[go: up one dir, main page]

WO2017111389A1 - Composé organique et diode électroluminescente organique comprenant ledit composé - Google Patents

Composé organique et diode électroluminescente organique comprenant ledit composé Download PDF

Info

Publication number
WO2017111389A1
WO2017111389A1 PCT/KR2016/014726 KR2016014726W WO2017111389A1 WO 2017111389 A1 WO2017111389 A1 WO 2017111389A1 KR 2016014726 W KR2016014726 W KR 2016014726W WO 2017111389 A1 WO2017111389 A1 WO 2017111389A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
aryl
alkyl
formula
boron
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2016/014726
Other languages
English (en)
Korean (ko)
Inventor
한송이
김영배
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Doosan Corp
Original Assignee
Doosan Corp
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 Doosan Corp filed Critical Doosan Corp
Publication of WO2017111389A1 publication Critical patent/WO2017111389A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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):
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
  • R 1 to R 3 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;
  • l and m are each independently an integer from 0 to 4.
  • n is an integer from 0 to 3;
  • R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 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 Arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different
  • Arylamine 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 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • 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 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.
  • 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 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 according to the present invention can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence 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 significantly improved performance and lifetime can also be manufactured.
  • the present invention provides a compound represented by Formula 1:
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
  • R 1 to R 3 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;
  • l and m are each independently an integer from 0 to 4.
  • n is an integer from 0 to 3;
  • R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 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 Arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different
  • Arylamine 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 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • the novel organic compound according to the present invention has a structure in which a carbazole moiety is bonded to fluorene and an aromatic ring or heteroaromatic ring.
  • the compound represented by the formula (1) is characterized in that the compound represented by the formula (1).
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
  • R 1 to R 3 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;
  • l and m are each independently an integer from 0 to 4.
  • n is an integer from 0 to 3;
  • R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 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 Arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different
  • Arylamine 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 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • position 1, 2 or 3 of carbazole and position 2 of fluorene are directly linked to the active site, By linking, the stability of the molecule can be increased.
  • the compound may be represented by any one of Formulas 2 to 4, but is not limited thereto.
  • the L 1 to L 4 may be selected independently from the group consisting of the following formula 5 to 7, but is not limited thereto:
  • Z 1 to Z 8 are each independently N or C (R 7 ), but in Formula 5, at least two of Z 1 to Z 6 are C (R 7 ) and at least 2 of Z 1 to Z 4 in Formula 6
  • the dog is C (R 7 ), in formula 7 at least one of Z 1 to Z 4 , at least one of Z 5 to Z 8 is C (R 7 );
  • R 7 is absent, 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 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group 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 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, and when there
  • the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 7 is heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group
  • two of the bonds formed as linkers in Z 1 to Z 6 are C (R 7 ), wherein R 7 may be absent.
  • two of the bonds formed as linkers in Z 1 to Z 4 are C (R 7 ), wherein R 7 may be absent.
  • any one of Z 1 to Z 4 and Z 5 to Z 8 which is bonded as a linker in the formula ( 7 ) is C (R 7 ), wherein R 7 is It may be absent.
  • the compound may be a compound represented by any one of the following Chemical Formulas 8 to 12, but is not limited thereto:
