WO2015199303A1 - Composé, et dispositif photoélectrique organique et dispositif d'affichage le comprenant - Google Patents

Composé, et dispositif photoélectrique organique et dispositif d'affichage le comprenant Download PDF

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WO2015199303A1
WO2015199303A1 PCT/KR2015/000049 KR2015000049W WO2015199303A1 WO 2015199303 A1 WO2015199303 A1 WO 2015199303A1 KR 2015000049 W KR2015000049 W KR 2015000049W WO 2015199303 A1 WO2015199303 A1 WO 2015199303A1
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group
substituted
unsubstituted
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이상신
유은선
이준엽
조용주
최윤호
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삼성에스디아이 주식회사
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    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • 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
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • 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
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

Definitions

  • a compound, an organic optoelectronic device, and a display device are provided.
  • Organic optoelectric diodes are devices that can switch between electrical and optical energy.
  • Organic optoelectronic devices can be divided into two types according to the principle of operation.
  • One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electric energy.
  • It is a light emitting device that generates light energy from energy.
  • Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
  • the organic light emitting diode (OLED) has attracted much attention recently as the demand for flat panel display devices increases.
  • the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material, and has a structure in which an organic layer is inserted between an anode and a cathode.
  • the organic layer may include a light emitting layer and an auxiliary layer
  • the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer to increase efficiency and stability of the organic light emitting device. And at least one layer selected from a hole blocking layer.
  • the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, is affected by the organic material included in the organic layer.
  • D 1 and D 2 are each independently represented by the following chemical formulas d-1 or d-2:
  • X 1 to X 8 are each independently N or CR a ,
  • L 1 is N, B, CR b or SiR c ,
  • M 1 is a single bond, 0 or S
  • L 2 is C or Si
  • R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group ego,
  • R and R c are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or unsubstituted Amine group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C1 to C30 carbonyl group, substituted or Unsubstituted CI to C30 carbonylamino group, substituted or unsubstituted C1 to C30
  • W 1 and W 2 are each independently a C1 to C10 alkyl group unsubstituted or substituted with a cyano group, nitro group, halogen group, amide group, sulfonyl group, phosphine group, or phosphoryl group; C6 to C20 aryl group unsubstituted or substituted with a cyano group, nitro group, halogen group, amide group, sulfonyl group, phosphine group, or phosphoryl group; Cyano group; Nitro group; Halogen group; Amide group; Sulfonyl group; Phosphine groups; Phosphoryl group; Or a combination thereof,
  • a, b, c and d are each independently an integer of 1 or more,
  • a compound for an organic optoelectronic device comprises an anode and a cathode facing each other, and a layer of an organic layer located between the anode and the cathode, the organic layer is a compound according to an embodiment of the present invention described above It provides an organic optoelectronic device comprising.
  • the above-described embodiment of the present invention is provided.
  • a display device including an organic optoelectronic device.
  • the organic optoelectronic device including the compound ol has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage.
  • FIG. 1 and 2 are cross-sectional views showing various embodiments of an organic light emitting device that can be manufactured using a compound according to an embodiment of the present invention.
  • 3 is a graph showing light emission spectra according to a comparative example.
  • 4 is a graph showing the absorption spectrum of Compound 1, the emission spectrum in solution, and the emission spectrum at a concentration of 1% of polystyrene (PS).
  • 5 is a current density-voltage graph according to a comparative example.
  • FIG. 6 is a graph showing current density-voltage-luminance according to an embodiment of the present invention.
  • FIG. 8 is a graph showing the external quantum efficiency according to an embodiment of the present invention at a specific current density and emission wavelength.
  • substituted means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted Ring C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, polouro group, trifluorouromethyl group, etc.
  • C1 to CH means a trifluoroalkyl group or a cyano group.
  • substituted halogen group hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C1 to C10 such as C3 to C30 cycloalkyl group, C6 to C30 aryl group, C 1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc.
  • Two adjacent substituents of the trifluoroalkyl group or the cyano group are fused to form a ring. It may be formed.
  • hetero means one to three heteroatoms selected from the group consisting of ⁇ , ⁇ , S and ⁇ , and the remainder is carbon unless otherwise defined.
  • an "alkyl group” is aliphatic
  • the alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.
