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WO2014092351A1 - Nouveau composé organique et élément électroluminescent organique comprenant celui-ci - Google Patents

Nouveau composé organique et élément électroluminescent organique comprenant celui-ci Download PDF

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WO2014092351A1
WO2014092351A1 PCT/KR2013/010483 KR2013010483W WO2014092351A1 WO 2014092351 A1 WO2014092351 A1 WO 2014092351A1 KR 2013010483 W KR2013010483 W KR 2013010483W WO 2014092351 A1 WO2014092351 A1 WO 2014092351A1
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aryl
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엄민식
이용환
백영미
신진용
박호철
이창준
김태형
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Doosan Corp
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • 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, 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 widely known as a hole injection layer, a hole transport layer, a hole blocking layer, and an electron transport layer, and anthracene derivatives are reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp).
  • Metal complex compounds containing Ir, such as 2 are used.
  • 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
  • an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
  • the present invention provides a compound represented by Formula 1:
  • R 1 to R 5 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 -C 40 alkyl group, a substituted or unsubstituted C 2 -C 40 alkenyl group , Substituted or unsubstituted C 2 -C 40 alkynyl group, substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkyloxy group, substituted or unsubstituted C 6 ⁇ C 40 arylamine group, substituted or unsubstituted C 3 ⁇ C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40
  • R 1 and R 2 are bonded to each other to form a condensed ring represented by the following Chemical Formula 2,
  • Dashed line means a site where condensation occurs by combining with at least one of R 1 and R 2, R 2 and R 3 , R 3 and R 4 of Formula 1;
  • X 1 is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
  • Ar 1 to Ar 6 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 ⁇ C 40 alkyl group, a substituted or unsubstituted C 2 ⁇ C 40 alkenyl group, a substituted or unsubstituted C 2 ⁇ C 40 alkynyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 aryloxy group , Substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine 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 1 to C
  • R 6 to R 9 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group , Substituted or unsubstituted C 2 -C 40 alkynyl group, substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkyloxy group, substituted or unsubstituted C 6 ⁇ C 40 arylamine group, substituted or unsubstituted C 3 ⁇ C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms,
  • the R One To R 9 , And Ar One To Ar 6 Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , Arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, C One ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl, C 2 ⁇ C 40 Alkynyl, C 6 ⁇ C 40 Aryl group, heteroaryl group having 5 to 40 nuclear atoms, C 6 ⁇ C 40 Aryloxy group, C One ⁇ C 40 Alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 A cycloalkyl group, a
  • 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 comprises the compound.
  • 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 comprises the compound.
  • the compound represented by Formula 1 of the present invention is excellent in thermal stability and phosphorescence properties, it may be applied to the light emitting layer of the organic EL device.
  • the novel compound according to the present invention is a structure in which an indole moiety is fused to an end of an indazole moiety to form a basic skeleton, and various substituents are bonded to the basic skeleton. Characterized in that the.
  • the 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')], and has a wide energy band gap, The bonding force of the electrons can be increased. Therefore, when the compound of Formula 1 is used in an organic EL device, the driving voltage, efficiency (light emitting efficiency, power efficiency), lifetime, and luminance of the device may be improved.
  • the compound represented by Formula 1 may have a wide bandgap due to an indole moiety bound to the end of an indazole moiety.
  • the compound has a bipolar (bipolar) characteristic of the entire molecule due to the various aromatic ring substituents bonded to the basic skeleton, it is possible to increase the binding force of the holes and electrons. Therefore, when the compound is applied to the organic EL device, since the light emitting layer can exhibit excellent properties as a host material as compared with the conventional CBP, the phosphorescence property of the device is improved and the hole injection ability and / or the transport ability, the luminous efficiency, Driving voltage, lifespan characteristics and the like can be improved.
  • the energy level may be adjusted according to the substituents to have a wide bandgap (sky blue to red), and thus may be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, and the like.
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the indole moiety, so that the glass transition temperature can be improved, thereby providing a higher thermal stability than the conventional CBP.
  • it is also effective in suppressing crystallization of the organic layer including the compound of Formula 1. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
  • the compound of Chemical Formula 1 according to the present invention when adopted as a hole injection / transport layer material of an organic EL device, a phosphorescent host material of blue, green and / or red color, the compound having the excellent efficiency and lifespan may be superior to the conventional CBP. Can be. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect on maximizing the performance in the full color organic light emitting panel.
  • R 1 to R 5 are the same as or different from each other, each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 ⁇ C 40 alkyl group, substituted Or an unsubstituted C 2 -C 40 alkenyl group, a substituted or unsubstituted C 2 -C 40 alkynyl group, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted nuclear atom 5 To 40 heteroaryl groups, substituted or unsubstituted C 6 to C 40 aryloxy groups, substituted or unsubstituted C 1 to C 40 alkyloxy groups, substituted or unsubstituted C 6 to C 40 arylamines Groups, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having
