WO2014065498A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2014065498A1
WO2014065498A1 PCT/KR2013/007669 KR2013007669W WO2014065498A1 WO 2014065498 A1 WO2014065498 A1 WO 2014065498A1 KR 2013007669 W KR2013007669 W KR 2013007669W WO 2014065498 A1 WO2014065498 A1 WO 2014065498A1
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group
synthesis
inv
mol
formula
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김태형
엄민식
김회문
백영미
박호철
이창준
신진용
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주식회사 두산
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifetime.
  • 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 a function.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
  • a host / dopant system may be used as a light emitting material.
  • 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.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are known as hole injection materials and electron transport materials, and anthracene derivatives are known as light emitting materials.
  • metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are blue, green, and red phosphorescent dopant materials.
  • CBP is used as a phosphorescent host material.
  • the conventional luminescent material has good luminescence properties, but the glass transition temperature is low, so the thermal stability is not good, and thus it is not a satisfactory level in terms of the lifetime of the organic EL device. Therefore, there is a demand for the development of an organic electroluminescent device including a light emitting material having excellent performance.
  • An object of the present invention is to provide an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifetime in order to solve the above problems.
  • the present invention to achieve the above object; 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 comprises a compound represented by Formula 1 and a compound represented by Formula 3 below. It provides an organic electroluminescent device.
  • Y 1 to Y 4 are each independently N or CR 3 , and one of Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 forms a condensed ring represented by the following Chemical Formula 2,
  • the dotted line means a site where condensation occurs with the compound of Formula 1, and Y 5 to Y 8 are each independently N or CR 4 ,
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein At least one of X 1 and X 2 is N (Ar 1 ),
  • R 1 to R 4 and Ar 1 to Ar 5 are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C Alkynyl group of 2 to C 40 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ aryloxy C 60, C 1 ⁇ C 40 alkyl silyl group, C 6 ⁇ aryl silyl group of C 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 is selected from ⁇ C 60 aryl boron group, the group consisting of C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C
  • R 1 to R 4 may be bonded to an adjacent group to form a condensed ring
  • Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60
  • XY is an organic ligand
  • X is an aryl heteroaryl of nuclear atoms of 3 to 40 group
  • Y is a C 6 ⁇ C 40 heteroaryl group of the aryl group or nuclear atoms of 3 to 40
  • R 11 to R 18 are each Independently, hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 the aryl group, the number of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ aryloxy C 60, C 1 ⁇ C 40 alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C
  • Alkyl used in the present invention means 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 thereof are methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl and the like.
  • Alkenyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl and the like.
  • Alkynyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
  • Non-limiting examples thereof include ethynyl, 2-propynyl and the like.
  • Cycloalkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon).
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl used in the present invention 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 preferably at least one carbon in the ring, preferably 1 To 3 carbons are substituted with a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • Aryl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms alone or in combination of two or more rings.
  • the two or more rings may be attached in a simple or condensed form with each other.
  • Non-limiting examples thereof include phenyl, biphenyl, triphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, indenyl and the like.
  • Heteroaryl used in the present invention 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 are substituted with heteroatoms 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; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Alkyloxy used in the present invention means a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and 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 used in the present invention means a monovalent functional group represented by R'O-, wherein R 'is an aryl having 6 to 60 carbon atoms.
  • R ' is an aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkylsilyl used in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • arylamine is substituted with aryl having 6 to 60 carbon atoms. Amine.
  • the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention provides 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 a compound represented by Formula 1 and the It provides an organic electroluminescent device comprising a compound represented by the formula (3).
  • Compound represented by the formula (1) is a condensed carbon ring or a condensed heterocyclic moiety, preferably a condensed heterocyclic moiety is connected to the indole-based skeleton, the energy level is controlled by a number of substituents wide band gap (sky blue ⁇ red) Therefore, when the compound represented by Formula 1 is used in the organic material layer of the organic electroluminescent device, the phosphorescence property may be improved, and the electron and / or hole transport ability and the light emitting ability may be enhanced.
  • the compound represented by Formula 1 of the present invention is preferably used in the hole transport layer, the electron transport layer and the light emitting layer of the organic material layer, and because of the indole-based skeleton exhibits excellent properties as a light emitting host material compared to the conventional CBP, More preferably used as the host material.
  • the compound represented by Chemical Formula 1 has various aromatic rings bonded to the indole-based backbone as a substituent to significantly increase the molecular weight of the compound, thereby improving glass transition temperature and higher thermal stability than conventional CBP.
