WO2017111389A1 - Organic compound and organic electroluminescent diode including same - Google Patents
Organic compound and organic electroluminescent diode including same Download PDFInfo
- Publication number
- WO2017111389A1 WO2017111389A1 PCT/KR2016/014726 KR2016014726W WO2017111389A1 WO 2017111389 A1 WO2017111389 A1 WO 2017111389A1 KR 2016014726 W KR2016014726 W KR 2016014726W WO 2017111389 A1 WO2017111389 A1 WO 2017111389A1
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- Prior art keywords
- group
- aryl
- alkyl
- formula
- boron
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000003118 aryl group Chemical group 0.000 claims description 96
- 125000000217 alkyl group Chemical group 0.000 claims description 73
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000005104 aryl silyl group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 33
- 125000005264 aryl amine group Chemical group 0.000 claims description 30
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- 125000004104 aryloxy group Chemical group 0.000 claims description 29
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 23
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- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 11
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
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- IHXBYGUILHCBGG-UHFFFAOYSA-N 2-(3-chlorophenyl)-9H-carbazole Chemical compound ClC=1C=C(C=CC=1)C1=CC=2NC3=CC=CC=C3C=2C=C1 IHXBYGUILHCBGG-UHFFFAOYSA-N 0.000 description 6
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- 230000000903 blocking effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 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
- 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
- the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB hole blocking layer
- BCP hole blocking layer
- electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
- metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
- the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of the organic material layer material which is excellent in performance is calculated
- an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
- the present invention provides a compound represented by the following formula (1):
- L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
- R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
- l and m are each independently an integer from 0 to 4.
- n is an integer from 0 to 3;
- R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different
- Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
- the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
- Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
- Alkenyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
- Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
- monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
- the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
- R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
- heterocycloalkyl include, but are not limited to, 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 60 carbon atoms.
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the compound represented by Formula 1 according to the present invention can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence properties.
- an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.
- the present invention provides a compound represented by Formula 1:
- L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
- R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
- l and m are each independently an integer from 0 to 4.
- n is an integer from 0 to 3;
- R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different
- Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
- the novel organic compound according to the present invention has a structure in which a carbazole moiety is bonded to fluorene and an aromatic ring or heteroaromatic ring.
- the compound represented by the formula (1) is characterized in that the compound represented by the formula (1).
- L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
- R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
- l and m are each independently an integer from 0 to 4.
- n is an integer from 0 to 3;
- R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different
- Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
- position 1, 2 or 3 of carbazole and position 2 of fluorene are directly linked to the active site, By linking, the stability of the molecule can be increased.
- the compound may be represented by any one of Formulas 2 to 4, but is not limited thereto.
- the L 1 to L 4 may be selected independently from the group consisting of the following formula 5 to 7, but is not limited thereto:
- Z 1 to Z 8 are each independently N or C (R 7 ), but in Formula 5, at least two of Z 1 to Z 6 are C (R 7 ) and at least 2 of Z 1 to Z 4 in Formula 6
- the dog is C (R 7 ), in formula 7 at least one of Z 1 to Z 4 , at least one of Z 5 to Z 8 is C (R 7 );
- R 7 is absent, hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, and when there
- the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 7 is heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group
- two of the bonds formed as linkers in Z 1 to Z 6 are C (R 7 ), wherein R 7 may be absent.
- two of the bonds formed as linkers in Z 1 to Z 4 are C (R 7 ), wherein R 7 may be absent.
- any one of Z 1 to Z 4 and Z 5 to Z 8 which is bonded as a linker in the formula ( 7 ) is C (R 7 ), wherein R 7 is It may be absent.
- the compound may be a compound represented by any one of the following Chemical Formulas 8 to 12, but is not limited thereto:
- the R 1 is preferably a substituent represented by any one of the following Formulas 13 to 17 can increase the electron transport capacity, but is not limited thereto:
- X 1 to X 8 are each independently N or C (R 10 );
- any one of X 1 to X 4 bonded to L 2 is C (R 10 ), wherein R 10 is absent;
- T 1 is N or C (R 10 );
- Y 1 is O, S, N (R 11 ) or C (R 12 ) (R 13 );
- p and q are each independently integers of 0 to 4.
- R 8 and R 9 is heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl, C cycloalkyl group of 3 ⁇ C 40 of , 3 to 40 heterocycloalkyl groups, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl jade group, C group 3 ⁇ C 40 alkylsilyl, C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ aryl phosphine of C 60 A panyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, wherein each of R
- R 10 to R 13 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of the R 10 in this case
- the substituents represented by Formula 13 to 17 may be selected from the group consisting of the following Formula A-1 to A-19, but is not limited thereto:
- t is an integer from 0 to 5;
- w is an integer from 0 to 4.
- v is an integer from 0 to 3;
- u is an integer from 0 to 2;
- R 14 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, A C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylsilyl group, or an adjacent group (e.g., L 1 or L 2 , or another adjacent R 18 or R 14
- R 10 to R 13 , p and q are the same as defined in Chemical Formulas 13 to 17.
- R 10 to R 14 may be each independently C 6 ⁇ C 60 An aryl group or a nuclear atom of 5 to 60 heteroaryl group.
- R 10 to R 14 are each independently a phenyl group, biphenyl group, naphthalenyl group, fluorenyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, quinolinyl group and quina It may be selected from the group consisting of a zolinyl group.
- Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
- the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
- organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
- the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
- the compound may be used alone or mixed 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, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
- the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.
- the compound represented by the formula (1) of the present invention has excellent hole transporting ability due to the carbazole moiety, and has excellent electron transporting ability of fluorene and aromatic ring or heteroaromatic ring connected thereto, thereby having bipolar characteristics in the molecule. Therefore, the bonding force between the holes and the electrons in the light emitting layer can be increased.
- the light emitting layer of the organic EL device may include a host material, and may include the compound represented by Formula 1 as the host material.
- the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
- the structure of the organic 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.
- an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer.
- at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.
- the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
- the organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
- examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
- metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 5 as a light emitting host material when forming the emission layer.
- Example 1 C 5 6.64 516 42.2
- Example 2 C 7 6.35 517 43.5
- Example 3 C 10 6.62 518 45.7
- Example 4 C 11 6.53 516 42.3
- Example 5 C 33 6.36 517 43.1
- Example 6 C 35 6.88 516 43.6
- Example 7 C 38 6.44 516 46.2
- Example 8 C 39 6.62 516 43.4
- Example 9 C 61 6.46 517 43.7
- Example 10 C 63 6.39 516 47.4
- Example 11 C 66 6.74 516 47.6
- Example 12 C 67 6.81 518 43.2
- Example 13 C 92 6.38 516 47.4
- Example 14 C 95 6.54 518 44.1
- Example 15 120 6.67 517 42.4
- Example 16 C 123 6.32 517 46.7
- Example 17 C 148 6.55 516 44.8
- Example 18 C 151 6.83 518 43.5
- Example 19 C 176 6.16 516 48.1
- Example 20 179 6.24 516 49.6
- Example 21
- the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / C 103 ⁇ C 244 compound + 10% (piq) 2 Ir (acac) (300 nm) / BCP (10 nm) / Alq 3 on the prepared ITO transparent electrode (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to fabricate an organic EL device.
- a red organic electroluminescent device was manufactured in the same manner as in Example 25, except that CBP was used instead of the C 103 compound as a light emitting host material when the emission layer was formed.
- 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.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent diode including same. The compound according to the present invention, when used in an organic layer of an organic electroluminescent diode and preferably, in a light-emitting layer, can improve the light emitting efficiency, the driving voltage, the lifespan, etc. of the organic electroluminescent diode.
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 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing 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 걸어주면 양극에서는 정공이 유기물층으로 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 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. 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 its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 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 for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 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, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 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 transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of the organic material layer material which is excellent in performance is calculated | required.
