Charge transport composite and method for high resolution patterning of charge transport layer comprising same, charge transport layer composition comprising same, organic

Abstract

The invention discloses a charge transport compound, a high-resolution patterning method of a charge transport layer comprising the same, a charge transport layer composition comprising the same, and an organic light emitting device comprising the same. A charge transport compound according to the present invention is characterized by comprising: a curable organic semiconductor; and an organic silicon dioxide precursor which forms a silicon (-Si-O-Si-) network structure with the curable organic semiconductor, the curable organic semiconductor containing a crosslinking functional group.

Description

Technical Field

[0001] The present invention relates to a charge transfer complex and a high-resolution patterning method of a charge transfer layer comprising the same, a charge transfer layer composition comprising the same, and an organic light-emitting device comprising the same. More specifically, the present invention relates to an organosilicon (-Si-O-Si-) embedded charge transfer complex with a high-durability organosilicon (-Si-O-Si-) network structure and a high-resolution patterning method of a charge transfer layer comprising the same, a charge transfer layer composition comprising the same, and an organic light-emitting device comprising the same. Background Art

[0002] As reality content and the real metaverse (five senses enhancement technology) based on building hyper-connected interactions between users and objects are rapidly emerging as the next-generation IT content power industry, vision-based hyper-reality and immersive VR / AR / MR / XR devices play a core role in human senses and cognition and have received widespread attention.

[0003] Microdisplays are key components responsible for the visual factors of hyper-reality VR / AR / MR / XR technologies. As a medium, they deliver information to users by stimulating vision, which is the most sensitive sense of humans, so the required technical performance is very high. Therefore, in order to provide users with an overwhelming sense of immersion and prevent adverse reactions to the human body (dizziness, vomiting), a microdisplay that can achieve the following performance is required: i) ultra-high-resolution RGB patterns of more than 3000ppi, ii) fast response speed, iii) color purity close to reality, and iv) low power consumption.

[0004] Organic Light-Emitting Diode (OLED) has the following advantages: i) excellent color reproducibility, ii) fast frame rate, iii) wide viewing angle, and iv) low power consumption. Therefore, it has attracted much attention as the next-generation display and can effectively meet the performance requirements of ultra-realistic VR / AR / MR / XR microdisplays. However, due to the inherent low durability of the hole transport layer material, the realization of ultra-high resolution RGB patterns is extremely limited. Therefore, the demand for ultra-precision micropatterning technology in the hole transport layer to solve this problem is rapidly increasing.

[0005] In order to achieve ultra-high resolution patterns of the hole transport layer, various patterning technologies are being developed, such as printing technology, ultra-precision metal mask (FMM) patterning, orthogonal lithography, self-assembly patterning, etc., but the resolution is still limited, and there are various problems such as uneven patterns, reduced luminescence performance due to the process, and limitations of multi-patterning processes based on solution processes. In contrast, photolithography and dry etching are the most optimized high-resolution patterning process technologies in the industry, which can easily and efficiently achieve precise ultra-fine patterns, but they must meet the durability of materials that can withstand the physical and chemical damage that inevitably occurs during the process, so they have the limitation of being difficult to apply to the hole transport layer.

[0006] For example, Korean Patent No. 1350658 discloses a technology in which a cross-linking agent (aziridine, carbodiimide, ethylene oxide, allyl compound, and silane coupling agent) is added to a material constituting a charge transport layer to ensure chemical resistance to a wet process, thereby developing an OLED device in which a charge transport layer is patterned with a sub-pixel as a unit through a photolithography process. However, since patterning is performed through a wet process rather than a dry process, an undercut phenomenon occurs due to isotropic etching, and there are limitations in that the pattern density and uniformity are low.

[0007] Tsai, Kuen-Wei et al. disclosed a technology for manufacturing OLED devices through a continuous solution process using a curable hole transport layer material (Oxe-DCDPA) introduced with oxetane, which introduces a multi-layer hole transport layer through a hole transport layer whose chemical resistance is ensured, and by manufacturing a multi-layer structured OLED device based on a solution process, while reducing the driving voltage, achieves excellent external quantum efficiency (26.1%) and luminous efficiency (94.8 cd / A), however, since high-resolution patterning of the hole transport layer is impossible, pixel crosstalk may occur when applied to high-resolution OLED devices.

[0008] Lim, Younhee et al. disclosed a technology for manufacturing OLED devices through a continuous solution process using a curable hole transport layer material (TEVS-TPD) introduced with an organosilicon cross-linking functional group. The technology ensures the chemical resistance of the hole transport layer through this material design, while increasing the conjugation length through the connection between organic semiconductor molecules, improving the charge mobility characteristics of the hole transport layer, thereby ensuring the OLED performance of external quantum efficiency (6.4%) and power efficiency (13.5lm / W). However, no research attempts have been made to achieve ultra-high resolution patterns of the hole transport layer, and pixel crosstalk may be caused when the above-mentioned unpatterned materials are applied to high-resolution OLED devices.

[0009] In other words, as far as the research on existing curable charge transport layers based on low-molecular organic semiconductors is concerned, the focus has mainly been on developing OLED devices for solution processes by ensuring the chemical resistance of the charge transport layer, and therefore no research attempts have been made to achieve ultra-high-resolution patterns of OLED common layers. In addition, charge transport layer patterning technology based on photolithography has been reported, but the patterning is achieved by wet etching, so there are limitations such as limited pattern resolution and low pattern uniformity, and there has been no research report on the technology to achieve ultra-fine patterns of several microns by using charge transport layer materials that are resistant to dry etching.

[0010] Therefore, there is a need to develop a charge transport layer that can improve light-emitting characteristics while improving etching resistance and chemical resistance so that it can be patterned by a photolithography process and a dry etching method. Summary of the invention

[0011] Technical issues

[0012] The purpose of the embodiments of the present invention is to provide a charge transfer complex having a silicone (-Si-O-Si-) network structure and a high-resolution patterning method of a charge transfer layer containing the same, a charge transfer layer composition containing the same, and an organic light-emitting device containing the same. The charge transfer complex can be directly applied to general lithography and dry etching methods as ultra-high resolution patterning technologies, which are technologies established based on commercial charge transport layer materials to ensure high durability (chemical resistance and etching resistance).

[0013] In particular, the purpose of the embodiments of the present invention is to provide a charge transfer complex and a high-resolution patterning method of a charge transfer layer containing the same, a charge transfer layer composition containing the same, and an organic light-emitting device containing the same. The charge transfer complex can realize an organic silicon (-Si-O-Si-) network structure through a simultaneous or cross-curing reaction between an introduced low-molecular-weight organic semiconductor and an organic silicon dioxide precursor, thereby enhancing chemical resistance and etching resistance without reducing photoelectric properties.

[0014] Furthermore, an embodiment of the present invention aims to provide a charge transfer complex and a high-resolution patterning method of a charge transfer layer comprising the same, a charge transfer layer composition comprising the same, and an organic light-emitting device comprising the same. The charge transfer complex introduces an organic silicon dioxide precursor into a curable low-molecular organic semiconductor that can form an organic silicon (Silicone, -Si-O-Si-) network through a cross-linking reaction with the organic semiconductor, thereby improving the luminescence efficiency while ensuring chemical resistance / etching resistance.

[0015] Technical Solution

[0016] The charge transfer complex of the embodiment of the present invention comprises: a curable organic semiconductor; and an organic silicon dioxide precursor, which forms an organic silicon (-Si-O-Si-) network structure with the curable organic semiconductor, wherein the curable organic semiconductor comprises a cross-linking functional group.

[0017] The cross-linking functional group may include at least one of a vinyl group, a vinyl derivative, an oxetane group, a boronic acid group, a trifluorovinyl ether, a benzocyclobutene, and an epoxide.

[0018] The cross-linking functional group may include a functional group represented by any one of the following Chemical Formulas 3 to 8:

[0019] Chemical formula 3:

[0020]

[0021] Chemical formula 4:

[0022]

[0023] Chemical formula 5:

[0024]

[0025] Chemical formula 6:

[0026]

[0027] Chemical formula 7:

[0028]

[0029] Chemical formula 8:

[0030]

[0031] (In the chemical formulas 3 to 9, R1 each independently includes hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, carbonyl, ether, silyl, siloxane, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, C1-C20 haloalkyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl, any one of a C30 aryloxy group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C7-C30 arylalkyl group, a substituted or unsubstituted C2-C30 alkenyloxy group, a substituted or unsubstituted C8-C30 alkenylaryl group, a substituted or unsubstituted C7-C30 arylalkoxy group, a substituted or unsubstituted C8-C30 arylalkenyl group and a substituted or unsubstituted C2-C20 alkoxycarbonyl group)

[0032] The curable organic semiconductor may be a hole transport compound bonded with the cross-linking functional group, and the hole transport compound may include at least one of triphenylamine derivatives, aromatic diamine derivatives, arylene diamine derivatives, carbazole derivatives, spiroarylene diamine derivatives, starburst amine derivatives, triarylamine derivatives, thiophene derivatives and triarylphosphine derivatives.

[0033] The curable organic semiconductor may include N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine henyl-4,4'-diamine, QUPD), 4,N4'-bis(4-(6-((3-ethyloxetane-3-yl)methoxy)hexyl)phenyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine, OTPD), N,N-bis(4-(6-((3-ethyloxetane-3-yl)methoxy)hexyl)phenyl)-3,5-di(9H-carbazol-9-yl)aniline at least one of 1,2-diaminobenzyl-2-yl-4-thiazolyl-9-yl)benzenamine (Oxe-DCDPA), 1,1,2-diaminobenzyl-2-yl-4-thiazolyl-9-yl)amine (Tris(4-carbazoyl-9-ylphenyl)amine, TCTA), N,N'-bis(tolyl)-N,N'-bis(vinylphenyl)-1,1'-biphenyl-4,4'-diamine (DV-TPD), tris[(p-trifluorovinyloxy-biphenyl)]amine (TPA-TFVE), MUPD and AUPD.

[0034] The curable organic semiconductor may be an electron transport compound bonded with the cross-linking functional group, and the electron transport compound may include at least one of an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, a benzoxazole derivative, a benzothiazole derivative, a benzimidazole derivative, a triazine derivative, a benzoquinone derivative, a pyridine derivative, an anthraquinone derivative, a polyquinoline derivative, and a polyfluorene derivative.

[0035] The curable organic semiconductor may include at least one of 4,6-bis[4-(5-{4-[(4-vinylbenzyloxy)methyl]phenyl}-4-(4-tert-butyl-phenyl)-4H-1,2,4-triazol-3-yl)phenyl]-2-methylpyrimidie (DV-46PymTAZ), SMH-E-10, 1,3,5-tris(5(4-vinylpheny l)pyridin-3-yl)benzene (TV-TmPY) and U-BmPyPB.

[0036] The luminescence intensity and durability of the charge transport complex can be adjusted according to the concentration of the organic silica precursor.

[0037] The concentration of the organic silica precursor may be 1.40 weight percent to 7.13 weight percent based on the charge transfer complex.

[0038] The organic silica precursor may include a compound represented by any one of the following Chemical Formulas 9 to 19:

[0039] Chemical formula 9:

[0040]

[0041] (In the chemical formula 9, R' contains 1 to 3 halogen elements and an alkoxy group (-O-(CH2) x -CH3, wherein X is an integer from 0 to 8), and m is an integer from 0 to 20)

[0042] Chemical formula 10:

[0043]

[0044] Chemical formula 11:

[0045]

[0046] Chemical formula 12:

[0047]

[0048] Chemical formula 13:

[0049]

[0050] (In the chemical formula 13, R' contains 1 to 3 halogen elements and an alkoxy group (-O-(CH2) x -CH3, wherein X is an integer from 0 to 8)

[0051] Chemical formula 14:

[0052]

[0053] Chemical formula 15:

[0054]

[0055] Chemical formula 16:

[0056]

[0057] Chemical formula 17:

[0058]

[0059] Chemical formula 18:

[0060]

[0061] Chemical formula 19:

[0062]

[0063] The silicone (-Si-O-Si-) network structure can be any one of a single phase network (SPN) bonded with silicone (-Si-O-Si-) and an interpenetrating polymer network (IPN) bonded with silicone (-Si-O-Si-).

