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WO2018016742A1 - Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2018016742A1
WO2018016742A1 PCT/KR2017/006274 KR2017006274W WO2018016742A1 WO 2018016742 A1 WO2018016742 A1 WO 2018016742A1 KR 2017006274 W KR2017006274 W KR 2017006274W WO 2018016742 A1 WO2018016742 A1 WO 2018016742A1
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compound
llozw
oav
8ΐοζ
substituted
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Korean (ko)
Inventor
정민우
이동훈
박태윤
조성미
문정욱
이정하
채미영
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020170075029A external-priority patent/KR101849747B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201780004123.4A priority Critical patent/CN108368078B/zh
Priority to US15/771,066 priority patent/US11903311B2/en
Priority to EP17831215.3A priority patent/EP3480194B1/fr
Priority to JP2019502221A priority patent/JP7210856B2/ja
Publication of WO2018016742A1 publication Critical patent/WO2018016742A1/fr
Anticipated expiration legal-status Critical
Priority to US17/842,520 priority patent/US12167689B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound compound and a light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • 3 ⁇ 4 is 0 or S
  • Li and L 2 are each independently a single bond; A substituted or unsubstituted C 6 - 60 arylene; Or substituted or unsubstituted 0, N, Si and S containing at least one hetero atom selected from the group consisting of ( 60 heteroarylene,
  • Yi to Y3 are each independently N or CR 3 , at least one of ⁇ to Y 3 is ⁇ ,
  • Ar 2 is substituted or unsubstituted C 6 -60 aryl
  • Ri to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 Haloalkyl; Substituted or unsubstituted d- 60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted
  • nl and n2 are each independently an integer of 0-3.
  • the present invention is a crab 1 electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. to provide.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compound represented by Chemical Formula 1 may be used as a host material of the light emitting layer.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • a bond connected to another substituent means a bond connected to another substituent, a single bond means a case where no separate atoms are present in the portion represented by and L 2 .
  • the ester group may be substituted with a linear, branched or cyclic alkyl group having 6 to 25 carbon atoms or 6 to aryl carbon atoms in the oxygen of the ester group.
  • the compound of the following structural formulae but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group is specifically trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1_ethyl-butyl, pentyl, n_ Pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methyltyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2-propyl
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2, 2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl— 1-yl, 2, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group
  • the heterocyclic group is a heterocyclic group including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group and triazole group , Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group , Quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, Benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, ,
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description about the aryl group or cycloalkyl group described above may be applied except that two substituents are formed by bonding.
  • the heterocyclic ring is not monovalent, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the present invention provides a compound represented by the formula (1). Specifically, the compound represented by Chemical Formula 1 is represented by the following Chemical Formulas 1-1 to 1-4:
  • Formulas 1-1 to 1-4 Yi to Y 3 , Ar la , Ar lb> Ar 2 , Ri, R 2 , nl and n2 are the same as defined in Formula 1 above.
  • L 2 are each independently, a single bond; Or a substituted or unsubstituted C 6 - 20 aryl may renil.
  • L 2 are each independently a single bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenylylene.
  • L 2 may be each independently, a single bond, or any one selected from the group consisting of:
  • ⁇ Is ⁇ , ⁇ 2 is CR 3 and Y 3 is CR 3 ;
  • ⁇ Is an ⁇ , ⁇ 2 is CH, ⁇ is 3 or ⁇ ;
  • ⁇ Is CH, ⁇ 2 is CH, and ⁇ 3 may be ⁇ .
  • X 2 is S, NZ 4 , or CZ 5 Z 6 ,
  • Zi to Z 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Substituted or unsubstituted d-20 haloalkyl; Substituted or unsubstituted C 6 - 20 aryl; Or heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S,
  • cl is an integer of 0 to 5
  • c2 is an integer of 0 to 4,
  • c3 is an integer of 0-3. At this time, cl represents the number of ⁇ . When cl is 2 or more, two or more ⁇ may be the same or different from each other. Description of c2 and c3 can be understood with reference to the description of cl and the structure of the formula. Specifically, for example, Ar la and Ar lb may each independently be any one selected from the group consisting of:
  • Ar 2 is substituted or unsubstituted C 6 -60 aryl.
  • aryl does not include a non-aromatic condensed ring.
  • the substituted or unsubstituted fluorenyl group is excluded from Ar 2 of the present invention.
  • Ar 2 is unsubstituted or deuterium; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Si (3 ⁇ 4) (3 ⁇ 4) (3 ⁇ 4); 60 is an aryl, - C (Q 4) ( Q 5) (Q 6) and C 6 - C 6 substitution of from the group consisting of 60 to aryl substituents each independently selected
  • Qi to Q 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or ' unsubstituted d-20 alkyl; Or substitution It may be a 20-aryl-unsubstituted C 6.
