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WO2018070835A1 - Composé organique et élément électroluminescent organique l'utilisant - Google Patents

Composé organique et élément électroluminescent organique l'utilisant Download PDF

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WO2018070835A1
WO2018070835A1 PCT/KR2017/011329 KR2017011329W WO2018070835A1 WO 2018070835 A1 WO2018070835 A1 WO 2018070835A1 KR 2017011329 W KR2017011329 W KR 2017011329W WO 2018070835 A1 WO2018070835 A1 WO 2018070835A1
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aryl
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한송이
엄민식
조현종
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Doosan Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—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 three or more hetero rings
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same. More particularly, the organic electroluminescent device having improved luminescence efficiency, driving voltage, lifespan, etc., by including the compound having excellent luminescence ability and the organic electroluminescent device in the at least one organic layer. It relates to an element.
  • 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.
  • 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.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent dopant materials having a great advantage in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopants. It is used as a material.
  • 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 luminous ability.
  • 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 provides a compound represented by the following formula (1).
  • L 1 and L 2 are the same or different, and each independently is a single bond, or selected from an aryl group and a nuclear atoms of 5 to 18 heteroaryl group consisting of alkylene groups of C 6 ⁇ C 18,
  • Plural R 1 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group and C 2 ⁇ C Selected from the group consisting of 40 alkynyl groups, or may combine with adjacent groups to form a condensed ring, provided they form at least one condensed ring,
  • X is selected from the group consisting of C (R 3 ) (R 4 ), O and S,
  • Ar 1 and Ar 2 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C the group of boron 60 aryl, C 6 ⁇ C 60 aryl phosphine group, is selected from the group consisting of C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇
  • n is an integer from 0 to 3
  • R 2 to R 4 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the group consisting of
  • the arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group of Ar 1 and Ar 2 , R 1 to R 4 , aryl group, heteroaryl group, Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium (D), halogen, 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 hetero cycloalkyl group, C of Aryl group of 6 to C 60
  • the present invention comprises an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, at least one of the one or more organic material layers containing the compound represented by the formula (1)
  • An electroluminescent device is provided.
  • the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the compound represented by Chemical Formula 1 may be used as a phosphorescent host of the emission layer.
  • 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.
  • the compound represented by Formula 1 of the present invention when used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device having a lower driving voltage, higher efficiency and longer lifespan than conventional host materials, and furthermore, performance and lifespan. This improved full color display panel can also be manufactured.
  • novel organic compound according to the present invention is directly bonded to 'benzocarbazole' 'acridine, phenoxazine or phenoxazine', or a linker (e.g., arylene or hetero). It is characterized in that the form bonded through an arylene group) as a basic skeleton, and various substituents are introduced into the basic skeleton and represented by the formula (1).
  • the compound of Formula 1 includes acridine, phenoxazine or phenoxyazine having sublimability and excellent thermal stability.
  • the life of the device can be extended and used for a long time.
  • the compound of Formula 1 has a band gap due to increased conjugation length when acridine, phenoxazine or phenoxyazine is combined with 'benzocarbazole' and combined with 'carbazole'. ) May decrease.
  • the compound of Formula 1 is combined with 'acridin, phenoxazine or phenoxyazine' benzocarbazole, 'conjugation (conjugation) length is increased compared to when combined with' carbazole 'bandgap ( band gap) may be reduced (see Table 1 below).
  • Such a compound of Formula 1 may be used in the organic material layer material of the organic EL device, when used as the light emitting layer material, it can be used as a red phosphorescent host material exhibiting a long wavelength.
  • the compound of Formula 1 may control HOMO and LUMO energy levels according to the type of various substituents introduced into the basic skeleton, and may have a high band transport as well as a wide bandgap.
  • a high electron-absorbing electron withdrawing group such as a nitrogen-containing heterocyclic ring (eg, pyridine group, pyrimidine group, quinazoline group, triazine group, etc.) to the basic skeleton, Since the whole molecule has a bipolar characteristic, the binding force between holes and electrons can be enhanced.
  • the compound of Formula 1 may be used as an organic material layer, particularly a light emitting layer material of the organic EL device.
  • the compound represented by Chemical Formula 1 has a higher molecular weight than the conventional organic electroluminescent device material [for example, 4,4-dicarbazolybiphenyl (hereinafter, referred to as 'CBP')], the glass transition temperature is high and the thermal stability is excellent. In addition to excellent luminous performance. Therefore, when the compound of Formula 1 is applied to the organic material layer of the organic EL device, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the compound of Formula 1 may be used as an organic material of the organic electroluminescent device, and preferably used as a light emitting layer material (blue, green and / or red phosphorescent host material).