[0064] The patterning method of the charge transport layer of the embodiment of the present invention may include: a step of forming a charge transport layer containing the charge transport complex of the embodiment of the present invention; a step of forming a photoresist on the charge transport layer; a step of patterning the photoresist to form a photoresist pattern; a step of dry etching the charge transport layer using the photoresist pattern as an etching mask to form a charge transport layer pattern; and a step of removing the photoresist pattern.

[0065] The charge transfer complex may include a silicone (-Si-O-Si-) network structure, and the silicone (-Si-O-Si-) network structure may be any one of a single phase network (SPN) bonded with silicone (-Si-O-Si-) and an interpenetrating polymer network (IPN) bonded with silicone (-Si-O-Si-).

[0066] In the step of forming the charge transport layer, at least two sub-charge transport layers having different concentrations of the organic silicon dioxide precursor may be formed on the substrate.

[0067] In the step of forming a charge transport layer pattern by dry etching the charge transport layer using the photoresist pattern as an etching mask, the charge transport layer can form a non-volatile blocking layer on the side of the charge transport layer pattern through the silicone (-Si-O-Si-) network structure of the charge transport complex.

[0068] The non-volatile barrier layer may include at least one of SixOy and SixOyFz (x, y, and z are integers of 1 to 4).

[0069] The size of the charge transport layer pattern may be 10 nm to 1000 μm.

[0070] The organic light-emitting device of an embodiment of the present invention comprises: a first electrode formed on a substrate; an organic light-emitting layer formed on the first electrode; a second electrode formed on the organic light-emitting layer; and a charge transfer layer formed at least one of an interface between the first electrode and the organic light-emitting layer and an interface between the organic light-emitting layer and the second electrode, and comprises a charge transfer complex according to any one of claims 1 to 9.

[0071] The luminescence intensity and durability of the charge transport layer can be adjusted according to the concentration of the organic silica precursor.

[0072] The charge transport layer may include at least two sub-charge transport layers having different concentrations of the organic silicon dioxide precursor.

[0073] The charge transport layer may include a first sub-charge transport layer and a second sub-charge transport layer at an interface between the first electrode and the organic light-emitting layer, and a concentration of an organic silicon dioxide precursor in the second sub-charge transport layer may be higher than a concentration of an organic silicon dioxide precursor in the first sub-charge transport layer.

[0074] The charge transport layer composition according to the embodiment of the present invention comprises: a curable organic semiconductor; and an organic silicon dioxide precursor.

[0075] The charge transport layer composition may include 92.87 weight percent to 98.6 weight percent of the curable organic semiconductor and 1.40 weight percent to 7.13 weight percent of the organic silica precursor.

[0076] Effects of the Invention

[0077] According to an embodiment of the present invention, a charge transfer complex having a silicone (-Si-O-Si-) network structure and a high-resolution patterning method of a charge transfer layer containing the same, a charge transfer layer composition containing the same, and an organic light-emitting device containing the same can be provided. The charge transfer complex can be directly applied to general photolithography and dry etching methods as ultra-high resolution patterning technologies, which are technologies established based on commercialized charge transfer layer materials to ensure high durability (chemical resistance and etching resistance).

[0078] In particular, according to an embodiment of the present invention, a charge transfer complex and a high-resolution patterning method of a charge transfer layer containing the same, a charge transfer layer composition containing the same, and an organic light-emitting device containing the same can be provided. The charge transfer complex can realize an organic silicon (-Si-O-Si-) network structure through a simultaneous or cross-curing reaction between an introduced low-molecular-weight organic semiconductor and an organic silicon dioxide precursor, thereby enhancing chemical resistance and etching resistance at the same time without reducing the photoelectric properties.

[0079] Furthermore, according to an embodiment of the present invention, a charge transfer complex and a high-resolution patterning method of a charge transfer layer containing the same, a charge transfer layer composition containing the same, and an organic light-emitting device containing the same can be provided. The charge transfer complex can improve the luminescence efficiency while ensuring chemical resistance / etching resistance by introducing an organic silicon dioxide precursor into a curable low-molecular organic semiconductor that can form an organic silicon (Silicone, -Si-O-Si-) network through a cross-linking reaction with the organic semiconductor. BRIEF DESCRIPTION OF THE DRAWINGS

[0080] Figure 1a A simplified diagram showing a charge transfer complex according to an embodiment of the present invention is shown in FIG. Figure 1b is a simplified diagram showing an organosilica precursor;

[0081] Figure 2 A simplified diagram showing a method for patterning a charge transport layer according to an embodiment of the present invention;

[0082] Figure 3a A simplified diagram is shown for comparing the wet etching process of the conventional hole transport layer with the dry etching of the patterning method of the charge transport layer of an embodiment of the present invention;

[0083] Figure 3b A simplified diagram showing a comparison between a conventional hole transport layer and a charge transport layer pattern obtained by a charge transport layer patterning method according to an embodiment of the present invention;

[0084] Figure 4 A cross-sectional view showing an organic light emitting device according to an embodiment of the present invention;

[0085] Figure 5 is a diagram showing the FT-IR analysis results of the cross-linking reaction of the charge transport complex of Example 1;

[0086] Figure 6 A diagram showing the results of ToF-SIMS analysis of a hole transport layer comprising QUPD (X-QUPD) and the charge transport complex of Example 1 (SPN-QUPD);

[0087] Figure 7 AFM measurement images of the hole transport layer including QUPD (X-QUPD) and the charge transport complex of Example 1 (SPN-QUPD);

[0088] Figure 8 An image showing a charge transport layer pattern of a hole transport layer comprising the charge transport complex (SPN-QUPD) of Example 1;

[0089] Fig. 9 A graph showing the width and height of a high resolution pattern of a hole transport layer of a hole transport layer comprising the charge transport complex (SPN-QUPD) of Example 1, Fig.10 is a graph showing the results of chemical resistance testing, Fig.11 is a graph showing the results of an etching resistance test;

[0090] Fig.12A diagram showing an organic light-emitting device (Example 2-1, Example 2-2, Example 2-3) including the charge transport complex of Example 1 having different concentrations of an organic silica precursor in a hole transport layer (SPN 4 mol%, 8 mol%, 16 mol%) and an image showing an energy band diagram;

[0091] Fig.13 is a diagram showing ultraviolet photoelectron spectroscopy (UPS), Fig.14 For a graph showing absorbance, Fig.15 A graph showing a band gap (energy gap) by a Tauc plot;

[0092] Fig.16 2 is a graph showing the change in current density and brightness of the organic light-emitting device of the comparative example and the organic light-emitting devices of Examples 2-1 to 2-3 as a function of voltage, Fig.17 For a graph showing power efficiency and external quantum efficiency as a function of brightness, Fig.18 To show the graph of current efficiency as a function of brightness, Fig.19 A graph is shown to summarize the brightness and maximum quantum efficiency as a function of the organosilica precursor content;

[0093] Fig. 20 A schematic diagram of an organic light-emitting device based on a bilayer hole transport layer of Example 3 and an image showing an energy band diagram;

[0094] Fig.21 is a graph showing the change in current density and brightness of the organic light-emitting device of Example 2-1 and the organic light-emitting device of Example 3 with voltage, Fig. 22 A graph is shown to compare power efficiency and external quantum efficiency as a function of brightness, Fig.23 A graph is shown to compare the current efficiency as a function of brightness. Fig.24 Graphs are shown for comparison of brightness and maximum quantum efficiency. DETAILED DESCRIPTION

[0095] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings and the contents described in the drawings, but the present invention is not limited to or restricted to the embodiments.

[0096] The terms used in this specification are only used to illustrate the embodiments and are not intended to limit the present invention. In this specification, unless the context clearly indicates otherwise, the singular form also includes the plural form. The "comprises" and / or "comprising" used in the specification means that the mentioned structural elements, steps, operations and / or devices do not exclude the existence or addition of more than one other structural elements, steps, operations and / or devices.

[0097] The terms “embodiment”, “example”, “aspect”, “example”, etc. used in this specification should not be interpreted as any aspect or design described being superior or advantageous over other aspects or designs.

[0098] Furthermore, the term "or" means "inclusive or" rather than "exclusive or." That is, unless otherwise stated or clear from the context, the expression "x employs a or b" means any of the natural inclusive permutations.

[0099] In addition, unless stated otherwise or clear from context, the singular expressions ("a" or "an") used in the specification and the claims should be construed as generally referring to "more than one."

[0100] The terms used in the following description are selected as commonly used and general in the relevant technical field, but other terms may exist according to technical development and / or changes, habits, preferences of technicians, etc. Therefore, the terms used in the following description should not be understood as limiting the technical ideas, but should be understood as illustrative terms for explaining the embodiments.

[0101] And, in some cases, there are terms arbitrarily selected by the applicant, in which case their detailed meanings will be described in the relevant description section. Therefore, the terms used in the following description should be understood based on the meaning of the terms and the overall content of the description, rather than simply based on the names of the terms.

[0102] On the other hand, terms such as "first" and "second" can be used to describe various structural elements, but the structural elements are not limited to these terms. These terms are only used to distinguish one structural element from another structural element.

[0103] Furthermore, when one part of a film, layer, region, structural element, etc. is referred to as being "on" or "over" another part, this not only means that it is directly on the other part, but also means that there are other films, layers, regions or structural elements in between.

[0104] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification can be used with the meaning that can be generally understood by those skilled in the art to which the present invention belongs. In addition, unless clearly specifically defined, the terms defined in the commonly used dictionaries will not be ideally or over-interpreted.

[0105] On the other hand, when describing the present invention, if it is determined that the detailed description of the related known functions or configurations may unnecessarily obscure the gist of the present invention, the detailed description will be omitted. In addition, the terminology used in this specification is a term used to appropriately express the embodiments of the present invention, and may change according to the intention of the user or operator or the custom of the field to which the present invention belongs. Therefore, the definition of these terms should be based on the overall content of the specification.

[0106] Figure 1a A simplified diagram showing a charge transfer complex according to an embodiment of the present invention is shown in FIG. Figure 1b is a simplified diagram showing an organosilica precursor.

[0107] Organic light-emitting devices (OLEDs) have the advantages of excellent color reproduction, fast response speed, wide viewing angle, and low power consumption. Therefore, they have attracted much attention as the next-generation display technology. They can be effectively applied to ultra-realistic and immersive VR / AR / MR / XR micro-displays to realize realistic content and real metaverse technology. As a result, ultra-high-resolution full-color (Full- co lor) OLED displays, where each R / G / B sub-pixel is directly patterned.

[0108] As the resolution of full-color OLEDs (above 300ppi) increases, the spacing between R / G / B sub-pixels becomes closer, and leakage current will occur between adjacent pixels along the charge transfer layer formed as a common layer in the OLED device, resulting in reduced pixel clarity and color reproducibility. When ultra-high-resolution (above 3000ppi) full-color OLEDs for microdisplays are realized, this pixel crosstalk phenomenon will become more serious. Therefore, there is an urgent need for the design of charge transfer layer materials that can achieve ultra-fine patterns and ultra-high-resolution pattern process methodology.

[0109] The charge transfer composite of the embodiment of the present invention can form organic silicon (Silicon eAn organic silica precursor with a Si--Si-O-Si-) network is applied to a low-molecular-weight curable organic semiconductor material with excellent charge conduction characteristics as a common layer of an organic light-emitting device to simultaneously improve the chemical resistance and etching resistance of the low-molecular-weight curable organic semiconductor, thereby achieving ultra-high-resolution patterns based on general photolithography and dry etching methods.

[0110] More specifically, the charge transfer composite of the embodiment of the present invention comprises a curable organic semiconductor and a silicone e The curable organic semiconductor contains a cross-linking functional group, and a bonded organic silicon (Silicon) can be formed by a simultaneous or cross-curing reaction between the cross-linking functional group of the curable organic semiconductor and the organic silica precursor. e , -Si-O-Si-)'s SPN or IPN.

[0111] Therefore, the charge transport composite of the embodiment of the present invention can be directly applied to the general photolithography and dry etching method as an ultra-high resolution pattern technology to realize ultra-fine patterns. The technology is to introduce organic silicon (Silicon) into the commercial charge transport layer material. e , -Si-O-Si-) network to ensure high durability (chemical resistance and etching resistance) and luminescent properties.