  • Ar 2 can be any one selected from the group consisting of:
  • Zn to X 14 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-eo haloalkyl; Si (3 ⁇ 4) (3 ⁇ 4) (3 ⁇ 4); C (Q 4 ) (3 ⁇ 4) (3 ⁇ 4) and C 6 -60 aryl,
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Or a substituted or unsubstituted C 6 ring - A 20 aryl,
  • cll is an integer from 0 to 5
  • cl2 is an integer of 0-7.
  • cl3 is an integer of 0 to 9
  • cl4 is an integer of 0 to 4
  • cl5 is an integer of 0 to 3
  • cl6 is an integer from 0 to 11
  • cl7 is an integer of 0 to 9
  • cl8 is an integer from 0 to 6
  • cl9 is an integer of 0-12. In this case, cll represents the number of Z u . When cll is 2 or more, two or more Z u may be the same or different from each other. Description of cl2 to cl9 can be understood with reference to the description of the cll and the structure of the formula.
  • 3 ⁇ 4 to Q 6 is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; methyl; Or phenyl.
  • Ar 2 is any one selected from the group consisting of
  • Ri to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; Cyano; Or substituted or unsubstituted Cwo alkyl.
  • Ri and R 2 may each independently be hydrogen, deuterium, cyano, methyl, or methyl substituted with deuterium, and 3 ⁇ 4 may be hydrogen.
  • nl represents the number of. When nl is 2 or more, two or more 3 ⁇ 4 may be the same or different from each other. Description of n2 may be understood with reference to the description of nl and the structure of Formula 1.
  • the compound may be selected from the group consisting of the following compounds: oz
  • Compound represented by the formula (1) such as a pyridinyl group, a pyrimidinyl group, or a triazinyl group at a specific position of the dibenzofuran or dibenzothiophene core
  • the N atom-containing heteroaryl substituent group has a structure in which an aromatic aryl substituent is linked to a specific position of the dibenzofuran or dibenzothiophene core, whereby the organic light emitting device using the non-aromatic condensed cyclic group such as fluorenyl group is connected. Compared with the organic light emitting device using the compound, it can exhibit high efficiency, low driving voltage and long life.
  • the compound represented by the formula (1) can be prepared by a manufacturing method such as Banung Formula 1 as follows: In Reaction Formula 1, 1 2 , Yi to Y 3 , Aria, Ar lb and Ar 2 are the same as defined in Formula 1.
  • the compound represented by Formula 1 may be prepared by appropriately replacing the starting material in accordance with the structure of the compound to be prepared with reference to Banung Formula 1.
  • the present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. to provide.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 may be used as a host material in the emission layer.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate by using a PVDC physical vapor deposition method such as sputtering or e-beam evaporat ion.
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer is formed thereon, by depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer anode material on a substrate from a cathode material (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • As the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide ( ⁇ ), indium zinc oxide (IZ0); ⁇ 0: ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PED0T), polypyrrole and polyaniline, but are not limited to sons no. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied mol ecular orbital (HO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injection material include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile-nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ) Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer receives holes from the hole injection layer
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material is suitable.
  • Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the light emitting insect may include a host material and a dopant material.
  • the host material may include a compound represented by Chemical Formula 1 described above. In addition, it may further include a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder type furans.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes : fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted.
  • arylamine As a compound in which at least one arylvinyl group is substituted, a substituent selected from one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • an electron transport material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Do.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, etherboom and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds and nitrogen-containing five-membered ring derivatives; and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis ( 10—hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl -8-quinolinato) (0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2 -Naphlato) gallium, etc., but is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • Phenylnaphthalene (l-brotno-4-phenylnaphthalene) (10.8 g, 38
  • Example 1 Synthesis Example 1 except that 4-chloro_2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) was used instead of compound Q-36 19.9 g, 38.1 ⁇ ol) and 2-bromophenanthrene.
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) of 1,300 A was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned.
  • a detergent was used as the detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the HI-1 compound as described above was thermally vacuum deposited to a thickness of 50 A on the ⁇ transparent electrode prepared as above to form a hole injection layer.
  • a hole transport layer was formed by thermal vacuum deposition of the HT-1 compound at a thickness of 250 A on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the HT-2 compound at a thickness of 50 A on the HT-1 deposition film.
  • Phosphorescent dopant YGD-1 was co-deposited at a weight ratio of 1 and 13 ⁇ 4 to form a light emitting layer having a thickness of 400 A.
  • ET-1 material was vacuum deposited to a thickness of 250 A on the light emitting layer, and the ET-2 material was co-deposited with Li in a 2% weight ratio to a thickness of 100 A to form an electron transport layer and an electron injection layer.
  • Aluminum was deposited to a thickness of 1000 A on the electron injection layer to form a cathode.
  • the organic light emitting diodes of Examples 2 to 49 were manufactured by the same method as Example 1, except that phosphorescent host materials and dopant contents were changed as shown in Tables 1 to 3 below to form the emission layer. . Comparative Example 1 to Comparative Example 10
  • the organic light emitting diodes of Comparative Examples 1 to 10 were manufactured using the same method as in Example 1, respectively.
