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WO2019098695A1 - Composé organique et dispositif électroluminescent organique l'utilisant - Google Patents

Composé organique et dispositif électroluminescent organique l'utilisant Download PDF

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WO2019098695A1
WO2019098695A1 PCT/KR2018/013980 KR2018013980W WO2019098695A1 WO 2019098695 A1 WO2019098695 A1 WO 2019098695A1 KR 2018013980 W KR2018013980 W KR 2018013980W WO 2019098695 A1 WO2019098695 A1 WO 2019098695A1
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aryl
layer
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formula
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Korean (ko)
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엄민식
심재의
박우재
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Doosan Corp
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Doosan Corp
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Priority to CN202311262737.6A priority Critical patent/CN117304173A/zh
Priority to CN201880074417.9A priority patent/CN111406052A/zh
Publication of WO2019098695A1 publication Critical patent/WO2019098695A1/fr
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same and more preferably to a compound having excellent electron transporting ability and light emitting ability and by incorporating it into one or more organic layers to improve characteristics such as luminous efficiency, And an organic electroluminescent device.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.
  • the light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color.
  • yellow and orange light emitting materials are also used as light emitting materials for realizing better color.
  • a host / dopant system can be used as a light emitting material.
  • the dopant material can 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.
  • hole injecting layer hole transporting layer.
  • NPB, BCP, Alq 3 and the like are widely known as materials used in the hole blocking layer and the electron transporting layer, and anthracene derivatives are reported as luminescent materials.
  • a metal complex compound containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like having advantages in terms of efficiency improvement as a light emitting material has a blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.
  • CBP 4,4-dicarbazolybiphenyl
  • the present invention relates to a novel compound capable of being used for an organic material layer material of an organic electroluminescence device, specifically a light emitting layer material, a life improving layer material, a light emitting auxiliary layer material, or an electron transporting layer material, And to provide the above objects.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.
  • an example of the present invention provides a compound represented by the following formula:
  • X 1 to X 3 are each nitrogen or CR 4 , and contain at least two or more nitrogen atoms,
  • One of Y 1 to Y 4 is nitrogen and the other is CR 5 , and when there are plural R 5 s , they are the same or different,
  • n is an integer of 1 to 3
  • L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,
  • R 1 is in combination with a selected from hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, and the group consisting of an aryl group of C 6 ⁇ C 60 of or, or adjacent groups (e.g., adjacent the other R 1, etc.) To form a fused ring, wherein the plurality of R < 1 > are the same or different from each other;
  • a is an integer of 0 to 4,
  • A is a substituent represented by the following formula (2) or (3)
  • Z 1 to Z 3 are each nitrogen or CR 6 , and contain at least two or more nitrogen atoms,
  • Z 4 to Z 6 are each nitrogen or CR 7 , and contain at least two or more nitrogen atoms,
  • Ar 1 to Ar 4 are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cyclo
  • a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group is selected from the group consisting of a C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6
  • R 2 to R 7 are the same or different and are each independently hydrogen, deuterium, 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
  • the aryl group and the heteroarylene group of L each independently represent a group selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, an alkoxy group, an aryloxy group, An amino group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms
  • the present invention provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by Formula 1
  • a light emitting device is provided.
  • the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injecting layer.
  • the compound represented by Formula 1 may be used as an electron transporting material for the electron transporting layer and the electron transporting layer.
  • the compound represented by the formula (1) according to an example of the present invention is excellent in heat resistance, carrier transport ability, and light emitting ability, and can be used as an organic material layer material of an organic electroluminescent device
  • the organic electroluminescent device including the compound according to an example of the present invention can significantly improve aspects such as light emitting performance, driving voltage, lifetime, and efficiency, and thus can be effectively applied to a full color display panel and the like.
  • a novel organic compound according to the present invention includes an electron-withdrawing group (EWG) in which two or more nitrogen (N) is contained in an electron-withdrawing group (EWG) in which pyridine compound is bonded to triazine or pyrimidine, and a linker to form an asymmetrically connected structure.
  • EWG electron-withdrawing group
  • pyridine compound is bonded to triazine or pyrimidine, and a linker to form an asymmetrically connected structure.
  • electron-donating groups containing two or more nitrogen atoms are triazine, pyrimidine, and triazolopyridine.
  • Compounds having various substituents introduced into these basic skeletons are represented by the above formula (1).
  • the compound represented by the formula (1) has a higher electron transporting ability than the conventional organic EL device materials and can exhibit a relatively high luminous efficiency.
  • the compound represented by the formula (1) has a high glass transition temperature and thus is excellent in thermal stability, It is excellent. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.
  • the compound is not only excellent in electron mobility but also excellent in high glass transition temperature and thermal stability. Accordingly, the compound represented by the general formula (1) of the present invention is excellent in electron transporting ability and light emitting property, and therefore, it is preferable that the compound represented by the general formula (1) It can be used as a material.
  • an electron transporting auxiliary layer laminated on the light emitting layer of green phosphorescence, the electron transporting layer and the electron transporting layer Preferably an electron transporting auxiliary layer laminated on the light emitting layer of green phosphorescence, the electron transporting layer and the electron transporting layer.
  • TTF triplet-triplet fusion
  • the number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device and the durability and stability of the device can be improved and the lifetime of the device can be efficiently increased.
  • Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.
  • the compound represented by the above formula (1) is not only very advantageous for electron transport, but also exhibits long life characteristics.