[0112] In other words, the charge transfer complex of the embodiment of the present invention can be effectively applied to micro displays, small high-resolution full-color displays, and other displays that require high resolution and may cause crosstalk between pixels. co lor)OLED display panel, etc.

[0113] In the following, each structural element of the charge transfer complex according to an embodiment of the present invention will be described in more detail.

[0114] The charge transfer complex according to the embodiment of the present invention comprises a curable organic semiconductor having a cross-linking functional group.

[0115] The curable organic semiconductor may include a charge transport compound (including at least one of a hole transport compound and an electron transport compound) bonded with a crosslinking functional group. For example, the curable organic semiconductor may be represented by the following chemical formula 1:

[0116] Chemical formula 1:

[0117] RAR.

[0118] (In the chemical formula 1, A is a hole transport compound or an electron transport compound, and R is a cross-linking functional group)

[0119] The curable organic semiconductor can be formed into an organic silicon by bonding the crosslinking functional group to the hole transport compound or the electron transport compound and crosslinking with the organic silicon dioxide precursor through a curing reaction. e , -Si-O-Si-) network structure.

[0120] The bonding position of the crosslinking functional group of the hole transport compound or the electron transport compound is not particularly limited.

[0121] The curable organic semiconductor can be a hole transport compound bonded with a cross-linking functional group, and the hole transport compound can include at least one of triphenylamine derivatives, aromatic diamine derivatives, arylene diamine derivatives, carbazole derivatives, spiroarylene diamine derivatives, starburst amine derivatives, triarylamine derivatives, thiophene derivatives and triarylphosphine derivatives.

[0122] Preferably, the curable organic semiconductor may include N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine henyl-4,4'-diamine, QUPD), N4,N4'-Bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyl)phenyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine ine, OTPD), N,N-bis(4-(6-((3-ethyloxetane-3-yl)methoxy)hexyloxy)phenyl)-3,5-di(9H-carbazol-9-yl)benzenamine, Oxe-DCDPA), vinyl Benzyl (Vinylbenzyl, VB)-tris (4-carbazoyl-9-ylphenyl) amine) (Tris (4-carbazoyl-9-ylphenyl) amine, TCTA), N, N'-bis (tolyl)-N, N'-bis (vinylphenyl)-1, 1'-biphenyl-4, 4'-diamine (N, N'-bis (tolyl)-N, N'-bis (vinylphenyl)-1, 1'-biphenyl-4, 4'-diamine ine, DV-TPD), tris[(p-trifluorovinyloxy-biphenyl)]amine (tris[(p-trifluorovinyloxy-biphenyl)]amine, TPA-TFVE), MUPD and AUPD. More preferably, the curable organic semiconductor may be N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine (N4,N4'-Bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine).4'-diamine, QUPD).

[0123] N4,N4'-Bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine (QUPD) can be represented by the following chemical formula 2:

[0124] Chemical formula 2:

[0125]

[0126] Furthermore, the curable organic semiconductor may be an electron transport compound bonded with a cross-linking functional group, and the electron transport compound may include at least one of an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, a benzoxazole derivative, a benzothiazole derivative, a benzimidazole derivative, a triazine derivative, a benzoquinone derivative, a pyridine derivative, an anthraquinone derivative, a polyquinoline derivative, and a polyfluorene derivative.

[0127] The curable organic semiconductor may include at least one of 4,6-bis[4-(5-{4-[(4-vinylbenzyloxy)methyl]phenyl}-4-(4-tert-butyl-phenyl)-4H-1,2,4-triazol-3-yl)phenyl]-2-methylpyrimidie (DV-46Pym TAZ), SMH-E-10, 1,3,5-tris(5(4-vinylphenyl)pyridin-3-yl)benzene (TV-TmPY) and U-BmPyPB.

[0128] The cross-linking functional group may include at least one of a vinyl group, a vinyl derivative, an oxetane group, a boronic acid group, a trifluorovinyl ether, a benzocyclobutene group, and an epoxide group.

[0129] Preferably, the cross-linking functional group may include a functional group represented by any one of the following Chemical Formulas 3 to 8:

[0130] Chemical formula 3:

[0131]

[0132] Chemical formula 4:

[0133]

[0134] Chemical formula 5:

[0135]

[0136] Chemical formula 6:

[0137]

[0138] Chemical formula 7:

[0139]

[0140] Chemical formula 8:

[0141]

[0142] (In the chemical formulas 3 to 8, R1 each independently includes hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, carbonyl, ether, silyl, siloxane, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, C1-C20 haloalkyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl, any one of a C30 aryloxy group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C7-C30 arylalkyl group, a substituted or unsubstituted C2-C30 alkenyloxy group, a substituted or unsubstituted C8-C30 alkenylaryl group, a substituted or unsubstituted C7-C30 arylalkoxy group, a substituted or unsubstituted C8-C30 arylalkenyl group and a substituted or unsubstituted C2-C20 alkoxycarbonyl group)

[0143] According to an embodiment, the cross-linking functional group may include, but is not limited to, a functional group that undergoes a spontaneous polymerization reaction when stimulated by heat or light irradiation.

[0144] The charge transport composite of the embodiment of the present invention introduces a crosslinking functional group into a curable organic semiconductor, so that a charge transport layer can be formed by a solution process, and the chemical resistance of the charge transport layer can be achieved by irradiating heat or ultraviolet (UV).

[0145] The charge transfer complex of the embodiment of the present invention comprises an organic silicon dioxide precursor that forms an organic silicon (-Si-O-Si-) network structure with a curable organic semiconductor.

[0146] like Figure 1b As shown, the organic silica precursor may include at least one of a bis (Bis) type organic silica precursor, a star (Star) type organic silica precursor and a cyclic (Cyclic) type organic silica precursor.

[0147] In the charge transfer complex of the embodiment of the present invention, if the curing functional group (e.g., crosslinking functional group) introduced into the binary / star / ring-type organic silica precursor is the same, the crosslinking reaction can be carried out in the same manner, but the organic silica precursor can be appropriately selected according to the purpose.

[0148] More specifically, in order to effectively construct an organosilicon (-Si-O-Si-) network by inducing a cross-linking reaction between a curable low-molecular charge transport compound (hole transport compound or electron transport compound) and an organosilicon precursor or precursor molecules, i) the intramolecular cross-linking reaction of the organosilicon precursor must be suppressed as much as possible, and ii) an effective organosilicon (-Si-O-Si-) network structure must be formed with a minimum content of the organosilicon precursor as an insulator.

[0149] In the case of a binary organic silica precursor, if the number of alkyl chains in the bridge chain is 5 or more or a rigid chemical structure such as benzene is introduced, a cross-linking reaction between the organic silica precursor molecules can be effectively induced. In the case of a star / ring organic silica precursor, since the organic silica precursor molecule has 3 or more cross-linking functional groups, a high-density organic silicon (-Si-O-Si-) network structure can be formed with a minimum content.

[0150] For example, the organic silica precursor may include a compound represented by any one of the following Chemical Formulas 9 to 19:

[0151] Chemical formula 9:

[0152]

[0153] (In the chemical formula 9, R' contains 1 to 3 halogen elements and an alkoxy group (-O-(CH2) x -CH3, wherein X is an integer from 0 to 8), and m is an integer from 0 to 20)

[0154] Chemical formula 10:

[0155]

[0156] Chemical formula 11:

[0157]

[0158] Chemical formula 12:

[0159]

[0160] Chemical formula 13:

[0161]

[0162] (In the chemical formula 13, R' contains 1 to 3 halogen elements and an alkoxy group (-O-(CH2) x -CH3, wherein X is an integer from 0 to 8)

[0163] Chemical formula 14:

[0164]

[0165] Chemical formula 15:

[0166]

[0167] Chemical formula 16:

[0168]

[0169] Chemical formula 17:

[0170]

[0171] Chemical formula 18:

[0172]

[0173] Chemical formula 19:

[0174]

[0175] For example, Chemical Formula 9 may include a compound represented by the following Chemical Formula 9-1, and Chemical Formula 13 may include a compound represented by the following Chemical Formula 13-1:

[0176] Chemical formula 9-1:

[0177]

[0178] (In the chemical formula 9-1, m is an integer between 0 and 20)

[0179] Chemical formula 13-1:

[0180]

[0181] The organic silica precursor represented by Chemical Formula 12 is hexavinyldisiloxane, the organic silica precursor represented by Chemical Formula 13 is 1,6-bis(trichlor osilylethyl)dodecafluorohexane, the organic silica precursor represented by Chemical Formula 14 is 3-ethyl-3-[[3-(triethoxysilyl)propoxy]methyl]oxetane, the organic silica precursor represented by Chemical Formula 15 is (3-glycidyloxypropyl)triethoxysilane, the organic silica precursor represented by Chemical Formula 16 is 3-(trimethoxysilyl)propyl methacrylate The organic silica precursor represented by Chemical Formula 17 is 2-(2-ethenylphenyl)ethyl-trimethoxy silane, the organic silica precursor represented by Chemical Formula 18 is 5,6-epoxyhexyltriethoxysilane, and the organic silica precursor represented by Chemical Formula 19 is 2-(methoxycarbonyl)ethyltrimethoxysilane.

[0182] The charge transfer complex of the embodiment of the present invention contains organic silicon (-Si-O-Si-) due to the organic silicon dioxide precursor, and thus may have a network structure including a structure represented by the following Chemical Formula 20:

[0183] Chemical formula 20:

[0184]

[0185] Therefore, a network structure (Silicone Integrated Network) bonded with silicone (-Si-O-Si-) is achieved through a simultaneous or cross-curing reaction between a curable organic semiconductor (a low-molecular charge transport compound with a cross-linking functional group introduced) and an organic silica precursor, thereby enhancing chemical resistance and etching resistance without reducing the optoelectronic properties.

[0186] In particular, the charge transfer complex of the embodiment of the present invention can not only ensure chemical resistance through the network structure (Silicone Integrated Network) bonded with silicone (-Si-O-Si-), but also form a non-volatile blocking layer on the material itself through the chemical reaction between the silicone molecules existing in the network and the dry etching gas, thereby achieving etching resistance at the same time.

[0187] Preferably, the network structure can be a single phase network (SPN) bonded with silicone (Silicone, -Si-O-Si-) or an interpenetrating polymer network (IPN) bonded with silicone (Silicone, -Si-O-Si-), which can be cured simultaneously or selectively according to the cross-linking functional groups contained in the curable organic semiconductor to form the aforementioned two types of silicone (Silicone, -Si-O-Si-) network structures.

[0188] In other words, a highly durable (etching resistance and chemical resistance) charge transport composite can be formed by a mutual cross-linking reaction between a charge transport compound (curable organic semiconductor) into which a cross-linking functional group is introduced and an organic silica precursor.

[0189] For example, when the curable organic semiconductor contains a first cross-linking functional group and the organic silica precursor contains a second cross-linking functional group, if the first cross-linking functional group is the same as the second cross-linking functional group, a simultaneous curing reaction between the curable organic semiconductor and the organic silica precursor is induced, so that the charge transfer complex of the embodiment of the present invention can have a single phase network (SPN) structure bonded with silicone (Silicone, -Si-O-Si-), wherein the curable organic semiconductor-organic silica precursor are both connected to silicone (Silicone, -Si-O-Si-).

[0190] Therefore, an SPN structure bonded with silicone (-Si-O-Si-) can be formed by a simultaneous cross-linking reaction between a curable organic semiconductor and an organic silica precursor.

[0191] For example, when the curable organic semiconductor contains a first cross-linking functional group and the organic silica precursor contains a second cross-linking functional group, if the first cross-linking functional group is different from the second cross-linking functional group, the curing reaction between the curable organic semiconductors containing the same first cross-linking functional group and the selective curing reaction between the organic silica precursors are induced independently, respectively, so that the charge transfer complex of the embodiment of the present invention may have an interpenetrating polymer network (IPN) structure bonded with silicone (-Si-O-Si-), wherein the silicone (-Si-O-Si-) network (organic silica precursor) formed by the curable organic semiconductor and the organic silica precursor is physically entangled.

[0192] Therefore, an IPN bonded with silicone (-Si-O-Si-) can be formed by a cross-linking reaction between curable organic semiconductors and a selective cross-linking reaction between organic silica precursors.