  • R 1 to R 5 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted heteroaryl having 5 to 40 nuclear atoms Group, and a substituted or unsubstituted C 6 ⁇ C 40 arylamine group.
  • Arylborone group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 hetero
  • R 1 and R 2, R 2 and R 3 , R 3 and R 4 may be condensed with each other to form a condensed ring represented by Chemical Formula 2.
  • R 1 and R 2 are condensed with each other to form a condensed ring represented by Formula 2, a compound represented by Formula 3 or 4 below is formed.
  • the dotted line refers to a site where condensation occurs with at least one of R 1 and R 2, R 2 and R 3 , R 3, and R 4 of Formula 1.
  • X 1 is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 ), preferably N (Ar 2 ) Can be.
  • Ar 1 to Ar 6 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 Alkynyl group of -C 40 , substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group of 5 to 40 nuclear atoms, substituted or unsubstituted C 6 -C 40 aryl jade Periodic, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine 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 1 to C
  • Arylborone group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycl
  • Ar 1 to Ar 6 are the same as or different from each other, each independently represent a substituted or unsubstituted C 6 ⁇ C 40 aryl group and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms Can be selected from.
  • the aryl group and heteroaryl group of Ar 1 to Ar 6 are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group , C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group , with one or more substituents selected from C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, and a C 6 ⁇ arylsilyl group the group consisting of C 40 And may be the same or different from each other when there are a plurality of substituents.
  • R 6 to R 9 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group , Substituted or unsubstituted C 2 -C 40 alkynyl group, substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkyloxy group, substituted or unsubstituted C 6 ⁇ C 40 arylamine group, substituted or unsubstituted C 3 ⁇ C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms,
  • Arylborone group, arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycl
  • R 1 to R 9 , and Ar 1 to Ar 6 may be each independently selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto. no. However, at least one of R 1 and R 2, R 2 and R 3 , R 3 and R 4 may be bonded to each other to form a condensed ring represented by Chemical Formula 2.
  • Ar 1 to Ar 6 may be more preferably selected from the group consisting of the following substituents A1 to A65.
  • Examples of the compound represented by Formula 1 according to the present invention include a compound represented by the following Formula 3 to Formula 8, but is not limited thereto.
  • Ar 1 , R 1 to R 9 , and X 1 are each as defined in Chemical Formula 1.
  • Representative examples of the compound represented by Formula 1 include the following compounds, but are not limited thereto.
  • unsubstituted alkyl is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl and the like.
  • Unsubstituted alkenyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, examples of which include vinyl, allyl (allyl), isopropenyl, 2-butenyl, and the like, but are not limited thereto.
  • Unsubstituted alkynyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, examples being ethynyl , 2-propynyl, and the like, but is not limited thereto.
  • Unsubstituted aryl means a monovalent substituent derived from an aromatic hydrocarbon of 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or fused form with one another. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Unsubstituted heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 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. It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Unsubstituted aryloxy is a monovalent substituent represented by RO-, wherein R is an aryl having 5 to 60 carbon atoms.
  • R is an aryl having 5 to 60 carbon atoms.
  • aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Unsubstituted alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and has a linear, branched or cyclic structure Interpret as included.
  • alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Unsubstituted arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Unsubstituted cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Unsubstituted heterocycloalkyl 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 or S Is substituted with a hetero atom such as Non-limiting examples thereof include morpholine, piperazine and the like.
  • Alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms
  • Fused ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1), preferably a compound represented by the formula (3) to a compound represented by the formula (8).
  • 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 Compound represented by the formula (1), preferably a compound represented by the formula (3) to a compound represented by the formula (8).
  • the compounds 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 Compound 1 may be a light emitting layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, wherein the host material may include the compound of formula (1).
  • the compound of Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, 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 according to the present invention described above is not particularly limited, and may be, for example, 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.
  • 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 the present invention can be used as a phosphorescent host of the light emitting layer.
  • An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent 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 according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, a light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.
  • at least one layer eg, a light emitting layer of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic 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.
  • 6- (2-nitrophenyl) -1H-indazole (11.04 g, 46.17 obtained in ⁇ Step 2> of Preparation Example 2 instead of 5- (2-nitrophenyl) -1H-indazole used in ⁇ Step 1> of Preparation Example 1 Except for using mmol), 6- (2-nitrophenyl) -1-phenyl-1H-indole was obtained by the same process as ⁇ Step 3> of Preparation Example 1.
