WO2016108596A2 - Novel compound and organic light-emitting device comprising same - Google Patents
Novel compound and organic light-emitting device comprising same Download PDFInfo
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- WO2016108596A2 WO2016108596A2 PCT/KR2015/014444 KR2015014444W WO2016108596A2 WO 2016108596 A2 WO2016108596 A2 WO 2016108596A2 KR 2015014444 W KR2015014444 W KR 2015014444W WO 2016108596 A2 WO2016108596 A2 WO 2016108596A2
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- formula
- light emitting
- halogen
- deuterium
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- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H—ELECTRICITY
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
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- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/20—Delayed fluorescence emission
- H10K2101/25—Delayed fluorescence emission using exciplex
Definitions
- the present invention relates to a novel compound and an organic light emitting device comprising the same.
- the present invention relates to an organic light emitting device that maximizes efficiency and lifetime by appropriately adjusting the exciplex wavelength by using the compound and a carbazole derivative as a host.
- an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
- LCD liquid crystal display
- the material used as the organic material layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
- the light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. According to the emission color can be divided into blue, green, red light emitting material and yellow and orange light emitting material required to implement a better natural color.
- a host / dopant system may be used as a light emitting material.
- the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.
- the present invention can be used as a light emitting host, an electron injection material, an electron transport material or a hole suppression material in the organic light emitting device, when applied to the organic light emitting device, long life, high efficiency, low voltage, high Tg,
- the purpose of the present invention is to provide a compound that can secure the stability of the thin film and, in particular, maximize the efficiency and lifespan of the organic light emitting device through the formation of exciplex and energy transfer into the dopant.
- the present invention has a long life, high efficiency, low voltage, high Tg, thin film stability including the compound, in particular to provide an organic light emitting device that maximizes efficiency and life through the formation of exciplex and energy transfer to dopant. do.
- Each X is independently N or CR 0 , at least two of X are N, wherein R 0 is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
- Y is O or S
- R 1 , R 2 and R 3 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alky
- n are each independently an integer of 0-2.
- the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
- the compound of the present invention and the organic light emitting device to which the compound is applied have the following characteristics.
- Fused ring in compound enables high Tg formation and improves thin film stability when driving organic light emitting device.
- FIG. 1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.
- the compound of the present invention is represented by the following formula (1).
- Each X is independently N or CR 0 , at least two of X are N, wherein R 0 is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
- Y is O or S
- R 1 , R 2 and R 3 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alky
- n and n are each independently an integer of 0 to 2, and specifically m and n are 1.
- the compound represented by Chemical Formula 1 may be one of those represented by the following Chemical Formulas 1-1 to 1-6.
- the compound of Formula 1 according to the present invention has excellent electron transport characteristics, excellent luminous efficiency, high color purity, high efficiency and long life, and thus can exhibit excellent device characteristics when applied to an organic light emitting device.
- the compound of Formula 1 has an LUMO energy level for easy electron injection, excellent electron transport characteristics, and excellent stability and long life due to low voltage, high efficiency, and high Tg when the light emitting layer and the electron transport layer of the organic light emitting device are applied. have.
- the compounds of the present invention can be prepared through the reaction scheme represented by any one of the following schemes 1-3.
- X and Y in the scheme are as defined in formula (1).
- the present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer.
- the compound of the present invention may be specifically used as a light emitting host, an electron injection material, an electron transport material or a hole suppression material, or may be used together with a known compound. More specifically, the compound of the present invention is used as a light emitting host, wherein the light emitting compound represented by the following formula (2) (light emitting host 2) is combined with the compound represented by the formula (1) of the present invention (light emitting host 1). It is good to use as.
- r 1 to r 8 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkyl group
- Ar is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 C 6-50 aryl group which is unsubstituted or substituted with an aryloxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
- n 1 to 4
- Ar and r 1 -r 8 may be connected to each other.
- the compound of Formula 2 may be any one of the compounds represented by the following Formulas 2-1 to 2-7.
- Ar 1 , Ar 2 , Ar 3 , Ar 4, Ar 5 in the formulas are each independently the same as the definition of Ar of Formula 2,
- R 1 , R 2 , R 3 , and R 4 are the same as defined in r 1 to r 8 of Chemical Formula 2,
- a and b are the integers of 0-3 each independently.
- the compound of Chemical Formula 2 may be a compound represented by Chemical Formula 2-3, and in this case, the homogeneity may be higher by including a structure substituted between carbazolephenyl moieties included in the chemical formula, and hole injection may be higher. It becomes easy and can lower a drive voltage.
- the mixing ratio of Chemical Formula 1 and Chemical Formula 2 may be 9: 1 to 2: 8 by weight.
- the driving voltage of the organic light emitting device may be low, resulting in high efficiency and long life.
- hole injection and transport may be excessive, thereby reducing efficiency and lifespan. .
- a flex eksi emission wavelength is formed through the first and second light emitting host in the present invention can be formed into 400-650 nm, by the selection of the light emitting host 1 and 2 to form a flex eksi wavelength of 450-500 nm green organic It can be used in a light emitting device, and can be used in a red organic light emitting device by forming an exciplex wavelength of 500-630 nm.
- the exciplex wavelength formed by the combination of the light emitting hosts may be formed at a shorter wavelength than that of the dopant which is a guest of the light emitting layer. This allows the energy transfer to be efficiently absorbed by the phosphor dopant absorbing the exciplex wavelength by the light emitting host combination to maximize efficiency and long life.
- the organic light emitting device of the present invention can manufacture an organic light emitting device using a known method of manufacturing an organic light emitting device, except that the organic light emitting device including at least one layer containing the compound represented by the formula (1), an example Referring to the manufacturing method of the organic light emitting device as follows.
- the organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between an anode and a cathode. It may contain one or more.
- HIL hole injection layer
- HTL hole transport layer
- EML emission layer
- ETL electron transport layer
- EIL electron injection layer
- an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
- the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
- the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
- the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
- the hole injection layer material may be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB).
- a well-known hole injection layer material may be used.
- TCTA 4,4 ', 4 "
- TCTA which is a phthalocyanine compound or a starburst type amine derivative such as copper phthalocyanine disclosed in US Pat. No. 4,356,429, may be used.
- the hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, or the like.
- the hole transport layer material a known hole transport layer material may be used.
- the known hole transport layer material includes carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1, Having an aromatic condensed ring such as 1-biphenyl] -4,4'-diamine (TPD) and N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Conventional amine derivatives and the like can be used.
- carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole
- the light emitting layer material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, cast, LB, or the like.
- a method such as vacuum deposition, spin coating, cast, LB, or the like.
- the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer.
- the light emitting layer material may be a known host or dopant, it is preferable to use the compound represented by the formula (1) of the present invention as a host, specifically, the compound represented by the formula (1) of the present invention (light emitting host 1) And the compound represented by the formula (2) (light emitting host 2) is preferably used at the same time, more specifically, the compound represented by the formula (1) (luminescent host 1) and the compound represented by the formula 2-3 (light emitting host 2) at the same time It is good to use.
- the light emitting host has an exciplex wavelength formed by a combination of the compound represented by Chemical Formula 1 (light emitting host 1) and the compound represented by Chemical Formula 2 (light emitting host 2) at a wavelength shorter than that of the dopant of the light emitting layer. It is advisable to select and use a dopant material.
- Fluorescent dopants that can be used include IDE102 or IDE105, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethyrylcrissen-, available from Idemitsu.
- 6,12-diamine can be used as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate), a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
- Ir (ppy) 3 tris (2-phenylpyridine) iridium
- blue phosphorescent dopant F2Irpic iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate
- RD61 red phosphorescent dopant from UDC
- a light emitting auxiliary layer may be further included between the hole transport layer and the light emitting layer, and known materials may be used as the light emitting auxiliary layer material.
- the hole suppressing material may be further laminated by a vacuum deposition method or a spin coating method.
- the hole-inhibiting substance that can be used may be used alone or in combination by selecting any of the compounds represented by the formula (1) or known materials used as the hole-inhibiting material.
- known materials include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and hole suppression materials described in Japanese Patent Laid-Open No. 11-329734 (A1).
- 8-hydroxy-2-methylquinolinolato) -aluminum biphenoxide a phenanthrolines-based compound (e.g., BDC (vasocuproin) from UDC) can be used.
- An electron transport layer is formed on the light emitting layer formed as above, wherein the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.
- the electron transport layer material may be a compound represented by Formula 1 or a known material, and examples of the known material include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3 ), or ET4 (6). , 6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine) can be used.
- an electron injection layer which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and as the electron injection layer material, the compound represented by Chemical Formula 1 or LiF, NaCl, Materials such as CsF, Li 2 O, BaO and the like can be used.
- the cathode forming metal is formed on the electron transport layer or the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode.
- the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
- a transmissive cathode using ITO or IZO may be used to obtain the front light emitting device.
- the organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.
- each organic material layer formed according to the present invention as described above can be adjusted according to the required degree, specifically 10 to 1,000 nm, more preferably 20 to 150 nm.
- the present invention has an advantage that the organic material layer including the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.
- the organic light emitting device of the present invention is excellent in durability against electrons and holes to ensure long life, low voltage driving and high efficiency of the organic light emitting device, excellent thin film stability, novel compounds of the present invention (light emitting host 1) and the cover
- the sol derivative (luminescent host 2) facilitates electron injection and transport, enables low voltage driving and high efficiency, and maximizes efficiency through exciplex formation and energy transfer to dopant, enabling high efficiency and long life. Can be.
- Compound 1-2 was synthesized using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1. %)
- Compound 1-3 was synthesized using 2-chloro-4,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1. %)
- Compound 1-6 was prepared using intermediate I2 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1. (60% yield).
- Compound 1-8 was synthesized by using intermediate I4 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of intermediate I1 and 2-bromotriphenylene in the same manner as Compound 1-1. %)
- Compound 1-11 was prepared by using intermediate I5 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1. (62% yield).
- Compound 1-13 was prepared using intermediate I6 and 4-chloro-2,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1. (60% yield).
- Compound 1-16 was synthesized using intermediates I8 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of intermediates I1 and 2-bromotriphenylene in the same manner as Compound 1-1. %)
- An organic light emitting device was manufactured according to the structure of FIG. 1.
- the organic light emitting device is in order from the bottom of the anode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transport layer 15 / cathode (electron injection electrode 16) Are stacked.
- the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of the Examples and Comparative Examples used the following materials.
- the energy formed by the exciplex is deposited on the glass substrate to host 1 / host 2 (1: 1) to find a combination of host 1 and host 2 for efficient energy transfer to phosphorescent dopant.
- the exciplex wavelength was measured and the results are shown in Table 1 below.
- Host1 Host2 Host 1 Host 2 compound T1 (eV) compound T1 (eV) Exciplex (nm) Combination Example 1 1-1 2.54 2-1 2.87 460 Combination Example 2 1-1 2.54 2-2 2.81 467 Combination Example 3 1-1 2.54 2-3 2.76 483 Combination Example 4 1-1 2.54 2-4 2.76 491 Combination Example 5 1-1 2.54 2-5 2.84 468 Combination Example 6 1-2 2.57 2-3 2.76 473 Combination Example 7 1-3 2.57 2-3 2.76 472 Combination Example 8 1-4 2.55 2-3 2.76 480 Combination Example 9 1-5 2.57 2-3 2.76 472 Combination Example 10 1-6 2.57 2-3 2.76 470 Combination Example 11 1-7 2.55 2-3 2.76 481 Combination Example 12 1-8 2.52 2-3 2.76 489 Combination Example 13 1-9 2.54 2-3 2.76 482 Combination Example 14 1-10 2.56 2-3 2.76 473 Combination Example 15 1-11 2.56 2-3 2.76 473 Combination Example 16 1-12 2.56 2-3 2.76 480 Combination Example 14
- ITO 1500 ⁇ thick thin glass substrate was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using oxygen plasma.
