WO2013147427A1 - Organic compound and organic electroluminescent element comprising same - Google Patents
Organic compound and organic electroluminescent element comprising same Download PDFInfo
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- WO2013147427A1 WO2013147427A1 PCT/KR2013/001721 KR2013001721W WO2013147427A1 WO 2013147427 A1 WO2013147427 A1 WO 2013147427A1 KR 2013001721 W KR2013001721 W KR 2013001721W WO 2013147427 A1 WO2013147427 A1 WO 2013147427A1
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- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- 239000010410 layer Substances 0.000 claims abstract description 61
- 239000012044 organic layer Substances 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000005104 aryl silyl group Chemical group 0.000 claims description 23
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 21
- 125000005264 aryl amine group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000011368 organic material Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
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- 238000003786 synthesis reaction Methods 0.000 description 257
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- 239000000463 material Substances 0.000 description 38
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- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 3
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- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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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 a function.
- the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission 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 hole blocking layer
- BCP hole blocking layer
- Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer
- 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 the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is 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 8 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a 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 A cycloalkyl group of -C 40 , a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms
- At least one of R 1 to R 8 is bonded to an adjacent group to form a condensed ring represented by the following formula (2),
- X 1 to X 4 are the same as or different from each other, and each independently CR 9 or N, wherein at least one of X 1 to X 4 is N,
- At least one R 9 is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, Substituted or unsubstituted C 2 to 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 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted
- Ar 1 is hydrogen, 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 to 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 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 , A substituted or unsubstituted C 1 ⁇ C 40 Alkylsilyl group, and a substituted or unsubstituted C
- substituents respectively introduced to the 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 - a heteroaryl group of C 40 aryl group, the number of nuclear atoms of 5 to 40, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 doedoe of the cycloalkyl group, the nuclear atoms of 3
- the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
- an organic electroluminescent device characterized in that it comprises a compound represented by the formula (1).
- At least one of the one or more organic material layers is preferably a light emitting layer.
- the compound represented by Chemical Formula 1 is a blue, green or red phosphorescent host material.
- 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 present invention not only has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], but also has a wide energy band gap to increase the bonding force between holes and electrons. It can be characterized in that it provides a compound represented by the formula (1).
- the driving voltage, efficiency (light emitting efficiency, power efficiency), lifetime, and luminance of the device can be improved.
- a heterocyclic moiety particularly an indole derivative moiety, is fused to a terminal of dibenzothiophene, and the energy level is controlled by various substituents, thereby wide bandgap. You will have (sky blue ⁇ red).
- the phosphorescent property of the device may be improved, and the hole injection ability and / or the transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics may be improved. Therefore, the present invention can be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, etc. due to the introduction of various substituents.
- the compound has a wide bandgap due to the indole derivative moiety fused to the terminal of dibenzothiophene, and can enhance the binding force between the hole and the electron, and as a host material of the light emitting layer as compared to the conventional CBP. It can exhibit excellent properties.
- the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the dibenzothiophene backbone, thereby improving the glass transition temperature, thereby having a higher thermal stability than the conventional CBP Can be. Therefore, the device including the compound of the present invention can greatly improve durability and lifespan characteristics.
- the compound of Formula 1 according to the present invention when adopted as a hole injection / transport layer, blue, green, and / or red phosphorescent host material of an organic EL device, the compound of Formula 1 may have an excellent effect on efficiency and lifetime compared to conventional CBP. have. 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 in maximizing the performance in the full color organic light emitting panel.
- R 1 to R 8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 ⁇ C 40 alkyl 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 arylamine group, substituted or unsubstituted C 1 to C 40 An alkylsilyl group, and a substituted or unsubstituted C 6 -C 40 arylsilyl group, and a condensed ring (preferably condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, condensed) Heteroaromatic ring or a combination thereof).
- R 1 to R 8 is bonded to an adjacent group to form a condensed ring represented by the formula (2).
- R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , or R 7 and R 8 are bonded to each other and are represented by Formula 2
- the remaining substituents that do not form a condensed ring represented by Formula 2 may be hydrogen.
- One or more substituents respectively introduced to the alkyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, and arylsilyl group of R 1 to R 8 are each independently deuterium, halogen, cyano group, C 1 to C 40
- X 1 to X 4 are the same as or different from each other, and each independently CR 9 or N, wherein one of X 1 to X 4 is N and the other is CR 9 desirable.
- Ar 1 is hydrogen, a substituted or unsubstituted C 6 ⁇ C 40 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryl It is preferably selected from the group consisting of an amine group and a substituted or unsubstituted C 6 -C 40 arylsilyl group.
- one or more substituents respectively introduced into the aryl group, heteroaryl group, arylamine group, and arylsilyl group of Ar 1 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 alkyl Oxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, and C 6 to C 40 It is selected from the group consisting of an arylsilyl group, a plurality of substituents may be the same or different from each other.
- Ar 1 is selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, wherein the aryl group and Each of the one or more substituents introduced into the heteroaryl group is 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 of the aryl group, the number of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ C 40 doedoe of the cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇
- At least one R 9 is 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 6 -C 40 aryl Groups, substituted or unsubstituted heteroaryl groups having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 arylamine groups, substituted or unsubstituted C 1 to C 40 alkylsilyl groups, and substitutions Or an unsubstituted C 6 -C 40 arylsilyl group.
- one or more substituents respectively introduced into the alkyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, arylsilyl group of R 9 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 atoms 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, a 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 It is selected from the group consisting of 6 ⁇ C 40 arylsilyl group, a plurality of substituents may be the same or
- R 1 to R 9 and Ar 1 may be each independently selected from the group consisting of hydrogen or the following substituents S1 to S138, but is not limited thereto.
- R 1 to R 8 is selected from the group consisting of hydrogen or the following substituents S1 to S138, at least one of R 1 to R 8 is combined with an adjacent group to form a condensed ring represented by the formula (2).
- Examples of the compound represented by Chemical Formula 1 according to the present invention include compounds represented by Chemical Formula 3 to compounds represented by Chemical Formula 8, but are not limited thereto.
- X 1 to X 4 , R 1 to R 9 , and Ar 1 are the same as defined in Formula 1, respectively.
- Specific examples of the compound represented by Formula 1 include, but are not limited to, a compound represented by Formula 9 to a compound represented by Formula 32.
- R 1 to R 9 are the same as defined in Formula 1, respectively.
- Ar 1 is the same as defined in Formula 1, preferably selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms;
- one or more substituents respectively introduced into the aryl group and the heteroaryl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky Neyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine Group, a C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 1 to C 40 alkylsilyl group, and a C 6 to C 40 ary
- 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 of which are 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 includes the compound represented by Chemical Formula 1, preferably the compound represented by Chemical Formula 3 to the compound represented by Chemical Formula 8, and more preferably the compound represented by Chemical Formula 9 to the compound represented by Chemical Formula 24. It provides an organic electroluminescent device.
- 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
- the compound represented by the formula (1) preferably the compound represented by the formula (3) to the compound represented by the formula (8), more preferably the compound represented by the formula (9) to the compound represented by the formula (24).
- the compounds of Formula 1 to 24 may be used alone or in combination of two or more.
- the one or more organic material layers 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, preferably a hole injection / transport layer, a light emitting layer or an electron transport layer, more preferably a light emitting layer Can be.
- 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 may 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 in the art, except that at least one layer (eg, the light emitting layer, the hole transport layer and / or electron transport layer) of the organic material layer is formed to include the compound represented by the formula (1) It can be prepared by forming other organic material layers and electrodes using known materials and methods.
- at least one layer eg, the light emitting layer, the hole transport layer and / or electron transport layer
- the organic material layer is formed to include the compound represented by the formula (1) It can be prepared by forming other organic material layers and electrodes using known materials and methods.
- 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.
- Preparation (1) was carried out in the same manner as in Preparation Step 1-1, to obtain 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
- Preparation Example 1 Same as Preparation Step 1-2 of Preparation Example 1, except that 7.64 g of 2,6-dichloro-3-nitropyridine was used instead of 2-chloro-3-nitropyridine used in Preparation Step 1-2 of Preparation Example 1. 6-chloro-2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine was obtained.
- the intermediate compound IMC-18 was obtained in the same manner as in Synthesis Step 18-1 of Synthesis Example 18.
- the intermediate compound IMC-18 was obtained in the same manner as in Synthesis Step 18-1 of Synthesis Example 18.
- the intermediate compound IMC-30 was obtained in the same manner as in Synthesis Step 30-1 of Synthesis Example 30.
- the intermediate compound IMC-30 was obtained in the same manner as in Synthesis Step 30-1 of Synthesis Example 30.
- the compound Mat-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured as follows.
- a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 mm 3 was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
- ITO Indium tin oxide
- Example 2 The same procedure as in Example 1 was repeated except that the compounds Mat-2 to Mat-35 synthesized in Synthesis Examples 2 to 35 were used instead of the compound Mat-1 used as the light emitting host material in Example 1 to form a light emitting layer.
- the compounds Mat-2 to Mat-35 synthesized in Synthesis Examples 2 to 35 were used instead of the compound Mat-1 used as the light emitting host material in Example 1 to form a light emitting layer.
- a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 used as a light emitting host material when forming the emission layer.
- the structure of CBP is as follows.
- a green organic EL device was manufactured in the same manner as in Example 1, except that Com-1 was used instead of the compound Mat-1 as a light emitting host material when forming the emission layer.
- the structure of Com-1 is as follows.
- Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
- Example 1 Mat-1 6.55 520 40.0
- Example 2 Mat-2 6.40 518 39.2
- Example 3 Mat-3 6.50 519 40.1
- Example 4 Mat-4 6.51 520 39.5
- Example 5 Mat-5 6.56 517 40.8
- Example 6 Mat-6 6.45 515 41.0
- Example 7 Mat-7 6.51 521 41.4
- Example 8 Mat-8 6.46 517 40.5
- Example 9 Mat-9 6.48 516 40.9
- Example 10 Mat-10 6.40 519 41.1
- Example 11 Mat-11 6.62 520 40.8
- Example 12 Mat-12 6.61 518 41.1
- Example 13 Mat-13 6.60 516 40.2
- Example 14 Mat-14 6.50 516 40.7
- Example 15 Mat-15 6.69 520 41.1
- Example 16 Mat-16 6.58 519 41.5
- Example 17 Mat-17 6.62 518 39.9
- Example 18 Mat-18 6.55 515 41.4
- Example 19 Mat-19 6.45 5
- the green organic EL devices manufactured in Examples 1 to 35 each using the compound represented by Formula 1 according to the present invention (Compounds Mat-1 to Mat-35) as the host material of the light emitting layer were prepared using conventional CBP. It was confirmed that the green organic EL devices of Comparative Examples 1 and 2 exhibited superior performance in terms of current efficiency and driving voltage.
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Abstract
The present invention relates to a compound represented by chemical formula 1 and to an organic electroluminescent element comprising same, and the compound represented by chemical formula 1 is comprised in one or more organic layer(s) and preferably luminescent layer(s) such that properties such as the light-emitting efficiency, the drive voltage and the life of the element can be improved.
Description
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.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.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후, 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. The study of organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene monocrystals in 1965, based on Bernanose's observation of organic thin film emission in the 1950s. By (Tang), an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed. Since then, in order to make a high efficiency, long life organic EL device, it has evolved to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있기 때문에, 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대한 연구가 많이 진행되고 있다. 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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광 재료로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히, 발광 재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료들은 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red) 도판트 재료로 사용되고 있으며, 현재까지는 CBP가 인광 호스트 재료로 높은 특성을 나타내고 있다.Hole injection layer, hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.
그러나, 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 OLED 소자에서의 수명 측면에서 만족할 만한 수준이 되지 못하는 실정이다. 따라서 더욱 성능이 뛰어난 재료의 개발이 요구되고 있다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and thermal stability is not very good, and thus, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of more excellent materials is required.
본 발명은 높은 유리 전이온도로 인해 열적 안정성이 우수하면서, 정공과 전자의 결합력을 향상시킬 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.It is an object of the present invention to provide a novel organic compound which is excellent in thermal stability due to a high glass transition temperature and can improve the binding force between holes and electrons.
또, 본 발명은 상기 신규 유기 화합물을 포함하여 구동전압, 발광효율 등이 향상된 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In addition, 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.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by Formula 1:
화학식 1 
Formula 1
상기 화학식 1에서,In Chemical Formula 1,
R1 내지 R8 은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 인접하는 기와 결합하여 축합(fused) 고리를 형성할 수 있으며, R 1 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a 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 A cycloalkyl group of -C 40 , a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 1 -C 40 alkylsilyl group, and a substituted or unsubstituted C 6 -C 40 Selected from the group consisting of arylsilyl groups, may be bonded to adjacent groups to form a fused ring,
이때 R1 내지 R8 중 적어도 하나는 인접하는 기와 결합하여 하기 화학식 2로 표시되는 축합 고리를 형성하고,At least one of R 1 to R 8 is bonded to an adjacent group to form a condensed ring represented by the following formula (2),
화학식 2 
Formula 2
상기 화학식 2 에서,In Chemical Formula 2,
X1 내지 X4는 서로 동일하거나 상이하고, 각각 독립적으로 CR9 또는 N이고, 이때 X1 내지 X4 중 적어도 하나는 N 이며,X 1 to X 4 are the same as or different from each other, and each independently CR 9 or N, wherein at least one of X 1 to X 4 is N,
하나 이상의 R9는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 이때 하나 이상의 R9는 인접한 기와 결합하여 축합 고리를 형성할 수 있으며,At least one R 9 is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, Substituted or unsubstituted C 2 to 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 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, and a substituted or unsubstituted C 6 to C 40 arylsilyl group Selected from the group wherein one or more R 9 may combine with adjacent groups to form a condensed ring,
Ar1은 수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,Ar 1 is hydrogen, 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 to 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 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 , A substituted or unsubstituted C 1 ~ C 40 Alkylsilyl group, and a substituted or unsubstituted C 6 ~ C 40 An arylsilyl group,
상기 R1 내지 R9 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 아릴알킬기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 및 아릴실릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R 1 to R 9 and Ar 1 And one or more substituents respectively introduced to the 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 - a heteroaryl group of C 40 aryl group, the number of nuclear atoms of 5 to 40, C 6 ~ C 40 of the aryloxy group, C 1 ~ alkyloxy group of C 40, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 doedoe of the cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, aryl silyl group the group consisting of C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 of the plurality of substituents are identical to each other Can be different.