  • 2,4-dibromo-1-nitrobenzene (21.18 g, 75.41 mmol) was used instead of 1-bromo-2-nitrobenzene used in ⁇ Step 2> of Preparation Example 1, and 5- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole instead of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.09 g, 90.49 mmol) was used in the same manner as in ⁇ Step 2> of Preparation Example 1 to obtain 6- (5-bromo-2-nitrophenyl) -1H-indazole.
  • 6- (5-bromo-2-nitrophenyl) -1H-indazole obtained in ⁇ Step 1> of Preparation Example 7 instead of 5- (2-nitrophenyl) -1H-indazole used in ⁇ Step 3> of Preparation Example 1 Except for using 14.69 g, 46.17 mmol), 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indazole was obtained in the same manner as in ⁇ Step 3> of Preparation Example 1.
  • Compound C-3 was prepared by the same procedure as in Synthesis Example 1, except that 2-bromo-6-phenylpyridine (6.22 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1. (4.12 g, yield: 71%) was obtained.
  • Compound C-9 (Compound C1) was carried out in the same manner as in Synthesis Example 1, except that (4-bromophenyl) triphenylsilane (11.04 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1. 4.68 g, yield: 57%).
  • Compound C-17 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-2 (3.76 g, 13.29 mmol) synthesized in Preparation Example 1 was used instead of Compound IC-1 used in Synthesis Example 10. 5.65 g, yield: 72%).
  • a compound C-18 (6.73) was prepared in the same manner as in Synthesis Example 11, except that IC-2 (3.76 g, 13.29 mmol) synthesized in Preparation Example 1 was used instead of compound IC-1 used in Synthesis Example 11. g, yield: 76%).
  • Compound C-19 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-2 (3.76 g, 13.29 mmol) synthesized in Preparation Example 1 was used instead of Compound IC-1 used in Synthesis Example 12. 7.26 g, yield: 82%).
  • a compound C-20 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-3 (3.76 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 10. 6.75 g, yield: 86%) was obtained.
  • Compound C-21 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-3 (3.76 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 11. 6.38 g, yield: 72%).
  • Compound C-22 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-3 (3.76 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 12. 6.91 g, yield: 78%).
  • Compound C-23 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-4 (3.76 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 10. 4.63 g, yield: 59%).
  • Compound C-24 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-4 (3.76 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 11. 5.58 g, yield: 63%).
  • a compound C-25 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-4 (3.76 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 12. 6.29 g, yield: 71%).
  • a compound C-26 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-5 (3.76 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 10. 6.83 g, yield: 87%).
  • Compound C-27 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-5 (3.76 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 11. 6.55 g, yield: 74%).
  • Compound C-28 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-5 (3.76 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 12. 6.64 g, yield: 75%).
  • Compound C-29 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-6 (3.76 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 10. 4.55 g, yield: 58%).
  • Compound C-30 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-6 (3.76 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 11. 4.34 g, yield: 49%).
  • a compound C-31 was prepared in the same manner as in Synthesis Example 12, except that Compound IC-6 (3.76 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 12. 6.11 g, yield: 69%).
  • Compound C-32 was prepared in the same manner as in Synthesis Example 10, except that Compound IC-7 (3.95 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 10. 6.43 g, yield: 80%) was obtained.
  • Compound C-33 was prepared in the same manner as in Synthesis Example 11, except that Compound IC-7 (3.95 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 11. 5.97 g, yield: 66%).
  • Compound C-34 was prepared in the same manner as in Synthesis Example 12, except that Compound IC-7 (3.95 g, 13.29 mmol) used in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 12. 6.51 g, yield: 72%).
  • a compound C-39 was prepared in the same manner as in Synthesis Example 35, except that Compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-8 used in Synthesis Example 35. 1.95 g, yield: 40%) was obtained.
  • a compound C-40 was prepared by the same procedure as in Synthesis Example 36, except that Compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-8 used in Synthesis Example 36. 1.76 g, yield: 32%).
  • a compound C-41 was prepared in the same manner as in Synthesis Example 37, except that Compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-8 used in Synthesis Example 37. 1.45 g, yield: 25%).
  • Compound C-42 was prepared by the same procedure as in Synthesis Example 38, except that Compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-8 used in Synthesis Example 38. 2.15 g, yield: 37%).
  • 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
  • An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C-1 used as a light emitting host material in forming the emission layer in Example 1.
  • the structure of CBP used is as follows.
  • Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
  • Example 1 Compound C-1 6.73 518 41.8
  • Example 2 Compound C-2 6.73 518 41.5
  • Example 3 Compound c-3 6.74 517 41.3
  • Example 4 Compound c-4 6.64 516 43.5
  • Example 5 Compound C-5 6.65 516 41.7
  • Example 6 Compound c-6 6.66 516 42.1
  • Example 7 Compound c-7 6.66 516 38.8
  • Example 8 Compound c-8 6.9 517 40.3
  • Example 9 Compound c-9 6.91 517 40.2
  • Example 10 Compound C-10 6.75 516 39.1
  • Example 11 Compound C-11 6.68 515 39.2
  • Example 12 Compound c-12 6.69 517 39.3
  • Example 13 Compound C-13 6.69 516 39.4
  • Example 14 Compound c-14 6.71 515 41.2
  • Example 15 Compound c-15 6.73 515 41.2
  • the green organic EL device of Examples 1 to 42 which uses the compounds C-1 to C-4 according to the present invention as a host material of the light emitting layer, is the green of Comparative Example 1 using conventional CBP. It was confirmed that the organic EL device exhibited better performance in terms of current efficiency and driving voltage.

