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WO2018194277A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2018194277A1
WO2018194277A1 PCT/KR2018/003400 KR2018003400W WO2018194277A1 WO 2018194277 A1 WO2018194277 A1 WO 2018194277A1 KR 2018003400 W KR2018003400 W KR 2018003400W WO 2018194277 A1 WO2018194277 A1 WO 2018194277A1
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group
aryl
alkyl
boron
host
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Korean (ko)
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이창준
김태형
박호철
김영모
송효범
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Doosan Corp
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Doosan Corp
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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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer

Definitions

  • the present invention relates to an organic electroluminescent device. More specifically, the present invention relates to an organic electroluminescent device using a first host, a second host, and a dopant in a light emitting layer.
  • Organic electroluminescent (EL) devices have diversification in the field of synthesis, have excellent optical performance, and have attracted great attention in the field of application of light emitting devices.
  • the driving principle of the organic EL device is as follows. When voltage is applied between the two electrodes, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • 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 light emission colors. In addition, 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 the light emission efficiency through 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 luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 hole blocking layer
  • anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
  • 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. Is being used.
  • CBP has shown excellent properties as a phosphorescent host material.
  • An object of the present invention is to solve the conventional problems and to provide a high efficiency, low voltage and long life through the organic EL device and its application.
  • the present invention is a.
  • organic electroluminescent layer disposed between the anode and the cathode, the organic EL layer comprising: a light emitting layer comprising: i) a first host, ii) a second host, and iii) a dopant;
  • the energy gap E of the first host 1H and the second host 2H satisfies that E 2H & gt ; E 1H ;
  • a half value width of the mixture of the first host and the second host is 40 nm or more and 100 nm or less;
  • the maximum light emission wavelength of the mixture of the first host and the second host is shifted to a longer wavelength at least 30 nm than the maximum light emission wavelength of the second host;
  • the electron affinity (EA) and ionization potential (IP) of the first host (1H), the second host (2H), and the dopant (D) satisfy all of the following relations (1) to (3): Provided is a light emitting device.
  • the organic electroluminescent device according to an example of the present invention may have high efficiency, low voltage and long life in phosphorescent green and red devices.
  • 1 shows an energy diagram of a first host, a second host, and a dopant.
  • FIG. 2 shows the maximum emission wavelength of the first host and the second host, the mixture of the first host and the second host, and the dopant.
  • Halogen in the present invention means any one of fluorine, chlorine, bromine or iodine or both.
  • alkyl refers to a monovalent substituent derived from a straight or branched chain 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 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 means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 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, fluorenyl, and the like.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 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 in which the two or more rings are 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, benzothiazolyl, carbazolyl, benzofuranyl, benzothiophenyl 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, puriny
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 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, 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 60 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, adamantyl, and the like.
  • Heterocycloalkyl as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of 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.
  • heterocycloalkyl include, but are not limited to, morpholinyl, piperazinyl, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • TTA triplet-triple annihilation and triplet-triplet annihilation
  • a mixture of at least two organic compounds is used, preferably a first host and a second host mixture.
  • the characteristic of this mixture is that the wavelength of each maximum emission is such that the second host is shorter than the first host.
  • the wavelength of the maximum emission of the mixture of the two hosts is shifted to a longer wavelength than the wavelength of the maximum emission of each host, and the half width of the emission spectrum (FWHM) becomes very wide and behaves like a third new material.
  • TTA triplet-triple extinction
  • the organic electroluminescent device for achieving the object of the present invention is as follows.
