WO2019190270A1 - Novel compound and organic light-emitting device comprising same - Google Patents

Novel compound and organic light-emitting device comprising same Download PDF

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WO2019190270A1
WO2019190270A1 PCT/KR2019/003723 KR2019003723W WO2019190270A1 WO 2019190270 A1 WO2019190270 A1 WO 2019190270A1 KR 2019003723 W KR2019003723 W KR 2019003723W WO 2019190270 A1 WO2019190270 A1 WO 2019190270A1
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group
unsubstituted
substituted
formula
compound
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PCT/KR2019/003723
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French (fr)
Korean (ko)
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함호완
안현철
강경민
김희주
김동준
한정우
임동환
이형진
안자은
김승호
권동열
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주식회사 동진쎄미켐
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Priority to CN201980023698.XA priority Critical patent/CN111936481B/en
Publication of WO2019190270A1 publication Critical patent/WO2019190270A1/en

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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

  • Novel compound and organic light emitting device including the same ⁇ NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DIVICE INCLUDING THE SAME ⁇
  • the present application relates to a novel compound and an organic light emitting device comprising the same.
  • the material used as the organic material layer in the organic light emitting diode can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
  • the light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
  • a host / dopant system may be used as a light emitting material.
  • the principle is that when a small amount of dopant having a small energy band gap and excellent luminous efficiency is mixed with the light emitting layer, the excitons generated from the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and host used.
  • the present application provides a novel organic compound, and an organic light emitting device comprising the same.
  • the problem to be solved by the present application is not limited to the problem described above, other problems that are not described will be clearly understood by those skilled in the art from the following description.
  • a first aspect of the present application provides a compound represented by Formula 1 below:
  • 1 is 0 or an integer of 1 to 4
  • 01 and II are each independently 0 or an integer of 1 to 3
  • a second aspect of the present application provides an organic light emitting device comprising an organic layer containing a compound according to the present application between a first electrode and a second electrode.
  • Compound according to an embodiment of the present invention is a tricyclic condensed ring group (dibenzofuran, dibenzothiophene or fluorene) and dibenzofuran is connected to the nitrogen of the arylamine through a linking group
  • dibenzofuran is connected to the nitrogen of the arylamine through a linking group
  • the compound according to an embodiment of the present invention is easy to block the electrons by maintaining a high LUM0 and T1 by introducing a tricyclic condensed ring group having excellent electron resistance to one side of the arylamine, and maximizes the exciton confinement effect in the light emitting layer Can be. Accordingly, high efficiency and long life organic light emitting device can be realized.
  • the compound according to an embodiment of the present invention can improve the arrangement of molecules when forming a thin film by forming the connection position 2 or 4 of the dibenzofuran having a small bulky property on one side of the arylamine, and implements low voltage And it is possible to implement a long life organic light emitting device by suppressing the roll-off phenomenon.
  • the compound according to an embodiment of the present invention may be increased by one side of the arylamine is connected to the dibenzofuran through a linking group, and having the aryl group on the other side. Accordingly, the hole mobility can be improved and a low driving voltage can be realized when applied to the organic light emitting device.
  • the compound according to an embodiment of the present invention includes a tricyclic condensed ring group expanded through dibenzofuran on one side of the arylamine to form a high Tg to prevent thin film recrystallization, accordingly organic light emitting device Driving stability of can be secured.
  • FIG. 1 shows a schematic view of an organic light emitting device according to an embodiment of the present disclosure.
  • the term "combination of these" included in the expression of the makushi form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the makushi form, Military history of elements 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • ⁇ aryl '' refers to an aromatic hydrocarbon ring group of 06-50, for example phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, phen ⁇ Heteroaryl '', meaning containing aromatic rings such as rillenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzo chrysenyl, anthracenyl, stilbenyl, pyrenyl, etc.
  • Is a 05-50 aromatic ring containing at least one hetero element for example pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindoleyl, furyl, benzofuranyl, isobenzofuranyl, dibenzo Furanyl, benzothiophenyl, dibenzothiophenyl, quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine ring, pyrazine ring, Pipe Dean ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring Thiophene
  • substituted or unsubstituted is halogen, amino group, nitrile group, nitro group or 0 20 alkyl group, 02 20 alkenyl group, Le 20 alkoxy group, 03 020 cycloalkyl group, 0 3 ⁇ 020 £ 1 heterocycloalkyl, 06 ⁇ 30 aryl and 03-030 £ 1 heteroaryl 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • ⁇ fluorane '' refers to a substituted or unsubstituted -20 alkyl group, a substituted or unsubstituted 05-30 aryl group, or a substituted or unsubstituted 03-30 heteroaryl group, wherein hydrogen bonded to carbon 9 is substituted. It may mean a substituted case.
  • the first aspect of the present application provides a compound represented by the following formula (1).
  • ⁇ 2 is substituted or unsubstituted Or a substituted or unsubstituted 05 to 030 hetero arylene group,
  • 1 is 0 or an integer of 1 to 4,
  • 01 and II are each independently 0 or an integer of 1 to 3, wherein 1, 01 or II is 2 or more It can be the same or different.
  • the compound according to the embodiment of the present invention is suitable for the light emitting auxiliary layer by connecting a tricyclic condensed ring group (dibenzofuran, dibenzothiophene or fluorene) and dibenzofuran with nitrogen of arylamine through a linking group. It is possible to form a level, thereby realizing an organic light emitting device having high efficiency.
  • the compound according to an embodiment of the present invention is easy to block electrons by maintaining a high !! ⁇ ) and 11 by introducing a tricyclic condensed ring group having excellent electron resistance on one side of the arylamine, and the exciton confinement effect in the light emitting layer Can be maximized. Accordingly, high efficiency and long life organic light emitting device can be realized.
  • the compound according to an embodiment of the present invention is arranged on the side of the aryl amine 2 or 4 of the dibenzofuran having a small bulky property as a connection position to arrange the arrangement of the molecules when forming a thin film It is possible to achieve excellent, and to achieve a long life of the organic light emitting device through the implementation of low voltage and suppression of the roll-off phenomenon.
  • linking position number of the tricyclic condensed ring compound may be as follows.
  • the compound according to an embodiment of the present invention may be increased by one side of the arylamine is connected to the dibenzofuran through a linking group, and having the aryl group on the other side.
  • hole mobility (3 ⁇ 416 010 ⁇ 1) can be improved, and low driving voltage can be realized when applied to organic light emitting devices.
  • the compound according to an embodiment of the present invention includes a tricyclic condensed ring group extended through dibenzofuran on one side of the arylamine to form a high solvent to prevent thin film recrystallization, thereby Driving stability can be secured. Seen .
  • the compound may be represented by the formula (2).
  • Fig. 7 shows hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted 30 alkyl group, substituted or unsubstituted 02 ⁇ 30 alkenyl group, substituted or unsubstituted (: 1 30 alkoxy group, substituted or unsubstituted ( : 1 3 ⁇ sulfide group, substituted or unsubstituted 06-030 ⁇ aryl group, or substituted or unsubstituted 05-030 £] heteroaryl group,
  • 0 is an integer of 1 to 4, is 0 or an integer of 1 to 4, the figure 7 may be the same or different when 0 or V is 2 or more, 13 may be the same or different when 0 is 2 or more. .
  • the compound represented by the formula (2) is a case in which 1 ⁇ 2 in the formula (1) includes phenylene, a form in which one or more phenylene is bonded between a dibenzofuran which is a substituent of arylamine and nitrogen of the arylamine to be.
  • the compound can maintain a high 11 due to the phenylene group at the same time forming a suitable 3 ⁇ 43 ⁇ 4 10 in the light emitting auxiliary layer, it can be more effective in blocking excitons.
  • the compound may be represented by the following formula (3). 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • 0 is an integer from 1 to 4, is 0 or an integer from 1 to 4,
  • ⁇ When 0 or 13 is 2 or more, ⁇ may be the same or different, and when 0 is 2 or more, I) may be the same or different.
  • Compound represented by the formula (3) is a direct bond in the formula (1), dibenzofuran and tricyclic condensed ring group (dibenzofuran, dibenzothiophene or fluorene series) is directly connected deep ⁇ ⁇ ) By forming a level, an organic light emitting device having high efficiency can be realized.
  • the compound is represented by the following formula (4) 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723 may be displayed.
  • X is 0 or
  • 1 or 2 can be the same or different
  • Fig. 7 is hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted LE 30 alkyl group, substituted or unsubstituted 02 ⁇ 30 ⁇ ] alkenyl group, substituted or unsubstituted LE 30 alkoxy group, substituted or unsubstituted 30 sulfide group, substituted or unsubstituted 06-030 ⁇ aryl group, or substituted or unsubstituted 05 30 heteroaryl group, 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • 0 is an integer of 1 to 4
  • I) is 0 or an integer of 1 to 4
  • Fig. 7 may be the same or different, and when 0 is 2 or more, I) may be the same or different.
  • high hole mobility and high 11 can be maintained, which is effective for low voltage driving, and can be effective for blocking electrons flowing from the light emitting layer into the hole transport layer.
  • the compound may be represented by the following formula (6).
  • 0 is an integer of 1 to 4
  • I) is 0 or an integer of 1 to 4
  • mother 7 When 0 or I? Is 2 or more, mother 7 may be the same or different, and when 0 is 2 or more, 13 may be the same or different.
  • the compound may be represented by the following formula (7) or formula (8).
  • X is 0 or
  • Fig. 7 is hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted (: 1 30 alkyl group, substituted or unsubstituted (: 2 30 alkenyl group, substituted or unsubstituted 01 ⁇ 030 £] alkoxy group, substituted Or an unsubstituted (: 1 30 sulfide group, a substituted or unsubstituted 06 30 aryl group, or a substituted or unsubstituted 05 ⁇ 030 £ 1 heteroaryl group,
  • 0 is an integer from 1 to 4, is 0 or an integer from 1 to 4,
  • the ⁇ 0 and II at the same time as fast hole mobility, and it is easy to block electrons and excitons, and thus may be effective in improving luminous efficiency and lifespan by improving roll-off phenomenon.
  • all 1, 111, II, 0, V may be 0.
  • 3 ⁇ 4 to parent 7 may be each independently hydrogen, (1 ⁇ 0 alkyl group, or phenyl group. More specifically, seed 1 to silver may be hydrogen or a phenyl group.
  • Formula 1 to Formula 3 and Formula 6 I? And I? ' Can be each independently an alkyl group of.
  • X in Formula 1 to Formula 5, Formula 7, and Formula 8 may be 0.
  • the formula 1 to formula 5 the formula 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • X may be.
  • urethane is phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl , Dibenzothiophenyl and combinations thereof
  • 2 represents biphenyl, phenylnaphthyl, terphenyl, fluorenyl, dialkyl fluorenyl, diaryl fluorenyl and dibenzofuranyl. , Dibenzothiophenyl and combinations thereof.
  • Chemical Formula 1 may be a substituted or unsubstituted 06 24 arylene group including at least one 1, 4-phenylene group or 1, 3-phenylene group.
  • At least one of 1, 2 and Ne 2 in the formula (1) may include a phenylten group having a meta bond.
  • 1 is biphenyl having a meta bond or terphenyl having a meta bond
  • 2 is terphenyl having a biphenyl having a meta bond or a meta bond.
  • any one or more of the following 3) to 0) may be satisfied:
  • At least one is a (: 14 or more aryl group) and the above-mentioned arylene group which consist only of a 6-membered ring.
  • the formula 1 to formula 8 in the above 1 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723 is selected from the group consisting of phenyl, biphenyl, terphenyl, dimethylfluorenyl and combinations thereof, wherein 2 is biphenyl, terphenyl, dimethylfluorene It may be selected from the group consisting of one and a combination thereof.
  • the compound represented by Formula 1 may be any one of the following compounds, but may not be limited thereto:
  • the second aspect of the present application provides an organic light emitting device comprising the compound represented by the formula (1).
  • the organic light emitting device may include one or more layers of organic insecticides containing a compound according to the present application between the first electrode and the second electrode.
  • the organic material layer may be a hole injection layer, a hole transport layer and a light emitting auxiliary layer, but may not be limited thereto.
  • the compounds of the present invention may be used alone or in combination with known compounds when forming the organic layer.
  • the organic light emitting device may include an organic material layer containing a hole transport material and an organic material layer containing a compound represented by Formula 1, but may not be limited thereto. 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • the organic light emitting device includes an anode (a hole injection layer ratio between a size 110 (16) and a cathode (0 ⁇ 110 (16)), a hole transport layer 0111), a light emitting layer ⁇ ⁇ ), an electron transport layer ,, an electron injection layer ( It may contain one or more organic layer, such as me.
  • the organic light emitting device may be manufactured as shown in FIG. 1.
  • the organic light emitting device is formed from the bottom of the anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection charge 600 / cathode (electron
  • the injection electrode 2000 may be stacked in this order.
  • the substrate 100 may be a substrate used in an organic light emitting device.
  • the substrate 100 may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Can be.
  • the hole injection electrode 1000 is used as an anode for hole injection of the organic light emitting device.
  • a material having a low work function is used to inject holes, and may be formed of transparent materials such as indum tin oxide ( ⁇ (1), indum zinc oxide (I ⁇ )) and graphene ( ⁇ 31 ⁇ 611 ⁇ 2). .
  • the hole injection layer material is deposited on the anode electrode by a method such as vacuum deposition, spin coating, casting, 1 solid (1! 1 ⁇ 1 1 10 (3 ⁇ 461; 1;) method, and the like.
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the desired hole injection layer, in general, 50-500 X:!! deposition temperature, 10_ 8 to 10_ 3 ⁇ degree of vacuum of 0.01 to 100% of the deposition rate of ⁇ , pan 10 ⁇ to 5 _ the layer thickness of the above can be properly selected. 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723
  • the hole transport layer 300 may be formed by deposition by the same method.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select it in almost the same conditions as the formation of the hole injection layer.
  • the hole transport layer 300 may use a compound according to the present invention. As described above, the compound according to the present invention may be used alone or a known compound may be used together. In addition, according to one embodiment of the present invention, the hole transport layer 300 may be one or more layers, and may include a hole transport layer formed only of a known material. In addition, according to the exemplary embodiment of the present invention, a light emitting auxiliary layer may be formed on the hole transport layer 300.
  • the light emitting layer 400 may be formed by depositing by the same method.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select in the same condition range as the formation of the hole injection layer.
  • the light emitting layer material may use a known compound as a host or dopant.
  • the hole-inhibiting substance that can be used at this time is not particularly limited, but is a known one used as a hole-inhibiting material 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723 Any one can be selected and used.
  • Hei 11-329734 (A), etc. are typically 831 (1 (bis (8 -Hydroxy-2-methylquinol linolato) -aluminum biphenoxide), phenanthroline Compounds (e.g., eg, Sans! 3 (Basocuproin)) and the like can be used.
  • An electron transport layer 500 is formed on the light emitting layer 400 formed as described above, wherein the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.
  • the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same conditions as the formation of the hole injection layer.
  • an electron injection layer material may be deposited on the electron transport certificate 500 to form an electron injection layer 600, wherein the electron transport layer may be formed by vacuum deposition, spin coating, or the like on the electron injection layer material. It can be formed by a method such as a cast method.
