WO2016105054A2 - Composé organique luminescent et élément électroluminescent organique faisant appel audit composé - Google Patents

Composé organique luminescent et élément électroluminescent organique faisant appel audit composé Download PDF

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WO2016105054A2
WO2016105054A2 PCT/KR2015/014035 KR2015014035W WO2016105054A2 WO 2016105054 A2 WO2016105054 A2 WO 2016105054A2 KR 2015014035 W KR2015014035 W KR 2015014035W WO 2016105054 A2 WO2016105054 A2 WO 2016105054A2
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aryl
mmol
alkyl
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WO2016105054A3 (fr
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한송이
김영배
김회문
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주식회사 두산
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to include a novel azepine compound having excellent hole injection and transport ability, light emitting ability, and the like in one or more organic material layers,
  • the present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to 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 the luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • 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 a great advantage 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 as blue, green, and red dopant materials. It is used.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent hole injection, transporting ability, light emitting ability, and the like.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.
  • the present invention to achieve the above object provides a compound represented by the following formula (1).
  • R 1 and R 2 are bonded to each other to form a condensed ring with the formula (2),
  • the dotted line is the part where condensation takes place
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 );
  • Y 1 to Y 12 are each independently selected from N or C (R 3 );
  • R 3 is plural, they are the same or different from each other, and the R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C Alkynyl group of 2 to C 40 , a cycloalkyl group of C 3 to C 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, C 1 C 6 -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 - of C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, each selected from C
  • Ar 1 to Ar 5 is 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 heterocycloheteronuclear Alkyl 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 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or A diaryl phosphinyl group and a C 6 -C 60 arylamine group;
  • R 3 Ar 1 to Ar 5 alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl
  • a phosphine group, a mono or diaryl phosphinyl group and an arylamine group are each independently a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇
  • the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
  • an organic electroluminescent device comprising a compound represented by the formula (1).
  • Alkyl as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from a C6-C40 aromatic hydrocarbon in which a single ring or two or more rings are combined.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form 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, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
  • R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.
  • cycloalkyl is meant herein monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl as used herein means 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, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
  • an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
  • Compounds of the present invention are dibenzoazine (5H-dibenzo [b, d] azepine), dibenzooxepine (dibenzo [b, d] oxepine), dibenzothiepine (dibenzo [b, d] thiepine), 5-membered heteroaromatic ring moiety, indene moiety, in which benzene is condensed to dibenzosilene (5H-dibenzo [b, d] silepine) or dibenzocycloheptene (5H-dibenzo [a, d] cycloheptene) moiety, or indole moiety is condensed to form a basic skeleton, characterized in that represented by the following formula (1):
  • R 1 and R 2 are bonded to each other to form a condensed ring with the formula (2),
  • the dotted line is the part where condensation takes place
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 );
  • Y 1 to Y 12 are each independently selected from N or C (R 3 );
  • R 3 if multiple individuals which are the same or different from each other, and the R 3 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C Alkynyl group of 2 to C 40 , a cycloalkyl group of C 3 to C 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, C 1 C 6 -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 - of C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, each selected from C
  • Ar 1 to Ar 5 is 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 heterocycloheteronuclear Alkyl 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 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or A diaryl phosphinyl group and a C 6 -C 60 arylamine group;
  • R 3 Ar 1 to Ar 5 alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl
  • a phosphine group, a mono or diaryl phosphinyl group and an arylamine group are each independently a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇
  • the compound represented by Chemical Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], the glass transition temperature is high, and thus the thermal stability is excellent. In addition, the carrier transporting ability, the light emitting ability and the like are excellent. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved.
  • the compound of Formula 1 has a high triplet energy, by introducing a specific substituent in the basic skeleton condensed with a broad singlet energy level and a high triplet energy level, the energy level can be controlled higher than the dopant It can be used as a host material.
  • the compound of the present invention since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer. Therefore, when the organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, the exciton is prevented from being diffused by the compound, and thus the first exciton is diffused. Unlike conventional organic electroluminescent devices that do not include a barrier layer, the number of excitons that substantially contribute to light emission in the light emitting layer may be increased, thereby improving the luminous efficiency of the device.
  • the compound represented by Chemical Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material other than the host of the light emitting layer.
  • the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport.
  • EWG electron-withdrawing electron
  • the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron.
  • EWG electron-withdrawing electron
  • the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used.
  • an electron donor group EWG
  • the hole injection and transport is smooth.
  • it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
  • the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics.
  • the compound of formula 1 according to 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), an electron transport / injection layer material and a hole transport / injection layer Material, light emitting auxiliary layer material, life improving layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, and life improving layer material.
  • the compound of Formula 1 has a variety of substituents, particularly aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby conventional light emission It may have a higher thermal stability than the material (eg CBP).
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
  • the compound of the present invention may combine R 1 and R 2 to form a condensed heteroaromatic ring or a condensed aromatic ring represented by the formula (2).
  • R 1 and R 2 may be bonded to form condensed indene, condensed indole, condensed benzothiophene, condensed benzofuran, condensed benzosilol and the like including one or more of N, O, S, and Si.
  • the compound of the present invention may be represented by the following formula (3) or (4).
  • X 1 , X 2 and Y 1 to Y 12 are as defined in Chemical Formulas 1 and 2.
  • X 1 and X 2 are each independently O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4) (Ar 5 ), and at least one of them is preferably N (Ar 1 ).
