WO2017090919A1 - Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant - Google Patents

Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant Download PDF

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WO2017090919A1
WO2017090919A1 PCT/KR2016/012921 KR2016012921W WO2017090919A1 WO 2017090919 A1 WO2017090919 A1 WO 2017090919A1 KR 2016012921 W KR2016012921 W KR 2016012921W WO 2017090919 A1 WO2017090919 A1 WO 2017090919A1
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group
compound
ring
organic
formula
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박형근
이선희
이윤석
소기호
박종광
정연석
문성윤
권재택
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덕산네오룩스 주식회사
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Priority to US15/779,122 priority Critical patent/US20190241548A1/en
Publication of WO2017090919A1 publication Critical patent/WO2017090919A1/fr

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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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof

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.
  • a hole injection material 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.
  • 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 required, and in particular, the development of materials for the light emitting auxiliary layer and the hole transport layer is urgently required.
  • Embodiments of the present invention to solve the problems of the above-described background, the discovery of a compound having a novel structure, and also when the compound is applied to an organic electric device greatly improve the luminous efficiency, stability and life of the device It turns out that you can.
  • an object of the present invention is to provide a novel compound, an organic electric device, and an electronic device using the same.
  • the present invention provides a compound represented by the following formula (1) and a composition for a hole-passing layer or a light-emitting auxiliary layer comprising the same, and an organic electric device comprising the compound.
  • 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.
  • the present invention provides a compound represented by the following formula (1).
  • a and B are each selected from the group consisting of the following formulas (1-1) and (1-2) and different from each other,
  • Ar 1 , Ar 2 and Ar 3 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; Is selected from the group consisting of
  • L 1 and L 2 are each independently 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 a C 2 ⁇ C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P, and
  • n is an integer from 0 to 4
  • m, p, o are integers from 0 to 3 and when m, n, o, p is 1 or more, R 1 , R 2 , R 3 and R 4 are each independently hydrogen.
  • the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, aryloxy group are each deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -L'-N (R a ) (R b ); Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -
  • the compound represented by the formula (1) includes a compound represented by the following formula (2) or formula (3).
  • R 1 , R 2 , R 3 , R 4 , m, n, o, p, L 1 , L 2 , Ar 1 , Ar 2 , Ar 3 is represented by the formula ( As defined in 1).
  • the compound represented by the formula (1) includes a compound represented as follows.
  • the present invention provides 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, wherein the organic material layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and a light emitting layer. It includes, the organic material layer provides an organic electric device comprising a compound represented by the formula (1).
  • the present invention is an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, the hole transport layer and the hole transport layer formed between the first electrode and the light emitting layer And a light emitting auxiliary layer formed between the light emitting layer, wherein the light emitting auxiliary layer contains a compound represented by the following Chemical Formula (1), and the hole transport layer contains a compound represented by the following Chemical Formula (5).
  • An organic electric device is provided.
  • the present invention is an organic electroluminescence comprising a composition in which at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer is a compound of the formula (1) alone or two or more compounds different in structure Provided is an element.
  • the hole transport layer or the light emitting auxiliary layer may include a composition in which the compound is mixed alone or in combination of two or more compounds having different structures.
  • the present invention provides an organic electroluminescent device comprising the compound of formula (1), wherein the light emitting auxiliary layer, the hole transport layer containing a compound represented by the following formula (5).
  • Ar 4 and Ar 5 are independently of each other C 6 ⁇ C 60 An 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 ); wherein L 'is a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene group; C 3 ⁇ C 60 A fused ring group of an aliphatic ring and an aromatic ring of C 6 ⁇ C 60 ; and a heterocyclic group of C 2 ⁇ C 60 , wherein R a and R
  • Ar 6 is selected from any one of the following formulas (5-a), (5-b) and (5-c).
  • a, b, c are integers from 0 to 4, R 5 , R 6 and R 7 are the same as or different from each other, and independently from each other deuterium; 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 ); or R 5 , R 6, and R 7 are each the same as or different from each other when a, b, and c are two or more, and A plurality of R 5 or a plurality of R 5
  • L 3 and L 5 are each independently a 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 including at least one heteroatom of O, N, S, Si, and P;
  • L 4 is a single bond of 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 including at least one heteroatom of O, N, S, Si, and P;
  • Ar 7 , Ar 8 and Ar 9 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; Is selected from the group consisting of
  • the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, aryloxy group are each deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -L'-N (R a ) (R b ); Import alkylthio of C 1 -C 20; An alkoxyl group of C 1 -C 20 ; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; Aryl group of C 6 -C 20 ; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -
  • the compound represented by the formula (5) includes a compound represented by the following formula (5-1 to 5-71).
  • 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 material layer may sequentially include the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the light emitting auxiliary layer 151, the electron transport layer 160, and the electron injection layer 170 on the first electrode 120. It may include.
  • 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.
  • an anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and thereon, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and a light emitting auxiliary layer 151.
