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WO2016105138A2 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

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

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Publication number
WO2016105138A2
WO2016105138A2 PCT/KR2015/014209 KR2015014209W WO2016105138A2 WO 2016105138 A2 WO2016105138 A2 WO 2016105138A2 KR 2015014209 W KR2015014209 W KR 2015014209W WO 2016105138 A2 WO2016105138 A2 WO 2016105138A2
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compound
aryl
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WO2016105138A9 (fr
WO2016105138A3 (fr
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손효석
김동연
조흥상
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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
    • C07D403/02—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
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to an arylamine-based compound having excellent heat resistance, electron blocking ability, and hole transporting ability, and the like as a material of the organic material layer, and thus low driving voltage. And an organic electroluminescent device having excellent luminous efficiency and improved lifetime characteristics.
  • the organic electroluminescent (EL) device (hereinafter, simply referred to as 'organic EL device'), which led to blue electroluminescence using anthracene single crystal in 1965, was used.
  • Tang proposed an organic EL device having a laminated structure divided into functional layers of a hole layer and a light emitting layer by Tang. Since then, in order to improve the efficiency and lifespan of the organic EL device, it has been developed in the form of introducing a characteristic organic material layer in the device, and also led to the development of specialized materials used therein.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • 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, it can be divided into yellow and orange light emitting materials required 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. Since the development of phosphorescent materials can theoretically improve luminous efficiency up to four times compared to fluorescence, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like represented by the following general formulas
  • anthracene derivatives have been reported as fluorescent dopant / host materials.
  • 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 , which are blue and green. It is used as a red dopant material.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the conventional light emitting materials are good in terms of the light emission characteristics, but because the glass transition temperature (Tg) is low thermal stability is not very good, it is not a satisfactory level in terms of life in the organic electroluminescent device. Therefore, there is a demand for the development of an organic EL device including a light emitting material having excellent performance.
  • Tg glass transition temperature
  • the device in order to realize the practical use and improvement of the characteristics of the organic EL device, not only the device should be composed of the organic material layer having the multilayer structure as described above, but also the material of the device, in particular, the hole transport material should have thermal and electrical stable properties. Because, due to the heat generated from the device when the voltage is applied, molecules with low thermal stability have low crystal stability, resulting in rearrangement. An inhomogeneous part exists due to such localized crystallization, and an electric field is generated in the heterogeneous part. This is because concentration results in deterioration and destruction of the device.
  • conventionally used hole transport materials include m-MTDATA [4, 4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) -triphenylamine, 2-TNATA. [4, 4 ', 4 "-tris (N- (naphthylene-2-yl) -N-phenylamino) -triphenylamine], TPD [N, N'-diphenyl-N, N'-di ( 3-methylphenyl) -4, 4'-diaminobiphenyl] and NPB [N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine].
  • m-MTDATA and 2-TNATA have a low glass transition temperature (Tg) of 78 ° C. and 108 ° C., respectively.
  • TPD and NPB have low glass transition temperatures (Tg) of 60 ° C. and 96 ° C., respectively, there is a fatal disadvantage of shortening the lifespan of devices. Accordingly, there is a demand for the development of an organic electroluminescent device capable of increasing thermal stability, having excellent hole transporting ability, and improving the luminous efficiency and power efficiency of the organic electroluminescent device.
  • An object of the present invention is to provide a novel organic compound having excellent heat resistance, electron blocking ability, hole transporting ability, and the like, which can be used as a light emitting auxiliary layer material, a hole transporting layer material, a hole injection layer material, and the like.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound described above, which has a low driving voltage, high luminous efficiency, and improved lifespan characteristics.
  • the present invention provides a compound represented by the following formula (1):
  • Ar 1 and Ar 2 are each independently a substituent represented by formula (2);
  • Ar 3 is a substituent represented by the following formula (3);
  • X 1 is selected from the group consisting of O, S, N (R 6 ) and C (R 7 ) (R 8 );
  • At least one of R 4 to R 8 forms a bond with L 1 or L 2 ;
  • R 1 to R 3 and R 6 to R 8 which do not form a bond with L 1 or L 2 are each independently hydrogen, deuterium, 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl group, 5 to 60 nuclear atoms Heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 A group consisting of an alkylboron group of C 6 to C 60, an aryl boron group of C 6 to C 60 , an arylphosphine group of C 6 to C 60 , a mono or diarylphosphinyl group of C 6 to C 60 ,
  • a and b are each independently an integer of 0 to 4.
