WO2018026197A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et appareil électronique le comprenant - Google Patents

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

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WO2018026197A1
WO2018026197A1 PCT/KR2017/008350 KR2017008350W WO2018026197A1 WO 2018026197 A1 WO2018026197 A1 WO 2018026197A1 KR 2017008350 W KR2017008350 W KR 2017008350W WO 2018026197 A1 WO2018026197 A1 WO 2018026197A1
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이문재
문성윤
권재택
김대성
박무진
박치현
최연희
송현주
이범성
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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
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
    • 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
    • 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
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • 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
    • 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

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 material layer is often formed of a multi-layered 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.
  • Patent Documents 1 to 5 report the performance according to hetero type and arrangement, substituent type, fused position, etc. with respect to the 5-ring cyclic compound in the polycyclic cyclic compound.
  • Patent Document 1 US Patent 5843607
  • Patent Document 2 Japanese Patent Laid-Open No. 1999-162650
  • Patent Document 3 Korean Laid-Open Patent 2008-0085000
  • Patent Document 4 US Patent Publication 2010-0187977
  • Patent Document 5 Korean Laid-Open Patent 2011-0018340
  • Patent Document 6 Korean Laid-Open Patent 2009-0057711
  • Patent Literature 1 and Patent Literature 2 use indolocarbazole cores in which the heteroatoms in the 5-membered cyclic compound consist only of nitrogen (N), and report examples using an aryl group substituted or unsubstituted with N of indolocarbazole. have.
  • N nitrogen
  • Patent Literature 1 and Patent Literature 2 use indolocarbazole cores in which the heteroatoms in the 5-membered cyclic compound consist only of nitrogen (N), and report examples using an aryl group substituted or unsubstituted with N of indolocarbazole. have.
  • N nitrogen
  • Patent Literature 1 and Patent Literature 2 use indolocarbazole cores in which the heteroatoms in the 5-membered cyclic compound consist only of nitrogen (N), and report examples using an aryl group substituted or unsubstituted with N of indolocarbazole. have.
  • N nitrogen
  • Patent Literature 1 and Patent Literature 2 use indolocarbazole
  • PTLs 3 and 4 are substituted with pyridine, pyrimidine, triazine, etc. containing an aryl group and N in an indolocarbazole core having N heteroatoms in the same 5-membered cyclic compound as Patent Documents 1 and 2
  • Patent Documents 1 and 2 Although the described compounds are described, only examples of use for phosphorescent green host materials are described, and no performance is described for other heterocyclic compounds substituted in the indolocarbazole core.
  • Patent Document 5 describes nitrogen (N), oxygen (O), sulfur (S), carbon, etc. as heteroatoms in the 5-ring cyclic compound, but in the performance measurement data, only the examples using the same isotype heteroatoms are present. The performance characteristics of the 5-membered cyclic compound containing hetero hetero atoms could not be confirmed.
  • 5-cyclic cyclic molecules When 5-cyclic cyclic molecules are generally stacked, they have strong electrical interactions with more adjacent ⁇ -electrons, which are closely related to charge carrier mobility, especially the NN-type homocyclic cyclic compounds.
  • the order of intermolecular arrangement has an edge-to-face shape, whereas heterocyclic heterocyclic compounds having different heteroatoms have a pi-stacking structure in which molecular packing structures face each other in reverse directions. structure) has the face-to-face arrangement order between molecules. It has been reported that due to the steric effect of the substituents substituted on the asymmetrically arranged heteroatoms N, which is the cause of the lamination structure, it causes relatively high carrier mobility and high oxidative stability. ( Org. Lett. 2008, 10, 1199)
  • Patent Document 6 examples of using as a fluorescent host material for various polycyclic cyclic compounds having 7 or more rings have been reported.
  • the LUMO and HOMO levels of the host material have a great influence on the efficiency and the lifetime of the organic EL device. Is it possible to efficiently control electron and hole injection in the emission layer? This is because it is possible to prevent the decrease in efficiency and the lifespan due to charge balance control, dopant quenching, and light emission at the hole transport layer interface in the light emitting layer.
  • the energy transfer in the light emitting layer for thermal activated delayed fluorescent (TADF) and exciplex can be identified by the PL lifetime (TRTP) method.
