WO2017052308A2 - Composé organique devant être utilisé dans un dispositif organique et procédé de fabrication de dispositif organique l'utilisant - Google Patents

Composé organique devant être utilisé dans un dispositif organique et procédé de fabrication de dispositif organique l'utilisant Download PDF

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WO2017052308A2
WO2017052308A2 PCT/KR2016/010717 KR2016010717W WO2017052308A2 WO 2017052308 A2 WO2017052308 A2 WO 2017052308A2 KR 2016010717 W KR2016010717 W KR 2016010717W WO 2017052308 A2 WO2017052308 A2 WO 2017052308A2
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compound
group
formula
organic
pyrimidine ring
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PCT/KR2016/010717
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WO2017052308A3 (fr
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이성구
서민혜
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한국생산기술연구원
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Priority claimed from KR1020150136847A external-priority patent/KR101789672B1/ko
Priority claimed from KR1020160045725A external-priority patent/KR101859123B1/ko
Priority claimed from KR1020160120760A external-priority patent/KR101888562B1/ko
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Publication of WO2017052308A2 publication Critical patent/WO2017052308A2/fr
Publication of WO2017052308A3 publication Critical patent/WO2017052308A3/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a compound for an organic device that can be applied to the hole blocking layer, the electron transport layer, the light emitting layer of the organic device, more specifically, hydrogen bonding, by combining at least two or more functional groups containing a pyrimidine ring
  • the present invention relates to a compound for an organic device, a method for manufacturing an organic thin film including the same, and an organic device, wherein the organic thin film may be formed through a solution process.
  • the organic photoelectric device which is attracting attention as a next-generation display device, forms an organic light emitting layer between a cathode and a cathode coated with a transparent cathode material such as ITO, and when a predetermined voltage is applied to the electrode, It is a device using the principle that the injected electrons are combined in the organic light emitting layer to emit light.
  • the organic photoelectric device is manufactured in a multi-layered structure including a charge blocking layer according to the characteristics of the hole injection layer, the hole transport layer, the electron transport layer, the electron injection layer and the light emitting layer in addition to the organic light emitting layer in order to achieve a level of industrially applicable performance. .
  • each layer constituting the organic device is generally formed by a vacuum deposition process.
  • the vacuum deposition method is a principle of forming a thin film by heating a sample in a high vacuum atmosphere of 10-4 Torr or less to heat and subliming the sample to a solid on a relatively low temperature substrate.
  • the vacuum deposition method can be applied only to monomolecular compounds having a high molecular weight and not crystallized by heat as the sublimation process of the compound is essential, and requires expensive vacuum deposition equipment and it is difficult to manufacture devices in large areas. Can be.
  • Republic of Korea Patent No. 10-0865661 name of the invention: “a polymer compound having a phenylcarbazole group and a polymer electroluminescent device using the same” hereinafter referred to as the prior art 1) to prepare a polymer compound having a phenylcarbazole group
  • a technique of forming a light emitting layer of an organic photoelectric device by spin coating a solution containing the same has been disclosed.
  • the polymer material When the polymer material is applied as in the prior art 1, it is possible to form a thin film through a low-cost solution process and can not be crystallized by heat, thereby exhibiting excellent thin film properties. Difficult to remove completely, the efficiency of the device is lower than the single-molecule organic material, there is a problem in that the organic thin film produced by applying this as the molecular weight distribution is present locally different physical properties.
  • Prior art 1 proposes a polymer compound containing a phenylcarbazole group as a compound for an organic device capable of a low-cost solution process, but the polymer compound has a low charge transfer ability compared to a monomolecular compound and is difficult to purify the compound with high purity. There is a problem in that it is limited in improving the efficiency of the device.
  • the technical problem to be achieved by the present invention is to provide a technique for a low molecular compound for an organic device capable of forming a thin film through a solution process due to its high solubility in organic solvents and excellent thin film properties.
  • the present invention has another object to contribute to the large area and low cost of the organic device by providing a technique for such a novel compound.
  • the technical problem to be achieved by the present invention is to improve the performance of the organic device when manufacturing the organic device having a multi-layer structure through a solution process, and to improve the solubility and thin film formation characteristics of the solvent organic to ensure sufficient stability It is intended to provide a device compound.
  • At least one functional group including a pyrimidine ring the functional group including the pyrimidine ring can be applied to the electron transport layer or hole blocking layer, characterized in that hydrogen bonds are possible
  • the functional group including the pyrimidine ring can be applied to the electron transport layer or hole blocking layer, characterized in that hydrogen bonds are possible
  • At least one functional group containing a pyrimidine ring at the terminal of the carbazole-based compound comprising carbazole, the functional group including the pyrimidine ring is capable of hydrogen bonding It provides a compound for an organic light emitting organic device characterized in that.
  • At least one functional group including a pyrimidine ring at the terminal of the compound having a hole transport property to form an organic thin film by hydrogen bonding between the functional group comprising the pyrimidine ring It provides a compound for an organic device, characterized in that.
  • another embodiment of the present invention provides a method of manufacturing an organic thin film. i) dissolving a compound for an organic device having two or more functional groups including a pyrimidine ring in a soluble second solvent to prepare a solution, ii) preparing a substrate, iii) the upper portion of the substrate Applying a solution, and iv) heat-treating the substrate to which the solution is applied at a temperature of 70 ° C. to 170 ° C. to form an organic thin film by hydrogen bonding in the working period including the pyrimidine ring. It provides a method for producing a thin film.
  • the solution process by improving the solubility of the compound by introducing at least two functional groups containing a pyrimidine ring capable of hydrogen bonding to the compound for the hole blocking layer, electron transport layer, light emitting layer of the conventional organic device.
  • a second effect that the solution containing the compound can form an organic thin film having excellent thermal stability by hydrogen bonding of the working period including the pyrimidine ring at a temperature of 70 °C to 170 °C,
  • Forming the organic thin film through a low-cost solution process has a fourth effect that can contribute to lowering the cost and mass production of the organic device.
  • the organic light emitting compound according to the present invention may be improved in solubility in various solvents by providing a functional group including a pyrimidine ring capable of hydrogen bonding.
  • the low molecular organic light-emitting compound is generally used to form an organic thin film mainly through the deposition process due to the problem of poor solubility, it is possible to provide properties suitable for various solution processes by the improved solubility according to the present invention.
  • 1 is a chemical formula of a compound for an organic device according to an embodiment of the present invention and a hydrogen bond structural formula thereof.
  • FIG. 2 is a cross-sectional view and an energy level diagram showing a stacked structure of an organic light emitting diode according to an embodiment of the present invention.
  • FIG. 3 is a diagram showing a 1 HNMR spectrum of the compound for organic devices (uracil-B3PyPB) according to an embodiment of the present invention.
  • FIG. 4 is a view showing UV-vis absorption spectrum and PL spectrum of the compound for organic devices (uracil-B3PyPB) according to an embodiment of the present invention.
  • FIG. 5 is a graph showing an electro-optical characteristic analysis result of the organic light emitting device manufactured according to an embodiment of the present invention and the organic light emitting device according to the prior art.
  • FIG. 6 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
  • FIG. 7 is a graph showing the UV-vis spectrum and PL spectrum of the organic light emitting compound (MCP-pym) and the organic light emitting compound (MCP) according to the prior art according to an embodiment of the present invention.
  • FIG 8 is a graph showing the EL spectrum and the PL spectrum of the blue phosphorescent dopant (Fir6) of the organic light emitting device according to an embodiment of the present invention.
  • FIG. 9 is a graph showing the current efficiency according to the change in the current density of the organic light emitting device manufactured according to an embodiment of the present invention.
  • FIG 10 is a view showing a hydrogen bonding structure of the compound for organic devices (uracil-TPA) according to an embodiment of the present invention.
  • FIG. 11 is a view showing a hydrogen bond structure of the compound for organic devices (uracil-TPD) according to an embodiment of the present invention.
  • V-I voltage-current
  • FIG. 13 is a graph showing changes in luminous efficiency with respect to current densities of Example 5 and Comparative Example 3.
  • FIG. 13 is a graph showing changes in luminous efficiency with respect to current densities of Example 5 and Comparative Example 3.
  • V-I voltage-current
  • FIG. 15 is a graph showing changes in luminous efficiency with respect to current densities of Example 6 and Comparative Example 3.
  • FIG. 15 is a graph showing changes in luminous efficiency with respect to current densities of Example 6 and Comparative Example 3.
  • V-I voltage-current
  • FIG. 17 is a graph showing changes in luminous efficiency with respect to current densities of Example 7, Example 8 and Comparative Example 4.
  • FIG. 17 is a graph showing changes in luminous efficiency with respect to current densities of Example 7, Example 8 and Comparative Example 4.
  • FIG. 18 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
  • the "functional group including a pyrimidine ring” refers to a group of atoms derived from a compound including a pyrimidine ring in which four carbon atoms and two nitrogen atoms form a ring structure, and hydrogen atoms constituting a pyrimidine ring. Or it shall include all substituted or unsubstituted atomic groups.
  • the “purine-based functional group” refers to an atomic group derived from purine, which is an aromatic ring compound having a structure in which a pyrimidine ring and an imidazole ring share one carbon-carbon bond, and are hydrogen atoms constituting a purine molecule or It is assumed to include all substituted or unsubstituted atomic groups.
