WO2020130378A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique le comprenant - Google Patents

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

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WO2020130378A1
WO2020130378A1 PCT/KR2019/016099 KR2019016099W WO2020130378A1 WO 2020130378 A1 WO2020130378 A1 WO 2020130378A1 KR 2019016099 W KR2019016099 W KR 2019016099W WO 2020130378 A1 WO2020130378 A1 WO 2020130378A1
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group
formula
organic
layer
ring
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Korean (ko)
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박종광
정연석
이윤석
박정환
고윤종
이제우
이중근
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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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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 for an organic electric element, an organic electric element using the same, and an electronic device thereof.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on the function.
  • the luminescent material may be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emission mechanism. have.
  • the luminescent material may be divided into blue, green, and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color according to the luminous color.
  • a host/dopant system may be used as a luminescent material.
  • the principle is that when a small amount of the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to produce light with high efficiency.
  • the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.
  • Efficiency, life, and driving voltage are related to each other.
  • the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase life.
  • simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and life of the device, an organic electrical device using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electric device using the compound represented by the formula and an electronic device thereof.
  • the driving voltage of the device can be lowered, and the luminous efficiency and lifetime of the device can be greatly improved.
  • 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
  • organic electric element 110 first electrode
  • first hole transport layer 340 first light emitting layer
  • second charge generation layer 420 second hole injection layer
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified.
  • an aryl group or an arylene group may include a monocyclic, ring aggregate, several conjugated ring systems, spiro compounds, and the like.
  • the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
  • fluorenyl group used in the present invention means a substituted or unsubstituted fluorenyl group
  • fluorenylene group means a substituted unsubstituted fluorenylene group unless otherwise specified.
  • Unsubstituted fluorenyl group or unsubstituted fluorenylene group means a monovalent or divalent functional group in which R, R'and R" are all hydrogen in the following structure, and a substituted fluorenyl group or a substituted fluorenylene group In the following structure, it means that at least one of R, R'and R" is a substituent other than hydrogen.
  • fluorenyl group or “fluorenylene group” used in the present invention includes the case where R and R'are bonded to each other in the following structure to form a spy compound together with the carbon to which they are attached.
  • spyro compound as used in the present invention has a'spyro linkage', and a spiro linkage refers to a linkage formed by two rings sharing only one atom. At this time, the atoms shared in the two rings are called'spyro atoms', and these are'monospyro-','dispiro-','trispyro' depending on the number of spy atoms in a compound, respectively. It is called a compound.
  • heterocyclic group used in the present invention includes aromatic rings such as “heteroaryl group” or “heteroarylene group” as well as non-aromatic rings, and each carbon number containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto.
  • aliphatic ring group used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like, unless otherwise indicated. It means a 3 to 60 ring, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it corresponds to the aliphatic ring.
  • the'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as an example of each symbol and its substituent may describe'the name of a group reflecting a singer', but is described as a'parent compound name' You may.
  • the monovalent'group' is'phenanthryl', and the divalent group can be classified as a singer such as'phenanthrylene', etc.
  • the parent compound name may be described as'phenanthrene'.
  • pyrimidine it can be described as'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidineylene, etc., as the'group name' of the corresponding singer. have.
  • a number, an alphabet, etc. indicating a position may be omitted.
  • pyrido[4,3-d]pyrimidine as pyridopyrimidine
  • benzofuro[2,3-d]pyrimidine as benzofuropyrimidine
  • 9,9-dimethyl-9H-flu Oren can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.
  • the substituent R 1 means non-existent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring.
  • the formula or compound may be omitted.
  • a is an integer of 1
  • one substituent R 1 is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different.
  • the number in the'number-condensed ring' indicates the number of condensed rings.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, and benzoquinazoline may be represented by a 3-condensed ring.
  • the number in the'number-atom' represents the number of elements forming the ring.
  • thiophene or furan may correspond to a 5-atom ring
  • benzene or pyridine may correspond to a 6-atom ring.
