WO2018110958A1 - Composé électroluminescent organique et élément électroluminescent organique l'utilisant - Google Patents

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

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WO2018110958A1
WO2018110958A1 PCT/KR2017/014607 KR2017014607W WO2018110958A1 WO 2018110958 A1 WO2018110958 A1 WO 2018110958A1 KR 2017014607 W KR2017014607 W KR 2017014607W WO 2018110958 A1 WO2018110958 A1 WO 2018110958A1
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group
aryl
triazine
chloro
synthesis example
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김회문
김영배
손호준
배형찬
한송이
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주식회사 두산
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • 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
    • C07D403/02—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
    • 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
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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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    • 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
    • C07D403/02—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
    • C07D403/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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    • 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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    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—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, a novel compound having excellent hole, electron injection and transporting ability, light emitting ability, etc.
  • the present invention relates to an organic EL device having improved characteristics such as 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 luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 hole blocking layer
  • anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
  • phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials. Is being used.
  • CBP has shown excellent properties as a phosphorescent host material.
  • 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 which exhibits a low driving voltage and high efficiency, including the novel organic compound.
  • the present invention provides a compound represented by the following formula (1).
  • L 1 and L 2 are the same as or different from each other, and each independently a single bond, or a C 6 to C 18 arylene group and a nuclear atom having 5 to 18 heteroarylene groups, and
  • Ar 1 and Ar 2 are the same as or different from each other,
  • Ar 1 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,
  • Ar 2 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 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and an alkyl of C 1 to C 40 Silyl 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 arylphosphine group, C 6 ⁇ C 60 aryl It is selected from the group consisting of a phosphine oxide group and C 6 ⁇ C 60 arylamine group,
  • the time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, 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 nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear
  • 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).
  • 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 a lower driving voltage, higher efficiency, and longer life than a conventional host material can be manufactured. Improved full color display panels can also be manufactured.
  • the present invention is based on carbazole (carbazole), and different moieties (eg, aryl group; nitrogen-containing heterocycle, etc.) are introduced at position 2 and N of the carbazole basic skeleton, respectively, It is characterized by forming an asymmetric structure represented.
  • carbazole carbazole
  • moieties eg, aryl group; nitrogen-containing heterocycle, etc.
  • an electron donor group having a large electron donor such as phenyl, biphenyl, terphenyl, naphthyl group is substituted at the carbazole position 2, and a basic skeleton of carbazole (eg, N position)
  • the electron-withdrawing group (EWG) having high electron absorption of a nitrogen-containing heterocycle e.g., pyridine group, pyrimidine group, triazine group, etc.
  • the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, and may have a wide bandgap and may have high carrier transport properties.
  • the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and excellent luminescence properties
  • the compound of Formula 1 may also be used 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.
  • the electron donor group (EDG) having a large electron donor such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, and the like
  • EDG electron donor group having a large electron donor such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, and the like
  • the injection and transport of holes may be smoothly performed. Therefore, in addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or light emitting auxiliary layer material.
  • the compound represented by Chemical Formula 1 may improve light emission characteristics of the organic EL device, and improve hole injection / transportation capability, electron injection / transportation capability, luminous efficiency, driving voltage, and lifetime 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 various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the above-described basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature (Tg), thereby making it a conventional light emitting material.
  • Tg glass transition temperature
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the compound represented by the formula (1) is Since it is also effective in suppressing crystallization, the organic electroluminescent device including the same may greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
  • L 1 and L 2 are the same as or different from each other, and may be a linker of a conventional divalent group known in the art. In one example, it may be selected from the group consisting of a single bond, or is C 6 ⁇ C 18 arylene group and a nuclear atoms of 5 to 18 hetero arylene group for.
  • L 1 and L 2 include a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, and furinyl And an ethylene group, a quinolinyl group, a pyrrolyylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like.
  • L 1 is preferably a single bond, a phenylene group, or a biphenylene group.