  • substituted or unsubstituted is a hydrogen atom of the compound selected from deuterium, halogen, linear or branched alkyl group, aryl group, heterocyclic group, cyano group, amino group, carboxyl group, hydroxy group, halogenated alkyl group It means that it is substituted with one or more functional groups, or have no functional groups.
  • pyridine means a heterocyclic compound containing one nitrogen atom.
  • the present invention relates to a compound for an organic device applied to a hole blocking layer (HBL) or an electron transport layer (ETL) of an organic device
  • the functional group including the pyrimidine ring of the present invention includes an atomic group capable of hydrogen bonding, as described above, when the compound for an organic device includes at least two or more functional groups, hydrogen of the functional period under a predetermined temperature condition It is characterized by forming an organic thin film by bonding.
  • uracil-B3PyPB a compound for an organic device having two functional groups including a pyrimidine ring according to an embodiment of the present invention.
  • Compound uracil-B3PyPB contains a pyrimidine ring containing two hydrogen atoms of B3PyPB (1,3-bis [3,5-di (pyridin-3-yl) phenyl] benzene), which is a material of a conventional hole blocking layer or electron transport layer. It can be prepared by substituting each functional group.
  • Figure 1 (b) is a view showing the hydrogen bond structural formula of the compound uracil-B3PyPB.
  • the compound uracil-B3PyPB has a functional group including a hydrogen group capable of hydrogen bonding at both ends thereof to form a network structure with hydrogen bonds in the working period under a predetermined temperature condition, thereby forming an organic thin film through a solution process. Formation may be possible.
  • the functional group containing the pyrimidine ring of the present invention may be one or more selected from pyrimidine-based functional groups and purine-based functional groups.
  • the pyrimidine-based functional group may be characterized in that it is derived from a pyrimidine-based compound represented by Formula 1a or 1b.
  • R1 to R6 may be the same as or different from each other, and each independently hydrogen, deuterium, halogen, linear or branched alkyl group, aryl group, heterocyclic group, cyano group, amino group, carboxyl group, hydroxy group, halogenated alkyl group, Selected from alkoxy groups)
  • the functional group derived from the pyrimidine-based compound represented by Formula 1a or Formula 1b may be selected from a plurality of substance groups represented by the following formulas, but is not limited thereto.
  • the purine-based functional group in one embodiment of the present invention may be characterized in that it is derived from one selected from the purine-based compound represented by the formula (2a) to 2f.
  • R7 to R21 may be the same as or different from each other, and each independently hydrogen, deuterium, halogen, straight or branched chain alkyl group, aryl group, heterocyclic group, cyano group, amino group, carboxyl group, hydroxy group, halogenated alkyl group, Selected from alkoxy groups)
  • the functional group derived from the purine-based compound represented by Formulas 2a to 2f may be selected from a plurality of substance groups represented by the following Formulas, but is not limited thereto.
  • the compound for an organic device of the present invention is a compound containing an electron-withdrawing group capable of stabilizing an anion radical or a part of atoms or atomic groups of a metal complex compound capable of accommodating electrons. It may be prepared by replacing at least one or more functional groups.
  • the compound for an organic device includes at least one hydrogen atom of at least one compound selected from metal complex compounds represented by the following [Formula 3-1] to [Formula 3-3] as a functional group including the pyrimidine ring. It may be prepared by substitution above.
  • the metal complex compound to which the functional group including the pyrimidine ring can be bound is not limited to the following [Formula 3-1], [Formula 3-2] and [Formula 3-3], It is noted that derivatives may also be possible.
  • M is one metal element selected from Al or Ga
  • the compound for an organic device is a pyrimidine compound of one kind of atoms or atomic groups selected from the hole blocking layer and / or the electron transport layer compound of the organic device represented by the following [Formula 4-1] to [Formula 4-16] It may be prepared by replacing at least one or more functional groups containing a ring.
  • the compound for an organic device of the present invention may be selected from any one of oxadizole group, azole group, and benzimidizole group.
  • the compound may be a compound represented by the following formula.
  • the compound for an organic device of the present invention includes a pyridine which is a group having electron-specificity, and part of one compound selected from the compounds represented by the following [Formula 4-1] to [Formula 4-16] It may be prepared by replacing at least one atom or atom group with a functional group including a pyrimidine ring.
  • the present invention can be achieved by substituting some of the atoms or the atomic groups of the derivatives derived from the following [Formula 4-1] to [Formula 4-16] with a functional group including the pyrimidine ring.
  • the compound for an organic device of the present invention includes a pyrimidine ring as part of a compound having an electron-withdrawing group other than the compound containing a pyridine structure represented by the above [Formula 4-1] to [Formula 4-16]
  • the electron withdrawing group may be prepared by substituting a functional group, and specifically, the electron withdrawing group may be silole, oxadiazole, triazole, imidazole, or perfluorinated oligo-p-phenyl. Perreninated oligo-p-phenylene, phenanthroline, triazine and the like.
  • the compound having an electron withdrawing group in addition to the above [Formula 4-1] to [Formula 4-27] may be selected from a plurality of substance groups represented by the following formula, and a portion of the selected compound or atom group It is noted that the present invention can be achieved by substitution with a functional group containing a midine ring.
  • the compound for an organic device according to the present invention is from the group consisting of the compounds represented by the above [Formula 3-1] to [Formula 3-3] and the formula [Formula 4-1] to [Formula 4-16] It may be prepared by substituting at least two or more of the atoms or atomic groups of the selected one compound with a functional group including the pyrimidine ring, the compound for an organic device having two or more functional groups as described above The hydrogen bond can form an easily stable organic thin film.
  • the compound for an organic device according to the present invention has a feature of controlling the hardness of the organic thin film formed according to the number of functional groups containing a pyrimidine ring.
  • the compound for an organic device according to the present invention includes an atomic group capable of hydrogen bonding to a functional group including a pyrimidine ring provided in the compound to form an organic thin film by hydrogen bonding between these atomic groups. Through the formation of a more dense network structure can exhibit the characteristic of increasing the hardness of the thin film.
  • the organic thin film is i) dissolving a compound for an organic device having two or more functional groups including a pyrimidine ring in a first solvent to prepare a solution, ii) preparing a substrate, iii 1) applying the solution to one surface of the substrate, iv) heat-treating the substrate to which the solution is applied for a predetermined time to form an organic thin film.
  • the compound for an organic device having two or more functional groups including a pyrimidine ring in step i) of the present invention may be soluble in the first solvent at room temperature, and in one embodiment of the present invention, the first solvent Is 1,2,3-trichlorobenzene (1,2,3-Trichlorobenzene), 1,2,4-trichlorobenzene (1,2,4-Trichlorobenzene), 1,3,5-trichlorobenzene (1 , 3,5-Trichlorobenzen), chloroform, chloroform, tetrahydrofuran and one or two or more mixed solvents selected from ethanol, but is not limited thereto.
  • the first solvent Is 1,2,3-trichlorobenzene (1,2,3-Trichlorobenzene), 1,2,4-trichlorobenzene (1,2,4-Trichlorobenzene), 1,3,5-trichlorobenzene (1 , 3,5-Trichlorobenzen), chloroform, chloroform, tetra
  • the substrate in step ii) of the present invention is not limited, and may be any substrate as long as the substrate is not melted by the solution and is not deformed in the heat treatment step described later.
  • Step iii) of the present invention is a step of applying a solution to one side of the substrate.
  • Application of the solution may be any known solution coating and coating method such as spin coating, inkjet printing, casting method, dip coating, spray coating without limitation.
  • Step iv) of the present invention is a step of forming an organic thin film by inducing hydrogen bonding by heat-treating the substrate to which the solution is applied for a predetermined time.
  • the functional group including the pyrimidine ring may include an atomic group capable of hydrogen bonding to form an organic thin film through hydrogen bonding therebetween, and the heat treatment may be preferably performed at a temperature in the range of 70 to 170 ° C. Can be. If the heat treatment temperature is less than 70 °C heat energy for hydrogen bonding may not be enough to form an organic thin film, if it exceeds 170 °C excessive heat may be applied to inhibit the stability of the substrate and the compound It is specified that the temperature is limited, but not necessarily limited thereto.
  • the compound for an organic device according to the present invention can be applied to the hole blocking layer and / or the electron transport layer of the organic light emitting device including the electron pulling characteristics or a group that can accept the electron well, the compound for an organic device according to the present invention It will be described with respect to the organic light emitting device manufactured to include.
  • the organic light emitting device of the present invention may include an anode, a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and a cathode, wherein the hole blocking layer and / or the electron transport layer in one embodiment of the present invention Therefore, the organic thin film may be formed from a solution containing a compound for an organic device having at least two functional groups including a pyrimidine ring.
  • the hole blocking layer may be formed including a compound represented by the following formula.
  • the Pym 1 to Pym 7 may be the same as or different from each other, at least two or more of Pym 1 to Pym 7 is a functional group containing the pyrimidine ring, the remainder is hydrogen, Pym 8 to Pym in the formula (6) 10 may be the same as or different from each other, at least two or more of Pym 8 to Pym 10 may be a functional group including the pyrimidine ring, and the remainder is hydrogen)
  • the hole blocking layer prepares a solution containing the compound represented by the above formula, and is applied on top of the light emitting layer to induce hydrogen bonding of the compound represented by the above formula under a predetermined temperature condition. Can be formed.
