JP6946186B2 - ヘテロ環化合物 - Google Patents
ヘテロ環化合物 Download PDFInfo
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- JP6946186B2 JP6946186B2 JP2017527611A JP2017527611A JP6946186B2 JP 6946186 B2 JP6946186 B2 JP 6946186B2 JP 2017527611 A JP2017527611 A JP 2017527611A JP 2017527611 A JP2017527611 A JP 2017527611A JP 6946186 B2 JP6946186 B2 JP 6946186B2
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 113
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 71
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 238000005401 electroluminescence Methods 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910005965 SO 2 Inorganic materials 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 230000005669 field effect Effects 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
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- 238000007639 printing Methods 0.000 description 4
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- 125000005259 triarylamine group Chemical group 0.000 description 4
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
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- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
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- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- 238000005092 sublimation method Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- UPNFMHMMXOKBOJ-UHFFFAOYSA-N zinc iridium(3+) oxygen(2-) Chemical compound [Ir+3].[O-2].[Zn+2] UPNFMHMMXOKBOJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- 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
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- 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
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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Description
(1)基板、
(2)電極、多くは、金属もしくは無機であるが、有機もしくはポリマー伝導性材料からも成る、
(3)電荷注入層(複数)もしくは中間層(複数)、たとえば、電極での不均性の補償用のためであり(「平坦化層」)、多くは、伝導性のドープされたポリマーから成る、
(4)有機半導体、
(5)可能ならば、さらなる電荷輸送層、電荷注入層もしくは電荷ブロック層、
(6)対電極、(2)で特定された材料、
(7)被包。
Xは、出現毎に同一か異なり、NまたはCR1、好ましくは、CR1であり、ただし、一つの環において、2個を超えないX基は、Nであり;
Zは、結合、C(R1)2、OまたはSであり;
L1は、結合、6〜60個の、好ましくは、6〜40個の、より好ましくは、6〜20個の炭素原子を有する芳香族環構造、または3〜60個の、好ましくは、3〜40個の、より好ましくは、3〜20個の炭素原子を有する複素環式芳香族環構造であり、夫々、1以上のR1基により置換されてよく、好ましくは、結合、6〜60個の、好ましくは、6〜40個の、より好ましくは、6〜20個の炭素原子を有するアリール基、または3〜60個の、好ましくは、6〜40個の、より好ましくは、6〜20個の炭素原子を有するヘテロアリール基であり、夫々、1以上のR1基により置換されてよく;
Ar1、Ar2、Ar3は、6〜40個の、好ましくは、6〜20個の炭素原子を有するアリール基、または3〜40個の、好ましくは、3〜20個の炭素原子を有するヘテロアリール基であり、夫々、1以上のR1基により置換されてよく;