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것이 특징인 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer One provides an organic electroluminescent device characterized in that it comprises a compound represented by the formula (1).
여기서, 상기 1층 이상의 유기물층 중 적어도 하나는 발광층인 것이 바람직하다. 이때, 상기 화학식 1로 표시되는 화합물은 청색, 녹색 또는 적색의 인광 호스트 재료이다.Here, at least one of the one or more organic material layers is preferably a light emitting layer. In this case, the compound represented by Chemical Formula 1 is a blue, green or red phosphorescent host material.
본 발명의 화학식 1 로 표시되는 화합물은 열적 안정성 및 인광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층에 적용될 수 있다.Since 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.
따라서, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 물질로 사용할 경우, 종래 호스트 물질에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능, 수명이 크게 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다. Therefore, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to the conventional host material can be manufactured, and further, performance In addition, a full color display panel with a greatly improved lifespan can be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 종래 유기 EL 소자용 재료 [예: 4,4-dicarbazolybiphenyl (이하, 'CBP'로 표시함)]보다 분자량이 클 뿐만 아니라, 넓은 에너지 밴드갭을 가지면서, 정공과 전자의 결합력을 높일 수 있는 상기 화학식 1로 표시되는 화합물을 제공하는 것을 특징으로 한다. 상기 화합물을 유기 EL 소자에 이용할 경우, 소자의 구동 전압, 효율(발광효율, 전력효율), 수명 및 휘도 측면이 향상될 수 있다.The present invention not only has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], but also has a wide energy band gap to increase the bonding force between holes and electrons. It can be characterized in that it provides a compound represented by the formula (1). When the compound is used in an organic EL device, the driving voltage, efficiency (light emitting efficiency, power efficiency), lifetime, and luminance of the device can be improved.
상기 화학식 1로 표시되는 화합물은, 디벤조싸이오펜(dibenzothiophene)의 말단에 헤테로환 모이어티, 특히 인돌 유도체 모이어티(moiety)가 융합되어 있고, 여러 치환체에 의해 에너지 레벨이 조절됨으로써, 넓은 밴드갭 (sky blue ~ red)을 갖게 된다. 이로 인해, 소자의 인광특성을 개선함과 동시에 정공 주입 능력 및/또는 수송 능력, 발광효율, 구동전압, 수명 특성 등이 개선될 수 있다. 따라서, 발광층뿐만 아니라, 여러 치환체의 도입으로 인해 정공 수송층, 정공 주입층 등으로도 응용될 수 있다. 특히, 상기 화합물은 디벤조싸이오펜(dibenzothiophene)의 말단에 융합된 인돌 유도체 모이어티로 인해 넓은 밴드갭을 가지면서, 정공과 전자의 결합력을 높일 수 있기 때문에, 종래 CBP에 비해 발광층의 호스트 재료로서의 우수한 특성을 나타낼 수 있다.In the compound represented by Formula 1, a heterocyclic moiety, particularly an indole derivative moiety, is fused to a terminal of dibenzothiophene, and the energy level is controlled by various substituents, thereby wide bandgap. You will have (sky blue ~ red). As a result, the phosphorescent property of the device may be improved, and the hole injection ability and / or the transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics may be improved. Therefore, the present invention can be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, etc. due to the introduction of various substituents. In particular, the compound has a wide bandgap due to the indole derivative moiety fused to the terminal of dibenzothiophene, and can enhance the binding force between the hole and the electron, and as a host material of the light emitting layer as compared to the conventional CBP. It can exhibit excellent properties.
특히, 디벤조싸이오펜 기본골격에, 다수 도입된 다양한 방향족 환(aromatic ring) 치환체로 인해 화합물의 분자량이 유의적으로 증대됨으로써, 유리전이온도가 향상되고, 이로 인해 종래 CBP 보다 높은 열적 안정성을 가질 수 있다. 따라서, 본 발명의 화합물을 포함하는 소자는 내구성 및 수명 특성을 크게 향상시킬 수 있다. In particular, the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the dibenzothiophene backbone, thereby improving the glass transition temperature, thereby having a higher thermal stability than the conventional CBP Can be. Therefore, the device including the compound of the present invention can greatly improve durability and lifespan characteristics.
아울러, 본 발명에 따른 화학식 1의 화합물을 유기 EL 소자의 정공 주입/수송층, 청색, 녹색 및/또는 적색의 인광 호스트 재료로 채택할 경우, 종래 CBP 대비 효율 및 수명 면에서 월등히 우수한 효과를 발휘할 수 있다. 따라서, 본 발명에 따른 화합물은 유기 EL 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 특히 이러한 소자 수명 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화에도 큰 효과가 있다.In addition, when the compound of Formula 1 according to the present invention is adopted as a hole injection / transport layer, blue, green, and / or red phosphorescent host material of an organic EL device, the compound of Formula 1 may have an excellent effect on efficiency and lifetime compared to conventional CBP. have. 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 in maximizing the performance in the full color organic light emitting panel.
상기 화학식 1로 표시되는 화합물에 있어서, 바람직하게는 R1 내지 R8이 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어지는 군에서 선택되고, 인접하는 기와 결합하여 축합 고리(바람직하게는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합임)를 형성할 수 있다.In the compound represented by Formula 1, preferably R 1 to R 8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1 ~ C 40 alkyl 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 arylamine group, substituted or unsubstituted C 1 to C 40 An alkylsilyl group, and a substituted or unsubstituted C 6 -C 40 arylsilyl group, and a condensed ring (preferably condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, condensed) Heteroaromatic ring or a combination thereof).
이때, R1 내지 R8 중 적어도 하나는 인접하는 기와 결합하여 상기 화학식 2로 표시되는 축합 고리를 형성한다. 예를 들어, R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6와 R7, 또는 R7과 R8이 서로 결합하여 상기 화학식 2로 표시되는 축합 고리를 형성할 경우, 상기 화학식 2로 표시되는 축합 고리를 형성하지 않은 나머지 치환기들은 수소일 수 있다.At this time, at least one of R 1 to R 8 is bonded to an adjacent group to form a condensed ring represented by the formula (2). For example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , or R 7 and R 8 are bonded to each other and are represented by Formula 2 When forming a condensed ring, the remaining substituents that do not form a condensed ring represented by Formula 2 may be hydrogen.
상기 R1 내지 R8의 알킬기, 아릴기, 헤테로아릴기, 아릴아민기, 알킬실릴기, 및 아릴실릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.One or more substituents respectively introduced to the alkyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, and arylsilyl group of R 1 to R 8 are each independently deuterium, halogen, cyano group, C 1 to C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a nuclear atom having 5 to 40 heteroaryl groups, a C 6 to C 40 aryloxy group , C 1 ~ C 40 Alkyloxy group, C 6 ~ C 40 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group And and C 6 ~ C 40 It is selected from the group consisting of arylsilyl group, a plurality of substituents may be the same or different from each other.
상기 화학식 2로 표시되는 축합 고리에 있어서, X1 내지 X4는 서로 동일하거나 상이하고, 각각 독립적으로 CR9 또는 N이고, 이때 X1 내지 X4 중 하나는 N 이고, 나머지는 CR9인 것이 바람직하다.In the condensed ring represented by Formula 2, X 1 to X 4 are the same as or different from each other, and each independently CR 9 or N, wherein one of X 1 to X 4 is N and the other is CR 9 desirable.
또, 상기 Ar1은 수소, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴아민기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 것이 바람직하다.In addition, Ar 1 is hydrogen, a substituted or unsubstituted C 6 ~ C 40 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ~ C 40 aryl It is preferably selected from the group consisting of an amine group and a substituted or unsubstituted C 6 -C 40 arylsilyl group.
이때, 상기 Ar1의 아릴기, 헤테로아릴기, 아릴아민기, 아릴실릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.In this case, one or more substituents respectively introduced into the aryl group, heteroaryl group, arylamine group, and arylsilyl group of Ar 1 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 alkyl Oxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, and C 6 to C 40 It is selected from the group consisting of an arylsilyl group, a plurality of substituents may be the same or different from each other.
보다 바람직하게는, 상기 Ar1이 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되며, 이때 상기 아릴기 및 헤테로아릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.More preferably, Ar 1 is selected from the group consisting of a substituted or unsubstituted C 6 ~ C 40 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, wherein the aryl group and Each of the one or more substituents introduced into the heteroaryl group is 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 of the aryl group, the number of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, a C 3 ~ C 40 doedoe of the cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ aryl silyl group consisting of C 40, a plurality of substituents are the same or different, can do.
또, 하나 이상의 R9는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어지는 군에서 선택되는 것이 바람직하다.In addition, at least one R 9 is 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 6 -C 40 aryl Groups, substituted or unsubstituted heteroaryl groups having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 arylamine groups, substituted or unsubstituted C 1 to C 40 alkylsilyl groups, and substitutions Or an unsubstituted C 6 -C 40 arylsilyl group.
이때, R9의 알킬기, 아릴기, 헤테로아릴기, 아릴아민기, 알킬실릴기, 아릴실릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.At this time, one or more substituents respectively introduced into the alkyl group, aryl group, heteroaryl group, arylamine group, alkylsilyl group, arylsilyl group of R 9 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 atoms 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, a 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 It is selected from the group consisting of 6 ~ C 40 arylsilyl group, a plurality of substituents may be the same or different from each other.
더욱 바람직하게는, R1 내지 R9 및 Ar1이 각각 독립적으로 수소, 또는 하기 치환기 S1 내지 S138로 이루어진 군에서 선택될 수 있는데, 이에 한정되는 것은 아니다. 다만, R1 내지 R8은 수소, 또는 하기 치환기 S1 내지 S138로 이루어진 군에서 선택되되, R1 내지 R8 중 적어도 하나는 인접하는 기와 결합하여 상기 화학식 2로 표시되는 축합 고리를 형성한다.More preferably, R 1 to R 9 and Ar 1 may be each independently selected from the group consisting of hydrogen or the following substituents S1 to S138, but is not limited thereto. However, R 1 to R 8 is selected from the group consisting of hydrogen or the following substituents S1 to S138, at least one of R 1 to R 8 is combined with an adjacent group to form a condensed ring represented by the formula (2).
본 발명에 따른 화학식 1로 표시되는 화합물의 예로는 하기 화학식 3으로 표시되는 화합물 내지 화학식 8로 표시되는 화합물 등이 있는데, 이에 한정되지 않는다.Examples of the compound represented by Chemical Formula 1 according to the present invention include compounds represented by Chemical Formula 3 to compounds represented by Chemical Formula 8, but are not limited thereto.
화학식 3 
Formula 3
화학식 4 
Formula 4
화학식 5 
Formula 5
화학식 6 
Formula 6
화학식 7 
Formula 7
화학식 8 
Formula 8
상기 화학식 3 내지 화학식 8 에서, In Chemical Formulas 3 to 8,
X1 내지 X4, R1 내지 R9, 및 Ar1은 각각 화학식 1에서 정의된 바와 동일하다.X 1 to X 4 , R 1 to R 9 , and Ar 1 are the same as defined in Formula 1, respectively.
상기 화학식 1로 표시되는 화합물의 구체적인 예로는 하기 화학식 9로 표시되는 화합물 내지 화학식 32로 표시되는 화합물 등이 있는데, 이에 한정되지 않는다.Specific examples of the compound represented by Formula 1 include, but are not limited to, a compound represented by Formula 9 to a compound represented by Formula 32.
화학식 9 
Formula 9
화학식 10 
Formula 10
화학식 11 
Formula 11
화학식 12 
Formula 12
화학식 13 
Formula 13
화학식 14 
Formula 14
화학식 15 
Formula 15
화학식 16 
Formula 16
화학식 17 
Formula 17
화학식 18 
Formula 18
화학식 19 
Formula 19
화학식 20 
Formula 20
화학식 21 
Formula 21
화학식 22 
Formula 22
화학식 23 
Formula 23
화학식 24 
Formula 24
화학식 25 
Formula 25
화학식 26 
Formula 26
화학식 27 
Formula 27
화학식 28 
Formula 28
화학식 29 
Formula 29
화학식 30 
Formula 30
화학식 31 
Formula 31
화학식 32 
Formula 32
상기 화학식 9 내지 32에서, In Chemical Formulas 9 to 32,
R1 내지 R9은 각각 화학식 1에서 정의한 바와 동일하고,R 1 to R 9 are the same as defined in Formula 1, respectively,
상기 Ar1 은 화학식 1에서 정의한 바와 동일하며, 바람직하게는 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되고, 이때 상기 아릴기 및 헤테로아릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.Ar 1 is the same as defined in Formula 1, preferably selected from the group consisting of a substituted or unsubstituted C 6 ~ C 40 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms; At this time, one or more substituents respectively introduced into the aryl group and the heteroaryl group are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine Group, a C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 1 to C 40 alkylsilyl group, and a C 6 to C 40 arylsilyl group, The substituents may be the same or different from one another.
