WO2022015047A1 - Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant Download PDF

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WO2022015047A1
WO2022015047A1 PCT/KR2021/009043 KR2021009043W WO2022015047A1 WO 2022015047 A1 WO2022015047 A1 WO 2022015047A1 KR 2021009043 W KR2021009043 W KR 2021009043W WO 2022015047 A1 WO2022015047 A1 WO 2022015047A1
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김진웅
엄민식
김회문
정화순
배형찬
손호준
한송이
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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
    • H10K50/00—Organic light-emitting devices
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero 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
    • C07D405/02—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
    • C07D405/14—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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent electron transport ability and an organic compound having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers. It relates to an electroluminescent device.
  • 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 luminous efficiency up to four times compared to fluorescence, and thus, 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 can apply a novel fluorene-based compound to an organic electroluminescent device, and by using the novel fluorene-based compound as an electron transport layer (ETL) material, which is a common layer of the organic electroluminescent device, low voltage, high efficiency and long life characteristics All aim to provide excellent novel organic compounds.
  • ETL electron transport layer
  • the present invention includes a material for an electron transport layer with improved lifespan and improved electron injection and transport capability, a hole transport layer material with improved hole injection and transport capability, and a material for the hole transport layer including the novel organic compound, which exhibits low driving voltage and high luminous efficiency, and includes the same
  • Another object of the present invention is to provide an organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1).
  • R1 To R2 are the same as or different from each other, and each independently a C 1 ⁇ C 40 alkyl group, or a C 6 ⁇ C 60 aryl group, or combine with each other to form a condensed ring,
  • L is independently a single bond, or is selected from the group consisting of a C 6 ⁇ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
  • n is an integer from 0 to 1
  • n is an integer from 0 to 3
  • a and B are each independently selected from the group consisting of hydrogen, a cyano group, a substituent represented by the following Chemical Formula 2, a substituent represented by the following Chemical Formula 3, and a substituent represented by the following Chemical Formula 4,
  • a plurality of X is the same as or different from each other, each independently C (R) or N,
  • R is hydrogen, deuterium, halogen, cyano group, nitro group, C1 ⁇ C40 alkyl group, C 2 ⁇ C4 0 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphine group, C 6 ⁇ C 60 Mono or diarylphosphinyl group and C 6 ⁇ C 60 Selected from the group consisting of an arylamine group, and forms a condensed ring of
  • R of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, an aryl group Phosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl Amine group, C 3 ⁇ C 40
  • l is an integer from 0 to 3
  • Ar1 is plural, the same or different from each other, and each independently is a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heteroaryl group, which may form a condensed ring with adjacent X,
  • Ar2 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • the present invention includes an anode, a cathode, and one or more organic material layers interposed between the positive and negative electrodes, wherein at least one of the one or more organic layers includes a compound represented by Formula 1 above.
  • a light emitting device is provided.
  • At least one of the one or more organic material layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, It is preferably a transport layer, an electron transport auxiliary layer and/or a light emitting layer.
  • the compound represented by Formula 1 is an electron transport layer material, an electron transport auxiliary layer material, and/or a light emitting layer material.
  • the compound of the present invention Since the compound of the present invention has excellent luminous efficiency, driving voltage, lifespan, etc., it can be usefully applied as an organic material layer material of an organic electroluminescent device. , life, efficiency, etc. are greatly improved, so that it can be effectively applied to a full-color display panel.
  • FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • the present invention provides a novel fluorene-based compound excellent in luminous efficiency, driving voltage, lifespan, and the like.
  • an aliphatic ring group such as a cyclohexyl group, in which a fluorene-based compound is substituted in a spiro form may be employed as a core or a linker, and the An electron withdrawing group (EWG) having excellent electron transport ability is bonded to the phenyl group of the structure to form a basic skeleton.
  • EWG An electron withdrawing group
  • the compound represented by Chemical Formula 1 having such a structure is electrochemically stable compared to the conventionally known dimethyl fluorene structure as an aliphatic ring group is formed in the fluorene-based compound.
