WO2013002514A2 - Dispositif électroluminescent organique utilisant des dérivés de diarylamine, et nouveau composé et nouvelle composition pour le dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique utilisant des dérivés de diarylamine, et nouveau composé et nouvelle composition pour le dispositif électroluminescent organique Download PDF

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WO2013002514A2
WO2013002514A2 PCT/KR2012/004939 KR2012004939W WO2013002514A2 WO 2013002514 A2 WO2013002514 A2 WO 2013002514A2 KR 2012004939 W KR2012004939 W KR 2012004939W WO 2013002514 A2 WO2013002514 A2 WO 2013002514A2
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group
aryl
substituted
mmol
deuterium
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PCT/KR2012/004939
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WO2013002514A3 (fr
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이선희
문성윤
이범성
최대혁
김동하
박정환
박정철
김기원
주진욱
박용욱
박정근
지희선
김혜령
소기호
강문성
박성제
황선필
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덕산하이메탈(주)
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Publication of WO2013002514A3 publication Critical patent/WO2013002514A3/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • 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]
    • H10K50/17—Carrier injection 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to an organic electric device comprising a novel compound as a hole injection layer material or a hole transport layer material, and more particularly, a hole injection layer material or a hole transport layer material having a low driving voltage, high luminous efficiency and improved device life characteristics.
  • an organic EL device capable of low-voltage driving with a self-luminous type has a superior viewing angle and contrast ratio compared to a liquid crystal display (LCD), which is the mainstream of flat panel display devices, and has a low backlight since no backlight is required. And it is possible to thin, and has an advantage in terms of power consumption.
  • the fast response speed and wide color reproduction range have attracted attention as a next generation display device.
  • an organic EL device is formed on a glass substrate in order of an anode made of a transparent electrode, an organic thin film including a light emitting region, and a metal electrode.
  • the organic thin film may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer in addition to the emitting layer (EML).
  • EIL electron injection layer
  • EBL electron blocking layer
  • HBL hole blocking layer
  • the light emitting excitation emits light as it transitions to ground states, in which a light emitting layer (guest) is doped into the light emitting layer (host) to increase the efficiency and stability of the light emitting state.
  • the life of the device is important, and various studies are being conducted to increase the life of the organic electronic device.
  • a low voltage driving and high voltage may be achieved by replacing an amine compound including carbazole having excellent life with deuterium or by mixing a compound substituted with deuterium. It aims to complete a lifetime element.
  • the present invention provides a compound represented by the following formula (1).
  • the present invention provides a composition for an organic electric device containing a mixture of two or more different compounds of the compound represented by Formula 1, wherein at least one of the two or more different compounds Is a compound containing deuterium.
  • the two or more different compounds may be mixed in any one compound in the range of 90% by weight or less of the total weight of the composition.
  • the present invention provides an organic electric device using the compound represented by the formula (1).
  • the present invention provides an organic electric device using a composition containing a mixture of two or more different compounds of the compounds represented by the formula (1), wherein at least of the two or more different compounds One is a compound containing deuterium.
  • the two or more different compounds may be mixed in a range of 90% by weight or less of any one compound of the total weight of the composition.
  • the present invention provides an organic electric device using the novel compound and the composition comprising the same as the hole injection layer material and the hole transport layer material, which is used in the present invention. It has the effect of improving the low voltage driving, high luminous efficiency and device life of the device.
  • 1 to 6 show examples of the organic electroluminescent device to which the compound of the present invention can be applied.
  • the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
  • the major challenge of the present organic electroluminescent device is the urgent need to overcome the problems of power consumption and lifespan as panel sizes of mobile phones and tablet PCs are enlarged.
  • the materials having excellent hole transporting ability that is, having high hole mobility, in order to lower the driving voltage are most likely to have a planar structure rich in electrons. Examples are naphthyl, fluorene and phenanthrene.
  • the compound of the above structure is introduced into the hole transport material as a substituent, the hole mobility increases to a certain number and has a good effect on the lifetime, but the number of introduction into the molecule is required in order to reach the low voltage driving target required by the current industry. Increasing the driving voltage lowers the driving voltage, but results in a drastic reduction in life.
  • ⁇ Charge Trap Coefficient (Free Carrier / total Carrier)
  • deuterium is substituted in an appropriate ratio by using a material having a good life, in a manner that can lower the driving voltage without introducing a plate-like molecular structure that adversely affects the life.