  • the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the total embroidery 500 of the organic light emitting device may use the compound according to the present invention, or may use the following materials, or the present invention.
  • the compound according to the present invention may be used together with a known material.
  • the cathode 2000 for electron injection is formed on the electron injection layer 600 by a method such as vacuum deposition or sputtering.
  • Various metals may be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.
  • the organic light emitting device of the present invention is not only an organic light emitting device having an anode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injection layer, and a cathode structure, but also a structure of organic light emitting devices having various structures. It is also possible to form one or two intermediate layers.
  • the thickness of each organic material layer formed in accordance with the present invention can be adjusted according to the required degree, specifically 1 to 1,000 to 1, more specifically 5 to 200.
  • the present invention is an organic material layer containing a compound represented by the formula (1) Since the thickness of the base layer can be adjusted in units of molecules, the surface is uniform and there is an excellent shape stability.
  • organic light emitting compound according to the present aspect may be applied to all of the contents described for the first aspect of the present application, but may not be limited thereto.
  • the embodiments of the present application will be described in more detail, and the scope of the present application is not limited by the present embodiment.
  • the compound represented by Formula 1 may be synthesized by the following reaction, but is not limited thereto.
  • Intermediate 3 ⁇ 4 may be synthesized through the following reaction for synthesis of the desired compound, but is not limited thereto. 2019/190270 1 »(: 1/10 ⁇ 019/003723
  • the intermediate was used to synthesize the target compounds 1-20. All.
  • Compound 12 was synthesized by the same method as Compound 1 using 1116 instead of «1 (yield 65%).
  • a glass substrate coated with indium tin oxide (IT0) having a thickness of 1500 A was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator on top of the IT0 substrate.
  • a thermal evaporator to form HI01 600 A, HATCN 50 A, HT01 250 A as a hole transport layer, Compound 1 100 A as a light emitting auxiliary layer, and then doping with BH01: BD01 3% in a light emitting layer to 250 A It produced.
  • ET01: Liq (l: l) 300 A was formed into an electron transport layer, followed by LiF 10 A and aluminum (Al) 1000 A, which were encapsulated in a glove box to produce an organic light emitting device. . Examples 22-40
  • the compound of the present invention is used as the light emitting auxiliary layer.
  • Examples 21 to 40 it can be seen that the efficiency and life is increased compared to Comparative Examples 1 to 11.
  • Examples 21 to 40 show fast hole mobility through linear linkage with dibenzothiophene, fluorene or dibenzofuran in which dibenzofuran is a tricyclic condensed ring. mobi li ty) to achieve low voltage characteristics.
  • Examples 21 to 40 was able to have a good efficiency by forming a deep HOMO by combining dibenzofuran, dibenzothiophene, fluorene or dibenzofuran which is a tricyclic condensed ring.
  • Examples 21 to 40 form a deep HOMO by including a linking group between the nitrogen of dibenzofuran and arylamine, and at the same time have low hole characteristics due to the rapid hole mobility due to the increase in the conjugation.
  • Examples 21 to 40 form a deep HOMO by including a linking group between the nitrogen of dibenzofuran and arylamine, and at the same time have low hole characteristics due to the rapid hole mobility due to the increase in the conjugation.
  • Examples 21 to 40 have positions of 2 or 4 of dibenzofuran having excellent electron resistance and low bulky properties. Combined with nitrogen, H0M0 and high LUM0, which is easy for hole transport, are maintained, and the intermolecular thin film arrangement is excellent.
  • Examples 21 to 40 have a benzofuran on one side of nitrogen, and having at least 12 aryl groups of carbon atoms on the other side, the conjugation can be increased, and hole mobility is increased. The improvement resulted in low voltage characteristics.
  • Examples 27 and 38 also include deeper phenylenes with meta bonds. 2019/190270 1 »(: 1 ⁇ 1 ⁇ 2019/003723

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Abstract

The present application relates to a novel compound and an organic light-emitting device comprising same, the novel compound according to one embodiment of the present invention being applied to an organic light-emitting device to allow same to be highly effective, and have extended lifespan, low driving voltage and operational stability.

Description

【명세서】  【Specification】
【발명의 명칭】  [Name of invention]
신규 화합물 및 이를 포함하는 유기발광 소자{NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DIVICE INCLUDING THE SAME}  Novel compound and organic light emitting device including the same {NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DIVICE INCLUDING THE SAME}
【기술분야】  Technical Field
본원은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. 【배경기술】  The present application relates to a novel compound and an organic light emitting device comprising the same. Background Art
유기발광다이오드에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발 광 재료， 정공주입재료， 정공수송 재료, 전자수송 재료， 전자주입 재료 등으로 분 류될 수 있다. 그리고 상기 발광 재료는 분자량에 따라 고분자와 저분자로 분류될 수 있고， 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료 와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있으며， 발광 재료는 발광색에 따라 청색， 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한， 색순도의 증가 와 에너지 전이를 통한 발광 효율을 증가시키기 위하여， 발광 물질로서 호스트/도 판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면， 호스트에 서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스 트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.  The material used as the organic material layer in the organic light emitting diode can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function. The light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. The light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material. The principle is that when a small amount of dopant having a small energy band gap and excellent luminous efficiency is mixed with the light emitting layer, the excitons generated from the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and host used.
현재까지 이러한 유기 발광 소자에 사용되는 물질로서 다양한 화합물들이 알 2019/190270 To date, various compounds are known as materials used in such organic light emitting devices. 2019/190270
려져 있으나， 이제까지 알려진 물질을 이용한 유기 발광 소자의 경우 높은 구동전 압, 낮은 효율 및 짧은 수명으로 인해 새로운 재료의 개발이 지속적으로 요구되고 있다. 따라서， 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수 명을 갖는 유기 발광소자를 개발하려는 노력이 지속되어 왔다. However, in the case of organic light emitting devices using materials known to date, there is a continuous demand for the development of new materials due to high driving voltage, low efficiency and short lifespan. Therefore, efforts have been made to develop organic light emitting devices having low voltage driving, high brightness and long life using materials having excellent characteristics.
【발명의 상세한설명】  Detailed Description of the Invention
【기술적 과제】  [Technical problem]
본원은신규한유기 화합물, 및 이를 포함하는 유기 발광 소자를 제공한다. 그러나 본원이 해결하고자 하는 과제는 이상에서 기술한 과제로 제한되지 않 으며, 기술되지 않은 다른 과제들은 아래의 기재로부터 당업자에게 명확하게 이해 될 수 있을 것이다.  The present application provides a novel organic compound, and an organic light emitting device comprising the same. However, the problem to be solved by the present application is not limited to the problem described above, other problems that are not described will be clearly understood by those skilled in the art from the following description.
【기술적 해결방법】  Technical Solution
본원의 제 1측면은 하기 화학식 1로 표시되는 화합물을 제공한다:  A first aspect of the present application provides a compound represented by Formula 1 below:
[화학식 1] [Formula 1]
Figure imgf000004_0001
Figure imgf000004_0001
!은 치환 또는 비치환의 06^50의 아릴기， 또는 치환 또는 비치환의 05-050 2019/190270 1»（：1/10公019/003723 의 해테로아릴기이고，Is a substituted or unsubstituted 06 ^ 50 aryl group, or a substituted or unsubstituted 05-050 2019/190270 1 »（: 1/10 公 019/003723 Heteroaryl group,
2는 치환또는 비치환의 （：12 50의 아릴기이고， 2 is a substituted or unsubstituted aryl group of 12 50:
Figure imgf000005_0001
독립적으로 수소， 할로겐, 니트로기， 니트릴기, 치 환 또는 비치환의 （：1 30의 알킬기， 치환 또는 비치환의 02~030£] 알케닐기， 치환 또 는 비치환의 （：1 0의 알콕시기， 치환또는 비치환의 （：1 30의 설파이드기 , 치환또는 비치환의 06 30의 아릴기， 또는 치환 또는 비치환의 05^30의 헤테로아릴기이고， 인 접한 복수의 ¾끼리 , 1?2끼리 ,
Figure imgf000005_0002
또는 I?과 요’ 는 서로 결합하여 환을 형성하거 나 형성하지 않을 수 있고， 묘4와 묘6 또는 ¾와 ¾은서로 결합하여 환을 형성하거나 형성하지 않을 수 있으며 ,
Figure imgf000005_0001
Independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted （: 1 30 alkyl group, substituted or unsubstituted 02-030 £] alkenyl group, substituted or unsubstituted （: 1 0 alkoxy group, substituted Or an unsubstituted （: 1 30 sulfide group, a substituted or unsubstituted 06 30 aryl group, or a substituted or unsubstituted 05 ^ 30 heteroaryl group, a plurality of adjacent ¾s, 1 to 2,
Figure imgf000005_0002
Or I? And Yo 'may be combined with each other to form a ring, or not, and tombs 4 and 6 or ¾ and ¾ may be combined to form or not form a ring.
은 직접결합 , 치환 또는 비치환의 06~030^ 아릴텐기， 또는 치환 또는 비치 환의 05-030^] 헤테로아릴렌기이고， Is a direct bond, substituted or unsubstituted 06-030 ^ arylten group, or substituted or unsubstituted 05-030 ^] heteroarylene group,
는 치환 또는 비치환의 06^30의 아릴텐기， 또는 치환 또는 비치환의 05~030 의 헤테로아릴렌기이고，  Is a substituted or unsubstituted 06 ^ 30 arylten group, or a substituted or unsubstituted 05-030 heteroarylene group,
1은 0 또는 1 내지 4의 정수이고， 01 및 II은 각각 독립적으로 0 또는 1 내지 3의 정수이며, 상기 1， [11 또는 ！!이 2 이상인 경우 ¾， ^2 및 묘3은 각각서로 같거나 다를수 있다.  1 is 0 or an integer of 1 to 4, 01 and II are each independently 0 or an integer of 1 to 3, and when 1, [11 or ！! is 2 or more, ¾, ^ 2 and seedling 3 are the same as each other. Can be different.
본원의 제 2 측면은 제 1 전극 및 제 2 전극사이에 본원에 따른 화합물을 함유 하는유기물층을포함하는 유기 발광소자를 제공한다.  A second aspect of the present application provides an organic light emitting device comprising an organic layer containing a compound according to the present application between a first electrode and a second electrode.
【발명의 효과】  【Effects of the Invention】
본 발명의 일 구현예에 따른 화합물은 3환축합고리기（다이벤조퓨란， 다이벤 조티오펜 또는 플루오렌）와 다이벤조퓨란이 연결기를 통하여 아릴아민의 질소와 연 결됨으로써 발광보조층에 적합한 HOMO 레벨을 형성할 수 있으며， 이에 따라 고효율 의 유기 발광소자를 구현할 수 있다. Compound according to an embodiment of the present invention is a tricyclic condensed ring group (dibenzofuran, dibenzothiophene or fluorene) and dibenzofuran is connected to the nitrogen of the arylamine through a linking group As a result, it is possible to form a suitable HOMO level for the light emitting auxiliary layer, thereby realizing an organic light emitting device having high efficiency.
또한， 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측에 전자 내성이 우수한 3환 축합고리기를 도입하여 높은 LUM0 및 T1을 유지하여 전자차단이 용이하 고, 발광층내 엑시톤 가둠 효과가 극대화될 수 있다. 이에 따라 고효율 및 장수명 의 유기 발광소자를 구현할수 있다.  In addition, the compound according to an embodiment of the present invention is easy to block the electrons by maintaining a high LUM0 and T1 by introducing a tricyclic condensed ring group having excellent electron resistance to one side of the arylamine, and maximizes the exciton confinement effect in the light emitting layer Can be. Accordingly, high efficiency and long life organic light emitting device can be realized.
또한, 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측에 벌키 특성이 작은 다이벤조퓨란의 2번 또는 4번을 연결 위치로 하여 박막 형성시 분자의 배열을 우수하게 할 수 있고， 저전압 구현 및 롤오프현상 억제를 통하여 장수명의 유기 발 광소자를 구현할수 있다.  In addition, the compound according to an embodiment of the present invention can improve the arrangement of molecules when forming a thin film by forming the connection position 2 or 4 of the dibenzofuran having a small bulky property on one side of the arylamine, and implements low voltage And it is possible to implement a long life organic light emitting device by suppressing the roll-off phenomenon.
또한， 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측이 연결기를 통 하여 다이벤조퓨란과 연결되고， 타측에 아릴기를 가짐에 따라 파이컨쥬게이션이 증 가할 수 있다. 이에 따라 홀모빌리티 (Hole mobi l i ty)를 개선할 수 있고, 유기 발광 소자에 적용시 낮은 구동전압을 구현할수 있다.  In addition, the compound according to an embodiment of the present invention may be increased by one side of the arylamine is connected to the dibenzofuran through a linking group, and having the aryl group on the other side. Accordingly, the hole mobility can be improved and a low driving voltage can be realized when applied to the organic light emitting device.
또한， 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측에 다이벤조퓨 란을 통하여 확장된 3환 축합고리기를 포함하여 높은 Tg를 형성하여 박막 재결정화 를 방지할수 있고, 이에 따라유기 발광 소자의 구동 안정성을 확보할수 있다. In addition, the compound according to an embodiment of the present invention includes a tricyclic condensed ring group expanded through dibenzofuran on one side of the arylamine to form a high Tg to prevent thin film recrystallization, accordingly organic light emitting device Driving stability of can be secured.
【도면의 간단한설명】 【Brief Description of Drawings】
도 1은 본원의 일 구현예에 따른 유기 발광 소자의 개략도를 나타낸 것이다. 1 shows a schematic view of an organic light emitting device according to an embodiment of the present disclosure.
【발명의 실시를 위한 최선의 형태】 [Best form for implementation of the invention]
이하, 첨부한도면을 참조하여 본 발명이 속하는 기술 분야에서 통상의 지식 2019/190270 1»（：1^1{2019/003723 Ordinary knowledge in the technical field to which the present invention belongs with reference to the accompanying drawings. 2019/190270 1 »（： 1 ^ 1 {2019/003723
을 가진 자가 용이하게 실시할 수 있도록 본원의 구현예 및 실시예를 상세히 설명 한다. Embodiments and examples of the present application will be described in detail so that those skilled in the art can easily carry out the present invention.
그러나 본원은 여러 가지 상이한 형태로 구현될 수 있으며 여기에서 설명하 는 구현예 및 실시예에 한정되지 않는다. 그리고 도면에서 본 발명을 명확하게 설 명하기 위해서 설명과 관계없는 부분은 생략하였으며， 명세서 전체를 통하여 유사 한부분에 대해서는 유사한 도면 부호를 붙였다.  As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention. In the drawings, parts irrelevant to the description are omitted in order to clearly describe the present invention, and like reference numerals designate like parts throughout the specification.
본원 명세서 전체에서， 어떤 부재가 다른 부재 ’’상에" 위치하고 있다고 할 때， 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐만 아니라 두 부재 사이에 또 다른부재가존재하는 경우도포함한다.  Throughout this specification, when a member is located on the other member '', this includes not only when a member is in contact with the other member, but also when there is another member between the two members.
