WO2017188597A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2017188597A1
WO2017188597A1 PCT/KR2017/002780 KR2017002780W WO2017188597A1 WO 2017188597 A1 WO2017188597 A1 WO 2017188597A1 KR 2017002780 W KR2017002780 W KR 2017002780W WO 2017188597 A1 WO2017188597 A1 WO 2017188597A1
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alkyl
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이용환
김영배
김회문
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주식회사 두산
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07—ORGANIC CHEMISTRY
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K50/14—Carrier transporting layers
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    • H10K50/17—Carrier injection layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
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    • 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
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission.
  • An organic electroluminescent device having efficiency and improved lifespan characteristics.
  • the organic electroluminescent (EL) device (hereinafter, simply referred to as 'organic EL device') of blue electroluminescence using anthracene single crystal was observed based on observation of Bernanose organic thin film emission in the 1950s. Research has continued. In 1987, Tang presented an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, long life organic EL device, it has evolved to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
  • 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, and yellow and orange light emitting materials required to realize a better natural color, depending on the light emission color.
  • 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.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp).
  • Metal complex compounds containing Ir, such as 2 are used.
  • 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
  • An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and capable of improving the bonding force between holes and electrons.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage, high luminous efficiency, and improved lifespan characteristics.
  • the present invention provides a compound represented by the following formula (1):
  • L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
  • Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
  • Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
  • n and m are each independently an integer of 0 to 3
  • R 1 and R 2 are the same as or different from each other, and 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, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
  • the arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 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 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, a C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ mono or diaryl phosphine of C 60 blood group
  • the present invention provides a composition for an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (9):
  • g and j are each independently an integer from 0 to 4.
  • h and i are each independently an integer from 0 to 3;
  • Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;
  • R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of each other Alkynyl group, C 6 ⁇ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ⁇ C 40 alkyl phosphine group, C 1 ⁇ alkyl Phosphinicosuccinic group of C 40, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl
  • the present invention 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 provides an organic electroluminescent device comprising the compound of 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 to C60 aromatic hydrocarbon combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form 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 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, 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 60 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 6 to 60 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 of the present invention is excellent in thermal stability and phosphorescence properties, it can be usefully applied as a material of the organic material layer of the organic electroluminescent device.
  • the organic electroluminescent device comprising the compound according to the present invention in the organic material layer enables to manufacture an organic electroluminescent device having excellent luminous performance, low driving voltage, high efficiency and long life, and furthermore, the performance and lifespan are greatly improved.
  • Color display panels can also be manufactured.
  • L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
  • Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
  • Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
  • n and m are each independently an integer of 0 to 3
  • R 1 and R 2 are the same as or different from each other, and 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, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
  • the arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 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 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, a C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ mono or diaryl phosphine of C 60 blood group
  • the present invention relates to a novel carbazole compound having excellent thermal stability and phosphorescence properties, and more particularly, a wide band gap (sky blue to red) by controlling energy levels by various substituents symmetric or asymmetric to the carbazole base skeleton. It provides a compound having). However, at this time, the coupling position thereof is not particularly limited.
  • novel organic compound provided by the present invention is characterized by represented by the following formula (1):
  • L 1 to L 4 are the same as or different from each other, and each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms,
  • Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
  • Ar 2 and Ar 3 are different from each other, each independently selected from the group consisting of hydrogen, an aryl group of C 6 ⁇ C 60 and a heteroaryl group of 5 to 60 nuclear atoms,
  • n and m are each independently an integer of 0 to 3
  • R 1 and R 2 are the same as or different from each other, and 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, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine group , C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group , A C 6 -C 60 arylphosphine group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group;
  • the arylene group and heteroarylene group of L 1 to L 4 , Ar 1 To aryl group and heteroaryl group of Ar 3 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 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, a C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ mono or diaryl phosphine of C 60 blood group
  • the compound of Formula 1 which is used as a phosphorescent host in the present invention, has a wide bandgap (sky blue to red) by controlling energy levels by various substituents symmetrical or asymmetric to the carbazole-based skeleton. Therefore, when the compound represented by Chemical Formula 1 is used in the organic material layer of the organic electroluminescent device, the phosphorescence property may be improved, and the electron and / or hole transport ability and the light emission capability may be enhanced.
  • the compound represented by Formula 1 of the present invention exhibits excellent properties as a light emitting host material compared to the conventional CBP due to the electrochemical stability due to the substitution of carbazole 3, 6 position, the host material of the light emitting layer More preferably used as.
  • the compound represented by Chemical Formula 1 has various aromatic rings bonded to the carbazole-based basic skeleton as a substituent to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature and thus higher than the conventional CBP. May have thermal stability.
  • the entire molecule has a bipolar (bipolar) nature of the various aromatic ring substituents to increase the binding force between the hole and the electron, it can exhibit excellent properties as a host material of the light emitting layer compared to the conventional CBP.
  • the compound represented by Formula 1 is an N-type material having an electron withdrawing property having a high electron absorbing property
  • the substituent bonded to the carbazole base skeleton is excellent when the hole transport compound is used as the second host.