[0193] Furthermore, if the charge transfer complex of the embodiment of the present invention contains an organic silica precursor, an organic silicon (Silicone, -Si-O-Si-) network can be formed even if a small amount of organic silica precursor is added, thereby effectively achieving high durability (chemical resistance and etching resistance). Therefore, depending on the type of cross-linking functional group, the charge transfer complex of the embodiment of the present invention can be prepared by flexibly selecting a structure (SPN) in which the organic silicon (Silicone, -Si-O-Si-) network is directly connected to a curable organic semiconductor or a physically entangled structure (IPN).

[0194] Therefore, depending on the type of cross-linking functional groups, since the charge transport complex of the embodiments of the present invention can be prepared by selecting a structure (SPN) in which a silicone (-Si-O-Si-) network is directly connected to a curable organic semiconductor or a physically entangled structure (IPN), various charge transport compounds (if bonded with a cross-linking functional group, the substance of the charge transport compound is not limited) and organic silica precursors can be used without restriction, the material group range is wide and the material versatility is excellent.

[0195] Furthermore, the charge transfer complex of the embodiment of the present invention ensures chemical resistance and etching resistance through a molecular structure entangled in three dimensions by bonding a network of silicone (-Si-O-Si-), so that high-resolution patterns can be achieved through a photolithography process.

[0196] The charge transfer complex of the embodiment of the present invention simultaneously enhances the chemical resistance and etching resistance of the low-molecular-weight curable organic semiconductor, so that ultra-fine patterns below several microns can be achieved by directly applying photolithography and dry etching, which are ultra-high resolution patterning technologies, to organic light-emitting materials. Therefore, it can be effectively applied to micro displays, head-up displays, and mobile ultra-high resolution OLEDs that require both excellent luminous efficiency and ultra-high resolution.

[0197] Therefore, if the charge transfer complex of the embodiment of the present invention is used, an ultra-high-resolution full-color OLED display with suppressed crosstalk between pixels can be developed, so it can be applied to VR / AR / MR / XR device technology and visual interface technology for the metaverse (five senses enhanced type), etc. Further, the charge transfer complex of the embodiment of the present invention is not limited to the charge transfer layer for OLED, but can be extended to low-molecular organic semiconductors for various electronic devices, so it can also be applied to the field of next-generation organic electronic devices such as neuromorphic devices and image sensors that require high-resolution patterns of organic semiconductors.

[0198] Furthermore, the charge transfer complex of the embodiments of the present invention can not only realize ultra-fine patterns (below 2 μm) based on photolithography and dry etching by ensuring high durability (chemical resistance and etching resistance), but also improve the charge transfer efficiency to the organic light-emitting layer by reducing the energy level difference between organic light-emitting bodies, thereby improving the photoelectric properties of the organic light-emitting device.

[0199] Therefore, the charge transfer complex of the embodiment of the present invention improves the performance of the organic light-emitting device by introducing a charge transfer layer material of an organic silicon (-Si-O-Si-) network using a low-molecular-weight curable organic semiconductor and an organic silicon dioxide precursor, and at the same time, an ultra-fine pattern of the charge transfer layer can be achieved through lithography and dry etching methods as established ultra-high resolution patterning technologies.

[0200] The luminescence intensity and durability of the charge transfer complex of the embodiment of the present invention can be adjusted according to the concentration of the organic silica precursor.

[0201] As the concentration of the organic silica precursor increases, the energy level (HOMO level) of the charge transfer complex moves to the deep level, inducing a decrease in the energy level (HOMO level) difference of the organic light-emitting layer, thereby improving the charge transfer efficiency to the organic light-emitting layer, thereby effectively improving the EQE and luminous efficiency of the organic light-emitting device.

[0202] Furthermore, as the concentration of the organic silica precursor increases, the durability (etching resistance, chemical resistance, etc.) of the charge transport complex improves, thereby making it possible to obtain a more uniform ultrafine pattern than before.

[0203] However, if an excessive amount of an organic silica precursor as an insulating material is included, the charge trapping phenomenon inside the charge transfer complex increases, resulting in a possible decrease in charge transfer efficiency, and the lowest unoccupied molecular orbital energy level (LUMO level) of the charge transfer complex becomes similar to the lowest unoccupied molecular orbital energy level (LUMO level) of the organic light-emitting layer, so the luminous efficiency may actually decrease as the electrons of the organic light-emitting layer move to the charge transfer complex. In addition, if the content of the organic silica precursor is small, sufficient durability cannot be ensured and it is difficult to achieve ultra-fine patterns, so it is necessary to appropriately adjust the content.

[0204] Furthermore, the charge transfer complex according to the embodiment of the present invention may be in the form of a composition.

[0205] The charge transport layer composition according to the embodiment of the present invention comprises a curable organic semiconductor and an organic silicon dioxide precursor.

[0206] Since the charge transport layer composition of the embodiment of the present invention includes the same structural elements as the charge transport complex of the embodiment of the present invention, the description of the same structural elements will be omitted.

[0207] The concentration of the curable organic semiconductor is not limited thereto and can be adjusted according to the type of the cross-linking functional group.

[0208] For example, when an oxetane group is included as a crosslinking functional group, the charge transport layer composition includes 92.87 to 98.60 weight percent of a curable organic semiconductor and 1.40 to 7.13 weight percent of an organic silica precursor relative to the charge transport layer composition.

[0209] The luminescence intensity and durability of the charge transfer complex of the embodiment of the present invention can be adjusted according to the concentration of the organic silica precursor.

[0210] More specifically, the etching resistance of the charge transport layer composition according to the embodiment of the present invention can be adjusted according to the concentration of the organic silicon dioxide precursor.

[0211] For example, as the concentration of the organic silica precursor increases, the amount of organic silicon (Sili cone) per unit volume of the charge transport layer increases, so the etching resistance can be increased. However, due to the insulating properties of the organic silica precursor, the OLED device characteristics decrease as the concentration increases, so the concentration needs to be properly adjusted.

[0212] According to an embodiment, the charge transport layer composition of an embodiment of the present invention may further include a residual amount of an organic solvent.

[0213] The solvent is not particularly limited, but for example, the solvent may include at least one of an alcohol solvent, a halogen-containing solvent, a hydrocarbon solvent, a ketone solvent, an ester solvent, and an amide solvent.

[0214] Examples of alcohol solvents include methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, 1-decanol, 1-undecanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, 1-pentadecanol, 1-hexadecanol, 1-heptadecanol, 1-octadecanol, 1-nonadecanol, 1-eicosanol, 1-heneicosanol, 1-docosanol, 1-tricosanol, 1-tetracosanol, 1-pentacosanol, 1-hexacosanol, 1-heptadecanol, 1-octadecanol, 1-nonadecanol, 1-eicosanol, 1-heneicosanol, 1-cosicosanol, 1-tricosanol, 1-tetracosanol, 1-pentacosanol, 1-hexacosanol, 1-heptacosalanol, 1-octacosanol, 1-1- - At least one of nonaconicotanol, 1-triacontol, polyunsaturated glycol, 2-methyl: 2-methylpropan-1-ol, 3-methyl: 3-methylbutan-1-ol, 2-propanol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, 2-methyl: 2-methylbutan-1-ol, cyclohexanol, 2-methyl: 2-methylpropan-2-ol, 2-methylbutan-2-ol, 2-methylpentan-2-ol, 2-methylhexan-2-ol, 2-methylheptan-2-ol, 3-methyl: 3-methylpentan-3-ol and 3-methyloctan-3-ol.

[0215] The halogen-containing solvent may include at least one of chlorobenzene, chloroform, tetrafluorodibromo ethylene, trichloroethylene, tetrachloroethyl ene, trifluorochloroethylene, 1,2,4-trichlorobenzene, carbon tetrachloride, dichloromethane, dichloroethane and dichlorobenzene.

[0216] The hydrocarbon solvent may include at least one of octane, nonane, decane, undecane, toluene, xylene, ethylbenzene, n-propylbenzene, iso-propylbenzene, mesitylene, n-butylbenzene, sec-butylbenzene, 1-phenylpentane, 2-phenylpentane, 3-phenylpentane, phenylcyclopentane, phenylcyclohexane, 2-ethylbiphenyl and 3-ethylbiphenyl.

[0217] The ether solvent may include at least one of 1,4-dioxane, 1,2-diethoxyethane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, anisole, ethoxybenzene, 3-methylanisole and m-dimethoxybenzene.

[0218] The ketone solvent may include at least one of 2-hexanone, 3-hexanone, cyclohexanone, 2-heptanone, 3-heptanone, 4-heptanone and cycloheptanone.

[0219] The ester solvent may include at least one of butyl acetate, butyl propionate, heptyl butyrate, propylene carbonate, methyl benzoate, ethyl benzoate, 1-propylbenzoate, and 1-butylbenzoate.

[0220] The amide solvent may include at least one of dimethylformamide, dimethylacetamide and N-methylpyrrolidone.

[0221] Figure 2 FIG. 4 is a simplified diagram illustrating a method for patterning a charge transport layer according to an embodiment of the present invention.

[0222] First, in the method for patterning a charge transport layer according to an embodiment of the present invention, step S110 of forming a charge transport layer including a charge transport complex according to an embodiment of the present invention on a substrate 110 is performed.

[0223] The substrate 110 may be an inorganic substrate or an organic substrate.

[0224] The inorganic substrate may include at least one of glass, quartz, Al2O3, SiC, Si, GaAs and InP.

[0225] The organic substrate may include at least one of Kapton foil, polyethyleneterephthalate (PET), polyimide (PI), polydimethylsiloxane (PDMS), polyethersulfone (PES), polyacrylate (PAR), polyetherimide (PEI), polyethylene naphthalate (PEN), polyphenylene sulfide (PPS), polyarylate, polycarbonate (PC), cellulose triacetate (CTA) and cellulose acetate propionate (CAP).

[0226] According to an embodiment, the method of patterning the charge transport layer according to an embodiment of the present invention may include a step of forming a hydrophilic group on the surface of the substrate 110 by performing ultraviolet-ozone treatment.

[0227] The ultraviolet-ozone treatment may improve surface adhesion between the substrate 110 and the charge transport layer 120 formed in a subsequent process by forming a hydrophilic group on the surface of the substrate 110 .

[0228] The hydrophilic group may be at least one of an -OH group, an -OOH group and a -OO- group. Preferably, the hydrophilic group may be an -OH group.

[0229] According to an embodiment, the patterning method of the charge transport layer of the embodiment of the present invention may also include the step of forming a multilayer film between the substrate 110 and the charge transport layer 120, and the multilayer film may include a first electrode, a hole injection layer, a hole transport layer, a hole blocking layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer and at least one of the second electrode.

[0230] The charge transport layer 120 may be formed by coating a coating solution including the charge transport complex according to an embodiment of the present invention.

[0231] The coating solution may include a charge transfer complex and a solvent.

[0232] Since the charge transfer complex and the solvent contain Figure 1a and Figure 1b The charge transfer complex of the embodiment of the present invention described in the foregoing description has the same structural elements, so the description of the same structural elements will be omitted.

[0233] The charge transfer complex may include a silicone (-Si-O-Si-) network structure, and the silicone (-Si-O-Si-) network structure may be any one of a single phase network (SPN) bonded with silicone (-Si-O-Si-) and an interpenetrating polymer network (IPN) bonded with silicone (-Si-O-Si-).

[0234] The charge transport layer 120 may be coated by at least one of spin coating, flexographic coating, roller coating, slot and spin coating, slot coating, spray coating, roll-to-roll, rod coating, dip coating, casting, extrusion coating, blade coating, gravure coating, and doctor coating.

[0235] According to an embodiment, in the method for patterning a charge transport layer of the embodiment of the present invention, the step S110 of forming a charge transport layer may further include the step of forming at least two sub-charge transport layers having different concentrations of an organic silicon dioxide precursor on the substrate 110 .

[0236] For example, the step S110 of forming the charge transport layer may include a step S111 of forming a first sub-charge transport layer on the substrate 110 and a step S112 of forming a second sub-charge transport layer on the first sub-charge transport layer.

