WO2022005247A1 - Composé organique et élément électroluminescent organique l'utilisant - Google Patents

Composé organique et élément électroluminescent organique l'utilisant Download PDF

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WO2022005247A1
WO2022005247A1 PCT/KR2021/008423 KR2021008423W WO2022005247A1 WO 2022005247 A1 WO2022005247 A1 WO 2022005247A1 KR 2021008423 W KR2021008423 W KR 2021008423W WO 2022005247 A1 WO2022005247 A1 WO 2022005247A1
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organic
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손호준
엄민식
김회문
정화순
배형찬
김진웅
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솔루스첨단소재 주식회사
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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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • 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

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  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, by including a compound having excellent electron transport ability and the same in one or more organic material layers, characteristics such as luminous efficiency, driving voltage, lifespan, as well as progressiveness It relates to an organic electroluminescent device having an improved driving voltage.
  • an organic electroluminescent device (hereinafter, referred to as 'organic EL device'), when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted.
  • 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, etc. according to their function.
  • the material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the emission color.
  • yellow and orange light-emitting materials are also used as light-emitting materials for realizing better natural colors.
  • a host/dopant system may be used as a light emitting material.
  • 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 a phosphorescent material can theoretically improve the luminous efficiency by 4 times compared to that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.
  • NPB hole injection layer
  • BCP hole blocking layer
  • Alq 3 hole blocking layer
  • anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials.
  • a metal complex compound containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc. is a blue, green, and red dopant material. is being used as So far, CBP has shown excellent properties as a phosphorescent host material.
  • the present invention is excellent in electron injection and transport ability, electrochemical stability, thermal stability, etc. to provide a novel organic compound that can be used as an organic layer material of an organic electroluminescent device, specifically, an electron transport layer material or an N-type charge generation layer material aim to
  • the present invention provides an organic compound represented by the following formula (1):
  • R 1 and R 2 are the same as or different from each other, and are each independently hydrogen, a C 1 ⁇ C 6 alkyl group, or a C 3 ⁇ C 60 cycloalkyl group,
  • R 1 and R 2 are C 1 ⁇ C 6 alkyl group
  • L 1 is a single bond
  • C 6 ⁇ C 60 Arylene group is selected from the group consisting of a heteroarylene group having 5 to 60 nuclear atoms,
  • Ar 1 is a C 6 ⁇ C 60 aryl group
  • the alkyl group and cycloalkyl group of R 1 and R 2 , the arylene group and heteroarylene group of L 1 , and the aryl group of Ar 1 are each independently deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group Group (amidino group), hydrazino group (hydrazino group), hydrazono group (hydrazono group), C 1 ⁇ C 60 Alkyl group, C 2 ⁇ C 60 Alkenyl group, C 2 ⁇ C 60 Alkynyl group, C 3 ⁇ C 60 cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C 3 ⁇ C 60 cycloalkenyl group, heterocycloalkenyl group having 3 to 60 nuclear atoms, C 6 ⁇ C 60 aryl group, C 1 ⁇ C 60 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C
  • the present invention is an anode; cathode; and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers provides an organic electroluminescent device comprising the above-described organic compound.
  • the organic material layer including the compound may be an electron transport layer.
  • the present invention provides an anode and a cathode spaced apart from each other; a plurality of light emitting units interposed between the anode and the cathode; An N-type charge generating layer and a P-type charge generating layer interposed between adjacent light emitting units, wherein each light emitting unit comprises a hole transporting layer, a light emitting layer and an electron transporting layer, wherein the N type charge generating layer comprises the above-mentioned compound It provides an organic electroluminescent device comprising.
  • the compound of the present invention Since the compound of the present invention has excellent electron transport ability, light emitting ability, electrochemical stability, thermal stability, etc., it can be used as an organic material layer material of an organic electroluminescent device.
  • the compound of the present invention when the compound of the present invention is used as at least any one of an electron transport layer material, an electron transport auxiliary layer material, and an N-type charge generation layer material, an organic material having superior light emitting performance, low driving voltage, high efficiency and long lifespan compared to conventional materials. It is possible to manufacture an electroluminescent device, and furthermore, a full color display panel with improved performance and lifespan can be manufactured.
  • FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
  • FIG. 2 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a second embodiment of the present invention.
  • FIG 3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a third embodiment of the present invention.
  • FIG. 4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to a fourth embodiment of the present invention.
  • 360 electron transport auxiliary layer, 400: a first light emitting unit
  • 410 a first hole transport layer
  • 420 a first light emitting layer
  • 430 a first electron transport layer
  • 440 a hole injection layer
  • 500 a second light emitting unit
  • 510 a second hole transport layer
  • 520 a second light emitting layer
  • 530 a second electron transport layer
  • the present invention is an electron transport layer material and electron transport auxiliary layer material that can improve the high efficiency, long life, driving voltage characteristics and progressive driving voltage characteristics of an organic electroluminescent device due to excellent electron injection and transport ability, electrochemical stability, thermal stability, etc.
  • a novel compound that can be used as an N-type charge generating layer material is provided.
  • an alkyl group having a short chain length is introduced into at least one of positions 2 and 9 of the phenanthroline moiety, and various aryl groups are directly or It includes a structure introduced through a linker group (eg, an arylene group such as a phenylene group, a biphenylene group, or a terphenylene group).
  • a linker group eg, an arylene group such as a phenylene group, a biphenylene group, or a terphenylene group.
  • the carbon/nitrogen position number of the phenanthroline moiety can be represented as follows.
  • the phenanthroline moiety is a moiety with high electron absorption, it may act as an electron withdrawing group (EWG).
  • EWG electron withdrawing group
  • a substituent capable of acting as an electron donor group (EDG) is introduced (coupled) to the phenanthroline moiety directly or through a linker group.
  • EDG electron donor group
  • the molecular weight of the compound having an aryl group introduced at No. 2 and/or No. 9 of the phenanthroline moiety is increased, and thus the sublimation temperature is also increased. It may be damaged (deteriorated).
  • the compound of the present invention introduces an alkyl group, particularly an alkyl group with a short chain length such as a methyl group and an ethyl group, to the 2nd and/or 9th position of the phenanthroline moiety, thereby blocking the active site through a minimal increase in molecular weight and thus thermally stability can be increased.
  • the compound of the present invention in which the alkyl group is introduced 2 and/or 9 times has a lower sublimation temperature than the compound in which the aryl group is introduced in the 2 and/or 9 positions of the phenanthroline moiety. Accordingly, the compound of the present invention can increase thermal stability and prevent device deterioration during device manufacturing, improve electron mobility, and realize a low driving voltage of the device.
  • the phenanthroline moiety comprises nitrogen (N) in the sp2 hybrid orbital, which is relatively rich in electrons.
  • N nitrogen
  • the phenanthroline moiety has a structure in which two nitrogens are adjacent to each other, covalent bonding with surrounding hydrogen (H) or coordination bonding with alkali or alkaline earth metals such as Li and Yb is possible.
  • H hydrogen
  • the compound of Formula 1 containing such a phenanthroline moiety is applied to an electron transport layer or an N-type charge generating layer, the phenanthroline moiety traps the doped alkali metal or alkaline earth metal to form intramolecular electrons. By increasing the density, electron injection and transport ability can be improved.
  • the compound of the present invention when the compound of the present invention is applied to the N-type charge generation layer of an OLED, nitrogen of the phenanthroline moiety binds to an alkali metal or alkaline earth metal that is a dopant of the N-type charge generation layer to form a gap. state) can be formed.
  • nitrogen of the phenanthroline moiety binds to an alkali metal or alkaline earth metal that is a dopant of the N-type charge generation layer to form a gap. state
  • electrons can be smoothly transferred from the N-type charge generation layer to the electron transport layer due to the gap state.
  • the compound of the present invention even when the compound of the present invention is applied to the electron transport layer of an OLED, electrons can be smoothly transferred to the light emitting layer. Therefore, when the compound of the present invention is used as an N-type charge generating layer material or an electron transport layer material, while lowering the driving voltage of the organic electroluminescent device, it is possible to increase the luminous efficiency and realize a long
  • the compound represented by Formula 1 according to the present invention has excellent electron injection and transport ability. Therefore, the compound of the present invention may be used as an organic material layer, preferably an electron transport layer material of an organic electroluminescent device. In addition, the compound of the present invention may be used as an N-type charge generating layer material of an organic electroluminescent device having a tandem structure.
