WO2016003171A1 - Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé Download PDF

Info

Publication number
WO2016003171A1
WO2016003171A1 PCT/KR2015/006723 KR2015006723W WO2016003171A1 WO 2016003171 A1 WO2016003171 A1 WO 2016003171A1 KR 2015006723 W KR2015006723 W KR 2015006723W WO 2016003171 A1 WO2016003171 A1 WO 2016003171A1
Authority
WO
WIPO (PCT)
Prior art keywords
unsubstituted
substituted
monocyclic
polycyclic
compound
Prior art date
Application number
PCT/KR2015/006723
Other languages
English (en)
Korean (ko)
Inventor
이정현
정수진
강상규
김기용
김동준
최진석
최대혁
음성진
이주동
Original Assignee
희성소재(주)
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
Priority claimed from KR1020140127222A external-priority patent/KR101579289B1/ko
Application filed by 희성소재(주) filed Critical 희성소재(주)
Priority to US15/318,901 priority Critical patent/US10446765B2/en
Priority to CN201580035950.0A priority patent/CN106661020B/zh
Priority to JP2016575816A priority patent/JP6513719B2/ja
Publication of WO2016003171A1 publication Critical patent/WO2016003171A1/fr

Links

Images

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/19—Tandem OLEDs

Definitions

  • the present invention relates to a novel heterocyclic compound and an organic light emitting device using the same.
  • An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light.
  • the organic thin film may be composed of a single layer or a multilayer, if necessary.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present invention provides a novel heterocyclic compound and an organic light emitting device using the same.
  • One embodiment of the present disclosure provides compounds of formula 1:
  • X is NR 3 , CR 4 R 5 , S, O or Se,
  • a is an integer of 0 to 4, and when a is 2 or more, R 1 are the same or different from each other,
  • b is an integer of 0 to 6, and when b is 2 or more, R 2 are the same or different from each other,
  • R 4 to R 9 are the same or different and each independently hydrogen; Substituted or unsubstituted C 1 to C 60 straight or branched alkyl; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl.
  • one embodiment of the present invention is an organic light emitting device including a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes an organic light emitting Device.
  • the compound described in this specification can be used as an organic layer material of an organic light emitting device.
  • the compound can be used as an electron transport layer, a hole blocking layer, a light emitting layer, and the like in an organic light emitting device.
  • the compound of Formula 1 can be used as a material for an electron transport layer, a hole blocking layer, and a light emitting layer of an organic light emitting device.
  • the compound of Formula 1 can be used as an electron transporting layer or a material of a light emitting layer.
  • FIGS. 1 to 3 illustrate a stacking order of electrodes and organic layers of an organic light emitting diode according to embodiments of the present invention.
  • Fig. 5 shows a PL measurement graph of Compound 1-12 at a wavelength of 233 nm.
  • FIG. 9 shows a PL measurement graph of a compound 1-124 at a wavelength of 240 nm.
  • FIG. 10 shows a PL measurement graph of Compound 1-318 at a wavelength of 309 nm.
  • FIG. 11 shows a PL measurement graph of Compound 2-36 at a wavelength of 282 nm.
  • Fig. 13 shows a PL measurement graph of compound 3-39 at a wavelength of 307 nm.
  • 16 shows a PL measurement graph of Compound 4-58 at a wavelength of 290 nm.
  • 17 shows a PL measurement graph of Compound 4-76 at a wavelength of 267 nm.
  • 19 is a graph showing the LTPL measurement at a wavelength of 309 nm of the compound 1-1.
  • 20 is a graph showing the LTPL measurement of Compound 1-12 at a wavelength of 338 nm.
  • 21 is a graph showing the LTPL measurement at a wavelength of 310 nm of Compound 1-36.
  • 24 is a graph showing the LTPL measurement at 408 nm wavelength of Compound 2-38.
  • 25 is a graph showing the LTPL measurement at a wavelength of 307 nm of the compound 3-39.
  • 26 is a graph showing the LTPL measurement at a wavelength of 268 nm of Compound 3-46.
  • 27 is a graph showing the LTPL measurement at 278 nm wavelength of Compound 4-56.
  • 29 is a graph showing the LTPL measurement at 365 nm wavelength of Compound 4-76.
  • the compounds described in this specification can be represented by the above formula (1).
  • the compound of Formula 1 may be used as an organic material layer material of an organic light emitting diode according to the structural features of the core structure and the substituent.
  • substituted or unsubstituted "halogen C 1 to C 60 linear or branched alkyl; C 2 to C 60 straight or branched chain alkenyl; C 2 to C 60 linear or branched alkynyl; C 1 to C 60 straight or branched chain alkoxy; C 3 to C 60 monocyclic or polycyclic cycloalkyl; A C 2 to C 60 monocyclic or polycyclic heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic aryl; C 2 to C 60 monocyclic or polycyclic heteroaryl; A C 1 to C 20 alkylamine, a C 6 to C 60 monocyclic or polycyclic arylamine, and a C 2 to C 60 monocyclic or polycyclic heteroaryl Amine, or substituted or unsubstituted with a substituent having two or more of the substituents bonded thereto, or substituted or unsubstituted with a substituent to which at least
  • R, R 'and R " are the same or different and each independently hydrogen, substituted or unsubstituted C 1 to C 60 linear or branched alkyl, substituted or unsubstituted C 3 to C 60 monocyclic Substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl, or substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl.