  • the rings formed by bonding with adjacent groups are C 6 ⁇ C 60 aromatic ring groups; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C 3 ⁇ C 60 Aliphatic ring group; may be selected from the group consisting of.
  • R 1 and R 2 between, R 2 and R 3 between, R 3 and R 4 between, R 5 and R 6 , as well as R 7 and R 8, which share one carbon, include R 1 and R 7 , R 1 and R 8, or R 4 and R 5, which are not immediately adjacent.
  • Substituents bound to ring constituent elements may also be included. That is, if there are substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to each other, they may be adjacent groups, but if no substituents are attached to the ring constituent element of the immediately adjacent position, it is bound to the next ring constituent element.
  • the substituted groups may be adjacent groups, and the substituents bonded to the same ring-constituting carbon may also be referred to as adjacent groups.
  • the expression'neighborhood groups may combine with each other to form a ring' is used in the same sense as'neighborhood groups combined with each other to selectively form a ring', and at least a pair of It means the case where adjacent groups combine with each other to form a ring.
  • first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term.
  • a component is described as being “connected”, “coupled” or “connected” to another component, the component may be directly connected to or connected to the other component, but another component between each component It should be understood that the element may be “connected”, “coupled” or “connected”.
  • a component such as a layer, film, region, plate, etc. is said to be “above” or “on” another component, it is not only when the other component is “directly above”, but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.
  • 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
  • an organic electric device 100 includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) And an organic material layer formed between the second electrode 170.
  • the first electrode 110 may be an anode (anode)
  • the second electrode 170 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 include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150 and an electron injection layer 160.
  • the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160 may be sequentially formed on the first electrode 110.
  • the light efficiency improving layer 180 may be formed on one surface of the first electrode 110 or the second electrode 170 that does not contact the organic material layer, and when the light efficiency improving layer 180 is formed The light efficiency of the organic electric device can be improved.
  • the light efficiency improving layer 180 may be formed on the second electrode 170.
  • the second electrode 170 is formed by forming the light efficiency improving layer 180.
  • SPPs surface plasmon polaritons
  • the light efficiency improving layer 180 serves as a buffer for the second electrode 170 can do.
  • a buffer layer or an auxiliary light emitting layer may be further formed between the hole transport layer 130 and the light emitting layer 140, which will be described with reference to FIG. 2.
  • the organic electric device 200 includes a hole injection layer 120, a hole transport layer 130, and a buffer layer 210 sequentially formed on the first electrode 110,
  • a light emitting auxiliary layer 220, a light emitting layer 140, an electron transport layer 150, may include an electron injection layer 160, a second electrode 170, the light efficiency improving layer 180 is formed on the second electrode Can be.
  • an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
  • the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.
  • the organic electrical device 300 includes two stacks of organic material layers (ST1, ST2) formed of a multilayer between the first electrode 110 and the second electrode 170. More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
  • ST1, ST2 organic material layers
  • CGL charge generating layer
  • the organic electric device includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode 170 and a light efficiency improving layer 180.
  • the first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first light emitting layer 340, and a first electron transport layer 350 ), and the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450.
  • the first stack and the second stack may be organic material layers having the same lamination structure, but may also be organic material layers of different lamination structures.
  • a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2.
  • the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361.
  • the charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the current efficiency generated in each light emitting layer, and serves to distribute charges smoothly.
  • the first light emitting layer 340 may include a light emitting material including a blue fluorescent dopant in the blue host, and the second light emitting layer 440 may be a green host doped with a greenish yellow dopant and a red dopant. Although it may be included, the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.
  • n may be an integer from 1 to 5, and when n is 2, a charge generating layer CGL and a third stack may be additionally stacked on the second stack ST2.
  • the compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer 210, a light emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layer (140, 340, 440) or may be used as a material of the light efficiency improving layer 180, but preferably the light emitting layer (140, 340, 440) and / or light efficiency improving layer It can be used as a material of (180).
