WO2017122978A1 - Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique fabriqué avec celui-ci - Google Patents

Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique fabriqué avec celui-ci Download PDF

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WO2017122978A1
WO2017122978A1 PCT/KR2017/000285 KR2017000285W WO2017122978A1 WO 2017122978 A1 WO2017122978 A1 WO 2017122978A1 KR 2017000285 W KR2017000285 W KR 2017000285W WO 2017122978 A1 WO2017122978 A1 WO 2017122978A1
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문성윤
이선희
최연희
김슬기
이학영
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덕산네오룩스 주식회사
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • 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 a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • Efficiency, lifespan, and driving voltage are related to each other, and as efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases. It shows a tendency to increase the life.
  • a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emitting auxiliary according to each light emitting layer (R, G, B). It is time to develop the floor.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.
  • the materials constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc., are stable and efficient. Supported by the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials continues to be demanded.
  • the combination of the hole transport layer or the light emitting layer and the light emitting layer more specifically, the light emitting auxiliary layer and the phosphorescent host, and the light emitting auxiliary layer, the phosphorescent host and the dopant, The development of the same device combination is also urgently required.
  • Patent Document 1 KR1020060032099 A
  • Embodiments of the present invention to solve the problems of the above-described background, revealed the optimal combination of the compound for the hole transport layer or the light emitting auxiliary layer and the compound for the light emitting layer, the luminous efficiency of the device when applying these compounds to the organic electronic device It has been found that the stability and lifespan can be greatly improved.
  • an object of the present invention is to provide an organic electric device and an electronic device using a combination of a compound for a hole transport layer or a light emitting auxiliary layer and a compound for a light emitting layer.
  • the present invention provides an organic electroluminescent device comprising a hole transport layer or a light emitting auxiliary layer comprising a compound represented by the following formula (1) and a compound represented by the following formulas (2) to (4) as a light emitting layer .
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group As used herein, the terms “alkenyl group”, “alkenyl group” or “alkynyl group” have a double or triple bond of 2 to 60 carbon atoms, respectively, unless otherwise stated, and include straight or branched chain groups. It is not limited to this.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but 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.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 instead of carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • 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.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • 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 alkoxyl 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, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of,
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode
  • the organic material layer is between the first electrode and the light emitting layer.
  • a hole transport layer and a light emitting layer formed between the light emitting auxiliary layer and the first electrode and the light emitting auxiliary layer, wherein the light emitting layer includes a host and a dopant material, respectively, and the hole transport layer or the light emitting auxiliary layer is represented by the following formula (1): It includes a compound represented by), the light emitting layer provides an organic electric device comprising at least one of the compounds represented by the formula (2) ⁇ (4).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b );
  • a, b, d, e, h, i, k are each independently an integer of 0 to 4
  • c, f, g are each independently an integer of 0 to 3
  • j is an integer of 0 to 2
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 and R 23 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2
  • L 1 , L 2 , L 3 , L 4 and L 5 are each independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 divalent heterocyclic group; Divalent fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And it is selected from the group consisting of divalent aliphatic hydrocarbon group,
  • X and Y are directly bonded to each other independently;
  • S, O, NR ', CR'R “or SiR'R” and W is S, O, NR', CR'R “or SiR'R”;
  • R ′ and R ′′ are each independently selected from hydrogen; C 6 ⁇ C 60 aryl group; C 3 ⁇ C 60 heterocyclic group; C 1 ⁇ C 50 Alkyl group; It is bonded to each other spiro Can form compounds,
  • l and m are each independently an integer of 0 ⁇ 1, l + m is 1 or more, when l and m is 0, it means a direct bond,
  • Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 and Z 16 are Each independently CR or N, R is hydrogen, an aryl group of C 6 -C 60 ; Containing at least one heteroatom of O, N, S, Si, P C 3 ⁇ C 60 Heterocyclic group; C 1 ⁇ C 50 Alkyl group; C 6 ⁇ C 60 arylamine group; A fluorene group; selected from the group consisting of: a ring formed by combining with a neighboring group,
  • L ' is a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And C 2 ⁇ C 60 Heterocyclic group; It is selected from the group consisting of, R a and R b are independently of each other C 6 ⁇ C 60 An aryl group; Fluorenyl group; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And a C 2 to C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P. ⁇
