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WO2016089080A1 - Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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Publication number
WO2016089080A1
WO2016089080A1 PCT/KR2015/012975 KR2015012975W WO2016089080A1 WO 2016089080 A1 WO2016089080 A1 WO 2016089080A1 KR 2015012975 W KR2015012975 W KR 2015012975W WO 2016089080 A1 WO2016089080 A1 WO 2016089080A1
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group
aryl
groups
phenyl
mmol
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Korean (ko)
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김성무
한송이
김재미
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Doosan Corp
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Doosan Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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]
    • H10K50/14—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
    • 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 comprising the same, and more particularly, by including a novel tertiary substituted benzene-based compound having excellent hole injection, transporting ability, and luminescent ability in one or more organic material layers,
  • the present invention relates to an organic EL device having improved characteristics such as efficiency, driving voltage, and lifetime.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used to achieve a better natural color. In addition, 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 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 including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 as blue, green, and red dopant materials. It is used.
  • 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
  • the existing materials have advantages in terms of light emission characteristics, but the thermal stability is low due to the low glass transition temperature, and thus the materials are not satisfactory in terms of lifespan of the organic EL device.
  • an object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.
  • an object of the present invention is to provide an organic electroluminescent device including the organic compound exhibiting a low driving voltage and high luminous efficiency.
  • the present invention provides a compound represented by the following formula (1):
  • Ar 1 is a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , alkylsilyl group of C 3 to C 40 , 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 arylphosphine group, C 6 to C 60 mono or diaryl phosph It is selected from the group consisting of a pinyl group and an arylamine group of C 6 ⁇ C 60 ,
  • Y 1 is O or S
  • Z 1 is selected from the group consisting of a single bond, C (R 11 ) (R 12 ), N (R 13 ), O and S;
  • L 1 and L 2 are each independently a single bond, C 6 ⁇ C 40 aryl group and a nuclear atoms of 5 to 4O hetero arylene group is selected from the group consisting of;
  • R 1 to R 9 and R 11 to R 13 are each independently hydrogen, 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 40 aryl group, nuclear atoms 5 to 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, A C 6 to C 40 arylphosphine group, a C 6 to C 40 mono or diarylphosphinyl group and a C 6 to C 40 arylsilyl group, or a condensed aromatic ring or condensation in
  • n is an integer from 0 to 4.
  • R 10 is 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 40 aryl group, nuclear atom 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 40 arylboron groups, C 6 to C 40 arylphosphine groups, C 6 to C 40 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ selected from the group consisting arylsilyl of C 40 or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaro
  • R 1 to R 9 forms a bond with L 2 ;
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 13 Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl 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 40 aryl group, 5 to 40 heteroaryl group of nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocyclo
  • the present invention is an organic electroluminescent device comprising (i) an anode, (ii i) cathode and (ii i) one or more organic material layers interposed between the anode and the cathode, at least one of the one or more organic material layers It provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention means a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon 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 60 carbon atoms in which a single ring or two or more rings are combined.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention 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; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 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, and is linear, branched or cyclic. It may include a 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 in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl in the present invention is meant 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 in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or 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 in the present invention 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 can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence properties.
  • an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.
  • the present invention provides a compound represented by Formula 1:
  • Ar 1 is a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , alkylsilyl group of C 3 to C 40 , 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 arylphosphine group, C 6 to C 60 mono or diaryl phosph It is selected from the group consisting of a pinyl group and an arylamine group of C 6 ⁇ C 60 ,
  • Y 1 is O or S
  • Z 1 is selected from the group consisting of a single bond, C (R 11 ) (R 12 ), N (R 13 ), O and S;
  • L 1 and L 2 are each independently 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;
  • R 1 to R 9 and R 11 to R 13 are each independently hydrogen, 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 40 aryl group, nuclear atoms 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, A C 6 to C 40 arylphosphine group, a C 6 to C 40 mono or diarylphosphinyl group and a C 6 to C 40 arylsilyl group, or a condensed aromatic ring or condensation in
  • n is an integer from 0 to 4.
  • R 10 is 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 40 aryl group, nuclear atom 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 40 arylboron groups, C 6 to C 40 arylphosphine groups, C 6 to C 40 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ selected from the group consisting arylsilyl of C 40 or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaro
  • R 1 to R 9 forms a bond with L 2 ;
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 13 Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl 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 40 aryl group, 5 to 40 heteroaryl group of nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocyclo
  • the present invention provides a novel tertiary substituted benzene compound having a higher molecular weight than the conventional organic electroluminescent device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)] and having excellent driving voltage characteristics and efficiency. to provide.