  • band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached to which positions even in the same core, research on the selection of the core and the combination of sub-substituents coupled thereto In particular, it is possible to achieve long life and high efficiency at the same time when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.
  • the present invention by using the compound represented by the formula (1) as the material of the light emitting layer (140, 340, 440) and / or light efficiency improving layer 180, the energy level and T 1 value between each organic layer, the unique properties of the material ( Mobility, interfacial characteristics, etc.) to optimize the lifespan and efficiency of organic electric devices at the same time.
  • the organic electroluminescent device may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 110, and a hole injection layer 120 thereon , After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, can be prepared by depositing a material that can be used as the cathode 170 thereon have.
  • a deposition method such as PVD or CVD
  • a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 110, and a hole injection layer 120 thereon
  • After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160 can be prepared by depositing a material that can be used as the cathode 170 thereon have.
  • an electron transport auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 and the electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150. It can also be formed as a stack structure.
  • the organic material layer is a solution process or a solvent process (e.g., spin coating process), nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blade using various polymer materials It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.
  • the organic electric device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • the organic electroluminescent device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
  • Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention and a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
  • R 1 to R 4 are independently of each other 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; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 alkenyl group; C 2 ⁇ C 30 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring.
  • At least one pair of neighboring R 1 , neighboring R 2 , and neighboring R 3 may be bonded to each other to form a ring represented by Chemical Formula 1-A.
  • * in Formula 1-A represents a position bonded to Formula 1
  • * in Formula 1-A is preferably bonded to the carbon of the neighboring * portion in Formula 1 below.
  • both rings may be of Formula 1-A, one of Formula 1-A, and the other may be an aromatic ring.
  • Rings formed by bonding adjacent groups to each other include an aromatic ring group of C 6 ⁇ C 60 ; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C 3 ⁇ C 60 Aliphatic ring group; may be selected from the group consisting of.
  • an aromatic ring of C 6 to C 20 preferably an aromatic ring of C 6 to C 14 , such as benzene, naphthalene, phenanthrene, or the like , May form a ring containing a benzene moiety.
  • a, c and d are each integers of 0 to 4
  • b is an integer of 0 to 5
  • each of them is an integer of 2 or more
  • each of a plurality of R 1, each of a plurality of R 2, each of a plurality of R 3 , a plurality of R 4 Each is the same or different.
  • R 1 to R 4 are an aryl group, preferably an aryl group of C 6 to C 30 , more preferably a C 6 to C 18 aryl group, such as phenyl, naphthyl, biphenyl, terphenyl, and the like.
  • R 1 to R 4 are heterocyclic groups, preferably C 2 to C 30 heterocyclic groups, more preferably C 2 to C 18 heterocyclic groups, such as pyridine, pyrimidine, triazine, carbazole, It may be phenyl-carbazole, quinoline, isoquinoline, quinazoline, benzoquinazoline, dibenzothiophene, dibenzofuran, benzothienopyrimidine, and the like.
  • R 1 to R 4 are alkenyl groups, preferably C 2 to C 10 alkenyl groups, such as ethene and propene.
  • X is N-(L-Ar 1 ), O, S or C(R')(R").
  • Ar 1 is 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; And C 3 ⁇ C 60 It may be selected from the group consisting of an aliphatic ring group.
  • Ar 1 is an aryl group, preferably an aryl group of C 6 to C 30 , more preferably an aryl group of C 6 to C 18 , such as phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene , Pyrene, and the like.
  • Ar 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, for example, imidazole, pyridine, pyrimidine, triazine, tetra Gin, dibenzofuran, dibenzothiophene, benzonaphthofuran, benzonaphthothiophene, carbazole, phenylcarbazole, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, quinoline, Isoquinoline, pyridopyrimidine, benzothienopyrimidine, benzofuropyrimidine, benzoindenopyrimidine, naphthofuropyrimidine, naphthothienopyrimidine, indolopyrimidine, phenylindolopyri It may be midine, benzothienopyridine, thiarene, in
  • Ar 1 is a fluorenyl group, it may be 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorene, 9,9'-spirobifluorene, and the like.