  • the time resolved transient PL (TRTP) method is a method of irradiating a pulsed light source to a host thin film and then observing the decay time of the spectrum over time. It is a measuring method.
  • TRTP measurement is a measurement method that can distinguish between fluorescence and phosphorescence, energy transfer method, exciplex energy transfer method, and TADF energy transfer method within a mixed host material.
  • the present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance control, efficiency and lifetime in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent organic electroluminescent device comprising a phosphorescent dopant It is an object to provide a compound which can be improved, an organic electric element using the same, and an electronic device thereof.
  • the present invention combines a specific first host material with a specific second host material as a main component to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device, thereby reducing the energy barrier between the light emitting layer and the adjacent layer. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and long life of the organic electric element.
  • 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 light emitting layer, and the light emitting layer is represented by the following Chemical Formula 1.
  • an organic electric device comprising a first host compound and a second host compound represented by the following Chemical Formula 2.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric element, and also to greatly improve the life of the element.
  • 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 in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, 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
  • 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 terms "ortho”, “meta”, “para” used in the present invention means the substitution position of all substituents
  • the ortho position is a substituent
  • the position of represents a neighboring compound, for example, in the case of benzene means 1, 2 digits
  • the meta (meta) position represents the next substitution position of the immediate substitution position and benzene is 1, 3 digits as an example
  • the para position means 1 or 4 digits when benzene is used as the next substitution position of the meta position.
  • Ortho- and meta- positions are non-linear types and para- positions are substituted by linear types. have.
  • the present invention provides 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, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. It provides an organic electric device comprising a first host compound represented by the formula (1) and a second host compound represented by the formula (2).
  • X 1 is CR a R b or the following Chemical Formula 1-a,
  • the dotted line represents a bond from X 1 ,
  • X 2 and X 3 are independently of each other NL 3 -Ar 4 , O, S, CR a R b or the formula 1-a, wherein the dotted line in the formula 1-a is a bond from X 2 or X 3 Indicates
  • R a and R b are independently of each other hydrogen; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; C 2 -C 20 Alkenyl group; It is selected from the group consisting of,
  • h and i are integers of 0 or 1, provided that h + i is 1 or more, where h or i is 0 means a direct bond,
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently a C 6 -C 60 aryl group; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Fluorenyl groups; A fused ring group of an aromatic ring of C 6 -C 60 and an aliphatic ring of C 3 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R c ) (R d ); wherein L a is a single bond; C 6 -C 60 arylene group; fluorenylene group; O, N, S A C 2 -C 60 heterocyclic group including at least one hetero atom of Si and P,
  • Ar 1 and Ar 2 may be bonded to each other to form a ring
  • n is an integer of 1 or 2, when n is 2, two Ar 1 is the same or different, and two Ar 2 is the same or different,
  • L 1 , L 2 and L 3 are each independently a single bond; C 6 -C 60 arylene group; Fluorenylene groups; A C 2 -C 60 heterocyclic group comprising at least one hetero atom of O, N, S, Si, and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; And an aliphatic hydrocarbon group; selected from the group consisting of,
  • a, b, c, e and g are each independently an integer from 0 to 10
  • d is an integer from 0 to 5
  • f is an integer from 0 to 2
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R c ) (R d ); or when a, b, c, d, e and g are 2 or more and f
  • A, B, C, D, E and F are independently of each other an aryl group of C 6 -C 20 or a heterocyclic group of C 2 -C 20 ,
  • E and F is a substituted or unsubstituted C 6 aryl group (phenyl group)
  • f is an integer of 2
  • R 6 may be bonded to each other to form a ring to form an aromatic or heterocyclic ring
  • 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 a -N (R c ) (R d ); 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 groups; C
  • the present invention provides a compound represented by Chemical Formulas 1 and 2.
  • L 1 , L 2, and L 3 of Formulas 1 and 2 provide organic electroluminescent devices, wherein the compound is any one of Formulas A-1 to A-13.