- NPB 250 ⁇ was formed into a hole injection layer HI01 600 ⁇ and a hole transport layer.
- the light emitting layer was doped with 10% of Compound 1-1 / Ir (ppy) 3 to form 300 ⁇ .
- a green organic light emitting diode was manufactured according to the same method as Example 1 except that Compound 1-2 was used instead of Compound 1-1 as the emission layer host.
- a green organic light emitting diode was manufactured according to the same method as Example 1-1 except that Compound 1-4 was used instead of Compound 1-1 as the emission layer host.
- a green organic light emitting diode was manufactured according to the same method as Example 1-1 except that Compound 1-8 was used instead of Compound 1-1 as the emission layer host.
- a green organic light emitting diode was manufactured according to the same method as Example 1-1 except that Compound 1-11 was used instead of Compound 1-1 as the emission layer host.
- ITO 1500 ⁇ thick thin glass substrate was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using oxygen plasma.
- NPB 250 ⁇ was formed into a hole injection layer HI01 600 ⁇ and a hole transport layer.
- the light emitting layer was doped with 10% of Compound 1-1: Compound 2-3 (6: 4w%) mixture / Ir (ppy) 3 to form 300 ⁇ .
- a green organic light emitting diode formed by using a mixture of Compound 1-2-1 to Compound 1-3 (6: 4w%) instead of Compound 1-1: Compound 2-3 as a light emitting layer host in the same manner as in Example 6. was produced.
- a green organic light emitting diode was manufactured according to the same method as CBP except that CBP was used as a light emitting layer host.
- a green organic light emitting diode was manufactured according to the same method as Ref. 1 except that Ref. 1 was used as the light emitting layer host.
- a green organic light emitting diode was manufactured according to the same method as Ref. 2 except for using the light emitting layer host of Example 1.
- a green organic light emitting diode was manufactured according to the same method as Ref. 3 except that Ref. 3 was used as the light emitting layer host.
- Example 1 4.31 17.31 44.68 35.31 0.301 0.621 55
- Example 2 4.50 17.19 43.21 35.03 0.301 0.619 52
- Example 3 4.31 17.30 44.88 35.22 0.300 0.620 50
- Example 4 4.32 17.33 44.81 35.51 0.300 0.622 55
- Example 5 4.30 17.35 44.21 35.99 0.299 0.620 54
- Example 6 3.98 18.20 54.02 43.24 0.300 0.619 83
- Example 7 4.05 18.11 53.01 41.12 0.300 0.618 72
- Example 8 4.00 18.25 53.65 40.01 0.302 0.619 72
- Example 9 3.98 18.10 54.18 43.12 0.300 0.620
- Example 10 4.02 18.12 53.25 43.91 0.300 0.623 75
- Example 11 4.03 18.06 53.11 40.00 0.301 0.622 81
- Example 12 4.09 53.92 43.91 0.301 0.620 74
- Example 13 4.03
- the embodiments of the present invention can confirm that the driving voltage is lower than the Comparative Examples 1 to 4 and have a high efficiency and a long life, it can be seen that the physical properties are excellent in all aspects.
- Examples of the present invention have a linkage of dibenzofuran and dibenzothiophene to triphenylene in comparison with Comparative Examples 2 to 4, and heteroaromatic is added to facilitate electron injection and transport, thereby lowering driving voltage and efficiency. And it turns out that a lifetime rises.
- the host 2 compound which is easy to inject and transport holes, it can be seen that the driving voltage is further lowered and the durability is long even at high current density.
- Examples 22 to 25 and Reference Example 1 inject electrons and holes by applying a voltage to a Keithley 2400 source measurement unit and use a Konica Minolta spectrophotometer (CS-2000). By measuring the luminance when the light is emitted by using the, the performance of the organic light emitting diodes of the Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 3. .
- the compound of the present invention and the organic light emitting device to which the compound is applied have the following characteristics.
- Fused ring in compound enables high Tg formation and improves thin film stability when driving organic light emitting device.
Abstract
A novel compound of the present invention is applicable to a light-emitting layer, an electron injection layer, an electron transport layer, or a hole suppression layer of an organic light-emitting device. By using the novel compound of the present invention and carbazole derivatives together as a host of the organic light-emitting device, an exciplex wavelength is properly controlled and thus the efficiency and lifespan of the organic light-emitting device can be maximized.
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기발광소자에 관한 것이다. 또한 본 발명은 상기 화합물과 카바졸 유도체를 호스트로 같이 사용함으로써 엑시플렉시 파장을 적절히 조절하여 효율 및 수명을 극대화 시킨 유기발광소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same. In addition, the present invention relates to an organic light emitting device that maximizes efficiency and lifetime by appropriately adjusting the exciplex wavelength by using the compound and a carbazole derivative as a host.
최근, 자체 발광형으로 저전압 구동이 가능한 유기발광소자는, 평판 표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어, 차세대 표시소자로서 주목을 받고 있다.Recently, an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices. In terms of power consumption and wide color reproduction range, it is attracting attention as a next-generation display device.
유기발광소자에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광 재료, 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. The material used as the organic material layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
상기 발광 재료는 분자량에 따라 고분자과 저분자로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있으며, 발광 재료는 발광 색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. The light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. According to the emission color can be divided into blue, green, red light emitting material and yellow and orange light emitting material required to implement a better natural color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.
현재까지 이러한 유기발광소자에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. To date, various compounds are known as materials used in such organic light emitting diodes, but in the case of organic light emitting diodes using materials known to date, there are many difficulties in practical use due to high driving voltage, low efficiency, and short lifespan.
따라서, 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다. Therefore, efforts have been made to develop organic light emitting devices having low voltage driving, high brightness and long life using materials having excellent properties.
상기와 같은 문제점을 해결하기 위해, 본 발명은 유기발광소자에 발광호스트, 전자주입재료, 전자수송재료 또는 정공억제재료로 사용가능하며, 유기발광소자에 적용시 장수명, 고효율, 저전압, 높은 Tg, 박막 안정성을 확보할 수 있으며, 특히 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 유기발광소자의 효율 및 수명을 극대화 할 수 있는 화합물을 제공하는 것을 목적으로 한다. In order to solve the above problems, the present invention can be used as a light emitting host, an electron injection material, an electron transport material or a hole suppression material in the organic light emitting device, when applied to the organic light emitting device, long life, high efficiency, low voltage, high Tg, The purpose of the present invention is to provide a compound that can secure the stability of the thin film and, in particular, maximize the efficiency and lifespan of the organic light emitting device through the formation of exciplex and energy transfer into the dopant.
또한 본 발명은 상기 화합물을 포함하여 장수명, 고효율, 저전압, 높은 Tg, 박막 안정성을 가지며, 특히 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 및 수명을 극대화 한 유기발광소자를 제공하는 것을 목적으로 한다.In addition, the present invention has a long life, high efficiency, low voltage, high Tg, thin film stability including the compound, in particular to provide an organic light emitting device that maximizes efficiency and life through the formation of exciplex and energy transfer to dopant. do.
상기 목적을 달성하기 위해 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:
[화학식 1][Formula 1]
상기 식에서,Where
X는 각각 독립적으로 N 또는 CR0이며, X중 적어도 2개는 N이며, 여기서 R0은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,Each X is independently N or CR 0 , at least two of X are N, wherein R 0 is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
Y는 O 또는 S이며,Y is O or S,
R1, R2 및 R3는 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며,R 1 , R 2 and R 3 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
m, n은 각각 독립적으로 0 내지 2의 정수이다.m and n are each independently an integer of 0-2.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기발광소자를 제공한다.In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
본 발명의 화합물과 상기 화합물을 적용한 유기발광소자는 다음의 특징을 가진다.The compound of the present invention and the organic light emitting device to which the compound is applied have the following characteristics.
1. 화합물 내의 트리페닐렌 구조의 도입으로 전자 및 정공에 대한 내구성 우수하여 유기발광소자의 장수명 확보.1. The long life of organic light emitting device is secured by the introduction of triphenylene structure in the compound.
2. 그린인광호스트로 적합한 삼중항 에너지 유지하여 유기발광소자의 고효율 확보.2. Securing high efficiency of organic light emitting device by maintaining triple energy suitable as green phosphorescent host.
3. 화합물 내에 헤테로아릴기 도입으로 전자주입 및 수송 용이함으로써 유기발광소자의 저전압 구동 및 고효율 확보.3. Low voltage driving and high efficiency of organic light emitting device by easy injecting and transporting electrons by introducing heteroaryl group into compound.
4. 화합물 내 Fused ring으로 높은 Tg 형성을 가능하게 하고, 유기발광소자 구동시 박막 안정성을 향상시킴.4. Fused ring in compound enables high Tg formation and improves thin film stability when driving organic light emitting device.
5. 유기발광소자에 적용시 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)를 이용하여, 정공주입, 전자주입 및 수송이 용이하게 하고, 저전압 구동, 고효율을 가능하게 함.5. When applied to an organic light emitting device, by using the novel compound (luminescent host 1) and carbazole derivative (luminescent host 2) of the present invention, hole injection, electron injection and transport are easy, low voltage driving and high efficiency are possible. Let it be.
6. 유기발광소자에 적용시 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)의 사용을 통하여 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 극대화시켜, 고효율 장수명을 가능하게 함.6. When applied to an organic light emitting device, through the use of the novel compound (light emitting host 1) and carbazole derivatives (light emitting host 2) of the present invention to maximize the efficiency through the formation of exciplex and energy transfer to dopant, high efficiency long life Make it possible.
도 1은 본 발명의 일 실시예에 따른 OLED의 단면을 개략적으로 도시한 것이다.1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.
도면의 부호Sign of drawing
10 : 기판10: substrate
11 : 양극11: anode
12 : 정공주입층12: hole injection layer
13 : 정공수송층13: hole transport layer
14 : 발광층14: light emitting layer
15 : 전자수송층15: electron transport layer
16: 음극16: cathode
본 발명의 화합물은 하기 화학식 1로 표시된다.The compound of the present invention is represented by the following formula (1).
[화학식 1][Formula 1]
상기 식에서,Where
X는 각각 독립적으로 N 또는 CR0이며, X중 적어도 2개는 N이며, 여기서 R0은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,Each X is independently N or CR 0 , at least two of X are N, wherein R 0 is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
Y는 O 또는 S이며,Y is O or S,
R1, R2 및 R3는 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며,R 1 , R 2 and R 3 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
m, n은 각각 독립적으로 0 내지 2의 정수이며, 구체적으로는 m 및 n은 1이다.m and n are each independently an integer of 0 to 2, and specifically m and n are 1.
본 발명에 있어서, 상기 화학식 1로 표시되는 화합물은 구체적으로 하기 화학식 1-1 내지 1-6으로 표시되는 것 중 하나일 수 있다.In the present invention, the compound represented by Chemical Formula 1 may be one of those represented by the following Chemical Formulas 1-1 to 1-6.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Formula 1-6]
상기 화학식들에서 X, Y는 화학식 1에서 정의한 바와 같다.X and Y in the above formulas are as defined in formula (1).
본 발명에 있어서, 상기 화학식 1로 표시되는 화합물의 구체적인 예는 다음과 같다:In the present invention, specific examples of the compound represented by Formula 1 are as follows:
본 발명에 따른 화학식 1의 화합물은 전자 전달 특성이 우수하고, 발광효율이 우수하며, 고색순도, 고효율 및 장수명을 가져, 유기발광소자에 적용시 우수한 소자특성을 나타낼 수 있다. 또한 화학식 1의 화합물은 전자주입이 용이한 LUMO 에너지 레벨을 가지며, 전자수송 특성이 우수하고, 유기발광소자의 발광층 및 전자수송층 적용시 우수한 저전압, 고효율, 높은 Tg로 인한 안정성 및 장수명을 가지게 할 수 있다.The compound of Formula 1 according to the present invention has excellent electron transport characteristics, excellent luminous efficiency, high color purity, high efficiency and long life, and thus can exhibit excellent device characteristics when applied to an organic light emitting device. In addition, the compound of Formula 1 has an LUMO energy level for easy electron injection, excellent electron transport characteristics, and excellent stability and long life due to low voltage, high efficiency, and high Tg when the light emitting layer and the electron transport layer of the organic light emitting device are applied. have.
