WO2015133808A1 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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WO2015133808A1
WO2015133808A1 PCT/KR2015/002071 KR2015002071W WO2015133808A1 WO 2015133808 A1 WO2015133808 A1 WO 2015133808A1 KR 2015002071 W KR2015002071 W KR 2015002071W WO 2015133808 A1 WO2015133808 A1 WO 2015133808A1
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aryl
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alkyl
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장지성
김영배
이인혁
김은진
김태형
백영미
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주식회사 두산
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material included in 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 material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
  • a host / dopant system may be used as a light emitting material to increase luminous efficiency through an 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.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
  • a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
  • the existing materials are not satisfactory in terms of lifespan of the organic EL device due to low thermal stability due to low glass transition temperature, and still need improvement in terms of emission characteristics.
  • an object of the present invention is to provide an organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.
  • Another object of the present invention is to provide an organic electroluminescent device including the organic compound and improved driving voltage and luminous efficiency.
  • the present invention provides a compound represented by the following formula (1).
  • Y 1 to Y 12 are each independently C (R 1 ) or N, wherein Y 1 and Y 2 , Y 2 and Y 3 , Y 3 and Y 4 , Y 5 and Y 6 , Y 6 and Y 7 , One of Y 7 and Y 8 , Y 9 and Y 10 , Y 10 and Y 11, and Y 11 and Y 12 are all C (R 1 ), and combine with each other to form a condensed ring represented by the following Chemical Formula 2,
  • X 1 and X 2 are each independently selected from the group consisting of N (Ar 1 ), O, S, C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein at least one is N (Ar 1 ),
  • Y 13 to Y 16 are each independently C (R 2 ) or N,
  • Ar 1 to Ar 5 is C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60 Aryl group, Nuclear atoms 5 to 60 heteroaryl C 6 -C 60 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -CC 60 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocyclo alkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ aryl phosphine of C 60 It is selected from the group consisting of a pin oxide group and an arylsilyl group of C 6 ⁇ C 60 ,
  • a plurality of R which does not form a condensed ring 1 and R 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 the arylboronic group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇
  • Ar 1 to Ar 5 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron of R 1 and R 2
  • the group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group are each independently C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 Of cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear 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 , C 6 to C 60 Aryloxy group, C 1 to C 40 al
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising.
  • alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. It may also include a form in which two or more rings are attached to each other (pendant) or condensed. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included, and may also include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 carbon atoms.
  • Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • an aromatic ring or a heteroaromatic ring is condensed to a tribenzoazepine-based structure as follows to form a basic skeleton, and is represented by Chemical Formula 1.
  • the aromatic ring or heteroaromatic ring condensed to the tribenzoazepine-based structure is not particularly limited, and examples thereof include indene, indole, benzothiophene, benzofuran, and benzosilol.
  • the host included in the phosphorescent layer should have a triplet energy gap higher than that of the dopant.
  • the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.
  • Compound represented by the formula (1) of the present invention has a specific substituent is introduced in the dibenzoazine-based structure having a broad singlet energy level and a high triplet energy level, when applied as a host of the light emitting layer to show a higher energy level than the dopant Can be.
  • the compound represented by Chemical Formula 1 of the present invention having a triplet energy of 2.3 eV or more prevents the excitons generated in the light emitting layer from diffusing to the adjacent electron transport layer or the hole transport layer, thereby increasing the number of excitons that contribute to light emission.
  • the luminous efficiency can be improved.
  • the compound represented by Formula 1 of the present invention may have a wide bandgap by adjusting HOMO and LUMO energy levels according to substituents introduced, and may have high carrier transport properties.
  • the electron withdrawal (EWG) having a high electron absorption and / or the electron donor (EDG) having a large electron donor are combined, the entire molecule may have a bipolar characteristic to increase the binding force between the hole and the electron.
  • the compound represented by Chemical Formula 1 of the present invention has various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, thereby improving the conventional organic material layer material (for example, it may have higher thermal stability than CBP).
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer.
  • the performance and lifespan characteristics of the organic EL device may be greatly improved.
  • the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • X 1 and X 2 are each independently N (Ar 1 ), O, S, C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 )
  • N (Ar 1 ), O or S is preferred, all N (Ar 1 ) is more preferred.
  • Y 1 to Y 12 are each independently C (R 1 ) or N, in consideration of the characteristics of the organic electroluminescent device, it is preferable to include one or all C (R 1 ).
  • Y 13 to Y 16 are each independently C (R 2 ) or N. In consideration of the characteristics of the organic electroluminescent device, it is preferable to include one N or all C (R 2 ).
  • the compound represented by Chemical Formula 1 of the present invention may be embodied in any one of the compounds represented by the following Chemical Formulas 3 to 11.
  • X 1 , X 2 , R 1, and R 2 are the same as defined in Chemical Formula 1, wherein a plurality of R 1 are the same as or different from each other, and a plurality of R 2 are the same as or different from each other. .
  • the compound represented by Chemical Formula 1 of the present invention may be further embodied as any one of the compounds represented by the following Chemical Formulas 12 to 20.
