WO2022108068A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- WO2022108068A1 WO2022108068A1 PCT/KR2021/012353 KR2021012353W WO2022108068A1 WO 2022108068 A1 WO2022108068 A1 WO 2022108068A1 KR 2021012353 W KR2021012353 W KR 2021012353W WO 2022108068 A1 WO2022108068 A1 WO 2022108068A1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- 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
- C07C211/57—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- 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]
- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
Definitions
- the present specification relates to a compound and an organic light emitting device including the same.
- the electroluminescent device is a type of self-luminous display device, and has advantages of a wide viewing angle, excellent contrast, and fast response speed.
- the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light.
- the organic thin film may be composed of a single layer or multiple layers, if necessary.
- the material of the organic thin film may have a light emitting function if necessary.
- a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used.
- a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.
- An object of the present specification is to provide a compound and an organic light emitting device including the same.
- X is O; S; or CR'R";
- R' and R" are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
- L1, L2, L11 and L12 are each independently, a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
- R11, R12 and Ar are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
- R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
- r is an integer from 0 to 8, and when 2 or more, R1 is the same or different,
- the "substituted or unsubstituted” means deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; And one or more substituents selected from the group consisting of a C2 to C60 heteroaryl group, or two or more substituents selected from the above exemplified substituents are substituted with a connected substituent, or it means unsubstituted.
- the first electrode a second electrode provided to face the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes the compound of Formula 1 above.
- the compound described herein may be used as an organic material layer of an organic light emitting device.
- the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a charge generating material, and the like in an organic light emitting device.
- the compound may be used as a material for a hole transport layer or an electron blocking layer of an organic light emitting device.
- an organic light emitting device having excellent driving voltage and lifespan can be provided.
- the compound of Formula 1 binds a substituent with enhanced hole characteristics to a fluorene skeleton substituted with an amine group, thereby controlling the band gap and T1 value (energy level value of the triplet state) through hole control.
- the unshared electron pair of the amine improves the flow of holes and improves the hole transport ability of the hole transport layer. It may have the effect of providing an organic light emitting device having excellent efficiency by suppressing deterioration.
- the planarity of the compound and the glass transition temperature are increased to have the characteristics of increasing the thermal stability of the compound.
- 1 to 4 are diagrams exemplarily showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present specification.
- substitution means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
- substituted or unsubstituted means deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; And one or more substituents selected from the group consisting of a C2 to C60 heteroaryl group, or two or more substituents selected from the above exemplified substituents are substituted with a connected substituent, or it means unsubstituted.
- "when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that may come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.
- the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen If not, hydrogen and deuterium may be mixed and used in the compound.
- deuterium is one of the isotopes of hydrogen, and as an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2 H.
- isotopes have the same atomic number (Z), but isotopes that have different mass numbers (A) have the same number of protons, but neutrons It can also be interpreted as an element with a different number of (neutron).
- 20% of the content of deuterium in the phenyl group represented by means that the total number of substituents the phenyl group can have is 5 (T1 in the formula), and among them, if the number of deuterium is 1 (T2 in the formula), it will be expressed as 20% can That is, the 20% content of deuterium in the phenyl group may be represented by the following structural formula.
- a phenyl group having a deuterium content of 0% it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.
- the halogen may be fluorine, chlorine, bromine or iodine.
- the alkyl group includes a straight or branched chain, and may be further substituted by other substituents.
- the number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
- Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group
- the alkenyl group includes a straight or branched chain, and may be further substituted by other substituents.
- the carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
- Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, st
- the alkynyl group includes a straight chain or a branched chain, and may be further substituted by other substituents.
- the carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
- the cycloalkyl group includes a monocyclic or polycyclic ring, and may be further substituted by other substituents.
- polycyclic means a group in which a cycloalkyl group is directly connected to another ring group or condensed.
- the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like.
- the carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20.
- the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes monocyclic or polycyclic, and may be further substituted by other substituents.
- polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
- the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
- the heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.
- the aryl group includes a monocyclic or polycyclic ring, and may be further substituted by other substituents.
- polycyclic means a group in which an aryl group is directly connected or condensed with another ring group.
- the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like.
- the aryl group includes a spiro group.
- the carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. When the aryl group is two or more rings, the carbon number may be 8 to 60, 8 to 40, or 8 to 30.
- aryl group examples include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.
- terphenyl group may be selected from the following structures.
- the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
- the heteroaryl group includes O, S, SO 2 , Se, N or Si as a hetero atom, includes monocyclic or polycyclic, and may be further substituted by other substituents.
- the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group.
- the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like.
- the heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.
- the number of carbon atoms may be 4 to 60, 4 to 40, or 4 to 25.
- the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, te
- examples of the aryl group described above may be applied, except that the arylene group is a divalent group.