또한 본 발명의 화합물은 하기 반응식 1 내지 3 중 어느 하나로 표시되는 반응식을 통하여 제조될 수 있다:In addition, the compounds of the present invention can be prepared through the reaction scheme represented by any one of the following schemes 1-3.
[반응식 1]Scheme 1
[반응식 2]Scheme 2
[반응식 3]Scheme 3
상기 반응식에서 X 및 Y는 화학식 1에서 정의한 바와 같다.X and Y in the scheme are as defined in formula (1).
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 유기물층에 포함하는 유기발광소자를 제공한다. 이때, 본 발명의 화합물은 구체적으로는 발광호스트, 전자주입재료, 전자수송재료 또는 정공억제재료로 단독으로 사용되거나 또는 공지의 화합물과 함께 사용될 수 있다. 더욱 구체적으로는 본 발명의 화합물을 발광호스트로 사용하는 것이며, 이 때 하기 화학식 2로 표시되는 발광화합물(발광호스트 2)을 본 발명의 화학식 1로 표시되는 화합물(발광호스트 1)과 함께 발광호스트로 같이 사용하는 것이 좋다. The present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer. In this case, the compound of the present invention may be specifically used as a light emitting host, an electron injection material, an electron transport material or a hole suppression material, or may be used together with a known compound. More specifically, the compound of the present invention is used as a light emitting host, wherein the light emitting compound represented by the following formula (2) (light emitting host 2) is combined with the compound represented by the formula (1) of the present invention (light emitting host 1). It is good to use as.
[화학식 2][Formula 2]
상기 화학식 2에서 r1 내지 r8은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며,In Formula 2, r 1 to r 8 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,Ar is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 C 6-50 aryl group which is unsubstituted or substituted with an aryloxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,
m은 1 내지 4의 정수이며, m is an integer from 1 to 4,
m이 2 내지 4일 때, Ar 및 r1-r8은 서로 연결될 수 있다.When m is 2 to 4, Ar and r 1 -r 8 may be connected to each other.
구체적으로 상기 화학식 2의 화합물은 하기 화학식 2-1 내지 2-7로 표시되는 화합물 중 어느 하나인 것이 좋다.Specifically, the compound of Formula 2 may be any one of the compounds represented by the following Formulas 2-1 to 2-7.
[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
[화학식 2-3][Formula 2-3]
[화학식 2-4][Formula 2-4]
[화학식 2-5][Formula 2-5]
[화학식 2-6] [Formula 2-6]
[화학식 2-7] [Formula 2-7]
상기 식들에서 Ar1, Ar2, Ar3, Ar4, Ar5는 각각 독립적으로 상기 화학식 2의 Ar의 정의와 같으며, Ar 1 , Ar 2 , Ar 3 , Ar 4, Ar 5 in the formulas are each independently the same as the definition of Ar of Formula 2,
R1, R2, R3, R4는 상기 화학식 2의 r1 내지 r8의 정의와 같으며, R 1 , R 2 , R 3 , and R 4 are the same as defined in r 1 to r 8 of Chemical Formula 2,
a, b 각각 독립적으로 0 내지 3의 정수이다.a and b are the integers of 0-3 each independently.
더욱 구체적으로 상기 화학식 2의 화합물은 상기 화학식 2-3로 표시되는 화합물인 것이 좋으며, 이 경우 화학식에 포함된 카바졸페닐부들 간에 치환된 구조를 포함함으로써 호모가 더 높아질 수 있으며, 정공주입이 보다 용이해지고, 구동전압을 낮출 수 있다.More specifically, the compound of Chemical Formula 2 may be a compound represented by Chemical Formula 2-3, and in this case, the homogeneity may be higher by including a structure substituted between carbazolephenyl moieties included in the chemical formula, and hole injection may be higher. It becomes easy and can lower a drive voltage.
본 발명의 유기발광소자가 상기 화학식 2의 화합물을 발광호스트로 사용할 경우, 화학식1 및 화학식2의 혼합비율은 중량비율로 9:1 내지 2:8인 것이 좋다. 상기 범위 내인 경우 유기발광소자의 구동전압이 낮고, 고효율 및 장수명을 가져올 수 있으나, 상기 범위를 벗어나 화학식 2로 표시되는 화합물이 너무 많은 경우 정공주입 및 수송이 과도해져 효율 및 수명이 감소할 수 있다.When the organic light emitting device of the present invention uses the compound of Chemical Formula 2 as a light emitting host, the mixing ratio of Chemical Formula 1 and Chemical Formula 2 may be 9: 1 to 2: 8 by weight. Within the above range, the driving voltage of the organic light emitting device may be low, resulting in high efficiency and long life. However, when there are too many compounds represented by Formula 2 outside the above range, hole injection and transport may be excessive, thereby reducing efficiency and lifespan. .
화학식 2의 구체적인 화합물은 다음과 같다.Specific compounds of the formula (2) are as follows.
본 발명에서 상기 발광호스트 1 및 2를 통하여 형성된 엑시플렉스 발광파장이 400-650 nm로 형성하는 것이 가능하며, 발광호스트 1 및 2의 선택에 의하여 450-500 nm의 엑시플렉스 파장을 형성하여 녹색유기발광소자에 사용할 수 있으며, 500-630 nm의 엑시플렉스 파장을 형성하여 적색유기발광소자에 사용할 수 있다.And a flex eksi emission wavelength is formed through the first and second light emitting host in the present invention can be formed into 400-650 nm, by the selection of the light emitting host 1 and 2 to form a flex eksi wavelength of 450-500 nm green organic It can be used in a light emitting device, and can be used in a red organic light emitting device by forming an exciplex wavelength of 500-630 nm.
구체적으로는 상기 발광호스트의 조합으로 형성된 엑시플렉스 파장이 발광층의 게스트인 도판트의 발광파장보다 단파장에서 형성되는 것이 좋다. 이는 발광호스트 조합에 의한 엑시플렉스 파장을 인광도판트가 흡수하여 발광하는 과정에 에너지 전이가 효율적으로 일어나 효율 극대화 및 고효율 장수명을 가능하게 한다.Specifically, the exciplex wavelength formed by the combination of the light emitting hosts may be formed at a shorter wavelength than that of the dopant which is a guest of the light emitting layer. This allows the energy transfer to be efficiently absorbed by the phosphor dopant absorbing the exciplex wavelength by the light emitting host combination to maximize efficiency and long life.
또한 본 발명의 유기발광소자는 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층을 포함하는 것을 제외하고는 공지의 유기발광소자의 제조방법을 사용하여 유기발광소자를 제조할 수 있으며, 일예로 유기발광소자의 제조방법을 설명하면 다음과 같다.In addition, the organic light emitting device of the present invention can manufacture an organic light emitting device using a known method of manufacturing an organic light emitting device, except that the organic light emitting device including at least one layer containing the compound represented by the formula (1), an example Referring to the manufacturing method of the organic light emitting device as follows.
상기 유기발광소자는 애노드(anode)와 캐소드(cathod) 사이에 정공주입층(HIL), 정공수송층(HTL), 발광층(EML), 전자수송층(ETL), 전자주입층(EIL) 등의 유기물층을 1 개 이상 포함할 수 있다.The organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between an anode and a cathode. It may contain one or more.
먼저, 기판 상부에 높은 일함수를 갖는 애노드 전극용 물질을 증착시켜 애노드를 형성한다. 이때, 상기 기판은 통상의 유기발광소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판을 사용하는 것이 좋다. 또한, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용할 수 있다. 상기 애노드 전극용 물질은 통상의 애노드 형성방법에 의해 증착할 수 있으며, 구체적으로 증착법 또는 스퍼터링법에 의해 증착할 수 있다.First, an anode is formed by depositing a material for an anode electrode having a high work function on the substrate. In this case, the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof. In addition, as the anode electrode material, transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used. The anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
그 다음, 상기 애노드 전극 상부에 정공주입층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 형성할 수 있다. 상기 정공주입층 물질은 공지의 정공주입층 물질이 사용될 수 있으며, 일예로 미국특허 제4,356,429호에 개시된 구리 프탈로시아닌 등의 프탈로시아닌 화합물 또는 스타버스트형 아민 유도체류인 TCTA(4,4',4"-트리(N-카바졸릴)트리페닐아민), m-MTDATA(4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민), m-MTDAPB(4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠), HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민) 등을 정공주입층 물질로 사용할 수 있다.Subsequently, the hole injection layer material may be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB). As the hole injection layer material, a well-known hole injection layer material may be used. For example, TCTA (4,4 ', 4 "), which is a phthalocyanine compound or a starburst type amine derivative such as copper phthalocyanine disclosed in US Pat. No. 4,356,429, may be used. Tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB (4,4', 4" -tris ( 3-methylphenylamino) phenoxybenzene), HI-406 (N 1 , N 1 '-(biphenyl-4,4'-diyl) bis (N 1-(naphthalen- 1 -yl) -N 4 , N 4 -Diphenylbenzene-1,4-diamine) and the like can be used as the hole injection layer material.
다음으로 상기 정공주입층 상부에 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있다.Next, the hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, or the like.
상기 정공수송층 물질은 공지의 정공수송층 물질이 사용될 수 있다. 구체적으로, 상기 공지의 정공수송층 물질로는 N-페닐카바졸, 폴리비닐카바졸 등의 카바졸 유도체, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD), N.N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축합환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.As the hole transport layer material, a known hole transport layer material may be used. Specifically, the known hole transport layer material includes carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1, Having an aromatic condensed ring such as 1-biphenyl] -4,4'-diamine (TPD) and N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) Conventional amine derivatives and the like can be used.
그 후, 상기 정공수송층 상부에 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. Thereafter, the light emitting layer material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, cast, LB, or the like. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer.
또한, 상기 발광층 재료는 공지의 호스트 또는 도펀트가 사용할 수 있으며, 본 발명의 화학식 1로 표시되는 화합물을 호스트로 사용하는 것이 좋으며, 구체적으로는 본 발명의 화학식 1로 표시되는 화합물(발광호스트 1)과 화학식 2로 표시되는 화합물(발광호스트 2)을 동시에 사용하는 것이 좋으며, 더욱 구체적으로는 화학식 1로 표시되는 화합물(발광호스트 1)과 화학식 2-3으로 표시되는 화합물(발광호스트 2)를 동시에 사용하는 것이 좋다. 상기 발광호스트로는 본 발명의 화학식 1로 표시되는 화합물(발광호스트 1)과 화학식 2로 표시되는 화합물(발광호스트 2)의 조합으로 형성된 엑시플렉스 파장이 발광층의 도판트의 발광파장보다 단파장에서 형성될 수 있도록 도판트 물질을 선택하여 사용하는 것이 좋다.In addition, the light emitting layer material may be a known host or dopant, it is preferable to use the compound represented by the formula (1) of the present invention as a host, specifically, the compound represented by the formula (1) of the present invention (light emitting host 1) And the compound represented by the formula (2) (light emitting host 2) is preferably used at the same time, more specifically, the compound represented by the formula (1) (luminescent host 1) and the compound represented by the formula 2-3 (light emitting host 2) at the same time It is good to use. The light emitting host has an exciplex wavelength formed by a combination of the compound represented by Chemical Formula 1 (light emitting host 1) and the compound represented by Chemical Formula 2 (light emitting host 2) at a wavelength shorter than that of the dopant of the light emitting layer. It is advisable to select and use a dopant material.