  • the whole molecule has a bipolar (bipolar) nature of the various aromatic ring substituents, the binding force between the holes and the electrons can be increased, and thus it can exhibit excellent characteristics as a host material of the light emitting layer compared to the conventional CBP.
  • all of the compounds represented by the formula (1) that do not form a condensed ring in Y 1 to Y 4 is CR 3 , wherein a plurality of R 3 may be the same or different from each other.
  • all of Y 5 to Y 8 of the compound represented by Formula 1 are CR 4 , and at this time, a plurality of R 4 may be identical to or different from each other.
  • R 1 to R 4 of Formula 1 are each independently hydrogen, an aryl group of C 6 ⁇ C 60 (eg phenyl, naphthyl, bis Phenyl) or a heteroaryl group having 5 to 60 nuclear atoms (for example, pyridine).
  • aryl group of C 6 ⁇ C 60 eg phenyl, naphthyl, bis Phenyl
  • a heteroaryl group having 5 to 60 nuclear atoms for example, pyridine
  • the compound represented by the formula (1) of the present invention is preferably selected from the group consisting of the compound represented by the formula (1a) to 1f.
  • X 1 and X 2 of Formula 1 are each independently N (Ar 1 ) or S is preferred. That is, it is preferable that X 1 is N (Ar 1 ) and X 2 is S, X 1 is S and X 2 is N (Ar 1 ), or both X 1 and X 2 are N (Ar 1 ).
  • the compound represented by the formula (1) of the present invention may be more specifically selected from the group consisting of compounds represented by the following formula C1 to C66.
  • R 1 to R 4 are as defined above, wherein a plurality of R 3 and R 4 may be the same or different from each other.
  • Ar 1 to Ar 5 are sounds as defined above, particularly C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ C 60 of which is selected from the group consisting of an aryl amine It is preferable.
  • Ar 1 to Ar 5 are each independently selected from the following substituent (functional group) groups (S1-S192).
  • the compound represented by Chemical Formula 3 has an iridium (Ir) as its center, and an aromatic ring is connected to one side, and an organic ligand is connected to the other side.
  • the compound represented by Formula 3 of the present invention may increase the energy gap between the HOMO and triplet MLCT states because the organic ligand is linked. Therefore, when the compound represented by Chemical Formula 3 is used in the organic material layer of the organic EL device, specifically, the hole injection layer, the hole transport layer, and the light emitting layer, phosphorescence characteristics may be improved and color purity may be increased.
  • the present invention is a compound represented by the formula (1) as a host material of the light emitting layer so that energy can be efficiently transferred between the host / dopant,
  • the compound represented by Formula 3 as a dopant material of the light emitting layer, it is possible to provide an organic EL device having excellent color purity as well as driving voltage, luminous efficiency, and lifetime characteristics.
  • X and Y are bonded to each other to form an organic ligand represented by XY, wherein X is a heteroaryl group having 3 to 40 nuclear atoms, preferably N- and containing heteroaryl group, Y is a heteroaryl group of C 6 ⁇ C 40 aryl group or a nuclear atoms of 3 to 40.
  • the aryl group or heteroaryl group of X and Y is halogen, cyano group, amino group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 2 ⁇ C 40 alkenyl, C alkynyl group of 2 ⁇ C 40, C 1 ⁇ C 40 alkoxy group, C 6 ⁇ C 40 aryl group and a nuclear atoms least one member selected from the group consisting of a heteroaryl group of from 5 to 40 substituents It may be substituted by.
  • the substituents may be bonded to adjacent groups to form a condensed ring or a spiro bond.
  • the compound represented by the formula (3) of the present invention is preferably selected from the group consisting of the compound represented by the formulas (3a to 3d).
  • Ra and R 21 to R 25 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 Heterocycloalkyl group, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 Is selected from the group consisting of an aryl phosphine oxide group and an arylamine group of C 6 ⁇ C 60 , may be combined with adjacent groups to form a condensed ring, wherein
  • X-Y which is an organic ligand in Chemical Formula 3, is preferably selected from the group consisting of structures represented by A1-A24 in consideration of characteristics of the organic electroluminescent device.
  • R 31 to R 42 of the structure represented by A1 to A24 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to C 40 atoms, aryl jade having 6 to C 60 atoms group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ aryl phosphine of C 60 It is selected from the group consisting of a pin group, a C 6 ⁇ C 60 aryl phosphine oxide group and a C 6 ⁇ C 60
  • Specific examples of the compound represented by Formula 3 of the present invention include, but are not limited to, the following compounds (1-170).