본원 명세서 전체에서， 어떤 부분이 어떤 구성 요소를 "포함” 한다고 할 때， 이는 특별히 반대되는 기재가 없는 한 다른 구성 요소를 제외하는 것이 아니라 다 른 구성 요소를 더 포함할 수 있는 것을 의미한다. 본원 명세서 전체에서 사용되는 정도의 용어 "약"， "실질적으로” 등은 언급된 의미에 고유한 제조 및 물질 허용오 차가 제시될 때 그 수치에서 또는 그 수치에 근접한 의미로 사용되고， 본원의 이해 를 돕기 위해 정확하거나 절대적인 수치가 언급된 개시 내용을 비양심적인 침해자 가 부당하게 이용하는 것을 방지하기 위해 사용된다. 본원 명세서 전체에서 사용되 는 정도의 용어 ”~（하는） 단계” 또는 의 단계’’는 ~ 를 위한 단계”를 의미하지 않는다.  Throughout this specification, when a part is said to "include" a certain component, it means that it can further include other components, except to exclude other components unless specifically stated otherwise. As used throughout the specification, the terms "about", "substantially", and the like, are used at, or in close proximity to, numerical values when manufacturing and material tolerances inherent in the meanings indicated are provided to aid the understanding herein. To prevent the unfair use of unscrupulous infringers by making disclosures that contain accurate or absolute figures. As used throughout this specification, the term “step of” or “step of” does not mean “step for”.
본원 명세서 전체에서, 마쿠시 형식의 표현에 포함된 "이들의 조합”의 용어 는 마쿠시 형식의 표현에 기재된 구성 요소들로 이루어진 군에서 선택되는 하나 이 상의 혼합 또는 조합을 의미하는 것으로서， 상기 구성 요소들로 이루어진 군에사 2019/190270 1»（：1^1{2019/003723 Throughout this specification, the term "combination of these" included in the expression of the makushi form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the makushi form, Military history of elements 2019/190270 1 »（： 1 ^ 1 {2019/003723
선택되는 하나 이상을 포함하는 것을 의미한다. It means to include one or more selected.
본원 명세서 전체에서， 및/또는 의 기재는， ^ 또는 8， 또는 쇼 및 ’를 의미한다.  Throughout this specification, the description of and and or, means ^ or 8, or show and '.
본원 명세서 전체에서， 용어 ’’아릴”은 06-50의 방향족 탄화수소 고리기， 예를 들어， 페닐， 벤질, 나프틸， 바이페닐， 터페닐， 플루오렌, 페난트레닐， 트리페닐레 닐， 페릴레닐， 크리세닐 , 플루오란테닐， 벤조플루오레닐， 벤조트리페닐레닐， 벤조 크리세닐， 안트라세닐， 스틸베닐 , 파이레닐 등의 방향족 고리를 포함하는 것을 의 미하며， ’’헤테로아릴’’은 적어도 1 개의 헤테로 원소를 포함하는 05-50의 방향족 고리 로서， 예를 들어， 피롤릴, 피라지닐, 피리디닐, 인돌릴， 이소인돌릴, 푸릴， 벤조퓨 라닐 , 이소벤조퓨라닐 , 다이벤조퓨라닐， 벤조티오페닐 , 다이벤조티오페닐 , 퀴놀릴 기 , 이소퀴놀릴， 퀴녹살리닐， 카르바졸릴 , 페난트리디닐 , 아크리디닐 , 페난트롤리 닐, 티에닐, 및 피리딘 고리, 피라진 고리， 피리미딘 고리, 피리다진 고리, 트리아 진 고리， 인돌 고리， 퀴놀린 고리， 아크리딘고리， 피롤리딘 고리， 디옥산 고리， 피 페리딘 고리， 모르폴린 고리， 피페라진 고리, 카르바졸 고리， 퓨란 고리， 티오펜 고리， 옥사졸 고리, 옥사디아졸 고리， 벤조옥사졸 고리, 티아졸 고리, 티아디아졸 고리， 벤조티아졸 고리， 트리아졸 고리， 이미다졸 고리, 벤조이미다졸 고리， 피란 고리， 다이벤조퓨란 고리， 다이벤조티오펜 고리로부터 형성되는 헤테로고리기를 포 함하는 것을 의미할 수 있다.  Throughout this specification, the term `` aryl '' refers to an aromatic hydrocarbon ring group of 06-50, for example phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, phen `` Heteroaryl '', meaning containing aromatic rings such as rillenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzo chrysenyl, anthracenyl, stilbenyl, pyrenyl, etc. Is a 05-50 aromatic ring containing at least one hetero element, for example pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindoleyl, furyl, benzofuranyl, isobenzofuranyl, dibenzo Furanyl, benzothiophenyl, dibenzothiophenyl, quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine ring, pyrazine ring, Pipe Dean ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring Thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzoimidazole ring, pyran ring, die It may be meant to include a heterocyclic group formed from a benzofuran ring, a dibenzothiophene ring.
본원 명세서 전체에서 용어 "치환 또는 비치환’’은 할로겐， 아미노기, 니트릴 기 , 니트로기 또는 0 20의 알킬기， 02 20의 알케닐기， 레20의 알콕시기 , 03 020의 시클로알킬기， 03~020£1 헤테로시클로알킬기， 06^30의 아릴기 및 03~030£1 헤테로아릴 2019/190270 1»(：1^1{2019/003723 Throughout this specification, the term "substituted or unsubstituted" is halogen, amino group, nitrile group, nitro group or 0 20 alkyl group, 02 20 alkenyl group, Le 20 alkoxy group, 03 020 cycloalkyl group, 0 3 ~ 020 £ 1 heterocycloalkyl, 06 ^ 30 aryl and 03-030 £ 1 heteroaryl 2019/190270 1 »(： 1 ^ 1 {2019/003723
기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환되거나 치환되지 않는 것 을 의미할 수 있다. 또한， 본원 명세서 전체에서 동일한 기호는 특별히 언급하지 않는 한 같은 의미를 가질 수 있다. It may mean that it is substituted or unsubstituted with one or more groups selected from the group consisting of groups. In addition, the same symbol throughout the present specification may have the same meaning unless otherwise specified.
본원 명세서 전체에서 용어 ’’플루오랜" 은 9번 탄소에 결합된 수소가 치환 또는 비치환의 -20의 알킬기， 치환 또는 비치환의 05-30의 아릴기 또는 치환 또는 비치환의 03-30의 헤테로아릴기로 치환된 경우를 의미할 수 있다.  Throughout this specification, the term `` fluorane '' refers to a substituted or unsubstituted -20 alkyl group, a substituted or unsubstituted 05-30 aryl group, or a substituted or unsubstituted 03-30 heteroaryl group, wherein hydrogen bonded to carbon 9 is substituted. It may mean a substituted case.
본원의 제 1 측면은 하기 화학식 1로 표시되는 화합물을 제공한다.  The first aspect of the present application provides a compound represented by the following formula (1).
[화학식 1]  [Formula 1]
Figure imgf000009_0001
Figure imgf000009_0001
!은 치환 또는 비치환의 0 5（）의 아릴기 , 또는 치환 또는 비치환의 05-050 의 헤테로아릴기이고, Is a substituted or unsubstituted 0 5 () aryl group or a substituted or unsubstituted 05-050 heteroaryl group,
2는 치환 또는 비치환의 （：12 50의 아릴기이고，  2 is a substituted or unsubstituted aryl group of 12 50:
요、， 내지 ¾은 각각 독립적으로 수소， 할로겐， 니트로기， 니트릴기， 치 환 또는 비치환의 （：1 30의 알킬기， 치환 또는 비치환의 30의 알케닐기， 치환 또 는 비치환의 （：1 30의 알콕시기， 치환 또는 비치환의 （：1 30의 설파이드기， 치환 또는 2019/190270 1»（：1^1{2019/003723 Are each independently hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted （: 1 30 alkyl group, substituted or unsubstituted 30 alkenyl group, substituted or unsubstituted (1: 1 30 Alkoxy group, substituted or unsubstituted （: 1 30 sulfide group, substituted or 2019/190270 1 »（： 1 ^ 1 {2019/003723
비치환의 06~030^ 아릴기， 또는 치환 또는 비치환의 05~030^ 해테로아릴기이고, 인 접한 복수의 끼리 , ¾끼리 , 끼리， 또는 I?과 묘’ 는 서로 결합하여 환을 형성하거 나 형성하지 않을 수 있고， 요4와 1?6 또는 묘5와 은 서로 결합하여 환을 형성하거나 형성하지 않을 수 있으며, Unsubstituted 06-030 ^ aryl group, or substituted or unsubstituted 05-030 ^ heteroaryl group, adjacent plurals, ¾, ¾, or I? And tomb 'combine with each other to form a ring or May not form, yo 4 and 1-6 or seedling 5 and may combine with each other to form a ring or not,
은 직접결합， 치환 또는 비치환의 （：6~（뇨의 아릴텐기， 또는 치환 또는 비치 환의 05-030^1 헤테로아릴렌기이고, Is a direct bond, a substituted or unsubstituted （: 6 to (urine arylten group, or a substituted or unsubstituted 05-030 ^ 1 heteroarylene group,
匕2는 치환 또는 비치환의
Figure imgf000010_0001
또는 치환 또는 비치환의 05~030 의 헤테로아릴렌기이고， 匕 2 is substituted or unsubstituted
Figure imgf000010_0001
Or a substituted or unsubstituted 05 to 030 hetero arylene group,
1은 0또는 1 내지 4의 정수이고,  1 is 0 or an integer of 1 to 4,
01 및 II은 각각 독립적으로 0 또는 1 내지 3의 정수이며, 상기 1， 01또는 II이 2 이상인
Figure imgf000010_0002
같거나 다를 수 있다. 01 and II are each independently 0 or an integer of 1 to 3, wherein 1, 01 or II is 2 or more
Figure imgf000010_0002
It can be the same or different.
본 발명의 일 구현예에 따른 화합물은 3환 축합고리기（다이벤조퓨란， 다이벤 조티오펜 또는 플루오렌）와 다이벤조퓨란이 연결기를 통하여 아릴아민의 질소와 연 결됨으로써 발광보조층에 적합한
Figure imgf000010_0003
레벨을 형성할 수 있으며, 이에 따라 고효율 의 유기 발광소자를 구현할수 있다. The compound according to the embodiment of the present invention is suitable for the light emitting auxiliary layer by connecting a tricyclic condensed ring group (dibenzofuran, dibenzothiophene or fluorene) and dibenzofuran with nitrogen of arylamine through a linking group.
Figure imgf000010_0003
It is possible to form a level, thereby realizing an organic light emitting device having high efficiency.
또한， 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측에 전자 내성이 우수한 3환 축합고리기를 도입하여 높은 !!■） 및 11을 유지하여 전자차단이 용이하 고， 발광층내 엑시톤 가둠 효과가 극대화될 수 있다. 이에 따라 고효율 및 장수명 의 유기 발광소자를 구현할수 있다.  In addition, the compound according to an embodiment of the present invention is easy to block electrons by maintaining a high !! ■) and 11 by introducing a tricyclic condensed ring group having excellent electron resistance on one side of the arylamine, and the exciton confinement effect in the light emitting layer Can be maximized. Accordingly, high efficiency and long life organic light emitting device can be realized.
또한， 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측에 벌키 특성이 작은 다이벤조퓨란의 2번 또는 4번을 연결 위치로 하여 박막 형성시 분자의 배열을 우수하게 할 수 있고， 저전압 구현 및 롤오프현상 억제를 통하여 장수명의 유기 발 광소자를 구현할수 있다. In addition, the compound according to an embodiment of the present invention is arranged on the side of the aryl amine 2 or 4 of the dibenzofuran having a small bulky property as a connection position to arrange the arrangement of the molecules when forming a thin film It is possible to achieve excellent, and to achieve a long life of the organic light emitting device through the implementation of low voltage and suppression of the roll-off phenomenon.
또한， 상기 3환축합고리 화합물의 연결 위치 번호는 하기와 같을 수 있다.  In addition, the linking position number of the tricyclic condensed ring compound may be as follows.
Figure imgf000011_0001
또한, 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측이 연결기를 통 하여 다이벤조퓨란과 연결되고， 타측에 아릴기를 가짐에 따라 파이컨쥬게이션이 증 가할 수 있다. 이에 따라 홀 모빌리티（¾16 010^ 1 를 개선할 수 있고， 유기 발 광소자에 적용시 낮은 구동 전압을 구현할 수 있다.
Figure imgf000011_0001
In addition, the compound according to an embodiment of the present invention may be increased by one side of the arylamine is connected to the dibenzofuran through a linking group, and having the aryl group on the other side. As a result, hole mobility (¾16 010 ^ 1) can be improved, and low driving voltage can be realized when applied to organic light emitting devices.
또한， 본 발명의 일 구현예에 따른 화합물은 아릴아민의 일측에 다이벤조퓨 란을 통하여 확장된 3환 축합고리기를 포함하여 높은 용를 형성하여 박막 재결정화 를 방지할수 있고， 이에 따라유기 발광 소자의 구동 안정성을 확보할 수 있다. 본 .발명의 일 구현예에서 , 상기 화합물은 하기 화학식 2로 표시될 수 있다.In addition, the compound according to an embodiment of the present invention includes a tricyclic condensed ring group extended through dibenzofuran on one side of the arylamine to form a high solvent to prevent thin film recrystallization, thereby Driving stability can be secured. Seen . In one embodiment of the invention, the compound may be represented by the formula (2).
[화학식 2] [Formula 2]
Figure imgf000011_0002
2019/190270 1»（：1^1{2019/003723
Figure imgf000011_0002
2019/190270 1 »（： 1 ^ 1 {2019/003723
상기 화학식 2에서 In Chemical Formula 2
X， 紅1， 2 ,
Figure imgf000012_0001
화학식 1에서의 정의 와 같고， X ， 紅 1 ， 2,
Figure imgf000012_0001
Same as the definition in Formula 1,
묘7은 수소， 할로겐， 니트로기， 니트릴기， 치환 또는 비치환의 30의 알킬 기 , 치환 또는 비치환의 02^30의 알케닐기， 치환 또는 비치환의 （：1 30의 알콕시기， 치환 또는 비치환의 （：1 3◦의 설파이드기 , 치환 또는 비치환의 06~030^ 아릴기， 또는 치환 또는 비치환의 05~030£] 헤테로아릴기이며，  Fig. 7 shows hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted 30 alkyl group, substituted or unsubstituted 02 ^ 30 alkenyl group, substituted or unsubstituted （: 1 30 alkoxy group, substituted or unsubstituted ( : 1 3 ◦ sulfide group, substituted or unsubstituted 06-030 ^ aryl group, or substituted or unsubstituted 05-030 £] heteroaryl group,
0는 1 내지 4의 정수이고， 는 0 또는 1 내지 4의 정수이며， 상기 0 또는 V 가 2이상인 경우 묘7은 서로 같거나 다를 수 있고， 0가 2 이상인 경우 13는 서로 같거 나 다를 수 있다.  0 is an integer of 1 to 4, is 0 or an integer of 1 to 4, the figure 7 may be the same or different when 0 or V is 2 or more, 13 may be the same or different when 0 is 2 or more. .