[0237] The first sub-charge transport layer and the second sub-charge transport layer have different concentrations of organic silicon dioxide precursors, and the concentration of the organic silicon dioxide precursor of the second sub-charge transport layer can be higher than the concentration of the organic silicon dioxide precursor of the first sub-charge transport layer. In this case, the first sub-charge transport layer is a charge transport layer in contact with the electrode, and the second sub-charge transport layer is a charge transport layer in contact with the organic light-emitting layer.

[0238] Since the luminous intensity and durability of the charge transport layer can be adjusted according to the concentration of the organic silica precursor, the energy level (HOMO level) difference between the first sub-charge transport layer, the second sub-charge transport layer and the organic light-emitting layer is reduced by stacking a second sub-charge transport layer having a higher concentration of organic silica precursor than the first sub-charge transport layer on the upper part of the first sub-charge transport layer, thereby improving the charge transfer efficiency and the luminous efficiency. At the same time, since the concentration of the organic silica precursor in the second sub-charge transport layer is high, it can provide better durability in the subsequent solution process.

[0239] Then, in the method for patterning a charge transport layer according to the embodiment of the present invention, a step S120 of forming a photoresist 130 on the charge transport layer 120 is performed.

[0240] In step S120 , a photoresist solution may be coated on the charge transport layer 120 , and then the substrate 110 coated with the photoresist solution may be heated and dried (pre-baked) or dried under reduced pressure and then heated to form the photoresist 130 .

[0241] The volatile components such as solvent in the substrate 110 coated with the photoresist 130 can be volatilized by heating. The heating temperature can be a relatively low temperature of 70° C. to 100° C., and heating drying (pre-baking) can be performed at 110° C. for 2 minutes.

[0242] The photoresist 130 may be coated by at least one of spin coating, flex coating, roller coating, slot and spin coating, slot coating, spray coating, roll-to-roll, rod coating, dip coating, casting, extrusion coating, blade coating, gravure coating, and doctor coating.

[0243] Then, in the method for patterning a charge transport layer according to the embodiment of the present invention, a step S130 of patterning the photoresist 130 to form a photoresist pattern 131 is performed.

[0244] In step S130, the photoresist 130 may be exposed using a mask engraved with a target pattern, and then the exposed photoresist 130 may be subjected to a development process using a developer solution to form a photoresist pattern 131. For example, the exposure may be performed by irradiating ultraviolet light using a mask for forming a target pattern. At this time, when the ultraviolet light is irradiated to the photoresist 130, the chemical structure of the photoresist at the portion irradiated by the ultraviolet light changes and can be easily dissolved in the developer.

[0245] Then, in the method for patterning the charge transport layer according to the embodiment of the present invention, step S140 of dry-etching the charge transport layer 120 using the photoresist pattern 131 as an etching mask to form the charge transport layer pattern 121 is performed.

[0246] The charge transport layer pattern 121 may be formed by performing etching and washing processes on the charge transport layer 120 using an etching gas.

[0247] The etching gas may include at least one of CF4, Cl2, BCl3, HCl, HBr, NF3, and SF6. According to an embodiment, the etching gas may use a mixed gas further including at least one of Ar, He, O2, and H2.

[0248] In particular, in step S140 of dry-etching the charge transport layer 120 using the photoresist pattern 131 as an etching mask to form a charge transport layer pattern 121, when the charge transport layer 120 is exposed to an etching gas, the charge transport layer 120 is etched to form the charge transport layer pattern 121, and at the same time, a non-volatile blocking layer 140 (blocking layer) can be formed on the side of the charge transport layer pattern 121 through the silicone (-Si-O-Si-) network structure of the charge transport complex.

[0249] The non-volatile barrier layer 140 may include at least one of SixOy and SixOyFz (x, y, and z are integers of 1 to 4).

[0250] For example, since the non-volatile barrier layer 140 is formed by the reaction between the material to be etched and the etching gas or gas radicals, the chemical reaction amount can be adjusted according to the material to be etched and the etching gas or gas radicals, for example, it can be SiO2, but not limited thereto.

[0251] More specifically, since the charge transport layer 120 itself can form a non-volatile blocking layer 140 through a chemical reaction between embedded organic silicon (-Si-O-Si-) molecules and a dry etching gas (e.g., Ar / O2 or CF4), an anisotropic ultra-fine pattern can be achieved based on photolithography and dry etching.

[0252] For example, SixOy can be formed by the reaction between O* (radicals) generated from O2 gas and Si or Si-O (SiO+O * →SixOy or SiO+O * →SixOy), SixOyFz can be generated from CF4 gas by * (free radicals) react with Si-O to form (Si-O+F * →SixOyFz).

[0253] Therefore, the patterning method of the charge transport layer in an embodiment of the present invention forms an organic silicon (-Si-O-Si-) network by introducing an organic silicon dioxide precursor into a low-molecular curable organic semiconductor, thereby ensuring both chemical resistance and etching resistance, and can achieve ultra-high resolution patterns (below 2 μm) through photolithography and dry etching.

[0254] Moreover, the patterning method of the charge transport layer of the embodiment of the present invention not only prevents the crosstalk between pixels that may occur in an ultra-high-resolution full-color OLED display, but also can induce the improvement of the characteristics of the OLED device by aligning the energy level (HOMO level) of the charge transport layer, thereby achieving a charge transport composite silicone (-Si-O-Si-) network (SPN and IPN) that simultaneously ensures high luminous efficiency and high durability, has excellent luminous properties, and can achieve ultra-fine patterns through general photolithography and dry etching.

[0255] In other words, the patterning method of the charge transfer layer in the embodiment of the present invention is to use ultra-high resolution patterning technology of a photolithography customized charge transfer complex and a non-volatile blocking layer 140, and to manufacture an ultra-high resolution full-color OLED micro-display device, which can be applied as a vision-based perceptual interface platform technology to achieve ultra-realistic and immersive virtual and augmented reality.

[0256] Finally, the charge transport layer patterning method according to the embodiment of the present invention includes a step S150 of removing the photoresist pattern 131 .

[0257] In step S150 , the photoresist pattern 131 is removed by a developing process, so that a charge transport layer pattern 121 may be formed on the substrate 110 .

[0258] The size (width) of the charge transport layer pattern 121 may be hundreds of nanometers to hundreds of micrometers. For example, the size of the charge transport layer pattern 121 may be 10 nm to 1000 μm, but is not limited thereto, and the size of the charge transport layer pattern 121 may be adjusted in various ways according to the size and purpose of the applied OLED display.

[0259] Figure 3a A simplified diagram is shown for comparing a conventional wet etching process for a hole transport layer with a dry etching process for a patterning method for a charge transport layer according to an embodiment of the present invention.

[0260] In the case of the prior art of improving durability by introducing a cross-linking functional group into the hole transport layer, since the chemical resistance of the hole transport layer material to solvents can only be simply ensured, photolithography and dry etching cannot be applied to achieve ultra-high resolution patterns.

[0261] In addition, there are also reports of cases where high-resolution patterns are achieved by directly applying photolithography to organic electronic materials, but this is limited to polymer materials rather than low-molecular organic semiconductors with high industrial applicability. Moreover, since it is mainly achieved through a wet etching process rather than a dry etching process, there are limitations in terms of low pattern density and uniformity.

[0262] Reference Figure 3a In the case of a wet etching process, there are limitations in terms of low pattern density and uniformity due to isotropic etching. In addition, over-etching may result in an undercut phenomenon in which the etched area is expanded.

[0263] In the case of dry etching process, due to its anisotropy, the etching speed in the vertical direction is faster, but as the depth of the etched pattern increases, the lateral direction is also etched at a lower speed, which limits the realization of anisotropic patterns. As a solution to the above example, there is a Bosch process, which realizes high aspect ratio etching by alternately repeating the passivation process and the etching process for forming a barrier layer during dry etching. However, this process has the problem of a scalloping effect (scalloping effect) in which the side of the pattern forms a sawtooth shape and requires a long process time.

[0264] Therefore, there is a problem that the pattern accuracy, pattern density, and uniformity of the charge transport layer pattern 121 are reduced.

[0265] However, in the patterning method of the charge transport layer in the embodiment of the present invention, since the charge transport layer 120 includes a charge transport complex having a network structure bonded with silicone (-Si-O-Si-), the charge transport layer 120 itself reacts with the etching gas during the dry etching process to form a non-volatile blocking layer 140 on the side of the charge transport layer pattern 121 for protecting the charge transport layer pattern 121, thereby improving the pattern accuracy, pattern density and uniformity.

[0266] Therefore, the patterning method of the charge transport layer of the embodiment of the present invention realizes a charge transport complex silicone (-Si-O-Si-) network (SPN and IPN) that ensures both high luminous efficiency and high durability, thereby maintaining the original excellent luminous properties of OLED and achieving ultra-fine patterns through general lithography and dry etching.

[0267] Figure 3b A simplified diagram is shown for comparing a conventional hole transport layer and a charge transport layer pattern obtained by a charge transport layer patterning method according to an embodiment of the present invention.

[0268] In the case of the existing hole transport layer, as the pixel density (minimum 300 ppi) increases, crosstalk will occur, resulting in a decrease in color purity, sharpness and gamut area.

[0269] More specifically, since the second electrode (e.g., cathode) is usually a common electrode and the hole transport layer is connected to a plurality of pixels (e.g., first pixel, second pixel), when the first pixel (active pixel) emits light, current flows to the second electrode through the hole transport layer and the organic light-emitting layer, causing the second pixel (passive pixel) to also emit light. In this way, crosstalk occurs when adjacent pixels emit light.

[0270] Therefore, if the pixel density of an organic light-emitting device is increased by ultra-fine patterns, crosstalk may become more severe and the light-emitting characteristics of the device may be rapidly degraded.

[0271] However, in the organic light-emitting device of the embodiment of the present invention, the hole transport layer is patterned by the patterning method of the charge transport layer of the embodiment of the present invention. Therefore, when the first pixel (active pixel) emits light through the high-resolution patterned charge transfer complex containing a silicone (-Si-O-Si-) network (SPN and IPN) structure, the current moves to the hole transport layer and the organic light-emitting layer of the second pixel (passive pixel), thereby preventing the second pixel (passive pixel) from emitting light together and preventing crosstalk.

[0272] Figure 4 FIG. 4 is a cross-sectional view showing an organic light emitting device according to an embodiment of the present invention.

[0273] The organic light-emitting device of the embodiment of the present invention may include: a first electrode 210, formed on a substrate; an organic light-emitting layer 230, formed on the first electrode 210; a second electrode 250, formed on the organic light-emitting layer 230; and a charge transport layer (at least one of a hole transport layer 220 and an electron transport layer 240), formed at least one of the interfaces between the first electrode 210 and the organic light-emitting layer 230 and between the organic light-emitting layer 230 and the second electrode 250, and including a charge transport complex of the embodiment of the present invention.

[0274] Therefore, the organic light-emitting device of the embodiment of the present invention contains the charge transfer complex of the embodiment of the present invention only in the hole transport layer 220, or contains the charge transfer complex of the embodiment of the present invention only in the electron transport layer 240, or both the hole transport layer 220 and the electron transport layer 240 may contain the charge transfer complex of the embodiment of the present invention.

[0275] If the organic light-emitting device of the embodiment of the present invention contains the charge transport complex of the embodiment of the present invention only in the hole transport layer 220 or the electron transport layer 240, the hole transport layer 220 or the electron transport layer 240 not containing the charge transport complex of the embodiment of the present invention may use a conventional hole transport layer 220 or electron transport layer 240 used in the art.

[0276] Refer to the following Figure 4 , describes an organic light-emitting device of an embodiment of the present invention in which the charge transfer complex of an embodiment of the present invention is included in the hole transport layer 220, but the organic light-emitting device of an embodiment of the present invention is not limited to this, and the charge transfer complex of an embodiment of the present invention can have the same structure and effect even if it is included in the electron transport layer 240.

[0277] In an organic light-emitting device, electrons (Electron) and holes (Hole) injected through the cathode (Cathode) and the anode (Anode) recombine in the organic light-emitting layer 230. At this time, the generated excitons (Exciton) fall to the ground state (Ground State), generating the principle of emitting visible light corresponding to the energy gap of the material in the organic light-emitting layer 230. Therefore, blue, green, and red light-emitting devices can be realized depending on how the organic light-emitting layer 230 is formed.