- heteroaryl group examples of the above-described heteroaryl group may be applied, except that the heteroarylene group is a divalent group.
- X may be O.
- X may be S.
- X is CR'R", R' and R" are each independently a substituted or unsubstituted C1 to C60 alkyl group; Or it may be a substituted or unsubstituted C6 to C60 aryl group.
- X is CR'R", R' and R" are each independently a C1 to C60 alkyl group; Or it may be a C6 to C60 aryl group.
- X is CR'R", R' and R" are each independently a C1 to C30 alkyl group; Or it may be a C6 to C30 aryl group.
- X is CR'R", R' and R" are each independently a C1 to C10 alkyl group; Or it may be a C6 to C10 aryl group.
- X is CR'R", R' and R" are each independently a C1 to C5 alkyl group; Or it may be a C6 to C10 aryl group.
- X is CR'R", R' and R" are each independently a methyl group; or a phenyl group.
- Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3.
- R21 and R22 are each independently a substituted or unsubstituted C1 to C10 alkyl group; Or a substituted or unsubstituted C6 to C20 aryl group,
- R21 and R22 of Formula 1-3 are each independently a substituted or unsubstituted C1 to C5 alkyl group; or a substituted or unsubstituted C6 to C10 aryl group.
- R21 and R22 are each independently a C1 to C5 alkyl group; or a C6 to C10 aryl group.
- R21 and R22 are each independently a methyl group; or a phenyl group.
- L1 and L2 are each independently, a direct bond; Or it may be a C6 to C60 arylene group.
- both L1 and L2 may be a direct bond.
- L1 is a C6 to C60 arylene group
- L2 may be a direct bond
- L1 is a C6 to C30 arylene group
- L2 may be a direct bond
- L1 may be a phenylene group
- L2 may be a direct bond
- L1 may be a direct bond
- L2 may be a C6 to C30 arylene group.
- L1 may be a direct bond
- L2 may be a phenylene group
- L11 and L12 are each independently, a direct bond; Or it may be a C6 to C60 arylene group.
- both L11 and L12 may be a direct bond.
- L11 is a C6 to C60 arylene group
- L12 may be a direct bond
- L11 is a C6 to C30 arylene group
- L12 may be a direct bond
- L11 may be a phenylene group
- L12 may be a direct bond
- L11 and L12 may each independently be a C6 to C60 arylene group.
- L11 and L12 may each independently be a C6 to C30 arylene group.
- L11 and L12 may each independently be a C6 to C10 arylene group.
- both L11 and L12 may be a phenylene group.
- R11 and R12 are each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
- R11 and R12 are each independently a substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
- R11 and R12 are each independently a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
- R11 and R12 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
- R11 and R12 are each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; 9,9'-spirobi[fluorene]; dibenzofuran group; or a dibenzothiophene group.
- R11 is a substituted or unsubstituted C6 to C60 aryl group
- R12 is a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group including O or S.
- R11 is a substituted or unsubstituted C6 to C30 aryl group
- R12 is a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group including O or S.
- R11 is a C6 to C30 aryl group unsubstituted or substituted with an alkyl group or an aryl group
- R12 is a C6 to C30 aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or it may be a C2 to C20 heteroaryl group including O or S.
- R11 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
- R11 is a phenyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; or 9,9'-spirobi[fluorene].
- R12 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
- R12 is a phenyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; 9,9'-spirobi[fluorene]; dibenzofuran group; or a dibenzothiophene group.
- Ar is a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
- Ar is a substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.
- Ar is a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
- Ar is a C6 to C20 aryl group; or a C2 to C20 heteroaryl group.
- Ar is a C6 to C20 aryl group; Or a C2 to C20 heteroaryl group including O or S.
- Ar is a phenyl group; biphenyl group; terphenyl group; naphthyl group; triphenylenyl group; dibenzofuran group; or a dibenzothiophene group.
- Ar is not substituted with an amine group.
- the amine group include -NH 2 ; monoalkylamine group; monoarylamine group; monoheteroarylamine group; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; and an arylheteroarylamine group.
- R1 is hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
- R1 is hydrogen; or deuterium.
- Chemical Formula 1 may be represented by Chemical Formula 2 below.
- Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
- the first electrode a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1 above.
- the first electrode may be an anode
- the second electrode may be a cathode
- the first electrode may be a negative electrode
- the second electrode may be an anode
- the organic light emitting device may be a blue organic light emitting device, and the compound of Formula 1 may be used as a material of the blue organic light emitting device.
- the compound of Formula 1 may be included in the hole transport layer or the electron blocking layer of the blue organic light emitting device.
- the organic light emitting device may be a green organic light emitting device, and the compound of Formula 1 may be used as a material of the green organic light emitting device.