  • R 1 and R 2 are the same as or different from each other, and each independently represent hydrogen, a C 1 -C 6 alkyl group, or a C 3 -C 60 cycloalkyl group. However, at least one of R 1 and R 2 is a C 1 ⁇ C 6 alkyl group.
  • R 1 and R 2 are the same as or different from each other, and each independently represent hydrogen, a C 1 -C 6 alkyl group, or a C 3 -C 60 cycloalkyl group, and at least one of R 1 and R 2 is a methyl group.
  • ethyl group, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group may be selected from the group consisting of isobutyl group and t-butyl group.
  • R 1 and R 2 may be the same as or different from each other, and each independently a C 1 ⁇ C 6 alkyl group.
  • R 1 and R 2 are the same as each other, and may be a C 1 ⁇ C 6 alkyl group.
  • both R 1 and R 2 may be a methyl group.
  • the C 1 to C 6 alkyl group may be selected from the group consisting of a methyl group, an ethyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a s-butyl group, an isobutyl group, and a t-butyl group.
  • the alkyl group and the cycloalkyl group of R 1 and R 2 are each independently deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group ( hydrazono group), C 1 ⁇ C 60 alkyl group, C 2 ⁇ C 60 alkenyl group, C 2 ⁇ C 60 alkynyl group, C 3 ⁇ C 60 cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C 3 ⁇ C 60 cycloalkenyl group, heterocycloalkenyl group having 3 to 60 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 60 alkylox Period, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 60 Alkylsilyl group, C 6 ⁇ C 60 A
  • the compound represented by Formula 1 may be a compound represented by Formula 1 below, but is not limited thereto.
  • L 1 and Ar 1 are as defined in Formula 1 above,
  • R 2 may be a C 1 ⁇ C 6 alkyl group, specifically a methyl group, an ethyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a s-butyl group, an isobutyl group, and a t-butyl group It may be selected from the group consisting of, and more specifically, may be a methyl group. In this case, R 2 may be the same as or different from the substituents of Formulas 2 to 5 corresponding to R 1 of Formula 1 above.
  • R 2 is a C 1 to C 6 alkyl group, specifically, a methyl group, an ethyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, s-butyl It may be selected from the group consisting of a group, an isobutyl group, and a t-butyl group, and in this case, it is the same as the substituent of Formulas 2 to 5 corresponding to R 1 in Formula 1 above.
  • L 1 is a single bond, or is selected from the group consisting of a C 6 ⁇ C 60 arylene group and a heteroarylene group having 5 to 60 nuclear atoms, specifically a single bond, or C 6 ⁇ C It is an aryl group and an atomic nucleus, and 30 may be selected from 5 to 30 heteroarylene group consisting.
  • the arylene group and the heteroarylene group of L 1 are each independently deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group group), C 1 ⁇ C 60 Alkyl group, C 2 ⁇ C 60 Alkenyl group, C 2 ⁇ C 60 Alkynyl group, C 3 ⁇ C 60 Cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C 3 ⁇ C 60 cycloalkenyl group, heterocycloalkenyl group having 3 to 60 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 60 alkyloxy group , C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 60 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C
  • L 1 may be a C 6 ⁇ C 60 arylene group.
  • L 1 may be a linker group represented by the following Chemical Formula L.
  • n is an integer from 0 to 3
  • a is an integer from 0 to 4,
  • R 3 is plural, they are the same as or different from each other,
  • R 3 is hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C 1 to C 60 Alkyl group, C 2 ⁇ C 60 alkenyl group, C 2 ⁇ C 60 alkynyl group, C 3 ⁇ C 60 cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C 3 ⁇ C 60 cycloalkenyl group, A heterocycloalkenyl group having 3 to 60 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 60 alkyloxy group, C 6 to C 60 Aryloxy Period, C 1 ⁇ C 60 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group
  • L 1 may be selected from the group consisting of the following linker groups L1 to L4.