  • An organic electroluminescent device having light emission performance, low driving voltage, high efficiency and long life can be manufactured.
  • the bandgap is equal to or greater than that of the compound of Formula 1 or a material having a greater LUMO value, when mixed with the compound of Formula 1 in an appropriate ratio, the injected holes and electrons are balanced to provide an organic light emitting device. Can help improve overall performance, especially lifespan.
  • Formula 1 may be represented by the following Formula 2:
  • L 1 to L 4 , Ar 1 to Ar 3 , n, m, R 1 and R 2 are each as defined in Formula 1.
  • the Ar 1 may be selected from the group consisting of substituents of the following Chemical Formulas 3 to 8:
  • a and b are each independently an integer of 0 to 4.
  • X 1 to X 5 and X 7 to X 12 are each independently N or C (R 3 );
  • X 6 is O or S
  • R 3 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an alkyl of C 1 ⁇ C 40 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 group, C 6 ⁇ mono or diaryl phosphine of C 60 blood
  • 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 3 to R 5 Boron group, aryl phosphine group, mono or diaryl phosphinyl group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, halogen C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60
  • Ar 2 and Ar 3 may be selected from the group consisting of the following substituents:
  • Z 1 to Z 5 are the same as or different from each other, and are each independently N or C (R 6 );
  • Y 1 and Y 2 are the same as or different from each other, and are each independently selected from the group consisting of a single bond, C (R 7 ) (R 8 ), N (R 9 ), O and S, but both Y 1 and Y 2 Not a single bond;
  • c is an integer from 0 to 3;
  • d and e are each independently an integer of 0 to 4.
  • f is an integer from 0 to 2;
  • R 6 to R 12 are the same as or different from each other, and are each independently selected from a group consisting of deuterium, a halogen, a cyano group, an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, or are bonded to an adjacent group To form a condensed ring,
  • the aryl group and heteroaryl group of R 6 to R 12 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 Alky Neyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine aryl boron group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 of Unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a C 6 -C 60 arylphosphine group, a C 6 -C 60
  • the compound represented by Formula 1 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto.
  • composition for an organic electroluminescent device comprising a compound represented by the formula (1) and a compound represented by the following formula (9):
  • g and j are each independently an integer from 0 to 4.
  • h and i are each independently an integer from 0 to 3;
  • Ar 4 and Ar 5 are the same as or different from each other, and are each independently a C 6 to C 60 aryl group or a nuclear atom having 5 to 40 heteroaryl groups;
  • R 13 to R 16 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of each other Alkynyl group, C 6 ⁇ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryl Amine group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 aryl boron group, C 1 ⁇ C 40 alkyl phosphine group, C 1 ⁇ alkyl Phosphinicosuccinic group of C 40, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl
  • Formula 9 may be represented by the following Formula 10 to 13.
  • Ar 4 and Ar 5 , g, h, i, j, R 13 to R 16 are each the same as defined in Formula 9.
  • the Ar 4 And Ar 5 may be the same as or different from each other, and may be each independently an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 5 to 40 nuclear atoms.
  • the compound represented by Formula 9 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto:
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device includes (i) an anode, (ii) a cathode and (iii) one or more organic material layers interposed between the anode and the cathode, At least one of the one or more organic material layers may include a compound represented by Formula 1, and preferably include a composition including at least one of compounds represented by Formula 1 and compounds represented by Formula 9, respectively. have.
  • At least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1).
  • the organic material layer including the compound of Formula 1 may be a light emitting layer.
  • the light emitting layer of the organic EL device may include a host material, wherein the host material may include the compound of formula (1).
  • the compound of Formula 1 when included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.
  • the compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material, and more preferably, the compound of Chemical Formula 9 is the first phosphorescent host of the emission layer, The compound of Formula 1 may be used as a second phosphorescent host of the emission layer.
  • the structure of the organic electroluminescent device is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron injection layer may be further stacked on the electron transport layer.
  • at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer may be represented by Formula 1 according to the present invention.
  • It may include a compound, preferably as a host of the light emitting layer may include a compound represented by the formula (1) according to the present invention, more preferably, the compound of formula 9 according to the present invention as a first phosphorescent host of the light emitting layer
  • the compound of Formula 1 may be used as a second phosphorescent host of the emission layer.
  • the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.
  • 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.
  • a ceramic crucible having high thermal conductivity is used as a method of forming the organic layer of the organic electroluminescent device by vacuum deposition, and should be designed so that stepwise and continuous evaporation control is possible and no organic splashing occurs.
  • the temperature of the evaporation source is not properly raised, the organic material that reaches the evaporation temperature in an excessively short time is splashed, and the inlet of the evaporation source is blocked, and thus the deposition rate of the organic material is not constant and thus the desired thin film characteristics are not obtained.
  • the organic material will be discolored or discolored during deposition.
  • the organic material has a characteristic of being deposited by melting or sublimation depending on the material.
