WO2021132956A1 - Organic compound and organic electroluminescent device using same - Google Patents

Organic compound and organic electroluminescent device using same Download PDF

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WO2021132956A1
WO2021132956A1 PCT/KR2020/017988 KR2020017988W WO2021132956A1 WO 2021132956 A1 WO2021132956 A1 WO 2021132956A1 KR 2020017988 W KR2020017988 W KR 2020017988W WO 2021132956 A1 WO2021132956 A1 WO 2021132956A1
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aryl
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compound
nuclear atoms
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손호준
엄민식
김회문
정화순
배형찬
김진웅
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솔루스첨단소재 주식회사
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H10K50/16—Electron 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, by including a compound having excellent electron transport ability and the same in one or more organic material layers, characteristics such as luminous efficiency, driving voltage, lifespan, as well as progressiveness It relates to an organic electroluminescent device having an improved driving voltage.
  • an organic electroluminescent device (hereinafter, referred to as an 'organic EL device'), when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.
  • the material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the emission color.
  • yellow and orange light emitting materials are also used as light emitting materials for realizing better natural colors.
  • a host/dopant system may be used as a light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound including heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention is focused on phosphorescent host materials as well as phosphorescent dopants.
  • NPB, BCP, Alq 3, etc. represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials.
  • a metal complex compound containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc. is a blue, green, and red dopant material. is being used as So far, CBP has shown excellent properties as a phosphorescent host material.
  • the present invention is excellent in electron injection and transport ability, electrochemical stability, thermal stability, etc. to provide a novel organic compound that can be used as an organic material layer material of an organic electroluminescent device, specifically, an electron transport layer material or an N-type charge generation layer material aim to
  • the present invention provides an organic compound represented by the following formula (1):
  • a and B is R 1 and the rest is a substituent represented by the following formula (2),
  • R 1 is a C 1 ⁇ C 60 alkyl group
  • n is an integer from 0 to 3
  • EWG is an electron withdrawing force with high electron absorption
  • n is an integer from 0 to 4,
  • R 2 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group , C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group
  • the alkyl group of R 1 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, C 6 to C 60 Arylox Period, C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Arylphos pingi, C 6 ⁇ aryl phosphine oxide of a C 60 group, C 6 ⁇ C 60 aryl amine group, the nuclear atoms of 5 to 60
  • the present invention is an anode; cathode; and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers provides an organic electroluminescent device comprising the above-described organic compound.
  • the organic material layer including the compound may be an electron transport layer.
  • the present invention provides an anode and a cathode spaced apart from each other; a plurality of light emitting units interposed between the anode and the cathode; an N-type charge generation layer and a P-type charge generation layer interposed between adjacent light emitting units, wherein each light emitting unit includes a hole transport layer, a light emitting layer and an electron transport layer, and the N type charge generation layer comprises the above-mentioned compound It provides an organic electroluminescent device comprising.
  • the compound of the present invention Since the compound of the present invention has excellent electron transport ability, light emitting ability, electrochemical stability, thermal stability, etc., it can be used as an organic material layer material of an organic electroluminescent device.
  • an organic electroluminescent device having superior light emitting performance, low driving voltage, high efficiency and long lifespan compared to conventional materials. can be manufactured, and furthermore, a full-color display panel with improved performance and lifespan can be manufactured.
  • FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
  • FIG. 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a second embodiment of the present invention.
  • FIG 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a third embodiment of the present invention.
  • FIG. 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a fourth embodiment of the present invention.
  • 360 electron transport auxiliary layer, 400: a first light emitting unit
  • 410 a first hole transport layer
  • 420 a first light emitting layer
  • 430 a first electron transport layer
  • 440 a hole injection layer
  • 500 a second light emitting unit
  • 510 a second hole transport layer
  • 520 a second light emitting layer
  • 530 a second electron transport layer
  • 600 charge generation layer
  • 610 n-type charge generation layer
  • the present invention is an electron transport layer material or electron transport auxiliary layer material that can improve the high efficiency, long life, driving voltage characteristics and progressive driving voltage characteristics of an organic electroluminescent device due to excellent electron injection and transport ability, electrochemical stability, thermal stability, etc. It provides a novel compound that can be used as
  • an alkyl group is introduced at one of the 7th and 9th carbon positions of the phenanthroline moiety, and an electron withdrawing group with high electron absorption in the rest EWG) is introduced directly or through a linker group (eg, a phenylene group, a biphenylene group, a terphenylene group).
  • a linker group eg, a phenylene group, a biphenylene group, a terphenylene group.
  • the compound represented by Formula 1 includes a structure in which EWG is introduced directly or through a linker group at the 7th carbon position of the phenanthroline moiety, and an alkyl group is introduced at the 9th carbon position.
  • the phenanthroline moiety is a moiety with high electron absorption.
  • EWG electron withdrawing group
  • the compound of Formula 1 exhibits an electron transfer rate is improved so that the electron injection and transport ability can be maximized. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device, it not only realizes the low driving voltage, high current efficiency, and long life characteristics of the device, but also improves the progressive driving voltage characteristic to increase the power consumption and decrease the lifespan of the device. can be prevented
  • the stability of the molecule may be increased.
  • the molecular weight can be minimally increased compared to a phenanthroline derivative in which hydrogen (H) or an aryl group is introduced. This can minimize the heat received by the compound of Formula 1 when manufacturing the device, thereby improving the thermal stability of the compound, thereby preventing the device from being deteriorated. Accordingly, the compounds of the present invention are thermally and electrochemically stable and have high triplet energy.
  • the compounds of the present invention contain nitrogen (N) in sp 2 hybrid orbitals that are relatively electron-rich.
  • the nitrogen may form a gap state by binding with an alkali metal or alkaline earth metal, which is a dopant of the N-type charge generation layer. Therefore, the formed gap state makes it possible to facilitate the transfer of electrons from the N-type charge generation layer to the electron transport layer.
  • the compound represented by Formula 1 has excellent electron injection and transport ability. Accordingly, the compound of the present invention may be used as an organic material layer, preferably an electron transport layer, of an organic electroluminescent device. In addition, the compound of the present invention may be used as an N-type charge generating layer material of an organic electroluminescent device having a tandem structure. As such, the compound represented by Formula 1 of the present invention is applied as an electron transport layer material or an N-type charge generation layer material of an organic electroluminescent device, thereby improving characteristics such as driving voltage, luminous efficiency and lifespan of the device. Of course, it is possible to prevent the increase of the progressive driving voltage, and furthermore, the performance of the full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.
  • one of A and B is R 1 , and a C 1 to C 60 alkyl group, and the remainder is a substituent represented by Formula 2 above.
  • the compound represented by Formula 1 may be a compound represented by Formula 3 below.
  • n, EWG, m, R 1 and R 2 are each as defined in Formula 1 above.
  • R 1 is a C 1 ⁇ C 60 alkyl group, for example, may be a C 1 ⁇ C 12 alkyl group.
  • the alkyl group of R 1 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, C 6 to C 60 Arylox Period, C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Arylphos pingi, C 6 ⁇ aryl phosphine oxide of a C 60 group, C 6 ⁇ C 60 aryl amine group, the nuclear atoms of 5 to 60
  • the compound represented by Formula 1 may be a compound represented by any one of Formulas 4 to 7, but is not limited thereto.
  • n, m, R 2 and EWG are each as defined in Formula 1 above.
  • n is an integer of 0 to 3.
  • the A moiety is meant to be a single bond (direct bond).
  • n is an integer of 1 to 3
  • the moiety is a divalent linker group, and means selected from the group consisting of a phenylene group, a biphenylene group and a terphenylene group.
  • m is an integer of 0 to 4.
  • R 2 when m is 0, it means that hydrogen is not substituted with a substituent R 2
  • m when m is an integer of 1 to 3, one or more R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group , nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6
  • the moiety may be a linker group selected from the group consisting of the following linker groups Link-1 to Link-5.
  • hydrogen of the following linker groups may be substituted with one or more substituents such as deuterium (D), halogen, cyano group, nitro group, and C 1 to C 12 alkyl group.
  • EWG is an electron withdrawing group with high electron absorption, and specifically may be a heteroaromatic ring having 5 to 30 nuclear atoms.
  • the heteroaromatic ring may contain one or more heteroatoms among N, S, O, and Se.
  • the EWG may be a substituent represented by the following Chemical Formula S1 or S2, but is not limited thereto.
  • X 1 to X 5 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 to X 5 is N, wherein a plurality of Ar 2 are the same as or different from each other,
  • Y 1 to Y 4 are the same or different from each other, and each independently is N or C(Ar 3 ), provided that at least one of Y 1 to Y 4 is N, wherein a plurality of Ar 3 are the same or different from each other,
  • Ar 1 To Ar 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ aryl phosphine oxide of a C 60 group, C 6 ⁇ C 60 of the
  • the Ar 1 To Ar 3 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl Boron group, arylphosphanyl group, arylphosphinyl group, arylamine group, heteroarylamine group and (aryl) (heteroaryl) amine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, nucleus A heteroaryl group having 5 to 60 atoms, C 1
  • the heterocycloalkyl group and the heteroaryl group each include at least one heteroatom selected from the group consisting of N, S, O and Se.
  • the condensed ring is a C 6 ⁇ C 60 alicyclic ring, 5 ⁇ 60 membered heteroalicyclic ring, C 6 ⁇ C 60 aromatic ring, 5 ⁇ 60 membered heteroaromatic ring, or a combination thereof In this case, when the condensed ring is polycyclic, each ring is the same as or different from each other.
  • the EWG may be a substituent represented by any one of the following Chemical Formulas S3 to S7, but is not limited thereto.
  • X 1 , X 3 and X 5 are each as defined in Formula S1, provided that at least one of X 1 , X 3 and X 5 is N,
  • X 1 and X 3 are each as defined in Formula S1, provided that at least one of X 1 and X 3 is N,
  • Z 1 is O or S
  • X 1 and X 5 are each as defined in Formula S1, provided that at least one of X 1 and X 5 is N,
  • Z 1 is O or S
  • Y 1 , Y 2 and Y 4 are each as defined in Formula S2 above, provided that at least one of Y 1 , Y 2 and Y 4 is N,
  • Ar 1 to Ar 3 are each as defined in the above formulas S1 and S2,
  • a is an integer from 0 to 4,
  • Ar 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group , C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphine group , C 6 ⁇ C 60 Arylphosphine oxide group, C 6 ⁇ C 60 An arylamine group, a heteroarylamine group
  • the compound represented by Formula 1 according to the present invention may be embodied as a compound represented by any one of the following Formulas 8 to 14, but is not limited thereto.
  • X 1 , X 3 and X 5 are the same or different from each other, and each independently represents N or C(Ar 2 ), provided that at least one of X 1 to X 5 is N, wherein a plurality of Ar 2 are the same as or different from each other and;
  • X 1 and X 3 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 and X 3 is N, wherein a plurality of Ar 2 are the same as or different from each other,
  • Z 1 is O or S
  • X 1 and X 5 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 and X 5 is N, wherein a plurality of Ar 2 are the same or different from each other,
  • Z 1 is O or S
  • Y 1 , Y 2 and Y 4 are the same as or different from each other, and each independently represent N or C(Ar 3 ), provided that at least one of Y 1 , Y 2 and Y 4 is N, wherein a plurality of Ar 3 are each other the same or different;
  • n, m, R 1 and R 2 are each as defined in Formula 1 above,
  • a is an integer from 0 to 4,
  • b and c are each 0 or 1
  • Ar 2 and Ar 3 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ⁇ C 40 alkyl group, a C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ aryl phosphine oxide of a C
  • Ar 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group , C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphine group , C 6 ⁇ C 60 Arylphosphine oxide group, C 6 ⁇ C 60 An arylamine group, a heteroarylamine group
  • the Ar 2 And Ar 3 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl A boron group, an arylphosphanyl group, an arylphosphinyl group, an arylamine group, a heteroarylamine group, an (aryl) (heteroaryl)amine group, and a condensed ring are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 Aryl group, heteroaryl group
  • the compound represented by Formula 1 according to the present invention described above is from the group consisting of the following compounds A-1 to A-60, B-1 to B-60, C-1 to C-60, and D-1 to D-60 may be embodied in the selected compound.
  • the compound represented by Formula 1 according to the present invention is not limited by those exemplified below.
  • alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms.
  • one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazo
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
  • R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkylsilyl means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl.
  • arylsilyl means a silyl substituted with aryl having 5 to 60 carbon atoms, and includes mono- as well as polyarylsilyl such as di- and tri-arylsilyl.
  • alkyl boron group means a boron group substituted with an alkyl having 1 to 40 carbon atoms
  • aryl boron group means a boron group substituted with an aryl group having 6 to 60 carbon atoms.
  • alkylphosphinyl group means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.
  • arylphosphinyl group means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
  • arylamine means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamines.
  • heteroarylamine means an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.
  • (aryl) (heteroaryl) amine means an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.
  • condensed ring refers to a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, or means a combination of these.
  • an aspect of the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') including the compound represented by Formula 1 described above.
  • FIG. 1 to 4 are cross-sectional views schematically showing organic electroluminescent devices according to first to fourth embodiments of the present invention.
  • the organic electroluminescent device according to the present invention is an anode (anode) 100, a cathode (cathode) 200, and one or more layers interposed between the anode and the cathode
  • the organic material layer 300 is included, and at least one of the one or more organic material layers includes the compound represented by Formula 1 above.
  • the compound may be used alone, or two or more may be used in combination.
  • the one or more organic material layers 300 may include any one of a hole injection layer 310 , a hole transport layer 320 , a light emitting layer 330 , an electron transport auxiliary layer 360 , an electron transport layer 340 , and an electron injection layer 350 . It may include one or more, of which at least one organic material layer 300 includes the compound represented by Formula 1 above. Specifically, the organic material layer including the compound of Formula 1 may be the electron transport layer 340 . That is, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material.
  • the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like.
  • the compound of Formula 1 is excellent in thermal stability and electrochemical stability, it is possible to improve the performance of the organic electroluminescent device.
  • Such a compound of Formula 1 may be used alone or may be mixed with an electron transport layer material known in the art.
  • the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
  • the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compounds, aluminum complexes (eg , Alq 3, tris(8-quinolinolato)-aluminium), and gallium complexes (eg, Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These may be used alone or two or more of them may be used in combination.
  • the structure of the organic electroluminescent device of the present invention described above is not particularly limited, but, for example, on a substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (Figs. see 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device is, as shown in FIG. 1 , on a substrate, an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340 and a cathode 200 may have a sequentially stacked structure.
  • an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200 .
  • an electron transport auxiliary layer 360 may be positioned between the light emitting layer 330 and the electron transport layer 340 (see FIG. 3 ).
  • the organic electroluminescent device of the present invention is a material and method known in the art, except that at least one of the organic layer 300 [eg, the electron transport layer 340] includes the compound represented by Formula 1 above. It can be manufactured by forming an organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
  • the substrate usable in the present invention is not particularly limited, and non-limiting examples include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof
  • metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
  • combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb
  • conductive polymers such as polythiophene, poly(3
  • examples of the cathode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer, the hole transport layer, the light emitting layer and the electron injection layer are not particularly limited, and common materials known in the art may be used.
  • the organic electroluminescent device is a tandem (tandem) type device, the anode 100 and the cathode 200 facing each other; a plurality of light emitting units 400 and 500 interposed between the anode 100 and the cathode 200; and a charge generation layer 600 interposed between adjacent light emitting units 400 and 500 and including an N-type charge generation layer 610 and a P-type charge generation layer 620 .
  • the N-type charge generation layer 610 includes the compound represented by the above-described Chemical Formula 1.
  • Such a tandem organic electroluminescent device has at least two light emitting units, and may be configured by interposing a charge generating layer between adjacent light emitting units to increase the number of light emitting units.
  • the plurality of light emitting units may include a first light emitting unit 400 and a second light emitting unit 500 .
  • each of the light emitting units 400 and 500 includes hole transport layers 410 and 510 , light emitting layers 420 and 520 , and electron transport layers 430 and 530 .
  • the first light emitting unit 400 includes a first hole transport layer 410 , a first light emitting layer 420 , and a first electron transport layer 430
  • the second light emitting unit 500 includes a hole transport layer 510 . , an emission layer 520 and an electron transport layer 530 .
  • the first light emitting unit 400 may additionally include a hole injection layer 440 .
  • the hole transport layers 410 and 510, the light emitting layers 420 and 520, the electron transport layers 430 and 530, and the hole injection layer 440 are not particularly limited, and common materials known in the art may be used.
  • the charge generation layer (CGL) 600 is disposed between the light emitting units 400 and 500 adjacent to each other, thereby controlling the charges between the light emitting units 400 and 500 to achieve a charge balance.
  • the charge generation layer 600 may include an N-type charge generation layer 610 positioned adjacent to the first light emitting unit 400 and supplying electrons to the first light emitting unit 400 ; and a P-type charge generation layer 620 positioned adjacent to the second light emitting unit 500 to supply holes to the second light emitting unit 500 .
  • the N-type charge generation layer 610 includes the compound represented by Chemical Formula 1 described above.
  • the compound of Formula 1 has excellent electron mobility and excellent electron injection and transport ability. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device as an N-type charge generating layer material, it is possible to prevent an increase in the progressive driving voltage and a decrease in the lifetime of the device.
  • the thickness of the N-type charge generation layer 610 is not particularly limited, and may be, for example, in the range of about 5 to 30 nm.
  • the P-type charge generation layer 620 may be formed of a metal or an organic material doped with P-type.
  • the metal includes Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni and Ti, and these metals may be used alone or as an alloy of two or more.
  • materials of the P-type dopant and the host used in the P-type doped organic material are not particularly limited as long as they are commonly used materials.
  • the P-type dopant includes F 4 -TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane), iodine, FeCl 3 , FeF 3 and SbCl 5 and the like.
  • non-limiting examples of the host include NPB (N,N'-bis(naphthaen-1-yl)-N,N'-bis(phenyl)-benzidine), TPD (N,N'-bis(3- There are methylphenyl)N,N'-bis(phenyl)-benzidine) and TNB(N,N,N',N'-tetra-naphthalenyl-benzidine), which may be used alone or in combination of two or more. have.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except for using each of the compounds shown in Table 1 below instead of Compound A-1 used as an electron transport layer material in the formation of the electron transport layer in Example 1 did.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound A-1 used as an electron transport layer material when forming the electron transport layer in Example 1.
  • the structures of Alq 3 used at this time are as follows, respectively.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compounds A to F were respectively used instead of the compound A-1 used as the electron transport layer material in the formation of the electron transport layer in Example 1 did.