  • CBP 4,4-dicarbazolybiphenyl
  • novel tertiary substituted benzene compound of the present invention can be represented by the following general formula (1):
  • Ar 1 is a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C Aryl group of 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , alkylsilyl group of C 3 to C 40 , 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 arylphosphine group, C 6 to C 60 mono or diaryl phosph A pinyl group and a C 6 -C 60 arylamine group;
  • Y 1 is O or S
  • Z 1 is selected from the group consisting of a single bond, C (R 11 ) (R 12 ), N (R 13 ), O and S;
  • L 1 and L 2 are each independently 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;
  • R 1 to R 9 and R 11 to R 13 are each independently hydrogen, 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 40 aryl group, nuclear atoms 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, A C 6 to C 40 arylphosphine group, a C 6 to C 40 mono or diarylphosphinyl group and a C 6 to C 40 arylsilyl group, or a condensed aromatic ring or condensation in
  • n is an integer from 0 to 4.
  • R 10 is 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 40 aryl group, nuclear atom 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 40 arylboron groups, C 6 to C 40 arylphosphine groups, C 6 to C 40 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ selected from the group consisting arylsilyl of C 40 or, by combining groups of adjacent, may form a fused aromatic ring, or a condensed heteroaro
  • R 1 to R 9 forms a bond with L 2 ;
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 13 Boron group, arylphosphine group, mono or diarylphosphinyl group and arylsilyl 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 40 aryl group, 5 to 40 heteroaryl group of nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocyclo
  • the compound of the present invention may have a triplet energy higher than that of the linearly bonded compound, in which each moiety is bonded in three directions with respect to benzene, as shown in Chemical Formula 1, and thus the dopant
  • the exciton transition to the furnace is easy, and in view of confining the excitons generated in the light emitting layer, the light emission efficiency can be increased when used in the light emitting layer.
  • the substituent connected to the benzene moiety by L 1 has an electron donating group (EDG) characteristic of electron donating
  • the substituent connected to L 2 by the benzene moiety is electron
  • EWG electron withdrawing group
  • the electron withdrawing group (EWG) with high electron absorption in one compound and the electron donating group with large electron donor EDG) so that the entire molecule is bipolar (bipolar) properties.
  • the compound of Formula 1 of the present invention may not only have a wide band gap, but also increase the binding force between holes and electrons. Accordingly, the phosphorescent property of the organic EL device may be improved, and the carrier injection ability, the transport ability, or the luminous efficiency may be improved.
  • the compound represented by the formula (1) of the present invention is significantly increased in molecular weight of the compound due to the bonding of the aromatic ring (aromatic ring) or heteroaromatic ring (heteroaromatic ring), the glass transition temperature is improved according to the conventional CBP (4 , 4-dicarbazolybiphenyl) shows a higher thermal stability, and due to the asymmetric structure is also effective in suppressing the crystallization of the organic layer.
  • the efficiency of the organic electroluminescent device and the conventional organic material layer for example, CBP
  • the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • Ar 1 may be a 6-membered nitrogen-containing heterocyclic moiety
  • the substituent linked to L 1 may be dibenzofuran (dibenzo [b, d] furan) or dibenzothiophene (dibenzo).
  • [b, d] thiophene) and the substituents linked by L 2 are from the group consisting of carbazole, phenoxazine, phenothiazine, phenazine and acridine
  • L 1 and L 2 are each independently a single bond, a phenylene group, a biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, car Basolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group It may be selected from the group consisting of, more preferably, L 1 and L 2 may be each independently selected from the group consisting of a single bond, a phenylene group and a biphenylene group.
  • Ar 1 may be a substituent represented by the formula (2):
  • L 3 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;
  • X 1 to X 5 are each independently N or C (R 14 );
  • R 14 is hydrogen, 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 40 aryl group, nuclear atom number 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy groups, C 1 to C 40 alkyloxy groups, C 6 to C 40 arylamine groups, C 3 to C 40 cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 40 arylboron groups, C 6 to C 40 arylphosphine groups, C 6 ⁇ C 40 mono or diaryl phosphine blood group and a C 6 ⁇ C 40 selected from the group consisting of aryl silyl, or as in the combination group and adjacent, may form a fused aromatic ring, or fused heteroaro
  • examples of the substituent represented by Formula 2 include a substituent represented by the following Formula A-1 to A-15, but is not limited thereto:
  • n is an integer from 0 to 4.