  • the R 1 is preferably a substituent represented by any one of the following Formulas 13 to 17 can increase the electron transport capacity, but is not limited thereto:
  • X 1 to X 8 are each independently N or C (R 10 );
  • any one of X 1 to X 4 bonded to L 2 is C (R 10 ), wherein R 10 is absent;
  • T 1 is N or C (R 10 );
  • Y 1 is O, S, N (R 11 ) or C (R 12 ) (R 13 );
  • p and q are each independently integers of 0 to 4.
  • R 8 and R 9 is heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl, C cycloalkyl group of 3 ⁇ C 40 of , 3 to 40 heterocycloalkyl groups, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl jade group, C group 3 ⁇ C 40 alkylsilyl, C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ aryl phosphine of C 60 A panyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, wherein each of R
  • R 10 to R 13 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, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of the R 10 in this case
  • the substituents represented by Formula 13 to 17 may be selected from the group consisting of the following Formula A-1 to A-19, but is not limited thereto:
  • t is an integer from 0 to 5;
  • w is an integer from 0 to 4.
  • v is an integer from 0 to 3;
  • u is an integer from 0 to 2;
  • R 14 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, A C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylsilyl group, or an adjacent group (e.g., L 1 or L 2 , or another adjacent R 18 or R 14
  • R 10 to R 13 , p and q are the same as defined in Chemical Formulas 13 to 17.
  • R 10 to R 14 may be each independently C 6 ⁇ C 60 An aryl group or a nuclear atom of 5 to 60 heteroaryl group.
  • R 10 to R 14 are each independently a phenyl group, biphenyl group, naphthalenyl group, fluorenyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, quinolinyl group and quina It may be selected from the group consisting of a zolinyl group.
  • 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 organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.
  • the compound represented by the formula (1) of the present invention has excellent hole transporting ability due to the carbazole moiety, and has excellent electron transporting ability of fluorene and aromatic ring or heteroaromatic ring connected thereto, thereby having bipolar characteristics in the molecule. Therefore, the bonding force between the holes and the electrons in the light emitting layer can be increased.
  • the light emitting layer of the organic EL device may include a host material, and may include the compound represented by 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 a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.
  • 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 may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution 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.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 5 as a light emitting host material when forming the emission layer.
  • Example 1 C 5 6.64 516 42.2
  • Example 2 C 7 6.35 517 43.5
  • Example 3 C 10 6.62 518 45.7
  • Example 4 C 11 6.53 516 42.3
  • Example 5 C 33 6.36 517 43.1
  • Example 6 C 35 6.88 516 43.6
  • Example 7 C 38 6.44 516 46.2
  • Example 8 C 39 6.62 516 43.4
  • Example 9 C 61 6.46 517 43.7
  • Example 10 C 63 6.39 516 47.4
  • Example 11 C 66 6.74 516 47.6
  • Example 12 C 67 6.81 518 43.2
  • Example 13 C 92 6.38 516 47.4
  • Example 14 C 95 6.54 518 44.1
  • Example 15 120 6.67 517 42.4
  • Example 16 C 123 6.32 517 46.7
  • Example 17 C 148 6.55 516 44.8
  • Example 18 C 151 6.83 518 43.5
  • Example 19 C 176 6.16 516 48.1
  • Example 20 179 6.24 516 49.6
  • Example 21
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red 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, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / C 103 ⁇ C 244 compound + 10% (piq) 2 Ir (acac) (300 nm) / BCP (10 nm) / Alq 3 on the prepared ITO transparent electrode (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to fabricate an organic EL device.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 25, except that CBP was used instead of the C 103 compound as a light emitting host material when the emission layer was formed.
  • 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)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et une diode électroluminescente organique le comprenant. Selon la présente invention, lorsque le composé est utilisé dans une couche organique d'une diode électroluminescente organique et de préférence, dans une couche émettant de la lumière, il peut améliorer l'efficacité lumineuse, la tension de commande, la durée de vie, etc. de ladite diode.
PCT/KR2016/014726 2015-12-21 2016-12-15 Composé organique et diode électroluminescente organique comprenant ledit composé Ceased WO2017111389A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020150183043A KR102587381B1 (ko) 2015-12-21 2015-12-21 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2015-0183043 2015-12-21