  • the present invention proposes a method of lowering the driving voltage by using a mixture of a compound having a similar structure substituted with heavy water.
  • the compound substituted with deuterium shows much thermodynamic behavior compared with the unsubstituted compound.
  • the intermolecular molecules generated by the shorter bond length of the compound consisting of carbon and deuterium having a shorter bond length according to the difference in carbon, hydrogen, carbon, and deuterium bond lengths It was confirmed that due to the weakening of van der Waals force can have a higher luminous efficiency.
  • the present invention used an amine compound including carbazole as an excellent material for life.
  • the carbazole-based amine compound has excellent life characteristics according to the present study, but has a disadvantage in that driving voltage is increased.
  • the prior art has not proved the effect of the improvement on this part, and in particular, the prior art which improves the driving characteristics through deuterium substitution at a specific position has not been reported yet.
  • the present invention provides a compound in which an amine group substituted with deuterium is bonded to maintain the excellent properties of the organic material layers of the organic electronic device described above and to meet the requirements of the organic material.
  • the present invention provides a compound represented by the following formula (1).
  • Ar 1 to Ar 3 are the same as or different from each other independently, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy group, C 1 C 20 -C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3 - a cycloalkyl group of C 20, C 6 ⁇ C 60 aryl group, a C 6 ⁇ C 20 substituted with a heavy hydrogen of the aryl group, a C 8 - arylalkenyl group, a silane group, a boron group, a germanium group of C 20, C 5 C 6 -C 60 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of -C 20
  • R 1 to R 4 are the same as or different from each other, and a hydrogen atom; heavy hydrogen; halogen; Nitro group; Nitrile group; Amino group; Hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 aryl thiophene group, a C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl group, C of 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, a heavy hydrogen of the One or more substituents selected from the group consisting of C 6 ⁇ C 20 aryl group, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron group, germanium group, C 5 ⁇ C 20 heterocyclic group Substi
  • R 'and R are each independently the same or different, hydrogen, deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy group, C 1 ⁇ C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3- C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron group, germanium group, C 5 ⁇ C 6 ⁇ C 60 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of C 20 heterocyclic groups; or C 1 ⁇ C 20 alkyl group, C 2
  • a is an integer of 1 to 3
  • b, c, and d are integers of 1 to 4, respectively.
  • the present invention provides a compound represented by the following formula (2).
  • Ar 1 , Ar 2 , Ar 3 , R ′, R ′′, R 1 , R 2 , a, b are the same as defined in Chemical Formula 1, respectively.
  • halo or halogen as used herein includes fluorine, chlorine, bromine, and iodine.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • heteroalkyl means an alkyl having one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 3 to 60 carbon atoms each having one or more heteroatoms unless otherwise specified, and is not limited thereto. It is not.
  • heterocycloalkyl and “heterocyclic group” include one or more heteroatoms and, unless stated otherwise, have from 2 to 60 carbon atoms.
  • heteroatom refers to N, O, S, P and Si.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • substituted in “substituted or unsubstituted” is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 Alkyl group, C 1 ⁇ C 20 Alkoxy group, C 1 C 20 -C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3 - a cycloalkyl group of C 20, C 6 ⁇ C 60 aryl group, a C 6 ⁇ C 20 substituted with a heavy hydrogen of the aryl group, a C 8 - arylalkenyl group, a silane group, a boron group, a germanium group of C 20, C 5 It means substituted with one or more substituents selected from the group consisting of ⁇ C 20 hetero
  • At least one of Ar 1 to Ar 3 of Formula 1 to Formula 5 may be independently any one selected from the group represented by Formula 6 below, which may be the same or different from each other.
  • at least one of Ar 1 , Ar 2 , and Ar 3 should contain deuterium. That is, at least one of a to v in Formula 6 is not 0.
  • a is an integer from 0 to 5
  • b is an integer from 0 to 7
  • c is an integer from 0 to 4
  • d is an integer from 0 to 5
  • e is an integer from 0 to 6
  • f is 0 to 5
  • It is an integer of, g is an integer of 0-4, h is an integer of 0-4, i is an integer of o-4, j is an integer of 0-4, k is an integer of 0-5.
