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WO2020045822A1 - Composé organique et diode électroluminescente organique l'utilisant - Google Patents

Composé organique et diode électroluminescente organique l'utilisant Download PDF

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Publication number
WO2020045822A1
WO2020045822A1 PCT/KR2019/008673 KR2019008673W WO2020045822A1 WO 2020045822 A1 WO2020045822 A1 WO 2020045822A1 KR 2019008673 W KR2019008673 W KR 2019008673W WO 2020045822 A1 WO2020045822 A1 WO 2020045822A1
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group
aryl
formula
mmol
groups
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Korean (ko)
Inventor
박정근
엄민식
홍진석
심재의
손효석
이용환
박우재
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Solus Advanced Materials Co Ltd
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Doosan Solus Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D409/14—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
    • 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

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent thermal stability and electron transport ability, and including the same in one or more organic material layers, such as characteristics such as luminous efficiency, driving voltage and lifetime.
  • This improved organic electroluminescent device is a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent thermal stability and electron transport ability, and including the same in one or more organic material layers, such as characteristics such as luminous efficiency, driving voltage and lifetime.
  • 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 layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to the light emission color.
  • yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
  • a host / dopant system may be used as the light emitting material in order to increase luminous efficiency through an 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. The development of such phosphorescent materials can theoretically improve the luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials.
  • Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials.
  • 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
  • An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device and can be used as a phosphorescent material and / or a highly efficient electron transport layer material having excellent thermal stability and luminescence performance.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage, high luminous efficiency, and has an improved lifetime.
  • the present invention provides a compound represented by the following formula (1).
  • X is O or S
  • l is an integer of 1 to 3
  • R 1 to R 5 are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 Alkynyl group of ⁇ C 40 , cycloalkyl group of C 3 ⁇ C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ aryl of C 60 boron group, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ ,
  • Ar 1 to Ar 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, amino, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 Alkynyl group of ⁇ C 40 , cycloalkyl group of C 3 ⁇ C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ is selected from the group consisting of C 60 aryl boron group, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine oxide group, and a C
  • Ar 1 to Ar 3 is an aryl group of C 6 to C 60 ,
  • a group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an aryl amine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl group, C 1 to C 40 alkyloxy group,
  • the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is represented by the formula (1) It provides an organic electroluminescent device comprising a compound.
  • the compound of the present invention has excellent thermal stability, electron transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifespan, and efficiency are greatly improved.
  • the present invention provides a novel compound that can be used as a phosphorescent light emitting material having excellent thermal stability and light emitting ability, and at the same time have excellent electron transporting ability and can be used as a highly efficient electron transporting layer material.
  • the novel compound according to the present invention comprises two dibenzoic moieties that are the same or different from each other, and at least one arylene-based linker (L) and a triazine ring are bonded between them to form a basic skeleton.
  • L arylene-based linker
  • a triazine ring which is an electron withdrawing group (EWG) is bonded to an intermediate core therebetween, and the triazine is centered.
  • EWG electron withdrawing group
  • a substituted or unsubstituted dibenzofuran is a linker (L) is bonded at position 4, the opposite side is a structure in which a substituted or unsubstituted dibenzofuran or dibenzothiophene bonded directly without a linker Has This results in asymmetry based on the long axis of the molecule.
  • the compound of the present invention described above has high triplet energy (T1) because dibenzofuran is not directly bonded to triazine, which is a kind of EWG group having high electron absorbing properties.
  • the high triplet energy as described above can prevent the exciton generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer.
  • the number of excitons contributing to light emission in the light emitting layer may be increased, and thus, the light emitting efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.
  • T1 triplet
  • a core having excellent electron transporting ability the electron and hole can be easily transferred, and the luminous efficiency can be greatly enhanced.
  • the linker is introduced at position 4, which is an active site of dibenzofuran
  • the stability of the molecule may be increased, and the steric hindrance of the compound may cause thermal stability. May increase.
  • at least one aryl group is introduced at position 6 of the dibenzo-based moiety such as dibenzofuran and dibenzothiophene