  • R, R 'and R " are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, C 6 to C 60 aryl and C 2 to C 60 hetero C 1 -C 60 straight or branched chain alkyl substituted or unsubstituted with one or more substituents selected from halogen, C 6 -C 60 aryl and C 2 -C 60 heteroaryl, A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl, substituted or unsubstituted with at least one substituent selected from deuterium, halogen, C 6 to C 60 aryl and C 2 to C 60 heteroaryl, unsubstituted C 6 to C 60 monocyclic or polycyclic aryl, or heavy hydrogen, halogen, C 6 to C aryl and at least one selected from the group consisting of heteroaryl of C 2 to C 60 of the 60 substituent is substituted or unsubsti
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • alkyl includes straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.
  • alkenyl includes straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkenyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • alkynyl includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkynyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • the cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic ring means a group in which cycloalkyl is directly connected to another ring group or condensed.
  • the other ring group may be a cycloalkyl group, but may be other ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like.
  • the carbon number of the cycloalkyl may be 3 to 60, specifically 3 to 40, more particularly 5 to 20.
  • heterocycloalkyl includes O, S, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the polycyclic ring means a group in which heterocycloalkyl is directly connected to another ring group or condensed.
  • the other ring group may be heterocycloalkyl, but may be other ring groups such as cycloalkyl, aryl, heteroaryl, and the like.
  • the heterocycloalkyl may have from 2 to 60 carbon atoms, specifically from 2 to 40, more specifically from 3 to 20 carbon atoms.
  • aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms and may be further substituted by other substituents.
  • the polycyclic ring means a group in which aryl is directly connected to another ring group or condensed.
  • the other ring group may be aryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl and the like.
  • Aryl includes a spiro group.
  • the carbon number of the aryl may be 6 to 60, specifically 6 to 40, more specifically 6 to 25.
  • aryl examples include phenyl, biphenyl, triphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, But are not limited to, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, and condensed rings thereof.
  • the spiro group is a group including a spiro structure and may have from 15 to 60 carbon atoms.
  • a spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorene group.
  • the spiro group includes groups of the following structural formulas.
  • heteroaryl includes S, O, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms and may be further substituted by other substituents.
  • polycyclic means a heteroaryl group directly bonded to another ring group or condensed therewith.
  • the other ring group may be heteroaryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like.
  • the heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40, more specifically 3 to 25 carbon atoms.
  • heteroaryl examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, Thiazolyl, thiazolyl, pyrazinyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, iso And examples thereof include quinolyl, quinolyl, quinazolinyl, isoquinazolinyl, quinolyl, naphthyridyl, acridyl, phenanthridinyl, imidazopyridyl, diazanaphthyl, triazinene, indolyl,
  • the amine is -NH 2; Dialkylamines; Diarylamine; Diheteroarylamine; Alkylarylamines; Alkylheteroarylamines; And arylheteroarylamine.
  • the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, diviphenylamine, anthracenylamine, 9-methyl-anthracenylamine, diphenylamine, phenyl Naphthylamine, ditolylamine, phenyltolylamine, triphenylamine, and the like, but are not limited thereto.
  • X in the formula (1) is NR 3 , and at least one of Y and R 3 is - (L) m - (Z) n ,
  • X in formula (1) is CR 4 R 5 , S, O or Se, Y is - (L) m - (Z) n ,
  • n 1 to 6
  • n is an integer of 1 to 5
  • R 4 , R 5 and R 10 to R 12 are each independently hydrogen; Substituted or unsubstituted C 1 to C 60 straight or branched alkyl; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl.
  • X in the formula (1) is NR 3 , and at least one of Y and R 3 is - (L) m - (Z) n ,
  • X is CR 4 R 5 , S, O or Se
  • Y is - (L) m - (Z) n ,
  • n 1 to 6
  • n is an integer of 1 to 5
  • R, R ', R ", R 4, R 5 and R 10 to R 12 are, and the same as or different from each other, each independently represent hydrogen, the heavy hydrogen, halogen, C 6 to monocyclic of C 60 or unsubstituted aryl, and C 2 to C 60 monocyclic or polycyclic heteroaryl, 1-alkyl of at least substituted with a substituent or a straight chain of the unsubstituted C 1 to C 60 unsubstituted or branched chain is selected from; deuterium, halogen, C 6 to C 60 monocyclic or polycyclic aryl and C 2 to C 60 monocyclic or polycyclic heteroaryl group unsubstituted or substituted by one or more substituents selected from C 3 to monocyclic of C 60 or polycyclic cycloalkyl; deuterium, halogen, a monocyclic of C 6 to C 60 or polycyclic aryl and C 2 to C 60 monocyclic or polycyclic heteroaryl group unsubstit