  • the alkyl group may be an alkyl group that is C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, with methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec -butyl and t-butyl Selected from the group consisting of:
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nuclear group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
  • Aryl group 'means a substituent in which all elements of the cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic ( That is, a ring) group that shares adjacent pairs of carbon atoms.
  • a “heterocyclic group” refers to a hetero atom selected from the group consisting of N, 0, S, P, and Si in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. Containing at least one, and the rest being carbon.
  • the heterocyclic group is a fused ring, the heterocyclic group may include one or more heteroatoms for each or each ring.
  • the heterocyclic group is a higher concept encompassing the heteroaryl group.
  • a substituted or unsubstituted aryl group and / or a substituted or unsubstituted C2 to C30 heterocyclic group a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, Substituted or unsubstituted phenan ⁇ reylene group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted peryleneyl group
  • a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a combination thereof, or a combination thereof may be in a fused form, but is not limited thereto.
  • a single bond refers to a bond directly connected without passing through carbon or a hetero atom other than carbon, and specifically, M means a single bond means that both atoms connected to M are directly connected. That is, when M, one of the six atoms constituting the hexagonal ring in the present specification, is a single bond, it forms a pentagonal ring.
  • the halogen group means a fluoro group, a chloro group, a bromo group or an iodine group, and in one example, may be a fluoro group.
  • thermal delayed fluorescence refers to a phenomenon in which fluorescence is emitted by using thermally activated delayed fluorescence (TADF) from a tritium excited state to a singlet excited state. Delayed fluorescence is called in the sense that long-lived light emission occurs because of the triplet excited state. Because it uses fluorescent singlet excited state and triplet excited state High efficiency fluorescence can be expressed.
  • TADF thermally activated delayed fluorescence
  • D 1 and D 2 are each independently represented by the following chemical formulas d-1 or d-2:
  • X 1 to X 8 are each independently N or CR a ,.
  • L 1 is N, B, CR b or SiR c ,
  • M 1 is a single bond, 0 or S
  • L 2 is C or Si
  • R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group ego,
  • R b and! are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or unsubstituted Substituted amine group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C1 to C30 carbonyl group, substituted or unsubstituted C1 to C30 carbonylamino group, substituted or unsubstituted C1 to C30 sulfamoylamino group, substituted Or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted silyl
  • W 1 and W 2 are each independently a C1 to C10 alkyl group unsubstituted or substituted with a cyano group, a nitro group, a halogen group, an amide group, a sulfonyl group, a phosphine group, or a phosphoryl group; C6 to C20 aryl group unsubstituted or substituted with a cyano group, a nitro group, a halogen group, an amide group, a sulfonyl group, a phosphine group, or a phosphoryl group; Cyano group; Nitro group; Halogen group; Amide group; Sulfonyl group; Phosphine groups; Phosphoryl group; Or a combination thereof,
  • a, b, c and d are each independently an integer of 1 or more,
  • the compound represented by the formula (I) of the present specification has a rotational degree of freedom due to the steric hindrance between the biphenyl core and the substituent by dividing the region of the electron donating group and the electron withdrawing group into the biphenyl core. It is lowered to have a rigid molecular structure.
  • This rigid molecular structure facilitates the separation of HOMO-LUMO, thereby reducing the energy gap between triplet excitation energy and singlet excitation energy.
  • This small energy gap facilitates the transition between the triplet to the singlet excited state of the triplet, so that the luminescence efficiency can be improved by designing a molecule that utilizes the fluorescence of the singlet as well as the fluorescence transferred from the triplet to the reverse system.
  • axtone is 25% in singlet excited state, in triplet excited state
  • the phosphorescent material has a limitation in terms of freedom of molecular design because a complex compound containing a metal or heavy metal such as Ir, Pt, C U , Be, etc. must be used.
  • the compound represented by the formula (I) according to the present invention can be used to It is a pure organic compound that does not contain and can increase the degree of freedom of molecular design, and can be used for high-efficiency light emitting materials due to delayed fluorescence.
  • D 1 and D 2 refer to a substituent as an electron donor, and may be represented by the following Chemical Formula d-1 or d-2.
  • X 1 to X 8 are as defined above, L 1 is N, B, CR b or SiR c , ⁇ 1 is a single bond, 0 or S, and L 2 Is C or Si, ⁇ 2 is
  • ⁇ and * is the junction point.