  • the organic material layer including the electron transport layer 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as a cathode thereon.
  • the present invention includes a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and a light emitting layer, and the organic material layer is represented by Chemical Formula (1).
  • the organic material layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and a light emitting layer, and the organic material layer is represented by Chemical Formula (1).
  • an organic electroluminescent device comprising a compound contained in).
  • the present invention includes a compound according to the formula (1) in at least one layer of the hole injection layer, hole transport layer, light emitting auxiliary layer, light emitting layer, the compound is one or a mixture of two or more compounds It provides an organic electric device comprising the composition.
  • the present invention provides an organic electroluminescent device comprising at least one kind of the compound in the light emitting auxiliary layer.
  • 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 also provides an organic electroluminescent device comprising a hole transport layer and a light emitting auxiliary layer comprising a compound represented by the formula (1), in another aspect a hole transport layer comprising a compound represented by the formula (1) or An organic electric device comprising a light emitting auxiliary layer is provided.
  • 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.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Sub 1-I 73.92 g, 200.2 mmol
  • Sub 1-2-2 112.0 g, 300.3 mmol
  • Sub 1-II (93.9 g, 200.2 mmol) and Sub 1-2-3 (116.8 g, 300.3 mmol) were obtained using the synthesis method of Sub 1-1 to obtain 90.8 g (yield: 75%) of the product.
  • Sub 1-III (74.1 g, 200.2 mmol) and Sub 1-2-4 (112.0 g, 300.3 mmol) were obtained using the synthesis method of Sub 1-1 to obtain 70.5 g (yield: 72%) of the product.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • Bromobenzene (37.1 g, 236.2 mmol) was added to a round bottom flask and dissolved with toluene (2200 mL), followed by aniline (20 g, 214.8 mmol), Pd 2 (dba) 3 (9.83 g, 10.7 mmol), P ( t -Bu ) 3 (4.34 g, 21.5 mmol) and NaO t -Bu (62 g, 644.3 mmol) were added in this order and stirred at 100 ° C.
  • Sub 2 is as follows, but is not limited thereto.
  • Sub 2-1 (8.0 g, 47.3 mmol) was added to a round bottom flask and dissolved with toluene (500 mL), then Sub 1-1 (26.2 g, 52.0 mmol), Pd 2 (dba) 3 (2.2 g, 2.4 mmol) ), P ( t -Bu) 3 (1 g, 4.73 mmol) and NaO t -Bu (13.6 g, 141.8 mmol) were added and stirred at 100 ° C. After the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 25.0g (yield: 81%).
  • L is L 3 or L 5 as defined in formula (2-a), formula (2-b), formula (2-c).
  • N-phenylnaphthalen-1-amine 4 -bromo-4'-iodo-1,1'-biphenyl in (65.8 g, 300 mmol) ( 129.2 g, 360 mmol), Na 2 SO 4 (42.6 g, 300 mmol), K 2 CO 3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the above synthesis method to give 89.2 g (yield: 66%) of the product.
  • Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 5 below.
  • N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-1-amine (10.8 g, 24 mmol) is dissolved in toluene, followed by N-phenylnaphthalen-1-amine (4.4 g, 20 mmol), Pd 2 (dba) 3 (0.05 equiv), PPh 3 (0.1 equiv) and NaO t -Bu (3 equiv) were then added, and the mixture was stirred and refluxed at 100 ° C. for 24 hours.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • 2,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 60 nm as a hole transporting compound on the membrane to form a hole transport layer.
  • inventive compounds and Comparative Examples were vacuum-deposited to a thickness of 20 nm as a light emission auxiliary layer material to form a light emission auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium] as a host.
  • the light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer by doping at 95: 5 weight.
  • 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 a light emitting auxiliary layer was formed using Comparative Compound 1 instead of the compound of the present invention.
  • Example 1 Compound Voltage Current density Brightness (cd / m2) Efficiency LifetimeT (95) CIE (x, y) Comparative Example (1) - 6.0 21.7 5000.0 23.0 61.8 (0.31, 0.61) Comparative Example (2) Comparative Compound 1 6.2 14.3 5000.0 35.0 94..5 (0.31, 0.60) Example (1) Compound (1-1) 5.6 10.9 5000.0 45.8 118.1 (0.31, 0.60) Example (2) Compound (1-2) 5.5 11.3 5000.0 44.3 114.2 (0.32, 0.61) Example (3) Compound (1-3) 5.6 11.2 5000.0 44.7 117.7 (0.31, 0.61) Example (4) Compound (1-4) 5.7 10.7 5000.0 46.7 114.1 (0.33, 0.60) Example (5) Compound (1-6) 5.7 10.8 5000.0 46.4 113.6 (0.31, 0.60) Example (6) Compound (1-7) 5.5 11.5 5000.0 43.4 119.9 (0.32, 0.61) Example (7) Compound (1-8) 5.5 11.5 5000.0 43.5 113.8 (0.32, 0.61)
  • Comparative Example 1 using the light emitting auxiliary layer and Comparative Examples 1 to 20 using the compound of the present invention were superior to Comparative Example 1, which did not use the light emitting auxiliary layer.
  • Inventive compounds substituted with positions 2 and 3 asymmetrically to dibenzotiophen or dibenzofuran showed the best results, compared to Comparative Compound 1, in which both carbazole and amine groups were substituted at position 2.
  • N 1 - (naphthalen-2- yl) -N 4 N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • the above-mentioned compound represented by the formula (13) as a hole transport compound was vacuum deposited to a thickness of 60 nm on this film to form a hole transport layer.
  • the inventive compound represented by the formula (1) was vacuum deposited to a thickness of 20 nm as a light emitting auxiliary layer material to form a light emitting auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • piq 2 Ir (acac)
  • bis- A light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer by doping 1-phenylisoquinolyl) iridium (III) acetylacetonate] at a weight of 95: 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.
  • 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 2, except that Comparative Compound 1 was used as the light emitting auxiliary layer.
  • the examples using the compound represented by the formula (5) as the hole transport layer and the compound represented by the formula (1) as the light emitting auxiliary layer are the same under different conditions, but the comparative compound 1 It can be seen that the driving voltage, lifespan, and especially luminous efficiency of the organic electroluminescent device are significantly improved than the comparative example used as the light emitting auxiliary layer. This is because when the physical and chemical properties of the compound represented by Formula 1 described in Table 5 together with the compound represented by Formula 5 constitute a device, the combination improves the performance of the device as a whole by synergistically synergistic action. It is feed.