  • Y 1 to Y 12 are each independently selected from N or C (R 3 ), and all of them are C (R 3 ) or one of them is N. desirable.
  • the compound of the present invention may be specifically selected from the group consisting of compounds represented by Formulas 1-1 to 1-18 below, but is not limited thereto.
  • Each of Y 1 to Y 12 and Ar 1 to Ar 5 is the same or different, in particular, a plurality of Ar 1 in Formulas 1-1 and 1-6 are the same as or different from each other, as defined in Formulas 1 and 2.
  • At least one of R 3 , Ar 1 to Ar 5 is an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 , It is selected from the group consisting of 5 to 60 heteroaryl groups and C 6 ⁇ C 60 arylamine group, the alkyl group, aryl group, heteroaryl group, arylamine group, each independently, deuterium, halogen, cyano group, It may be substituted with at least one member selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 arylamine group. When substituted with a plurality of substituents, they may be the same or different from each other.
  • At least one of R 3 to Ar 1 to Ar 5 except for forming a condensation in the formula (1) and 2 may be a substituent represented by the formula (5) or a phenyl group.
  • L 1 is a single bond or is selected from the group consisting of C 6 to C 18 arylene groups and heteroarylene groups having 5 to 18 nuclear atoms, preferably single bond, phenylene group, biphenylene group, carbazolyl group Can;
  • Z 1 to Z 5 are each independently N or C (R 11 ), provided that at least one of Z 1 to Z 5 is N and when there are a plurality of R 11 , they are the same or different from each other;
  • R 11 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 6 -C 40 aryl group, 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy groups, C 1 to C 40 alkyloxy groups, C 3 to C 40 cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C 6 ⁇ C 40 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 mono or diaryl phosphinyl group and C 6 ⁇ C 40 arylsilyl group selected from the group consisting of, or in combination with adjacent groups (e.g., L, other adjacent R 11 ) conden
  • the arylphosphine 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 40 aryl group, 5 to 40 heteroaryl groups, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 An arylamine group, a C 3 to C 40
  • Examples of the substituent represented by Formula 5 include a substituent represented by the following A-1 to A-15, but is not limited thereto.
  • L 1 and R 11 are each as defined in Formula 5,
  • n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R 12 , and when n is an integer of 1 to 4, R 12 is deuterium, halogen, cyano group, nitro C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 6 Aryl group of ⁇ C 40 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ⁇ C 40 60 C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 group of the arylboronic, C 6 ⁇ mono or diaryl phosphine of C 40 aryl phosphine
  • the arylphosphine 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 40 aryl group, 5 to 40 heteroaryl groups, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 An arylamine group, a C 3 to C 40 cycl
  • At least one of R 3 to Ar 1 to Ar 5 except for forming a condensation in the formula (1) and 2 may be a substituent represented by the following formula (6).
  • L 2 is a single bond or is selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, or a phenylene group, a biphenylene group, or a carbazolyl group.
  • R 13 and R 14 are each independently a C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C 6 ⁇ selected from the group consisting of an aryl amine of the C 60 Or R 13 and R 14 may combine to form a condensed ring;
  • the alkyl group, aryl group, heteroaryl group and arylamine group of R 13 and R 14 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 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, alkyloxy group of C 1 ⁇ C 40 of the, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ alkyl silyl group of C 40, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 mono or diary
  • the compounds of the present invention may be specifically represented as compounds of the structures exemplified below, but are not limited thereto.
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers.
  • a compound represented by the formula (1) includes a compound represented by the formula (1).
  • the compound may be used alone, or two or more kinds thereof may be mixed and used.
  • 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 auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by Formula 1 have.
  • the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.
  • the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, electron blocking layer, light emission
  • the auxiliary layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.
  • the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.
  • the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly
  • 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, it is possible to use conventional materials known in the art.
  • a target compound A-26 (5.65 g, yield 75%) was obtained by the same method as Synthesis Example 1, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.
  • a target compound B-26 (5.80 g, yield 77%) was obtained by the same method as Synthesis Example 10, except using, 1'-biphenyl] -4-amine (4.76 g, 10.00 mmol).
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. 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.
  • ITO Indium tin oxide
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound A-14 as a light emitting host material when forming the emission layer.
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. 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.
  • ITO Indium tin oxide
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / A-41 to L-53 + 10% (piq) 2 Ir (acac) (30nm) / BCP (10 nm) /
  • An organic electroluminescent device was manufactured by laminating in order of Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • a red organic electroluminescent device was manufactured in the same manner as in Example 33, except that CBP was used instead of the compound of Synthesis Example 6 as a light emitting host material when forming the emission layer.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • M-MTDATA 60nm) / Compound A-26 (80nm) / DS-H522 + 5% DS-501 (30nm) / BCP (10nm) / Alq3 (30) synthesized in Example 5 on the prepared ITO transparent electrode
  • An organic EL device was manufactured in the order of nm) / LiF (1 nm) / Al (200 nm).
  • DS-H522 and DS-501 used in device fabrication are products of Doosan Electronics BG, and the structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 , and BCP are as follows.
  • An organic EL device was manufactured in the same manner as in Example 61, except that A-64 to L-64 were used instead of the compound A-26 used as the hole transport layer material in forming the hole transport layer in Example 61.
  • An organic EL device was manufactured in the same manner as in Example 61, except that NPB was used as the hole transport layer material instead of Compound A-26 used as the hole transport layer material when forming the hole transport layer in Example 61.
  • the structure of the NPB used is as follows.
  • Example 61 A-26 4.8 20.8
  • Example 62 A-64 4.9 20.3
  • Example 64 B-64 4.8 20.4
  • Example 65 C-26 4.8 20.4
  • Example 66 C-64 4.7 20.2
  • Example 67 D-26 4.7 21.3
  • Example 68 D-64 4.6 21.5
  • Example 69 E-26 4.8 21.2
  • Example 70 E-64 4.9 22.3
  • Example 71 F-26 4.9 21.1
  • Example 72 F-64 4.8 20.4
  • Example 73 G-26 4.8 20.9
  • Example 74 G-64 4.7 22.1
  • Example 75 H-26 5.0 20.8
  • Example 76 H-64 5.1 21.4
  • Example 77 I-26 4.8 21.6
  • Example 78 I-64 4.9 21.7
  • Example 80 J-64 4.7 20.7
  • Example 81 K-26 5.1 20.9
  • Example 82 K-64 5.0 20.4
  • the organic EL device (the organic EL device manufactured in each of Examples 61 to 84) using the compounds (A-26 to L-64) according to the present invention as the hole transport layer was conventionally used NPB. Compared with the organic EL device (organic EL device of Comparative Example 3), it was found that the device exhibited better performance in terms of current efficiency and driving voltage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)