  • the predetermined temperature conditions are the same as the heat treatment conditions described above in the method for manufacturing the organic thin film.
  • anode, the hole injection layer, the hole transport layer, the light emitting layer, and the cathode constituting the organic light emitting device may be formed of a material known in the art using a known method (deposition, solution process, etc.). However, for the smooth operation of the device using known materials, the device must be made in consideration of the energy level of the compounds constituting each layer.
  • 2 is a cross-sectional view of an organic light emitting device according to an embodiment of the present invention manufactured in consideration of energy levels of compounds constituting each layer, and a diagram illustrating energy levels of compounds constituting each layer.
  • the organic light emitting device is a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), a hole blocking layer ( HBL), the electron transport layer (ETL), and the electron injection layer (EIL) can be prepared by sequentially forming.
  • a hole injection layer, an electron transport layer, or an electron injection layer may use a known organic material
  • the hole blocking layer may use uracil-B3PyPB, which is a compound for an organic device, according to an embodiment of the present invention.
  • the functional group containing the pyrimidine ring of the present invention is not only a hole blocking material, but also specifies that at least two or more bonded to the hole transport layer or the light emitting layer material may enable the formation of an organic thin film through hydrogen bonding.
  • the hole transport layer illustrated in FIG. 2A includes uracil-TCTA prepared by combining a derivative of uracil, which is a kind of a functional group containing a pyrimidine ring, to TCTA, a known hole transport material.
  • the light emitting layer may include a uracil-CzTP and a dopant prepared by binding the derivative of uracil to CzTP, which is a known host material.
  • the compound for an organic device and the organic thin film prepared by using the same according to the present invention are not limited to an organic light emitting device, and are not applicable to various organic devices such as an organic photosensitive member, an organic transistor, an organic solar cell, and an organic image sensor. It can be obvious.
  • UV spectra and PL (photoluminescence) spectra were analyzed to determine the optical properties of the compound uracil-B3PyPB prepared according to Example 1.
  • UV spectra and PL spectra were measured by dissolving uracil-B3PyPB in chloroform, the results of which are shown in FIG. 4.
  • the compound uracil-B3PyPB prepared according to an embodiment of the present invention is compared with the compound B3PyPB (UV absorption peak 250 nm, PL peak 357 nm) for an organic device having no functional group (uracil), Although shifted toward longer wavelengths, it was found to have almost the same optical characteristics. Therefore, the compound uracil-B3PyPB prepared according to an embodiment of the present invention may be determined to have solubility and thin film formation property in a solvent as well as the inherent optical properties of B3PyPB as having a functional group.
  • the energy levels of the compounds according to Examples 1 and 2 were measured using CV (cyclic voltammetry) to find out whether the prepared compounds have suitable energy levels for the hole blocking layer and / or the electron transport layer of the organic device.
  • CV cyclic voltammetry
  • ferrocene having an E 1/2 (half wave potential) of 0.35 V was used as a reference material.
  • the HOMO level value of the compound uracil-B3PyPB was found to be 6.37 eV.
  • the LUMO value of the compound uracil-B3PyPB was calculated from the optical bandgap energy known from the UV-vis absorption spectrum and the HOMO value calculated above, and the LUMO value was found to be 3.37 eV.
  • This value is similar to the energy level of the compound used in the hole blocking layer of the conventional organic light emitting device means that the compound prepared according to an embodiment of the present invention can be applied to the hole blocking layer of the organic light emitting device.
  • Figure 2 (b) is a view showing the energy level of the compound for an organic device prepared according to Example 1 and the compound for a conventional organic device.
  • the compound uracil-B3PyPB prepared according to one embodiment of the present invention can be used as a hole blocking layer.
  • the energy level of uracil-TAZ calculated by the same method was confirmed that the HOMO 5.72eV, LUMO 1.74eV, it can be applied to the organic light emitting device.
  • ITO glass substrate was used as the anode, and the ITO substrate was immersed in acetone for 30 minutes, ultrasonically cleaned and dried, and then immersed in isopropyl alcohol and distilled water in the same manner to remove impurities.
  • PEDOT: PSS (PH4083, Celvios) was coated on the surface coated with ITO by spin coating, and dried at a temperature of 120 ° C. for 30 minutes to form a hole injection layer.
  • Uracil-TCTA was prepared by combining three functional groups containing a pyrimidine ring according to the present invention to TCTA (Tris (4-carbazoyl-9-ylphenyl) amine), which is known as a compound for a hole transport layer, at different positions.
  • TCTA Tris (4-carbazoyl-9-ylphenyl) amine
  • the prepared uracil-TCTA was dissolved in trichlorobenzene at a concentration of 20wt% to prepare a solution, which was coated on top of the hole injection layer by spin coating, followed by heat treatment at a temperature of 100 ° C. for 30 minutes. To form a hole transport layer.
  • CzTP (6,6-bis [(3,5-diphenyl) phenyl] -9-phenyl-carbazole), which is known as a host material of the conventional light emitting layer
  • four functional groups containing a pyrimidine ring according to the present invention are respectively placed at different positions.
  • Uracil-CzTP was prepared by binding. After dissolving the prepared uracil-CzTP in chlorobenzene, the light emitting layer solution prepared by adding 8 wt% of Ir (mppy) 3, which is a green phosphorescent dopant, was applied by spin coating to the upper portion of the hole transport layer. Heat treatment for minutes to form a light emitting layer.
  • uracil-B3PyPB prepared according to one embodiment of the present invention was dissolved in trichlorobenzene at a concentration of 20 wt% to prepare a solution, and then coated on top of the light emitting layer by spin coating. Heat treatment at temperature for 30 minutes to form a hole blocking layer.
  • Alq3 Tris (8-hydroxy-quinolinato) aluminium
  • LiF and Al were sequentially vacuum deposited on the electron transport layer under the same conditions as above to form a cathode.
  • the organic light emitting device is composed of ITO / PH4083 / uracil-TCTA (40nm) / uracil-CzTP + Ir (mppy) 3 (8wt%) (30nm) / uracil-B3PyPB (10nm) / Alq3 (30nm) / LiF / Al. Made of structure.
  • the structural formulas of the urail-TCTA and uracil-CzTP are as follows, and the preparation thereof was performed in a reaction similar to those of Examples 1 and 2.
  • TAPC (Di- [4- (N, N-ditolyl-amino) -phenyl] cyclohexan) as hole transport material and CBP (4,4'-Bis (carbazol-9-yl) biphenyl) as host material as light emitting layer material %
  • the dopant Ir (mppy) 3 8wt%, TPBi (2,2 ', 2 "-(1,3,5-benzinetriyl) -tris (1-phenyl-1-H- Benzimidazole)) using an organic light emitting device was manufactured under the same conditions as in Example 2, except that by vacuum deposition under the same conditions as above to form a hole transport layer, a light emitting layer, a hole blocking layer.
  • the organic light emitting device was manufactured in the structure of ITO / PH4083 / TATC (30nm) / CBP + Ir (mppy) 3 (8wt%) (30nm) / TPBi (10nm) / Alq3 (30nm) / LiF / Al.
  • FIG. 5 (a) is a graph showing the voltage-current curve of each organic light emitting device manufactured according to Example 3 and Comparative Example 1,
  • Figure 5 (b) is a graph showing the luminous efficiency according to the current density. .
  • the organic light emitting device manufactured by applying the compound for an organic device according to an embodiment of the present invention has a stable multilayer thin film without the phenomenon that the lower layer is dissolved even though the hole transport layer, the light emitting layer, and the hole blocking layer are formed through a solution process.
  • a solution process e.g., a solution process for a solution process for a solution process.
  • the organic light emitting diode of Comparative Example 1 manufactured by forming a multilayer organic thin film by a solution process and vacuum depositing all layers except the hole transport layer of the organic light emitting diode of Example 3 It can be seen that the optical characteristics are almost the same. Therefore, when the organic light emitting device is manufactured by applying the compound for an organic device according to the present invention, the multilayer thin film can be manufactured by a solution process, thereby greatly reducing the device manufacturing cost and contributing to the large area and mass production of the device.
  • the multilayer thin film can be manufactured by a solution process, thereby greatly reducing the device manufacturing cost and contributing to the large area and mass production of the device.
  • the multilayer thin film can be manufactured by a solution process, thereby greatly reducing the device manufacturing cost and contributing to the large area and mass production of the device.
  • carbazole means a compound in which two benzene rings are bonded to both sides of a heterocycle including nitrogen, and includes both substituted or unsubstituted structures thereof.
  • carbazole compound in the present invention means a compound comprising a substituted or unsubstituted carbazole.
  • the pyrimidine ring means a heterocyclic ring composed of four carbon atoms and two nitrogen atoms, and includes all substituted or unsubstituted pyrimidine rings.
  • a purine-based functional group means a compound including a substituted or unsubstituted purine molecule
  • a purine molecule means an aromatic ring compound having a structure in which a pyrimidine ring and an imidazole ring share one carbon-carbon bond. do.
  • the organic light emitting compound according to the present invention may have at least one functional group including a pyrimidine ring at the terminal of the carbazole compound, and the functional group including the pyrimidine ring may be characterized in that hydrogen bonding is possible.