  • Example 1 A-1 3.9 457 8.1 Example 2 A-2 4.1 456 7.9 Example 3 A-6 4.2 456 7.3 Example 4 A-9 4.1 457 7.9 Example 5 A-14 4.2 456 7.3 Example 6 A-17 3.9 458 8.0 Example 7 A-20 4.0 458 7.8 Example 8 A-21 4.1 454 7.5 Example 9 A-35 4.0 457 7.9 Example 10 A-36 4.2 458 7.6 Example 11 A-37 4.0 454 7.9 Example 12 A-38 4.0 454 7.8 Example 13 A-40 4.3 455 7.8 Example 14 A-43 4.0 455 8.0 Example 15 A-44 4.2 457 7.5 Example 16 A-47 4.2 457 7.5 Example 17 A-49 4.1 457 7.8 Example 18 A-50 4.3 455 7.7 Example 19 A-55 4.0 454 7.7 Example 20 A-56 4.2 455 7.6 Example 21 A-57 4.1 455 7.8 Example 22 A-60 4.3 457 7.4
  • the blue organic electroluminescent device of Examples 1-88 using the compound of the present invention for the electron transport layer As shown in Table 1, the blue organic electroluminescent device of Examples 1-88 using the compound of the present invention for the electron transport layer, the blue organic electroluminescent device of Comparative Example 1 using the conventional Alq 3 for the electron transport layer, and Compound A It was found that ⁇ F exhibited superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 2 to 7 in which the electron transport layer was used.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • An organic electroluminescent device was manufactured in the same manner as in Example 89, except that each of the compounds shown in Table 2 below was used instead of Compound A-1 used as the N-type charge generation layer material in Example 89.
  • An organic electroluminescent device was manufactured in the same manner as in Example 89, except that Compounds A to F were respectively used instead of Compound A-1 used as the N-type charge generation layer material in Example 89.
  • the structures of Compounds A to F are as described in Comparative Examples 2 to 7.
  • Example 90 A-2 8.3 15.9 Example 91 A-6 8.3 15.7
  • Example 92 A-9 8.2 15.5
  • Example 94 A-17 8.5 15.3
  • Example 96 A-21 8.2 15.7
  • Example 98 A-36 8.2 15.5
  • Example 99 A-37 8.6 15.3
  • Example 101 A-40 8.2 15.8 Example 102 A-43 8.4 15.4
  • Example 103 A-44 8.3 15.7
  • Example 106 A-50 8.3 15.9 Example 107 A-55 8.5 15.5
  • Example 110 A-60 8.3 15.6
  • Example 111 B-1 8.3 15.5
  • the blue organic electroluminescent devices of Examples 89 to 176 using the compound of the present invention for the N-type charge generating layer were compared to the blue organic electroluminescent devices of Comparative Examples 8 to 13 by using the compounds A to F. It was found that excellent performance was shown in terms of driving voltage and current efficiency.

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Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using same, and, more specifically, to a compound having excellent electron injection and transport capabilities, and an organic electroluminescent device comprising same in at least one organic layer, thereby having improved progressive driving voltage and properties such as luminous efficiency, driving voltage, lifespan, and the like.

Description

유기 화합물 및 이를 이용한 유기 전계 발광 소자Organic compound and organic electroluminescent device using same
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 전자 수송 능력이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성은 물론, 진행성 구동 전압이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, by including a compound having excellent electron transport ability and the same in one or more organic material layers, characteristics such as luminous efficiency, driving voltage, lifespan, as well as progressiveness It relates to an organic electroluminescent device having an improved driving voltage.
유기 전계 발광 소자(이하, '유기 EL 소자'라 함)는 두 전극 사이에 전압을 걸어 주면 애노드에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥 상태로 떨어질 때 빛이 나게 된다. 이때 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In an organic electroluminescent device (hereinafter, referred to as an 'organic EL device'), when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.
유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그 밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색 순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다. The material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the emission color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound including heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. To date, the hole injection layer, the hole transport layer. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq 3, etc. represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials. In particular, among the light emitting materials, as a phosphorescent material having a great advantage in terms of efficiency improvement , a metal complex compound containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc. is a blue, green, and red dopant material. is being used as So far, CBP has shown excellent properties as a phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, conventional organic material layer materials have advantages in terms of light emitting properties, but have low glass transition temperatures and very poor thermal stability, so they are not at a satisfactory level in terms of lifespan in organic EL devices. Accordingly, there is a demand for the development of an organic layer material having excellent performance.
본 발명은 전자 주입 및 수송능, 전기화학적 안정성, 열적 안정성 등이 모두 우수하여 유기 전계 발광 소자의 유기물층 재료, 구체적으로 전자 수송층 재료나 N형 전하생성층 재료로 사용될 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다. The present invention is excellent in electron injection and transport ability, electrochemical stability, thermal stability, etc. to provide a novel organic compound that can be used as an organic material layer material of an organic electroluminescent device, specifically, an electron transport layer material or an N-type charge generation layer material aim to
또한, 본 발명은 전술한 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, it is another object of the present invention to provide an organic electroluminescent device that exhibits a low driving voltage and high luminous efficiency, including the novel organic compound described above, and has an improved lifespan.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 유기 화합물을 제공한다:In order to achieve the above object, the present invention provides an organic compound represented by the following formula (1):
Figure PCTKR2020017988-appb-C000001
Figure PCTKR2020017988-appb-C000001
(상기 화학식 1에서,(In Formula 1,
상기 A 및 B 중 하나는 R1이고, 나머지는 하기 화학식 2로 표시되는 치환체이며,One of A and B is R 1 and the rest is a substituent represented by the following formula (2),
상기 R1은 C1~C60의 알킬기이고,Wherein R 1 is a C 1 ~ C 60 alkyl group,
Figure PCTKR2020017988-appb-C000002
Figure PCTKR2020017988-appb-C000002
n은 0 내지 3의 정수이고,n is an integer from 0 to 3,
EWG는 전자흡수성이 큰 전자 끌게기이고,EWG is an electron withdrawing force with high electron absorption,
m은 0 내지 4의 정수이고,m is an integer from 0 to 4,
R2는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되고,R 2 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group , C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group , C 6 ~ C 60 Arylphosphine oxide group, C 6 ~ C 60 Arylamine group, heteroarylamine group having 5 to 60 nuclear atoms, (C 6 ~ C 60 Aryl) (nuclear atoms 5 to 60 heteroaryl) selected from the group consisting of an amine group,
상기 R1의 알킬기는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상으로 치환되거나 또는 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이함).The alkyl group of R 1 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, C 6 to C 60 Arylox Period, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Arylphos pingi, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C 60 aryl amine group, the nuclear atoms of 5 to 60 heteroaryl amine, (aryl C 6 ~ C 60) (nuclear atoms of 5 to 60 heteroaryl) unsubstituted or substituted with one or more selected from the group consisting of an amine group, wherein when the substituents are plural, the plural substituents are the same or different from each other).
또, 본 발명은 애노드; 캐소드; 및 상기 애노드와 캐소드 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 전술한 유기 화합물을 포함하는 유기 전계 발광 소자를 제공한다. 이때, 상기 화합물을 포함하는 유기물층은 전자 수송층일 수 있다.In addition, the present invention is an anode; cathode; and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers provides an organic electroluminescent device comprising the above-described organic compound. In this case, the organic material layer including the compound may be an electron transport layer.
또한, 본 발명은 서로 이격 배향된 애노드와 캐소드; 상기 애노드와 캐소드 사이에 개재된 복수의 발광 유닛; 서로 인접한 발광 유닛 사이에 개재된 N형 전하 생성층 및 P형 전하 생성층을 포함하고, 상기 각 발광 유닛은 정공 수송층, 발광층 및 전자 수송층을 포함하고, 상기 N형 전하 생성층은 전술한 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention provides an anode and a cathode spaced apart from each other; a plurality of light emitting units interposed between the anode and the cathode; an N-type charge generation layer and a P-type charge generation layer interposed between adjacent light emitting units, wherein each light emitting unit includes a hole transport layer, a light emitting layer and an electron transport layer, and the N type charge generation layer comprises the above-mentioned compound It provides an organic electroluminescent device comprising.
본 발명의 화합물은 전자수송능, 발광능, 전기화학적 안정성, 열적 안정성 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있다. 특히, 본 발명의 화합물을 발광층의 호스트, 전자 수송층 재료 및 전자수송 보조층 재료 중 적어도 어느 하나로 사용될 경우, 종래 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명 특성을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.Since the compound of the present invention has excellent electron transport ability, light emitting ability, electrochemical stability, thermal stability, etc., it can be used as an organic material layer material of an organic electroluminescent device. In particular, when the compound of the present invention is used as at least one of a host of a light emitting layer, an electron transport layer material, and an electron transport auxiliary layer material, an organic electroluminescent device having superior light emitting performance, low driving voltage, high efficiency and long lifespan compared to conventional materials. can be manufactured, and furthermore, a full-color display panel with improved performance and lifespan can be manufactured.
도 1은 본 발명의 제1 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
도 2는 본 발명의 제2 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다. 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a second embodiment of the present invention.
도 3은 본 발명의 제3 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a third embodiment of the present invention.
도 4는 본 발명의 제4 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a fourth embodiment of the present invention.
** 부호의 설명 **** Explanation of symbols **
100: 애노드, 200: 캐소드,100: anode, 200: cathode,
300: 유기물층, 310: 정공주입층,300: organic layer, 310: hole injection layer,
320: 정공수송층, 330: 발광층,320: hole transport layer, 330: light emitting layer,
340: 전자수송층, 350: 전자주입층,340: electron transport layer, 350: electron injection layer,
360: 전자 수송 보조층, 400: 제1 발광 유닛, 360: electron transport auxiliary layer, 400: a first light emitting unit;
410: 제1 정공수송층, 420: 제1 발광층,410: a first hole transport layer, 420: a first light emitting layer,
430: 제1 전자수송층, 440: 정공주입층, 430: a first electron transport layer, 440: a hole injection layer,
500: 제2 발광 유닛, 510: 제2 정공수송층,500: a second light emitting unit, 510: a second hole transport layer,
520: 제2발광층, 530: 제2 전자수송층,520: a second light emitting layer, 530: a second electron transport layer,
600: 전하생성층, 610: n형 전하생성층, 600: charge generation layer, 610: n-type charge generation layer,
620: p형 전하생성층620: p-type charge generation layer
이하, 본 발명에 대해 설명한다.EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.
<신규 화합물><New compound>
본 발명은 전자 주입 및 수송능, 전기화학적 안정성, 열적 안정성 등이 우수하여 유기 전계 발광 소자의 고효율, 장수명, 구동전압 특성 및 진행성 구동전압 특성을 향상시킬 수 있는 전자수송층 재료 또는 전자수송 보조층 재료로 사용될 수 있는 신규 화합물을 제공한다.The present invention is an electron transport layer material or electron transport auxiliary layer material that can improve the high efficiency, long life, driving voltage characteristics and progressive driving voltage characteristics of an organic electroluminescent device due to excellent electron injection and transport ability, electrochemical stability, thermal stability, etc. It provides a novel compound that can be used as
구체적으로, 상기 화학식 1로 표시되는 화합물은 페난트롤린 모이어티(phenanthroline moiety)의 7번 및 9번 탄소 위치 중 하나에 알킬기가 도입되고, 나머지에는 전자 흡수성이 큰 전자 끌개기(electron withdrawing group, EWG)가 직접 또는 링커기(예, 페닐렌기, 비페닐렌기, 터페닐렌기)를 통해 도입되어 이루어진 구조를 포함한다. 여기서, 페난트롤린 모이어티의 탄소/질소 위치 번호는 하기와 같이 나타낼 수 있다.Specifically, in the compound represented by Chemical Formula 1, an alkyl group is introduced at one of the 7th and 9th carbon positions of the phenanthroline moiety, and an electron withdrawing group with high electron absorption in the rest EWG) is introduced directly or through a linker group (eg, a phenylene group, a biphenylene group, a terphenylene group). Here, the carbon/nitrogen position number of the phenanthroline moiety can be represented as follows.
Figure PCTKR2020017988-appb-I000001
Figure PCTKR2020017988-appb-I000001
일례로, 상기 화학식 1로 표시되는 화합물은 페난트롤린 모이어티의 7번 탄소 위치에 EWG가 직접 또는 링커기를 통해 도입되고, 9번 탄소 위치에 알킬기가 도입된 구조를 포함한다. For example, the compound represented by Formula 1 includes a structure in which EWG is introduced directly or through a linker group at the 7th carbon position of the phenanthroline moiety, and an alkyl group is introduced at the 9th carbon position.
상기 화학식 1의 화합물에서, 페난트롤린 모이어티는 전자 흡수성이 큰 모이어티이다. 이러한 페난트롤린 모이어티의 7번 및 9번 위치 중 하나(특히, 7번 위치)에 전자 흡수성이 큰 전자 끌개기(EWG)가 직접 또는 링커기를 통해 도입됨으로써, 화학식 1의 화합물은 전자 이동 속도가 향상되어 전자 주입 및 수송능이 극대화될 수 있다. 따라서, 상기 화학식 1의 화합물이 유기 전계 발광 소자에 적용될 경우, 소자의 저구동전압, 고전류효율 및 장수명 특성을 구현시킬 뿐만 아니라, 진행성 구동 전압 특성을 향상시켜 소자의 소비전력의 상승 및 수명 저하를 방지할 수 있다.In the compound of Formula 1, the phenanthroline moiety is a moiety with high electron absorption. By introducing an electron withdrawing group (EWG) with high electron absorption at one of positions 7 and 9 (particularly, position 7) of the phenanthroline moiety directly or through a linker group, the compound of Formula 1 exhibits an electron transfer rate is improved so that the electron injection and transport ability can be maximized. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device, it not only realizes the low driving voltage, high current efficiency, and long life characteristics of the device, but also improves the progressive driving voltage characteristic to increase the power consumption and decrease the lifespan of the device. can be prevented
또한, 페난트롤린 모이어티에 나머지 위치, 특히 활성 사이트(active site)인 9번 위치에 알킬기가 도입될 경우, 분자의 안정성이 증가될 수 있다. 또한, 페난트롤린 모이어티의 9번 위치에 알킬기가 도입됨으로써, 수소(H)나 아릴기가 도입된 페난트롤린 유도체에 비해, 분자량을 최소한으로 증가시킬 수 있다. 이는 소자의 제작시, 상기 화학식 1의 화합물이 받는 열을 최소화할 수 있어 화합물의 열적 안정성을 개선시킬 수 있고, 이로 인해 소자의 열화를 방지할 수 있다. 따라서, 본 발명의 화합물은 열적, 전기화학적으로 안정하고, 삼중항 에너지가 높다. In addition, when an alkyl group is introduced at the remaining positions of the phenanthroline moiety, particularly at position 9, which is the active site, the stability of the molecule may be increased. In addition, by introducing an alkyl group at the 9th position of the phenanthroline moiety, the molecular weight can be minimally increased compared to a phenanthroline derivative in which hydrogen (H) or an aryl group is introduced. This can minimize the heat received by the compound of Formula 1 when manufacturing the device, thereby improving the thermal stability of the compound, thereby preventing the device from being deteriorated. Accordingly, the compounds of the present invention are thermally and electrochemically stable and have high triplet energy.
게다가, 본 발명의 화합물은 전자가 상대적으로 풍부한 sp2 혼성 오비탈의 질소(N)를 포함한다. 상기 질소는 N형 전하 생성층의 도펀트인 알칼리 금속 또는 알칼리 토금속과 결합(binding)하여 갭 스테이트(gap state)를 형성할 수 있다. 따라서, 형성된 갭 스테이트에 의해, N형 전하 생성층에서 전자 수송층으로의 전자의 전달을 원활하게 할 수 있다.In addition, the compounds of the present invention contain nitrogen (N) in sp 2 hybrid orbitals that are relatively electron-rich. The nitrogen may form a gap state by binding with an alkali metal or alkaline earth metal, which is a dopant of the N-type charge generation layer. Therefore, the formed gap state makes it possible to facilitate the transfer of electrons from the N-type charge generation layer to the electron transport layer.
전술한 바와 같이, 상기 화학식 1로 표시되는 화합물은 전자 주입 및 수송 능력이 우수하다. 따라서, 본 발명의 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게 전자 수송층 재료로 사용될 수 있다. 또한, 본 발명의 화합물은 탠덤 구조의 유기 전계 발광 소자의 N형 전하 생성층 재료로 사용될 수 있다. 이와 같이, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 전자수송층 재료 또는 N형 전하 생성층 재료로 적용됨으로써, 소자의 구동 전압, 발광 효율 및 수명 등의 특성을 향상시킬 수 있음은 물론, 진행성 구동 전압의 상승을 방지할 수 있고, 나아가 상기 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.As described above, the compound represented by Formula 1 has excellent electron injection and transport ability. Accordingly, the compound of the present invention may be used as an organic material layer, preferably an electron transport layer, of an organic electroluminescent device. In addition, the compound of the present invention may be used as an N-type charge generating layer material of an organic electroluminescent device having a tandem structure. As such, the compound represented by Formula 1 of the present invention is applied as an electron transport layer material or an N-type charge generation layer material of an organic electroluminescent device, thereby improving characteristics such as driving voltage, luminous efficiency and lifespan of the device. Of course, it is possible to prevent the increase of the progressive driving voltage, and furthermore, the performance of the full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.
상기 화학식 1로 표시되는 화합물에서, A 및 B 중에서 하나는 R1으로, C1~C60의 알킬기이고, 나머지는 상기 화학식 2로 표시되는 치환체이다.In the compound represented by Formula 1, one of A and B is R 1 , and a C 1 to C 60 alkyl group, and the remainder is a substituent represented by Formula 2 above.
일례로, 상기 화학식 1로 표시되는 화합물은 하기 화학식 3으로 표시되는 화합물일 수 있다. For example, the compound represented by Formula 1 may be a compound represented by Formula 3 below.
Figure PCTKR2020017988-appb-C000003
Figure PCTKR2020017988-appb-C000003
상기 화학식 3에서,In Formula 3,
n, EWG, m, R1 및 R2는 각각 상기 화학식 1에서 정의한 바와 같다.n, EWG, m, R 1 and R 2 are each as defined in Formula 1 above.
상기 화학식 1에서, R1은 C1~C60의 알킬기이며, 일례로 C1~C12의 알킬기일 수 있다. In Formula 1, R 1 is a C 1 ~ C 60 alkyl group, for example, may be a C 1 ~ C 12 alkyl group.
상기 R1의 알킬기는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이하다. 여기서, 상기 헤테로시클로알킬기 및 헤테로아릴기는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로원자를 포함한다.The alkyl group of R 1 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, C 6 to C 60 Arylox Period, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Arylphos pingi, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C 60 aryl amine group, the nuclear atoms of 5 to 60 heteroaryl amine, (aryl C 6 ~ C 60) (nuclear atoms of 5 to 60 heteroaryl) unsubstituted or substituted with one or more substituents selected from the group consisting of an amine group, wherein when the substituents are plural, the plurality of substituents are the same or different from each other. Here, the heterocycloalkyl group and the heteroaryl group each include at least one heteroatom selected from the group consisting of N, S, O and Se.