본 발명은 상기한 문제점을 해결하기 위해, 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규 화합물 및 상기 화합물을 이용한 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
L1 내지 L4는 각각 독립적으로 단일결합, C6~C60의 아릴렌기 및 핵원자수 5 내지 60개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며;R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ for C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ is selected from the group consisting of an aryl amine of the C 60 of the;
l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
n은 0 내지 3의 정수이며;n is an integer from 0 to 3;
R4 내지 R6은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R4 내지 R6 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Arylphosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R6의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 6 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
본 발명에서의 "알킬"은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
본 발명에서의 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다."Alkenyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
본 발명에서의 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다."Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
본 발명에서의 "아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, may have 8 to 60 carbon atoms), and the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
본 발명에서의 "헤테로아릴"은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 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 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서의 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 "아릴아민"은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 "시클로알킬"은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 "헤테로시클로알킬"은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다."Heterocycloalkyl" in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 "알킬실릴"은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 "축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
본 발명에 따른 화학식 1로 표시되는 화합물은 열적 안정성 및 인광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명에 따른 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 가지는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능, 수명이 크게 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by Formula 1 according to the present invention can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence properties. In particular, when the compound represented by Chemical Formula 1 according to 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 a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.
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,
L1 내지 L4는 각각 독립적으로 단일결합, C6~C60의 아릴렌기 및 핵원자수 5 내지 60개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며;R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ for C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ is selected from the group consisting of an aryl amine of the C 60 of the;
l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
n은 0 내지 3의 정수이며;n is an integer from 0 to 3;
R4 내지 R6은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R4 내지 R6 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Arylphosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R6의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 6 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New Organic Compounds
본 발명에 따른 신규 유기 화합물은 카바졸 모이어티에 플루오렌과 방향족 고리 또는 헤테로방향족 고리가 결합된 구조를 가진다. 정공 수송성을 지닌 카바졸과 플루오렌과 방향족 고리 또는 헤테로방향족 고리의 높은 전자 수송성 구조를 동시에 포함하여 분자 내 양극성의 특성을 갖기 때문에 발광층 내에서 정공과 전자의 결합력을 높일 수 있다. 구체적으로, 하기 화학식 1로 표시되는 화합물인 것을 특징으로 한다.The novel organic compound according to the present invention has a structure in which a carbazole moiety is bonded to fluorene and an aromatic ring or heteroaromatic ring. Including a high electron transport structure of carbazole, fluorene, aromatic ring, or heteroaromatic ring with carbazole having hole transporting properties at the same time to increase the binding force between the hole and the electron in the light emitting layer. Specifically, it is characterized in that the compound represented by the formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
L1 내지 L4는 각각 독립적으로 단일결합, C6~C60의 아릴렌기 및 핵원자수 5 내지 60개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며;R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ for C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ is selected from the group consisting of an aryl amine of the C 60 of the;
l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
n은 0 내지 3의 정수이며;n is an integer from 0 to 3;
R4 내지 R6은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R4 내지 R6 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Arylphosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R6의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 6 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 1로 표시되는 화합물에서 카바졸의 1, 2 또는 3번 위치와 플루오렌의 2번 위치는 활성 위치(site)로 이 위치가 직접적으로 연결되거나 혹은 링커로 연결됨으로써 분자의 안정성을 높일 수 있으며. 구체적으로는 하기 화학식 2 내지 4 중 어느 하나로 표시되는 화합물일 수 있으나, 이에 제한되는 것은 아니다:According to a preferred embodiment of the present invention, in the compound represented by the formula (1), position 1, 2 or 3 of carbazole and position 2 of fluorene are directly linked to the active site, By linking, the stability of the molecule can be increased. Specifically, the compound may be represented by any one of Formulas 2 to 4, but is not limited thereto.
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에서,In Chemical Formulas 2 to 4,
l, m, n, L1 내지 L4 및 R1 내지 R6 각각은 상기 화학식 1에서 정의된 바와 같다.1, m, n, L 1 to L 4 and R 1 to R 6 are each as defined in Chemical Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 내지 L4, 보다 바람직하게는 L1 및 L2는 각각 독립적으로 하기 화학식 5 내지 7로 이루어진 군에서 선택될 수 있으나, 이에 제한되는 것은 아니다:According to a preferred embodiment of the present invention, the L 1 to L 4 , more preferably L 1 and L 2 may be selected independently from the group consisting of the following formula 5 to 7, but is not limited thereto:
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 5 내지 7에서,In Chemical Formulas 5 to 7,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z1 내지 Z8은 각각 독립적으로 N 또는 C(R7)이나, 상기 화학식 5에서 Z1 내지 Z6 중 적어도 2개는 C(R7)이고, 화학식 6에서 Z1 내지 Z4 중 적어도 2개는 C(R7)이며, 화학식 7에서는 Z1 내지 Z4 중 적어도 하나, Z5 내지 Z8 중 적어도 하나는 C(R7)이며;Z 1 to Z 8 are each independently N or C (R 7 ), but in Formula 5, at least two of Z 1 to Z 6 are C (R 7 ) and at least 2 of Z 1 to Z 4 in Formula 6 The dog is C (R 7 ), in formula 7 at least one of Z 1 to Z 4 , at least one of Z 5 to Z 8 is C (R 7 );
R7은 부재이거나, 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R7이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 7 is absent, hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, and when there are a plurality of R 7 , they are the same or different from each other;
상기 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 7 is heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 the arylboronic group, one member selected from the group consisting of C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl group of the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 5에서 Z1 내지 Z6 중 링커로서 결합이 이루어지는 2개는 C(R7)이고, 이때 상기 R7는 부재일 수 있다. According to a preferred embodiment of the present invention, in Formula 5, two of the bonds formed as linkers in Z 1 to Z 6 are C (R 7 ), wherein R 7 may be absent.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 6에서 Z1 내지 Z4 중 링커로서 결합이 이루어지는 2개는 C(R7)이며, 이때 상기 R7는 부재일 수 있다. According to one preferred embodiment of the present invention, in Formula 6, two of the bonds formed as linkers in Z 1 to Z 4 are C (R 7 ), wherein R 7 may be absent.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 7에서 링커로서 결합이 이루어지는 Z1 내지 Z4 중 어느 하나와, Z5 내지 Z8 중 어느 하나는 C(R7)이며, 이때 상기 R7는 부재일 수 있다. According to a preferred embodiment of the present invention, any one of Z 1 to Z 4 and Z 5 to Z 8 which is bonded as a linker in the formula ( 7 ) is C (R 7 ), wherein R 7 is It may be absent.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 8 내지 12 중 어느 하나로 표시되는 화합물일 수 있으나, 이에 제한되는 것은 아니다:According to one preferred embodiment of the present invention, the compound may be a compound represented by any one of the following Chemical Formulas 8 to 12, but is not limited thereto:
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
상기 화학식 8 내지 12에서,In Chemical Formulas 8 to 12,
l, m, n, L1, L2 및 R1 내지 R6 각각은 상기 화학식 1에서 정의된 바와 같다.1, m, n, L 1 , L 2 and R 1 to R 6 are each as defined in Chemical Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1은 하기 화학식 13 내지 17 중 어느 하나로 표시되는 치환기인 것이 전자 수송력을 높일 수 있어 바람직하나, 이에 제한되는 것은 아니다:According to one preferred embodiment of the present invention, the R 1 is preferably a substituent represented by any one of the following Formulas 13 to 17 can increase the electron transport capacity, but is not limited thereto:
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17][Formula 17]
상기 화학식 13 내지 17에서, In Chemical Formulas 13 to 17,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
X1 내지 X8은 각각 독립적으로 N 또는 C(R10)이며;X 1 to X 8 are each independently N or C (R 10 );
상기 화학식 14에서 L2에 결합되는 X1 내지 X4 중 어느 하나는 C(R10)이고, 이때 상기 R10은 부재이며;In Formula 14, any one of X 1 to X 4 bonded to L 2 is C (R 10 ), wherein R 10 is absent;
T1은 N 또는 C(R10)이며;T 1 is N or C (R 10 );
Y1은 O, S, N(R11) 또는 C(R12)(R13)이며;Y 1 is O, S, N (R 11 ) or C (R 12 ) (R 13 );