상기 화학식 2로 표시되는 화합물은 상기 화학식 1에서 1^2가 페닐렌을 포함 하는 경우로， 아릴아민의 치환기인 다이벤조퓨란과 아릴아민의 질소 사이에 한 개 이상의 페닐렌이 연결기로 결합되는 형태이다. 이러한 경우, 발광보조층에 적절한 抑¾10 형성과 동시에 페닐렌기로 인해 화합물이 높은 11을 유지할 수 있어， 엑시톤 차단에 더욱 효과적일 수 있다. The compound represented by the formula (2) is a case in which 1 ^ 2 in the formula (1) includes phenylene, a form in which one or more phenylene is bonded between a dibenzofuran which is a substituent of arylamine and nitrogen of the arylamine to be. In this case, the compound can maintain a high 11 due to the phenylene group at the same time forming a suitable ¾¾ 10 in the light emitting auxiliary layer, it can be more effective in blocking excitons.
본 발명의 일 구현예에서， 상기 화합물은 하기 화학식 3으로 표시될 수 있 다. 2019/190270 1»（：1^1{2019/003723 In one embodiment of the present invention, the compound may be represented by the following formula (3). 2019/190270 1 »（： 1 ^ 1 {2019/003723
[화학식 3] [Formula 3]
Figure imgf000013_0001
I은 상기 화학식 1에서의 정의와 같고，
Figure imgf000013_0001
I is as defined in Formula 1 above,
은 수소 , 할로겐， 니트로기， 니트릴기 , 치환 또는 비치환의 01-030^1 알킬 기 , 치환 또는 비치환의 0·（ 의 알케닐기 , 치환 또는 비치환의 （：1 3<3의 알콕시기， 치환 또는 비치환의 （：1 30의 설파이드기， 치환 또는 비치환의 06 30의 아릴기， 또는 치환 또는 비치환의 05~030£] 헤테로아릴기이며，  Silver hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted 01-030 ^ 1 alkyl group, substituted or unsubstituted 0 · （alkenyl group, substituted or unsubstituted （: 1 3 <3 alkoxy group, substituted or Unsubstituted （: 1 30 sulfide group, substituted or unsubstituted 06 30 aryl group, or substituted or unsubstituted 05 to 030 £] heteroaryl group,
0는 1 내지 4의 정수이고， 는 0 또는 1 내지 4의 정수이며 ,  0 is an integer from 1 to 4, is 0 or an integer from 1 to 4,
상기 0 또는 13가 2이상인 경우 如은 서로 같거나 다를 수 있고， 0가 2 이상인 경우 I）는 서로 같거나 다를 수 있다. When 0 or 13 is 2 or more, 如 may be the same or different, and when 0 is 2 or more, I) may be the same or different.
상기 화학식 3으로 표시되는 화합물은 상기 화학식 1에서 이 직접결합인 경우로， 다이벤조퓨란과 3환 축합고리기（다이벤조퓨란， 다이벤조티오펜 또는 플루 오렌계열）가 직접연결되어 깊은 恥볘） 레벨을 형성하여 고효율의 유기 발광 소자를 구현할 수 있다.  Compound represented by the formula (3) is a direct bond in the formula (1), dibenzofuran and tricyclic condensed ring group (dibenzofuran, dibenzothiophene or fluorene series) is directly connected deep 恥 볘) By forming a level, an organic light emitting device having high efficiency can be realized.
본 발명의 일 구현예에서 , 상기 화합물은 하기 화학식 4 또는 화학식 5 로 2019/190270 1»（：1^1{2019/003723 표시될 수 있다. In one embodiment of the present invention, the compound is represented by the following formula (4) 2019/190270 1 »(： 1 ^ 1 {2019/003723 may be displayed.
[화학식 4]  [Formula 4]
Figure imgf000014_0002
Figure imgf000014_0002
상기 화학식 4 및 화학식 5에서, In Chemical Formulas 4 and 5,
Figure imgf000014_0001
1 및 II은 상기 화학식 1에서의 정의와 같고，
Figure imgf000014_0001
1 and II are as defined in Formula 1,
X는 0또는 이며，  X is 0 or
1?2는서로 같거나 다를 수 있고，  1 or 2 can be the same or different,
묘7은 수소， 할로겐， 니트로기， 니트릴기， 치환 또는 비치환의 레30의 알킬 기， 치환 또는 비치환의 02<30^] 알케닐기， 치환 또는 비치환의 레30의 알콕시기， 치환또는 비치환의 에30의 설파이드기 , 치환또는 비치환의 06~030^ 아릴기 , 또는 치환또는 비치환의 05 30의 헤테로아릴기이고, 2019/190270 1»（：1^1{2019/003723 Fig. 7 is hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted LE 30 alkyl group, substituted or unsubstituted 02 <30 ^] alkenyl group, substituted or unsubstituted LE 30 alkoxy group, substituted or unsubstituted 30 sulfide group, substituted or unsubstituted 06-030 ^ aryl group, or substituted or unsubstituted 05 30 heteroaryl group, 2019/190270 1 »（： 1 ^ 1 {2019/003723
0는 1 내지 4의 정수이며， I）는 0 또는 1 내지 4의 정수이며， 0 is an integer of 1 to 4, I) is 0 or an integer of 1 to 4,
상기 0 또는 I）가 2이상인 경우 묘7은 서로 같거나 다를 수 있고， 0가 2 이상 인 경우 I）는 서로 같거나 다를 수 있다.  When 0 or I) is 2 or more, Fig. 7 may be the same or different, and when 0 is 2 or more, I) may be the same or different.
이러한 경우， 빠른 홀 모빌리티와 동시에 높은 11·）를 유지할 수 있어, 저전 압 구동에 효과적이며， 발광층으로부터 정공수송층으로 유입되는 전자를 차단하는 데 효과적일 수 있다.  In this case, high hole mobility and high 11) can be maintained, which is effective for low voltage driving, and can be effective for blocking electrons flowing from the light emitting layer into the hole transport layer.
본 발명의 일 구현예에서, 상기 화합물은 하기 화학식 6으로 표시될 수 있 다.  In one embodiment of the present invention, the compound may be represented by the following formula (6).
[화학식 6]  [Formula 6]
Figure imgf000015_0001
， , ， ， ， 기 화학식 1에서의 정의와 같 은 수소, 할로겐, 니트로기， 니트릴기， 치환 또는 비치환의 레 의 알킬 기， 치환 또는 비치환의 02~030^ 알케닐기 , 치환 또는 비치환의 （：1 30의 알콕시기， 치환 또는 비치환의 （：1 30의 설파이드기， 치환 또는 비치환의 06~030£] 아릴기 , 또는 치환 또는 비치환의 05~030£1 헤테로아릴기이며， 2019/190270 1»（：1^1{2019/003723
Figure imgf000015_0001
Hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted 02 to 030 ^ alkenyl group, substituted or unsubstituted as defined in formula (1) 1 30 alkoxy group, substituted or unsubstituted （: 1 30 sulfide group, substituted or unsubstituted 06-030 £] aryl group, or substituted or unsubstituted 05-030 £ 1 heteroaryl group, 2019/190270 1 »（： 1 ^ 1 {2019/003723
0는 1 내지 4의 정수이고, I）는 0또는 1 내지 4의 정수이며， 0 is an integer of 1 to 4, I) is 0 or an integer of 1 to 4,
상기 0 또는 I?가 2이상인 경우 모7은 서로 같거나 다를 수 있고, 0가 2 이상 인 경우 13는서로 같거나 다를 수 있다.  When 0 or I? Is 2 or more, mother 7 may be the same or different, and when 0 is 2 or more, 13 may be the same or different.
이러한 경우， 플루오렌을 통한 빠른 홀모빌리티 및 높은 용로 저전압 구동 및 구동안정성 개선에 유리할수 있다.  In this case, it can be advantageous for fast hole mobility through fluorene and high voltage for low voltage driving and driving stability improvement.
본 발명의 일 구현예에서， 상기 화합물은 하기 화학식 7또는 화학식 8로 표 시될 수 있다.  In one embodiment of the present invention, the compound may be represented by the following formula (7) or formula (8).
[화학식 7]  [Formula 7]
Figure imgf000016_0001
Figure imgf000016_0001
상기 화학식 7 및 화학식 8에서， In Chemical Formulas 7 and 8,
Figure imgf000016_0002
1 및 II은 상기 화학식 1에서의 정의와 같고， 2019/190270 1»（：1^1{2019/003723
Figure imgf000016_0002
1 and II are as defined in Formula 1, 2019/190270 1 »（： 1 ^ 1 {2019/003723
X는 0 또는 이며， X is 0 or
요2는 서로 같거나 다를 수 있고，  2 can be the same or different,
묘7은 수소， 할로겐， 니트로기， 니트릴기, 치환 또는 비치환의 （：1 30의 알킬 기， 치환 또는 비치환의 （：2 30의 알케닐기 , 치환 또는 비치환의 01~030£] 알콕시기， 치환 또는 비치환의 （：1 30의 설파이드기， 치환 또는 비치환의 06 30의 아릴기, 또는 치환 또는 비치환의 05~030£1 헤테로아릴기이고， Fig. 7 is hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted （: 1 30 alkyl group, substituted or unsubstituted （： 2 30 alkenyl group, substituted or unsubstituted 01 ~ 030 £] alkoxy group, substituted Or an unsubstituted （: 1 30 sulfide group, a substituted or unsubstituted 06 30 aryl group, or a substituted or unsubstituted 05 ~ 030 £ 1 heteroaryl group,
0는 1 내지 4의 정수이며， 는 0 또는 1 내지 4의 정수이며，  0 is an integer from 1 to 4, is 0 or an integer from 1 to 4,
상기 0 또는 13가 2이상인 경우 은 서로 같거나 다를 수 있고， 0가 2 이상 인 경우 I）는 서로 같거나 다를 수 있다.  When 0 or 13 is 2 or more, may be the same or different, and when 0 is 2 or more, I) may be the same or different.
이러한 경우， 빠른 홀모빌리티와 동시에 높은 ^0 및 II을 가질 수 있어, 전자 및 엑시톤 차단이 용이하여 롤오프현상 개선을 통한 발광효율 및 수명개선에 효과적일 수 있다.  In this case, it may have high ^ 0 and II at the same time as fast hole mobility, and it is easy to block electrons and excitons, and thus may be effective in improving luminous efficiency and lifespan by improving roll-off phenomenon.
본 발명의 일 구현예에 따르면， 상기 화학식 1 내지 화학식 8에서 1 , 111, II , 0 , V 가 모두 0일 수 있다. 또한, 본 발명의 일 구현예에 따르면， 상기 화학식 1 내지 화학식 8에서 ¾ 내지 모7은 각각 독립적으로 수소， （：1~ 0의 알킬기， 또는 페닐 기일 수 있다. 보다 구체적으로， 묘1 내지 은 수소, 또는 페닐기일 수 있다.  According to one embodiment of the present invention, in Formulas 1 to 8, all 1, 111, II, 0, V may be 0. In addition, according to an embodiment of the present invention, in the above Chemical Formulas 1 to 8, ¾ to parent 7 may be each independently hydrogen, (1 ~ 0 alkyl group, or phenyl group. More specifically, seed 1 to silver may be hydrogen or a phenyl group.
또한， 본 발명의 일 구현예에 따르면， 상기 화학식 1 내지 화학식 3， 및 화 학식 6에서 I? 및 I? '는 각각 독립적으로 의 알킬기일 수 있다.  In addition, according to an embodiment of the present invention, in Formula 1 to Formula 3, and Formula 6 I? And I? 'Can be each independently an alkyl group of.
또한， 본 발명의 일 구현예에 따르면， 상기 화학식 1 내지 화학식 5 , 화학식 7, 및 화학식 8에서 X는 0일 수 있다.  In addition, according to an embodiment of the present invention, X in Formula 1 to Formula 5, Formula 7, and Formula 8 may be 0.
또한， 본 발명의 일 구현예에 따르면， 상기 화학식 1 내지 화학식 5 , 화학식 2019/190270 1»（：1^1{2019/003723 In addition, according to an embodiment of the present invention, the formula 1 to formula 5, the formula 2019/190270 1 »（： 1 ^ 1 {2019/003723
7 및 화학식 8에서 X는 일 수 있다. In Formula 7 and Formula 8, X may be.
본 발명의 일 구현예에 따르면, 상기 화학식 1 내지 화학식 8에서 요 은 페 닐, 나프틸， 비페닐, 터페닐， 플루오렌일, 디알킬플루오렌일, 디아릴플루오렌일， 다이벤조퓨란일， 다이벤조티오펜일 및 이들의 조합으로 이루어진 군에서 선택되고， 상기 2는 비페닐, 페닐나프틸， 터페닐, 플루오렌일, 디알킬플루오렌일, 디아릴플 루오렌일， 다이벤조퓨란일， 다이벤조티오펜일 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.  According to an embodiment of the present invention, in the above Chemical Formulas 1 to 8, urethane is phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl , Dibenzothiophenyl and combinations thereof, and 2 represents biphenyl, phenylnaphthyl, terphenyl, fluorenyl, dialkyl fluorenyl, diaryl fluorenyl and dibenzofuranyl. , Dibenzothiophenyl and combinations thereof.
또한, 본 발명의 일 구현예에 따르면, 상기 화학식 1에서 는 적어도 하나 의 1 , 4 -페닐렌기 또는 1， 3 -페닐렌기를 포함하는 치환또는 비치환의 06 24의 아릴렌 기일 수 있다.  Further, according to one embodiment of the present invention, in Chemical Formula 1 may be a substituted or unsubstituted 06 24 arylene group including at least one 1, 4-phenylene group or 1, 3-phenylene group.
본 발명의 일 구현예에 따르면， 상기 화학식 1에서 상기 1， 2 및 느2 중 적어도 하나는 메타 결합을 갖는 페닐텐기를 포함할수 있다.  According to one embodiment of the present invention, at least one of 1, 2 and Ne 2 in the formula (1) may include a phenylten group having a meta bond.
또한 , 본 발명의 일 구현예에 따르면， 상기 화학식 1에서 상기 1은 메타 결합을 갖는 비페닐 또는 메타 결합을 갖는 터페닐이거나， 상기 2는 메타 결합을 갖는 비페닐 또는 메타 결합을갖는 터페닐일 수 있다.  Further, according to one embodiment of the present invention, in Formula 1, 1 is biphenyl having a meta bond or terphenyl having a meta bond, or 2 is terphenyl having a biphenyl having a meta bond or a meta bond. Can be.
또한， 본 발명의 일 구현예에 따르면， 상기 화학식 1에서 하기 3) 내지 0) 중 어느 하나 이상을 만족할수 있다:  In addition, according to one embodiment of the present invention, in Formula 1, any one or more of the following 3) to 0) may be satisfied:
3.) 1 및 2는 비페닐기 ; 3.) 1 and 2 are biphenyl groups;
Figure imgf000018_0001
적어도하나는 6원환만으로구성된 (：14이상의 아릴기; 및 이상의 아릴렌기이다.
Figure imgf000018_0001
At least one is a (: 14 or more aryl group) and the above-mentioned arylene group which consist only of a 6-membered ring.
본 발명의 일 구현예에 따르면, 상기 화학식 1 내지 화학식 8에서 상기 1 2019/190270 1»（：1^1{2019/003723 은 페닐， 비페닐, 터페닐， 디메틸플루오렌일 및 이들의 조합으로 이루어진 군에서 선택되고， 상기 2는 비페닐， 터페닐, 디메틸플루오렌일 및 이들의 조합으로 이루 어진 군에서 선택될 수 있다. According to an embodiment of the present invention, the formula 1 to formula 8 in the above 1 2019/190270 1 »（： 1 ^ 1 {2019/003723 is selected from the group consisting of phenyl, biphenyl, terphenyl, dimethylfluorenyl and combinations thereof, wherein 2 is biphenyl, terphenyl, dimethylfluorene It may be selected from the group consisting of one and a combination thereof.
