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WO2016105161A2 - Composé organique et élément électroluminescent organique comprenant ce composé - Google Patents

Composé organique et élément électroluminescent organique comprenant ce composé Download PDF

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WO2016105161A2
WO2016105161A2 PCT/KR2015/014260 KR2015014260W WO2016105161A2 WO 2016105161 A2 WO2016105161 A2 WO 2016105161A2 KR 2015014260 W KR2015014260 W KR 2015014260W WO 2016105161 A2 WO2016105161 A2 WO 2016105161A2
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aryl
alkyl
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boron
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WO2016105161A3 (fr
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김성무
한송이
김재미
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Doosan Corp
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    • 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
    • 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
    • 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]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

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.
  • an object of the present invention is to provide an organic electroluminescent device including the novel organic compound exhibiting low driving voltage, high luminous efficiency and improved lifespan characteristics.
  • the present invention provides a compound represented by the following formula (1):
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein X 1 and At least one of X 2 is N (Ar 1 );
  • L 1 is selected from the group consisting of a single bond, an arylene group having 6 to 40 carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;
  • a, b, c and d are each independently an integer from 0 to 4.
  • e is an integer from 0 to 3;
  • f is an integer from 0 to 2;
  • Ar 1 to Ar 5 are each independently hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ alkynyl group of C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 40 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 alkylboron group, C 6 -C 60 arylboron group, C 1- alkylphosphonate of C 40 pingi, C 1 ⁇ C 40 alkyl phosphonic blood group, C 6 ⁇ C 60 aryl phosphine pingi, mono- or diaryl phosphine of C 6 ⁇ C 60 blood
  • R 1 to R 6 are each independently a heavy hydrogen (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C 6 ⁇ C 60 , an alkyloxy group of C 1 ⁇ C 40 , an arylamine group of C 6 ⁇ C 60 , C 3 ⁇ C 40 Cycloalkyl group of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 an alkyl phosphine group, C 1 ⁇ C 40 alkyl phosphonic blood group, C of 6 ⁇ C 60 aryl phosphine group, a mono- or diaryl
  • the arylene group and heteroarylene group of L 1 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar 1 to Ar 5 and R 1 to R 6 , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40
  • the compound represented by Formula 1 may be represented by any one of the following Formula 2 to Formula 7:
  • L 1 , X 1 to X 2 , R 1 to R 6 , Ar 1 to Ar 5 , a, b, c, d, e and f are each as defined in Chemical Formula 1.
  • X 1 and X 2 are both N (Ar 1 ), a plurality of Ar 1 may be the same or different from each other.
  • L 1 may be a single bond, a phenylene group or a biphenylene group.
  • Ar 1 to Ar 5 are each independently hydrogen, deuterium (D), C 6 ⁇ C 60 aryl group, nuclear atoms of 5 to 40 heteroaryl groups And R 5 and R 6 may both be hydrogen.
  • R 1 to R 4 are each independently in the group consisting of deuterium (D), C 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl groups of nuclear atoms Can be selected.
  • both e and f may be zero.
  • At least one of Ar 1 to Ar 5 and R 1 to R 4 in the formula (1) may be a substituent represented by the following formula (8):
  • L 2 is selected from the group consisting of a single bond, an arylene group having 6 to 40 carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;
  • Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), wherein at least one of Z 1 to Z 5 is N;
  • R 11 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 Alkynyl group of ⁇ C 40 , aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ⁇ C 60 C 1 ⁇ C 40 alkyloxy group, C 3 ⁇ C 40 cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ selected from
  • the arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 An arylamine group, a C 3 to C 40
  • the substituent represented by Formula 8 may be a substituent represented by any one of the following Formula A-1 to Formula A-15:
  • n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R 21 , and when n is an integer of 1 to 4, R 21 is deuterium, halogen, cyano group, nitro C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 6 Aryl group of ⁇ C 60 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ⁇ C 60 C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkyl silyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphine group, C 6 to C 60 mono or diaryl phosphinyl group
  • the arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 An arylamine group, a C 3 to C 40 cycl
  • L 2 and R 11 are each as defined in Chemical Formula 8 above.
  • the substituent represented by any one of Formulas A-1 to A-5 is characterized in that it is selected from the group consisting of the following substituents:
  • * means a portion to which a bond is made.
  • the present invention also includes (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 is one of Formula 1 It provides an organic electroluminescent device characterized in that it comprises a compound.
  • At least one of the one or more organic material layer containing the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, Preferably it may be a light emitting layer, more preferably the compound represented by the formula (1) may be used as a green or red phosphorescent host of the light emitting layer.