  • L and L' are each independently a single bond; C 6 ⁇ C 60 Arylene group; Fluorylene group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring group; And combinations thereof.
  • L and L'are arylene groups preferably an arylene group of C 6 to C 30 , more preferably an arylene group of C 6 to C 18 , such as phenyl, naphthalene, biphenyl, and the like.
  • L and L'are heterocyclic groups it is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, for example, imidazole, pyridine, pyrimidine , Triazine, tetrazine, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzoquinoxaline, isoquinoline, benzothienopyrimidine, benzofuropyrimidine, benzoindenopyrimidine, benzothiazole It may be enopyridine, naphthofuropyrimidine, naphthocyenopyrimidine, pyridopyrimidine, and the like.
  • R a and R b are independently of each other C 6 ⁇ C 60 aryl group; Fluorenyl group; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; And C 2 to C 60 heterocyclic groups including at least one hetero atom among O, N, S, Si, and P.
  • R'and R" are independently of each other hydrogen; deuterium; halogen; C 6 ⁇ C 60 aryl group; fluorenyl group; C 2 ⁇ containing at least one hetero atom of O, N, S, Si and P a heterocyclic group of C 60; C 3 ⁇ C 60 alicyclic group; C 1 ⁇ C 30 alkyl; C 2 ⁇ C 30 alkenyl group a; C 2 ⁇ C 30 alkynyl of; of C 1 ⁇ C 30 alkoxy group; and C ⁇ 6 is selected from the group consisting of an aryloxy group of C 30, may bond to one another to form a ring together R 'and R ".
  • R'and R" are alkyl groups, they may preferably be C 1 to C 10 alkyl groups, such as methyl, propyl, and the like.
  • R'and R" are aryl groups, it may be preferably an aryl group of C 6 to C 30 , more preferably an aryl group of C 6 to C 18 , such as phenyl, biphenyl, naphthyl, terphenyl, and the like.
  • the Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 5.
  • R 1 ⁇ R 4, X , a ⁇ d is were the same as those defined in Formula 1
  • R 1 ' ⁇ R 3 ' is the same as the definition of R 1 ⁇ R 4 as defined in formula (I), respectively
  • b' is an integer from 0 to 3.
  • R 1 to R 4 , Ar 1 , L, a, b, and d are the same as defined in Chemical Formula 1, and c is an integer of 0 to 2.
  • R 1 to R 4 are independently of each other 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; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring. Where L', R a and R b are as defined in Formula 1.
  • the Chemical Formula 1-1 may be represented by one of the following Chemical Formulas 1-1-A to 1-1-F.
  • R 1 to R 4 , L, Ar 1 , and a to d are as defined in Formula 1-1.
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the present invention provides an organic electric device including 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 is represented by Chemical Formula 1 It includes one single compound or two or more compounds.
  • the organic material layer includes at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, preferably the compound is included in the light emitting layer, more preferably It is used as a host material for the light emitting layer.
  • the present invention provides an electronic device including a display device including the organic electroluminescent device represented by Chemical Formula 1 and a control unit driving the display device.
  • the compound represented by Chemical Formula 1 according to the present invention may be synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.
  • Y is independently of each other Cl, Br or I, n', m', o'are each an integer of 0-2, n'+m'+o' ⁇ 1, n, m, o are 0-2 And n+m+o ⁇ 1, provided that m'is 1 and n', o'is 0, the synthesis of the final compound can be obtained through the synthesis of Sub1.
  • Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 2 below, but is not limited thereto.
  • Compound belonging to Sub 1 may be the following compounds, but is not limited thereto, and the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1.
  • Triphenylphosphine oxide (14.3 g, 54.6 mmol) and o-DCB (109 ml) were added to P-9a (9.0 g, 21.8 mmol) and refluxed at 240° C. for 12 hours. Upon completion of the reaction, the temperature of the intermediate product was cooled to room temperature and concentrated. after. The concentrated organic material was separated by a silica gel column to obtain 6.9 g of product (yield: 83.5%).