  • the present invention provides an organic electric device, characterized in that the compound represented by the formula (1) is a compound represented by the following formula (5) or (6).
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , a, b, c, d, e, f, g, h, Ar 1 , Ar 2 , L 1 , L 2 , L 3 are as defined in formula (1) above.
  • the present invention provides an organic electric device, characterized in that the compound represented by the formula (2) is a compound represented by any one of the following formulas (7) to (12).
  • R 9 , R 10 , R 11 , i, j, k, Ar 3 , L 4 , X, Y are as defined in formula (1) above.
  • the present invention provides an organic electric device, characterized in that the compound represented by the formula (3) is a compound represented by any one of the following formulas (13) to (16).
  • the present invention provides an organic electric device characterized in that the compound represented by the formula (4) is represented by the following formula (17).
  • R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 22 , R 23 , L ', R a and R b are as defined in formula (1) above,
  • R 24 is hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); n is an integer of 0 to 4, and adjacent R 24 may combine with each other to form a ring,
  • L 6 are independently a single bond to each other; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 divalent heterocyclic group; Divalent fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And it is selected from the group consisting of divalent aliphatic hydrocarbon group,
  • T is S, O, NR ', CR'R "or SiR'R", and R' and R "are as defined in Formula 1 above. ⁇
  • the present invention provides an organic electroluminescent device characterized in that the compound represented by the formula (1), formula (5) or (6) is selected from any one of the compounds represented as follows.
  • the present invention provides an organic electric device characterized in that the compound represented by the formula (2) or formula (7) to (12) is represented by any one of the compounds represented as follows.
  • the present invention provides an organic electronic device, characterized in that the compound represented by the formula (3) or formula (13) to (16) is any one of the compounds represented as follows.
  • the present invention provides an organic electroluminescent device characterized in that the compound represented by the formula (4) or formula (17) is a compound represented by any one of the following.
  • the present invention provides an organic electric device comprising a compound represented by the following formula (18) dopant in the light emitting layer.
  • R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 and R 32 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 60 Aryl group; Containing at least one heteroatom of O, N, S, Si, P C 3 ⁇ C 60 Heterocyclic group; C 1 ⁇ C 50 Alkyl group; A C 1 to C 50 alkoxy group; C 2 -C 20 alkenyl group; -L'-N (R a ) (R b ); R 25 and R 26 , R 26 and R 27 , R 27 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and R 31 , R 31 and R 32 Can combine with each other to form a ring,
  • L is an integer from 1 to 3
  • A is an independent ligand represented by the following formula (18-1) or formula (18-2) and has a covalent bond with C, a coordination bond with N, a covalent bond with O, and a coordination bond with another O To form a complex with Ir,
  • R 33 , R 34 are independently of each other hydrogen; heavy hydrogen; C 6 ⁇ C 60 Aryl group; Containing at least one heteroatom of O, N, S, Si, P C 3 ⁇ C 60 Heterocyclic group; C 1 ⁇ C 50 Alkyl group; A C 1 to C 50 alkoxy group; C 2 -C 20 alkenyl group; -L'-N (R a ) (R b ); is selected from the group consisting of).
  • the present invention provides an organic electric device, characterized in that the compound represented by the formula (18) is any one of the compounds represented as follows.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, and a first electrode 120 and a second electrode formed on a substrate 110.
  • An organic material layer including a compound represented by Chemical Formula 1 is provided between 180.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 are disposed thereon.
  • the organic material layer including the electron injection layer 170 it can be prepared by depositing a material that can be used as a cathode thereon.
  • the present invention may further include an optical efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device.
  • the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, the organic layer is an electron transport material containing the compound It provides an organic electric element, characterized in that.
  • the present invention provides an organic electric device, characterized in that the same or different compounds of the compound represented by the formula (1) are mixed and used in the organic material layer.
  • the present invention provides a hole transport layer or light emitting auxiliary layer composition comprising a compound represented by the formula (1), and provides an organic electric device comprising the hole transport layer or light emitting auxiliary layer.
  • the present invention is a display device comprising the above-mentioned organic electric element; And a controller for driving the display device.
  • the organic electronic device provides an electronic device according to the present invention, wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound represented by the formula (1) according to the present invention (final product) is prepared by reacting Sub 1 with Sub 2, as shown in Scheme 1 below.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Sub 1 An example of Sub 1 is as follows, but is not limited thereto.
  • Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • Sub 2-2-1 (7.7 g, 24 mmol) was dissolved in toluene, then Sub 2-1-1 (5.2 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P (t-Bu ) 3 (0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, and the mixture was stirred and refluxed at 100 ° C. for 24 hours.
  • Sub 2 is as follows, but is not limited thereto.
  • Sub 1 (13) (9.5g, 24mmol) was dissolved in toluene
  • Sub 2 (24) was added (11.5g, 20mmol) and Pd 2 (dba) 3 (0.5g, 0.6mmol), P (t-Bu ) 3 (0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, and the mixture was stirred and refluxed at 100 ° C. for 24 hours.
  • Sub 9-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5 M inhexane) was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction was lowered to -78 °C, trimethyl borate was added dropwise, and stirred at room temperature for 12 hours. After the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the resulting product by concentration of the organic solvent was separated by column chromatography to give the desired Sub 9-2.
  • n-BuLi 2.5 M inhexane
  • Sub 9-2, 1-iodo-2-nitrobenzene, Pd (PPh 3 ) 4 , and K 2 CO 3 obtained were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 9-3.
  • Sub 9-3 and triphenylphosphine obtained were dissolved in o-dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and then the concentrated product was separated by column chromatography to obtain the desired Sub 9-4.
  • triphenylen-2-ylboronic acid (5.4g, 20mmol) was dissolved in THF and then 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (7.8g, 20mmol), Pd (PPh 3 ) 4 (0.03 equiv), K 2 CO 3 (3 equiv), and water are added followed by stirring under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 7.5g (yield: 70%) of the product.
  • Sub 18 is as follows, but is not limited thereto.
  • Product 19-1 of Scheme 8 is prepared by reacting with the following Scheme 10, but is not limited thereto.
  • Pentane-2,4-dione (10 equivalents), Na 2 CO 3 (10 equivalents), and 2-ethoxy ethanol were added to Sub 18 (3) (1 equivalent) and reacted at 130 ° C. for 24 hours under nitrogen. After the reaction was completed, the obtained solid material was filtered through column chromatography and dried for 3 hours under a vacuum pump to obtain a final compound.
  • Pentane-2,4-dione (10 equiv), Na 2 CO 3 (10 equiv) and 2-ethoxy ethanol were added to an Ir compound (1 equiv) and reacted at 130 ° C. for 24 hours under nitrogen. After the reaction was completed, the obtained solid material was filtered through column chromatography and dried for 3 hours under a vacuum pump to give the final compound 19-6.
  • Sub 19 is the same as the example of Sub 18.
  • -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a hole injection layer having a thickness of 60 nm, and then 4,4-bis [N- (1) as a hole transport compound on the hole injection layer.
  • -Naphthyl -N-phenylamino] biphenyl
  • -NPD -Naphthyl
  • -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.
  • the inventive compound represented by Chemical Formula 1 as a light emitting auxiliary layer material was vacuum deposited to a thickness of 20 nm to form a light emitting auxiliary layer.
  • the above-described compound represented by the formulas (2) to (4) is represented as a host on the light-emitting auxiliary layer, and 18-1 of the compound represented by the formula (18) as a dopant is 95
  • a light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer by doping at a weight of 5: 5.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq the electron transport layer Tris (8-quinolinol) aluminum
  • Alq3 the electron transport layer Tris (8-quinolinol) aluminum
  • the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measurement result was measured at a luminance of 5000 cd / m2.
  • the T95 life was measured using a life measurement instrument manufactured by McScience.
  • the following table shows the results of device fabrication and evaluation.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light emitting auxiliary layer was not used.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used as the light emitting auxiliary layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used as a host.
  • the compound represented by the formula (1) is used as the light emitting auxiliary layer, and the compound represented by the formulas (2) to (4) is represented by the host of the light emitting layer, represented by the formula (18).
  • Examples in which the compound is used as a dopant of the light emitting layer do not use the light emitting auxiliary layer (Comparative Examples 1 to 3)
  • Comparative Compound 1 is used as the light emitting auxiliary layer (Comparative Examples 4 to 6)
  • Comparative Compound 2 is applied to the light emitting layer. It can be seen that the driving voltage, efficiency, and lifespan of the organic electroluminescent light emitter are remarkably improved from those of Comparative Examples 7 to 12 used for the present invention.
  • Comparative Examples 4 to 12 and Examples 1 to 18 using Comparative Compound 1 or Inventive Compound as light emitting auxiliary layers compared to Comparative Examples 1 to 3 without using the light emitting auxiliary layer, improved driving voltage, lifetime, and particularly efficiency. Able to know. That is, it shows that the use of the light emitting auxiliary layer can increase the efficiency than the unused device.
  • Examples 1 to 12 using Comparative Compound 1 and Comparative Compound 2 as the light emitting auxiliary layer or the host compound Example 1 using the compound represented by the formula (1) as a light emitting auxiliary layer as a host compound 1 to 18 showed remarkable results in driving voltage, efficiency, and lifetime.
  • the compound represented by Formula 1 has characteristics such as deep HOMO, high T1 and high passion stability compared to Comparative Compound 1,
  • the compounds represented by 2) to (4) as a phosphorescent host the combination of these devices is considered to be synergistically electrochemically improving the performance of the whole device.