  • the carbazole compound is selected from carbazole compounds represented by the following Formulas 5a to 5f, and may include at least one functional group including a pyrimidine ring in the benzene ring of the carbazole compound.
  • the organic light emitting compound according to the present invention has excellent hole transporting properties, and has a triplet bandgap, thereby providing a functional group including a pyrimidine ring capable of hydrogen bonding to a carbazole compound applied as a phosphorescent host material. Not only properties but also solubility in various solvents can be secured to enable a solution process.
  • the organic light emitting compound may be preferably, but is not limited to a functional group such as an alkyl group, except for a functional group containing a pyrimidine ring to the carbazole compound. However, when it is not provided with a functional group such as an alkyl group, it may be preferable because the synthesis of the compound is simpler and the formation of the organic thin film is easy.
  • the functional group including the pyrimidine ring may be selected from pyrimidine-based functional groups and purine-based functional groups.
  • the pyrimidine-based functional group is formed from a compound represented by the following Chemical Formula 7a or 7b. It can be a functional group.
  • R 6 to R 11 in Formulas 7a and 7b may be the same as or different from each other, and each independently H, D, F, Cl, Br, I, an amino group, linear alkyl having 1 to 12 carbon atoms, and having 1 to 10 carbon atoms.
  • the pyrimidine-based functional group formed from the compound represented by Formula 7a may be selected from a plurality of substance groups represented by the following Formulas, but is not limited thereto.
  • the pyrimidine-based functional group formed from the compound represented by the formula (7b) may be selected from a plurality of groups represented by the following formula, but is not limited thereto.
  • the purine-based functional group in one embodiment of the present invention may be formed from a compound selected from the formula 8c to 8h.
  • R 12 to R 25 may be the same as or different from each other, and each independently H, D, F, Cl, Br, I, an amino group, linear alkyl having 1 to 12 carbon atoms, and having 1 to 10 carbon atoms.
  • the purine-based functional group may be selected from a plurality of substance groups represented by the following formula, but is not limited thereto.
  • the organic light emitting compound according to the present invention may be preferably provided with at least two or more functional groups containing a pyrimidine ring.
  • the organic light emitting compound according to the present invention can improve the solubility by providing a functional group containing a pyrimidine ring at the end of the carbazole compound having a low solubility in a solvent solution is difficult, furthermore, a functional group comprising a pyrimidine ring
  • An organic light emitting compound having two or more can form an organic thin film by hydrogen bonding between the functional group containing a pyrimidine ring.
  • the functional group including the pyrimidine ring according to the present invention includes a bond capable of hydrogen bonding such as an amide group and a carbonyl group in the compound. Therefore, when two or more functional groups including a pyrimidine ring are provided in the compound for an organic device, the organic thin film may be formed by inducing the above-described hydrogen bonding functional period.
  • the organic light emitting compound having two or more functional groups including a pyrimidine ring may be a compound represented by the following Chemical Formula 6, but is not limited thereto.
  • R 1 to R 5 may be the same as or different from each other, at least two or more of R 1 to R 5 are functional groups including a pyrimidine ring, and the rest are hydrogen.
  • the organic light emitting compound according to the present invention may be characterized in that the hardness of the thin film can be adjusted according to the number of functional groups including a pyrimidine ring provided at the terminal.
  • the organic light emitting compound according to the present invention forms a network structure through hydrogen bonding between functional groups including a pyrimidine ring provided at the terminal, and when the number of functional groups including a pyrimidine ring provided in the organic light emitting compound is increased, hydrogen By bonding, a thinner film having a more dense structure can be formed.
  • the organic thin film layer is a first step of preparing a solution by dissolving the organic light emitting compound in a solvent, a second step of preparing a substrate for coating the solution, comprising an organic light emitting compound on one side of the substrate
  • the third step of applying a solution it may be prepared including a step of forming a thin film by heat treatment the substrate to which the solution is applied for a predetermined time.
  • the organic light emitting compound according to the present invention may be characterized by having improved solubility by having a functional group including a pyrimidine ring, and being soluble in the solvent of the first step at room temperature.
  • the solvent is one, two or more selected from 1,2,3-Trichlorobenzene, 1,2,4-Trichlorobenzene, 1,3,5-Trichlorobenzen, chloroform, chloroform, Tetrahydrofuran and ethanol. It may be a mixed solvent including, but is not limited thereto.
  • a trichlorobenzene solvent the organic light emitting compound according to the present invention is more uniformly dissolved at room temperature, and there is an advantage that an organic thin film of high purity can be formed because it does not cause side reactions upon heating.
  • the method may further include adding a light emitting dopant between the first step and the second step.
  • the organic light emitting compound according to the present invention can be applied as a host material for the light emitting layer as it comprises a carbazole compound having a hole transporting property and phosphorescence properties as described above. Therefore, a light emitting layer solution may be prepared by further adding a light emitting dopant in a predetermined ratio to the solution of the first step.
  • the light emitting dopant may be added in an amount of 1 to 10 wt% with respect to 100 parts by weight of the total solution, and more preferably in a ratio of 5 to 10 wt%. This will be described in detail in the method of manufacturing an organic light emitting device to be described later.
  • the solution in the third step of the present invention is selected from the group consisting of spin coating, gravure offset printing, reverse offset printing, screen printing, roll-to-roll printing, slot die coating, dip coating, spray coating, doctor blade coating, inkjet coating It may be applied to one side of the substrate in any one way, but is not limited thereto.
  • the step of heat-treating the substrate to which the solution is applied may be carried out at a temperature of 70 to 170 °C
  • the organic light emitting compound according to the present invention comprises a pyrimidine ring at a predetermined temperature conditions It can be cured by hydrogen bonding in the working period to form a thin film.
  • the temperature is less than 70 °C
  • the heat treatment temperature exceeds 170 °C it is limited to the above temperature because it is not possible to ensure the stability of the substrate and the compound due to excessive heat, but is not limited thereto.
  • FIG. 6 is a cross-sectional view of an organic light emitting device manufactured according to an exemplary embodiment of the present invention.
  • the organic light emitting device comprises the steps of i) preparing a positive electrode substrate, ii) forming a hole injection layer on top of the positive electrode substrate, iii) forming a hole transport layer on top of the hole injection layer, iv) forming a light emitting layer on top of the hole transport layer, v) forming a hole blocking layer on top of the light emitting layer, vi) forming an electron transport layer on top of the hole blocking layer, vi) electrons on top of the electron transport layer Forming an injection layer and vii) forming a cathode on top of the electron injection layer.
  • the manufacturing method of the organic light emitting diode according to the present invention will be described in detail in the manner described in detail for each manufacturing step.
  • the anode substrate may be used without limitation as long as it is a substrate coated with a cathode material known in the art.
  • the anode substrate may be a substrate coated with a transparent electrode material such as indium tin oxide (ITO), fluorine tin oxide (FTO), or indium zinc oxide (IZO), but is not limited thereto. no.
  • the next step is to form a hole injection layer (HIL) on the anode substrate.
  • the hole injection layer is formed to include a compound that facilitates the hole injection by lowering the injection energy barrier of the hole injected from the anode, such as 4,4 ', 4 "-Tris (N, N-diphenyl-amino ) triphenylamine (NATA), 4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino) triphenylamine (m-MTDATA) and poly (3,4-ethylenedioxythiophene): poly (styrene Sulfonic acid) (PEDOT: PSS) and the like are known, and any material for a known hole injection layer may be used without limitation.
  • the hole injection layer may be formed by spin coating a PEDOT: PSS solution.
  • the next step is to form a hole transport layer (HTL) on top of the hole injection layer
  • the hole transport layer is formed by including a compound that serves to transport to the light emitting layer without losing holes injected from the anode Can be.
  • the hole transport layer is NPB (N, N'-bis (1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine), ⁇ -NPD (N, N '-Bis- (3-methylphenyl) -N, N'-bis- (phenyl) -benzidine (TPD), bis (N- (1-naphthyl-N-phenyl) benzidine), CBP (4,4- N, N'-dicarbazole-biphenyl), but is not limited thereto.
  • the hole injection layer is generally formed by vacuum depositing the above-described compound for hole injection layer.
  • the hole transport layer may be formed using a hole transport material having properties suitable for a solution process.
  • the hole transport material may be a compound having two or more functional groups including a pyrimidine ring in the terminal benzene ring of a known triphenylamine compound, and specifically, The compound represented by the following formula may be provided with two or more functional groups containing a pyrimidine ring to provide the same effect as the organic light emitting compound according to the present invention to form a hole transport layer through a solution process To be able.
  • R 1 to R 4 may be the same as or different from each other, at least two or more of R 1 to R 4 is a functional group including a pyrimidine ring, the remainder is hydrogen.
  • the next step is to form an Emitting Material Layer (EML) on top of the hole transport layer.
  • EML Emitting Material Layer
  • the light emitting layer may be formed by including a light emitting compound alone, or may be formed by mixing a light emitting dopant with a host material having charge transport characteristics. In the case of forming the light emitting layer by including the light emitting compound alone, the light emitting property is very excellent, but the charge transporting ability is low, so that it is difficult to manufacture a high efficiency organic light emitting device. It may be desirable to form a light emitting layer.
  • the present invention is characterized by using a carbazole compound having at least two functional groups containing a pyrimidine ring as a host material.
  • Carbazole-based compounds are generally known to be suitable as host materials because of their excellent charge transport properties, thermal stability, and high triplet energy.