Abstract

La présente invention concerne un nouveau composé ayant une excellente capacité d'émission de lumière, et un élément électroluminescent organique présentant des caractéristiques améliorées, telles que le rendement lumineux, la tension d'attaque et la durée de vie, par le fait qu'il contient le nouveau composé dans une ou plusieurs couches de matériau organique.
PCT/KR2015/014035 2014-12-24 2015-12-21 Composé organique luminescent et élément électroluminescent organique faisant appel audit composé WO2016105054A2 (fr)

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WO2017099360A1 (fr) * 2015-12-08 2017-06-15 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
CN108290900A (zh) * 2015-12-08 2018-07-17 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
CN109096125A (zh) * 2017-06-20 2018-12-28 三星显示有限公司 稠环化合物和包括该稠环化合物的有机发光装置
JP2020132579A (ja) * 2019-02-20 2020-08-31 国立大学法人静岡大学 化合物、蓄電池用活物質、ｎ型半導体材料、水素貯蔵材料、及び化合物の製造方法

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KR102656920B1 (ko) * 2016-12-20 2024-04-16 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102663762B1 (ko) * 2019-06-24 2024-05-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102663763B1 (ko) * 2019-07-22 2024-05-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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JP5804797B2 (ja) 2011-06-28 2015-11-04 キヤノン株式会社 ベンゾトリフェニレノフラン化合物およびそれを有する有機発光素子

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017099360A1 (fr) * 2015-12-08 2017-06-15 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
CN108290900A (zh) * 2015-12-08 2018-07-17 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
CN109096125A (zh) * 2017-06-20 2018-12-28 三星显示有限公司 稠环化合物和包括该稠环化合物的有机发光装置
JP2019006765A (ja) * 2017-06-20 2019-01-17 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 縮合環化合物、及びそれを含む有機発光素子
US11706973B2 (en) 2017-06-20 2023-07-18 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
JP2020132579A (ja) * 2019-02-20 2020-08-31 国立大学法人静岡大学 化合物、蓄電池用活物質、ｎ型半導体材料、水素貯蔵材料、及び化合物の製造方法
JP7212220B2 (ja) 2019-02-20 2023-01-25 国立大学法人静岡大学 化合物、蓄電池用活物質、ｎ型半導体材料、水素貯蔵材料、及び化合物の製造方法

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