WO2018038544A1 - 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 - Google Patents
유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 Download PDFInfo
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- WO2018038544A1 WO2018038544A1 PCT/KR2017/009238 KR2017009238W WO2018038544A1 WO 2018038544 A1 WO2018038544 A1 WO 2018038544A1 KR 2017009238 W KR2017009238 W KR 2017009238W WO 2018038544 A1 WO2018038544 A1 WO 2018038544A1
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- QKUSGKJWHGTFLK-UHFFFAOYSA-N CC1(C)c2cc(N(c(cc3)cc4c3-c3c(cccc5)c5ccc3C43c4c(cccc5)c5ccc4-c4ccccc34)c3ccc(cccc4)c4c3)ccc2-c2c1cccc2 Chemical compound CC1(C)c2cc(N(c(cc3)cc4c3-c3c(cccc5)c5ccc3C43c4c(cccc5)c5ccc4-c4ccccc34)c3ccc(cccc4)c4c3)ccc2-c2c1cccc2 QKUSGKJWHGTFLK-UHFFFAOYSA-N 0.000 description 1
- VGLPLHXTYNIXHZ-UHFFFAOYSA-N CCC(C)(N([AlH2])[AlH2])I Chemical compound CCC(C)(N([AlH2])[AlH2])I VGLPLHXTYNIXHZ-UHFFFAOYSA-N 0.000 description 1
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- QNWXGMOXTNCMIR-UHFFFAOYSA-N O=Nc(c1ccccc1cc1)c1-c(cc1)cc2c1c1cc3ccccc3cc1[o]2 Chemical compound O=Nc(c1ccccc1cc1)c1-c(cc1)cc2c1c1cc3ccccc3cc1[o]2 QNWXGMOXTNCMIR-UHFFFAOYSA-N 0.000 description 1
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
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- UKZFYVPGJCRNFN-UHFFFAOYSA-N [O-][N+](c(c(Br)c1)ccc1-c(cc1c2c3cccc2)ccc1[n]3-c1ccccc1)=O Chemical compound [O-][N+](c(c(Br)c1)ccc1-c(cc1c2c3cccc2)ccc1[n]3-c1ccccc1)=O UKZFYVPGJCRNFN-UHFFFAOYSA-N 0.000 description 1
- DKIWWLDENDLYJA-UHFFFAOYSA-N [O-][N+](c(c(cccc1)c1cc1)c1-c1ccc2[s]c(c3ccccc3cc3)c3c2c1)=O Chemical compound [O-][N+](c(c(cccc1)c1cc1)c1-c1ccc2[s]c(c3ccccc3cc3)c3c2c1)=O DKIWWLDENDLYJA-UHFFFAOYSA-N 0.000 description 1
- LUMHTXRRZWUYQX-UHFFFAOYSA-N [O-][N+](c1cc(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)ccc1-c(cc1)cc2c1[s]c1c2ccc2c1cccc2)=O Chemical compound [O-][N+](c1cc(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)ccc1-c(cc1)cc2c1[s]c1c2ccc2c1cccc2)=O LUMHTXRRZWUYQX-UHFFFAOYSA-N 0.000 description 1
- QTKPRFHSJPMDQM-UHFFFAOYSA-N [O-][N+](c1ccccc1-c1ccc2[s]c3c(cccc4)c4ccc3c2c1)=O Chemical compound [O-][N+](c1ccccc1-c1ccc2[s]c3c(cccc4)c4ccc3c2c1)=O QTKPRFHSJPMDQM-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 238000005885 boration reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- TZPGEPHTYYWURH-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-[n]2c(cc(c3c4)[o]c5c3c(cccc3)c3c3ccccc53)c4c3ccccc23)cc(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1cc(-[n]2c(cc(c3c4)[o]c5c3c(cccc3)c3c3ccccc53)c4c3ccccc23)cc(-c2ccccc2)c1 TZPGEPHTYYWURH-UHFFFAOYSA-N 0.000 description 1
- CTPPXEPSKPYLTM-UHFFFAOYSA-N c1ccc(c2c(cc3)c(cc(c(ccc4ccccc44)c4[s]4)c4c4)c4[nH]2)c3c1 Chemical compound c1ccc(c2c(cc3)c(cc(c(ccc4ccccc44)c4[s]4)c4c4)c4[nH]2)c3c1 CTPPXEPSKPYLTM-UHFFFAOYSA-N 0.000 description 1
- AKELWABOXZJXBY-UHFFFAOYSA-N c1ccc2[nH]c(cc(c3c4)[o]c5c3c(cccc3)c3c3ccccc53)c4c2c1 Chemical compound c1ccc2[nH]c(cc(c3c4)[o]c5c3c(cccc3)c3c3ccccc53)c4c2c1 AKELWABOXZJXBY-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
Definitions
- the present invention relates to a compound for an organic electric device, an organic electric device using the same and an electronic
- organic luminescence refers to the use of organic materials to produce electrical energy.
- the organic electroluminescent device using organic light emitting phenomenon usually has a structure including an anode and a cathode, and an organic layer between them, where the organic layer is a different material to increase the efficiency and stability of the organic electronic device.
- the structure may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
- Materials used as organic layers in organic electric devices may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions.
- the gaps (HOMO, LUMO), electrical characteristics, chemical characteristics, and physical properties have various characteristics. Therefore, application and development of various organic electric element layers using them has been in progress.
- Patent Document 1 United States Patent Publication 5843607
- Patent Document 2 Japanese Patent Application Laid-Open No. 1999-162650
- Patent Document 3 Korean Patent Publication No. 2 008-008 5 000
- Patent Document 4 US Patent Publication 2010-0187977
- Patent Document 5 Korean Laid-Open Patent Publication 2011-0018340
- Patent Document 6 Korean Laid-Open Patent Publication 2009-0057711
- Patent Literature 1 and Patent Literature 2 use indolocarbazole cores composed exclusively of heteroatomic nitrogen (N) in a 5-ring ring compound, and examples using N-substituted or unsubstituted aryl groups of indolocarbazole.
- N heteroatomic nitrogen
- Patent Literature 1 and Patent Literature 2 use indolocarbazole cores composed exclusively of heteroatomic nitrogen (N) in a 5-ring ring compound, and examples using N-substituted or unsubstituted aryl groups of indolocarbazole.
- N heteroatomic nitrogen
- Patent Literature 1 and Patent Literature 2 use indolocarbazole cores composed exclusively of heteroatomic nitrogen (N) in a 5-ring ring compound, and examples using N-substituted or unsubstituted aryl groups of indolocarbazole.
- Patent Document 3 and Patent Document 4 have the same 5 rings as Patent Document 1 and Patent Document 2;
- Patent Document 5 discloses heteroatoms in a 5-ring compound, such as nitrogen (N), oxygen (0), sulfur (S), and carbon, but all of the same types of performance measurement data.
- 5-membered ring compound molecules When 5-membered ring compound molecules are generally stacked, they have strong electrical interactions as the number of adjacent ⁇ -electrons increases, which is closely related to the charge carrier mobility, especially the NN type phosphorus 5-membered ring compound.
- silver molecules When silver molecules are stacked, the arrangement order between molecules has an edge-to-face shape, while heterocyclic heterocyclic compounds having different heteroatoms have a pie-laminated structure in which the packing structure of the molecules faces in the reverse direction (antiparallel cofacial ⁇ -).
- the stacking structure has a face-to-face arrangement order, and due to the steric effect of the substituents substituted by heteroatom N, which is asymmetric, the cause of the lamination structure is relatively high carrier mobility and high It has been reported to cause oxidative stability. (Org. Lett. 2008, 10, 1199)
- Patent Document 6 an example of using a fluorescent host material for a variety of ring compounds having more than 7 rings is reported.
- the LUMO and HOMO levels of host materials have a great influence on the efficiency and lifespan of organic electronic devices. This effectively regulates electron and hole injection in the light emitting layer. This can be achieved by reducing charge balance in the light emitting layer, doping quenching and light emission at the hole transport layer.
- TADF is used for fluorescent and phosphorescent host materials. Increasing the efficiency and lifespan of organic electronic devices using delayed fluorescent, Exciplex, etc. are being studied. In particular, much research is being conducted on the identification of energy transfer methods to host materials.
- the time resolved transient PL (TRTP) method is a method of examining the decay time of spectra over time after examining the Fils light source on the host thin film.
- TRTP time resolved transient PL
- the present invention has been proposed to solve the above problems of phosphorescent host materials.
- the present invention provides a method for controlling charge balance in a light emitting layer by adjusting HOMO levels for host materials of phosphorescent organic devices including phosphorescent shifts. It aims to provide a compound which can improve efficiency and lifespan, an organic electronic device using the same, and an electronic device thereof.
- the present invention provides efficient hole injection in the light emitting layer of phosphorescent organic devices.
- the energy barrier of the light emitting layer and the adjacent layer can be made small, and the charge balance in the light emitting layer is maximized, resulting in high efficiency and adherence to organic electric elements. To provide people.
- the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is represented by the following formula:
- An organic electric device characterized by comprising a first host compound represented by 1 and a second host compound represented by the following formula (2).
- the present invention provides an organic electric element and its electronic device using the compound represented by the above formula.
- FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
- organic electrical element 110 substrate
- first, second, A, B, (a), and (b) may be used. These terms refer to the components as other components. It is merely to be distinguished, and the terminology does not limit the nature, turn or order of the components. If a component is “connected”, “coupled” or “connected” to another component, that component May be directly connected or connected to the other components, but it should be understood that another component may be “connected”, “coupled” or “connected” between each component.
- alkyl or “alkyl group” used in the present invention is 1 to 1 unless otherwise specified.
- a straight chain alkyl group Having a single bond of 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, Radicals of saturated aliphatic functional groups, including cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, cycloalkyl-substituted alkyl groups.
- haloalkyl group or "halogenalkyl group” used in the present invention means an alkyl group substituted with halogen unless otherwise stated.
- heteroalkyl group used in the present invention means that one or more carbon atoms constituting the alkyl group are replaced by heteroatoms.
- alkenyl group alkenyl group "or” alkynyl group "used in the present invention has a double or triple bond of 2 to 60 carbon atoms, unless otherwise stated, and includes straight or branched chain groups. It is not limited to this.
- cycloalkyl as used in the present invention, unless stated otherwise, is from 3 to 60.
- Alkyl forming a ring with carbon number, but not limited thereto.
- alkoxy group used in the present invention are oxygen
- alkyl group having a radical attached refers to an alkyl group having a radical attached, and unless otherwise stated, has a carbon number of 1 to 60, but is not limited thereto.
- alkenoxyl group used in the present invention, or
- Alkenyloxy group means an alkenyl group to which oxygen radicals are attached, and unless otherwise stated, has a carbon number of 2 to 60, but is not limited thereto.
- aryloxyl group or "aryloxy group” used in the present invention is an oxygen radical.
- aryl group and arylene group used in the present invention have a carbon number of 6 to 60, but are not limited to each other, unless otherwise specified.
- the aryl group or arylene group is a single ring. Or aromatic rings of a multi-ring, including aromatic rings formed by neighboring substituents participating in a bond or reaction.
- the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
- aryl or "ar” means radicals substituted with an aryl group.
- an arylalkyl group is an alkyl group substituted with an aryl group
- an arylalkenyl group is an alkenyl group substituted with an aryl group
- substituted with an aryl group The radical has the number of carbons described in this specification.
- an aryl alkoxy group means an alkoxy group substituted with an aryl group, and an alkoxyl carbonyl group is substituted with an alkoxyl group.
- a carbonyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group, wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.
- heteroalkyl means an alkyl containing one or more heteroatoms, unless stated otherwise.
- Heteroaryl group or “heteroarylene group” is one or more of each, unless stated otherwise.
- a C2-C60 aryl group or arylene group containing a hetero atom, including, but not limited to, at least one of a single ring and a polycyclic ring, may be formed by combining adjacent functional groups.
- heterocyclic group used in the present invention includes one or more heteroatoms, having 2 to 60 carbon atoms, at least one of a single ring and a polycyclic ring, unless otherwise stated, and a heteroaliphatic group. Rings and heteroaromatic rings. Neighboring functional groups may be formed by binding.
- a “heterocyclic group” may also include a ring containing S0 2 instead of carbon forming a ring.
- a “heterocyclic group” includes the following compounds.
- aliphatic used in the present invention means aliphatic hydrocarbons having 1 to 60 carbon atoms
- aliphatic ring means aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
- ring used in the present invention is a carbon number of 3 to 60
- a fused ring consisting of an aliphatic ring or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof, including saturated or unsaturated rings.
- hetero compounds or heteroradicals other than the above-mentioned hetero compounds include, but are not limited to, one or more hetero atoms.
- carbonyl used in the present invention is represented by -COR ', where R' is hydrogen, an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 30 carbon atoms, or carbon number A cycloalkyl group of 3 to 30, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.
- ether used in the present invention is represented by -R-0-R ', wherein R or R' are independently hydrogen, alkyl groups having 1 to 20 carbon atoms, An aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
- Unsubstituted in “unsubstituted” is deuterium, halogen, amino group, nitrile group, nitro group, C, ⁇ C 20 alkyl group, C ⁇ . Alkoxyl group, d ⁇ c 20 alkylamine group, C: 20 alkyl Thiophene group, C 6
- One substituent ⁇ is bound to any one of the carbons forming the benzene ring, where a is an integer of 2 or 3, respectively, as follows, where R 1 may be the same or different from each other, and a is an integer of 4 to 6 In a similar manner to this, the bond to the carbon of the benzene ring is omitted, while the indication of hydrogen bonded to the carbon forming the benzene ring is omitted.
- meta position refers to the position of substitution of all substituents
- ortho position refers to the compound in which the position of the substituent is immediately neighboring.
- the meta position is the next substitution position of the immediate substitution position, and when benzene is used, it means 1 or 3 digits, and the pam position is
- the next substitution position of the meta position means 1 or 4 digits when benzene is used as an example.
- a more detailed example of a replacement location is shown below, ortho-,
- the meta- (meta-) position is replaced with a non-linear type, and the para- (para-) position is replaced with a linear type.
- the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer.
- An organic electric device characterized by comprising a first host compound represented by the following formula (1) and a second host compound represented by the following formula (2).
- X 1 is CR a R b or the following Chemical Formula 1-a
- X 2 and X 3 are independently of each other ⁇ - ⁇ 4 , 0, S, CR a R b or the formula 1-a, wherein the dashed line in the formula 1-a from X 2 or X 3 Represents the union of
- R a and R b are independently of each other hydrogen; C 6 -C 6 aryl group; Fluorenyl group; C 2 -C 60 containing at least one heteroatom selected from the group consisting of 0, N, S, Si and P Heterocyclic group; C 3 - C 6 o alicyclic and fused ring groups of the aromatic ring of the 60 -C; -C 50 alkyl group; It is selected from the group consisting of alkene diary of.
- h and i are integers of 0 or 1, except that h + i is 1 or more, where h or i is 0, which means a direct bond;
- Ar 1 , Ar 2 , Ar 3 and Ar 4 are independently of each other an aryl group of-.
- n is an integer of 1 or 2, and when n is 2, two Ar 1 are the same or
- U, L 2 and L 3 are independently a single bond; An arylene group of -C 60 ;
- f is an integer from 0 to 2
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently of each other hydrogen; deuterium; tritium;
- a plurality of R 2 blacks may combine with a plurality of R 3
- A, B, C, D, E and F are independently of each other C 6 -C 20 aryl group or C r C 20
- both ⁇ and F are substituted or unsubstituted C 6 aryl groups (phenyl groups), Wherein the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group, aryloxy group are each deuterium; A silane group substituted or unsubstituted with an alkyl group of ⁇ -0 or an aryl group of 20 ; a siloxane group; a boron group;
- C 3 -C 20 ⁇ cycloalkyl group The arylalkyl of C 7 -C 20 may be further substituted with one or more substituents selected from the group consisting of -C 20 arylalkenyl groups, and these substituents may combine with each other to form a ring, wherein the ring is a carbon number A fused ring consisting of 3 to 60 aliphatic rings or aromatic rings having 6 to 60 carbon atoms or heterocycles having 2 to 60 carbon atoms or a combination thereof, including saturated or unsaturated rings. ⁇
- the present invention provides a compound represented by the formula (1) and (2).
- L 1 , and L 3 of Chemical Formulas 1 and 2 are any of the following Chemical Formulas A-1 to A-13.
- Y is NL 4 -Ar 5 , 0, S, CR e R f or Formula 1-b
- L 4 is the same as the definition of L 3 ,
- Ar 5 is the same as the definition of Ar 4 ,
- R e and R f are the same as those defined for R a ,
- R 11 and R 12 are the same as those defined in R ',
- a ', c', d 'and e' are independently integers of 0 to 4, and b 'is 0 to 6
- h' is an integer of 0 to 2
- i ' is an integer of 0 or 1
- R 8 , R 9 and R 10 are independently of each other hydrogen; dihydrogen; tritium; halogen; cyano group; nitro group; C 6 -o aryl group; Fluorenyl group; C 2 -C 60 heterocycles containing at least one heteroatom selected from the group consisting of 0, N, S, Si and P; A C 2 -C 20 alkenyl;;.
- La is the same as the definition of 1 above, and Re and R «are the definitions of Re and R «.
- l ⁇ Z ⁇ Z 2 and Z 3 are independently CR 13 or N, and Z 1 , Z 2 3 ⁇ 4 Z 3 ⁇ at least
- Heteroaromatic rings can be formed. ⁇
- the present invention also provides an organic electronic device comprising a compound of which the first host compound represented by Chemical Formula 1 is any one of Chemical Formulas 1-1 to 1-5. [123] * Formula i_i Formula 1-2
- Y is NL 4 -Ar 5 , 0, S, CR e R f or Formula 1-b
- L 4 is the same as the definition of L 3 ,
- Ar 5 is the same as defined in Ar 4 ,
- R e and R f are the same as those defined in R a ,
- R "and R 12 are the same as those defined in R 1 ,
- a ', c' and d ' are independently integers of 0 to 4
- f and g' are independently integers of 0 to 3
- h ' is 0 to 2 integers
- R 9 are each independently hydrogen; deuterium; tritium; halogen; cyano group; nitro group; C 6 -aryl group; Fluorenyl group C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of 0, N, S, Si and P; A fused ring group of a C 3 -C 60 aliphatic ring and a C 6 -C 60 aromatic ring, a -C ⁇ alkyl group, a C 2 -C 20 alkenyl group; An alkynyl group of C 2 -C 20 ; C, -C 30 uial cock group; An aryloxy group of 30 ; and -N (R c ) (R «); or a ', c', d ', f and g' are 2 or more and h ' 2 is the same as or different from each other, and a plurality of Rs or a plurality of R 9s or neighboring R 8 and
- the first host compound represented by the formula 1 It includes the compound represented by any one of 1-6 to 1-20.
- R a , R b , R 1 , R 2 , R 3 , R 4 , a, b, c, d, L ', Ar 1 , Ar 2 and n are as defined above
- A, B, C and D are C 10 aryl groups.
- the present invention is the first host compound represented by the formula 1
- W is N- ⁇ 6 , 0, S, CR g R h or the following formula 1-c,
- L 5 is the same as the definition of L 3
- Ar 6 is the same as the definition of Ar 4 .