  • Y is NL 4 -Ar 5 , O, S, CR e R f or the following Chemical Formula 1-b,
  • L 4 is the same as the definition of L 3 ,
  • Ar 5 is the same as the definition of Ar 4 ,
  • R e and R f are the same as defined above for R a ,
  • R 11 and R 12 are as defined for the R 1,
  • a ', c', d 'and e' are independently of each other an integer from 0 to 4, b 'is an integer from 0 to 6, f' and g 'are independently from each other an integer from 0 to 3, h 'is an integer from 0 to 2, i' is an integer from 0 or 1,
  • R 8 , R 9 and R 10 are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R c ) (R d ); or when a ', b', c ', d', e ', f' and g 'are 2 or more and h '
  • L a is the same as the definition of L a
  • R c and R d are the same as the definition of R c and R d ,
  • Z 1 , Z 2 and Z 3 are independently of each other CR 13 or N, at least one of Z 1 , Z 2 and Z 3 is N,
  • R 13 is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R c ) (R d ); and adjacent R 8 and R 13 may combine with each other to form an aromatic ring or a heteroaromatic ring. ⁇
  • the present invention provides an organic electroluminescent device comprising a compound wherein the first host compound represented by Formula 1 is any one of the following Formula 1-1 to Formula 1-5.
  • Y is NL 4 -Ar 5 , O, S, CR e R f or the following Chemical Formula 1-b,
  • L 4 are as defined in the L 3
  • Ar 5 is the same as the definition of Ar 4 ,
  • R e and R f are the same as defined above for R a ,
  • R 11 and R 12 are the same as defined above R 1 ,
  • a ', c' and d ' are independently of each other an integer from 0 to 4
  • f' and g ' are independently of each other an integer from 0 to 3
  • h' is an integer from 0 to 2
  • R 8 and R 9 are independently of each other hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R c ) (R d ); or when a ', c', d ', f' and g 'are 2 or more and h' is 2 A plurality of R 8 's may
  • the present invention also includes a compound in which the first host compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-6 to 1-20.
  • R a , R b , R 1 , R 2 , R 3 , R 4 , a, b, c, d, L 1 , Ar 1 , Ar 2 and n are as defined above,
  • A, B, C and D are C 10 aryl groups.
  • the first host compound represented by Formula 1 of the present invention includes a compound represented by any one of the following formula 1-21 to formula 1-23.
  • W is NL 5 -Ar 6 , O, S, CR g R h or the following Chemical Formula 1-c,
  • the dotted line represents a bond from W
  • R g and R h are the same as defined above for R a ,
  • R 15 and R 16 are the same as defined above in R 1 ,
  • o and p are the same as the definition of a above,
  • l is an integer of 0 to 3
  • m is an integer of 0 to 4
  • R 13 and R 14 are each independently hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; C 6 -C 30 aryloxy group; And -L a -N (R c ) (R d ); and a plurality of R 13 or a plurality of R 14 or neighboring R 13 and R 14 are bonded to each other to form an aromatic ring or heteroaromatic.
  • L a is the same as the definition of L a
  • R c and R d are the same as the definition of R c and R d ,
  • the general formula (1) in the general formula (1) it provides an organic electroluminescent device comprising a compound when n is 1. In addition, in the general formula (1) provides an organic electric device comprising a compound when n is 2.
  • A, B, C, D, E and F provides an organic electric device comprising a compound represented by any one of the following formulas B-1 to B-7.
  • Z 4 to Z 51 are CR i or N,
  • R i is the same as defined above for R a ,
  • the present invention includes a compound in which the second host compound represented by Chemical Formula 2 is represented by the following Chemical Formula 3 or Chemical Formula 4.
  • E, F, R 5 , R 6 , R 7 , e, f, g, L 2 , Ar 3 , X 2 and X 3 are as defined above. ⁇
  • the present invention provides an organic electroluminescent device, characterized in that R 6 of Formula 2 necessarily forms an aromatic ring or heteroaromatic ring.
  • the present invention also includes a compound in which the second host compound represented by Formula 2 is represented by any one of the following Formulas 5-1 to 5-40.
  • R 5 , R 6 , R 7 , e, f, g, L 2 , Ar 3 , X 2 and X 3 are as defined above,
  • R 17 is hydrogen; heavy hydrogen; Tritium; halogen; Cyano group; Nitro group; C 6 -C 60 aryl group; Fluorenyl groups; Heterocyclic group of O, N, S, C 2 -C 60 containing at least one heteroatom selected from the group consisting of Si and P; A fused ring group of an aliphatic ring of C 3 -C 60 and an aromatic ring of C 6 -C 60 ; An alkyl group of C 1 -C 50 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; An alkoxyl group of C 1 -C 30 ; An aryloxy group of C 6 -C 30 ; and q is 2, each of which is the same or different from each other. ⁇
  • the second host compound represented by the formula (2) includes a compound selected from the group consisting of the following formulas 6-1 to 6-8.
