WO2017209488A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2017209488A1
WO2017209488A1 PCT/KR2017/005637 KR2017005637W WO2017209488A1 WO 2017209488 A1 WO2017209488 A1 WO 2017209488A1 KR 2017005637 W KR2017005637 W KR 2017005637W WO 2017209488 A1 WO2017209488 A1 WO 2017209488A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
compound
heteroaryl
alkyl group
Prior art date
Application number
PCT/KR2017/005637
Other languages
English (en)
Korean (ko)
Inventor
심재의
한송이
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 WO2017209488A1 publication Critical patent/WO2017209488A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • 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
    • H10K50/16—Electron transporting 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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 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 hole blocking layer
  • BCP hole blocking layer
  • electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
  • 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 the organic material layer material which is excellent in performance is calculated
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1):
  • X is O or N (R 1 );
  • Z 1 to Z 12 are each independently N or C (R 2 ), but at least one of Z 1 to Z 12 is N;
  • n is an integer from 0 to 4.
  • Ar 1 is a substituent represented by the following Chemical Formula 2, and when there are a plurality of Ar 1 , they are the same as or different from each other;
  • R 1 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups;
  • R 2 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups, and when there are a plurality of R 2 , they are the same or different from each other; To;
  • the alkyl group, aryl group and heteroaryl group of R 1 and R 2 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5
  • substituents selected from the group consisting of from 60 to 60 heteroaryl groups and C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, 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 single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 3 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups;
  • the arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, aryl group and heteroaryl group of R 3 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C When substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group of 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60 , and substituted with a plurality of substituents , They are the same or different from each other.
  • 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 is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.
  • 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 C2-C40 straight or branched chain unsaturated hydrocarbon 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 at least one carbon-carbon triple bond, 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.
  • 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 to 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 of 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 represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
  • an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
  • X is O or N (R 1 );
  • Z 1 to Z 12 are each independently N or C (R 2) or at least one of the Z 1 to Z 12 are N;
  • n is an integer from 0 to 4.
  • Ar 1 is a substituent represented by the following Chemical Formula 2, and when there are a plurality of Ar 1 , they are the same as or different from each other;
  • R 1 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups;
  • R 2 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups, and when there are a plurality of R 2 , they are the same or different from each other; To;
  • the alkyl group, aryl group and heteroaryl group of R 1 and R 2 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5
  • substituents selected from the group consisting of from 60 to 60 heteroaryl groups and C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, 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 single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 3 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups;
  • the arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, aryl group and heteroaryl group of R 3 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C When substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group of 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60 , and substituted with a plurality of substituents , They are the same or different from each other.
  • novel compounds of the present invention can be represented by the following formula (1):
  • X is O or N (R 1 );
  • Z 1 to Z 12 are each independently N or C (R 2 ), but at least one of Z 1 to Z 12 is N;
  • n is an integer of 0 to 4, preferably an integer of 1 to 3;
  • Ar 1 is a substituent represented by the following Chemical Formula 2, and when there are a plurality of Ar 1 , they are the same as or different from each other;
  • R 1 is hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and the number of 5 to 60 heteroaryl group is selected from the group consisting of atomic nuclei;
  • R 2 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom of 5 to 60 heteroaryl groups, and when there are a plurality of R 2 , they are the same or different from each other; To;
  • the alkyl group, aryl group and heteroaryl group of R 1 and R 2 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5
  • substituents selected from the group consisting of from 60 to 60 heteroaryl groups and C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, 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 single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 3 is hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and the number of 5 to 60 heteroaryl group is selected from the group consisting of atomic nuclei;