  • the phenanthroline moiety and the substituent Ar 1 are bonded to the para (para) or meta (meta) position around the linker group, or to the para-para or meta-meta position. Accordingly, the compound of the present invention forms a plate-like structure to induce stacking between molecules, and thus electron mobility is increased to have better electron transport properties.
  • the interaction between the phenanthroline moiety and the substituent Ar 1 is minimized, the structural stability of the molecule is increased, and the steric hindrance in the compound is minimized to minimize the physical and electrochemical stability of the compound itself , thermal stability can be significantly increased.
  • the compound of the present invention is effective in inhibiting crystallization of the organic layer, compared to the compound in which the phenanthroline moiety and the substituent Ar 1 are bonded to the ortho position around the linker group or introduced in the ortho-ortho position, Durability and lifespan characteristics of the organic electroluminescent device can be greatly improved.
  • Hydrogen of the linker groups L1 to L4 is deuterium (D), halogen, cyano group, nitro group, C 1 to C 12 alkyl group, C 6 to C 10 aryl group, heteroaryl group having 5 to 9 nuclear atoms, etc. may be substituted with one or more substituents of
  • Ar 1 may be a C 6 ⁇ C 60 aryl group, specifically, a C 6 ⁇ C 30 aryl group.
  • the compound of Formula 1 in which Ar 1 is a C 6 to C 60 aryl group may improve efficiency and driving voltage while maintaining the inherent lowest unoccupied molecular orbital (LUMO) energy level of the phenanthroline derivative.
  • LUMO lowest unoccupied molecular orbital
  • the aryl group of Ar 1 is deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, C 1 ⁇ C 60 of alkyl group, C 2 ⁇ C 60 alkenyl group, C 2 ⁇ C 60 alkynyl group, C 3 ⁇ C 60 cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C 3 ⁇ C 60 cycloalkenyl group , Heterocycloalkenyl group of 3 to 60 nuclear atoms, C 6 ⁇ C 60 Aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 60 Alkyloxy group, C 6 ⁇ C 60 Aryl Oxy group, C 1 ⁇ C 60 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron
  • Ar 1 may be a substituent selected from the group consisting of the following substituents S1 to S22.
  • the compound of Formula 1, wherein Ar 1 is the following substituent S3 or S4 is different from the compound of Formula 1 having other substituents, because the abrupt phase change in the low vacuum chamber during the manufacture of the organic electroluminescent device is minimized. Fairness can be improved.
  • the compound represented by Formula 1 according to the present invention may be embodied as a compound represented by Formula 6 or 7, but is not limited thereto.
  • R 1 and R 2 are the same as or different from each other, and are each independently a C 1 ⁇ C 6 alkyl group,
  • Ar 1 is a substituent selected from the group consisting of the following substituents S1 to S22,
  • n 0 or 1.
  • the compound represented by Formula 1 according to the present invention described above may be embodied as any one of Compounds 1 to 120 below.
  • the compound represented by Formula 1 according to the present invention is not limited by those exemplified below.
  • alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 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 linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. 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 unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon 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 means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms.
  • one or more carbons in the ring preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure.
  • R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • 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.
  • alkylsilyl means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl.
  • arylsilyl means a silyl substituted with aryl having 5 to 60 carbon atoms, and includes mono- as well as polyarylsilyl such as di- and tri-arylsilyl.
  • alkyl boron group means a boron group substituted with an alkyl having 1 to 40 carbon atoms
  • aryl boron group means a boron group substituted with an aryl group having 6 to 60 carbon atoms.
  • alkylphosphinyl group means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.
  • arylphosphinyl group means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.
  • arylamine means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamines.
  • heteroarylamine refers to an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.
  • (aryl) (heteroaryl) amine means an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.
  • condensed ring refers to a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, or It means a combination of these.
  • the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') including the compound represented by the above-described formula (1).
  • FIG. 1 to 4 are cross-sectional views schematically showing organic electroluminescent devices according to first to fourth embodiments of the present invention.
  • the organic electroluminescent device according to the present invention is an anode (anode) 100, a cathode (cathode) 200, and one or more layers interposed between the anode and the cathode
  • the organic material layer 300 is included, and at least one of the one or more organic material layers includes the compound represented by Formula 1 above.