  • E, F, R 5 , R 6 , R 7 , R a , R b , e, f, g, L 2 , L 3 , Ar 3 and Ar 4 are as defined above. ⁇
  • the first host compound represented by Chemical Formula 1 includes a compound represented by any one of the following Compounds 1-1 to 1-70 and Compounds 2-1 to 2-115.
  • the second host compound represented by Chemical Formula 2 includes a compound represented by any one of the following Compounds 3-1 to 3-115.
  • 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 120 is a cathode and the second electrode 180 may be a cathode. This 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 electron transport auxiliary layer, and 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 band gap, electrical characteristics, interface characteristics, etc. may vary depending on which substituents are bonded at which positions, so the selection of the cores and the combination of sub-substituents bound thereto are very good.
  • long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.
  • 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 formed 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 light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
  • the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer or both, the hole transport band layer is represented by Formula 1 It is possible to provide an organic electric device comprising a compound represented by.
  • the present invention provides an optical efficiency improvement layer formed on at least one side of the 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 in the organic electric device. It provides an organic electric element further comprising.
  • 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 material layer according to the present invention can be formed in various ways Therefore, the scope of the present invention is not limited by the formation method.
  • the present invention provides an organic electroluminescent device included in the light emitting layer by mixing the compound represented by Formula 1 and Formula 2 in any one ratio of 1: 9 to 9: 1 in the light emitting layer of the organic material layer.
  • the present invention provides an organic electroluminescent device, characterized in that the compound represented by the formula (1) and the formula (2) in the light emitting layer of the organic material layer is mixed in any one ratio of 1: 9 or 5: 5 used in the light emitting layer. . More preferably, the mixing ratio of the compound represented by Formula 1 and Formula 2 is included in the light emitting layer at 2: 8 or 3: 7.
  • the organic electric element according to an embodiment of the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, side-by-side arrangement of R (Red), G (Green), and B (Blue) light emitting parts in a mutual plane, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the present invention is a display device including the above-described organic electric element; And a controller for driving the display device.
  • the organic electroluminescent 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 monochrome 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.
  • Final product 1 Compound represented by Formula 1 according to the present invention (final product 1) is synthesized by reacting Sub 1 and Sub 2, as shown in Scheme 1, but is not limited thereto.
  • X 1 , C, D, R 3 , R 4 , c, d, Ar 1 , Ar 2 , L 1 and n are the same as defined in Formula 1 above, Hal 1 is Br or Cl.
  • the synthesis method for Sub 1 of Scheme 1 is Korean Patent Registration No. 10-1520955 (Registration date of May 11, 2015), Korean Patent Registration No. 10-1530885 (Registration date of June 17, 2015), Korea Patent Registration 10 of the applicant -1530886 (Registration date of June 17, 2015), Korea Patent Registration No. 10-1614740 (Registration date of April 18, 2016), Korea Application Patent 2013-0056221 (Application dated May 20, 2013), Korea Application Patent 2015-0035780 (2015.03 .16 dated), the Korean Patent Application 2015-0083505 (application dated June 12, 2015) was used in the synthesis method.
  • L 1 is not a single bond, it may be synthesized by the reaction route of Scheme 2, but is not limited thereto, and Hal 1 is Br or Cl.
  • Sub 1-36 (CAS Registry Number: 1800333-62-3) (50.31 g, 125.49 mmol) in Bis (pinacolato) diboron (35.05 g, 138.04 mmol), Pd (dppf) Cl 2 (3.07 g, 3.76 mmol), KOAc (36.95 g, 376.47 mmol), DMF (630 ml) were added and 37.69 g (yield: 61%) of product was obtained using the Sub 1-I-26 synthesis method.
  • the compound belonging to Sub 1 may be, but is not limited to, the following compounds.
  • Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 1.
  • the synthesis method for Sub 2 of Scheme 1 used the synthesis method disclosed in the applicant's Korean Patent No. 10-1251451 (Registration date of April 5, 2013). It may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • the compound belonging to Sub 2 may be, but is not limited to, the following compounds.
  • Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 2.