  • L is a direct bond;
  • Z is a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl, wherein said heteroaryl is at least one selected from N, O and S as a heteroatom One.
  • Z is X 1 and X 2 are substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic aromatic heterocyclic ring.
  • Y 1 to Y 5 are the same or different and each independently represent S, NY 'or CY'Y "
  • Y 'and Y are the same or different and each is independently hydrogen, substituted or unsubstituted alkyl, a linear or branched unsubstituted C 1 to C 60; of the substituted or unsubstituted C 6 to C 60 monocyclic or Aryl of a polycyclic ring.
  • X is NR 3
  • at least one of Y and R 3 is - (L) m - (Z) n , Substituted phenylene;
  • heteroarylene substituted or unsubstituted C 5 Z, m and n are the same as in the above-mentioned one condition, wherein Z is bonded at the para or meta position relative to the atom bonded to the core L.
  • X in the above first embodiment is NR 3
  • Y is - (L) m - (Z) n
  • R 3 is the same as in the above- L
  • Z, m and n are the same as in the first embodiment described above
  • Z is bonded to the para position with respect to the atom bonded to the core of L.
  • X in the above first embodiment is NR 3
  • Y is - (L) m - (Z) n
  • R 3 is the same as in the above- L
  • Z, m and n are the same as in the above-mentioned first embodiment
  • Z is bonded to the meta position with respect to the atom bonded to the core of L.
  • X in the above first embodiment is NR 3
  • R 3 is - (L) m - (Z) n
  • X in the above first embodiment is NR 3
  • R 3 is - (L) m - (Z) n
  • X is CR 4 R 5 , S, O or Se
  • Y is - (L) m - (Z) n
  • R 4 , R 5 , Z, m and n are the same as in the above-mentioned one embodiment
  • Z is bonded to the para or meta position with respect to the atom bonded to the core of L.
  • X of the above-described second condition is CR 4 R 5, and S, O or Se
  • Y is - (L) m - (Z ) and n
  • R 4, R 5 , L, Z, m and n are the same as in the second embodiment described above, and Z is bonded to the para position with respect to the atom bonded to the core of L.
  • X of the above-described second condition is CR 4 R 5, and S, O or Se
  • Y is - (L) m - (Z ) and n
  • R 4, R 5 , L, Z, m and n are the same as in the above-mentioned second embodiment
  • Z is bonded to the meta position with respect to the atom bonded to the core of L.
  • L is substituted or unsubstituted phenylene; Or substituted or unsubstituted pyridylenes.
  • L is phenylene; Or pyridylene.
  • Formula 1 according to the above-described embodiment is represented by any one of the following Formulas 2 to 7:
  • Formula 1 according to the above-described embodiment is represented by any one of the following Formulas 8 to 12:
  • Formula 8 according to the above-described embodiment is represented by any one of the following Formulas 13 to 24:
  • R 11 and R 12 are the same or different and each independently hydrogen; Substituted or unsubstituted C 1 to C 60 straight or branched alkyl; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl,
  • the formulas (2) to (7) according to the above-described embodiments are represented by the following formulas (25) to (30), respectively.
  • X ' represents CR 4 R 5 , O, S or Se
  • R 4 , R 5 , R 11 and R 12 are the same or different from each other, and each independently hydrogen; Substituted or unsubstituted C 1 to C 60 straight or branched alkyl; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl,
  • the formula (1) may be selected from the following compounds.
  • Ar is bonded to the para position to an atom bonded to the core of the phenyl, and the above formulas (13) and (25) can be selected from the following compounds.
  • Ar is bonded to the meta position with respect to the atom bonded to the core of the phenyl, and the above formulas (13) and (25) can be selected from the following compounds.
  • Ar is bonded to the para position with respect to the atom bonded to the core of the phenyl, and the formula (14) may be selected from the following compounds.
  • Ar is bonded to a meta-position with respect to an atom bonded to the core of the phenyl, and Formula 14 may be selected from the following compounds.
  • Ar is bonded at the meta position with respect to an atom bonded to the core of the phenyl, .
  • Ar is bonded to the para position with respect to an atom bonded to the core of the phenyl, and the formula (17) may be selected from the following compounds.
  • Ar is bonded to the meta position with respect to an atom bonded to the core of the phenyl, and the formula (17) may be selected from the following compounds.
  • Ar is bonded to the para position with respect to the atom bonded to the core of the phenyl, May be selected from the following compounds.
  • Ar is bonded to the meta position with respect to the atom bonded to the core of the phenyl, May be selected from the following compounds.
  • Ar is bonded to the para position with respect to an atom bonded to the core of the phenyl, and Formula 20 may be selected from the following compounds.
  • Ar is bonded to the meta position with respect to the atom bonded to the core of the phenyl, and Formula 20 may be selected from the following compounds.
  • Ar is bonded to the para position with respect to an atom bonded to the core of the phenyl, and the above formulas 24 and 30 may be selected from the following compounds.
