Preparation of Quantum Dot Films 2 to 6 and Quantum Dot Films A to C
[0306] Quantum-dot films 2 to 6 and quantum-dot films A to C are each prepared in the same (or substantially the same) manner as in the preparation of quantum-dot film 1, except that quantum-dot compositions 2 to 6 and quantum-dot compositions A to C are respectively used instead of quantum-dot composition 1.
[0307] Evaluation Example 4 (Evaluation of refractive index)
[0308] For each of the quantum dot-containing films 1 to 6, the quantum dot-containing film A, and the quantum dot-containing film B, the first matrix material (i.e., the first matrix material) in the quantum dot-containing composite was evaluated at a relative humidity of 50% at a temperature of 25° C. using an ellipsometer M-2000 (JA Woollam) based on a wavelength of 589 nm according to the Cauchy Film Model. Figure 1 The first matrix material 113 in the film containing quantum dots and the second matrix material in the film containing quantum dots (ie, Figure 1 The results are summarized in Table 5.
[0309] Table 5
[0310]
[0311]
[0312] Referring to Table 5, it is confirmed that the refractive index of the first matrix material in quantum dot film 1 to quantum dot film 6 is greater than the refractive index of the second matrix material, and the refractive index of the first matrix material in quantum dot film A and quantum dot film B is not greater than the refractive index of the second matrix material.
[0313] Evaluation Example 5 (Evaluation of Light Conversion Efficiency)
[0314] A blue backlight unit (blue BLU) equipped with a diffusion film (emitting blue light with a maximum emission wavelength of 455 nm) was prepared. Next, a bare glass was set on the blue BLU, and a spectrometer (CAS 140CT manufactured by Instrument Systems) was used to measure the emission amount of blue light to set a reference point. Then, the bare glass substrate was replaced with a glass substrate on which each of the quantum dot films 1 to 6 and the quantum dot films A to C were formed. The spectrometer was used to measure the decrease in the absorption peak relative to the blue light, and the increase in the peak converted to the green light to evaluate the light conversion efficiency of the quantum dot films 1 to 6 and the quantum dot films A to C, and the results are shown in Table 6.
[0315] Table 6
[0316] Film number containing quantum dots Light conversion rate (%) 1 37 2 35 3 38 4 32 5 39 6 40 A 21 B 22 C 23
[0317] Referring to Table 6, it was confirmed that the quantum dot film 1 to the quantum dot film 6 had excellent light conversion efficiency compared with the quantum dot film A to the quantum dot film C.
[0318] According to one or more embodiments of the present disclosure, an optical member including a quantum dot-containing material has excellent light conversion efficiency, and thus, the use of the quantum dot-containing material may enable the realization of various high-quality devices.
[0319] As used herein, the term "use" and variations thereof may be considered synonymous with the term "utilize" and variations thereof, respectively.
[0320] Additionally, the terms "substantially," "about," and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that those skilled in the art would recognize.
[0321] In addition, any numerical range stated herein is intended to include all sub-ranges of the same numerical precision contained in the stated range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the stated minimum value 1.0 and the stated maximum value 10.0 (including the stated minimum value 1.0 and the stated maximum value 10.0), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated here is intended to include all smaller numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all larger numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any sub-range contained in the scope explicitly stated here.
[0322] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
[0323] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the claims and their equivalents.
Claims
1. A quantum dot-containing material, comprising: A quantum dot composite comprising quantum dots and a first host material; as well as The second matrix material, wherein the quantum dots are dispersed in the first matrix material, The quantum dot-containing complex is dispersed in the second matrix material, The quantum dot-containing material is a thin film, The refractive index of the first matrix material is greater than the refractive index of the second matrix material, The first matrix material includes a first polymer obtained by polymerizing a first monomer by solution polymerization, The second matrix material includes a second polymer obtained by polymerizing a second monomer by photopolymerization, The second monomer includes an acrylic monomer, and A difference between the refractive index of the first host material and the refractive index of the second host material is 0.05 to 0.
60.
2. The quantum dot material according to claim 1, in, The quantum dots include III-V semiconductor compounds and II-VI semiconductor compounds.
3. The quantum dot-containing material according to claim 1, in, The refractive index of the first host material is 1.55 to 2.00, and the refractive index of the second host material is 1.30 to 1.
55.
4. The quantum dot-containing material according to claim 1, The first monomer is a water-soluble vinyl monomer, a water-soluble acrylic monomer, a water-soluble acrylamide monomer or any combination thereof.
5. The quantum dot-containing material according to claim 1, in, The quantum dot-containing complex is a spherical particle.
6. The quantum dot-containing material according to claim 1, in, The average particle size D50 of the quantum dot-containing composite is 40 nm to 1,000 nm.
7. A method for preparing a material containing quantum dots, the method comprising the following steps: preparing a first composition including quantum dots, a first monomer, a polymerization initiator, and a solvent; preparing a second composition by converting the first monomer in the first composition into at least a portion of a first matrix material, the second composition comprising a quantum dot-containing composite and the solvent, the quantum dot-containing composite comprising the quantum dots and the first matrix material in which the quantum dots are dispersed; obtaining the quantum dot-containing complex by removing the solvent from the second composition; preparing a third composition including the quantum dot complex, a second monomer, a polymerization initiator, and a solvent; as well as The quantum dot-containing material is prepared by converting the second monomer in the third composition into at least a portion of a second matrix material, wherein the quantum dot-containing material includes the quantum dot-containing composite and the second matrix material in which the quantum dot-containing composite is dispersed. wherein the refractive index of the first matrix material is greater than the refractive index of the second matrix material, The quantum dot-containing material is a thin film, The first matrix material includes a first polymer obtained by polymerizing the first monomer by solution polymerization, The second matrix material includes a second polymer obtained by polymerizing the second monomer by photopolymerization, The second monomer includes an acrylic monomer, and A difference between the refractive index of the first host material and the refractive index of the second host material is 0.05 to 0.
60.
8. The method according to claim 7, wherein: The solvent in the first composition is water, The first monomer includes a water-soluble vinyl monomer, a water-soluble acrylic monomer, a water-soluble acrylamide monomer or any combination thereof. The polymerization initiator in the first composition is a water-soluble polymerization initiator, and The step of preparing the second composition is performed using solution polymerization.
9. The method according to claim 8, wherein: The quantum dot-containing complex is a spherical particle.
10. The method according to claim 8, wherein: The step of obtaining the quantum dot-containing complex is performed by freeze drying.
11. The method according to claim 8, wherein: The step of preparing the quantum dot-containing material is performed using photopolymerization.
12. The method according to claim 8, wherein: The refractive index of the first monomer is greater than the refractive index of the second monomer. 13 . An optical component comprising the quantum dot material according to claim 1 .
14. The optical component according to claim 13, wherein The optical component is a color conversion component.
15. A device comprising the quantum dot-containing material according to claim 1.
16. The device according to claim 15, wherein: The device also includes a light source, and The quantum dot containing material is disposed in a path of light emitted from the light source.
17. The apparatus according to claim 16, wherein: The light source is an organic light emitting device or a light emitting diode.
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