이러한 R1에 따라, 상기 화학식 1로 표시되는 화합물은 하기 화학식 4 내지 7 중 어느 하나로 표시되는 화합물일 수 있는데, 이에 한정되지 않는다.Depending on R 1 , the compound represented by Formula 1 may be a compound represented by any one of Formulas 4 to 7, but is not limited thereto.
Figure PCTKR2020017988-appb-C000004
Figure PCTKR2020017988-appb-C000004
Figure PCTKR2020017988-appb-C000005
Figure PCTKR2020017988-appb-C000005
Figure PCTKR2020017988-appb-C000006
Figure PCTKR2020017988-appb-C000006
Figure PCTKR2020017988-appb-C000007
Figure PCTKR2020017988-appb-C000007
상기 화학식 4 내지 7에서,In Formulas 4 to 7,
n, m, R2 및 EWG은 각각 상기 화학식 1에서 정의한 바와 같다.n, m, R 2 and EWG are each as defined in Formula 1 above.
상기 화학식 2에서, n은 0 내지 3의 정수이다. 이때, n이 0인 경우, 상기 화학식 2의
Figure PCTKR2020017988-appb-I000002
모이어티는 단일결합(직접결합)인 것을 의미한다. 한편, n이 1 내지 3의 정수인 경우, 상기 화학식 2의
Figure PCTKR2020017988-appb-I000003
모이어티는 2가의 링커기로, 페닐렌기, 비페닐렌기 및 터페닐렌기로 이루어진 군에서 선택된 것을 의미한다. In Formula 2, n is an integer of 0 to 3. In this case, when n is 0, the
Figure PCTKR2020017988-appb-I000002
A moiety is meant to be a single bond (direct bond). On the other hand, when n is an integer of 1 to 3,
Figure PCTKR2020017988-appb-I000003
The moiety is a divalent linker group, and means selected from the group consisting of a phenylene group, a biphenylene group and a terphenylene group.
상기 화학식 2에서, m은 0 내지 4의 정수이다. 이때, m이 0인 경우, 수소가 치환기 R2로 치환되지 않은 것을 의미하고, m이 1 내지 3의 정수인 경우, 1 이상의 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되고, 구체적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.In Formula 2, m is an integer of 0 to 4. In this case, when m is 0, it means that hydrogen is not substituted with a substituent R 2 , and when m is an integer of 1 to 3, one or more R 2 are the same as or different from each other, and each independently deuterium, halogen, cyano group , nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group, C 6 ~ C 60 Aryl phosphine oxide Group, C 6 ~ C 60 arylamine group, heteroarylamine group of 5 to 60 nuclear atoms, (C 6 ~ C 60 aryl) (heteroaryl of 5 to 60 nuclear atoms) amine group selected from the group consisting of and specifically deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nucleus It may be selected from the group consisting of a heterocycloalkyl group having 3 to 40 atoms, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.
일례로, 상기 화학식 2의
Figure PCTKR2020017988-appb-I000004
모이어티는 하기 링커기 Link-1 내지 Link-5로 이루어진 군에서 선택된 링커기일 수 있다. 이때, 하기 링커기들의 수소는 중수소(D), 할로겐, 시아노기, 니트로기, C1~C12의 알킬기 등의 1 이상의 치환기로 치환될 수 있다.For example, the formula (2)
Figure PCTKR2020017988-appb-I000004
The moiety may be a linker group selected from the group consisting of the following linker groups Link-1 to Link-5. In this case, hydrogen of the following linker groups may be substituted with one or more substituents such as deuterium (D), halogen, cyano group, nitro group, and C 1 to C 12 alkyl group.
Figure PCTKR2020017988-appb-I000005
Figure PCTKR2020017988-appb-I000005
또, 상기 화학식 2에서, EWG는 전자흡수성이 큰 전자끌게기로, 구체적으로 핵원자수 5~30의 헤테로방향족고리일 수 있다. 이때, 상기 헤테로방향족고리는 N, S, O, Se 중 1개 이상의 헤테로원자를 함유할 수 있다. In addition, in Formula 2, EWG is an electron withdrawing group with high electron absorption, and specifically may be a heteroaromatic ring having 5 to 30 nuclear atoms. In this case, the heteroaromatic ring may contain one or more heteroatoms among N, S, O, and Se.
일례로, 상기 EWG는 하기 화학식 S1 또는 S2로 표시되는 치환체일 수 있는데, 이에 한정되지 않는다.For example, the EWG may be a substituent represented by the following Chemical Formula S1 or S2, but is not limited thereto.
[화학식 S1][Formula S1]
Figure PCTKR2020017988-appb-I000006
Figure PCTKR2020017988-appb-I000006
[화학식 S2][Formula S2]
Figure PCTKR2020017988-appb-I000007
Figure PCTKR2020017988-appb-I000007
상기 화학식 S1 및 S2에서,In the above formulas S1 and S2,
X1 내지 X5는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 내지 X5 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고,X 1 to X 5 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 to X 5 is N, wherein a plurality of Ar 2 are the same as or different from each other,
Y1 내지 Y4는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar3)이고, 다만 Y1 내지 Y4 중 적어도 하나는 N이며, 이때 복수의 Ar3은 서로 동일하거나 상이하고,Y 1 to Y 4 are the same or different from each other, and each independently is N or C(Ar 3 ), provided that at least one of Y 1 to Y 4 is N, wherein a plurality of Ar 3 are the same or different from each other,
Ar1 내지 Ar3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기(예, Ar1-Ar3, Ar3-Ar3, Ar2-Ar2)와 서로 결합하여 축합 고리를 형성할 수 있고, Ar 1 To Ar 3 Are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C 60 of the arylamine group, the nuclear atoms of 5 to 60 hetero arylamine group, and (C 6 -C 60 aryl) (heteroaryl of 5 to 60 nuclear atoms) an amine group, or an adjacent group (eg, Ar 1 -Ar 3 , Ar 3 -Ar 3 , Ar 2 - Ar 2 ) and may combine with each other to form a condensed ring,
상기 Ar1 내지 Ar3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 아릴포스피닐기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이하다. 여기서, 상기 헤테로시클로알킬기 및 헤테로아릴기는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로원자를 포함한다. 또, 상기 축합 고리는 C6~C60의 지환족 고리, 5원~60원의 헤테로지환족 고리, C6~C60의 방향족 고리, 5원~60원의 헤테로방향족 고리,혹은 이들의 조합된 형태이며, 이때 상기 축합 고리가 다환일 경우, 각 고리는 서로 동일하거나 또는 상이하다.The Ar 1 To Ar 3 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl Boron group, arylphosphanyl group, arylphosphinyl group, arylamine group, heteroarylamine group and (aryl) (heteroaryl) amine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, nucleus A heteroaryl group having 5 to 60 atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, an aryl amine of the C 6 ~ C 60 group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 to C 60 aryl) (heteroaryl having 5 to 60 nuclear atoms) substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group and, in this case, when the substituents are plural, the plurality of substituents are the same as or different from each other. Here, the heterocycloalkyl group and the heteroaryl group each include at least one heteroatom selected from the group consisting of N, S, O and Se. In addition, the condensed ring is a C 6 ~ C 60 alicyclic ring, 5 ~ 60 membered heteroalicyclic ring, C 6 ~ C 60 aromatic ring, 5 ~ 60 membered heteroaromatic ring, or a combination thereof In this case, when the condensed ring is polycyclic, each ring is the same as or different from each other.
구체적으로, 상기 EWG는 하기 화학식 S3 내지 S7 중 어느 하나로 표시되는 치환체일 수 있고, 이에 한정되지 않는다.Specifically, the EWG may be a substituent represented by any one of the following Chemical Formulas S3 to S7, but is not limited thereto.
[화학식 S3][Formula S3]
Figure PCTKR2020017988-appb-I000008
Figure PCTKR2020017988-appb-I000008
[화학식 S4][Formula S4]
Figure PCTKR2020017988-appb-I000009
Figure PCTKR2020017988-appb-I000009
[화학식 S5][Formula S5]
Figure PCTKR2020017988-appb-I000010
Figure PCTKR2020017988-appb-I000010
[화학식 S6][Formula S6]
Figure PCTKR2020017988-appb-I000011
Figure PCTKR2020017988-appb-I000011
[화학식 S7][Formula S7]
Figure PCTKR2020017988-appb-I000012
Figure PCTKR2020017988-appb-I000012
[화학식 S8][Formula S8]
Figure PCTKR2020017988-appb-I000013
Figure PCTKR2020017988-appb-I000013
[화학식 S9][Formula S9]
Figure PCTKR2020017988-appb-I000014
Figure PCTKR2020017988-appb-I000014
상기 화학식 S3에서,In Formula S3,
X1, X3 및 X5는 각각 상기 화학식 S1에서 정의된 바와 같고, 다만 X1, X3 및 X5 중 적어도 하나는 N이며,X 1 , X 3 and X 5 are each as defined in Formula S1, provided that at least one of X 1 , X 3 and X 5 is N,
상기 화학식 S4 및 S5에서,In Formulas S4 and S5,
X1 및 X3는 각각 상기 화학식 S1에서 정의된 바와 같고, 다만 X1 및 X3 중 적어도 하나는 N이며,X 1 and X 3 are each as defined in Formula S1, provided that at least one of X 1 and X 3 is N,
Z1은 O 또는 S이고, Z 1 is O or S,
상기 화학식 S6 및 S7에서,In the above formulas S6 and S7,
X1 및 X5는 각각 상기 화학식 S1에서 정의된 바와 같고, 다만 X1 및 X5 중 적어도 하나는 N이며,X 1 and X 5 are each as defined in Formula S1, provided that at least one of X 1 and X 5 is N,
Z1은 O 또는 S이고, Z 1 is O or S,
상기 화학식 S8 및 S9에서, In the above formulas S8 and S9,
Y1, Y2 및 Y4는 각각 상기 화학식 S2에서 정의된 바와 같고, 다만 Y1, Y2 및 Y4 중 적어도 하나는 N이며,Y 1 , Y 2 and Y 4 are each as defined in Formula S2 above, provided that at least one of Y 1 , Y 2 and Y 4 is N,
상기 화학식 S3 내지 S9에서,In Formulas S3 to S9,
Ar1 내지 Ar3는 각각 상기 화학식 S1 및 S2에서 정의된 바와 같고,Ar 1 to Ar 3 are each as defined in the above formulas S1 and S2,
a는 0 내지 4의 정수이고, a is an integer from 0 to 4,
Ar4는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된다.Ar 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group , C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group , C 6 ~ C 60 Arylphosphine oxide group, C 6 ~ C 60 An arylamine group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 ~ C 60 aryl) (5 nuclear atoms) to 60 heteroaryl) selected from the group consisting of an amine group.
본 발명에 따른 화학식 1로 표시되는 화합물은, 하기 화학식 8 내지 14 중 어느 하나로 표시되는 화합물로 구체화될 수 있는데, 이에 한정되지 않는다.The compound represented by Formula 1 according to the present invention may be embodied as a compound represented by any one of the following Formulas 8 to 14, but is not limited thereto.
Figure PCTKR2020017988-appb-C000008
Figure PCTKR2020017988-appb-C000008
Figure PCTKR2020017988-appb-C000009
Figure PCTKR2020017988-appb-C000009
Figure PCTKR2020017988-appb-C000010
Figure PCTKR2020017988-appb-C000010
Figure PCTKR2020017988-appb-C000011
Figure PCTKR2020017988-appb-C000011
Figure PCTKR2020017988-appb-C000012
Figure PCTKR2020017988-appb-C000012
Figure PCTKR2020017988-appb-C000013
Figure PCTKR2020017988-appb-C000013
Figure PCTKR2020017988-appb-C000014
Figure PCTKR2020017988-appb-C000014
상기 화학식 8 및 9에서, In Formulas 8 and 9,
X1, X3 및 X5는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 내지 X5 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고;X 1 , X 3 and X 5 are the same or different from each other, and each independently represents N or C(Ar 2 ), provided that at least one of X 1 to X 5 is N, wherein a plurality of Ar 2 are the same as or different from each other and;
상기 화학식 10 및 11에서, In Formulas 10 and 11,
X1 및 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 및 X3 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고,X 1 and X 3 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 and X 3 is N, wherein a plurality of Ar 2 are the same as or different from each other,
Z1은 O 또는 S이고;Z 1 is O or S;
상기 화학식 12 및 13에서, In Formulas 12 and 13,
X1 및 X5는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 및 X5 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고,X 1 and X 5 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 and X 5 is N, wherein a plurality of Ar 2 are the same or different from each other,
Z1은 O 또는 S이고;Z 1 is O or S;
상기 화학식 14에서, In the formula (14),
Y1, Y2 및 Y4는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar3)이고, 다만 Y1, Y2 및 Y4 중 적어도 하나는 N이며, 이때 복수의 Ar3은 서로 동일하거나 상이하고;Y 1 , Y 2 and Y 4 are the same as or different from each other, and each independently represent N or C(Ar 3 ), provided that at least one of Y 1 , Y 2 and Y 4 is N, wherein a plurality of Ar 3 are each other the same or different;
상기 화학식 8 내지 14에서,In Formulas 8 to 14,
n, m, R1 및 R2는 각각 상기 화학식 1에서 정의된 바와 같고,n, m, R 1 and R 2 are each as defined in Formula 1 above,
a는 0 내지 4의 정수이고,a is an integer from 0 to 4,
b 및 c는 각각 0 또는 1이며,b and c are each 0 or 1,
Ar2 및 Ar3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기(예, Ar2-Ar2, Ar3-Ar3)와 서로 결합하여 축합 고리를 형성할 수 있고, Ar 2 and Ar 3 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ~ C 40 alkyl group, a C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C 60 of the arylamine group, the nuclear atoms of 5 to 60 hetero arylamine group, And (C 6 ~ C 60 aryl) (nuclear atoms 5 to 60 heteroaryl) selected from the group consisting of an amine group, or adjacent groups (eg, Ar 2 -Ar 2 , Ar 3 -Ar 3 ) and bonded to each other to form a condensed ring,
Ar4는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되며,Ar 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group , C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group , C 6 ~ C 60 Arylphosphine oxide group, C 6 ~ C 60 An arylamine group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 ~ C 60 aryl) (5 nuclear atoms) to 60 heteroaryl) selected from the group consisting of an amine group,
상기 Ar2 및 Ar3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 아릴포스피닐기, 아릴아민기, 헤테로아릴아민기, (아릴)(헤테로아릴)아민기 및 축합 고리는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이하다.The Ar 2 And Ar 3 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl A boron group, an arylphosphanyl group, an arylphosphinyl group, an arylamine group, a heteroarylamine group, an (aryl) (heteroaryl)amine group, and a condensed ring are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C With one or more substituents selected from the group consisting of an arylamine group of 60, a heteroarylamine group of 5 to 60 nuclear atoms, and an (C 6 -C 60 aryl) (heteroaryl of 5 to 60 nuclear atoms) amine group It is substituted or unsubstituted, and when the substituents are plural, the plural substituents are the same as or different from each other.
전술한 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화합물 A-1~A-60, B-1~B-60, C-1~C-60, D-1~D-60로 이루어진 군에서 선택된 화합물로 구체화될 수 있다. 그러나, 본 발명에 따른 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by Formula 1 according to the present invention described above is from the group consisting of the following compounds A-1 to A-60, B-1 to B-60, C-1 to C-60, and D-1 to D-60 may be embodied in the selected compound. However, the compound represented by Formula 1 according to the present invention is not limited by those exemplified below.
Figure PCTKR2020017988-appb-I000015
Figure PCTKR2020017988-appb-I000015
Figure PCTKR2020017988-appb-I000016
Figure PCTKR2020017988-appb-I000016
Figure PCTKR2020017988-appb-I000017
Figure PCTKR2020017988-appb-I000017
Figure PCTKR2020017988-appb-I000018
Figure PCTKR2020017988-appb-I000018
Figure PCTKR2020017988-appb-I000019
Figure PCTKR2020017988-appb-I000019
Figure PCTKR2020017988-appb-I000020
Figure PCTKR2020017988-appb-I000020
Figure PCTKR2020017988-appb-I000021
Figure PCTKR2020017988-appb-I000021
Figure PCTKR2020017988-appb-I000022
Figure PCTKR2020017988-appb-I000022
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkenyl (alkenyl)" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서"알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, 모노-뿐만 아니라 디-, 트리-알킬실릴을 포함한다. 또, "아릴실릴"은 탄소수 5 내지 60의 아릴로 치환된 실릴을 의미하고, 모노-뿐만 아니라 디-, 트리-아릴실릴 등의 폴리아릴실릴을 포함한다.In the present invention, "alkylsilyl" means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl. In addition, "arylsilyl" means a silyl substituted with aryl having 5 to 60 carbon atoms, and includes mono- as well as polyarylsilyl such as di- and tri-arylsilyl.
본 발명에서 "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미한다.In the present invention, "alkyl boron group" means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and "aryl boron group" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.
본 발명에서 "알킬포스피닐기"는 탄소수 1 내지 40의 알킬로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-알킬포스피닐기를 포함한다. 또, 본 발명에서 "아릴포스피닐기"는 탄소수 6 내지 60의 모노아릴 또는 디아릴로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-아릴포스피닐기를 포함한다. In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, in the present invention, "arylphosphinyl group" means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
본 발명에서 "아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-아릴아민를 포함한다.In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamines.
본 발명에서 "헤테로아릴아민"은 핵원자수 5 내지 60의헤테로아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-헤테로아릴아민를 포함한다.In the present invention, "heteroarylamine" means an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.
본발명에서 (아릴)(헤테로아릴)아민은 탄소수 6 내지 60의 아릴 및 핵원자수 5 내지 60의헤테로아릴로 치환된 아민을 의미한다.In the present invention, (aryl) (heteroaryl) amine means an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.
본 발명에서 "축합고리"는 탄소수 3 내지 40의 축합지방족 고리, 탄소수 6 내지 60의 축합 방향족 고리, 핵원자수 3 내지 60의축합헤테로지방족 고리, 핵원자수 5 내지 60의축합헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, "condensed ring" refers to a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, or means a combination of these.
<유기 전계 발광 소자><Organic electroluminescent device>
한편, 본 발명면은 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(이하, '유기 EL 소자')를 제공한다.On the other hand, an aspect of the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') including the compound represented by Formula 1 described above.
도 1 내지 도 4는 본 발명의 제1 내지 제4 실시 형태에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.1 to 4 are cross-sectional views schematically showing organic electroluminescent devices according to first to fourth embodiments of the present invention.
이하, 도 1 내지 도 3을 참고하여, 본 발명의 제1 내지 제3 실시 형태에 따른 유기 전계 발광 소자에 대해 상세히 설명한다.Hereinafter, an organic electroluminescent device according to first to third embodiments of the present invention will be described in detail with reference to FIGS. 1 to 3 .