[0278] The organic light-emitting device of the embodiment of the present invention includes: a first electrode 210 formed on a substrate; a hole transport layer 220 formed on the first electrode 210 and containing a charge transport complex of the embodiment of the present invention; an organic light-emitting layer 230 formed on the hole transport layer 220; an electron transport layer 240 formed on the organic light-emitting layer 230; and a second electrode 250 formed on the electron transport layer 240.

[0279] Therefore, the organic light-emitting device of the embodiment of the present invention can simultaneously ensure chemical resistance to solvents and resistance to dry etching gases by using a hole transport layer 220 containing a charge transport complex of the embodiment of the present invention, and thus, can achieve a several micron level by directly applying photolithography and dry etching methods to the hole transport layer 220 material.

[0280] Furthermore, the organic light-emitting device of the embodiment of the present invention not only realizes an ultra-high resolution pattern of the hole transport layer 220 by using the hole transport layer 220 comprising the charge transport complex of the embodiment of the present invention, but also improves the charge transfer efficiency by reducing the energy level (HO MO level) difference between the organic light-emitting layer 230 (organic light-emitting body) and the hole transport layer 220 (charge transfer complex), thereby effectively improving the EQE and luminous efficiency of the OLED device used for the solution process.

[0281] First, the organic light emitting device according to the embodiment of the present invention includes a first electrode 210 formed on a substrate.

[0282] According to an embodiment, the first electrode 210 may be formed on a substrate, or the first electrode 210 may function as both an electrode and a substrate.

[0283] The substrate may use a conventional substrate used in an organic light-emitting device, but is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance.

[0284] The first electrode 210 may be patterned in units of pixels to inject holes into the organic light emitting layer 230 . For example, the first electrode 210 may be an anode.

[0285] The first electrode 210 may be connected to one of a source electrode and a drain electrode of the thin film transistor to receive a driving current applied from the thin film transistor.

[0286] The first electrode 210 may be made of a known electrode material used in an organic light-emitting device. Preferably, the first electrode 210 may include at least one of gold (Au), palladium (Pd), platinum (Pt), indium tin oxide (ITO), aluminum zinc oxide (AZO), fluorine-doped tin oxide (FTO), indium zinc oxide (IZO), zinc oxide (ZnO), carbon nanotubes (CNTs), graphene, polyethylene dioxythiophene: polystyrene sulfonic acid (PEDOT:PSS) and silver nanowires (AgNWs).

[0287] More preferably, the first electrode 210 may include indium tin oxide (ITO) as a transparent electrode having a large work function to allow holes to be easily injected into the highest occupied molecular orbital (HOMO) energy level of the organic light emitting layer 230 .

[0288] The organic light emitting device according to the embodiment of the present invention includes a hole transport layer 220 including the charge transport complex according to the embodiment of the present invention.

[0289] The hole transport layer 220 may include a charge transport complex according to an embodiment of the present invention, and may be a charge transport layer pattern patterned by the charge transport layer patterning method according to an embodiment of the present invention.

[0290] Since the hole transport layer 220 includes the same structural elements as the charge transport complex and the patterning method of the charge transport layer according to the embodiment of the present invention, the description of the same structural elements will be omitted.

[0291] The charge transport layer may include at least two sub-charge transport layers having different concentrations of the organic silicon dioxide precursor.

[0292] The at least two sub-charge transport layers having different concentrations may have a concentration gradient such that the concentration of the organic silicon dioxide precursor increases in a direction from the electrode (the first electrode 210 ) to the organic light emitting layer 230 .

[0293] For example, when the charge transport complex of the embodiment of the present invention is included in the hole transport layer 220, the hole transport layer 220 includes a first sub-charge transport layer and a second sub-charge transport layer between the first electrode 210 and the organic light-emitting layer 230, and the concentration of the organic silicon dioxide precursor of the second sub-charge transport layer can be higher than the concentration of the organic silicon dioxide precursor of the first sub-charge transport layer. In this case, the first sub-charge transport layer is a charge transport layer in contact with the first electrode 210, and the second sub-charge transport layer is a charge transport layer in contact with the organic light-emitting layer 230.

[0294] If the hole transport layer 220 is formed as a multilayer, the charge injection efficiency may be improved by aligning the energy level (HOMO level) of the hole transport layer 220 with the energy level (HOMO level) of the organic light emitting layer 230 .

[0295] In other words, as the content of the organic silica precursor increases, the energy level (HOMO level) of the charge transport complex moves to the deep level, and therefore, the alignment of the energy level (HOMO level) can be improved by adjusting the content of the organic silica precursor contained in the first sub-charge transport layer and the second sub-charge transport layer (the content of the organic silica precursor in the first sub-charge transport layer < the content of the organic silica precursor in the second sub-charge transport layer). Therefore, the concentration of the organic silica precursor contained in the first sub-charge transport layer and the second sub-charge transport layer is not particularly limited, but the concentration of the organic silica precursor in the second sub-charge transport layer should be higher than the concentration of the organic silica precursor in the first sub-charge transport layer.

[0296] According to an embodiment, the hole transport layer 220 may include at least one of a hole injection layer and an electron blocking layer.

[0297] The hole injection layer is a layer that smoothly injects holes from the anode of the first electrode 210 into the organic light-emitting layer 230, and has a single layer or a multilayer structure of more than two layers. The hole injection material is a material that can well receive the holes injected from the first electrode 210 at a low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode 210 material and the HOMO of the surrounding organic layer.

[0298] For example, the hole injection material includes metal porphyrine, oligothiophene, aromatic amine series organic matter, hexacyanohexaazatriphenylene series organic matter, quinacridone series organic matter, perylene series organic matter, anthraquinone, polyaniline and multi-component compound series conductive polymers, but is not limited thereto.

[0299] The electron blocking layer is a layer that blocks electrons from reaching the first electrode 210 and can be generally formed under the same conditions as the electron injection layer. For example, the electron blocking layer includes HT-B mCP, etc., but is not limited thereto.

[0300] The organic light emitting device according to the embodiment of the present invention includes an organic light emitting layer 230 formed on a hole transport layer 220 .

[0301] The organic light emitting layer 230 is a layer that generates excitons by combining holes injected from the first electrode 210 and passing through the hole transport layer 220 with electrons injected from the second electrode 250 and passing through the electron transport layer 240, and emits light when the generated excitons change from an excited state to a ground state, and may be composed of a single layer or a plurality of layers.

[0302] The organic light emitting layer 230 may include at least one of a green light emitting layer, a red light emitting layer, a blue light emitting layer, and a white light emitting layer.

[0303] According to the embodiment, the organic light emitting layer 230 may emit phosphorescent light through triplet excitons, and the phosphorescent light emitting layer 230 may have a much higher quantum efficiency than fluorescent light emitting, so the phosphorescent organic light emitting device may improve the efficiency of the organic electroluminescent device.

[0304] Also, the organic light emitting layer 230 may improve the internal quantum efficiency of the organic light emitting device by using a phosphorescent substance that emits phosphorescent light through triplet excitons, thereby improving the efficiency of the organic light emitting device.

[0305] The material forming the organic light emitting layer 230 is not particularly limited. More specifically, the organic light emitting layer 230 may include at least one of a blue material, a green material, and a red material, wherein the blue material includes oxadiazole dimer dyes (Bis-DAPOXP), spiro compounds (Spiro-DPVBi, Spiro-6P), triarylamine compounds, bis (styryl) amine (DPVBi, DSA), 4,4'-bis (9-ethyl-3-carbazole vinylidene) -1,1'-biphenyl (BCzVBi), perylene (perylene) ene), 2,5,8,11-tetra-tert-butylperylene (TPBe), 9H-carbazole-3,3'-(1,4-phenylene-di-2,1-ethylene-diyl)bis[9-ethyl-(9C)] (BCzVB), 4,4-bis[4-(di-p-toluylamino)phenylvinyl]biphenyl (DPAVBi), 4-(di-p-toluylamino)-4'-[(di-p-toluylamino)phenylvinyl]stilbene (DPAVB), 4,4'-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi) and bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium III (FIrPic), and the green substance includes at least one of 3-(2-benzothiazolyl)-7-(diethylamino)coumarin (Coumarin 6), 2,3,6,7-tetrahydro-1,1,7,7,-tetramethyl-1H,5H,11H-10-(2-benzothiazolyl)quinolizine [9,9a,1gh] coumarin (C545T), N,N'-dimethylquinacridone (DMQA) and tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), the red substance includes tetraphenylnaphthacene (Tetraphenylnaphthacene) (Rubrene), tris (1-phenylisoquinoline) iridium (III) (Ir (piq) 3), bis (2-benzo [b] thiophene-2-yl-pyridine) ( acetylacetonate) iridium(III) (Ir(btp)2(acac)), tris(dibenzoylmethane)phenanthroline europium(III) (Eu(dbm)3(phen)), tris[4,4'-di-tert-butyl-(2,2')-bipyridyl]ruthenium(III) complex (Ru(dtb-bpy)3*2(PF6)), DCM1, DCM2, Eu(thenoyltrifluoroacetone)3(Eu(TTA)3) and butyl-6-(1,1,7,7-tetramethyljuradol-9-enyl)-4H-pyran) ( ...7-tetramethyljulolidyl-9-enyl)-4H-pyran: DCJTB).

[0306] Furthermore, the organic light emitting layer 230 may include a polymer and a nitrogen-containing aromatic compound, but is not limited thereto. The polymer is a phenylene, phenylene vinylene, thiophene, fluorene, and spiro-fluorene polymer.

[0307] Furthermore, the organic light emitting layer 230 may further include a light emitting dopant in a light emitting layer host.

[0308] The material of the fluorescent light-emitting host may include tris(8-hydroxyquinoline)aluminum (Alq3), 9,10-di(naphthyl-2-yl)anthracene (AN D), 3-tert-butyl-9,10-di(naphthyl-2-yl)anthracene (TBADN), 4,4'-bis(2,2-diphenyl-vinyl-1-yl)-4,4'-dimethylphenyl (DPVBi), tert-(9,9-diarylfluorene) (TDAF), 2-(9,9'-spirobifluorene-2-yl)-9,9'-spirobifluorene (BSDF), 2,7-bis(9,9'-spirobifluorene-2-yl)-9,9'-spirobifluorene (TSDF), bis(9,9-diarylfluorene) (BDAF) and 4,4'-bis(2,2-diphenyl-vinyl-1-yl)-4,4'-di(tert-butyl)phenyl (p-TDPVBi), and the material of the phosphorescent host may include at least one of 1,3-bis(carbazole-9-yl) benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (tCP), 4,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 4,4'-bis(9-carbazol-2,2'-dimethylbiphenyl (CBDP), 4,4'-bis(carbazol-9-yl)-9,9-dimethyl-fluorene (DMFL-CBP), 4,4'-bis(carbazol-9-yl)-9,9-bis(9-phenyl-9H-carbazol)fluorene (FL-4CBP), 4,4'-bis(carbazol-9-yl)-9,9-dimethyltoluene-ylfluorene (DPFL-CBP) and 9,9-bis(9-phenyl-9H-carbazol)fluorene (FL-2CBP).

[0309] The dopant may include at least one of a fluorescent dopant and a phosphorescent dopant.

[0310] For example, the phosphorescent dopant may include an organic metal compound, the metal including one of iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thorium (Tm), rhodium (Rh) and copper (Cu). The fluorescent dopant may include at least one of the following DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6 and C545T.

[0311] The organic light emitting device according to the embodiment of the present invention includes an electron transport layer 240 formed on the organic light emitting layer 230 .

[0312] The electron transport layer 240 is a layer that transports electrons to the organic light emitting layer 230 . The electron transport material is a material that can well receive electrons injected from the second electrode 250 and transport them to the organic light emitting layer 230 . Materials with high electron mobility are suitable.

[0313] If the electron transport layer 240 includes the charge transport complex according to an embodiment of the present invention, the electron transport layer 240 may include the same structural elements as the charge transport complex according to an embodiment of the present invention.

[0314] Furthermore, the electron transport layer 240 may include at least two sub-charge transport layers having different concentrations, and the at least two sub-charge transport layers having different concentrations may have a concentration gradient so that the concentration of the organic silicon dioxide precursor increases along a direction from the electrode (the second electrode 250 ) to the organic light-emitting layer 230 .