  • Ar is bonded to the meta position with respect to the atom bonded to the core of the phenyl, and the above formulas 24 and 30 may be selected from the following compounds.
  • Ar is bonded to a para position with respect to an atom bonded to the core of the phenyl, and the formula (23) may be selected from the following compounds.
  • Ar is bonded to the meta position with respect to an atom bonded to the core of the phenyl, and the formula (23) may be selected from the following compounds.
  • the above-mentioned compounds can be produced on the basis of the preparation examples described later. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed. The type or position of the substituent at the remaining positions may be changed as required by those skilled in the art using techniques known in the art.
  • core structures may be prepared as shown in the following general formulas 1 to 9.
  • Substituent groups may be attached by methods known in the art, and the substituent position or number of substituent groups may be varied according to techniques known in the art.
  • X and Y are the same as the general formula (1) according to the above-described embodiment, and are an example of the reaction for producing the core structure of the general formula (2).
  • Ar is the same as the above-described embodiment, and is an example of the reaction for producing the core structure of the general formula (13).
  • Ar is the same as R 3 defined in formula (1) according to the above-described embodiment, and is an example of the reaction for producing the core structure of formula (14).
  • Ar is the same as the above-described embodiment, and is an example of a reaction for producing the core structure of the formulas (15) to (16).
  • Ar is the same as the above-described embodiment, and is an example of the reaction for producing the core structure of the general formula (17).
  • Ar is the same as the above-described embodiment, and is an example of the reaction for producing the core structure of the general formulas (18) to (19).
  • Ar is the same as R 3 defined in formula (1) according to the above-described embodiment, and is an example of a reaction for producing the core structure of formula (20).
  • Ar is the same as R 3 defined in formula (1) according to the above-described embodiment, and is an example of a reaction for producing the core structure represented by formula (23).
  • Ar is the same as the above-described embodiment, and is an example of a reaction for producing the core structure of the general formula (24).
  • the organic light emitting device comprising the compound of Formula 1 described above.
  • the organic light emitting device according to the present application includes a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, and at least one of the organic layers includes the compound of Formula 1.
  • FIGS. 1 to 3 illustrate the stacking process of the electrodes and organic layers of the organic light emitting diode according to the embodiments of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of the organic light emitting device known in the art can be applied to the present application.
  • an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown.
  • the present invention is not limited to such a structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG.
  • FIG. 3 illustrates the case where the organic material layer is a multilayer. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • a hole injection layer 301 a hole transport layer 302
  • a light emitting layer 303 a hole transport layer 302
  • a hole blocking layer 304 a hole blocking layer
  • an electron transport layer 305 an electron injection layer 306.
  • the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except the light emitting layer may be omitted, and other necessary functional layers may be further added.
  • the organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer contains the compound of the above formula (1).
  • the compound of formula (I) may constitute one or more layers of the organic material layer of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.
  • the compound of Formula 1 may be used as an electron transport layer, a hole blocking layer, and a material of a light emitting layer in an organic light emitting device.
  • the compound of Formula 1 may be used as an electron transport layer or a material of a light emitting layer of an organic light emitting device.
  • the compound of Formula 1 may be used as a material of a phosphorescent host in an electron transport layer or a light emitting layer.
  • the cathode material materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used.
  • the cathode material materials having relatively low work functions can be used, and metals, metal oxides, conductive polymers, and the like can be used.
  • a known hole injecting material may be used.
  • a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p.
  • a pyrazoline derivative an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material may be used.
  • Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, Derivatives thereof, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used as well as low molecular weight materials and high molecular weight materials.
  • LiF is typically used in the art, but the present application is not limited thereto.
  • red, green or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used.
  • a fluorescent material may be used as a light emitting material, but it may be used as a phosphorescent material.