도 1 내지 도 3에 도시된 바와 같이, 본 발명에 따른 유기 전계 발광 소자는 애노드(anode)(100), 캐소드(cathode)(200) 및 상기 애노드와 캐소드 사이에 개재(介在)된 1층 이상의 유기물층(300)을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.1 to 3, the organic electroluminescent device according to the present invention is an anode (anode) 100, a cathode (cathode) 200, and one or more layers interposed between the anode and the cathode The organic material layer 300 is included, and at least one of the one or more organic material layers includes the compound represented by Formula 1 above. In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층(300)은 정공 주입층(310), 정공 수송층(320), 발광층(330), 전자 수송 보조층(360), 전자 수송층(340), 및 전자 주입층(350) 중 어느 하나 이상을 포함할 수 있고, 이 중에서 적어도 하나의 유기물층(300)은 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 전자수송층(340)일 수 있다. 즉, 상기 화학식 1로 표시되는 화합물은 전자수송층 물질로 유기 전계 발광 소자에 포함된다. 이러한 유기 전계 발광 소자에서, 전자는 상기 화학식 1의 화합물 때문에, 캐소드 또는 전자주입층에서 전자수송층으로 용이하게 주입되고, 또한 전자수송층에서 발광층으로 빠르게 이동할 수 있기 때문에, 발광층에서의 정공과 전자의 결합력이 높다. 그러므로, 본 발명의 유기 전계 발광 소자는 발광효율, 전력효율, 휘도 등이 우수하다. 게다가,상기 화학식 1의 화합물은 열적 안정성,전기화학적 안정성이 우수하여, 유기 전계 발광 소자의 성능을 향상시킬 수 있다.The one or more organic material layers 300 may include any one of a hole injection layer 310 , a hole transport layer 320 , a light emitting layer 330 , an electron transport auxiliary layer 360 , an electron transport layer 340 , and an electron injection layer 350 . It may include one or more, of which at least one organic material layer 300 includes the compound represented by Formula 1 above. Specifically, the organic material layer including the compound of Formula 1 may be the electron transport layer 340 . That is, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons are easily injected from the cathode or electron injection layer to the electron transport layer because of the compound of Formula 1, and can also rapidly move from the electron transport layer to the emission layer, so the bonding force between holes and electrons in the emission layer this is high Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like. In addition, the compound of Formula 1 is excellent in thermal stability and electrochemical stability, it is possible to improve the performance of the organic electroluminescent device.
이와 같은 화학식 1의 화합물은 단독으로 사용되거나, 또는 당 분야에 공지된 전자수송층 재료와 혼용될 수 있다.Such a compound of Formula 1 may be used alone or may be mixed with an electron transport layer material known in the art.
본 발명에서 상기 화학식 1의 화합물과 혼용될 수 있는 전자수송층 재료는 당 분야에서 통상적으로 공지된 전자수송 물질을 포함한다. 사용 가능한 전자 수송 물질의 비제한적인 예로는 옥사졸계 화합물, 이소옥사졸계 화합물, 트리아졸계 화합물, 이소티아졸(isothiazole)계 화합물, 옥사디아졸계 화합물, 티아다아졸(thiadiazole)계 화합물, 페릴렌(perylene)계 화합물, 알루미늄 착물(예: Alq3, tris(8-quinolinolato)-aluminium), 갈륨 착물(예: Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)) 등이 있다. 이들을 단독으로 사용하거나 또는 2종 이상 혼용할 수 있다. In the present invention, the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compounds, aluminum complexes (eg , Alq 3, tris(8-quinolinolato)-aluminium), and gallium complexes (eg, Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These may be used alone or two or more of them may be used in combination.
본 발명에서, 상기 화학식 1의 화합물과 전자수송층 재료를 혼용할 경우, 이들의 혼합 비율은 특별히 제한되지 않으며, 당 분야에 공지된 범위 내에서 적절히 조절될 수 있다. In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and may be appropriately adjusted within a range known in the art.
전술한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 예컨대 기판 위에, 애노드(100), 1층 이상의 유기물층(300) 및 캐소드(200)가 순차적으로 적층될 수 있다(도 1 내지 도 3 참조). 뿐만 아니라, 도시되지 않았지만, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but, for example, on a substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (Figs. see 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
일례에 따르면, 유기 전계 발광 소자는 도 1에 도시된 바와 같이, 기판 위에, 애노드(100), 정공주입층(310), 정공수송층(320), 발광층(330), 전자수송층(340) 및 캐소드(200)가 순차적으로 적층된 구조를 가질 수 있다. 선택적으로, 도 2에 도시된 바와 같이, 상기 전자수송층(340)과 캐소드(200) 사이에 전자주입층(350)이 위치할 수 있다. 또한, 상기 발광층(330)과 전자수송층(340) 사이에 전자수송 보조층(360)이 위치할 수 있다(도 3 참조). According to an example, the organic electroluminescent device is, as shown in FIG. 1 , on a substrate, an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340 and a cathode 200 may have a sequentially stacked structure. Optionally, as shown in FIG. 2 , an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200 . Also, an electron transport auxiliary layer 360 may be positioned between the light emitting layer 330 and the electron transport layer 340 (see FIG. 3 ).
본 발명의 유기 전계 발광 소자는 상기 유기물층(300) 중 적어도 하나[예, 전자수송층(340]가 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device of the present invention is a material and method known in the art, except that at least one of the organic layer 300 [eg, the electron transport layer 340] includes the compound represented by Formula 1 above. It can be manufactured by forming an organic material layer and an electrode.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥 코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
본 발명에서 사용 가능한 기판은 특별히 한정되지 않으며, 비제한적인 예로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 있다.The substrate usable in the present invention is not particularly limited, and non-limiting examples include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.
또, 애노드 물질의 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지는 않는다.In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.
또, 캐소드 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은(Ag), 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지는 않는다.Further, examples of the cathode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
또한, 정공주입층, 정공수송층, 발광층 및 전자 주입층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the light emitting layer and the electron injection layer are not particularly limited, and common materials known in the art may be used.
이하, 도 4를 참조하여, 본 발명의 제4 실시 형태에 따른 유기 전계 발광 소자에 대해 설명한다.Hereinafter, an organic electroluminescent device according to a fourth embodiment of the present invention will be described with reference to FIG. 4 .
도 4에 도시된 바와 같이, 본 발명의 제4 실시 형태에 따른 유기 전계 발광 소자는 탠덤(tandem)형 소자로, 서로 대향된 애노드(100)와 캐소드(200); 상기 애노드(100)와 캐소드(200) 사이에 개재된 복수의 발광 유닛(400, 500); 및 서로 인접한 발광 유닛(400, 500) 사이에 개재되고, N형 전하 생성층(610) 및 P형 전하 생성층(620)을 포함하는 전하 생성층(600)을 포함한다. 이때, 상기 N형 전하 생성층(610)이 전술한 화학식 1로 표시되는 화합물을 포함한다.As shown in Figure 4, the organic electroluminescent device according to the fourth embodiment of the present invention is a tandem (tandem) type device, the anode 100 and the cathode 200 facing each other; a plurality of light emitting units 400 and 500 interposed between the anode 100 and the cathode 200; and a charge generation layer 600 interposed between adjacent light emitting units 400 and 500 and including an N-type charge generation layer 610 and a P-type charge generation layer 620 . In this case, the N-type charge generation layer 610 includes the compound represented by the above-described Chemical Formula 1.
이러한 탠덤형 유기 전계 발광 소자는 발광 유닛이 최소 2개이며, 전하 생성층을 인접한 발광 유닛들 사이에 개재하여 발광 유닛의 수를 늘려 구성할 수 있다. 일례에 따르면, 복수의 발광 유닛은 제1 발광 유닛(400), 및 제2 발광 유닛(500)을 포함할 수 있다.Such a tandem organic electroluminescent device has at least two light emitting units, and may be configured by interposing a charge generating layer between adjacent light emitting units to increase the number of light emitting units. According to an example, the plurality of light emitting units may include a first light emitting unit 400 and a second light emitting unit 500 .
이때, 각 발광 유닛(400, 500)은 정공 수송층(410, 510), 발광층(420, 520) 및 전자 수송층(430, 530)을 포함한다. 구체적으로, 제1 발광 유닛(400)은 제1 정공 수송층(410), 제1 발광층(420) 및 제1 전자 수송층(430)을 포함하고, 제2 발광 유닛(500)은 정공 수송층(510), 발광층(520) 및 전자 수송층(530)을 포함할 수 있다. 선택적으로, 상기 제1 발광 유닛(400)은 정공 주입층(440)을 추가적으로 포함할 수 있다.In this case, each of the light emitting units 400 and 500 includes hole transport layers 410 and 510 , light emitting layers 420 and 520 , and electron transport layers 430 and 530 . Specifically, the first light emitting unit 400 includes a first hole transport layer 410 , a first light emitting layer 420 , and a first electron transport layer 430 , and the second light emitting unit 500 includes a hole transport layer 510 . , an emission layer 520 and an electron transport layer 530 . Optionally, the first light emitting unit 400 may additionally include a hole injection layer 440 .
상기 정공 수송층(410, 510), 발광층(420, 520), 전자 수송층(430, 530) 및 정공 주입층(440)은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.The hole transport layers 410 and 510, the light emitting layers 420 and 520, the electron transport layers 430 and 530, and the hole injection layer 440 are not particularly limited, and common materials known in the art may be used.
상기 전하 생성층 (Charge Generation Layer, CGL)(600)은 서로 인접한 발광 유닛(400, 500) 사이에 배치됨으로써, 발광 유닛(400, 500) 사이의 전하를 조절하여 전하 균형이 이루어지도록 한다. The charge generation layer (CGL) 600 is disposed between the light emitting units 400 and 500 adjacent to each other, thereby controlling the charges between the light emitting units 400 and 500 to achieve a charge balance.
전하 생성층(600)은 제1 발광 유닛(400)과 인접하게 위치하여 제1 발광 유닛(400)에 전자를 공급하는 N형 전하 생성층(610); 및 제2 발광 유닛(500)과 인접하게 위치하여 제2 발광 유닛(500)에 정공을 공급하는 P형 전하 생성층(620)을 포함한다. The charge generation layer 600 may include an N-type charge generation layer 610 positioned adjacent to the first light emitting unit 400 and supplying electrons to the first light emitting unit 400 ; and a P-type charge generation layer 620 positioned adjacent to the second light emitting unit 500 to supply holes to the second light emitting unit 500 .
상기 N형 전하 생성층(610)은 전술한 화학식 1로 표시되는 화합물을 포함한다. 상기 화학식 1의 화합물은 전자 이동성이 우수하여 전자 주입 및 수송 능력이 우수하다. 따라서, 상기 화학식 1의 화합물을 N형 전하 생성층 재료로 유기 전계 발광 소자에 적용할 경우, 소자의 진행성 구동 전압의 증가 및 수명 저하를 방지할 수 있다. The N-type charge generation layer 610 includes the compound represented by Chemical Formula 1 described above. The compound of Formula 1 has excellent electron mobility and excellent electron injection and transport ability. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device as an N-type charge generating layer material, it is possible to prevent an increase in the progressive driving voltage and a decrease in the lifetime of the device.
상기 N형 전하 생성층(610)의 두께는 특별히 한정되지 않으며, 예컨대 약 5 내지 30 ㎚ 범위일 수 있다.The thickness of the N-type charge generation layer 610 is not particularly limited, and may be, for example, in the range of about 5 to 30 nm.
상기 P형 전하 생성층(620)은 금속 또는 P형이 도핑된 유기 물질로 이루어질 수 있다. 여기서, 상기 금속은 Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni 및 Ti 등이 있고, 이들은 단독으로 사용되거나, 또는 2개 이상의 합금으로 사용될 수 있다. 또한, 상기 P형이 도핑된 유기 물질에 사용되는 P형 도펀트와 호스트의 물질은 통상적으로 사용되는 물질이라면 특별히 한정되지 않는다. 예를 들면, 상기 P형 도펀트는 F4-TCNQ(2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane), 요오드, FeCl3, FeF3 및 SbCl5 등이 있는데, 이들은 단독으로 사용되거나 2종 이상이 혼합되어 사용될 수 있다. 또, 상기 호스트의 비제한적인 예로는 NPB(N,N'-bis(naphthaen-1-yl)-N,N'-bis(phenyl)-benzidine), TPD(N,N'-bis(3-methylphenyl)N,N'-bis(phenyl)-benzidine) 및 TNB(N,N,N',N'-tetra-naphthalenyl-benzidine) 등이 있는데, 이들은 단독으로 사용되거나 2종 이상이 혼합되어 사용될 수 있다.The P-type charge generation layer 620 may be formed of a metal or an organic material doped with P-type. Here, the metal includes Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni and Ti, and these metals may be used alone or as an alloy of two or more. In addition, materials of the P-type dopant and the host used in the P-type doped organic material are not particularly limited as long as they are commonly used materials. For example, the P-type dopant includes F 4 -TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane), iodine, FeCl 3 , FeF 3 and SbCl 5 and the like. , these may be used alone or in combination of two or more. In addition, non-limiting examples of the host include NPB (N,N'-bis(naphthaen-1-yl)-N,N'-bis(phenyl)-benzidine), TPD (N,N'-bis(3- There are methylphenyl)N,N'-bis(phenyl)-benzidine) and TNB(N,N,N',N'-tetra-naphthalenyl-benzidine), which may be used alone or in combination of two or more. have.
상기 애노드(100) 및 캐소드(200)에 대한 설명은 전술한 제1~제3 실시 형태 부분에 설명한 바와 동일하기 때문에, 생략한다.Since the description of the anode 100 and the cathode 200 is the same as that described in the first to third embodiments described above, they are omitted.
이하, 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.
[합성예 1] 화합물 A-1의 합성[Synthesis Example 1] Synthesis of compound A-1
Figure PCTKR2020017988-appb-I000023
Figure PCTKR2020017988-appb-I000023
4-chloro-2-methyl-1,10-phenanthroline (5 g, 21.8 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (7.7 g, 21.8 mmol), Pd(OAc)2 (0.2 g, 1.1 mmol), Xphos (1.0g, 2.2 mmol),및 Cs2CO3 (14.3 g, 43.7 mmol)을 Toluene 50ml, EtOH 10ml, H2O 10ml에 넣고 12 시간 동안 가열 환류하였다.반응 종결 후 메틸렌클로라이드로 유기층을 추출한 다음, MgSO4를 넣고 필터하였다. 필터된 유기층에서 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 A-1 (7.9 g, 수율 72 %)을 얻었다.4-chloro-2-methyl-1,10-phenanthroline (5 g, 21.8 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (7.7 g , 21.8 mmol), Pd(OAc) 2 (0.2 g, 1.1 mmol), Xphos (1.0 g, 2.2 mmol), and Cs 2 CO 3 (14.3 g, 43.7 mmol) in 50 ml of Toluene, 10 ml of EtOH, 10 ml of H 2 O The mixture was heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound A-1 (7.9 g, yield 72%) was obtained by column chromatography.
[LCMS] : 502[LCMS]: 502
[합성예 2] 화합물 A-2의 합성[Synthesis Example 2] Synthesis of compound A-2
Figure PCTKR2020017988-appb-I000024
Figure PCTKR2020017988-appb-I000024
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-2 (8.2 g, 수율 75 %)를 얻었다.(3-(4,6-diphenyl-1,3,5-triazin) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 A target compound A-2 (8.2 g, yield 75%) was obtained in the same manner as in [Synthesis Example 1] except that -2-yl)phenyl)boronic acid was used.
[LCMS] : 502[LCMS]: 502
[합성예 3] 화합물 A-6의 합성[Synthesis Example 3] Synthesis of compound A-6
Figure PCTKR2020017988-appb-I000025
Figure PCTKR2020017988-appb-I000025
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-6 (8.8 g, 수율 70 %)을 얻었다.(3'-(4,6-diphenyl-1,3,5-) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The same procedure as in [Synthesis Example 1] was performed except that triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used, and the target compound A-6 (8.8 g, yield 70) was carried out in the same manner as in [Synthesis Example 1]. %) was obtained.
[LCMS] : 578[LCMS]: 578
[합성예 4] 화합물 A-9의 합성[Synthesis Example 4] Synthesis of compound A-9
Figure PCTKR2020017988-appb-I000026
Figure PCTKR2020017988-appb-I000026
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-9 (9.5 g, 수율 75 %)를 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 (3-(4-([1,1'-biphenyl]-4 -yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 1], except that the target compound A-9 (9.5 g, yield 75%) was obtained.
[LCMS] : 578[LCMS]: 578
[합성예 5] 화합물 A-14의 합성[Synthesis Example 5] Synthesis of compound A-14
Figure PCTKR2020017988-appb-I000027
Figure PCTKR2020017988-appb-I000027
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-14 (7.8 g, 수율 71 %)를 얻었다.(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The same procedure as in [Synthesis Example 1] was performed except that acid was used to obtain the target compound A-14 (7.8 g, yield 71%).
[LCMS] : 501[LCMS] : 501
[합성예 6] 화합물 A-17의 합성[Synthesis Example 6] Synthesis of compound A-17
Figure PCTKR2020017988-appb-I000028
Figure PCTKR2020017988-appb-I000028
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)boronic acid을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-17 (9.6 g, 수율 76 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 (3'-(2,6-diphenylpyrimidin-4-yl)-[ A target compound A-17 (9.6 g, yield 76%) was obtained in the same manner as in [Synthesis Example 1] except that 1,1'-biphenyl]-4-yl)boronic acid was used.
[LCMS] : 577[LCMS]: 577
[합성예 7] 화합물 A-20의 합성[Synthesis Example 7] Synthesis of compound A-20
Figure PCTKR2020017988-appb-I000029
Figure PCTKR2020017988-appb-I000029
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-20 (8.8 g, 수율 70 %)을 얻었다.(4-(6-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 1], except that the target compound A-20 (8.8 g, yield 70%) was obtained.
[LCMS] : 577[LCMS]: 577
[합성예 8] 화합물 A-21의 합성[Synthesis Example 8] Synthesis of compound A-21
Figure PCTKR2020017988-appb-I000030
Figure PCTKR2020017988-appb-I000030
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-21 (8.8 g, 수율 70 %)을 얻었다.(3-(6-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-21 (8.8 g, yield 70%) was obtained in the same manner as in [Synthesis Example 1] except that -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 577[LCMS]: 577
[합성예 9] 화합물 A-35의 합성[Synthesis Example 9] Synthesis of compound A-35
Figure PCTKR2020017988-appb-I000031
Figure PCTKR2020017988-appb-I000031
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (4-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-35 (8.5 g, 수율 68 %)를 얻었다.(4-(2-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-35 (8.5 g, yield 68%) was obtained in the same manner as in [Synthesis Example 1] except that -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 577[LCMS]: 577
[합성예 10] 화합물 A-36의 합성[Synthesis Example 10] Synthesis of compound A-36
Figure PCTKR2020017988-appb-I000032
Figure PCTKR2020017988-appb-I000032
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-36 (7.5 g, 수율 60 %)을 얻었다.(3-(2-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used, and the same procedure as in [Synthesis Example 1] was performed to obtain the target compound A-36 (7.5 g, yield 60%).