  • the compound may be used alone, or two or more may be used in combination.
  • the one or more organic material layers 300 may include any one of a hole injection layer 310 , a hole transport layer 320 , a light emitting layer 330 , an electron transport auxiliary layer 360 , an electron transport layer 340 , and an electron injection layer 350 . It may include one or more, of which at least one organic material layer 300 includes the compound represented by Formula 1 above. Specifically, the organic material layer including the compound of Formula 1 may be the electron transport layer 340 . That is, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material.
  • the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like.
  • the compound of Formula 1 is excellent in thermal stability and electrochemical stability, it is possible to improve the performance of the organic electroluminescent device.
  • Such a compound of Formula 1 may be used alone or may be mixed with an electron transport layer material known in the art.
  • the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
  • the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compounds, aluminum complexes (eg , Alq 3, tris(8-quinolinolato)-aluminium), and gallium complexes (eg, Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These may be used alone or in combination of two or more.
  • the structure of the organic electroluminescent device of the present invention described above is not particularly limited, but, for example, on a substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (Figs. 1 to Figs. see 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device on a substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and the cathode 200 may have a sequentially stacked structure.
  • an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200 .
  • an electron transport auxiliary layer 360 may be positioned between the light emitting layer 330 and the electron transport layer 340 (refer to FIG. 3 ).
  • At least one of the organic layer 300 includes the compound represented by Formula 1 in the organic electroluminescent device of the present invention It can be manufactured by forming an organic material layer and an electrode with
  • 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 method.
  • the substrate usable in the present invention is not particularly limited, and non-limiting examples include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof
  • metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
  • combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb
  • conductive polymers such as polythiophene, poly(3
  • examples of the cathode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer, the hole transport layer, the light emitting layer and the electron injection layer are not particularly limited, and common materials known in the art may be used.
  • the organic electroluminescent device is a tandem (tandem) type device, the anode 100 and the cathode 200 facing each other; a plurality of light emitting units 400 and 500 interposed between the anode 100 and the cathode 200; and a charge generation layer 600 interposed between adjacent light emitting units 400 and 500 and including an N-type charge generation layer 610 and a P-type charge generation layer 620 .
  • the N-type charge generation layer 610 includes the compound represented by the above-described Chemical Formula 1.
  • Such a tandem organic electroluminescent device has at least two light emitting units, and may be configured by interposing a charge generating layer between adjacent light emitting units to increase the number of light emitting units.
  • the charge generation layer 600 including the N-type charge generation layer 610 and the P-type charge generation layer 620 is disposed between the adjacent light emitting units, and the N-type charge generation layer 610 is formed as described above. It includes a compound represented by the formula (1).
  • the organic electroluminescent device includes an anode 100 and a cathode 200 facing each other; a first light emitting unit 400 disposed on the anode 100; a second light emitting unit 500 disposed on the first light emitting unit 400; and a charge generation layer 600 interposed between the first and second light emitting units 400 and 500 and including an N-type charge generation layer 610 and a P-type charge generation layer 620 .
  • the N-type charge generation layer 610 includes the compound represented by the above-described Chemical Formula 1.
  • Each of the light emitting units 400 and 500 includes hole transport layers 410 and 510 , light emitting layers 420 and 520 , and electron transport layers 430 and 530 .
  • the first light emitting unit 400 includes a first hole transport layer 410 , a first light emitting layer 420 , and a first electron transport layer 430
  • the second light emitting unit 500 includes a hole transport layer 510 .
  • an emission layer 520 and an electron transport layer 530 may be included.
  • the first light emitting unit 400 may additionally include a hole injection layer 440 .
  • the hole transport layers 410 and 510, the light emitting layers 420 and 520, the electron transport layers 430 and 530, and the hole injection layer 440 are not particularly limited, and common materials known in the art may be used.
  • the charge generation layer (CGL) 600 is disposed between the light emitting units 400 and 500 adjacent to each other, thereby controlling the charges between the light emitting units 400 and 500 to achieve a charge balance.
  • the charge generation layer 600 includes an N-type charge generation layer 610 positioned adjacent to the first light emitting unit 400 to supply electrons to the first light emitting unit 400 ; and a P-type charge generation layer 620 positioned adjacent to the second light emitting unit 500 to supply holes to the second light emitting unit 500 .
