WO2018212463A1 - Composé électroluminescent organique, et élément électroluminescent organique l'utilisant - Google Patents

Composé électroluminescent organique, et élément électroluminescent organique l'utilisant Download PDF

Info

Publication number
WO2018212463A1
WO2018212463A1 PCT/KR2018/004346 KR2018004346W WO2018212463A1 WO 2018212463 A1 WO2018212463 A1 WO 2018212463A1 KR 2018004346 W KR2018004346 W KR 2018004346W WO 2018212463 A1 WO2018212463 A1 WO 2018212463A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
mmol
formula
aryl
compound
Prior art date
Application number
PCT/KR2018/004346
Other languages
English (en)
Korean (ko)
Inventor
손호준
김영배
배형찬
Original Assignee
주식회사 두산
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 주식회사 두산 filed Critical 주식회사 두산
Publication of WO2018212463A1 publication Critical patent/WO2018212463A1/fr

Links

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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/24—[b,e]-condensed with two six-membered rings
    • 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
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • H10K85/657—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent electron transport ability, and the compound in at least one organic material layer, such as characteristics such as luminous efficiency, driving voltage, lifetime This is an improved organic electroluminescent device.
  • organic electroluminescent (EL) devices led to blue electroluminescence using anthracene single crystals in 1950, when Bernanose observed organic thin film emission.
  • organic EL devices proposed an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer, and then, in order to make a high efficiency and long life organic EL device, each characteristic organic material layer in the device was introduced. This has led to the development of specialized materials used for this.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 hole blocking layer
  • anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
  • phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials. Is being used.
  • CBP has shown excellent properties as a phosphorescent host material.
  • An object of the present invention is to provide a novel compound that can be used as a hole transport layer material, an electron transport layer material having excellent hole injection ability, hole transport ability, electron injection ability, electron transport ability and the like.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel compound having a low driving voltage, high luminous efficiency, and an improved lifetime.
  • an example of the present invention provides a compound represented by the following formula (1).
  • a and B are the same as or different from each other, and are independently represented by the following formula (2),
  • L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nucleus Heterocycloalkyl group of 3 to 40 atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group selected from the group or combine with adjacent groups to form a
  • the arylene group and heteroarylene group of L are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear aryl, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40
  • another example of the present invention is an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above. It provides an organic electroluminescent device comprising the compound represented.
  • the at least one organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, and is preferably used as a hole transport layer and / or an electron transport layer material.
  • the organic material layer material of the organic electroluminescent device preferably the electron transport layer material, or It can be used as a hole transport layer material.
  • the organic electroluminescent device including the compound according to an example of the present invention in the hole transport layer or the electron transport layer can be greatly improved in terms of driving voltage, efficiency, lifetime, and the like. Can be applied effectively.
  • the organic compound of the present invention is a compound having, as a basic skeleton, a structure in which two or more substituents are linked directly or through a linker group to an oxathylene-based mother core, and has a structure represented by Chemical Formula 1.
  • the compound represented by Formula 1 of the present invention has a structure in which two or more electron withdrawing groups (EWG) are connected directly or through a linker group to one phenyl group portion of oxanthylene, or one phenyl group of oxanthylene Two or more arylamines, etc., in the portion have a structure connected directly or through a linker group.
  • EWG electron withdrawing groups
  • Such compounds include oxanthylene-based nuclei having high electron donating group (EDG) properties and substituents having high electron-absorbing electron withdrawing properties (eg, N-containing heterocycles, aromatic rings, and arylamines). Etc.) are formed by combining.
  • EDG electron donating group
  • substituents having high electron-absorbing electron withdrawing properties eg, N-containing heterocycles, aromatic rings, and arylamines.
  • Etc. are formed by combining.
  • the compound of Formula 1 may be used as an organic material layer material, preferably a hole transport layer material and an electron transport layer material of the organic EL device.
  • the compound represented by the formula (1) by introducing a variety of aromatic ring substituents significantly increase the molecular weight of the compound, the glass transition temperature can be improved, thereby higher thermal than conventional CBP (4,4-dicarbazolylphenyl) It may have stability.
  • the organic electroluminescent device including the compound according to the present invention may be effectively improved in durability and lifespan even in suppressing crystallization of the organic material layer.
  • the compound represented by Formula 1 of the present invention can be used as an organic material layer material of the organic electroluminescent device, preferably a hole transport layer / electron transport layer material.
  • the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
  • An organic compound according to one embodiment of the present invention is represented by the following formula (1).
  • a and B are the same as or different from each other, and are independently represented by the following formula (2),