  • the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and any one or more of the one or more organic material layers may be represented by the above chemical formula. Except for including the compounds represented by 1 and 3 may be made of materials and structures known in the art.
  • the organic EL device of the present invention may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. It may also be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode (anode or cathode) and the organic material layer.
  • At least one of the hole injection layer, the hole transport layer, and the light emitting layer corresponding to the organic material layer may preferably include a compound represented by Chemical Formulas 1 and 3. More preferably, the compound represented by Formula 1 of the present invention may be used as a phosphorescent host of the light emitting layer, and the compound represented by Formula 3 may be used as a phosphorescent dopant of the light emitting layer.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); A combination of a metal and an oxide 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 and the like can be used.
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al and the like.
  • the electron injection layer and the electron transport layer may be used without particular limitation as long as it is a material known in the art.
  • the manufacturing method of the organic EL device of the present invention is not particularly limited as long as it is known in the art, but the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method may include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer.
  • a 5- (2-nitrophenyl) -1-o-tolyl-1H-indole was obtained in the same manner as in ⁇ Step 3> of Preparation Example 1, except that 1-bromo-2-methylbenzene was used instead of iodobenzene.
  • a 1- (biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole was obtained in the same manner as in ⁇ Step 3> of Preparation Example 1, except that 4-bromobiphenyl was used instead of iodobenzene.
  • IC-11 was obtained by the same process as ⁇ Step 4> of Preparation Example 1.
  • a 1- (biphenyl-3-yl) -5- (2-nitrophenyl) -1H-indole was obtained in the same manner as in ⁇ Step 3> of Preparation Example 1, except that 3-bromobiphenyl was used instead of iodobenzene.
  • IC-13 was obtained by performing the same procedure as in Step 4>.
  • IC-20 was obtained by performing the same procedure as in the following.
  • 6-chloro-1H-indole 25 g, 0.17 mol
  • bromobenzene 31.19 g, 0.20 mol
  • Pd (OAc) 2 (1.86 g, 5 mol)
  • Triphenylphosphine (2.17 g, 5 mol%)
  • K 2 CO 3 68.64 g, 0.50 mol
  • 1,4-dioxane 300 ml
  • IC-22 was obtained by performing the same procedure as in the following.
  • 6-chloro-2-phenyl-1H-indole instead of 6-chloro-1H-indole was carried out the same process as in ⁇ Step 1> of Preparation Example 22 6-chloro-2,3-diphenyl -1 H-indole was obtained.
  • IC-34 was obtained by the same procedure as in ⁇ Step 2> of Preparation Example 33 using the 4- (2-benzhydrylphenyl) -1H-indole instead of 4- (2-isopropylphenyl) -1H-indole.
  • IC-37 was obtained by the same procedure as ⁇ Step 3> of Preparation Example 36, except that 6- (2-nitrophenyl) benzofuran was used instead of 5- (2-nitrophenyl) benzofuran.
  • IC-41 was obtained by the same procedure as in ⁇ Step 2> of Preparation Example 38 above. .
  • IC-42 was obtained by the same procedure as ⁇ Step 3> of Preparation Example 36, except that 5- (2-nitrophenyl) benzo [b] selenophene was used instead of 5- (2-nitrophenyl) benzofuran.
  • IC-1 (3 g, 10.63 mmol), 3-bromobiphenyl (3.72 g, 15.94 mmol), Cu powder (0.07 g, 1.06 mmol), K 2 CO 3 (1.47 g, 10.63 mmol), Na 2 SO under a nitrogen stream. 4 (1.51 g, 10.63 mmol) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C. for 24 hours.
  • Inv-2 (2.13 g, 46%) was obtained by the same procedure as in Synthesis Example 1, except that 3- (4-bromophenyl) pyridine was used instead of 3-bromobiphenyl.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 3-bromobiphenyl. -5 (3.21 g, 50%) was obtained.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 3-bromobiphenyl. -6 (3.47 g, 49%) was obtained.
  • Inv-10 (3.53 g, 50%) was carried out in the same manner as in Synthesis Example 1, except that 4- (5-bromobiphenyl-3-yl) -2,6-diphenylpyrimidine was used instead of 3-bromobiphenyl. )
  • the target compound was prepared in the same manner as in Synthesis Example 3, except that (4-chlorophenyl) triphenylsilane was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. 14 (4.92 g, 75%) was obtained.
