WO2016108596A2 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
light emitting
halogen
deuterium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2015/014444
Other languages
English (en)
Korean (ko)
Other versions
WO2016108596A3 (fr
Inventor
함호완
김봉기
김성훈
안현철
김희주
김동준
이형진
임동환
안자은
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongjin Semichem Co Ltd
Original Assignee
Dongjin Semichem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dongjin Semichem Co Ltd filed Critical Dongjin Semichem Co Ltd
Priority to CN202011404218.5A priority Critical patent/CN112457844B/zh
Priority to CN201580071738.XA priority patent/CN107108585B/zh
Priority claimed from KR1020150188867A external-priority patent/KR20160080090A/ko
Publication of WO2016108596A2 publication Critical patent/WO2016108596A2/fr
Publication of WO2016108596A3 publication Critical patent/WO2016108596A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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.

Landscapes

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

Abstract

Cette invention concerne un nouveau composé applicable à une couche électroluminescente, une couche d'injection d'électrons, une couche de transport d'électrons, ou une couche de suppression de trous de dispositif électroluminescent organique. L'utilisation conjointe du nouveau composé selon l'invention et de dérivés de carbazole à titre d'hôte du dispositif électroluminescent organique permet de contrôler correctement une longueur d'onde exciplexe et de maximiser ce faisant l'efficacité et la durée de vie du dispositif électroluminescent organique.
PCT/KR2015/014444 2014-12-29 2015-12-29 Nouveau composé et dispositif électroluminescent organique le comprenant Ceased WO2016108596A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202011404218.5A CN112457844B (zh) 2014-12-29 2015-12-29 新颖化合物及包含其的有机发光器件
CN201580071738.XA CN107108585B (zh) 2014-12-29 2015-12-29 新颖化合物及包含其的有机发光器件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2014-0192192 2014-12-29
KR20140192192 2014-12-29
KR1020150188867A KR20160080090A (ko) 2014-12-29 2015-12-29 신규한 화합물 및 이를 포함하는 유기발광소자
KR10-2015-0188867 2015-12-29

Publications (2)

Publication Number Publication Date
WO2016108596A2 true WO2016108596A2 (fr) 2016-07-07
WO2016108596A3 WO2016108596A3 (fr) 2016-09-15

Family

ID=56285122

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2015/014444 Ceased WO2016108596A2 (fr) 2014-12-29 2015-12-29 Nouveau composé et dispositif électroluminescent organique le comprenant

Country Status (2)

Country Link
KR (3) KR20230164634A (fr)
WO (1) WO2016108596A2 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102017119592B3 (de) * 2017-08-25 2018-11-08 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
WO2018225940A1 (fr) * 2017-06-07 2018-12-13 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2019049965A1 (fr) * 2017-09-11 2019-03-14 保土谷化学工業株式会社 Composé à structure cyclique de de type pyrimidine et élément électroluminescent organique
WO2019164301A1 (fr) * 2018-02-21 2019-08-29 주식회사 엘지화학 Composé et diode électroluminescente organique le comprenant
CN110225909A (zh) * 2017-06-07 2019-09-10 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
CN110520419A (zh) * 2017-07-19 2019-11-29 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
WO2020040571A1 (fr) * 2018-08-22 2020-02-27 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2020053689A1 (fr) * 2018-09-14 2020-03-19 Semiconductor Energy Laboratory Co., Ltd. Élément électroluminescent, appareil électroluminescent, dispositif électronique et dispositif d'éclairage
CN111315740A (zh) * 2017-09-15 2020-06-19 喜星素材株式会社 杂环化合物与包含其的有机发光装置
US10919880B2 (en) 2017-08-25 2021-02-16 Cynora Gmbh Organic molecules, in particular for use in optoelectronic devices
JP2021521254A (ja) * 2018-08-22 2021-08-26 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
CN114163421A (zh) * 2016-11-07 2022-03-11 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
US11685859B2 (en) 2017-12-12 2023-06-27 Lg Chem, Ltd. Organic light emitting device
US11700768B2 (en) 2017-04-27 2023-07-11 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
US11903311B2 (en) 2016-07-20 2024-02-13 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
US12492191B2 (en) * 2019-10-18 2025-12-09 Lg Chem, Ltd. Organic light emitting device