  • the carbazole compound according to the present invention may have a functional group including a pyrimidine ring capable of hydrogen bonding at the terminal thereof to improve solubility, thereby enabling a solution process, and hydrogen of a working period including a pyrimidine ring. It is advantageous to form a thin film easily through bonding.
  • the luminescent dopant may be selected from a phosphorescent emission or a fluorescence emitting compound.
  • the phosphorescent emission is tripletd through the intersystem crossing. It may be preferable to use a compound having phosphorescence properties as a light emitting dopant because it has a longer life and higher efficiency than fluorescent light emission as a mechanism for light emission after the non-light emission transition to excitons, and the triplet excitons light up while transitioning to the ground state.
  • their triplet energy level should be considered.
  • the energy transfer from the host to the dopant is more stable, thereby improving the efficiency of the device. This is because if the triplet energy of the host is lower than the triplet energy of the dopant, energy loss occurs due to the endothermic energy transition, which causes a decrease in luminous efficiency of the device. On the other hand, when the triplet energy level of the host is higher than the triplet energy of the dopant, light emission due to the exothermic energy transfer may appear, thereby realizing high light emission efficiency.
  • a suitable dopant for the host material according to the present invention may be a blue phosphorescent dopant, specifically (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium ( Dopants selected from III) (FirPic) or Bis (2,4-difluorophenylpyridinato) -tetrakis (1-pyrazolyl) borate iridium (III) (Fir6) may be used, but are not limited thereto.
  • the light emitting layer is mixed with an organic light emitting compound having two or more functional groups including a pyrimidine ring as a host material and a solvent to prepare a mixed solution, the light emitting dopant based on 100 parts by weight of the mixed solution It may be formed by coating a solution prepared by adding 1 to 10wt%.
  • the next step is to form a hole blocking layer (HBL) on top of the light emitting layer.
  • the hole blocking layer serves to suppress the movement of holes that do not combine with electrons in the light emitting layer, and in one embodiment of the present invention, the hole blocking layer is Balq, 2,2 ', 2 "-(1,3,5- It may be formed by depositing a material such as benzinetriyl) -tris (1-phenyl-1-H-benzimidazole) (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP).
  • TPBi 1-phenyl-1-H-benzimidazole
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • the next step is to form an Electron Transport Layer (ETL) on top of the hole blocking layer.
  • ETL Electron Transport Layer
  • the electron transport layer may improve the coupling probability of holes and electrons in the light emitting layer by serving to transport electrons injected from the cathode to the light emitting layer.
  • the electron transport layer is Alq3 (Tris (8-hydroxy-quinolinato) aluminium), Balq (Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminium), BeBq2 (Bis (10- It may be formed by depositing one or more materials selected from the group consisting of hydroxybenzo [h] quinolinato) beryllium).
  • the next step is to form an Electron Injection Layer (EIL) on top of the electron transport layer.
  • the electron injection layer serves to facilitate the injection of electrons from the cathode by lowering the potential barrier during electron injection.
  • the electron injection layer is LiF, 8-Hydroxyquinolinolato-lithium (Liq), 1, It may be formed by depositing one or more materials selected from the group consisting of 3,5-tri [(3-pyridyl) -phen-3-yl] benzene (TmPyPB).
  • the next step is to form a cathode on top of the electron injection layer.
  • the negative electrode material may be formed by depositing a material having a small work function value such as lithium (Li), magnesium (Mg), calcium (Ca), aluminum (Al), Al: Li, Ba: Li, or Ca: Li. .
  • an organic light emitting device When manufacturing an organic light emitting device, it should be designed to maximize the efficiency of the device in consideration of the energy level of the compounds constituting each layer.
  • preferred embodiments and experimental examples of an organic light emitting device manufactured by using an organic light emitting compound having a functional group including a pyrimidine ring according to an embodiment of the present invention are described, but are not limited thereto.
  • the organic light emitting compound having a functional group including a pyrimidine ring according to the present invention and the organic thin film layer prepared by using the same may be applied to various organic devices other than the organic light emitting device, specifically, an organic transistor (TFT), organic It can be applied without limitation, such as photosensitive member (OPC), photodiode, organic laser and organic image sensor.
  • TFT organic transistor
  • OPC photosensitive member
  • photodiode organic laser and organic image sensor.
  • An ITO glass substrate was used as the cathode substrate, and the ITO substrate was ultrasonically washed and dried for 30 minutes with acetone, isopropyl alcohol, and distilled water to remove impurities.
  • PEDOT: PSS (PH4083, Celvios) was coated on the surface coated with ITO by spin coating, and then dried at a temperature of 120 ° C. for 30 minutes to form a hole injection layer.
  • TPD-pym was dissolved in trichlorobenzene to prepare a 30 wt% solution, which was then coated by spin coating and dried at 100 ° C. to form a hole transport layer.
  • a light emitting layer solution prepared by adding Fir6, a blue phosphorescent dopant, at 9wt% was applied by spin coating on the hole transport layer, and then at 100 ° C. It dried and the light emitting layer was formed.
  • TPBi was vacuum-deposited on the top of the light emitting layer under conditions of a vacuum degree of 1 ⁇ 10 ⁇ 7 Pa and a deposition rate of 2 nm / s to form a hole blocking layer.
  • Alq3 Tris- (8-hydroxyquinoline) aluminum
  • LiF is deposited on the electron transport layer to form an electron injection layer
  • Al is vacuumed thereon. Evaporation to form a cathode.
  • the organic light emitting device was manufactured in the structure of ITO / PH4083 / TPD-pym / MCP-pym + Fir6 (9wt%) / TPBi / Alq3 / LiF / Al.
  • NPB N, N'-bis (1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine
  • a device was manufactured under the same conditions as in Example 4, except that the solution for the light emitting layer prepared by adding the material MCP and the dopant Fir6 at 9wt% was vacuum deposited to form the light emitting layer.
  • UV spectra and PL (photoluminescence) spectra were measured to evaluate the optical properties of the compound MCP-pym prepared according to Example 4.
  • UV spectra were measured by dissolving MCP-pym in chloroform
  • PL spectra were measured by dissolving MCP-pym in chloroform. The results are shown in FIG.
  • the compound MCP-pym prepared by combining a functional group containing a pyrimidine ring to MCP has an optical characteristic almost similar to the MCP according to the prior art. Therefore, the organic light emitting compound according to the present invention can be judged to affect only the solubility and thin film formation properties without inhibiting the optical properties of the MCP.
  • Example 4 In order to evaluate the electro-optical characteristics of the organic light emitting device manufactured according to Example 4, the current density, current efficiency, and EL (electroluminescence) intensity of the organic light emitting device were measured. 8 shows the EL spectrum of the organic light emitting diode manufactured according to Example 4 and the PL spectrum of Fir6, which is a blue phosphorescent dopant, and according to the current density change of the organic light emitting diode according to Example 4 and Comparative Example 2 in FIG. A graph of the current efficiency change is shown.
  • the organic light emitting diode according to the exemplary embodiment of the present invention exhibits a maximum peak at around 460 nm and exhibits blue emission spectrum characteristics.
  • the emission spectrum characteristics of the organic light emitting diode according to the present invention almost overlap the emission spectrum of FiR6, which is a blue phosphorescent dopant shown in FIG.
  • the organic light emitting device according to an embodiment of the present invention can be seen that the maximum current efficiency is 14cd / A, which is about 2.5 times improved compared to the device of Comparative Example 2 manufactured through the deposition process Value. Therefore, when the organic light emitting compound according to the present invention is applied to an organic light emitting device, it is possible to enable a solution process, it can be seen that the organic light emitting device having a stable multilayer structure without dissolving adjacent layers through the solution process.
  • the pyrimidine ring in the present invention means a heterocyclic ring composed of four carbon atoms and two nitrogen atoms, and includes all substituted or unsubstituted pyrimidine rings.
  • a purine-based functional group means a compound including a substituted or unsubstituted purine molecule, and a purine molecule means an aromatic ring compound having a structure in which a pyrimidine ring and an imidazole ring share one carbon-carbon bond. do.
  • substituted or unsubstituted deuterium Halogen group; Alkyl groups; Aryl group; Hetiaryl group; Fluorenyl group; It means substituted with one or more functional groups selected from the group consisting of cyano groups, or having no functional groups.
  • the compound for an organic device according to the present invention includes at least one functional group including a pyrimidine ring at the terminal of the compound having hole transport properties, and the functional group including the pyrimidine ring is capable of hydrogen bonding. Can be.
  • the compound having a hole transport property may be selected from compounds represented by the following formula (9) or formula (10), and has at least one functional group including a pyrimidine ring at the terminal of the compound And, the functional group containing a pyrimidine ring can be characterized in that capable of hydrogen bonding.
  • Ar1, Ar2 and Ar3 may be the same as or different from each other, and each independently a substituted or unsubstituted phenyl group or naphthyl group.
  • n 2 or 3
  • Ar4 and Ar5 may be the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group, naphthyl group, phenanthrenyl group,
  • L is a direct bond
  • Ar6 is selected from the group consisting of a substituted or unsubstituted phenylene group, biphenylene group, naphthyleneyl group, fluorenyl group, cyclohexyl group, spirobifluorenyl group, triphenylamine group and diphenylmethylene group.