  • R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group ego,
  • R b and! are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or unsubstituted A substituted amine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 carbonyl group, a substituted or unsubstituted C1 to C30 carbonylamino group, a substituted or unsubstituted C1 to C30
  • C1 to C30 sulfonyl group substituted or unsubstituted C1 to C30 alkylthio group, substituted or unsubstituted C1 to C30 heterocyclothiyl group, substituted or unsubstituted C1 to C30 ureide group, halogen group, cyano group, hydroxide It is a siloxane group, an amino group, a nitro group, a carboxyl group, or a combination thereof.
  • X 1 to X 8 are each independently N or CR a
  • R a , al and R 32 are each independently hydrogen, deuterium, substituted or unsubstituted C10 alkyl group in C1, substituted or unsubstituted C1 to C10 alkenyl group, substituted or unsubstituted C1 to C10 alkoxy group, or A substituted or unsubstituted C6 to C20 aryl group,
  • R b is as defined above.
  • D 1 and D 2 are each independently a substituted or unsubstituted carbazole group, a substituted or unsubstituted acridine group, a substituted or unsubstituted phenoxazine group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted Fluorenyl group, or a substituted or unsubstituted amine group.
  • substituted means a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkenyl group, a substituted or unsubstituted C1 to C10 alkoxy group, or a substituted or unsubstituted C6 to Mean substituted by C20 aryl group.
  • substituents include methyl group, ethyl group, propyl group, isobutyl group, meso groups,
  • the W 1 and W 2 means a substituent as an electron acceptor, each independently, a cyano group, a nitro group, a halogen group, A C1 to C10 alkyl group unsubstituted or substituted with an amide group, sulfonyl group, phosphine group, or phosphoryl group; Cyano group, nitro group, halogen group, amide group C6 to C20 aryl group unsubstituted or substituted with a sulfonyl group, a phosphine group, or a phosphoryl group; Cyano group; Nitro group; Halogen group; Amide group; Sulfonyl group; Phosphine groups; Phosphoryl group; Or combinations thereof.
  • amide group, sulfonyl group, phosphine group, and phosphoryl group are each a functional group represented by -CONR, -SO 3 R, -PRR ', -PORR',
  • R and R ' are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkenyl group, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.
  • Formula I may be represented by the following Formula 1-1 or 1-2 depending on the zoning of the substituents.
  • D ', D 2 defined in the W 1 and W 2 are as described above, a 3 ⁇ a + b ⁇ 6, 3 ⁇ c + d ⁇ 6. Since a substituent functioning as an electron donor or an electron acceptor is simultaneously present at a position adjacent to the biphenyl core, it is possible to more effectively prevent rotational freedom due to steric hindrance between substituents, and thus formation of a rigid molecular structure can be expected. Since the molecular structure further increases the probability of intercalation transition due to thermal activation, theoretically 100% of internal quantum efficiency can be achieved, and the light emission efficiency can be further improved by suppressing triplet-triple extinction. . Specific examples of compounds according to one embodiment of the invention are listed below
  • the compound may be for an organic optoelectronic device.
  • the present invention in another embodiment, it includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer provides an organic optoelectronic device comprising the compound.
  • the organic layer may include a light emitting layer, and the light emitting layer may include the compound.
  • the compound may be included as a thermal delayed fluorescent material of the light emitting layer.
  • the light emitting layer may further include a host material in addition to the thermal delayed fluorescent material.
  • the compound may be used in the organic layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, and lower the driving voltage.
  • the organic optoelectronic device may be an organic light emitting device.
  • a cross-sectional view of an organic light emitting device is A cross-sectional view of an organic light emitting device.
  • the organic light emitting diodes 100 and 200 may include an anode 120, a cathode 110, and at least one layer positioned between the anode and the cathode.
  • It has a structure including the organic thin film layer 105.
  • the anode 120 comprises an anode material, which is typically
  • a material having a large work function is preferable to facilitate hole injection into the organic thin film layer.
  • the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide ( ⁇ ), and indium zinc oxide (IZO). And metal oxides such as ZnO and A1 or combinations of metals and oxides such as Sn0 2 and Sb, and poly (3-methylthiophene), poly (3,4- (ethylene-1, Conductive materials such as 2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole, and polyaniline, and the like, but are not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • the negative electrode 1 10 includes a negative electrode material, which is usually used as a negative electrode material.