  • the N-type charge generation layer 610 includes the compound represented by Chemical Formula 1 described above.
  • the compound of Formula 1 has excellent electron mobility and excellent electron injection and transport ability. Therefore, when the compound of Formula 1 is applied to an organic electroluminescent device as an N-type charge generating layer material, an increase in the progressive driving voltage and a decrease in the lifetime of the device can be prevented.
  • the N-type charge generation layer 610 includes one host having electron transport properties, and the one host is the compound represented by Formula 1 above. Unlike the N-type charge generation layer including two hosts, the n-type charge generation layer 610 of the present invention may have improved process efficiency during manufacturing through co-deposition.
  • the N-type charge generation layer 610 may further include an N-type dopant.
  • the N-type dopant usable in the present invention is not particularly limited as long as it is a material generally used in the N-type charge generating layer in the art, and for example, alkali metals such as Li, Na, K, Rb, Cs, Fr; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, Ra and the like; Group 15 metals such as Bi (bismuth) and Sb (antimony); La(lanthanum), Ce(cerium), Pr(preseodyminum), Nd(neodymium), Pm(promethium), Sm(samarium), europium(europium), Gd(gadolinium), Tb(terbium), Dy(dysprosium), lanthanide-based metals such as Ho(holmium), Er(erbium), Tm(thulium), Yb(ytterbium), Lu(lutetium), and the like; and one or more metal compounds described above.
  • alkali metals such as Li
  • an organic N-type dopantyl having electron donor properties and capable of donating at least a portion of an electron charge to an organic host eg, a cargo of Formula 1
  • organic host eg, a cargo of Formula 1
  • examples thereof include bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF), Tetrathiafulvalene (TTF), and the like.
  • the thickness of the N-type charge generation layer 610 is not particularly limited, and may be, for example, in the range of about 5 to 30 nm.
  • the P-type charge generation layer 620 may be formed of a metal or an organic material doped with P-type.
  • the metal includes Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni and Ti, and these may be used alone or as an alloy of two or more.
  • materials of the P-type dopant and the host used in the P-type doped organic material are not particularly limited as long as they are commonly used materials.
  • the P-type dopant includes F 4 -TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane), iodine, FeCl 3 , FeF 3 and SbCl 5 and the like.
  • non-limiting examples of the host include NPB (N,N'-bis(naphthaen-1-yl)-N,N'-bis(phenyl)-benzidine), TPD (N,N'-bis(3- There are methylphenyl)N,N'-bis(phenyl)-benzidine) and TNB(N,N,N',N'-tetra-naphthalenyl-benzidine), which can be used alone or in combination of two or more. have.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds of Table 1 was used instead of the compound 1 used as the electron transport layer material in Example 1.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compounds A to H were respectively used instead of the compound 1 used as the electron transport layer material in Example 1.
  • the compound of the present invention used in the organic electroluminescent device of Examples 1 to 36 has a lower sublimation temperature than the compound (compounds C, D) containing a phenanthroline moiety substituted with an aryl group during the fabrication of the device. , it was possible to prevent deterioration of the device.
  • the devices of Examples 1 to 36 including the compound of the present invention containing a phenanthroline moiety substituted with an alkyl group at the 2nd and 9th positions of phenanthroline as an electron transport layer material have an alkyl group at another position It was found that compared to the devices of Comparative Examples 5 to 6 including a compound containing a substituted phenanthroline moiety as an electron transport layer material, it exhibited superior performance in terms of driving voltage, emission peak and current efficiency.
  • the device of Comparative Example 6 using the compound includes the devices of Comparative Examples 1 and 2 using a compound containing a phenanthroline moiety unsubstituted with an alkyl group and phenantrol in which an aryl group is substituted at positions 2 and/or 9 Compared to the devices of Comparative Examples 3 and 4 using a compound containing a lean moiety, the efficiency characteristics were slightly improved, but the characteristics of the devices were not significantly improved because the intrinsic active site of phenanthroline could not be blocked.