p 및 q는 각각 독립적으로 0 내지 4의 정수이며;p and q are each independently integers of 0 to 4;
R8 및 R9는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R8 및 R9 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 8 and R 9 is heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl, C cycloalkyl group of 3 ~ C 40 of , 3 to 40 heterocycloalkyl groups, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryl jade group, C group 3 ~ C 40 alkylsilyl, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 A panyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, wherein each of R 8 and R 9 is the same or different from each other;
R10 내지 R13은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R10이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 to R 13 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of the R 10 in this case, plural personal they the same or different, and ;
상기 R8 내지 R13의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 8 to R 13 boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 13 내지 17로 표시되는 치환기는 하기 화학식 A-1 내지 A-19로 이루어진 군에서 선택될 수 있으나, 이에 제한되는 것은 아니다:According to a preferred embodiment of the present invention, the substituents represented by Formula 13 to 17 may be selected from the group consisting of the following Formula A-1 to A-19, but is not limited thereto:
상기 화학식 A-1 내지 A-19에서, In Chemical Formulas A-1 to A-19,
*은 결합이 이루어지는 부분을 의미하고,* Means the part where the coupling is made,
t는 0 내지 5의 정수이며;t is an integer from 0 to 5;
w는 0 내지 4의 정수이며;w is an integer from 0 to 4;
v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
R14는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기(예컨대, L1 또는 L2, 또는 인접하는 다른 R18 또는 R14 등)와 결합하여 축합 고리를 형성할 수 있고, 상기 R14가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 14 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, A C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylsilyl group, or an adjacent group (e.g., L 1 or L 2 , or another adjacent R 18 or R 14 And the like) to form a condensed ring, and when there are a plurality of R 14 , they are the same or different from each other;
상기 R14의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 14 , heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 At least one member selected from the group consisting of an aryl boron group, a C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylsilyl group When unsubstituted or substituted with a substituent on the substituent, and substituted with a plurality of substituents, they may be the same as or different from each other,
R10 내지 R13, p 및 q는 상기 화학식 13 내지 17에서 정의된 바와 같다.R 10 to R 13 , p and q are the same as defined in Chemical Formulas 13 to 17.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 내지 R14는 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60개의 헤테로아릴기일 수 있다.According to a preferred embodiment of the present invention, R 10 to R 14 may be each independently C 6 ~ C 60 An aryl group or a nuclear atom of 5 to 60 heteroaryl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 내지 R14는 각각 독립적으로 페닐기, 비페닐기, 나프탈레닐기, 플루오레닐기, 피리디닐기, 피리미디닐기, 카바졸릴기, 퀴놀리닐기 및 퀴나졸리닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 10 to R 14 are each independently a phenyl group, biphenyl group, naphthalenyl group, fluorenyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, quinolinyl group and quina It may be selected from the group consisting of a zolinyl group.
본 발명의 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다:Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
본 발명에서 상기 화학식 1로 표시되는 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.In the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
2. 유기 2. Organic
전계Electric field
발광 소자 Light emitting element
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.
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 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2 이상 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 It includes a compound represented by the formula (1). In this case, the compound may be used alone or mixed two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 수명 개선층, 전자 수송층, 전자수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 바람직하게는 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 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, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1. Preferably, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.
본 발명의 화학식 1로 표시되는 화합물은 카바졸 모이어티로 인하여 정공 수송 능력이 우수하며, 그에 연결된 플루오렌과 방향족 고리 또는 헤테로방향족 고리의 높은 전자 수송 능력이 우수하여, 분자 내 양극성의 특성을 갖기 때문에 발광층 내에서 정공과 전자의 결합력을 높일 수 있다. The compound represented by the formula (1) of the present invention has excellent hole transporting ability due to the carbazole moiety, and has excellent electron transporting ability of fluorene and aromatic ring or heteroaromatic ring connected thereto, thereby having bipolar characteristics in the molecule. Therefore, the bonding force between the holes and the electrons in the light emitting layer can be increased.
따라서, 본 발명의 일례에 따르면, 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 이와 같이, 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 녹색의 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.Therefore, according to an example of the present invention, the light emitting layer of the organic EL device may include a host material, and may include the compound represented by Formula 1 as the host material. As such, when the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 발광층과 전자 수송층 사이에는 전자 수송 보조층이 추가로 적층될 수 있고, 상기 전자수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 본 발명에서 상기 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 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, an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer. In the present invention, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.
또, 본 발명의 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 EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 적어도 하나 이상(예컨대, 발광층)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 of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
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, 이에 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 있으나, 이에 한정되지는 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 있으나, 이에 한정되지는 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 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[[
준비예Preparation
1] One]
CF1 의Of CF1
합성 synthesis
<단계 1> 2-(3-<Step 1> 2- (3-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 3-브로모-9H-카바졸 (20 g, 81.3 mmol), (3-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2-(3-클로로페닐)-9H-카바졸 (19.4 g, 수율 86 %)을 획득하였다. 3-bromo-9H-carbazole (20 g, 81.3 mmol), (3-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound 2- (3-chlorophenyl) -9H-carbazole (19.4 g, yield 86%) by column chromatography.
1H-NMR: δ 7.38 (d, 1H), 7.46 (m, 4H), 7.61 (m, 2H), 7.77 (d, 1H), 8.03 (s, 1H), 8.15 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 7.38 ( d, 1H), 7.46 (m, 4H), 7.61 (m, 2H), 7.77 (d, 1H), 8.03 (s, 1H), 8.15 (d, 2H), 10.3 ( s, 1 H)
<단계 <Step
2> CF1의2> of CF1
합성 synthesis
질소 기류 하에서 2-(3-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos ( 5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 2- (3-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF1 (18.4 g, 수율 78%)을 얻었다.After completion of the reaction, the mixture 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 CF1 (18.4 g, yield 78%).
1H-NMR: δ 1.68 (s, 6H), 7.32 (t, 3H), 7.58 (m, 9H), 7.75 (s, 2H), 7.88 (d, 3H), 8.13 (d, 1H), 10.3 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.32 (t, 3H), 7.58 (m, 9H), 7.75 (s, 2H), 7.88 (d, 3H), 8.13 (d, 1H), 10.3 ( s, 1 H)
[[
준비예Preparation
2] 2]
CF2 의CF2
합성 synthesis
<단계 1> 2-(4-<Step 1> 2- (4-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 3-브로모-9H-카바졸 (20 g, 81.3 mmol), (4-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2-(4-클로로페닐)-9H-카바졸 (18.9 g, 수율 84 %)을 획득하였다. In a nitrogen stream of 3-bromo -9H- carbazole (20 g, 81.3 mmol), (4- chlorophenyl) Boro acid (15.3 g, 97.5 mmol), Pd (PPh 3) 4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the title compound 2- (4-chlorophenyl) -9H-carbazole (18.9 g, yield 84%).
1H-NMR: δ 7.27 (t, 1H), 7.58 (m, 5H), 7.76 (d, 1H), 8.14 (d, 4H), 10.3 (s, 1H) 1 H-NMR: δ 7.27 (t, 1H), 7.58 (m, 5H), 7.76 (d, 1H), 8.14 (d, 4H), 10.3 (s, 1H)
<단계 2> <Step 2>
CF2 의CF2
합성 synthesis
질소 기류 하에서 2-(4-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 2- (4-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol ), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF2 (17.9 g, 수율 76%) 을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography to obtain CF2 (17.9 g, yield 76%).
1H-NMR: δ 1.68 (s, 6H), 7.26 (m, 7H), 7.64 (t, 5H), 7.75 (s, 2H), 7.91 (d, 3H), 8.11 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.26 (m, 7H), 7.64 (t, 5H), 7.75 (s, 2H), 7.91 (d, 3H), 8.11 (d, 1H)
[[
준비예Preparation
3] CF3의 합성 3] Synthesis of CF3
<단계 1> 2-(2-<Step 1> 2- (2-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 3-브로모-9H-카바졸 (20 g, 81.3 mmol), (2-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2-(2-클로로페닐)-9H-카바졸 (18.1 g, 수율 80 %)을 획득하였다. 3-bromo-9H-carbazole (20 g, 81.3 mmol), (2-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound 2- (2-chlorophenyl) -9H-carbazole (18.1 g, yield 80%).