  • L 1 or not form a bond and L 2 R 4 and R 5 are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl, C alkenyl group of 2 ⁇ C 40, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ , or selected from the group consisting of an aryl
  • Ar 4 And the Ar 5 are each independently C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or of said Ar 4 and Ar 5 each other Can form bonds;
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, a C 6 -C 18 arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
  • the aryl group, heteroaryl group and arylamine group of R 1 to R 8 and Ar 4 to Ar 5 , alkyl group, cycloalkyl group, heterocycloalkyl group, alkyloxy group, aryloxy group, alkylsilyl group of R 1 to R 8 , Arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group and mono or diaryl phosphinyl group, L 1 to L 3 arylene group, heteroarylene group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, a nuclear atoms 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a fluorenyl group and a pyridinyl group do.
  • Ar 4 and Ar 5 are each independently characterized as a C 6 ⁇ C 18 aryl group or a nuclear atom of 5 to 18 heteroaryl groups.
  • At least one of Ar 4 and Ar 5 is characterized in that the substituent represented by the formula (2).
  • X 1 is O or S
  • at least one of R 4 and R 5 is characterized in that to form a bond with L 1 or L 2 .
  • X 1 is N (R 6 ), and at least one of R 4 to R 6 is characterized in that to form a bond with L 1 or L 2 .
  • X 1 is C (R 7 ) (R 8 ), and at least one of R 4 to R 5 and R 7 to R 8 is L 1 or L 2 and It is characterized by forming a bond.
  • X 1 is C (R 7 ) (R 8 ), and R 7 and R 8 are each independently a methyl group or a phenyl group, or R 7 and R 8 are It is characterized by forming a substituent represented by the formula (7).
  • the compound represented by Formula 1 is characterized in that represented by any one of the following formula (4) to formula (6).
  • X 2 is selected from the group consisting of O, S, N (R 6 ) and C (R 7 ) (R 8 );
  • n are each independently an integer from 0 to 3;
  • p and q are each independently integers of 0 to 4.
  • R 9 and R 10 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 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Is selected from the group consisting of an aryl phosphine group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylamine group, or may be combined with an adjacent group to form a con
  • the present invention (i) an anode; (ii) a negative electrode; And (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by Formula 1 above.
  • At least one organic material layer including the compound represented by Chemical Formula 1 may be selected from the group consisting of a hole transport layer, an electron blocking layer, and a light emitting auxiliary 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 an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 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
  • aryloxy 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 provided in the present invention is excellent in heat resistance, electron blocking ability and hole transporting ability, and can be usefully applied as a material of the organic material layer of the organic EL device.
  • the organic electroluminescent device including the compound of the present invention in one or more organic material layers has a low driving voltage, excellent luminous performance and efficiency, lifespan characteristics are improved, and can be effectively applied to a full color display panel.
  • the present invention provides a compound represented by Formula 1:
  • Ar 1 and Ar 2 are each independently a substituent represented by formula (2);
  • Ar 3 is a substituent represented by the following formula (3);
  • X 1 is selected from the group consisting of O, S, N (R 6 ) and C (R 7 ) (R 8 );
  • At least one of R 4 to R 8 forms a bond with L 1 or L 2 ;
  • R 1 to R 3 and R 6 to R 8 which do not form a bond with L 1 or L 2 are each independently hydrogen, deuterium, 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl group, 5 to 60 nuclear atoms Heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 A group consisting of an alkylboron group of C 6 to C 60, an aryl boron group of C 6 to C 60 , an arylphosphine group of C 6 to C 60 , a mono or diarylphosphinyl group of C 6 to C 60 ,
  • a and b are each independently an integer of 0 to 4.
  • L 1 or not form a bond and L 2 R 4 and R 5 are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl, C alkenyl group of 2 ⁇ C 40, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ , or selected from the group consisting of an aryl
  • Ar 4 And the Ar 5 are each independently C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or of said Ar 4 and Ar 5 each other Can form bonds;
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, a C 6 -C 18 arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
  • the aryl group, heteroaryl group and arylamine group of R 1 to R 8 and Ar 4 to Ar 5 , alkyl group, cycloalkyl group, heterocycloalkyl group, alkyloxy group, aryloxy group, alkylsilyl group of R 1 to R 8 , Arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group and mono or diaryl phosphinyl group, L 1 to L 3 arylene group, heteroarylene group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, a nuclear atoms 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60
  • the present invention is an arylamine-based compound having excellent heat resistance, electron blocking ability, and hole transporting ability, and has one arylamine group and two dibenzo moieties (dibenzofuran, dibenzo) centered on a 1,3,5-substituted benzene ring. It is intended to provide a novel organic compound characterized in that the base core (thiophene), carbazole, fluorene is bonded.