  • L is an integer from 0 to 2
  • m is an integer from 0 to 5
  • n is an integer from 0 to 4
  • o, p, q and r are integers from 0 to 3
  • s and t are integers from 0 to 5
  • u And v is an integer of 0-4.
  • the compound represented by Formula 1 may be any one of the following Compounds 2-1 to 4-40, but is not limited thereto.
  • the compounds represented by Formula 1 may be one of the compounds shown in Formula 8, but is not limited thereto.
  • the substituents of the compounds represented by the formula (1) are practically difficult to exemplify all the compounds in a broad relationship, the exemplary compounds are exemplarily described, but the compounds represented by the formula (1) not shown in the formula (8) also Some can be configured.
  • the present invention provides a composition for an organic electric device containing a mixture of two or more different compounds of the compound represented by Formula 1, wherein at least one of the two or more different compounds Is a compound containing deuterium.
  • the two or more different compounds may be mixed in a range in which one compound does not exceed 90% by weight of the total weight of the composition.
  • the present invention provides an organic electric device using the compound represented by the formula (1).
  • the present invention provides an organic electric device using a composition containing a mixture of two or more different compounds of the compounds represented by the formula (1), wherein at least of the two or more different compounds One is a compound containing deuterium.
  • the two or more different compounds may be mixed in a range of any one compound does not exceed 90% by weight of the total weight of the composition.
  • a composition containing the compound having the above structural formula or a mixture thereof may be used in a soluble process.
  • the composition containing the compound or a mixture thereof may form an organic material layer of the organic electric element to be described later by a solution process (soluble process).
  • the organic material layer may be formed using a variety of polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by methods such as law.
  • the present invention provides a composition containing the compound represented by Formula 1, and a mixture thereof.
  • the compound or composition of the present invention is a metal oxide from the anode electrode, which is one of the causes of the hole injection layer material having high uniformity and low crystallization when forming a thin film while minimizing the characteristics of the organic material layer of the organic electronic device, and shortening the lifespan, as much as possible.
  • the demand for a hole injection layer material having a stable property that is, a high glass transition temperature, for Joule heating generated while driving the device while delaying penetration diffusion into the organic layer. It can satisfy the requirements of materials that can withstand a long time, that is, materials with strong heat resistance characteristics.
  • the present inventors have confirmed a large number of thermodynamic behaviors of the compound of the present invention substituted with deuterium, compared with the compound not substituted with deuterium, and the bond length is higher depending on the difference in carbon, hydrogen, carbon, and deuterium bond lengths. It is confirmed that the compound composed of small carbon and deuterium has higher luminous efficiency due to the weakening of the intermolecular van der Waals force generated by the small bond length, and when it is substituted with deuterium, it is zero point energy (ie, bottom). As the energy of the state is lowered and the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, thereby reducing the electrical polarizability and the intermolecular interaction. It was found that by weakening, the thin film volume could be increased.
  • the properties of the compound of the present invention substituted with deuterium may create an effect of lowering the crystallinity of the thin film, that is, an amorphous state, and in general, in order to increase the lifespan and driving characteristics of the organic electroluminescent device, We decided it would be very effective to implement.
  • the compound of the present invention substituted with deuterium has a lower visible light absorption characteristic than the low carbon and hydrogen bonding material, which can be an advantage to increase the efficiency in light emitting devices such as organic electroluminescent devices .
  • the compound of the present invention substituted with deuterium has a great increase in heat resistance.
  • phenylaniline-d5 34.85 g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL)
  • N-phenyl-d5-naphthalen-1-amine 44.86g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub 1-1, to give 62.85 g (69%) of the product.
  • N-phenyl-d5-naphthalen-2-amine 44.86g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub 1-1, to give 61.93 g (68%) of the product.
  • N-phenyl-d5-biphenyl-4-amine 50.07 g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub 1-1, to obtain 65.48 g (68%) of the product.
  • N-phenyl-d5-phenylthiophen-2-amine 51.28g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub 1-1, to obtain 63.37 g (65%) of the product.
  • N- (4-methoxyphenyl) -aniline-2,3,4,5,6-d5 40.86g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were prepared in the same manner as in Sub 1-1. Obtained 59.21 g (68%).
  • N-phenyl-d5-dibenzo [b, d] furan-2-amine 52.87 g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g , 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were prepared in the same manner as in Sub 1-1, and the product was 64.40 g (65 %) Got.