- the compound of Formula 1 may be included in the hole transport layer or the electron blocking layer of the green organic light emitting diode.
- the organic light emitting device may be a red organic light emitting device, and the compound of Formula 1 may be used as a material of the red organic light emitting device.
- the compound of Formula 1 may be included in the hole transport layer or the electron blocking layer of the red organic light emitting device.
- the organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.
- the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
- the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
- the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
- the organic material layer may include a hole transport layer, and the hole transport layer may include the compound of Formula 1 above.
- the organic material layer may include an electron blocking layer, and the electron blocking layer may include the compound of Formula 1 above.
- the organic light emitting device of the present invention may further include one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
- 1 to 4 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present specification.
- the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.
- an organic light-emitting device in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially stacked on a substrate 100 is illustrated.
- an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
- the organic light emitting device according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 304 , an electron transport layer 305 and an electron injection layer 306
- the organic light emitting device according to FIG. 4 is It includes a hole injection layer 301 , a hole transport layer 302 , an electron blocking layer 303 , a light emitting layer 304 , an electron transport layer 305 , and an electron injection layer 306 .
- the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.
- the organic material layer including the compound of Formula 1 may further include other materials as needed.
- materials other than the compound of Formula 1 are exemplified below, but these are for illustration only and not for limiting the scope of the present application, and are known in the art. materials may be substituted.
- anode material Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used.
- the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
- anode material Materials having a relatively low work function may be used as the anode material, and a metal, metal oxide, conductive polymer, or the like may be used.
- the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or Advanced Material, 6, p.677 (1994).
- starburst-type amine derivatives such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4′′-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/Dodecylbenzenesulfonic acid or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor
- a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low molecular weight or high molecular material may be used.
- Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone.
- Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.
- LiF is typically used in the art, but the present application is not limited thereto.
- a red, green, or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as individual sources, or may be premixed and deposited as a single source for use.
- a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material.
- a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used alone, but materials in which a host material and a dopant material together participate in light emission may be used.
- a compound including an anthracene may be used as the host material, but the present disclosure is not limited thereto.
- a pyrene derivative including diamine may be used as the dopant material, but is not limited thereto.
- a host of a light emitting material When a host of a light emitting material is mixed and used, a host of the same type may be mixed and used, or a host of a different type may be mixed and used. For example, any two or more types of an N-type host material or a P-type host material may be selected and used as the host material of the light emitting layer.
- the organic light emitting device may be a top emission type, a back emission type, or a double side emission type according to a material used.
- the compound according to an exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.
- 1-phenylnaphthalen-2-yl trifluoromethanesulfonate (1-phenylnaphthalen-2-yl trifluoromethanesulfonate) (A) (15 g, 0.042 mol, 1eq), (3-chloro-2- (methoxycarbonyl) phenyl ) Boronic acid ((3-chloro-2-(methoxycarbonyl)phenyl)boronic acid) (B) (10g, 0.046mol, 1.1eq), K 2 CO 3 (12.9g, 0.094mol, 2.2eq), Pd(PPh) 3 ) 4 (tetrakis (triphenylphosphine) palladium (0)) (2.4 g, 0.0021 mol, 0.005 eq) was added with 1,4-dioxane (150 ml) and H 2 O (45 ml) and 6 at 100 ° C.
- Table 2 is a measurement value of 1 H NMR (CDCl 3 , 200Mz)
- Table 3 is a measurement value of the FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).
- the transparent electrode indium tin oxide (ITO) thin film obtained from glass for OLED (manufactured by Samsung-Corning) was ultrasonically washed for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then placed in isopropanol and stored. was used.
- the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.
- a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 ⁇ in one cell in the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% compared to the host material thereon.
- lithium fluoride LiF
- Al cathode As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 ⁇ , and an Al cathode was deposited to a thickness of 1,000 ⁇ to fabricate an OLED device.
- all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under 10 -8 to 10 -6 torr for each material and used for OLED manufacturing.
- An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 4 was used instead of the NPB used in forming the hole transport layer in Comparative Example 1.
- electroluminescence (EL) characteristics were measured with M7000 of McScience, and the reference luminance was 6000 cd through the life measuring device (M6000) manufactured by McScience with the measurement result. At /m 2 , T 95 was measured.
- Table 4 shows the results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the blue organic light emitting diode manufactured according to the present invention.
- Example 1 2 4.80 6.60 (0.134, 0.100) 45 Example 2 16 4.78 6.64 (0.134, 0.100) 49 Example 3 42 4.75 6.69 (0.134, 0.100) 47 Example 4 50 4.73 6.70 (0.134, 0.101) 48 Example 5 60 4.79 6.68 (0.134, 0.101) 50 Example 6 138 4.81 6.61 (0.134.