사용 가능한 형광 도펀트로는 이데미츠사(Idemitsu사)에서 구입 가능한 IDE102 또는 IDE105, 또는 BD142(N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)를 사용할 수 있으며, 인광 도펀트로는 녹색 인광 도펀트 Ir(ppy)3(트리스(2-페닐피리딘) 이리듐), 청색 인광 도펀트인 F2Irpic(이리듐(Ⅲ) 비스[4,6-다이플루오로페닐)-피리디나토-N,C2'] 피콜린산염), UDC사의 적색 인광 도펀트 RD61 등이 공동 진공증착(도핑)될 수 있다. Fluorescent dopants that can be used include IDE102 or IDE105, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethyrylcrissen-, available from Idemitsu. 6,12-diamine) can be used as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate), a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
또한 상기 정공수송층과 발광층 사이에는 발광보조층을 더욱 포함할 수 있으며, 발광보조층 재료로는 공지의 물질들이 사용될 수 있다.In addition, a light emitting auxiliary layer may be further included between the hole transport layer and the light emitting layer, and known materials may be used as the light emitting auxiliary layer material.
또한, 발광층에 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시킬 수 있다. 이때 사용할 수 있는 정공억제물질은 화학식 1로 표시되는 화합물 또는 정공억제재료로 사용되고 있는 공지의 재료 중에서 임의의 것을 선택해서 단독 또는 혼합하여 사용할 수 있다. 공지의 재료를 예를 들면, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 Balq(비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드), 페난트롤린(phenanthrolines)계 화합물(예: UDC사 BCP(바쏘쿠프로인)) 등을 사용할 수 있다.In addition, in order to prevent the triplet exciton or hole from diffusing into the electron transport layer, the hole suppressing material (HBL) may be further laminated by a vacuum deposition method or a spin coating method. In this case, the hole-inhibiting substance that can be used may be used alone or in combination by selecting any of the compounds represented by the formula (1) or known materials used as the hole-inhibiting material. Examples of known materials include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and hole suppression materials described in Japanese Patent Laid-Open No. 11-329734 (A1). (8-hydroxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound (e.g., BDC (vasocuproin) from UDC) can be used.
상기와 같이 형성된 발광층 상부에는 전자수송층이 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성할 수 있다.An electron transport layer is formed on the light emitting layer formed as above, wherein the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.
상기 전자수송층 재료는 상기 화학식 1로 표시되는 화합물 또는 공지의 재료가 사용될 수 있으며, 공지의 재료의 예로는 퀴놀린 유도체, 특히 트리스(8-퀴놀리놀라토)알루미늄(Alq3),또는 ET4(6,6'-(3,4-디메시틸-1,1-디메틸-1H-실올-2,5-디일)디-2,2'-비피리딘)을 사용할 수 있다. The electron transport layer material may be a compound represented by Formula 1 or a known material, and examples of the known material include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3 ), or ET4 (6). , 6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine) can be used.
또한, 전자수송층 상부에 캐소드로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(EIL)이 적층될 수 있으며, 전자주입층 물질로는 상기 화학식 1로 표시되는 화합물 또는 LiF, NaCl, CsF, Li2O,BaO등의 물질을 이용할 수 있다.In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and as the electron injection layer material, the compound represented by Chemical Formula 1 or LiF, NaCl, Materials such as CsF, Li 2 O, BaO and the like can be used.
마지막으로 전자수송층 또는 전자주입층 상부에 캐소드 형성용 금속을 진공증착법이나 스퍼터링법 등의 방법에 의해 형성하고 캐소드로 사용한다. 여기서 캐소드 형성용 금속으로는 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물, 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 있다. 또한, 전면 발광소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.Finally, the cathode forming metal is formed on the electron transport layer or the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode. The cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this. In addition, a transmissive cathode using ITO or IZO may be used to obtain the front light emitting device.
본 발명의 유기발광소자는 애노드, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 캐소드 구조의 유기발광소자뿐만 아니라, 다양한 구조의 유기발광소자의 구조가 가능하며, 필요에 따라 1층 또는 2층의 중간층을 더 형성하는 것도 가능하다.The organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.
상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 구체적으로는 10 내지 1,000 ㎚이며, 더욱 구체적으로는 20 내지 150 ㎚인 것이 좋다.The thickness of each organic material layer formed according to the present invention as described above can be adjusted according to the required degree, specifically 10 to 1,000 nm, more preferably 20 to 150 nm.
또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며, 형태안정성이 뛰어난 장점이 있다.In addition, the present invention has an advantage that the organic material layer including the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.
본 발명의 유기발광소자는 전자 및 정공에 대한 내구성 우수하여 유기발광소자의 장수명, 저전압 구동 및 고효율의 확보가 가능하며, 박막 안정성이 우수하며, 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)를 이용하여, 전자주입 및 수송이 용이하게 하고, 저전압 구동, 고효율을 가능하게 하며, 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 극대화시켜, 고효율 장수명을 가능하게 할 수 있다.The organic light emitting device of the present invention is excellent in durability against electrons and holes to ensure long life, low voltage driving and high efficiency of the organic light emitting device, excellent thin film stability, novel compounds of the present invention (light emitting host 1) and the cover The sol derivative (luminescent host 2) facilitates electron injection and transport, enables low voltage driving and high efficiency, and maximizes efficiency through exciplex formation and energy transfer to dopant, enabling high efficiency and long life. Can be.
이하, 본 발명의 이해를 돕기 위하여 구체적인 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다. Hereinafter, specific examples are provided to help understanding of the present invention, but the following examples are merely to illustrate the present invention, and the scope of the present invention is not limited to the following examples.
[화학식1]의 합성Synthesis of [Formula 1]
중간체I1의 합성Synthesis of Intermediate I1
[I1-1의 합성][Synthesis of I1-1]
둥근바닥플라스크에 triphenylen-2-ylboronic acid 8.4g, 2,8-dibromodibenzo[b,d]furan 10.0g을 톨루엔 280ml에 녹이고 K2CO3(2M) 46ml와 Pd(PPh3)4 1.1g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 재결정하여 중간체 I1-1 8.1g (수율 56%)를 얻었다.In a round bottom flask, 8.4 g of triphenylen-2-ylboronic acid and 10.0 g of 2,8-dibromodibenzo [b, d] furan were dissolved in 280 ml of toluene, and 46 ml of K 2 CO 3 (2M) and 1.1 g of Pd (PPh 3 ) 4 were added. After stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure and recrystallized to obtain 8.1 g of Intermediate I1-1 (yield 56%).
[I1의 합성][Synthesis of I1]
상기 중간체 I1-1 8.1g, bis(pinacolato)diboron 5.6g, Pd(dppf)Cl2 0.06g, KOAc 5.04g을 1,4-Dioxane 200ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 유기층을 MC추출하고 컬럼정제하여 중간체 I1 7.0g (수율 79%)를 얻었다.8.1 g of intermediate I1-1, 5.6 g of bis (pinacolato) diboron, 0.06 g of Pd (dppf) Cl 2 , and 5.04 g of KOAc were dissolved in 200 ml of 1,4-Dioxane and stirred under reflux. The reaction was confirmed by TLC, and the organic layer was extracted with MC and purified by column to obtain 7.0 g of intermediate I1 (yield 79%).
중간체I2의 합성Synthesis of Intermediate I2
상기 중간체 I1-1 및 I1 합성과 같은 방법으로 2,8-dibromodibenzo[b,d]furan 대신 4,6-dibromodibenzo[b,d]furan을 이용하여 중간체 I2를 합성하였다.(수율 50%)Intermediate I2 was synthesized using 4,6-dibromodibenzo [b, d] furan instead of 2,8-dibromodibenzo [b, d] furan in the same manner as the synthesis of Intermediates I1-1 and I1. (Yield 50%)
중간체I3의 합성Synthesis of Intermediate I3
[I3-1의 합성][Synthesis of I3-1]
둥근바닥플라스크에 2-bromotriphenylene 15.0g, dibenzo[b,d]furan-4-ylboronic acid 10.5g을 톨루엔 380ml에 녹이고 K2CO3(2M) 75ml와 Pd(PPh3)4 1.7g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 재결정하여 중간체 I3-1 15.2g (수율 66%)를 얻었다.To a round bottom flask was added 2-bromotriphenylene 15.0g, dibenzo [b , d] furan-4-ylboronic acid 10.5g was dissolved in toluene 380ml K 2 CO 3 (2M) 75ml and Pd (PPh 3) was placed under reflux for 4 1.7g Stirred. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure and recrystallized to obtain 15.2 g of Intermediate I3-1 (yield 66%).
[I3-2의 합성][Synthesis of I3-2]
상기 중간체 I3-1 15.0g을 DMF 150ml에 녹인 후 DMF 70ml에 N-Bromosuccinimide 7.5g 녹인 용액을 천천히 적가하고 16시간 교반하였다. TLC로 반응을 확인하고 증류수로 석출하고 재결정하여 중간체 I3-2 13.5g (수율 75%)를 얻었다.After dissolving 15.0 g of the intermediate I3-1 in 150 ml of DMF, a solution of 7.5 g of N-Bromosuccinimide was slowly added dropwise to 70 ml of DMF and stirred for 16 hours. The reaction was confirmed by TLC, precipitated with distilled water, and recrystallized to obtain 13.5 g of an intermediate I3-2 (yield 75%).
[I3의 합성][Synthesis of I3]
상기 중간체 I1-1 13.5g, bis(pinacolato)diboron 9.4g, Pd(dppf)Cl2 0.1g, KOAc 8.4g을 1,4-Dioxane 350ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 유기층을 MC추출하고 컬럼정제하여 중간체 I3 10.8g (수율 73%)를 얻었다.13.5 g of the intermediate I1-1, 9.4 g of bis (pinacolato) diboron, 0.1 g of Pd (dppf) Cl 2 , and 8.4 g of KOAc were dissolved in 350 ml of 1,4-Dioxane and stirred under reflux. The reaction was confirmed by TLC, and the organic layer was extracted with MC and purified by column to obtain 10.8 g (yield 73%) of intermediate I3.
중간체I4의 합성Synthesis of Intermediate I4
상기 중간체 I3-1 내지 I3 합성과 같은 방법으로 2-bromotriphenylene 대신 2-chloro-4,6-diphenyl-1,3,5-triazine을 이용하여 중간체 I4를 합성하였다.(수율 47%)Intermediate I4 was synthesized using 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-bromotriphenylene in the same manner as the synthesis of Intermediate I3-1 to I3. (Yield 47%)
중간체I5의 합성Synthesis of Intermediate I5
상기 중간체 I1-1 및 I1 합성과 같은 방법으로 2,8-dibromodibenzo[b,d]furan 대신 2,8-dibromodibenzo[b,d]thiophene을 이용하여 중간체 I5를 합성하였다.(수율 53%)Intermediate I5 was synthesized using 2,8-dibromodibenzo [b, d] thiophene instead of 2,8-dibromodibenzo [b, d] furan in the same manner as the synthesis of intermediates I1-1 and I1. (Yield 53%)
중간체I6의 합성Synthesis of Intermediate I6
상기 중간체 I1-1 및 I1 합성과 같은 방법으로 2,8-dibromodibenzo[b,d]furan 대신 4,6-dibromodibenzo[b,d]thiophene을 이용하여 중간체 I6를 합성하였다.(수율 48%)Intermediate I6 was synthesized using 4,6-dibromodibenzo [b, d] thiophene instead of 2,8-dibromodibenzo [b, d] furan in the same manner as the synthesis of intermediates I1-1 and I1. (Yield 48%)
중간체I7의 합성Synthesis of Intermediate I7
상기 중간체 I3-1 내지 I3 합성과 같은 방법으로 dibenzo[b,d]furan-4-ylboronic acid 대신 dibenzo[b,d]thiophen-4-ylboronic acid 을 이용하여 중간체 I7을 합성하였다.(수율 51%)Intermediate I7 was synthesized using dibenzo [b, d] thiophen-4-ylboronic acid instead of dibenzo [b, d] furan-4-ylboronic acid in the same manner as the synthesis of intermediates I3-1 to I3. (Yield 51% )
중간체I8의 합성Synthesis of Intermediate I8
상기 중간체 I3-1 내지 I3 합성과 같은 방법으로 2-bromotriphenylene 및 dibenzo[b,d]furan-4-ylboronic acid 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 및 dibenzo[b,d]thiophen-4-ylboronic acid 을 이용하여 중간체 I8을 합성하였다.(수율 45%)2-chloro-4,6-diphenyl-1,3,5-triazine and dibenzo [b instead of 2-bromotriphenylene and dibenzo [b, d] furan-4-ylboronic acid by the same method as the synthesis of intermediates I3-1 to I3 Intermediate I8 was synthesized using, d] thiophen-4-ylboronic acid (yield 45%).
