WO2020130553A1 - Composé organique et élément électroluminescent organique l'utilisant - Google Patents

Composé organique et élément électroluminescent organique l'utilisant Download PDF

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WO2020130553A1
WO2020130553A1 PCT/KR2019/017842 KR2019017842W WO2020130553A1 WO 2020130553 A1 WO2020130553 A1 WO 2020130553A1 KR 2019017842 W KR2019017842 W KR 2019017842W WO 2020130553 A1 WO2020130553 A1 WO 2020130553A1
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손호준
엄민식
김회문
배형찬
김진웅
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두산솔루스 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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 light-emitting compound and an organic electroluminescent device using the same, more specifically, a compound having excellent thermal stability, light-emitting ability, electron injection/transporting ability, and one or more organic material layers, thereby luminous efficiency and driving voltage. , It relates to an organic electroluminescent device having improved properties such as life.
  • an organic electroluminescent device In an organic electroluminescent device (hereinafter referred to as an'organic EL device'), when current or voltage is applied to two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected hole meets the electron, an exciton is formed, and the exciton falls to the ground state to emit light.
  • 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 its function.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like represented by the following formula
  • anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have great advantages in terms of efficiency improvement, are blue, green, and red dopant materials.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device. Therefore, development of an organic material layer material having excellent performance is required.
  • An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device, and can be used as an electron transport layer material having excellent thermal stability, light emission performance, and electron injection and transport ability.
  • Another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
  • X 1 to X 3 are the same as or different from each other, and each independently N or CR 2 , provided that at least one of X 1 to X 3 is N, and when CR 2 is plural, a plurality of R 2 s are the same or different from each other Different,
  • Y is O or S
  • Z 1 to Z 10 are the same or different from each other, and each independently is N or CR 3 , but at least one of Z 1 to Z 10 is N, and when CR 3 is plural, a plurality of R 3 s are the same or different from each other Different,
  • a and b are each an integer from 1 to 3
  • L 1 and L 2 are the same as or different from each other, and each independently a single bond or an arylene group of C 6 to C 60 ,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms,
  • c is an integer from 0 to 4, wherein a plurality of R 3 are the same or different from each other,
  • R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to alkynyl group of C 40, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 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 arylboronic group, C 6 ⁇ C 60 aryl phosphine group, and selected from the group consisting of C 6 ⁇ C 60 aryl phosphine oxide group
  • the arylene groups of L 1 and L 2 , aryl groups and heteroaryl groups of Ar 1 and Ar 2 , alkyl groups of R 1 to R 3 , alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently 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, 3 to 40 nuclear atoms heterocycloalkyl group, C Aryl group of 6 ⁇ C 60 , heteroaryl group of 5
  • the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, at least among the one or more organic material layers
  • an organic electroluminescent device comprising the compound represented by Chemical Formula 1.
  • the compound of the present invention is excellent in thermal stability, luminescence, electron transport/injection, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
  • FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
  • FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to another example of the present invention.
  • the present invention provides a novel compound that can be used as a high-efficiency electron transport layer material because of excellent thermal stability and electron injection/transport performance.
  • the compound of Formula 1 according to the present invention is a core made of N-containing 6-membered heteroaromatic ring and N-containing aza phenanthrene ring attached directly or through a linker to one side of a dibenzoic moiety. ) Structure. Accordingly, since the compound of the present invention has a plate-like structure while having asymmetry based on the long axis of the molecule, it is excellent in thermal stability, luminescence, electron transport/injection, and the like. When the compound of Formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminous efficiency and current efficiency, and has a long life.
  • the N-containing 6-membered heteroaromatic ring eg, triazine ring, pyrimidine ring, etc.
  • EWG electron withdrawing group
  • N-containing aza phenanthrene The ring is an electron withdrawing group (EWG).
  • EWG electron withdrawing group
  • These N-containing 6-membered heteroaromatic rings and N-containing aza phenanthrene rings are introduced at one side of the benzene moiety of the dibenzoic moiety.
  • the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring may be introduced to each other in a meta position with respect to the dibenzoic moiety.
  • the compound of the present invention has a plate-like structure to induce stacking between molecules, thus increasing electron mobility and thus having better electron transport properties.