  • it may exhibit a synergy effect in thermal stability.
  • structural steric hindrance may occur structurally.
  • Such tilted structures have a relatively high thermal stability effect.
  • the decomposition temperature (Td) is lowered to be purified at a relatively low temperature during sublimation purification has excellent thermal stability.
  • the compound represented by Chemical Formula 1 includes two dibenzo-based moieties, and at least one linker (L) and a triazine ring are bonded between them to form a basic skeleton, all of which are meta-meta (meta- meta) position.
  • These meta-meta bonds have a twisted structure based on the long axis of the molecule, thus extending the distance between these moieties to minimize the interaction between them and the physical and electrochemical properties of the compound itself. Increase stability.
  • the meta-meta bond is effective in inhibiting crystallization of the organic layer, compared to the linking group connected by ortho-para, or meta-para, and the like.
  • An organic electroluminescent device comprising can greatly improve durability and lifespan characteristics.
  • the compound represented by Chemical Formula 1 has structural asymmetry as the linker (L) is present only on one side. Such asymmetry of the molecule may inhibit crystallization to improve processability of the compound represented by Formula 1 and durability of the device.
  • the compound represented by Chemical Formula 1 may be used as one of materials of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic material layers of the organic electroluminescent device, because of excellent light emission characteristics. It is preferably used as a material of the light emitting layer of green phosphorescence and red phosphorescence, or an electron transport layer material.
  • the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green, red, blue phosphorescent host material), electron transport layer / injection layer material, light emitting auxiliary layer material, It can be used as an electron transport auxiliary layer material, more preferably a light emitting layer material, an electron transport layer material, an electron transport auxiliary layer material.
  • the organic electroluminescent device of the present invention including the compound of Formula 1 can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
  • At least one arylene linker and triazine is bonded between two dibenzo moieties that are the same or different from each other, the above-mentioned two dibenzo moieties and triazine groups It is characterized by a structure in which at least one or more aryl groups are introduced.
  • X introduced into the dibenzoic moiety may be O or S.
  • X introduced into the dibenzoic moiety may be O or S.
  • Ar 1 to Ar 3 may be introduced into two dibenzo-based moieties and triazine rings, respectively.
  • the Ar 1 to Ar 3 are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, nuclear atom 5-60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, a C 6 ⁇ C 60 aryl silyl group, a C 1 ⁇ C 40 group of an alkyl boron, C group of 6 to arylboronic of C 60, C 1 ⁇ C 40
  • Ar 1 to Ar 3 when at least one of Ar 1 to Ar 3 is an aryl group, they may be the same as or different from each other, and each of them may be selected from the following structural formulas.
  • R 1 to R 5 introduced in Formula 1 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ , or selected from the group consist
  • R 1 to R 5 are the same as or different from each other, and each independently composed of hydrogen, an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , and a heteroaryl group of 5 to 60 nuclear atoms It is preferably selected from the group.
  • l is an integer of 1-3, Preferably it is 1 or 2.
  • it may be a phenylene group or a biphenylene group.
  • a group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an aryl amine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl group, C 1 to C 40 alkyloxy group,
  • the compound of Formula 1 according to the present invention may be variously modified depending on the bonding position of the R 3 containing compound, which is an arylene-based linker, and a dibenzoic moiety including Ar 3 .
  • the compound represented by Chemical Formula 1 may be embodied in any one of the following Chemical Formulas 2 to 9.
  • the compound of Formula 1 according to the present invention can be variously modified depending on the position of Ar 1 introduced into the dibenzofuran moiety.
  • the compound represented by Chemical Formula 1 may be embodied in any one of the following Chemical Formulas 10 to 13.
  • a linker eg, an R 3 -containing arylene group
  • Ar 1 introduced at position 6
  • Compounds are preferred.
  • position 6 of dibenzofuran is the active site. Since the compound represented by the above formula (10) blocks the active position of dibenzofuran through substitution, it shows an excellent effect in terms of structural stability compared to the compound substituted at other positions (eg, formulas 11 to 13). In addition, when the substitution at the sixth position, because the steric hindrance is the largest it can have a high thermal stability.
  • the compound represented by Chemical Formula 1 of the present invention may have a meta-meta (meta-meta) bonding structure in a molecular structure.
  • the ring containing X and the ring containing R 3 are bonded to each other in a meta position, and with respect to the ring containing R 3 , Ar 2
  • the triazine ring and the ring including Ar 1 may be bonded to each other in a meta position.
  • the compound having a meta-meta-bonded structure has a twisted structure that is zigzag-shaped based on the long axis of the molecule, thereby minimizing the interaction between these moieties and the physical properties of the compound itself. It can increase the electrochemical stability.
  • Such compounds may be more embodied by the following formula (14).