[화학식 1]의 합성Synthesis of [Formula 1]
화합물 1-1Compound 1-1
둥근바닥플라스크에 상기 중간체 I1 5.0g, 2-chloro-4,6-diphenyl-1,3,5-triazine 2.8g을 톨루엔 120ml에 녹이고 K2CO3(2M) 15ml와 Pd(PPh3)4 0.33g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 재결정하여 화합물 1-1 4.0g (수율 67%)를 얻었다.In a round bottom flask, 5.0 g of the intermediate I1 and 2.8 g of 2-chloro-4,6-diphenyl-1,3,5-triazine were dissolved in 120 ml of toluene, 15 ml of K 2 CO 3 (2M) and Pd (PPh 3 ) 4 0.33 g was added and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure and recrystallized to obtain 4.0 g (yield 67%) of compound 1-1.
m/z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)
화합물 1-2Compound 1-2
상기 화합물 1-1과 같은 방법으로 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-chloro-2,6-diphenylpyrimidine을 이용하여 화합물 1-2를 합성하였다.(수율 62%)Compound 1-2 was synthesized using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1. %)
m/z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)
화합물 1-3Compound 1-3
상기 화합물 1-1과 같은 방법으로 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenylpyrimidine을 이용하여 화합물 1-3을 합성하였다.(수율 65%)Compound 1-3 was synthesized using 2-chloro-4,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1. %)
m/z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)
화합물 1-4Compound 1-4
상기 화합물 1-1과 같은 방법으로 중간체 I1 대신 중간체 I2를 이용하여 화합물 1-4를 합성하였다.(수율 59%)Compound 1-4 was synthesized using the intermediate I2 instead of the intermediate I1 in the same manner as the compound 1-1. (Yield 59%)
m/z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)
화합물 1-5의 합성Synthesis of Compound 1-5
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 중간체 I2 및 4-chloro-2,6-diphenylpyrimidine을 이용하여 화합물 1-5를 합성하였다.(수율 63%)Compound 1-5 was prepared by using intermediate I2 and 4-chloro-2,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1. Synthesis (yield 63%)
m/z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)
화합물 1-6의 합성Synthesis of Compound 1-6
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 중간체 I2 및 2-chloro-4,6-diphenylpyrimidine 을 이용하여 화합물 1-6을 합성하였다.(수율 60%)Compound 1-6 was prepared using intermediate I2 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1. (60% yield).
m/z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23 (2.1%)
화합물 1-7Compound 1-7
상기 화합물 1-1과 같은 방법으로 중간체 I1 대신 중간체 I3을 이용하여 화합물 1-7을 합성하였다.(수율 64%)Compound 1-7 was synthesized by using Intermediate I3 instead of Intermediate I1 in the same manner as in Compound 1-1. (Yield 64%)
m/z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)
화합물 1-8Compound 1-8
상기 화합물1-1과 같은 방법으로 중간체 I1 및 2-bromotriphenylene 대신 중간체 I4 및 2-chloro-4,6-diphenyl-1,3,5-triazine를 이용하여 화합물1-8을 합성하였다.(수율 60%)Compound 1-8 was synthesized by using intermediate I4 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of intermediate I1 and 2-bromotriphenylene in the same manner as Compound 1-1. %)
m/z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%), 626.21 (1.1%)
화합물 1-9Compound 1-9
상기 화합물 1-1과 같은 방법으로 중간체 I1 대신 중간체 I5를 이용하여 화합물 1-9을 합성하였다.(수율 60%)Compound 1-9 was synthesized using the intermediate I5 instead of the intermediate I1 in the same manner as the compound 1-1. (Yield 60%)
m/z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20 (2.0%), 642.19 (1.9%)m / z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20 (2.0%), 642.19 (1.9%)
화합물 1-10Compound 1-10
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 중간체 I5 및 4-chloro-2,6-diphenylpyrimidine을 이용하여 화합물 1-10을 합성하였다.(수율 65%)Compound 1-10 using intermediate I5 and 4-chloro-2,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1 Synthesis (yield 65%)
m/z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)
화합물 1-11Compound 1-11
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 중간체 I5 및 2-chloro-4,6-diphenylpyrimidine을 이용하여 화합물 1-11을 합성하였다.(수율 62%)Compound 1-11 was prepared by using intermediate I5 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1. (62% yield).
m/z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)
화합물 1-12Compound 1-12
상기 화합물 1-1과 같은 방법으로 중간체 I1 대신 중간체 I6을 이용하여 화합물 1-12를 합성하였다.(수율 65%)Compound 1-12 was synthesized using the intermediate I6 instead of the intermediate I1 in the same manner as the compound 1-1. (Yield 65%)
m/z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20 (2.0%), 642.19 (1.9%)m / z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20 (2.0%), 642.19 (1.9%)
화합물 1-13Compound 1-13
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 중간체 I6 및 4-chloro-2,6-diphenylpyrimidine을 이용하여 화합물 1-13을 합성하였다.(수율 60%)Compound 1-13 was prepared using intermediate I6 and 4-chloro-2,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1. (60% yield).
m/z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)
화합물 1-14Compound 1-14
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 중간체 I6 및 2-chloro-4,6-diphenylpyrimidine을 이용하여 화합물 1-14를 합성하였다.(수율 62%)Compound 1-14 using intermediate I6 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in compound 1-1 above (62% yield).
m/z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%), 643.21 (2.0%)
화합물 1-15Compound 1-15
상기 화합물 1-1과 같은 방법으로 중간체 I1 대신 중간체 I7을 이용하여 화합물 1-15를 합성하였다.(수율 65%)Compound 1-15 was synthesized using the intermediate I7 instead of the intermediate I1 in the same manner as the compound 1-1. (Yield 65%)
2,4-diphenyl-6-(6-(triphenylen-2-yl)dibenzo[b,d]thiophen-2-yl)-1,3,5-triazine2,4-diphenyl-6- (6- (triphenylen-2-yl) dibenzo [b, d] thiophen-2-yl) -1,3,5-triazine
화합물 1-16Compound 1-16
상기 화합물 1-1과 같은 방법으로 중간체 I1 및 2-bromotriphenylene 대신 중간체 I8및 2-chloro-4,6-diphenyl-1,3,5-triazine을 이용하여 화합물1-16을 합성하였다.(수율 66%)Compound 1-16 was synthesized using intermediates I8 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of intermediates I1 and 2-bromotriphenylene in the same manner as Compound 1-1. %)
m/z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20 (2.0%), 642.19 (1.9%)m / z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20 (2.0%), 642.19 (1.9%)
[화학식 2]의 합성Synthesis of [Formula 2]
화합물 2-1Compound 2-1
둥근바닥플라스크에 3-phenyl-9H-carbazole 5.0g, 3,3'-dibromo-1,1'-biphenyl 3.21g, t-BuONa 2.96g, Pd2(dba)3 0.75g, (t-Bu)3P 0.5ml를 톨루엔 100ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물 2-1 8.64g (수율 66%)를 얻었다.3-phenyl-9H-carbazole 5.0g, 3,3'-dibromo-1,1'-biphenyl 3.21g, t-BuONa 2.96g, Pd 2 (dba) 3 0.75g, (t-Bu) 0.5 ml of 3 P was dissolved in 100 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified and recrystallized to obtain 8.64 g of Compound 2-1 (yield 66%).
m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)m / z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)
화합물 2-2Compound 2-2
둥근바닥플라스크에 9-([1,1':3',1''-terphenyl]-5'-yl)-3-bromo-9H-carbazole 8.0g, (4-(9H-carbazol-9-yl)phenyl)boronic acid 4.85g을 톨루엔 200ml에 녹이고 K2CO3(2M) 25ml와 Pd(PPh3)4 0.6g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 MC로 추출하고 감압여과한 후 재결정하여 화합물 2-2 7.62g (수율 71%)를 얻었다.In a round bottom flask, 9-([1,1 ': 3', 1 ''-terphenyl] -5'-yl) -3-bromo-9H-carbazole 8.0g, (4- (9H-carbazol-9-yl 4.85 g of) phenyl) boronic acid was dissolved in 200 ml of toluene, and 25 ml of K 2 CO 3 (2M) and 0.6 g of Pd (PPh 3 ) 4 were added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure and recrystallized to obtain 7.62 g (71%) of compound 2-2.
m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)m / z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)
화합물 2-3Compound 2-3
둥근바닥플라스크에 9H,9'H-3,3'-bicarbazole 10.0g, 3-bromo-1,1'-biphenyl 14.1g, t-BuONa 4.4g, Pd2(dba)3 1.1g, (t-Bu)3P 2.5ml를 톨루엔 200ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물 2-3 14.2g (수율 73%)를 얻었다.9H, 9'H-3,3'-bicarbazole, 10.0g, 3-bromo-1,1'-biphenyl 14.1g, t-BuONa 4.4g, Pd 2 (dba) 3 1.1g, (t- Bu) 3 P 2.5 ml was dissolved in 200 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified and recrystallized to obtain 14.2 g of compound 2-3 (yield 73%).
m/z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)m / z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27 (2.2%)
화합물 2-4Compound 2-4
둥근바닥플라스크에 9-phenyl-9H,9'H-3,3'-bicarbazole 5.0g, 3-bromo-1,1'-biphenyl 4.0g, t-BuONa 1.8g, Pd2(dba)3 0.5g, (t-Bu)3P 0.5ml를 톨루엔 70ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물 2-4 5.33g (수율 67%)를 얻었다.5.0g, 3-bromo-1,1'-biphenyl 4.0g, t-BuONa 1.8g, Pd 2 (dba) 3 0.5g 9-phenyl-9H, 9'H-3,3'-bicarbazole 0.5 ml of (t-Bu) 3 P was dissolved in 70 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified and recrystallized to give 5.33 g (yield 67%) of Compound 2-4.
m/z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)m / z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)
화합물 2-5Compound 2-5
둥근바닥플라스크에 9-([1,1'-biphenyl]-3-yl)-3,6-dibromo-9H-carbazole 5.0g, 9H-carbazole 3.7g, t-BuONa 1.5g, Pd2(dba)3 0.4g, (t-Bu)3P 0.9ml를 톨루엔 70ml에 녹인 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제 및 재결정하여 화합물 2-5 4.22g (수율 62%)를 얻었다.In a round bottom flask, 9-([1,1'-biphenyl] -3-yl) -3,6-dibromo-9H-carbazole 5.0g, 9H-carbazole 3.7g, t-BuONa 1.5g, Pd 2 (dba) 3 0.4 g, (t-Bu) 3 P, 0.9 ml was dissolved in 70 ml of toluene, and stirred at reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified and recrystallized to obtain 4.22 g (yield 62%) of compound 2-5.
m/z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)m / z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%), 650.25 (1.1%)
유기발광소자의 제조Fabrication of Organic Light Emitting Diode
도 1에 기재된 구조에 따라 유기발광소자를 제조하였다. 유기발광소자는 아래로부터 양극(정공주입전극(11))/정공주입층(12)/정공수송층(13)/발광층(14)/전자수송층(15)/음극(전자주입전극(16)) 순으로 적층되어 있다.An organic light emitting device was manufactured according to the structure of FIG. 1. The organic light emitting device is in order from the bottom of the anode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transport layer 15 / cathode (electron injection electrode 16) Are stacked.