  • Ar 1 , R 1 and R 2 are the same as defined in Formula 1, wherein a plurality of R 1 are the same as or different from each other, a plurality of R 2 is the same as or different from each other.
  • Ar 1 to Ar 5 is a C 6 ⁇ C 60 aryl group, a heteroaryl group of 5 to 60 nuclear atoms in consideration of the wide bandgap and thermal stability of the compound to be 6 ⁇ C 60 aryl group and a C 6 ⁇ amine selected from the group consisting of aryl silyl C 60 are preferred.
  • Ar 1 is C 6 ⁇ C 60 heteroaryl group of the aryl group or 5 to 60 nuclear atoms is more preferable.
  • R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, It is preferably selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms and an arylamine group having 6 to 60 carbon atoms.
  • At least one of Ar 1 , R 1, and R 2 is preferably a substituent represented by the following general formula (21).
  • L is are selected from the group consisting of a single bond, a C 6 ⁇ C 40 aryl group and a nuclear atoms of 5 to 40 hetero arylene group for, particularly preferably a single bond, phenylene or biphenylene.
  • Z 1 to Z 5 are each independently N or C (R 17 ), wherein at least one includes N, specifically, 1 to 3 N are preferable.
  • R 17 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 , 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 may be selected from the group consisting of a pin group, C 6 ⁇ C 60 aryl phosphine oxide group and C 6
  • arylene group, heteroarylene group of L alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group of R 17 ,
  • Arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group
  • the substituent represented by Formula 21 may be embodied by any one of substituents represented by the following Formulas A-1 to A-15.
  • L And R 17 is the same as defined in Formula 21, wherein a plurality of R 17 is the same or different from each other,
  • R 21 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, aryloxy nuclear atoms 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60, alkyloxy group of C 1 ⁇ C 40 , C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group And, C 6 ⁇ C 60 An aryl phosphine oxide group and C 6 ⁇ C 60 It may be selected from the group consisting of aryl
  • the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cyclo Alkyl group, heterocycloalkyl group of 3 to 40 nuclear 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 , aryl of C 6 to C 60 Oxy group, C 1
  • n is an integer of 0-4.
  • Ar 1 to Ar 5 , R 1 and R 2 are each independently selected from the group consisting of hydrogen or a substituent represented by S1 to S204.
  • the compound represented by Formula 1 of the present invention may be embodied by the compounds exemplified below, but the compound represented by Formula 1 of the present invention is not limited to the following compounds.
  • the present invention includes an anode, a cathode and at least one organic layer interposed between the anode and the cathode, and at least one of the at least one organic layer includes the compound represented by Formula 1 It provides an organic electroluminescent device.
  • the compound may be used alone, or two or more may be used in combination.
  • the at least one organic material layer may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the organic material layer including the compound represented by Chemical Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and in this case, the host material may include a compound represented by Formula 1 above.
  • the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the structure of the organic EL device of the present invention is not particularly limited, but may be 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.
  • An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention is another organic material layer using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Formula 1 above. And it can be manufactured by forming an electrode.
  • the organic material layer 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.
  • a silicon wafer quartz, glass plate, metal plate, plastic film, sheet, or the like may be used.
  • 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), 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 or polyaniline; And carbon black and the like can be used.
  • 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), poly
  • the negative electrode material may be magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or a metal such as lead or an alloy thereof, and a multilayer such as LiF / Al or LiO 2 / Al. Structural materials and the like can be used.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.
  • 6-chloro-9H-tribenzo [b, d, f] azepine 150 g, 540.0 mol
  • 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2, 2'-bi (1,3,2-dioxaborolane) 150 g, 594 mmol
  • Pd (dppf) Cl 2 14 g, 16 mmol
  • KOAc 152 g, 1620.0 mmol
  • 1,4-dioxane 2000 ml
  • Compound 1- was prepared by the same procedure as in Synthesis Example 1, except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.5 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine. 6 (2.7 g, yield 65%) was obtained.
  • Compound 1- was prepared by the same procedure as in Synthesis Example 11, except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.5 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine. 16 (2.6 g, yield 65%) was obtained.
  • the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1-1 as a light emitting host material when forming the emission layer.
  • Example 1 Sample Host Driving voltage (V) Light emitting peak (nm) Current efficiency (cd / A) Example 1 1-1 6.50 517 42.0 Example 2 1-2 6.60 518 41.9 Example 3 1-3 6.60 517 40.9 Example 4 1-4 6.55 516 40.8 Example 5 1-5 6.50 518 41.2 Example 6 1-6 6.45 518 40.5 Example 7 1-7 6.60 517 41.9 Example 8 1-8 6.70 517 41.1 Example 9 1-11 6.55 518 42.1 Example 10 1-12 6.60 518 41.8 Example 11 1-13 6.50 518 41.0 Example 12 1-14 6.55 516 40.8 Example 13 1-15 6.50 518 41.1 Example 14 1-16 6.55 518 40.9 Example 15 1-17 6.60 517 41.9 Example 16 1-18 6.65 518 41.1 Example 17 2-1 6.50 517 42.2 Example 18 2-2 6.50 518 41.7 Example 19 2-3 6.60 517 41.9 Example 20 2-4 6.55 516 40.8 Example 21 2-5 6.55 518 41.4 Example 22 2-6 6.45 518 40.5 Example 23 2-7 6.60 5
  • a red organic electroluminescent device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a red organic electroluminescent device was manufactured in the same manner as in Example 49, except that CBP was used instead of Compound 1-9 as a light emitting host material when forming the emission layer.
  • Example 49 1-9 4.80 12.5
  • Example 50 1-10 4.50 12.1
  • Example 51 1-19 4.70 12.4
  • Example 52 1-20 4.60 12.7
  • Example 53 2-9 4.60 12.0
  • Example 54 2-10 4.55 11.8
  • Example 55 3-9 4.75 12.2
  • Example 56 3-10 4.60 11.5
  • Example 58 4-10 4.60 11.7
  • Example 59 5-9 4.90 12.3
  • the efficiency (luminescence efficiency and messenger efficiency), lifetime, brightness and driving of the organic electroluminescent device Voltage and the like can be improved. Therefore, the present invention can improve the performance and lifespan of a full color organic electroluminescent panel.