  • the material has a small work function to facilitate electron injection into the organic thin film layer.
  • the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or alloys thereof, and LiF / Al. , Multilayer structures such as Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
  • a metal electrode such as aluminum may be used as the cathode.
  • FIG. 1 illustrates that only the light emitting layer 130 exists as the organic layer 105.
  • the organic layer 105 may exist only as the light emitting layer 130.
  • FIG. 2 includes an electron transport layer as the organic layer 105.
  • the organic layer 105 includes the light emitting layer 230 and the hole transport layer 140, in which the light emitting layer 230 and the hole transport layer 140 exist. It may be two-layered. In this case, the light emitting layer 230 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ⁇ .
  • the organic layer 105 may further include an electron injection layer, an auxiliary electron transport layer, an electron transport layer, a major transport layer, an auxiliary major transport layer, a major injection layer, and the like.
  • the light emitting layers 130 and 230 and the hole transport layer 140 forming the organic layer 105, an electron injection layer, an auxiliary electron transport layer, an electron transport layer, an electron transport layer, and an auxiliary hole, which may not be added, may be added.
  • Any one selected from the group consisting of a hole transport layer, a hole injection layer, and a combination thereof includes the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device may be used in the light emitting layers 130 and 230, and may be used as a green fluorescent material in the light emitting layer.
  • the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
  • Another embodiment of the present invention provides a display device including the organic optoelectronic device.
  • intermediate 1 (1.0 g, 6.1 mmol) is slowly added to THF as a 1 M solution. After stirring for 2 hours at room temperature, the reaction was terminated by pouring methanol or distilled water. The reaction product was extracted with MC and subjected to column chromatography using a mixed developing solvent of chloroform / nucleic acid to obtain 2.3 g of intermediate 2.
  • the intermediate 2 (1.0 g, 2.2 mmol) obtained in Synthesis Example 2 was added with a mixed THF / DMPU solvent, and the temperature was lowered to -90 ° C. or lower under a nitrogen atmosphere, followed by stirring for 30 minutes.
  • 2 M concentration of LDA (0.3 g, 2.4 mmol) was added slowly to the reaction.
  • iodine (0.3 g, 1.1 mmol) was dissolved in THF and slowly added to the reaction.
  • the reaction was terminated by adding hydrochloric acid having a concentration of ⁇ .
  • the reaction product was extracted with MC and washed three times with distilled water.
  • the extract was dried over anhydrous magnesium sulfate and the solvent was removed.
  • the reaction product was purified by column chromatography using a mixed developing solvent of chloroform / nucleic acid, and finally sublimed purification gave 0.5 g of a pure yellow solid.
  • the emission spectrum (blue) and the emission spectrum (light green) at PS 1% concentration can be confirmed.
  • the luminescence spectrum suitable for the green luminescent material is shown through the fluorescence spectrum (purple) at low temperature.
  • the difference between the calculated singlet energy (SO 2.60 eV and triplet energy (TO 2.47 eV) is 0.13 eV, which is relatively small.
  • a compound of Intermediate 3 was obtained in 82% yield in a similar manner to the preparation of Intermediate 2, except using 9H-carbazole as 3,6-dimethyl-9H-carbazole.
  • each thin film was laminated with a vacuum degree of 5.0 ⁇ 10 ⁇ 4 Pa by vacuum deposition.
  • ⁇ -NPD was formed at a thickness of 35 nm on ⁇
  • mCP was formed at a thickness of 10 nm.
  • the comparative compound represented by the formula d and mCP were co-deposited from another evaporation source to form a 15 nm thick layer to form a light emitting layer. At this time, the concentration of the comparative compound represented by the formula (d) was 3.0 weight 0 /.
  • ⁇ is formed at a thickness of 10 nm
  • TPBi is formed thereon at a thickness of 40 nm
  • lithium fluoride (LiF) is vacuum deposited at 0.8 nm, followed by deposition of aluminum (A1) at a thickness of 100 nm.
  • Al aluminum
  • the organic electroluminescent element manufactured by the semiconductor parameter. analyzer (Ajirent ⁇ technology company make: E5273A), optical power meter measurement device (new pot) Company: 1930 C) and an optical spectrometer (manufactured by Ocean Optics: USB2000).