R1は、出現毎に同一か異なり、H、D、F、Cl、Br、I、B(OR2)2、CHO、C(=O)R2、CR2=C(R2)2、CN、C(=O)OR2、C(=O)N(R2)2、Si(R2)3、N(R2)2、NO2、P(=O)(R2)2、OSO2R2、OR2、S(=O)R2、S(=O)2R2、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR2基により置換されてよく、ここで、1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)2、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上のR2基により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または1以上のR2基で置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせであり;同時に、2個以上の隣接するR1置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R2は、出現毎に同一か異なり、H、D、F、Cl、Br、I、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、OSO2R3、OR3、S(=O)R3、S(=O)2R3、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR2基により置換されてよく、ここで、1以上の隣接しないCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)2、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上のR3基により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または1以上のR3基で置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせであり;同時に、2個以上の隣接するR2置換基は、一緒になってモノあるいはポリ環式の脂肪族もしくは芳香族環構造形成してもよく;
R3は、出現毎に同一か異なり、H、D、Fまたは1〜20個の炭素原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基(ここで、水素原子は、Fで置き代えられてもよい。)であり;同時に、2個以上の隣接するR3置換基は、一緒になってモノあるいはポリ環式の脂肪族もしくは芳香族環構造を形成してもよく;
ただし、
少なくとも一つのAr2および/またはAr3基は、式(IIa)または式(IIb)の基であり;
Xは、出現毎に同一か異なり、NまたはCR1、好ましくは、CR1であり、ただし、一つの環において、2個を超えないX基は、Nであり;
L2は、結合、6〜60個の、好ましくは、6〜40個の、より好ましくは、6〜20個の炭素原子を有する芳香族環構造、または3〜60個の、好ましくは、3〜40個の、より好ましくは、3〜20個の炭素原子を有する複素環式芳香族環構造であり、夫々、1以上のR1基により置換されてよく、好ましくは、結合、6〜60個の、好ましくは、6〜40個の、より好ましくは、6〜20個の炭素原子を有するアリール基、または3〜60個の、好ましくは、3〜40個の、より好ましくは、3〜20個の炭素原子を有するヘテロアリール基であり、夫々、1以上のR1基により置換されてよく;
R1は、上記定義のとおりであり、および破線は、L2が、L1と同じ窒素原子に結合するような結合位置を表す。
ると理解される。アルキニル基は、たとえば、エチニル、プロピニル、ブチニル、ペンチニル、ヘキシニル、ヘプチニルまたはオクチニルを意味すると理解される。C1〜C40-アルコキシ基は、たとえば、メトキシ、トリフルオロメトキシ、エトキシ、n-プロポキシ、i-プロポキシ、n-ブトキシ、i-ブトキシ、s-ブトキシ、t-ブトキシまたは2-メチルブトキシを意味すると理解される。
hは、出現毎に独立して、0、1、2、3または4、好ましくは、0、1または2、より好ましくは、0または1であり;
Ar4は、6〜40個の炭素原子を有するアリール基、または3〜40個の炭素原子を有するヘテロアリール基であり、夫々、1以上のR1基により置換されてよく、および
記号Ar1、Ar2、Ar3、L1およびZは、上記定義されるとおりである。
さらに、驚くべき効果は、式(IIa)または(IIb)のフルオレン構造において9位の炭素原子に結合する2個のR1基は、夫々、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり、ここで、2個の環構造が、互いに結合する式(I)の化合物により示される。
Yは、O、SまたはNR2、好ましくは、OまたはSであり;
jは、出現毎に独立して、0、1、2または3であり;
hは、出現毎に独立して、0、1、2、3または4であり;
gは、出現毎に独立して、0、1、2、3、4または5であり;
破線の結合は、付属位置の印であり、
R2は、上記で定義されるとおりである。
この場合に、アミノ基、好ましくは、2級アミノ基を含む少なくとも一つの窒素含有ヘテロ環基を含む基、好ましくは、カルバゾール基を含む化合物は、少なくとも一つのフルオレン基に結合することができる。さらに、少なくとも一つのフルオレン基を含み、アミノ基、好ましくは、2級アミノ基を含む化合物は、窒素含有ヘテロ環基、好ましくは、カルバゾール基を含む基に結合することができる。