  • Sub 1-1 (9.70 g, 42.41 mmol) obtained in the above synthesis was dissolved in toluene (445 ml) in a round bottom flask, and then Sub 2-14 (14.99 g, 46.65 mmol) and Pd 2 (dba) 3 (1.17 g) , 1.27 mmol), P ( t -Bu) 3 (0.51 g, 2.54 mmol), NaO t -Bu (12.23 g, 127.23 mmol) were added and stirred at 100 ° C.
  • the compound represented by Chemical Formula 2 according to the present invention (final product 2) is synthesized by reacting Sub 3 and Sub 4, as shown in Scheme 4 below, but is not limited thereto.
  • E, F, R 5 , R 6 , R 7 , e, f, g, h, i, L 2 , Ar 3 , X 2 and X 3 are the same as defined in Formula 2, Hal 1 is Br or Cl to be.
  • Sub 3 of Scheme 4 may be synthesized by the reaction route of Scheme 5, but is not limited thereto.
  • Carbazole derivatives which are starting materials used in the synthesis of Sub 3-I-1, were prepared by the synthesis method disclosed in Korean Patent Registration No. 10-1535606 (registered date of July 3, 2015).
  • Dibenzothiophene derivative or dibenzofuran which is a starting material used in the synthesis of Sub 3-I-1, was prepared by the synthesis method disclosed in Korean Patent Application No. 2014-0074261 (filed on June 18, 2014) of the present applicant.
  • Fluorene derivatives which are starting materials used in the synthesis of Sub 3-I-1, are disclosed in Korean Patent Application No. 2013-0056221 (filed May 20, 2013) and Korean Patent Application No. 2015-0083505 (filed June 12, 2015). It was prepared by the synthetic method.
  • Triphenylphosphine (53.14 g, 202.60 mmol) and o -dichlorobenzene (405 ml) were added to Sub 3-II-16 (34.97 g, 81.04 mmol) obtained in the above synthesis, and 21.69 g of the product was obtained using the Sub 3-1 synthesis method. Yield: 67%).
  • Triphenylphosphine (43.23 g, 164.81 mmol) and o -dichlorobenzene (330 ml) were added to Sub 3-II-90 (27.39 g, 65.92 mmol) obtained in the above synthesis, and the product was obtained using 14.92 g ( Yield: 59%).
  • Compounds belonging to Sub 3 may be the following compounds, but are not limited thereto.
  • Table 4 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 3.
  • Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 6, but is not limited thereto. At this time, Hal 1 and Hal 2 are Br or Cl.
  • Compounds belonging to Sub 4 may be the following compounds, but are not limited thereto.
  • Table 5 shows Field Desorption-Mass Spectrometry (FD-MS) values of some compounds belonging to Sub 4.
  • Sub 3-1 (10.00 g, 26.15 mmol) obtained in the above synthesis was dissolved in toluene (275 ml) in a round bottom flask, and then Sub 4-1 (CAS Registry Number: 108-86-1) (4.52 g, 28.76 mmol) ), Pd 2 (dba) 3 (0.72 g, 0.78 mmol), P ( t -Bu) 3 (0.32 g, 1.57 mmol), NaO t -Bu (7.54 g, 78.44 mmol) were added and stirred at 100 ° C. .
  • Example 1 to [ Example 95] Red organic electroluminescent device ( Light emitting layer Mixed phosphorescent host)
  • NPB N-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine
  • the hole transport layer was formed by vacuum deposition to a thickness of 60 nm, and a mixture of the compound of the present invention represented by Formula 1 and Formula 2 (described in Table 7) 3: 7 was used as a host on the hole transport layer.
  • 30 nm thick light emitting layer was deposited on the hole transport layer by doping (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] at 5% by weight.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of the present invention represented by Formula 2 as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used alone.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used alone.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 4 was used alone.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 2 were used as a host.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 and Comparative Compound 4 were used as a host.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 1 to 95 and Comparative Examples 1 to 9 of the present invention
  • the T95 life was measured using a McScience Lifetime Measurement Equipment at 2500 cd / m 2 reference luminance, and the measurement results are shown in Table 7 below.
