WO2012177006A2 - Composé destiné à des éléments électroniques organiques, éléments électroniques organiques utilisant ce composé, et dispositif électronique pour ce composé - Google Patents

Composé destiné à des éléments électroniques organiques, éléments électroniques organiques utilisant ce composé, et dispositif électronique pour ce composé Download PDF

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WO2012177006A2
WO2012177006A2 PCT/KR2012/004631 KR2012004631W WO2012177006A2 WO 2012177006 A2 WO2012177006 A2 WO 2012177006A2 KR 2012004631 W KR2012004631 W KR 2012004631W WO 2012177006 A2 WO2012177006 A2 WO 2012177006A2
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group
aryl
substituted
deuterium
mmol
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PCT/KR2012/004631
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Korean (ko)
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WO2012177006A3 (fr
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문성윤
이선희
이범성
최대혁
김동하
박정환
박정철
김기원
주진욱
박용욱
박정근
지희선
김혜령
소기호
강문성
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덕산하이메탈(주)
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Priority claimed from KR1020110060643A external-priority patent/KR101111406B1/ko
Priority claimed from KR1020110069298A external-priority patent/KR101108519B1/ko
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Publication of WO2012177006A2 publication Critical patent/WO2012177006A2/fr
Publication of WO2012177006A3 publication Critical patent/WO2012177006A3/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
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a compound and composition for an organic electric device capable of improving low voltage driving, high luminous efficiency and device life, an organic electric device including the same, and an electronic device thereof.
  • organic electroluminescent devices capable of low voltage driving with self-luminous type have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), which are mainstream flat panel displays, and require no backlight.
  • LCDs liquid crystal displays
  • Light weight and thinness are possible, and it 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 may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to light emission characteristics of the light emitting 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.
  • a light emitting layer guest
  • host light emitting layer
  • the life of the device is important, and various studies are being conducted to increase the life of the organic electronic device.
  • various studies have been conducted on organic materials inserted into the hole transport layer or the buffer layer for excellent life characteristics of the organic electric device, and for this purpose, a thin film after deposition is provided while providing high hole transport characteristics from the anode to the organic layer.
  • a hole injection layer material having high uniformity and low crystallinity in forming.
  • 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 current major challenge of the organic light emitting device is the urgent need to overcome the problems of power consumption and lifespan as the size of the panel of a mobile phone or a tablet PC is increased.
  • ⁇ Charge Trap Coefficient (Free Carrier / total Carrier)
  • An object of the present invention is to provide a compound and a composition, an organic electric device using the same, and an electronic device, which can improve the high luminous efficiency, low driving voltage, color purity and lifetime of the device.
  • the present invention provides a compound represented by the following formula (1).
  • the present invention provides a composition in which the compound represented by Chemical Formula 1 and the following Chemical Formula 2 is mixed.
  • the present invention provides a composition for an organic electric device containing a composition in which two or more different compounds from among the compounds represented by Formula 1 are mixed.
  • at least one of two or more different compounds may be a compound including deuterium, and 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 is an organic electroluminescent device using a composition in which two or more different compounds of the compounds represented by the formula (1) or / and the compound represented by the formula (1) and the compound represented by the formula (2) An organic electric device using the mixed composition is provided.
  • the at least one compound constituting the composition may be a compound substituted with deuterium, it may be mixed in a range not exceeding 90% by weight of the total weight of the composition.
  • the present invention is a compound represented by the formula (1), a mixture of two or more different compounds of the compound represented by the formula (1), or / and the compound represented by the formula (1) and formula (2)
  • a display device including an organic electric element comprising the mixed composition And a controller for driving the display device.
  • 1 to 6 show examples of the organic electroluminescent device to which the compound of the present invention can be applied.
  • 7 to 9 are graphs comparing the brightness, current density and efficiency of the compounds of the present invention to which deuterium is introduced and the compounds to which deuterium is not introduced, 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 the term “substituted or unsubstituted” as used herein refers to deuterium, halogen, amino, nitrile, nitro, C 1 -C 20 alkyl, C 1 -C 20 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to 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 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
  • the present invention is a method for lowering the driving voltage without introducing a plate-like molecular structure that adversely affects the life using a material having a good life, and a method for replacing deuterium at an appropriate ratio, and similarly substituted with heavy water.
  • a method of lowering the driving voltage is proposed.
  • the zero point energy that is, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and thus the electrical polarization is also reduced. It was confirmed that the electrolytic polarizability can be reduced, and the thin film volume can be increased by weakening the intermolecular interaction. This property can reduce the crystallinity of the thin film, i.e., create an amorphous state, and in general, it was determined that it would be very effective to realize the necessary amorphous state in order to increase OLED lifetime and driving characteristics.