  • it has a flat form using a cyclic group such as pyrazine to improve the electron transfer rate and has a high triplet energy according to a short conjugation length and is generated in the light emitting layer It is possible to prevent diffusion (migration) of excitons to an adjacent electron transport layer or hole transport layer.
  • the compound of Formula 1 of the present invention when used in an organic electroluminescent device because the number of excitons contributing to light emission in the light emitting layer is increased, excellent thermal stability and carrier transport ability (especially, electron transport ability and light emitting ability) can be expected.
  • the driving voltage, efficiency, lifespan, etc. of the device can be improved, and excellent efficiency increase due to the triplet-triplet fusion (TTF) effect can be exhibited as the latest ETL material by high triplet energy.
  • TTF triplet-triplet fusion
  • the compounds represented by Formula 1 of the present invention can easily control HOMO and LUMO energy levels depending on the direction or position of a substituent, and thus can exhibit high electron transport properties in an organic electroluminescent device using such a compound.
  • At least one dibenzo-based moiety eg, dibenzofuran (DBF) or dibenzothiophene (DBT)
  • DPF dibenzofuran
  • DBT dibenzothiophene
  • EWG electron-withdrawing group
  • the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and/or red phosphorescent host material), electron transport layer/injection layer material, electron When applied as a transport auxiliary layer material, a hole transport layer/injection layer material, a light emitting auxiliary layer material, and a life improvement layer material, the performance and lifespan characteristics of the organic electroluminescent device can be greatly improved. As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.
  • a light emitting layer material blue, green and/or red phosphorescent host material
  • electron transport layer/injection layer material electron
  • electron When applied as a transport auxiliary layer material, a hole transport layer/injection layer material, a light emitting auxiliary layer material, and a life improvement layer material, the performance and lifespan characteristics of the organic electroluminescent device can be greatly improved. As a result, such an organic electroluminescent device can
  • R1 to R2 are the same as or different from each other, and are each independently a C1 ⁇ C40 alkyl group, or a C6 ⁇ C60 aryl group, or combine with each other to form a condensed ring
  • L is independently is a single bond, or is selected from the group consisting of a C6 ⁇ C18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms
  • n is an integer from 0 to 1
  • m is an integer from 0 to 3
  • a And B is each independently selected from the group consisting of hydrogen, a cyano group, a substituent represented by the following formula (2), a substituent represented by the following formula (3), and a substituent represented by the following formula (4).
  • * is a portion where a bond is formed, a plurality of Xs are the same or different from each other, and each independently represents C(R) or N, and R is hydrogen, deuterium, halogen, cyano group, or nitro group.
  • R of an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, an aryl group Phosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl Amine group, C 3 ⁇ C 40
  • the compound represented by Formula 2 may be represented by any one of Formulas 5 to 8.
  • Y is hydrogen, deuterium, halogen, cyano group, nitro group, C1 ⁇ C40 alkyl group, C2 ⁇ C4 0 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 aryl phosphine is selected from the pingi, C 6 ⁇ C 60 mono or diaryl phosphine group P and the group consisting of C
  • X and Ar1 are each as defined in Formula 1;
  • the compound represented by Formula 3 may be represented by any one of Formulas 9 to 11.
  • X is as defined in formula (1).
  • Formula 5 may be embodied as Formula 13 below.
  • Formula 5 may be embodied as Formula 14 or Formula 15 below.
  • Ar1 is as defined in Formula 1.
  • Formula 9 may be embodied as Formula 16 below.
  • Ar1 is as defined in Formula 1.
  • Chemical Formula 10 may be embodied as Chemical Formula 17 below.
  • Ar1 is as defined in Formula 1.
  • Formula 11 may be embodied as Formula 18 below.
  • Ar1 is as defined in Formula 1.
  • the L may be a single bond or a linker selected from the following L-1 to L-18.
  • * is a portion where a bond is formed.
  • the compound represented by Formula 1 according to an example of the present invention described above may be further specified as a compound represented by any one selected from the group consisting of the compounds exemplified below.