  • the light emitting material a material which emits light by coupling holes and electrons respectively injected from the anode and the cathode may be used. However, materials in which both the host material and the dopant material participate in light emission may also be used.
  • A-2 38.8g (105.0mmol), 2- bromoaniline (2-bromoaniline) 36.1g (210.0mmol ), tetrakis (triphenylphosphine) palladium (0) 6.1g (5.25mmol), K 3 PO 4 67.0 g (315.0 mmol) was refluxed and stirred at 400 ° C in 1,4-dioxane and 80 mL of H 2 O at 120 ° C for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. The solvent was removed by filtration with silica gel and washed with hexane to obtain 17.5 g (50%) of the target compound A-3 .
  • reaction mixture was cooled to room temperature, and a solid was formed.
  • the solid was filtered and then washed with dicholoromethane, ethyl acetate (EA), and methanol (MeOH). Thereafter, the solid was completely dissolved in dichloromethane in an excess amount, and then filtered with silica gel to obtain 10.3 g (78%) of the desired compound 1-12 .
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. The solvent was removed by filtration with silica gel and washed with hexane to obtain 19.0 g (81%) of the target compound C-1 .
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 9.5 g (79%) of the desired compound 1-113 .
  • reaction mixture was extracted with distilled water and dichloromethane.
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.92 g (54%) of the desired compound 1-119 .
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 9.5 g (68%) of the desired compound 1-157 .
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. The solvent was removed by filtration with silica gel and washed with hexane to obtain 21.2 g (89%) of the target compound F-1 .
  • the solvent was dissolved in dichloromethane (150 mL), and the mixture was stirred at room temperature for 16 hours with 10 mL of 30% aqueous H 2 O 2 solution.
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 6.3 g (51%) of the title compound 1-190 .
  • reaction mixture was extracted with distilled water and dichloromethane.
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain the desired compound 2-107 12.1 g (68%).
  • reaction mixture was extracted with distilled water and dichloromethane.
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain the desired compound 2-123 9.79 g (71%).
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. The solvent was removed by filtration with silica gel and washed with hexane to obtain 13.9 g (57%) of the target compound J-1 .
  • K-1 10.0g (20.02mmol), a phenanthrene-9-Daily Nick Acid (phenanthren-9-ylboronic acid) 5.34g (24.03mmol), tetrakis (triphenylphosphine) palladium (0) 1.16g (1.0 mmol) and 12.75 g (60.06 mmol) of K 3 PO 4 were refluxed and stirred at 120 ° C in 200 mL of 1,4-dioxane and 40 mL of H 2 O for 8 hours.
  • reaction mixture was extracted with distilled water and dichloromethane.
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator.
  • the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain the desired compound 3-43 10.6 g (77%).
  • the solid was filtered and washed with dichloromethane, ethyl acetate (EA), and methanol (MeOH). Thereafter, the solid was completely dissolved in dichloromethane in an excess amount, and then filtered with silica gel to obtain 6.6 g (55%) of the target compound 4-1 .
  • the solid was filtered and washed with ethyl acetate (EA) and methanol (MeOH). Thereafter, the solid was completely dissolved in dichloromethane in an excess amount, and then filtered with silica gel to obtain 4.4 g (55%) of the target compound 2-38 .
  • EA ethyl acetate
  • MeOH methanol
  • the organic layer was dried over anhydrous MgSO 4 and the solvent was removed using a rotary evaporator.
  • the solid was filtered and washed with ethyl acetate (EA) and methanol (MeOH). After that, the solid was boiled with 1,2-dichloroethane in an excess amount and filtered to obtain 6.6 g (78%) of the target compound 4-56 .
  • EA ethyl acetate
  • MeOH methanol
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain the target compound 2-148 8.9 g (67%).
  • reaction mixture was extracted with distilled water and dichloromethane.
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent. g (68%).
  • A-5 A mixture of 10.0 g (20.02 mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole 7.36 g (18.02 mmol), Pd 2 (dba) 3 1.83 g (2.0 mmol), XPhos 1.9 g And NaOtBu (8.1 g, 40.04 mmol) were stirred in toluene (100 mL) at 120 ⁇ ⁇ for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with MC to completely blow it. The resulting solid was purified by column to obtain 8.11 g (49%) of the desired compound 5-55.
  • 9,9 '- (5-bromo-1,3-phenylene) bis (9H-carbazole) was used instead of 2-chloro-4,6-diphenyl-1,3,5- . ≪ / RTI > (Yield: 55%).
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 10.9 g (84%) of the target compound 11-36 .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un dispositif électroluminescent organique comprenant ce composé.
PCT/KR2015/006723 2014-06-30 2015-06-30 Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé WO2016003171A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US15/318,901 US10446765B2 (en) 2014-06-30 2015-06-30 Heterocyclic compound and organic light emitting element using same
CN201580035950.0A CN106661020B (zh) 2014-06-30 2015-06-30 杂环化合物以及使用该杂环化合物的有机发光器件
JP2016575816A JP6513719B2 (ja) 2014-06-30 2015-06-30 ヘテロ環化合物およびこれを用いた有機発光素子