  • the interaction between the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring is minimized, and the physical and electrochemical stability of the compound itself can be increased.
  • the compound of Formula 1 according to the present invention is also effective in inhibiting crystallization of the organic layer compared to a compound in which an N-containing 6-membered heteroaromatic ring and an N-containing azaphenanthrene ring are introduced at ortho or para positions with each other. There is, it is possible to significantly improve the durability and life characteristics of the organic electroluminescent device.
  • an N-containing 6-membered heteroaromatic ring can be introduced (bonded) at position 6, which is the active site of the dibenzoic moiety.
  • the stability of the molecule of the compound of the present invention may be increased, and steric hindrance of the compound may occur, and thus the passion stability may be significantly increased.
  • the N-containing aza phenanthrene ring is introduced at the 8-position of the N-containing 6-membered heteroaromatic ring and the meta-position dibenzoic moiety, the synergistic effect of passion stability can be further exerted.
  • the compounds of the present invention are structurally asymmetric.
  • the asymmetry of these molecules suppresses crystallization, so that the processability of the compound according to the present invention and the durability of the device can be improved.
  • an organic electroluminescent device having a low driving voltage, high efficiency, and long life compared to a conventional electron transport layer material (eg, Alq 3, etc.) can be manufactured.
  • a full color display panel with improved high efficiency and long life characteristics can be manufactured.
  • the compound represented by Formula 1 according to the present invention since the compound represented by Formula 1 according to the present invention has excellent electron transport/injection properties, it can be used as one of the electron transport layer and the electron injection layer, which is an organic material layer of the organic electroluminescent device, and is preferable. It can be used as an electron transport layer material. Accordingly, the compound represented by Formula 1 of the present invention may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer/injection layer material, an electron transport auxiliary layer material, more preferably an electron transport layer material.
  • the organic electroluminescent device of the present invention including the compound of Formula 1 can greatly improve the performance and lifespan characteristics, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can also be maximized.
  • Y introduced into the dibenzoic moiety may be O or S.
  • Y introduced into the dibenzoic moiety may be O or S.
  • L 1 and L 2 are The moieties may be coupled to each other in a meta position.
  • the N-containing 6-membered heteroaromatic ring and the N-containing aza phenanthrene ring are dibenzoic moieties ( Moieties) are coupled to each other in a meta position on one side of the benzene site.
  • the compound of the present invention since the compound of the present invention has a plate-like structure, by inducing stacking between molecules, electron mobility is increased and electron injection/transport performance is excellent.
  • the compound of Formula 1 according to the present invention may be a compound represented by the following Formula 2, but is not limited thereto.
  • X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
  • L 1 and L 2 are divalent linkers, which are the same or different from each other, and are each independently a single bond, or an arylene group of C 6 to C 60 .
  • L 1 is an arylene group of C 6 ⁇ C 60
  • L 2 may be a single bond, specifically L 1 is a phenylene group
  • L 2 may be a single bond.
  • the compound of Formula 1 according to the present invention may be a compound of Formula 3 or 4 below.
  • X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
  • Z 1 to Z 10 are the same as or different from each other, and each independently N or CR 3 , provided that at least one of Z 1 to Z 10 is N.
  • one of Z 1 to Z 10 is N, and the other may be CR 3 ;
  • two of Z 1 to Z 10 is N, and the other may be CR 3 .
  • the CR 3 is plural, a plurality of R 3 s are the same as or different from each other.
  • any one of Z 1 to Z 4 , Z 9 and Z 10 is CR 3 , and carbon (C) is bonded to L 2 , and in this case, R 3 is not present.
  • any one of Z 1 , Z 3 and Z 10 is CR 3 and carbon (C) is bonded to L 2 , in which case R 3 is not present.
  • the compound of Formula 1 according to the present invention may be a compound represented by any one of the following Formulas 5 to 7.
  • X 1 to X 3 , Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are as defined in Formula 1, respectively.
  • X 1 to X 3 are the same or different from each other, and each independently is N or CR 2 , but at least one of X 1 to X 3 is N, and when CR 2 is plural, plural R 2 of the same or different from each other. Preferably, at least two of X 1 to X 3 may be N.