  • 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.
  • novel compound according to the present invention is represented by Chemical Formula 1, wherein various substituents are introduced as acridine, phenoxazine or phenoxyazine are directly bonded to benzocarbazole or through a linker.
  • L 1 and L 2 are the same as or different from each other, each independently may be a single bond or a divalent linking group.
  • the divalent linking group is selected from the group consisting of C 6 ⁇ C 18 arylene group and 5 to 18 heteroarylene group of nuclear atoms.
  • Non-limiting examples of the arylene group and hetero arylene group are phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, And a furinylene group, a quinolinyl group, a pyrroylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, and a pyrimidinylene group.
  • L 1 and L 2 are the same as or different from each other, and each independently may be a single bond or a C 6 ⁇ C 18 arylene group.
  • Plural R 1 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group and C 2 ⁇ C It may be selected from the group consisting of 40 alkynyl groups, or may combine with adjacent groups to form a condensed ring, provided they form at least one condensed ring.
  • the plurality of R 1 is combined with one R 1 and the other R 1 to form one condensed ring, the remaining R 1 may be hydrogen.
  • Such a compound of Formula 1 may be embodied as a compound represented by the following Formulas 3 to 8.
  • X is selected from the group consisting of C (R 1 ) (R 2 ), O and S.
  • Ar 1 and Ar 2 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 arylboronic group, C 6 ⁇ C 60 aryl phosphine group, is selected from C 6 ⁇ C 60 aryl phosphine oxide group, and the group consisting of C 6 ⁇ C 60 aryl
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently C 1 ⁇ C 40 Alkyl group, C 6 ⁇ C 60 An aryl group, a nuclear atom of 5 to 60 heteroaryl group and C 6 It may be selected from the group consisting of arylamine group of ⁇ C 60 . More preferably, Ar 1 may be a C 6 ⁇ C 60 aryl group or a nuclear atom of 5 to 60 heteroaryl group, Ar 2 may be a C 6 ⁇ C 60 aryl group.
  • Such a compound may be used as a light emitting layer material of an organic electroluminescent device, and preferably, a red phosphorescent host material.
  • n is an integer of 0-3. In this case, when m is 0, it means that hydrogen is not substituted with a substituent R 2 . When m is an integer of 1 to 3, it means that hydrogen is substituted with a substituent R 2 , a plurality of R 2 are the same or different from each other, and each independently deuterium (D), halogen, cyano group, nitro group, C 1 a ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 of the An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , an alkylsilyl group of C 1 to C 40 , and a C 6 to C 60 group aryl sily
  • R 3 and R 4 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the group consisting of
  • R 3 and R 4 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, a number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ , or selected from the group consisting of an aryl amine of the C 60 of, or adjacent groups combine to form a condensed ring.
  • D deuterium
  • halogen cyano group
  • nitro group C 1 ⁇ C 40 alkyl group
  • C 6 ⁇ C 60 aryl group a number of nuclear atoms of 5 to 60 heteroaryl group
  • a C 6 ⁇ or selected from the group consisting of an aryl amine of the C 60 of, or adjacent groups combine to form a condensed ring.
  • the arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group of Ar 1 and Ar 2 , R 1 to R 4 , aryl group, heteroaryl group, Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium (D), halogen, 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 hetero cycloalkyl group, C of Aryl group of 6 to C 60
  • the compound represented by Formula 1 may be embodied in at least one of the following Formulas 3 to 5. However, this is not particularly limited.
  • L 1 , L 2 , Ar 1 , Ar 2 , m, R 2 are the same as defined in Formula 1, respectively.
  • the compound represented by the formula (1) may be more specifically at least one of the following formulas (6) to (8). However, this is not particularly limited.
  • L 1 , L 2 , Ar 1 , Ar 2 , m, and R 2 are the same as defined in Chemical Formula 1, respectively.
  • Ar 1 may be a substituent represented by the following formula (9).
  • Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 5 ), wherein when R 5 is a plurality, they are the same or different from each other.
  • R 5 is hydrogen, deuterium (D), 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, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 An aryl phosphine group, a C 6 ⁇ C 60 aryl phosphine oxide group and a C 6 ⁇ C 60 arylamine group may be selected from, or may be combined with an adjacent group to form a
  • the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently deuterium (D), 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 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 Alkyloxy group, C 6
  • Substituents represented by the formula (9) may be more specific with any one of the following A-1 to A-15. However, this is not particularly limited.