  • Example 1 In place of the comparative example compound represented by the dopant d, using the compound 1 prepared in Example 1 it was doped with 5 weight 0/0, mCP, and 100 to each TmPyPB: 0: 90: 10, 75: 25 Doped hosts were mixed at the ratio of. Except for this, organic light emitting diodes were manufactured in the same manner as in the device comparison example, respectively, in Example 1-A, Example 1-B, and Example 1-C. 6 is shown. Device Examples 2-A, 2-B, and 2-C
  • the compound 1 prepared in Example 1 was used to be doped at 1 weight 0 /., 3 weight%, and 5 weight%, and mCP and TmPyPB were 50:50. Doped hosts were weighted by weight. Except for this, an organic light emitting diode was manufactured in the same manner as in Comparative Example, and the device example 2-A, the device example 2-B, and the device example 2-C were manufactured, and the quantum efficiency results are shown in FIG. 8. .
  • FIG. 6 is a graph showing current density-voltage-luminance according to an embodiment of the present invention.
  • FIG. 8 is a graph showing the external quantum efficiency of the organic light emitting device manufactured according to an embodiment of the present invention at a specific current density and emission wavelength.
  • the maximum external quantum efficiency is excellent at the same emission wavelength and similar current density as compared to the device to which the compound of the comparative example is applied. have. That is, when the compound of the comparative example is applied in FIG. 7, the external quantum efficiency is 11% or less, whereas when the compound of the example is applied in FIG. 8, the external quantum efficiency of 18.7% is achieved.
  • the doping concentration of the dopant according to the present embodiment the first weight 0/0, and can identify represents the best efficiency.
  • the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé représenté par la formule chimique I, un dispositif photoélectronique organique comprenant ce composé; et un dispositif d'affichage comprenant le dispositif photoélectronique organique.
PCT/KR2015/000049 2014-06-24 2015-01-05 Composé, et dispositif photoélectrique organique et dispositif d'affichage le comprenant WO2015199303A1 (fr)

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KR10-2014-0077570 2014-06-24
KR1020140077570A KR101783650B1 (ko) 2014-06-24 2014-06-24 화합물, 이를 포함하는 유기광전자소자 및 표시장치

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WO2018001820A1 (fr) * 2016-07-01 2018-01-04 Cynora Gmbh Dérivés dicarbazolbiphényle destinés à être utilisés dans des dispositifs optoélectroniques
DE102016112082A1 (de) * 2016-07-01 2018-01-04 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen
WO2018037069A1 (fr) * 2016-08-24 2018-03-01 Cynora Gmbh Biphényles à substitution hétérocyclique, en particulier destinés à être utilisés dans des dispositifs optoélectroniques
DE102017103542B3 (de) * 2017-02-21 2018-03-29 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
DE102017109593A1 (de) * 2017-05-04 2018-11-08 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
CN109553567A (zh) * 2017-09-27 2019-04-02 辛诺拉有限公司 有机分子，特别是用于光电子器件中的有机分子
CN109666025A (zh) * 2017-10-16 2019-04-23 辛诺拉有限公司 有机分子，特别是用于光电子器件中的有机分子
DE102018114290B3 (de) * 2018-06-14 2019-06-06 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
DE102018107166A1 (de) * 2018-03-26 2019-09-26 Cynora Gmbh Organische Moleküle, insbesondere für die Verwendung in optoelektronischen Vorrichtungen
WO2019195104A1 (fr) * 2018-04-02 2019-10-10 Kyulux, Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
CN110799496A (zh) * 2017-11-28 2020-02-14 株式会社Lg化学 化合物及包含其的有机发光器件
EP3647392A4 (fr) * 2017-06-27 2020-06-03 Kyulux, Inc. Matériau électroluminescent, composé, phosphore à longue persistance et élément électroluminescent
CN112218861A (zh) * 2018-10-22 2021-01-12 株式会社Lg化学 多环化合物及包含其的有机发光元件