- Example 7 144 4.83 6.63 (0.134, 0.101) 44 Example 8 194 4.78 6.73 (0.134, 0.100) 49 Example 9 202 4.81 6.70 (0.134, 0.100) 49 Example 10 212 4.84 6.68 (0.134, 0.100) 46 Example 11 240 4.79 6.60 (0.134, 0.100) 47 Example 12 256 4.76 6.81 (0.134, 0.101) 49 Example 13 268 4.88 6.74 (0.134, 0.101) 50 Example 14 272 4.83 6.70 (0.134, 0.100) 46 Example 15 277 4.75 6.69 (0.134, 0.100) 44 Example 16 289 4.69 6.68 (0.134, 0.101) 46 Example 17 294 4.82 6.70 (0.134, 0.100) 47 Example 18 340 4.76 6.71 (0.134, 0.100) 45 Example 19 420 4.77 6.68 (0.134, 0.100) 45 Example 20 454 4.80 6.73 (0.134, 0.101) 48 Example 21 464 4.81 6.66 (0.134, 0.100) 49 Example 22 473 4.79 6.68 (0.134, 0.100
- the organic light emitting device using the hole transport layer material of the blue organic light emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to the comparative example.
- the transparent electrode indium tin oxide (ITO) thin film obtained from glass for OLED (manufactured by Samsung-Corning) was ultrasonically washed for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then placed in isopropanol and stored. was used.
- the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.
- a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 ⁇ in one cell in the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% compared to the host material thereon.
- lithium fluoride LiF
- Al cathode As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 ⁇ , and an Al cathode was deposited to a thickness of 1,000 ⁇ to fabricate an OLED device.
- all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under 10 -8 to 10 -6 torr for each material and used for OLED manufacturing.
- electroluminescence (EL) characteristics were measured with M7000 of McScience, and the reference luminance was 6000 cd through the life measuring device (M6000) manufactured by McScience with the measurement result. At /m 2 , T 95 was measured.
- Example 25 2 4.73 6.68 (0.134, 0.100) 49
- Example 26 16 4.75 6.70 (0.134, 0.100) 47
- Example 27 42 4.80 6.74 (0.134, 0.100) 48
- Example 28 50 4.77 6.61 (0.134, 0.101) 49
- Example 29 60 4.76 6.63 (0.134, 0.101) 50
- Example 30 138 4.73 6.69 (0.134, 0.101) 46
- Example 31 144 4.72 6.68 (0.134, 0.101) 46
- Example 32 194 4.76 6.72 (0.134, 0.100) 48
- Example 33 202 4.71 6.80 (0.134, 0.100) 44
- Example 34 212 4.79 6.73 (0.134, 0.100) 47
- Example 35 240 4.70 6.66 (0.134, 0.100) 46
- Example 36 256 4.80 6.69 (0.134, 0.101) 49
- Example 37 268 4.73 6.71 (0.134, 0.101) 50
- Example 38 272 4.80 6.73 (0.134, 0.100) 51
- Example 39 277 4.73
- the organic light-emitting device using the electron blocking layer material of the blue organic light-emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan compared to the comparative example.
- the efficiency and lifespan of the OLED device are reduced.
- a compound having a high LUMO level is used as the electron blocking layer to prevent this phenomenon, electrons passing through the light emitting layer to the anode are blocked by the energy barrier of the electron blocking layer. Therefore, the probability that holes and electrons form excitons increases and the possibility of emission as light from the light emitting layer increases, so it is judged that the compound of the present invention is excellent in all aspects of driving, efficiency, and lifespan.
- the unshared electron pair of the amine can improve hole flow and improve the hole transport ability of the hole transport layer, and when used as an electron blocking layer, the hole transport layer It is possible to suppress the deterioration of the hole transport material caused by the electrons entering into it, and by combining the amine moiety and the substituent with enhanced hole characteristics, the planarity and glass transition temperature of the amine derivative are increased, thereby increasing the thermal conductivity of the compound. It was confirmed that the stability was improved.
- the hole transport ability is improved and the stability of the molecule is also increased through control of the band gap and the T1 value (the energy level of the triplet state), so that the driving voltage of the device is lowered, and the light efficiency is lowered. It was confirmed that the lifetime characteristics of the device were improved by the thermal stability of the compound.