- R g and R h are the same as in the above definition
- R 15 and R 16 are the same as those defined in R 1 ,
- R 13 and R 14 are each independently hydrogen; deuterium; tritium; halogen; cyano group; A nitro group; an aryl group of C 6 -C 60; fluorene group;. 0, N, S, a heterocyclic C 2 -C 6 containing at least one heteroatom selected from the group consisting of Si and P group; A fused ring of an aliphatic ring of C 3 -C 60 and an aromatic ring of ⁇ -0 ; an alkyl group of c r c 5 .
- An organic electronic device comprising.
- An organic electronic device comprising a compound of the formula n when n is 2.
- an organic electronic device comprising the compound represented by any one of the following A, B, C, D, E and F of Formulas B-1 to B-7. [173] Formula Bl Formula B-2 Formula B-3 Formula B-4
- Z 4 to Z 51 are CR i or N,
- R i is the same as the definition of R a ,
- the present invention includes a compound represented by Formula 2 or Formula 4 below, a second host compound represented by Formula 2.
- E, F, R 5 , R 6 , R 7 , e, f, g, L 2 , Ar 3 , X 2 and X 3 are as defined above. ⁇
- the present invention also provides an organic electric device characterized in that R 6 of Formula 2 necessarily forms an aromatic ring or a heteroaromatic ring.
- It includes a compound represented by any one of 5-1 to 5-24.
- R 5 , R 6 , R 7 , e, f, g, ⁇ Ar 3 , X 2 and X 3 are as defined above. ⁇
- the second host compound represented by the formula 2 includes a compound selected from the group consisting of the following formulas 6-1 to 6-8.
- the first host compound represented by Chemical Formula 1 includes a compound represented by any one of the following Compounds 1 ′ 1 to 1-70 and Compounds 2-1 to 2-115.
- the second host compound represented by Chemical Formula 2 in the present invention includes a compound represented by any one of the following Compounds 3-1 to 3-115.
- the organic electronic device 100 includes a first electrode 120, a second electrode 180, and a first electrode 120 and a second electrode formed on a substrate 110.
- An organic layer comprising a compound represented by Formula 1 is provided between the electrodes 180.
- the first electrode 120 may be an anode (anode)
- the second electrode 180 may be a cathode (cathode)
- inverted In the case of the mold, the first electrode 120 may be a cathode and the second electrode 180 may be an anode.
- the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 sequentially on the first electrode 120. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
- the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the electron transport auxiliary layer, the buffer layer 141, etc. may be further included, and the electron transport layer may be further included. (160) may serve as a hole blocking layer.
- the organic electronic device according to the present invention may further include a protective layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
- the band gap, the electrical characteristics and the interfacial characteristics can be different depending on where the coupling is attached to even the same core.
- the combination is also very important, especially when the optimal combination of energy i eve i and T1 values between each organic layer and the material's inherent properties (mobility, interfacial properties, etc.) can be achieved at the same time.
- An organic electroluminescent device is PVD (physical vapor).
- an electron transport layer (160) and an electron injection layer (170) can be produced by forming an organic layer containing thereon and depositing a material usable as a cathode thereon.
- An electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
- the hole transport band layer includes a hole transport layer, a light emitting auxiliary layer or both, the hole transport band layer is Contains a compound represented by the formula (1) Organic electric devices can be provided
- the present invention provides a light efficiency improvement layer formed on at least one of the one side of the side of the first electrode in the organic electrical device which is opposite to the organic material layer or the one side of the second electrode is opposite to the organic material layer. It provides an organic electric device further comprising.
- the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a two-roll process, and the organic layer according to the present invention can be formed in various ways. Therefore, the scope of the present invention is not limited by the method of formation.
- the present invention provides an organic electroluminescent device comprising a compound represented by Formula 1 and Formula 2 in any one ratio of 1: 9 to 9: 1 in the light emitting layer of the organic layer is included in the light emitting layer.
- the present invention is an organic electrical device characterized in that the compound represented by the formula (1) and the formula (2) in the light emitting layer of the organic layer is mixed in any one ratio of 1: 9 or 5: 5 to be used in the light emitting layer More preferably, the compounding ratio of the compound represented by Chemical Formula 1 and Chemical Formula 2 is included in the light emitting layer at 2: 8 or 3: 7.
- It may be a luminescent type, a back emitting type or a double emitting type.
- the White Organic Light Emitting Device has the advantage of being able to be manufactured using the color filter technology of existing LCDs, while being easy to achieve high resolution and excellent fairness.
- Various structures have been proposed and patented. Representatively, R (Red), G (Green), and B (Blue) light emitting parts are arranged side-by-side in parallel with each other. There is a stacking method that is stacked up and down, and the electroluminescence by the blue (B) organic light emitting layer and the light from the inorganic phosphor are used.
- CCM color conversion material
- the present invention also provides an electronic device comprising a display device including the organic electric element described above; and a control unit for driving the display device.
- the present invention provides an electronic device characterized by at least one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white light emitting device.
- the electronic device may be a current or future wired and wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
- Compounds belonging to Sub 1 may be, but are not limited to, the following compounds.
- Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 1.
- Sub 1-1 Sub 1-2 Sub 1-3 Sub 1-4 Sub 1-5 Sub 1- «Sub 1-7 Sub 1-8 Sub 1-9
- Compounds belonging to Sub 2 may be, but are not limited to, the following compounds.
- Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 2.
- Sub 1-42 (12.00 g, 29.93 mmol) obtained in the above synthesis was added to Sub 2-14 (10.58 g, 32.93 mmol), Pd 2 (dba) 3 (0.82 g, 0.90 mmol), and P (i-Bu. ) 3 (0.36 g, 1.80 mmol), NaOr-Bu (8.63 g, 89.80 mmol) and toluene (315 ml) were added, and 14.78 g (yield: 72%) of the product was obtained using the 1-1 synthesis method.
- Sub 1-66 (12.70 g, 31.68 mmol) obtained in the above synthesis was added with Sub 2-82 (11.69 g, 34.85 mmol), Pd 2 (dba) 3 (0.87 g, 0.95 mmol), and P (i-Bu. ) 3 (0.38 g, 1.90 mmol), NaOt-Bu (9.13 g, 95.03 mmol) and toluene (330 ml) were added, and 14.41 g (yield: 65%) of the product was obtained using the 1-1 synthesis method.
- Sub 1-78 (12.40 g, 27.50 mmol) obtained in the above synthesis was added with Sub 2-38 (10.15 g, 30.25 mmol), Pd 2 (dba) 3 (0.76 g, 0.82 mmol), and P (i-Bu. ) 3 (0.33 g, 1.65 mmol), NaOi-Bu (7.93 g, 82.49 mmol) and toluene (290 ml) were added to give 14.23 g (yield: 69%) of the product using the 1-1 synthesis method.
- Sub 1-73 (13.25 g, 25.91 mmol) obtained in the above synthesis was added to Sub 2-7 (13.98 g, 56.99 mmol), Pd 2 (dba) 3 (1.42 g, 1.55 mmol), and P (t-Bu. ) 3 (0.06 g, 0.31 mmol), NaOr-Bu (14.94 g, 155.44 mmol) and toluene (415 ml) were added and 13.72 g (yield: 57%) of the product was obtained using the 1-1 synthesis method.
- Sub 1-75 (15.00 g, 23.90 mmol) obtained in the above synthesis was added to Sub 2-11 (7.77 g, 26.29 mmol), Pd 2 (dba) 3 (0.66 g, 0.72 mmol), and P (i-Bu. ) 3 (0.29 g, 1.43 mmol), NaOi-Bu (6.89 g, 71.70 mmol) and toluene (250 ml) were added and 12.28 g (yield: 61%) of the product was obtained using the 1-1 synthesis method.
- the compound represented by Chemical Formula 2 (final product 2) is synthesized by repeating Sub 3 and Sub 4 as shown in Reaction Formula 4 below, but is not limited thereto.
- E, F, R 5 , R 6 , R 7 , e, f, g, h, i, U, Ar 3 , X 2 and X 3 are the same as defined in Formula 2, Hal 1 is Br or C1 .
- Sub 3 of Reaction Equation 4 above may be synthesized by the reaction path of Reaction Equation 5 below, but is not limited thereto.
- Carbazole derivatives the starting materials used in the synthesis of Sub 3-1-1, are disclosed in Korean Patent No. 10-1535606 (published Jul. 3, 2015).
- Fluorene derivative the starting material used in the synthesis of Sub 3-1-1, is disclosed in Korean Patent Application No. 2013-0056221 (filed on May 20, 2013) and Korean Patent Application No. 2015-0083505 (Jun. 12, 2015) It was manufactured by the synthesis method disclosed in
- Compounds belonging to Sub 3 may be the following compounds, but are not limited thereto.
- Table 4 shows FD-MS (Field Desorption-Mass) of some compounds belonging to Sub 3.
- Sub 3-1 Sub 3-2 Sub 3-3 Sub 3-4 Sub 3-5 Sub 3-6 Sub 3-7 Sub 3-8
- Sub 4 of the reaction formula 4 may be synthesized by the reaction route of the reaction formula 6, but is not limited thereto, wherein Hal 1 and Hal 2 are Br or C1.
- Sub 3-1 (10.35 g, 27.06 mmol) obtained in the above synthesis was dissolved in toluene (285 ml) in a round bottom flask, and Sub 4-1 (CAS Registry Number: 108-86-1) (4.67 g, 29.77 mmol), Pd 2 (dba) 3 (0.74 g, 0.81 mmol), P (i-Bu) 3 (0.33 g, 1.62 mmol), NaOi-Bu (7.80 g, 81.18 mmol) and added at 100 ° C.
- Sub 3-54 (9.27 g, 21.43 mmol) obtained in the above synthesis was added to Sub 4-12 (CAS Registry Number: 97511-04-1) (6.20 g, 23.58 mmol), Pd 2 (dba) 3 (0.59). g, 0.64 mmol) P (r-Bu) 3 (0.26 g, 1.29 mmol), NaO / -Bu (6.18 g, 64 ⁇ 30 mmol) and toluene (225 ml) were added and the above 3-1 synthesis method was used. 9.09 g (yield 69%) of product were obtained.
- Sub 3-13 (9.14 g, 24.47 mmol) obtained in the above synthesis was added to Sub- 2 7 (CAS Registry Number: 80984-79-8) (8.40 g, 26.92 mmol) and Pd 2 (dba) 3 (0.67). g, 0.73 mmol) P (i-Bu) 3 (0.30 g, 1.47 mmol), NaOt-Bu (7.06 g, 73.42 mmol) and toluene (260 ml) were added and the product 10.21 g was obtained using the 3-1 synthesis method. (Yield 69%) was obtained.
- NPB N, N'-Bis (l-naphthalenyl) -N, N'-bis-phenyl- (l, l'-biphenyl) -4,4'-diamine
- a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping [bis- (l-phenylisoquinolyl) iridium (m) acetylacetonate] at 5% by weight.
- As a hole blocking layer ( ⁇ , ⁇ -bisphenyl) -4-oleito ) Bi- (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm and used as an electron transport layer.
- Bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviated as BeBq 2 hereinafter) was deposited to a thickness of 50 nm. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm with an electron injection layer, followed by A1. Is deposited to a thickness of 150 nm
- the organic electroluminescent element was manufactured by using it.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used alone as a host.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used alone as a host.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used alone as a host.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 4 was used alone as a host.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 2 were mixed and used as a host.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 and Comparative Compound 4 were used as a host.
- the electroluminescence (EL) characteristics were measured with the PR-650 (photoresearch), and T95 life was measured using McScience's life measurement equipment at 2500 cd / m 2 standard luminance. The results are shown in Table 7.
- Comparative Example 1 to Comparative Example 7 wherein the compound of the present invention, the comparative compound 1 to the comparative compound 4, represented by the formula (2) is used alone as a phosphorescent host, the compound of the present invention (3-6, 3-61) , Comparative Examples 1 to 3 using 3-74) showed higher efficiency and longer life than Comparative Examples 4 to 7 using comparative compounds.
- Comparative Example 8 and Comparative Example 9 which were used as phosphorescent hosts by comparing Comparative Compound 2 or Comparative Compound 3 and Comparative Compound 4, showed higher efficiency. Comparing Comparative Example 8 and Comparative Example 9, it is possible to compare the five rings having the same nitrogen atom.
- the present inventors judge that a substance having a compound of Chemical Formula 1 and a Chemical Formula 2 has a new characteristic other than that for each substance.
- PL lifetime was measured by using the compound of the present invention and the compound of the present invention.
- the compound of the present invention (1) and (2) were mixed, it was confirmed that a new PL wavelength was formed unlike the compound alone. It was found that the decrease and extinction time of the formed PL wavelength increased from about 60 times to as much as about 360 times less than the reduction and extinction time of the materials of Formula 1 and Formula 2, respectively.
- the combination of the present invention is superior to 9 because the polycyclic compound represented by Chemical Formula 1, which is characterized by not only electrons but also hole stability and high T1, is represented by Chemical Formula 1.
- the T1 and the high LUMO energy values improve the electron blocking ability, allowing more holes to move quickly and easily in the light emitting layer, which increases the charge balance in the light emitting layer of holes and electrons, resulting in better light emission inside the light emitting layer rather than the hole transport layer. It is also judged that the degradation of the HTL interface is also reduced, thereby maximizing the driving voltage, efficiency and lifetime of the entire device.
- An organic electroluminescent device was manufactured in the same manner as in Example 68, except that the mixing cost of the materials was used differently as described in Table 8.
- An organic electroluminescent device was manufactured in the same manner as in Example 9, except that the mixing cost of the materials was used differently as described in Table 8.
- the electroluminescence (EL) characteristics were measured with the PR-650 (photoresearch), and the T95 life was measured using the McScience Life Measurement Equipment at 2500 cd / m 2 reference luminance. The results are shown in Table 8.
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Abstract
본 발명에 따른 화합물의 혼합물을 인광 호스트 물질로 이용함으로써, 유기전기소자의 높은 발광효율, 낮은 구동전압을 달성할 수 있으며, 또한 소자의 수명을 크게 향상시킬 수 있는 유기전기소자 및 그 전자장치를 제공한다.
Description
명세서
발명의명칭:유기전기소자용화합물，이를이용한유기전기소자 및그전자장치
기술분야
[I] 본발명은유기전기소자용화합물,이를이용한유기전기소자및그전자
장치에관한것이다.
배경기술
[2] 일반적으로유기발광현상이란유기물질올이용하여전기에너지를
빛에너지로전환시켜주는현상을말한다.유기발광현상을이용하는 유기전기소자는통상양극과음극및이사이에유기물층을포함하는구조를 가진다.여기서유기물층은유기전기소자의효율과안정성을높이기위하여 각기다른물질로구성된다층의구조로이루어진경우가많으며 ,예컨대 정공주입층,정공수송층,발광층，전자수송층및전자주입층등으로이루어질수 있다.
[3] 유기전기소자에서유기물층으로사용되는재료는기능에따라，발광재료와 전하수송재료，예컨대정공주입재료,정공수송재료，전자수송재료，전자주입 재료등으로분류될수있다.
[4] 헤테로원자를포함하고있는다환고리화합물의경우물질구조에따른특성의 차이가매우커서유기전기소자의재료로다양한층에적용되고있다.
[5] 특히환의개수및 fused위치,헤테로원자의종류와배열에따라밴드
갭 (HOMO, LUMO),전기적특성，화학적특성，물성등이상이한특징을갖고 있어，이를이용한다양한유기전기소자의층에대한적용개발이진행되어 왔다.
[6] 그대표적인예로하기특허문헌 1내지특허문헌 5에서는다환고리화합물중
5환고리화합물에대해헤테로종류및배열,치환기종류, fused위치둥에따른 성능을보고하고있다.
[7] [특허문헌 1]：미국둥록특허 5843607
[8] [특허문헌 2]：일본공개특허 1999-162650
[9] [특허문헌 3] :한국공개특허 2008-0085000
[10] [특허문헌 4]：미국공개특허 2010-0187977
[II] [특허문헌 5]：한국공개특허 2011-0018340
[12] [특허문헌 6]：한국공개특허 2009-0057711
[13] 특허문헌 1및특허문헌 2는 5환고리화합물내헤테로원자가질소 (N)로만 구성된인돌로카바졸코어를사용하였으며 ,인돌로카바졸의 N에치환또는 비치환된아릴기를사용한실시예를보고하고있다.하지만상기선행발명 1의 경우치환기로알킬기，아미노기，알콕시기등이치환또는비치환된단순
아릴기만존재하여다환고리화합물의치환기효과에대해서입증하기에는 매우부족하였으며，정공수송재료로서의사용만기재되어 있고，인광호스트 재료로서의사용은기재되어 있지않았다.
[14] 특허문헌 3및특허문헌 4는상기특허문헌 1및특허문헌 2와동일한 5환
고리화합물내헤테로원자가 N인인돌로카바졸코어에각각아릴기와 N을 함유하는피리딘，피리미딘，트리아진등이치환된화합물을기재하고있지만, 인광그린호스트물질에대한사용예만기재되어 있으며,인돌로카바졸코어에 치환되는다른헤테로고리화합물에대한성능에대해서는기재되어 있지 않았다.
[15] 특허문헌 5는 5환고리화합물내헤테로원자를질소 (N),산소 (0)，황 (S),탄소 등이기재되어 있으나，성능측정 데이터에는모두서로동일한동형
헤테로원자를사용한실시예만존재하여，이형헤테로원자를포함하는 5환 고리화합물의성능적특성을확인할수없었다.
[16] 따라서상기특허문헌에서는동형헤테로원자를포함하는 5환고리화합물이 갖는낮은전하캐리어 이동도및낮은산화안정성에대한해결방안이 기재되어있지않았다.
[17] 5환고리화합물분자가일반적으로적층될때,인접한 π-전자가많아짐에따라 강한전기적상호작용을갖게되는데，이는전하캐리어 이동도와밀접한연관이 있으며，특히 N-N type인동형의 5환고리화합물은분자가적층될때,분자간의 배열순서가 edge-to-face형태를갖게되는반면,헤테로원자가서로다른이형의 5환고리화합물은분자의패킹구조가역방향으로마주보는파이 -적층 구조 (antiparallelcofacial π-stacking structure)를가져분자간의배열순서가 face-to-face형태를갖게된다.이적층구조의원인인비대칭으로배치된 헤테로원자 N에치환되는치환기의 입체효과로인하여상대적으로높은캐리어 이동도및높은산화안정성을야기시킨다고보고되었다. (Org. Lett. 2008, 10, 1199)
[18] 특허문헌 6에서는 7환이상의다양한다환고리화합물에 대하여형광호스트 물질로사용한예가보고되었다.
[19] 상기내용과같이다환고리화합물에대한 fused위치및고리개수，
헤테로원자의배열,종류에따른특성변화에대해서는아직도개발이층분히 이루어지지않은상태이다.
[20] 특히 인광발광도펀트재료를이용하는인광형유기전기소자에 있어서호스트 물질의 LUMO및 HOMO level은유기전기소자의효율및수명에매우큰영향을 주는요인으로서 이는발광층내전자및정공주입을효율적으로조절 가능하냐에따라발광층내 charge balance조절,도펀트뒌칭 (quenching)및 정공수송층계면에서의발광으로인한효율저하및수명저하를방지할수있기 때문이다.