  • the compound In the case of deposition by the sublimation method, the compound immediately forms a organic layer through a sublimation process in the solid state, whereas in the case of the melting method The solid is vaporized through the liquid to form an organic layer.
  • the melting method since the material undergoes one more phase change than the sublimation method, it is difficult to control the deposition temperature or the uniformity.
  • the compound represented by Chemical Formula 1 according to the present invention may be deposited by a sublimation method and may have uniform thin film properties, thereby improving light emission characteristics.
  • the compound of Formula 1 according to the present invention when used as a hole injection / transport layer material or a blue, green and / or red phosphorescent host material, an electron injection / transport layer material of an organic electroluminescent device, For example, compared to CBP), the efficiency and lifespan of the organic EL device can be greatly improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • the positive electrode material usable 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 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.
  • usable negative electrode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.
  • Step 1 3- Chloro -6- ( Triphenyl 2-yl) -9H- Carbazole (3-chloro-6- ( triphenylen -2-yl) -9H-carbazole)
  • Step 1 3- Chloro -6- (3- (phenanthren-9-yl) phenyl) -9H- Carbazole synthesis
  • 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in ⁇ step 2> of Preparation Example 5 3-chloro-6- ( Naphthalene-2 instead of (9,9-dimethyl-9H-flowen-2-yl) boronic acid using 3- (phenanthren-9-yl) phenyl) -9H-carbazole (4.53 g, 10 mmol)
  • A-6 was obtained by the same procedure as in ⁇ Step 2> of Preparation Example 5, except that ilboonic acid (1.71 g, 10.0 mmol) was used.
  • Step 1 3-([1,1 ': 3', 1 "- Terphenyl ] -5'-day) -6- Chloro -9H- Carbazole Synthesis of (3-([1,1 ': 3', 1 ''-terphenyl] -5'-yl) -6-chloro-9H-carbazole)
  • Step 1 3- Chloro -6- ( Fluoranthene -3-yl) -9H- Carbazole (3-chloro-6- ( fluoranthen Synthesis of -3-yl) -9H-carbazole)
  • Step 1 4- (6- Chloro -9H- Carbazole -3 days)- N, N - Diphenylaniline synthesis
  • Step 1 N-([1,1'- Biphenyl ] -4-yl) -N- (4- (6- Chloro -9H- Carbazole Synthesis of -3-yl) phenyl) -9,9-dimethyl-9H-flowen-2-amine
  • 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, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • m-MTDATA, TCTA, PD-1, BCP used is as follows.
  • m-MTDATA 60 nm
  • TCTA 80 nm
  • 50% was prepared using the following H-27 as the first host and the compound of Table 2 as the second host.
  • An organic EL device was fabricated by stacking 1 host + 50% second host + 10% PD-1 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order. .
  • Example 10 50% H-27 + 50% J-97 5.49 43.2 200
  • Example 11 50% H-27 + 50% J-98 5.45 43.1 180
  • Example 12 50% H-27 + 50% J-102 5.59 43.3 155
  • Example 13 50% H-27 + 50% J-106 5.35 43.5
  • Example 14 50% H-27 + 50% J-110 5.49 43.2 150
  • Example 15 50% H-27 + 50% J-114 5.35 42.5
  • Example 16 50% H-27 + 50% J-118 5.52 44.2 165
  • Example 17 50% H-27 + 50% J-122 5.44 43.6 170
  • An organic EL device was manufactured in the same manner as in Example 1, except that 100% of the following CBP was used as a host material in forming the emission layer in Example 1.
  • An organic EL device was manufactured in the same manner as in Example 1, except that 100% of J-97 was used as a host material in forming the emission layer in Example 1.
  • the organic EL device of Examples 1 to 17 using the compound represented by Chemical Formula 6 of the present invention as the first host material of the light emitting layer uses CBP or J-97 as the sole host material. It was confirmed that the organic EL devices of Comparative Examples 1 and 2 exhibited superior performance in terms of current efficiency and driving voltage.
  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission.
  • An organic electroluminescent device having efficiency and improved lifespan characteristics.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant et, plus spécifiquement, un nouveau composé à base de carbazole ayant des caractéristiques de stabilité thermique, de phosphorescence, etc. excellentes ; l'invention concerne également un dispositif électroluminescent organique comprenant ledit composé dans une ou plusieurs couches organiques, ayant ainsi une faible tension d'attaque, un rendement lumineux élevé et des caractéristiques de durée de vie améliorées.
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CN112279847A (zh) * 2019-07-25 2021-01-29 南京高光半导体材料有限公司 一种绿色磷光主体材料及含有该材料的oled发光器件
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CN110105330A (zh) * 2019-05-31 2019-08-09 武汉华星光电半导体显示技术有限公司 一种高效蓝绿到橙红光热活化延迟荧光材料及其制备方法和应用
CN110105330B (zh) * 2019-05-31 2021-09-24 武汉华星光电半导体显示技术有限公司 一种高效蓝绿到橙红光热活化延迟荧光材料及其制备方法和应用
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