본 발명의 일 구현예에 따르면 , 상기 화학식 1로 표시되는 화합물은 하기의 화합물 중 어느 하나일 수 있으며， 이에 제한되지 않을수 있다: According to an embodiment of the present invention, the compound represented by Formula 1 may be any one of the following compounds, but may not be limited thereto:
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000039_0001
Figure imgf000040_0001
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Figure imgf000042_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
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Figure imgf000054_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
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Figure imgf000058_0001
Figure imgf000055_0001
Figure imgf000056_0001
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Figure imgf000059_0001
Figure imgf000060_0001
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Figure imgf000062_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
2019/190270 1»（：1^1{2019/003723
Figure imgf000070_0001
Figure imgf000071_0001
2019/190270 1 »（： 1 ^ 1 {2019/003723
Figure imgf000072_0001
Figure imgf000072_0001
본원의 제 2측면은상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 상기 유기 발광소자는 제 1 전극 및 제 2 전극사이에 본원에 따 른 화합물을 함유하는유기물충을 1층 이상 포함할수 있다.  The second aspect of the present application provides an organic light emitting device comprising the compound represented by the formula (1). The organic light emitting device may include one or more layers of organic insecticides containing a compound according to the present application between the first electrode and the second electrode.
본 발명의 일 구현예에 있어서， 상기 유기물층은 정공주입층， 정공수송층 및 발광보조층일 수 있으나, 이에 제한되지 않을 수 있다. 또한 본 발명의 화합물은 유기층을 형성할 때 단독으로사용되거나 공지의 화합물과 함께 사용될 수 있다. 본 발명의 일 구현예에 있어서， 상기 유기 발광소자는 정공수송물질을 함유 하는 유기물층 및 상기 화학식 1로 표시되는 화합물을 함유하는 유기물층을 포함할 수 있으나， 이에 제한되지 않을 수 있다. 2019/190270 1»（：1^1{2019/003723 In one embodiment of the present invention, the organic material layer may be a hole injection layer, a hole transport layer and a light emitting auxiliary layer, but may not be limited thereto. In addition, the compounds of the present invention may be used alone or in combination with known compounds when forming the organic layer. In one embodiment of the present invention, the organic light emitting device may include an organic material layer containing a hole transport material and an organic material layer containing a compound represented by Formula 1, but may not be limited thereto. 2019/190270 1 »（： 1 ^ 1 {2019/003723
상기 유기 발광 소자는 애노드 (크110(16)와 캐소드 (0^110(16) 사이에 정공주입 층어比)， 정공수송층 0111)， 발광층犯此)， 전자수송충犯孔)， 전자주입층 ( 나 등의 유기물층을 1층 이상포함할수 있다. The organic light emitting device includes an anode (a hole injection layer ratio between a size 110 (16) and a cathode (0 ^ 110 (16)), a hole transport layer 0111), a light emitting layer 犯 此), an electron transport layer ，, an electron injection layer ( It may contain one or more organic layer, such as me.
예를 들어 , 상기 유기 발광 소자는 도 1에 기재된 구조와 같이 제조될 수 있 다. 유기 발광 소자는 아래로부터 애노드 (정공주입전극 ( 1000) ) / 정공주입층 (200) / 정공수송층 (300) / 발광층 (400) / 전자수송층 (500) / 전자주입충 (600) / 캐소드 (전자주입전극 (2000) ) 순으로 적층될 수 있다.  For example, the organic light emitting device may be manufactured as shown in FIG. 1. The organic light emitting device is formed from the bottom of the anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection charge 600 / cathode (electron The injection electrode 2000 may be stacked in this order.
도 1에서 기판 ( 100)은 유기 발광 소자에서 사용되는 기판을 사용할 수 있으 며， 특히 기계적 강도， 열적 안정성, 투명성, 표면평활성， 취급용이성， 및 방수성 이 우수한투명한유리 기판또는플렉시블이 가능한 플라스틱 기판일 수 있다. 정공주입전극 (1000)은 유기 발광 소자의 정공 주입을 위한 애노드로 사용된 다. 정공의 주입이 가능하도록 낮은 일함수를 갖는 물질을 이용하며, 인둠틴옥사이 드 (比⑴, 인둠징크옥사이드 ( I及))， 그래핀 (奸31±61½)과 같은 투명한 재질로 형성될 수 있다.  In FIG. 1, the substrate 100 may be a substrate used in an organic light emitting device. In particular, the substrate 100 may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Can be. The hole injection electrode 1000 is used as an anode for hole injection of the organic light emitting device. A material having a low work function is used to inject holes, and may be formed of transparent materials such as indum tin oxide (比 ⑴, indum zinc oxide (I 及)) and graphene (핀 31 ± 61½). .
상기 애노드 전극 상부에 정공주입층 물질을 진공증착법 , 스핀코팅법 , 캐스 트법， 1고(1 !1§따1 내10(¾61;1; )법 등과 같은 방법에 의해 증착하여 정공주입층 (200) 을 형성할 수 있다. 상기 진공증착법에 의해 정공주입충을 형성하는 경우 그 증착 조건은 정공주입층 (200)의 재료로서 사용하는 화합물， 목적하는 정공주입층의 구조 및 열적특성 등에 따라 다르지만, 일반적으로 50-500 X：의 증착온도, 10_8내지 10_3 !·!·의 진공도, 0.01 내지 100 入八%의 증착속도， 10 入 내지 5 _의 층 두께 범 위에서 적절히 선택할수 있다. 2019/190270 1»（：1^1{2019/003723 The hole injection layer material is deposited on the anode electrode by a method such as vacuum deposition, spin coating, casting, 1 solid (1! 1 § 1 1 10 (¾61; 1;) method, and the like. In the case of forming the hole injection worm by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the desired hole injection layer, in general, 50-500 X:!! deposition temperature, 10_ 8 to 10_ 3 · degree of vacuum of 0.01 to 100% of the deposition rate of入八, pan 10入to 5 _ the layer thickness of the above can be properly selected. 2019/190270 1 »（： 1 ^ 1 {2019/003723
다음으로 상기 정공주입층 (200) 상부에 정공수송층 물질을 진공증착법, 스핀 코팅법， 캐스트법，
Figure imgf000074_0001
같은 방법에 의해 증착하여 정공수송층 (300)을 형성 할 수 있다. 상기 진공증착법에 의해 정공수송층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조 건 범위에서 선택하는 것이 좋다. Next, the hole transport layer material on the hole injection layer 200 is vacuum deposited, spin coated, cast,
Figure imgf000074_0001
The hole transport layer 300 may be formed by deposition by the same method. In the case of forming the hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select it in almost the same conditions as the formation of the hole injection layer.
상기 정공수송층 (300)은 본 발명에 따른 화합물을사용할 수 있으며， 상술한 바와 같이， 본 발명에 따른 화합물을 단독으로 사용하거나 공지의 화합물을 함께 사용할 수 있다. 또한, 본 발명의 일 구현예에 따르면 정공수송층 (300)은 1층 이상 일 수 있으며， 공지의 물질로만 형성된 정공수송층을 함께 포함할 수 있다. 또한， 본 발명의 일 구현예에 따르면 상기 정공수송층 (300) 상에 발광보조층을 형성할 수 있다.  The hole transport layer 300 may use a compound according to the present invention. As described above, the compound according to the present invention may be used alone or a known compound may be used together. In addition, according to one embodiment of the present invention, the hole transport layer 300 may be one or more layers, and may include a hole transport layer formed only of a known material. In addition, according to the exemplary embodiment of the present invention, a light emitting auxiliary layer may be formed on the hole transport layer 300.
상기 정공수송층 (300) 또는 발광보조층 상부에 발광층 물질을 진공증착법， 스핀코팅법， 캐스트법，
Figure imgf000074_0002
같은 방법에 의해 증착하여 발광층 (400)을 형성 할 수 있다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용 하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 또한, 상기 발광층 재료는 공지의 화합물을 호스트 또는 도펀트로사용할수 있다. Vacuum deposition, spin coating, casting, or the like of the light emitting layer material on the hole transport layer 300 or the light emitting auxiliary layer
Figure imgf000074_0002
The light emitting layer 400 may be formed by depositing by the same method. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select in the same condition range as the formation of the hole injection layer. In addition, the light emitting layer material may use a known compound as a host or dopant.
또한， 발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항여기자 또는 정 공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공억제재료어 를 추가 로 진공증착법 또는 스핀코팅법에 의해 적층시킬 수 있다. 이때 사용할 수 있는 정 공억제물질은 특별히 제한되지는 않으나， 정공억제재료로 사용되고 있는 공지의 것 2019/190270 1»（：1^1{2019/003723 에서 임의의 것을 선택해서 이용할 수 있다. 예를 들면， 옥사디아졸 유도체나 트리 아졸 유도체， 페난트롤린 유도체， 또는 일본특개평 11-329734(사)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 831(1(비스 (8 -하이드록시 -2 -메틸퀴놀 리놀나토)-알루미늄 비페녹사이드)， 페난트롤린
Figure imgf000075_0001
화합물 (예: 예(：사沈!3 (바쏘쿠프로인) ) 등을사용할수 있다. In addition, when used with a phosphorescent dopant in the light emitting layer may be further laminated by a vacuum deposition method or a spin coating method to prevent the triplet exciter or hole diffused into the electron transport layer. The hole-inhibiting substance that can be used at this time is not particularly limited, but is a known one used as a hole-inhibiting material 2019/190270 1 »（： 1 ^ 1 {2019/003723 Any one can be selected and used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Unexamined Patent Application, First Publication No. Hei 11-329734 (A), etc., are typically 831 (1 (bis (8 -Hydroxy-2-methylquinol linolato) -aluminum biphenoxide), phenanthroline
Figure imgf000075_0001
Compounds (e.g., eg, Sans! 3 (Basocuproin)) and the like can be used.
상기와 같이 형성된 발광층 (400) 상부에는 전자수송층 (500)이 형성되는데， 이때 상기 전자수송층은 진공증착법， 스핀코팅법, 캐스트법 등의 방법으로 형성할 수 있다. 또한， 상기 전자수송층의 증착조건은 사용하는 화합물에 따라 다르지만， 일반적으로 정공주입층의 형성과 거의 동일한조건 범위에서 선택하는 것이 좋다. 그 뒤, 상기 전자수송증 (500) 상부에 전자주입증 물질을 증착하여 전자주입 층 (600)을 형성할 수 있으며, 이때 상기 전자수송층은 통상의 전자주입층 물질을 진공증착법， 스핀코팅법, 캐스트법 등의 방법으로 형성할수 있다.  An electron transport layer 500 is formed on the light emitting layer 400 formed as described above, wherein the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like. In addition, although the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same conditions as the formation of the hole injection layer. Thereafter, an electron injection layer material may be deposited on the electron transport certificate 500 to form an electron injection layer 600, wherein the electron transport layer may be formed by vacuum deposition, spin coating, or the like on the electron injection layer material. It can be formed by a method such as a cast method.
상기 유기 발광 소자의 정공주입층 (200)， 정공수송층 (300)， 발광층 (400) , 전 자수송충 (500)은 본 발명에 따른 화합물을 사용하거나 아래와 같은 물질을 사용할 수 있으며, 또는 본 발명에 따른 화합물과 공지의 물질을 함께 사용할 수 있다. The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the total embroidery 500 of the organic light emitting device may use the compound according to the present invention, or may use the following materials, or the present invention. The compound according to the present invention may be used together with a known material.
2019/190270 1»（：1^1{2019/003723 2019/190270 1 »（： 1 ^ 1 {2019/003723
Figure imgf000076_0001
Figure imgf000076_0001
전자주입층 (600) 위에 전자 주입을 위한 캐소드 (2000)을 진공증착법이나 스 퍼터링법 등의 방법에 의해 형성한다. 캐소드로는 다양한 금속이 사용될 수 있다. 구체적인 예로 알루미늄， 금， 은 등의 물질이 있다.  The cathode 2000 for electron injection is formed on the electron injection layer 600 by a method such as vacuum deposition or sputtering. Various metals may be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.
본 발명의 유기 발광 소자는 애노드， 정공주입층, 정공수송층, 발광층, 전자 수송층， 전자주입층， 캐소드 구조의 유기 발광 소자뿐만 아니라, 다양한 구조의 유 기 발광 소자의 구조가 가능하며， 필요에 따라 1층 또는 2층의 중간층을 더 형성하 는 것도 가능하다.  The organic light emitting device of the present invention is not only an organic light emitting device having an anode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injection layer, and a cathode structure, but also a structure of organic light emitting devices having various structures. It is also possible to form one or two intermediate layers.
상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도 에 따라 조절할 수 있으며， 구체적으로는 1 내지 1 , 000 에1이며， 더욱 구체적으로는 5 내지 200 있다.  As described above, the thickness of each organic material layer formed in accordance with the present invention can be adjusted according to the required degree, specifically 1 to 1,000 to 1, more specifically 5 to 200.
또한본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유 기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며， 형태안정성 이 뛰어난 장점이 있다. In addition, the present invention is an organic material layer containing a compound represented by the formula (1) Since the thickness of the base layer can be adjusted in units of molecules, the surface is uniform and there is an excellent shape stability.
본 측면에 따른 유기 발광 화합물에 대하여 본원의 제 1 측면에 대하여 기재 된 내용이 모두 적용될 수 있으나, 이에 제한되지 않을 수 있다. 이하， 본원의 실시예를 통하여 보다 구체적으로 설명하며， 본 실시예에 의하 여 본원의 범위가 제한되는 것은 아니다.  For the organic light emitting compound according to the present aspect may be applied to all of the contents described for the first aspect of the present application, but may not be limited thereto. Hereinafter, the embodiments of the present application will be described in more detail, and the scope of the present application is not limited by the present embodiment.
[실시예 ] EXAMPLE
화학식 1로 표시되는 화함물의 합성  Synthesis of Compounds of Formula 1
화학식 1로 표시되는 화합물은 하기와 같은 반응으로 합성될 수 있으며， 이 에 제한되지 않는다.
Figure imgf000077_0001
The compound represented by Formula 1 may be synthesized by the following reaction, but is not limited thereto.
Figure imgf000077_0001
중가체 의 합성  Synthesis of Heavy Weight
목적 화합물 합성을 위해 중간체 ¾은 하기와 같은 반응을 통하여 합성될 수 있으며， 이에 제한되지 않는다. 2019/190270 1»(：1/10公019/003723 Intermediate ¾ may be synthesized through the following reaction for synthesis of the desired compound, but is not limited thereto. 2019/190270 1 »(： 1/10 公 019/003723
Figure imgf000078_0001
Figure imgf000078_0001
둥근바닥플라스크에 （1오 해 [ 1）,（1]八1대!1-4:-711x）1·이1 801（1 20.0요， 4,6- 1，01110（1 61 0[1），（3]1±101）】161½ 35.5용을 1，4-（1比0 11 900미1에 녹이고 {¾¾3（2]\0 1401111 와 ?（1（?1¾3）4 3.3용을 넣은 후 환류 교반하였다. 11（：로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 【로 추출하고 감압여과한 후 재결정하여 중간체
Figure imgf000078_0002
수율 62%）을 얻었다. （1）, （1] 八 1 to 1 round : 1-4 : -711x 1 이 1 801 (1 20.0 yo, 4,6- 1,01110 （1 61 0 [1）) ， （3] 1 ± 101）】 161½ 35.5 Dissolve in 1,4- （1 比 0 11 900mi1 and add {¾¾3 （2] \ 0 1401111 and? (1 (? 1¾3) 4 3.3 and then reflux. Stirred. The reaction was confirmed with 11 (：), and the reaction was terminated after adding water. The organic layer was extracted with [, filtered under reduced pressure and recrystallized from intermediate
Figure imgf000078_0002
Yield 62%).