  • Ar 1 and Ar 2 may be the same as or different from each other, more specifically, Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 to 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 hetero aryl group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 60 of the aryloxy group, C 1 ⁇ C 40 alkyl silyl group, the group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ may be
  • Ar 2 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 Of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and a C 1 to C 40 group Alkylsilyl group, C 6 ⁇ C 60 Aryl silyl 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 It may be selected from the group consisting of aryl phosphine oxide group and C 6 ⁇ C 60 arylamine group.
  • Ar 1 and Ar 2 are different from each other, Ar 1 is a heteroaryl group having 5 to 19 nuclear atoms, Ar 2 is preferably an C 6 ⁇ C 18 aryl group. Specifically Ar 2 may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and triphenylene.
  • the aryl group and heteroaryl group of Ar 1 and Ar 2 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ⁇ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms Can be.
  • the time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, 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 nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear
  • Ar 1 may be a substituent represented by the following Chemical Formula 2.
  • Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 1 ), but at least one of Z 1 to Z 5 is preferably N.
  • a plurality of R 1 may be the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, an alkyl group of C 1 ⁇ C 40, C 2 ⁇ C 40 alkenyl group, C 2 to 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 ⁇ 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 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C aryl phosphine oxide 60 group and
  • R 1 is preferably selected from the group consisting of hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, and a heteroaryl group of 5 to 40 nuclear atoms.
  • the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 Alkynyl group of ⁇ C 40 , cycloalkyl group of C 3 ⁇ C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms,
  • Substituents represented by the formula (2) may be more embodied in any one of the substituent group consisting of the formula A-1 to A-15.
  • R 1 is as defined in Formula 2 above,
  • n is an integer of 0 to 4, when n is 0, it means that hydrogen is not substituted with a substituent R 2 , when n is an integer of 1 to 4, R 2 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 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 alkyl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ aryl phosphine oxide of
  • Alkyl group of the R 2 an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group,
  • the arylphosphine group, the arylphosphine oxide group and the 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 alky Neyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, an aryl
  • Ar 1 may be a substituent represented by the following Chemical Formula 3.
  • Z is the same as or different from each other, and each independently N or C (R 3 ), but preferably at least one of the plurality of Z is N.
  • R 3 when the R 3 is plural, plural R 3 may be the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, an alkyl group of C 1 ⁇ C 40, C 2 ⁇ C 40 Alkenyl group, C 2 to 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 hetero aryl group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 60 of the aryloxy group, C 1 ⁇ C 40 alkyl silyl group, the group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and
  • X may be O or S.
  • R 4 to R 5 are the same or different and are each independently 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 Alkynyl group of ⁇ C 40 , cycloalkyl group of C 3 ⁇ C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ 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 ⁇ an aryl boronic of C 60, C 6 ⁇ C 60 aryl phosphine group, a group of C 6 ⁇ C 60 aryl phosphin
  • R 4 is a C 6 ⁇ C 18 aryl group
  • R 5 is hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, and a nuclear atom of 5 to 40 hetero It is preferably selected from the group consisting of aryl groups.
  • R 4 may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and triphenylene.
  • n is an integer of 0 to 7, and when n is 2 or more, a plurality of R 5 may be the same or different from each other.
  • n 0, it means that hydrogen is not substituted with a substituent R 5 , and when n is 1 to 7, R 5 may independently have the aforementioned substituents except for hydrogen.
  • Z and R 4 are each as defined in Chemical Formula 3 described above.
  • the compound represented by the formula (1) of the present invention described above may be more specifically represented by the compound represented by any one of formulas 1-1 to 7-23 illustrated below.
  • the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 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 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, 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 as used herein means 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 monovalent substituents derived from non-aromatic hydrocarbons 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 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.
  • 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 may be used in combination.
  • 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 of 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 compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material.
  • the compound represented by Formula 1 of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, and more preferably a phosphorescent host of the light emitting layer.
  • 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 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.
  • 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
  • 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.
  • 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 1-1 as a light emitting host material when forming the emission layer.