실시예 및 비교예의 정공주입층(12), 정공수송층(13), 발광층(14), 전자수송층(15)은 아래과 같은 물질을 사용하였다.The hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of the Examples and Comparative Examples used the following materials.
유기발광소자 제작에 앞서 엑시플렉스에 의해 형성된 에너지가 인광도판트로 에너지 전이를 효율적으로 하기 위한 호스트 1 및 호스트 2의 조합을 알아보기 위해 유리 기판에 호스트1/호스트2 (1:1)를 증착하여 엑시플렉스 파장을 측정하였으며, 그 결과를 하기 표 1에 나타내었다.Prior to fabrication of the organic light emitting diode, the energy formed by the exciplex is deposited on the glass substrate to host 1 / host 2 (1: 1) to find a combination of host 1 and host 2 for efficient energy transfer to phosphorescent dopant. The exciplex wavelength was measured and the results are shown in Table 1 below.
표 1
Table 1
| 호스트1 | 호스트2 | 호스트1:호스트2 | |||
| 화합물 | T1 (eV) | 화합물 | T1 (eV) | 엑시플렉스(nm) | |
| 조합예1 | 1-1 | 2.54 | 2-1 | 2.87 | 460 |
| 조합예2 | 1-1 | 2.54 | 2-2 | 2.81 | 467 |
| 조합예3 | 1-1 | 2.54 | 2-3 | 2.76 | 483 |
| 조합예4 | 1-1 | 2.54 | 2-4 | 2.76 | 491 |
| 조합예5 | 1-1 | 2.54 | 2-5 | 2.84 | 468 |
| 조합예6 | 1-2 | 2.57 | 2-3 | 2.76 | 473 |
| 조합예7 | 1-3 | 2.57 | 2-3 | 2.76 | 472 |
| 조합예8 | 1-4 | 2.55 | 2-3 | 2.76 | 480 |
| 조합예9 | 1-5 | 2.57 | 2-3 | 2.76 | 472 |
| 조합예10 | 1-6 | 2.57 | 2-3 | 2.76 | 470 |
| 조합예11 | 1-7 | 2.55 | 2-3 | 2.76 | 481 |
| 조합예12 | 1-8 | 2.52 | 2-3 | 2.76 | 489 |
| 조합예13 | 1-9 | 2.54 | 2-3 | 2.76 | 482 |
| 조합예14 | 1-10 | 2.56 | 2-3 | 2.76 | 473 |
| 조합예15 | 1-11 | 2.56 | 2-3 | 2.76 | 473 |
| 조합예16 | 1-12 | 2.56 | 2-3 | 2.76 | 480 |
| 조합예17 | 1-13 | 2.58 | 2-3 | 2.76 | 470 |
| 조합예18 | 1-14 | 2.57 | 2-3 | 2.76 | 470 |
| 조합예19 | 1-15 | 2.59 | 2-3 | 2.76 | 481 |
| 조합예20 | 1-16 | 2.52 | 2-3 | 2.76 | 488 |
| 조합비교예1 | CBP | 2.64 | 2-3 | 2.76 | X |
| 조합비교예2 | Ref.1 | 2.53 | 2-3 | 2.76 | X |
| 조합비교예3 | Ref.2 | 2.54 | 2-3 | 2.76 | X |
| 조합비교예4 | Ref.3 | 2.43 | 2-3 | 2.76 | 512 |
| Host1 | Host2 | Host 1: Host 2 | |||
| compound | T1 (eV) | compound | T1 (eV) | Exciplex (nm) | |
| Combination Example 1 | 1-1 | 2.54 | 2-1 | 2.87 | 460 |
| Combination Example 2 | 1-1 | 2.54 | 2-2 | 2.81 | 467 |
| Combination Example 3 | 1-1 | 2.54 | 2-3 | 2.76 | 483 |
| Combination Example 4 | 1-1 | 2.54 | 2-4 | 2.76 | 491 |
| Combination Example 5 | 1-1 | 2.54 | 2-5 | 2.84 | 468 |
| Combination Example 6 | 1-2 | 2.57 | 2-3 | 2.76 | 473 |
| Combination Example 7 | 1-3 | 2.57 | 2-3 | 2.76 | 472 |
| Combination Example 8 | 1-4 | 2.55 | 2-3 | 2.76 | 480 |
| Combination Example 9 | 1-5 | 2.57 | 2-3 | 2.76 | 472 |
| Combination Example 10 | 1-6 | 2.57 | 2-3 | 2.76 | 470 |
| Combination Example 11 | 1-7 | 2.55 | 2-3 | 2.76 | 481 |
| Combination Example 12 | 1-8 | 2.52 | 2-3 | 2.76 | 489 |
| Combination Example 13 | 1-9 | 2.54 | 2-3 | 2.76 | 482 |
| Combination Example 14 | 1-10 | 2.56 | 2-3 | 2.76 | 473 |
| Combination Example 15 | 1-11 | 2.56 | 2-3 | 2.76 | 473 |
| Combination Example 16 | 1-12 | 2.56 | 2-3 | 2.76 | 480 |
| Combination Example 17 | 1-13 | 2.58 | 2-3 | 2.76 | 470 |
| Combination Example 18 | 1-14 | 2.57 | 2-3 | 2.76 | 470 |
| Combination Example 19 | 1-15 | 2.59 | 2-3 | 2.76 | 481 |
| Combination Example 20 | 1-16 | 2.52 | 2-3 | 2.76 | 488 |
| Combination Comparison Example 1 | CBP | 2.64 | 2-3 | 2.76 | X |
| Comparative Example 2 | Ref.1 | 2.53 | 2-3 | 2.76 | X |
| Comparative Example 3 | Ref.2 | 2.54 | 2-3 | 2.76 | X |
| Comparative Example 4 | Ref.3 | 2.43 | 2-3 | 2.76 | 512 |
상기 표 1에서 나타난 바와 같이 조합비교예1 내지 조합비교예3은 엑시플렉스에 의한 파장이 관측되지 않았으며, 조합비교예4의 경우 510nm 이상에서 파장이 관측되었다. 이는 녹색영역의 인광도판트의 흡수파장(최우측 450nm-500nm영역)을 고려할 때 에너지 전이가 비효율적으로 일어난다는 것을 알 수 있다. As shown in Table 1, in Comparative Comparative Examples 1 to 3, wavelengths due to exciplex were not observed, and in Comparative Comparative Example 4, wavelengths were observed at 510 nm or more. This can be seen that the energy transfer occurs inefficiently considering the absorption wavelength of the phosphor in the green region (450nm-500nm region of the rightmost).
유기발광소자의 제조 Fabrication of Organic Light Emitting Diode
실시예 1 Example 1
인듐틴옥사이드(ITO)가 1500Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층 HI01 600Å, 정공수송층으로 NPB 250Å을 제막하였다. 다음으로 상기 발광층으로 화합물1-1/Ir(ppy)3 10%로 도핑하여 300Å 제막하였다. 다음으로 전자수송층으로 ET01:Liq(1:1) 300Å 제막한 후 LiF 10Å, 알루미늄(Al) 1000Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 녹색 유기발광소자를 제작하였다.An indium tin oxide (ITO) 1500 Å thick thin glass substrate was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using oxygen plasma. Using an evaporator, NPB 250 주 was formed into a hole injection layer HI01 600 Å and a hole transport layer. Next, the light emitting layer was doped with 10% of Compound 1-1 / Ir (ppy) 3 to form 300 Å. Next, ET01: Liq (1: 1) 300 Å was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 막, which were encapsulated in a glove box to produce a green organic light emitting device.
실시예 2Example 2
상기 실시예 1의 발광층 호스트로 화합물 1-1 대신 화합물 1-2를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Example 1 except that Compound 1-2 was used instead of Compound 1-1 as the emission layer host.
실시예 3Example 3
상기 실시예1의 발광층 호스트로 화합물 1-1 대신 화합물 1-4를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Example 1-1 except that Compound 1-4 was used instead of Compound 1-1 as the emission layer host.
실시예 4Example 4
상기 실시예 1의 발광층 호스트로 화합물 1-1 대신 화합물 1-8을 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Example 1-1 except that Compound 1-8 was used instead of Compound 1-1 as the emission layer host.
실시예 5Example 5
상기 실시예 1의 발광층 호스트로 화합물 1-1 대신 화합물 1-11을 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Example 1-1 except that Compound 1-11 was used instead of Compound 1-1 as the emission layer host.
실시예 6Example 6
인듐틴옥사이드(ITO)가 1500Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층 HI01 600Å, 정공수송층으로 NPB 250Å를 제막하였다. 다음으로 상기 발광층으로 화합물 1-1:화합물 2-3(6:4w%)혼합물/Ir(ppy)3 10%로 도핑하여 300Å 제막하였다. 다음으로 전자수송층으로 ET01:Liq(1:1) 300Å 제막한 후 LiF 10Å, 알루미늄(Al) 1000Å 제막하고, 이 소자를 글로브 박스에서 밀봉(Encapsulation)함으로써 녹색 유기발광소자를 제작하였다.An indium tin oxide (ITO) 1500 Å thick thin glass substrate was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using oxygen plasma. Using an evaporator, NPB 250 주 was formed into a hole injection layer HI01 600 Å and a hole transport layer. Next, the light emitting layer was doped with 10% of Compound 1-1: Compound 2-3 (6: 4w%) mixture / Ir (ppy) 3 to form 300 Å. Next, ET01: Liq (1: 1) 300 Å was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 막, which were encapsulated in a glove box to produce a green organic light emitting device.
실시예 7 내지 실시예 21Examples 7-21
실시예 6과 같은 방법으로 발광층 호스트로 화합물 1-1:화합물 2-3 대신 각각 화합물 1-2 내지 1-16:화합물 2-3(6:4w%) 혼합물을 사용하여 제막한 녹색 유기발광소자를 제작하였다.A green organic light emitting diode formed by using a mixture of Compound 1-2-1 to Compound 1-3 (6: 4w%) instead of Compound 1-1: Compound 2-3 as a light emitting layer host in the same manner as in Example 6. Was produced.
비교예 1 Comparative Example 1
상기 실시예 1의 발광층 호스트로 CBP를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as CBP except that CBP was used as a light emitting layer host.
비교예 2 Comparative Example 2
상기 실시예 1의 발광층 호스트로 Ref.1을 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Ref. 1 except that Ref. 1 was used as the light emitting layer host.
비교예 3 Comparative Example 3
상기 실시예1의 발광층 호스트로 Ref.2를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Ref. 2 except for using the light emitting layer host of Example 1.
비교예 4Comparative Example 4
상기 실시예1의 발광층 호스트로 Ref.3을 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다.A green organic light emitting diode was manufactured according to the same method as Ref. 3 except that Ref. 3 was used as the light emitting layer host.
유기발광소자의 성능평가Performance Evaluation of Organic Light Emitting Diode
키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 및 비교예의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 2에 나타내었다.Inject electrons and holes by applying voltage to a Keithley 2400 source measurement unit and measure the luminance when light is emitted using the Konica Minolta Spectroradiometer (CS-2000) Thus, the performance of the organic light emitting diodes of Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 2.