  • organic electroluminescent layer disposed between the anode and the cathode, the organic EL layer comprising: a light emitting layer comprising: i) a first host, ii) a second host, and iii) a dopant;
  • the energy gap E of the first host 1H and the second host 2H satisfies that E 2H & gt ; E 1H ;
  • a half value width of the mixture of the first host and the second host is 40 nm or more and 100 nm or less;
  • the maximum light emission wavelength of the mixture of the first host and the second host is shifted to a longer wavelength at least 30 nm than the maximum light emission wavelength of the second host;
  • the range of the half value width of the mixture of the first host and the second host is limited to the range of actual experimental results.
  • the maximum emission wavelength of the mixture of the first host and the second host may be shifted to a longer wavelength than the maximum emission wavelength of the second host, and a value of 30 nm may mean a minimum value of long wavelength shift.
  • EA D is the electron affinity of the dopant
  • EA 2H refers to the electron affinity of the second host.
  • IP 1H means ionization potential of the first host
  • IP 2H means ionization potential of the second host
  • IP D means ionization potential of the dopant
  • the difference in electron affinity between the dopant and the second host indicates the extent to which electrons injected from the electrode can effectively move from the host to the dopant or energy can move effectively from the host to the dopant, and a value of 0.5 is not generally known. It is characterized by the characteristics of the material and the object of the present invention.
  • the difference between the dopant and the first host is related to the movement of holes injected from the electrode, and the value of 0.5 is not generally known and is characterized by the characteristics of the material of the company and the purpose of the present invention.
  • the difference between the ionization potential of the first host and the second host is greater than 0, so that the ionization potential of the first host is smoothly injected and the electrons are smoothly injected from the cathode, as shown in FIG.
  • the two hosts have an off-set energy level so that the electron affinity of the second host has an appropriate position.
  • the electron affinity EA of the first host 1H and the second host 2H may be an organic electroluminescent device satisfying the following relation (4):
  • EA 1H refers to the electron affinity of the first host
  • EA 2H means the electron affinity of the second host
  • the maximum light emission wavelength of the mixture of the first host and the second host may be an organic electroluminescent device having a shorter wavelength than the maximum light emission wavelength of the dopant.
  • the first host may be a compound represented by Chemical Formula 1
  • the second host may be an organic electroluminescent device which is a compound represented by Chemical Formula 2 or Chemical Formula 3 below:
  • n are each independently an integer from 1 to 4.
  • X 1 is selected from the group consisting of O, S, Se, N (R 3 ), C (R 4 ) (R 5 ) and Si (R 6 ) (R 7 ),
  • R 1 and R 2 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, wherein each of R 1 and R 2 are a plurality of Are the same as
  • R 3 to R 7 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 7 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • Y 1 is N (R 8 ) or C (R 9 ) (R 10 );
  • Z 1 to Z 4 are each independently N or C (Ar 1 );
  • Z 5 to Z 10 are each independently N or C (Ar 2 );
  • R 8 to R 10 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • Ar 1 and Ar 2 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • the aromatic ring, the non-aromatic condensed polycyclic ring, the aromatic hetero ring, and the non-aromatic condensed heteropoly ring formed by bonding are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C
  • Rossi claw alkyl group C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl sulfonyl group, C 6 ⁇ C 60 aryl sulfonyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 of Aryl boron group, C 6 -C 60 arylphosphanyl group, C 6 -C 60 mono or diaryl phosphinyl group, C 1 -C 40 alkylcarbonyl group, C 6 -C 60 arylcarbonyl group and C When unsubstituted or substituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, they are the same as or different from each other.
  • any one of R 1 and R 2 may be an organic electroluminescent device, which is a substituent represented by the following formula (4) or (5):
  • p is an integer from 0 to 7;
  • q is an integer from 0 to 11;
  • X 2 is selected from the group consisting of O, S, Se, N (R 13 ), C (R 14 ) (R 15 ) and Si (R 16 ) (R 17 ),
  • R 11 and R 12 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine P is selected from the group the group consisting of C 6 ⁇ with an aryl amine of the C 60, wherein R 11 and R1
  • R 13 to R 17 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 11 to R 17 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • Ar 1 and Ar 2 may each independently be an organic electroluminescent device that is a compound including a structure represented by the following formula (6):