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  • Physics & Mathematics (AREA)
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Abstract

La présente invention concerne un composé organique pouvant être utilisé en tant que matériau pour un élément électroluminescent organique, et se réfère à un élément électroluminescent organique comprenant ce composé, et, plus spécifiquement, à un composé organique possédant des caractéristiques exceptionnelles de stabilité thermique et de capacité d'émission lumineuse, ainsi qu'à un élément électroluminescent organique comprenant ce composé organique en tant que matériau d'une couche de substance organique, et qui possède des propriétés améliorées d'efficacité lumineuse, de tension d'attaque et de durée de vie.
PCT/KR2013/010483 2012-12-10 2013-11-19 Nouveau composé organique et élément électroluminescent organique comprenant celui-ci Ceased WO2014092351A1 (fr)

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KR102307359B1 (ko) * 2014-12-22 2021-10-05 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

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WO2006047017A1 (fr) * 2004-09-20 2006-05-04 Janssen Pharmaceutica N.V. Nouvel heteroatome tetracyclique contenant des derives utiles en tant que modulateurs du recepteur de l'hormone steroide sexuelle
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KR20120127550A (ko) * 2011-05-11 2012-11-22 삼성디스플레이 주식회사 축합환 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치

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KR20120127550A (ko) * 2011-05-11 2012-11-22 삼성디스플레이 주식회사 축합환 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치

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WO2016011390A1 (fr) * 2014-07-18 2016-01-21 Biogen Ma Inc. Agents d'inhibition de l'irak 4
US10246456B2 (en) 2014-07-18 2019-04-02 Biogen Ma Inc. IRAK4 inhibiting agents
US10577367B2 (en) 2014-07-18 2020-03-03 Biogen Ma Inc. IRAK4 inhibiting agents

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