  • the compound having the hole transport property represented by Formula 9 or Formula 10 may be selected from a plurality of substance groups represented by the following Formulas, but is not limited thereto, and pyrimidine capable of hydrogen bonding to the benzene ring of the compound At least one functional group including a ring may be provided.
  • the compound having a hole transport property is at least one compound selected from a silicon compound, a phosphine oxide compound, and an arylamine compound, a functional group containing the pyrimidine ring at the terminal of the compound At least one may be provided.
  • the silicon-based compound may be selected from a plurality of material groups represented by the following chemical formulas, but is not limited thereto.
  • the phosphine oxide-based compound may be a plurality of substance groups represented by the following formulas.
  • the sulfide-based compound may be a compound represented by the following formula.
  • the arylamine-based compound may be a plurality of substance groups represented by the following formula.
  • the compound having the hole transport characteristics may be a hydrocarbon compound.
  • the hydrocarbon compound may be a plurality of substance groups represented by the following formulas.
  • the functional group including the pyrimidine ring may be a pyrimidine-based functional group and a purine-based functional group.
  • the pyrimidine-based functional group may be formed from a compound represented by the following Formulas 11a and 11b.
  • R 1 to R 6 may be the same as or different from each other, and each independently H, D, F, Cl, Br, I, an amino group, linear alkyl having 1 to 12 carbon atoms, and having 1 to 10 carbon atoms.
  • the pyrimidine-based functional group formed from the compound represented by Formula 11a may be selected from a plurality of substance groups represented by the following Formulas, but is not limited thereto.
  • a pyrimidine-based functional group formed from the compound represented by Formula 11b may be selected from a plurality of substance groups represented by the following Formulas, but is not limited thereto.
  • a purine-based functional group may be formed from a compound represented by the following Chemical Formulas 11c to 11h, but is not limited thereto.
  • the purine-based functional group may be selected from a plurality of substance groups represented by the following formulae, but is not limited thereto.
  • the compound for an organic device may be preferably provided with at least two or more functional groups including a pyrimidine ring.
  • the compound for an organic device according to the present invention may be improved in solubility by having a functional group including a pyrimidine ring at the terminal of the low molecular weight compound having a low solubility in a solvent, which makes it difficult to process the solution.
  • a stable organic thin film can be formed by hydrogen bonding of a functional period including a pyrimidine ring.
  • the functional group including the pyrimidine ring according to the present invention includes a bond capable of hydrogen bonding such as an amide group and a carbonyl group in the compound. Therefore, when two or more functional groups including a pyrimidine ring are provided in the compound for an organic device, the organic thin film may be formed by inducing the above-described hydrogen bonding functional period.
  • FIGS. 10 and 11 Structural formulas showing hydrogen bonding structures between compounds for an organic device according to an exemplary embodiment of the present invention are described in FIGS. 10 and 11. With reference to this will be described the hydrogen bonding properties of the compound according to an embodiment of the present invention.
  • Compound for an organic device according to an embodiment of the present invention can form a three-dimensional bond between the compound, as shown in Figure 10 and 11, and finally formed by adjusting the number of functional groups containing a pyrimidine ring
  • the hardness of the thin film can be controlled. More specifically, it is possible to provide a plurality of binding sites for binding functional groups through chemical reactions at the ends of the compounds having hole transporting properties according to the present invention, and to control the number of functional groups bound to the compounds having hole transporting properties. have.
  • the hardness of the thin film increases as a thin film having a more dense structure is formed by hydrogen bonding in the functional period including the pyrimidine ring.
  • the compound for an organic device having two or more functional groups including a pyrimidine ring may be a compound represented by the following Formula 9a.
  • Pym1 to Pym3 may be the same as or different from each other, and at least two or more of Pym1 to Pym3 are functional groups including a pyrimidine ring, and the rest are hydrogen.
  • the compound for an organic device having two or more functional groups containing a pyrimidine ring may be a compound represented by the following formula (10a).
  • Pym 4 to Pym 9 may be the same as or different from each other, at least two or more of Pym 4 to Pym 9 are functional groups including a pyrimidine ring, and the rest are hydrogen.
  • the first solvent may be a mixed solvent including one or two or more selected from dimethyl sulfoxide (DMSO), dimethylformamide (DMF), acetonitrile (ACN), and hexamethylphosphoamide (HMPA). It should be noted that this is not limiting. However, it may be preferable to use a polar aprotic solvent that can lower the activation energy to improve the reaction efficiency, more preferably the first solvent may be a high boiling point and chemically stable DMSO.
  • DMSO dimethyl sulfoxide
  • DMF dimethylformamide
  • ACN acetonitrile
  • HMPA hexamethylphosphoamide
  • the hole transport compound may be a compound represented by the following Formula 12a.
  • the compound containing the pyrimidine ring is added to the solution of the second step and reacted for a predetermined time to prepare a compound for an organic device represented by the formula (13a).
  • the compound containing a pyrimidine ring may be a compound represented by the following Chemical Formula 13a.
  • n means an integer of 0 to 10, and when n is 0, it means that “-COOH” is directly bonded to the pyrimidine ring.
  • the compound including the added pyrimidine ring may be bonded to the terminal of the hole transport compound under a catalyst to form a compound for an organic device represented by Formula 9a.
  • the third step may be carried out at a temperature of 20 to 70 °C for 4 to 15 hours, in this case, when the reaction temperature is less than 20 °C, the reaction efficiency is low, the reaction time is long, the final yield of the obtained compound If the reaction temperature exceeds 60 ° C, hydrogen bonding between the compounds proceeds, which is not preferable because the viscosity may be excessively increased.
  • one embodiment of the present invention may further comprise the step of removing the unreacted material and the solvent by washing several times with an organic solvent after the third step is completed, to improve the purity.
  • the compound for an organic device is a step of starting a reaction by mixing a potassium phosphate (potassium phosphate) and a third solvent as a catalyst and stirred for a predetermined time, represented by the formula 12b to the third solvent
  • a potassium phosphate potassium phosphate
  • a third solvent as a catalyst
  • the pyrimidine-based compound is dissolved in the first solvent, it is added to the solution of the second step, and reacted for a predetermined time
  • the main step is to prepare a compound for an organic device having a pyrimidine-based functional group, and further comprising the step of washing and purifying the product.
  • RX 1 to RX 6 may be the same as or different from each other, and at least two or more of RX 1 to RX 6 are alkyl halide groups.
  • alkyl halide group in the present invention may be represented by the general formula -CnH2n X, where X means a halogen such as F, Br, I, Cl, etc.) Pyrimidine ring by heterogeneous decomposition of CX bond under catalyst A binding site for introducing a functional group including a compound may be formed to prepare a compound for an organic device.
  • the compound containing a pyrimidine ring may be a compound represented by the following Chemical Formula 13b.
  • n is an integer of 2 to 10.
  • the third step of the present invention may be preferably carried out for 2 to 80 hours at a temperature of 20 to 60 °C.
  • the reaction temperature is less than 20 ° C, the reaction time may be long and the yield may decrease due to the decrease in the reaction rate, and when the reaction temperature is 60 ° C or higher, it may be difficult to secure the stability of the reactants.
  • the method of forming an organic thin film layer dissolving a compound for an organic device having two or more functional groups including a pyrimidine ring in a second solvent to prepare a solution, preparing a substrate Step, the step of applying the solution on top of the substrate, the step of heat-treating the substrate to which the solution is applied for a predetermined time to form a thin film, and having two or more functional groups containing a pyrimidine ring
  • the compound for an organic device may be characterized by being soluble in a second solvent at room temperature.
  • the fourth solvent is 1,2,3-trichlorobenzene (1,2,3-Trichlorobenzene), 1,2,4-trichlorobenzene (1,2,4-Trichlorobenzene), 1,3,5- Trichlorobenzene (1,3,5-Trichlorobenzen), chloroform (chloroform), tetrahydrofuran (Tetrahydrofuran) and may be a mixed solvent containing one or two or more selected from ethanol, but is not limited thereto. Specify it.
  • the substrate for applying the solution may be selected from glass and plastic substrates such as polyimide (PI), polyethylene terephthalate (PET), polyethylenetaphthalate (PEN), polycarbonate (PC), and the like.
  • PI polyimide
  • PET polyethylene terephthalate
  • PEN polyethylenetaphthalate
  • PC polycarbonate
  • any material may not be deformed under the above temperature conditions, and a glass substrate coated with a transparent electrode material such as an ITO substrate, an FTO substrate, and an AZO substrate may be used. State that
  • the method of applying the solution to the substrate is selected from the group consisting of spin coating, gravure offset printing, reverse offset printing, screen printing, roll-to-roll printing, slot die coating, immersion coating, spray coating, doctor blade coating, inkjet coating It can be done in either way.
  • the step of heat-treating the substrate to which the solution is applied for a predetermined time is carried out at a temperature of 70 to 170 °C, characterized in that the thin film is formed by the hydrogen bond of the working period provided in the compound for an organic device.
  • the organic light emitting compound according to the present invention may be cured by hydrogen bonding in a working period including a pyrimidine ring at a predetermined temperature condition to form a thin film.
  • the temperature is less than 70 °C, it may be difficult to form a thermally stable organic thin film because the curing temperature is not sufficient, there may be a problem that the process time is long.