  • 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 represented by Formula 1 according to the present invention has excellent thermal stability and phosphorescence properties, it may be used as a material of the organic material layer of the organic EL device.
  • the compound represented by Formula 1 according to the present invention when used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to the conventional host material, It also enables the manufacture of full color display panels with significantly improved performance and longevity.
  • the present invention provides a compound represented by Formula 1:
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein X 1 and At least one of X 2 is N (Ar 1 );
  • L 1 is selected from the group consisting of a single bond, an arylene group having 6 to 40 carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;
  • a, b, c and d are each independently an integer from 0 to 4.
  • e is an integer from 0 to 3;
  • f is an integer from 0 to 2;
  • Ar 1 to Ar 5 are each independently hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ alkynyl group of C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 40 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 alkylboron group, C 6 -C 60 arylboron group, C 1- alkylphosphonate of C 40 pingi, C 1 ⁇ C 40 alkyl phosphonic blood group, C 6 ⁇ C 60 aryl phosphine pingi, mono- or diaryl phosphine of C 6 ⁇ C 60 blood
  • R 1 to R 6 are each independently a heavy hydrogen (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C 6 ⁇ C 60 , an alkyloxy group of C 1 ⁇ C 40 , an arylamine group of C 6 ⁇ C 60 , C 3 ⁇ C 40 Cycloalkyl group of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 an alkyl phosphine group, C 1 ⁇ C 40 alkyl phosphonic blood group, C of 6 ⁇ C 60 aryl phosphine group, a mono- or diaryl
  • the arylene group and heteroarylene group of L 1 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar 1 to Ar 5 and R 1 to R 6 , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40
  • the present invention relates to a novel carbazole compound having excellent thermal stability and phosphorescence properties, and more particularly, includes at least two carbazole moieties, and dibenzo moieties are bonded to form a basic skeleton.
  • 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):
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein X 1 and At least one of X 2 is N (Ar 1 ), preferably X 1 and X 2 are both N (Ar 1 ), and a plurality of Ar 1 are the same as or different from each other;
  • L 1 is a divalent (divalent) connecting group (linker) of the group known to the art, and is selected from a single bond, C 6 ⁇ C 40 arylene group and a nuclear atoms of 5 to 40 heteroarylene group the group consisting of, preferably Phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group , Imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group, and more preferably a single bond, a phenylene group or a biphenylene group;
  • a, b, c and d are each independently an integer from 0 to 4.
  • e is an integer from 0 to 3
  • f is an integer from 0 to 2, preferably both e and f are 0;
  • Ar 1 to Ar 5 are each independently hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ alkynyl group of C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 40 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 alkylboron group, C 6 -C 60 arylboron group, C 1- alkylphosphonate of C 40 pingi, C 1 ⁇ C 40 alkyl phosphonic blood group, C 6 ⁇ C 60 aryl phosphine pingi, C 6 ⁇ C 60 mono or diaryl phosphine blood group and
  • R 1 to R 6 are each independently a heavy hydrogen (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C 6 ⁇ C 60 , an alkyloxy group of C 1 ⁇ C 40 , an arylamine group of C 6 ⁇ C 60 , C 3 ⁇ C 40 Cycloalkyl group of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 an alkyl phosphine group, C 1 ⁇ C 40 alkyl phosphonic blood group, C of 6 ⁇ C 60 aryl phosphine group, a mono- or diaryl
  • the arylene group and heteroarylene group of L 1 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar 1 to Ar 5 and R 1 to R 6 , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40
  • the dibenzo moiety which may be included in the compound represented by Formula 1 of the present invention may be selected from the following structures.
  • the carbazole moiety is variously used as a material for an organic EL device, in particular, a phosphorescent host material.
  • the carbazole moiety has a high triplet energy of 3.0 eV and a low HOMO energy level of 6.0 eV, which is mainly used in blue phosphorescent hosts. Therefore, in the case of the compound represented by Formula 1 of the present invention in which two dibenzo moieties are bonded to one benzene ring of a carbazole moiety, the triplet energy is less than 3.0 eV, and the HOMO energy level is increased to increase energy.
  • the band gap is suitable for blue / green / red phosphorescent hosts.
  • a carbazole moiety and one of the dibenzo moieties are bonded to one benzene ring of a carbazole moiety to generate steric hinderance.
  • the compound molecules are distorted to solve the problem of deterioration of the luminescence property due to ⁇ - ⁇ -stacking, thereby preventing the formation of excitation dimers (eximers), thereby improving the luminescence efficiency. do.
  • the carbazole moiety has the characteristics of an electron donating group (EDG) having a large electron donating property.