Publications (1)

Publication Number Publication Date
WO2017111389A1 true WO2017111389A1 (fr) 2017-06-29

Family

ID=59089587

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/014726 Ceased WO2017111389A1 (fr) 2015-12-21 2016-12-15 Composé organique et diode électroluminescente organique comprenant ledit composé

Country Status (2)

Country Link
KR (1) KR102587381B1 (fr)
WO (1) WO2017111389A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107417677A (zh) * 2017-08-09 2017-12-01 上海道亦化工科技有限公司 一种咔唑吡啶类有机电致发光化合物及其有机电致发光器件
CN109928962A (zh) * 2017-12-18 2019-06-25 江苏三月光电科技有限公司 一种以咔唑为核心的化合物、制备方法及其在有机电致发光器件上的应用
CN111138297A (zh) * 2019-10-31 2020-05-12 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
US11925106B2 (en) 2018-12-28 2024-03-05 Samsung Electronics Co., Ltd. Condensed cyclic compound, composition including the same, and organic light-emitting device including the condensed cyclic compound

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102530155B1 (ko) * 2017-10-23 2023-05-10 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090065201A (ko) * 2007-12-17 2009-06-22 주식회사 하나화인켐 유기 발광 화합물 및 이를 구비한 유기 발광 소자
KR20130012479A (ko) * 2011-07-25 2013-02-04 삼성전자주식회사 셀룰러 통신 시스템에서의 부하 분산 방법 및 그 장치
KR20140073695A (ko) * 2012-12-06 2014-06-17 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20140114490A (ko) * 2013-03-14 2014-09-29 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150045295A (ko) * 2013-10-18 2015-04-28 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
KR20150075169A (ko) * 2013-12-24 2015-07-03 희성소재 (주) 함질소 다환 화합물 및 이를 이용한 유기발광소자

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102044720B1 (ko) * 2012-03-05 2019-11-14 도레이 카부시키가이샤 발광 소자
KR20130121479A (ko) * 2012-04-27 2013-11-06 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101614583B1 (ko) * 2013-10-25 2016-04-21 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090065201A (ko) * 2007-12-17 2009-06-22 주식회사 하나화인켐 유기 발광 화합물 및 이를 구비한 유기 발광 소자
KR20130012479A (ko) * 2011-07-25 2013-02-04 삼성전자주식회사 셀룰러 통신 시스템에서의 부하 분산 방법 및 그 장치
KR20140073695A (ko) * 2012-12-06 2014-06-17 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20140114490A (ko) * 2013-03-14 2014-09-29 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150045295A (ko) * 2013-10-18 2015-04-28 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
KR20150075169A (ko) * 2013-12-24 2015-07-03 희성소재 (주) 함질소 다환 화합물 및 이를 이용한 유기발광소자

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107417677A (zh) * 2017-08-09 2017-12-01 上海道亦化工科技有限公司 一种咔唑吡啶类有机电致发光化合物及其有机电致发光器件
CN109928962A (zh) * 2017-12-18 2019-06-25 江苏三月光电科技有限公司 一种以咔唑为核心的化合物、制备方法及其在有机电致发光器件上的应用
US11925106B2 (en) 2018-12-28 2024-03-05 Samsung Electronics Co., Ltd. Condensed cyclic compound, composition including the same, and organic light-emitting device including the condensed cyclic compound
CN111138297A (zh) * 2019-10-31 2020-05-12 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
US11098022B2 (en) 2019-10-31 2021-08-24 Shaanxi Lighte Optoelectronics Material Co. Ltd. Nitrogen-containing compound, electronic component and electronic device

Also Published As

Publication number Publication date
KR102587381B1 (ko) 2023-10-12
KR20170074047A (ko) 2017-06-29

Similar Documents

Publication Publication Date Title
WO2017179809A1 (fr) Composé organique électroluminescent et élément électroluminescent organique l'utilisant
WO2018038401A1 (fr) Composé organique et dispositif à électroluminescence organique comprenant un tel composé
WO2016089080A1 (fr) Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
WO2016105161A2 (fr) Composé organique et élément électroluminescent organique comprenant ce composé
WO2014010810A1 (fr) Nouveau composé et dispositif électroluminescent le comprenant
WO2017111439A1 (fr) Composé organique et dispositif électroluminescent organique comprenant ledit composé
WO2018216921A2 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2020027463A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2014142488A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018080068A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2020159019A1 (fr) Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2020209679A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018230782A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2019004584A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2015133804A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2018212463A1 (fr) Composé électroluminescent organique, et élément électroluminescent organique l'utilisant
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2015125986A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2015133808A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2014081134A1 (fr) Nouveau composé et élément électroluminescent organique comprenant ledit composé

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: 16879256

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 26/09/2018)

122 Ep: pct application non-entry in european phase

Ref document number: 16879256

Country of ref document: EP

Kind code of ref document: A1