  • the heat treatment temperature exceeds 170 °C it is limited to the above temperature because it is not possible to ensure the stability of the substrate and the compound due to excessive heat, but is not limited thereto.
  • the compound for an organic device and the organic thin film layer prepared by using the same according to the present invention may be applied to various organic devices including an organic photoconductor, an organic transistor, an organic solar cell, an organic light emitting device, and an organic image sensor.
  • organic devices including an organic photoconductor, an organic transistor, an organic solar cell, an organic light emitting device, and an organic image sensor.
  • a method for manufacturing an organic light emitting diode according to an embodiment of the present invention will be described in detail, but the application field of the organic compound according to the present invention is not limited thereto.
  • FIG. 18 is a schematic view showing a cross-sectional view of an organic light emitting device according to an embodiment of the present invention.
  • the method of manufacturing an organic light emitting diode includes a first step of preparing a substrate, a second step of forming an anode on the top of the substrate, a third step of forming a hole injection layer on the top of the anode, A fourth step of forming a hole transport layer on top of the hole injection layer, a fifth step of forming a light emitting layer on top of the hole transport layer, a sixth step of forming a hole blocking layer on top of the light emitting layer, and an electron transport layer formed on the hole blocking layer
  • the seventh step is performed, including the eighth step of forming a cathode on the upper portion of the electron transport layer, the hole injection layer is characterized in that formed by the method for producing an organic thin film according to the present invention.
  • the first step of preparing the substrate and the second step of forming the anode may be any substrate and anode material commonly used in the manufacture of the organic light emitting device.
  • the substrate is glass
  • the positive electrode material may be indium tin oxide (ITO), but is not limited thereto.
  • the hole injection layer (HIL) provided on the upper portion of the anode is formed to include a compound that facilitates the hole injection by lowering the injection energy barrier of the hole injected from the anode, such as 4 , 4 ', 4 "-Tris (N, N-diphenyl-amino) triphenylamine (NATA), 4,4', 4" -Tris (N-3-methylphenyl-N-phenyl-amino) triphenylamine (m-MTDATA)
  • poly (3,4-ethylenedioxythiophene): poly (styrenesulphonic acid) (PEDOT: PSS) and the like are known, and any material for a known hole injection layer may be used without limitation.
  • the hole injection layer may be formed by spin coating a PEDOT: PSS solution.
  • a hole transport layer serves to transport the hole injected from the anode to the light emitting layer without losing the hole, and may be formed including the compound for an organic device according to an embodiment of the present invention.
  • the hole transport layer may be formed by applying a coating solution prepared by using a compound for an organic device having two or more functional groups including a pyrimidine ring and heating to a temperature of 70 to 170 °C.
  • an emitting material layer is a layer that emits light through recombination of holes injected from the anode and electrons injected from the cathode, and emits red, blue, and green light according to binding energy in the emitting layer.
  • the white light emitting layer may be formed by forming a plurality of light emitting layers.
  • the light emitting layer may be formed by including a compound having luminescence or phosphorescence properties alone, or may be formed by doping a compound having fluorescence or phosphorescence properties to a host material having hole or electron transporting properties.
  • a light emitting layer In the case of a single compound, it may be desirable to form a light emitting layer by adding a dopant to a host material because the light emitting property is very excellent, but the hole or electron transport ability is difficult to produce a high efficiency organic photoelectric device.
  • the host material and dopant can be used without limitation as long as it is a known compound.
  • Known host materials include fluorescent conjugated polymers such as poly (p-phenylenevinylene), polypropylene (p-phenylene), polypropylene (PT), polythiophene (PT), polyfluorene (PF), poly (9.9-dioctylfluorene) (PFO), and Carbazole-based compounds such as CBP (4,4-N, N'-dicarbazole-biphenyl) or MCP (N, N'-dicarbazolyl-3,5-benzene) and the like.
  • fluorescent conjugated polymers such as poly (p-phenylenevinylene), polypropylene (p-phenylene), polypropylene (PT), polythiophene (PT), polyfluorene (PF), poly (9.9-dioctylfluorene) (PFO), and Carbazole-based compounds such as CBP (4,4-N, N'-dicarbazole-biphenyl) or MCP (N, N'-dicarba
  • Green phosphorescent dopant including Tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), Bis (2-phenylpyridine) (acetylacetonate) iridium (III) (Ir (ppy) 2 (acac)) (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III) (FirPic), Bis (2,4-difluorophenylpyridinato) -tetrakis (1-pyrazolyl) borate iridium (III) ( Blue phosphorescent dopants including Fir6), Tris (1-phenylisoquinoline) iridium (III) (Ir (piq) 3), Tris (2-phenylquinoline) iridium (III) (Ir (2-phq) 3), and the like. It may be, but not limited to, a red phosphorescent do
  • the hole blocking layer plays a role of suppressing the movement of holes that do not combine with electrons in the light emitting layer
  • the hole blocking layer is Balq, 2,2 ', 2 "-(1,3,5-benzinetriyl) -tris (1-phenyl-1-H-benzimidazole) (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc. It can be formed by depositing a material of.
  • the electron transport layer serves to transport the electrons injected from the cathode to the light emitting layer, thereby improving the coupling probability of holes and electrons in the light emitting layer.
  • the electron transport layer is Alq3 (Tris (8-hydroxy-quinolinato) aluminium), Balq (Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminium), BeBq2 (Bis (10- It may be formed by depositing one or more materials selected from the group consisting of hydroxybenzo [h] quinolinato) beryllium).
  • the electron injection layer serves to facilitate the injection of electrons from the cathode by lowering the potential barrier during electron injection.
  • the electron injection layer is LiF, 8 -Hydroxyquinolinolato-lithium (Liq), 1,3,5-tri [(3-pyridyl) -phen-3-yl] benzene (TmPyPB) may be formed by depositing one or more materials selected from the group consisting of.
  • the next step is to form a cathode on top of the electron injection layer.
  • the negative electrode material may be formed by depositing a material having a small work function value such as lithium (Li), magnesium (Mg), calcium (Ca), aluminum (Al), Al: Li, Ba: Li, or Ca: Li. have.
  • a solution prepared by dissolving 1 g of N, N-bis (4-aminophenyl) benzene-1,4-diamine in 50 ml of DMSO was slowly added to a round bottom flask and stirred for 30 minutes.
  • a solution prepared by dissolving 1.85 g of orotic acid in 100 ml of DMSO was slowly added to a round bottom flask and stirred at 40 ° C. for 12 hours.
  • a glass substrate provided with ITO having a thickness of 20 nm and a sheet resistance of 15 ⁇ s / ⁇ was used as the anode.
  • the ITO substrate was ultrasonically washed and dried for 30 minutes with acetone, isopropyl alcohol, and distilled water to remove impurities.
  • uracil-TPA was dissolved in trichlorobenzene to prepare a 20 wt% solution, the solution was coated on the top of the anode by spin coating, and then cured at a temperature of 100 ° C. for 30 minutes. An injection layer was formed.
  • NPB N, N'-bis (1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine
  • the hole transport layer was formed by vacuum deposition under conditions of a vacuum degree of 1 ⁇ 10 ⁇ 7 Pa and a deposition rate of 2 nm / s.
  • a hole blocking layer was formed by vacuum depositing TPBi (tris (N-arylbenzimidazole) under the same deposition conditions on the light emitting layer, and on the top thereof, Alq3 (Tris- (8-hydroxyquinoline) aluminum), An organic light emitting device was manufactured by vacuum deposition of LiF and Al as cathodes.
  • TPBi tris (N-arylbenzimidazole)
  • Alq3 Tris- (8-hydroxyquinoline) aluminum
  • the organic light emitting device has the structure of ITO / uracil-TPA (30nm) / NPB (30nm) / CBP + Ir (PPy) 3 (7wt%) (30nm) / TPBi (10nm) / Alq3 (30nm) / LiF / Al was prepared.
  • An organic light-emitting device was manufactured under the same conditions as in Example 5, except that uracil-TPD was dissolved in trichlorobenzene as a hole injection material to prepare a 30 wt% solution and formed on top of the positive electrode.
  • the organic light emitting device has the structure of ITO / uracil-TPD (35nm) / NPB (30nm) / CBP + Ir (PPy) 3 (7wt%) (30nm) / TPBi (10nm) / Alq3 (30nm) / LiF / Al was prepared.
  • Example 5 The same ITO substrate as in Example 5 was prepared and ultrasonically washed and dried with acetone, isopropyl alcohol and distilled water for 30 minutes to remove impurities.
  • a hole injection material PEDOT: PSS (PH4083, Celvios) was coated on the surface coated with ITO by spin coating, and dried at a temperature of 120 ° C. for 30 minutes to form a hole injection layer.
  • NPB NPB
  • a hole transport material was deposited on the hole injection layer under the same conditions as in Example 5 to form a hole transport layer, and a light emitting layer was formed on the same material as in Example 5 and under the same conditions.
  • Example 5 Except for the use of BCP (bathocuproine) as the hole blocking layer, a hole blocking layer, an electron transport layer and a cathode were formed under the same conditions as in Example 5 to prepare an organic light emitting device.
  • BCP bathoproine
  • the organic light emitting device was manufactured in the structure of ITO / PEDOT: PSS / NPB (30nm) / CBP + Ir (PPy) 3 (7wt%) (30nm) / BCP (10nm) / Alq3 (30nm) / LiF / Al. .