  • R 5 is the same as defined in Chemical Formula 9.
  • p is an integer of 0-4. When p is 0, it means that hydrogen is not substituted with a substituent R 6 .
  • R 6 is deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 aryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ aryloxy C 60, C 1 ⁇ C 40 alkyl silyl group, an aryl boronic of C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 aryl pho
  • the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently deuterium (D), 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 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 Alkyloxy group, C 6
  • the compound represented by the formula (1) of the present invention described above may be further embodied as a compound represented by any one of the compounds 1 to 576 exemplified below.
  • the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • alkyl means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
  • alkyl 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.
  • alkenyl 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.
  • alkynyl include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 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, and the like.
  • heteroaryl means a monovalent substituent derived from 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, 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 alkyl having 1 to 40 carbon atoms.
  • alkyloxy may comprise a linear, branched or cyclic structure. Examples of such 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, adamantine, and the like.
  • Heterocycloalkyl as used herein means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 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.
  • alkyl boron is boron substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron means boron substituted with aryl having 6 to 60 carbon atoms.
  • arylphosphine means phosphine substituted with aryl having 6 to 60 carbon atoms
  • arylphosphine oxide group means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O. do.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • 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 may be used in combination.
  • the at least one organic material layer 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 containing the compound of Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may comprise a host material (preferably a phosphorescent host material).
  • the light emitting layer of the organic EL 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, an emission auxiliary layer, an emission layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of 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 the light emitting layer is represented by the formula (1) It may include a compound.
  • an electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic EL 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 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 a compound represented by the formula (1). have.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • 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 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.
  • 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 oxides with metals such as ZnO: Al or SnO 2: Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene),
  • 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.
  • Core 8 (65.9) was carried out in the same manner as in Preparation Example 2, except that 9-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 78%).
  • Core 9 (64.1) was carried out in the same manner as in Preparation Example 3, except that 9-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 80%) was obtained.
  • Core 11 (67.1) was carried out in the same manner as in Preparation Example 5, except that 9-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 81%).
  • Core 13 (60.6) was carried out in the same manner as in Preparation Example 1, except that 8-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 72%) was obtained.
  • Core 14 (57.5) was carried out in the same manner as in Preparation Example 2, except that 8-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 68%).
  • Core 15 (56.1) was carried out in the same manner as in Preparation Example 3, except that 8-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 70%).
  • Core 16 (52.8) was carried out in the same manner as in Preparation Example 4, except that 8-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 66%).
  • Core 17 (57.2) was carried out in the same manner as in Preparation Example 5, except that 8-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 69%).
  • Core 23 (57.9) was carried out in the same manner as in Preparation Example 5, except that 11-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 70%).
  • Core 24 (53.1) was carried out in the same manner as in Preparation Example 6, except that 11-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo [c] carbazole. g, yield 64%).
  • a target compound (6.21 g, yield 88%) was obtained in the same manner as Synthesis Example 1 except for using Core 3 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (6.13 g, yield 85%) was obtained in the same manner as Synthesis Example 1 except for using Core 5 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (5.63 g, yield 77%) was obtained in the same manner as Synthesis Example 1 except for using Core 7 (5.00 g, 10.00 mmol) instead of Core 1.
  • Core 8 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 1 to obtain the target compound (5.73 g, yield 71%).
  • a target compound (5.43 g, yield 77%) was obtained in the same manner as Synthesis Example 1 except for using Core 9 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (5.34 g, yield 74%) was obtained in the same manner as Synthesis Example 1 except for using Core 11 (5.00 g, 10.00 mmol) instead of Core 1.
  • Core 12 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 1 to obtain the target compound (5.26 g, yield 66%).
  • Core 12 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, use Core 12 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol). Except for using the same procedure as in Synthesis Example 1 to obtain the target compound (4.85 g, 63% yield).
  • a target compound (4.24 g, yield 58%) was obtained in the same manner as Synthesis Example 1 except for using Core 13 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (4.16 g, yield 59%) was obtained in the same manner as Synthesis Example 1 except for using Core 15 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (4.25 g, yield 59%) was obtained in the same manner as Synthesis Example 1 except for using Core 17 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (5.05 g, yield 69%) was obtained in the same manner as Synthesis Example 1 except for using Core 19 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (4.79 g, yield 68%) was obtained in the same manner as Synthesis Example 1 except for using Core 21 (5.00 g, 10.00 mmol) instead of Core 1.
