WO2018093107A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2018093107A1
WO2018093107A1 PCT/KR2017/012837 KR2017012837W WO2018093107A1 WO 2018093107 A1 WO2018093107 A1 WO 2018093107A1 KR 2017012837 W KR2017012837 W KR 2017012837W WO 2018093107 A1 WO2018093107 A1 WO 2018093107A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
aryl
alkyl
boron
mmol
Prior art date
Application number
PCT/KR2017/012837
Other languages
English (en)
Korean (ko)
Inventor
김홍석
김영배
김회문
손호준
배형찬
Original Assignee
주식회사 두산
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 두산 filed Critical 주식회사 두산
Publication of WO2018093107A1 publication Critical patent/WO2018093107A1/fr

Links

Images

Classifications

    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • 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 and the like according to its function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials.
  • metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
  • the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
  • the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent holes, electron injection and transport ability, light emitting ability and the like.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.
  • the present invention provides a compound represented by the following formula (1):
  • X 1 is selected from the group consisting of S, O, N (Ar 1 ) and C (Ar 2 ) (Ar 3 );
  • X 2 and X 3 are each independently N or C (Ar 4 );
  • Ring A is represented by one of formulas 2 to 4;
  • the dotted line means the part where condensation takes place
  • n is an integer from 0 to 4.
  • n is an integer from 0 to 6;
  • Ar 1 to Ar 4 and R 1 are each independently a substituent represented by Formula 5, and when there are a plurality of R 1 , they are the same as or different from each other;
  • L 1 and L 2 are each independently selected from the group consisting of a direct bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ 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 phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
  • the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means 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.
  • monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
  • the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1-40 alkyl, and is linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons 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 in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.
  • FIG. 1 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • organic layer 31 hole transport layer
  • the present invention provides a compound represented by the following formula (1):
  • X 1 is selected from the group consisting of S, O, N (Ar 1 ) and C (Ar 2 ) (Ar 3 );
  • X 2 and X 3 are each independently N or C (Ar 4 );
  • Ring A is represented by one of formulas 2 to 4;
  • the dotted line means the part where condensation takes place
  • n is an integer from 0 to 4.
  • n is an integer from 0 to 6;
  • Ar 1 to Ar 4 and R 1 are each independently a substituent represented by Formula 5, and when there are a plurality of R 1 , they are the same as or different from each other;
  • L 1 and L 2 are each independently selected from the group consisting of a direct bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ 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 phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
  • the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • novel compounds of the present invention can be represented by the following formula (1):
  • X 1 is selected from the group consisting of S, O, N (Ar 1 ) and C (Ar 2 ) (Ar 3 );
  • X 2 and X 3 are each independently N or C (Ar 4 );
  • Ring A is represented by one of formulas 2 to 4;
  • the dotted line means the part where condensation takes place
  • n is an integer from 0 to 4.
  • n is an integer from 0 to 6;
  • Ar 1 to Ar 4 and R 1 are each independently a substituent represented by Formula 5, and when there are a plurality of R 1 , they are the same as or different from each other;
  • L 1 and L 2 are each independently selected from the group consisting of a direct bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ 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 phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
  • the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • R 1 is represented by the formula (5)
  • L 1 and L 2 are at the same time a direct bond and R 2 is except for hydrogen.
  • the organic compound of the present invention is a compound having a structure in which one or more substituents connected directly to or connected to a moiety having a 5-membered aromatic ring or a 5-membered aromatic hetero ring are linked through a linker group. Can be displayed.
  • the 5-membered aromatic ring or 5-membered aromatic hetero ring may be an indole moiety, an indazole moiety, an indene moiety, a benjofuran moiety, a benjoiophene, a triazolo, etc., but is not limited thereto.