하기 화학식들은 본 발명에 따른 화학식 1의 화합물의 대표적인 예들이나, 본 발명에 따른 화학식 1의 화합물이 하기 예시된 것들에 한정되는 것은 아니다.The following formulas are representative examples of the compound of formula 1 according to the present invention, but the compound of formula 1 according to the present invention is not limited to those illustrated below.
본 발명에서 사용된 "비치환된 알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 포함한다. As used herein, "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.
"비치환된 알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있으며, 이에 한정되는 것은 아니다. “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.
"비치환된 알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에타인일(ethynyl), 2-프로파인일(2-propynyl) 등이 있는데, 이에 제한되는 것은 아니다.“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 of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
"비치환된 아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된(fused) 형태로 부착될 수 있다. 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 포함되며 이에 한정되는 것은 아니다."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.
"비치환된 헤테로아릴"은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된(fused) 형태로 부착될 수 있고, 나아가 아릴기와의 축합된 형태도 포함하는 것으로 해석한다. 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리를 포함하고, 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등도 포함하는 것으로 해석한다."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. Examples of heteroaryl 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.
"비치환된 아릴옥시"는 RO-로 표시되는 1가의 치환기로서, 상기 R은 탄소수 5 내지 60의 아릴이다. 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있다."Unsubstituted aryloxy" is a monovalent substituent represented by RO-, wherein R is an aryl having 5 to 60 carbon atoms. Examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
"비치환된 알킬옥시"는 R'O-로 표시되는 1가의 치환기로서, 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 포함될 수 있으며 이에 한정되지는 않는다. "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. Examples of alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
"비치환된 아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다."Unsubstituted arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms.
"비치환된 시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine)등이 포함되지만 이에 한정되는 것은 아니다. "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.
"비치환된 헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이의 비-제한적인 예로는 모르폴린, 피페라진 등이 있다."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.
"알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다."Alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.
"축합(fused) 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Fused ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
한편, 본 발명은 전술한 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3로 표시되는 화합물 내지 화학식 8로 표시되는 화합물, 보다 바람직하게는 화학식 9로 표시되는 화합물 내지 화학식 24로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.Meanwhile, the present invention includes the compound represented by Chemical Formula 1, preferably the compound represented by Chemical Formula 3 to the compound represented by Chemical Formula 8, and more preferably the compound represented by Chemical Formula 9 to the compound represented by Chemical Formula 24. It provides an organic electroluminescent device.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3로 표시되는 화합물 내지 화학식 8로 표시되는 화합물, 보다 바람직하게는 화학식 9로 표시되는 화합물 내지 화학식 24로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1 내지 24의 화합물은 단독으로 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, 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 The compound represented by the formula (1), preferably the compound represented by the formula (3) to the compound represented by the formula (8), more preferably the compound represented by the formula (9) to the compound represented by the formula (24). In this case, the compounds of Formula 1 to 24 may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 바람직하게는 정공 주입/수송층, 발광층 또는 전자수송층일 수 있고, 보다 바람직하게는 발광층일 수 있다.The one or more organic material layers 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, preferably a hole injection / transport layer, a light emitting layer or an electron transport layer, more preferably a light emitting layer Can be.
본 발명의 일례에 따르면, 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. 이와 같이, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다.According to one embodiment of the present invention, 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). As such, when the compound of Formula 1 is 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.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판, 양극, 정공주입층, 정공수송층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 이때, 본 발명의 화합물은 발광층의 인광 호스트로 이용될 수 있다. 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다. 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. In this case, 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. In this case, the compound of the present invention may be used as a phosphorescent host of the light emitting layer. An electron injection layer may be further stacked on the electron transport layer.
또한, 본 발명에 따른 유기 전계 발광 소자의 구조는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.In addition, 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.
본 발명에 따른 유기 전계 발광 소자는 상기 유기물층 중 1층 이상(예컨대, 발광층, 정공수송층 및/또는 전자수송층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device according to the present invention is in the art, except that at least one layer (eg, the light emitting layer, the hole transport layer and / or electron transport layer) of the organic material layer is formed to include the compound represented by the formula (1) It can be prepared by forming other organic material layers and electrodes using known materials and methods.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.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.
또, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지 않는다.In addition, 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.
또, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지 않는다.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.
이하 본 발명을 준비예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 준비예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 준비예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through a preparation example. However, the following preparation examples are merely illustrative of the present invention and the present invention is not limited by the following preparation examples.
[준비예 1] 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 및 5H-benzothieno[3,2-f]pyrido[3,2-b]indole의 합성Preparation Example 1 Synthesis of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole and 5H-benzothieno [3,2-f] pyrido [3,2-b] indole
<준비단계 1-1> 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane의 합성Preparation Step 1-1 Synthesis of 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
질소 기류 하에서 2-bromodibenzo[b,d]thiophene 33.68 g (0.128 mol)을 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 48.58 g (0.191 mol), 팔라듐비스디페닐포스피노페로센디클로로(Pd(dppf)Cl2) 5.20 g (5 mol %), 포타슘아세테이트(KOAc) 37.55 g (0.383 mol), 및 N,N-디메틸포름아미드(N,N-dimethylformamide, DMF) 900 ml와 혼합한 다음, 130 ℃에서 12시간 동안 교반한 후, 반응을 종결시키고, 에틸아세테이트로 유기층을 추출한 다음, MgSO4로 수분이 제거하였다. 이후, 용매가 제거된 유기층을 컬럼크로마토그래피로 정제하여, 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 21.05 g (yield : 53 %)을 획득하였다. 33.68 g (0.128 mol) of 2-bromodibenzo [b, d] thiophene under nitrogen stream was added to 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1, 3,2-dioxaborolane) 48.58 g (0.191 mol), palladiumbisdiphenylphosphinoferrocenedichloro (Pd (dppf) Cl 2 ) 5.20 g (5 mol%), potassium acetate (KOAc) 37.55 g (0.383 mol), and After mixing with 900 ml of N, N-dimethylformamide (DMF), stirring at 130 ° C. for 12 hours, terminating the reaction, extracting the organic layer with ethyl acetate, and then moistening with MgSO 4 . This was removed. Then, the solvent-free organic layer was purified by column chromatography, and 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 21.05 g (yield: 53%) was obtained.
1H-NMR : δ 1.24 (s, 12H), 7.50 (m, 3H), 7.99 (m, 3H), 8.53 (d, 1H) 1 H-NMR: δ 1.24 (s, 12H), 7.50 (m, 3H), 7.99 (m, 3H), 8.53 (d, 1H)
<준비단계 1-2> 2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine의 합성Preparation Step 1-2 Synthesis of 2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine
질소 기류 하에서 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 12.28 g (39.6 mmol)을, 2-chloro-3-nitropyridine 6.28 g (39.6 mmol), NaOH 4.75 g (118.8 mmol), 및 THF/H2O (200 ml/100 ml)와 혼합한 후 교반하였다. 이후, 40 ℃에서 상기 혼합물에 Pd(PPh3)4 1.15 g (5 mol%)을 넣고, 80 ℃에서 12 시간 동안 교반하였다. 반응 종결 후, 메틸렌클로라이드로 유기층을 추출한 다음, MgSO4를 넣고 필터링하였다. 이후, 필터링된 유기층에서 용매를 제거한 다음, 컬럼크로마토그래피로 정제하여, 2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine 7.76 g (yield: 64 %)을 획득하였다. 12.28 g (39.6 mmol) of 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane under nitrogen stream, 2-chloro-3- 6.28 g (39.6 mmol) nitropyridine, 4.75 g (118.8 mmol) NaOH, and THF / H 2 O (200 ml / 100 ml) were mixed and stirred. Thereafter, 1.15 g (5 mol%) of Pd (PPh 3 ) 4 was added to the mixture at 40 ° C., and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. Thereafter, the solvent was removed from the filtered organic layer, and then purified by column chromatography to obtain 7.76 g (yield: 64%) of 2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine.
1H-NMR : δ 7.53 (m, 3H), 7.90 (m, 2H), 8.41 (m, 4H), 8.96 (d, 1H) 1 H-NMR: δ 7.53 (m, 3H), 7.90 (m, 2H), 8.41 (m, 4H), 8.96 (d, 1H)
<준비단계 1-3> 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 및 5H-benzothieno[3,2-f]pyrido[3,2-b]indole의 합성Preparation Step 1-3 Synthesis of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole and 5H-benzothieno [3,2-f] pyrido [3,2-b] indole
질소 기류 하에서 2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine 5.85 g (19.10 mmol)을, triphenylphosphine(PPh3) 12.52 g (47.72 mmol), 및 1,2-dichlorobenzene 50 ml와 혼합한 후, 12시간 교반하였다. 반응 종료 후, 1,2-dichlorobenzene를 제거한 다음, 디클로로메탄으로 유기층을 추출하였다. 이후, 추출된 유기층에서 MgSO4로 물을 제거한 다음, 컬럼크로마토그래피로 정제하여, 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 1.99 g (yield: 38 %)과 5H-benzothieno[3,2-f]pyrido[3,2-b]indole 1.89 g (yield: 36 %)을 획득하였다. 5.85 g (19.10 mmol) of 2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine under nitrogen stream, 12.52 g (47.72 mmol) of triphenylphosphine (PPh 3 ), and 50 ml of 1,2-dichlorobenzene After mixing with, the mixture was stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, and then the organic layer was extracted with dichloromethane. Subsequently, water was removed from the extracted organic layer with MgSO 4 , and then purified by column chromatography, 12H-benzothieno [2,3-g] pyrido [3,2-b] indole 1.99 g (yield: 38%) and 5H 1.89 g (yield: 36%) of -benzothieno [3,2-f] pyrido [3,2-b] indole was obtained.
12H-benzothieno[2,3-g]pyrido[3,2-b]indole에 대한 1H-NMR: δ 7.22 (t, 1H) 7.51 (m, 3H), 7.89 (m, 3H), 8.51 (m, 2H), 10.64 (s, 1H) 1 H-NMR for 12H-benzothieno [2,3-g] pyrido [3,2-b] indole: δ 7.22 (t, 1H) 7.51 (m, 3H), 7.89 (m, 3H), 8.51 (m , 2H), 10.64 (s, 1H)
5H-benzothieno[3,2-f]pyrido[3,2-b]indole에 대한 1H-NMR: δ 7.21 (t, 1H) 7.54 (m, 2H), 7.84 (m, 4H), 8.44 (m, 2H), 10.63 (s, 1H) 1 H-NMR for 5H-benzothieno [3,2-f] pyrido [3,2-b] indole: δ 7.21 (t, 1H) 7.54 (m, 2H), 7.84 (m, 4H), 8.44 (m , 2H), 10.63 (s, 1H)
[준비예 2] 3-chloro-12H-benzothieno[2,3-g]pyrido[3,2-b]indole 및 2-chloro-5H-benzothieno[3,2-f]pyrido[3,2-b]indole 의 합성Preparation Example 2 3-chloro-12H-benzothieno [2,3-g] pyrido [3,2-b] indole and 2-chloro-5H-benzothieno [3,2-f] pyrido [3,2-b Synthesis of] indole
<준비단계 2-1><Preparation Step 2-1>
준비예 1의 준비단계 1-1과 동일하게 수행하여 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane를 얻었다.Preparation (1) was carried out in the same manner as in Preparation Step 1-1, to obtain 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
<준비단계 2-2> 6-chloro-2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine의 합성Preparation Step 2-2 Synthesis of 6-chloro-2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine
준비예 1의 준비단계 1-2에서 사용된 2-chloro-3-nitropyridine 대신 2,6-dichloro-3-nitropyridine 7.64 g 을 사용하는 것을 제외하고는, 준비예 1의 준비단계 1-2와 동일하게 수행하여 6-chloro-2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine을 얻었다.Preparation Example 1 Same as Preparation Step 1-2 of Preparation Example 1, except that 7.64 g of 2,6-dichloro-3-nitropyridine was used instead of 2-chloro-3-nitropyridine used in Preparation Step 1-2 of Preparation Example 1. 6-chloro-2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine was obtained.