  • the excellent electron transporting ability of such a compound can have high efficiency and fast mobility in an organic electroluminescent device, and it is easy to control HOMO and LUMO energy levels according to the direction or position of a substituent. Therefore, high electron transportability can be exhibited in the organic electroluminescent device using such a compound.
  • the compound represented by the formula (1) according to the present invention can be represented by any one of the following formulas (4) to (8).
  • X 1 to X 3 , Y 1 to Y 4 , L, A and n are as defined in formula (1).
  • L in the formula (1) may be a single bond or a structure represented by the following formulas L-1 to L-5.
  • a in the formula (1) may be selected from the group consisting of the structures represented by the following A-1 to A-12.
  • a in the formula (1) may be selected from the group consisting of the structures represented by the following A-13 to A-26.
  • Ar 1 to Ar 4 may each independently be an aryl group selected from the following structures.
  • the compound represented by formula (1) according to the present invention may be further represented by any of compounds 1 to 160 shown below.
  • the compounds represented by formula (1) of the present invention are not limited by the following examples.
  • alkyl means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl, and the like.
  • alkenyl means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond.
  • alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond.
  • alkynyls 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. Also, a form in which two or more rings are pendant or condensed with each other may 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 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by 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 further, a condensed form with an aryl group may be included.
  • heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy means a monovalent functional group represented by R “O-, and R" is aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy means a monovalent functional group represented by R'O-, and R 'is alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic . ≪ / RTI > Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Cycloalkyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Non-limiting examples thereof include 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, Quot; means a boron group substituted with aryl having 6 to 60 carbon atoms
  • arylphosphine group means a phosphine group substituted with aryl having 1 to 60 carbon atoms, &Quot
  • arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • condensed rings means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
  • the compound represented by formula (1) according to the present invention can be synthesized in various ways by referring to the synthesis process of the following examples. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).
  • the organic electroluminescent device includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1).
  • the compounds may be used alone or in combination of two or more.
  • the at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer. ≪ / RTI > compounds. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is a light emitting layer, an electron transporting auxiliary layer and an electron transporting layer.
  • the light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent host material).
  • the light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially stacked .
  • At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, and the electron transporting layer may include the compound represented by the formula (1), and preferably the light emitting layer or the electron transporting layer comprises the compound represented by the formula . ≪ / RTI >
  • an electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent device of the present invention may be a structure in which an electrode and an electron transporting auxiliary layer are added together with the organic material layer described above.
  • at least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting supporting layer and the electron transporting layer may include the compound represented by the above formula (1)
  • the transport layer may contain a compound represented by the above formula (1).
  • the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.
  • the positive electrode material examples 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), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
  • ZnO Al or SnO 2: a combination of a metal and an oxide such as Sb
  • Conductive polymers such as polythiophene, poly (3
  • 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; And multi-layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting layer, the hole transporting layer, and the light emitting auxiliary layer are not particularly limited, and ordinary materials known in the art can be used.
  • a mixed solvent of ethanol / methanol (1: 1, 2.15 L) was added to 298 g of hydroxylamine hydrochloride. 399 ml of triethylamine was added to the reaction solution and stirred for 1 hour. 215 g of [(2-pyridinylamino) thioxomethyl] -, ethyl ester synthesized above was added and the temperature was gradually raised, and the mixture was heated to reflux for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered.
  • PPY-2 was used instead of PPY-1 in Synthesis Example 1 and ID-1 was used instead of (4- (4,6-diphenyl-1,3,5-triazin- Compound 6 (2.9 g, yield 56%) was prepared in the same manner except that
  • Compound 76 (2.1 g, yield 41%) was prepared in the same manner as in Synthesis Example 9, except that PPY-6 was used instead of PPY-3.
  • glass substrate coated with ITO (Indium tin oxide) thin film of 1500 ⁇ thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • a blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that Alq 3 was used instead of Compound 1 as the electron transport layer material.
  • a blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that Compound 1 was not used as an electron transport layer material.
  • NPB, ADN and Alq3 used in Examples 1 to 14 and Comparative Examples 1 and 2 are as follows.
  • Each of the blue organic electroluminescent devices fabricated in Examples 1 to 14 and Comparative Examples 1 and 2 was measured for driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm 2, Respectively.
  • Example 1 Compound 1 3.5 455 8.1
  • Example 2 Compound 3 3.3 455 8.3
  • Example 3 Compound 6 3.4 456 7.9
  • Example 4 Compound 11 3.6 453 8.3
  • Example 5 Compound 13 3.2 454 8.1
  • Example 6 Compound 16 3.4 456 8.3
  • Example 7 Compound 21 3.5 455 8.7
  • Example 8 Compound 31 3.9 456 8.2
  • Example 9 Compound 36 3.7 454 8.3
  • Example 10 Compound 41 3.5 453 8.1
  • Example 11 Compound 43 3.3 455 8.3
  • Example 12 Compound 46 3.7 455 8.1
  • Example 13 Compound 71 3.8 454 8.8
  • Example 14 Compound 76 4.3 454 7.3 Comparative Example 1 Alq 3 4.8 457 5.6 Comparative Example 2 - 4.7 459 6.1

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé dans une couche de matière organique d'un dispositif électroluminescent organique, de préférence, pour une couche électroluminescente, une couche auxiliaire d'émission, une couche auxiliaire de transport d'électrons ou une couche de transport d'électrons, ce qui permet d'améliorer l'efficacité d'émission, la tension de commande, la durée de vie, etc. dans le dispositif électroluminescent organique.
PCT/KR2018/013980 2017-11-15 2018-11-15 Composé organique et dispositif électroluminescent organique l'utilisant Ceased WO2019098695A1 (fr)

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