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Abstract
Description
화합물 | 1H NMR(CDCl3, 200Mz) |
2 | δ= 8.55(1H, d), 8.08(1H, d), 7.51(15H, m), 7.20(3H, m), 7.07(1H, t), 6.81(1H, t), 6.69(4H, m) 6.39(1H, d) |
16 | δ= 8.55(1H, d), 8.08(1H, d), 7.87(1H, d), 7.55~7.38(18H, m), 7.28(2H, m), 7.07(1H, t), 6.75(1H, s), 6.69(2H, m), 6.58(1H, d), 6.39(1H, d), 1.72(6H, s) |
42 | δ= 8.55(1H, d), 8.08(1H, d), 7.64(1H, d), 7.51(23H, m), 6.69(4H, m) 6.33(1H, d) |
50 | δ= 8.55(1H, d), 8.08(1H, d), 7.87(2H, d), 7.55(11H, m), 7.38(5H, m), 7.28(2H, m), 6.75(2H, s), 6.58(2H, m) 6.33(1H, d), 1.72(12H, s) |
60 | δ= 8.55(1H, d), 8.08(1H, d), 7.87(2H, d), 7.55~7.38(24H, m), 7.11(4H, m), 6.75(2H, s), 6.58(2H, m), 6.33(1H, d), 1.72(6H, s) |
138 | δ= 8.55(1H, d), 8.08(1H, d), 7.82(2H, m), 7.55~7.41(21H, m), 7.06(1H, s), 6.88(1H, d), 6.69(4H, m) |
144 | δ= 8.55(1H, d), 8.08(1H, d), 7.87(3H, m), 7.62~7.38(17H, m), 7.28(1H, t), 7.06(1H, s), 6.88(1H, d), 6.69(3H, m), 6.58(1H, d), 1.72(6H, s) |
194 | δ= 8.56(1H, d), 8.01(2H, m), 7.84(1H, d), 7.54(14H, m), 7.20(2H, m), 6.81(2H, m), 6.63(5H, m), 1.78(6H, s) |
202 | δ= 8.56(1H, d), 8.01(2H, m), 7.84(1H, d), 7.54(21H, m), 6.81(1H, s), 6.69(5H, m), 1.78(6H, s) |
212 | δ= 8.56(1H, d), 8.01(2H, m), 7.87(2H, m), 7.51(16H, m), 7.25(5H, m), 7.16(1H, t), 6.87(1H, t), 6.81(1H, s), 6.75(1H, s), 6.64(3H, m), 1.78(6H, s), 1.72(6H, s) |
240 | δ= 8.56(1H, d), 8.01(2H, m), 7.87(1H, d), 7.62~7.38(18H, m), 7.28(2H, m), 6.75(1H, s), 6.69(2H, m), 6.58(1H, d), 6.44(1H, d), 1.78(6H, s), 1.72(6H, s) |
256 | δ= 8.56(1H, d), 8.01(2H, m), 7.87(2H, d), 7.75(2H, d), 7.62~7.16(23H, m), 6.75(2H, s), 6.58(2H, d), 6.44(1H, d), 1.78(6H, s), 1.72(6H, s) |
268 | δ= 8.56(1H, d), 8.01(2H, m), 7.84(1H, d), 7.54~7.26(24H, m), 7.08(7H, m), 6.87(1H, t), 6.81(1H, s), 6.64(4H, m) |
272 | δ= 8.56(1H, d), 8.01(2H, m), 7.87(2H, d), 7.55~7.26(24H, m), 7.11(4H, m), 6.81(1H, s), 6.75(1H, s), 6.64(4H, m), 1.72(6H, s) |
277 | δ= 8.56(1H, d), 8.01(2H, m), 7.85(4H, m), 7.66(1H, d), 7.54~7.26(25H, m), 7.11(4H, m), 6.81(1H, s), 6.69(5H, m) |
289 | δ= 8.56(1H, d), 8.01(2H, m), 7.54~7.26(23H, m), 6.81(2H, m), 6.63(4H, m), 6.44(1H, d) |
294 | δ= 8.56(1H, d), 8.01(2H, m), 7.54~7.20(28H, m), 7.11(4H, m), 6.81(1H, t), 6.63(4H, m), 6.44(1H, d) |
340 | δ= 8.55(1H, d), 8.08(1H, d), 7.95(1H, d), 7.75(1H, d), 7.64(1H, s), 7.55~7.38(24H, m), 6.69(6H, m) |
420 | δ= 8.56(1H, d), 8.15(1H, d), 8.01(2H, m), 7.83(1H, s), 7.69(1H, d), 7.55~7.38(23H, m), 6.69(6H, m), 1.78(6H, s) |
454 | δ= 8.55(1H, d), 8.08(1H, d), 7.87(1H, d), 7.55(18H, m), 7.26(6H, m), 7.07(1H, t), 6.75(1H, t), 6.69(2H, d), 6.58(1H, d), 6.39(1H, d), 1.72(6H, s) |