  • the arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, aryl group and heteroaryl group of R 3 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C When substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group of 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60 , and substituted with a plurality of substituents , They are the same or different from each other.
  • the compound represented by the formula (1) of the present invention is EWG (electron) in a spiro [acridin- fluorene] -based moiety or a spiro [fluorene-xanthene] -based core containing at least one hetero atom N combined with -withdrawing group, the electrochemical stability is very good and electron mobility is much higher than that of the conventional spiro [acridin-fluorene] moiety or spiro [fluorene-xanthene] compound. In particular, it is excellent only in the high glass transition temperature and thermal stability exhibits the characteristics that the blue luminous efficiency is increased.
  • the compound represented by the formula (1) of the present invention has excellent electron transport ability and light emission characteristics, and thus, any one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer, which are the organic material layers of the organic EL device. Can be used as a material.
  • the light emitting layer, the electron transport layer and the electron transport auxiliary layer further laminated on the electron transport layer may be used as the material of any one of the material, more preferably the electron transport layer or the electron transport auxiliary layer.
  • the electron transport auxiliary layer since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect.
  • the excitons generated in the light emitting layer may diffusing to the electron transporting layer or the hole transporting layer adjacent to the light emitting layer due to the physicochemical properties having a wide band gap due to the low HOMO and high LUMO energy level.
  • the number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.
  • Most of the materials developed are capable of low voltage operation and have good intermolecular bonds, resulting in excellent amorphous morphology in device fabrication.
  • the compound is a compound represented by any one of the following formulas 3 to 10 has excellent electron transport ability.
  • the compound may be represented by any one of the following Chemical Formulas 3 to 6, 8, and 9, and more preferably, the compound represented by any one of the following Chemical Formulas 3 to 5, 8, and 9:
  • R 4 to R 14 are each independently selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a nuclear atom having 5 to 60 heteroaryl groups;
  • the alkyl group, aryl group and heteroaryl group of R 4 to R 14 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5
  • substituents selected from the group consisting of from 60 to 60 heteroaryl groups and C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, they are the same as or different from each other;
  • R 1 , Ar 1 and m are each as defined in Chemical Formula 1.
  • the compound is a compound represented by the following formula (11) is excellent in electron transport ability:
  • X, Z 1 to Z 12 and Ar 1 are each as defined in Chemical Formula 1.
  • L 1 and L 2 are each independently selected from the group consisting of phenylene group, biphenylene group, naphthalenyl group, fluorenyl group and carbazolyl group,
  • L 1 and the phenyl group, a biphenyl of the L 2 group, a naphthyl Frontale group, a fluorenyl group and carbazolyl groups are each independently a heavy hydrogen, an alkenyl group of C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 of, C 6 ⁇
  • substituents selected from the group consisting of an aryl group of C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60
  • they are substituted with a plurality of substituents. They are the same or different from each other.
  • Ar 1 may be a substituent represented by any one of the following Formulas 12 to 14:
  • R 3 is as defined in Formula 2 above.
  • R 3 is preferably a heteroaryl group having 5 to 60 nuclear atoms, more preferably 5 to 60 heteroaryl groups including at least two or more N atoms. Can be.
  • R 3 is selected from the group consisting of pyrimidine, pyrazine, triazine, imidazole, benzimidazole, phenanthromidazole, imidazopyridine, quinazoline and triazolopyridine ,
  • R 3 pyrimidine, pyrazine, triazine, imidazole, benzimidazole, phenanthryl Troy imidazole, imidazopyridine, quinazoline and triazolo pyridine are each independently a heavy hydrogen, C alkyl group of 1 ⁇ C 40, C 2 Unsubstituted or substituted with one or more substituents selected from the group consisting of -C 40 alkenyl group, C 6 -C 60 aryl group, nuclear atom 5-60 heteroaryl group, and C 6 -C 60 arylamine group; , When substituted with a plurality of substituents, they may be the same or different from each other.
  • R 3 may be a substituent represented by any one of the following A1 to A13:
  • p is an integer from 0 to 3;
  • q is an integer from 0 to 2;
  • R 15 is selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ with an aryl amine of the C 60 of the R 15 is In the case of a plurality, they are the same or different from each other;
  • R 16 is selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups and 6 to C 60 arylamine group;
  • the alkyl group, aryl group, heteroaryl group and arylamine group of R 15 and R 16 are each independently deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 6 ⁇ C 60 aryl group, When substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups having 5 to 60 nuclear atoms and arylamine groups having 6 to C 60 atoms, they are the same as or different from each other.
  • R 15 may be 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, more Preferably it may be a C 6 ⁇ C 60 aryl group.
  • R 16 may be selected from the group consisting of hydrogen, 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 and It will, more preferably be aryl date of C 6 ⁇ C 60.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • 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 moiety of spirofluorene xanthene or spiroacridine fluorene of the compound represented by Formula 1 is basically excellent in electrochemical stability, high glass transition temperature and carrier transport ability, The mobility is also very good, showing the characteristics that the blue luminous efficiency is increased.