[21] 형광및인광발광용호스트물질의경우최근들어 TADF(Thermal activated
delayed fluorescent), Exciplex등을이용한유기전기소자의효율증가및수명 증가등을연구하고있으며,특히호스트물질에서도펀트물질로의에너지전달 방법규명에많은연구가진행되고있다.
[22] TADF (Thermal activated delayed fluorescent), exciplex에 대한발광층내에너지 전달규명은여러가지방법들이 있지만, PL lifetime (TRTP)측정법으로손쉽게 확인할수있다.
[23] TRTP (Time resolved transient PL)측정법은필스광원을호스트박막에조사한 후,시간에따른스펙트럼의감소 (Decay time)를관찰하는방식으로서에너지 전달및발광지연시간관찰올통해에너지전달방식을규명할수있는 측정방법이다.상기 TRTP측정은형광과인광의구분및 mixed호스트물질 내에서의에너지전달방식 , exciplex에너지전달방식， TADF에너지전달방식 등을구분해즐수있는측정법이다.
[24] 이처럼호스트물질로부터도편트물질로에너지가전달되는방식에따라효율 및수명에영향을주는다양한요인들이존재하며，물질에따라에너지전달 방식이상이하여，아직까지안정되고효율적인유기전기소자용호스트재료의 개발이충분히이루어지지않은상태이다.따라서새로운재료의개발이 계속 요구되고있으며，특히발광층의호스트물질에대한개발이 절실히요구되고 있다.
발명의상세한설명
기술적과제
[25] 본발명은상기와같은인광호스트물질의문제점을해결하기위하여 제안된 것으로,인광도편트를포함하는인광발광형유기전기소자의호스트물질에 대한 HOMO level조절을통한발광층내 charge balance조절및효율，수명을 향상시킬수있는화합물,이를이용한유기전기소자및그전자장치를 제공하는것을목적으로한다ᅳ
과제해결수단
[26] 본발명은인광발광형유기전기소자의발광층내효율적인정공주입을
조절하기위해주성분으로서특정의제 1호스트재료에특정의제 2호스트 재료를조합하여 함유함으로써,발광층과인접층의에너지장벽을작게할수 있고,발광층내 charge balance를최대화시켜유기전기소자의고효율，고수명을 제공하는것이다.
[27] 본발명은제 1전극，제 2전극및상기제 1전극과상기제 2전극사이에형성된 유기물층을포함하는유기전기소자에 있어서，상기유기물층은，발광층을 포함하고,상기발광층은하기화학식 1로표시되는제 1호스트화합물및하기 화학식 2로표시되는제 2호스트화합물을포함하는것을특징으로하는 유기전기소자를제공한다.
[28] 화학식 1화학식 2
[29]
[30] 또한，본발명은상기화학식들로표시되는화합물을이용한유기전기소자및 그전자장치를제공한다.
발명의효과
[31] 본발명에따른혼합물을인광호스트물질로이용함으로써,유기전기소자의 높은발광효율，낮은구동전압을달성할수있으며，또한소자의수명을크게 향상시킬수있다.
도면의간단한설명
[32] 도 1은본발명에따른유기전기발광소자의 예시도이다.
[33] 100 :유기전기소자 110 :기판
[34] 120：제 1전극 (양극) 130：정공주입층
[35] 140：정공수송층 141：버퍼층
[36] 150：발광층 151：발광보조층
[37] 160：전자수송층 170：전자주입층
[38] 180：제 2전극 (음극)
발명의실시를위한형태
[39] 이하，본발명의실시예를참조하여상세하게설명한다.본발명을설명함에 있어，관련된공지구성또는기능에대한구체적인설명이본발명의요지를 흐릴수있다고판단되는경우에는그상세한설명은생략한다.
[40] 또한，본발명의구성요소를설명하는데있어서，제 1，제 2， A, B, (a),(b)등의 용어를사용할수있다 이러한용어는그구성요소를다른구성요소와 구별하기위한것일뿐，그용어에의해해당구성요소의본질이나차례또는 순서등이한정되지않는다.어떤구성요소가다른구성요소에 "연결 "， "결합" 또는 "접속"된다고기재된경우，그구성요소는그다른구성요소에직접적으로 연결되거나또는접속될수있지만,각구성요소사이에또다른구성요소가 "연결 "， "결합"또는 "접속 "될수도있다고이해되어야할것이다.
[41] 본명세서및첨부된청구의범위에서사용된바와같이,달리언급하지않는 한,하기용어의의미는하기와같다.
[42] 본명세서에서사용된용어 "할로"또는 "할로겐"은다른설명이없는한
불소 (F),브롬 (Br),염소 (C1)또는요오드 (I)이다.
[43] 본발명에사용된용어 "알킬"또는 "알킬기 "는다른설명이없는한 1내지
60의탄소수의단일결합을가지며，직쇄알킬기,분지쇄알킬기,
사이클로알킬 (지환족)기,알킬-치환된사이클로알킬기,사이클로알킬-치환된 알킬기를비롯한포화지방족작용기의라디칼을의미한다.
[44] 본발명에사용된용어 "할로알킬기"또는 "할로겐알킬기"는다른설명이 없는 한할로겐으로치환된알킬기를의미한다.
[45] 본발명에사용된용어 "헤테로알킬기 "는알킬기를구성하는탄소원자증하나 이상이해테로원자로대체된것을의미한다.
[46] 본발명에사용된용어 "알켄일기 "알케닐기"또는 "알킨일기"는다른설명이 없는한각각 2내지 60의탄소수의 이중결합또는삼중결합을가지며，직쇄형 또는측쇄형사슬기를포함하며，여기에제한되는것은아니다.
[47] 본발명에사용된용어 "시클로알킬 "은다른설명이없는한 3내지 60의
탄소수를갖는고리를형성하는알킬을의미하며，여기에제한되는것은아니다.
[48] 본발명에사용된용어 "알콕실기 ", "알콕시기 "，또는 "알킬옥시기"는산소
라디칼이부착된알킬기를의미하며，다른설명이없는한 1내지 60의탄소수를 가지며 ,여기에제한되는것은아니다.
[49] 본발명에사용된용어 "알켄옥실기 ", "알켄옥시기 ", "알켄일옥실기 ",또는
"알켄일옥시기 "는산소라디칼이부착된알켄일기를의미하며，다른설명이 없는한 2내지 60의탄소수를가지며,여기에제한되는것은아니다.
[50] 본발명에사용된용어 "아릴옥실기"또는 "아릴옥시기 "는산소라디칼이
부착된아릴기를의미하며 ,다른설명이없는한 6내지 60의탄소수를가지며， 여기에제한되는것은아니다.
[51] 본발명에사용된용어 "아릴기"및 "아릴렌기"는다른설명이없는한각각 6 내지 60의탄소수를가지며,이에제한되는것은아니다.본발명에서아릴기 또는아릴렌기는단일고리또는다중고리의방향족을의미하며，이웃한 치환기가결합또는반웅에참여하여형성된방향족고리를포함한다.예컨대， 아릴기는페닐기,비페닐기,플루오렌기,스파이로플루오렌기일수있다.
[52] 접두사 "아릴"또는 "아르 "는아릴기로치환된라디칼을의미한다.예를들어 아릴알킬기는아릴기로치환된알킬기이며,아릴알켄일기는아릴기로치환된 알켄일기이며，아릴기로치환된라디칼은본명세서에서설명한탄소수를 가진다.
[53] 또한접두사가연속으로명명되는경우먼저기재된순서대로치환기가
나열되는것을의미한다.예를들어,아릴알콕시기의경우아릴기로치환된 알콕시기를의미하며，알콕실카르보닐기의 경우알콕실기로치환된
카르보닐기를의미하며，또한아릴카르보닐알켄일기의경우아릴카르보닐기로 치환된알켄일기를의미하며여기서아릴카르보닐기는아릴기로치환된 카르보닐기이다.
[54] 본명세서에서사용된용어 "헤테로알킬 "은다른설명이없는한하나이상의 헤테로원자를포함하는알킬을의미한다.본발명에사용된용어
"헤테로아릴기"또는 "헤테로아릴렌기"는다른설명이없는한각각하나이상의
헤테로원자를포함하는탄소수 2내지 60의아릴기또는아릴렌기를의미하며, 여기에제한되는것은아니며，단일고리및다증고리중적어도하나를 포함하며，이웃한작용기기가결합하여형성될수도있다.
[55] 본발명에사용된용어 "헤테로고리기"는다른설명이없는한하나이상의 헤테로원자를포함하고, 2내지 60의탄소수를가지며,단일고리및다중고리 중적어도하나를포함하며，헤테로지방족고리및헤테로방향족고리를 포함한다.이웃한작용기가결합하여형성될수도있다.
[56] 본명세서에서사용된용어 ' '헤테로원자"는다른설명이없는한 N, 0, S, P 또는 Si를나타낸다.
[57] 또한 "헤테로고리기"는고리를형성하는탄소대신 S02를포함하는고리도 포함할수있다.예컨대, "헤테로고리기"는다음화합물을포함한다.
[59] 다른설명이없는한，본발명에사용된용어 "지방족' '은탄소수 1내지 60의 지방족탄화수소를의미하며， "지방족고리"는탄소수 3내지 60의지방족 탄화수소고리를의미한다.
[6이 다른설명이없는한，본발명에사용된용어 "고리 "는탄소수 3내지 60의
지방족고리또는탄소수 6내지 60의방향족고리또는탄소수 2내지 60의 헤테로고리또는이들의조합으로이루어진융합고리를말하며，포화또는 불포화고리를포함한다.
[61] 전술한헤테로화합물이외의그밖의다른헤테로화합물또는헤테로라디칼은 하나이상의헤테로원자를포함하며,여기에제한되는것은아니다ᅳ
[62] 다른설명이없는한，본발명에사용된용어 "카르보닐"이란 -COR'로표시되는 것이며，여기서 R'은수소，탄소수 1내지 20의알킬기 ,탄소수 6내지 30의 아릴기，탄소수 3내지 30의사이클로알킬기,탄소수 2내지 20의알켄일기, 탄소수 2내지 20의알킨일기,또는이들의조합인것이다.
[63] 다른설명이없는한,본발명에사용된용어 "에테르"란 -R-0-R'로표시되는 것이며,여기서 R또는 R'은각각서로독립적으로수소,탄소수 1내지 20의 알킬기,탄소수 6내지 30의아릴기，탄소수 3내지 30의사이클로알킬기，탄소수 2내지 20의알켄일기，탄소수 2내지 20의알킨일기，또는이들의조합인것이다.
[64] 또한명시적인설명이없는한，본발명에서사용된용어 "치환또는
비치환된"에서 "치환"은중수소，할로겐，아미노기，니트릴기,니트로기 , C,~C20 의알킬기, C^ 。의알콕실기, d~c20의알킬아민기， C :20의알킬티오펜기, C6
~C2。의아릴티오펜기， C2~C20의알켄일기， C2~C2。의알킨일기, ~C20의
시클로알킬기, C6~C20의아릴기，중수소로치환된 C6~C20의아릴기, C8~C20의 아릴알켄일기，실란기，붕소기，게르마늄기및 C2~C20의헤테로고리기로
이루어진군으로부터선택되는 1개이상의치환기로치환됨을의미하며，이들 치환기에제한되는것은아니다.
[65] 또한명시적인설명이없는한，본발명에서사용되는화학식은하기화학식의 지수정의에의한치환기정의와동일하게적용된다.
[67] 여기서， a가 0의정수인경우치환기 R1은부존재하며， a가 1의정수인경우
하나의치환기 ^은벤젠고리를형성하는탄소중어느하나의탄소에결합하며 a가 2또는 3의정수인경우각각다음과같이결합하며이때 R1은서로 동일하거나다를수있으며, a가 4내지 6의정수인경우이와유사한방식으로 벤젠고리의탄소에결합하며，한편벤젠고리를형성하는탄소에결합된수소의 표시는생략한다.
(a=2) <a=3
[69] 또한명시적인설명이없는한，본발명에서사용된용어 "오소 (ortho)",
"메타 (meta)", "파라 (para)"는모든치환기의치환위치를뜻하며，오소 (ortho) 위치란치환기의위치가바로이웃하는화합물을나타내고，일예로벤젠일경우 1， 2자리를뜻하고,메타 (meta)위치란바로이웃치환위치의다음치환위치를 나타내며벤젠을예시로했을때 1， 3자리를뜻하며，파라 (pam)위치란
메타 (meta)위치의다음치환위치로써 벤젠을예시로했을때 1, 4자리를뜻한다. 보다상세한치환위치 예에대한설명은하기와같고,오소 -(ortho-),
메타 -(meta-)위치는 non-linear한 type,파라 -(para-)위치는 linear한 type으로 치환됨을확인할수있다.
[70] [ortho-위치의 예시]
[72] [meta-위치의 예시]
[74] [para-위치의 예시]
[76] 이하，본발명의 일측면에따른화합물및이를포함하는유기전기소자에
대하여설명한다.
[77] 본발명은제 1전극，제 2전극및상기제 1전극과상기제 2전극사이에형성된 유기물층을포함하는유기전기소자에 있어서，상기유기물층은발광층을 포함하고，상기발광층은인광성발광층으로서하기화학식 1로표시되는제 1호스트화합물및하기화학식 2로표시되는제 2호스트화합물을포함하는 것을특징으로하는유기전기소자를제공한다.
[78] 화학식 1화학식 2
[79]
[80] {상기화학식 1및화학식 2에서,
[81] 1) X1은 CRaRb또는하기화학식 1-a이고
[82] 화학식 1-a
[84] 상기화학식 1-a에서，점선은 Χΐ으로부터의결합을나타내며，
[85] 2) X2및 X3은서로독립적으로 Ν-ΙΛΑΓ4, 0, S, CRaRb또는상기화학식 1-a이며 , 이때상기화학식 1-a에서점선은 X2또는 X3으로부터의결합을나타내고,
[86] 3) Ra및 Rb는서로독립적으로수소; C6-C6。의아릴기；플루오렌일기； 0, N, S, Si 및 P로이루어진군에서선택된적어도하나의해테로원자를포함하는 C2-C60의
헤테로고리기； C3- o의지방족고리와 C6-C60의방향족고리의융합고리기； -C50 의알킬기; - 。의알켄일기;로이루어진군에서선택되며，
[87] 4) h및 i는 0또는 1의정수이고，단， h+i는 1이상이며 ,여기서 h또는 i가 0일 경우는직접결합을의미하고,
[88] 5) Ar1, Ar2, Ar3및 Ar4는서로독립적으로 - 。의아릴기； 0, N, S, Si및 P로 이루어진군에서선택된적어도하나의헤테로원자를포함하는 C2-C60의 헤테로고리기；플루오렌일기; C6- 。의방향족고리와 C3-C6。의지방족고리의 융합고리기; CrC50의알킬기; C2-C20의알켄일기; C2-C2。의알킨일기; d-C30의 알콕실기; C6-C30의아릴옥시기;및 -La-N(Rc)(Rd);로이루어진군에서선택되고, (여기서상기 La는단일결합; C6-C60의아릴렌기 ;플루오렌일렌기 ; 0, N, S, Si및 Ρ 중적어도하나의헤테로원자를포함하는 C2-C60의헤테로고리기; C3-C60의 지방족고리와 C6-C6。의방향족고리의융합고리기;및지방족탄화수소기로 이루어진군에서선택되며,상기 Rc및 Rd는서로독립적으로 C6-C60의아릴기; 플루오렌일기 ; 0, N, S, Si및 P로이루어진군에서선택된적어도하나의 헤테로원자를포함하는 C2-C60의헤테로고리기; -C6。의지방족고리와 C6-C60의 방향족고리의융합고리기;로이루어진군에서선택됨)
[89] 6)또한 Ari과 Ar2는서로결합하여고리를형성할수있고,
[90] 7) n은 1또는 2의정수이며， n이 2일경우 2개의 Ar1은각각동일하거나
상이하고, 2개의 Ar2는각각동일하거나상이하며,
[91] 8) U, L2및 L3은서로독립적으로단일결합; -C60의아릴렌기 ;
플루오렌일렌기； 0, N, S, Si및 P중적어도하나의헤테로원자를포함하는 C2-C6C 의헤테로고리기; C3-C60의지방족고리와 C6-C6。의방향족고리의융합고리기;및 지방족탄화수소기；로이루어진군에서선택되며，
[92] 9) 3，1)， (：， 6및 는서로독립적으로 0내지 10의정수이고， d는 0내지 5의
정수이고, f는 0내지 2의정수이며,
[93] 10) R1, R2, R3, R4, R5, R6및 R7은서로독립적으로수소;중수소;삼증수소;
할로겐;시아노기;나이트로기; C6-C60의아릴기;플루오렌일기； 0, N, S, Si및 P로 이루어진군에서선택된적어도하나의헤테로원자를포함하는 C2-C60의 헤테로고리기; c3-c6。의지방족고리와 c6-c60의방향족고리의융합고리기; d-C50 의알킬기； c2-c2。의알켄일기； CrC20의알킨일기； CrC30의알콕실기； C6-C30의 아릴옥시기；및 -La-N(Rc)(Rd);로이루어진군에서선택되고,또는상기 a, b, c, d, e 및 g가 2이상인경우및 f가 2인경우는각각복수로서서로동일하거나 상이하며복수의 R1끼리혹은복수의 R2끼리흑은복수의 R3끼리혹은복수의 R4 끼리혹은복수의 R5끼리혹은복수의 R6끼리혹은복수의 R7끼리서로결합하여 고리를형성할수있으며,
[94] 11) A, B, C, D, E및 F는서로독립적으로 C6-C20의아릴기또는 CrC20의
헤테로고리기이며 ,
[95] 단 , Ε및 F모두치환또는비치환된 C6의아릴기 (페닐기)인경우에는제외하며，
[96] 여기서，상기아릴기,플루오렌닐기，아릴렌기，헤테로고리기，융합고리기, 알킬기，알켄일기,알콕시기,아릴옥시기는각각중수소;할로겐; ^- 0의알킬기 또는 20의아릴기로치환또는비치환된실란기；실록산기;붕소기;
게르마늄기 ;시아노기 ;니트로기 ; -La-N(Rc)(Rd); C,-C2。의알킬싸이오기 ; Cr o의 알콕실기； d- o의알킬기； C2-C2。의알켄일기； C2-C20의알킨일기； C6-C20의 아릴기；중수소로치환된 C6-C20의아릴기；플루오렌일기; C2-C2。의해테로고리기; C3-C20^시클로알킬기; C7-C20의아릴알킬가및 -C20의아릴알켄일기로 이루어진군에서선택된하나이상의치환기로더욱치환될수있으며,또한 이들치환기들은서로결합하여고리를형성할수도있으며,여기서 '고리 '란 탄소수 3내지 60의지방족고리또는탄소수 6내지 60의방향족고리또는 탄소수 2내지 60의헤테로고리또는이들의조합으로이루어진융합고리를 말하며，포화또는불포화고리를포함한다. }
[97] 더불어본발명은상기화학식 1및 2로표시되는화합물을제공한다.