1H-NMR : δ 7.14 (d, 1H), 7.52 (m, 2H), 7.92 (m, 2H), 8.51 (m, 4H) 1 H-NMR: δ 7.14 (d, 1H), 7.52 (m, 2H), 7.92 (m, 2H), 8.51 (m, 4H)
<준비단계 2-3> 3-chloro-12H-benzothieno[2,3-g]pyrido[3,2-b]indole 및 2-chloro-5H-benzothieno[3,2-f]pyrido[3,2-b]indole의 합성Preparation step 2-3 3-chloro-12H-benzothieno [2,3-g] pyrido [3,2-b] indole and 2-chloro-5H-benzothieno [3,2-f] pyrido [3,2 -b] synthesis of indole
준비예 1의 준비단계 1-3에서 사용된 2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine 대신 6-chloro-2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine 6.51 g 을 사용하는 것을 제외하고는, 준비예 1의 준비단계 1-3과 동일하게 수행하여 3-chloro-12H-benzothieno[2,3-g]pyrido[3,2-b]indole 및 2-chloro-5H-benzothieno[3,2-f]pyrido[3,2-b]indole을 얻었다.6-chloro-2- (dibenzo [b, d] thiophen-2-yl instead of 2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine used in Preparation Steps 1-3 of Preparation Example 1 Except for using 6.51 g of 3-nitropyridine, the same procedure as in Preparation Step 1-3 of Preparation Example 1 was carried out to provide 3-chloro-12H-benzothieno [2,3-g] pyrido [3,2-b. ] indole and 2-chloro-5H-benzothieno [3,2-f] pyrido [3,2-b] indole were obtained.
12H-benzothieno[2,3-g]pyrido[3,2-b]indole에 대한 1H-NMR: δ 7.31 (t, 1H) 7.50 (m, 3H), 7.86 (m, 2H), 8.46 (m, 2H), 10.64 (s, 1H) 1 H-NMR for 12H-benzothieno [2,3-g] pyrido [3,2-b] indole: δ 7.31 (t, 1H) 7.50 (m, 3H), 7.86 (m, 2H), 8.46 (m , 2H), 10.64 (s, 1H)
5H-benzothieno[3,2-f]pyrido[3,2-b]indole에 대한 1H-NMR: δ 7.30 (t, 1H) 7.52 (m, 2H), 7.85 (m, 3H), 8.45 (m, 2H), 10.63 (s, 1H) 1 H-NMR for 5H-benzothieno [3,2-f] pyrido [3,2-b] indole: δ 7.30 (t, 1H) 7.52 (m, 2H), 7.85 (m, 3H), 8.45 (m , 2H), 10.63 (s, 1H)
[준비예 3] 5H-benzothieno[2,3-e]pyrido[3,2-b]indole의 합성Preparation Example 3 Synthesis of 5H-benzothieno [2,3-e] pyrido [3,2-b] indole
<준비단계 3-1> 2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine의 합성Preparation Step 3-1 Synthesis of 2- (dibenzo [b, d] thiophen-4-yl) -3-nitropyridine
준비예 1의 준비단계 2-1에서 사용된 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 대신 dibenzo[b,d]thiophen-4-ylboronic acid 9.03 g 을 사용하는 것을 제외하고는, 준비예 1의 준비단계 1-2와 동일하게 수행하여 2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine을 얻었다.Instead of 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane used in Preparation Step 2-1 of Preparation Example 1, dibenzo [b, A 2- (dibenzo [b, d] thiophen-4-yl) -3- was carried out in the same manner as in Preparation Step 1-2 of Preparation Example 1, except that 9.03 g of d] thiophen-4-ylboronic acid was used. nitropyridine was obtained.
1H-NMR : δ 7.26 (t, 1H), 7.54 (m, 3H), 7.99 (m, 1H) , 8.45 (m, 4H), 8.90 (d, 1H) 1 H-NMR: δ 7.26 (t, 1H), 7.54 (m, 3H), 7.99 (m, 1H), 8.45 (m, 4H), 8.90 (d, 1H)
<준비단계 3-2> 5H-benzothieno[2,3-e]pyrido[3,2-b]indole의 합성Preparation Step 3-2 Synthesis of 5H-benzothieno [2,3-e] pyrido [3,2-b] indole
준비예 1의 준비단계 1-3에서 사용된 2-(dibenzo[b,d]thiophen-2-yl)-3-nitropyridine 대신 2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine 5.85 g을 사용하는 것을 제외하고는, 준비예 1의 준비단계 1-3과 동일하게 수행하여 5H-benzothieno[2,3-e]pyrido[3,2-b]indole를 얻었다.Instead of 2- (dibenzo [b, d] thiophen-2-yl) -3-nitropyridine used in Preparation Steps 1-3 of Preparation Example 1, 2- (dibenzo [b, d] thiophen-4-yl) -3- 5H-benzothieno [2,3-e] pyrido [3,2-b] indole was obtained in the same manner as in Preparation Step 1-3 of Preparation Example 1, except that 5.85 g of nitropyridine was used.
1H-NMR: δ 7.23 (t, 1H), 7.50 (m, 3H), 7.97 (m, 3H) , 8.44 (m, 2H), 10.60 (s, 1H) 1 H-NMR: δ 7.23 (t, 1H), 7.50 (m, 3H), 7.97 (m, 3H), 8.44 (m, 2H), 10.60 (s, 1H)
[준비예 4] 2-chloro-5H-benzothieno[2,3-e]pyrido[3,2-b]indole 의 합성Preparation Example 4 Synthesis of 2-chloro-5H-benzothieno [2,3-e] pyrido [3,2-b] indole
<준비단계 4-1> 6-chloro-2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine의 합성Preparation Step 4-1 Synthesis of 6-chloro-2- (dibenzo [b, d] thiophen-4-yl) -3-nitropyridine
준비예 1의 준비단계 1-2에서 사용된 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 대신 dibenzo[b,d]thiophen-4-ylboronic acid 9.03 g을 사용하고, 2-chloro-3-nitropyridine 대신 2,6-dichloro-3-nitropyridine 7.64 g을 사용하는 것을 제외하고는, 준비예 1의 준비단계 1-2와 동일하게 수행하여 6-chloro-2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine을 얻었다.Dibenzo [b, instead of 2- (dibenzo [b, d] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane used in Preparation Step 1-2 of Preparation Example 1 d) Preparation Step 1-2 of Preparation Example 1, except that 9.03 g of thiophen-4-ylboronic acid was used and 7.64 g of 2,6-dichloro-3-nitropyridine instead of 2-chloro-3-nitropyridine was used. 6-chloro-2- (dibenzo [b, d] thiophen-4-yl) -3-nitropyridine was obtained in the same manner.
1H-NMR : δ 7.16 (t, 1H), 7.44 (m, 3H), 7.87 (m, 1H) , 8.45 (m, 4H) 1 H-NMR: δ 7.16 (t, 1H), 7.44 (m, 3H), 7.87 (m, 1H), 8.45 (m, 4H)
<준비단계 4-2> 2-chloro-5H-benzothieno[2,3-e]pyrido[3,2-b]indole의 합성Preparation Step 4-2 Synthesis of 2-chloro-5H-benzothieno [2,3-e] pyrido [3,2-b] indole
준비예 1의 준비단계 1-3에서 사용된 2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine 대신 6-chloro-2-(dibenzo[b,d]thiophen-4-yl)-3-nitropyridine 6.51 g을 사용하는 것을 제외하고는, 준비예 1의 준비단계 1-3과 동일하게 수행하여 2-chloro-5H-benzothieno[2,3-e]pyrido[3,2-b]indole을 얻었다.6-chloro-2- (dibenzo [b, d] thiophen-4-yl instead of 2- (dibenzo [b, d] thiophen-4-yl) -3-nitropyridine used in Preparation Steps 1-3 of Preparation Example 1 ) 2-nitro-5H-benzothieno [2,3-e] pyrido [3,2-b, except that 6.51 g of 3-nitropyridine is used, in the same manner as in Preparation Step 1-3 of Preparation Example 1. ] indole was obtained.
1H-NMR: δ 7.33 (m, 2H), 7.51 (m, 2H), 8.00 (m, 2H) , 8.47 (m, 2H), 10.61 (s, 1H) 1 H-NMR: δ 7.33 (m, 2H), 7.51 (m, 2H), 8.00 (m, 2H), 8.47 (m, 2H), 10.61 (s, 1H)
[합성예 1] Mat-1의 합성Synthesis Example 1 Synthesis of Mat-1
질소 기류 하에서 준비예 1에서 제조된 화합물 12H-benzothieno[2,3-g]pyrido[3,2-b]indole (2.43 g, 8.86 mmol)을, 1-bromobenzene (4.17 g, 26.56 mmol), Cu powder(0.11 g, 1.77 mmol), K2CO3(2.44 g, 17.71 mmol), Na2SO4(2.52 g, 17.71 mmol) 및 nitrobenzene(100 ml)와 혼합한 다음, 190 ℃에서 12시간 동안 교반하였다. Compound 12H-benzothieno [2,3-g] pyrido [3,2-b] indole (2.43 g, 8.86 mmol) prepared in Preparation Example 1 under nitrogen stream was dissolved in 1-bromobenzene (4.17 g, 26.56 mmol) and Cu. mixed with powder (0.11 g, 1.77 mmol), K 2 CO 3 (2.44 g, 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml), then stirred at 190 ° C. for 12 hours It was.
반응이 종결된 후, nitrobenzene을 제거한 다음, 메틸렌클로라이드로 유기층을 분리하고, MgSO4를 사용하여 물을 제거하였다. 이후, 유기층에서 용매를 제거한 다음, 컬럼크로마토그래피로 정제하여, 화합물 Mat-1 (2.08 g, 수율 67%)을 얻었다. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . Thereafter, the solvent was removed from the organic layer, and then purified by column chromatography, obtaining a compound Mat-1 (2.08 g, 67% yield).
GC-Mass (이론치: 350.44 g/mol, 측정치: 350 g/mol)GC-Mass (Theoretical value: 350.44 g / mol, Measured value: 350 g / mol)
[합성예 2] Mat-2의 합성Synthesis Example 2 Synthesis of Mat-2
합성예 1에서 사용된 1-bromobenzene 대신 2-bromonaphthalene 7.57 g을 사용하는 것을 제외하고는, 상기 합성예 1과 동일하게 수행하여 화합물 Mat-2 (2.31g, 수율 65%)을 얻었다.Compound Mat-2 (2.31g, yield 65%) was obtained in the same manner as in Synthesis Example 1, except that 7.57 g of 2-bromonaphthalene was used instead of 1-bromobenzene used in Synthesis Example 1.
GC-Mass (이론치: 400.49 g/mol, 측정치: 400 g/mol)GC-Mass (Theoretical value: 400.49 g / mol, Measured value: 400 g / mol)
[합성예 3] Mat-3의 합성Synthesis Example 3 Synthesis of Mat-3
합성예 1에서 사용된 1-bromobenzene 대신 2-bromopyridine 4.20 g을 사용하는 것을 제외하고는, 상기 합성예 1과 동일하게 수행하여 화합물 Mat-3 (2.12g, 수율 68%)을 얻었다.Compound Mat-3 (2.12g, yield 68%) was obtained in the same manner as in Synthesis Example 1, except that 4.20 g of 2-bromopyridine was used instead of 1-bromobenzene used in Synthesis Example 1.
GC-Mass (이론치: 351.42 g/mol, 측정치: 351 g/mol)GC-Mass (Theoretical value: 351.42 g / mol, Measured value: 351 g / mol)
[합성예 4] Mat-4의 합성Synthesis Example 4 Synthesis of Mat-4
합성예 1에서 사용된 1-bromobenzene 대신 1-bromo-3,5-diphenylbenzene 8.21 g을 사용하는 것을 제외하고는, 상기 합성예 1과 동일하게 수행하여 화합물 Mat-4 (2.81g, 수율 63%)을 얻었다.Compound Mat-4 (2.81g, 63% yield) in the same manner as in Synthesis Example 1, except that 8.21 g of 1-bromo-3,5-diphenylbenzene was used instead of 1-bromobenzene used in Synthesis Example 1. Got.
GC-Mass (이론치: 502.63 g/mol, 측정치: 502 g/mol)GC-Mass (Theoretical value: 502.63 g / mol, Measured value: 502 g / mol)
[합성예 5] Mat-5의 합성Synthesis Example 5 Synthesis of Mat-5
질소 기류 하에서 준비예 1 에서 제조된 화합물 12H-benzothieno[2,3-g]pyrido[3,2-b]indole(1.60 g, 5.85 mmol)을, 2-chloro-4,6-diphenyl-1,3,5-triazine (2.10 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol) 및 DMF(80 ml)와 혼합한 다음, 상온에서 3시간 동안 교반하였다. 반응이 종결된 후, 물을 넣고 고체 화합물을 필터링한 후 컬럼 크로마토그래피로 정제하여, 화합물 Mat-5 (2.51g, 수율 85%)을 얻었다.Compound 12H-benzothieno [2,3-g] pyrido [3,2-b] indole (1.60 g, 5.85 mmol) prepared in Preparation Example 1 under nitrogen stream was replaced with 2-chloro-4,6-diphenyl-1, 3,5-triazine (2.10 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol) and DMF (80 ml) were mixed and then stirred at room temperature for 3 hours. After the reaction was terminated, water was added and the solid compound was filtered and purified by column chromatography, obtaining a compound Mat-5 (2.51 g, yield 85%).
GC-Mass (이론치: 505.59 g/mol, 측정치: 505 g/mol)GC-Mass (Theoretical value: 505.59 g / mol, Measured value: 505 g / mol)
[합성예 6] Mat-6의 합성Synthesis Example 6 Synthesis of Mat-6
합성예 5에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.30 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여 화합물 Mat-6 (3.19g, 수율 83%)을 얻었다.3.30 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 5 Except for using the same as in Synthesis Example 5 to obtain a compound Mat-6 (3.19g, 83% yield).