  • 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.
  • deuterium may be introduced into the aryl group bonded to the amine group to improve device characteristics of the organic electroluminescent device.
  • biphenyl bi-phenl
  • the present invention provides a compound represented by the following formula (1).
  • Ar 1 to Ar 3 are each independently the same or different;
  • Halogen group amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 alkenyl group, C 1 ⁇ C 20 alkoxy group, C 3 ⁇ C 30 cycloalkyl group, C 2 ⁇ C heterocycloalkyl group, C 6 ⁇ C 60 aryl group and C 2 ⁇ C 20 with one or more substituents selected from the group consisting of heterocyclic group-substituted or unsubstituted C 6 ⁇ C 60 of the arylamine group of 30; And
  • C 1 ⁇ alkenyl group of the C 20 alkyl group C 2 ⁇ C 20 of, C 1 ⁇ C 20 alkoxy group, C 6 ⁇ aryl group of C 20 aryl group, a C 6 ⁇ C 20 substituted with deuterium, C 7 C 1 -C 50 alkyl group unsubstituted or substituted with a substituent selected from the group consisting of-C 20 arylalkyl group, C 8 ⁇ C 20 aryl alkenyl group, C 3 ⁇ C 20 heterocyclic group, nitrile group and acetylene group Selected from the group consisting of;
  • At least one of Ar 1 to Ar 3 includes one or more deuterium
  • R 1 and R 2 are each independently the same or different and are hydrogen; heavy hydrogen; halogen; Nitro group; Nitrile group; Amino group;
  • C 1 ⁇ alkenyl group of the C 20 alkyl group C 2 ⁇ C 20 of, C 1 ⁇ C 20 alkoxy group, C 6 ⁇ aryl group of C 20 aryl group, a C 6 ⁇ C 20 substituted with deuterium, C 7 C 1 -C 50 alkyl group unsubstituted or substituted with a substituent selected from the group consisting of-C 20 arylalkyl group, C 8 ⁇ C 20 aryl alkenyl group, C 3 ⁇ C 20 heterocyclic group, nitrile group and acetylene group Selected from the group consisting of;
  • R 1 and R 2 may be bonded to adjacent groups to form an alicyclic, aromatic or heterocyclic ring,
  • L is C 6 -C 60 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of a nitro group, a nitrile group, a halogen group, an alkyl group, an alkoxy group, an amino group, an arylamine group and a heterocyclic group Ren group; Or a C 2 -C 60 heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of nitro, nitrile, halogen, alkyl, alkoxy, amino and aryl groups,
  • a is an integer of 0-4, b is an integer of 0-3, c is an integer of 0-2.
  • the present invention provides a composition in which two or more different compounds among the compounds represented by Formula 1 are mixed.
  • two or more different compounds may be mixed in a range in which one compound does not exceed 90% by weight of the total composition.
  • the present invention provides a composition for an organic electric device, a mixture of a compound represented by the formula (1) and a compound represented by the following formula (2).
  • the composition of any one compound may be mixed in the range of 90% by weight or less of the total weight of the composition.
  • Ar 1 to Ar 3 is the same as the substituent definition of Ar 1 to Ar 3 of Formula 1,
  • R 1 to R 4 is the same as the substituent definition of R 1 or R 2 in Formula 1, wherein R 1 to R 4 may be bonded to an adjacent group to form an alicyclic, aromatic or heterocycle ,
  • R 'and R are each independently the same or different, hydrogen, deuterium, halogen, amino, nitrile, nitro, 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 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, of a C 2 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, C 6 ⁇ C 20 aryl amine group, a silane C 6 -C 60 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a boron group, a germanium group,
  • (4) a is an integer of 1 to 3
  • b, c and d are integers of 1 to 4, respectively.
  • Ar 3 includes one or more deuterium
  • Ar 2 may be represented by the following formula.
  • R 3 and R 4 are each independently the same or different and are halogen; Nitro group; Nitrile group; Amino group;
  • C 1 ⁇ alkenyl group of the C 20 alkyl group C 2 ⁇ C 20 of, C 1 ⁇ C 20 alkoxy group, C 6 ⁇ aryl group of C 20 aryl group, a C 6 ⁇ C 20 substituted with deuterium, C 7 C 1 -C 50 alkyl group unsubstituted or substituted with a substituent selected from the group consisting of-C 20 arylalkyl group, C 8 ⁇ C 20 aryl alkenyl group, C 3 ⁇ C 20 heterocyclic group, nitrile group and acetylene group Selected from the group consisting of;
  • R 3 and R 4 may combine with adjacent groups to form an alicyclic, aromatic or heterocyclic ring,
  • R 'and R 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 ⁇ C 20 cycloalkyl group, an aryl group of C 6 ⁇ C 60, of a C 6 ⁇ C 20 substituted with a heavy hydrogen aryl, C 8 ⁇ C 20 aryl alkenyl group, C 6 ⁇ C 20 aryl amine group, a silane C 6 -C 60 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a boron group,
  • At least one of Ar 1 , Ar 2 , and Ar 3 may be selected from the group consisting of the following Formula 3.