  • a target compound (4.47 g, yield 62%) was obtained in the same manner as Synthesis Example 1 except for using Core 23 (5.00 g, 10.00 mmol) instead of Core 1.
  • Core 23 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) Except for using the same procedure as in Synthesis Example 1 to obtain the target compound (4.70 g, 61% yield).
  • 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) / 90% of each compound of Table 2 + 10% (piq) 2 Ir (acac) (300 nm) / 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 1, except that CBP was used instead of the compound 13 as a light emitting host material when the emission layer was formed.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 13 as a light-emitting host material in forming the emission layer.
  • Example 1 Compound 13 4.7 11.9 Example 2 Compound 15 4.7 11.6 Example 3 Compound 17 4.7 12.4 Example 4 Compound37 4.7 13.2 Example 5 Compound39 4.8 12.5 Example 6 Compound41 4.8 12.6 Example 7 Compound61 4.8 12.3 Example 8 Compound 63 4.7 12.2 Example 9 Compound65 4.7 12.5 Example 10 Compound86 4.8 11.7 Example 11 Compound93 4.8 11.6 Example 12 Compound94 4.7 11.5 Example 13 Compound 110 4.7 12.4 Example 14 Compound117 4.8 12.4 Example 15 Compound118 4.8 12.3 Example 16 Compound134 4.8 11.7 Example 17 Compound141 4.8 12.3 Example 18 Compound142 4.8 12.6 Example 19 Compound157 4.8 12.6 Example 20 Compound159 4.7 12.4 Example 21 Compound161 4.7 11.2 Example 22 Compound181 4.7 11.1 Example 23 Compound183 4.7 11.3 Example 24 Compound185 4.7 11.5 Example 25 Compound205 4.8 12.3 Example 26 Compound207 4.8 12.2
  • the red organic electroluminescent devices (Examples 1 to 72) using the compound according to the present invention in the light emitting layer are red organic electroluminescent devices (Comparative Examples 1 or 2) using CBP or Compound A in the light emitting layer. Compared with the current efficiency and driving voltage it was found that better performance.
  • red organic electroluminescent devices (Examples 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31 and 34) using the compound according to the present invention in the light emitting layer are It turned out that it shows long lifetime compared with the red organic electroluminescent element (comparative example 1 or 2) which used CBP or the compound A for the light emitting layer.

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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique utilisant celui-ci et, plus particulièrement, à un nouveau composé ayant d'excellente capacité d'émission de lumière et un élément organique électroluminescent présentant des caractéristiques améliorées, telles qu'une efficacité d'émission de lumière élevée, une faible tension d'attaque et une longue durée de vie, en contenant le nouveau composé dans au moins une couche de matériau organique.
PCT/KR2017/011329 2016-10-14 2017-10-13 Composé organique et élément électroluminescent organique l'utilisant Ceased WO2018070835A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112390783A (zh) * 2019-08-19 2021-02-23 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件

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CN109988154A (zh) * 2019-01-16 2019-07-09 浙江华显光电科技有限公司 一种磷光主体化合物及其使用该化合物的有机电致发光器件

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140064621A (ko) * 2012-11-19 2014-05-28 삼성디스플레이 주식회사 아민 유도체를 포함하는 유기 el 재료 및 그것을 사용한 유기 el 소자
KR20140103008A (ko) * 2013-02-14 2014-08-25 (주)씨에스엘쏠라 유기 발광 화합물 및 이를 이용한 유기 발광 소자
KR20140141071A (ko) * 2013-05-31 2014-12-10 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2014204464A1 (fr) * 2013-06-20 2014-12-24 Universal Display Corporation Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive
KR20150138105A (ko) * 2014-05-29 2015-12-09 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001160489A (ja) 1999-12-01 2001-06-12 Toyota Central Res & Dev Lab Inc 有機電界発光素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140064621A (ko) * 2012-11-19 2014-05-28 삼성디스플레이 주식회사 아민 유도체를 포함하는 유기 el 재료 및 그것을 사용한 유기 el 소자
KR20140103008A (ko) * 2013-02-14 2014-08-25 (주)씨에스엘쏠라 유기 발광 화합물 및 이를 이용한 유기 발광 소자
KR20140141071A (ko) * 2013-05-31 2014-12-10 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
WO2014204464A1 (fr) * 2013-06-20 2014-12-24 Universal Display Corporation Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive
KR20150138105A (ko) * 2014-05-29 2015-12-09 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112390783A (zh) * 2019-08-19 2021-02-23 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件

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