  • the compound of the present invention may be represented by the following formula (1).
  • Ar 1 and Ar 2 are each independently a substituent represented by formula (2);
  • Ar 3 is a substituent represented by the following formula (3);
  • X 1 is selected from the group consisting of O, S, N (R 6 ) and C (R 7 ) (R 8 );
  • At least one of R 4 to R 8 forms a bond with L 1 or L 2 ;
  • R 1 to R 3 and R 6 to R 8 which do not form a bond with L 1 or L 2 are each independently hydrogen, deuterium, 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl group, 5 to 60 nuclear atoms Heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 A group consisting of an alkylboron group of C 6 to C 60, an aryl boron group of C 6 to C 60 , an arylphosphine group of C 6 to C 60 , a mono or diarylphosphinyl group of C 6 to C 60 ,
  • a and b are each independently an integer of 0 to 4.
  • L 1 or not form a bond and L 2 R 4 and R 5 are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl, C alkenyl group of 2 ⁇ C 40, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ , or selected from the group consisting of an aryl
  • Ar 4 and Ar 5 are each independently selected from the group consisting of C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group and C 6 ⁇ C 60 arylamine group, or Ar 4 and Ar 5 May form a bond with each other to form, for example, a 5-membered heterocyclic ring, more specifically, a carbazole structure, or Ar 4 and Ar 5 may be each independently an aryl group or a nuclear atom of C 6 to C 60 . It is preferably a number of 5 to 60 heteroaryl groups, more preferably each of Ar 4 and Ar 5 is a substituent represented by the formula (2);
  • L 1 to L 3 is selected from a single bond, a C 6 ⁇ C 18 arylene group and a nuclear atoms of 5 to 18 heteroaryl group consisting of alkylene group for each independently, preferably a single bond, phenylene, biphenylene , Fluorenyl and pyridinyl groups;
  • the organic light emitting compound of Chemical Formula 1 has better stability than the conventional hole transporting material and has excellent life characteristics of the material, and thus, the driving life of the device is very excellent and power consumption is improved by inducing an increase in power efficiency.
  • An advantage is that OLED devices can be manufactured.
  • the arylamine group, the dibenzo moiety (dibenzofuran, dibenzothiophene), carbazole, and fluorene each have electron donor group (EDG) characteristics, and thus have stable and good hole mobility. Therefore, the compound represented by Formula 1 of the present invention, in which the moiety is bonded in an asymmetric structure, is thermally stable and has advantages as a hole transporting material that can maximize efficiency characteristics by improving hole mobility.
  • the compound of Formula 1 of the present invention is used to increase the efficiency of the fluorescent blue device, the role of which has a hole mobility (Hole mobility) above a certain level (higher than Hole Mobility of NPB), T1 value is It is higher than the blue fluorescent light emitting layer, preventing the triplet excitons from flowing into the BIL, and limiting the inside of the light emitting layer to convert the triplet excitons into singlet excitons through TTA (TTF), thereby increasing efficiency.
  • Hole mobility hole mobility
  • NPB Hole Mobility of NPB
  • the hole-related layer (Hole-related layer) and the light emitting layer (EML)
  • the emission auxiliary layer restricts the triplet excitons from being injected into the hole-related layer, and at the same time has a delta Est ( ⁇ 0.5 eV) characteristic of less than a certain level, thereby entering the emission auxiliary layer in a small amount. It may serve to move the triplet excitons to the singlet level. This transitions back to the singlet level of the EML to participate in the exciton generation, and consequently to the triplet level of the EML to eliminate the loss of efficiency that can occur when no emission auxiliary layer is provided, or the efficiency of the phosphorescent light emitting layer (EML). Serves to increase.
  • EML phosphorescent light emitting layer
  • the compound represented by Chemical Formula 1 according to the present invention has a basic structure rich in electrons (electron rich), excellent hole mobility and high triplet energy, carbazole moiety, dibenzofuran, dibenzothiophene Since it includes a fluorene moiety, there is an advantage as a light emitting auxiliary layer material that can maximize efficiency characteristics.
  • X 1 may be selected from the group consisting of O, S, N (R 6 ), and C (R 7 ) (R 8 ), but as an example.
  • X 1 is O or S
  • at least one of R 4 to R 5 may form a bond with L 1 or L 2
  • R 4 to R 6 At least one of may form a bond with L 1 or L 2
  • X 1 is C (R 7 ) (R 8 )
  • at least one of R 4 to R 5 and R 7 to R 8 May form a bond with L 1 or L 2 .