  • the compound represented by Formula 1 of the present invention is that EWG is bonded to a 5-membered aromatic ring or 5-membered aromatic hetero, such as indole, indazole indene, benjofuran, benzothiophene, triazolo, etc. Since it has an energy level similar to that of sol, it can be adjusted higher than the energy level of the dopant, and thus can be applied as a host material.
  • the moieties of benjofuran and benzojofen are rich in electrons, and therefore, mobility can be increased when used as an electron transport layer material of an organic electroluminescent device, so that the luminous efficiency can be increased and the driving voltage can be expected to decrease.
  • the 5-membered aromatic ring or 5-membered aromatic hetero ring of the present invention has a lower molecular weight than conventional compounds, it is possible to deposit at a lower temperature than other materials at the time of deposition, thereby improving processability and thermal stability. Can be.
  • the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green phosphorescent host material), an electron transport layer / injection layer material light emitting auxiliary layer material, life improvement layer material, more Preferably it can be used as a light emitting layer material, an electron injection layer material, an electron transporting layer material.
  • the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
  • the compound may be represented by any one of the following formulas 6 to 11.
  • Ring A and Ar 1 to Ar 4 are each as defined in Chemical Formula 1.
  • the compound is preferably represented by any one of the formulas (6) and (8) to (11) to secure a low driving voltage and high luminous efficiency, more preferably to any one of the formulas (8) to (10) It may be represented, more preferably may be represented by the formula (8) or (10).
  • Ar 1 to Ar 4 are each independently a C 6 ⁇ C 60 aryl group or a nuclear atom of 5 to 60 heteroaryl group,
  • the aryl group and heteroaryl group of Ar 1 to Ar 4 are each independently C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 arylamine group, C 6 ⁇ C 60 aryl group and 5 to 60 nuclear atoms When substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
  • Ar 1 to Ar 4 are each independently a phenyl group, a biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group , Carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxyyl group,
  • the phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group and spirofluorenyl group of Ar 1 to Ar 4 and dibenzo-deoxy carbonyl groups are each independently a C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl amine group, C 6 ⁇ C 60 aryl group and the number of nuclear atoms of 5 to 60 hetero aryl group from the group consisting of When substituted or unsubstituted with one or more selected substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
  • Ar 1 to Ar 4 are each independently a phenyl group, a biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group , Carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxyyl group,
  • dibenzodioxynyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, naphthalenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, and di
  • substituents selected from the group consisting of a benzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxyyl group, and substitute
  • L 1 and L 2 are each independently a direct bond or a linker represented by any one of the formulas A-1 to A-6, but is not limited thereto:
  • Z 1 to Z 8 are each independently N or C (Ar 5 );
  • Any two of Z 1 to Z 6 which are bonded as a linker in Formula A-1 is C (Ar 5 ), wherein Ar 5 is absent;
  • Any one of Z 1 to Z 4 and Z 5 to Z 8 which are bonded as a linker in Formula A-3 is C (Ar 5 ), wherein Ar 5 is absent;
  • Any one of Z 1 to Z 4 which is bonded as a linker in Formula A-4 is C (Ar 5 ), wherein Ar 5 is absent;
  • X 5 and X 6 are each independently O, S, N (Ar 6 ) or C (Ar 7 ) (Ar 8 );
  • X 7 is N or C (Ar 9 );
  • Ar 5 to Ar 9 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, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ 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 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a group that is selected or adjacent from the group consisting of an aryl amine of the C 6 ⁇ C 60 bond to
  • An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl of Ar 5 to Ar 9 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40
  • L 1 and L 2 are each independently a direct bond or a linker represented by any one of the formulas B-1 to B-11, but is not limited thereto:
  • Ar 6 to Ar 9 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, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ 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 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of Ar 6 to Ar 9 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms
  • Ar 6 to Ar 9 are each independently hydrogen, an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 and A heteroaryl group having 5 to 60 nuclear atoms;