[LCMS] : 577[LCMS]: 577
[합성예 11] 화합물 A-37의 합성[Synthesis Example 11] Synthesis of compound A-37
Figure PCTKR2020017988-appb-I000033
Figure PCTKR2020017988-appb-I000033
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-37 (8.1 g, 수율 63 %)을 얻었다.(3-(4-(dibenzo[b,d]furan-3-) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 1] except that the target compound A-37 (8.1 g, yield) 63%) was obtained.
[LCMS] : 592[LCMS]: 592
[합성예 12] 화합물 A-38의 합성[Synthesis Example 12] Synthesis of compound A-38
Figure PCTKR2020017988-appb-I000034
Figure PCTKR2020017988-appb-I000034
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3'-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-38 (9.2 g, 수율 63 %)을 얻었다.(3'-(4-(dibenzo[b,d]furan-3) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The same procedure as in [Synthesis Example 1] except that -yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used to obtain the target compound A-38 (9.2 g, yield 63%).
[LCMS] : 668[LCMS]: 668
[합성예 13] 화합물 A-40의 합성[Synthesis Example 13] Synthesis of compound A-40
Figure PCTKR2020017988-appb-I000035
Figure PCTKR2020017988-appb-I000035
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-40 (8.5 g, 수율 66 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1, (3-(6-(dibenzo[b,d]furan-3- A target compound A-40 (8.5 g, yield 66%) was obtained in the same manner as in [Synthesis Example 1] except that yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 591[LCMS]: 591
[합성예 14] 화합물 A-43의 합성[Synthesis Example 14] Synthesis of compound A-43
Figure PCTKR2020017988-appb-I000036
Figure PCTKR2020017988-appb-I000036
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (4-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-43 (8.0 g, 수율 69 %)을 얻었다.(4-(2-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-43 (8.0 g, yield 69%) was obtained in the same manner as in [Synthesis Example 1] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 531[LCMS]: 531
[합성예 15] 화합물 A-44의 합성[Synthesis Example 15] Synthesis of compound A-44
Figure PCTKR2020017988-appb-I000037
Figure PCTKR2020017988-appb-I000037
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-44 (8.0 g, 수율 69 %)을 얻었다.(3-(2-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-44 (8.0 g, yield 69%) was obtained in the same manner as in [Synthesis Example 1] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 531[LCMS]: 531
[합성예 16] 화합물 A-47의 합성[Synthesis Example 16] Synthesis of compound A-47
Figure PCTKR2020017988-appb-I000038
Figure PCTKR2020017988-appb-I000038
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-47 (7.8 g, 수율 70 %)을 얻었다.(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-47 (7.8 g, yield 70%) was obtained in the same manner as in [Synthesis Example 1] except that -yl)phenyl)boronic acid was used.
[LCMS] : 515[LCMS]: 515
[합성예 17] 화합물 A-49의 합성[Synthesis Example 17] Synthesis of compound A-49
Figure PCTKR2020017988-appb-I000039
Figure PCTKR2020017988-appb-I000039
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (4-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-49 (8.0 g, 수율 69 %)을 얻었다.(4-(4-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-49 (8.0 g, yield 69%) was obtained in the same manner as in [Synthesis Example 1] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 531[LCMS]: 531
[합성예 18] 화합물 A-50의 합성[Synthesis Example 18] Synthesis of compound A-50
Figure PCTKR2020017988-appb-I000040
Figure PCTKR2020017988-appb-I000040
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-50 (8.0 g, 수율 69 %)을 얻었다.(3-(4-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 The target compound A-50 (8.0 g, yield 69%) was obtained in the same manner as in [Synthesis Example 1] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 531[LCMS]: 531
[합성예 19] 화합물 A-55의 합성[Synthesis Example 19] Synthesis of compound A-55
Figure PCTKR2020017988-appb-I000041
Figure PCTKR2020017988-appb-I000041
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (4-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-55 (7.6 g, 수율 65 %)을 얻었다.(4-(6,8-diphenyl-[1,2,4] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1) The target compound A-55 (7.6 g, yield 65%) was obtained in the same manner as in [Synthesis Example 1] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 540[LCMS]: 540
[합성예 20] 화합물 A-56의 합성[Synthesis Example 20] Synthesis of compound A-56
Figure PCTKR2020017988-appb-I000042
Figure PCTKR2020017988-appb-I000042
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-56 (7.6 g, 수율 65 %)을 얻었다.(3-(6,8-diphenyl-[1,2,4] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1) The target compound A-56 (7.6 g, yield 65%) was obtained in the same manner as in [Synthesis Example 1] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 540[LCMS]: 540
[합성예 21] 화합물 A-57의 합성[Synthesis Example 21] Synthesis of compound A-57
Figure PCTKR2020017988-appb-I000043
Figure PCTKR2020017988-appb-I000043
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-57 (6.8 g, 수율 67 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1 (4-(6-phenyl-[1,2,4]triazolo[ A target compound A-57 (6.8 g, yield 67%) was obtained in the same manner as in [Synthesis Example 1] except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used.
[LCMS] : 464[LCMS]: 464
[합성예 22] 화합물 A-60의 합성[Synthesis Example 22] Synthesis of compound A-60
Figure PCTKR2020017988-appb-I000044
Figure PCTKR2020017988-appb-I000044
합성예 1에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신 (3-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 A-60 (6.8 g, 수율 67 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 1, (3-(8-phenyl-[1,2,4]triazolo[ A target compound A-60 (6.8 g, yield 67%) was obtained in the same manner as in [Synthesis Example 1] except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used.
[LCMS] : 464[LCMS]: 464
[합성예 23] 화합물 B-1의 합성[Synthesis Example 23] Synthesis of compound B-1
Figure PCTKR2020017988-appb-I000045
Figure PCTKR2020017988-appb-I000045
합성예 1에서 사용된 4-chloro-2-methyl-1,10-phenanthroline 대신4-chloro-2-ethyl-1,10-phenanthroline 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 B-1 (8.1 g, 수율 72 %)을 얻었다.The same procedure as in [Synthesis Example 1] was performed except that 4-chloro-2-ethyl-1,10-phenanthroline was used instead of 4-chloro-2-methyl-1,10-phenanthroline used in Synthesis Example 1. The target compound B-1 (8.1 g, yield 72%) was obtained.
[LCMS] : 516[LCMS]: 516
[합성예 24] 화합물 B-2의 합성[Synthesis Example 24] Synthesis of compound B-2
Figure PCTKR2020017988-appb-I000046
Figure PCTKR2020017988-appb-I000046
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-2 (8.1 g, 수율 72 %)을 얻었다.(3-(4,6-diphenyl-1,3,5-triazin) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 A target compound B-2 (8.1 g, yield 72%) was obtained in the same manner as in [Synthesis Example 23] except that -2-yl)phenyl)boronic acid was used.
[LCMS] : 516[LCMS]: 516
[합성예 25] 화합물 B-6의 합성[Synthesis Example 25] Synthesis of compound B-6
Figure PCTKR2020017988-appb-I000047
Figure PCTKR2020017988-appb-I000047
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-6 (9.0 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3'-(4,6-diphenyl-1,3,5- The same procedure as in [Synthesis Example 23] was performed except that triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used, and the target compound B-6 (9.0 g, yield 70) %) was obtained.
[LCMS] : 592[LCMS]: 592
[합성예 26] 화합물 B-9의 합성[Synthesis Example 26] Synthesis of compound B-9
Figure PCTKR2020017988-appb-I000048
Figure PCTKR2020017988-appb-I000048
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-9 (9.0 g, 수율 70 %)를 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3-(4-([1,1'-biphenyl]-4 -yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 23], except that the target compound B-9 (9.0 g, yield 70%) was obtained.
[LCMS] : 592[LCMS]: 592
[합성예 27] 화합물 B-14의 합성[Synthesis Example 27] Synthesis of compound B-14
Figure PCTKR2020017988-appb-I000049
Figure PCTKR2020017988-appb-I000049
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-14 (8.0 g, 수율 71 %)를 얻었다.(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 The same procedure as in [Synthesis Example 23] was performed except that acid was used to obtain the target compound B-14 (8.0 g, yield 71%).
[LCMS] : 515[LCMS]: 515
[합성예 28] 화합물 B-17의 합성[Synthesis Example 28] Synthesis of compound B-17
Figure PCTKR2020017988-appb-I000050
Figure PCTKR2020017988-appb-I000050
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)boronic acid을 사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-17 (9.0 g, 수율 76 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3'-(2,6-diphenylpyrimidin-4-yl)-[ The same procedure as in [Synthesis Example 23] was performed except that 1,1'-biphenyl]-4-yl)boronic acid was used to obtain the target compound B-17 (9.0 g, yield 76%).
[LCMS] : 591[LCMS]: 591
[합성예 29] 화합물 B-20의 합성[Synthesis Example 29] Synthesis of compound B-20
Figure PCTKR2020017988-appb-I000051
Figure PCTKR2020017988-appb-I000051
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-20 (9.0 g, 수율 70 %)을 얻었다.(4-(6-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used, and the same procedure as in [Synthesis Example 23] was performed to obtain the target compound B-20 (9.0 g, yield 70%).
[LCMS] : 591[LCMS]: 591
[합성예 30] 화합물 B-21의 합성[Synthesis Example 30] Synthesis of compound B-21
Figure PCTKR2020017988-appb-I000052
Figure PCTKR2020017988-appb-I000052
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-21 (9.0 g, 수율 70 %)을 얻었다.(3-(6-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 23] to obtain the target compound B-21 (9.0 g, yield 70%).
[LCMS] : 591[LCMS]: 591
[합성예 31] 화합물 B-35의 합성[Synthesis Example 31] Synthesis of compound B-35
Figure PCTKR2020017988-appb-I000053
Figure PCTKR2020017988-appb-I000053
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-35 (8.8 g, 수율 68 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (4-(2-([1,1'-biphenyl]-4 -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used, and the same procedure as in [Synthesis Example 23] was performed to obtain the target compound B-35 (8.8 g, yield 68%).
[LCMS] : 591[LCMS]: 591
[합성예 32] 화합물 B-36의 합성[Synthesis Example 32] Synthesis of compound B-36
Figure PCTKR2020017988-appb-I000054
Figure PCTKR2020017988-appb-I000054
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-36 (7.7 g, 수율 60 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3-(2-([1,1'-biphenyl]-4 -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used, and the same procedure as in [Synthesis Example 23] was performed to obtain the target compound B-36 (7.7 g, yield 60%).
[LCMS] : 591[LCMS]: 591
[합성예 33] 화합물 B-37의 합성[Synthesis Example 33] Synthesis of compound B-37
Figure PCTKR2020017988-appb-I000055
Figure PCTKR2020017988-appb-I000055
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-37 (8.3 g, 수율 63 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3-(4-(dibenzo[b,d]furan-3- yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 23] except that the target compound B-37 (8.3 g, yield) 63%) was obtained.
[LCMS] : 606[LCMS]: 606
[합성예 34] 화합물 B-38의 합성[Synthesis Example 34] Synthesis of compound B-38
Figure PCTKR2020017988-appb-I000056
Figure PCTKR2020017988-appb-I000056
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid을 사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-38 (9.4 g, 수율 63 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3'-(4-(dibenzo[b,d]furan-3 -yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid The same procedure as in [Synthesis Example 23] except that to obtain the target compound B-38 (9.4 g, yield 63%).
[LCMS] : 682[LCMS]: 682
[합성예 35] 화합물 B-40의 합성[Synthesis Example 35] Synthesis of compound B-40
Figure PCTKR2020017988-appb-I000057
Figure PCTKR2020017988-appb-I000057
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-40 (8.7 g, 수율 66 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3-(6-(dibenzo[b,d]furan-3- A target compound B-40 (8.7 g, yield 66%) was obtained in the same manner as in [Synthesis Example 23] except that yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 605[LCMS]: 605
[합성예 36] 화합물 B-43의 합성[Synthesis Example 36] Synthesis of compound B-43
Figure PCTKR2020017988-appb-I000058
Figure PCTKR2020017988-appb-I000058
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-43 (8.2 g, 수율 69 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 23 (4- (2-phenylbenzo [4,5] thieno [3,2 The target compound B-43 (8.2 g, yield 69%) was obtained in the same manner as in [Synthesis Example 23] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 545[LCMS]: 545
[합성예 37] 화합물 B-44의 합성[Synthesis Example 37] Synthesis of compound B-44
Figure PCTKR2020017988-appb-I000059
Figure PCTKR2020017988-appb-I000059
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-44 (8.2 g, 수율 69 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 23 (3- (2-phenylbenzo [4,5] thieno [3,2 -d]pyrimidin-4-yl)phenyl)boronic acid was used, and the same procedure as in [Synthesis Example 23] was performed to obtain the target compound B-44 (8.2 g, yield 69%).
[LCMS] : 545[LCMS]: 545
[합성예 38] 화합물 B-47의 합성[Synthesis Example 38] Synthesis of compound B-47
Figure PCTKR2020017988-appb-I000060
Figure PCTKR2020017988-appb-I000060
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-47 (8.1 g, 수율 70 %)을 얻었다.(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 The target compound B-47 (8.1 g, yield 70%) was obtained in the same manner as in [Synthesis Example 23] except that -yl)phenyl)boronic acid was used.
[LCMS] : 529[LCMS]: 529
[합성예 39] 화합물 B-49의 합성[Synthesis Example 39] Synthesis of compound B-49
Figure PCTKR2020017988-appb-I000061
Figure PCTKR2020017988-appb-I000061
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-49 (8.2 g, 수율 69 %)을 얻었다.(4-(4-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 The target compound B-49 (8.2 g, yield 69%) was obtained in the same manner as in [Synthesis Example 23] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 545[LCMS]: 545
[합성예 40] 화합물 B-50의 합성[Synthesis Example 40] Synthesis of compound B-50
Figure PCTKR2020017988-appb-I000062
Figure PCTKR2020017988-appb-I000062
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-50 (8.2 g, 수율 69 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 23 (3- (4-phenylbenzo [4,5] thieno [3,2 The target compound B-50 (8.2 g, yield 69%) was obtained in the same manner as in [Synthesis Example 23] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 545[LCMS]: 545
[합성예 41] 화합물 B-55의 합성[Synthesis Example 41] Synthesis of compound B-55
Figure PCTKR2020017988-appb-I000063
Figure PCTKR2020017988-appb-I000063
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-55 (7.8 g, 수율 65 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (4-(6,8-diphenyl-[1,2,4] The target compound B-55 (7.8 g, yield 65%) was obtained in the same manner as in [Synthesis Example 23] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 554[LCMS]: 554
[합성예 42] 화합물 B-56의 합성[Synthesis Example 42] Synthesis of compound B-56
Figure PCTKR2020017988-appb-I000064
Figure PCTKR2020017988-appb-I000064
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-56 (7.8 g, 수율 65 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3-(6,8-diphenyl-[1,2,4] The target compound B-56 (7.8 g, yield 65%) was obtained in the same manner as in [Synthesis Example 23] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 554[LCMS]: 554
[합성예 43] 화합물 B-57의 합성[Synthesis Example 43] Synthesis of compound B-57
Figure PCTKR2020017988-appb-I000065
Figure PCTKR2020017988-appb-I000065
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-57 (7.0 g, 수율 67 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (4-(6-phenyl-[1,2,4]triazolo[ The same procedure as in [Synthesis Example 23] was performed except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used to obtain the target compound B-57 (7.0 g, yield 67%).
[LCMS] : 478[LCMS]: 478
[합성예 44] 화합물 B-60의 합성[Synthesis Example 44] Synthesis of compound B-60
Figure PCTKR2020017988-appb-I000066
Figure PCTKR2020017988-appb-I000066
합성예 23에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 B-60 (7.0 g, 수율 67 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 23 (3-(8-phenyl-[1,2,4]triazolo[ The same procedure as in [Synthesis Example 23] was performed except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used to obtain the target compound B-60 (7.0 g, yield 67%).
[LCMS] : 478[LCMS]: 478
[합성예 45] 화합물 C-1의 합성[Synthesis Example 45] Synthesis of compound C-1
Figure PCTKR2020017988-appb-I000067
Figure PCTKR2020017988-appb-I000067
합성예 1에서 사용된 4-chloro-2-methyl-1,10-phenanthroline대신4-chloro-2-isopropyl-1,10-phenanthroline을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 C-1 (8.3 g, 수율 72 %)을 얻었다.The same procedure as in [Synthesis Example 1] was performed except that 4-chloro-2-isopropyl-1,10-phenanthroline was used instead of 4-chloro-2-methyl-1,10-phenanthroline used in Synthesis Example 1 The target compound C-1 (8.3 g, yield 72%) was obtained.
[LCMS] : 530[LCMS]: 530
[합성예 46] 화합물 C-2의 합성[Synthesis Example 46] Synthesis of compound C-2
Figure PCTKR2020017988-appb-I000068
Figure PCTKR2020017988-appb-I000068
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-2 (8.3 g, 수율 72 %)을 얻었다.(3-(4,6-diphenyl-1,3,5-triazin) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 A target compound C-2 (8.3 g, yield 72%) was obtained in the same manner as in [Synthesis Example 45] except that -2-yl)phenyl)boronic acid was used.
[LCMS] : 530[LCMS]: 530
[합성예 47] 화합물 C-6의 합성[Synthesis Example 47] Synthesis of compound C-6
Figure PCTKR2020017988-appb-I000069
Figure PCTKR2020017988-appb-I000069
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-6 (9.0 g, 수율 68 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3'-(4,6-diphenyl-1,3,5- The same procedure as in [Synthesis Example 45] was performed except that triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used, and the target compound C-6 (9.0 g, yield 68) %) was obtained.
[LCMS] : 606[LCMS]: 606
[합성예 48] 화합물 C-9의 합성[Synthesis Example 48] Synthesis of compound C-9
Figure PCTKR2020017988-appb-I000070
Figure PCTKR2020017988-appb-I000070
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-9 (9.2 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3-(4-([1,1'-biphenyl]-4 -yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 45], except that the target compound C-9 (9.2 g, yield 70%) was obtained.
[LCMS] : 606[LCMS]: 606
[합성예 49] 화합물 C-14의 합성[Synthesis Example 49] Synthesis of compound C-14
Figure PCTKR2020017988-appb-I000071
Figure PCTKR2020017988-appb-I000071
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-14 (8.3 g, 수율 72 %)을 얻었다.(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The same procedure as in [Synthesis Example 45] was performed except that acid was used to obtain the target compound C-14 (8.3 g, yield 72%).
