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WO2015126161A2 - 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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WO2015126161A2
WO2015126161A2 PCT/KR2015/001634 KR2015001634W WO2015126161A2 WO 2015126161 A2 WO2015126161 A2 WO 2015126161A2 KR 2015001634 W KR2015001634 W KR 2015001634W WO 2015126161 A2 WO2015126161 A2 WO 2015126161A2
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WO2015126161A3 (fr
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김홍석
김영배
이인혁
김은진
라종규
김태형
백영미
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Doosan Corp
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/30—Coordination compounds
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    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, a novel compound having excellent hole injection ability, hole transporting ability, light emission ability, etc. and the compound as a material of an organic material layer,
  • the present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • 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 material may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, it can be divided into yellow and orange light emitting materials required to achieve a better natural color. In addition, 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. Since the development of phosphorescent materials can theoretically improve luminous efficiency up to four times compared to fluorescence, attention is being paid not only to phosphorescent dopants but also to phosphorescent host materials.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 and the like represented by the following formulas
  • anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which are blue and green. It is used as a red dopant material.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the conventional light emitting materials are good in terms of the light emission characteristics, but because the glass transition temperature is low, the thermal stability is not very good, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, there is a demand for development of a light emitting material having excellent performance.
  • An object of the present invention is to provide a novel compound that can be used as a light emitting layer material, a hole transporting layer material and a hole injection layer material with excellent light emitting ability, hole transporting ability and hole injection ability.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel compound having a low driving voltage, a high luminous efficiency, and an improved lifetime.
  • the present invention provides a compound represented by Formula 1:
  • Cy is a nitrogen-containing heterocycle represented by the following Chemical Formula 2 or 3;
  • X 1 is selected from the group consisting of O, S, N (R 1 ), and C (R 2 ) (R 3 );
  • X 2 to X 8 are the same as or different from each other, and each independently N or C (R 4 ), wherein when R 4 is plural, they may be the same or different from each other;
  • R 1 to R 10 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 3 to C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, Substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 40 alkylsilyl group, substituted or unsubstituted C 6 ⁇ C 60 arylsilyl group, substituted or unsubstituted C 1 ⁇ C 40 Al
  • L is a single bond or is selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms;
  • the arylene group and heteroarylene group of L the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group of R 1 to R 10 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group each independently deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of, C 1 ⁇ C 40 Alkylsilyl group, C 6
  • 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 characterized in that it comprises a.
  • At least one organic material layer including the compound represented by Formula 1 is selected from the group consisting of a hole transport layer, a hole injection layer and a light emitting layer, preferably a hole transport layer and / or a light emitting layer, more preferably may be a light emitting layer have.
  • the compound represented by Formula 1 when included in the light emitting layer, the compound may be a phosphorescent host material of the light emitting layer.
  • the organic electroluminescent device including the compound according to the present invention in the hole injection layer, the hole transport layer and / or the light emitting layer can greatly improve aspects of light emission performance, driving voltage, lifetime, efficiency, and the like, and thus, a full color display panel. It can be effectively applied to the back.
  • the novel organic compound according to the present invention is composed of an indolizine moiety, a quinolizine moiety, and the like of an indole moiety or a fused indole moiety.
  • Direct bond single bond
  • arylene group a hetero arylene group to form a basic skeleton, a structure in which a variety of substituents are bonded to this basic skeleton, characterized in that represented by the formula (1).
  • Compound represented by the formula (1) has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] has a high glass transition temperature, and also excellent thermal stability, It has excellent hole injecting ability, hole transporting ability and light emitting ability. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the moiety such as the indolizine moiety or the quinolizine moiety is an electron withdrawing electron (EWG) having high electron absorption
  • the indole moiety Indole moiety or fused indole moiety is an electron donor with a large electron donor (EDG).
  • EWG electron withdrawal group
  • EDG electron donor group
  • the compound of Formula 1 has both an electron withdrawal group (EWG) and an electron donor group (EDG), so that the entire molecule has a bipolar characteristic, thereby increasing the binding force between the hole and the electron. Accordingly, the compound of Formula 1 may exhibit excellent light emission characteristics, and may be usefully applied as a blue, green, or red phosphorescent layer material of an organic EL device.
  • the compound represented by Chemical Formula 1 may not only improve phosphorescence characteristics of the organic EL device, but also improve hole injection / transport ability, emission efficiency, driving voltage, lifetime characteristics, and the like. Depending on the kind of substituents to be used, the electron transport ability and the like can also be improved. Accordingly, the compound of formula 1 according to the present invention is preferably an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole transport layer material and a hole injection layer material, more preferably Can be used as the phosphorescent layer material.
  • a light emitting layer material blue, green and / or red phosphorescent host material
  • a hole transport layer material and a hole injection layer material more preferably Can be used as the phosphorescent layer material.
  • the compound of the general formula (1) by introducing a variety of substituents, especially aryl groups and / or heteroaryl groups in the basic skeleton, significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, the conventional light emitting material (Eg, CBP) can have a higher thermal stability.
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics. As such, the performance and lifespan characteristics of the organic EL device may be improved, thereby maximizing the performance of the full color organic light emitting panel.
  • X 1 is selected from the group consisting of O, S, N (R 1 ), and C (R 2 ) (R 3 ), preferably X 1 is C (R 2 ) ( R 3 ).
  • X 2 to X 8 are the same as or different from each other, and each independently N or C (R 4 ), when R 4 is a plurality, they may be the same or different from each other.
  • one of X 2 to X 8 is N and the other is C (R 4 ).
  • X 7 is N
  • X 2 to X 6 and X 8 are all C (R 4 ).
  • X 3 is N
  • X 2 and X 4 to X 8 are all C (R 4 ).
  • the plurality of R 4 may be the same or different from each other.
  • examples of the nitrogen-containing heterocycle represented by Formula 2 include a nitrogen-containing heterocycle represented by the following Formula 2a, but are not limited thereto.
  • a plurality of R 4 are the same or different from each other,
  • R 2 to R 4 are the same as defined in Chemical Formula 1, respectively.
  • examples of the nitrogen-containing heterocycle represented by Formula 3 include a nitrogen-containing heterocycle represented by the following Formula 3a, but are not limited thereto.