  • the alkyl group, aryl group and heteroaryl group of Ar 6 to Ar 9 are each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60
  • substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and substituted with a plurality of substituents, they are the same or different from each other.
  • L 1 and L 2 may be each independently a direct bond or a linker selected from the group consisting of Formulas B-1, B-2 and B-6 to B-11.
  • R 2 may be a substituent represented by Formula 12:
  • Y 1 to Y 5 are each independently N or C (Ar 10 );
  • Ar 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ 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 phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, and when there are a plurality of Ar 10 , they are the same or different from each other;
  • the substituent represented by Formula 12 may be a substituent represented by the following formula (13):
  • R 3 and R 4 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, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ 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 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
  • Y 1 , Y 3 and Y 5 are each as defined in Chemical Formula 12.
  • the substituent represented by Formula 12 may be a substituent represented by any one of the following formulas C-1 to C-5:
  • R 3 and R 4 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, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ 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 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
  • R 3 and R 4 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Selected,
  • the alkyl group, aryl group and heteroaryl group of R 3 and R 4 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
  • R 3 and R 4 are each independently a phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of
  • a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group are each independently a C 1 -C 40 alkyl group, a C 6 -C 60 aryl group And it is unsubstituted or substituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups, they are the same or different from each other.
  • R 3 and R 4 are each independently a phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of
  • a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group are each independently a methyl group, an ethyl group, a propanyl group, a butyl group, a phenyl group, a biphenyl group, When substituted or unsubstituted with one or more substituents selected from the group consisting of a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group, they are substituted with a plurality of substituents. They are the same or different from each other.
  • R 2 may be a substituent represented by Formula 14:
  • R 5 and R 6 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, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ 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 phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to form
  • Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 5 and R 6 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • R 5 and R 6 are each independently a group consisting of an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms Selected,
  • the alkyl group, aryl group and heteroaryl group of R 5 and R 6 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
  • R 5 and R 6 are each independently a phenyl group, a biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of
  • a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group are each independently a C 1 -C 40 alkyl group, a C 6 -C 60 aryl group And it is unsubstituted or substituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups, they are the same or different from each other.
  • R 5 and R 6 are each independently a phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of
  • a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group are each independently a methyl group, an ethyl group, a propanyl group, a butyl group, a phenyl group, a biphenyl group, When substituted or unsubstituted with one or more substituents selected from the group consisting of a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group, they are substituted with a plurality of substituents. They are the same or different from each other.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone or mixed two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode
  • the electron injection layer 36 may be further included between the holes 20.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31.
  • the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.
  • the electron injection layer 36 is stacked on top of the electron transport layer to facilitate the injection of electrons from the cathode to perform a function that ultimately improves the power efficiency, which is specially used in the art It can be used without limitation, and materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
  • a light emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light emitting layer 32.