[0315] For example, when the charge transfer complex of an embodiment of the present invention is included in the electron transport layer 240, the electron transport layer 240 includes a third sub-charge transport layer and a fourth sub-charge transport layer between the second electrode 250 and the organic light-emitting layer 230, and the concentration of the organic silicon dioxide precursor of the fourth sub-charge transport layer can be higher than the concentration of the organic silicon dioxide precursor of the third sub-charge transport layer.

[0316] At this time, the third sub-charge transport layer is a charge transport layer in contact with the second electrode 250 , and the fourth sub-charge transport layer is a charge transport layer in contact with the organic light emitting layer 230 .

[0317] When the electron transport layer 240 does not contain the charge transport complex of the embodiment of the present invention, for example, the electron transport layer 240 may contain 2,2′,2″-(1,3,5-benzenetriyl)-tris(1-phenyl-1-H-benzimidazole) (2,2′,2″-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole, TPBi), tris(8-hydroxyquinoline)aluminum (Tris(8-hydroxyquinoline)Aluminum, Alq3), phenyl-C61-butyric acidmethyl ester (Phenyl-C61-butyric acidmethyl ester, PCBM), 3-(4-biphenyl)-4-phenyl-5-(4-tertbutylphenyl)-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (BPhen), Bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum ( phenylphenoxy)aluminum, BAlq), diphenylphosphineoxide-4-(triphenylsilyl)phenyl, TSPO1, bis-4,6-(3,5-di-4-pyridylphenyl)-2-methylpyrimidine, B4PyMPM, and two pyridine-containing triphenylbenzene derivatives of 1,3,5-tris(3-pyridin-3-yl-phenyl)benzene. Pyridine-containing triphenylbenzene derivativesof 1,3,5-tri(m-pyrid-3-yl-phenyl)benzene, TmPyPB), tris-[3-(3-pyridyl)mesityl]borane, 3TPYMB), 1,3,5-tri(p-pyridin-3-yl-phenyl)benzene, TpPyPB), 1,3,5-tris[3,5-bis(3-pyridyl)phenyl]benzene, 1,3,5-tris[3,5-bis(3-pyridyl)phenyl]benzene, 1,3,5-tris[3,5-bis(3-pyridyl)phenyl]At least one of 5-bis(3-pyridinyl)phenyl]benzene (TPPB) and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP).

[0318] According to an embodiment, the electron transport layer 240 may include at least one of an electron injection layer and a hole blocking layer.

[0319] The electron injection layer is a layer that injects electrons from the second electrode 250, has the ability to transport electrons, and has excellent electron injection effects from the second electrode 250 and excellent electron injection effects for the organic light-emitting layer 230. The electron injection layer preferably contains a compound that prevents excitons generated in the organic light-emitting layer 230 from moving to the hole injection layer and has excellent thin film forming ability. For example, the electron injection layer includes fluorenone, anthraquinone dimethane, diphenoquinone, dioxythiopyran, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but is not limited thereto.

[0320] The hole blocking layer is a layer that blocks holes from reaching the second electrode 250 and can be formed under the same conditions as the hole injection layer. For example, the hole blocking layer includes oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

[0321] The organic light emitting device according to the embodiment of the present invention includes a second electrode 250 formed on an electron transport layer 240 , and the electron transport layer 240 is formed on a substrate.

[0322] For example, the second electrode 250 may be a cathode. The second electrodes 250 may be commonly connected to a power supply voltage to inject electrons into the organic light emitting layer 230 .

[0323] The second electrode 250 may be made of a known electrode material used in an organic light-emitting device. Preferably, the second electrode 250 may include at least one of lithium fluoride / aluminum (LiF / Al), aluminum (Al), silver (Ag), gold (Au), copper (Cu), palladium (Pd), platinum (Pt), magnesium (Mg), magnesium silver (Mg:Ag), ytterbium (Yb), and calcium (Ca).

[0324] More preferably, the second electrode 250 can use a metal electrode with a low work function and excellent internal reflectivity to easily inject electrons into the lowest unoccupied molecular orbital (LUMO) energy level of the organic light-emitting layer 230, and the second electrode 250 can include at least one of lithium fluoride / aluminum (LiF / Al), aluminum (Al), silver (Ag), copper (Cu), palladium (Pd), magnesium (Mg), magnesium silver (Mg:Ag) and ytterbium (Yb).

[0325] The first electrode 210 and the second electrode 250 are electrically separated from each other and provide power to the organic light emitting device. In addition, the first electrode 210 and the second electrode 250 can increase light efficiency by reflecting light generated from the organic light emitting device and can also discharge heat generated from the organic light emitting device to the outside.

[0326] Example 1: SPN+QUPD

[0327] In a 4 ml vial, QUPD (curable organic semiconductor) was dissolved in chlorobenzene solvent and a solution was prepared by stirring for 6 hours under a nitrogen environment. 3-ethyl-3-[[3-(triethoxysilyl)propoxy]methyl]oxetane (organic silica precursor) was added to the prepared solution at 1.40 to 6.07 weight percent (4 mol% to 16 mol%) relative to the curable organic semiconductor, and then stirred for 1 hour under a nitrogen environment. The stirred solution was completely coated on a substrate coated with PEDOT:PSS (AI4083), and then a hole transport layer film was formed by spin coating (2000 rpm, 60 seconds).

[0328] The formed film was heat treated at 180°C for 3 hours under a nitrogen environment to carry out an oxetane crosslinking reaction and an organic silicon network formation reaction between the curable organic semiconductor and the organic silicon dioxide precursor, and finally prepare a hole transport layer composition bonded with silicone (Silicone, -Si-O-Si-).

[0329] Comparative Example: QUPD

[0330] In a 4 ml vial, QUPD (curable organic semiconductor) was dissolved in chlorobenzene solvent and stirred for 6 hours under a nitrogen atmosphere to prepare a solution. The prepared solution was completely coated on a substrate coated with PEDOT:PSS (AI4083), and then a hole transport layer thin film was formed by spin coating (2000 rpm, 60 seconds).

[0331] Example 2-1: 4 mol% SPN+QUPD

[0332] After coating PEDOT:PSS (Al4083) onto the entire ITO (anode) substrate, a thin film was prepared by spin coating (4000 rpm, 60 seconds), and then a charge injection layer was formed by heat treatment at 120° C. for 1 hour.

[0333] In a 4 ml vial, QUPD (curable organic semiconductor) was dissolved in chlorobenzene solvent and stirred for 6 hours under a nitrogen environment to prepare a solution. 3-ethyl-3-[[3-(triethoxysilyl)propoxy]methyl]oxetane (organic silica precursor) was added at 4 mol% relative to the curable organic semiconductor to the prepared solution, and then stirred for 1 hour under a nitrogen environment. The stirred solution was completely coated on a substrate coated with PEDOT:PSS (AI4083), and then a hole transport layer film was formed by spin coating (2000 rpm, 60 seconds).

[0334] The formed film was heat treated at 180°C for 3 hours in a nitrogen environment to perform an oxetane crosslinking reaction and an organic silicon network formation reaction between the curable organic semiconductor and the organic silicon dioxide precursor, and finally prepare a hole transport layer bonded with silicone (Silicone, -Si-O-Si-).

[0335] The host (CBP)-dopant (Ir(ppy)3) mixed solution is applied to the entire formed hole transport layer, and a thin film is prepared by spin coating (2000rpm, 60 seconds), and then an organic light-emitting layer is formed by heat treatment at 180°C for 30 minutes. 2,2′,2"-(1,3,5-benzenetriyl)-tris(1-phenyl-1-H-benzimidazole) (2,2′,2"-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), TPBi) as a sub-transport layer and LiF:Al / Al as a cathode electrode are deposited on the formed organic light-emitting layer to finally manufacture an organic light-emitting diode device.

[0336] Example 2-2: 8 mol% SPN+QUPD

[0337] The same method as in Example 2-1 was used except that the amount of the organic silica precursor added in Example 2-1 was changed to 8 mol %.

[0338] Example 2-3: 16 mol% SPN+QUPD

[0339] The same method as in Example 2-1 was used except that the amount of the organic silica precursor added in Example 2-1 was changed to 16 mol %.

[0340] Example 3: Bilayer

[0341] After coating PEDOT:PSS (Al4083) onto the entire ITO (anode) substrate, a thin film was prepared by spin coating (4000 rpm, 60 seconds), and then a charge injection layer was formed by heat treatment at 120° C. for 1 hour. A mixed solution of N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine (QUPD) and an organic silica precursor (QUPD-oxetane precursor) (the content of the organic silica precursor is 4 mol% to 1.4 weight percentage relative to the weight of the main body) is used as a cross-linked low molecular semiconductor material and a thin film is prepared by spin coating (2000 rpm, 60 seconds) under a nitrogen environment, and then heat treated at 180°C for 3 hours to form a cross-linked first charge transport layer on the charge injection layer. A mixed solution of QUPD and an organic silica precursor (QUPD-oxetane precursor) (the content of the organic silica precursor was 16 mol% to 6 weight percent relative to the weight of the host) was used and a thin film was prepared by spin coating (2000 rpm, 60 seconds) under a nitrogen environment, and then heat treated at 180°C for 3 hours to form a cross-linked second charge transport layer on the formed first charge transport layer. A host (CBP)-dopant (Ir(ppy)3) solution (host: 95 weight percent, dopant: 5 weight) was applied to the entire formed second charge transport layer, and an organic light-emitting layer thin film was prepared by spin coating (2000 rpm, 60 seconds). 2,2′,2"-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi) as a sub-transport layer and LiF:Al / Al as a cathode electrode are deposited on the formed organic light-emitting layer to finally manufacture an organic light-emitting diode device.

[0342] Figure 5 1 is a graph showing the results of Fourier-transform infrared spectroscopy (FT-IR) analysis of the cross-linking reaction of the charge transport complex of Example 1.

[0343] Reference Figure 5 It can be seen that in the charge transfer composite of Example 1, a silicone-oxetane organic silica precursor is introduced into the curable low molecular weight organic semiconductor (QUPD) material, thereby forming a silicone cone network structure (oxetane (978cm)) through the CROP reaction of oxetane (Oxetane) and the condensation reaction of silicone (Silicone). -1 )↓ and ether (1107cm -1 )↑).

[0344] Figure 6 Graphs showing the results of Time-of-Flight Secondary Ion Mass Spectrometry (ToF-SIMS) analysis of a hole transport layer comprising QUPD (X-QUPD) and the charge transport complex of Example 1 (SPN-QUPD). Figure 7 Atomic force microscope (AFM) measurement images of the hole transport layer including QUPD (X-QUPD) and the charge transport complex of Example 1 (SPN-QUPD).

[0345] Reference Figure 6 and Figure 7 It can be seen that in the hole transport layer including the charge transport complex (SPN-QUPD) of Example 1, a silicone network is uniformly formed inside the QUPD film without microphase separation.

[0346] Figure 8 is an image showing a charge transport layer pattern of a hole transport layer including the charge transport complex (SPN-QUPD) of Example 1.

[0347] Reference Figure 8 It can be seen that the hole transport layer including the charge transport complex (SPN-QUPD) of Example 1 can realize an ultra-fine pattern of 2 μm level by photolithography and dry etching.

[0348] Fig. 9A graph showing the width and height of a high resolution pattern of a hole transport layer of a hole transport layer comprising the charge transport complex (SPN-QUPD) of Example 1, Fig.10 is a graph showing the results of chemical resistance testing, Fig.11 is a graph showing the results of an etching resistance test.

[0349] Reference Figures 9 to 11 It can be seen that the hole transport layer including the charge transport complex (SPN-QUPD) of Example 1 can simultaneously ensure chemical resistance and etching resistance (reduced by about 20% or more) through the silicone network embedded QUPD material.

[0350] In particular, the hole transport layer comprising the charge transport complex (SPN-QUPD) of Example 1 (wherein 4 mol% of the organic silica precursor is contained in the charge transport complex) has the high dry etching resistance of SI-HTL, and can achieve ultra-fine patterns of 2 μm level (further, 1 μm level) through photolithography and dry etching.

[0351] Fig.12 A simplified diagram showing organic light-emitting devices (Example 2-1, Example 2-2, Example 2-3) containing the charge transport complex of Example 1 having different concentrations of an organic silica precursor in a hole transport layer (SPN 4 mol%, 8 mol%, 16 mol%) and an image showing an energy band diagram.