[98] 또한，상기화학식 1및 2의 L1, 및 L3가하기화학식 A-1내지 A-13중에어느
[105] {상기화학식 A-1내지화학식 A-13에서，
[106] 1) Y는 N-L4-Ar5, 0, S, CReRf또는하기화학식 1-b이고
[107] 화학식 1-b
(R")j (R12)k (¾ ί)
109] 상기화학식 1-b에서,점선은 Y로부터의결합을나타내고,
110] 2) L4는상기 L3의정의와동일하고，
H I] 3) Ar5는상기 Ar4의정의와동일하며 ,
112] 4) Re및 Rf는상기 Ra의정의와동일하고,
113] 5) R11및 R12는상기 R'의정의와동일하고,
114] 6) G및 H는상기 A의정의와동일하고,
115] 7) j및 k는상기 a의정의와동일하고，
116] 8) a', c', d'및 e'은서로독립적으로 0내지 4의정수이고， b'은 0내지 6의
정수이며, f 및 g'은서로독립적으로 0내지 3의정수이고， h'는 0내지 2의 정수이며, i'는 0또는 1의정수이고,
[117] 9) R8, R9및 R10은서로독립적으로수소;증수소;삼중수소;할로겐;시아노기； 나이트로기; C6- o의아릴기;플루오렌일기 ; 0, N, S, Si및 P로이루어진군에서 선택된적어도하나의헤테로원자를포함하는 C2-C60의헤테로고리기; C3-C60의 지방족고리와 C6-C6。의방향족고리의융합고리기； d-C5(^알킬기； C2-C20의 알켄일기; C2-C20의알킨일기; CrC30의알콕실기; C6-C30의아릴옥시기;및 -1 -N(Rc)(Rd);로이루어진군에서선택되고，또는상기 a', b', c', d', e', f 및 g'가 2 이상인경우및 h'가 2인경우는각각복수로서서로동일하거나상이하며복수의 R8끼리혹은복수의 R9끼리혹은복수의 R10끼리혹은이웃한 R8과 R9또는 R9과 R 은서로결합하여방향족고리또는헤테로방향족고리를형성할수있고,
[118] 10) La는상기 1 의정의와동일하고， Re및 R«는상기 Re및 R«의정의와
동일하고,
[119] l^ Z^ Z2및 Z3은서로독립적으로 CR13또는 N이고, Z1, Z2 ¾ Z3 ^적어도
하나는 N이며,
[120] 12) 은수소;중수소;삼중수소;할로겐;시아노기 ;나이트로기 ; C6-C60의
아릴기；플루오렌일기； 0， N, S, Si및 P로이루어진군에서선택된적어도하나의 헤테로원자를포함하는 C2-C6。의헤테로고리기； C3-C6。의지방족고리와 C6-C60의 방향족고리의융합고리기; d-C50의알킬기; C2-C20의알켄일기; C2-C2。의 알킨일기; -C30의 알콕실기; C6-C3。의아릴옥시기;및 -I/-N(Re)(Rd);로이루어진 군에서선택되고，이웃한 R8과 은서로결합하여방향족고리또는
헤테로방향족고리를형성할수있다. }
[121] 또한본발명은상기화학식 1로나타내는제 1호스트화합물이하기화학식 1-1내지화학식 1-5중어느하나인화합물을포함하는유기전기소자를 제공한다.
[123] *화학식 i_i화학식 1-2화학식 1-3
[127] {상기화학식 1-1내지화학식 1-5에서,
[128] 1) X1, C, D, R3, R4, c, d, Ar1및 Ar2는상기에서정의된바와같고
[129] 2) Y는 N-L4-Ar5, 0, S, CReRf또는하기화학식 1-b이고，
[130] 화학식 1-b
[132] 상기화학식 1-b에서,점선은 Y로부터의결합을나타내며，
[133] 3) L4는상기 L3의정의와동일하고，
[134] 4) Ar5는상기 Ar4의정의와동일하고，
[135] 5) Re및 Rf는상기 Ra의정의와동일하고，
[136] 6) R"및 R12는상기 R1의정의와동일하고，
[137] 7) G및 H는상기 A의정의와동일하고,
[138] 8) j및 k는상기 a의정의와동일하고,
[139] 9) a', c'및 d'은서로독립적으로 0내지 4의정수이고， f 및 g'은서로독립적으로 0내지 3의정수이고 h'는 0내지 2의정수이며,
[140] 10) 및 R9는서로독립적으로수소;중수소;삼중수소;할로겐;시아노기； 나이트로기 ; C6- 。의아릴기;플루오렌일기； 0， N, S, Si및 P로이루어진군에서 선택된적어도하나의헤테로원자를포함하는 C2-C60의헤테로고리기; C3-C60의 지방족고리와 C6-C60의방향족고리의융합고리기； -C ^알킬기； C2-C20의 알켄일기; C2-C20의알킨일기; C,-C30의알콕실기; ^30의아릴옥시기;및 - -N(Rc)(R«);로이루어진군에서선택되고，또는상기 a', c', d', f 및 g'가 2이상인 경우및 h'가 2인경우는각각복수로서서로동일하거나상이하며복수의 Rs끼리 혹은복수의 R9끼리혹은이웃한 R8과 R9가서로결합하여방향족고리또는 헤테로방향족고리를형성할수있다. }
[141] 또한본발명은,상기화학식 1로나타내는제 1호스트화합물이하기화학식
1-6내지화학식 1-20중어느하나로표시되는화합물을포함한다.
화학식 1-6화학식 1-7화학식 1-8
[148] 화학식 1-15화학식 1-16화학식 1-17
[152] {상기화학식 1-6내지화학식 1-20에서，
[153] 1) Ra, Rb, R1, R2, R3, R4, a, b, c, d, L', Ar1, Ar2및 n은상기에서정의된바와같고 [154] 2) A, B, C및 D는 C10의아릴기이다. }
[155] 또한본발명은상기화학식 1로나타내는제 1호스트화합물이하기화학식
1-21내지화학식 1-23중어느하나로표시되는화합물을포함한다.
[156] 화학식 1-21화학식 1-22화학식 1-23
[158] {상기화학식 1-21내지화학식 1-23에서，
[159] 1) C, D, R3, R4, c, d, L1, Ar1및 Ar2는상기에서정의된바와같고
[160] 2) W는 Ν-ΙΛΑΓ6, 0, S, CRgRh또는하기화학식 1-c이며，
[161]
[162] 상기화학식 l-c에서，점선은 W로부터의결합을나타내고，
[163] 3) L5는상기 L3의정의와동일하고， Ar6는상기 Ar4의정의와동일하며，
[164] 4) Rg및 Rh는상기 의정의와동일하고，
[165] 5) R15및 R16은상기 R1의정의와동일하고,
[166] 6) I및 J는상기 A의정의와동일하고,
[167] 7) 0및 p는상기 a의정의와동일하고，
[168] 8) 1은 0내지 3의정수이고, m은 0내지 4의정수이며,
[169] 9) R13및 R14는서로독립적으로수소;중수소；삼중수소;할로겐；시아노기; 나이트로기； C6-C60의아릴기；플루오렌일기； 0， N, S, Si및 P로이루어진군에서 선택된적어도하나의헤테로원자를포함하는 C2-C6。의헤테로고리기; C3-C60의 지방족고리와 ^- 0의방향족고리의융합고리기; crc5。의알킬기; c2-c20의 알켄일기； C2-C20의알킨일기； C,-C30의알콕실기； C6-C30의아릴옥시기；및 -La -N(Rc)(Rd);로이루어진군에서선택되고，복수의 R'3끼리흑은복수의 Ri4끼리 흑은이웃한 R13과 R'4가서로결합하여방향족고리또는헤테로방향족고리를 형성할수있고,
[170] 10) 2개의 Ar2는각각동일하거나상이하고， 2개의 W는각각동일하거나
상이하며,복수의 R13및복수의 R14는서로동일하거나상이하다.)
[171] 또한본발명의일예에서,상기화학식 1에서 n이 1인경우의화합물을
포함하는유기전기소자를제공한다.또한상기화학식 1에서 n이 2인경우의 화합물을포함하는유기전기소자를제공한다ᅳ .
[172] 본발명의 일예로，상기 A, B, C, D, E및 F가하기화학식 B-1내지화학식 B-7 중어느하나로표시되는화합물을포함하는유기전기소자를제공한다.
[173] 화학식 B-l화학식 B-2화학식 B-3화학식 B-4
[175] 화학식 B-5화학식 B-6화학식 B-7
[177] {상기화학식 B-l내지화학식 B-7에서,
[178] (1) Z4내지 Z51은 CRi또는 N이며,
[179] (2) Ri는상기 Ra의정의와동일하고,
[180] (3) *는축합되는위치를나타낸다. }
[181] 또다른측면에서본발명은상기화학식 2로나타내는제 2호스트화합물 0 하기화학식 3또는화학식 4로표시되는화합물을포함한다.
[182] 화학식 3화학식 4
[184] {상기화학식 3및 4에서，
[185] E, F, R5, R6, R7, e, f, g, L2, Ar3, X2및 X3은상기에서정의된바와같다. }
[186] 또한본발명은상기화학식 2의 R6이방향족고리또는헤테로방향족고리를 반드시형성하고있는것을특징으로하는유기전기소자를제공한다.
[187]
[188] 또한본발명은,상기화학식 2로나타내는제 2호스트화합물이하기화학식
5-1내지화학식 5-24증어느하나로표시되는화합물을포함한다.
[189] 화학식 5-1화학식 5-2화학식 5-3
화학식 5-4화학식 5-5화학식 5-6
[193] 화학식 5-7화학식 5-8화학식 5-9
[195] 화학식 5-10화학식 5-11화학식 5-12
[197] 화학식 5-13화학식 5-14화학식 5-15
[199] 화학식 5-16화학식 5-17화학식 5-18
[201] 화학식 5-19화학식 5-20화학식 5-21
[203] 화학식 5-22화학식 5-23화학식 5-24
[205] {상기화학식 5-1내지화학식 5-24에서，
[206] R5, R6, R7, e, f, g, ΙΛ Ar3, X2및 X3은상기에서정의된바와같다. }
[207] 본발명은，상기화학식 2로나타내는제 2호스트화합물이하기화학식 6-1 내지화학식 6-8로이루어진군에서선택되는화합물을포함한다.
[208] 화학식 6-1화학식 6-2화학식 6-3화학식 6-4
[210] 화학식 6-5화학식 6-6화학식 6-7화학식 6-8
[212] {상기화학식 6-1내지화학식 6-8에서,
[213] E, F, R5, R6, R7, R\ R e, f, g, L2, L3, Ar3및 Ar4는상기에서정의된바와같다. } [2141 본발명에서상기화학식 1로나타내는제 1호스트화합물이하기화합물 1ᅳ 1 내지화합물 1-70및화합물 2-1내지화합물 2-115증어느하나로표시되는 화합물을포함한다.
2-111 2-112 2-113 2-114 2-115
[252] 또한본발명에서상기화학식 2로나타내는제 2호스트화합물이하기화합물 3-1내지화합물 3-115중어느하나로표시되는화합물을포함한다.
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[275]
3-111 3-112 3-113 3-114 3-115
[276] 도 1을참조하여설명하면，본발명에따른유기전기소자 (100)는기판 (110) 상에형성된제 1전극 (120)，제 2전극 (180)및제 1전극 (120)과제 2전극 (180) 사이에화학식 1로표시되는화합물을포함하는유기물층올구비한다.이때，제 1전극 (120)은애노드 (양극)이고,제 2전극 (180)은캐소드 (음극)일수있으며， 인버트형의경우에는제 1전극 (120)이캐소드이고제 2전극 (180)이애노드일수 있다.
[277] 유기물층은제 1전극 (120)상에순차적으로정공주입층 (130)，정공수송층 (140), 발광층 (150),전자수송층 (160)및전자주입층 (170)을포함할수있다.이때， 발광층 (150)을제외한나머지층들이형성되지않을수있다.정공저지층， 전자저지층，발광보조층 (151)，전자수송보조층,버퍼층 (141)등을더포함할수도 있고，전자수송층 (160)등이정공저지층의역할을할수도있을것이다.
[278] 또한,미도시하였지만본발명에따른유기전기소자는제 1전극과제 2전극중 적어도일면증상기유기물층과반대되는일면에형성된보호층을더포함할수 있다.
[279] 한편，동일한코어일지라도어느위치에어느치환기를결합시키냐에따라 밴드갭 (band gap),전기적특성,계면특성등이달라질수있으므로，코어의선택 및이에결합된서브 (sub)-치환체의조합도아주중요하며，특히각유기물층 간의에너지 ievei및 T1값,물질의고유특성 (mobility,계면특성등)둥이최적의 조합을이루었을때긴수명과높은효율을동시에달성할수있다.
[280] 본발명의일실시예에따른유기전기발광소자는 PVD(physical vapor
deposition)방법을이용하여제조될수있다.예컨대,기판상에금속또는 전도성을가지는금속산화물또는이들의합금을증착시켜양극을형성하고，그 위에정공주입층 (130)，정공수송층 (140)，발광층 (150),전자수송층 (160)및 전자주입층 (170)올포함하는유기물층을형성한후,그위에음극으로사용할수 있는물질을증착시킴으로써제조될수있다.
[281] 또한,정공수송층 (140)과발광층 (150)사이에발광보조층 (151)을,
발광층 (150)과전자수송층 (160)사이에전자수송보조층을추가로더형성할수 있다.
[282] 또한,상기제 1전극과발광층사이에 1층이상의정공수송대역층을포함하고, 상기정공수송대역층은정공수송층，발광보조층또는이둘을모두포함하며， 상기정공수송대역층이상기화학식 1로표시되는화합물을포함하는
유기전기소자를제공할수있다ᅳ
[283] 이에따라,본발명은상기유기전기소자에서상기제 1전극의 일측면중상기 유기물층과반대되는일측또는상기제 2전극의 일측면중상기유기물층과 반대되는일측중적어도하나에형성되는광효율개선층을더포함하는 유기전기소자를제공한다.
[284] 또한본발명에서상기유기물층은스핀코팅공정，노즐프린팅공정,잉크젯 프린팅공정,슬롯코팅공정,딥코팅공정및를투롤공정중어느하나에의해 형성되고,본발명에따른유기물층은다양한방법으로형성될수있으므로，그 형성방법에의해본발명의권리범위가제한되는것은아니다.
[285] 또한본발명은상기유기물층의발광층에서상기화학식 1및상기화학식 2로 나타내는화합물이 1:9내지 9: 1중어느하나의비율로흔합되어발광층에 포함되는유기전기소자를제공한다ᅳ
[286] 또한,본발명은상기유기물층의발광층에서상기화학식 1및상기화학식 2로 나타내는화합물이 1:9또는 5:5중어느하나의비율로흔합되어발광층에 사용되는것을특징으로하는유기전기소자를제공한다.보다바람직하게는 상기화학식 1및상기화학식 2로나타내는화합물의흔합비율이 2:8또는 3:7로 발광층에포함된다.
[287]
[288] 본발명의 일실시예에따른유기전기소자는사용되는재료에따라전면
발광형，후면발광형또는양면발광형일수있다.
[289] WOLED(White Organic Light Emitting Device)는고해상도실현이용이하고 공정성이우수한한편，기존의 LCD의칼라필터기술을이용하여제조될수있는 이점이 있다.주로백라이트장치로사용되는백색유기발광소자에대한다양한 구조들이제안되고특허화되고있다.대표적으로， R(Red), G(Green), B(Blue) 발광부들을상호평면적으로병렬배치 (side-by-side)방식 , R, G, B발광층이 상하로적층되는적층 (stacking)방식이 있고,청색 (B)유기발광층에의한 전계발광과이로부터의광을이용하여무기형광체의
자발광 (photo-luminescence)을이용하는색변환물질 (color conversion material, CCM)방식등이 있는데,본발명은이러한 WOLED에도적용될수있을것이다.
[290] 또한본발명은상기한유기전기소자를포함하는디스플레이장치；및상기 디스플레이장치를구동하는제어부；를포함하는전자장치를제공한다.
[291] 또다른측면에서상기유기전기소자는유기전기발광소자，유기태양전지, 유기감광체,유기트랜지스터，및단색또는백색조명용소자중적어도하나인 것을특징으로하는전자장치를본발명에서제공한다.이때,전자장치는현재 또는장래의유무선통신단말기일수있으며,휴대폰등의이동통신단말기， PDA,전자사전， PMP,리모콘,네비게이션,게임기 ,각종 TV,각종컴퓨터등모든 전자장치를포함한다.
[292] 이하에서，본발명의상기화학식 1및 2로표시되는화합물의합성예및본
발명의유기전기소자의제조예에관하여실시예를들어구체적으로
설명하지만，본발명의하기실시예로한정되는것은아니다.
[293] [합성예 1]
[294] 본발명에따른화학식 1로표시되는화합물 (final product 1)은하기반응식 1과 같이 Sub 1과 Sub 2를반웅시켜합성되며，이에한정되는것은아니다 . X^ C E 3, R4, c d, Ar1, Ar2, L1및 n은상기화학식 1에서정의된것과동일하며， Hal1은 Br 또는 C1이다.
[295] <반웅식 1>
[296]
Sub Sub 2 Final Product 1
[297] I. Sub 1의합성
[298] 상기반웅식 1의 Sub 1에대한합성방법은본출원인의한국등록특허
10-1520955호 (2015.05.11일자둥록공고)，한국둥록특허 10-1530885호
(2015.06.17일자등록공고),한국등록특허 10-1530886호 (2015.06.17일자 등록공고),한국둥록특허 10-1614740호 (2016.04.18일자등록공고)，
한국출원특허 2013-0056221 (2013.05.20일자출원)，한국출원특허 2015-0035780 (2015.03.16일자출원),한국출원특허 2015-0083505 (2015.06.12일자출원)에 개시된합성방법을사용하였다. L'이단일결합이아닐경우하기반웅식 2의 반웅경로에의해합성될수있으나,이에한정되는것은아니며, Hal1은 Br또는 C1이다.
[299] ：반웅식 2>
Sub 1-1 Sub 1
[301] Sub 1에속하는구체적화합물의합성예는다음과같다.
[302] 1. Sub 1-26합성예
[304] (1) Sub 1-1-26합성
[305] Sub 1-23 (CAS Registry Number: 171408-76-7) (38.80 g, 98.15 mmol)을
등근바닥플라스크에 DMF (490 ml)로녹인후에， Bis(pinacolato)diboron (27.42 g,
107.97 mmol), Pd(dppf)Cl2 (2.40 g, 2.94 mmol), KOAc (28.90 g, 294.46 mmol)를 첨가하고 90°C에서교반하였다.반웅이완료되면증류를통해 DMF를제거하고 CH2C12와물로추출하였다.유기층을 MgS04로건조하고농축한후생성된 화합물을 silicagel column및재결정하여생성물 32.13 g (수율: 74%)을얻었다.
[306] (2) Sub 1-26합성
[307] 상기합성에서얻어진 Sub 1-1-26 (32.13 g, 72.63 mmol)을등근바닥플라스크에 THF (370 ml)로녹인후에， 1,4-dibromobenzene (CAS Registry Number: 106-37-6) (22.27 g, 94.42 mmol), Pd(PPh3)4 (2.52 g, 2.18 mmol), NaOH (8.72 g, 217.89 mmol), 물 (185 ml)을첨가하고 80°C에서교반하였다.반웅이완료되면 CH2C12와물로 추출한후유기층을 MgS04로건조하고농축한후생성된화합물을 silicagel column및재결정하여생성물 23.97 g (수율: 70%)을얻었다.