둥근바닥플라스크에 상기 ¾1-1 25.0융， 비3（ 113（：01 0）（1 01*011 20당을 1,4- （110X311450 에 녹이고 ^0 17.2§과 （1（（¾?0이20.28을 넣은 후 환류 교반하였다. 11（：로 반응을확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을【로 추출하고 감압여과한후 재결정하여 중간체 1-2 （20.8§, 수율 75%）을 얻었다. \¥0 2019/190270 둥근바닥플라스크에 상기 111-2 22.
Figure imgf000079_0001
In a round-bottom flask, ¾1-1 25.0 mol, ratio 3 （113 （： 01 0） （1 01 * 011 20 per 1,4- （110X311450） is dissolved in ^ 0 17.2 § and （1 （(¾? 2 is 20.2 8 was added and stirred under reflux. The reaction was confirmed with 11 (：), and the reaction was terminated after adding water. The organic layer was extracted with [, filtered under reduced pressure and recrystallized to obtain intermediate 1-2 (20.8 § , yield 75%). \ ¥ 0 2019/190270 above round bottom flask 111-2 22.
Figure imgf000079_0001
0110X311 55（½1에 녹이고 ¾0）3（2 ） 6¾1와 ?（1作1¾3）4 1.5용을 넣은 후 환류 교반하였 다. 11（：로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 로 추출 하고 감압여과한후 재결정하여 중간체 1¾11 （14.（¾， 수율 60%）을 얻었다. 0110X311 55 (½1 was dissolved in ¾0) 3 (2) 6¾1 and? (1 作 1¾3) 4 1.5 yong were added and stirred under reflux. The reaction was confirmed with 11 (：), and the reaction was terminated after adding water. The organic layer was extracted with, filtered under reduced pressure and recrystallized to obtain intermediate 1¾11 (14. (¾, yield 60%).
중가체 ¾2 내지 11의 함성  Moisture of heavy weight ¾2 to 11
하기 표 1과 같이 출발물질을 달리하여， 상기 I 과 같은 방법으로 하기 2 내지 1¾111을 합성하였다.  By varying the starting material as shown in Table 1, the following 2 to 1¾111 was synthesized by the same method as described above.
Figure imgf000079_0002
2019/190270 1»(：1/10公019/003723
Figure imgf000080_0001
Figure imgf000079_0002
2019/190270 1 »(： 1/10 公 019/003723
Figure imgf000080_0001
[표 1] TABLE 1
Figure imgf000080_0003
Figure imgf000080_0003
심시예 1 내지 20： 화합물 합성 Examination Examples 1 to 20: Compound Synthesis
상기 중간체
Figure imgf000080_0002
사용하여 목적 화합물 1 내지 20을 합성하였 다. The intermediate
Figure imgf000080_0002
Was used to synthesize the target compounds 1-20. All.
실시예 1 : 화합물 1의 합성  Example 1 Synthesis of Compound 1
Figure imgf000081_0001
Figure imgf000081_0001
둥근바닥플라스크에 1¾11 3.0g, （[1，1’- 1311611 1]-4- 1）01 116 2.1¾， 卜 此0 0.9 （!2（此3）3 0.2용， （ 此）3? 0.3 를 톨루엔 80 에 녹인 후 환류 교반하 였다. 11（：로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 【로 추 출하고 감압여과한후 컬럼정제 및 재결정하여 화합물 13.0§ （수율 67%）을 얻었다. 미/¾ : 729.27 （100.0%）, 730.27 （58.9%）, 731.27 （17.4%）, 732.28 （3.2%） 실시예 2 : 화합물 2의 합성 In a round bottom flask, 1¾11 3.0g, （[1，1'- 1311611 1] -4-1） 01 116 2.1¾, 卜 0.90 0.9 （! 2 （此 3） 3 For 0.2 ， （（） 3? 0.3 was dissolved in toluene 80 and stirred under reflux. The reaction was confirmed with 11: and the reaction was terminated after adding water. The organic layer was extracted with [, filtered under reduced pressure, purified by column and recrystallized to obtain compound 13.0 § (yield 67%). US / ¾: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%) Example 2 Synthesis of Compound 2
Figure imgf000081_0002
Figure imgf000081_0002
di ( [1， 1’ -biphenyl ]-4-yl ) amine 대신 N-( [1, l'-biphenyl ]-4-yl ) naphtha len- 1-amine을 이용하여 화합물 1과 같은 방법으로 화합물 2를 합성하였다 (수율 63%). m/z： 703.25 (100.0%), 704.25 (56.6%), 705.26 (16.2%), 706.26 (3.1%) 2019/190270 1»(：1/10公019/003723 실시예 3 : 화합물 3의 합성 Compound 2 using N- ([1, l'-biphenyl] -4-yl) naphtha len-1-amine instead of di ([1 ， 1 '-biphenyl] -4-yl) amine Was synthesized (yield 63%). m / z: 703.25 (100.0%), 704.25 (56.6%), 705.26 (16.2%), 706.26 (3.1%) 2019/190270 1 »(： 1/10 公 019/003723 Example 3: Synthesis of Compound 3
Figure imgf000082_0001
Figure imgf000082_0001
di([l，l’-biphenyl ]-4-yl)amine 대신 N-( [1, 1'~bipheny1 ]-4-y1 )naphtha1en- 2-amine을 이용하여 화합물1과 같은 방법으로 화합물3을 합성하였다 (수율65%). m/z： 703.25 (100.0%), 704.25 (56.6%), 705.26 (16.2%), 706.26 (3.1%) 실시예 4 : 화합물 4의 합성 Compound 3 was prepared in the same manner as Compound 1 using N- ([1, 1 ' ~ bipheny1] -4-y1) naphtha1en-2-amine instead of di ([l ， l'-biphenyl] -4-yl) amine. Synthesized (yield 65%). m / z: 703.25 (100.0%), 704.25 (56.6%), 705.26 (16.2%), 706.26 (3.1%) Example 4: Synthesis of Compound 4
Figure imgf000082_0002
Figure imgf000082_0002
di ( [1, 1'-biphenyl ]-4-yl )amine 대신 N-( [1,1’-biphenyl]-4-y1 )-9,9- dimethyl-9H-f1uoren-2-amine 을 이용하여 화합물1과 같은 방법으로 화합물4를 합 성하였다 (수율66¾0.  N- ([1,1'-biphenyl] -4-y1) -9,9-dimethyl-9H-f1uoren-2-amine instead of di ([1, 1'-biphenyl] -4-yl) amine Compound 4 was synthesized in the same manner as compound 1 (yield 66¾0.
m/z： 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%) 2019/190270 1»(：1/10公019/003723 실시예 5 : 화합물 5의 합성 m / z ： 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%) 2019/190270 1 »(： 1/10 公 019/003723 Example 5 Synthesis of Compound 5
Figure imgf000083_0001
Figure imgf000083_0001
di( [1, 1' -biphenyl ]-4-yl )amine 대신 N-( [1, 1' -biphenyl ]-4-yl )-9,9- dimethyl -9H- f 1 uor en-3-am i ne 을 이용하여 화합물 1과 같은 방법으로 화합물 5를 합 성하였다 (수율 65%).  N- ([1, 1 '-biphenyl] -4-yl) -9,9-dimethyl -9H- f 1 uor en-3-am instead of di ([1, 1' -biphenyl] -4-yl) amine Compound 5 was synthesized in the same manner as compound 1 using i ne (yield 65%).
m/z： 769.30 (100.0%), 770.30 (62.5%)， 771.30 (19.3%)， 772.31 (4.1%) 실시예 6 : 화합물 6의 함성  m / z: 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%) Example 6: Synthesis of Compound 6
Figure imgf000083_0002
Figure imgf000083_0002
di ( [1 , 1 ' -biphenyl ]-4-yl ) amine 대신 N-( [1, 1' -biphenyl ]-4-yl )-9, 9 - 0161:117卜9}1 1110^1)-4-81111116을 이용하여 화합물 1과 같은 방법으로 화합물 6을 합성 하였다 (수율 62%).  instead of di ([1, 1 '-biphenyl] -4-yl) amine N- ([1, 1' -biphenyl] -4-yl) -9, 9-0161: 117 卜 9} 1 1110 ^ 1)- Compound 6 was synthesized in the same manner as in compound 1 using 4-81111116 (yield 62%).
m/z： 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%) 2019/190270 실시예 7 : 화합물 7의 합성 m / z ： 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%) 2019/190270 Example 7 Synthesis of Compound 7
Figure imgf000084_0001
Figure imgf000084_0001
«1 대신 «10을 이용하여 화합물 1과 같은 방법으로 화합물 7을 합성하였다 (수율 67%).  Compound 7 was synthesized in the same manner as compound 1 using «10 instead of« 1 (yield 67%).
111/2： 805.30 (100.0%)， 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%) 실시예 8 : 화합물 8의 합성  111/2: 805.30 (100.0%), 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%) Example 8: Synthesis of Compound 8
Figure imgf000084_0002
여 화합물 1과 같은 방법으로 화합물 8을 합성하였다 (수율 69%).
Figure imgf000084_0002
Compound 8 was synthesized in the same manner as in compound 1 (yield 69%).
미八 : 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%) 실시예 9 : 화합물 9의 합성  Mizo: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%) Example 9: Synthesis of Compound 9
Figure imgf000084_0003
2019/190270 1»(：1^1{2019/003723
Figure imgf000084_0003
2019/190270 1 »(： 1 ^ 1 {2019/003723
¾1 대신 1¾13을 이용하여 화합물 1과 같은 방법으로 화합물 9를 합성하였다 (수율 68%). Compound 9 was synthesized in the same manner as compound 1 using 1¾13 instead of ¾1 (yield 68%).
111/2： 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%) 실시예 10 : 화합물 10의 합성  111/2: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%) Example 10: Synthesis of Compound 10
Figure imgf000085_0001
Figure imgf000085_0001
¾1 대신 4를 이용하여 화합물 1과 같은 방법으로 화합물 10을 합성하였다 (수율 65%) . Compound 10 was synthesized in the same manner as compound 1, using 4 instead of ¾1 (yield 65%).
7 (58.9%), 731.27 (17.4%), 732.28 (3.2%)  7 (58.9%), 731.27 (17.4%), 732.28 (3.2%)
Figure imgf000085_0002
Figure imgf000085_0002
ml 대신 5를 이용하여 화합물 1과 같은 방법으로 화합물 11을 합성하였다 (수율 62%).  Compound 11 was synthesized in the same manner as compound 1 using 5 instead of ml (yield 62%).
m/z■- 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%) 2019/190270 1»(：1^1{2019/003723 실시예 12 : 화합물 12의 합성 m / z ■ -745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%) 2019/190270 1 »(： 1 ^ 1 {2019/003723 Example 12: Synthesis of Compound 12
Figure imgf000086_0001
Figure imgf000086_0001
«1 대신 1116을 이용하여 화합물 1과 같은 방법으로 화합물 12를 합성하였다 (수율 65%) .  Compound 12 was synthesized by the same method as Compound 1 using 1116 instead of «1 (yield 65%).
미八 : 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)  Miyoshi: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)
실시예 13 : 화합물 13의 합성  Example 13: Synthesis of Compound 13
Figure imgf000086_0002
Figure imgf000086_0002
1¾11 대신 11\{7을 이용하여 화합물 1과 같은 방법으로 화합물 13을 합성하였다 Compound 13 was synthesized in the same manner as Compound 1 using 11 \ {7 instead of 1¾11.
(수율 62%). (Yield 62%).
며八: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 48.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%) 2019/190270 1»(그1^1{2019/003723 실시예 14 : 화합물 14의 합성 八 8: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 48.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%) 2019/190270 1 »(1 ^ 1 {2019/003723 Example 14: Synthesis of Compound 14
Figure imgf000087_0001
Figure imgf000087_0001
«1 대신 8을 이용하여 화합물 1과 같은 방법으로 화합물 14를 합성하였다 (수율 65%) .  Compound 14 was synthesized by the same method as Compound 1 using 8 instead of «1 (yield 65%).
미八: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)  Micah: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)
실시예 15 : 화합물 15의 합성  Example 15 Synthesis of Compound 15
Figure imgf000087_0002
Figure imgf000087_0002
«1 대신 9를 이용하여 화합물 1과 같은 방법으로 화합물 15를 합성하였다 Compound 15 was synthesized in the same manner as Compound 1 using 9 instead of 1
(수율·)·. (yield·)·.
«1八 : 755.32 (100.0%), 756.32 (62.1%), 757.33 (19.0%), 758.33 (3.9%) 2019/190270 «1 八: 755.32 (100.0%), 756.32 (62.1%), 757.33 (19.0%), 758.33 (3.9%) 2019/190270
실시예 16 : 화합물 16의 합성 Example 16: Synthesis of Compound 16
Figure imgf000088_0001
화합물 1과 같은 방법으로 화합물 16을 합성하였다
Figure imgf000088_0001
Compound 16 was synthesized in the same manner as in compound 1.
(수율 65%) .
Figure imgf000088_0002
(Yield 65%).
Figure imgf000088_0002
꽤比6을 이용하여 화합물 1과 같은 방법으로 화합물 17을 합성하였다 (수율 65%) .
Figure imgf000088_0003
2019/190270 Compound 6 was synthesized in the same manner as in compound 1 using quite non6 (yield 65%).
Figure imgf000088_0003
2019/190270
[1，1’ :3’ ,1’’~1 1±611 1]-4- 16을 이용하여 화합물 1과 같은 방법으로 화합물 18을 합성하였다 (수율 60%). [1,1 ': 3', 1 '' ~ 1 1 ± 611 1] -4- using 16 was synthesized from Compound 18 in the same way as the compound 1 (yield 60%).