  • the compound of Formula 1 when the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety, EWG properties are stronger and electron mobility is faster than that of a pyridine moiety. Accordingly, the compound of Formula 1 according to the present invention may have better electron transporting properties when the N-containing 6-membered heteroaromatic ring is a triazine moiety or pyrimidine moiety.
  • the compound of Formula 1 according to the present invention may be a compound represented by the following Formula 8 or 9.
  • Y, Z 1 to Z 10 , a, b, c, L 1 , L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
  • Ar 1 and Ar 2 are the same as or different from each other, and are each independently selected from the group consisting of C 6 to C 60 aryl groups and heteroaryl groups having 5 to 60 nuclear atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and may each independently be a phenyl group or a biphenylene group.
  • Ar 1 may be a phenyl group
  • Ar 2 may be a phenyl group or a biphenyl group.
  • the chemical stability of the compound according to the present invention can be improved.
  • the N-containing 6-membered heteroaromatic ring is a triazine moiety or a pyrimidine moiety
  • their chemical stability is improved due to blocking of the phenyl group, thereby improving the chemical stability of the compound itself. It can be improved further.
  • R 1 to R 3 are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 Alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 hetero atoms
  • Aryl 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 is selected from the group consisting of C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and
  • Aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently 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, 3 to 3 nuclear atoms Heterocycloalkyl group of 40, C 6 ⁇ C 60 aryl group
  • the compound represented by Chemical Formula 1 according to the present invention may be more specifically embodied as any one of the following Chemical Formulas 10 to 15.
  • Y, Z 1 to Z 10 , a, b, c, L 2 , Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
  • the compound represented by Chemical Formula 1 according to the present invention may be further embodied as any one of the following Chemical Formulas 16 to 27.
  • Y, Z 1 to Z 10 , c, Ar 1 , Ar 2 , R 1 are each as defined in Formula 1.
  • the compounds represented by Formula 1 according to the present invention described above are the following exemplary compounds, such as compounds A-1 to A-12, B-1 to B-12, C-1 to C-12, D-1 to D- 12, E-1 to E-12, F-1 to F-12, G-1 to G-12, H-1 to H-12, I-1 to I-12, and J-1 to J-12 It can be further specified as.
  • the compound represented by Formula 1 according to the present invention is not limited by those illustrated below.
  • alkyl means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of this include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl (alkenyl) means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like but is not limited thereto.
  • alkynyl (alkynyl) means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.
  • Cycloalkyl in the present invention 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 refers to 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 morpholine, piperazine, and the like, but are not limited thereto.
  • 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 a condensed form. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is 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 condensed form with an aryl group may also 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, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole
  • alkyloxy refers to a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It 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 phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
  • Alkylsilyl in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl.
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
  • alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms.
  • alkylphosphinyl group means a phosphine group substituted with 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 aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
  • an organic electroluminescent device (hereinafter referred to as'organic EL device') comprising the compound represented by Chemical Formula 1 described above.
  • the organic electroluminescent device includes an anode (anode), a cathode (cathode) and at least one organic material layer interposed between the anode and the cathode ( ⁇ ), at least one of the one or more organic material layers It includes a compound represented by the formula (1). At this time, the compound may be used alone, or may be used by mixing two or more.
  • the organic material layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer
  • the electron transport layer includes a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 is an electron transport layer material and is included in the organic electroluminescent device.
  • electrons are easily injected from the cathode to the electron transport layer because of the compound of Formula 1, and can also quickly move from the electron transport layer to the light emitting layer, and thus the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, for example, on the substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (FIGS. 1 and 2). Reference).
  • an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device as shown in Figure 1, on the substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and The cathode 200 may have a structure sequentially stacked.
  • an electron injection layer may be positioned between the electron transport layer 340 and the cathode 200.
  • 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 material layer 300 (eg, the electron transport layer 340) includes a compound represented by Chemical Formula 1 It can be prepared by forming an organic 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 spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
  • the substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
  • examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide 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 and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb
  • Conductive polymers such as polythiophene, poly(3-methylthiophene),
  • examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys 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 transport layer are not particularly limited, and a conventional material known in the art may be used.