464 | δ= 8.55(1H, d), 8.08(1H, d), 7.87(1H, d), 7.55(20H, m), 7.28(5H, m), 6.75(1H, t), 6.69(2H, d), 6.58(1H, d), 6.33(1H, d), 1.72(6H, s) |
473 | δ= 8.56(1H, d), 8.01(2H, m), 7.87(2H, d), 7.55(10H, m), 7.28(7H, m), 6.75(3H, m), 6.63(4H, m), 1.78(6H, s), 1.72(6H, s) |
483 | δ= 8.55(1H, d), 8.00(5H, d), 7.73(1H, d), 7.59(7H, m), 7.38(2H, m), 7.20(4H, m), 7.07(1H, t), 6.75(2H, m), 6.63(3H, m), 6.39(1H, d), 1.72(6H, s) |
495 | δ= 8.55(1H, d), 8.08(1H, d), 8.00(2H, m), 7.87(3H, m), 7.73(1H, d), 7.55(10H, m), 7.38(4H, m), 7.28(2H, m), 6.75(2H, s), 6.58(2H, m), 6.33(1H, d), 1.72(12H, s) |
화합물 | FD-MS | 화합물 | FD-MS |
2 | m/z= 537.21 | 16 | m/z= 653.27 |
42 | m/z= 613.24 | 50 | m/z= 693.30 |
60 | m/z= 817.33 | 138 | m/z= 629.22 |
144 | m/z= 669.25 | 194 | m/z= 563.26 |
202 | m/z= 639.29 | 212 | m/z= 755.36 |
240 | m/z= 679.32 | 256 | m/z= 841.37 |
268 | m/z= 763.32 | 272 | m/z= 803.36 |
277 | m/z= 853.33 | 289 | m/z= 611.26 |
294 | m/z= 763.32 | 340 | m/z= 689.27 |
420 | m/z= 715.32 | 454 | m/z= 729.30 |
464 | m/z= 729.30 | 473 | m/z= 679.32 |
483 | m/z= 627.26 | 495 | m/z= 743.32 |
화합물 | 구동전압 (V) |
발광효율 (cd/A) |
CIE (x, y) |
수명 (T95) |
|
실시예 1 | 2 | 4.80 | 6.60 | (0.134, 0.100) | 45 |
실시예 2 | 16 | 4.78 | 6.64 | (0.134, 0.100) | 49 |
실시예 3 | 42 | 4.75 | 6.69 | (0.134, 0.100) | 47 |
실시예 4 | 50 | 4.73 | 6.70 | (0.134, 0.101) | 48 |
실시예 5 | 60 | 4.79 | 6.68 | (0.134, 0.101) | 50 |
실시예 6 | 138 | 4.81 | 6.61 | (0.134. 0.101) | 45 |
실시예 7 | 144 | 4.83 | 6.63 | (0.134, 0.101) | 44 |
실시예 8 | 194 | 4.78 | 6.73 | (0.134, 0.100) | 49 |
실시예 9 | 202 | 4.81 | 6.70 | (0.134, 0.100) | 49 |
실시예 10 | 212 | 4.84 | 6.68 | (0.134, 0.100) | 46 |
실시예 11 | 240 | 4.79 | 6.60 | (0.134, 0.100) | 47 |
실시예 12 | 256 | 4.76 | 6.81 | (0.134, 0.101) | 49 |
실시예 13 | 268 | 4.88 | 6.74 | (0.134, 0.101) | 50 |
실시예 14 | 272 | 4.83 | 6.70 | (0.134, 0.100) | 46 |
실시예 15 | 277 | 4.75 | 6.69 | (0.134, 0.100) | 44 |
실시예 16 | 289 | 4.69 | 6.68 | (0.134, 0.101) | 46 |
실시예 17 | 294 | 4.82 | 6.70 | (0.134, 0.100) | 47 |
실시예 18 | 340 | 4.76 | 6.71 | (0.134, 0.100) | 45 |
실시예 19 | 420 | 4.77 | 6.68 | (0.134, 0.100) | 45 |
실시예 20 | 454 | 4.80 | 6.73 | (0.134, 0.101) | 48 |
실시예 21 | 464 | 4.81 | 6.66 | (0.134, 0.100) | 49 |
실시예 22 | 473 | 4.79 | 6.68 | (0.134, 0.100) | 47 |
실시예 23 | 483 | 4.78 | 6.51 | (0.134, 0.100) | 45 |
실시예 24 | 495 | 4.77 | 6.69 | (0.134, 0.101) | 48 |
비교예 1 | NPB | 5.40 | 6.16 | (0.134, 0.101) | 37 |
비교예 2 | HT1 | 5.22 | 6.24 | (0.134, 0.101) | 36 |
비교예 3 | HT2 | 5.19 | 6.21 | (0.134, 0.100) | 35 |
비교예 4 | HT3 | 5.17 | 6.20 | (0.134, 0.100) | 38 |
비교예 5 | HT4 | 5.19 | 6.19 | (0.134, 0.101) | 35 |