  • R 7 and R 8 are each independently a methyl group or a phenyl group, or R 7 and R 8 are each other It may be combined to form a substituent represented by Formula 7, but is not limited thereto.
  • the compound represented by Chemical Formula 1 is characterized in that represented by any one of the following Chemical Formulas 4 to:
  • X 2 is selected from the group consisting of O, S, N (R 6 ) and C (R 7 ) (R 8 );
  • n are each independently an integer from 0 to 3;
  • p and q are each independently integers of 0 to 4.
  • R 9 and R 10 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 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Is selected from the group consisting of an aryl phosphine group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylamine group, or may be combined with an adjacent group to form a con
  • X 1 , L 1 to L 3, R 1 to R 5 , Ar 4 , Ar 5 , a and b are as defined in Chemical Formulas 1 to 3.
  • the compound represented by Chemical Formula 1 may be further embodied as a compound represented by any one of the chemical formulas illustrated below.
  • the compound represented by the formula (1) of the present invention is not limited by those illustrated below:
  • the compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • organic electroluminescent device comprising the compound represented by the formula (1).
  • 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 organic layer includes a compound represented by the formula (1).
  • the compound represented by Formula 1 may be used alone or two or more kinds thereof are mixed.
  • the one or more organic material layers may include any one or more of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transporting layer, an electron transporting layer, an electron injection layer, and an electron blocking layer, wherein at least one organic material layer It may include a compound represented by the formula (1).
  • the organic material layer including the compound represented by Chemical Formula 1 may be selected from the group consisting of a light emission auxiliary layer, a hole transport layer, and an electron blocking layer, and more preferably, a hole transport layer.
  • the compound represented by Formula 1 when included in the organic electroluminescent device as a light emitting layer material, it can be expected to improve the luminous efficiency, brightness, power efficiency, thermal stability and device life of the organic electroluminescent device.
  • the structure of the organic EL device according to the present invention is not particularly limited.
  • an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device may include a life improvement layer or an electron transport auxiliary layer between the light emitting layer and the electron transport layer.
  • the compound represented by Chemical Formula 1 may also be used as a life improvement layer or an electron transport auxiliary layer.
  • the organic electroluminescent device of the present invention is manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one of the organic material layers is formed to include the compound represented by Chemical Formula 1. Can be.
  • 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 that can be used in the manufacture of the organic electroluminescent device in the present invention is not particularly limited, and examples thereof include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or a sheet, and the like.
  • 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 and polyaniline; Or carbon black, but is 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
  • examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • hole injection layer material, the hole transport layer material, the electron injection layer material and the electron transport layer material are not particularly limited, and conventional materials known in the art may be used.
  • a target compound was prepared by the same procedure as in Synthesis Example 9, except that 4- (dibiphenyl-4-ylamino) phenylboronic acid (3.45 g, 7.82 mmol) was used instead of 4- (diphenylamino) phenylboronic acid. 5.29 g (yield: 79%) was obtained.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • M-MTDATA 60 nm) / A-1 to M-24 compound (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (ITO transparent electrode prepared as above)
  • An organic EL device was manufactured in the order of 30 nm) / LiF (1 nm) / Al (200 nm).
  • DS-H522 and DS-501 used in device fabrication are products of Doosan Electronics BG, and the structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 , and BCP are as follows.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compounds A-2 to L-24 were used instead of Compound A-1 used as the hole transport layer in forming the hole transport layer in Example 1. .
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that NPB was used as the hole transport layer instead of Compound A-1, which was used as the hole transport layer in forming the hole transport layer.
  • the structure of the NPB used is as follows.
  • Example A-1 Compound A-1 4.1 22.2 Example A-2 Compound A-2 4.3 20.1 Example A-3 Compound A-3 4.4 21.3 Example A-4 Compound A-4 4 22.6 Example A-5 Compound A-5 4.5 19.5 Example A-6 Compound A-6 4.7 20.1 Example A-7 Compound A-7 4.3 21.6 Example A-8 Compound a-8 4.5 20.5 Example A-9 Compound A-9 4.7 20.6 Example A-10 Compound A-10 4.4 21.6 Example A-11 Compound A-11 5 20.1 Example A-12 Compound a-12 5.1 18.6 Example A-13 Compound a-13 4.3 22 Example A-14 Compound a-14 4.6 21.2 Example A-15 Compound a-15 4.5 21.2 Example A-16 Compound a-16 4.4 22.3 Example A-17 Compound a-17 5.1 18.3 Example A-18 Compound A-18 5 18.9 Example A-19 Compound a-19 4.5 21.7 Example A-20 Compound A-20 4.7 21.2 Example A-21 Compound a-21 4.8 20.8
  • the organic electroluminescent device (the organic electroluminescent devices manufactured in Examples A-1 to A-330, respectively) using the compound according to the present invention as the hole transport layer is an organic EL device using a conventional NPB. Compared with the (organic EL device of Comparative Example 1), it was found to show better performance in terms of current efficiency and driving voltage.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • An organic electroluminescent device was manufactured by laminating in order of / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • An organic electroluminescent device was manufactured in the same manner as in Example B-1, except that Compounds A-2 to M-24 were used instead of Compound A-1 in Example B-1.