  • a plurality of R 4 are the same as or different from each other, and are defined in Chemical Formula 1.
  • L is a single bond or is selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 60 arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, preferably May be a single bond or phenylene.
  • R 1 to R 10 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 3 to C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, Substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 40 alkylsilyl group, substituted or unsubstituted C 6 ⁇ C 60 arylsilyl group, substituted or unsubstituted C 1 ⁇ C 40 Al
  • the arylene group and heteroarylene group of L the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl of the R 1 to R 10 group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently selected from deuterium, halogen, cyano, 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 alkyl
  • the moiety may be a moiety represented by one of Formulas B-1 to B-29, but is not limited thereto.
  • R 5 to R 10 are each as defined in Chemical Formula 1,
  • R 21 to R 22 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group , Substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted A substituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, and a substituted or unsubstituted C 6 to C 60 arylamine group, or an adjacent group; May combine to form a condensed ring, provided that when R 21 is plural, they are the same or different from each other,
  • the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group and arylamine group of R 21 and R 22 are each independently deuterium, halogen, cyano, C 1 ⁇ C 40
  • n is an integer of 0-4.
  • unsubstituted 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, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • unsubstituted alkenyl 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. do. Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl and the like.
  • unsubstituted alkynyl refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms having at least one carbon-carbon triple bond. do. Non-limiting examples thereof include ethynyl, 2-propynyl and the like.
  • unsubstituted 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.
  • saturated cyclic hydrocarbon saturated cyclic hydrocarbon
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • unsubstituted 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 at least one carbon in the ring , Preferably 1 to 3 carbons are substituted with a hetero atom such as N, O or S.
  • a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • unsubstituted aryl 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. 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.
  • unsubstituted 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 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.
  • unsubstituted alkyloxy refers to a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic. ) May include a structure.
  • alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • unsubstituted aryloxy refers to a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms.
  • R'O- a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • unsubstituted alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms
  • arylamine has 6 to 40 carbon atoms. Amine substituted with 40 aryl.
  • alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms
  • arylphosphine group is carbon atoms It means a phosphine group substituted with 1 to 60 aryl
  • aryl phosphine oxide group means a phosphine oxide group substituted with an aryl having 1 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 combination thereof.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • 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, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound represented by Formula 1 may be used alone or in combination of two or more.
  • 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, at least one of the 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 phosphorescent layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
  • the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
  • the structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate.
  • an electron injection layer may be further interposed between the electron transport layer and the cathode.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be.
  • the compound of Formula 1 may be used as a phosphorescent host of the light emitting layer.
  • the organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and 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.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may 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 or polyaniline; And carbon black, but are 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; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • 1,3-dichloroimidazo [1,5-a] pyridine (3.8g, 20.5mmol), phenylboronic acid (2.5g, 20.5mmol), Pd (PPh 3 ) 4 (1.2g, 5mol%) under nitrogen stream, and Potassium carbonate (8.5 g, 61.5 mmol) was added to Toluene / H 2 O / Ethanol (80 ml / 40 ml / 40 ml) and stirred at 110 ° C. for 4 hours.
  • TP-2 (3.3g, 11.9mmol, Yield: 58% by following the same procedure as Preparation Example 1 )
  • 1,4-dichloro-8H-pyrido [1,2-c] pyrimidine (4.0g, 20.0mmol), phenylboronic acid (2.4g, 20.0mmol), Pd (PPh 3 ) 4 (1.1g, 5 mol) under nitrogen stream %), And potassium carbonate (8.3 g, 60.0 mmol) were added to Toluene / H 2 O / Ethanol (80 ml / 40 ml / 40 ml) and stirred at 110 ° C. for 2 hours.
  • TP-1 (2.8g, 12.3mmol), 3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (3.8g, 13.5mmol), Pd 2 (dba) synthesized in Preparation Example 1 under nitrogen stream 3 (0.6g, 5 mol%), tritert - butylphosphine (0.1g, 0.6mmol) and sodium tert-butoxide (3.6g, 36.9mmol) were added to Toluene (70ml) and stirred at 110 ° C for 3 hours.
  • TP-2 (3.3g, 11.9mmol), 3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (3.7g, 13.1mmol), Pd 2 (dba) synthesized in Preparation Example 2 under nitrogen stream 3 (0.6g, 5 mol%), tritert - butylphosphine (0.1g, 0.6mmol) and sodium tert-butoxide (3.4g, 35.7mmol) were added to Toluene (80ml) and stirred at 110 ° C for 4 hours.
  • TP-3 (3.7g, 12.1mmol), 3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (3.8g, 13.3mmol), Pd 2 (dba) synthesized in Preparation Example 3 under nitrogen stream 3 (0.6g, 5 mol%), tritert - butylphosphine (0.1g, 0.6mmol) and sodium tert-butoxide (3.5g, 36.3mmol) were added to Toluene (90ml) and stirred at 110 ° C for 3 hours.
  • TP-4 (3.0 g, 12.4 mmol), 3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (3.9 g, 13.6 mmol), Pd 2 (dba) used in Preparation Example 4 under nitrogen stream 3 (0.6g, 5 mol%), tritert - butylphosphine (0.1g, 0.6mmol) and sodium tert-butoxide (3.6g, 37.2mmol) were added to Toluene (60ml) and stirred at 110 ° C for 3 hours. After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R57 (3.3g, 6.8mmol, yield: 55%).
  • TP-6 (4.0g, 12.6mmol), 3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (3.9g, 13.9mmol), Pd 2 (dba) used in Preparation Example 6 under nitrogen stream 3 (0.6g, 5 mol%), tritert - butylphosphine (0.1g, 0.6mmol) and sodium tert-butoxide (3.4g, 37.8mmol) were added to Toluene (70ml) and stirred at 110 ° C for 3 hours. After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R59 (3.8g, 6.8mmol, yield: 54%).
  • 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
  • M-MTDATA 60 nm) / TCTA (80 nm) / Compound R1 + 10% (piq) 2 Ir (acac) (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to fabricate an organic EL device.
  • a red organic EL device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 was used instead of the compound R1 used as a host material in forming the emission layer in Example 1.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound R1 used as the light emitting host material in forming the emission layer in Example 1.
  • Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
  • Example 1 R1 4.2 621 11.9
  • Example 2 R2 4.2 620 12.1
  • Example 3 R3 4.2 620 12.5
  • Example 4 R15 4.2 621 12.2
  • Example 5 R16 4.2 622 12.0
  • Example 6 R17 4.1 621 12.0
  • Example 7 R29 4.3 620 12.1
  • Example 8 R30 4.2 621 12.3
  • Example 9 R31 4.3 621 12.1
  • Example 10 R43 4.3 620 11.8
  • Example 11 R44 4.2 620 11.6
  • Example 12 R45 4.2 621 12.2
  • Example 13 R57 4.1 620 12.2
  • Example 14 R58 4.2 620 12.1
  • Example 15 R59 4.0 621 11.8
  • Example 16 R71 4.3 621 12.1
  • Example 17 R72 4.2 621 12.0
  • Example 18 R73 4.2 621 12.1
  • Example 19 R85 4.1 620 12.