  • Example 1 1-1 6.64 516 42.2 Example 2 1-2 6.35 517 47.4 Example 3 1-4 6.62 518 49.2 Example 4 1-7 6.53 516 44.8 Example 5 1-8 6.36 517 43.1 Example 6 1-10 6.88 516 43.6 Example 7 1-12 6.44 516 47.4 Example 8 1-14 6.62 516 43.4 Example 9 1-17 6.46 517 49.2 Example 10 1-19 6.39 516 47.4 Example 11 1-20 6.74 516 47.6 Example 12 1-22 6.81 518 43.2 Example 13 2-1 6.38 516 47.4 Example 14 2-2 6.54 518 44.1 Example 15 2-4 6.67 517 42.4 Example 16 2-7 6.32 517 46.7 Example 17 2-8 6.55 516 44.8 Example 18 2-10 6.83 518 43.5 Example 19 2-12 6.16 516 48.1 Example 20 2-14 6.24 516 49.6 Example 21 2-17 6.26 517 49.9 Example 22 2-19 6.18 518 47.4
  • the green organic EL device of Examples 1 to 84 using the compound (1-1 to 7-23) according to the present invention as a light emitting layer of the green organic EL device is a comparative example using conventional CBP. Compared with the green organic EL device of 1, it was found to exhibit better performance in terms of efficiency and driving voltage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé ayant une excellente capacité d'émission de lumière ; et un élément électroluminescent organique comprenant celui-ci dans une ou plusieurs couches de matériau organique, ce qui permet d'obtenir des caractéristiques améliorées telles que l'efficacité d'émission de lumière, la tension de commande et la durée de vie.
PCT/KR2017/014607 2016-12-15 2017-12-13 Composé électroluminescent organique et élément électroluminescent organique l'utilisant WO2018110958A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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CN111009612A (zh) * 2018-10-04 2020-04-14 三星Sdi株式会社 用于有机光电装置的组合物、有机光电装置及显示装置
CN111146348A (zh) * 2018-11-02 2020-05-12 三星Sdi株式会社 有机光电设备和显示设备
CN111162185A (zh) * 2018-11-07 2020-05-15 三星Sdi株式会社 有机光电器件及显示器件
EP3689867A1 (fr) * 2019-01-30 2020-08-05 Novaled GmbH Composition, couche semi-conductrice organique et dispositif électronique
US20200266357A1 (en) * 2019-02-15 2020-08-20 Samsung Sdi Co., Ltd. Composition for optoelectronic device and organic optoelectronic device and display device
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US11223019B2 (en) 2017-06-22 2022-01-11 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
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US20220140251A1 (en) * 2017-06-22 2022-05-05 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device and composition for organic optoelectronic device
US11605782B2 (en) 2018-12-04 2023-03-14 Samsung Sdi Co., Ltd. Organic optoelectronic device and display device
US12029112B2 (en) 2019-02-15 2024-07-02 Samsung Sdi Co., Ltd. Composition for optoelectronic device and organic optoelectronic device and display device

Families Citing this family (2)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140046541A (ko) * 2012-10-04 2014-04-21 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20140082273A (ko) * 2012-12-24 2014-07-02 덕산하이메탈(주) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20140103842A (ko) * 2013-02-15 2014-08-27 에스에프씨 주식회사 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자
KR20150043669A (ko) * 2013-10-15 2015-04-23 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160051210A (ko) * 2014-10-31 2016-05-11 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140046541A (ko) * 2012-10-04 2014-04-21 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20140082273A (ko) * 2012-12-24 2014-07-02 덕산하이메탈(주) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20140103842A (ko) * 2013-02-15 2014-08-27 에스에프씨 주식회사 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자
KR20150043669A (ko) * 2013-10-15 2015-04-23 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160051210A (ko) * 2014-10-31 2016-05-11 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자

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US11605782B2 (en) 2018-12-04 2023-03-14 Samsung Sdi Co., Ltd. Organic optoelectronic device and display device
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WO2020157204A1 (fr) * 2019-01-30 2020-08-06 Novaled Gmbh Composition, couche semiconductrice organique et dispositif électronique
EP3689867A1 (fr) * 2019-01-30 2020-08-05 Novaled GmbH Composition, couche semi-conductrice organique et dispositif électronique
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