[LCMS] : 529[LCMS]: 529
[합서예 50] 화합물 C-17의 합성[Synthesis Example 50] Synthesis of compound C-17
Figure PCTKR2020017988-appb-I000072
Figure PCTKR2020017988-appb-I000072
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)boronic acid을 사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-17 (10.2 g, 수율 77 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3'-(2,6-diphenylpyrimidin-4-yl)-[ The target compound C-17 (10.2 g, yield 77%) was obtained in the same manner as in [Synthesis Example 45] except that 1,1'-biphenyl]-4-yl)boronic acid was used.
[LCMS] : 605[LCMS]: 605
[합성예 51] 화합물 C-20의 합성[Synthesis Example 51] Synthesis of compound C-20
Figure PCTKR2020017988-appb-I000073
Figure PCTKR2020017988-appb-I000073
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-20 (9.2 g, 수율 70 %)을 얻었다.(4-(6-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The target compound C-20 (9.2 g, yield 70%) was obtained in the same manner as in [Synthesis Example 45] except that -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 605[LCMS]: 605
[합성예 52] 화합물 C-21의 합성[Synthesis Example 52] Synthesis of compound C-21
Figure PCTKR2020017988-appb-I000074
Figure PCTKR2020017988-appb-I000074
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-21 (9.5 g, 수율 72 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3-(6-([1,1'-biphenyl]-4 The target compound C-21 (9.5 g, yield 72%) was obtained in the same manner as in [Synthesis Example 45] except that -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 605[LCMS]: 605
[합성예 53] 화합물 C-35의 합성[Synthesis Example 53] Synthesis of compound C-35
Figure PCTKR2020017988-appb-I000075
Figure PCTKR2020017988-appb-I000075
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-35 (8.0 g, 수율 68 %)을 얻었다.(4-(2-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The target compound C-35 (8.0 g, yield 68%) was obtained in the same manner as in [Synthesis Example 45] except that -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 605[LCMS]: 605
[합성예 54] 화합물 C-36의 합성[Synthesis Example 54] Synthesis of compound C-36
Figure PCTKR2020017988-appb-I000076
Figure PCTKR2020017988-appb-I000076
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-36 (8.3 g, 수율 63 %)을 얻었다.(3-(2-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The target compound C-36 (8.3 g, yield 63%) was obtained in the same manner as in [Synthesis Example 45] except that -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 605[LCMS]: 605
[합성예 55] 화합물 C-37의 합성[Synthesis Example 55] Synthesis of compound C-37
Figure PCTKR2020017988-appb-I000077
Figure PCTKR2020017988-appb-I000077
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-37 (9.0 g, 수율 67 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3-(4-(dibenzo[b,d]furan-3- yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 45] except that the target compound C-37 (9.0 g, yield) 67%) was obtained.
[LCMS] : 620[LCMS]: 620
[합성예 56] 화합물 C-38의 합성[Synthesis Example 56] Synthesis of compound C-38
Figure PCTKR2020017988-appb-I000078
Figure PCTKR2020017988-appb-I000078
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid을 사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-38 (10.5 g, 수율 69 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3'-(4-(dibenzo[b,d]furan-3 The same procedure as in [Synthesis Example 45] except that -yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was used to obtain the target compound C-38 (10.5 g, yield 69%).
[LCMS] : 696[LCMS] : 696
[합성예 57] 화합물 C-40의 합성[Synthesis Example 57] Synthesis of compound C-40
Figure PCTKR2020017988-appb-I000079
Figure PCTKR2020017988-appb-I000079
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-40 (8.8 g, 수율 65 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3-(6-(dibenzo[b,d]furan-3- The same procedure as in [Synthesis Example 45] was performed except that yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used to obtain the target compound C-40 (8.8 g, yield 65%).
[LCMS] : 619[LCMS]: 619
[합성예 58] 화합물 C-43의 합성[Synthesis Example 58] Synthesis of compound C-43
Figure PCTKR2020017988-appb-I000080
Figure PCTKR2020017988-appb-I000080
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-43 (8.3 g, 수율 68 %)을 얻었다.(4-(2-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The target compound C-43 (8.3 g, yield 68%) was obtained in the same manner as in [Synthesis Example 45] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 559[LCMS]: 559
[합성예 59] 화합물 C-44의 합성[Synthesis Example 59] Synthesis of compound C-44
Figure PCTKR2020017988-appb-I000081
Figure PCTKR2020017988-appb-I000081
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-44 (8.4 g, 수율 69 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 45 (3- (2-phenylbenzo [4,5] thieno [3,2 The target compound C-44 (8.4 g, yield 69%) was obtained in the same manner as in [Synthesis Example 45] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 559[LCMS]: 559
[합성예 60] 화합물 C-47의 합성[Synthesis Example 60] Synthesis of compound C-47
Figure PCTKR2020017988-appb-I000082
Figure PCTKR2020017988-appb-I000082
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-47 (8.2 g, 수율 62 %)을 얻었다.(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The target compound C-47 (8.2 g, yield 62%) was obtained in the same manner as in [Synthesis Example 45] except that -yl)phenyl)boronic acid was used.
[LCMS] : 543[LCMS]: 543
[합성예 61] 화합물 C-49의 합성[Synthesis Example 61] Synthesis of compound C-49
Figure PCTKR2020017988-appb-I000083
Figure PCTKR2020017988-appb-I000083
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-49 (8.5 g, 수율 70 %)을 얻었다.(4-(4-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 The target compound C-49 (8.5 g, yield 70%) was obtained in the same manner as in [Synthesis Example 45] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 559[LCMS]: 559
[합성예 62] 화합물 C-50의 합성[Synthesis Example 62] Synthesis of compound C-50
Figure PCTKR2020017988-appb-I000084
Figure PCTKR2020017988-appb-I000084
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-50 (8.4 g, 수율 69 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 45 (3- (4-phenylbenzo [4,5] thieno [3,2 The target compound C-50 (8.4 g, yield 69%) was obtained in the same manner as in [Synthesis Example 45] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 559[LCMS]: 559
[합성예 63] 화합물 C-55의 합성[Synthesis Example 63] Synthesis of compound C-55
Figure PCTKR2020017988-appb-I000085
Figure PCTKR2020017988-appb-I000085
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-55 (7.9 g, 수율 64 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (4-(6,8-diphenyl-[1,2,4] The target compound C-55 (7.9 g, yield 64%) was obtained in the same manner as in [Synthesis Example 45] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 568[LCMS]: 568
[합성예 64] 화합물 C-56의 합성[Synthesis Example 64] Synthesis of compound C-56
Figure PCTKR2020017988-appb-I000086
Figure PCTKR2020017988-appb-I000086
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-56 (7.9 g, 수율 64 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3-(6,8-diphenyl-[1,2,4] The target compound C-56 (7.9 g, yield 64%) was obtained in the same manner as in [Synthesis Example 45] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 568[LCMS]: 568
[합성예 65] 화합물 C-57의 합성[Synthesis Example 65] Synthesis of compound C-57
Figure PCTKR2020017988-appb-I000087
Figure PCTKR2020017988-appb-I000087
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-57 (7.5 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (4-(6-phenyl-[1,2,4]triazolo[ The same procedure as in [Synthesis Example 45] was performed except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used to obtain the target compound C-57 (7.5 g, yield 70%).
[LCMS] : 492[LCMS]: 492
[합성예 66] 화합물 C-60의 합성[Synthesis Example 66] Synthesis of compound C-60
Figure PCTKR2020017988-appb-I000088
Figure PCTKR2020017988-appb-I000088
합성예 45에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 C-60 (7.5 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 45 (3-(8-phenyl-[1,2,4]triazolo[ The same procedure as in [Synthesis Example 45] was performed except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used to obtain the target compound C-60 (7.5 g, yield 70%).
[LCMS] : 492[LCMS]: 492
[합성예 67] 화합물 D-1의 합성[Synthesis Example 67] Synthesis of compound D-1
Figure PCTKR2020017988-appb-I000089
Figure PCTKR2020017988-appb-I000089
합성예 1에서 사용된 4-chloro-2-methyl-1,10-phenanthroline 대신2-(tert-butyl)-4-chloro-1,10-phenanthroline 을사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 D-1 (8.9 g, 수율 75 %)을 얻었다.The same as in [Synthesis Example 1] except that 2-(tert-butyl)-4-chloro-1,10-phenanthroline was used instead of 4-chloro-2-methyl-1,10-phenanthroline used in Synthesis Example 1 The process was carried out to obtain the target compound D-1 (8.9 g, yield 75%).
[LCMS] : 544[LCMS]: 544
[합성예 68] 화합물 D-2의 합성[Synthesis Example 68] Synthesis of compound D-2
Figure PCTKR2020017988-appb-I000090
Figure PCTKR2020017988-appb-I000090
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-2 (853 g, 수율 72 %)을 얻었다.(3-(4,6-diphenyl-1,3,5-triazin) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 A target compound D-2 (853 g, yield 72%) was obtained in the same manner as in [Synthesis Example 67] except that -2-yl)phenyl)boronic acid was used.
[LCMS] : 544[LCMS]: 544
[합성예 69] 화합물 D-6의 합성[Synthesis Example 69] Synthesis of compound D-6
Figure PCTKR2020017988-appb-I000091
Figure PCTKR2020017988-appb-I000091
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-6 (9.2 g, 수율 68 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3'-(4,6-diphenyl-1,3,5- Triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid was carried out in the same manner as in [Synthesis Example 67] except that the target compound D-6 (9.2 g, yield 68) %) was obtained.
[LCMS] : 620[LCMS]: 620
[합성예 70] 화합물 D-9의 합성[Synthesis Example 70] Synthesis of compound D-9
Figure PCTKR2020017988-appb-I000092
Figure PCTKR2020017988-appb-I000092
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-9 (962 g, 수율 71 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(4-([1,1'-biphenyl]-4 -yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 67], except that the target compound D-9 (962 g, Yield 71%) was obtained.
[LCMS] : 620[LCMS]: 620
[합성예 71] 화합물 D-14의 합성[Synthesis Example 71] Synthesis of compound D-14
Figure PCTKR2020017988-appb-I000093
Figure PCTKR2020017988-appb-I000093
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-14 (8.2 g, 수율 69 %)을 얻었다.(3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 The same procedure as in [Synthesis Example 67] was performed except that acid was used to obtain the target compound D-14 (8.2 g, yield 69%).
[LCMS] : 543[LCMS]: 543
[합성예 72] 화합물 D-17의 합성[Synthesis Example 72] Synthesis of compound D-17
Figure PCTKR2020017988-appb-I000094
Figure PCTKR2020017988-appb-I000094
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)boronic acid을 사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-17 (9.4 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3'-(2,6-diphenylpyrimidin-4-yl)-[ The same procedure as in [Synthesis Example 67] was performed except that 1,1'-biphenyl]-4-yl)boronic acid was used to obtain the target compound D-17 (9.4 g, yield 70%).
[LCMS] : 619[LCMS]: 619
[합성예 73] 화합물 D-20의 합성[Synthesis Example 73] Synthesis of compound D-20
Figure PCTKR2020017988-appb-I000095
Figure PCTKR2020017988-appb-I000095
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-20 (9.4 g, 수율 70 %)을 얻었다.(4-(6-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 The target compound D-20 (9.4 g, yield 70%) was obtained in the same manner as in [Synthesis Example 67] except that -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 619[LCMS]: 619
[합성예 74] 화합물 D-21의 합성[Synthesis Example 74] Synthesis of compound D-21
Figure PCTKR2020017988-appb-I000096
Figure PCTKR2020017988-appb-I000096
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-21 (8.9 g, 수율 66 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(6-([1,1'-biphenyl]-4 -yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used, and the same procedure as in [Synthesis Example 67] was performed to obtain the target compound D-21 (8.9 g, yield 66%).
[LCMS] : 619[LCMS]: 619
[합성예 75] 화합물 D-35의 합성[Synthesis Example 75] Synthesis of compound D-35
Figure PCTKR2020017988-appb-I000097
Figure PCTKR2020017988-appb-I000097
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-35 (9.2 g, 수율 68 %)을 얻었다.(4-(2-([1,1'-biphenyl]-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 The target compound D-35 (9.2 g, yield 68%) was obtained in the same manner as in [Synthesis Example 67] except that -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 619[LCMS]: 619
[합성예 76] 화합물 D-36의 합성[Synthesis Example 76] Synthesis of compound D-36
Figure PCTKR2020017988-appb-I000098
Figure PCTKR2020017988-appb-I000098
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-36 (8.8 g, 수율 65 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(2-([1,1'-biphenyl]-4 The target compound D-36 (8.8 g, yield 65%) was obtained in the same manner as in [Synthesis Example 67] except that -yl)-6-phenylpyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 619[LCMS]: 619
[합성예 77] 화합물 D-37의 합성[Synthesis Example 77] Synthesis of compound D-37
Figure PCTKR2020017988-appb-I000099
Figure PCTKR2020017988-appb-I000099
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-37 (9.7 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(4-(dibenzo[b,d]furan-3- yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid was carried out in the same manner as in [Synthesis Example 67] except that the target compound D-37 (9.7 g, yield) 70%) was obtained.
[LCMS] : 634[LCMS] : 634
[합성예 78] 화합물 D-38의 합성[Synthesis Example 78] Synthesis of compound D-38
Figure PCTKR2020017988-appb-I000100
Figure PCTKR2020017988-appb-I000100
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3'-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid을 사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-38 (10.2 g, 수율 66 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3'-(4-(dibenzo[b,d]furan-3 -yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid The same procedure as in [Synthesis Example 67] except that to obtain the target compound D-38 (10.2 g, yield 66%).
[LCMS] : 710[LCMS]: 710
[합성예 79] 화합물 D-40의 합성[Synthesis Example 79] Synthesis of compound D-40
Figure PCTKR2020017988-appb-I000101
Figure PCTKR2020017988-appb-I000101
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid을 사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-40 (9.4 g, 수율 68 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(6-(dibenzo[b,d]furan-3- The same procedure as in [Synthesis Example 67] was performed except that yl)-2-phenylpyrimidin-4-yl)phenyl)boronic acid was used to obtain the target compound D-40 (9.4 g, yield 68%).
[LCMS] : 633[LCMS] : 633
[합성예 80] 화합물 D-43의 합성[Synthesis Example 80] Synthesis of compound D-43
Figure PCTKR2020017988-appb-I000102
Figure PCTKR2020017988-appb-I000102
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-43 (8.5 g, 수율 68 %)을 얻었다.(4-(2-phenylbenzo[4,5]thieno[3,2] instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 The target compound D-43 (8.5 g, yield 68%) was obtained in the same manner as in [Synthesis Example 67] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 573[LCMS]: 573
[합성예 81] 화합물 D-44의 합성[Synthesis Example 81] Synthesis of compound D-44
Figure PCTKR2020017988-appb-I000103
Figure PCTKR2020017988-appb-I000103
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-44 (8.7 g, 수율 70 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 67 (3- (2-phenylbenzo [4,5] thieno [3,2 The target compound D-44 (8.7 g, yield 70%) was obtained in the same manner as in [Synthesis Example 67] except that -d]pyrimidin-4-yl)phenyl)boronic acid was used.
[LCMS] : 573[LCMS]: 573
[합성예 82] 화합물 D-47의 합성[Synthesis Example 82] Synthesis of compound D-47
Figure PCTKR2020017988-appb-I000104
Figure PCTKR2020017988-appb-I000104
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-47 (7.9 g, 수율 65 %)을 얻었다.(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4) instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 The target compound D-47 (7.9 g, yield 65%) was obtained in the same manner as in [Synthesis Example 67] except that -yl)phenyl)boronic acid was used.
[LCMS] : 557[LCMS]: 557
[합성예 83] 화합물 D-49의 합성[Synthesis Example 83] Synthesis of compound D-49
Figure PCTKR2020017988-appb-I000105
Figure PCTKR2020017988-appb-I000105
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-49 (7.7 g, 수율 62 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 67 (4- (4-phenylbenzo [4,5] thieno [3,2 The target compound D-49 (7.7 g, yield 62%) was obtained in the same manner as in [Synthesis Example 67] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 573[LCMS]: 573
[합성예 84] 화합물 D-50의 합성[Synthesis Example 84] Synthesis of compound D-50
Figure PCTKR2020017988-appb-I000106
Figure PCTKR2020017988-appb-I000106
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-50 (8.6 g, 수율 69 %)을 얻었다.Instead of (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid used in Synthesis Example 67 (3- (4-phenylbenzo [4,5] thieno [3,2 The target compound D-50 (8.6 g, yield 69%) was obtained in the same manner as in [Synthesis Example 67] except that -d]pyrimidin-2-yl)phenyl)boronic acid was used.
[LCMS] : 573[LCMS]: 573
[합성예 85] 화합물 D-55의 합성[Synthesis Example 85] Synthesis of compound D-55
Figure PCTKR2020017988-appb-I000107
Figure PCTKR2020017988-appb-I000107
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-55(8.8 g, 수율 69 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (4-(6,8-diphenyl-[1,2,4] The target compound D-55 (8.8 g, yield 69%) was obtained in the same manner as in [Synthesis Example 67] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 582[LCMS]: 582
[합성예 86] 화합물 D-56의 합성[Synthesis Example 86] Synthesis of compound D-56
Figure PCTKR2020017988-appb-I000108
Figure PCTKR2020017988-appb-I000108
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-56(9.0 g, 수율 71 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(6,8-diphenyl-[1,2,4] The target compound D-56 (9.0 g, yield 71%) was obtained in the same manner as in [Synthesis Example 67] except that triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid was used. .
[LCMS] : 582[LCMS]: 582
[합성예 87] 화합물 D-57의 합성[Synthesis Example 87] Synthesis of compound D-57
Figure PCTKR2020017988-appb-I000109
Figure PCTKR2020017988-appb-I000109
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(4-(6-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-57(7.7 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (4-(6-phenyl-[1,2,4]triazolo[ The same procedure as in [Synthesis Example 67] was performed except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used to obtain the target compound D-57 (7.7 g, yield 70%).
[LCMS] : 506[LCMS]: 506
[합성예 88] 화합물 D-60의 합성[Synthesis Example 88] Synthesis of compound D-60
Figure PCTKR2020017988-appb-I000110
Figure PCTKR2020017988-appb-I000110
합성예 67에서 사용된 (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid대신(3-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)phenyl)boronic acid 을사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 D-60 (7.7 g, 수율 70 %)을 얻었다.Instead of (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid used in Synthesis Example 67 (3-(8-phenyl-[1,2,4]triazolo[ The same procedure as in [Synthesis Example 67] was performed except that 1,5-a]pyridin-2-yl)phenyl)boronic acid was used to obtain the target compound D-60 (7.7 g, yield 70%).
[LCMS] : 506[LCMS]: 506
[실시예 1] 청색 유기 전계 발광 소자의 제작[Example 1] Fabrication of blue organic electroluminescent device
합성예 1에서 합성된 화합물A-1를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.After high-purity sublimation purification of the compound A-1 synthesized in Synthesis Example 1 by a commonly known method, a blue organic electroluminescent device was manufactured as follows.