1H-NMR: δ 7.54 (m, 9H), 8.16 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 7.54 (m, 9H), 8.16 (d, 2H), 10.3 (s, 1H)
<단계 2> CF3의 합성<Step 2> Synthesis of CF3
질소 기류 하에서 2-(2-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos ( 5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 2- (2-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF3 (16.7 g, 수율 71%)을 얻었다.After completion of the reaction, the mixture 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 CF3 (16.7 g, yield 71%).
1H-NMR: δ 1.68 (s, 6H), 7.45 (m, 10H), 7.89 (d, 7H), 8.13 (d, 1H), 10.3 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.45 (m, 10H), 7.89 (d, 7H), 8.13 (d, 1H), 10.3 (s, 1H)
[[
준비예Preparation
4] CF4의 합성 4] Synthesis of CF4
<단계 1> 2-(3-<Step 1> 2- (3-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 2-브로모-9H-카바졸 (20 g, 81.3 mmol), (3-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2-(3-클로로페닐)-9H-카바졸 (18.9 g, 수율 84 %)을 획득하였다. 2-bromo-9H-carbazole (20 g, 81.3 mmol), (3-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%) , NaOH (9.8 g, 243.8 mmol) to 400 ml / put in 100 ml THF / H 2 O was stirred at 80 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound 2- (3-chlorophenyl) -9H-carbazole (18.9 g, yield 84%).
1H-NMR: δ 7.38 (d, 1H), 7.46 (m, 4H), 7.61 (m, 2H), 7.77 (d, 1H), 8.03 (s, 1H), 8.15 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 7.38 (d, 1H), 7.46 (m, 4H), 7.61 (m, 2H), 7.77 (d, 1H), 8.03 (s, 1H), 8.15 (d, 2H), 10.3 ( s, 1 H)
<단계 <Step
2> CF4의2> of CF4
합성 synthesis
질소 기류 하에서 2-(3-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos ( 5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 2- (3-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF4 (16.2 g, 수율 69%) 을 얻었다.After completion of the reaction, the mixture 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 CF4 (16.2 g, yield 69%).
1H-NMR: δ 1.70 (s, 6H), 7.34 (t, 3H), 7.61 (m, 9H), 7.78 (m, 2H), 7.91 (d, 2H), 8.15 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 1.70 (s, 6H), 7.34 (t, 3H), 7.61 (m, 9H), 7.78 (m, 2H), 7.91 (d, 2H), 8.15 (d, 2H), 10.3 ( s, 1 H)
[[
준비예Preparation
5] CF5의 합성 5] Synthesis of CF5
<단계 1> 2-(4-<Step 1> 2- (4-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 2-브로모-9H-카바졸 (20 g, 81.3 mmol), (4-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2-(4-클로로페닐)-9H-카바졸 (18.7 g, 수율 83 %)을 획득하였다. 2-bromo-9H-carbazole (20 g, 81.3 mmol), (4-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound 2- (4-chlorophenyl) -9H-carbazole (18.7 g, 83% yield) using column chromatography.
1H-NMR: δ 7.27 (t, 1H), 7.58 (m, 5H), 7.76 (d, 1H), 8.14 (d, 4H), 10.3 (s, 1H) 1 H-NMR: δ 7.27 (t, 1H), 7.58 (m, 5H), 7.76 (d, 1H), 8.14 (d, 4H), 10.3 (s, 1H)
<단계 <Step
2> CF5의2> CF5
합성 synthesis
질소 기류 하에서 2-(4-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%) 및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 2- (4-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF5 (17.6 g, 수율 75%) 을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the obtained organic layer and purified by column chromatography to obtain CF5 (17.6 g, yield 75%).
1H-NMR: δ 1.70 (s, 6H), 7.27 (m, 7H), 7.58 (m, 5H), 7.78 (m, 2H), 7.90 (d, 2H), 8.15 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 1.70 (s, 6H), 7.27 (m, 7H), 7.58 (m, 5H), 7.78 (m, 2H), 7.90 (d, 2H), 8.15 (d, 2H), 10.3 ( s, 1 H)
[[
준비예Preparation
6] 6]
CF6 의CF6
합성 synthesis
<단계 1> 2-(2-<Step 1> 2- (2-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 2-브로모-9H-카바졸 (20 g, 81.3 mmol), (2-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2-(2-클로로페닐)-9H-카바졸 (18.7 g, 수율 83 %)을 획득하였다. 2-bromo-9H-carbazole (20 g, 81.3 mmol), (2-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound 2- (2-chlorophenyl) -9H-carbazole (18.7 g, 83% yield) using column chromatography.
1H-NMR: δ 7.54 (m, 9H), 8.16 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 7.54 (m, 9H), 8.16 (d, 2H), 10.3 (s, 1H)
<단계 2> CF6의 합성<Step 2> Synthesis of CF6
질소 기류 하에서 2-(2-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos ( 5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 2- (2-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF6 (15 g, 수율 64%) 을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography to obtain CF6 (15 g, yield 64%).
1H-NMR: δ 1.70 (s, 6H), 7.48 (m, 10H), 7.89 (d, 6H), 8.15 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 1.70 (s, 6H), 7.48 (m, 10H), 7.89 (d, 6H), 8.15 (d, 2H), 10.3 (s, 1H)
[[
준비예Preparation
7] CF7의 합성 7] Synthesis of CF7
<단계 1> 1-(3-<Step 1> 1- (3-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 1-브로모-9H-카바졸 (20 g, 81.3 mmol), (3-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 1-(3-클로로페닐)-9H-카바졸 (18.5 g, 수율 82 %)을 획득하였다. 1-bromo-9H-carbazole (20 g, 81.3 mmol), (3-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound 1- (3-chlorophenyl) -9H-carbazole (18.5 g, yield 82%).
1H-NMR: δ 7.41 (m, 6H), 7.62 (d, 1H), 7.84 (d, 1H), 8.09 (d, 3H), 10.3 (s, 1H) 1 H-NMR: δ 7.41 (m, 6H), 7.62 (d, 1H), 7.84 (d, 1H), 8.09 (d, 3H), 10.3 (s, 1H)
<단계 2> CF7의 합성<Step 2> Synthesis of CF7
질소 기류 하에서 1-(3-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 1- (3-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF7 (18.6 g, 수율 79%) 을 얻었다.After completion of the reaction, the mixture 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 CF7 (18.6 g, yield 79%).
1H-NMR: δ 1.70 (s, 6H), 7.34 (t, 4H), 7.68 (m, 8H), 7.76 (s, 1H), 7.90 (d, 3H), 8.10 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 1.70 (s, 6H), 7.34 (t, 4H), 7.68 (m, 8H), 7.76 (s, 1H), 7.90 (d, 3H), 8.10 (d, 2H), 10.3 ( s, 1 H)
[[
준비예Preparation
8] CF8의 합성 8] Synthesis of CF8
<단계 1> 1-(4-<Step 1> 1- (4-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 1-브로모-9H-카바졸 (20 g, 81.3 mmol), (4- 클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 1-(4-클로로페닐)-9H-카바졸 (19.2 g, 수율 85 %)을 획득하였다. 1-bromo-9H-carbazole (20 g, 81.3 mmol) under a nitrogen stream, (4- Chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the title compound 1- (4-chlorophenyl) -9H-carbazole (19.2 g, yield 85%).
1H-NMR: δ 7.33 (t, 2H), 7.65 (m, 6H), 7.85 (d, 1H), 8.10 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 7.33 (t, 2H), 7.65 (m, 6H), 7.85 (d, 1H), 8.10 (d, 2H), 10.3 (s, 1H)
<단계 2> CF8의 합성<Step 2> Synthesis of CF8
질소 기류 하에서 1-(4-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos ( 5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 1- (4-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF8 (17.2 g, 수율 73%) 을 얻었다.After completion of the reaction, the mixture 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 CF8 (17.2 g, yield 73%).