  • L 1 and L 2 are each independently selected from the group consisting of a direct bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 18 is hydrogen, 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 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , 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 phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
  • the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • L 1 and L 2 may be each independently a direct bond or a linker selected from the group consisting of Formulas C-1 to C-4, may be an organic electroluminescent device.
  • R 18 is selected from the group consisting of an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms,
  • the alkyl group, aryl group and heteroaryl group of R 18 are each independently one or more substituents selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl groups When substituted with or unsubstituted with a plurality of substituents, they may be organic electroluminescent devices which are the same or different compounds.
  • R 18 may be an organic electroluminescent device which is a substituent represented by one of the following Chemical Formulas 7 to 9:
  • r is an integer from 0 to 7;
  • s is an integer from 0 to 8;
  • V 1 to V 5 are each independently N or C (R 27 );
  • X 3 is selected from the group consisting of O, S, Se, N (R 28 ), C (R 29 ) (R 30 ) and Si (R 31 ) (R 32 ),
  • X 4 is selected from the group consisting of N, C (R 33 ) and Si (R 34 ),
  • R 19 and R 20 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • R 27 to R 34 are each independently hydrogen, 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 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 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 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • the aromatic ring, the non-aromatic condensed polycyclic ring, the aromatic hetero ring, and the non-aromatic condensed heteropoly ring formed by bonding are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group,
  • Rossi claw alkyl group C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl sulfonyl group, C 6 ⁇ C 60 aryl sulfonyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 of Aryl boron group, C 6 -C 60 arylphosphanyl group, C 6 -C 60 mono or diaryl phosphinyl group, C 1 -C 40 alkylcarbonyl group, C 6 -C 60 arylcarbonyl group and C When unsubstituted or substituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, they are the same as or different from each other.
  • the substituents represented by Formulas 7 to 9 may be organic electroluminescent devices, which are substituents represented by any one of the following Formulas 10 to 13:
  • t is an integer from 0 to 11;
  • o and i are integers from 0 to 8;
  • u and j are integers from 0 to 7;
  • k is an integer from 0 to 4.
  • k ' is an integer from 0 to 6;
  • X 5 and X 7 are each independently selected from the group consisting of O, S, Se, N (R 28 ), C (R 29 ) (R 30 ) and Si (R 31 ) (R 32 ),
  • X 6 is selected from the group consisting of N, C (R 33 ) and Si (R 34 ),
  • R 21 to R 26 and R 24 ′ each independently represent hydrogen, 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 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 Aryl group, 5 to 60 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 alkylsulfonyl group, C 6 -C 60 arylsulfonyl group , C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl
  • R 28 to R 34 are as defined in claim 9.
  • the first host may be a compound represented by Chemical Formula 1
  • R 1 may be an organic electroluminescent device which is a substituent represented by Chemical Formula 4.
  • n are each independently an integer from 1 to 4.
  • p is an integer from 0 to 7;
  • X 1 is N (R 3 );
  • X 2 is N (R 13 );
  • R 3 and R 13 are each independently selected from the group consisting of an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms;
  • the alkyl group, aryl group and heteroaryl group of R 3 and R 13 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
  • X 1 may be an organic EL device, characterized in that S.
  • At least one of Z 5, Z 7 and Z 9 may be an organic electroluminescent device, characterized in that N.
  • Z 5, Z 7 and Z 9 may be N, an organic electroluminescent device characterized in that.
  • the second host is a compound represented by Chemical Formula 3;
  • R 18 may be an organic electroluminescent device, which is a substituent represented by Formula 9:
  • s is an integer from 0 to 8;
  • Z 5, Z 7 , Z 9 and X 4 are N;
  • Z 6, Z 8 and Z 10 are each independently C (Ar 2 );
  • Ar 2 and R 20 are each independently selected from the group consisting of an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms;
  • the alkyl group, aryl group and heteroaryl group of Ar 2 and R 20 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
  • the first host is a compound represented by the formula A-1 and A-2
  • the second host is a compound represented by any one of the formula B-1 to B-10 It may be selected from the group consisting of.
  • the first host is selected from the group consisting of compounds represented by any one of the following formulas A-1 to A-3,
  • the second host may be selected from the group consisting of compounds represented by any one of Formulas B-1 to B-11, but is not limited thereto.
  • An organic electroluminescent device is an anode, a cathode and an organic electroluminescent layer disposed between the anode and the cathode, i) a first host and ii) a second host, and iii A light emitting layer containing a dopant.