GC-Mass (이론치: 657.78 g/mol, 측정치: 657 g/mol)GC-Mass (Theoretical value: 657.78 g / mol, Measured value: 657 g / mol)
[합성예 7] Mat-7의 합성Synthesis Example 7 Synthesis of Mat-7
합성예 5에서 사용된 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 3-chloro-9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole 3.40 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여 화합물 Mat-7 (3.14g, 수율 80%)을 얻었다.3-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl)-instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 5 A compound Mat-7 (3.14 g, yield 80%) was obtained in the same manner as in Synthesis Example 5, except that 3.40 g of 9H-carbazole was used.
GC-Mass (이론치: 670.78 g/mol, 측정치: 670 g/mol)GC-Mass (Theoretical value: 670.78 g / mol, Measured value: 670 g / mol)
[합성예 8] Mat-8의 합성Synthesis Example 8 Synthesis of Mat-8
질소 기류 하에서 준비예 1에서 제조된 화합물 5H-benzothieno[3,2-f]pyrido[3,2-b]indole (2.43 g, 8.86 mmol)을, 1-bromobenzene (4.17 g, 26.56 mmol), Cu powder(0.11 g, 1.77 mmol), K2CO3(2.44 g, 17.71 mmol), Na2SO4(2.52 g, 17.71 mmol) 및 nitrobenzene(100 ml)과 혼합한 다음, 190 ℃에서 12시간 동안 교반하였다. Compound 5H-benzothieno [3,2-f] pyrido [3,2-b] indole (2.43 g, 8.86 mmol) prepared in Preparation Example 1 under nitrogen stream was mixed with 1-bromobenzene (4.17 g, 26.56 mmol) and Cu. mixed with powder (0.11 g, 1.77 mmol), K 2 CO 3 (2.44 g, 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml), then stirred at 190 ° C. for 12 hours It was.
반응이 종결된 후, nitrobenzene을 제거한 다음, 메틸렌클로라이드로 유기층을 분리하고, MgSO4를 사용하여 물을 제거하였다. 이후, 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여, 화합물 Mat-8 (2.01 g, 수율 65%)을 얻었다. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . Thereafter, the solvent was removed from the organic layer and purified by column chromatography to obtain a compound Mat-8 (2.01 g, yield 65%).
GC-Mass (이론치: 350.44 g/mol, 측정치: 350 g/mol)GC-Mass (Theoretical value: 350.44 g / mol, Measured value: 350 g / mol)
[합성예 9] Mat-9의 합성Synthesis Example 9 Synthesis of Mat-9
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 5H-benzothieno[3,2-f]pyrido[3,2-b]indole 1.60 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여, 화합물 Mat-9 (2.60g, 수율 88%)을 얻었다.1.60 g of 5H-benzothieno [3,2-f] pyrido [3,2-b] indole was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Except that, in the same manner as in Synthesis Example 5, to obtain a compound Mat-9 (2.60g, 88% yield).
GC-Mass (이론치: 505.59 g/mol, 측정치: 505 g/mol)GC-Mass (Theoretical value: 505.59 g / mol, Measured value: 505 g / mol)
[합성예 10] Mat-10의 합성Synthesis Example 10 Synthesis of Mat-10
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 5H-benzothieno[3,2-f]pyrido[3,2-b]indole 1.60 g을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.30 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여 화합물 Mat-10 (3.19g, 수율 83%)을 얻었다.1.60 g of 5H-benzothieno [3,2-f] pyrido [3,2-b] indole was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. , Except that 3.30 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine is used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine In the same manner as in Synthesis Example 5, the compound Mat-10 (3.19 g, yield 83%) was obtained.
GC-Mass (이론치: 657.78 g/mol, 측정치: 657 g/mol)GC-Mass (Theoretical value: 657.78 g / mol, Measured value: 657 g / mol)
[합성예 11] Mat-11의 합성Synthesis Example 11 Synthesis of Mat-11
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 5H-benzothieno[3,2-f]pyrido[3,2-b]indole 1.60 g을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 3-chloro-9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole 3.40 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여 화합물 Mat-11 (3.17g, 수율 81 %)을 얻었다.1.60 g of 5H-benzothieno [3,2-f] pyrido [3,2-b] indole was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. , 3-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same as in Synthesis Example 5 to obtain a compound Mat-11 (3.17g, 81% yield).
GC-Mass (이론치: 670.78 g/mol, 측정치: 670 g/mol)GC-Mass (Theoretical value: 670.78 g / mol, Measured value: 670 g / mol)
[합성예 12] Mat-12의 합성Synthesis Example 12 Synthesis of Mat-12
합성예 8에서 사용된 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 8.25 g을 사용하는 것을 제외하고는, 상기 합성예 8과 동일하게 수행하여 화합물 Mat-12 (2.77g, 수율 62%)을 얻었다.Compound Mat-12 (2.77g, 62% yield) in the same manner as in Synthesis Example 8, except that 8.25 g of 2-bromo-4,6-diphenylpyridine was used instead of 1-bromobenzene used in Synthesis Example 8. Got.
GC-Mass (이론치: 503.62 g/mol, 측정치: 503 g/mol)GC-Mass (Theoretical value: 503.62 g / mol, Measured value: 503 g / mol)
[합성예 13] Mat-13의 합성Synthesis Example 13 Synthesis of Mat-13
질소 기류 하에서 준비예 3에서 제조된 화합물 5H-benzothieno[2,3-e]pyrido[3,2-b]indole (2.43 g, 8.86 mmol)을, 1-bromobenzene (4.17 g, 26.56 mmol), Cu powder(0.11 g, 1.77 mmol), K2CO3(2.44 g, 17.71 mmol), Na2SO4(2.52 g, 17.71 mmol) 및 nitrobenzene(100 ml)과 혼합한 다음, 190 ℃에서 12시간 동안 교반하였다. Compound 5H-benzothieno [2,3-e] pyrido [3,2-b] indole (2.43 g, 8.86 mmol) prepared in Preparation Example 3 under nitrogen stream was mixed with 1-bromobenzene (4.17 g, 26.56 mmol) and Cu. mixed with powder (0.11 g, 1.77 mmol), K 2 CO 3 (2.44 g, 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml), then stirred at 190 ° C. for 12 hours It was.
반응이 종결된 후, nitrobenzene을 제거한 다음, 메틸렌클로라이드로 유기층을 분리하고, MgSO4를 사용하여 물을 제거하였다. 이후, 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여, 화합물 Mat-13 (2.04 g, 수율 66%)을 얻었다. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . Thereafter, the solvent was removed from the organic layer, and the residue was purified by column chromatography to obtain a compound Mat-13 (2.04 g, yield 66%).
GC-Mass (이론치: 350.44 g/mol, 측정치: 350 g/mol)GC-Mass (Theoretical value: 350.44 g / mol, Measured value: 350 g / mol)
[합성예 14] Mat-14의 합성Synthesis Example 14 Synthesis of Mat-14
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 준비예 3에서 제조된 화합물 5H-benzothieno[2,3-e]pyrido[3,2-b]indole 1.60 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여 화합물 Mat-14 (2.48g, 수율 84%)을 얻었다.Compound 5H-benzothieno [2,3-e] pyrido [3,2-b prepared in Preparation Example 3 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5 ] Indole was carried out in the same manner as in Synthesis Example 5, except that 1.60 g of the compound Mat-14 (2.48 g, yield 84%) was obtained.
GC-Mass (이론치: 505.59 g/mol, 측정치: 505 g/mol)GC-Mass (Theoretical value: 505.59 g / mol, Measured value: 505 g / mol)
[합성예 15] Mat-15의 합성Synthesis Example 15 Synthesis of Mat-15
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 준비예 3에서 제조된 화합물 5H-benzothieno[2,3-e]pyrido[3,2-b]indole 1.60 g 을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.30 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-15 (3.12g, 수율 81%)을 얻었다.Compound 5H-benzothieno [2,3-e] pyrido [3,2-b prepared in Preparation Example 3 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5 ] 60 g of indole and 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 3.30 g, the same procedure as in Synthesis Example 5 was performed to obtain Mat-15 (3.12 g, yield 81%) as a target compound.
GC-Mass (이론치: 657.78 g/mol, 측정치: 657 g/mol)GC-Mass (Theoretical value: 657.78 g / mol, Measured value: 657 g / mol)
[합성예 16] Mat-16의 합성Synthesis Example 16 Synthesis of Mat-16
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 준비예 3에서 제조된 화합물 5H-benzothieno[2,3-e]pyrido[3,2-b]indole 1.60 g 을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 3-chloro-9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole 3.40 g을 사용하는 것을 제외하고는, 상기 합성예 5와 동일하게 수행하여 화합물 Mat-16 (3.13g, 수율 80 %)을 얻었다.Compound 5H-benzothieno [2,3-e] pyrido [3,2-b prepared in Preparation Example 3 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5 ] indole 1.60 g and 3-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 3.40 g) -9H-carbazole, the compound Mat-16 (3.13g, 80% yield) was obtained in the same manner as in Synthesis example 5.
GC-Mass (이론치: 670.78 g/mol, 측정치: 670 g/mol)GC-Mass (Theoretical value: 670.78 g / mol, Measured value: 670 g / mol)
[합성예 17] Mat-17의 합성Synthesis Example 17 Synthesis of Mat-17
합성예 13에서 사용된 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 8.25 g을 사용하는 것을 제외하고는, 상기 합성예 13과 동일하게 수행하여 화합물 Mat-17 (2.68g, 수율 60 %)을 얻었다.Compound Mat-17 (2.68g, 60% yield) in the same manner as in Synthesis Example 13, except that 8.25 g of 2-bromo-4,6-diphenylpyridine was used instead of 1-bromobenzene used in Synthesis Example 13. Got.
GC-Mass (이론치: 503.62 g/mol, 측정치: 503 g/mol)GC-Mass (Theoretical value: 503.62 g / mol, Measured value: 503 g / mol)
[합성예 18] Mat-18의 합성Synthesis Example 18 Synthesis of Mat-18
<합성단계 18-1> 중간 화합물 IMC-18의 제조Synthesis Step 18-1 Preparation of the Intermediate Compound IMC-18
질소 기류 하에서, 준비예 2에서 제조된 화합물 12H-benzothieno[2,3-g]pyrido[3,2-b]indole (2.43 g, 7.88 mmol)을, phenylboronic acid (1.15 g, 9.47 mmol), NaOH(0.95 g, 23.67 mmol) 및 THF/H2O(100 ml/50 ml)과 혼합하고, 교반한 다음, 40 ℃에서 Pd(PPh3)4 (0.46 g, 5 mol%)를 넣고, 80 ℃에서 12시간 동안 교반하였다. 반응이 종결된 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피로 정제하여, 중간 화합물 IMC-18 (2.34 g, 수율 85%)을 얻었다.Under nitrogen stream, compound 12H-benzothieno [2,3-g] pyrido [3,2-b] indole (2.43 g, 7.88 mmol) prepared in Preparation Example 2 was dissolved in phenylboronic acid (1.15 g, 9.47 mmol), NaOH. (0.95 g, 23.67 mmol) and THF / H 2 O (100 ml / 50 ml) were mixed and stirred, then Pd (PPh 3 ) 4 (0.46 g, 5 mol%) was added at 40 ° C., and 80 ° C. Stir at 12 h. After the reaction was terminated, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain the intermediate compound IMC-18 (2.34 g, yield 85%).
<합성단계 18-2> 화합물 Mat-18의 제조Synthesis Step 18-2 Preparation of Compound Mat-18
합성예 1에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 18의 합성단계 18-1에서 얻은 IMC-18 2.34 g을 사용하고, 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 6.21 g을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 최종 화합물 Mat-18 (2.52 g, 수율 65%)을 얻었다.Instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 1, 2.34 g of IMC-18 obtained in Synthesis Step 18-1 of Synthesis Example 18 was used, and instead of 1-bromobenzene Except for using 6.21 g of 2-bromo-4,6-diphenylpyridine, the same procedure as in Synthesis Example 1 was carried out to obtain a final compound Mat-18 (2.52 g, yield 65%).
GC-Mass (이론치: 579.71 g/mol, 측정치: 579 g/mol)GC-Mass (Theoretical value: 579.71 g / mol, Measured value: 579 g / mol)
[합성예 19] Mat-19의 합성Synthesis Example 19 Synthesis of Mat-19
<합성단계 19-1> 중간 화합물 IMC-18의 제조Synthesis Step 19-1 Preparation of Intermediate Compound IMC-18
합성예 18의 합성단계 18-1과 동일하게 수행하여 중간 화합물 IMC-18를 얻었다.The intermediate compound IMC-18 was obtained in the same manner as in Synthesis Step 18-1 of Synthesis Example 18.
<합성단계 19-2> 화합물 Mat-19의 제조Synthesis Step 19-2 Preparation of Compound Mat-19
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 19의 합성단계 19-1에서 얻은 중간 화합물 IMC-18 2.04 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-19 (2.88 g, 수율 85%)를 얻었다.Except for using 2.04 g of the intermediate compound IMC-18 obtained in Synthesis Step 19-1 of Synthesis Example 19 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Was carried out in the same manner as in Synthesis example 5 to obtain a final compound Mat-19 (2.88 g, yield 85%).