  • the emission auxiliary layer may serve to transport holes to the emission layer 32 and to adjust the thickness of the organic layer 30.
  • the emission auxiliary layer may include a hole transport material, and may be made of the same material as the hole transport layer 31.
  • a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer, and thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. .
  • Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.
  • the compound represented by Chemical Formula 1 is that EWG is bonded to a 5-membered aromatic ring or 5-membered aromatic hetero, such as indole, indazole indene, benjofuran, benzothiophene, triazolo, etc. Since the energy level is higher than the energy level of the dopant, it can be applied as a host material.
  • the moieties of benzofuran and benzothiophene are rich in electrons, and thus, when used as an electron transporting layer material of an organic electroluminescent device, the mobility of the benzofuran and the benzothiophene can be expected to be increased and the driving voltage can be increased.
  • the 5-membered aromatic ring or 5-membered aromatic hetero ring of the present invention has a lower molecular weight than conventional compounds, it is possible to deposit at a lower temperature than other materials at the time of deposition, thereby improving processability and thermal stability. Can be.
  • the compound represented by Chemical Formula 1 of the present invention may be used as any one of a material of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic material layers of an organic electroluminescent device. It can be used as a material of any one of the transport layer and the electron transport auxiliary layer further laminated on the electron transport layer, more preferably the electron transport layer, or the material of the electron transport auxiliary layer.
  • the compound represented by Formula 1 may be used as a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, preferably a phosphorescent host (blue, green). And / or red phosphorescent host materials).
  • the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.
  • the organic material layers for example, an electron transport auxiliary layer
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may 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), 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 are 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A1, (5.5g, 17.1 mmol, 70% yield).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A2, (6.8g, 17.1mmol, yield 70%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A5, (7.5g, 19.0 mmol, yield 78%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A7, (6.3g, 18.0 mmol, 74% yield).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A8, (8.1 g, 18.0 mmol, yield 74%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A9, (6.8 g, 18.0 mmol, yield 74%).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A11, (6.3 g, 17.1 mmol, 70% yield).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A12, (7.6g, 17.1 mmol, yield 70%).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A14, (8.9 g, 17.1 mmol, 70% yield).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A15, (15.8g, 19.0 mmol, yield 78%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A16, (6.3g, 17.1 mmol, yield 70%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A18, (15.8g, 19.0 mmol, yield 78%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A19, (6.3g, 17.1 mmol, yield 70%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A20, (7.6g, 17.1 mmol, yield 70%).
  • the mixture was extracted with ethyl acetate and then water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A21, (15.8g, 19.0 mmol, yield 78%).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A22, (5.4 g, 17.1 mmol, yield 70%).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A23, (6.7 g, 17.1 mmol, 70% yield).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A24, (7.2 g, 18.3 mmol, yield 75%).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A26, (6.3 g, 17.1 mmol, 70% yield).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A27, (6.3g, 17.1 mmol, yield 70%).
  • the mixture was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A28, (6.3 g, 17.1 mmol, 70% yield).
  • the mixture was extracted with ethyl acetate and then water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A31, (6.1g, 18.3 mmol, yield 75%).
  • the resultant was extracted with ethyl acetate, water was removed with MgSO 4 and purified by column chromatography to obtain the target compound A32, (5.5g, 17.1 mmol, yield 70%).
  • the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound R207, (8.0g, 12.8 mmol, 75% yield).
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
  • ITO Indium tin oxide
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / R7, R10, R13, R125, R27, R47, R67, R87, R107, R127, R147, R167, R187, R207, R210, on the prepared ITO transparent electrode
  • An organic electroluminescent device was manufactured by laminating Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound R7 as a light emitting host material when forming the emission layer.