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

Abstract

La présente invention porte sur un composé organique et sur un dispositif électroluminescent organique comprenant ce composé électroluminescent organique. Ledit composé organique de la présente invention est utilisé pour une couche de matériau organique, de préférence une couche d'émission de lumière, d'un dispositif électroluminescent organique, ce qui permet d'améliorer le rendement d'émission de lumière, la tension de commande, la durée de vie, etc. du dispositif électroluminescent organique.
PCT/KR2015/002071 2014-03-04 2015-03-04 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2015133808A1 (fr)

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WO2017026643A1 (fr) * 2015-08-13 2017-02-16 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
TWI641598B (zh) * 2016-08-19 2018-11-21 彩豐精技股份有限公司 化合物及其有機電子裝置
CN113929691A (zh) * 2021-11-22 2022-01-14 烟台九目化学股份有限公司 一种含氧杂卓并咔唑结构化合物及其应用

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KR102663762B1 (ko) * 2019-06-24 2024-05-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102663763B1 (ko) * 2019-07-22 2024-05-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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TWI641598B (zh) * 2016-08-19 2018-11-21 彩豐精技股份有限公司 化合物及其有機電子裝置
CN113929691A (zh) * 2021-11-22 2022-01-14 烟台九目化学股份有限公司 一种含氧杂卓并咔唑结构化合物及其应用
CN113929691B (zh) * 2021-11-22 2024-02-02 烟台九目化学股份有限公司 一种含氧杂卓并咔唑结构化合物及其应用

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