GC-Mass (이론치: 581.69 g/mol, 측정치: 581 g/mol)GC-Mass (Theoretical value: 581.69 g / mol, Measured value: 581 g / mol)
[합성예 20] Mat-20의 합성Synthesis Example 20 Synthesis of Mat-20
<합성단계 20-1> 중간 화합물 IMC-18의 제조Synthesis Step 20-1 Preparation of Intermediate Compound IMC-18
합성예 18의 합성단계 18-1과 동일하게 수행하여 중간 화합물 IMC-18를 얻었다.The intermediate compound IMC-18 was obtained in the same manner as in Synthesis Step 18-1 of Synthesis Example 18.
<합성단계 20-2> 화합물 Mat-20의 제조Synthesis Step 20-2 Preparation of Compound Mat-20
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 20의 합성단계 20-1에서 얻은 중간 화합물 IMC-18을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.30 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여, 최종 화합물 Mat-20 (3.43 g, 수율 80%)를 얻었다.Instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5, the intermediate compound IMC-18 obtained in Synthesis Step 20-1 of Synthesis Example 20 was used, and 2-chloro- Synthesis example, except that 3.30 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine was used instead of 4,6-diphenyl-1,3,5-triazine. 5, the resulting compound Mat-20 (3.43 g, yield 80%) was obtained.
GC-Mass (이론치: 733.88 g/mol, 측정치: 733 g/mol/) GC-Mass (Theoretical value: 733.88 g / mol, Measured value: 733 g / mol /)
[합성예 21] Mat-21의 합성Synthesis Example 21 Synthesis of Mat-21
<합성단계 21-1> 중간 화합물 IMC-21의 제조Synthesis Step 21-1 Preparation of the Intermediate Compound IMC-21
합성예 18의 합성단계 18-1에서 사용된 phenylboronic acid 대신 pyridin-3-ylboronic acid을 사용하는 것을 제외하고는, 합성예 18의 합성단계 18-1과 동일하게 수행하여 중간 화합물 IMC-21를 제조하였다.Preparation of the intermediate compound IMC-21 was carried out in the same manner as in Synthesis Step 18-1 of Synthesis Example 18, except that pyridin-3-ylboronic acid was used instead of phenylboronic acid used in Synthesis Step 18-1 of Synthesis Example 18. It was.
<합성단계 21-2> 화합물 Mat-21의 제조Synthesis Step 21-2 Preparation of Compound Mat-21
합성예 1에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 21의 합성단계 21-1에서 얻은 중간 화합물 IMC-21 3.11 g을 사용하고, 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 8.25 g을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 최종 화합물 Mat-21 (3.24 g, 수율 63%)을 얻었다.3.11 g of intermediate compound IMC-21 obtained in Synthesis Step 21-1 of Synthesis Example 21 was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 1. A final compound Mat-21 (3.24 g, 63% yield) was obtained in the same manner as in Synthesis Example 1, except that 8.25 g of 2-bromo-4,6-diphenylpyridine was used instead of bromobenzene.
GC-Mass (이론치: 580.70 g/mol, 측정치: 580 g/mol)GC-Mass (Theoretical value: 580.70 g / mol, Measured value: 580 g / mol)
[합성예 22] Mat-22의 합성Synthesis Example 22 Synthesis of Mat-22
<합성단계 22-1> 중간 화합물 IMC-21의 제조Synthesis Step 22-1 Preparation of the Intermediate Compound IMC-21
합성예 21의 합성단계 21-1과 동일하게 수행하여 중간 화합물 IMC-21을 얻었다.Intermediate compound IMC-21 was obtained in the same manner as in Synthesis Step 21-1 of Synthesis Example 21.
<합성단계 22-2> 화합물 Mat-22의 제조Synthesis Step 22-2 Preparation of Compound Mat-22
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 22의 합성단계 22-1에서 얻은 중간 화합물 IMC-21 2.06 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-22 (2.79 g, 수율 82%)를 얻었다.Except for using 2.06 g of the intermediate compound IMC-21 obtained in Synthesis Step 22-1 of Synthesis Example 22 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Was carried out in the same manner as in Synthesis example 5 to obtain a final compound Mat-22 (2.79 g, yield 82%).
GC-Mass (이론치: 582.68g/mol, 측정치: 582 g/mol) GC-Mass (Theoretical value: 582.68 g / mol, Measured value: 582 g / mol)
[합성예 23] Mat-23의 합성Synthesis Example 23 Synthesis of Mat-23
<합성단계 23-1> 중간 화합물 IMC-21의 제조Synthesis Step 23-1 Preparation of Intermediate Compound IMC-21
합성예 21의 합성단계 21-1과 동일하게 수행하여 중간 화합물 IMC-21을 얻었다.Intermediate compound IMC-21 was obtained in the same manner as in Synthesis Step 21-1 of Synthesis Example 21.
<합성단계 23-2> 화합물 Mat-23의 제조Synthesis Step 23-2 Preparation of Compound Mat-23
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 23의 합성단계 23-1에서 얻은 중간 화합물 IMC-21 2.05 g을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.30 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-23 (3.39 g, 수율 79%)를 얻었다.Instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5, 2.05 g of the intermediate compound IMC-21 obtained in Synthesis Step 23-1 of Synthesis Example 23 was used, and 2- Except for using 3.30 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of chloro-4,6-diphenyl-1,3,5-triazine, In the same manner as in Synthesis example 5, the final compound Mat-23 (3.39 g, yield 79%) was obtained.
GC-Mass (이론치: 734.87 g/mol, 측정치: 734 g/mol) GC-Mass (Theoretical value: 734.87 g / mol, Measured value: 734 g / mol)
[합성예 24] Mat-24의 합성Synthesis Example 24 Synthesis of Mat-24
<합성단계 24-1> 중간 화합물 IMC-24의 제조Synthesis Step 24-1 Preparation of Intermediate Compound IMC-24
질소 기류 하에서, 준비예 2에서 제조된 화합물 5H-benzothieno[3,2-f]pyrido[3,2-b]indole (2.43 g, 7.88 mmol)을, phenylboronic acid (1.15 g, 9.47 mmol), NaOH(0.95 g, 23.67 mmol) 및 THF/H2O(100 ml/50 ml)과 혼합하고 교반한 다음, 40 ℃에서 0.46 g (5 mol%)의 Pd(PPh3)4를 넣고, 80 ℃에서 12시간 동안 교반하였다. 반응이 종결된 후, 메틸렌클로라이드로 유기층을 추출하고, MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피로 정제하여, 중간 화합물 IMC-24 (2.23 g, 수율 81%)을 얻었다.Under nitrogen stream, compound 5H-benzothieno [3,2-f] pyrido [3,2-b] indole (2.43 g, 7.88 mmol) prepared in Preparation Example 2 was dissolved in phenylboronic acid (1.15 g, 9.47 mmol), NaOH. (0.95 g, 23.67 mmol) and THF / H 2 O (100 ml / 50 ml) were mixed and stirred, then 0.46 g (5 mol%) of Pd (PPh 3 ) 4 was added at 40 ° C., at 80 ° C. Stir for 12 hours. After the reaction was terminated, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography to obtain the intermediate compound IMC-24 (2.23 g, yield 81%).
<합성단계 24-2> 화합물 Mat-24의 제조Synthesis Step 24-2 Preparation of Compound Mat-24
합성예 1에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 24의 합성단계 24-1에서 얻은 중간 화합물 IMC-24 2.23 g을 사용하고, 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 5.92 g을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 최종 화합물 Mat-24 (2.40 g, 수율 65%)을 얻었다.In place of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 1, 2.23 g of the intermediate compound IMC-24 obtained in Synthesis Step 24-1 of Synthesis Example 24 was used, and 1- A final compound Mat-24 (2.40 g, yield 65%) was obtained in the same manner as in Synthesis Example 1 except that 5.92 g of 2-bromo-4,6-diphenylpyridine was used instead of bromobenzene.
GC-Mass (이론치: 579.71 g/mol, 측정치: 579 g/mol)GC-Mass (Theoretical value: 579.71 g / mol, Measured value: 579 g / mol)
[합성예 25] Mat-25의 합성Synthesis Example 25 Synthesis of Mat-25
<합성단계 25-1> 중간 화합물 IMC-24의 제조Synthesis Step 25-1 Preparation of the Intermediate Compound IMC-24
합성예 24의 합성단계 24-1과 동일하게 수행하여 중간 화합물 IMC-24를 얻었다.Intermediate compound IMC-24 was obtained in the same manner as in Synthesis Step 24-1 of Synthesis Example 24.
<합성단계 25-2> 화합물 Mat-25의 제조Synthesis Step 25-2 Preparation of Compound Mat-25
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 25의 합성단계 25-1에서 얻은 중간 화합물 IMC-24 2.23 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-25 (2.96 g, 수율 80%)를 얻었다.Except for using 2.23 g of the intermediate compound IMC-24 obtained in Synthesis Step 25-1 of Synthesis Example 25 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Was carried out in the same manner as in Synthesis example 5 to obtain a final compound Mat-25 (2.96 g, yield 80%).
GC-Mass (이론치: 581.69 g/mol, 측정치: 581 g/mol)GC-Mass (Theoretical value: 581.69 g / mol, Measured value: 581 g / mol)
[합성예 26] Mat-26의 합성Synthesis Example 26 Synthesis of Mat-26
<합성단계 26-1> 중간 화합물 IMC-24의 제조Synthesis Step 26-1 Preparation of the Intermediate Compound IMC-24
합성예 24의 합성단계 24-1과 동일하게 수행하여 중간 화합물 IMC-24를 얻었다.Intermediate compound IMC-24 was obtained in the same manner as in Synthesis Step 24-1 of Synthesis Example 24.
<합성단계 26-2> 화합물 Mat-26의 제조Synthesis Step 26-2 Preparation of the Compound Mat-26
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 26의 합성단계 26-1에서 얻은 중간 화합물 IMC-24 2.23 g을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.58 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-26 (3.63 g, 수율 78%)를 얻었다.2.23 g of the intermediate compound IMC-24 obtained in Synthesis Step 26-1 of Synthesis Example 26 was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Except for using 3.58 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of chloro-4,6-diphenyl-1,3,5-triazine, The final compound Mat-26 (3.63 g, yield 78%) was obtained in the same manner as in Synthesis example 5.
GC-Mass (이론치: 731.90 g/mol, 측정치: 731 g/mol/) GC-Mass (Theoretical value: 731.90 g / mol, Measured value: 731 g / mol /)
[합성예 27] Mat-27의 합성Synthesis Example 27 Synthesis of Mat-27
<합성단계 27-1> 중간 화합물 IMC-27의 제조Synthesis Step 27-1 Preparation of the Intermediate Compound IMC-27
합성예 24의 합성단계 24-1에서 사용된 phenylboronic acid 대신 pyridin-3-ylboronic acid을 사용하는 것을 제외하고는, 합성예 24와 동일하게 수행하여 중간 화합물 IMC-27를 얻었다.Intermediate compound IMC-27 was obtained in the same manner as in Synthesis Example 24 except for using pyridin-3-ylboronic acid instead of phenylboronic acid used in Synthesis Step 24-1 of Synthesis Example 24.
<합성단계 27-2> 화합물 Mat-27의 제조Synthesis Step 27-2 Preparation of the Compound Mat-27
합성예 1에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 27의 합성단계 27-1에서 얻은 중간 화합물 IMC-27 3.11 g을 사용하고, 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 8.25 g을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 최종 화합물 Mat-27 (3.24 g, 수율 63%)을 얻었다.3.11 g of the intermediate compound IMC-27 obtained in Synthesis Step 27-1 of Synthesis Example 27 was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 1. A final compound Mat-27 (3.24 g, 63% yield) was obtained in the same manner as in Synthesis Example 1, except that 8.25 g of 2-bromo-4,6-diphenylpyridine was used instead of bromobenzene.
GC-Mass (이론치: 580.70 g/mol, 측정치: 580 g/mol)GC-Mass (Theoretical value: 580.70 g / mol, Measured value: 580 g / mol)
[합성예 28] Mat-28의 합성Synthesis Example 28 Synthesis of Mat-28
<합성단계 28-1> 중간 화합물 IMC-27의 제조Synthesis Step 28-1 Preparation of the Intermediate Compound IMC-27
합성예 27의 합성단계 27-1과 동일하게 수행하여 중간 화합물 IMC-27를 얻었다.Intermediate compound IMC-27 was obtained in the same manner as in Synthesis Step 27-1 of Synthesis Example 27.
<합성단계 28-2> 화합물 Mat-28의 제조Synthesis Step 28-2 Preparation of the Compound Mat-28
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 28의 합성단계 28-1에서 얻은 중간 화합물 IMC-27 2.23 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-28 (2.96 g, 수율 80%)를 얻었다.Except for using 2.23 g of the intermediate compound IMC-27 obtained in Synthesis Step 28-1 of Synthesis Example 28 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Was carried out in the same manner as in Synthesis example 5 to obtain a final compound Mat-28 (2.96 g, yield 80%).
GC-Mass (이론치: 582.68g/mol, 측정치: 582 g/mol) GC-Mass (Theoretical value: 582.68 g / mol, Measured value: 582 g / mol)
[합성예 29] Mat-29의 합성Synthesis Example 29 Synthesis of Mat-29
<합성단계 29-1> 중간 화합물 IMC-27의 제조Synthesis Step 29-1 Preparation of the Intermediate Compound IMC-27
합성예 27의 합성단계 27-1과 동일하게 수행하여 중간 화합물 IMC-27를 얻었다.Intermediate compound IMC-27 was obtained in the same manner as in Synthesis Step 27-1 of Synthesis Example 27.