  • Example 1 R7 4.2 515 12.5 Example 2 R10 4.3 515 12.1 Example 3 R13 4.2 515 12.3 Example 4 R125 4.1 515 12.2 Example 5 R27 4.2 515 12.2 Example 6 R47 4.2 515 12.1 Example 7 R67 4.3 515 12.3 Example 8 R87 4.3 515 12.1 Example 9 R107 4.3 515 12.0 Example 10 R127 4.2 515 12.1 Example 11 R147 4.2 515 12.2 Example 12 R167 4.2 515 12.1 Example 13 R187 4.2 515 12.2 Example 14 R207 4.2 515 12.1 Example 15 R210 4.1 515 12.4 Example 16 R227 4.3 515 12.3 Example 17 R247 4.2 515 12.1 Example 18 R267 4.2 515 12.2 Example 19 R287 4.1 515 12.1 Example 20 R307 4.2 515 12.0 Example 21 R310 4.2 515 12.2 Example 22 R347 4.2 515 12.2 Example 23 R3
  • the compounds according to the present invention (R7, R10, R13, R125, R27, R47, R67, R87, R107, R127, R147, R167, R187, R207, R210, R227, R247, R267, When R287, R307, R310, R347, R367, R387, R390, R407, R427, R447, R467, R507, R527, R567, R587, R607, R687, R767, R487) are used as the light emitting layer of the green organic electroluminescent device. (Examples 1 to 37) Compared with the green organic electroluminescent device (Comparative Example 1) using the conventional CBP, it can be seen that it shows better performance in terms of efficiency and driving voltage.
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • DS-205 Doosan Electronics 80 nm
  • NPB 15 nm
  • DS-405 Doosan Electronics, 30 nm) / R7, R10, R13, R207, R287 , R447, R527, R607, R687, R767 (5 nm) / Alq 3 (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to manufacture an organic EL device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 38, except for depositing Alq 3 , which is an electron transporting layer material, at 30 nm instead of 25 nm as an electron transporting auxiliary material.
  • NPB, AND and Alq 3 used in Examples 38 to 48 and Comparative Example 2 are as follows.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 38, except that A1 of the following structural formula was used instead of R7 as the electron transport auxiliary layer material.
  • Example 38 R7 4.0 455 9.8 Example 39 R10 3.9 455 9.2 Example 40 R13 4.1 455 9.4 Example 41 R207 4.2 455 7.8 Example 42 R287 4.2 455 7.8 Example 43 R447 4.0 455 7.5 Example 45 R527 4.2 455 7.4 Example 46 R607 2.5 455 8.2 Example 47 R687 2.8 455 8.3 Example 48 R767 3.5 455 7.2 Comparative Example 2 Alq 3 4.8 458 6.2 Comparative Example 3 A1 4.7 457 6.5
  • the blue organic electroluminescent devices (Examples 38 to 48) using the compound of the present invention in the electron transport auxiliary layer are blue organic electroluminescent devices without the electron transport auxiliary layer (Comparative Examples 2 and 3). Compared with the current efficiency, the light emission peak and the driving voltage it was found that excellent performance.
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • DS-205 Doosan Electronics, 80 nm
  • NPB 15 nm
  • ADN + 5% DS-405 Doosan Electronics, 30 nm
  • R10, R13, R207, R287, Compounds of R447, R527, R607, R687, R767, and R807 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to prepare an organic EL device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 49, except that Alq 3 was used instead of R7 as the electron transporting layer material.
  • a blue organic EL device was manufactured in the same manner as in Example 49, except that R7 was not used as the electron transporting material.
  • Example 49 R7 4.1 455 8.7
  • Example 50 R10 4.2 455 8.1
  • Example 51 R13 4.0 455 8.1
  • Example 52 R207 4.1 455 8.2
  • Example 53 R287 4.2 455 8.3
  • Example 54 R447 4.0 455 7.8
  • Example 55 R527 4.0 455 8.1
  • Example 56 R607 3.1 455 7.9
  • Example 57 R687 2.8 455 7.5
  • Example 58 R767 3.9 455 7.0
  • Example 59 R807 3.5 455 6.5 Comparative Example 4 Alq 3 4.7 458 5.5 Comparative Example 5 - 4.8 460 6.2
  • the blue organic electroluminescent devices (Examples 49 to 59) using the compound of the present invention in the electron transporting layer are the blue organic electroluminescent devices (Comparative Example 4) using the conventional Alq 3 in the electron transporting layer and Compared with the blue organic electroluminescent element (Comparative Example 5) without an electron transport layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.
  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé dans une couche de composé organique d'un élément électroluminescent organique, de préférence dans une couche électroluminescente, une couche de transfert d'électrons ou une couche auxiliaire de transport d'électrons. Par conséquent, l'efficacité lumineuse, la tension de commande, la durée de vie, etc. de l'élément électroluminescent organique peuvent être améliorés.
PCT/KR2017/012837 2016-11-16 2017-11-14 Composé organique et élément électroluminescent organique le comprenant WO2018093107A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0152770 2016-11-16
KR1020160152770A KR20180055206A (ko) 2016-11-16 2016-11-16 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2018093107A1 true WO2018093107A1 (fr) 2018-05-24