  • R 21 is deuterium (D), halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 40 arylamine group, C 1 ⁇ C 40 Alkylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 40 Aryl boron group , C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 mono or diaryl phosphinyl group and C 6 ⁇ C 40 arylsilyl group, or combine with adjacent groups to form a condensed ring
  • R 21 is plural, they are the same as or different from each other;
  • the silyl groups 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 40 aryl group, nuclear atom A number of 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy groups, C 1 to C 40 alkyloxy groups, C 6 to C 40 arylamine groups, C 3 to C 40 cycloalkyl groups, nuclear atoms C 3 to C 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 40 aryl boron group, C 6 to C 40 arylphosphine group, C substituted with 6 ⁇ C 40 mono or diaryl phosphine blood group and one or more substituents selected from the group consisting of a C 6 ⁇ C 40 aryl silyl or of being unsubstitute
  • L 3 is a single bond, a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, It may be selected from the group consisting of indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group, More preferably, L 3 may be a single bond or a phenylene group or a biphenylene group.
  • the compound represented by Formula 1 may be any one of the compounds represented by the following Formulas 3 to 7, but is not limited thereto.
  • a compound of formula 3 or formula 6 is preferred:
  • Ar 1 , Y 1 , Z 1 , L 1 , L 2 , R 1 to R 10 and m are as defined in Formula 1 above.
  • 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.
  • the compound may be used alone, or two or more may be used in combination.
  • the at least one organic material layer may be 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.
  • the organic material layer including the compound represented by Chemical Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and in this case, the host material may include a compound represented by Formula 1 above.
  • 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 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 layer, an electron transport layer, and a cathode are sequentially stacked.
  • An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic EL 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 of the present invention is another organic material layer 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 Formula 1 above. And it can be manufactured by forming 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 silicon wafer quartz, glass plate, metal plate, plastic film, sheet, or the like may 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 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 and the like can be used, but is 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 metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly
  • the negative electrode material may be magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or a metal such as lead or an alloy thereof, and a multilayer such as LiF / Al or LiO 2 / Al. Structural materials and the like may be used, 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.
  • the present invention will be described in detail with reference to Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
  • the target compound 3- (3-bromo-5- (dibenzo [b, d] thiophen-4-yl) phenyl) -9-phenyl-9H -Carbazole (21.0 g, 36.1 mmol, yield 72%) was obtained.
  • the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 9- (3'-chloro-5 '-(dibenzo [b, d] thiophen-4-yl)-[1,1'- Biphenyl] -3-yl) -9H-carbazole (16.1 g, 30.1 mmol, yield 60%) was obtained.
  • the target compound 2- (3,5-dibromophenyl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine ( 32.3 g, 62.1 mmol, 62% yield).
  • dibenzo [b, d] thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid.
  • Example 14 Preparation of Example 14 except that dibenzo [b, d] thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 10- (3-bromo-5- (dibenzo [b, d] thiophen-2-yl) phenyl) -9,9-dimethyl-9,10-dihydroa by following the same procedure as in step 2> Credin (18.4 g, 33.6 mmol, yield 67%) was obtained.
  • Step of Preparation 14 except dibenzo [b, d] furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo [b, d] thiophen-4-ylboronic acid. 2> by the same process as 10- (3-bromo-5- (dibenzo [b, d] furan-2-yl) phenyl-9,9-dimethyl-9,10-dihydroacridine ( 16.4 g, 30.9 mmol, yield 62%).
  • CDT-2 (6.27 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 41 (5.94 g, 81% yield).
  • CDT-2 (6.27 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 52 (5.82 g, 72% yield).
  • CDT-6 5.51 g, 10.00 mmol
  • CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 136 (4.60 g, yield 70%).
  • CDT-8 5.35 g, 10.00 mmol
  • CDT-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound C 176 (5.81 g, 81% yield).
  • CDT-9 (6.28 g, 10.00 mmol) instead of CDT-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 126 (5.28 g, 72% 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
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 11 as a light emitting host material when forming the emission layer.