1H-NMR: δ 1.70 (s, 6H), 7.33 (m, 8H), 7.58 (m, 4H), 7.75 (s, 1H), 7.90 (d, 3H), 8.10 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 1.70 (s, 6H), 7.33 (m, 8H), 7.58 (m, 4H), 7.75 (s, 1H), 7.90 (d, 3H), 8.10 (d, 2H), 10.3 ( s, 1 H)
[[
준비예Preparation
9] 9]
CF9 의Of CF9
합성 synthesis
<단계 1> 1-(2-<Step 1> 1- (2-
클로로페닐Chlorophenyl
)-9H-) -9H-
카바졸의Carbazole
합성 synthesis
질소 기류 하에서 1-브로모-9H-카바졸 (20 g, 81.3 mmol), (2-클로로페닐)보로닉산 (15.3 g, 97.5 mmol), Pd(PPh3)4
(4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 1-(2-클로로페닐)-9H-카바졸 (18.7 g, 수율 83 %)을 획득하였다. 1-bromo-9H-carbazole (20 g, 81.3 mmol), (2-chlorophenyl) boronic acid (15.3 g, 97.5 mmol), Pd (PPh 3 ) 4 under nitrogen stream (4.7 g, 5 mol%), NaOH (9.8 g, 243.8 mmol) was added 400 ml / 100 ml of THF / H 2 O, and the mixture was stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound 1- (2-chlorophenyl) -9H-carbazole (18.7 g, 83% yield).
1H-NMR: δ 7.45 (m, 7H), 7.71 (d, 1H), 7.85 (d, 1H), 8.10 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 7.45 (m, 7H), 7.71 (d, 1H), 7.85 (d, 1H), 8.10 (d, 2H), 10.3 (s, 1H)
<단계 2> <Step 2>
CF9 의Of CF9
합성 synthesis
질소 기류 하에서 1-(2-클로로페닐)-9H-카바졸 (15 g, 54.01 mmol), (9,9-디메틸-플루오렌-2-일)보로닉산 (15.4 g, 64.8 mmol), Cs2CO3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd(OAc)2
(0.6 g, 5 mol%)및 1,4-디옥산/H2O (400 ml/100 ml)를 혼합한 다음 120℃에서 12시간 동안 교반하였다. 1- (2-chlorophenyl) -9H-carbazole (15 g, 54.01 mmol), (9,9-dimethyl-fluoren-2-yl) boronic acid (15.4 g, 64.8 mmol), Cs 2 under nitrogen stream CO 3 (35.19 g, 108.01 mmol), X-phos (5.2 g, 10.8 mmol), Pd (OAc) 2 (0.6 g, 5 mol%) and 1,4-dioxane / H 2 O (400 ml / 100 ml) were mixed and then stirred at 120 ° C. for 12 hours.
반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 CF9 (15.8 g, 수율 67%)을 얻었다.After completion of the reaction, the mixture 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 CF9 (15.8 g, yield 67%).
1H-NMR: δ 1.70 (s, 6H), 7.47 (m, 10H), 7.79 (s, 1H), 7.84 (m, 5H), 8.10 (d, 2H), 10.3 (s, 1H) 1 H-NMR: δ 1.70 (s, 6H), 7.47 (m, 10H), 7.79 (s, 1H), 7.84 (m, 5H), 8.10 (d, 2H), 10.3 (s, 1H)
[[
합성예Synthesis Example
1] C 5의 합성 1] Synthesis of C 5
CF1 (10 g, 22.9 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진 (6.2 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 5 (11.64 g, 수율 76%)을 얻었다.CF1 (10 g, 22.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (6.2 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol) and sodium tert-butoxide (4.4 g, 45.9 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C 5 (11.64 g, yield 76%) by column chromatography.
Mass : [(M+H)+] : 667Mass: [(M + H) + ]: 667
[[
합성예Synthesis Example
2] C 7의 합성 2] Synthesis of C 7
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-([1,1'-비페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 (7.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 7 (11.3 g, 수율 74%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (7.9 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 7 (11.3 g, yield 74%).
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
3] C 10의 합성 3] Synthesis of C 10
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 4-(4-브로모페닐)-2,6-디페닐피리미딘 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 7 (12.3 g, 수율 72%)를 얻었다.Except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (8.9 g, 22.9 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Then, the same procedure as in Synthesis Example 1 was performed, to obtain C 7 (12.3 g, yield 72%) as a target compound.
Mass : [(M+H)+] : 742Mass: [(M + H) + ]: 742
[[
합성예Synthesis Example
4] C 11의 합성 4] Synthesis of C 11
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 C 11 (13.3 g, 수율 78%)를 얻었다.2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 Except for using mmol), the same procedure as in Synthesis Example 1 was performed to obtain C 11 (13.3 g, yield 78%) as a target compound.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
5] C 33의 합성 5] Synthesis of C 33
CF2 (10 g, 22.9 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진 (6.2 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 33 (12 g, 수율 79%)을 얻었다.CF2 (10 g, 22.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (6.2 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol) and sodium tert-butoxide (4.4 g, 45.9 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain a target compound C 33 (12 g, yield 79%) by column chromatography.
Mass : [(M+H)+] : 667Mass: [(M + H) + ]: 667
[[
합성예Synthesis Example
6] C 35의 합성 6] Synthesis of C 35
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-([1,1'-비페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 (7.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 35 (12.5 g, 수율 73%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (7.9 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 5 to obtain the target compound C 35 (12.5 g, 73% yield).
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
7] C 38의 합성 7] Synthesis of C 38
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 4-(4-브로모페닐)-2,6-디페닐피리미딘 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 38 (12.6 g, 수율 74%)를 얻었다.Except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (8.9 g, 22.9 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Then, the same procedure as in Synthesis Example 5 was performed to obtain C 38 (12.6 g, yield 74%) as a target compound.
Mass : [(M+H)+] : 742Mass: [(M + H) + ]: 742
[[
합성예Synthesis Example
8] C 39의 합성 8] Synthesis of C 39
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 C 39 (12.9 g, 수율 76%)를 얻었다.2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 Except for using mmol), the same procedure as in Synthesis Example 5 was carried out to obtain a target compound C 39 (12.9 g, yield 76%).
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
9] C 61의 합성 9] Synthesis of C 61
CF3 (10 g, 22.9 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진 (6.2 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 61 (9.8 g, 수율 64%)을 얻었다.CF3 (10 g, 22.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (6.2 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol) and sodium tert-butoxide (4.4 g, 45.9 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C 61 (9.8 g, 64% yield) by column chromatography.
Mass : [(M+H)+] : 667Mass: [(M + H) + ]: 667
[[
합성예Synthesis Example
10] C 63의 합성 10] Synthesis of C 63
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-([1,1'-비페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 (7.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 9와 동일한 과정을 수행하여 목적 화합물인 C 63 (10.7 g, 수율 63%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (7.9 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 9 to obtain the target compound C 63 (10.7 g, 63% yield).
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
11] C 66의 합성 11] Synthesis of C 66
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 4-(4-브로모페닐)-2,6-디페닐피리미딘 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 9와 동일한 과정을 수행하여 목적 화합물인 C 66 (11.4 g, 수율 67%)를 얻었다.Except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (8.9 g, 22.9 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Then, the same procedure as in Synthesis Example 9 was performed to obtain C 66 (11.4 g, yield 67%) as a target compound.
Mass : [(M+H)+] : 742Mass: [(M + H) + ]: 742
[[
합성예Synthesis Example
12] C 67의 합성 12] Synthesis of C 67
2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 9와 동일한 과정을 수행하여 목적 화합물인 C 67 (12.9 g, 수율 62%)를 얻었다.2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 Except for using mmol), the same procedure as in Synthesis Example 9 was performed to obtain C 67 (12.9 g, yield 62%) as a target compound.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
13] C 13] C
92 의92 of
합성 synthesis
CF4 (10 g, 22.9 mmol)와 2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 (10.7 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 92 (12.8 g, 수율 68%)을 얻었다.CF4 (10 g, 22.9 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine ( 10.7 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol), sodium tert-butoxide (4.4 g, 45.9 mmol) Into ml ml toluene and stirred at 110 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain a target compound C 92 (12.8 g, yield 68%) by column chromatography.