  • 2-TNATA -1,4-diamine
  • 4-TNATA 4,4-bis[N-(1) on the hole injection layer.
  • -Naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPB”) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
  • dopant the compound P-9 of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) 2 Ir(acac)"). It was used as a material, but a dopant was doped so that the weight ratio was 95:5, and a 30 nm-thick light emitting layer was deposited.
  • a hole blocking layer by vacuum-depositing (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq”) on the light emitting layer to a thickness of 10 nm was formed, and a tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq 3 ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.
  • BAlq (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer
  • Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 below was used instead of the compound P-9 as the host material of the light emitting layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A was used instead of Compound P-9 of the present invention as a host material for the light emitting layer.
  • Electroluminescence (EL) characteristics were measured with PR-650 of photoresearch by applying a direct bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 20 and Comparative Example 1 of the present invention, 2500 cd T95 lifespan was measured using the life measurement equipment of Max Science at /m 2 standard luminance. The measurement results are shown in Table 4 below.
  • Comparative Compound A and the compound of the present invention are identical in that they contain a benzo[mn]indolo[3,2,1-de]acridine moiety, but the compound of the present invention is additionally condensed with indole, indene, benzothiophene, and benzofuran There is a difference in that there is.
  • the compound of the present invention is structurally different from Comparative Compound A, chemical and physical properties such as HOMO, LUMO, T1, charge balance of holes and electrons, hole mobility, and electron mobility are significantly different, and accordingly, the present invention
  • the driving voltage, luminous efficiency and lifespan were significantly improved.

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

Abstract

La présente invention concerne un élément électrique organique et un dispositif électronique le comprenant, l'élément électrique organique comprenant : un composé représenté par la formule chimique 1 ; une première électrode ; une seconde électrode ; et une couche organique entre la première électrode et la seconde électrode, et un dispositif électronique comprenant l'élément électrique organique. La couche de matériau organique fournie par la présente invention comprend le composé représenté par la formule chimique 1, ce qui permet de réduire la tension de commande du l'élément électrique organique, et d'améliorer l'efficacité lumineuse ainsi que la durée de vie.
PCT/KR2019/016099 2018-12-19 2019-11-22 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique le comprenant WO2020130378A1 (fr)

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KR10-2018-0164779 2018-12-19
KR20180164779 2018-12-19
KR10-2019-0150771 2019-11-21
KR1020190150771A KR102381326B1 (ko) 2018-12-19 2019-11-21 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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WO2023207992A1 (fr) * 2022-04-26 2023-11-02 北京八亿时空液晶科技股份有限公司 Dérivé d'indole, élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage

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KR20120081539A (ko) * 2011-01-11 2012-07-19 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
CN103664894A (zh) * 2012-08-30 2014-03-26 昆山维信诺显示技术有限公司 一种6H-萘并[2,1,8,7-klmn]吖衍生物及其应用
KR20160080307A (ko) * 2014-12-26 2016-07-08 삼성디스플레이 주식회사 유기 발광 소자
KR20170096942A (ko) * 2016-02-16 2017-08-25 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2018138306A1 (fr) * 2017-01-30 2018-08-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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KR20120081539A (ko) * 2011-01-11 2012-07-19 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
CN103664894A (zh) * 2012-08-30 2014-03-26 昆山维信诺显示技术有限公司 一种6H-萘并[2,1,8,7-klmn]吖衍生物及其应用
KR20160080307A (ko) * 2014-12-26 2016-07-08 삼성디스플레이 주식회사 유기 발광 소자
KR20170096942A (ko) * 2016-02-16 2017-08-25 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2018138306A1 (fr) * 2017-01-30 2018-08-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023207992A1 (fr) * 2022-04-26 2023-11-02 北京八亿时空液晶科技股份有限公司 Dérivé d'indole, élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage

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