  • Example 1 C 11 6.83 517 41.1
  • Example 2 C 12 6.82 518 40.7
  • Example 3 C 13 6.49 518 38.9
  • Example 4 C 14 6.81 518 39.1
  • Example 5 C 15 6.82 518 40.7
  • Example 6 C 21 6.49 518 38.9
  • Example 7 C 22 6.81 518 39.1
  • Example 8 C 23 6.66 516 41.7
  • Example 9 C 41 6.68 518 41.7
  • Example 10 C 52 6.63 517 39.3
  • Example 11 Example 11
  • Example 13 C 101 6.66 517 41.1
  • Example 14 C 112 6.71 518 42.2
  • Example 15 121 6.82 517 42.2
  • Example 16 131 6.81 518 41.1
  • Example 18 C 146 6.82 518 39.3
  • Example 19 C 151 6.82 518 39.1
  • Example 20 C 161 6.81 518 39.1
  • Example 21 Example 21
  • Example 21 Example 21
  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly, by including a novel tertiary substituted benzene-based compound having excellent hole injection, transporting ability, and luminescent ability in one or more organic material layers,
  • the present invention relates to an organic EL device having improved characteristics such as efficiency, driving voltage, and lifetime.

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  • Organic Chemistry (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé à base de benzène trisubstitué présentant d'excellents résultats en matière d'injection de trous, de capacité de transfert et de pouvoir luminescent, ainsi qu'un dispositif électroluminescent organique comprenant un tel composé. Le composé selon la présente invention peut améliorer l'efficacité d'émission de lumière, la tension de commande et la durée de vie du dispositif électroluminescent organique s'il est utilisé dans une couche de matériau organique, de préférence une couche luminescente, du dispositif électroluminescent organique.
PCT/KR2015/012975 2014-12-02 2015-12-01 Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé Ceased WO2016089080A1 (fr)

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EP3527557A1 (fr) * 2018-02-16 2019-08-21 Novaled GmbH Composés n-hétéroarylène
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US12022730B2 (en) 2018-11-27 2024-06-25 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
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JP7115745B2 (ja) 2016-08-19 2022-08-09 株式会社Kyulux 電荷輸送材料、化合物、遅延蛍光材料および有機発光素子
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CN107857759A (zh) * 2017-12-04 2018-03-30 吉林奥来德光电材料股份有限公司 有机发光化合物及制法和有机发光器件
WO2019114610A1 (fr) * 2017-12-14 2019-06-20 广州华睿光电材料有限公司 Composé organique de type carbazole-tribenzène, superpolymère, mélange et composition et utilisation correspondante
CN111247133A (zh) * 2017-12-14 2020-06-05 广州华睿光电材料有限公司 咔唑三苯有机化合物、高聚物、混合物、组合物及其应用
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WO2019121112A1 (fr) * 2017-12-21 2019-06-27 Cynora Gmbh Molécules organiques destinées à être utilisées dans des dispositifs optoélectroniques
EP3527557A1 (fr) * 2018-02-16 2019-08-21 Novaled GmbH Composés n-hétéroarylène
CN110386924A (zh) * 2018-04-17 2019-10-29 三星显示有限公司 有机电致发光器件和用于其的含氮化合物
US12133458B2 (en) 2018-04-17 2024-10-29 Samsung Display Co., Ltd. Organic electroluminescence device and nitrogen-containing compound for organic electroluminescence device
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US12275736B2 (en) 2018-11-27 2025-04-15 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
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US11746117B2 (en) 2018-11-27 2023-09-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising same
US12098156B2 (en) 2018-11-27 2024-09-24 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
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US11814374B2 (en) 2019-07-23 2023-11-14 Lg Display Co., Ltd. Organic compound, and organic light emitting diode and organic light emitting display device including the same
CN112300128B (zh) * 2019-07-23 2023-08-29 乐金显示有限公司 有机化合物及包含其的有机发光二极管和有机发光显示装置
WO2021129102A1 (fr) * 2019-12-27 2021-07-01 陕西莱特光电材料股份有限公司 Composé hétérocyclique, son procédé de synthèse, dispositif électroluminescent organique et appareil électronique
CN111320608A (zh) * 2019-12-27 2020-06-23 陕西莱特光电材料股份有限公司 杂环化合物及其合成方法和有机电致发光器件和电子设备
EP4265612A4 (fr) * 2020-12-21 2025-07-02 Lt Materials Co Ltd Composé hétérocyclique, dispositif électroluminescent organique le comprenant, procédé de fabrication correspondant et composition pour couche de matériau organique
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