<합성단계 29-2> 화합물 Mat-29의 제조Synthesis Step 29-2 Preparation of the Compound Mat-29
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 29의 합성단계 29-1에서 얻은 중간 화합물 IMC-27 2.23 g을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.58 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-29 (3.51 g, 수율 75%)를 얻었다.In place of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5, 2.23 g of the intermediate compound IMC-27 obtained in Synthesis Step 29-1 of Synthesis Example 29 was used, and 2- Except for using 3.58 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of chloro-4,6-diphenyl-1,3,5-triazine, In the same manner as in Synthesis example 5, the final compound Mat-29 (3.51 g, yield 75%) was obtained.
GC-Mass (이론치: 734.87 g/mol, 측정치: 734 g/mol) GC-Mass (Theoretical value: 734.87 g / mol, Measured value: 734 g / mol)
[합성예 30] Mat-30의 합성Synthesis Example 30 Synthesis of Mat-30
<합성단계 30-1> 중간 화합물 IMC-30의 제조Synthesis Step 30-1 Preparation of Intermediate Compound IMC-30
질소 기류 하에서, 준비예 4에서 제조된 화합물 2-chloro-5H-benzothieno[2,3-e]pyrido[3,2-b]indole (2.43 g, 7.88 mmol)을, phenylboronic acid (1.15 g, 9.47 mmol), NaOH(0.95 g, 23.67 mmol) 및 THF/H2O(100 ml/50 ml)과 혼합하고 교반한 다음, 40 ℃에서 0.46 g (5 mol%)의 Pd(PPh3)4를 넣고, 80 ℃에서 12시간 동안 교반하였다. 반응이 종결된 후, 메틸렌클로라이드로 유기층을 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피로 정제하여, 중간 화합물 IMC-30 (2.40g, 수율 87%)을 얻었다.Under nitrogen stream, the compound 2-chloro-5H-benzothieno [2,3-e] pyrido [3,2-b] indole (2.43 g, 7.88 mmol) prepared in Preparation Example 4 was dissolved in phenylboronic acid (1.15 g, 9.47). mmol), NaOH (0.95 g, 23.67 mmol) and THF / H 2 O (100 ml / 50 ml) were mixed and stirred, then 0.46 g (5 mol%) of Pd (PPh 3 ) 4 was added at 40 ° C. And stirred at 80 ° C. for 12 h. After the reaction was terminated, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After the solvent was removed from the obtained organic layer, the residue was purified by column chromatography to obtain an intermediate compound IMC-30 (2.40 g, yield 87%).
<합성단계 30-2> 화합물 Mat-30의 제조Synthesis Step 30-2 Preparation of Compound Mat-30
합성예 1에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 30의 합성단계 30-1에서 얻은 중간 화합물 IMC-30 2.40 g을 사용하고, 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 6.37 g을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 최종 화합물 Mat-30 (2.42 g, 수율 61%)을 얻었다.Instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 1, using 2.40 g of the intermediate compound IMC-30 obtained in Synthesis Step 30-1 of Synthesis Example 30, A final compound Mat-30 (2.42 g, 61% yield) was obtained in the same manner as in Synthesis Example 1, except that 6.37 g of 2-bromo-4,6-diphenylpyridine was used instead of bromobenzene.
GC-Mass (이론치: 579.71 g/mol, 측정치: 579 g/mol)GC-Mass (Theoretical value: 579.71 g / mol, Measured value: 579 g / mol)
[합성예 31] Mat-31의 합성Synthesis Example 31 Synthesis of Mat-31
<합성단계 31-1> 중간 화합물 IMC-30의 제조Synthesis Step 31-1 Preparation of Intermediate Compound IMC-30
합성예 30의 합성단계 30-1과 동일하게 수행하여 중간 화합물 IMC-30을 얻었다.The intermediate compound IMC-30 was obtained in the same manner as in Synthesis Step 30-1 of Synthesis Example 30.
<합성단계 31-2> 화합물 Mat-31의 제조Synthesis Step 31-2 Preparation of the Compound Mat-31
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 31의 합성단계 31-1에서 얻은 중간 화합물 IMC-30 2.40 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-31 (3.34 g, 수율 84%)를 얻었다.Except for using 2.40 g of the intermediate compound IMC-30 obtained in Synthesis Step 31-1 of Synthesis Example 31 instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Was carried out in the same manner as in Synthesis example 5 to obtain a final compound Mat-31 (3.34 g, yield 84%).
GC-Mass (이론치: 581.69 g/mol, 측정치: 581 g/mol)GC-Mass (Theoretical value: 581.69 g / mol, Measured value: 581 g / mol)
[합성예 32] Mat-32의 합성Synthesis Example 32 Synthesis of Mat-32
<합성단계 32-1> 중간 화합물 IMC-30의 제조Synthesis Step 32-1 Preparation of the Intermediate Compound IMC-30
합성예 30의 합성단계 30-1과 동일하게 수행하여 중간 화합물 IMC-30을 얻었다.The intermediate compound IMC-30 was obtained in the same manner as in Synthesis Step 30-1 of Synthesis Example 30.
<합성단계 32-2> 화합물 Mat-32의 제조Synthesis Step 32-2 Preparation of the Compound Mat-32
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 32의 합성단계 32-1에서 얻은 중간 화합물 IMC-30 2.40 g을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.57 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-32 (3.92 g, 수율 78%)를 얻었다.2.40 g of the intermediate compound IMC-30 obtained in Synthesis Step 32-1 of Synthesis Example 32 was used instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5. Except for using 3.57 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of chloro-4,6-diphenyl-1,3,5-triazine, In the same manner as in Synthesis example 5, the final compound Mat-32 (3.92 g, yield 78%) was obtained.
GC-Mass (이론치: 733.88 g/mol, 측정치: 733 g/mol/) GC-Mass (Theoretical value: 733.88 g / mol, Measured value: 733 g / mol /)
[합성예 33] Mat-33의 합성Synthesis Example 33 Synthesis of Mat-33
<합성단계 33-1> 중간 화합물 IMC-33의 제조Synthesis Step 33-1 Preparation of the Intermediate Compound IMC-33
합성예 30의 합성단계 30-1에서 사용된 phenylboronic acid 대신 pyridin-3-ylboronic acid 을 사용하는 것을 제외하고는, 합성예 30의 합성단계 30-1과 동일하게 수행하여 중간 화합물 IMC-33을 얻었다.Intermediate compound IMC-33 was obtained in the same manner as in Synthesis Step 30-1 of Synthesis Example 30, except that pyridin-3-ylboronic acid was used instead of phenylboronic acid used in Synthesis Step 30-1 of Synthesis Example 30. .
<합성단계 33-2> 화합물 Mat-33의 제조Synthesis Step 33-2 Preparation of the Compound Mat-33
합성예 1에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 33의 합성단계 33-1에서 얻은 중간 화합물 IMC-33 2.40 g을 사용하고, 1-bromobenzene 대신 2-bromo-4,6-diphenylpyridine 6.36 g을 사용하는 것을 제외하고는, 합성예 1과 동일하게 수행하여 최종 화합물 Mat-33 (2.38 g, 수율 60%)을 얻었다.Instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 1, 2.40 g of the intermediate compound IMC-33 obtained in Synthesis Step 33-1 of Synthesis Example 33 was used, and 1- A final compound Mat-33 (2.38 g, yield 60%) was obtained in the same manner as in Synthesis Example 1 except that 6.36 g of 2-bromo-4,6-diphenylpyridine was used instead of bromobenzene.
GC-Mass (이론치: 580.70 g/mol, 측정치: 580 g/mol)GC-Mass (Theoretical value: 580.70 g / mol, Measured value: 580 g / mol)
[합성예 34] Mat-34의 합성Synthesis Example 34 Synthesis of Mat-34
<합성단계 34-1> 중간 화합물 IMC-33의 제조Synthesis Step 34-1 Preparation of the Intermediate Compound IMC-33
합성예 33의 합성단계 33-1과 동일하게 수행하여 중간 화합물 IMC-33을 얻었다.Intermediate compound IMC-33 was obtained in the same manner as in Synthesis Step 33-1 of Synthesis Example 33.
<합성단계 34-2> 화합물 Mat-34의 제조Synthesis Step 34-2 Preparation of the Compound Mat-34
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 34의 합성단계 34-1에서 얻은 중간 화합물 IMC-33을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-34 (2.91 g, 수율 79%)를 얻었다.Except for using the intermediate compound IMC-33 obtained in Synthesis Step 34-1 of Synthesis Example 34 instead of the 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5, In the same manner as in Synthesis example 5, the final compound Mat-34 (2.91 g, yield 79%) was obtained.
GC-Mass (이론치: 582.68g/mol, 측정치: 582 g/mol) GC-Mass (Theoretical value: 582.68 g / mol, Measured value: 582 g / mol)
[합성예 35] Mat-35의 합성Synthesis Example 35 Synthesis of Mat-35
<합성단계 35-1> 중간 화합물 IMC-33의 제조Synthesis Step 35-1 Preparation of the Intermediate Compound IMC-33
합성예 33의 합성단계 33-1과 동일하게 수행하여 중간 화합물 IMC-33을 얻었다.Intermediate compound IMC-33 was obtained in the same manner as in Synthesis Step 33-1 of Synthesis Example 33.
<합성단계 35-2> 화합물 Mat-35의 제조Synthesis Step 35-2 Preparation of the Compound Mat-35
합성예 5에서 사용된 12H-benzothieno[2,3-g]pyrido[3,2-b]indole 대신 합성예 35의 합성단계 35-1에서 얻은 중간 화합물 IMC-33을 사용하고, 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine 3.85 g을 사용하는 것을 제외하고는, 합성예 5와 동일하게 수행하여 최종 화합물 Mat-35 (3.57 g, 수율 71%)를 얻었다.Instead of 12H-benzothieno [2,3-g] pyrido [3,2-b] indole used in Synthesis Example 5, the intermediate compound IMC-33 obtained in Synthesis Step 35-1 of Synthesis Example 35 was used, and 2-chloro- Synthesis example, except that 3.85 g of 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine was used instead of 4,6-diphenyl-1,3,5-triazine. 5, the resultant compound Mat-35 (3.57 g, yield 71%) was obtained.
GC-Mass (이론치: 734.87 g/mol, 측정치: 734 g/mol) GC-Mass (Theoretical value: 734.87 g / mol, Measured value: 734 g / mol)
[실시예 1] - 녹색 유기 EL 소자의 제작Example 1 Fabrication of Green Organic EL Devices
합성예 1에서 합성된 화합물 Mat-1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 EL 소자를 제조하였다.The compound Mat-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 mm 3 was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, 합성예 1의 화합물 Mat-1를 호스트로 이용하여, m-MTDATA(60 nm) / TCTA(80 nm) / 화합물 Mat-1 + 10 % Ir(ppy)3(300nm) / BCP(10 nm) / Alq3(30 nm) / LiF(1 nm) / Al(200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. On the prepared ITO transparent electrode, using the compound Mat-1 of Synthesis Example 1 as a host, m-MTDATA (60 nm) / TCTA (80 nm) / compound Mat-1 + 10% Ir (ppy) 3 ( An organic EL device was fabricated by laminating in order of 300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
m-MTDATA, TCTA, Ir(ppy)3, 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , and BCP are as follows.
[실시예 2 ~ 35] - 유기 EL 소자의 제조Examples 2 to 35-Fabrication of Organic EL Device
실시예 1에서 발광층 형성시 발광 호스트 물질로서 사용된 화합물 Mat-1 대신 합성예 2 내지 35에서 각각 합성된 화합물 Mat-2 내지 Mat-35를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 유기 EL 소자를 제조하였다.The same procedure as in Example 1 was repeated except that the compounds Mat-2 to Mat-35 synthesized in Synthesis Examples 2 to 35 were used instead of the compound Mat-1 used as the light emitting host material in Example 1 to form a light emitting layer. To an organic EL device.
[비교예 1] 녹색 유기 EL 소자의 제작Comparative Example 1 Fabrication of Green Organic EL Device
발광층 형성시 발광 호스트 물질로서 사용된 화합물 Mat-1 대신 CBP를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 EL 소자를 제작하였다. CBP의 구조는 하기와 같다.A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 used as a light emitting host material when forming the emission layer. The structure of CBP is as follows.
[비교예 2] 녹색 유기 EL 소자의 제작Comparative Example 2 Fabrication of Green Organic EL Device
발광층 형성시 발광 호스트 물질로서 화합물 Mat-1 대신 Com-1을 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 EL 소자를 제작하였다. Com-1의 구조는 하기와 같다.A green organic EL device was manufactured in the same manner as in Example 1, except that Com-1 was used instead of the compound Mat-1 as a light emitting host material when forming the emission layer. The structure of Com-1 is as follows.
[실험예]Experimental Example
실시예 1 내지 35, 및 비교예 1 및 2에서 각각 제조된 녹색 유기 EL 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For green organic EL devices prepared in Examples 1 to 35, and Comparative Examples 1 and 2, respectively, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.