  • the target compound a [2-(2-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine] using column chromatography (61.6 g, 80% yield).
  • the target compound a (61.6 g, 141.9 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, synthesized in ⁇ Step 1>) 3,2-dioxaborolane) (43.3 g, 170.4 mmol), Pd(dppf)Cl 2 (3.5 g, 4.3 mmol), Xphos (6.7 g, 14.2 mmol), and KOAc (27.9 g, 283.9 mmol) 1,4 -Dioxane was added to 500 ml, and heated to reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and filtered using MgSO 4 . After removing the solvent from the filtered organic layer, the target compound A (52.9 g, yield 71%) was obtained using column chromatography.
  • the target compound B [2,4] was prepared in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound b obtained in ⁇ Step 1> was used instead of the compound a used in Step 2 of Preparation Example 1 -diphenyl-6-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)-1 ,3,5-triazine] (52.1 g, Overall yield 35%).
  • the target compound c [2 was performed in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound c obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1.
  • 4-diphenyl-6-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)- 1,3,5-triazine] (55.1 g, Overall yield 38%).
  • the target compound D [2- was performed in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound d obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1.
  • ([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]furan-4-yl)-1,3,5-triazine] (55.5 g, Overall yield 40%).
  • the target compound E was prepared in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound e obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1 [4- ([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]furan-4-yl)pyrimidine] (53.2 g, Overall yield 37%).
  • the target compound F [2 was performed in the same manner as in ⁇ Step 2> of Preparation Example 1, except that the compound f obtained in ⁇ Step 1> was used instead of the compound a used in ⁇ Step 2> of Preparation Example 1 4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen-4-yl)-1,3,5 -triazine] (50.4 g, Overall yield 33%).
  • the target compound I was prepared in the same manner as in ⁇ Step 2> of Preparative Example 6, except that Compound i obtained in ⁇ Step 1> was used instead of the compound f used in ⁇ Step 2> of Preparative Example 6 [2- ([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]thiophen-4-yl)-1,3,5-triazine] (55.2 g, Overall yield 36%).
  • the target compound J was performed in the same manner as in ⁇ Step 2> of Preparation Example 6, except that the compound j obtained in ⁇ Step 1> was used instead of the compound f used in ⁇ Step 2> of Preparation Example 6 ([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b ,d]thiophen-4-yl)pyrimidine] (55.2 g, Overall yield 36%).
  • Target compound A of preparation example 1 (5 g, 9.5 mmol), 2-bromophenanthridine (2.5 g, 9.5 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 28.5 mmol) )
  • Toluene 10 ml of EtOH and 10 ml of H 2 O, and heated to reflux for 12 hours.
  • the organic layer was extracted with methylene chloride, and filtered using MgSO 4 .
  • the target compound A-1 (4.1 g, yield 75%) was obtained using column chromatography.
  • a target compound A-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-4 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-5 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-6 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-7 (3.7 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-8 (3.7 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-9 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-10 (3.4 g (yield 62%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 1, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound A-12 (3.3 g, yield 61%) was obtained by performing the same procedure as in Synthesis Example 1, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 1.
  • a target compound B-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 13, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-3 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-4 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 13, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 13, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-8 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 13, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-10 (3.1 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 13, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound B-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 13, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 13.
  • a target compound C-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 26, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-3 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-4 (3.9 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 26, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 26, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-8 (3.5 g, yield 65%) was obtained by performing the same process as in Synthesis Example 26, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-10 (3.1 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 26, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound C-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 26, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 26.
  • a target compound D-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-4 (3.6 g, yield 66%) was obtained by performing the same procedure as in Synthesis Example 37, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-6 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-7 (3.1 g (yield 58%) was obtained by performing the same procedure as in Synthesis Example 37, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-8 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 37, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-9 (3.0 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-10 (3.1 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound D-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 37, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 37.