  • 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, an emission auxiliary layer, an emission layer, an electron transport layer, and a cathode are sequentially stacked. .
  • an electron injection layer may be further 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 between the electrode and the organic EL layer interface.
  • an electron transport auxiliary layer may be added between the emission layer and the electron transport layer.
  • the organic electroluminescent device of the present invention is an organic EL layer by a material and method known in the art, except that the organic electroluminescent device comprises a light emitting layer comprising i) a first host, ii) a second host, and iii) a dopant. And it can be manufactured by forming an electrode.
  • the organic EL layer can 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 EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like can be used.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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 are not limited thereto.
  • a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophen
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And 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 may be used.
  • Compounds A-1, A-2 and A-3 used as the first host, and Compounds B-1 to B-11 used as the second host are as follows.
  • Ionization potential was measured by CV (cyclic voltammetry) method (Princeton, 273A), energy gap was measured by UV-Vis spectrophotometer, (JASCO, V-500) was used. Electron affinity was calculated from the measured values of ionization potential and energy gap.
  • the emission wavelength was measured by PL (photoluminescence) spectrum, and (PerkinElmer, LS-55) was used.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV-OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to the evaporator.
  • ITO Indium tin oxide
  • M-MTDATA 60 nm) / TCTA (80 nm) / organic compound + 10% Ir (ppy) 3 / (300nm) / BCP (10 nm) / Alq 3 (30nm) / LiF (1)
  • the organic EL device was fabricated by laminating in order of nm) / Al (200 nm).
  • the structure of m-MTDATA, TCTA, Ir (ppy) 3 , BCP is as follows. In the case of organic compounds, the No. The ratio of the 1st host and the 2nd host of the same number of 1-17 was mixed and used in the ratio of 5: 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the following CBP was used instead of the organic compound as a light-emitting host material in the manufacture of the organic EL device.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that A-1 was used instead of the organic compound as a light-emitting host material when fabricating the organic EL device.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that B-1 was used instead of the organic compound as a light-emitting host material in fabricating the organic EL device.
  • Example 1 A-2 B-1 0.30 0.62 0.32 0.24 0.41
  • Example 2 A-1 B-2 0.06 0.60 0.54 0.39 0.06
  • Example 3 A-2 B-2 0.08 0.75 0.67 0.24 0.06
  • Example 4 A-1 B-3 0.17 0.32 0.15 0.39 0.45
  • Example 5 A-1 B-4 0.10 0.20 0.10 0.44 0.42
  • Example 6 A-1 B-5 0.03 0.50 0.47 0.39 0.13
  • Example 7 A-2 B-5 0.05 0.65 0.60 0.24 0.13
  • Example 8 A-1 B-6 0.23 0.49 0.26 0.39 0.34
  • Example 9 A-2 B-6 0.25 0.64 0.39 0.24 0.34
  • Example 10 A-1 B-7 0.28 0.63 0.35 0.39 0.39 0.
  • the lifetime T95% is the time taken to reduce from the initial luminance to 95%.
  • Example 1 A-2 B-1 5.5 57.4 516 126
  • Example 2 A-1 B-2 5.4 54.9 516 165
  • Example 3 A-2 B-2 5.6 55.8 517 120
  • Example 4 A-1 B-3 5.6 55.7 516 121
  • Example 5 A-1 B-4 5.7 52.5 516 180
  • Example 6 A-1 B-5 5.7 56.8 517 75
  • Example 7 A-2 B-5 5.7 56.1 516 70
  • Example 8 A-1 B-6 5.8 51.2 517 68
  • Example 9 A-2 B-6 5.7 50.6 516 65
  • Example 10 A-1 B-7 5.9 51.6 517 81
  • Example 11 A-2 B-7 5.9 52.3 517 79
  • Example 12 A-1 B-8 5.7 53.6 517 76
  • Example 13 A-2 B-8 5.7 52.9 516 79
  • the green organic EL device (Examples 1 to 17) using the compound according to the present invention in the light emitting layer has better performance in terms of current efficiency, driving voltage, and lifetime compared to Comparative Examples 1 to 4. It was found to indicate.

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Abstract

La présente invention concerne un nouveau composé présentant d'excellentes performances de luminescence et un dispositif électroluminescent organique qui comprend le nouveau composé dans une ou dans plusieurs couches organiques de celui-ci et qui présente ainsi une amélioration des caractéristiques telles que l'efficacité lumineuse, la tension d'attaque et la durée de vie.
PCT/KR2018/003400 2017-04-17 2018-03-23 Dispositif électroluminescent organique Ceased WO2018194277A1 (fr)

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US12435073B2 (en) 2019-08-19 2025-10-07 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

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KR102070941B1 (ko) * 2017-06-21 2020-01-29 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102238703B1 (ko) * 2018-11-09 2021-04-09 주식회사 엘지화학 유기 발광 소자
KR102524743B1 (ko) * 2019-10-18 2023-04-24 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
WO2022181157A1 (fr) 2021-02-25 2022-09-01 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
KR102759979B1 (ko) * 2022-05-20 2025-01-23 단국대학교 천안캠퍼스 산학협력단 압전성 유기 화합물 및 이를 포함하는 압전 소자

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