  • Inv-17 (2.45 g, 53%) was prepared by the same procedure as in Synthesis Example 1, except that IC-3 and 3- (4-bromophenyl) pyridine were used instead of IC-1 and 3-bromobiphenyl. Got.
  • IC-3 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Exc-22 (6.07 g, 77%) was obtained by the same procedure as in Synthesis Example 3, except that -1,3,5-triazine was used.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that IC-3 and 4- (5-bromobiphenyl-3-yl) -2,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl. -25 (3.04 g, 43%) was obtained.
  • Inv-27 (2.66 g, 48%) was obtained by the same procedure as in Synthesis Example 1, except that IC-3 and (4-bromophenyl) diphenylborane were used instead of IC-1 and 3-bromobiphenyl. .
  • Inv-28 (2.54 g, 44%) was obtained by the same procedure as in Synthesis Example 1, except that IC-3 and (4-bromophenyl) diphenylphosphine were used instead of IC-1 and 3-bromobiphenyl. .
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that IC-11 and 3,3 '-(5-bromo-1,3-phenylene) dipyridine were used instead of IC-1 and 3-bromobiphenyl. -44 (2.34 g, 51%) was obtained.
  • Inv-48 (2.64) was prepared by the same procedure as in Synthesis Example 1, except that IC-12 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl. g, 47%).
  • Inv-56 (1.99 g, 49%) was prepared by the same procedure as in Synthesis Example 1, except that IC-16 and 2- (4-bromophenyl) pyrimidine were used instead of IC-1 and 3-bromobiphenyl Got.
  • Inv-61 (1.62 g, 48%) was obtained by the same procedure as in Synthesis Example 1, except that IC-19 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.
  • Inv-62 (1.94 g, 47%) was prepared in the same manner as in Synthesis Example 1, except that IC-19 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl )
  • Inv-67 (2.84) was prepared by the same procedure as in Synthesis Example 1, except that IC-22 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl. g, 51%).
  • Inv-70 (2.07 g, 51%) was prepared by the same procedure as in Synthesis Example 1, except that IC-24 and 2- (4-bromophenyl) pyridine were used instead of IC-1 and 3-bromobiphenyl. Got.
  • Exc-72 (1.83 g, 53%) was obtained by the same procedure as in Synthesis Example 1, except that IC-25 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.
  • Inv-73 (2.25 g, 52%) was prepared in the same manner as in Synthesis Example 1, except that IC-25 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl. )
  • Inv-75 (1.55 g, 45%) was obtained in the same manner as in Synthesis Example 1, except that IC-26 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.
  • Inv-76 (1.83 g, 47%) was prepared by the same procedure as in Synthesis Example 1, except that IC-26 and 4- (4-bromophenyl) pyridine were used instead of IC-1 and 3-bromobiphenyl. Got.
  • Inv-77 (1.48 g, 43%) was obtained in the same manner as in Synthesis Example 1, except that IC-27 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.
  • Inv-79 (1.75 g, 45%) was obtained in the same manner as in Synthesis Example 1, except that IC-27 and 4-bromobiphenyl were used instead of IC-1 and 3-bromobiphenyl.
  • Inv-80 (2.12 g, 49%) was prepared in the same manner as in Synthesis Example 1, except that IC-27 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl. )
  • Inv-81 (1.79 g, 52%) was obtained in the same manner as in Synthesis Example 1, except that IC-28 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.
  • Inv-82 (1.99 g, 46%) was prepared in the same manner as in Synthesis Example 1, except that IC-28 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl. )
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that IC-20 and 2,2 '-(5-bromo-1,3-phenylene) dipyridine were used instead of IC-1 and 3-bromobiphenyl. -84 (2.61 g, 53%) was obtained.
  • Inv-88 (3.45 g, yield: 65%) was obtained in the same manner as in Synthesis Example 87, except that IC-29b (2.23 g, 10.0 mmol) was used instead of IC-29a.
  • Inv-89 (3.33 g, yield: 63%) was obtained in the same manner as in Synthesis Example 87, except that IC-30 (2.23 g, 10.0 mmol) was used instead of IC-29a.
  • Exv-90 (3.18 g, yield: 60%) was obtained in the same manner as in Synthesis Example 87, except that IC-31a (2.23 g, 10.0 mmol) was used instead of IC-29a.
  • Exv-91 (3.28 g, yield: 62%) was obtained in the same manner as in Synthesis Example 87, except that IC-31b (2.23 g, 10.0 mmol) was used instead of IC-29a.