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101091803B1 (ko) * 2009-07-07 2011-12-08 서울대학교산학협력단 금속산화물 안정화제를 포함한 다공성 지르코니아 담체에 담지된 니켈 촉매, 그 제조방법 및 상기 촉매를 이용한 에탄올의 자열개질반응에 의한 수소 제조방법
KR101531612B1 (ko) * 2010-12-02 2015-06-25 제일모직 주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20120129733A (ko) * 2011-05-20 2012-11-28 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
WO2014021280A1 (fr) * 2012-07-31 2014-02-06 出光興産株式会社 Élément organique électroluminescent
KR101600453B1 (ko) * 2013-09-13 2016-03-08 주식회사 엠비케이 신규한 유기발광화합물 및 이를 포함하는 유기전기발광소자
KR101764969B1 (ko) * 2014-05-26 2017-08-04 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12167689B2 (en) 2016-07-20 2024-12-10 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
US11903311B2 (en) 2016-07-20 2024-02-13 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
CN114163421A (zh) * 2016-11-07 2022-03-11 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
US11700768B2 (en) 2017-04-27 2023-07-11 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
CN110225909A (zh) * 2017-06-07 2019-09-10 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
US12421215B2 (en) 2017-06-07 2025-09-23 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
WO2018225940A1 (fr) * 2017-06-07 2018-12-13 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
CN110520419A (zh) * 2017-07-19 2019-11-29 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
US11851423B2 (en) * 2017-07-19 2023-12-26 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
CN110520419B (zh) * 2017-07-19 2023-05-26 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
DE102017119592B3 (de) * 2017-08-25 2018-11-08 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen
US10919880B2 (en) 2017-08-25 2021-02-16 Cynora Gmbh Organic molecules, in particular for use in optoelectronic devices
US12221430B2 (en) 2017-09-11 2025-02-11 Hodogaya Chemical Co., Ltd. Compound having pyrimidine ring structure and organic electroluminescence device
JPWO2019049965A1 (ja) * 2017-09-11 2020-08-20 保土谷化学工業株式会社 ピリミジン環構造を有する化合物および有機エレクトロルミネッセンス素子
WO2019049965A1 (fr) * 2017-09-11 2019-03-14 保土谷化学工業株式会社 Composé à structure cyclique de de type pyrimidine et élément électroluminescent organique
JP7159173B2 (ja) 2017-09-11 2022-10-24 保土谷化学工業株式会社 ピリミジン環構造を有する化合物および有機エレクトロルミネッセンス素子
JP2022166299A (ja) * 2017-09-15 2022-11-01 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
CN111315740A (zh) * 2017-09-15 2020-06-19 喜星素材株式会社 杂环化合物与包含其的有机发光装置
US11515484B2 (en) 2017-09-15 2022-11-29 Lt Materials Co., Ltd. Heterocyclic compound and organic light emitting element comprising same
JP2025076476A (ja) * 2017-09-15 2025-05-15 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物およびこれを含む有機発光素子
JP2021501126A (ja) * 2017-09-15 2021-01-14 エルティー・マテリアルズ・カンパニー・リミテッドＬＴ Ｍａｔｅｒｉａｌｓ Ｃｏ．， Ｌｔｄ． ヘテロ環化合物およびこれを含む有機発光素子
US11685859B2 (en) 2017-12-12 2023-06-27 Lg Chem, Ltd. Organic light emitting device
WO2019164301A1 (fr) * 2018-02-21 2019-08-29 주식회사 엘지화학 Composé et diode électroluminescente organique le comprenant
WO2020040571A1 (fr) * 2018-08-22 2020-02-27 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
US12096686B2 (en) 2018-08-22 2024-09-17 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
JP2021521254A (ja) * 2018-08-22 2021-08-26 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
JP2020047921A (ja) * 2018-09-14 2020-03-26 株式会社半導体エネルギー研究所 発光デバイス、発光装置、電子機器、および照明装置
JP7537866B2 (ja) 2018-09-14 2024-08-21 株式会社半導体エネルギー研究所 発光デバイス、発光装置、電子機器、および照明装置
US12120900B2 (en) 2018-09-14 2024-10-15 Semiconductor Energy Laboratory Co., Ltd. Light-emitting device, light-emitting apparatus, electronic device, and lighting device
WO2020053689A1 (fr) * 2018-09-14 2020-03-19 Semiconductor Energy Laboratory Co., Ltd. Élément électroluminescent, appareil électroluminescent, dispositif électronique et dispositif d'éclairage
JP7170930B1 (ja) 2018-09-14 2022-11-14 株式会社半導体エネルギー研究所 発光デバイス、発光装置、電子機器、および照明装置
JP2022174178A (ja) * 2018-09-14 2022-11-22 株式会社半導体エネルギー研究所 発光デバイス、発光装置、電子機器、および照明装置
US12492191B2 (en) * 2019-10-18 2025-12-09 Lg Chem, Ltd. Organic light emitting device

Also Published As

Publication number Publication date
WO2016108596A3 (fr) 2016-09-15
KR20230169876A (ko) 2023-12-18
KR20230164634A (ko) 2023-12-04
KR102774124B1 (ko) 2025-03-04
KR102776293B1 (ko) 2025-03-04
KR20230169001A (ko) 2023-12-15

Similar Documents

Publication Publication Date Title
WO2016108596A2 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020106032A1 (fr) Nouveau composé de bore et dispositif électroluminescent organique le comprenant
WO2019054833A1 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2016117848A1 (fr) Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci
WO2011081423A2 (fr) Composé de triphénylène et dispositif à électroluminescence organique incluant celui-ci
WO2020050619A1 (fr) Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2019235902A1 (fr) Composé polycyclique et élément électronique organique le comprenant
WO2020138963A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2013191428A1 (fr) Composé hétérocyclique contenant de l'azote et élément électronique organique comprenant ce composé
WO2017065415A1 (fr) Diode électroluminescente organique présentant un taux amélioré de réduction de la luminance dans la zone des niveaux de gris inférieurs
WO2022050710A1 (fr) Composé dérivé aromatique polycyclique et dispositif électroluminescent organique l'utilisant
WO2019164218A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2016089165A2 (fr) Nouveau composé et élément électroluminescent le comprenant
WO2019108033A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2020159279A1 (fr) Composé polycyclique et élément électroluminescent organique le comprenant
WO2021015417A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique
WO2022086124A1 (fr) Composé polycyclique et dispositif électroluminescent organique l'utilisant
WO2020138964A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2020009363A1 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2020096421A1 (fr) Composé hétérocyclique et diode électroluminescente organique le comprenant
WO2022108258A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2023128521A1 (fr) Dispositif électroluminescent organique
WO2016021923A2 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2016060463A2 (fr) Nouveau composé et élément électroluminescent organique comprenant le nouveau composé
WO2024091024A1 (fr) Composé et dispositif électroluminescent organique le comprenant

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 201580071738.X

Country of ref document: CN

122 Ep: pct application non-entry in european phase

Ref document number: 15875690

Country of ref document: EP

Kind code of ref document: A2