  • EWG electron withdrawing group
  • the compound of the present invention has a large electron absorbing group (EWG) and a large electron donating group.
  • the entire molecule is bipolar, including all the electron donating groups (EDGs). Since the bipolar compound represented by Formula 1 of the present invention can increase the binding force between holes and electrons, the bipolar compound is not only advantageous as a host in the phosphorescent light emitting layer but also may be applied to a hole transport layer, a hole injection layer, and an electron transport layer.
  • the compound represented by the formula (1) of the present invention has a higher thermal stability than the conventional CBP (4,4-dicarbazolybiphenyl) as the molecular weight of the compound is significantly increased due to the substituent introduced into the molecule to improve the glass transition temperature Indicates.
  • the compound represented by the formula (1) of the present invention is also effective in suppressing the crystallization of the organic material layer.
  • the compound represented by Formula 1 may be a compound represented by any one of the following Formula 2 to Formula 7:
  • L 1 , X 1 to X 2 , R 1 to R 6 , Ar 1 to Ar 5 , a, b, c, d, e and f are each as defined in Chemical Formula 1.
  • At least one of Ar 1 to Ar 5 and R 1 to R 4 may be a substituent represented by the following formula (8).
  • L 2 is selected from the group consisting of a single bond, an arylene group having 6 to 40 carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;
  • Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), wherein at least one of Z 1 to Z 5 is N;
  • R 11 is heavy hydrogen, 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 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl groups, C 6 ⁇ C 60 aryloxy group C 1 ⁇ C 40 alkyloxy group, C 3 ⁇ C 40 cyclo alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl amine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ aryl of C 60 Boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylsilyl group or
  • the arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 An arylamine group, a C 3 to C 40
  • At least one of Ar 1 to Ar 5 and R 1 to R 4 in Formula 1 may be a substituent represented by any one of the following Formula A-1 to Formula A-15:
  • n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R 21 , and when n is an integer of 1 to 4, R 21 is deuterium, halogen, cyano group, nitro C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 6 Aryl group of ⁇ C 60 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ⁇ C 60 C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkyl silyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphine group, C 6 to C 60 mono or diaryl phosphinyl group
  • the arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 An arylamine group, a C 3 to C 40 cycl
  • L 2 and R 11 are each as defined in Chemical Formula 8 above.
  • the substituent represented by any one of Formulas A-1 to A-15 is preferably selected from the group consisting of the following substituents. However, this is not particularly limited:
  • * means a part to which a bond is made.
  • 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:
  • 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 includes a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may be used alone, or two or more may be mixed and used.
  • 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.
  • 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, and as described above, 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.
  • 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.
  • examples of 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> 4- Bromo -2- Chloro -9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H- Carbazole synthesis
  • 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 C 21 as a light emitting host material when forming the emission layer.
  • Example 1 C 21 6.61 518 38.6
  • Example 2 C 23 6.70 517 39.3
  • Example 3 Example 3
  • Example 4 C 29 6.81 518 39.9
  • Example 5 C 30 6.73 517 40.2
  • Example 6 C 51 6.74 518 40.8
  • Example 7 C 53 6.77 518 40.7
  • Example 8 C 58 6.71 516 39.2
  • Example 9 C 59 6.68 517 39.8
  • Example 10 C 60 6.63 517 39.4
  • Example 11 C 81 6.49 518 38.5
  • Example 12 C 83 6.87 517 39.1
  • Example 13 C 88 6.66 517 41.3
  • Example 14 C 89 6.70 517 40.4
  • Example 16 C 111 6.81 518 41.5
  • Example 18 C 123 6.81 518 39.6 Comparative Example 1 CBP 6.93 516 38.2
  • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant, et plus particulièrement, un nouveau composé à base de carbazole présentant une stabilité thermique et des propriétés phosphorescentes excellentes et un élément électroluminescent organique comprenant celui-ci dans une ou plusieurs couches organiques associées et, de ce fait, nécessitant une faible tension de commande et ayant un rendement lumineux élevé et de meilleures caractéristiques de durée de vie.
PCT/KR2015/014260 2014-12-26 2015-12-24 Composé organique et élément électroluminescent organique comprenant ce composé Ceased WO2016105161A2 (fr)

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JP2019108315A (ja) * 2017-12-20 2019-07-04 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用化合物、液状組成物、インク組成物、薄膜、及び有機エレクトロルミネッセンス素子
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TWI660954B (zh) * 2016-12-20 2019-06-01 南韓商喜星素材股份有限公司 有機發光裝置以及用於有機發光裝置的有機材料層的組成物
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