  • Exv-92 (3.50 g, yield: 77%) was obtained in the same manner as Synthesis Example 85 except for using IC-32 (2.23 g, 10.0 mmol) instead of IC-29a.
  • Inv-93 (3.26 g, Yield 58%) was obtained by the same procedure as in Synthesis Example 1, except that IC-33 and 1-bromo-4-phenylisoquinoline were used instead of IC-1 and 3-bromobiphenyl. Got it.
  • IC-1 (10 g, 35.44 mmol), 2-chloro-4-phenylquinazoline (10.2 g, 42.53 mmol), Cu powder (0.22 g, 3.544 mmol), K 2 CO 3 (9.8 g, 70.88 mmol) under a nitrogen stream, Na 2 SO 4 (10 g, 70.88 mmol) and nitrobenzene (350 ml) were mixed and stirred at 190 ° C. for 12 hours.

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  • Crystallography & Structural Chemistry (AREA)
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Abstract

La présente invention concerne un dispositif électroluminescent organique, dans lequel une couche électroluminescente utilisant un composé à base d'indole et un composé d'iridium en tant que matériau hôte et matériau dopant, respectivement, est introduite dans le dispositif électroluminescent organique de telle sorte que le dispositif électroluminescent organique peut comprendre une efficacité lumineuse, une tension de commande, des caractéristiques de durée de vie, et analogues, améliorés.
PCT/KR2013/007669 2012-10-24 2013-08-27 Dispositif électroluminescent organique WO2014065498A1 (fr)

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EP2894157A1 (fr) * 2014-01-14 2015-07-15 Samsung Electronics Co., Ltd Composé cyclique condensé et dispositif électroluminescent organique le contenant
WO2015190718A1 (fr) * 2014-06-09 2015-12-17 주식회사 두산 Dispositif électroluminescent organique
EP3026056A1 (fr) * 2014-11-28 2016-06-01 Samsung Electronics Co., Ltd. Composé organométallique et dispositif électroluminescent organique l'incluant
CN105646590A (zh) * 2014-11-28 2016-06-08 三星电子株式会社 有机金属化合物和包括其的有机发光器件
CN106892925A (zh) * 2015-12-19 2017-06-27 西安瑞联新材料股份有限公司 一种基于吡咯并咔唑衍生物的oled材料及其制备方法
CN110373182A (zh) * 2019-07-10 2019-10-25 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和器件
US11168093B2 (en) 2018-12-21 2021-11-09 Celgene Corporation Thienopyridine inhibitors of RIPK2

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KR102261104B1 (ko) * 2012-12-26 2021-06-04 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR102191019B1 (ko) * 2012-12-26 2020-12-14 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR102307761B1 (ko) * 2014-12-24 2021-10-05 솔루스첨단소재 주식회사 이리듐 착물의 제조방법 및 이에 의해 제조된 이리듐 착물을 이용한 유기 전계 발광 소자
KR102409384B1 (ko) * 2015-02-04 2022-06-15 삼성전자주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
KR102456076B1 (ko) * 2015-09-03 2022-10-19 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자

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Publication number Priority date Publication date Assignee Title
EP2894157A1 (fr) * 2014-01-14 2015-07-15 Samsung Electronics Co., Ltd Composé cyclique condensé et dispositif électroluminescent organique le contenant
CN104774210A (zh) * 2014-01-14 2015-07-15 三星电子株式会社 稠环化合物和包括其的有机发光器件
US9865820B2 (en) 2014-01-14 2018-01-09 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN104774210B (zh) * 2014-01-14 2019-02-01 三星电子株式会社 稠环化合物和包括其的有机发光器件
WO2015190718A1 (fr) * 2014-06-09 2015-12-17 주식회사 두산 Dispositif électroluminescent organique
EP3026056A1 (fr) * 2014-11-28 2016-06-01 Samsung Electronics Co., Ltd. Composé organométallique et dispositif électroluminescent organique l'incluant
CN105646590A (zh) * 2014-11-28 2016-06-08 三星电子株式会社 有机金属化合物和包括其的有机发光器件
US12089487B2 (en) 2014-11-28 2024-09-10 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
CN106892925A (zh) * 2015-12-19 2017-06-27 西安瑞联新材料股份有限公司 一种基于吡咯并咔唑衍生物的oled材料及其制备方法
US11168093B2 (en) 2018-12-21 2021-11-09 Celgene Corporation Thienopyridine inhibitors of RIPK2
CN110373182A (zh) * 2019-07-10 2019-10-25 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和器件

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