  • L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nucleus Heterocycloalkyl group of 3 to 40 atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , aryloxy group of C 6 to C 60 , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group selected from the group or combine with adjacent groups to form a
  • the arylene group and heteroarylene group of L are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear aryl, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40
  • R in Chemical Formula 2 may be a substituent represented by the following Chemical Formula 3.
  • Z 1 to Z 5 are independently C (R 1 ) or N, at least one of which is N;
  • R 1 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha It is selected from the group consisting of a nil group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group.
  • R in Formula 2 may be selected from the group consisting of S 1 to S 49 , but is not limited thereto.
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 5.
  • L 1 and L 2 are the same as or different from each other, and are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 2 and R 3 are hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
  • Z 6 to Z 11 are independently C (R 4 ) or N, at least one being N;
  • p and q are independently 1 or 2;
  • R 4 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha It is selected from the group consisting of a nil group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group.
  • Chemical Formula 5 may be any one of the following Chemical Formulas 7 to 9.
  • L 1 , L 2 , R 2 , R 3 , Z 6 to Z 11 , p and q are each as defined in Chemical Formula 5.
  • R in Chemical Formula 2 may be a substituent represented by the following Chemical Formula 4.
  • Ar 2 and Ar 3 independently represent a substituted or unsubstituted aryl group, and Ar 2 and Ar 3 may form a nitrogen-containing heterocycle together with the nitrogen to which they are bonded.
  • R in Formula 2 may be selected from the group consisting of S 50 to S 56 , but is not limited thereto.
  • the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 6.
  • L 3 and L 4 are the same as or different from each other, and each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms;
  • Ar 4 to Ar 7 independently represent a substituted or unsubstituted aryl group, and Ar 4 and Ar 5 and Ar 6 and Ar 7 may form a nitrogen-containing heterocycle together with the nitrogen to which they are bonded.
  • Chemical Formula 6 may be any one of the following Chemical Formulas 10 to 12.
  • L 3 , L 4 and Ar 4 to Ar 7 are the same as defined in Chemical Formula 6.
  • the compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • alkyl refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples of which are methyl, ethyl, propyl, isobutyl, sec -Butyl, pentyl, iso-amyl, hexyl and the like.
  • Cycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms. Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and having at least one carbon of the ring, preferably 1 to 3 carbon atoms. Carbon is substituted with a hetero atom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine and the like.
  • Aryl means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • Heteroaryl is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons It is substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indole Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-iso Sazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Alkoxyoxy means a monovalent functional group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms, which may include a linear, branched or cyclic structure. Can be. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Aryloxy means a monovalent functional group represented by R “O-, and said R" is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • alkylboron group is alkyl having 1 to 40 carbon atoms.
  • Means an boron group substituted with "aryl boron group” means a boron group substituted with an aryl having 6 to 60 carbon atoms
  • arylphosphine group means a phosphine group substituted with an aryl having 1 to 60 carbon atoms
  • Arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • the compound represented by Formula 1 according to the present invention may be synthesized according to a general synthetic method. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device includes an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, at least one of the at least one organic material layer is It is characterized by including the compound represented by 1.
  • the compound may include one kind or two or more kinds.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1).
  • the organic material layer including the compound of Formula 1 may be a hole transport layer and / or an electron transport layer.
  • the structure of the organic electroluminescent device according to the present invention is not particularly limited, and may be, for example, a structure in which one or more organic layers are stacked between electrodes.
  • Non-limiting examples thereof include (1) an anode, a light emitting layer, a cathode; (2) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode; Or (3) structures such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode.
  • the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device according to the present invention is an organic material layer and an electrode using materials and methods known in the art, except that at least one or more layers of the organic material layer are formed to include the compound represented by Formula 1 of the present invention. It can be prepared by forming a.
  • the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet can be used.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • 1,4-dibromodibenzo [b, e] [1,4] dioxine (50.0 g, 146.2 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2' -bi (1,3,2-dioxaborolane) (74.3 g, 292.4 mmol) and Pd (dppf) 2 (3.6 g, 4.4 mmol), KOAc (28.7 g, 292.4 mmol) in 1000 mL Toluene, 200 mL EtOH, H It was added to 200 ml of 2 O and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 1 (20.0 g, 45.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH, and 100 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 1 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.8 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H 2 O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • the target compound 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-2-yl) -1,3,5-triazine (22.1 g, yield 78%) Got it.