  • the compound represented by Formula 1 of 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.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 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 40 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
  • 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 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.
  • arylamine refers to an amine substituted with an aryl having 6 to 40 carbon atoms.
  • 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 and piperazine.
  • alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl refers to 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.
  • the compound represented by Formula 1 adopts fused fluorene as a core, and an electron withdrawing group (EWG) having excellent electron transport ability is bonded to the phenyl group of the core structure to release electrons Since the receiving property is strong, when the compound of Formula 1 is applied as an electron transport layer, electrons can be well received from the cathode, and thus electrons can be smoothly transferred to the light emitting layer. Therefore, the present invention can be used as the compound for the electron transport layer represented by the formula (1).
  • EWG electron withdrawing group
  • the electron transport layer serves to receive electrons from the cathode and move the electrons to the light emitting layer. Accordingly, the stronger the material used for the electron transport layer, the more suitable it is to move electrons.
  • the electron transport layer serves to move electrons injected from the cathode to an adjacent layer, specifically, a light emitting layer, and the compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material. , 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, and non-limiting examples of the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, and a tria.
  • Sol-based compounds isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, aluminum complexes (eg, Alq3 (tris(8-quinolinolato)) -aluminum (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complex (eg Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These are used alone or in two types more can be mixed.
  • organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a 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 is and a compound represented by Formula 1 above.
  • the compound may be used alone or in mixture of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer is represented by Formula 1 including compounds.
  • the organic material layer including the compound of Formula 1 is a light emitting layer, an electron transport layer, and 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, and in this case, the compound of Formula 1 may be included as the host material.
  • the light emitting layer of the present invention may include a known compound in the art other than the compound of Formula 1 as a host.
  • the compound represented by Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic electroluminescent device (luminous efficiency and power efficiency), lifespan, luminance, and driving voltage can be improved.
  • the compound represented by 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 electroluminescent 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.
  • 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 the compound represented by Formula 1, preferably the light emitting layer, more preferably a phosphorescent host may include a compound represented by Formula 1 above.
  • an electron injection layer may be additionally stacked on the electron transport layer.
  • the structure of the organic electroluminescent device of the present invention may be 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 of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by 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 method.
  • the substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet may be used.
  • a cathode material a cathode material known in the art may be used 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), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2: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.
  • any negative electrode material known in the art may be used without limitation.
  • a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.
  • the target compound D-1 (35.64 g, yield 72%) was obtained by column chromatography.
  • quinolin-8-ylboronic acid or quinolin-5-ylboronic acid is used instead of the above compounds and quinolin-6-ylboronic acid, A-24, A-25, A-26, B-24, B-25, respectively.
  • B-26, C-24, C-25, C-26, A-27, A-28, A-29, B-27, B-28, B-29, C-27, C-28, C -29 can be obtained.
  • the target compound B-39 (27.29 g, yield 72%) was obtained by column chromatography.
  • the target compound B-43 (27.67 g, yield 72%) was obtained by column chromatography.
  • 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, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and vacuum evaporator The substrate was transferred to
  • Each compound of m-MTDATA (60 nm)/TCTA (80 nm)/ A-5-8, B-5-8, C-5-8 + 10% Ir(ppy) 3 ( 30 nm)/BCP (10 nm)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic EL device.
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound A-5 as a light emitting host material when the light emitting layer was formed.
  • Example 1 A-5 5.43 515 44.2
  • Example 2 A-6 5.52 517 42.2
  • Example 3 A-7 5.34 518 45.2
  • Example 4 A-8 5.69 516 43.5
  • Example 5 B-5 5.43 515 44.2
  • Example 6 B-6 5.69 514 43.5
  • Example 7 B-7 5.43 515 44.2
  • Example 8 B-8 5.55 517 42.3
  • Example 9 C-5 5.44 518 49.1
  • Example 10 C-6 5.53 517 44.8
  • Example 11 C-7 5.35 517 45.4
  • Example 12 C-8 5.69 516 43.6 Comparative Example 1 CBP 6.52 516 38.2
  • 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 13, except that Alq3 was used instead of Compound A-5 as the electron transport layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 13, except that Compound A-5 was not used as the electron transport layer material.