먼저. ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.first. A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (㈜두산전자, 30nm)/화합물 A-1 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. 이때, 사용된 NPB 및 ADN의 구조는 다음과 같다.On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics, 30 nm)/Compound A-1 (30 nm) /LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic electroluminescent device. At this time, the structures of the NPB and ADN used are as follows.
Figure PCTKR2020017988-appb-I000111
Figure PCTKR2020017988-appb-I000111
[실시예 2~88] 청색 유기 전계 발광 소자의 제작[Examples 2-88] Fabrication of blue organic electroluminescent device
실시예 1에서 전자수송층의 형성시전자 수송층 물질로 사용된 화합물 A-1 대신 하기 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except for using each of the compounds shown in Table 1 below instead of Compound A-1 used as an electron transport layer material in the formation of the electron transport layer in Example 1 did.
[비교예 1] 청색 유기 전계 발광 소자의 제작[Comparative Example 1] Fabrication of a blue organic electroluminescent device
실시예 1에서 전자수송층의 형성시전자 수송층 물질로 사용된 화합물 A-1 대신 Alq3를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 Alq3의 구조는 각각 다음과 같다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound A-1 used as an electron transport layer material when forming the electron transport layer in Example 1. The structures of Alq 3 used at this time are as follows, respectively.
Figure PCTKR2020017988-appb-I000112
Figure PCTKR2020017988-appb-I000112
[비교예 2 내지 7] 청색 유기 전계 발광 소자의 제작[Comparative Examples 2 to 7] Preparation of blue organic electroluminescent device
실시예 1에서 전자수송층의 형성시전자 수송층 물질로 사용된 화합물 A-1 대신 하기 화합물 A 내지 F를 각각 사용하는 것을 제외하고는, 상기 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compounds A to F were respectively used instead of the compound A-1 used as the electron transport layer material in the formation of the electron transport layer in Example 1 did.
Figure PCTKR2020017988-appb-I000113
Figure PCTKR2020017988-appb-I000113
[평가예 1][Evaluation Example 1]
실시예 1 내지 88 및 비교예 1 내지 7에서 각각 제조된청색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.For the blue organic electroluminescent devices prepared in Examples 1 to 88 and Comparative Examples 1 to 7, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. indicated.
샘플Sample 전자 수송층electron transport layer 구동전압(V)Driving voltage (V) 발광피크(nm)Emission peak (nm) 전류효율(cd/A)Current efficiency (cd/A)
실시예 1Example 1 A-1A-1 3.93.9 457457 8.18.1
실시예 2Example 2 A-2A-2 4.14.1 456456 7.97.9
실시예 3Example 3 A-6A-6 4.24.2 456456 7.37.3
실시예 4Example 4 A-9A-9 4.14.1 457457 7.97.9
실시예 5Example 5 A-14A-14 4.24.2 456456 7.37.3
실시예 6Example 6 A-17A-17 3.93.9 458458 8.08.0
실시예 7Example 7 A-20A-20 4.04.0 458458 7.87.8
실시예 8Example 8 A-21A-21 4.14.1 454454 7.57.5
실시예 9Example 9 A-35A-35 4.04.0 457457 7.97.9
실시예 10Example 10 A-36A-36 4.24.2 458458 7.67.6
실시예 11Example 11 A-37A-37 4.04.0 454454 7.97.9
실시예 12Example 12 A-38A-38 4.04.0 454454 7.87.8
실시예 13Example 13 A-40A-40 4.34.3 455455 7.87.8
실시예 14Example 14 A-43A-43 4.04.0 455455 8.08.0
실시예 15Example 15 A-44A-44 4.24.2 457457 7.57.5
실시예 16Example 16 A-47A-47 4.24.2 457457 7.57.5
실시예 17Example 17 A-49A-49 4.14.1 457457 7.87.8
실시예 18Example 18 A-50A-50 4.34.3 455455 7.77.7
실시예 19Example 19 A-55A-55 4.04.0 454454 7.77.7
실시예 20Example 20 A-56A-56 4.24.2 455455 7.67.6
실시예 21Example 21 A-57A-57 4.14.1 455455 7.87.8
실시예 22Example 22 A-60A-60 4.34.3 457457 7.47.4
실시예 23Example 23 B-1B-1 4.04.0 456456 7.97.9
실시예 24Example 24 B-2B-2 4.34.3 457457 7.97.9
실시예 25Example 25 B-6B-6 4.24.2 456456 8.08.0
실시예 26Example 26 B-9B-9 4.14.1 456456 7.77.7
실시예 27Example 27 B-14B-14 4.24.2 456456 7.37.3
실시예 28Example 28 B-17B-17 3.93.9 458458 7.97.9
실시예 29Example 29 B-20B-20 3.93.9 458458 7.87.8
실시예 30Example 30 B-21B-21 4.14.1 454454 7.67.6
실시예 31Example 31 B-35B-35 4.14.1 457457 7.97.9
실시예 32Example 32 B-36B-36 4.24.2 458458 7.67.6
실시예 33Example 33 B-37B-37 4.04.0 454454 7.97.9
실시예 34Example 34 B-38B-38 4.14.1 454454 7.87.8
실시예 35Example 35 B-40B-40 4.34.3 455455 7.77.7
실시예 36Example 36 B-43B-43 4.24.2 455455 7.97.9
실시예 37Example 37 B-44B-44 4.34.3 457457 7.67.6
실시예 38Example 38 B-47B-47 4.34.3 457457 7.47.4
실시예 39Example 39 B-49B-49 4.04.0 457457 7.77.7
실시예 40Example 40 B-50B-50 4.14.1 455455 7.67.6
실시예 41Example 41 B-55B-55 4.04.0 454454 7.87.8
실시예 42Example 42 B-56B-56 4.34.3 455455 7.67.6
실시예 43Example 43 B-57B-57 4.14.1 455455 7.77.7
실시예 44Example 44 B-60B-60 4.34.3 457457 7.47.4
실시예 45Example 45 C-1C-1 3.93.9 456456 8.18.1
실시예 46Example 46 C-2C-2 4.14.1 457457 7.87.8
실시예 47Example 47 C-6C-6 4.14.1 456456 7.37.3
실시예 48Example 48 C-9C-9 4.14.1 456456 7.77.7
실시예 49Example 49 C-14C-14 4.24.2 456456 7.37.3
실시예 50Example 50 C-17C-17 3.93.9 458458 8.08.0
실시예 51Example 51 C-20C-20 4.04.0 458458 8.08.0
실시예 52Example 52 C-21C-21 4.14.1 454454 7.57.5
실시예 53Example 53 C-35C-35 4.14.1 457457 7.97.9
실시예 54Example 54 C-36C-36 4.34.3 458458 7.67.6
실시예 55Example 55 C-37C-37 4.14.1 454454 7.97.9
실시예 56Example 56 C-38C-38 4.04.0 454454 7.87.8
실시예 57Example 57 C-40C-40 4.34.3 455455 7.87.8
실시예 58Example 58 C-43C-43 4.04.0 455455 8.08.0
실시예 59Example 59 C-44C-44 4.14.1 457457 7.67.6
실시예 60Example 60 C-47C-47 4.14.1 457457 7.67.6
실시예 61Example 61 C-49C-49 4.24.2 457457 7.87.8
실시예 62Example 62 C-50C-50 4.14.1 455455 7.57.5
실시예 63Example 63 C-55C-55 4.14.1 454454 7.77.7
실시예 64Example 64 C-56C-56 4.24.2 455455 7.67.6
실시예 65Example 65 C-57C-57 3.93.9 455455 7.97.9
실시예 66Example 66 C-60C-60 4.14.1 457457 7.57.5
실시예 67Example 67 D-1D-1 4.04.0 456456 8.18.1
실시예 68Example 68 D-2D-2 4.14.1 457457 7.97.9
실시예 69Example 69 D-6D-6 4.14.1 456456 7.37.3
실시예 70Example 70 D-9D-9 4.24.2 456456 7.97.9
실시예 71Example 71 D-14D-14 4.24.2 456456 7.37.3
실시예 72Example 72 D-17D-17 3.93.9 458458 8.08.0
실시예 73Example 73 D-20D-20 4.04.0 458458 7.87.8
실시예 74Example 74 D-21D-21 4.34.3 454454 7.57.5
실시예 75Example 75 D-35D-35 4.04.0 457457 7.97.9
실시예 76Example 76 D-36D-36 4.34.3 458458 7.67.6
실시예 77Example 77 D-37D-37 3.93.9 454454 7.97.9
실시예 78Example 78 D-38D-38 4.04.0 454454 7.87.8
실시예 79Example 79 D-40D-40 4.14.1 455455 7.87.8
실시예 80Example 80 D-43D-43 4.14.1 455455 8.08.0
실시예 81Example 81 D-44D-44 4.24.2 457457 7.57.5
실시예 82Example 82 D-47D-47 4.24.2 457457 7.57.5
실시예 83Example 83 D-49D-49 4.04.0 457457 7.87.8
실시예 84Example 84 D-50D-50 4.24.2 455455 7.77.7
실시예 85Example 85 D-55D-55 4.14.1 454454 7.77.7
실시예 86Example 86 D-56D-56 4.24.2 455455 7.67.6
실시예 87Example 87 D-57D-57 4.04.0 455455 7.87.8
실시예 88Example 88 D-60D-60 4.24.2 457457 7.47.4
비교예 1Comparative Example 1 Alq3 Alq 3 4.74.7 458458 5.65.6
비교예 2Comparative Example 2 화합물 Acompound A 4.54.5 460460 6.76.7
비교예 3Comparative Example 3 화합물 Bcompound B 4.54.5 459459 6.66.6
비교예 4Comparative Example 4 화합물 Ccompound C 4.64.6 457457 6.06.0
비교예 5Comparative Example 5 화합물 Dcompound D 4.54.5 458458 6.36.3
비교예 6Comparative Example 6 화합물 Ecompound E 4.44.4 456456 6.76.7
비교예 7Comparative Example 7 화합물 Fcompound F 4.84.8 459459 6.06.0
상기 표 1에 나타낸 바와 같이, 본 발명의 화합물을 전자 수송층에 사용한 실시예 1~88의 청색 유기 전계 발광 소자는 종래의 Alq3를 전자 수송층에 사용한 비교예 1의 청색 유기 전계 발광 소자 및 화합물 A~F를 전자수송층에 사용한 비교예 2~7의 청색 유기 전계 발광 소자에 비해 구동전압, 발광피크 및 전류효율 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1, the blue organic electroluminescent device of Examples 1-88 using the compound of the present invention for the electron transport layer, the blue organic electroluminescent device of Comparative Example 1 using the conventional Alq 3 for the electron transport layer, and Compound A It was found that ~F exhibited superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 2 to 7 in which the electron transport layer was used.
[실시예 89] 유기 전계 발광 소자의 제작[Example 89] Preparation of organic electroluminescent device
합성예에서 합성된 화합물 A-1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.After high-purity sublimation purification of Compound A-1 synthesized in Synthesis Example by a commonly known method, a blue organic electroluminescent device was manufactured as follows.
먼저. ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.first. A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (㈜두산전자, 30nm)/Alq3 (30 nm)/화합물 A-1(15 nm) /DS-505 (㈜두산전자, 15 nm) /NPB (15 nm)/CBP + 10 % (piq)2Ir(acac) (40 nm)/Alq3 (30 nm)/LiF(1 nm)/Al(200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. 이때, 사용된 NPB, ADN의 구조는 실시예 1에 기재된 바와 동일하고, Alq3의 구조는 비교예 1에 기재된 바와 동일하며, CBP 및 (piq)2Ir(acac)의 구조는 다음과 같다.On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics, 30 nm)/Alq 3 (30 nm)/compound A-1(15 nm) /DS-505 (Doosan Electronics, 15 nm) /NPB (15 nm)/CBP + 10 % (piq) 2 Ir(acac) (40 nm)/Alq 3 (30 nm)/ LiF (1 nm)/Al (200 nm) was laminated in the order to fabricate an organic electroluminescent device. At this time, the structures of NPB and ADN used are the same as those described in Example 1, the structures of Alq 3 are the same as those described in Comparative Example 1, and the structures of CBP and (piq) 2 Ir(acac) are as follows.
Figure PCTKR2020017988-appb-I000114
Figure PCTKR2020017988-appb-I000115
Figure PCTKR2020017988-appb-I000114
Figure PCTKR2020017988-appb-I000115
[실시예 90~176] 유기 전계 발광 소자의 제작[Examples 90-176] Fabrication of organic electroluminescent device
실시예 89에서 N형 전하생성층 물질로 사용된 화합물 A-1 대신 하기 표 2에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 89와 동일하게 수행하여 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 89, except that each of the compounds shown in Table 2 below was used instead of Compound A-1 used as the N-type charge generation layer material in Example 89.
[비교예 8 내지 13] 유기 전계 발광 소자의 제작[Comparative Examples 8 to 13] Fabrication of an organic electroluminescent device
실시예 89에서 N형 전하생성층 물질로 사용된 화합물 A-1 대신 화합물 A 내지 화합물 F를 각각 사용하는 것을 제외하고는, 상기 실시예 89 와 동일하게 수행하여유기 전계 발광 소자를 제작하였다. 이때, 화합물 A 내지 화합물 F의 구조는 비교예 2 내지 7에 기재된 바와 같다.An organic electroluminescent device was manufactured in the same manner as in Example 89, except that Compounds A to F were respectively used instead of Compound A-1 used as the N-type charge generation layer material in Example 89. In this case, the structures of Compounds A to F are as described in Comparative Examples 2 to 7.
[평가예 2][Evaluation Example 2]
실시예 89 내지 176 및 비교예 8 내지 13에서 각각 제작한 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 2에 나타내었다.For the organic electroluminescent devices prepared in Examples 89 to 176 and Comparative Examples 8 to 13, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. It was.
샘플Sample N형 전하생성층N-type charge generation layer 구동전압(V)Driving voltage (V) 전류효율(cd/A)Current efficiency (cd/A)
실시예 89Example 89 A-1A-1 8.68.6 15.015.0
실시예 90Example 90 A-2A-2 8.38.3 15.915.9
실시예 91Example 91 A-6A-6 8.38.3 15.715.7
실시예 92Example 92 A-9A-9 8.28.2 15.515.5
실시예 93Example 93 A-14A-14 8.38.3 15.615.6
실시예 94Example 94 A-17A-17 8.58.5 15.315.3
실시예 95Example 95 A-20A-20 8.38.3 15.315.3
실시예 96Example 96 A-21A-21 8.28.2 15.715.7
실시예 97Example 97 A-35A-35 8.58.5 15.215.2
실시예 98Example 98 A-36A-36 8.28.2 15.515.5
실시예 99Example 99 A-37A-37 8.68.6 15.315.3
실시예 100Example 100 A-38A-38 8.48.4 15.015.0
실시예 101Example 101 A-40A-40 8.28.2 15.815.8
실시예 102Example 102 A-43A-43 8.48.4 15.415.4
실시예 103Example 103 A-44A-44 8.38.3 15.715.7
실시예 104Example 104 A-47A-47 8.28.2 15.715.7
실시예 105Example 105 A-49A-49 8.68.6 15.515.5
실시예 106Example 106 A-50A-50 8.38.3 15.915.9
실시예 107Example 107 A-55A-55 8.58.5 15.515.5
실시예 108Example 108 A-56A-56 8.48.4 15.815.8
실시예 109Example 109 A-57A-57 8.68.6 14.814.8
실시예 110Example 110 A-60A-60 8.38.3 15.615.6
실시예 111Example 111 B-1B-1 8.38.3 15.515.5
실시예 112Example 112 B-2B-2 8.28.2 15.715.7
실시예 113Example 113 B-6B-6 8.38.3 15.715.7
실시예 114Example 114 B-9B-9 8.38.3 15.815.8
실시예 115Example 115 B-14B-14 8.28.2 15.615.6
실시예 116Example 116 B-17B-17 8.48.4 15.215.2
실시예 117Example 117 B-20B-20 8.58.5 15.215.2
실시예 118Example 118 B-21B-21 8.38.3 15.715.7
실시예 119Example 119 B-35B-35 8.58.5 15.215.2
실시예 120Example 120 B-36B-36 8.28.2 15.615.6
실시예 121Example 121 B-37B-37 8.58.5 15.115.1
실시예 122Example 122 B-38B-38 8.48.4 15.015.0
실시예 123Example 123 B-40B-40 8.38.3 15.615.6
실시예 124Example 124 B-43B-43 8.58.5 15.115.1
실시예 125Example 125 B-44B-44 8.28.2 15.515.5
실시예 126Example 126 B-47B-47 8.38.3 15.715.7
실시예 127Example 127 B-49B-49 8.48.4 15.015.0
실시예 128Example 128 B-50B-50 8.28.2 15.715.7
실시예 129Example 129 B-55B-55 8.58.5 15.015.0
실시예 130Example 130 B-56B-56 8.38.3 15.615.6
실시예 131Example 131 B-57B-57 8.58.5 15.215.2
실시예 132Example 132 B-60B-60 8.28.2 15.415.4
실시예 133Example 133 C-1C-1 8.68.6 15.315.3
실시예 134Example 134 C-2C-2 8.38.3 15.915.9
실시예 135Example 135 C-6C-6 8.38.3 15.915.9
실시예 136Example 136 C-9C-9 8.28.2 15.715.7
실시예 137Example 137 C-14C-14 8.38.3 15.715.7
실시예 138Example 138 C-17C-17 8.58.5 15.415.4
실시예 139Example 139 C-20C-20 8.38.3 15.315.3
실시예 140Example 140 C-21C-21 8.28.2 15.715.7
실시예 141Example 141 C-35C-35 8.58.5 15.115.1
실시예 142Example 142 C-36C-36 8.28.2 15.815.8
실시예 143Example 143 C-37C-37 8.68.6 15.115.1
실시예 144Example 144 C-38C-38 8.48.4 15.215.2
실시예 145Example 145 C-40C-40 8.28.2 15.715.7
실시예 146Example 146 C-43C-43 8.48.4 15.215.2
실시예 147Example 147 C-44C-44 8.38.3 15.815.8
실시예 148Example 148 C-47C-47 8.28.2 15.815.8
실시예 149Example 149 C-49C-49 8.68.6 15.015.0
실시예 150Example 150 C-50C-50 8.38.3 15.815.8
실시예 151Example 151 C-55C-55 8.58.5 15.315.3
실시예 152Example 152 C-56C-56 8.48.4 15.815.8
실시예 153Example 153 C-57C-57 8.68.6 15.415.4
실시예 154Example 154 C-60C-60 8.38.3 15.715.7
실시예 155Example 155 D-1D-1 8.58.5 15.415.4
실시예 156Example 156 D-2D-2 8.38.3 15.915.9
실시예 157Example 157 D-6D-6 8.28.2 15.815.8
실시예 158Example 158 D-9D-9 8.28.2 15.915.9
실시예 159Example 159 D-14D-14 8.28.2 15.815.8
실시예 160Example 160 D-17D-17 8.58.5 15.215.2
실시예 161Example 161 D-20D-20 8.38.3 15.315.3
실시예 162Example 162 D-21D-21 8.28.2 15.715.7
실시예 163Example 163 D-35D-35 8.58.5 15.215.2
실시예 164Example 164 D-36D-36 8.38.3 15.815.8
실시예 165Example 165 D-37D-37 8.68.6 15.115.1
실시예 166Example 166 D-38D-38 8.58.5 15.115.1
실시예 167Example 167 D-40D-40 8.28.2 15.615.6
실시예 168Example 168 D-43D-43 8.58.5 15.215.2
실시예 169Example 169 D-44D-44 8.38.3 15.715.7
실시예 170Example 170 D-47D-47 8.38.3 15.715.7
실시예 171Example 171 D-49D-49 8.68.6 15.115.1
실시예 172Example 172 D-50D-50 8.28.2 15.815.8
실시예 173Example 173 D-55D-55 8.58.5 15.015.0
실시예 174Example 174 D-56D-56 8.48.4 15.715.7
실시예 175Example 175 D-57D-57 8.68.6 15.115.1
실시예 176Example 176 D-60D-60 8.28.2 15.815.8
비교예 8Comparative Example 8 화합물 Acompound A 9.29.2 12.412.4
비교예 9Comparative Example 9 화합물 Bcompound B 9.09.0 12.812.8
비교예 10Comparative Example 10 화합물 Ccompound C 9.29.2 12.212.2
비교예 11Comparative Example 11 화합물 Dcompound D 9.89.8 13.613.6
비교예 12Comparative Example 12 화합물 Ecompound E 9.79.7 13.513.5
비교예 13Comparative Example 13 화합물 Fcompound F 9.99.9 14.014.0
상기 표 2에 나타낸 바와 같이, 본 발명의 화합물을 N형 전하생성층에 사용한 실시예 89~176의 청색 유기 전계 발광 소자는 화합물 A~F를 비교예 8~13의 청색 유기 전계 발광 소자에 비해 구동전압 및 전류효율 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 2, the blue organic electroluminescent devices of Examples 89 to 176 using the compound of the present invention for the N-type charge generating layer were compared to the blue organic electroluminescent devices of Comparative Examples 8 to 13 by using the compounds A to F. It was found that excellent performance was shown in terms of driving voltage and current efficiency.