Mass : [(M+H)+] : 820Mass: [(M + H) + ]: 820
[[
합성예Synthesis Example
14] C 95의 합성 14] Synthesis of C 95
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 13와 동일한 과정을 수행하여 목적 화합물인 C 95 (11.1 g, 수율 65%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine instead of 2- (3-bromophenyl) Except for using -4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 13 to give the target compound C 95 (11.1 g, yield 65 %) Was obtained.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
15] C 103의 합성 15] Synthesis of C 103
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (5.5 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 13와 동일한 과정을 수행하여 목적 화합물인 C 103 (8.7 g, 수율 59%)를 얻었다.2-chloro-4-phenylquinazoline instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (5.5 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 13 to obtain the target compound C 103 (8.7 g, 59% yield).
Mass : [(M+H)+] : 640Mass: [(M + H) + ]: 640
[[
합성예Synthesis Example
16] C 104의 합성 16] Synthesis of C 104
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-(4-(나프탈렌-1-일)페닐)퀴나졸린 (8.4 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 13와 동일한 과정을 수행하여 목적 화합물인 C 104 (10.0 g, 수율 57%)를 얻었다.2-chloro-4- (4- instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (naphthalen-1-yl) phenyl) quinazolin (8.4 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 13 to obtain the target compound C 104 (10.0 g, yield 57%).
Mass : [(M+H)+] : 766Mass: [(M + H) + ]: 766
[[
합성예Synthesis Example
17] C 120의 합성 17] Synthesis of C 120
CF5 (10 g, 22.9 mmol)와 2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 (10.7 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 120 (13.9 g, 수율 74%)을 얻었다.CF5 (10 g, 22.9 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine ( 10.7 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol), sodium tert-butoxide (4.4 g, 45.9 mmol) Into ml ml toluene and stirred at 110 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C 120 (13.9 g, 74% yield).
Mass : [(M+H)+] : 820Mass: [(M + H) + ]: 820
[[
합성예Synthesis Example
18] C 123의 합성 18] Synthesis of C 123
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 17와 동일한 과정을 수행하여 목적 화합물인 C 123 (12.9 g, 수율 76%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine instead of 2- (3-bromophenyl) Except for using -4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 17 to obtain the target compound C 123 (12.9 g, yield 76 %) Was obtained.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
[[
합성예Synthesis Example
19] C 131의 합성 19] Synthesis of C 131
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (5.5 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 17 와 동일한 과정을 수행하여 목적 화합물인 C 131 (9.7 g, 수율 66%)를 얻었다.2-chloro-4-phenylquinazoline instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (5.5 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 17 to obtain the target compound C 131 (9.7 g, 66% yield).
Mass : [(M+H)+] : 640Mass: [(M + H) + ]: 640
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합성예Synthesis Example
20] C 132의 합성 20] Synthesis of C 132
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-(4-(나프탈렌-1-일)페닐)퀴나졸린 (8.4 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 13와 동일한 과정을 수행하여 목적 화합물인 C 132 (12.1 g, 수율 69%)를 얻었다.2-chloro-4- (4- instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (naphthalen-1-yl) phenyl) quinazolin (8.4 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 13 to obtain the target compound C 132 (12.1 g, 69% yield).
Mass : [(M+H)+] : 766Mass: [(M + H) + ]: 766
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합성예Synthesis Example
21] C 148의 합성 21] Synthesis of C 148
CF6 (10 g, 22.9 mmol)와 2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 (10.7 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 148 (12.0 g, 수율 64%)을 얻었다.CF6 (10 g, 22.9 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine ( 10.7 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol), sodium tert-butoxide (4.4 g, 45.9 mmol) Into ml ml toluene and stirred at 110 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C 148 (12.0 g, 64% yield).
Mass : [(M+H)+] : 820Mass: [(M + H) + ]: 820
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합성예Synthesis Example
22] C 151의 합성 22] Synthesis of C 151
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 21 와 동일한 과정을 수행하여 목적 화합물인 C 151 (10.6 g, 수율 62%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine instead of 2- (3-bromophenyl) Except for using -4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 21 C 151 (10.6 g, yield 62) %) Was obtained.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
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합성예Synthesis Example
23] C 159의 합성 23] Synthesis of C 159
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (5.5 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 21 와 동일한 과정을 수행하여 목적 화합물인 C 159 (8.4 g, 수율 57%)를 얻었다.2-chloro-4-phenylquinazoline instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (5.5 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 21 to obtain the target compound C 159 (8.4 g, yield 57%).
Mass : [(M+H)+] : 640Mass: [(M + H) + ]: 640
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합성예Synthesis Example
24] C 160의 합성 24] Synthesis of C 160
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-(4-(나프탈렌-1-일)페닐)퀴나졸린 (8.4 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 21와 동일한 과정을 수행하여 목적 화합물인 C 160 (9.3 g, 수율 53%)를 얻었다.2-chloro-4- (4- instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (naphthalen-1-yl) phenyl) quinazolin (8.4 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 21 to obtain the target compound C 160 (9.3 g, yield 53%).
Mass : [(M+H)+] : 766Mass: [(M + H) + ]: 766
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합성예Synthesis Example
25] C 176의 합성 25] Synthesis of C 176
CF7 (10 g, 22.9 mmol)와 2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 (10.7 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 176 (12.8 g, 수율 68%)을 얻었다.CF7 (10 g, 22.9 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine ( 10.7 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol), sodium tert-butoxide (4.4 g, 45.9 mmol) Put in ml toluene and stirred at 110 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain a target compound C 176 (12.8 g, yield 68%) by column chromatography.
Mass : [(M+H)+] : 820Mass: [(M + H) + ]: 820
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합성예Synthesis Example
26] C 179의 합성 26] Synthesis of C 179
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 25 와 동일한 과정을 수행하여 목적 화합물인 C 179 (11.4 g, 수율 67%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine instead of 2- (3-bromophenyl) Except for using -4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 mmol), the same procedure as in Synthesis Example 25 was carried out to give the title compound C 179 (11.4 g, yield 67). %) Was obtained.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
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합성예Synthesis Example
27] C 187의 합성 27] Synthesis of C 187
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (5.5 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 25 와 동일한 과정을 수행하여 목적 화합물인 C 187 (9.1 g, 수율 62%)를 얻었다.2-chloro-4-phenylquinazoline instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (5.5 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 25 to obtain the target compound C 187 (9.1 g, yield 62%).
Mass : [(M+H)+] : 640Mass: [(M + H) + ]: 640
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합성예Synthesis Example
28] C 188의 합성 28] Synthesis of C 188
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-(4-(나프탈렌-1-일)페닐)퀴나졸린 (8.4 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 25와 동일한 과정을 수행하여 목적 화합물인 C 188 (10.7 g, 수율 61%)를 얻었다.2-chloro-4- (4- instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (naphthalen-1-yl) phenyl) quinazolin (8.4 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 25 to obtain the target compound C 188 (10.7 g, 61% yield).
Mass : [(M+H)+] : 766Mass: [(M + H) + ]: 766
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합성예Synthesis Example
29] C 204의 합성 29] Synthesis of C 204
CF8 (10 g, 22.9 mmol)와 2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 (10.7 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 204 (13.4 g, 수율 71%)을 얻었다.CF8 (10 g, 22.9 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine ( 10.7 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol), sodium tert-butoxide (4.4 g, 45.9 mmol) Put in ml toluene and stirred at 110 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C 204 (13.4 g, yield 71%).
Mass : [(M+H)+] : 820Mass: [(M + H) + ]: 820
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합성예Synthesis Example
30] C 207의 합성 30] Synthesis of C 207
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 29 와 동일한 과정을 수행하여 목적 화합물인 C 207 (17.1 g, 수율 73%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine instead of 2- (3-bromophenyl) C 207 (17.1 g, Yield 73) was carried out in the same manner as in Synthesis Example 29, except that -4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 mmol) was used. %) Was obtained.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
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합성예Synthesis Example
31] C 215의 합성 31] Synthesis of C 215
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (5.5 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 29 와 동일한 과정을 수행하여 목적 화합물인 C 215 (9.5 g, 수율 65%)를 얻었다.2-chloro-4-phenylquinazoline instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (5.5 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 29 to obtain the target compound C 215 (9.5 g, 65% yield).