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2014-0081206 2014-06-30
KR20140081206 2014-06-30
KR1020140127222A KR101579289B1 (ko) 2014-06-30 2014-09-23 헤테로고리 화합물 및 이를 이용한 유기발광소자
KR10-2014-0127222 2014-09-23

Publications (1)

Publication Number Publication Date
WO2016003171A1 true WO2016003171A1 (fr) 2016-01-07

Family

ID=55019625

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2015/006723 WO2016003171A1 (fr) 2014-06-30 2015-06-30 Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé

Country Status (1)

Country Link
WO (1) WO2016003171A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017537085A (ja) * 2014-11-11 2017-12-14 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN110036013A (zh) * 2016-11-30 2019-07-19 喜星素材株式会社 杂环化合物以及使用此杂环化合物的有机发光装置
JP2020504911A (ja) * 2016-12-26 2020-02-13 エルティー・マテリアルズ・カンパニー・リミテッドＬＴ Ｍａｔｅｒｉａｌｓ Ｃｏ．， Ｌｔｄ． 有機発光素子
WO2021103769A1 (fr) * 2019-11-25 2021-06-03 广东阿格蕾雅光电材料有限公司 Composé et dispositif électroluminescent organique le contenant
CN113735848A (zh) * 2020-05-27 2021-12-03 上海和辉光电股份有限公司 一种电致发光化合物及其制备方法和应用
TWI764958B (zh) * 2016-11-30 2022-05-21 南韓商Ｌｔ素材股份有限公司 雜環化合物以及使用此雜環化合物的有機發光裝置