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  • Spectroscopy & Molecular Physics (AREA)
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  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé pour une couche de matériau organique, de préférence, une couche émettant de la lumière, du dispositif électroluminescent organique, ce qui permet d'améliorer l'efficacité lumineuse, la tension de commande, la durée de vie, et analogues, du dispositif électroluminescent organique.
PCT/KR2015/001634 2014-02-21 2015-02-17 Composé organique et dispositif électroluminescent organique comprenant un tel composé Ceased WO2015126161A2 (fr)

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WO2018143663A1 (fr) * 2017-02-01 2018-08-09 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
CN109890815A (zh) * 2016-11-04 2019-06-14 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置

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JP2001160489A (ja) 1999-12-01 2001-06-12 Toyota Central Res & Dev Lab Inc 有機電界発光素子
JP5509634B2 (ja) 2009-03-16 2014-06-04 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料
KR20120083243A (ko) * 2011-01-17 2012-07-25 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20140009263A (ko) * 2011-02-11 2014-01-22 유니버셜 디스플레이 코포레이션 유기 발광 디바이스 및 이것에 사용되는 재료

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109890815A (zh) * 2016-11-04 2019-06-14 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
CN109890815B (zh) * 2016-11-04 2022-12-13 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
WO2018143663A1 (fr) * 2017-02-01 2018-08-09 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
US11289662B2 (en) 2017-02-01 2022-03-29 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same

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