  • a target compound E-2 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 49, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-3 (3.5 g, yield 64%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-4 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 49, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-5 (3.8 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-6 (3.8 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-7 (3.3 g, yield 61%) was obtained by performing the same procedure as in Synthesis Example 49, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-8 (3.4 g, yield 64%) was obtained by performing the same procedure as in Synthesis Example 49, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-9 (3.1 g, yield 58%) was obtained by performing the same process as in Synthesis Example 49, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-10 (3.1 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-11 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 49, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound E-12 (3.2 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 49, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 49.
  • a target compound F-3 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-4 (3.9 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 61, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-5 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-6 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-7 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 61, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-8 (3.4 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 61, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-9 (3.3 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-10 (3.2 g, yield 58%) was obtained by performing the same process as in Synthesis Example 61, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 61, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound F-12 (3.2 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 61, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 61.
  • a target compound G-2 (3.7 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 73, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-4 (3.6 g (yield 67%) was obtained by performing the same procedure as in Synthesis Example 73, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-6 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-7 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 73, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 73, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-11 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 73, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound G-12 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 73, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 73.
  • a target compound H-2 (3.7 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 85, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-3 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-4 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 85, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-6 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-7 (3.5 g, yield 65%) was obtained by performing the same procedure as in Synthesis Example 85, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 85, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-9 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-11 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 85, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound H-12 (2.8 g, yield 53%) was obtained by performing the same procedure as in Synthesis Example 85, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 85.
  • a target compound I-2 (4.1 g, yield 76%) was obtained by performing the same procedure as in Synthesis Example 97, except that 3-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-3 (4.1 g, yield 76%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-4 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 97, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-5 (3.6 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-7 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 97, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-8 (3.4 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 97, except that 5-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-9 (3.2 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-10 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 97, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound I-12 (2.9 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 97, except that 2-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 97.
  • a target compound J-3 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 109, except that 6-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • a target compound J-4 (3.8 g, yield 70%) was obtained by performing the same procedure as in Synthesis Example 109, except that 8-bromophenanthridine was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • a target compound J-6 (3.7 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 109, except that 6-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • a target compound J-7 (3.8 g, yield 70%) was obtained by performing the same process as in Synthesis Example 109, except that 6-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • a target compound J-9 (3.2 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[h]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • a target compound J-10 (3.1 g, yield 54%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[f]quinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • a target compound J-11 (3.3 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 109, except that 9-bromobenzo[f]isoquinoline was used instead of 2-bromophenanthridine used in Synthesis Example 109.
  • the compound A-1 synthesized in the synthesis example was subjected to a high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.
  • a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 ⁇ was washed with distilled water.
  • ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed for 5 minutes using UV.
  • the substrate was transferred to a vacuum evaporator.
  • DS-205 Doosan Electronics, 80 nm
  • NPB Doosan Electronics
  • DS-405 Doosan Electronics(30 nm)/ Compound A-1 (30 nm) / LiF (1 nm) / Al (200 nm) was stacked in order to prepare an organic electroluminescent device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 below was used instead of Compound A-1 used as the electron transport layer material in Example 1.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 was used instead of Compound A-1 used as the electron transport layer material in Example 1. At this time, the structures of Alq 3 used are as follows.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 used as the electron transport layer material in Example 1 was not used.
  • the blue organic electroluminescent devices of Examples 1 to 120 using the compounds (A-1 to J-12) according to the present invention as electron transport layer materials were compared using Alq 3 , a conventional electron transport layer material. It was found that the blue organic electroluminescent device of Example 1 and the blue organic electroluminescent device of Comparative Example 2 without an electron transport layer showed better performance in terms of driving voltage, emission peak, and current efficiency.

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Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique le comprenant, et plus particulièrement un composé organique ayant une capacité d'injection et de transport d'électrons, une luminescence et une stabilité thermique excellentes, ainsi qu'un élément électroluminescent organique qui comprend ce composé et possède de ce fait une efficacité lumineuse, une tension de commande, une durée de vie, etc., améliorées.
PCT/KR2019/017842 2018-12-17 2019-12-17 Composé organique et élément électroluminescent organique l'utilisant WO2020130553A1 (fr)

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KR1020180163616A KR20200074804A (ko) 2018-12-17 2018-12-17 유기 화합물 및 이를 이용한 유기 전계 발광 소자
KR10-2018-0163616 2018-12-17

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