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996028447A1 (fr) * 1995-03-09 1996-09-19 Kyowa Hakko Kogyo Co., Ltd. Derives de pyrrolocarbazole

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996028447A1 (fr) * 1995-03-09 1996-09-19 Kyowa Hakko Kogyo Co., Ltd. Derives de pyrrolocarbazole

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
G. ZHU ET AL.: "Synthesis of Quinolinyl/Isoquinolinyl[a]pyrrolo [3,4-c] Carbazoles as Cyclin D1/CDK4 Inhibitors", BIOORG. MED. CHEM. LETT., vol. 13, 2003, pages 1231 - 1235, XP002406115 *
KLEMM ET AL.: "Synthesis of 1H Indolo[2,3-i]phenanthridine(I", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 9, no. 4, 1972, pages 927, XP055250376 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017537085A (ja) * 2014-11-11 2017-12-14 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN110036013A (zh) * 2016-11-30 2019-07-19 喜星素材株式会社 杂环化合物以及使用此杂环化合物的有机发光装置
TWI764958B (zh) * 2016-11-30 2022-05-21 南韓商Ｌｔ素材股份有限公司 雜環化合物以及使用此雜環化合物的有機發光裝置
JP2020504911A (ja) * 2016-12-26 2020-02-13 エルティー・マテリアルズ・カンパニー・リミテッドＬＴ Ｍａｔｅｒｉａｌｓ Ｃｏ．， Ｌｔｄ． 有機発光素子
EP3561892A4 (fr) * 2016-12-26 2020-07-29 LT Materials Co., Ltd. Dispositif électroluminescent organique
WO2021103769A1 (fr) * 2019-11-25 2021-06-03 广东阿格蕾雅光电材料有限公司 Composé et dispositif électroluminescent organique le contenant
CN113735848A (zh) * 2020-05-27 2021-12-03 上海和辉光电股份有限公司 一种电致发光化合物及其制备方法和应用
CN113735848B (zh) * 2020-05-27 2023-04-07 上海和辉光电股份有限公司 一种电致发光化合物及其制备方法和应用

Similar Documents

Publication Publication Date Title
WO2017078494A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
WO2017099490A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
WO2015199489A2 (fr) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
WO2018182294A1 (fr) Composé à base de benzocarbazole et dispositif électroluminescent organique comprenant celui-ci
WO2021150092A1 (fr) Dispositif électroluminescent organique
WO2021020942A1 (fr) Élément électroluminescent organique
WO2021112403A1 (fr) Élément électronique organique comprenant un composé organique, et dispositif électronique le comprenant
WO2019066250A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci
WO2022015084A1 (fr) Élément électroluminescent organique
WO2020009467A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2019221545A1 (fr) Diode électroluminescente organique
WO2016003171A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
WO2019225938A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2016068633A2 (fr) Composé polycyclique contenant de l'azote et dispositif électroluminescent organique utilisant ce composé
WO2017018795A2 (fr) Composé hétérocyclique et diode électroluminescente organique utilisant ce composé
WO2018124588A1 (fr) Dispositif électroluminescent organique
WO2016175624A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
WO2020153758A1 (fr) Composition, diode optoélectronique organique et dispositif d'affichage
WO2019017741A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2021020946A1 (fr) Élément électroluminescent organique
WO2021020948A1 (fr) Dispositif électroluminescent organique
WO2021215669A1 (fr) Composé d'élément optoélectronique organique, composition d'élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage
WO2016068640A2 (fr) Composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2014025209A1 (fr) Nouveau composé et dispositif électroluminescent organique comprenant celui-ci
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel 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: 15814968

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 15318901

Country of ref document: US

ENP Entry into the national phase

Ref document number: 2016575816

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15814968

Country of ref document: EP

Kind code of ref document: A1