  • the materials represented by Chemical Formula 1 are structurally characterized by combining a core core and an electron-withdrawing group (EWG), and are particularly excellent in electron mobility and excellent in high glass transition temperature and thermal stability. Therefore, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer, an electron transport layer or an electron transport auxiliary layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
  • the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer.
  • At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include the compound represented by the formula (1), preferably the light emitting layer, electron transport layer or electron
  • the transport auxiliary layer may include a compound represented by Chemical Formula 1.
  • the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention is a material known in the art, except that at least one of the organic material layers (for example, an electron transporting layer or an electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 above. And other organic material layers and electrodes using the method.
  • the organic material layers for example, an electron transporting layer or an electron transporting 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.
  • examples of the anode 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), 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
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • reaction mixture was cooled to room temperature and 500 mL of an ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Then, the organic layer thus obtained was dried over anhydrous MgSO 4, and evaporated under reduced pressure and then purified by a silica gel column chromatography to obtain the title compound 26.9 g (yield: 78%).
  • 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, 30nm
  • Compound 1, 7, 17, 21 , 24, 44, 53, 78, 81, 91, 99, 121, 151, 166, 183 each compound (30 nm) / LiF (1 nm) / Al (200 nm) by laminating the organic electroluminescent device Produced.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of compound 1 as an electron transporting material.
  • a blue organic EL device was manufactured in the same manner as in Example 1, except that Compound 1 was not used as the electron transporting material.
  • Example 1 Compound 1 4.0 452 7.8 Example 2 Compound 7 3.8 452 8.5 Example 3 Compound 17 3.3 453 8.8 Example 4 Compound 21 3.4 452 8.5 Example 5 Compound 24 4.2 453 7.9 Example 6 Compound 44 4.0 452 8.2 Example 7 Compound 53 3.6 455 8.4 Example 8 Compound 78 3.5 450 8.0 Example 9 Compound 81 3.6 452 8.1 Example 10 Compound 91 3.4 453 8.5 Example 11 Compound 99 3.6 450 8.3 Example 12 Compound 121 4.1 454 7.9 Example 13 Compound 151 3.3 452 8.8 Example 14 Compound 166 3.6 455 8.5 Example 15 Compound 183 3.9 455 8.6 Comparative Example 1 Alq 3 5.4 458 5.8 Comparative Example 2 - 5.2 458 6.2
  • the blue organic electroluminescent devices (Examples 1 to 13) using the compound of the present invention in the electron transporting layer were prepared using a blue organic electroluminescent device (comparative example 1) using Alq 3 as the electron transporting layer. Compared with the blue organic electroluminescent device (Comparative Example 2) without an electron transporting layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.
  • 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, Hwashin Tech
  • DS-205 Doosan Electronics, 80 nm
  • NPB 15 nm
  • ADN + 5% DS-405 Doosan Electronics, 30nm
  • 5 nm / Alq 3 (25 nm) / LiF (1 nm) / Al ( 200 nm) was laminated in order to prepare an organic EL device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 16, except that Compound 6 was not used as an electron transport auxiliary layer material, and Alq 3 , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm. .
  • Example 16 Compound 6 4.2 455 7.8 Example 17 Compound 15 3.4 452 8.2 Example 18 Compound 22 3.3 450 8.9 Example 19 Compound 28 3.2 452 8.5 Example 20 Compound 32 3.5 455 8.3 Example 21 Compound 39 3.3 452 8.6 Example 22 Compound 58 3.8 451 8.2 Example 23 Compound 67 3.7 452 8.4 Example 24 Compound 71 3.8 453 8.0 Example 25 Compound 74 3.5 451 8.6 Example 26 Compound 94 3.6 452 8.3 Example 27 Compound 102 3.2 451 8.8 Example 28 Compound 110 3.4 452 8.4 Example 29 Compound 116 3.7 453 8.1 Example 30 Compound 130 3.6 452 8.3 Example 31 Compound 152 3.3 450 8.7 Example 32 Compound 160 3.5 453 8.4 Example 33 Compound 173 3.4 452 8.7 Example 34 Compound 175 3.5 451 8.9 Comparative Example 3 - 4.8 4
  • the blue organic electroluminescent devices (Examples 16 to 34) using the compound of the present invention in the electron transport auxiliary layer were compared to the blue organic electroluminescent devices (Comparative Example 3) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, light emission peak, and driving voltage.
  • 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)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant, le composé, selon la présente invention, étant destiné à être utilisé pour une couche organique du dispositif électroluminescent organique, de préférence, une couche électroluminescente, une couche de transport d'électrons ou une couche de transport d'électrons auxiliaire, ce qui permet d'améliorer l'efficacité d'émission de lumière, la tension de commande, la durée de vie, etc. du dispositif électroluminescent organique.
PCT/KR2017/005637 2016-06-02 2017-05-30 Composé organique et dispositif électroluminescent organique le comprenant WO2017209488A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0068871 2016-06-02
KR1020160068871A KR102610868B1 (ko) 2016-06-02 2016-06-02 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2017209488A1 true WO2017209488A1 (fr) 2017-12-07