  • the current flowing through the unit device was measured by using a current-voltmeter while changing the voltage of the organic light emitting diode from 0 V to 14 V.
  • the luminous efficiency according to the change of the current density was measured by using a luminance meter while changing the current density from 0 mA / Cm2 to 500 mA / Cm2. The results are shown in FIGS. 12 to 15.
  • FIG. 12 is a voltage-current (V-I) curve of Example 4 and Comparative Example 3.
  • V-I voltage-current
  • Example 14 is a voltage-current (V-I) curve of Example 6 and Comparative Example 3.
  • V-I voltage-current
  • Example 6 As in the result of Example 5, the organic light emitting device according to Example 6 was found to have a higher power than the organic light emitting device according to Comparative Example 3. However, in Example 6, it was found that the power difference between Comparative Example 3 and the comparative example 3 is smaller than the power difference between Example 5 and Comparative Example 3, through which the uracil-TPD than the uracil-TPA hole layer of the organic light emitting device It can be seen that more effective material.
  • 15 is a graph showing changes in luminous efficiency with respect to current densities of Example 6 and Comparative Example 3. FIG. Referring to this, the luminous efficiency of the organic light emitting device according to Example 6 shows a larger reduction ratio as the current density increases, but it can be seen that the initial luminous efficiency is almost similar to that of the organic light emitting device according to the comparison 3. .
  • PEDOT: PSS PH4083, Celvios
  • a compound represented by the formula (uracil-TPD) was dissolved in trichlorobenzene to prepare a 30 wt% solution, and the solution was coated on the top of the hole injection layer by spin coating, followed by a temperature of 100 ° C. Curing for 30 minutes to form a hole transport layer having a thickness of 25mm.
  • alkyl-MCP alkyl-substituted-1,3-Bis (N-carbazolyl) benzene
  • a blue phosphorescent dopant FIr6 was mixed at 7wt% to prepare a light emitting layer solution.
  • the light emitting layer solution was spin-coated on top of the hole transport layer to form a light emitting layer.
  • TPBi, Alq3, LiF and Al were deposited under the same conditions and methods as in Example 5 to fabricate the device.
  • the organic light emitting device was manufactured in the structure of ITO / PEDOT: PSS / uracil-TPD (25nm) / alkyl-MCP + FIr6 (7wt%) (30nm) / TPBi (10nm) / Alq3 (30nm) / LiF / Al. .
  • the alkyl-MCP is a compound represented by the following formula.
  • An organic light emitting diode was manufactured according to the same conditions and methods as in Example 3, except that a light transport layer having a thickness of 20 mm was formed on the hole injection layer and 9 wt% of a blue phosphorescent dopant was mixed to prepare a light emitting layer solution. Finally, the organic light emitting device was manufactured in the structure of ITO / PEDOT: PSS / uracil-TPD (20nm) / alkyl-MCP + FIr6 (9wt%) (30nm) / TPBi (10nm) / Alq3 (30nm) / LiF / Al. .
  • Example 7 Except for depositing NPB in the same manner as in Example 1 to form a hole transport layer and the light emitting layer solution prepared by dissolving MCP and FIr6 (7wt%) in chlorobenzene is deposited on top of the hole transport layer to form a light emitting layer An organic light emitting diode was manufactured under the same condition as in Example 7. Finally, the organic light emitting device was manufactured in the structure of ITO / PEDOT: PSS / alkyl-MCP + FIr 6 (9 wt%) (30 nm) / TPBi (10 nm) / Alq 3 (30 nm) / LiF / Al.
  • Example 7 and Example 8 even though the hole injection layer, the hole transport layer and the light emitting layer were all coated by the spin coating method, that is, the solution process, it was confirmed that a stable multilayer thin film was formed without dissolving the lower layer portion.
  • the current and the current according to the change of the voltage of the organic light emitting device according to Examples 7, 8 and Comparative Example 4 The luminous efficiency was measured according to the change of density.
  • Example 7 and Example 8 analyzed the performance change of the organic light emitting device according to the thickness by varying the thickness of the hole transport layer. Measurements were performed under the same conditions and methods as described above, and the results are shown in FIGS. 16 and 17.
  • V-I voltage-current
  • Example 17 is a graph showing changes in luminous efficiency with respect to current densities of Example 7, Example 8 and Comparative Example 4.
  • FIG. Referring to this, it can be seen that the organic light emitting diode according to Example 7 and Example 8 is higher than the luminous efficiency of the organic light emitting diode according to Comparative Example 4.
  • Example 7 coated with the uracil-TPD in a thickness of 25nm it can be seen that the initial luminous efficiency is improved by about 2 times compared to Comparative Example 4.
  • the compound for an organic device according to the present invention has a property of excellent solubility in a solution by having a pyrimidine-based functional group at the terminal of a skeleton containing triphenylamine, and a solution prepared therefrom. It was confirmed that the formation of a stable organic thin film at a relatively low temperature (100 °C) compared to the prior art, it is possible to manufacture a multi-layered organic device without dissolving the lower layer. In addition, when the compound having the pyrimidine-based functional group is used as a hole layer, in particular a hole transport layer, it was confirmed that the luminous efficiency is greatly improved compared to the device manufactured through the conventional deposition process.

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Abstract

L'invention concerne, dans un mode de réalisation, un composé pour un dispositif organique, le composé comprenant un groupe fonctionnel comprenant un cycle pyrimidine et/ou un groupe fonctionnel comprenant un cycle pyrimidine, qui est inclus au niveau d'une terminaison d'un composé à base de carbazole comprenant du carbazole, un film mince organique étant formé par une liaison hydrogène entre les groupes fonctionnels.
PCT/KR2016/010717 2015-09-25 2016-09-23 Composé organique devant être utilisé dans un dispositif organique et procédé de fabrication de dispositif organique l'utilisant WO2017052308A2 (fr)

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KR10-2015-0136848 2015-09-25
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KR1020160045725A KR101859123B1 (ko) 2016-04-14 2016-04-14 유기소자의 정공차단층 및/또는 전자수송층에 사용될 수 있는 신규한 화합물 및 이를 포함하는 유기박막의 제조방법 및 유기발광소자
KR10-2016-0045725 2016-04-14
KR1020160120760A KR101888562B1 (ko) 2015-09-25 2016-09-21 유기소자용 화합물 및 이를 포함하는 유기발광소자
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CN108912105A (zh) * 2018-08-03 2018-11-30 瑞声科技（南京）有限公司 一种对称取代的双咔唑化合物及其应用
KR20180130859A (ko) * 2017-05-30 2018-12-10 한국생산기술연구원 유기소자 박막 형성용 코팅액, 이의 제조방법 및 이에 의해 제조된 유기소자
CN110157241A (zh) * 2019-05-13 2019-08-23 深圳市华星光电半导体显示技术有限公司 一种喷墨打印墨水及其应用
KR102056936B1 (ko) * 2018-02-26 2019-12-17 한국생산기술연구원 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20200069184A (ko) * 2018-12-06 2020-06-16 한국생산기술연구원 피리미딘계 작용기 함유 단분자 화합물, 상기 화합물의 광가교물을 포함한 유기물층 및 이를 포함하는 유기전자소자
US11359106B2 (en) 2019-05-13 2022-06-14 Shenzhen China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Inkjet printing ink and application thereof

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KR20100114749A (ko) * 2009-04-16 2010-10-26 에스에프씨 주식회사 알루미늄 착물 유도체 및 이를 이용한 유기전계발광소자
KR20130122321A (ko) * 2012-04-30 2013-11-07 순천향대학교 산학협력단 화합물을 활용한 유기발광소자
US9074043B2 (en) * 2012-08-17 2015-07-07 Harvatek Corporation Compound for carrier transport, element and electronic device using the same

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KR20180130859A (ko) * 2017-05-30 2018-12-10 한국생산기술연구원 유기소자 박막 형성용 코팅액, 이의 제조방법 및 이에 의해 제조된 유기소자
KR102029676B1 (ko) 2017-05-30 2019-10-10 한국생산기술연구원 유기소자 박막 형성용 코팅액, 이의 제조방법 및 이에 의해 제조된 유기소자
KR102056936B1 (ko) * 2018-02-26 2019-12-17 한국생산기술연구원 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN108912105A (zh) * 2018-08-03 2018-11-30 瑞声科技（南京）有限公司 一种对称取代的双咔唑化合物及其应用
KR20200069184A (ko) * 2018-12-06 2020-06-16 한국생산기술연구원 피리미딘계 작용기 함유 단분자 화합물, 상기 화합물의 광가교물을 포함한 유기물층 및 이를 포함하는 유기전자소자
KR102127006B1 (ko) * 2018-12-06 2020-06-25 한국생산기술연구원 피리미딘계 작용기 함유 단분자 화합물, 상기 화합물의 광가교물을 포함한 유기물층 및 이를 포함하는 유기전자소자
CN110157241A (zh) * 2019-05-13 2019-08-23 深圳市华星光电半导体显示技术有限公司 一种喷墨打印墨水及其应用
WO2020228264A1 (fr) * 2019-05-13 2020-11-19 深圳市华星光电半导体显示技术有限公司 Encre d'impression à jet d'encre et son application
US11359106B2 (en) 2019-05-13 2022-06-14 Shenzhen China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Inkjet printing ink and application thereof

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