  • X may be O or S.
  • At least one of Ar 1 to Ar 3 may be a C 6 ⁇ C 60 aryl group, specifically, two or more of Ar 1 to Ar 3 , or all three may be an aryl group. In this case, when at least two or more of Ar 1 to Ar 3 is an aryl group, a plurality of aryl groups may be the same or different from each other.
  • R 1 to R 5 may each independently be selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, in particular an arylene-based R 3 introduced into the linker (L) may be a C 6 ⁇ C 60 aryl group, or a heteroaryl group having 5 to 60 nuclear atoms. L may also be 1 or 2.
  • the compound represented by the general formula (1) of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by P-1 to P-188.
  • the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • Alkyl as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
  • R means aryl having 5 to 40 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 an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • arylamine refers to an amine substituted with aryl having 6 to 40 carbon atoms.
  • Cycloalkyl as used herein means 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 as used herein means monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such 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 40 carbon atoms
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • 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, 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 in combination of two or more.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 Compound.
  • the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, an electron transport auxiliary layer.
  • the light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, wherein the host material may include the compound of Formula 1 above.
  • the light emitting layer of the present invention may further include a compound known in the art other than the compound of Formula 1 as a host.
  • the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light emitting layer is increased, and thus the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.
  • the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of the light emitting layer having high efficiency.
  • the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a light emitting layer, more preferably a phosphorescent host May include a compound represented by Chemical Formula 1.
  • an electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic EL device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted between the electrode and the organic material layer interface.
  • the organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode 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 above. have.
  • 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 used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like.
  • the positive electrode material may use any positive electrode material known in the art without limitation.
  • metals such as vanadium, chromium, copper, zinc, gold or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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.
  • the negative electrode material may use any negative electrode material known in the art without limitation.
  • metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof;
  • multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art can be used without limitation.
  • the 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 EL device was manufactured in the same manner as in Example 1, except that CBP, 1, and 2 were used instead of the compound P-1 as a light emitting host material when forming the emission layer.
  • the green organic EL devices of Examples 1 to 12 which use the compounds P-1 to P-185 according to the present invention as the light emitting layer of the green organic EL device, are conventionally referred to as CBP, compounds 1 and 2
  • CBP carbon-catalyzed polystyrene
  • Comparative Examples 1-3 which were used, it turned out that it shows more excellent performance in terms of efficiency and a drive voltage.
  • Example 2 which includes a P-11 compound having an aryl group introduced at position 6 of dibenzofuran, has better performance in terms of driving voltage and current efficiency than Example 1, which includes P-1 having no aryl group introduced therein. Indicates. This is because the position 6 of the active position of the dibenzofuran is blocked by the substitution, thereby increasing the structural stability significantly, it can be judged to have better physical properties through the biggest steric hindrance.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol and the like
  • UV OZONE cleaner Power sonic 405, Hwashin Tech
  • DS-205 Doosan Electronics, 80 nm
  • NPB 15 nm
  • DS-405 Doosan Electronics, 30 nm
  • electron transport layer material of Table 2 below (30 nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.
  • a blue organic EL device was manufactured in the same manner as in Example 13, except that Alq 3 was used instead of compound P-1 as the electron transporting layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound T-1, instead of Compound P-1, was used as the electron transporting layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound T-2, instead of Compound P-1, was used as the electron transporting layer material.
  • NPB, AND, Alq 3, T-1, and T-2 used in Examples 13 to 24 and Comparative Examples 4 to 6 are as follows.
  • the blue organic electroluminescent devices of Examples 13 to 24 using the compounds P-1 to P-185 synthesized in the above Synthesis Example have a meta-meta (m, m-) bond in the molecular structure, Compared with the blue organic electroluminescent devices of Comparative Examples 5 and 6, in which a compound having p, p-biphenylene or m, p-biphenylene is used for the electron transport layer, it has excellent performance in terms of driving voltage, emission peak, and current efficiency. It could be seen that.