  • Target compound of Preparation Example 1 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.7 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H 2 O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 2 (20.0 g, 45.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH, and 100 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 2 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.8 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H 2 O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • the target compound 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine (22.1 g, yield 78%) Got it.
  • Target compound of Preparation Example 2 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.7 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H 2 O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 3 (20.0 g, 45.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH, and 100 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 3 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.8 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H 2 O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • the target compound 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (4- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine (22.1 g, yield 78%) Got it.
  • Target compound of Preparation Example 3 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.7 g, 45.9 mmol) and Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol) and K 2 CO 3 (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H 2 O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered.
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 ( 0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-3 (3.8 g, yield 70%) by column chromatography.
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 ( 0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound A-6 (4.0 g, 72% yield).
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-9 (3.7 g, yield 65%) using column chromatography.
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-14 (3.5 g, yield 60%) using column chromatography.
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (4.9 g , 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-17 (3.8 g, 64% yield) using column chromatography.
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 ( 0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound B-3 (3.8 g, yield 70%) by column chromatography.
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 ( 0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain the title compound B-6 (4.0 g, 72% yield).
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-9 (3.7 g, yield 65%).
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-14 (3.5 g, yield 60%).
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (4.9 g , 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-17 (3.8 g, 64% yield).
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 4-chloro-2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-23 (3.3 g, yield 60%).
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 ( 0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-3 (3.8 g, yield 70%).
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 ( 0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-6 (4.0 g, 72% yield).
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-9 (3.7 g, yield 65%).
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-14 (3.5 g, yield 60%).
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (4.9 g , 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain a target compound C-17 (3.8 g, yield 64%) by column chromatography.
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 4-chloro-2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (4.7 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol) and K 2 CO 3 (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-23 (3.3 g, yield 60%).
  • Target compound of Preparation Example 4 (3 g, 5.5 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g, 5.5 mmol) and Pd (PPh 3 ) 4 ( 0.3 g, 0.3 mmol) and K 2 CO 3 (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound D-2 (2.6 g, 65% yield).
  • Target compound of Preparation Example 4 (3 g, 5.5 mmol) and 4- (4-chlorophenyl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (2.3 g, 5.5 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.3 mmol) and K 2 CO 3 (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound D-8 (2.7 g, 62% yield) using column chromatography.
  • Target compound of Preparation Example 5 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (1.7 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.2 g, 0.3 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound E-9 (2.7 g, 67% yield) by column chromatography.
  • Target compound of Preparation Example 5 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (1.8 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.2 g, 0.3 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the target compound E-10 (2.5 g, 61% yield).
  • Target compound of Preparation Example 6 (3 g, 4.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-3-yl) -6-phenyl-1,3,5-triazine (1.9 g , 4.9 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound F-11 (2.7 g, 66% yield) using column chromatography.
  • Target compound of Preparation Example 6 (3 g, 4.9 mmol) and (4-cyanophenyl) boronic acid (0.7 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol), K 2 CO 3 (2.0 g , 14.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound F-12 (1.9 g, 66% yield) by column chromatography.
  • Target compound of Preparation Example 7 (3 g, 5.5 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g, 5.5 mmol) and Pd (PPh 3 ) 4 ( 0.3 g, 0.3 mmol) and K 2 CO 3 (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound G-2 (2.6 g, yield 65%).
  • Target compound of Preparation Example 7 (3 g, 5.5 mmol) and 4- (4-chlorophenyl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (2.3 g, 5.5 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.3 mmol) and K 2 CO 3 (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound G-8 (2.7 g, 62% yield).
  • Target compound of Preparation Example 8 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (1.7 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.2 g, 0.3 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound H-9 (2.7 g, yield 67%).
  • Target compound of Preparation Example 8 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (1.8 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.2 g, 0.3 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound H-10 (2.5 g, 61% yield).