  • a green organic electroluminescent device was manufactured in the same manner as in Example B-1, except that Compound A-1 was not used in Example B-1.
  • Example B-1 Compound A-1 6.7 41.9
  • Example B-2 Compound A-2 6.85 42.1
  • Example B-3 Compound A-3 6.8 44.8
  • Example B-4 Compound A-4 6.8 47.5
  • Example B-5 Compound A-5 6.85 41.5
  • Example B-6 Compound A-6 6.9 41.9
  • Example B-7 Compound A-7 6.95 42.4
  • Example B-8 Compound a-8 6.8 42.3
  • Example B-9 Compound A-9 6.9 45.2
  • Example B-10 Compound A-10 6.8 44.6
  • Example B-11 Compound A-11 6.7 44.1
  • Example B-12 Compound a-12 6.65 43.6
  • Example B-13 Compound a-13 6.7 42.6
  • Example B-14 Compound a-14 6.9 44.1
  • Example B-15 Compound a-15 6.8 42.8
  • Example B-16 Compound a-16 6.7 41.4
  • Example B-17 Compound a-17 6.7 41.8
  • Example B-18 Compound A-18 6.65 45.3
  • Example B-19 Compound a-19 6.7 45.1
  • the green organic electroluminescent device (the green organic electroluminescent devices manufactured in Examples B-1 to B-330, respectively) using the compound represented by Formula 1 according to the present invention as a light emitting material
  • the conventional green organic electroluminescent device (the organic electroluminescent device of Comparative Example 2) using only CBP as a material of the light emitting layer, it was found that the performance was better in terms of current efficiency and driving voltage.
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • each compound (40 nm) / CBP + 10% (piq) 2 Ir (acac) of m-MTDATA (60 nm) / TCTA (80 nm) / A-1 to M-24 ( 30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare an organic EL device.
  • a red organic electroluminescent device was manufactured in the same manner as in Example C-1, except that Compound A-1 was not used in Example C-1.
  • the red organic electroluminescent devices (the red organic electroluminescent devices manufactured in Examples C-1 to C-330, respectively) using the compound represented by Formula 1 according to the present invention as a light emitting material, Compared with the red organic electroluminescent element (the organic electroluminescent element of Comparative Example 3) using only the conventional CBP as the material of the light emitting layer, it was found to exhibit better performance in terms of current efficiency and driving voltage.
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • each compound (15 nm) / ADN + 5% DS-405 (of DS-205 (Doosan) (80 nm) / NPB (15 nm) / A-1 to M-24 ( Doosan Corporation) (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
  • ADN The structure of ADN used is as follows.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example D-1, except that A-1 was not used in Example D-1.
  • the blue organic electroluminescent devices (the blue organic electroluminescent devices manufactured in Examples D-1 to D-330, respectively) using the compound represented by Formula 1 according to the present invention as a light emitting material, Compared with the conventional blue organic electroluminescent element (the organic electroluminescent element of Comparative Example 4), it was found to exhibit better performance in terms of current efficiency and driving voltage.
  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to an arylamine-based compound having excellent heat resistance, electron blocking ability, and hole transporting ability, and the like as a material of the organic material layer, and thus low driving voltage. And an organic electroluminescent device having excellent luminous efficiency and improved lifetime characteristics.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique qui comprend un nouveau composé ayant une excellente résistance thermique, une excellente aptitude au transport de trous, et une excellente puissance d'arrêt d'électrons etc., dans une ou plusieurs couches organiques, de manière à avoir une faible tension d'attaque, une performance et une efficacité élevées d'émission de lumière, et des caractéristiques de durée de vie améliorées.
PCT/KR2015/014209 2014-12-26 2015-12-23 Composé organique et dispositif électroluminescent organique comprenant un tel composé Ceased WO2016105138A2 (fr)

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