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

Abstract

La présente invention concerne un composé destiné à être utilisé dans une couche de transport de trous ou une couche émettant de la lumière auxiliaire, le composé étant capable d'améliorer l'efficacité d'émission, la stabilité et la durée de vie d'un élément, un élément électronique organique utilisant un composé pour une couche électroluminescente, et un dispositif électronique fabriqué avec celui-ci.
PCT/KR2017/000285 2016-01-11 2017-01-09 Composé pour élément électronique organique, élément électronique organique l'utilisant et dispositif électronique fabriqué avec celui-ci WO2017122978A1 (fr)

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CN112300127A (zh) * 2019-07-25 2021-02-02 乐金显示有限公司 有机化合物、包含该化合物的有机发光二极管和有机发光显示装置
CN113166129A (zh) * 2018-10-23 2021-07-23 德山新勒克斯有限公司 用于有机电子元件的化合物，使用该化合物的有机电子元件及其电子设备
US20220144855A1 (en) * 2019-01-18 2022-05-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN114989069A (zh) * 2022-04-28 2022-09-02 陕西莱特光电材料股份有限公司 含氮化合物和电子元件及电子装置

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WO2023096210A1 (fr) * 2021-11-26 2023-06-01 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé
KR102373387B1 (ko) * 2021-11-26 2022-03-11 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN115521242A (zh) * 2022-03-29 2022-12-27 陕西莱特光电材料股份有限公司 有机化合物和电子元件及电子装置
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KR20240010599A (ko) 2022-07-14 2024-01-24 에스케이 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20240052471A (ko) * 2022-10-14 2024-04-23 삼성에스디아이 주식회사 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치

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CN113166129A (zh) * 2018-10-23 2021-07-23 德山新勒克斯有限公司 用于有机电子元件的化合物，使用该化合物的有机电子元件及其电子设备
US20220144855A1 (en) * 2019-01-18 2022-05-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN112300127A (zh) * 2019-07-25 2021-02-02 乐金显示有限公司 有机化合物、包含该化合物的有机发光二极管和有机发光显示装置
CN112300127B (zh) * 2019-07-25 2023-09-12 乐金显示有限公司 有机化合物、包含该化合物的有机发光二极管和有机发光显示装置
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CN114989069B (zh) * 2022-04-28 2023-10-10 陕西莱特光电材料股份有限公司 含氮化合物和电子元件及电子装置
WO2023207375A1 (fr) * 2022-04-28 2023-11-02 陕西莱特光电材料股份有限公司 Composé azoté, élément électronique et dispositif électronique

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