미八 : 805.30 (100.0%), 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%) 실시예 19 : 화합물 19의 합성  Mizo: 805.30 (100.0%), 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%) Example 19: Synthesis of Compound 19
Figure imgf000089_0001
Figure imgf000089_0001
di ( [1, l'-bipheny 1 ] -4-y"amine 대신 N-(4-(phenanthren-9-y 1 )pheny 1 ) - [1 , 1’ -biphenyl ]-4_amine을 이용하여 화합물 1과 같은 방법으로 화합물 19를 합성하 였다 (수율 63%).  di ([1, l'-bipheny 1] -4-y "amine instead of N- (4- (phenanthren-9-y 1) pheny 1)-[1, 1 '-biphenyl] -4_amine 1 Compound 19 was synthesized in the same manner as (yield 63%).
m/z： 829.30 (100.0%), 830.30 (68.0%), 831.30 (22.8%), 832.31 (5.2%) 실시예 20 : 화합물 20의 합성  m / z: 829.30 (100.0%), 830.30 (68.0%), 831.30 (22.8%), 832.31 (5.2%) Example 20: Synthesis of Compound 20
Figure imgf000089_0002
Figure imgf000089_0002
di ([ 1,1' -biphenyl ]-4-yl)amine대신 N-([l, l'-biphenyl ]-4-yl )triphenylen- -amine을 이용하여 화합물 1과 같은 방법으로 화합물 20을 합성하였다 (수율 64%). m/z： 803.28 (100.0%), 804.29 (65.4%), 805.29 (21.4%), 806.29 (4.7%) 심시예 21 내지 40 : 유기 발광 소자 제조 실시예 21 Compound 20 was synthesized by the same method as Compound 1 using N-([l, l'-biphenyl] -4-yl) triphenylen- -amine instead of di ([1,1 '-biphenyl] -4-yl) amine. (Yield 64%). m / z: 803.28 (100.0%), 804.29 (65.4%), 805.29 (21.4%), 806.29 (4.7%) Trial Examples 21 to 40: Fabrication of organic light emitting device Example 21
인둠틴옥사이드 ( IT0)가 1500 A 두께가 박막 코팅된 유리 기판을 증류수 초음 파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올， 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시킨 다음 산소 플 라즈마를 이용하여 상기 기판을 5분간 세정한 후 IT0 기판 상부에 열 진공 증착 기 (thermal evaporator)를 이용하여 정공주입중 HI01 600 A , HATCN 50 A , 정공수 송층으로 HT01 250 A , 발광보조층으로 화합물 1 100 A 을 제막한 후 상기 발광층 으로 BH01：BD01 3%로 도핑하여 250 A 제막하였다. 다음으로 전자전달층으로 ET01：Liq(l：l) 300 A 제막한 후 LiF 10 A , 알루미늄 (Al ) 1000 A 제막하고， 이 소자를 글로브 박스에서 밀봉 (Encapsulat ion)함으로써 유기발광소자를 제작하였다. 실시예 22내지 실시예 40  A glass substrate coated with indium tin oxide (IT0) having a thickness of 1500 A was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator on top of the IT0 substrate. Using a thermal evaporator to form HI01 600 A, HATCN 50 A, HT01 250 A as a hole transport layer, Compound 1 100 A as a light emitting auxiliary layer, and then doping with BH01: BD01 3% in a light emitting layer to 250 A It produced. Next, ET01: Liq (l: l) 300 A was formed into an electron transport layer, followed by LiF 10 A and aluminum (Al) 1000 A, which were encapsulated in a glove box to produce an organic light emitting device. . Examples 22-40
실시예 21과 같은 방법으로 화합물 1대신 화합물 2내지 20을사용하여 제막한 유기발광소자를 제하하였다 .  In the same manner as in Example 21, instead of Compound 1, Compound 2 to 20 was used to remove the organic light-emitting device formed into a film.
비교예 1내지 비교예 11  Comparative Example 1 to Comparative Example 11
실시예 21과 같은 방법으로 화합물 1대신 Ref . l 내지 Ref . 11을 사용하여 제 막한유기발광소자를 제작하였다. In the same manner as in Example 21, Ref. l to Ref. 11 was used to fabricate the organic light emitting device.
Figure imgf000091_0001
Figure imgf000091_0001
유기발광소자의 성능평가  Performance Evaluation of Organic Light Emitting Diode
키슬리 2400 소스 메져먼트유닛(Kiethley 2400 source measurement unit) 으 로 전압을 인가하여 전자 및 정공을 주입하고 코니카미놀타(Konica Minolta) 분광 복사계 (CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 21 내 지 40 및 비교예 1 내지 11의 유기 발광 소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며， 그 결과를 하기 표 2에 나타내 었다. 2019/190270 1»（：1/10公019/003723Inject electrons and holes by applying voltage to the Keithley 2400 source measurement unit and measure the luminance when light is emitted using the Konica Minolta Spectroradiometer (CS-2000). By measuring, the performance of the organic light emitting diodes of Examples 21 to 40 and Comparative Examples 1 to 11 were evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 2 below. 2019/190270 1 »（： 1/10 公 019/003723
[표 2]TABLE 2
Figure imgf000092_0001
Figure imgf000092_0001
상기 표 2 에 나타나는 바와 같이 , 발광보조층으로 본 발명의 화합물을사용 한 실시예 21 내지 40은 비교예 1 내지 비교예 11과 비교하여 효율 및 수명이 상승 하는 것을 확인할수 있다. As shown in Table 2, the compound of the present invention is used as the light emitting auxiliary layer. Examples 21 to 40 it can be seen that the efficiency and life is increased compared to Comparative Examples 1 to 11.
보다구체적으로， 비교예 1， 2와 비교하여 , 실시예 21 내지 40은 다이벤조퓨 란이 3환 축합고리인 다이벤조티오펜, 플루오렌 또는 다이벤조퓨란과 선형 연결을 통하여 빠른홀 모빌리티 (Hole mobi l i ty)를 가져 저전압특성을 구현하였다.  More specifically, in comparison with Comparative Examples 1 and 2, Examples 21 to 40 show fast hole mobility through linear linkage with dibenzothiophene, fluorene or dibenzofuran in which dibenzofuran is a tricyclic condensed ring. mobi li ty) to achieve low voltage characteristics.
또한, 비교예 3과 비교하여 , 실시예 21 내지 40은 다이벤조퓨란이 3환 축합 고리인 다이벤조티오펜， 플루오렌 또는 다이벤조퓨란과 결합하여 깊은 HOMO를 형성 하여 우수한 효율을 가질 수 있었다.  In addition, compared with Comparative Example 3, Examples 21 to 40 was able to have a good efficiency by forming a deep HOMO by combining dibenzofuran, dibenzothiophene, fluorene or dibenzofuran which is a tricyclic condensed ring.
또한， 비교예 4， 5와 비교하여, 실시예 21 내지 40은 다이벤조퓨란과아릴아 민의 질소사이에 연결기를 포함하여 깊은 HOMO를 형성하고， 동시에 파이컨쥬게이션 증가로 빠른홀 모빌리티를 가져 저전압특성을 구현하였다.  In addition, compared with Comparative Examples 4 and 5, Examples 21 to 40 form a deep HOMO by including a linking group between the nitrogen of dibenzofuran and arylamine, and at the same time have low hole characteristics due to the rapid hole mobility due to the increase in the conjugation. Was implemented.
또한, 비교예 6, 7, 8, 9와 비교하여， 실시예 21 내지 40은 전자내성이 우수 하고 벌키 특성 (bulkiness)이 적은 다이벤조퓨란의 2번 또는 4번 위치가 연결기를 통하여 아릴아민의 질소와 결합되어 정공수송에 용이한 H0M0 및 높은 LUM0를 유지 하고, 분자간 박막배열이 우수하며， 박막내 모빌리티 개선으로 롤오프 현상이 억제 되어 수명이 개선되었다.  In addition, in comparison with Comparative Examples 6, 7, 8, and 9, Examples 21 to 40 have positions of 2 or 4 of dibenzofuran having excellent electron resistance and low bulky properties. Combined with nitrogen, H0M0 and high LUM0, which is easy for hole transport, are maintained, and the intermolecular thin film arrangement is excellent.
또한, 비교예 10， 11과 비교하여， 실시예 21 내지 40은 질소가 일측에 다이 벤조퓨란을 가지고， 타측에 탄소수 12개 이상의 아릴기를 가짐으로서 파이컨쥬게이 션이 증가할 수 있고, 홀 모빌리티를 개선하여 저전압 특성을 구현하는 결과를 보 였다.  In addition, in comparison with Comparative Examples 10 and 11, Examples 21 to 40 have a benzofuran on one side of nitrogen, and having at least 12 aryl groups of carbon atoms on the other side, the conjugation can be increased, and hole mobility is increased. The improvement resulted in low voltage characteristics.
또한， 실시예 27 및 38은 메타 결합을 갖는 페닐텐을 포함하여 더욱 깊은 2019/190270 1»（：1^1{2019/003723 Examples 27 and 38 also include deeper phenylenes with meta bonds. 2019/190270 1 »（： 1 ^ 1 {2019/003723
를 가져 효율 및 수명이 더욱 향상되었다. 전술한 본원의 설명은 예시를 위한 것이며, 본원이 속하는 기술분야의 통상 의 지식을 가진 자는 본원의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다 른 구체적인 형태로 쉽게 변형이 가능하다는 것을 이해할 수 있을 것이다. 그러므 로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으 로 이해해야만 한다. 예를 들어， 단일형으로 설명되어 있는 각 구성 요소는 분산 되어 실시될 수도 있으며, 마찬가지로 분산된 것으로 설명되어 있는 구성 요소들도 결합된 형태로 실시될 수 있다. The efficiency and lifespan are further improved. The foregoing description of the application is intended for illustration, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present application. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.
본원의 범위는 상기 상세한 설명보다는 후술하는 특허청구범위에 의하여 나 타내어지며， 특허청구범위의 의미 및 범위， 그리고 그 균등 개념으로부터 도출되는 모든 변경 또는 변형된 형태가본원의 범위에 포함되는 것으로 해석되어야 한다. ［부호의 설명］  The scope of the present application is indicated by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and equivalent concepts are included in the scope of the present application. Should be. [Explanation of code]
100： 기판  100 ： Board
200： 정공주입층  200 ： Hole injection layer
300： 정공수송층  300 ： hole transport layer
400： 발광층  400 ： light emitting layer
500： 전자수송층  500 ： electron transport layer
600： 전자주입층  600 ： electron injection layer
1000： 애노드  1000 ： Anode
2000： 캐소드 2019/190270 1»（：1/10公019/003723 2000 ： cathode 2019/190270 1 »（： 1/10 公 019/003723
제출시 공란 Blank at submission

Claims

2019/190270 1»（：1^1{2019/003723 【청구의 범위】 【청구항 1】 하기 화학식 1로 표시되는 화합물; 2019/190270 1 »（： 1 ^ 1 {2019/003723 [Claim of claims] [Claim 1] A compound represented by the following formula (1);
[화학식 1]  [Formula 1]
Figure imgf000096_0001
Figure imgf000096_0001
!은 치환 또는 비치환의 0 50의 아릴기 , 또는 치환 또는 비치환의 05-050 의 헤테로아릴기이고， ! Is a substituted or unsubstituted 0 50 aryl group, or a substituted or unsubstituted 05-050 heteroaryl group,
2는 치환 또는 비치환의 （：12 50의 아릴기이고,  2 is a substituted or unsubstituted aryl group of (： 12 50),
묘, ， ¾ 내지 ¾은 각각 독립적으로 수소, 할로겐, 니트로기， 니트릴기， 치 환 또는 비치환의 레30의 알킬기, 치환 또는 비치환의 02~030^ 알케닐기， 치환 또 는 비치환의 0公¾0의 알콕시기， 치환 또는 비치환의 （：1 30의 설파이드기， 치환 또는 비치환의 06~030^ 아릴기， 또는 치환 또는 비치환의 05~030£1 헤테로아릴기이고， 인 접한 복수의 묘1끼리 , ¾끼리， 1?3끼리， 또는 I?과 I?’ 는 서로 결합하여 환을 형성하거 나 형성하지 않을 수 있고， 요4와 1?6 또는 요5와 모6은 서로 결합하여 환을 형성하거나 형성하지 않을 수 있으며， 0 2019/190270 1»（：1^1{2019/003723
Figure imgf000097_0001
The seedlings, ¾ to ¾ each independently represent hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted LE 30 alkyl group, substituted or unsubstituted 02-030 ^ alkenyl group, substituted or unsubstituted 0 公 ¾0 Alkoxy group, substituted or unsubstituted (1: 30 sulfide group, substituted or unsubstituted 06-030 ^ aryl group, or substituted or unsubstituted 05-030 £ 1 heteroaryl group, adjacent multiple seedlings, ¾ 1 to 3, or I? And I? ' May combine with each other to form a ring or not, and John 4 and 1-6 or Yo 5 and 6 may combine with each other to form a ring or not, 0 2019/190270 1 »（： 1 ^ 1 {2019/003723
Figure imgf000097_0001
환의 05-030£1 해테로아릴렌기이고， It is a 05-030 £ 1 heteroarylene group of the ring,
는 치환 또는 비치환의 06~030^ 아릴텐기， 또는 치환 또는 비치환의 05~030 의 헤테로아릴렌기이고,  Is a substituted or unsubstituted 06-030 ^ arylten group, or a substituted or unsubstituted 05-030 heteroarylene group,
1은 0 또는 1 내지 4의 정수이고,  1 is 0 or an integer of 1 to 4,
독립적으로 0 또는 1 내지 3의 정수이며 , 는 II이 2 이상인 경우 ， ¾ 및 1?3은 각각 서로 같거나 다를 수
Figure imgf000097_0002
Are independently 0 or an integer from 1 to 3, where II is 2 or more, ¾ and 1 to 3 may each be the same or different.
Figure imgf000097_0002
【청구항 2]  [Claim 2]
제 1항에 있어서，  The method of claim 1,
상기 화합물은 하기 화학식 2로 표시되는 화합물;  The compound is a compound represented by the formula (2);
[화학식 2]  [Formula 2]
Figure imgf000097_0003
상기 화학식 2에서，
Figure imgf000097_0003
In Chemical Formula 2,
X , 1， 2 , 묘,
Figure imgf000097_0004
화학식 1에서의 정의 와 같고, X, 1, 2, Tomb,
Figure imgf000097_0004
As defined in Formula 1,
묘7은 수소， 할로겐， 니트로기, 니트릴기, 치환 또는 비치환의 （：1~030의 알킬 2019/190270 1»（：1^1{2019/003723 Fig. 7 shows hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted alkyl of 1 ~ 030 2019/190270 1 »（： 1 ^ 1 {2019/003723
기， 치환 또는 비치환의 02~公¾)의 알케닐기 , 치환 또는 비치환의 (：1 30의 알콕시기， 치환 또는 비치환의 에 의 설파이드기， 치환 또는 비치환의 06~030£1 아릴기， 또는 치환 또는 비치환의 05 30의 헤테로아릴기이며, Groups, substituted or unsubstituted 02- 公 ¾) alkenyl groups, substituted or unsubstituted (: 1-30 alkoxy groups, substituted or unsubstituted sulfide groups, substituted or unsubstituted 06-030 £ 1 aryl groups, or substituted Or an unsubstituted 05 30 heteroaryl group,
0는 1 내지 4의 정수이고， 13는 0 또는 1 내지 4의 정수이며, 상기 0 또는 V 가 2 이상인 경우 모7은 서로 같거나 다를 수 있고, 0가 2 이상인 경우 는 서로 같 거나 다를 수 있다.  0 is an integer from 1 to 4, 13 is 0 or an integer from 1 to 4, when 0 or V is 2 or more, 7 may be the same or different, and when 0 is 2 or more may be the same or different. .