以下の合成スキームにおいて、化合物は、構造を単純化するために、置換基を少数にして示される。これは、プロセスにおいて任意の所望のさらなる置換基の存在を排除するものではない。
HOMO(eV)=((HEh*27.212)−0.9899)/1.1206
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
本出願の文脈では、これらの値は、材料のHOMOおよびLUMOエネルギー準位とみなすべきである。
以上の正孔を伝導する層(HTL)中に正孔を伝導する化合物として含む電子素子、好ましくは、有機エレクトロルミッセンス素子を提供する。特に、1以上の本発明の化合物および/または少なくとも一つの本発明のオリゴマー、ポリマーもしくはデンドリマーを、正孔注入層中で正孔注入材料として、電子ブロック層(EBL)中で、電子ブロック材料として使用することができる。特に、1以上の本発明の化合物および/または少なくとも一つの本発明のオリゴマー、ポリマーもしくはデンドリマーを、マトリックス材料として、好ましくは、1以上の発光層(EML)中で正孔を伝導するマトリックス材料として使用することができる。この文脈において、特に好ましいのは、HTLまたはEMLでの使用である。
以下の合成を、別段の指定がない限り、無水溶媒中で保護ガス雰囲気下で実施する。金属錯体をさらに、遮光して、または黄色光下で処理する。溶媒および試薬を、たとえば、Sigma-ALDRICHまたはABCRから購入することができる。個々の化合物に対して示されている角括弧中のそれぞれの数字は、文献から知られている化合物のCAS番号に関連する。
最初に、500mlの四ツ口フラスコに、15.0g(61.0ミリモル、1.0当量)の4-ブロモ-9H-カルバゾール1a(CAS 3652-89-9)を、13.6ml(122ミリモル、2.0当量)のヨードベンゼン2aと、16.8g(122ミリモル、2.0当量)の炭酸カリウムとともに入れ、これらを180mlの無水DMFに溶解させる。30分間の窒素流による脱気後、1.38g(6.10ミリモル、0.10当量)の1,3-ジ(2-ピリジル)-1,3-プロパンジオンと、1.16g(6.10ミリモル、0.10当量)のヨウ化銅(I)とを添加する。混合物を110℃で終夜、撹拌し、反応が完了した後、溶媒をロータリーエバポレーターで除去する。残留物を250mlのDCMに取込み、濃塩化アンモニウム溶液を添加し、混合物をセライトを通して濾過する。その後、相を分離させ、水相を各回、100mlのDCMで二度抽出し、結合した有機相を最後に、水で洗浄する。硫酸ナトリウムで脱水し、減圧下で溶媒を除去した後、油状の残留物をヘプタンとともに、シリカゲルを通して濾過し、溶媒を再度、ロータリーエバポレーターで除去する。19.0g(59.0ミリモル、97%)の無色のオイル3aが得られる。
500mlの四ツ口フラスコで、18.9g(58.7ミリモル、1.0当量)の4-ブロモ-9-フェニル-9H-カルバゾール3と、9.17g(58.7ミリモル、1.0当量)の4-クロロフェニルボロン酸(CAS 1679-18-1)と、6.22g(58.7ミリモル、1.0当量)の炭酸ナトリウムとを、150mlのトルエンと、36mlのエタノールと、77mlの水とに溶解させる。30分間の窒素流による脱気後、678mg(0.587ミリモル、0.01当量)のテトラキス(トリフェニルホスフィン)-パラジウムを添加し、混合物を終夜、還流下で加熱する。反応が完了した後、相を分離させ、水相をトルエンで三度抽出し、結合した有機相を次いで、水で洗浄する。有機相を硫酸ナトリウムで脱水し、溶液をロータリーエバポレーターで濃縮する。残留物を250mlのエタノールに入れ、形成された固形物を吸引濾過する。19.9g(56.4ミリモル、96%)の所望の生成物5aが得られる。
最初に、1lの四ツ口フラスコに、14.0g(51.4ミリモル、1.0当量)の4-ブロモ-9,9-ジメチルフルオレン7aと、さらに10.5g(60.8ミリモル、1.2当量)のビフェニル-4-アミン6aと、12.9g(134ミリモル、2.6当量)のナトリウムtert-ブトキシドとを入れ、これらを300mlの無水p-キシレンに溶解させる。その後、混合物を45分間、脱気し、346mg(1.54ミリモル、0.03当量)の酢酸パラジウム(II)と、1.71g(3.09ミリモル、0.06当量)の1,1’-ビス(ジフェニルホスフィノ)フェロセンとを添加し、混合物を140℃で終夜、撹拌する。反応が完了した後、溶媒を減圧下で除去し、残留物をジクロロメタンに取込み、ヘプタンを添加する。沈殿した固形物を吸引濾過し、真空乾燥キャビネットで乾燥させると、11.0g(30.5ミリモル、59%)の所望の生成物8aが得られる。
11.0g(30.5ミリモル、1.0当量)の二級アミン8aと、さらに11.9g(33.6ミリモル、1.1当量)の4-(4-クロロフェニル)-9-フェニル-9H-カルバゾール5aとを、250mlの無水トルエンに溶解させ、アルゴンで約30分間飽和させる。その後、279mg(0.305ミリモル、0.1当量)のトリス(ジベンジリデンアセトン)ジパラジウムと、250mg(0.610ミリモル、0.02当量)の2-ジシクロヘキシルホスフィノ-2’,6’-メトキシビフェニルとを添加し、混合物を加熱して還流させる。反応が完了した後、混合物を分液漏斗に移し、300mlの水で二度抽出する。水相を再度、トルエンとともに振ることにより抽出し、結合した有機相を硫酸ナトリウムで脱水させる。溶媒をロータリーエバポレーターで除去した後、残留した固形物が得られ、これを少量のジクロロメタンに取込み、エタノールに入れる。得られた固形物を熱抽出と、トルエン/ヘプタンからの三度の再結晶化とにより精製し、最後に昇華させる。7.04g(10.4ミリモル、34%)の最終段階9aが、HPLC純度>99.9%で得られる。