  • D is deuterium
  • k and i are integers of 0 to 2
  • n, o, q, r, q 'and r' is an integer of 0 to 3
  • b, e, f, g, l, t 'and u' are integers from 0 to 4
  • a, c, c ', h, j, m, p, s, t, u and s' are integers from 0 to 5
  • b' is 0 It is an integer of -6
  • a 'and d are integers of 0-7.
  • the index may be determined such that at least one of Ar 1 to Ar 3 includes deuterium.
  • Ar 1 to Ar 3 which contains the heavy hydrogen in Ar 1 to Ar 3 of the general formula (2) is not the type is limited to such.
  • the compound represented by Formula 1 may be any one of the following Compounds (P-1) to (P-132), but is not limited thereto.
  • the compounds represented by Formula 1 may be one of the compounds shown in Formula 5, but is not limited thereto.
  • the substituents of the compounds represented by the general formula (1) are practically difficult to exemplify all the compounds in a broad relationship, the exemplary compounds have been described by way of example, but the compounds represented by the general formula (1) not shown in the general formula (5) also Some can be configured.
  • the compound represented by Formula 2 may be any one of the following Compounds (P2-1) to (P2-120), but is not limited thereto.
  • Compounds represented by Formula 2 may be one of the compounds shown in Formula 6, but is not limited thereto.
  • the substituents of the compounds represented by the formula (2) are practically difficult to exemplify all the compounds in a broad relationship, the exemplary compounds have been described by way of example, but the compounds represented by the formula (2) not shown in the formula (6) also Some can be configured.
  • compositions containing a compound having the above structural formula or a mixture thereof can 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.
  • an organic electric device including a first electrode, a second electrode, and at least one organic material layer containing the compound represented by Formula 1 alone or in a mixture.
  • the mixture may be a mixture of two or more different compounds among the compounds represented by the formula (1) or a mixture of the compound represented by the formula (1) and the compound represented by the formula (2).
  • the organic material layer may be at least one of a light emitting layer, a hole injection layer, and a hole transport layer.
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • the composition of the present invention is a metal oxide organic layer from the positive electrode electrode which is one of the causes of the hole injection layer material having high uniformity and low crystallization when forming a thin film, and shortening the life while maximizing the characteristics of the organic material layer of the organic electric device as described below Stabilization of Joule heating generated during device operation while delaying penetration diffusion into the device, namely the demand for a hole injection layer material having a high glass transition temperature, and withstanding the deposition method in the formation of an organic electroluminescent device It can meet the requirements of materials that can be used, that is, materials with strong heat resistance characteristics.
  • thermodynamic behaviors of a composition comprising a mixture of compounds substituted with deuterium or a compound not substituted with deuterium or the compound itself substituted with deuterium, and confirmed carbon, hydrogen and carbon, deuterium bonds. According to the difference in length, it was confirmed that a compound composed of carbon and deuterium having a smaller bond length has a higher luminous efficiency due to the weakening of the intermolecular van der Waals forces generated by a short bond length. As the zero point energy, or ground energy, is lowered, and the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, thereby reducing the electrical polarizability. Thin film volume by weakening intermolecular interactions It was confirmed that increase.
  • 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 mixture of the deuterium-substituted compound has a low visible light absorption characteristics than the low carbon, hydrogen bonding material, it was determined that this can be an advantage to increase the efficiency in light emitting devices such as organic electroluminescent devices.
  • the mixture of the compound of the present invention substituted with deuterium has a great increase in heat resistance.
  • Carbazole (50.2 g, 300 mmol) and bromobenzene (56.5 g, 360 mmol) were mixed in 2800 mL of toluene, followed by Pd 2 (dba) 3 (8.24 g, 9 mmol), PPh 3 (7.87 g, 30 mmol), NaO t -Bu (86.5 g, 900 mmol) was added, and the mixture was stirred at reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO 4 , concentrated and the resulting organic was purified and recrystallized by a silica gel column to give 52.5 g (75%) of the product.
  • NBS N-bromosuccimide
  • Sub 1-2 (45.1 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl 2 (dppf) catalyst (3.43 g, 4.2 mmol), KOAc ( 41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound, and the obtained compound was separated through a silica gel column and recrystallized to obtain 35.2 g (68%) of the borate compound.