  • N-phenyl-d5-4-fluorophenyl-1-amine 38.45 g, 200 mmol
  • 4-bromo-4'-iodobiphenyl 86.16 g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub 1-1, to obtain 56.73 g (67%) of the product.
  • naphthalene-2-anime 28.64g, 200 mmol
  • 2-bromo-9,9-dimethyl-9H-fluorene 65.56g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were prepared in the same manner as in the Experiments of Sub 1-1, to obtain 45.62 g (68%) of the product.
  • naphthalene-1-anime 28.64g, 200 mmol
  • 2-bromo-9,9-dimethyl-9H-fluorene 65.56g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL) were obtained in the same manner as in the Experiments of Sub 1-1, to obtain 44.95 g (67%) of the product.
  • biphenyl-4-amine 33.84g, 200 mmol
  • 2-bromo-9,9-dimethyl-9H-fluorene 65.56g, 240 mmol
  • Pd 2 (dba) 3 5.5 g, 6 mmol
  • PPh 3 5.25 g, 20 mmol
  • NaO t -Bu 57.7 g, 600 mmol
  • toluene (1930 mL)
  • each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electroluminescent device including the organic electroluminescent device the conditions required for each organic material layer are satisfied.
  • a material can be prepared.
  • the compound according to the present invention can be used for various purposes in the organic electroluminescent device according to the type and nature of the substituent.
  • the compounds of the present invention can act as various layers other than the host of the phosphorescent or fluorescent light emitting layer because they are freely controlled by the core and the substituents.
  • the organic electric device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electric device except for forming one or more organic material layers using the above-described compounds.
  • the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.
  • the compound of the present invention can be used in a soluble process.
  • the compound may form an organic material layer of the organic electronic device, which will be described later, by a solution process.
  • the organic material layer may be formed by using various polymer materials, rather than a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be produced in fewer layers by the method.
  • Organic electroluminescent devices in which the compounds of the present invention may be used include, for example, organic electroluminescent devices (OLEDs), organic solar cells, organic photoconductor (OPC) drums, organic transistors (OTFTs), monochrome or white illumination devices, and the like.
  • OLEDs organic electroluminescent devices
  • OPC organic photoconductor
  • OFTs organic transistors
  • monochrome or white illumination devices and the like.
  • organic electroluminescent device As an example of the organic electroluminescent device to which the compounds of the present invention can be applied, an organic electroluminescent device (OLED) will be described.
  • OLED organic electroluminescent device
  • the present invention is not limited thereto, and the above-described compounds may be applied to various organic electroluminescent devices.
  • Another embodiment of the present invention is an organic electroluminescent device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer comprises an organic electroluminescent device comprising the compounds of the present invention to provide.
  • 1 to 6 show examples of the organic electroluminescent device to which the compound of the present invention can be applied.
  • the organic electroluminescent device except that at least one layer of the organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer to include the compound of the present invention.
  • a hole injection layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer to include the compound of the present invention.
  • FIG. 1 The structure of the organic electroluminescent device according to another embodiment of the present invention is illustrated in Figures 1 to 6, but is not limited to these structures.
  • reference numerals 101, 201, 301, 401, 501, 601 are substrates, 102, 202, 302, 402, 502, 602 are anodes, 103, 203, 303 are hole injection layers (HIL), 104, 204, 304
  • HIL hole injection layers
  • HTL hole transport layer
  • EML light emitting layer
  • ETL electron transport layer
  • ETL electron injection layer
  • 108 108
  • 208, 308, 408, 508, and 608 represent a cathode.
  • the organic electroluminescent device further includes a hole blocking layer (HBL) that prevents the movement of holes, an electron blocking layer (EBL) that prevents the movement of electrons, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located.
  • the protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
  • the compound of the present invention may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.
  • the compound of the present invention is used in place of or in combination with one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer and a protective layer It may be used to form.
  • the organic layer may be used not only in one layer but also in two or more layers.
  • it can be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material and a passivation (kepping) material according to the compound of the present invention, in particular a host or in a luminescent material and host / dopant alone Can be used as a dopant, can be used as a hole injection, a hole transport layer.
  • the organic electroluminescent device is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • PVD physical vapor deposition
  • an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure.