표 1
Table 1
| 샘플 | 호스트 | 구동 전압(V) | EL 피크(nm) | 전류효율(cd/A) |
| 실시예 1 | Mat-1 | 6.55 | 520 | 40.0 |
| 실시예 2 | Mat-2 | 6.40 | 518 | 39.2 |
| 실시예 3 | Mat-3 | 6.50 | 519 | 40.1 |
| 실시예 4 | Mat-4 | 6.51 | 520 | 39.5 |
| 실시예 5 | Mat-5 | 6.56 | 517 | 40.8 |
| 실시예 6 | Mat-6 | 6.45 | 515 | 41.0 |
| 실시예 7 | Mat-7 | 6.51 | 521 | 41.4 |
| 실시예 8 | Mat-8 | 6.46 | 517 | 40.5 |
| 실시예 9 | Mat-9 | 6.48 | 516 | 40.9 |
| 실시예 10 | Mat-10 | 6.40 | 519 | 41.1 |
| 실시예 11 | Mat-11 | 6.62 | 520 | 40.8 |
| 실시예 12 | Mat-12 | 6.61 | 518 | 41.1 |
| 실시예 13 | Mat-13 | 6.60 | 516 | 40.2 |
| 실시예 14 | Mat-14 | 6.50 | 516 | 40.7 |
| 실시예 15 | Mat-15 | 6.69 | 520 | 41.1 |
| 실시예 16 | Mat-16 | 6.58 | 519 | 41.5 |
| 실시예 17 | Mat-17 | 6.62 | 518 | 39.9 |
| 실시예 18 | Mat-18 | 6.55 | 515 | 41.4 |
| 실시예 19 | Mat-19 | 6.45 | 518 | 40.3 |
| 실시예 20 | Mat-20 | 6.52 | 519 | 41.6 |
| 실시예 21 | Mat-21 | 6.51 | 515 | 40.9 |
| 실시예 22 | Mat-22 | 6.63 | 517 | 41.0 |
| 실시예 23 | Mat-23 | 6.49 | 516 | 40.7 |
| 실시예 24 | Mat-24 | 6.52 | 520 | 39.8 |
| 실시예 25 | Mat-25 | 6.60 | 515 | 39.9 |
| 실시예 26 | Mat-26 | 6.51 | 518 | 39.8 |
| 실시예 27 | Mat-27 | 6.60 | 518 | 40.5 |
| 실시예 28 | Mat-28 | 6.50 | 516 | 39.6 |
| 실시예 29 | Mat-29 | 6.52 | 515 | 40.4 |
| 실시예 30 | Mat-30 | 6.50 | 519 | 40.5 |
| 실시예 31 | Mat-31 | 6.61 | 520 | 41.0 |
| 실시예 32 | Mat-32 | 6.60 | 521 | 39.9 |
| 실시예 33 | Mat-33 | 6.59 | 516 | 41.3 |
| 실시예 34 | Mat-34 | 6.63 | 517 | 39.7 |
| 실시예 35 | Mat-35 | 6.58 | 520 | 40.2 |
| 비교예 1 | CBP | 6.93 | 516 | 38.2 |
| 비교예 2 | Com-1 | 6.70 | 520 | 38.5 |
| Sample | Host | Drive voltage (V) | EL peak (nm) | Current efficiency (cd / A) |
| Example 1 | Mat-1 | 6.55 | 520 | 40.0 |
| Example 2 | Mat-2 | 6.40 | 518 | 39.2 |
| Example 3 | Mat-3 | 6.50 | 519 | 40.1 |
| Example 4 | Mat-4 | 6.51 | 520 | 39.5 |
| Example 5 | Mat-5 | 6.56 | 517 | 40.8 |
| Example 6 | Mat-6 | 6.45 | 515 | 41.0 |
| Example 7 | Mat-7 | 6.51 | 521 | 41.4 |
| Example 8 | Mat-8 | 6.46 | 517 | 40.5 |
| Example 9 | Mat-9 | 6.48 | 516 | 40.9 |
| Example 10 | Mat-10 | 6.40 | 519 | 41.1 |
| Example 11 | Mat-11 | 6.62 | 520 | 40.8 |
| Example 12 | Mat-12 | 6.61 | 518 | 41.1 |
| Example 13 | Mat-13 | 6.60 | 516 | 40.2 |
| Example 14 | Mat-14 | 6.50 | 516 | 40.7 |
| Example 15 | Mat-15 | 6.69 | 520 | 41.1 |
| Example 16 | Mat-16 | 6.58 | 519 | 41.5 |
| Example 17 | Mat-17 | 6.62 | 518 | 39.9 |
| Example 18 | Mat-18 | 6.55 | 515 | 41.4 |
| Example 19 | Mat-19 | 6.45 | 518 | 40.3 |
| Example 20 | Mat-20 | 6.52 | 519 | 41.6 |
| Example 21 | Mat-21 | 6.51 | 515 | 40.9 |
| Example 22 | Mat-22 | 6.63 | 517 | 41.0 |
| Example 23 | Mat-23 | 6.49 | 516 | 40.7 |
| Example 24 | Mat-24 | 6.52 | 520 | 39.8 |
| Example 25 | Mat-25 | 6.60 | 515 | 39.9 |
| Example 26 | Mat-26 | 6.51 | 518 | 39.8 |
| Example 27 | Mat-27 | 6.60 | 518 | 40.5 |
| Example 28 | Mat-28 | 6.50 | 516 | 39.6 |
| Example 29 | Mat-29 | 6.52 | 515 | 40.4 |
| Example 30 | Mat-30 | 6.50 | 519 | 40.5 |
| Example 31 | Mat-31 | 6.61 | 520 | 41.0 |
| Example 32 | Mat-32 | 6.60 | 521 | 39.9 |
| Example 33 | Mat-33 | 6.59 | 516 | 41.3 |
| Example 34 | Mat-34 | 6.63 | 517 | 39.7 |
| Example 35 | Mat-35 | 6.58 | 520 | 40.2 |
| Comparative Example 1 | CBP | 6.93 | 516 | 38.2 |
| Comparative Example 2 | Com-1 | 6.70 | 520 | 38.5 |
실험 결과, 본 발명에 따른 화학식 1로 표시되는 화합물(화합물 Mat-1 내지 Mat-35)을 발광층의 호스트 물질로 사용하는 실시예 1 내지 35에서 각각 제조된 녹색 유기 EL 소자는 종래 CBP를 사용하는 비교예 1 및 비교예 2 의 녹색 유기 EL 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.As a result of the experiment, the green organic EL devices manufactured in Examples 1 to 35 each using the compound represented by Formula 1 according to the present invention (Compounds Mat-1 to Mat-35) as the host material of the light emitting layer were prepared using conventional CBP. It was confirmed that the green organic EL devices of Comparative Examples 1 and 2 exhibited superior performance in terms of current efficiency and driving voltage.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속하는 것은 당연하다.Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.
Claims (6)
- 하기 화학식 1로 표시되는 화합물: Compound represented by the following formula (1):[화학식 1] [Formula 1]
(상기 화학식 1에서,(In Formula 1,R1 내지 R8 은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 인접하는 기와 결합하여 축합(fused) 고리를 형성할 수 있으며, R 1 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a 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 A cycloalkyl group of -C 40 , a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 1 -C 40 alkylsilyl group, and a substituted or unsubstituted C 6 -C 40 Selected from the group consisting of arylsilyl groups, may be bonded to adjacent groups to form a fused ring,이때 R1 내지 R8 중 적어도 하나는 인접하는 기와 결합하여 하기 화학식 2로 표시되는 축합 고리를 형성하고,At least one of R 1 to R 8 is bonded to an adjacent group to form a condensed ring represented by the following formula (2),[화학식 2] [Formula 2]
상기 화학식 2 에서,In Chemical Formula 2,X1 내지 X4는 서로 동일하거나 상이하고, 각각 독립적으로 CR9 또는 N이고, 이때 X1 내지 X4 중 적어도 하나는 N 이며,X 1 to X 4 are the same as or different from each other, and each independently CR 9 or N, wherein at least one of X 1 to X 4 is N,하나 이상의 R9는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 이때 하나 이상의 R9는 인접한 기와 결합하여 축합 고리를 형성할 수 있으며,At least one R 9 is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, Substituted or unsubstituted C 2 to 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 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, and a substituted or unsubstituted C 6 to C 40 arylsilyl group Selected from the group wherein one or more R 9 may combine with adjacent groups to form a condensed ring,Ar1은 수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, 치환 또는 비치환된 C6~C40의 아릴아민기, 치환 또는 비치환된 C3~C40의 시클로알킬기, 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기, 치환 또는 비치환된 C1~C40의 알킬실릴기, 및 치환 또는 비치환된 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,Ar 1 is hydrogen, 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 to 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 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 , A substituted or unsubstituted C 1 ~ C 40 Alkylsilyl group, and a substituted or unsubstituted C 6 ~ C 40 An arylsilyl group,상기 R1 내지 R9 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 아릴알킬기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 및 아릴실릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이할 수 있음).The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R 1 to R 9 and Ar 1 And one or more substituents respectively introduced to the 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 - a heteroaryl group of C 40 aryl group, the number of nuclear atoms of 5 to 40, C 6 ~ C 40 of the aryloxy group, C 1 ~ alkyloxy group of C 40, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 doedoe of the cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, aryl silyl group the group consisting of C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 of the plurality of substituents are identical to each other Or may be different). - 제1항에 있어서,The method of claim 1,하기 화학식 3 내지 8 중 하나로 표시되는 화합물: A compound represented by one of the following Chemical Formulas 3 to 8:[화학식 3][Formula 3];
;[화학식 4][Formula 4];
;[화학식 5][Formula 5];
;[화학식 6][Formula 6];
;[화학식 7][Formula 7]; 및
; And[화학식 8][Formula 8]
(상기 화학식 3 내지 화학식 8 에서, (In the above Chemical Formulas 3 to 8,X1 내지 X4, R1 내지 R9, 및 Ar1은 각각 제1항에서 정의한 바와 동일함).X 1 to X 4 , R 1 to R 9 , and Ar 1 are the same as defined in claim 1 , respectively). - 제1항에 있어서, The method of claim 1,하기 화학식 9 내지 32 중 하나로 표시되는 화합물: A compound represented by one of the following Chemical Formulas 9 to 32:[화학식 9][Formula 9];
;[화학식 10][Formula 10];
;[화학식 11][Formula 11];
;[화학식 12][Formula 12];
;[화학식 13][Formula 13];
;[화학식 14][Formula 14];
;[화학식 15][Formula 15];
;[화학식 16][Formula 16];
;[화학식 17][Formula 17];
;[화학식 18][Formula 18];
;[화학식 19][Formula 19];
;[화학식 20][Formula 20];
;[화학식 21][Formula 21];
;[화학식 22][Formula 22];
;[화학식 23][Formula 23];
;[화학식 24][Formula 24];
;[화학식 25][Formula 25];
;[화학식 26][Formula 26];
;[화학식 27][Formula 27];
;[화학식 28][Formula 28];
;[화학식 29][Formula 29];
;[화학식 30][Formula 30];
;[화학식 31][Formula 31]; 및
; And[화학식 32][Formula 32]
(상기 화학식 9 내지 32에서,(In Chemical Formulas 9 to 32,R1 내지 R9 및 Ar1은 각각 제1항에서 정의한 바와 동일함).R 1 to R 9 and Ar 1 are the same as defined in claim 1 respectively). - 제3항에 있어서, The method of claim 3,상기 Ar1 은 치환 또는 비치환된 C6~C40의 아릴기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기로 이루어진 군으로부터 선택되며, Ar 1 is selected from the group consisting of a substituted or unsubstituted C 6 ~ C 40 aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,이때 상기 아릴기 및 헤테로아릴기에 각각 도입되는 하나 이상의 치환기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되되, 복수개의 치환기는 서로 동일하거나 상이한 것이 특징인 화합물.In this case, each of the one or more substituents introduced into the aryl group and the heteroaryl group is 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 , C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, and C 6 ~ C 40 An arylsilyl group, a plurality of substituents Are characterized in that they are the same or different from one another.
- 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자에 있어서,In an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중 적어도 하나는 제 1항 내지 제4항 중 어느 한 항에 기재된 화합물을 포함하는 것이 특징인 유기 전계 발광 소자. At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 4.
- 제5항에 있어서, The method of claim 5,상기 화합물을 포함하는 적어도 하나의 유기물층은 발광층인 것이 특징인 유기 전계 발광 소자.At least one organic material layer comprising the compound is an organic electroluminescent device, characterized in that the light emitting layer.
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| WO2006016193A1 (en) * | 2004-08-07 | 2006-02-16 | Oled-T Limited | Electroluminescent materials and devices |
| US20110108821A1 (en) * | 2008-07-29 | 2011-05-12 | Merck Patent Gmbh | Organic electroluminescent device |
| US20120319091A1 (en) * | 2010-01-21 | 2012-12-20 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescent element comprising same |
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| WO2006016193A1 (en) * | 2004-08-07 | 2006-02-16 | Oled-T Limited | Electroluminescent materials and devices |
| US20110108821A1 (en) * | 2008-07-29 | 2011-05-12 | Merck Patent Gmbh | Organic electroluminescent device |
| US20120319091A1 (en) * | 2010-01-21 | 2012-12-20 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescent element comprising same |
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| CN107011360A (en) * | 2017-03-14 | 2017-08-04 | 上海大学 | A kind of heterocycle and δ carboline derivatives and application |
| CN107011360B (en) * | 2017-03-14 | 2020-08-11 | 上海大学 | Heterocyclic-carboline derivative and application thereof |
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