Claims (12)

  1. 하기 화학식 1로 표시되는 유기 화합물:An organic compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2020017988-appb-I000116
    Figure PCTKR2020017988-appb-I000116
    (상기 화학식 1에서,(In Formula 1,
    상기 A 및 B 중 하나는 R1이고, 나머지는 하기 화학식 2로 표시되는 치환체이며,One of A and B is R 1 and the rest is a substituent represented by the following formula (2),
    상기 R1은 C1~C60의 알킬기이고,Wherein R 1 is a C 1 ~ C 60 alkyl group,
    [화학식 2][Formula 2]
    Figure PCTKR2020017988-appb-I000117
    Figure PCTKR2020017988-appb-I000117
    n은 0 내지 3의 정수이고,n is an integer from 0 to 3,
    EWG는 전자흡수성이 큰 전자끌게기이고,EWG is an electron withdrawing agent with high electron absorption,
    m은 0 내지 4의 정수이고,m is an integer from 0 to 4,
    R2는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되고,R 2 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group , C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group , C 6 ~ C 60 Arylphosphine oxide group, C 6 ~ C 60 An arylamine group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 ~ C 60 aryl) (5 nuclear atoms) to 60 heteroaryl) selected from the group consisting of an amine group,
    상기 R1의 알킬기는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상으로 치환되거나 또는 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이함).The alkyl group of R 1 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, C 6 to C 60 Arylox Period, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Arylphos pingi, C 6 ~ C aryl phosphine oxide groups of 60, C 6 ~ C 60 aryl amine group, the nuclear atoms of 5 to 60 hetero arylamine group, and (aryl C 6 ~ C 60) (nuclear atoms 5 to 60 heteroaryl) unsubstituted or substituted with one or more selected from the group consisting of an amine group, wherein when the substituents are plural, the plural substituents are the same or different from each other).
  2. 제1항에 있어서,According to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 3으로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by Formula 3 below:
    [화학식 3][Formula 3]
    Figure PCTKR2020017988-appb-I000118
    Figure PCTKR2020017988-appb-I000118
    (상기 화학식 3에서,(In Formula 3,
    n, m, R2, EWG 및 R1은 각각 제1항에서 정의한 바와 같음).n, m, R 2 , EWG and R 1 are each as defined in claim 1 ).
  3. 제1항에 있어서,According to claim 1,
    상기 R1은 C1~C12의 알킬기인, 화합물.The R 1 is a C 1 ~ C 12 Alkyl group, the compound.
  4. 제1항에 있어서,According to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 4 내지 7 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of Formulas 4 to 7:
    [화학식 4][Formula 4]
    Figure PCTKR2020017988-appb-I000119
    Figure PCTKR2020017988-appb-I000119
    [화학식 5][Formula 5]
    Figure PCTKR2020017988-appb-I000120
    Figure PCTKR2020017988-appb-I000120
    [화학식 6][Formula 6]
    Figure PCTKR2020017988-appb-I000121
    Figure PCTKR2020017988-appb-I000121
    [화학식 7][Formula 7]
    Figure PCTKR2020017988-appb-I000122
    Figure PCTKR2020017988-appb-I000122
    (상기 화학식 4 내지 7에서,(In Formulas 4 to 7,
    n, m, R2 및 EWG은 각각 제1항에서 정의한 바와 같음).n, m, R 2 and EWG are each as defined in claim 1).
  5. 제1항에 있어서,According to claim 1,
    상기 화학식 2의
    Figure PCTKR2020017988-appb-I000123
    모이어티는 하기 링커기 Link-1 내지 Link-5로 이루어진 군에서 선택된 링커기인, 화합물:    of Formula 2
    Figure PCTKR2020017988-appb-I000123
    A compound, wherein the moiety is a linker group selected from the group consisting of the following linker groups Link-1 to Link-5:
    Figure PCTKR2020017988-appb-I000124
    .
    Figure PCTKR2020017988-appb-I000124
    .
  6. 제1항에 있어서,According to claim 1,
    상기 EWG는 하기 화학식 S1 또는 S2로 표시되는 치환체인, 화합물:The EWG is a substituent represented by the following formula S1 or S2, a compound:
    [화학식 S1][Formula S1]
    Figure PCTKR2020017988-appb-I000125
    Figure PCTKR2020017988-appb-I000125
    [화학식 S2][Formula S2]
    Figure PCTKR2020017988-appb-I000126
    Figure PCTKR2020017988-appb-I000126
    (상기 화학식 S1 및 S2에서,(In the formulas S1 and S2,
    X1 내지 X5는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 내지 X5 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고,X 1 to X 5 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 to X 5 is N, wherein a plurality of Ar 2 are the same as or different from each other,
    Y1 내지 Y4는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar3)이고, 다만 Y1 내지 Y4 중 적어도 하나는 N이며, 이때 복수의 Ar3은 서로 동일하거나 상이하고,Y 1 to Y 4 are the same or different from each other, and each independently is N or C(Ar 3 ), provided that at least one of Y 1 to Y 4 is N, wherein a plurality of Ar 3 are the same or different from each other,
    Ar1 내지 Ar3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 서로 결합하여 축합 고리를 형성할 수 있고, Ar 1 To Ar 3 Are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C 60 of the arylamine group, the nuclear atoms of 5 to 60 hetero arylamine group, And (C 6 ~ C 60 Aryl) (Nuclear atoms 5 to 60 heteroaryl) selected from the group consisting of an amine group, or may be combined with an adjacent group to form a condensed ring,
    상기 Ar1 내지 Ar3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 아릴포스피닐기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이함).The Ar 1 To Ar 3 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl Boron group, arylphosphanyl group, arylphosphinyl group, arylamine group, heteroarylamine group and (aryl) (heteroaryl) amine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, nucleus A heteroaryl group having 5 to 60 atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, an aryl amine of the C 6 ~ C 60 group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 to C 60 aryl) (heteroaryl having 5 to 60 nuclear atoms) substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group and, when the substituents are plural, the plurality of substituents are the same or different from each other).
  7. 제6항에 있어서,7. The method of claim 6,
    상기 EWG는 하기 화학식 S3 내지 S7 중 어느 하나로 표시되는 치환체인, 화합물:The EWG is a substituent represented by any one of the following formulas S3 to S7, a compound:
    [화학식 S3][Formula S3]
    Figure PCTKR2020017988-appb-I000127
    Figure PCTKR2020017988-appb-I000127
    [화학식 S4][Formula S4]
    Figure PCTKR2020017988-appb-I000128
    Figure PCTKR2020017988-appb-I000128
    [화학식 S5][Formula S5]
    Figure PCTKR2020017988-appb-I000129
    Figure PCTKR2020017988-appb-I000129
    [화학식 S6][Formula S6]
    Figure PCTKR2020017988-appb-I000130
    Figure PCTKR2020017988-appb-I000130
    [화학식 S7][Formula S7]
    Figure PCTKR2020017988-appb-I000131
    Figure PCTKR2020017988-appb-I000131
    [화학식 S8][Formula S8]
    Figure PCTKR2020017988-appb-I000132
    Figure PCTKR2020017988-appb-I000132
    [화학식 S9][Formula S9]
    Figure PCTKR2020017988-appb-I000133
    Figure PCTKR2020017988-appb-I000133
    (상기 화학식 S3에서,(In Formula S3,
    X1, X3 및 X5는 각각 제6항에서 정의된 바와 같고, 다만 X1, X3 및 X5 중 적어도 하나는 N이며,X 1 , X 3 and X 5 are each as defined in claim 6, provided that at least one of X 1 , X 3 and X 5 is N,
    상기 화학식 S4 및 S5에서,In Formulas S4 and S5,
    X1 및 X3는 각각 제6항에서 정의된 바와 같고, 다만 X1 및 X3 중 적어도 하나는 N이며,X 1 and X 3 are each as defined in claim 6, provided that at least one of X 1 and X 3 is N,
    Z1은 O 또는 S이고, Z 1 is O or S,
    상기 화학식 S6 및 S7에서,In the above formulas S6 and S7,
    X1 및 X5는 각각 제6항에서 정의된 바와 같고, 다만 X1 및 X5 중 적어도 하나는 N이며,X 1 and X 5 are each as defined in claim 6, provided that at least one of X 1 and X 5 is N,
    Z1은 O 또는 S이고, Z 1 is O or S,
    상기 화학식 S8 및 S9에서, In the above formulas S8 and S9,
    Y1, Y2 및 Y4는 각각 제6항에서 정의된 바와 같고, 다만 Y1, Y2 및 Y4 중 적어도 하나는 N이며,Y 1 , Y 2 and Y 4 are each as defined in claim 6, provided that at least one of Y 1 , Y 2 and Y 4 is N,
    상기 화학식 S3 내지 S9에서,In Formulas S3 to S9,
    Ar1 내지 Ar3는 각각 제6항에서 정의된 바와 같고,Ar 1 to Ar 3 are each as defined in claim 6,
    a는 0 내지 4의 정수이고, a is an integer from 0 to 4,
    Ar4는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택됨).Ar 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group , C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group , C 6 ~ C 60 Arylphosphine oxide group, C 6 ~ C 60 An arylamine group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 ~ C 60 aryl) (5 nuclear atoms) to 60 heteroaryl) selected from the group consisting of amine groups).
  8. 제1항에 있어서,According to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화학식 8 내지 14 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of Formulas 8 to 14:
    [화학식 8][Formula 8]
    Figure PCTKR2020017988-appb-I000134
    Figure PCTKR2020017988-appb-I000134
    [화학식 9][Formula 9]
    Figure PCTKR2020017988-appb-I000135
    Figure PCTKR2020017988-appb-I000135
    [화학식 10][Formula 10]
    Figure PCTKR2020017988-appb-I000136
    Figure PCTKR2020017988-appb-I000136
    [화학식 11][Formula 11]
    Figure PCTKR2020017988-appb-I000137
    Figure PCTKR2020017988-appb-I000137
    [화학식 12][Formula 12]
    Figure PCTKR2020017988-appb-I000138
    Figure PCTKR2020017988-appb-I000138
    [화학식 13][Formula 13]
    Figure PCTKR2020017988-appb-I000139
    Figure PCTKR2020017988-appb-I000139
    [화학식 14][Formula 14]
    Figure PCTKR2020017988-appb-I000140
    Figure PCTKR2020017988-appb-I000140
    (상기 화학식 8 및 9에서,(In Formulas 8 and 9,
    X1, X3 및 X5는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 내지 X5 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고;X 1 , X 3 and X 5 are the same or different from each other, and each independently represents N or C(Ar 2 ), provided that at least one of X 1 to X 5 is N, wherein a plurality of Ar 2 are the same as or different from each other and;
    상기 화학식 10 및 11에서,In Formulas 10 and 11,
    X1 및 X3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 및 X3 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고,X 1 and X 3 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 and X 3 is N, wherein a plurality of Ar 2 are the same as or different from each other,
    Z1은 O 또는 S이고;Z 1 is O or S;
    상기 화학식 12 및 13에서, In Formulas 12 and 13,
    X1 및 X5는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar2)이고, 다만 X1 및 X5 중 적어도 하나는 N이며, 이때 복수의 Ar2는 서로 동일하거나 상이하고,X 1 and X 5 are the same or different from each other, and each independently is N or C(Ar 2 ), provided that at least one of X 1 and X 5 is N, wherein a plurality of Ar 2 are the same or different from each other,
    Z1은 O 또는 S이고;Z 1 is O or S;
    상기 화학식 14에서, In the formula (14),
    Y1, Y2 및 Y4는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(Ar3)이고, 다만 Y1, Y2 및 Y4 중 적어도 하나는 N이며, 이때 복수의 Ar3은 서로 동일하거나 상이하고;Y 1 , Y 2 and Y 4 are the same as or different from each other, and each independently represent N or C(Ar 3 ), provided that at least one of Y 1 , Y 2 and Y 4 is N, wherein a plurality of Ar 3 are each other the same or different;
    상기 화학식 8 내지 14에서,In Formulas 8 to 14,
    n, m, R1 및 R2는 각각 제1항에서 정의된 바와 같고,n, m, R 1 and R 2 are each as defined in claim 1,
    a는 0 내지 4의 정수이고,a is an integer from 0 to 4,
    b 및 c는 각각 0 또는 1이며,b and c are each 0 or 1,
    Ar2 및 Ar3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 서로 결합하여 축합 고리를 형성할 수 있고, Ar 2 and Ar 3 are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 ~ C 40 alkyl group, a C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, C 6 ~ C 60 of the arylamine group, the nuclear atoms of 5 to 60 hetero arylamine group, And (C 6 ~ C 60 Aryl) (Nuclear atoms 5 to 60 heteroaryl) selected from the group consisting of an amine group, or may be combined with an adjacent group to form a condensed ring,
    Ar4는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택되며,Ar 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group , C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group , C 6 ~ C 60 Arylphosphine oxide group, C 6 ~ C 60 An arylamine group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 ~ C 60 aryl) (5 nuclear atoms) to 60 heteroaryl) selected from the group consisting of an amine group,
    상기 Ar2 및 Ar3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 아릴포스피닐기, 아릴아민기, 헤테로아릴아민기 및 (아릴)(헤테로아릴)아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, 핵원자수 5 내지 60의 헤테로아릴아민기, 및 (C6~C60의 아릴)(핵원자수 5 내지 60의 헤테로아릴)아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 이때 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이함).The Ar 2 And Ar 3 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl Boron group, arylphosphanyl group, arylphosphinyl group, arylamine group, heteroarylamine group and (aryl) (heteroaryl) amine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~ C 60 aryl group, nucleus A heteroaryl group having 5 to 60 atoms, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 1 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, an aryl amine of the C 6 ~ C 60 group, a heteroarylamine group having 5 to 60 nuclear atoms, and (C 6 to C 60 aryl) (heteroaryl having 5 to 60 nuclear atoms) substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group and, in this case, when the substituents are plural, the plurality of substituents are the same or different from each other).
  9. 제1항에 있어서,According to claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화합물 A-1~A-60, B-1~B-60, C-1~C-60, 및 D-1~D-60로 이루어진 군에서 선택된 화합물:The compound represented by Formula 1 is a compound selected from the group consisting of the following compounds A-1 to A-60, B-1 to B-60, C-1 to C-60, and D-1 to D-60:
    Figure PCTKR2020017988-appb-I000141
    Figure PCTKR2020017988-appb-I000141
    Figure PCTKR2020017988-appb-I000142
    Figure PCTKR2020017988-appb-I000142
    Figure PCTKR2020017988-appb-I000143
    Figure PCTKR2020017988-appb-I000143
    Figure PCTKR2020017988-appb-I000144
    Figure PCTKR2020017988-appb-I000144
    Figure PCTKR2020017988-appb-I000145
    Figure PCTKR2020017988-appb-I000145
    Figure PCTKR2020017988-appb-I000146
    Figure PCTKR2020017988-appb-I000146
    Figure PCTKR2020017988-appb-I000147
    Figure PCTKR2020017988-appb-I000147
    Figure PCTKR2020017988-appb-I000148
    .
    Figure PCTKR2020017988-appb-I000148
    .
  10. 애노드; 캐소드; 및 상기 애노드와 캐소드 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며,anode; cathode; and one or more organic material layers interposed between the anode and the cathode,
    상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제9항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 9.
  11. 제10항에 있어서,11. The method of claim 10,
    상기 화합물을 포함하는 유기물층은 전자 수송층인 유기 전계 발광 소자.The organic material layer containing the compound is an electron transport layer organic electroluminescent device.
  12. 서로 이격 배향된 애노드와 캐소드; an anode and a cathode oriented apart from each other;
    상기 애노드와 캐소드 사이에 개재된 복수의 발광 유닛; 및a plurality of light emitting units interposed between the anode and the cathode; and
    서로 인접한 발광 유닛 사이에 개재된 N형 전하 생성층 및 P형 전하 생성층An N-type charge generation layer and a P-type charge generation layer interposed between adjacent light emitting units
    을 포함하고,including,
    상기 각 발광 유닛은 정공 수송층, 발광층 및 전자 수송층을 포함하고,Each light emitting unit includes a hole transport layer, a light emitting layer and an electron transport layer,
    상기 N형 전하 생성층은 제1항 내지 제9항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.The N-type charge generating layer is an organic electroluminescent device comprising the compound according to any one of claims 1 to 9.
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