[308] 2. Sub 1-73합성예
[310] (1) Sub 1-1-73합성
[311] Sub 1-36 (CAS Registry Number: 1800333-62-3) (50.31 g, 125.49 mmol)에
Bis(pinacolato)diboron (35.05 g, 138.04 mmol), Pd(dppf)Cl2(3.07 g, 3.76 mmol), KOAc (36.95 g, 376.47 mmol), DMF (630 ml)를첨가하고상기 Sub 1-1-26합성법을 사용하여생성물 37.69 g (수율: 61%)을얻었다.
[312] (2) Sub 1-73합성
[313] 상기합성에서얻어진 Sub 1-1-73 (37.69 g, 76.54 mmol)에
1 -bromo-2,4-dichlorobenzene (CAS Registry Number: 1193-72-2) (22.48 g, 99.50 mmol), Pd(PPh3)4 (2.65 g, 2.30 mmol), NaOH (9.18 g, 229.62 mmol), THF (390 ml), 물 (195 ml)을첨가하고상기 Sub 1-26합성법을사용하여생성물 24.66 g (수율: 63%)을얻었다.
[314] 3. Sub 1-75합성예
(1) Sub 1-1-75합성
[317] Sub 1-63 (CAS Registry Number: 1793062-76-6) (46.40 g, 115.74 mmol)에
Bis(pinacolato)diboron (32.33 g, 127.31 mmol), Pd(dppf)Cl2 (2.84 g, 3.47 mmol), KOAc (34.08 g, 347.21 mmol), DMF (580 ml)를첨가하고상기 Sub 1-1-26합성법을 사용하여생성물 37.04 g (수율: 65%)을얻었다.
[318] (2) Sub 1-75합성
[319] 상기합성에서얻어진 Sub 1-1-75 (37.04 g, 75.22 mmol)에
2,8-dibromodibenzo[b,d]thiophene (CAS Registry Number: 31574-87-5) (33.45 g, 97.78 mmol), Pd(PPh3)4 (2.61 g, 2.26 mmol), NaOH (9.03 g, 225.66 mmol), THF (380 ml),물 (190 ml)을첨가하고상기 Sub 1-26합성법을사용하여생성물 32.10 g (수율 : 68%)을얻었다.
[320] 4. Sub 1-76합성예
Sub 1^t6 Sub 1-1-76 Sub 1-76
[322] (1) Sub 1-1-76합성
[323] Sub 1-46 (CAS Registry Number: 1800298-96-7) (39.31 g, 98.05 mmol)에
Bis(pinacolato)diboron (27.39 g, 107.86 mmol), Pd(dppf)Cl2 (2.40 g, 2.94 mmol), KOAc (28.87 g, 294.16 mmol), DMF (490 ml)를첨가하고상기 Sub 1-1-26합성법을 사용하여생성물 33.80 g (수율: 70%)을얻었다.
[324] (2) Sub 1-76합성
[325] 상기합성에서얻어진 Sub 1-1-76 (33.80 g, 68.64 mmol)에
2,7-dibromo-9,9-dimethyl-9H-fluorene (CAS Registry Number: 28320-32-3) (31.42 g, 89.23 mmol), Pd(PPh3)4 (2.38 g, 2.06 mmol), NaOH (8.24 g, 205.92 mmol), THF (350 ml),물 (175 ml)을첨가하고상기 Sub 1-26합성법을사용하여생성물 28.89 g (수율 : 66%)을얻었다.
[326] Sub 1에속하는화합물은아래와같은화합물일수있으나，이에한정되는것은 아니며，표 1은 Sub 1에속하는일부화합물의 FD-MS(Field Desorption-Mass Spectrometry)값을나타낸것이다.
Sub 1-1 Sub 1-2 Sub 1-3 Sub 1-4 Sub 1-5 Sub 1-« Sub 1-7 Sub 1-8 Sub 1-9
[ Έ] [8εε] CZ600/Z.T0ZaM/X3d S8£0/810Z OAV
(00-LL =\DlzUiD)£V9LP=^ P£-\ qns (\6WP=\DLlU6zD)0V00 =^ εε-ι qns CZ600/Z.T0ZaM/X3d »S8£0/8I0Z OAV
9£
[339] II. Sub 2의함성
[340] 상기반웅식 1의 Sub 2에대한합성방법은본출원인의한국등록특허제
10-1251451호 (2013.04.05일자등록공고)에개시된합성방법을사용하였다.하기 반웅식 3의반웅경로에의해합성될수있으나,이에한정되는것은아니다.
[341] <반웅식 3>
[342] Pd2(dba)3 1 P(t-Bu)3 / NaOt-Bu Ar1
Ar1 H2N Ar2 /
HN.
Toluene
¾r2
Sub 2
[343] Sub 2에속하는구체적화합물의합성예는다음과같다.
[344] 1. Sub 2-11합성예
[346] 출발물질인 3-bromo-l,l'-biphenyl (CAS Registry Number: 2113-57-7) (10.99 g, 47.15 mmol)을등근바닥플라스크에 toluene (330 ml)으로녹인후에,
naphthalen-2-amine (CAS Registry Number: 91-59-8) (7.43 g, 51.86 mmol), Pd2(dba)3 (1.30 g, 1.41 mmol), P(i-Bu)3 (0.76 g, 3.77 mmol), NaOi-Bu (13.59 g, 141.44 mmol)을 첨가하고 80°C에서교반하였다.반응이완료되면 CH2C12와물로추출한후 유기층을 MgS04로건조하고농축한후생성된화합물을 silicagel column및 재결정하여생성물 11.14 g (수율: 80%)을얻었다.
[347] 2. Sub 2-17합성예
Sub 2-17
[349] 출발물질인 l-(4-bromophenyl)naphthalene (CAS Registry Number: 204530-94-9) (20.23 g, 71.44 mmol)에 [l,l'-biphenyl]-4-amine (CAS Registry Number: 92-67-1) (13.30 g, 78.59 mmol), Pd2(dba)3 (1.96 g, 2.14 mmol), P(t-Bu)3 (1.16 g, 5.72 mmol), NaOt-Bu (20.60 g, 214.33 mmol), toluene (500 ml)을첨가하고상기 Sub 2-11 합성법을사용하여생성물 22.29 g (수율: 84%)을얻었다.
[350] 3. Sub 2-35합성예
[352] 출발물질인 2-chlorodibenzo[f,h]quinoline (CAS Registry Number: 1417779-49-7) (20.60 g, 78.11 mmol)에 4-(tert-butyl)aniline (CAS Registry Number: 769-92-6) (12.82 g, 85.92 mmol), Pd2(dba)3 (2.15 g, 2.34 mmol), P(t-Bu)3 (1.26 g, 6.25 mmol), NaOi-Bu (22.52 g, 234.34 mmol), toluene (550 ml)을첨가하고상기 Sub 2-11 합성법을사용하여생성물 15.88 g (수율: 54%)을얻었다.
[353] 4. Sub 2-82합성예
[354]
[356] Sub 2에속하는화합물은아래와같은화합물일수있으나,이에한정되는것은 아니며，표 2는 Sub 2에속하는일부화합물의 FD-MS(Field Desorption-Mass Spectrometry)값을나타낸것이다.
Sub 2-1 Sub 2-2 Sub 2-3 Sub 2-4 Sub 2-5 Sub 2-6 Sub 2-7 Sub 2-8 Sub 2-9 Sub 2-10 Sub 2-11
Sub 2-22 Sub 2-23 Sub 2-24 Sub 2-25 Sub 2-26 Sub 2-27 Sub 2-28 Sub 2-29 Sub 2-30 Sub 2-31
Sub 2-32Sub 2-33 Sub 2-34 Sub 2-35 Sub 2-36 Sub 2-37 Sub 2-38 Sub 2-39 Sub 2-40 Sub 2-41
[ΖΈ [99£]
8CZ600/Z.T0ZaM/X3d S8£0/810Z OAV
£Z600/Ll0ZW^/13d »S8£0/8I0Z OAV
[367]
[368] III. Final products 1합성
[369] Sub 1 (1당량)을등근바닥플라스크에 Toluene으로녹인후에， Sub 2 (1당량), Pd2(dba)3(0.03당량)， (t-Bu)3P (0.06당량), NaOt-Bu (3당량)을 100oC에서 교반하였다.반웅이완료되면 CH2C12와물로추출한후유기층을 MgS04로 건조하고농축한후생성된화합물을 silicagel column및재결정하여 Final product 1을얻었다.
[370] 1. 1-1합성예
[372] 상기합성에서얻어진 Sub 1-1 (9.70 g, 42.41 mmol)을등근바닥플라스크에
toluene (445 ml)으로녹인후에, Sub 2-14 (14.99 g, 46.65 mmol), Pd2(dba)3 (1.17 g, 1.27 mmol), P(t-Bu)3 (0.51 g, 2.54 mmol), NaOi-Bu (12.23 g, 127.23 mmol)을 첨가하고 100°C에서교반하였다.반응이완료되면 CH2C12와물로추출한후 유기층을 MgS04로건조하고농축한후생성된화합물을 silicagel column및 재결정하여생성물 16.34 g (수율： 75%)을얻었다.
[373] 2. 1-23합성예
[375] 상기합성에서얻어진 Sub 1-12 (10.00 g, 28.34 mmol)에 Sub 2-62 (15.14 g, 31.17 mmol), Pd2(dba)3 (0.78 g, 0.85 mmol), P(t-Bu)3 (0.34 g, 1.70 mmol), NaOt-Bu (8.17 g, 85.02 mmol), toluene (300 ml)을첨가하고상기 1-1합성법을사용하여생성물 15.46 g (수율： 68%)을얻었다.
[376] 3. 1-56합성예
Sub 1-25 -56
[378] 상기합성에서얻어진 Sub 1-25 (9.90 g, 28.22 mmol)에 Sub 2-17 (11.53 g, 31.04 mmol), Pd2(dba)3 (0.78 g, 0.85 mmol), P(i-Bu)3 (0.34 g, 1.69 mmol), NaOt-Bu (8.14 g: 84.65 mmol), toluene (300 ml)을첨가하고상기 1-1합성법을사용하여생성물 15.10 g (수율 : 78%)을얻었다.
[379] 4. 1-62합성예
[381] 상기합성에서 얻어진 Sub 1-26 (11.00 g, 23.33 mmol)에 Sub 2-43 (9.28 g, 25.67 mmol), Pd2(dba)3 (0.64 g, 0.70 mmol), P(r-Bu)3 (0.28 g, 1.40 mmol), NaOt-Bu (6.73 g, 70.00 mmol), toluene (245 ml)을첨가하고상기 1-1합성법을사용하여생성물 12.46 g (수율 : 71%)을얻었다.
[382] 5. 2-10합성예
[384] 상기합성에서 얻어진 Sub 1-33 (12.60 g, 31.43 mmol)에 Sub 2-38 (11.60 g, 34.57 mmol), Pd2(dba)3 (0.86 g, 0.94 mmol), P(r-Bu)3 (0.38 g, 1.89 mmol), NaOi-Bu (9.06 g, 94.29 mmol), toluene (330 ml)을첨가하고상기 1-1합성법을사용하여생성물 13.86 g (수율 : 63%»)을얻었다.
[385] 6. 2-31합성예
[387] 상기합성에서얻어진 Sub 1-38 (11.90 g, 29.68 mmol)에 Sub 2-43 (11.80 g, 32.65 mmol), Pd2(dba)3 (0.82 g, 0.89 mmol), P(t-Bu)3 (0.36 g, 1.78 mmol), NaOt-Bu (8.56 g, 89.05 mmol), toluene (310 ml)을첨가하고상기 1-1합성법을사용하여생성물 14.65 g (수율： 68%)을얻었다.
[388] 7. 2-41합성예
[390] 상기합성에서얻어진 Sub 1-42 (12.00 g, 29.93 mmol)에 Sub 2-14 (10.58 g, 32.93 mmol), Pd2(dba)3 (0.82 g, 0.90 mmol), P(i-Bu)3 (0.36 g, 1.80 mmol), NaOr-Bu (8.63 g, 89.80 mmol), toluene (315 ml)을첨가하고상기 1-1합성법을사용하여생성물 14.78 g (수율： 72%)올얻었다.
[391] 8. 2-48합성예
[393] 상기합성에서 얻어진 Sub 1-43 (11.30 g, 28.19 mmol)에 Sub 2-39 (11.21 g, 31.00 mmol), Pd2(dba)3 (0.77 g, 0.85 mmol), P(i-Bu)3 (0.34 g, 1.69 mmol), NaOr-Bu (8.13 g, 84.56 mmol), toluene (295 ml)을첨가하고상기 1-1합성법을사용하여 생성물 14.32 g (수율 : 70%)을얻었다.
[394] 9. 2-55합성예
[396] 상기합성에서얻어진 Sub 1-45 (13.00 g, 32.43 mmol)에 Sub 2-79 (12.54 g, 35.67 mmol), Pd2(dba)3 (0.89 g, 0.97 mmol), P(i-Bu)3 (0.39 g, 1.95 mmol), NaOt-Bu (9.35 g, 97.28 mmol), toluene (340 ml)을첨가하고상기 1-1합성법을사용하여생성물 11.84 g (수율 : 51%)을얻었다ᅳ
[397] 10. 2-79합성예
[399] 상기합성에서 얻어진 Sub 1-61 (12.80 g, 30.05 mmol)에 Sub 2-35 (12.45 g, 33.06 mmol), Pd2(dba)3 (0.83 g, 0.90 mmol), P(i-Bu)3 (0.36 g, 1.80 mmol), NaOt-Bu (8.67 g, 90.16 mmol), toluene (315 ml)을첨가하고상기 1-1합성법을사용하여생성물 10.59 g (수율: 46%)을얻었다.
[400] 11. 2-98합성예
[402] 상기합성에서얻어진 Sub 1-66 (12.70 g, 31.68 mmol)에 Sub 2-82 (11.69 g, 34.85 mmol), Pd2(dba)3 (0.87 g, 0.95 mmol), P(i-Bu)3 (0.38 g, 1.90 mmol), NaOt-Bu (9.13 g, 95.03 mmol), toluene (330 ml)을첨가하고상기 1-1합성법올사용하여생성물 14.41 g (수율： 65%)을얻었다.
[403] 12. 2-102합성예
[405] 상기합성에서얻어진 Sub 1-78 (12.40 g, 27.50 mmol)에 Sub 2-38 (10.15 g, 30.25 mmol), Pd2(dba)3 (0.76 g, 0.82 mmol), P(i-Bu)3 (0.33 g, 1.65 mmol), NaOi-Bu (7.93 g, 82.49 mmol), toluene (290 ml)을첨가하고상기 1-1합성법을사용하여생성물 14.23 g (수율 : 69%)을얻었다.
[406] 13. 2-109합성예
[407]
[408] 상기합성에서 얻어진 Sub 1-73 (13.25 g, 25.91 mmol)에 Sub 2-7 (13.98 g, 56.99 mmol), Pd2(dba)3 (1.42 g, 1.55 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol), NaOr-Bu (14.94 g, 155.44 mmol), toluene (415 ml)을첨가하고상기 1-1합성법을사용하여생성물 13.72 g (수율： 57%)을얻었다.
[409] 14. 2-114합성예
[411] 상기합성에서 얻어진 Sub 1-75 (15.00 g, 23.90 mmol)에 Sub 2-11 (7.77 g, 26.29 mmol), Pd2(dba)3 (0.66 g, 0.72 mmol), P(i-Bu)3 (0.29 g, 1.43 mmol), NaOi-Bu (6.89 g, 71.70 mmol), toluene (250 ml)을첨가하고상기 1-1합성법을사용하여생성물 12.28 g (수율 : 61%)을얻었다.
[412] 15. 2-115합성예
Sub 1-76 Sub 2-14
[414] 상기합성에서얻어진 Sub 1-76 (14.65 g, 22.98 mmol)에 Sub 2-14 (8.12 g, 25.27 mmol), Pd2(dba)3 (0.63 g, 0.69 mmol), P(i-Bu)3 (0.28 g, 1.38 mmol), NaOi-Bu (6.62 g: 68.93 mmol), toluene (240 ml)을첨가하고상기 1-1합성법을사용하여생성물 12.91 g (수율 : 64%)을얻었다.
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[416]
[417] [합성예 2]
[418] 본발명에따른화학식 2로표시되는화합물 (final product 2)은하기 반웅식 4와 같이 Sub 3과 Sub 4를반웅시켜합성되며,이에한정되는것은아니다. E, F, R5, R6 , R7, e, f, g, h, i, U, Ar3, X2및 X3은화학식 2에서정의된것과동일하며， Hal1은 Br 또는 C1이다.
[419]
Sub 3 Sub 4 Final Product 2
[421] L Sub 3의함성
[422] 상기반웅식 4의 Sub 3은하기반웅식 5의반웅경로에의해합성될수있으나， 이에한정되는것은아니다.
[423] <반웅식 5>
Sub 3-11
[426] Sub 3-1-1의합성에서사용되는출발물질인카바졸유도체는본출원인의 한국등록특허제 10-1535606호 (2015.07.03일자등록공고)에개시된
합성방법으로제조되었다.
[427] Sub 3-1-1의합성에서사용되는출발물질인다이벤조싸이오펜유도체또는 다이벤조퓨란은본출원인의한국출원특허 2014-0074261 (2014.06.18일자 출원)에개시된합성방법으로제조되었다.
[428] Sub 3-1-1의합성에서사용되는출발물질인플루오렌유도체는본출원인의 한국출원특허 2013-0056221 (2013.05.20일자출원)，한국출원특허 2015-0083505 (2015.06.12일자출원)에개시된합성방법으로제조되었다.
[429] Sub 3에속하는구체적화합물의합성예는다음과같다.
[430] 1. Sub 3-1합성예
Sub 3-1-1 Sub 3-11-1 Sub 3-1
[432] (1) Sub 3-1-1합성
[433] 출발물질인 3-bromo-9-phenyl-9H-carbazole (CAS Registry Number: 1153-85-1) (74.15 g, 230.13 mmol)을등근바닥플라스크에 DMF (1150 ml)로녹인후에 , Bis(pinacolato)diboron (64.28 g, 253.14 mmol), Pd(dppf)Cl2 (5.64 g, 6.90 mmol), KOAc (67.75 g, 690.39 mmol)를첨가하고 120oC에서교반하였다.반웅이 완료되면증류를통해 DMF를제거하고 CH2C12와물로추출하였다.유기층을 MgS04로건조하고농축한후생성된화합물을 silicagel column및재결정하여 생성물 64.58 g (수율: 76%)을얻었다.
[434] (2) Sub 3-II-1합성
[435] 상기합성에서얻어진 Sub 3-1-1 (64.58 g, 174.89 mmol)를등근바닥플라스크에
THF (780 ml)로녹인후에， 2-bromo-l-nitronaphthalene (CAS Registry Number: 4185-62-0) (44.08 g, 174.89 mmol), Pd(PPh3)4 (6.06 g, 5.25 mmol), K2C03 (72.51 g: 524.66 mmol),물 (390 ml)을첨가하고 80°C에서교반하였다.반웅이완료되면 CH2C12와물로추출한후유기층을 MgS04로건조하고농축한후생성된 화합물을 silicagel column및재결정하여생성물 5그 99 g (수율: 80%)을얻었다.