  • the organic layer may be formed using a variety of polymer materials, but not by a deposition process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made with a small number of layers.
  • the organic electroluminescent device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process.
  • the substrate is a support of the organic electroluminescent device, and a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, or the like can be used.
  • the positive electrode material may be a material having a large work function to facilitate hole injection into the organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention 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 oxides with metals such as ZnO: Al or SnO 2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the hole injection layer is located on the anode.
  • the conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
  • the hole injection material is a material that can be injected well from the anode at a low voltage, the highest occupied molecular orbital (HOMO) of the hole injection material may be between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO occupied molecular orbital
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is positioned on the hole injection layer.
  • the hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons.
  • applications for vehicle body display require heat resistance to the device, and may be a material having a glass transition temperature (Tg) of 70 ° C. or higher.
  • NPD NPB
  • spiro-arylamine compounds perylene-arylamine compounds
  • azacycloheptatriene compounds bis (diphenylvinylphenyl) anthracene and silicon germanium oxide.
  • the organic light emitting layer is positioned on the hole transport layer.
  • the organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and may be a material having good quantum efficiency for fluorescence or phosphorescence.
  • Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenollithium salt ), Bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 '[ (1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; D
  • DCJTB [2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H
  • doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile
  • a polymer of polyphenylene vinylene (PPV) -based polymer or poly fluorene may be used for the organic light emitting layer.
  • the electron transport layer is positioned on the organic light emitting layer.
  • the electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons.
  • Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer is stacked on the electron transport layer.
  • the electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like.
  • the electron injection layer may be formed in a thickness range of 100 ⁇ 300 ⁇ .
  • the cathode is positioned on the electron injection layer. This cathode serves to inject electrons.
  • the material used as the cathode may use the material used for the anode, and may be a metal having a low work function for efficient electron injection.
  • a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used.
  • an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 ⁇ m or less may also be used.
  • the compound of the present invention can be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, and white, It can be used as a host or dopant material of various colors.
  • the organic electroluminescent device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device.
  • This terminal means a current or future wired or wireless communication terminal.
  • the terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.
  • the organic electroluminescent device was manufactured according to a conventional method using various compounds obtained through the above-described synthesis method as light emitting host materials and hole transporting layers, respectively.
  • a 2-TNATA film was vacuum-deposited as a hole injection layer on the ITO layer (anode) formed on the organic substrate to form a thickness of 10 nm.
  • the compound of the present invention and the compound of Comparative Example were vacuum deposited to a thickness of 20 nm with a hole transport layer, and then a comparative experiment was performed.
  • Tris (8-quinolinol) aluminum was then deposited to a thickness of 40 nm with an electron injection layer. Thereafter, LiF, an alkyl halide metal, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device using this Al / LiF as a cathode.
  • the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices prepared as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m2 reference luminance.
  • the T90 life was measured using a life measurement instrument manufactured by McScience.
  • Table 5 shows the results of device fabrication and evaluation.
  • the example compounds substituted with deuterium compared to the NPB of the comparative example shows a characteristic that the driving voltage is lowered, showing a high result not only in the driving voltage drop but also in luminous efficiency and lifetime.
  • Example 2-28 Example (3-28), Example (4-28) and the other examples of compounds showing low driving voltage and high lifetime.
  • the hole transport layer was measured, but the result of device evaluation was obtained using the mixture of 50:50.
  • Example 2-28, Example 3-28, and Example 4-28 which showed excellent results with NPB of Comparative Example Compound (1), are given as comparative examples in Table 6, and Compound 2-28 and 3- Comparative device evaluation was measured using a mixture of 28, 4-28 and other compounds at 50:50 as the hole transport layer.

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  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique qui comprend un composé à base d'amine contenant un carbazole en tant que matières pour une couche d'injection de trous ou une couche de transport de trous, le dispositif ayant une commande haute tension, un rendement lumineux élevé et une longue durée de vie étant donné que les matières contenant du deutérium ayant d'excellentes caractéristiques de commande et des matières ayant une excellente durée de vie sont mélangées et utilisées.