표 2
TABLE 2
| Op. V | QE(%) | Cd/A | lm/w | CIEx | CIEy | 수명@10000nit | |
| 실시예 1 | 4.31 | 17.31 | 44.68 | 35.31 | 0.301 | 0.621 | 55 |
| 실시예 2 | 4.50 | 17.19 | 43.21 | 35.03 | 0.301 | 0.619 | 52 |
| 실시예 3 | 4.31 | 17.30 | 44.88 | 35.22 | 0.300 | 0.620 | 50 |
| 실시예 4 | 4.32 | 17.33 | 44.81 | 35.51 | 0.300 | 0.622 | 55 |
| 실시예 5 | 4.30 | 17.35 | 44.21 | 35.99 | 0.299 | 0.620 | 54 |
| 실시예 6 | 3.98 | 18.20 | 54.02 | 43.24 | 0.300 | 0.619 | 83 |
| 실시예 7 | 4.05 | 18.11 | 53.01 | 41.12 | 0.300 | 0.618 | 72 |
| 실시예 8 | 4.00 | 18.25 | 53.65 | 40.01 | 0.302 | 0.619 | 72 |
| 실시예 9 | 3.98 | 18.10 | 54.18 | 43.12 | 0.300 | 0.620 | 80 |
| 실시예 10 | 4.02 | 18.12 | 53.25 | 43.91 | 0.300 | 0.623 | 75 |
| 실시예 11 | 4.03 | 18.06 | 53.11 | 40.00 | 0.301 | 0.622 | 81 |
| 실시예 12 | 4.00 | 18.09 | 53.92 | 43.91 | 0.301 | 0.620 | 74 |
| 실시예 13 | 4.03 | 18.15 | 53.01 | 40.22 | 0.299 | 0.620 | 73 |
| 실시예 14 | 3.97 | 18.21 | 53.95 | 43.01 | 0.301 | 0.622 | 78 |
| 실시예 15 | 4.02 | 18.23 | 53.28 | 41.00 | 0.300 | 0.620 | 71 |
| 실시예 16 | 4.00 | 18.00 | 53.25 | 42.78 | 0.300 | 0.622 | 74 |
| 실시예 17 | 3.97 | 18.07 | 53.91 | 43.54 | 0.299 | 0.620 | 82 |
| 실시예 18 | 4.00 | 18.09 | 53.00 | 40.11 | 0.302 | 0.619 | 76 |
| 실시예 19 | 4.04 | 18.07 | 53.01 | 40.01 | 0.303 | 0.615 | 76 |
| 실시예 20 | 4.00 | 18.04 | 53.65 | 43.72 | 0.301 | 0.620 | 79 |
| 실시예 21 | 4.00 | 18.00 | 53.47 | 42.00 | 0.300 | 0.618 | 74 |
| 비교예 1 | 5.02 | 6.43 | 13.12 | 7.72 | 0.301 | 0.623 | - |
| 비교예 2 | 5.01 | 11.51 | 30.01 | 24.83 | 0.301 | 0.621 | 33 |
| 비교예 3 | 5.00 | 11.10 | 32.01 | 25.95 | 0.302 | 0.625 | 30 |
| 비교예 4 | 4.64 | 12.70 | 37.40 | 30.40 | 0.310 | 0.611 | 39 |
| Op. V | QE (%) | Cd / A | lm / w | CIEx | CIEy | Lifespan @ 10000nit | |
| Example 1 | 4.31 | 17.31 | 44.68 | 35.31 | 0.301 | 0.621 | 55 |
| Example 2 | 4.50 | 17.19 | 43.21 | 35.03 | 0.301 | 0.619 | 52 |
| Example 3 | 4.31 | 17.30 | 44.88 | 35.22 | 0.300 | 0.620 | 50 |
| Example 4 | 4.32 | 17.33 | 44.81 | 35.51 | 0.300 | 0.622 | 55 |
| Example 5 | 4.30 | 17.35 | 44.21 | 35.99 | 0.299 | 0.620 | 54 |
| Example 6 | 3.98 | 18.20 | 54.02 | 43.24 | 0.300 | 0.619 | 83 |
| Example 7 | 4.05 | 18.11 | 53.01 | 41.12 | 0.300 | 0.618 | 72 |
| Example 8 | 4.00 | 18.25 | 53.65 | 40.01 | 0.302 | 0.619 | 72 |
| Example 9 | 3.98 | 18.10 | 54.18 | 43.12 | 0.300 | 0.620 | 80 |
| Example 10 | 4.02 | 18.12 | 53.25 | 43.91 | 0.300 | 0.623 | 75 |
| Example 11 | 4.03 | 18.06 | 53.11 | 40.00 | 0.301 | 0.622 | 81 |
| Example 12 | 4.00 | 18.09 | 53.92 | 43.91 | 0.301 | 0.620 | 74 |
| Example 13 | 4.03 | 18.15 | 53.01 | 40.22 | 0.299 | 0.620 | 73 |
| Example 14 | 3.97 | 18.21 | 53.95 | 43.01 | 0.301 | 0.622 | 78 |
| Example 15 | 4.02 | 18.23 | 53.28 | 41.00 | 0.300 | 0.620 | 71 |
| Example 16 | 4.00 | 18.00 | 53.25 | 42.78 | 0.300 | 0.622 | 74 |
| Example 17 | 3.97 | 18.07 | 53.91 | 43.54 | 0.299 | 0.620 | 82 |
| Example 18 | 4.00 | 18.09 | 53.00 | 40.11 | 0.302 | 0.619 | 76 |
| Example 19 | 4.04 | 18.07 | 53.01 | 40.01 | 0.303 | 0.615 | 76 |
| Example 20 | 4.00 | 18.04 | 53.65 | 43.72 | 0.301 | 0.620 | 79 |
| Example 21 | 4.00 | 18.00 | 53.47 | 42.00 | 0.300 | 0.618 | 74 |
| Comparative Example 1 | 5.02 | 6.43 | 13.12 | 7.72 | 0.301 | 0.623 | - |
| Comparative Example 2 | 5.01 | 11.51 | 30.01 | 24.83 | 0.301 | 0.621 | 33 |
| Comparative Example 3 | 5.00 | 11.10 | 32.01 | 25.95 | 0.302 | 0.625 | 30 |
| Comparative Example 4 | 4.64 | 12.70 | 37.40 | 30.40 | 0.310 | 0.611 | 39 |
상기 표 2에 나타나는 바와 같이 본 발명의 실시예들은 비교예 1 내지 4에 비하여 구동전압이 낮고 고효율 및 장수명을 가지는 것을 확인할 수 있으며, 모든 면에서 물성이 우수한 것을 알 수 있다. 본 발명의 실시예들은 비교예 2 내지 비교예 4와 비교하여 트리페닐렌에 다이벤조퓨란 및 다이벤조티오펜을 연결기로 가지며 헤테로아로마틱이 추가되어 전자주입 및 수송이 용이하게 함으로써 구동전압이 낮고 효율 및 수명이 상승하는 것을 알 수 있다. 여기에 정공주입 및 수송이 용이한 호스트2 화합물을 같이 사용함으로써 더욱 구동전압이 낮아지고 고전류 밀도에서도 내구성이 좋아 장수명을 가지는 것을 확인할 수 있다. 이는 전자주입 및 수송이 용이한 호스트 1 화합물에 정공주입 및 수송이 용이한 호스트 2 화합물을 사용함으로써 구동전압을 낮추고, 발광층내 엑시톤을 효과적으로 가둬 효율을 증가시키고, 고전류 밀도에서 롤오프현상을 억제하며, 내구성이 좋아 장수명을 가지는 것을 알 수 있다.As shown in Table 2, the embodiments of the present invention can confirm that the driving voltage is lower than the Comparative Examples 1 to 4 and have a high efficiency and a long life, it can be seen that the physical properties are excellent in all aspects. Examples of the present invention have a linkage of dibenzofuran and dibenzothiophene to triphenylene in comparison with Comparative Examples 2 to 4, and heteroaromatic is added to facilitate electron injection and transport, thereby lowering driving voltage and efficiency. And it turns out that a lifetime rises. By using the host 2 compound, which is easy to inject and transport holes, it can be seen that the driving voltage is further lowered and the durability is long even at high current density. This reduces the driving voltage, effectively traps the excitons in the light emitting layer, increases the efficiency, and suppresses the roll-off phenomenon at high current density by using the host 2 compound that facilitates hole injection and transport in the host 1 compound that facilitates electron injection and transport. It is understood that durability is good and it has long life.
실시예 22Example 22
실시예 6과 같은 방법으로 발광층 호스트로 화합물 1-1:화합물 2-3(7:3w%) 을 사용하여 제막한 녹색 유기발광소자를 제작하였다.In the same manner as in Example 6, a green organic light emitting diode was manufactured by using Compound 1-1: Compound 2-3 (7: 3w%) as a light emitting layer host.
실시예 23Example 23
실시예 6과 같은 방법으로 발광층 호스트로 화합물 1-1:화합물 2-3(8:2w%) 을 사용하여 제막한 녹색 유기발광소자를 제작하였다.In the same manner as in Example 6, a green organic light emitting diode was manufactured by using Compound 1-1: Compound 2-3 (8: 2w%) as a light emitting layer host.
실시예 24Example 24
실시예 6과 같은 방법으로 발광층 호스트로 화합물 1-1:화합물 2-3(4:6w%) 을 사용하여 제막한 녹색 유기발광소자를 제작하였다.In the same manner as in Example 6, a green organic light emitting diode was manufactured by using Compound 1-1: Compound 2-3 (4: 6w%) as a light emitting layer host.
실시예 25Example 25
실시예 6과 같은 방법으로 발광층 호스트로 화합물 1-1:화합물 2-3(2:8w%) 을 사용하여 제막한 녹색 유기발광소자를 제작하였다.In the same manner as in Example 6, a green organic light emitting diode was manufactured by using Compound 1-1: Compound 2-3 (2: 8w%) as a light emitting layer host.
참고예 1Reference Example 1
실시예 6과 같은 방법으로 발광층 호스트로 화합물 1-1:화합물 2-3(1:9w%) 을 사용하여 제막한 녹색 유기발광소자를 제작하였다.In the same manner as in Example 6, a green organic light emitting diode was manufactured by using Compound 1-1: Compound 2-3 (1: 9w%) as a light emitting layer host.
상기 실시예 22 내지 25및 참고예 1에 대하여 키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 및 비교예의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 3에 나타내었다.Examples 22 to 25 and Reference Example 1 inject electrons and holes by applying a voltage to a Keithley 2400 source measurement unit and use a Konica Minolta spectrophotometer (CS-2000). By measuring the luminance when the light is emitted by using the, the performance of the organic light emitting diodes of the Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 3. .