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  • Optics & Photonics (AREA)

Abstract

La présente invention concerne : un nouveau composé qui présente une excellente stabilité thermique, une excellente capacité de transport d'électrons et une excellente capacité d'émission de lumière ; ainsi qu'une diode électroluminescente organique qui comprend au moins une couche organique contenant le composé et qui présente ainsi des caractéristiques améliorées en termes d'efficacité lumineuse, de tension de commande, de durée de vie, et des caractéristiques similaires.
PCT/KR2019/008673 2018-08-30 2019-07-12 Composé organique et diode électroluminescente organique l'utilisant Ceased WO2020045822A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114031605A (zh) * 2021-12-06 2022-02-11 武汉天马微电子有限公司 一种含有氰基萘的有机化合物及其在有机发光器件和面板中的应用
WO2022173265A1 (fr) * 2021-02-15 2022-08-18 (주)피엔에이치테크 Composé organique luminescent et dispositif électroluminescent organique le comprenant
CN116724036A (zh) * 2021-01-08 2023-09-08 出光兴产株式会社 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备
US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12171108B2 (en) 2020-10-20 2024-12-17 Samsung Display Co., Ltd. Organic electroluminescence device
KR102643044B1 (ko) * 2022-05-06 2024-03-04 솔루스첨단소재 주식회사 유기 전계 발광 소자용 조성물 및 이를 포함하는 유기 전계 발광 소자
KR102643046B1 (ko) * 2022-05-27 2024-03-04 솔루스첨단소재 주식회사 유기 전계 발광 소자용 조성물 및 이를 포함하는 유기 전계 발광 소자

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160085206A (ko) * 2015-01-07 2016-07-15 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
KR20170089599A (ko) * 2016-01-27 2017-08-04 에스에프씨 주식회사 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20170113320A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR20180063710A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2018103749A1 (fr) * 2016-12-08 2018-06-14 广州华睿光电材料有限公司 Dérivé cyclique fusionné de triazine et son application dans un dispositif électronique organique

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101516078B1 (ko) 2013-09-16 2015-04-29 삼성전기주식회사 인쇄회로기판 및 인쇄회로기판 제조 방법
KR102418440B1 (ko) * 2017-09-29 2022-07-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102617841B1 (ko) * 2018-05-29 2023-12-26 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102729618B1 (ko) * 2018-08-09 2024-11-13 덕산네오룩스 주식회사 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160085206A (ko) * 2015-01-07 2016-07-15 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
KR20170089599A (ko) * 2016-01-27 2017-08-04 에스에프씨 주식회사 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20170113320A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR20180063710A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2018103749A1 (fr) * 2016-12-08 2018-06-14 广州华睿光电材料有限公司 Dérivé cyclique fusionné de triazine et son application dans un dispositif électronique organique

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
CN116724036A (zh) * 2021-01-08 2023-09-08 出光兴产株式会社 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备
EP4276098A4 (fr) * 2021-01-08 2025-01-15 Idemitsu Kosan Co., Ltd Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et appareil électronique
WO2022173265A1 (fr) * 2021-02-15 2022-08-18 (주)피엔에이치테크 Composé organique luminescent et dispositif électroluminescent organique le comprenant
CN114031605A (zh) * 2021-12-06 2022-02-11 武汉天马微电子有限公司 一种含有氰基萘的有机化合物及其在有机发光器件和面板中的应用
CN114031605B (zh) * 2021-12-06 2023-09-29 武汉天马微电子有限公司 一种含有氰基萘的有机化合物及其在有机发光器件和面板中的应用

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