Mass : [(M+H)+] : 640Mass: [(M + H) + ]: 640
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합성예Synthesis Example
32] C 216의 합성 32] Synthesis of C 216
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-(4-(나프탈렌-1-일)페닐)퀴나졸린 (8.4 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 29와 동일한 과정을 수행하여 목적 화합물인 C 216 (11.6 g, 수율 66%)를 얻었다.2-chloro-4- (4- instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (naphthalen-1-yl) phenyl) quinazoline (8.4 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 29 to obtain the target compound C 216 (11.6 g, 66% yield).
Mass : [(M+H)+] : 766Mass: [(M + H) + ]: 766
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합성예Synthesis Example
33] C 232의 합성 33] Synthesis of C 232
CF9 (10 g, 22.9 mmol)와 2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 (10.7 g, 22.9 mmol) 및 Pd2(dba)3 (1.1 g, 1.15 mmol), P(t-Bu)3 (0.9 g, 4.6 mmol), 나트륨 tert-부톡사이드 (4.4 g, 45.9 mmol) 을 150 ml 톨루엔 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C 232 (10.9 g, 수율 58%)을 얻었다.CF9 (10 g, 22.9 mmol) and 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine ( 10.7 g, 22.9 mmol) and Pd 2 (dba) 3 (1.1 g, 1.15 mmol), P (t-Bu) 3 (0.9 g, 4.6 mmol), sodium tert-butoxide (4.4 g, 45.9 mmol) Put in ml toluene and stirred at 110 ℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C 232 (10.9 g, yield 58%).
Mass : [(M+H)+] : 820Mass: [(M + H) + ]: 820
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합성예Synthesis Example
34] C 235의 합성 34] Synthesis of C 235
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (8.9 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 33 와 동일한 과정을 수행하여 목적 화합물인 C 235 (10.2 g, 수율 60%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine instead of 2- (3-bromophenyl) Except for using -4,6-diphenyl-1,3,5-triazine (8.9 g, 22.9 mmol) was carried out in the same manner as in Synthesis Example 33 to give the target compound C 235 (10.2 g, yield 60 %) Was obtained.
Mass : [(M+H)+] : 743Mass: [(M + H) + ]: 743
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합성예Synthesis Example
35] C 243의 합성 35] Synthesis of C 243
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-페닐퀴나졸린 (5.5 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 33 와 동일한 과정을 수행하여 목적 화합물인 C 243 (7.5 g, 수율 51%)를 얻었다.2-chloro-4-phenylquinazoline instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (5.5 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 33 to obtain the target compound C 243 (7.5 g, yield 51%).
Mass : [(M+H)+] : 640Mass: [(M + H) + ]: 640
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합성예Synthesis Example
36] C 244의 합성 36] Synthesis of C 244
2-([1,1'-비페닐]-4-일)-4-(3-브로모페닐)-6-페닐-1,3,5-트리아진 대신 2-클로로-4-(4-(나프탈렌-1-일)페닐)퀴나졸린 (8.4 g, 22.9 mmol)을 사용하는 것을 제외하고는 합성예 33와 동일한 과정을 수행하여 목적 화합물인 C 244 (8.4 g, 수율 48%)를 얻었다.2-chloro-4- (4- instead of 2-([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine Except for using (naphthalen-1-yl) phenyl) quinazolin (8.4 g, 22.9 mmol) was carried out the same procedure as in Synthesis Example 33 to obtain the target compound C 244 (8.4 g, yield 48%).
Mass : [(M+H)+] : 766Mass: [(M + H) + ]: 766
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실시예Example
1 ~ 24] 녹색 유기 1 to 24] green organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
합성예 1 ~ 34에서 합성한 화합물 C 5 ~ C 235를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compounds C 5 to C 235 synthesized in Synthesis Examples 1 to 34 were subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 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.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ C 5 ~ C 235의 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / C 5 to C 235 each compound + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 ( 30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device.
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
[비교예 1] 녹색 유기 전계 발광 소자의 제작Comparative Example 1 Fabrication of Green Organic Electroluminescent Device
발광층 형성시 발광 호스트 물질로서 화합물 C 5 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 5 as a light emitting host material when forming the emission layer.
[평가예 1][Evaluation Example 1]
실시예 1 ~ 24 및 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the green organic electroluminescent devices fabricated in Examples 1 to 24 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | C 5C 5 | 6.646.64 | 516516 | 42.242.2 |
| 실시예 2Example 2 | C 7C 7 | 6.356.35 | 517517 | 43.543.5 |
| 실시예 3Example 3 | C 10C 10 | 6.626.62 | 518518 | 45.745.7 |
| 실시예 4Example 4 | C 11C 11 | 6.536.53 | 516516 | 42.342.3 |
| 실시예 5Example 5 | C 33C 33 | 6.366.36 | 517517 | 43.143.1 |
| 실시예 6Example 6 | C 35C 35 | 6.886.88 | 516516 | 43.643.6 |
| 실시예 7Example 7 | C 38C 38 | 6.446.44 | 516516 | 46.246.2 |
| 실시예 8Example 8 | C 39C 39 | 6.626.62 | 516516 | 43.443.4 |
| 실시예 9Example 9 | C 61C 61 | 6.466.46 | 517517 | 43.743.7 |
| 실시예 10Example 10 | C 63C 63 | 6.396.39 | 516516 | 47.447.4 |
| 실시예 11Example 11 | C 66C 66 | 6.746.74 | 516516 | 47.647.6 |
| 실시예 12Example 12 | C 67C 67 | 6.816.81 | 518518 | 43.243.2 |
| 실시예 13Example 13 | C 92C 92 | 6.386.38 | 516516 | 47.447.4 |
| 실시예 14Example 14 | C 95C 95 | 6.546.54 | 518518 | 44.144.1 |
| 실시예 15Example 15 | C 120C 120 | 6.676.67 | 517517 | 42.442.4 |
| 실시예 16Example 16 | C 123C 123 | 6.326.32 | 517517 | 46.746.7 |
| 실시예 17Example 17 | C 148C 148 | 6.556.55 | 516516 | 44.844.8 |
| 실시예 18Example 18 | C 151C 151 | 6.836.83 | 518518 | 43.543.5 |
| 실시예 19Example 19 | C 176C 176 | 6.166.16 | 516516 | 48.148.1 |
| 실시예 20Example 20 | C 179C 179 | 6.246.24 | 516516 | 49.649.6 |
| 실시예 21Example 21 | C 204C 204 | 6.266.26 | 517517 | 49.949.9 |
| 실시예 22Example 22 | C 207C 207 | 6.186.18 | 518518 | 48.448.4 |
| 실시예 23Example 23 | C 232C 232 | 6.266.26 | 516516 | 49.249.2 |
| 실시예 24Example 24 | C 235C 235 | 6.126.12 | 517517 | 48.648.6 |
| 비교예 1Comparative Example 1 | CBPCBP | 6.93 6.93 | 516 516 | 38.2 38.2 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물 (C 5 ~ C 235)을 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우(실시예 1 ~ 24) 종래 CBP를 사용한 녹색 유기 전계 발광 소자(비교예 1)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 1, when the compound (C 5 ~ C 235) according to the present invention is used as the light emitting layer of the green organic electroluminescent device (Examples 1 ~ 24), the green organic electroluminescent device using the conventional CBP (compared to Compared with Example 1) it can be seen that the better performance in terms of efficiency and driving voltage.
[실시예 25 ~ 36] 적색 유기 전계 발광 소자의 제작Examples 25 to 36 Fabrication of Red Organic Electroluminescent Devices
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 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.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ C 103 ~ C 244 의 화합물 + 10 % (piq)2Ir(acac) (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / C 103 ~ C 244 compound + 10% (piq) 2 Ir (acac) (300 nm) / BCP (10 nm) / Alq 3 on the prepared ITO transparent electrode (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to fabricate an organic EL device.
[비교예 2] 적색 유기 전계 발광 소자의 제작Comparative Example 2 Fabrication of Red Organic Electroluminescent Device
발광층 형성시 발광 호스트 물질로서 상기 C 103 화합물 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 25와 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 25, except that CBP was used instead of the C 103 compound as a light emitting host material when the emission layer was formed.