[0352] Reference Fig.12 The organic light-emitting device of the comparative example has a structure of ITO / PEFOT:PSS / QUPD / CBP:Ir(ppy)3 / TPBi / LiF / Al, the organic light-emitting device of Example 2-1 has a structure of ITO / PEFOT:PSS / SPN-QUPD 4mol% / CBP:Ir(ppy)3 / TPBi / LiF / Al, the organic light-emitting device of Example 2-2 has a structure of ITO / PEFOT:PSS / SPN-QUPD8mol% / CBP:Ir(ppy)3 / TPBi / LiF / Al, and the organic light-emitting device of Example 2-3 has a structure of ITO / PEFOT:PSS / SPN-QUPD 16mol% / CBP:Ir(ppy)3 / TPBi / LiF / Al.

[0353] Furthermore, it can be seen that in the case of a hole transport layer, the photoelectric properties and energy level structure are very important for the high performance of OLEDs. In the organic light-emitting devices of Examples 2-1 to 2-3, even if a silicone network is embedded in the hole transport layer, it still maintains UV properties and band gap.

[0354] Furthermore, it can be seen that in the organic light-emitting devices of Examples 2-1 to 2-3, as the content of the organic silicon dioxide precursor increases, the HOMO energy level of the SI-HTL moves to a deep energy level due to the electron-withdrawing inductive effect of organic silicon (-Si-O-).

[0355] Fig.13 is a diagram showing ultraviolet photoelectron spectroscopy (UPS), Fig.14 For a graph showing absorbance, Fig.15 This is a diagram showing the band gap (energy gap) using a Tauc plot.

[0356] Reference Figures 13 to 15 It can be seen that as the content of the organic silica precursor in the hole transport layer included in the organic light-emitting device of Example 2-1 to Example 2-3 increases, the energy level (HOMO level) alignment with the low molecular organic light emitting body (green) of the organic light-emitting layer is improved.

[0357] Fig.16 2 is a graph showing the change in current density and brightness of the organic light-emitting device of the comparative example and the organic light-emitting devices of Examples 2-1 to 2-3 as a function of voltage, Fig.17 For a graph showing power efficiency and external quantum efficiency as a function of brightness, Fig.18 To show the graph of current efficiency as a function of brightness, Fig.19 A graph is shown to summarize the brightness and maximum quantum efficiency as a function of the organosilica precursor content.

[0358] Reference Figures 16 to 19 It can be seen that by observing the luminescence characteristics of the OLED device based on the silicone network embedded QUPD, according to the content of the organic silica precursor contained in the charge transfer complex of the embodiment of the present invention, the luminescence performance of the hole transport layer included in the organic light-emitting devices of Examples 2-1 to 2-3 is improved compared with the organic light-emitting devices of the comparative example, and in particular, the organic light-emitting device of Example 2-1 exhibits the most excellent luminescence performance.

[0359] More specifically, the organic light-emitting device of Example 2-1 (introducing 4 mol% of organic silicon network embedded QUPD) can ensure 14320 cd / m 2 Improved luminescent properties of luminance of 1.5 times (increased by 1.5 times @8 V compared to Crosslinked QUPD (Comparative Example)) and EQE of 6.9% (increased by about 1.2 times compared to Crosslinked QUPD (Comparative Example)).

[0360] Fig. 20 1 is a schematic diagram of an organic light-emitting device of Example 3 and an image showing an energy band diagram.

[0361] Reference Fig. 20 The organic light-emitting device of Example 3 has a structure of ITO / PEFOT:PSS / SPN-QUPD 4mol% / SPN-QUPD 16mol% / CBP:Ir(ppy)3 / TPBi / LiF / Al.

[0362] Furthermore, it can be seen that in the case of a hole transport layer, the optoelectronic properties and energy level structure are very important for the high performance of OLEDs. In the organic light-emitting device of Example 3, a bilayer concentration of organic silica precursor is used as a hole transport layer, so that the HOMO energy level is well aligned with the organic light-emitting layer (CBP).

[0363] Fig.21 is a graph showing the change in current density and brightness of the organic light-emitting device of Example 2-1 and the organic light-emitting device of Example 3 with voltage, Fig. 22 A graph is shown to compare power efficiency and external quantum efficiency as a function of brightness, Fig.23 A graph is shown to compare the current efficiency as a function of brightness. Fig.24 Graphs are shown for comparison of brightness and maximum quantum efficiency.

[0364] Reference Figure 21 to Figure 24 It can be seen that the organic light-emitting device of Example 3 uses a bilayer concentration of organic silica precursor as a hole transport layer, so that the HOMO energy level is well aligned with the organic light-emitting layer (CBP), and therefore the luminescence performance is improved compared with the organic light-emitting device of Example 2-1.

[0365] On the other hand, the embodiments of the present invention disclosed in this specification and the accompanying drawings are provided only as specific examples to aid understanding, and are not intended to limit the scope of the present invention. It is obvious to those skilled in the art that, in addition to the embodiments disclosed herein, other variations based on the technical ideas of the present invention may also be implemented.

Claims

1. A charge transfer complex, characterized in that Include: Curable organic semiconductors; and An organic silicon dioxide precursor forms an organic silicon network structure with the curable organic semiconductor, The curable organic semiconductor includes a cross-linking functional group.

2. The charge transfer complex according to claim 1, characterized in that The cross-linking functional group includes at least one of vinyl, vinyl derivatives, oxetane, boric acid, trifluorovinyl ether, benzocyclobutene and epoxide.

3. The charge transfer complex according to claim 2, characterized in that The cross-linking functional group includes a functional group represented by any one of the following Chemical Formulas 3 to 8: In the chemical formulae 3 to 8, R1 each independently includes hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, carbonyl, ether, silyl, siloxane, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, C1-C20 haloalkyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C The present invention further comprises any one of a substituted or unsubstituted C1-C20 aryloxy group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C7-C30 arylalkyl group, a substituted or unsubstituted C2-C30 alkenyloxy group, a substituted or unsubstituted C8-C30 alkenylaryl group, a substituted or unsubstituted C7-C30 arylalkoxy group, a substituted or unsubstituted C8-C30 arylalkenyl group and a substituted or unsubstituted C2-C20 alkoxycarbonyl group.

4. The charge transfer complex according to claim 1, characterized in that The curable organic semiconductor is a hole transport compound bonded with the cross-linking functional group, and the hole transport compound includes at least one of triphenylamine derivatives, aromatic diamine derivatives, arylene diamine derivatives, carbazole derivatives, spiroarylene diamine derivatives, starburst amine derivatives, triarylamine derivatives, thiophene derivatives and triarylphosphine derivatives.

5. The charge transfer complex according to claim 4, characterized in that The curable organic semiconductor includes N4,N4'-bis(4-(6-((3-ethyloxetane-3-yl)methoxy)hexyloxy)phenyl)-N4,N4'-bis(4-methoxyphenyl)biphenyl-4,4'-diamine, N4,N4'-bis(4-(6-((3-ethyloxetane-3-yl)methoxy)hexyl)phenyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine, N,N-bis( At least one of 4-(6-((3-ethyloxetane-3-yl)methoxy)hexyloxy)phenyl)-3,5-di(9H-carbazol-9-yl)aniline, vinylbenzyl-tri(4-carbazol-9-ylphenyl)amine), N,N'-bis(tolyl)-N,N'-bis(vinylphenyl)-1,1'-biphenyl-4,4'-diamine, tris[(p-trifluoroethyleneoxy-biphenyl)]amine, MUPD and AUPD.

6. The charge transfer complex according to claim 1, characterized in that The curable organic semiconductor is an electron transport compound bonded with the cross-linking functional group, and the electron transport compound includes at least one of an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, a benzoxazole derivative, a benzothiazole derivative, a benzimidazole derivative, a triazine derivative, a benzoquinone derivative, a pyridine derivative, an anthraquinone derivative, a polyquinoline derivative and a polyfluorene derivative.

7. The charge transfer complex according to claim 6, characterized in that The curable organic semiconductor includes at least one of 4,6-bis[4-(5-{4-[(4-vinylbenzyloxy)methyl]phenyl}-4-(4-tert-butyl-phenyl)-4H-1,2,4-triazol-3-yl)phenyl]-2-methylpyrimidine, SMH-E-10, 1,3,5-tris(5(4-vinylphenyl)pyridin-3-yl)benzene and U-BmPyPB.

8. The charge transfer complex according to claim 1, characterized in that The luminescence intensity and durability of the charge transport complex are adjusted according to the concentration of the organic silica precursor.

9. The charge transfer complex according to claim 8, characterized in that The concentration of the organic silica precursor is 1.40 weight percent to 7.13 weight percent based on the charge transport complex.

10. The charge transfer complex according to claim 1, characterized in that The organic silica precursor includes a compound represented by any one of the following Chemical Formulas 9 to 19: In the chemical formula 9, R' includes any one of 1 to 3 halogen elements and alkoxy groups, wherein the alkoxy group is -O-(CH2) x -CH3, wherein X is an integer from 0 to 8, and m is an integer from 0 to 20, In the chemical formula 13, R' includes any one of 1 to 3 halogen elements and alkoxy groups, wherein the alkoxy group is -O-(CH2) x -CH3, wherein X is an integer from 0 to 8, 11. The charge transfer complex according to claim 10, characterized in that The organosilicon network structure is any one of a single-phase network bonded with organosilicon and an interpenetrating polymer network bonded with organosilicon.

12. A method for patterning a charge transport layer, characterized in that: include: A step of forming a charge transport layer comprising the charge transport complex according to any one of claims 1 to 11 on a substrate; forming a photoresist on the charge transport layer; The step of patterning the photoresist to form a photoresist pattern; The step of dry etching the charge transport layer using the photoresist pattern as an etching mask to form a charge transport layer pattern; as well as The step of removing the photoresist pattern.

13. The method for patterning a charge transport layer according to claim 12, characterized in that: The charge transfer complex comprises an organic silicon network structure, and the organic silicon network structure is any one of a single-phase network bonded with organic silicon and an interpenetrating polymer network bonded with organic silicon.

14. The method for patterning a charge transport layer according to claim 12, characterized in that: In the step of forming a charge transport layer, at least two sub-charge transport layers having different concentrations of an organic silicon dioxide precursor are formed on the substrate.

15. The method for patterning a charge transport layer according to claim 12, characterized in that: In the step of dry-etching the charge transport layer using the photoresist pattern as an etching mask to form a charge transport layer pattern, the charge transport layer forms a non-volatile blocking layer on the side of the charge transport layer pattern through the organic silicon network structure of the charge transport complex.

16. The method for patterning a charge transport layer according to claim 15, characterized in that: The non-volatile barrier layer includes at least one of SixOy and SixOyFz, wherein x, y and z are integers of 1-4.

17. The method for patterning a charge transport layer according to claim 12, characterized in that: The size of the charge transport layer pattern is 10 nm to 1000 μm.

18. An organic light-emitting device, characterized in that: include: A first electrode formed on the substrate; an organic light-emitting layer, formed on the first electrode; a second electrode formed on the organic light-emitting layer; as well as A charge transport layer formed at least one of an interface between the first electrode and the organic light emitting layer and an interface between the organic light emitting layer and the second electrode, and comprising the charge transport complex according to any one of claims 1 to 9.

19. The organic light emitting device according to claim 18, characterized in that: The luminescence intensity and durability of the charge transport layer are adjusted according to the concentration of the organic silica precursor.

20. The organic light emitting device according to claim 19, characterized in that: The charge transport layer includes at least two sub-charge transport layers having different concentrations of the organic silicon dioxide precursor.

21. The organic light emitting device according to claim 20, characterized in that: The charge transport layer includes a first sub-charge transport layer and a second sub-charge transport layer at an interface between the first electrode and the organic light-emitting layer, and the concentration of the organic silicon dioxide precursor in the second sub-charge transport layer is higher than that in the first sub-charge transport layer.

22. A charge transport layer composition, characterized in that: Include: Curable organic semiconductors; and Organosilica precursors.

23. The charge transport layer composition according to claim 22, characterized in that The charge transport layer composition includes 92.87 weight percent to 98.60 weight percent of the curable organic semiconductor and 1.40 weight percent to 7.13 weight percent of the organic silica precursor.

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