[436] (3) Sub 3-1합성
[437] 상기합성에서얻어진 3-II-1 (57.99 g, 139.92 mmol)를등근바닥플라스크에 o -dichlorobenzene (700 ml)으로녹인후에， triphenylphosphine (91.75 g, 349.79 mmol)을첨가하고 200 에서교반하였다.반옹이완료되면증류를통해 o -dichlorobenzene을제거하고 CH2C12와물로추출하였다.유기층을 MgS04로 건조하고농축한후생성된화합물을 silicagel column및재결정하여생성물 20.34 g (수율： 38%)을얻었다.
[438]
[439] 2. Sub 3-8합성예
[441] (1) Sub 3-1-8합성
[442] 출발물질인 2-bromodibenzo[b,d]thiophene (CAS Registry Number: 22439-61-8)
(64.76 g, 246.10 mmol)에 Bis(pinacolato)diboron (68.74 g, 270.70 mmol), Pd(dppf)Cl 2 (6.03 g, 7.38 mmol), KOAc (72.46 g, 738.29 mmol), DMF (1230 ml)를첨가하고 상기 Sub 3-1-1합성법을사용하여생성물 59.55 g (수율: 78%)을얻었다.
[443] (2) Sub 3-II-8합성
[444] 상기합성에서얻어진 Sub 3-1-8 (59.55 g, 191.96 mmol)에
2-bromo-l-nitronaphthalene (CAS Registry Number: 4185-62-0) (48.39 g, 191.96 mmol), Pd(PPh3)4 (6.65 g, 5.76 mmol), K2C03 (79.59 g, 575.88 mmol), THF (850 ml), 물 (425 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 51.85 g (수율: 76%)을얻었다.
[445] (3) Sub 3-8합성
[446] 상기합성에서얻어진 Sub 3-II-8 (51.85 g, 145.89 mmol)에 triphenylphosphine (95.66 g, 364.72 mmol), o-dichlorobenzene (730 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 16.04 g (수율: 34%)를얻었다.
[447]
[448] 3. Sub 3-11, Sub 3-13합성예
Sub 3-11-13
[450] (1) Sub 3-1-11합성
[451] 출발물질인 8-biOmobenzo[b]naphtho[2,l-d]thiophene (CAS Registry Number:
1628067-29-7) (166.05 g, 530.16 mmol)에 Bis(pinacolato)diboron (148.09 g, 583.17 mmol), Pd(dppf)Cl2( 12.99 g, 15.90 mmol), KOAc ( 156.09 g, 1590.47 mmol), DMF (2650 ml)를첨가하고상기 Sub 3-1-1합성법올사용하여생성물 131.79 g (수율: 69%)을얻었다.
[452] (2) Sub 3-II-11합성
[453] 상기합성에서얻어진 Sub 3-1-11 (55.69 g, 154.57 mmol)에
1 -bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) (31.23 g, 154.57 mmol), Pd(PPh3)4 (5.36 g, 4.64 mmol), K2C03 (64.09 g, 463.72 mmol), THF (680 ml),물 (340 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 42.30 g (수율: 77%)을 얻었다.
[454] (3) Sub 3-11합성
[455] 상기합성에서얻어진 Sub 3-II-11 (42.30 g, 119.02 mmol)에 triphenylphosphine (78.04 g, 297.54 mmol), o-dichlorobenzene (595 ml)을첨가하고상기 Sub 3-1 합성법을사용하여 생성물 11.93 g (수율: 31%)을얻었다.
[456] (4) Sub 3-Π-13합성
[457] 상기합성에서 얻어진 Sub 3-1-11 (48.67 g, 135.09 mmol)에
2-bromo- 1 -nitronaphthalene (CAS Registry Number: 4185-62-0) (34.05 g, 135.09 mmol), Pd(PPh3)4 (4.68 g, 4.05 mmol), K2C03 (56.01 g, 405.27 mmol), THF (600 ml), 물 (300 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 39.99 g (수율: 73%)을얻었다.
[458] (5) Sub 3-13합성
[459] 상기합성에서얻어진 Sub 3-II-13 (39.99 g, 98.63 mmol)에 triphenylphosphine (64.67 g, 246.57 mmol), o-dichlorobenzene (490 ml)을첨가하고상기 Sub 3-1
합성법을사용하여생성물 12.16 g (수율: 33%)을얻었다.
[460]
[461] -l
[463] (1) Sub 3-1-15합성
[464] 출발물질인 10-bromobenzo[b]naphtho[l,2-d]thiophene (CAS Registry Number:
1656983-12-8) (66.70 g, 212.96 mmol)에 Bis(pinacolato)diboron (59.49 g, 234.25 mmol), Pd(dppf)Cl2(5.22 g, 6.39 mmol), KOAc (62.70 g, 638.87 mmol), DMF (1065 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 53.71 g (수율: 70%)을 얻었다.
[465] (2) Sub 3-II-15합성
[466] 상기합성에서 얻어진 Sub 3-1-15 (53.71 g, 149.08 mmol)에
1 -bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) (30.12 g, 149.08 mmol), Pd(PPh3)4 (5.17 g, 4.47 mmol), K2C03 (61.81 g, 447.24 mmol), THF (660 ml),물 (330 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 39.74 g (수율: 75%)을 얻었다.
[467] (3) Sub 3-15합성
[468] 상기합성에서 얻어진 Sub 3-II-15 (39.74 g, 111.81 mmol)에 triphenylphosphine (73.32 g, 279.54 mmol), o-dichlorobenzene (560 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 11.57 g (수율 : 32%)을얻었다.
[469]
[470] 5. Sub 3-19합성예
[472] (1) Sub 3-II-19합성
[473] 상기합성에서얻어진 Sub 3-1-11 (26.70 g, 74.11 mmol)에
3-(4-bromo-3-nitrophenyl)-9-phenyl-9H-carbazole (CAS Registry Number:
1526986-96-8) (32.85 g, 74.11 mmol), Pd(PPh3)4 (2.57 g, 2.22 mmol), K2C03 (30.73 g, 222.33 mmol), THF (330 ml),물 (165 ml)을첨가하고상기 Sub 3-II-1합성법을 사용하여생성물 3().07 g (수율: 68%)을얻었다.
[474] (2) Sub 3-19합성
[475] 상기합성에서 얻어진 Sub 3-II-19 (30.07 g, 50.39 mmol)에 triphenylphosphine (33.04 g, 125.98 mmol), o-dichlorobenzene (250 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 10.24 g (수율: 36%)을얻었다.
[476]
[477]
[478] *6. Sub 3-32합성예
[480] (1) Sub 3-1-32합성
[481] 출발물질인 12-bromophenanthro[9, 10-b]benzofuran (CAS Registry Number:
1627917-35-4) (69.00 g, 198.73 mmol)에 Bis(pinacolato)diboron (55.51 g, 218.60 mmol), Pd(dppf)Cl2 (4.87 g, 5.96 mmol), KOAc (58.51 g, 596.18 mmol), DMF (995 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 52.50 g (수율: 67%)올 얻었다.
[482] (2) Sub 3-Π-32합성
[483] 상기합성에서얻어진 Sub 3-1-32 (52.50 g, 133.15 mmol)에
1 -bromo-2-nitrobenzene (CAS Registry Number: 577-19-5) (26.90 g, 133.15 mmol), Pd(PPh3)4 (4.62 g, 3.99 mmol), K2C03 (55.21 g, 399.46 mmol), THF (590 ml),물 (295 ml)을첨가하고상기 Sub 3-Π-1합성법을사용하여생성물 40.44 g (수율: 78%)을 얻었다.
[484] (3) Sub 3-32합성
[485] 상기합성에서얻어진 Sub 3-II-32 (40.44 g, 103.85 mmol)에 triphenylphosphine (68.10 g, 259.61 mmol), o-dichlorobenzene (520 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 14.48 g (수율: 39%)을얻었다.
[486]
[487] 7. Sub 3-38합성예
[488]
[489] (1) Sub 3-1-38합성
[490] 출발물질인 3-bromo-9,9-dimethyl-9H-fluorene (CAS Registry Number:
1190360-23-6) (61.30 g, 224.40 mmol)에 Bis(pinacolato)diboron (62.68 g, 246.84 mmol), Pd(dppf)Cl2(5.50 g, 6.73 mmol), KO Ac (66.07 g, 673.21 mmol), DMF (1120 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 47.43 g (수율: 66%)을 얻었다.
[491] (2) Sub 3-Π-38합성
[492] 상기합성에서얻어진 Sub 3-1-38 (47.43 g, 148.11 mmol)에
1 -bromo-2-nitronaphthalene (CAS Registry Number: 4185-55-1) (37.33 g, 148.11 mmol), Pd(PPh3)4 (5.13 g, 4.44 mmol), K2C03 (61.41 g, 444.32 mmol), THF (660 ml), 물 (330 ml)을첨가하고상기 Sub 3-II-l합성법을사용하여생성물 37.89 g (수율: 70%)을얻었다.
[493] (3) Sub 3-38합성
[494] 상기합성에서얻어진 Sub 3-II-38 (37.80 g, 103.69 mmol)에 triphenylphosphine (67.99 g, 259.22 mmol), o-dichlorobenzene (520 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 12.45 g (수율: 36« )을얻었다.
[495]
[496] -54합성예
Sub 3-1-54 Sub 3-11-64 Sub 3-54
[498] (1) Sub 3-1-54합성
[499] 출발물질인 9-bromo-l 1 -phenyl- 1 lH-benzo[a]carbazole (CAS Registry Number:
1374003-98-1) (53.63 g, 144.06 mmol)에 Bis(pmacolato)diboron (40.24 g, 158.47 mmol), Pd(dppf)Cl2(3.53 g, 4.32 mmol), KOAc (42.41 g, 432.19 mmol), DMF (720 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 50.14 g (수율: 83%)을 얻었다.
[500] (2) Sub 3-Π-54합성
[501] 상기합성에서얻어진 Sub 3-1-54 (50.14 g, 119.57 mmol)에
2-bromo-3-nitronaphthalene (CAS Registry Number: 67116-33-0) (30.14 g, 119.57 mmol), Pd(PPh3)4 (4.15 g, 3.59 mmol), K2C03 (49.57 g, 358.72 mmol), THF (530 ml), 물 (265 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 41.10 g (수율: 74%)을얻었다.
[502] (3) Sub 3-54합성
[503] 상기합성에서얻어진 Sub 3-II-54 (41.10 g, 88.48 mmol)에 triphenylphosphine (58.02 g, 221.20 mmol), o-dichlorobenzene (440 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 15.69 g (수율: 41%)을얻었다.
[504]
[505] -58합성예
[507] (1) Sub 3-1-58합성
[508] 출발물질인 9-bromobenzo[b]naphtho[2,l-d]thiophene (CAS Registry Number:
1628073-09-5) (59.90 g, 191.25 mmol)에 Bis(pinacolato)diboron (53.42 g, 210.37 mmol), Pd(dppf)Cl2(4.69 g, 5.74 mmol), KOAc (56.31 g, 573.74 mmol), DMF (955 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 46.85 g (수율: 68«¾)올 얻었다.
[509] (2) Sub 3-II-58합성
[510] 상기합성에서 얻어진 Sub 3-1-58 (46.85 g, 130.04 mmol)에
2-bromo- 1 -nitronaphthalene (CAS Registry Number: 4185-62-0) (32.78 g, 130.04 mmol), Pd(PPh3)4 (4.51 g, 3.90 mmol), K2C03 (53.91 g, 390.11 mmol), THF (580 ml), 물 (290 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 39.54 g (수율: 75%)을얻었다.
[511] (3) Sub 3-58합성
[512] 상기합성에서얻어진 Sub 3-II-58 (39.54 g, 97.52 mmol)에 triphenylphosphine (63.94 g, 243.79 mmol), o-dichlorobenzene (490 ml)을첨가하고상기 Sub 3-1 합성법을사용하여 생성물 11.29 g (수율 : 31%)올얻었다.
[513]
[514] 10. Sub 3-70합성예
[516] (1) Sub 3-1-70합성
[517] 출발물질인 3-bromonaphtho[2,3-b]benzofuran (CAS Registry Number:
1256544-32-7) (42.53 g, 143.13 mmol)에 Bis(pinacolato)diboron (39.98 g, 157.44 mmol), Pd(dppf)Cl2(3.51 g, 4.29 mmol), KOAc (42.14 g, 429.38 mmol), DMF (715 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 39.41 g (수율: 80%)을 얻었다.
[518] (2) Sub 3-Π-70합성
[519] 상기합성에서얻어진 Sub 3-1-70 (39.41 g, 114.49 mmol)에
2-bromo- 1 -nitronaphthalene (CAS Registry Number: 4185-62-0) (28.86 g, 114.49 mmol), Pd(PPh3)4 (3.97 g, 3.43 nunol), K2C03 (47.47 g, 343.47 mmol), THF (500 ml), 물 (250 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 37.00 g (수율: 83%)을얻었다.
[520] (3) Sub 3-70합성
[521] 상기합성에서얻어진 Sub 3-II-70 (37.00 g, 95.02 mmol)에 triphenylphosphine (62.30 g, 237.54 mmol), o-dichlorobenzene (475 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 11.89 g (수율: 35%)을얻었다.
[522]
[523]
[525] (1) Sub 3-1-82합성
[526] 출발물질인 9-bromo-l 1,11-dimethyl-l lH-benzo[a]fluorene (CAS Registry
Number: 1198396-29-0) (76.23 g, 235.84 mmol)에 Bis(pinacolato)diboron (65.88 g, 259.42 mmol), Pd(dppf)Cl2 (5.78 g, 7.08 mmol), KOAc (69.44 g, 707.51 mmol), DMF (1180 ml)를첨가하고상기 Sub 3-1-1합성법을사용하여생성물 55.02 g (수율:
63%)올얻었다.
[527] (2) Sub 3-Π-82합성
[528] 상기합성에서얻어진 Sub 3-1-82 (55.02 g, 148.58 mmol)에
l-bromo-2-nitronaphthalene (CAS Registry Number: 4185-55-1) (37.45 g, 148.58 mmol), Pd(PPh3)4 (5.15 g, 4.46 mmol), K2C03 (61.60 g, 445.75 mmol), THF (660 ml), 물 (330 ml)을첨가하고상기 Sub 3-II-1합성법을사용하여생성물 45.07 g (수율: 73%)을얻었다.
[529] (3) Sub 3-82합성
[530] 상기합성에서얻어진 Sub 3-II-82 (45.07 g, 108.47 mmol)에 triphenylphosphine
(71.13 g, 271.19 mmol), o-dichlorobenzene (540 ml)을첨가하고상기 Sub 3-1 합성법을사용하여생성물 12.90 g (수율: 31%)을얻었다.
[531] Sub 3에속하는화합물은아래와같은화합물일수있으나，이에한정되는것은 아니며，표 4는 Sub 3에속하는일부화합물의 FD-MS(Field Desorption-Mass
Spectrometry)값을나타낸것이다.
Sub 3-1 Sub 3-2 Sub 3-3 Sub 3-4 Sub 3-5 Sub 3-6 Sub 3-7 Sub 3-8
Sub 3-33 Sub 3-34 Sub 3-35 Sub 3-36 Sub 3-37 Sub 3-38 Sub 3-39 Sub 3-40 Sub 3< 1
Sub 3-79 Sub 3-80 Sub 3-81 Sub 3-82 Sub 3-83 Sub 3-84 Sub 3-85
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[544]
[545] II. Sub 4의함성
[546] 상기반웅식 4의 Sub 4는반웅식 6의반웅경로에의해합성될수있으나,이에 한정되는것은아니다.이때， Hal1및 Hal2는 Br또는 C1이다.
[547] <반웅식 6>
[549] Sub 4에속하는구체적화합물의합성예는다음과같다.
[550]
[551] 1. Sub 4-20합성예
[553] 줄발물질인 4-bromo-2-chloro-6-phenylpyrimidine (CAS Registry Number:
1412955-57-7) (21.85 g, 81.07 mmol)을둥근바닥플라스크에 THF (280 ml)로녹인 후에， 4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-l,3,2-dioxaborolane (CAS Registry Number: 256652-04-7) (22.66 g, 89.17 mmol), Pd(PPh3)4(3.75 g, 3.24 mmol), K2C03 (33.61 g, 243.20 mmol),물 (140 ml)을첨가하고 90°C에서교반하였다.반웅이 완료되면 CH2C12와물로추출한후유기층을 MgS04로건조하고농축한후 생성된화합물올 silicagel column및재결정하여생성물 19.52 g (수율: 76%)을 얻었다.
[554] 2. Sub 4-32합성예
[557] 3. Sub 4-46, Sub 4-48합성예
[559] (1) Sub 4-1-46합성
[560] 출발물질인 l-amino-2-naphthoic acid (CAS Registry Number: 4919-43-1) (75.11 g, 401.25 mmol)를등근바닥플라스크에 urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol)와함께넣고 160oC에서교반하였다. TLC로반웅을확인한후， 100°C까지냉각시키고물 (200 ml)을첨가하여 1시간동안교반하였다.반웅이 완료되면생성된고체를감압여과하고물로세척후건조하여생성물 63.86 g (수율 : 75«¾)올얻었다.
[561] (2) Sub 4-II-46합성
[562] 상기합성에서얻어진 Sub 4-1-46 (63.86 g, 300.94 mmol)을등근바닥플라스크에 P0C13 (200 ml)를상온에서녹인후에， NN-Diisopropylethylamine (97.23 g, 752.36 mmol)을천천히적가시킨후， 90°C에서교반하였다.반응이완료되면농축한후 얼음물 (500 ml)을넣고상온에서 1시간동안교반하였다.생성된고체를 감압여과하고건조하여생성물 67.47 g (수율: 90%)을얻었다.
[563] (3) Sub 4-46합성
[564] 상기합성에서얻어진 Sub 4-II-46 (33.60 g, 134.89 mmol)에
4,4,5,5-tetramethyl-2-phenyl- 1 ,3,2-dioxaborolane (CAS Registry Number:
24388-23-6) (30.28 g, 148.38 mmol), Pd(PPh3)4(6.23 g, 5.40 mmol), K2C03 (55.93 g, 404.67 mmol), THF (470 ml),물 (235 ml)올첨가하고상기 Sub 4-20합성법을 사용하여생성물 22.36 g (수율: 57%)을얻었다.
[565] (4) Sub 4-48합성
[566] 상기합성에서얻어진 Sub 4-II-46 (27.05 g, 108.60 mmol)에
4,4,5,5-tetramethyl-2-(naphthalen- 1-yl)- 1 ,3,2-dioxaborolane (CAS Registry Number: 68716-52-9) (30.36 g, 119.45 mmol), Pd(PPh3)4 (5.02 g, 4.34 mmol), K2C03 (45.03 g: 325.79 mmol), THF (380 ml),물 (190 ml)을첨가하고상기 Sub 4-20합성법을 사용하여생성물 22.21 g (수율: 60%)을얻었다.
[567] 4. Sub 4-59합성예
[569] [인 2,4-dichlorobenzo[4,5]thieno[3,2-(i]pyrimidine (CAS Registry Number:
160199-05-3) (38.00 g, 148.95 mmol)에
4,4,5,5-tetramethyl-2-phenyl- 1 ,3,2-dioxaborolane (CAS Registry Number:
24388-23-6) (33.44 g, 163.84 mmol), Pd(PPh3)4(6.88 g, 5.96 mmol), K2C03 (61.76 g, 446.85 mmol), THF (520 ml),물 (260 ml)을첨가하고상기 Sub 4-20합성법을 사용하여생성물 17.68 g (수율: 40%)을얻었다.