  • the compounds of the present invention represented by the compounds of the present invention (3-6, 3-61, 3) using the compounds of the present invention represented by the general formula (2) and Comparative Compounds 1 to 4 alone as phosphorescent hosts It was confirmed that Comparative Examples 1 to 3 using -74) showed higher efficiency and higher lifetime than Comparative Examples 4 to 7 using the comparative compound.
  • Comparative Examples 8 and 9 which are used as a phosphorescent host by mixing Comparative Compound 1, Comparative Compound 2, or Comparative Compound 3, and Comparative Compound 4 than Comparative Examples 1 to 7 using the single substance, exhibit higher efficiency. I could confirm that. Comparing Comparative Example 8 and Comparative Example 9, a heterocyclic polycyclic compound having heteroatoms (N, S) different from each other in the 5-ring cyclic compound is compared to Comparative Example 8 in which a 5-ring heterocyclic compound having the same nitrogen atom is mixed. It was confirmed that Comparative Example 9 using the mixture included showed a higher efficiency.
  • Example 1 to Example 95 used as a host by mixing the compound of the formula 1 and the compound of the present invention exhibits a significantly higher efficiency and life, It was confirmed that the driving voltage was shown.
  • the inventors of the present invention determine that each of the substances of the compound of Formula 1 and the compound of Formula 2 have new characteristics other than those of the substances, based on the experimental results, the substance of Formula 1, the substance of Formula 2 , PL lifetime was measured using the mixture of the present invention.
  • the compound of Formula 1 and Formula 2 of the present invention were mixed, it was confirmed that a new PL wavelength was formed differently from the case of a single compound. It was confirmed that the decrease and disappearance time increased from about 60 times to as much as about 360 times.
  • the transmission is believed to increase efficiency and lifetime. This can be said to be an important example that the mixed thin film shows the exciplex energy transfer and light emission process when using the mixture of the present invention as a result.
  • the combination of the present invention is superior to Comparative Example 8 to Comparative Compound 9, which is used as a phosphorescent host mixed with a comparative compound, because the polycyclic cyclic compound represented by the formula (2) is characterized by not only electrons but also stability against holes and high T1.
  • the compound represented by Formula 1 having strong hole properties is mixed, electron blocking ability is improved due to high T1 and high LUMO energy values, and more holes are quickly and easily moved to the light emitting layer. As a result, the charge balance in the light emitting layer of holes and electrons is increased, so that light is emitted inside the light emitting layer rather than at the hole transport layer interface. .
  • Example 96 to [ Example 98] Mixed ratio Red organic electroluminescent device ( Light emitting layer Mixed phosphorescent host)
  • An organic electroluminescent device was manufactured in the same manner as in Example 68, except for using a different mixing cost of materials as described in Table 8.
  • Example 99 to [ Example 101] Mixed ratio Red organic electroluminescent device ( Light emitting layer Mixed phosphorescent host)
  • An organic electroluminescent device was manufactured according to the same method as Example 9 except for using a different mixing cost of materials as described in Table 8.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 9, 68 and 96-101 of the present invention
  • the T95 lifetime was measured using the McScience Lifetime Measurement Equipment at 2500 cd / m 2 reference luminance, and the measurement results are shown in Table 8 below.
  • the mixture of the compound of the present invention was measured by manufacturing a device by ratio (2: 8, 3: 7, 4: 6, 5: 5).
  • the results of the mixture of compound 1-56 and compound 3-61 showed similarly excellent driving voltage, efficiency and lifetime for 2: 8 and 3: 7.
  • the ratio of the first host was increased, the results of driving voltage, efficiency, and lifespan were gradually decreased, which was the same in the mixture of Compound 2-48 and Compound 3-6. This may be explained because the charge balance in the light emitting layer is maximized when an appropriate amount of the compound represented by Chemical Formula 1 having strong hole characteristics such as 2: 8 and 3: 7 is mixed.

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Abstract

Un mélange de composés selon la présente invention est utilisé en tant que matériau hôte phosphorescent, ce qui permet d'obtenir un rendement d'émission de lumière élevé et une faible tension d'excitation d'un élément électrique organique; et à fournir un élément électrique organique capable d'améliorer de manière significative la durée de vie de l'élément et un appareil électronique utilisant celui-ci.
PCT/KR2017/008350 2016-08-03 2017-08-02 Composé pour élément électrique organique, élément électrique organique l'utilisant, et appareil électronique le comprenant WO2018026197A1 (fr)

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