  • the devices of Examples 1 to 36 using the compound of the present invention containing a phenanthroline moiety in which an aryl group is introduced at the 4th position while the alkyl group is introduced at No. 2 and No. 9 is an alkyl group at No. 2 and No.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • the substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 37, except that each of the compounds of Table 1 was used instead of the compound 1 used as the N-type charge generation layer material in Example 37.
  • An organic electroluminescent device was manufactured in the same manner as in Example 37, except that Compounds A to H were used instead of Compound 1 used as an N-type charge generation layer material in Example 37. At this time, since the compounds A to H used are the same as those described in Comparative Examples 1 to 8, they are omitted.
  • Example 37 compound 1 8.3 15.9 Example 38 compound 2 8.3 15.7 Example 39 compound 3 8.2 15.5 Example 40 compound 4 8.3 15.9 Example 41 compound 5 8.5 15.3 Example 42 compound 6 8.3 15.3 Example 43 compound 7 8.2 15.7 Example 44 compound 8 8.3 15.8 Example 45 compound 9 8.2 15.5 Example 46 compound 10 8.5 15.3 Example 47 compound 11 8.4 15.4 Example 48 compound 12 8.2 15.9 Example 49 compound 13 8.4 15.7 Example 50 compound 14 8.3 15.7 Example 51 compound 15 8.2 15.8 Example 52 compound 16 8.4 15.5 Example 53 compound 17 8.3 15.9 Example 54 compound 18 8.4 15.6 Example 55 compound 19 8.4 15.8 Example 56 compound 20 8.4 15.6 Example 57 compound 21 8.3 15.7 Example 58 compound 22 8.3 15.5 Example 59 compound 23 8.2 15.7 Example 60 compound 24 8.3 15.7 Example 61 compound 25 8.3 15.7 Example 62 compound 28 8.2 15.6 Example 63 compound 32 8.4 15.6 Example 64 compound 34 8.4 15.6 Example 65 compound 61
  • the compound of the present invention used in the organic electroluminescent device of Examples 37 to 72 has a lower sublimation temperature than the compound (compounds C, D) containing a phenanthroline moiety substituted with an aryl group during the fabrication of the device. , it was possible to prevent deterioration of the device.
  • Examples 37 to 72 comprising the compound of the present invention containing a phenanthroline moiety substituted with an alkyl group at the 2nd and 9th positions of phenanthroline as an N-type charge generating layer material are different. It was found that, compared to the devices of Comparative Examples 13 to 14, which included a compound containing a phenanthroline moiety substituted with an alkyl group at the position as an N-type charge generating layer material, it exhibited superior performance in terms of driving voltage, emission peak and current efficiency.
  • the device of Comparative Example 14 using the compound includes the devices of Comparative Examples 9 to 10 using a compound containing a phenanthroline moiety unsubstituted with an alkyl group, and phenanthroline in which an aryl group is substituted at positions 2 and/or 9
  • the efficiency characteristics were slightly improved, but the device characteristics were not significantly improved because the intrinsic active site of phenanthroline could not be blocked. .
  • the devices of Examples 37 to 72 using the compound of the present invention containing a phenanthroline moiety in which an aryl group is introduced at the 4th position while the alkyl group is introduced at No. 2 and No. 9 is an alkyl group at No. 2 and No.
  • the driving voltage is lower than that of the devices of Comparative Examples 15 to 16 using a compound containing a phenanthroline in which an aryl group is introduced at a position other than 4 (eg, position 3 or 5), and luminous efficiency was high From this, it was confirmed that even in the case of a compound having a phenanthroline moiety in which an alkyl group is substituted at both positions 2 and 9, the position at which the aryl group is introduced also greatly affects the device characteristics.

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  • Organic Chemistry (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique l'utilisant et, plus spécifiquement, un composé ayant d'excellentes capacités d'injection et de transport d'électrons, et un élément électroluminescent organique qui comprend ce dernier dans au moins une couche organique, et est ainsi amélioré en termes de tension de commande progressive, ainsi que de propriétés telles que l'efficience lumineuse, la tension de commande, la durée de vie, et analogues.
PCT/KR2021/008423 2020-07-03 2021-07-02 Composé organique et élément électroluminescent organique l'utilisant WO2022005247A1 (fr)

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