  • the host materials A to I used in the comparative examples are as follows.
  • T95 means the time required to reduce the luminance to 953 ⁇ 4 when the initial luminance at the light density of 50 mA / cm 2 is 100%.
  • a HI-1 compound as described below was thermally vacuum deposited to a thickness of 150 A to form a hole injection layer.
  • phosphorescent dopant GD-1 was co-deposited on the hole transport layer at a weight ratio of Compound 47 and 5% prepared in Synthesis Example 15-3 to form a light emitting layer having a thickness of 400 A.
  • a hole blocking layer was formed by vacuum depositing an ET-3 material to a thickness of 50 A on the light emitting layer, and a 250 A electron transport layer was formed by vacuum depositing an ET-4 material and LiQ in a weight ratio of 1: 1 on the hole blocking layer.
  • Lithium fluoride (UF) having a thickness of 10 A was sequentially deposited on the electron transport layer, and Mg was deposited with Ag at a weight ratio of 10> to form an electron injection layer having a thickness of 200 A.
  • Aluminum was deposited to a thickness of 1000A on the cathode to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec. — 7 to 5 x 10 "8 torr
  • Example 50 Except for changing the phosphorescent host material and dopant content in forming the light emitting layer with Tables 4 and 5, the same method as in Example 50 was performed. Using each of the organic light emitting diodes of Examples 51 to 90, respectively. Comparative Examples 11 to 19
  • the organic light emitting diodes of Comparative Examples 11 to 19 were manufactured by the same method as Example 50, except that the phosphorescent host material and the dopant content were changed as shown in Table 6 when forming the emission layer.
  • the host materials A to I used in the comparative examples are as described above.
  • T95 means the time required for the luminance to decrease to 95% when the initial luminance at the light density of 20 mA / cm 2 is 100%.
  • the organic light emitting device manufactured by using the compound according to the present invention as a phosphorescent host material exhibits superior performance in terms of driving voltage, current efficiency, and lifetime compared to the organic light emitting device of the Comparative Example. can confirm.
  • the organic light emitting device according to the embodiment is a phosphorescence that is commonly used The lifespan was increased by at least 150% compared to the organic light emitting diodes according to Comparative Examples 9 and 19 using the compound I as a host material.
  • the organic light emitting device according to Examples 4, 8, and 50 is the organic light emitting device according to Comparative Examples 1, 6, 11, and 16 using compounds A and F having different substitution positions of the compound and triazinyl group according to the present invention, respectively.
  • the organic light emitting diode according to Example 28 also exhibited an increase in lifespan of about 370% or more compared to the organic light emitting diode according to Comparative Example 3 using the compound C.
  • the organic light emitting diode according to Examples 30 and 31 also includes Compound G. Compared to the organic light emitting device according to Comparative Example 7, using the above, the lifespan was increased by about 250% or more. In addition, it was found that the driving voltage, current efficiency, and lifespan of the organic light emitting diode according to Comparative Example 5 using the compound E containing no triazinyl group were significantly lower than those of the organic light emitting diode according to the embodiment.
  • the organic light emitting device according to Comparative Examples 8 and 18 using the compound H substituted with the dimethyl fluorenyl group also shows a significantly lower lifespan than the organic light emitting device according to the embodiment, which is used when manufacturing or driving the device. It is believed that this is due to the generation of impurities generated as radicals formed by dimethylfluorenyl in the air.

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé hétérocyclique et sur un dispositif électroluminescent organique le comprenant.
PCT/KR2017/006274 2016-07-20 2017-06-15 Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant Ceased WO2018016742A1 (fr)

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CN201780004123.4A CN108368078B (zh) 2016-07-20 2017-06-15 杂环化合物和包含其的有机发光器件
US15/771,066 US11903311B2 (en) 2016-07-20 2017-06-15 Heterocyclic compound and organic light emitting device comprising the same
EP17831215.3A EP3480194B1 (fr) 2016-07-20 2017-06-15 Composés hétérocycliques et dispositifs électroluminescents organiques les comprenant
JP2019502221A JP7210856B2 (ja) 2016-07-20 2017-06-15 新規なヘテロ環式化合物およびこれを利用した有機発光素子
US17/842,520 US12167689B2 (en) 2016-07-20 2022-06-16 Heterocyclic compound and organic light emitting device comprising the same

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KR10-2016-0092202 2016-07-20
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KR10-2017-0075029 2017-06-14

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WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
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WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045851A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045842A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045843A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025073675A1 (fr) 2023-10-04 2025-04-10 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025104058A1 (fr) 2023-11-16 2025-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
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WO2025195961A1 (fr) 2024-03-19 2025-09-25 Merck Patent Gmbh Dispositifs électroluminescents organiques
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EP4254526A4 (fr) * 2020-11-26 2024-10-30 SFC Co., Ltd. Dispositif électroluminescent organique comprenant un nouveau composé organique dans une couche d'émission
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JPWO2022149476A1 (fr) * 2021-01-08 2022-07-14
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