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé capable d'améliorer le rendement lumineux, la stabilité et la durée de vie d'un élément ; un élément électronique organique l'utilisant ; et un dispositif électronique le comprenant.
PCT/KR2016/012921 2015-11-26 2016-11-10 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant WO2017090919A1 (fr)

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CN108117543A (zh) * 2016-11-29 2018-06-05 东进世美肯株式会社 新颖化合物及包含其的有机电致发光器件
CN112125872A (zh) * 2019-06-24 2020-12-25 Lt素材株式会社 杂环化合物和使用其的有机发光器件
JP2021504352A (ja) * 2017-11-24 2021-02-15 メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ 有機エレクトロルミネッセンス素子のための材料
CN114464759A (zh) * 2020-11-09 2022-05-10 三星Sdi株式会社 有机光电子装置和显示装置
JP2022545596A (ja) * 2019-09-27 2022-10-28 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
EP4043449A4 (fr) * 2019-10-11 2023-12-20 Idemitsu Kosan Co., Ltd Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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CN108117543A (zh) * 2016-11-29 2018-06-05 东进世美肯株式会社 新颖化合物及包含其的有机电致发光器件
CN108117543B (zh) * 2016-11-29 2023-09-12 东进世美肯株式会社 新颖化合物及包含其的有机电致发光器件
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JP2021504352A (ja) * 2017-11-24 2021-02-15 メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ 有機エレクトロルミネッセンス素子のための材料
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CN112125872B (zh) * 2019-06-24 2023-11-10 Lt素材株式会社 杂环化合物和使用其的有机发光器件
CN112125872A (zh) * 2019-06-24 2020-12-25 Lt素材株式会社 杂环化合物和使用其的有机发光器件
JP2022545596A (ja) * 2019-09-27 2022-10-28 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
JP7298947B2 (ja) 2019-09-27 2023-06-27 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
EP4043449A4 (fr) * 2019-10-11 2023-12-20 Idemitsu Kosan Co., Ltd Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN114464759A (zh) * 2020-11-09 2022-05-10 三星Sdi株式会社 有机光电子装置和显示装置

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