비교예 6 | HT5 | 5.21 | 6.23 | (0.134, 0.100) | 38 |
비교예 7 | HT6 | 5.22 | 6.25 | (0.134, 0.100) | 39 |
화합물 | 구동전압 (V) |
발광효율 (cd/A) |
CIE (x, y) |
수명 (T95) |
|
실시예 25 | 2 | 4.73 | 6.68 | (0.134, 0.100) | 49 |
실시예 26 | 16 | 4.75 | 6.70 | (0.134, 0.100) | 47 |
실시예 27 | 42 | 4.80 | 6.74 | (0.134, 0.100) | 48 |
실시예 28 | 50 | 4.77 | 6.61 | (0.134, 0.101) | 49 |
실시예 29 | 60 | 4.76 | 6.63 | (0.134, 0.101) | 50 |
실시예 30 | 138 | 4.73 | 6.69 | (0.134, 0.101) | 46 |
실시예 31 | 144 | 4.72 | 6.68 | (0.134, 0.101) | 46 |
실시예 32 | 194 | 4.76 | 6.72 | (0.134, 0.100) | 48 |
실시예 33 | 202 | 4.71 | 6.80 | (0.134, 0.100) | 44 |
실시예 34 | 212 | 4.79 | 6.73 | (0.134, 0.100) | 47 |
실시예 35 | 240 | 4.70 | 6.66 | (0.134, 0.100) | 46 |
실시예 36 | 256 | 4.80 | 6.69 | (0.134, 0.101) | 49 |
실시예 37 | 268 | 4.73 | 6.71 | (0.134, 0.101) | 50 |
실시예 38 | 272 | 4.80 | 6.73 | (0.134, 0.100) | 51 |
실시예 39 | 277 | 4.73 | 6.69 | (0.134, 0.101) | 47 |
실시예 40 | 289 | 4.71 | 6.75 | (0.134, 0.100) | 45 |
실시예 41 | 294 | 4.77 | 6.80 | (0.134, 0.100) | 49 |
실시예 42 | 340 | 4.70 | 6.77 | (0.134, 0.100) | 48 |
실시예 43 | 420 | 4.70 | 6.69 | (0.134, 0.100) | 47 |
실시예 44 | 454 | 4.72 | 6.68 | (0.134, 0.101) | 49 |
실시예 45 | 464 | 4.70 | 6.69 | (0.134, 0.101) | 46 |
실시예 46 | 473 | 4.73 | 6.71 | (0.134, 0.100) | 49 |
실시예 47 | 483 | 4.77 | 6.70 | (0.134, 0.100) | 48 |
실시예 48 | 495 | 4.75 | 6.74 | (0.134, 0.100) | 47 |
비교예 8 | NPB | 5.31 | 6.11 | (0.134, 0.101) | 36 |
비교예 9 | HT1 | 5.36 | 6.14 | (0.134, 0.100) | 35 |
비교예 10 | HT2 | 5.30 | 6.18 | (0.134, 0.100) | 36 |
비교예 11 | HT3 | 5.33 | 6.16 | (0.134, 0.100) | 37 |
비교예 12 | HT4 | 5.30 | 6.10 | (0.134, 0.100) | 36 |
비교예 13 | HT5 | 5.34 | 6.20 | (0.134, 0.101) | 37 |
비교예 14 | HT6 | 5.29 | 6.22 | (0.134, 0.101) | 38 |
Claims (9)
- 하기 화학식 1의 화합물:[화학식 1]상기 화학식 1에 있어서,X는 O; S; 또는 CR'R"이고,R' 및 R"는 각각 독립적으로, 치환 또는 비치환된 C1 내지 C60의 알킬기; 치환 또는 비치환된 C6 내지 C60의 아릴기; 또는 치환 또는 비치환된 C2 내지 C60의 헤테로아릴기이며,L1, L2, L11 및 L12는 각각 독립적으로, 직접결합; 치환 또는 비치환된 C6 내지 C60의 아릴렌기; 또는 치환 또는 비치환된 C2 내지 C60의 헤테로아릴렌기이고,R11, R12 및 Ar은 각각 독립적으로, 치환 또는 비치환된 C1 내지 C60의 알킬기; 치환 또는 비치환된 C3 내지 C60의 시클로알킬기; 치환 또는 비치환된 C6 내지 C60의 아릴기; 또는 치환 또는 비치환된 C2 내지 C60의 헤테로아릴기이며,R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 C1 내지 C60의 알킬기; 치환 또는 비치환된 C3 내지 C60의 시클로알킬기; 치환 또는 비치환된 C6 내지 C60의 아릴기; 또는 치환 또는 비치환된 C2 내지 C60의 헤테로아릴기이며,r은 0 내지 8의 정수이고, 2 이상인 경우 R1은 같거나 상이하고,상기"치환 또는 비치환"이란 중수소; 할로겐기; 시아노기; C1 내지 C60의 알킬기; C2 내지 C60의 알케닐기; C2 내지 C60의 알키닐기; C3 내지 C60의 시클로알킬기; C2 내지 C60의 헤테로시클로알킬기; C6 내지 C60의 아릴기; 및 C2 내지 C60의 헤테로아릴기로 이루어진 군으로부터 선택된 1 이상의 치환기, 또는 상기 예시된 치환기 중에서 선택된 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 비치환된 것을 의미한다.