CN113939501A (zh) * 2019-06-14 2022-01-14 国立大学法人九州大学 间苯二腈化合物、发光材料及使用其的发光元件
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WO2019107932A1 (fr) * 2017-11-28 2019-06-06 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
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KR102550691B1 (ko) * 2018-06-15 2023-07-04 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자

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US11136294B2 (en) 2016-07-01 2021-10-05 Cynora Gmbh Organic molecules for use in optoelectronic devices
CN109415317A (zh) * 2016-07-01 2019-03-01 辛诺拉有限公司 用于光电器件的二咔唑联苯衍生物
DE102016112082B4 (de) * 2016-07-01 2018-01-11 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen
CN109476598A (zh) * 2016-07-01 2019-03-15 辛诺拉有限公司 用于光电器件的二咔唑联苯衍生物
WO2018001820A1 (fr) * 2016-07-01 2018-01-04 Cynora Gmbh Dérivés dicarbazolbiphényle destinés à être utilisés dans des dispositifs optoélectroniques
DE102016112082A1 (de) * 2016-07-01 2018-01-04 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen
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WO2018037069A1 (fr) * 2016-08-24 2018-03-01 Cynora Gmbh Biphényles à substitution hétérocyclique, en particulier destinés à être utilisés dans des dispositifs optoélectroniques
DE102017103542B3 (de) * 2017-02-21 2018-03-29 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
US11825743B2 (en) 2017-02-21 2023-11-21 Samsung Display Co., Ltd. Organic molecules for use in organic optoelectronic devices
WO2018153510A1 (fr) * 2017-02-21 2018-08-30 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques organiques
JP2019533739A (ja) * 2017-05-04 2019-11-21 サイノラ ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機分子、特に光電子デバイスに用いる有機分子
DE102017109593A1 (de) * 2017-05-04 2018-11-08 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
DE102017109593B4 (de) * 2017-05-04 2018-12-13 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
US11832516B2 (en) 2017-06-27 2023-11-28 Kyulux, Inc. Light-emitting material, compound, long-persistent phosphor and light-emitting element
EP3647392A4 (fr) * 2017-06-27 2020-06-03 Kyulux, Inc. Matériau électroluminescent, composé, phosphore à longue persistance et élément électroluminescent
CN109553567B (zh) * 2017-09-27 2021-12-14 辛诺拉有限公司 有机分子，特别是用于光电子器件中的有机分子
US10978646B2 (en) 2017-09-27 2021-04-13 Cynora Gmbh Organic molecules for use in optoelectronic devices
CN109553567A (zh) * 2017-09-27 2019-04-02 辛诺拉有限公司 有机分子，特别是用于光电子器件中的有机分子
CN109666025A (zh) * 2017-10-16 2019-04-23 辛诺拉有限公司 有机分子，特别是用于光电子器件中的有机分子
US10998504B2 (en) 2017-10-16 2021-05-04 Cynora Gmbh Organic molecules for use in optoelectronic devices
CN109666025B (zh) * 2017-10-16 2021-12-14 辛诺拉有限公司 有机分子，特别是用于光电子器件中的有机分子
US11450827B2 (en) 2017-11-17 2022-09-20 Samsung Display Co., Ltd. Organic light-emitting device
CN110799496A (zh) * 2017-11-28 2020-02-14 株式会社Lg化学 化合物及包含其的有机发光器件
US11104645B2 (en) 2018-03-26 2021-08-31 Cynora Gmbh Organic molecules for use in optoelectronic devices
DE102018107166A1 (de) * 2018-03-26 2019-09-26 Cynora Gmbh Organische Moleküle, insbesondere für die Verwendung in optoelektronischen Vorrichtungen
DE102018107166B4 (de) 2018-03-26 2020-06-25 Cynora Gmbh Organische Moleküle, insbesondere für die Verwendung in optoelektronischen Vorrichtungen
WO2019195104A1 (fr) * 2018-04-02 2019-10-10 Kyulux, Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
DE102018114290B3 (de) * 2018-06-14 2019-06-06 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
CN112334447A (zh) * 2018-06-14 2021-02-05 辛诺拉有限公司 用于光电器件的有机分子
CN112218861A (zh) * 2018-10-22 2021-01-12 株式会社Lg化学 多环化合物及包含其的有机发光元件
CN112218861B (zh) * 2018-10-22 2023-08-04 株式会社Lg化学 多环化合物及包含其的有机发光元件
CN113939501A (zh) * 2019-06-14 2022-01-14 国立大学法人九州大学 间苯二腈化合物、发光材料及使用其的发光元件
EP3985081A4 (fr) * 2019-06-14 2024-01-24 Univ Kyushu Nat Univ Corp Composés isophtalonitriles, matériau luminescent, et élément luminescent les comprenant

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