  • Target compound of Preparation Example 9 (3 g, 4.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-3-yl) -6-phenyl-1,3,5-triazine (1.9 g , 4.9 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound I-11 (2.7 g, 66% yield).
  • Target compound of Preparation Example 9 (3 g, 4.9 mmol) and (4-cyanophenyl) boronic acid (0.7 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol), K 2 CO 3 (2.0 g , 14.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound I-12 (1.9 g, yield 66%).
  • Target compound of Preparation Example 10 (3 g, 5.5 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g, 5.5 mmol) and Pd (PPh 3 ) 4 ( 0.3 g, 0.3 mmol) and K 2 CO 3 (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to give the title compound J-2 (2.6 g, yield 65%).
  • Target compound of Preparation Example 10 (3 g, 5.5 mmol) and 4- (4-chlorophenyl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (2.3 g, 5.5 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.3 mmol) and K 2 CO 3 (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to give the title compound J-8 (2.7 g, 62% yield).
  • Target compound of Preparation Example 11 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (1.7 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.2 g, 0.3 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound K-9 (2.7 g, 67% yield).
  • Target compound of Preparation Example 11 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (1.8 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.2 g, 0.3 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound K-10 (2.5 g, 61% yield).
  • Target compound of Preparation Example 12 (3 g, 4.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-3-yl) -6-phenyl-1,3,5-triazine (1.9 g , 4.9 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol) and K 2 CO 3 (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound L-11 (2.7 g, 66% yield) using column chromatography.
  • Target compound of Preparation Example 12 (3 g, 4.9 mmol) and (4-cyanophenyl) boronic acid (0.7 g, 4.9 mmol) and Pd (PPh 3 ) 4 (0.3 g, 0.2 mmol), K 2 CO 3 (2.0 g , 14.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound L-12 (1.9 g, yield 66%).
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol), 4-bromo-N, N-diphenylaniline (4.5 g, 13.8 mmol), Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol), K 2 CO 3 ( 2.8 g, 20.6 mmol) was added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound M-2 (3.3 g, yield 71%).
  • Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 9- (4-bromophenyl) -9H-carbazole (4.4 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol), K 2 CO 3 (2.8 g, 20.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound M-6 (3.1 g, yield 68%).
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol), 4-bromo-N, N-diphenylaniline (4.5 g, 13.8 mmol), Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol), K 2 CO 3 ( 2.8 g, 20.6 mmol) was added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound N-2 (3.0 g, yield 65%) using column chromatography.
  • Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 9- (4-bromophenyl) -9H-carbazole (4.4 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol), K 2 CO 3 (2.8 g, 20.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound N-6 (2.9 g, yield 63%) by column chromatography.
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol), 4-bromo-N, N-diphenylaniline (4.5 g, 13.8 mmol), Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol), K 2 CO 3 ( 2.8 g, 20.6 mmol) was added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound O-2 (2.7 g, yield 60%).
  • Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 9- (4-bromophenyl) -9H-carbazole (4.4 g, 13.8 mmol) and Pd (PPh 3 ) 4 (0.4 g, 0.3 mmol), K 2 CO 3 (2.8 g, 20.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H 2 O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound O-6 (2.9 g, yield 63%).
  • Compound A-3 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows. Glass substrates were washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • a blue organic electroluminescent device was manufactured as follows. Glass substrates were washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • DS-205 Doosan Electronics, 80 nm
  • NPB 15 nm
  • ADN 5%
  • DS-405 Doosan Electronics, 30 nm
  • Compound A-3 30 nm
  • LiF (1 nm) / Al 200 nm
  • a blue organic EL device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound A-3 as the electron transporting layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET-1 instead of Compound A-3 was used as the electron transporting layer material.
  • a blue organic EL device was manufactured in the same manner as in Example 1, except that Compound A-3 was not used as the electron transporting material.
  • Example 1 A-3 3.4 458 6.8
  • Example 2 A-6 3.6 456 6.9
  • Example 3 A-9 3.2 457 6.8
  • Example 4 A-14 3.2 456 7.0
  • Example 5 A-17 4.6 457 7.1
  • Example 6 A-23 3.6 456 6.7
  • Example 7 B-3 3.9 456 6.9
  • Example 8 B-6 3.6 457 6.7
  • Example 9 B-9 3.6 456 7.0
  • Example 10 B-14 3.2 457 7.1
  • Example 11 B-17 3.2 456 6.8
  • Example 12 B-23 3.6 456 6.9
  • Example 13 C-3 3.9 457 6.9
  • Example 14 C-6 3.9 452 6.8
  • Example 15 C-9 3.3 448 6.7
  • Example 17 C-17 4.1 456 6.9
  • Example 18 C-23 3.2 456 6.8
  • Example 19 D-2 3.2 457 6.4
  • Example 20 D-8 4.1 465 6.8
  • Example 21 E-9 3.7 455 6.9
  • the blue organic electroluminescent devices (Examples 1 to 36) using the compound represented by Chemical Formula 1 according to the present invention in the electron transporting layer include a blue organic electroluminescent device using a conventional Alq3 as the electron transporting layer ( Compared with the comparative example 1) and the blue organic electroluminescent element (comparative example 2) without an electron carrying layer, it turned out that it shows the outstanding performance in driving voltage, light emission peak, and a current efficiency.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 37, except that NPB was used instead of the compound M-2 used as the hole transport layer in Example 37.
  • the blue organic EL device (Examples 37 to 42) using the compound represented by Formula 1 according to the present invention as a hole transporting layer material is an organic electroluminescent device using conventional NPB as the hole transporting layer material. Compared with (Comparative Example 4), it was found to show better performance in terms of current efficiency and driving voltage.