  • NPB, AND, and Alq3 used in Examples 13 to 130 and Comparative Examples 2 and 3 are as follows.
  • Example 13 A-5 3.8 456 6.8
  • Example 14 A-6 4.0 457 6.6
  • Example 15 A-7 3.6 456 6.6
  • Example 16 A-8 4.0 453 6.5
  • Example 17 A-9 3.8 456 6.7
  • Example 18 A-10 3.8 456 6.8
  • Example 19 A-11 4.0 456 6.6
  • Example 20 A-12 4.0 457 6.6
  • Example 21 A-13 3.8 456 6.8
  • Example 22 A-14 4.0 453 6.5
  • Example 23 A-15 4.1 453 6.5
  • Example 24 A-16 3.8 456 6.8
  • Example 25 A-17 4.0 456 6.6
  • Example 26 A-18 3.6 456 6.6
  • Example 27 A-19 3.8 456 6.8
  • Example 28 A-20 4.0 457 6.6
  • Example 29 A-21 3.8 456 6.7
  • Example 30 A-22 3.8 456 6.8
  • Example 31 A-23 3.9 457 6.6
  • Example 32 A-24 3.6 456 6.8
  • Example 33 A-25 3.7 456 6.5
  • the blue organic electroluminescent device (Examples 13 to 130) using the compound of the present invention for the electron transport layer is a blue organic electroluminescent device using the conventional Alq3 for the electron transport layer (Comparative Example 2) and electrons It was found that the blue organic EL device without a transport layer (Comparative Example 3) exhibited superior performance in terms of driving voltage, emission peak and current efficiency.
  • 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. and transferred the substrate to a vacuum evaporator.
  • ITO indium tin oxide
  • NPB, ADN and Alq3 used at this time are as follows.
  • Example 131 in the same manner as in Example 131, except that compound D-1 used as an electron transport auxiliary layer material was not used, and Alq3, an electron transport layer material, was deposited at 30 nm instead of 25 nm. An electroluminescent device was fabricated.
  • the blue organic electroluminescent device of Examples 131 to 138 including an electron transport auxiliary layer formed of the compound according to the present invention is Comparative Example 4 comprising an electron transport layer made of Alq3 without an electron transport auxiliary layer It was found that the organic electroluminescent device exhibited superior performance in terms of current efficiency and driving voltage.
  • organic layer 31 hole transport layer

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Abstract

La présente invention concerne un nouveau composé présentant d'excellentes performances électroluminescentes et un dispositif électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé comme matériau pour une couche organique d'un dispositif électroluminescent organique, de préférence un matériau pour une couche de transport d'électrons ou un matériau pour une couche de transport d'électrons auxiliaire, et permet ainsi d'améliorer l'efficacité de luminescence, la tension d'attaque, la durée de vie et d'autres paramètres similaires du dispositif électroluminescent organique.
PCT/KR2021/009043 2020-07-14 2021-07-14 Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant WO2022015047A1 (fr)

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CN114716418A (zh) * 2022-03-14 2022-07-08 上海钥熠电子科技有限公司 杂环烷烃衍生物、有机光电器件和显示或照明装置
EP4299573A1 (fr) 2022-06-30 2024-01-03 Novaled GmbH Compose, materiau semi-conducteur organique le comprenant, dispositif electronique organique le comprenant et procede de preparation du dispositif electronique organique
CN114716418B (zh) * 2022-03-14 2024-06-07 上海钥熠电子科技有限公司 杂环烷烃衍生物、有机光电器件和显示或照明装置

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EP4299573A1 (fr) 2022-06-30 2024-01-03 Novaled GmbH Compose, materiau semi-conducteur organique le comprenant, dispositif electronique organique le comprenant et procede de preparation du dispositif electronique organique
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