[570] 5. Sub 4-64합성예
[572] 출발물질인 2,4-dichlorobenzo[4,5]thieno[3,2- /]pyrimidme (CAS Registry Number:
160199-05-3) (35.15 g, 137.78 mmol)에
2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (CAS Registry Number: 947770-80-1) (44.58 g, 151.56 mmol), Pd(PPh3)4 (6.37 g, 5.51 mmol), K2C03 (57.13 g, 413.33 mmol), THF (480 ml),물 (240 ml)을첨가하고상기 Sub 4-20 합성법을사용하여생성물 22.92 g (수율: 43%)을얻었다.
[573] 6. Sub 4-71합성예
Sub 4-71
[575] 출발물질인 2,4-dichlorobenzofuro[2,3-d]pyrimidine (CAS Registry Number:
1801325-92-7) (41.43 g, 173.30 mmol)에
4,4,5,5-tetramethyl-2-phenyl- 1 ,3,2-dioxaborolane (CAS Registry Number:
24388-23-6) (38.90 g, 190.63 mmol), Pd(PPh3)4(8.01 g, 6.93 mmol), K2C03 (71.86 & 519.91 mmol), THF (600 ml),물 (300 ml)을첨가하고상기 Sub 4-20합성법을 사용하여생성물 18.49 g (수율: 38%)을얻었다.
[576] Sub 4에속하는화합물은아래와같은화합물일수있으나，이에한정되는것은 아니며，표 5는 Sub 4에속하는일부화합물의 FD-MS(Field Desorption-Mass Spectrometry)값을나타낸것이다.
，
Sub 4-33 Sub 4-34 Sub 4-35 Sub 4-36
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[588]
[589] III. Final Product 2합성
[590] Sub 3 (1당량)을등근바닥플라스크에 Toluene으로녹인후에， Sub 4 (1.1당량)， Pd2(dba)3 (0.03당량), (t-Bu)3P (0.06당량), NaOt-Bu (3당량)을 100°C에서 교반하였다.반웅이완료되면 CH2C12와물로추출한후유기층을 MgS04로 건조하고농축한후생성된화합물을 silicagel column및재결정하여 Final product 2를얻었다.
[591] 1. 3-1합성예
[593] 상기합성에서얻어진 Sub 3-1 (10.35 g, 27.06 mmol)을둥근바닥플라스크에 toluene (285ml)으로녹인후에， Sub 4-1 (CAS Registry Number: 108-86-1) (4.67 g, 29.77 mmol), Pd2(dba)3 (0.74 g, 0.81 mmol), P(i-Bu)3 (0.33 g, 1.62 mmol), NaOi-Bu (7.80 g, 81.18 mmol)을첨가하고 100°C에서교반하였다.반웅이완료되면 C¾C12 와물로추출한후유기층을 MgS04로건조하고농축한후생성된화합물을 silicagel column및재결정하여생성물 9.55 g (수율: 77%)을얻었다.
[594] 2. 3-7합성예
[596] 상기합성에서얻어진 Sub 3-15 (7.60 g, 23.50 mmol)에 Sub 4-59 (7.67 g, 25.85 mmol), Pd2(dba)3 (0.65 g, 0.70 mmol) P(t-Bu)3 (0.29 g, 1.41 mmol), NaOt-Bu (6.78 & 70.50 mmol), toluene (250 ml)을첨가하고상기 3-1합성법을사용하여생성물 9.74 g (수율 : 71%)을얻었다.
[597] 3. 3-8합성예
[599] 상기합성에서얻어진 Sub 3-11 (8.00 g, 24.74 mmol)에 Sub 4-46 (7.91 g, 27.21 mmol), Pd2(dba)3 (0.68 g, 0.74 mmol) P(i-Bu)3 (0.30 g, 1.48 mmol), NaOt-Bu (7.13 g, 74.21 mmol), toluene (260 ml)을첨가하고상기 3-1합성법을사용하여생성물 10.43 g (수율： 73%)을얻었다.
[600] 4. 3-11합성예
[602] 상기합성에서 얻어진 Sub 3-32 (8.12 g, 22.72 mmol)에 Sub 4-6 (CAS Registry Number: 103068-20-8) (7.73 g, 24.99 mmol), Pd2(dba)3 (0.62 g, 0.68 mmol) P(t-Bu): (0.28 g, 1.36 mmol), NaOr-Bu (6.55 g, 68.16 mmol), toluene (240 ml)을첨가하고 상기 3-1합성법을사용하여생성물 9.85 g (수율: 74%)을얻었다.
[603] 5. 3-16합성예
[605] 상기합성에서 얻어진 Sub 3-82 (8.40 g, 21.90 mmol)에 Sub 4-11 (CAS Registry Number: 1153-85-1) (7.76 g, 24.09 mmol), Pd2(dba)3 (0.60 g, 0.66 mmol) P(r-Bu)3 (0.27 g, 1.31 mmol), NaOi-Bu (6.32 g, 65.71 mmol), toluene (230 ml)을첨가하고 상기 3-1합성법을사용하여생성물 9.31 g (수율: 68%)을얻었다.
[606] 6. 3-17합성예
Sub 3-54 Sub 4-12 3-17
[608] 상기합성에서 얻어진 Sub 3-54 (9.27 g, 21.43 mmol)에 Sub 4-12 (CAS Registry Number: 97511-04-1) (6.20 g, 23.58 mmol), Pd2(dba)3 (0.59 g, 0.64 mmol) P(r-Bu)3 (0.26 g, 1.29 mmol), NaO/-Bu (6.18 g, 64ᅳ 30 mmol), toluene (225 ml)을첨가하고 상기 3-1합성법을사용하여생성물 9.09 g (수율: 69%)을얻었다.
[609] 7. 3-47합성예
[611] 상기합성에서얻어진 Sub 3-70 (8.09 g, 22.64 mmol)에 Sub 4-71 (6.99 g, 24.90 mmol), Pd2(dba)3 (0.62 g, 0.68 mmol) P(i-Bu)3 (0.27 g, 1.36 mmol), NaOr-Bu (6.53 g: 67.91 mmol), toluene (240 ml)을첨가하고상기 3-1합성법을사용하여생성물 10.08 g (수율 : 74%)올얻었다.
[612] 8. 3-49합성예
[614] 상기합성에서얻어진 Sub 3-1 (9.48 g, 24.79 mmol)에 Sub 4-37 (CAS Registry Number: 29874-83-7) (6.56 g, 27.26 mmol), Pd2(dba)3 (0.68 g, 0.74 mmol) P(i-Bu)3 (0.30 g, 1.49 mmol), NaOi-Bu (7.15 g, 74.36 mmol), toluene (260 ml)을첨가하고 상기 3-1합성법을사용하여생성물 10.18 g (수율: 70%)을얻었다.
[615] 9. 3-52합성예
[617] 상기합성에서 얻어진 Sub 3-38 (7.50 g, 22.49 mmol)에 Sub 4-32 (9.58 g, 24.74 mmol), Pd2(dba)3 (0.62 g, 0.67 mmol) P(i-Bu)3 (0.27 g, 1.35 mmol), NaOt-Bu (6.49 g. 67.48 mmol), toluene (235 ml)을첨가하고상기 3-1합성법을사용하여생성물 9.64 g (수율 : 67%)을얻었다.
[618] 10. 3-70합성예
[620] 상기합성에서얻어진 Sub 3-58 (7.79 g, 20.86 mmol)에 Sub 4-48 (7.82 g, 22.94 mmol), Pd2(dba)3 (0.57 g, 0.63 mmol) P(r-Bu)3 (0.25 g, 1.25 mmol), NaOi-Bu (6.01 g., 62.58 mmol), toluene (220 ml)을첨가하고상기 3-1합성법을사용하여생성물 10.32 g (수율: 73%)을얻었다.
[621] 11. 3-81합성예
[623] 상기합성에서얻어진 Sub 3-8 (그 11 g, 21.98 mmol)에 Sub 4-20 (7.66 g, 24.18 mmol), Pd2(dba)3 (0.60 g, 0.66 mmol) P(f-Bu)3 (0.27 g, 1.32 mmol), NaOi-Bu (6.34 g, 65.95 mmol), toluene (230 ml)을첨가하고상기 3-1합성법을사용하여생성물 9.42 g (수율 : 71%)을얻었다.
[624] 12. 3-93합성예
[626] 상기합성에서 얻어진 Sub 3-13 (9.14 g, 24.47 mmol)에 Sub -27 (CAS Registry Number: 80984-79-8) (8.40 g, 26.92 mmol), Pd2(dba)3 (0.67 g, 0.73 mmol) P(i-Bu)3 (0.30 g, 1.47 mmol), NaOt-Bu (7.06 g, 73.42 mmol), toluene (260 ml)을첨가하고 상기 3-1합성법을사용하여생성물 10.21 g (수율: 69%)을얻었다.
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[628]
[629] 한편 ,상기에서는화학식 1및화학식 2로표시되는본발명의 예시적합성예를 설명하였지만,이들은모두 Buchwald-Hartwig cross coupling반웅, Miyaura boration반웅， Suzuki cross-coupling반웅， Intramolecular acid-induced cyclization 반응 mater. Chem. 1999, 9， 2095.), Pd(II)-catalyzed oxidative cyclization반웅 ( Org. Lett. 2011, 13, 5504), Grignard반응, Cyclic Dehydration반응및 PPh3-mediated reductive cyclization반웅 (/. Org. Chem. 2005, 70, 5014.)등에기초한것으로 구체적합성예에명시된치환기이외에화학식 1및화학식 2에정의된다른 치환기 (Ar1내지 Ar3, L1내지 , R1내지 R7, X1, X2, X3, A, B, C, D, E, F등의 치환기)가결합되더라도상기반웅이진행된다는것을당업자라면쉽게이해할 수있을것이다.
[630] 유기전기소자의제조평가
[631] [실시예 1]내지 [실시예 95]적색유기전기발광소자 (발광층흔합인광호스트) [632] 먼저,유리기판에형성된 ITO층 (양극)위에우선정공주입층으로서
4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA로약기함)'막을 진공증착하여 60 nm두께로형성하였다.이어서，
N,N'-Bis(l-naphthalenyl)-N,N'-bis-phenyl-(l,l'-biphenyl)-4,4'-diamine (이하 NPB로 약기함)을 60 mn두께로진공증착하여정공수송충을형성하였다.정공수송충 상부에호스트로서화학식 1과화학식 2로표시되는본발명화합물 (표 7에
기재)을 3:7로흔합한흔합물을사용하였으며 ,도판트로서는 (piq)2Ir(acac)
[bis-(l-phenylisoquinolyl)iridium(m)acetylacetonate]을 5%중량으로도핑함으로써 상기정공수송층위에 30nm두께의발광층을증착하였다.정공저지층으로 (Ι,Γ-비스페닐) -4-올레이토)비스 (2-메틸 -8-퀴놀린올레이토)알루미늄 (이하 BAlq로약기함)을 10 nm두께로진공증착하고,전자수송층으로
Bis(10-hydroxybenzo[h]quinolinato)beryllium (이하 BeBq2로약칭함)을 50 nm 두께로성막하였다.이후,전자주입층으로할로젠화알칼리금속인 LiF를 0.2 nm 두께로증착하고,이어서 A1을 150 nm의두께로증착하여음극으로
사용함으로써유기전기발광소자를제조하였다.
[633] [비교예 1]내지 [비교예 3]
[634] 화학식 2로표시되는본발명화합물을단독으로호스트로사용하는것을
제외하고는상기실시예 1과동일한방법으로유기전기발광소자를제작하였다.
[635] [비교예 4]
[636] 비교화합물 1을단독으로호스트로사용하는것을제외하고는상기실시예 1과 동일한방법으로유기전기발광소자를제작하였다.
[637] [비교예 5]
[638] 비교화합물 2를단독으로호스트로사용하는것을제외하고는상기실시예 1과 동일한방법으로유기전기발광소자를제작하였다.
[639] [비교예 6]
[640] 비교화합물 3을단독으로호스트로사용하는것올제외하고는상기실시예 1과 동일한방법으로유기전기발광소자를제작하였다.
[641] [비교예 7]
[642] 비교화합물 4를단독으로호스트로사용하는것을제외하고는상기실시예 1과 동일한방법으로유기전기발광소자를제작하였다.
[643] [비교예 8]
[644] 비교화합물 1과비교화합물 2를혼합하여호스트로사용하는것을제외하고는 상기실시예 1과동일한방법으로유기전기발광소자를제작하였다.
[645] [비교예 9]
[646] 비교화합물 3과비교화합물 4를흔합하여호스트로사용하는것을제외하고는 상기실시예 1과동일한방법으로유기전기발광소자를제작하였다.
[647] 비교화합물 1비교화합물 2비교화합물 3비교화합물 4
[649] 본발명의실시예 1내지실시예 95및비교예 1내지비교예 9에의해제조된
유기전기발광소자들에순바이어스직류전압을가하여포토리서치
(photoresearch)사의 PR-650으로전기발광 (EL)특성을측정하였으며 , 2500 cd/m2 기준휘도에서맥사이언스사의수명측정장비를통해 T95수명을측정하였으며， 그측정결과는하기표 7과같다.
표 7]
[651]
[652] 상기표 7의결과로부터알수있듯이，화학식 1과화학식 2로표시되는본
발명의유기전기발광소자용재료를흔합하여인광호스트로사용할경우 (실시예 1내지실시예 95),단일물질을사용한소자 (비교예 1내지비교예 7)에 비해구동전압,효율및수명을현저히개선시키는것을확인할수있었다ᅳ
[653] 상세히설명하면,화학식 2로표시되는본발명의화합물，비교화합물 1내지 비교화합물 4를단독으로인광호스트로사용한비교예 1내지비교예 7에 있어서는본발명화합물 (3-6, 3-61, 3-74)을사용한비교예 1내지비교예 3이 비교화합물을사용한비교예 4내지비교예 7보다높은효율과높은수명을 나타내는것을확인할수있었다.
[654] 또한상기단독물질을사용한비교예 1내지비교예 7보다비교화합물 1과
비교화합물 2또는비교화합물 3과비교화합물 4를흔합하여인광호스트로 사용한비교예 8，비교예 9가좀더높은효율을나타내는것을확인할수있었다. 비교예 8과비교예 9를비교하여보면,동일한질소원자를갖는 5환의
헤테로고리화합물을흔합한비교예 8보다 5환고리화합물증서로상이한 헤테로원자 (N, S)를갖는이형다환고리화합물을포함한흔합물올사용한 비교예 9가좀더높은효율을나타내는것을확인할수있었다.
[655] 그리고상기비교예 1내지비교예 9의경우보다본발명화합물인화학식 1과 화학식 2의화합물을흔합하여호스트로사용한실시예 1내지실시예 95가 현저히높은효율및수명을나타내는것을확인할수있었으며,낮은
구동전압을나타내는것올확인할수있었다.
[656] 본발명자들은상기실험결과를근거로화학식 1의물질과화학식 2의물질을 흔합한물질의경우각각물질에대한특성이외의다른신규한특성을갖는다고 판단하여，화학식 1의물질，화학식 2의물질,본발명흔합물을각각사용하여 PL lifetime을측정하였다.그결과본발명화합물인화학식 1과화학식 2를 흔합하였을경우단독화합물일때와달리새로운 PL파장이형성되는것을 확인할수있었으며,새롭게형성된 PL파장의감소및소멸시간은화학식 1및 화학식 2의물질각각의감소및소멸시간보다작게는약 60배에서많게는약 360배까지증가하는하는것을확인할수있었다.이는본발명화합물을 흔합하여사용할경우각각의물질이갖는에너지준위를통해전자와정공이 이동되는것뿐만아니라,흔합으로인하여형성된새로운에너지준위를갖는 신규영역에 (exciplex)의한전자,정공이동또는에너지전달로효율및수명이
증가하는것으로판단된다.이는결과적으로상기본발명흔합물을사용할경우 혼합박막이 exciplex에너지전달및발광프로세스를보이는중요한예라고할 수있다.
[657] 또한비교화합물을흔합한인광호스트로사용한비교예 8내지비교화합물
9보다본발명의조합이우수한이유는 electron뿐만아니라 hole에대한안정성 , 높은 T1등의특징이있는화학식 2로표시되는다환고리화합물에 hole특성이 강한화학식 1로표시되는화합물을흔합할경우,높은 T1과높은 LUMO에너지 값으로인해전자블로킹능력이향상되고,발광층에더많은 hole이빠르고쉽게 이동하게된다.이에따라정공과전자의발광층내 charge balance가증가되어 정공수송층계면이아닌발광층내부에서발광이잘이루어지고，그로인해 HTL 계면에열화또한감소하여소자전체의구동전압，효율그리고수명이극대화 된다고판단된다.또한화학식 1로표시되는화합물에서는아민에축합된 (fused) 스파이로플루오렌이치환된본발명화합물이구동전압，효율，수명면에서 가장우수한결과를나타냄을확인할수있었고,그중에서도축합된스파이로 플루오렌과함께아민에다이메틸플루오렌이치환될경우는발광효율적인 측면에서더개선되는것을확인할수있었다.즉，결론적으로화학식 1과 화학식 2의조합이전기화학적으로시너지작용을하여소자전체의성능을 향상된것으로사료된다.
[658]
[659] [실시예 96]내지 [실시예 98]흔합비율별적색유기전기발광소자 (발광층혼합 인광호스트)
[660] 표 8에기재된대로물질의혼합비용을다르게사용한것을제외하고는상기 실시예 68과동일한방법으로유기전기발광소자를제작하였다.
[661]
[662] [실시예 99]내지 [실시예 101]흔합비율별적색유기전기발광소자 (발광층 혼합인광호스트)
[663] 표 8에기재된대로물질의혼합비용을다르게사용한것을제외하고는상기 실시예 9와동일한방법으로유기전기발광소자를제작하였다.
[664] 본발명의실시예 9，실시예 68,실시예 96내지실시예 101에의해제조된
유기전기발광소자들에순바이어스직류전압을가하여포토리서치
(photoresearch)사의 PR-650으로전기발광 (EL)특성을측정하였으며， 2500 cd/m2 기준휘도에서맥사이언스사의수명측정장비를통해 T95수명을측정하였으며， 그측정결과는하기표 8과같다.
[665]
[666] [표 8]
[667]
[668] 상기표 8과같이본발명의화합물의흔합물을비율별 (2:8, 3:7, 4:6， 5:5)로
소자를제작하여측정하였다.결과를자세히설명하면,화합물 1-56과화합물
3-61의흔합물결과에서는 2:8， 3:7의경우구동전압,효율및수명의결과가 유사하게우수했지만 4:6， 5:5와같이제 1호스트의비율이증가하면서구동전압, 효율및수명의결과가점점떨어지는것을확인하였고,이는화합물 2-48과 화합물 3-6의흔합물결과에서도동일한양상을띄었다.이는 2:8， 3:7과같이 hole 특성이강한화학식 1로표시되는화합물이적정한양이흔합될경우，발광층내 charge balance가극대화되기때문이라설명할수있다.