種々のOLEDについてのデータを、以下の例C1〜I14で提示する(表1および2を参照)。
燐光OLEDの発光層(EML)で、電子を伝導する化合物(たとえば、以下挙げる例の化合物IC1)と組み合わせて、正孔を輸送するマトリックス材料として使用するとき、本発明の材料は、先行技術と比べて、とくにOLEDの寿命に関して、著しい改善を与える。本発明の化合物9aと9hを使用することにより、先行技術の化合物PAと比べて、50%を超える寿命の改善を観察することができる(例C1、I1およびI2、またはC2とI15)。
Claims (8)
- 少なくとも一つの式(Ic)の化合物を含む電子素子;
L1は、(L−1)〜(L−5)から選ばれ;
gは、出現毎に独立して、0、1、2、3、4または5であり;
jは、出現毎に独立して、0、1、2または3であり;
Ar1、Ar2、Ar3は、6〜20個の炭素原子を有するアリール基、または3〜20個の炭素原子を有するヘテロアリール基であり、夫々、1以上のR1基により置換されてよく;
R1は、出現毎に同一か異なり、H、D、F、1〜6個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個の炭素原子を有する分岐あるいは環式アルキルもしくはアルコキシ基(ここで、1以上の水素原子は、D、もしくはFで置き代えられてよい。)または、5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;同時に、2個の隣接するR 1基は、一緒になって、または、R 1基は、R2基と一緒になって、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を互いに形成してもよく;
R2は、出現毎に同一か異なり、H、D、F、Cl、Br、I、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、OSO2R3、OR3、S(=O)R3、S(=O)2R3、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR3基により置換されてよく、ここで、1以上の隣接しないCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)2、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上のR3基により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、または1以上のR3基で置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせであり;同時に、2個以上の隣接するR2置換基は、一緒になって、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を形成してもよく;
R3は、出現毎に同一か異なり、H、D、Fまたは1〜20個の炭素原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基(ここで、水素原子は、Fで置き代えられてもよい。)であり;同時に、2個以上の隣接するR3置換基は、一緒になって、モノあるいはポリ環式の脂肪族もしくは芳香族環構造を形成してもよく;
hは、出現毎に独立して、0、1、2、3または4であり;
Ar4は、6〜40個の炭素原子を有するアリール基、または3〜40個の炭素原子を有するヘテロアリール基であり、夫々、1以上のR1基により置換されてよく;
ただし、
少なくとも一つのAr2および/またはAr3基は、式(IIc)、(IId)、(IIe)または(IIf)の基であり;
すべてXは、CR1であり、ここで、多くとも4個のXであるCR1は、CH基ではなく;
R4は、H、フェニル、ビフェニルもしくはナフチルまたはメチル、エチル、プロピルもしくはブチルであり;
L2は、結合であり;
R1は、上記定義のとおりであり、および破線は、L2が、L1と同じ窒素原子に結合するような結合位置を表す。 - hは、0または1であることを特徴とする、請求項1記載の電子素子。
- 2個のR4は、同一であることを特徴とする、請求項1記載の電子素子。
- R4は、フェニルまたはメチルであることを特徴とする、請求項1記載の電子素子。
- Ar1とAr3は、1以上のR1基により置換されてよい6〜12個の芳香族環原子を有する芳香族環構造であることを特徴とする、請求項1記載の電子素子。
- 電子素子は有機エレクトロルミッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機ソーラーセル、有機光学検査素子、有機光受容器、有機電場消光素子、発光電子化学セルおよび有機レーザーダイオードより成る群から選ばれる請求項1記載の電子素子。
- 電子素子は有機エレクトロルミッセンス素子である、請求項7記載の電子素子。
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CN107001270B (zh) | 2020-09-15 |
TW201634447A (zh) | 2016-10-01 |
CN107001270A (zh) | 2017-08-01 |
US20170324038A1 (en) | 2017-11-09 |
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