표 3
TABLE 3
| Op. V | QE(%) | Cd/A | lm/w | CIEx | CIEy | 수명@10000nit | |
| 실시예 6 | 3.98 | 18.20 | 54.02 | 43.24 | 0.300 | 0.619 | 83 |
| 실시예 22 | 4.00 | 18.45 | 55.65 | 44.00 | 0.302 | 0.620 | 90 |
| 실시예 23 | 4.03 | 18.40 | 55.18 | 43.72 | 0.300 | 0.619 | 86 |
| 실시예 24 | 3.96 | 18.01 | 53.01 | 42.12 | 0.300 | 0.619 | 80 |
| 실시예 25 | 3.93 | 16.10 | 43.18 | 35.12 | 0.300 | 0.622 | 60 |
| 참고예 1 | 3.90 | 12.10 | 33.18 | 25.12 | 0.300 | 0.624 | 42 |
| Op. V | QE (%) | Cd / A | lm / w | CIEx | CIEy | Lifespan @ 10000nit | |
| Example 6 | 3.98 | 18.20 | 54.02 | 43.24 | 0.300 | 0.619 | 83 |
| Example 22 | 4.00 | 18.45 | 55.65 | 44.00 | 0.302 | 0.620 | 90 |
| Example 23 | 4.03 | 18.40 | 55.18 | 43.72 | 0.300 | 0.619 | 86 |
| Example 24 | 3.96 | 18.01 | 53.01 | 42.12 | 0.300 | 0.619 | 80 |
| Example 25 | 3.93 | 16.10 | 43.18 | 35.12 | 0.300 | 0.622 | 60 |
| Reference Example 1 | 3.90 | 12.10 | 33.18 | 25.12 | 0.300 | 0.624 | 42 |
상기 표 3에서 화학식1 및 화학식2의 조합비율에 따른 소자특성을 확인하였다. 결과적으로 화학식1 및 화학식2의 비율이 1:9의 경우 효율 및 수명이 감소하는 결과를 얻었고, 이는 비교예 1과 비교하여 화학식2로 인해 정공주입 및 수송이 과도해진 결과라 할 수 있다. 구체적으로 화학식1 및 화학식2의 비율은 9:1 내지 2:8에서 발광호스트 조합에 의한 유리한 특성을 확인할 수 있었다.In Table 3, the device characteristics according to the combination ratio of Chemical Formula 1 and Chemical Formula 2 were confirmed. As a result, when the ratio of Chemical Formula 1 and Chemical Formula 2 is 1: 9, efficiency and lifespan were reduced, which is a result of excessive hole injection and transport due to Chemical Formula 2 compared with Comparative Example 1. Specifically, the ratio of the formulas (1) and (2) was confirmed to be advantageous properties by the light-emitting host combination in 9: 1 to 2: 8.
본 발명의 화합물과 상기 화합물을 적용한 유기발광소자는 다음의 특징을 가진다.The compound of the present invention and the organic light emitting device to which the compound is applied have the following characteristics.
1. 화합물 내의 트리페닐렌 구조의 도입으로 전자 및 정공에 대한 내구성 우수하여 유기발광소자의 장수명 확보.1. The long life of organic light emitting device is secured by the introduction of triphenylene structure in the compound.
2. 그린인광호스트로 적합한 삼중항 에너지 유지하여 유기발광소자의 고효율 확보.2. Securing high efficiency of organic light emitting device by maintaining triple energy suitable as green phosphorescent host.
3. 화합물 내에 헤테로아릴기 도입으로 전자주입 및 수송 용이함으로써 유기발광소자의 저전압 구동 및 고효율 확보.3. Low voltage driving and high efficiency of organic light emitting device by easy injecting and transporting electrons by introducing heteroaryl group into compound.
4. 화합물 내 Fused ring으로 높은 Tg 형성을 가능하게 하고, 유기발광소자 구동시 박막 안정성을 향상시킴.4. Fused ring in compound enables high Tg formation and improves thin film stability when driving organic light emitting device.
5. 유기발광소자에 적용시 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)를 이용하여, 정공주입, 전자주입 및 수송이 용이하게 하고, 저전압 구동, 고효율을 가능하게 함.5. When applied to an organic light emitting device, by using the novel compound (luminescent host 1) and carbazole derivative (luminescent host 2) of the present invention, hole injection, electron injection and transport are easy, low voltage driving and high efficiency are possible. Let it be.
6. 유기발광소자에 적용시 본 발명의 신규한 화합물(발광호스트 1)과 카바졸 유도체(발광호스트 2)의 사용을 통하여 엑시플렉스 형성 및 도판트로의 에너지 전이를 통한 효율 극대화시켜, 고효율 장수명을 가능하게 함.6. When applied to an organic light emitting device, through the use of the novel compound (light emitting host 1) and carbazole derivatives (light emitting host 2) of the present invention to maximize the efficiency through the formation of exciplex and energy transfer to dopant, high efficiency long life Make it possible.
Claims (14)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 식에서,WhereX는 각각 독립적으로 N 또는 CR0이며, X중 적어도 2개는 N이며, 여기서 R0은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,Each X is independently N or CR 0 , at least two of X are N, wherein R 0 is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,Y는 O 또는 S이며,Y is O or S,R1, R2 및 R3는 각각 독립적으로 수소; 중수소; 할로겐; 아미노기; 니트릴기; 니트로기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며,R 1 , R 2 and R 3 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,m, n은 각각 독립적으로 0 내지 2의 정수이다.m and n are each independently an integer of 0-2. - 제1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 1-1 내지 1-6 중 어느 하나로 표시되는 화합물:Formula 1 is a compound represented by any one of the following formula 1-1 to 1-6:[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Formula 1-6]
상기 화학식들에서 X, Y는 화학식 1에서 정의한 바와 같다.X and Y in the above formulas are as defined in formula (1). - 제1항에 있어서, The method of claim 1,상기 화학식 1은 하기 화학식들 중 어느 하나로 표시되는 화합물:Formula 1 is a compound represented by any one of the following formula:
- 애노드(anode), 캐소드(cathode) 및 두 전극 사이에 제1항 기재의 화학식 1로 표시되는 화합물을 함유하는 1층 이상의 유기물층을 포함하는 유기발광소자.An organic light emitting device comprising an anode, a cathode and at least one organic layer containing a compound represented by the formula (1) according to claim 1 between two electrodes.
- 제4항에 있어서,The method of claim 4, wherein상기 유기물층이 발광층, 전자주입층, 전자수송층 또는 정공억제층인 유기발광소자.And an organic light emitting layer, an electron injection layer, an electron transport layer, or a hole suppression layer.
- 제5항에 있어서,The method of claim 5,상기 발광층이 상기 화학식 1로 표시되는 화합물을 발광호스트로 포함하는 유기발광소자.An organic light emitting device in which the light emitting layer comprises a compound represented by Chemical Formula 1 as a light emitting host.
- 제5항에 있어서,The method of claim 5,상기 발광층이 상기 화학식 1로 표시되는 화합물(발광호스트 1) 및 하기 화학식 2로 표시되는 화합물(발광호스트 2)을 포함하는 유기발광소자:An organic light emitting device including the compound represented by Chemical Formula 1 (light emitting host 1) and the compound represented by Chemical Formula 2 (light emitting host 2):[화학식 2][Formula 2]
상기 화학식 2에서 r1 내지 r8은 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이며,In Formula 2, r 1 to r 8 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl jade C 6-50 aryl group which is unsubstituted or substituted with a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,Ar is deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 C 6-50 aryl group which is unsubstituted or substituted with an aryloxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group,m은 1 내지 4의 정수이며, m is an integer from 1 to 4,m이 2 내지 4일 때, Ar 및 r1~r8은 서로 연결될 수 있다.When m is 2 to 4, Ar and r1 to r8 may be connected to each other. - 제7항에 있어서,The method of claim 7, wherein상기 화학식 2로 표시되는 화합물이 하기 화학식 2-1 내지 2-7로 표시되는 화합물 중 어느 하나인 유기발광소자:An organic light emitting device in which the compound represented by Formula 2 is any one of the compounds represented by Formulas 2-1 to 2-7:[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
[화학식 2-3][Formula 2-3]
[화학식 2-4][Formula 2-4]
[화학식 2-5][Formula 2-5]
[화학식 2-6] [Formula 2-6]
[화학식 2-7] [Formula 2-7]
상기 식들에서 Ar1, Ar2, Ar3, Ar4, Ar5는 각각 독립적으로 상기 화학식 2의 Ar의 정의와 같으며, Ar 1 , Ar 2 , Ar 3 , Ar 4, Ar 5 in the formulas are each independently the same as the definition of Ar of Formula 2,R1, R2, R3, R4는 상기 화학식 2의 r1 내지 r8의 정의와 같으며, R 1 , R 2 , R 3 , and R 4 are the same as defined in r 1 to r 8 of Chemical Formula 2,a, b는 각각 독립적으로 0 내지 3의 정수이다.a and b are the integers of 0-3 each independently. - 제8항에 있어서,The method of claim 8,상기 화학식 2로 표시되는 화합물이 하기 화학식 2-3인 유기발광소자.An organic light emitting device of which the compound represented by Formula 2 is represented by Formula 2-3.[화학식 2-3][Formula 2-3]
상기 식에서 Ar1, Ar2, Ar3는 각각 독립적으로 상기 화학식 2의 Ar의 정의와 같으며, Wherein Ar 1 , Ar 2 , and Ar 3 are each independently the same as the definition of Ar in Formula 2,R1, R2는 상기 화학식 2의 r1 내지 r8의 정의와 같으며, R 1 and R 2 are the same as defined in r 1 to r 8 of Chemical Formula 2,a는 0 내지 3의 정수이다.a is an integer of 0-3. - 제7항에 있어서,The method of claim 7, wherein상기 화학식 2로 표시되는 화합물이 하기 화학식들 중 어느 하나인 유기발광소자:An organic light emitting device in which the compound represented by Formula 2 is any one of the following Formulas:
- 제7항에 있어서,The method of claim 7, wherein상기 발광호스트 1 및 2를 통하여 형성된 엑시플렉스 발광파장이 400-650 nm인 유기발광소자.An organic light emitting diode having an exciplex light emitting wavelength formed through the light emitting hosts 1 and 2 is 400-650 nm.
- 제7항에 있어서,The method of claim 7, wherein상기 녹색발광호스트 1 및 2를 통하여 형성된 엑시플렉스 발광파장이 450~500nm인 유기발광소자.An organic light emitting diode having an exciplex emission wavelength of 450 to 500 nm formed through the green light emitting hosts 1 and 2.
- 제7항에 있어서,The method of claim 7, wherein상기 발광호스트로써 화학식 1 및 화학식2의 혼합비율이 중량비율로 9:1내지 2:8인 유기발광소자.An organic light emitting diode according to claim 1, wherein the mixing ratio of Chemical Formula 1 and Chemical Formula 2 is 9: 1 to 2: 8 by weight.
- 제7항에 있어서,The method of claim 7, wherein상기 발광호스트 1 및 2를 통하여 형성된 엑시플렉스 발광파장이 발광층의 게스트인 도판트의 발광파장보다 단파장에서 형성되는 것을 특징으로 하는 유기발광소자.And an exciplex light emitting wavelength formed through the light emitting hosts 1 and 2 is formed at a shorter wavelength than that of a dopant which is a guest of the light emitting layer.
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| US11903311B2 (en) | 2016-07-20 | 2024-02-13 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101091803B1 (en) * | 2009-07-07 | 2011-12-08 | 서울대학교산학협력단 | Nickel catalyst supported on porous zirconia containing metal oxide stabilizer, preparation method thereof and method for producing hydrogen by autothermal reforming of ethanol using said catalyst |
| KR101531612B1 (en) * | 2010-12-02 | 2015-06-25 | 제일모직 주식회사 | Compound for organic photoelectric device and organic photoelectric device including the same |
| KR20120129733A (en) * | 2011-05-20 | 2012-11-28 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
| KR101600453B1 (en) * | 2013-09-13 | 2016-03-08 | 주식회사 엠비케이 | New organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR101764969B1 (en) * | 2014-05-26 | 2017-08-04 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
-
2015
- 2015-12-29 WO PCT/KR2015/014444 patent/WO2016108596A2/en active Application Filing
-
2023
- 2023-11-24 KR KR1020230165052A patent/KR20230169876A/en not_active Application Discontinuation
- 2023-11-24 KR KR1020230165053A patent/KR20230169001A/en not_active Application Discontinuation
- 2023-11-24 KR KR1020230165051A patent/KR20230164634A/en not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20230164634A (en) | 2023-12-04 |
| KR20230169876A (en) | 2023-12-18 |
| WO2016108596A3 (en) | 2016-09-15 |
| KR20230169001A (en) | 2023-12-15 |
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