PCT/KR2012/004939 2011-06-29 2012-06-22 Dispositif électroluminescent organique utilisant des dérivés de diarylamine, et nouveau composé et nouvelle composition pour le dispositif électroluminescent organique WO2013002514A2 (fr)

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WO2014034795A1 (fr) * 2012-08-31 2014-03-06 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique utilisant ledit dérivé
WO2016009823A1 (fr) * 2014-07-16 2016-01-21 東レ株式会社 Dérivé de monoamine, matériau d'élément luminescent le contenant, et élément luminescent
US9634263B2 (en) 2013-03-26 2017-04-25 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
CN107963973A (zh) * 2016-10-20 2018-04-27 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN109096268A (zh) * 2018-09-11 2018-12-28 长春海谱润斯科技有限公司 一种有机电致发光化合物及其有机电致发光器件
JP2019127487A (ja) * 2018-01-26 2019-08-01 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子及び有機電界発光素子用モノアミン化合物
CN110627666A (zh) * 2019-09-12 2019-12-31 中国科学院化学研究所 一种芴基四胺芘空穴传输材料及其在钙钛矿太阳能电池中的应用
WO2020225071A1 (fr) * 2019-05-03 2020-11-12 Merck Patent Gmbh Dispositif électronique
CN113135880A (zh) * 2020-01-17 2021-07-20 江苏三月科技股份有限公司 一种含二苯基芴的有机化合物及其应用
US11251377B2 (en) 2017-07-14 2022-02-15 Lg Chem, Ltd. Organic light emitting device
US11377570B2 (en) 2018-08-31 2022-07-05 Lg Chem, Ltd. Ink composition for organic light emitting device
CN117069597A (zh) * 2023-10-16 2023-11-17 烟台丰蓬液晶材料有限公司 一种化合物及其应用
US11849632B2 (en) 2019-03-20 2023-12-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
US11871656B2 (en) 2018-01-26 2024-01-09 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device

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KR102285858B1 (ko) * 2016-01-13 2021-08-04 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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US10014477B2 (en) 2012-08-31 2018-07-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
WO2014034795A1 (fr) * 2012-08-31 2014-03-06 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique utilisant ledit dérivé
US11444246B2 (en) 2012-08-31 2022-09-13 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US11362279B2 (en) 2012-08-31 2022-06-14 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US9634263B2 (en) 2013-03-26 2017-04-25 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
US10347847B2 (en) 2013-03-26 2019-07-09 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
US10446766B2 (en) 2013-03-26 2019-10-15 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
WO2016009823A1 (fr) * 2014-07-16 2016-01-21 東レ株式会社 Dérivé de monoamine, matériau d'élément luminescent le contenant, et élément luminescent
CN107963973A (zh) * 2016-10-20 2018-04-27 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN107963973B (zh) * 2016-10-20 2023-07-25 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
US11251377B2 (en) 2017-07-14 2022-02-15 Lg Chem, Ltd. Organic light emitting device
US11805697B2 (en) 2018-01-26 2023-10-31 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
JP2019127487A (ja) * 2018-01-26 2019-08-01 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子及び有機電界発光素子用モノアミン化合物
US11871656B2 (en) 2018-01-26 2024-01-09 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
US11377570B2 (en) 2018-08-31 2022-07-05 Lg Chem, Ltd. Ink composition for organic light emitting device
CN109096268A (zh) * 2018-09-11 2018-12-28 长春海谱润斯科技有限公司 一种有机电致发光化合物及其有机电致发光器件
US11849632B2 (en) 2019-03-20 2023-12-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
CN113728453A (zh) * 2019-05-03 2021-11-30 默克专利有限公司 电子器件
WO2020225071A1 (fr) * 2019-05-03 2020-11-12 Merck Patent Gmbh Dispositif électronique
CN110627666A (zh) * 2019-09-12 2019-12-31 中国科学院化学研究所 一种芴基四胺芘空穴传输材料及其在钙钛矿太阳能电池中的应用
CN113135880A (zh) * 2020-01-17 2021-07-20 江苏三月科技股份有限公司 一种含二苯基芴的有机化合物及其应用
CN113135880B (zh) * 2020-01-17 2024-05-07 江苏三月科技股份有限公司 一种含二苯基芴的有机化合物及其应用
CN117069597A (zh) * 2023-10-16 2023-11-17 烟台丰蓬液晶材料有限公司 一种化合物及其应用
CN117069597B (zh) * 2023-10-16 2024-01-02 烟台丰蓬液晶材料有限公司 一种化合物及其应用

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