  • Sub 1-1-1 (63.88 g, 200 mmol) obtained in the above synthesis was added with 600 mL of methylene chloride and NBS (N-bromosuccimide) (59.4 g, 210 mmol) using the sub 1-2 synthesis method of Example 1 To give 55.8 g (70%) of the product.
  • reaction temperature was adjusted to 0 ° C. and a solution of 9-phenyl carbazole (2.92 g, 120 mmol) in 1,2-dichloroethane (52 mL) was added dropwise for 1 hour.
  • N-phenyl-d5-naphthalen-1-amine 22.43 g, 100 mmol
  • 2,7-dibromo-9,9-dimethyl fluorene 38.73 g, 110 mmol
  • Pd 2 (dba) 3 (2.75 g, 3 mmol)
  • PPh 3 (2.63 g, 10 mmol)
  • NaO t -Bu 28.9 g, 300 mmol
  • toluene 970 mL
  • N-phenyl-d5-naphthalen-2-amine 22.43 g, 100 mmol
  • 2,7-dibromo-9,9-diphenyl fluorene 52.38 g, 110 mmol
  • Pd 2 (dba) 3 (2.75 g, 3 mmol)
  • PPh 3 (2.63 g, 10 mmol)
  • NaO t -Bu 28.9 g, 300 mmol
  • toluene 970 mL
  • 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-1b-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 obtained in the same manner as in the Experiments of Sub-1b-1 to obtain 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-1b-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 Sub-1b-1 Experiment 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-1b-1. 59.21 g (68%) was obtained.
  • 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 the Experiment of Sub-1b-1, and the product was 64.40 g ( 65%).
  • 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 the Sub-1b-1 experiment to give 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 obtained in the same manner as the Sub-1b-1 experiment 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 Sub-1b-1 experiment to obtain 44.95 g (67%) of the product.
  • 1-amino-4-phenyl-naphthalene-d6 (45.06g, 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) and toluene (1930 mL) were prepared in the same manner as in Sub-1b-1, and the product was 53.45 g (64 %) Got.
  • each of the substituents of the compounds represented by the formula (1) or (2) is a broad relationship, the compounds represented by the formula (1) or formula (2) that is illustratively described a synthesis example of representative compounds, but not illustratively described as a synthesis example Also part of the present specification.
  • 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 electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials 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 (organic TFTs), 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.
  • reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron injection layer
  • ETL electron transport layer
  • 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 luminescent 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 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.
  • electrodes 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.
  • Various compounds of the present invention obtained through synthesis were used as light emitting host materials or hole transport layers, respectively, to fabricate organic electroluminescent devices according to a conventional method.
  • a 2-TNATA film was vacuum-deposited as a hole injection layer on the ITO layer (anode) formed on the organic substrate, and formed into a thickness of 10 nm.
  • the compound of the present invention (compounds 1 and 2) was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm with an electron injection layer.
  • 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.
  • An organic electric device was manufactured in the same manner as above, but the following compound was used as the hole transport layer material.
  • the electroluminescence (EL) characteristics were measured by PR-650 of photoresearch company .
  • the T90 lifetime was measured using a life-time measurement device manufactured by McScience Inc. at 300 cd / m 2 reference luminance. The results are shown in the following table.
  • the driving voltage decreases, it is judged to have high efficiency and long life, and it is expected to solve the short life problem due to the high driving voltage which is a problem in the OLED device.
  • 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.

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  • Physics & Mathematics (AREA)
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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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Abstract

La présente invention se rapporte à des éléments électroniques organiques comprenant un matériau de couche d'injection de trous ainsi qu'une couche de transport de trous qui présentent une excitation à basse tension des éléments électroniques organiques améliorée, qui assurent à un dispositif une plus longue durée de vie, et qui ont une grande efficacité d'émission de lumière, grâce au mélange et à l'utilisation de deux matériaux, l'un comportant de l'hydrogène lourd et ayant des caractéristiques d'excitation supérieures, et l'autre ayant une durée de vie supérieure.
PCT/KR2012/004631 2011-06-22 2012-06-12 Composé destiné à des éléments électroniques organiques, éléments électroniques organiques utilisant ce composé, et dispositif électronique pour ce composé WO2012177006A2 (fr)

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KR1020110060643A KR101111406B1 (ko) 2011-06-22 2011-06-22 유기전기소자, 유기전기소자용 신규 화합물 및 조성물
KR10-2011-0060643 2011-06-22
KR1020110069298A KR101108519B1 (ko) 2011-07-13 2011-07-13 유기전기소자용 조성물 및 이를 이용하는 유기전기소자
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