Family

ID=60478647

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2017/005637 WO2017209488A1 (fr) 2016-06-02 2017-05-30 Composé organique et dispositif électroluminescent organique le comprenant

Country Status (2)

Country Link
KR (1) KR102610868B1 (fr)
WO (1) WO2017209488A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108276336A (zh) * 2018-01-30 2018-07-13 瑞声光电科技(常州)有限公司 一种有机光电功能材料，及发光器件及其制备方法和应用
CN108774258A (zh) * 2018-09-10 2018-11-09 西安瑞联新材料股份有限公司 一种含硼杂环化合物及其在有机光电器件中的应用
CN108948030A (zh) * 2018-07-23 2018-12-07 西安瑞联新材料股份有限公司 一种氮杂芴螺蒽杂环化合物及其在有机电致发光元件中的应用
CN111377952A (zh) * 2018-12-28 2020-07-07 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件
CN111961054A (zh) * 2019-05-20 2020-11-20 北京绿人科技有限责任公司 含氮杂环的有机化合物及其应用和有机电致发光器件
CN111961055A (zh) * 2019-05-20 2020-11-20 北京绿人科技有限责任公司 含氮螺环结构的有机化合物及其应用和有机电致发光器件

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102684985B1 (ko) * 2018-12-07 2024-07-12 엘지디스플레이 주식회사 신규 화합물, 이를 포함하는 유기발광소자 및 유기발광 표시장치

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140045266A (ko) * 2012-10-08 2014-04-16 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
WO2014123391A1 (fr) * 2013-02-07 2014-08-14 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2015136880A1 (fr) * 2014-03-11 2015-09-17 保土谷化学工業株式会社 Composé spiro- ayant une structure azafluorène cyclique, matériau luminescent et élément électroluminescent organique
KR101593368B1 (ko) * 2015-04-22 2016-02-11 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101716069B1 (ko) * 2012-11-12 2017-03-13 메르크 파텐트 게엠베하 전자 소자용 재료

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140045266A (ko) * 2012-10-08 2014-04-16 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
WO2014123391A1 (fr) * 2013-02-07 2014-08-14 주식회사 엘지화학 Composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2015136880A1 (fr) * 2014-03-11 2015-09-17 保土谷化学工業株式会社 Composé spiro- ayant une structure azafluorène cyclique, matériau luminescent et élément électroluminescent organique
KR101593368B1 (ko) * 2015-04-22 2016-02-11 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
OHKUMA, H. ET AL.: "Thermally Activated Delayed Fluorescence from a Spiro- diazafluorene Derivative", CHEM. LETT., vol. 43, no. 7, 2014, pages 1017 - 1019, XP055192030 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108276336A (zh) * 2018-01-30 2018-07-13 瑞声光电科技(常州)有限公司 一种有机光电功能材料，及发光器件及其制备方法和应用
CN108276336B (zh) * 2018-01-30 2021-03-12 瑞声光电科技(常州)有限公司 一种有机光电功能材料，及发光器件及其制备方法和应用
CN108948030A (zh) * 2018-07-23 2018-12-07 西安瑞联新材料股份有限公司 一种氮杂芴螺蒽杂环化合物及其在有机电致发光元件中的应用
CN108774258A (zh) * 2018-09-10 2018-11-09 西安瑞联新材料股份有限公司 一种含硼杂环化合物及其在有机光电器件中的应用
CN108774258B (zh) * 2018-09-10 2021-04-09 陕西蒲城海泰新材料产业有限责任公司 一种含硼杂环化合物及其在有机光电器件中的应用
CN111377952A (zh) * 2018-12-28 2020-07-07 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件
CN111377952B (zh) * 2018-12-28 2022-11-15 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件
CN111961054A (zh) * 2019-05-20 2020-11-20 北京绿人科技有限责任公司 含氮杂环的有机化合物及其应用和有机电致发光器件
CN111961055A (zh) * 2019-05-20 2020-11-20 北京绿人科技有限责任公司 含氮螺环结构的有机化合物及其应用和有机电致发光器件
CN111961054B (zh) * 2019-05-20 2021-11-02 北京绿人科技有限责任公司 含氮杂环的有机化合物及其应用和有机电致发光器件
CN111961055B (zh) * 2019-05-20 2021-11-02 北京绿人科技有限责任公司 含氮螺环结构的有机化合物及其应用和有机电致发光器件

Also Published As

Publication number Publication date
KR20170136836A (ko) 2017-12-12
KR102610868B1 (ko) 2023-12-07

Similar Documents

Publication Publication Date Title
WO2015190718A1 (fr) Dispositif électroluminescent organique
WO2020159019A1 (fr) Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
WO2018080068A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2018230782A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017003009A1 (fr) Composé émettant de la lumière organique et dispositif électroluminescent organique l'utilisant
WO2017111544A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2014010810A1 (fr) Nouveau composé et dispositif électroluminescent le comprenant
WO2017111543A1 (fr) Composé organique et dispositif électroluminescent organique comprenant ce composé
WO2019103397A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2015111864A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2015133804A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017188596A1 (fr) Composé organique électroluminescent et dispositif organique électroluminescent l'utilisant
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2013168927A2 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2015125986A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020116881A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2017105041A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2015133808A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2018186551A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2015099477A2 (fr) Nouveau composé organique et dispositif électroluminescent organique l'utilisant

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: 17806981

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 17806981

Country of ref document: EP

Kind code of ref document: A1