Family

ID=62146657

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2017/012837 WO2018093107A1 (fr) 2016-11-16 2017-11-14 Composé organique et élément électroluminescent organique le comprenant

Country Status (2)

Country Link
KR (1) KR20180055206A (fr)
WO (1) WO2018093107A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019004584A1 (fr) * 2017-06-30 2019-01-03 주식회사 두산 Composé organique et dispositif électroluminescent organique le comprenant
CN109134443A (zh) * 2018-09-12 2019-01-04 陕西莱特光电材料股份有限公司 一种新型有机电致发光层材料及其制备方法与应用
CN113227063A (zh) * 2019-02-15 2021-08-06 株式会社Lg化学 新型化合物及利用其的有机发光器件
CN114846011A (zh) * 2020-02-21 2022-08-02 株式会社Lg化学 杂环化合物和包含其的有机发光器件
CN116082283A (zh) * 2021-11-05 2023-05-09 江苏三月科技股份有限公司 一种含萘并五元含氧杂环结构的化合物及包含其的有机电致发光器件

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20200067064A (ko) * 2018-12-03 2020-06-11 두산솔루스 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN111747935B (zh) * 2019-03-29 2023-09-05 南京高光半导体材料有限公司 一种有机电致发光化合物及其制备方法
CN112239452B (zh) * 2020-10-14 2022-05-10 武汉尚赛光电科技有限公司 一种电子传输型杂蒽衍生物及其有机电致发光器件
CN112358473B (zh) * 2020-10-14 2022-09-27 武汉尚赛光电科技有限公司 一种杂蒽衍生物及其应用和有机电致发光器件
KR20220067040A (ko) * 2020-11-17 2022-05-24 엘티소재주식회사 헤테로 고리 화합물, 이를 포함하는 유기발광소자, 및 유기물층 형성용 조성물
KR20230133515A (ko) 2022-03-11 2023-09-19 롬엔드하스전자재료코리아유한회사 유기 전계 발광 재료, 복수 종의 호스트 재료, 및 이를 포함하는 유기 전계 발광 소자
WO2023190987A1 (fr) * 2022-03-31 2023-10-05 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110134581A (ko) * 2010-06-09 2011-12-15 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20130117726A (ko) * 2012-04-18 2013-10-28 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
KR20140103008A (ko) * 2013-02-14 2014-08-25 (주)씨에스엘쏠라 유기 발광 화합물 및 이를 이용한 유기 발광 소자
KR20140118926A (ko) * 2013-03-29 2014-10-08 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20160057018A (ko) * 2014-11-12 2016-05-23 (주)위델소재 아민 화합물 및 이를 이용한 유기전계 발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110134581A (ko) * 2010-06-09 2011-12-15 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20130117726A (ko) * 2012-04-18 2013-10-28 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
KR20140103008A (ko) * 2013-02-14 2014-08-25 (주)씨에스엘쏠라 유기 발광 화합물 및 이를 이용한 유기 발광 소자
KR20140118926A (ko) * 2013-03-29 2014-10-08 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20160057018A (ko) * 2014-11-12 2016-05-23 (주)위델소재 아민 화합물 및 이를 이용한 유기전계 발광소자

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019004584A1 (fr) * 2017-06-30 2019-01-03 주식회사 두산 Composé organique et dispositif électroluminescent organique le comprenant
CN109134443A (zh) * 2018-09-12 2019-01-04 陕西莱特光电材料股份有限公司 一种新型有机电致发光层材料及其制备方法与应用
CN113227063A (zh) * 2019-02-15 2021-08-06 株式会社Lg化学 新型化合物及利用其的有机发光器件
CN113227063B (zh) * 2019-02-15 2024-05-14 株式会社Lg化学 化合物及利用其的有机发光器件
CN114846011A (zh) * 2020-02-21 2022-08-02 株式会社Lg化学 杂环化合物和包含其的有机发光器件
CN116082283A (zh) * 2021-11-05 2023-05-09 江苏三月科技股份有限公司 一种含萘并五元含氧杂环结构的化合物及包含其的有机电致发光器件

Also Published As

Publication number Publication date
KR20180055206A (ko) 2018-05-25

Similar Documents

Publication Publication Date Title
WO2018093107A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018038401A1 (fr) Composé organique et dispositif à électroluminescence organique comprenant un tel composé
WO2017179809A1 (fr) Composé organique électroluminescent et élément électroluminescent organique l'utilisant
WO2018080066A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2018110958A1 (fr) Composé électroluminescent organique et élément électroluminescent organique l'utilisant
WO2016089080A1 (fr) Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
WO2018216921A2 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2020209679A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2013094999A2 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2014142488A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018080067A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2018038464A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2014092354A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2015111864A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2014025209A1 (fr) Nouveau composé et dispositif électroluminescent organique comprenant celui-ci
WO2016105054A2 (fr) Composé organique luminescent et élément électroluminescent organique faisant appel audit composé
WO2019004584A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017023125A1 (fr) Composé organique photoémetteur et dispositif électroluminescent organique l'utilisant
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2020027463A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2014046392A1 (fr) Composé organique et élément électroluminescent le comportant
WO2014027822A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2015111942A2 (fr) Composé organique et élément électroluminescent organique le contenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17872383

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 20.09.2019)

122 Ep: pct application non-entry in european phase

Ref document number: 17872383

Country of ref document: EP

Kind code of ref document: A1

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 20/09/2019)