상기 실시예 25 ~ 36 및 비교예2 에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir (acac), CBP, and BCP used in Examples 25 to 36 and Comparative Example 2 are as follows.
[평가예 2][Evaluation Example 2]
실시예 25 ~ 36 및 비교예 2에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For each organic electroluminescent device manufactured in Examples 25 to 36 and Comparative Example 2, the driving voltage and current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 25Example 25 | C 103C 103 | 4.944.94 | 12.712.7 |
| 실시예 26Example 26 | C 104C 104 | 4.854.85 | 12.612.6 |
| 실시예 27Example 27 | C 131C 131 | 4.734.73 | 12.912.9 |
| 실시예 28Example 28 | C 132C 132 | 4.964.96 | 13.813.8 |
| 실시예 29Example 29 | C 159C 159 | 4.924.92 | 12.612.6 |
| 실시예 30Example 30 | C 160C 160 | 4.844.84 | 13.613.6 |
| 실시예 31Example 31 | C 187C 187 | 4.284.28 | 14.814.8 |
| 실시예 32Example 32 | C 188C 188 | 4.144.14 | 15.815.8 |
| 실시예 33Example 33 | C 215C 215 | 4.324.32 | 14.714.7 |
| 실시예 34Example 34 | C 216C 216 | 4.254.25 | 14.614.6 |
| 실시예 35Example 35 | C 243C 243 | 4.284.28 | 15.815.8 |
| 실시예 36Example 36 | C 244C 244 | 4.344.34 | 15.615.6 |
| 비교예 2Comparative Example 2 | CBPCBP | 5.255.25 | 8.28.2 |
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 적색 유기 전계 발광 소자의 발광층의 재료로 사용하였을 경우(실시예 25 ~ 36) 종래 CBP를 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교 예2)와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2 above, when the compound according to the present invention was used as a material of the light emitting layer of the red organic electroluminescent device (Examples 25 to 36), a red organic electroluminescent device using a conventional CBP as a material of the light emitting layer (comparative example) Compared with 2), it shows excellent performance in terms of efficiency and driving voltage.
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.
Claims (10)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,L1 내지 L4는 각각 독립적으로 단일결합, C6~C60의 아릴렌기 및 핵원자수 5 내지 60개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며;R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ for C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ is selected from the group consisting of an aryl amine of the C 60 of the;l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;n은 0 내지 3의 정수이며;n is an integer from 0 to 3;R4 내지 R6은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R4 내지 R6 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 4 to R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Arylphosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 An arylamine group, and when a plurality of each of R 4 to R 6 They are the same as each other or Different;상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R6의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R 1 to R 6 , Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C When substituted or unsubstituted with one or more substituents selected from the group consisting of 6 to C 60 arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 화합물은 하기 화학식 2 내지 4 중 어느 하나로 표시되는 화합물인 화합물:The compound is a compound represented by any one of the following formulas 2 to:[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에서,In Chemical Formulas 2 to 4,l, m, n, L1 내지 L4 및 R1 내지 R6 각각은 제1항에서 정의된 바와 같다.l, m, n, L 1 to L 4 and R 1 to R 6 are each as defined in claim 1. - 제1항에 있어서,The method of claim 1,상기 L1 내지 L4는 각각 독립적으로 하기 화학식 5 내지 7로 이루어진 군에서 선택되는 화합물:Wherein L 1 to L 4 are each independently to a compound selected from the group consisting of Formulas 5 to 7:[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 5 내지 7에서,In Chemical Formulas 5 to 7,*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;Z1 내지 Z8은 각각 독립적으로 N 또는 C(R7)이나, 상기 화학식 5에서 Z1 내지 Z6 중 적어도 2개는 C(R7)이고, 화학식 6에서 Z1 내지 Z4 중 적어도 2개는 C(R7)이며, 화학식 7에서는 Z1 내지 Z4 중 적어도 하나, Z5 내지 Z8 중 적어도 하나는 C(R7)이며;Z 1 to Z 8 are each independently N or C (R 7 ), but in Formula 5, at least two of Z 1 to Z 6 are C (R 7 ) and at least 2 of Z 1 to Z 4 in Formula 6 The dog is C (R 7 ), in formula 7 at least one of Z 1 to Z 4 , at least one of Z 5 to Z 8 is C (R 7 );R7은 부재이거나, 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R7이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 7 is absent, hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, and when there are a plurality of R 7 , they are the same or different from each other;상기 R7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 7 is heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 the arylboronic group, one member selected from the group consisting of C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl group of the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 화합물은 하기 화학식 8 내지 12 중 어느 하나로 표시되는 화합물:The compound is a compound represented by any one of the following formula 8 to 12:[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
상기 화학식 8 내지 12에서,In Chemical Formulas 8 to 12,l, m, n, L1, L2 및 R1 내지 R6 각각은 제1항에서 정의된 바와 같다.l, m, n, L 1 , L 2 and R 1 to R 6 are each as defined in claim 1. - 제1항에 있어서,The method of claim 1,상기 R1은 하기 화학식 13 내지 17 중 어느 하나로 표시되는 치환기인 화합물:R 1 is a compound represented by any one of Formulas 13 to 17:[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17][Formula 17]
상기 화학식 13 내지 17에서, In Chemical Formulas 13 to 17,*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;X1 내지 X8은 각각 독립적으로 N 또는 C(R10)이며;X 1 to X 8 are each independently N or C (R 10 );상기 화학식 14에서 L2에 결합되는 X1 내지 X4 중 어느 하나는 C(R10)이고, 이때 상기 R10은 부재이며;In Formula 14, any one of X 1 to X 4 bonded to L 2 is C (R 10 ), wherein R 10 is absent;T1은 N 또는 C(R10)이며;T 1 is N or C (R 10 );Y1은 O, S, N(R11) 또는 C(R12)(R13)이며;Y 1 is O, S, N (R 11 ) or C (R 12 ) (R 13 );p 및 q는 각각 독립적으로 0 내지 4의 정수이며;p and q are each independently integers of 0 to 4;R8 및 R9는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R8 및 R9 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 8 and R 9 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Is selected from the group consisting of an arylphosphanyl group, a C 6 ~ C 60 mono or diaryl phosphinyl group and a C 6 ~ C 60 arylamine group, and when there are a plurality of R 8 and R 9 are each the same or Different;R10 내지 R13은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R10이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 to R 13 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of the R 10 in this case, plural personal they the same or different, and ;상기 R8 내지 R13의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 8 to R 13 boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 R1은 하기 화학식 A-1 내지 A-19로 이루어진 군에서 선택되는 치환기인 화합물:Wherein R 1 is a substituent selected from the group consisting of Formulas A-1 to A-19:
상기 화학식 A-1 내지 A-19에서, In Chemical Formulas A-1 to A-19,*은 결합이 이루어지는 부분을 의미하고,* Means the part where the coupling is made,t는 0 내지 5의 정수이며;t is an integer from 0 to 5;w는 0 내지 4의 정수이며;w is an integer from 0 to 4;v는 0 내지 3의 정수이며;v is an integer from 0 to 3;u는 0 내지 2의 정수이며;u is an integer from 0 to 2;p 및 q는 각각 독립적으로 0 내지 4의 정수이며;p and q are each independently integers of 0 to 4;R10 내지 R13은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R10이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 to R 13 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of the R 10 in this case, plural personal they the same or different, and ;R14는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R14가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 14 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ C 60 selected from the group consisting of aryl silyl or a, combination group adjacent to which they are attached may form a condensed ring, when the individual has the R 14 a plurality These Same or different from each other;상기 R10 내지 R14의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 10 to R 14 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other. - 제6항에 있어서,The method of claim 6,상기 R10 내지 R14는 각각 독립적으로 C6~C60의 아릴기 또는 핵원자수 5 내지 60개의 헤테로아릴기인 화합물.Wherein R 10 to R 14 are each independently C 6 ~ aryl group or a nuclear atoms of 5 to 60 heteroaryl group in the C 60 compound.
- 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물:Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of:
- (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1.
- 제9항에 있어서,The method of claim 9,상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 수송 보조층, 전자 주입층, 수명 개선층, 발광층 및 발광 보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.The organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.
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