[669] 이상의설명은본발명을예시적으로설명한것에불과한것으로，본발명이 속하는기술분야에서통상의지식을가지는자라면본발명의본질적인 특성에서벗어나지않는범위에서다양한변형이가능할것이다.따라서，본 명세서에개시된실시 예들은본발명을한정하기위한것이아니라설명하기 위한것이고，이러한실시 예에의하여본발명의사상과범위가한정되는것은
아니다ᅳ본발명의보호범위는아래의청구범위에의하여해석되어야하며，그와 동등한범위내에있는모든기술은본발명의권리범위에포함하는것으로 해석되어야할것이다
Claims
청구범위
[청구항 1] 제 1전극,제 2전극및상기제 1전극과상기제 2전극사이에형성된
유기물층을포함하는유기전기소자에 있어서，상기유기물층은발광층을 포함하고，상기발광층은인광성발광층으로서하기화학식 1로표시되는 제 1호스트화합물및하기화학식 2로표시되는제 2호스트화합물을 포함하는것을특징으로하는유기전기소자
{상기화학식 1및화학식 2에서，
1) X1은 CR b또는하기화학식 1-a이고
1-a
상기화학식 1-a에서，점선은 X1으로부터의결합을나타내며，
2) X2및 X3은서로독립적으로 Ν-ΙΛΑΓ4, 0， S, CR b또는상기화학식 1-a이며，이때상기화학식 1-a에서점선은 X2또는 X3으로부터의결합을 나타내고,
3) Ra및 Rb는서로독립적으로수소; C6-C60의아릴기;플루오렌일기; 0, N,
5, Si및 P로이루어진군에서선택된적어도하나의헤테로원자를 포함하는 C2-C6。의헤테로고리기; C3-C6。의지방족고리와 C6-C60의 방향족고리의융합고리기; ^- 0의알킬기; C2-C2。의알켄일기;로 이루어진군에서선택되며,
4) h및 i는 0또는 1의 정수이고,단， h+i는 1이상이며 ,여기서 h또는 i가 0일경우는직접결합을의미하고,
5) Ar1, Ar2, Ar3및 Αι4는서로독립적으로 C6-C60의아릴기； 0, N, S, Si및 P로이루어진군에서선택된적어도하나의헤테로원자를포함하는
6。의헤테로고리기；플루오렌일기; C6-C6。의방향족고리와 C3-C6。의 지방족고리의융합고리기； -C50의알킬기； C2-C20의알켄일기； C2-C2。의 알킨일기； d-C30의알콕실기； C6-C30의아릴옥시기；및 -La-N(R (Rd);로 이루어진군에서선택되고, (여기서상기 1 는단일결합; C6-C60의
아릴렌기;플루오렌일렌기; O, N, S, Si및 P중적어도하나의
해테로원자를포함하는 C2-C60의헤테로고리기; ^- 0의지방족고리와 C6
- 。의방향족고리의융합고리기;및지방족탄화수소기로이루어진 군에서선택되며，상기 및 Rd는서로독립적으로 C6-C60의아릴기； 플루오렌일기； 0, N, S, Si및 P로이루어진군에서선택된적어도하나의 헤테로원자를포함하는 C2-C60의헤테로고리기; CrC60의지방족고리와 C6 -C60의방향족고리의융합고리기;로이루어진군에서선택됨)
6)또한 Ari과 Ar2는서로결합하여고리를형성할수있고,
7) η은 1또는 2의정수이며， η이 2일경우 2개의 Ar!은각각동일하거나 상이하고, 2개의 Ar2는각각동일하거나상이하며,
8) ΙΛ L2및 L3은서로독립적으로단일결합; C6-C60의아릴렌기 ;
플루오렌일렌기 ; 0, N, S, Si및 P증적어도하나의헤테로원자를
포함하는 C2-C60의헤테로고리기； C3-C60의지방족고리와 Qr o의 방향족고리의융합고리기;및지방족탄화수소기;로이루어진군에서 선택되며,
9) 3, 1)， <;， 6및 는서로독립적으로 0내지 10의정수이고, d는 0내지 5의 정수이고， f는 0내지 2의정수이며,
10) R1, R2, R3, R4, R5, R6및 R7은서로독립적으로수소;중수소;삼중수소; 할로겐;시아노기；나이트로기； C6-C60의아릴기；플루오렌일기； 0, N, S, Si 및 P로이루어진군에서선택된적어도하나의헤테로원자를포함하는 C2 -Qo의헤테로고리기; C3-C60의지방족고리와 C6-C60의방향족고리의 융합고리기; crc50의알킬기; c2-c2。의 알켄일기; c2-c20의 알킨일기; crc
30의알콕실기; C6-C30의아릴옥시기;및 -La-N(Rc)(Rd);로이루어진군에서 선택되고，또는상기 a, b, c, d, e및 g가 2이상인경우및 f가 2인경우는 각각복수로서서로동일하거나상이하며복수의 Ri끼리혹은복수의 R2 끼리혹은복수의 R3끼리혹은복수의 R4끼리혹은복수의 R5끼리혹은 복수의 R6끼리혹은복수의 R7끼리서로결합하여고리를형성할수 있으며,
11) A, B, C, D, E및 F는서로독립적으로 C6-C20의아릴기또는 C2-C2。의 헤테로고리기이며,
단 , Ε및 F모두치환또는비치환된 C6의아릴기 (페닐기)인경우에는 제외하며，
여기서，상기아릴기，플루오렌닐기，아릴렌기,해테로고리기,
융합고리기,알킬기,알켄일기,알콕시기,아릴옥시기는각각중수소; 할로겐; d- o의알킬기또는 C6-C20의아릴기로치환또는비치환된 실란기；실록산기;붕소기;게르마늄기；시아노기;니트로기; -La-N(Rc)(Rd); ^- 0의알킬싸이오기 ; d-C2。의알콕실기; CrC20의알킬기; CrC20의 알켄일기； C2-C2。의알킨일기； C6-C2。의아릴기；중수소로치환된 C6-C20의
아릴기；플루오렌일기; C2-C2。의해테로고리기; C3-C20의시클로알킬기; c7 -c20의아릴알킬기및 c8-c20의아릴알켄일기로이루어진군에서선택된 하나이상의치환기로더욱치환될수있으며，또한이들치환기들은서로 결합하여고리를형성할수도있으며，여기서 '고리 '란탄소수 3내지 60의 지방족고리또는탄소수 6내지 60의방향족고리또는탄소수 2내지 60의 헤테로고리또는이들의조합으로이루어진융합고리를말하며，포화 또는불포화고리를포함한다.)
[청구항 2] 제 2항에 있어서,상기화학식 1및 2의 L1, 및 L3가하기화학식 A-1 내지 A-13중에어느하나인화합물인것을특징으로하는유기전기소자 -1 A-2 A-3 A-4 A-5 A-6
{상기화학식 A-1내지화학식 A-13에서,
1) Y는 N-L4-Ar5, 0, S, CReRf또는하기화학식 1-b이고
화학식 1-b
상기화학식 1-b에서，점선은 Y로부터의결합을나타내고
2) L4는상기 청구항 1에서 L3의정의와동일하고,
3) Ar5는상기청구항 1에서 Ar4의정의와동일하며，
4) Re및 Rf는상기 청구항 1에서 Ra의정의와동일하고，
5) R"및 R12는상기청구항 1에서 R1의정의와동일하고，
6) G및 H는상기청구항 1에서 A의정의와동일하고,
7) j및 k는상기청구항 1에서 a의정의와동일하고，
8) &'， (：'，(1'및 ^은서로독립적으로0내지 4의정수이고， b'은 0내지 6의 정수이며， f 및 g'은서로독립적으로 0내지 3의정수이고， h'는 0내지 2의 정수이며, i'는 0또는 1의정수이고，
9) R8, R9및 R10은서로독립적으로수소;중수소;삼중수소;할로겐;
시아노기；나이트로기 ; C6-C6。의아릴기；플루오렌일기; 0， N, S, Si및 P로 이루어진군에서선택된적어도하나의헤테로원자를포함하는 C2-C60의 헤테로고리기; CrC60의지방족고리와 C6-C6。의방향족고리 ^융합고리기; ^- 0의알킬기; C2-C20의알켄일기; C2-C20의알킨일기; d-C3。의
알콕실기; C6-C3。의아릴옥시기;및 -La-N(Rc)(Rd);로이루어진군에서 선택되고，또는상기 a', b', c', d', e', f 및 g'가 2이상인경우및 h'가 2인 경우는각각복수로서서로동일하거나상이하며복수의 R8끼리혹은 복수의 R9끼리혹은복수의 R10끼리흑은이웃한 R8과 R9또는 R9과 R10은 서로결합하여방향족고리또는헤테로방향족고리를형성할수있고,
10) La는상기청구항 1에서 La의정의와동일하고, Rc및 Rd는상기청구항 1에서 및 Rd의정의와동일하고，
Ι ^ Ζ', Ζ2및 Z3은서로독립적으로 CR13또는 Ν이고， Ζ', Ζ2및 Ζ3중적어도 하나는 Ν이며,
12) R'3은수소;중수소;삼중수소;할로겐;시아노기；나이트로기； C6-C60의 아릴기;플루오렌일기; 0，^ 5， 및1>로이루어진군에서선택된적어도 하나의헤테로원자를포함하는 C2- o의헤테로고리기; C3-C60의 지방족고리와 C6- 。의방향족고리의융합고리기; C,-C5。의알킬기; C2-C20 의알켄일기; C2-C2。의알킨일기; d-C3。의알콕실기; C6-C3。의아릴옥시기; 및 -La-N(Rc)(Rd);로이루어진군에서선택되고,이웃한 R8과 R13은서로 결합하여방향족고리또는헤테로방향족고리를형성할수있다.)
[청구항 3] 제 1항에 있어서,상기화학식 1로나타내는제 1호스트화합물이하기 화학식 1-1내지화학식 1_5중어느하나로표시되는것을특징으로하는 유기전기소자
-3
화학식 1-4화학식 1-5
{상기화학식 1-1내지화학식 1-5에서,
1) X1, C, D, R3, R4, c, d, Ar1및 Ar2는상기청구항 1에서정의된바와같고
2) Y는 N-L4-Ar5, 0， S, CReRf또는하기화학식 1-b이고,
화학식 1-b
상기화학식 1-b에서，점선은 Y로부터의결합을나타내며,
3) L4는상기청구항 1에서 L3의정의와동일하고，
4) Ar5는상기청구항 1에서 Ar4의정의와동일하고，
5) Re및 Rf는상기청구항 1에서 Ra의정의와동일하고,
6) R11및 R12는상기청구항 1에서 R1의정의와동일하고，
7) G및 H는상기청구항 1에서 A의정의와동일하고，
8) j및 k는상기청구항 1에서 a의정의와동일하고，
9) a', c'및 d'은서로독립적으로 0내지 4의정수이고, f 및 g'은서로 독립적으로 0내지 3의정수이고 h'는 0내지 2의정수이며,
10) R8및 R9는서로독립적으로수소;중수소;삼증수소;할로겐;
시아노기 ;나이트로기 ; C6-C60의아릴기 ;플루오렌일기 ; 0, N, S, Si및 P로 이루어진군에서선택된적어도하나의헤테로원자를포함하는 C2-C6。의 헤테로고리기; c3-c60의지방족고리와 c6-c6。의방향족고리의융합고리기; crc50의알킬기； C2-C2。의알켄일기； C2-C20의알킨일기； d-C3。의
알콕실기; 30의아릴옥시기;및 -La-N(Re)(Rd);로이루어진군에서 선택되고,또는상기 a', c', d', f 및 g'가 2이상인경우및 h'가 2인경우는 각각복수로서서로동일하거나상이하며복수의 R8끼리흑은복수의 R9 끼리혹은이웃한 R8과 R9가서로결합하여방향족고리또는 헤테로방향족고리를형성할수있고,
11) , 및 는상기 청구항 1에서 ΙΛ 및 RD의정의와동일하다. }
[청구항 4] 제 1항에 있어서,상기화학식 1로나타내는제 1호스트화합물이하기 화학식 1-6내지화학식 1-20중어느하나로표시되는것을특징으로 하는유기전기소자
화학식 1-6화학식 1-7화학식 1-8
화학식 1-9화학식 1-10화학식 1-11
화학식 1-12화학식 1-13화학식 1-14
화학식 1-15화학식 1-16화학식 1-17
화학식 1-18화학식 1-19화학식 1-20
{상기화학식 1-6내지화학식 1-20에서，
1) Ra, Rb, R1, R2, R3, R4, a, b, c, d, L1, Ar1, Ar2및 n은상기청구항 1에서 정의된바와같고，
2) A, B, C및 D는 C10의아릴기이다. }
[청구항 5] 제 1항에 있어서，상기화학식 1로나타내는제 1호스트화합물이하기 화학식 1-21내지화학식 1-23중어느하나로표시되는것을특징으로 하는유기전기소자
화학식 1-21화학식 1-22화학식 1-23
{상기화학식 1-21내지화학식 1-23에서,
1) C, D, R3, R4, c, d, L1, Ar1및 Ar2는상기청구항 1에서정의된바와같고
2) W는 Ν-ΙΛΑτ6, 0, S, CR h또는하기화학식 1-c이며， 퐈학식 1-c
상기화학식 1-c에서，점선은 W로부터의결합을나타내고，
3) L5는상기청구항 1에서 L3의정의와동일하고， Ar«는상기청구항 1에서 Ar4의정의와동일하며，
4) Rg및 Rh는상기 청구항 1에서 Ra의정의와동일하고,
5) R15및 R16은상기청구항 1에서 R1의정의와동일하고,
6) I및 J는상기청구항 1에서 A의정의와동일하고，
7) o및 p는상기청구항 1에서 a의정의와동일하고，
8) 1은 0내지 3의정수이고， m은 0내지 4의정수이며,
9) R13및 R14는서로독립적으로수소;중수소;삼중수소;할로겐;
시아노기；나이트로기 ; C6-C60의아릴기；플루오렌일기; 0, N, S, Si및 P로 이루어진군에서선택된적어도하나의헤테로원자를포함하는 C2-C60의 헤테로고리기; - 。의지방족고리와 C6-C60의방향족고리의융합고리 / CrC5。의알킬기； C2-C2。의알켄일기； C2-C20의알킨일기； C,-C3。의 알콕실기; C6-C30의아릴옥시기;및 -La-N(Re)(Rd);로이루어진군에서 선택되고，복수의 Ri3끼리혹은복수의 R"끼리혹은이웃한 R13과 R14가 서로결합하여방향족고리또는헤테로방향족고리를형성할수있고，
10) 1Λ Rc및 Rd는상기청구항 1에서 L 및 Rd의정의와동일하며，
11) 2개의 Ar2는각각동일하거나상이하고, 2개의 W는각각동일하거나 상이하며,복수의 R'3및복수의 R"는서로동일하거나상이하다. }
[청구항 6] 제 1항에 있어서，상기화학식 1에서 n이 1인경우의화합물인것을
특징으로하는유기전기소자
[청구항 7] 제 1항에 있어서，상기화학식 1에서 n이 2인경우의화합물인것을
특징으로하는유기전기소자
[청구항 8] 제 1항에 있어서，상기화학식 1및화학식 2에서 A, B, C, D, E및 F가하기 화학식 B-1내지화학식 B-7로이루어진군에서선택되는것을특징으로 하는유기전기소자
화학식 B-1화학식 B-2화학식 B-3화학식 B-4
-5화학식 Β-6화 -7
{상기화학식 B-1내지화학식 B-7에서,
(1) Z4내지 Z51은 CRi또는 N이며,
(2) R는상기청구항 1에서 Ra의정의와동일하고,
(3) *는축합되는위치를나타낸다. }
[청구항 9] 제 1항에 있어서，상기화학식 2로나타내는제 2호스트화합물이하기 화학식 3또는화학식 4로표시되는것을특징으로하는유기전기소자 화학식 3화학식 4
{상기화학식 3및 4에서，
E, F, R5, R6, R7, e, f, g, , Ar3, X2및 X3은상기청구항 1에서정의된바와 같다. }
[청구항 10] 제 1항에있어서，상기화학식 2의 R6이방향족고리또는헤테로방향족 고리를반드시형성하고있는것을특징으로하는유기전기소자
[청구항 11] 제 1항에 있어서，상기화학식 2로나타내는제 2호스트화합물이하기 화학식 5-1내지화학식 5-24중어느하나로표시되는것을특징으로 하는유기전기소자
화학식 5-1화학식 5-2화학식 5-3
화학식 5-7화학식 5-8화학식 5-9
화학식 5-10화학식 5-11화학식 5-12
화학식 5-16화학식 5-17화학식 5-18
화학식 5-19화학식 5-20화학식 5-21
-22화학식 5-23화학식 5-24
{상기화학식 5-1내지화학식 5-24에서，
R5, R6, R7, e, f, g, ΙΛ Ar3, X2및 X3은상기청구항 1에서정의된바와같다. } [청구항 12] 제 1항에 있어서，상기화학식 2로나타내는제 2호스트화합물이하기 화학식 6-1내지화학식 6-8중어느하나로표시되는것을특징으로하는 유기전기소자
-1화학식 6-2화학식 6-3화학식 6-4
화학식 6-5화학식 6-6화학식 6-7화학식 6-8
{상기화학식 6-1내지화학식 6-8에서
E, F, R5, R6, R7, Ra, Rb, e, f, g，！ Λ L3, Ar3및 Ar4는상기청구항 1에서정의된 바와같다. }
[청구항 13] 제 1항에있어서，상기화학식 1로나타내는제 1호스트화합물이하기 화합물 1-1내지화합물 1-70및화합물 2-1내지화합물 2-115중어느
1-21 1-22 1-23 1-24 1-25
701
OAVii s/s8ss8
:2/1Μ20-Ϊ006Ώ 8
PCT/KR2017/009238
8CZ600/Z.T0ZaM/X3d »S8£0/8I0Z OAV
ΠΙ
8CZ600/Z.lOZaM/X3d »S8£0/810Z OAV
zu
[청구항 15] 제 1항에있어서,제 1전극과발광층사이에 1층이상의
정공수송대역층을포함하고,상기정공수송대역층은정공수송층, 발광보조층또는이둘을모두포함하며，상기정공수송대역층이상기 화학식 1로표시되는화합물을포함하는것을특징으로하는 유기전기소자
[청구항 16] 제 1항에있어서，상기화학식 1및상기화학식 2로나타내는화합물 o
1:9내지 9:1중어느하나의비율로흔합되어발광층에사용되는것을 특징으로하는유기전기소자
[청구항 17] 제 1항에있어서,상기화학식 1및상기화학식 2로나타내는화합물 o
1:9또는 5:5로흔합되어발광층에사용되는것을특징으로하는 유기전기소자
[청구항 18] 제 1항에있어서,상기화학식 1및상기화학식 2로나타내는화합물 o
2:8또는 3:7로흔합되어발광층에사용되는것을특징으로하는 유기전기소자
[청구항 19] 제 1항의유기전기소자를포함하는디스플레이장치；및상기
디스플레이장치를구동하는제어부;를포함하는전자장치
[청구항 20] 제 19항에있어서，상기유기전기소자는유기전기발광소자，
유기태양전지，유기감광체，유기트랜지스터및단색또는백색 조명용소자중적어도어느하나인것을특징으로하는전자장치
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| CN110229071A (zh) * | 2019-06-06 | 2019-09-13 | 北京诚志永华显示科技有限公司 | 芴衍生物有机电致发光器件 |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR102170190B1 (ko) | 2020-10-26 |
| KR20180022325A (ko) | 2018-03-06 |
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