- 청구항 1에 있어서,상기 Ar은 C6 내지 C20의 아릴기; 또는 C2 내지 C20의 헤테로아릴기인 것인 화합물.
- 청구항 1에 있어서,상기 R11은 치환 또는 비치환된 C6 내지 C60의 아릴기이고,상기 R12는 치환 또는 비치환된 C6 내지 C60의 아릴기; 또는 치환 또는 비치환되고 O 또는 S를 포함하는 C2 내지 C60의 헤테로아릴기인 것인 화합물.
- 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 유기물층을 포함하는 유기 발광 소자로서,상기 유기물층은 청구항 1 내지 6 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 7에 있어서,상기 유기물층은 정공 수송층을 포함하고,상기 정공 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 7에 있어서,상기 유기물층은 전자 저지층을 포함하고,상기 전자 저지층은 상기 화합물을 포함하는 것인 유기 발광 소자.
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CN202180075604.0A CN116529245A (zh) | 2020-11-19 | 2021-09-10 | 化合物以及包括其的有机发光元件 |
US18/032,221 US20230391740A1 (en) | 2020-11-19 | 2021-09-10 | Compound and organic light-emitting device comprising same |
EP21894841.2A EP4249477A1 (en) | 2020-11-19 | 2021-09-10 | Compound and organic light-emitting device comprising same |
JP2023523067A JP2023550882A (ja) | 2020-11-19 | 2021-09-10 | 化合物およびそれを含む有機発光素子 |
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KR1020200155675A KR102531630B1 (ko) | 2020-11-19 | 2020-11-19 | 화합물 및 이를 포함하는 유기 발광 소자 |
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CN104672126A (zh) * | 2014-12-31 | 2015-06-03 | 北京鼎材科技有限公司 | 一种苯并萘并五元杂环衍生物及其应用 |
KR20150066202A (ko) * | 2013-12-06 | 2015-06-16 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20170124957A (ko) * | 2016-05-03 | 2017-11-13 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN110317195A (zh) * | 2018-03-29 | 2019-10-11 | 北京鼎材科技有限公司 | 有机化合物及其在有机电致发光器件中的应用 |
WO2020231197A1 (ko) * | 2019-05-14 | 2020-11-19 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치 |
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KR20200127628A (ko) * | 2019-05-03 | 2020-11-11 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치 |
-
2020
- 2020-11-19 KR KR1020200155675A patent/KR102531630B1/ko active IP Right Grant
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- 2021-09-10 EP EP21894841.2A patent/EP4249477A1/en active Pending
- 2021-09-10 CN CN202180075604.0A patent/CN116529245A/zh active Pending
- 2021-09-10 JP JP2023523067A patent/JP2023550882A/ja active Pending
- 2021-09-10 US US18/032,221 patent/US20230391740A1/en active Pending
- 2021-09-28 TW TW110135924A patent/TW202229509A/zh unknown
Patent Citations (6)
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US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
KR20150066202A (ko) * | 2013-12-06 | 2015-06-16 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN104672126A (zh) * | 2014-12-31 | 2015-06-03 | 北京鼎材科技有限公司 | 一种苯并萘并五元杂环衍生物及其应用 |
KR20170124957A (ko) * | 2016-05-03 | 2017-11-13 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN110317195A (zh) * | 2018-03-29 | 2019-10-11 | 北京鼎材科技有限公司 | 有机化合物及其在有机电致发光器件中的应用 |
WO2020231197A1 (ko) * | 2019-05-14 | 2020-11-19 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치 |
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CN116529245A (zh) | 2023-08-01 |
US20230391740A1 (en) | 2023-12-07 |
EP4249477A1 (en) | 2023-09-27 |
TW202229509A (zh) | 2022-08-01 |
JP2023550882A (ja) | 2023-12-06 |
KR20220069165A (ko) | 2022-05-27 |
KR102531630B1 (ko) | 2023-05-15 |
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