Landscapes

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

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le contenant. Selon la présente invention, le composé est utilisé pour une couche organique de l'élément électroluminescent organique, de préférence, pour une couche d'injection de trous, une couche de transport de trous, une couche électroluminescente, une couche de transport d'électrons ou une couche d'injection d'électrons de manière à permettre l'amélioration de l'efficacité d'émission de lumière, de la tension de commande, de la durée de vie et similaires de l'élément électroluminescent organique.
PCT/KR2018/004346 2017-05-16 2018-04-13 Composé électroluminescent organique, et élément électroluminescent organique l'utilisant WO2018212463A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020170060509A KR102424983B1 (ko) 2017-05-16 2017-05-16 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR10-2017-0060509 2017-05-16

Publications (1)

Publication Number Publication Date
WO2018212463A1 true WO2018212463A1 (fr) 2018-11-22

Family

ID=64274193

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/004346 WO2018212463A1 (fr) 2017-05-16 2018-04-13 Composé électroluminescent organique, et élément électroluminescent organique l'utilisant

Country Status (2)

Country Link
KR (1) KR102424983B1 (fr)
WO (1) WO2018212463A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102236281B1 (ko) * 2018-08-17 2021-04-05 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20200067064A (ko) * 2018-12-03 2020-06-11 두산솔루스 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20200075614A (ko) * 2018-12-18 2020-06-26 두산솔루스 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140025120A (ko) * 2012-08-21 2014-03-04 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20140134884A (ko) * 2013-05-15 2014-11-25 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150077263A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR20160141672A (ko) * 2015-06-01 2016-12-09 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20170026813A (ko) * 2015-08-28 2017-03-09 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR0161417B1 (ko) 1995-07-11 1999-02-01 김광호 가스흐름이 개선된 종형확산로
KR102268119B1 (ko) * 2013-08-30 2021-06-21 엘지디스플레이 주식회사 파이렌 화합물 및 이를 포함하는 유기전계발광소자
KR102510392B1 (ko) * 2015-09-10 2023-03-16 삼성디스플레이 주식회사 카바졸계 화합물 및 이를 포함한 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140025120A (ko) * 2012-08-21 2014-03-04 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20140134884A (ko) * 2013-05-15 2014-11-25 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150077263A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR20160141672A (ko) * 2015-06-01 2016-12-09 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20170026813A (ko) * 2015-08-28 2017-03-09 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MATSUMOTO, M.: "Product class 2: 1,4-dioxins and benzo- and dibenzo-fused derivatives", SCIENCE OF SYNTHESIS, 2004, pages 15 - 38 *

Also Published As

Publication number Publication date
KR102424983B1 (ko) 2022-07-26
KR20180125775A (ko) 2018-11-26

Similar Documents

Publication Publication Date Title
WO2018038401A1 (fr) Composé organique et dispositif à électroluminescence organique comprenant un tel composé
WO2016089080A1 (fr) Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
WO2018110958A1 (fr) Composé électroluminescent organique et élément électroluminescent organique l'utilisant
WO2018216921A2 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2013094999A2 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2020141949A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2014142488A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2014010810A1 (fr) Nouveau composé et dispositif électroluminescent le comprenant
WO2011145876A2 (fr) Composé organique hybride innovant et dispositif électroluminescent organique l'utilisant
WO2017179809A1 (fr) Composé organique électroluminescent et élément électroluminescent organique l'utilisant
WO2011081451A2 (fr) Composés triphénylés, et dispositif électroluminescent organique les utilisant
WO2014092354A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020027463A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2016105054A2 (fr) Composé organique luminescent et élément électroluminescent organique faisant appel audit composé
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2014027814A1 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2015125986A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2017023125A1 (fr) Composé organique photoémetteur et dispositif électroluminescent organique l'utilisant
WO2018147638A1 (fr) Composé organique et élément électroluminescent organique l'utilisant
WO2020009381A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2017105041A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18802807

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 120A DATED 09.03.2020)

122 Ep: pct application non-entry in european phase

Ref document number: 18802807

Country of ref document: EP

Kind code of ref document: A1