【청구항 3]  [Claim 3]
제 1항에 있어서，  The method of claim 1,
상기 화합물은 하기 화학식 3으로 표시되는 화합물;  The compound is a compound represented by the following formula (3);
[화학식 3]  [Formula 3]
Figure imgf000098_0001
상기 화학식 3에서，
Figure imgf000098_0001
In Chemical Formula 3,
X， 1， 2 , 모， ， 1?1내지 요6， 1 , m 및 II은 상기 화학식 1에서의 정의와 같 고，  X, 1, 2, parent, 1 to 1 to 6, 1, m and II are the same as the definition in Formula 1,
요7은 수소， 할로겐， 니트로기, 니트릴기, 치환 또는 비치환의 레30의 알킬 기， 치환 또는 비치환의 30의 알케닐기 , 치환 또는 비치환의 0030의 알콕시기 , 치환 또는 비치환의 003()의 설파이드기， 치환 또는 비치환의 06-030^1 아릴기, 또는 0 2019/190270 1＞（그1'/1 技019/0037：23 (7) hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted LE 30 alkyl group, substituted or unsubstituted 30 alkenyl group, substituted or unsubstituted 0030 alkoxy group, substituted or unsubstituted 003 () sulfide Groups, substituted or unsubstituted 06-030 ^ 1 aryl groups, or 0 2019/190270 1 ＞ （1 '/ 1 技 019/0037 ： 23
치환또는 비치환의 05~030£1 헤테로아릴기이며, A substituted or unsubstituted 0 5 ~ 030 £ 1 heteroaryl group,
0는 1 내지 4의 정수이고， I）는 0또는 1 내지 4의 정수이며，  0 is an integer of 1 to 4, I) is 0 or an integer of 1 to 4,
상기 0 또는 I）가 2 이상인 경우요7은 서로 같거나 다를 수 있고， 0가 2 이상 인 경우 I）는 서로 같거나다를 수 있다.  When 0 or I) is 2 or more, 7 may be the same or different, and when 0 is 2 or more, I) may be the same or different.
【청구항 4]  [Claim 4]
제 1항에 있어서,  The method of claim 1,
상기 화합물은 하기 화학식 4또는 화학식 5로 표시되는 화합물;  The compound is a compound represented by the following formula (4) or (5);
[화학식 4]  [Formula 4]
Figure imgf000099_0001
Figure imgf000099_0001
상기 화학식 4 및 화학식 5에서， In Chemical Formulas 4 and 5,
1， 2, ¾내지 ¾， 1 및 II은상기 화학식 1에서의 정의와 같고, 2019/190270 1»（：1^1{2019/003723 1, 2, ¾ to ¾, 1 and II are the same as defined in Formula 1, 2019/190270 1 »（： 1 ^ 1 {2019/003723
X는 0 또는 이며， X is 0 or
¾는 서로 같거나 다를 수 있고，  ¾ can be the same or different from each other,
모7은 수소, 할로겐, 니트로기, 니트릴기， 치환 또는 비치환의 01~030£] 알킬 기， 치환 또는 비치환의 比 30의 알케닐기 , 치환 또는 비치환의 0（：30의 알콕시기， 치환 또는 비치환의 30의 설파이드기， 치환 또는 비치환의 06~030^ 아릴기 , 또는 치환 또는 비치환의 05~030£] 헤테로아릴기이고， Parent 7 is hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted 01-030 £] alkyl group, substituted or unsubstituted more than 30 alkenyl group, substituted or unsubstituted 0 (： 30 alkoxy group, substituted or unsubstituted 30 sulfide group of a ring, substituted or unsubstituted 06-030 ^ aryl group, or substituted or unsubstituted 05-030 £] heteroaryl group,
0는 1 내지 4의 정수이며 , 는 0 또는 1 내지 4의 정수이며 ,  0 is an integer from 1 to 4, is 0 or an integer from 1 to 4,
상기 0 또는 I）가 2 이상인 경우 1?7은 서로 같거나 다를 수 있고， 0가 2 이상 인 경우 I）는 서로 같거나 다를 수 있다.  When 0 or I) is 2 or more, 1 to 7 may be the same or different, and when 0 is 2 or more, I) may be the same or different.
【청구항 5】  [Claim 5]
제 1항에 있어서,  The method of claim 1,
상기 화합물은 하기 화학식 6으로 표시되는 화합물;  The compound is a compound represented by the formula (6);
[화학식 6]  [Formula 6]
Figure imgf000100_0001
, , , ， , 기 화학식 1에서의 정의와 같 2019/190270 1*（:17X112019/0037:23
Figure imgf000100_0001
,,,,,, The same as defined in Chemical Formula 1 2019/190270 1 * （: 17X112019 / 0037: 23
요7은 수소， 할로겐， 니트로기， 니트릴기， 치환 또는 비치환의 ~ 3◦의 알킬 기 , 치환 또는 비치환의 02~(：30의 알케닐기， 치환 또는 비치환의 :◦의 알콕시기， 치환또는 비치환의 003()의 설파이드기, 치환 또는 비치환의 06~030^ 아릴기, 또는 치환또는 비치환의 05^30의 해테로아릴기이며， John 7 is hydrogen, halogen, a nitro group, a nitrile group, a substituted or unsubstituted, ~ 3◦ alkyl group, a substituted or unsubstituted, 02 to (30 alkenyl group, a substituted or unsubstituted: ◦ of alkoxy groups, substituted or unsubstituted It is a 003 () sulfide group of a ring, a substituted or unsubstituted 06-030 ^ aryl group, or a substituted or unsubstituted 05 ^ 30 heteroaryl group,
0는 1 내지 4의 정수이고， I)는 0 또는 1 내지 4의 정수이며， 0 is an integer from 1 to 4, I ) is 0 or an integer from 1 to 4,
상기 0 또는 ?가 2 이상인 경우 1?7은 서로 같거나 다를 수 있고， 0가 2 이상 인 경우 13는 서로 같거나 다를 수 있다.  When 0 or? Is 2 or more, 1 to 7 may be the same or different from each other, and when 0 is 2 or more, 13 may be the same or different.
【청구항 6]  [Claim 6]
제 1항에 있어서，  The method of claim 1,
상기 화합물은 하기 화학식 7또는 화학식 8로 표시되는 화합물;  The compound is a compound represented by the following formula (7) or formula (8);
[화학식 7]  [Formula 7]
Figure imgf000101_0001
Figure imgf000101_0001
[화학식 8] [Formula 8]
Figure imgf000102_0001
Figure imgf000102_0001
상기 화학식 7 및 화학식 8에서, In Chemical Formulas 7 and 8,
1， 2, ¾내지 1¾, 1 및 II은 상기 화학식 1에서의 정의와 같고, 1, 2, ¾ to 1¾, 1 and II are the same as defined in Formula 1,
X는 0또는 £이며, X is 0 or £,
요2는 서로 같거나 다를 수 있고，  2 can be the same or different,
묘7은 수소， 할로겐 , 니트로기 , 니트릴기 , 치환 또는 비치환의 레30의 알킬 기 , 치환 또는 비치환의 02~030·^ 알케닐기， 치환 또는 비치환의 （：1 30의 알콕시기 , 치환또는 비치환의 （：1 30의 설파이드기， 치환 또는 비치환의 06^30의 아릴기， 또는 치환또는 비치환의 05 030의 헤테로아릴기이고，  Fig. 7 is hydrogen, halogen, nitro group, nitrile group, substituted or unsubstituted LE 30 alkyl group, substituted or unsubstituted 02-030. ^ Alkenyl group, substituted or unsubstituted （: 1 30 alkoxy group, substituted or unsubstituted. Ring (s): 1 30 sulfide group, substituted or unsubstituted 06 ^ 30 aryl group, or substituted or unsubstituted 05 030 heteroaryl group,
0는 1 내지 4의 정수이며， I）는 0또는 1 내지 4의 정수이며,  0 is an integer of 1 to 4, I) is 0 or an integer of 1 to 4,
상기 0 또는 I）가 2 이상인 경우 1?7은 서로 같거나 다를 수 있고, 0가 2 이상 인 경우 는서로 같거나 다를 수 있다.  When 0 or I) is 2 or more, 1 to 7 may be the same or different, and when 0 is 2 or more, they may be the same or different.
【청구항 7]  [Claim 7]
제 1항에 있어서，  The method of claim 1,
상기 묘1내지 묘6는 각각독립적으로 수소, 또는 페닐기인 화합물.  Compounds 1 to 6 are each independently hydrogen or a phenyl group.
【청구항 8] 2019/190270 1»（：1/10公019/003723 [Claim 8] 2019/190270 1 »（： 1/10 公 019/003723
제 2항 내지 제 6항 중 어느 한 항에 있어서， The method according to any one of claims 2 to 6,
상기 ¾ 내지 은 각각 독립적으로 수소， 또는 페닐기인 화합물.  The ¾ to are each independently hydrogen or a phenyl group.
【청구항 9]  [Claim 9]
제 1항 내지 제 3항 또는 제 5항 중 어느 한 항에 있어서,  The method according to any one of claims 1 to 3 or 5,
상기 묘 및 묘’는 각각 독립적으로 （：1 3의 알킬기인 화합물.  The seedlings and seedlings' are each independently a alkyl group of (1: 1).
【청구항 10】  [Claim 10]
저 11항 내지 제 4항 또는 제 6항 중 어느 한 항에 있어서，  The method according to any one of claims 11 to 4 or 6,
상기 X는 0인 화합물.  X is 0.
【청구항 11】  [Claim 11]
제 1항 내지 제 4항 또는 제 6항 중 어느 한 항에 있어서,  The method according to any one of claims 1 to 4 or 6,
상기 X는 인 화합물.  X is a phosphorus compound.
【청구항 12】  [Claim 12]
제 1항 내지 제 6항 중 어느 한항에 있어서，  The method according to any one of claims 1 to 6,
상기 1은 페닐, 나프틸， 비페닐， 터페닐， 플루오렌일， 디알킬플루오렌일, 디아릴플루오렌일， 다이벤조퓨란일， 다이벤조티오펜일 및 이들의 조합으로 이루어 진 군에서 선택되고，  1 is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof Being
상기 2는 비페닐， 페닐나프틸， 터페닐, 플루오렌일， 디알킬플루오렌일， 디 아릴플루오렌일， 다이벤조퓨란일, 다이벤조티오펜일 및 이들의 조합으로 이루어진 군에서 선택되는 화합물.  2 is a compound selected from the group consisting of biphenyl, phenylnaphthyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof .
【청구항 13】  [Claim 13]
제 1항에 있어서， 2019/190270 1»（：1^1{2019/003723 The method of claim 1, 2019/190270 1 »（： 1 ^ 1 {2019/003723
상기 1^2는 적어도 하나의 1,4 -페닐렌 또는 1,3 -페닐렌을포함하는 치환또는 비치환의 06-024^ 아릴렌인 화합물 . Wherein 1 ^ 2 is substituted or unsubstituted 0 6 -024 ^ arylene including at least one 1,4-phenylene or 1,3-phenylene.
【청구항 14】  [Claim 14]
제 1항내지 제 6항중 어느 한항에 있어서，  The method of any one of claims 1 to 6,
상기 !은 페닐， 비페닐， 터페닐， 디메틸플루오렌일 및 이들의 조합으로 이 루어진 군에서 선택되고，  Wherein! Is selected from the group consisting of phenyl, biphenyl, terphenyl, dimethylfluorenyl and combinations thereof,
상기 2는 비페닐， 터페닐， 디메틸플루오렌일 및 이들의 조합으로 이루어진 군에서 선택되는화합물.  2 is a compound selected from the group consisting of biphenyl, terphenyl, dimethylfluorenyl and combinations thereof.
【청구항 15】  [Claim 15]
제 1항에 있어서，  The method of claim 1,
상기 1, 2 및 중 적어도 하나는 메타 결합을 갖는 페닐텐기를 포함하 는 화합물. At least one of 1, 2, and 2 includes a phenylten group having a meta bond.
【청구항 16】  [Claim 16]
제 15항에 있어서，  The method of claim 15,
상기 1은 메타 결합을 갖는 비페닐 또는 메타 결합을 갖는 터페닐이거나, 상기 2는 메타결합을갖는비페닐 또는 메타결합을 갖는 터페닐인 화합물.  1 is biphenyl having a meta bond or terphenyl having a meta bond, or 2 is biphenyl having a meta bond or terphenyl having a meta bond.
【청구항 17】  [Claim 17]
제 1항 내지 제 6항 중 어느 한 항에 있어서， 하기 3,)내지 (：) 중 어느 하나 이상을만족하는화합물:  The compound according to any one of claims 1 to 6, which satisfies at least one of the following 3,) to (:):
크) 1및 2는 비페닐기;  C) 1 and 2 are biphenyl groups;
I)) 1및 2중적어도하나는 6원환만으로구성된 4이상의 아릴기; 및 0 2019/190270 1»（：1/10公019/003723 I)) four or more aryl groups consisting of one and at least one six-membered ring only; And 0 2019/190270 1 »（： 1/10 公 019/003723
0) 1^2는 (：10이상의 아릴렌기이다. 0) 1 ^ 2 is an arylene group of (: 10 or more.
【청구항 18】  [Claim 18]
제 1항에 있어서，  The method of claim 1,
상기 화합물은 하기 화합물 중 어느 하나인 화합물.  The compound is any one of the following compounds.
Figure imgf000105_0001
Figure imgf000106_0001
Figure imgf000107_0001
Figure imgf000105_0001
Figure imgf000106_0001
Figure imgf000107_0001
Figure imgf000108_0001
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Figure imgf000118_0001
Figure imgf000119_0001
Figure imgf000118_0001
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Figure imgf000120_0001
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Figure imgf000122_0001
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Figure imgf000127_0001
Figure imgf000127_0001
Figure imgf000128_0001
Figure imgf000129_0001
Figure imgf000130_0001
ί
Figure imgf000128_0001
Figure imgf000129_0001
Figure imgf000130_0001
ί
Figure imgf000131_0001
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Figure imgf000133_0001
Figure imgf000131_0001
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Figure imgf000137_0001
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Figure imgf000140_0001
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Figure imgf000146_0001
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Figure imgf000148_0001
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Figure imgf000147_0001
Figure imgf000148_0001
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Figure imgf000150_0001
Figure imgf000151_0001
Figure imgf000151_0001
Figure imgf000152_0001
Figure imgf000152_0001
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Figure imgf000154_0001
Figure imgf000155_0001
Figure imgf000156_0001
2019/190270 1»（：1^1{2019/003723
Figure imgf000153_0001
Figure imgf000154_0001
Figure imgf000155_0001
Figure imgf000156_0001
2019/190270 1 » （： 1 ^ 1 {2019/003723
Figure imgf000157_0001
Figure imgf000157_0001
【청구항 19】  [Claim 19]
제 1 전극 및 제 2 전극사이에 제 1항 내지 제 6항 중 어느 한 항에 따른 화합 물을함유하는유기물층을포함하는유기 발광소자.  An organic light emitting device comprising an organic layer containing a compound according to any one of claims 1 to 6 between a first electrode and a second electrode.
【청구항 20]  [Claim 20]
제 19항에 있어서，  The method of claim 19,
상기 유기물층은 정공주입층, 정공수송층 및 발광보조층중 1층 이상인 유기 발광소자.  The organic material layer is an organic light emitting device of at least one of a hole injection layer, a hole transport layer and a light emitting auxiliary layer.
PCT/KR2019/003723 2018-03-30 2019-03-29 Novel compound and organic light-emitting device comprising same WO2019190270A1 (en)

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