JP6302932B2 - 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 - Google Patents
有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 Download PDFInfo
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- JP6302932B2 JP6302932B2 JP2015549243A JP2015549243A JP6302932B2 JP 6302932 B2 JP6302932 B2 JP 6302932B2 JP 2015549243 A JP2015549243 A JP 2015549243A JP 2015549243 A JP2015549243 A JP 2015549243A JP 6302932 B2 JP6302932 B2 JP 6302932B2
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- 150000001875 compounds Chemical class 0.000 title claims description 53
- 239000000463 material Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000011368 organic material Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- -1 fluoreneyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 description 95
- 238000003786 synthesis reaction Methods 0.000 description 94
- 239000010410 layer Substances 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 60
- 239000000047 product Substances 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 230000000052 comparative effect Effects 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000001308 synthesis method Methods 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 229960001866 silicon dioxide Drugs 0.000 description 14
- 239000007858 starting material Substances 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 6
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- CWLWLLMRBYQJIO-UHFFFAOYSA-N 5-bromo-11h-benzo[a]carbazole Chemical compound N1C2=C3C=CC=C[C]3C(Br)=CC2=C2[C]1C=CC=C2 CWLWLLMRBYQJIO-UHFFFAOYSA-N 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 2
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 238000005885 boration reaction Methods 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 1
- WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 1
- MFHHEKUJHVFSFV-UHFFFAOYSA-N 1,4-dibromo-2-nitronaphthalene Chemical compound C1=CC=CC2=C(Br)C([N+](=O)[O-])=CC(Br)=C21 MFHHEKUJHVFSFV-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 description 1
- QSNSZGYDLUPWSV-UHFFFAOYSA-N 2,4-dichloropyrido[2,3-d]pyrimidine Chemical compound C1=CC=NC2=NC(Cl)=NC(Cl)=C21 QSNSZGYDLUPWSV-UHFFFAOYSA-N 0.000 description 1
- UVVFNZJVLRJSMW-UHFFFAOYSA-N 2,4-dichloropyrido[3,2-d]pyrimidine Chemical compound N1=CC=CC2=NC(Cl)=NC(Cl)=C21 UVVFNZJVLRJSMW-UHFFFAOYSA-N 0.000 description 1
- VYMNCOOEVDIPTL-UHFFFAOYSA-N 2-bromo-6-iodonaphthalene Chemical compound C1=C(I)C=CC2=CC(Br)=CC=C21 VYMNCOOEVDIPTL-UHFFFAOYSA-N 0.000 description 1
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 1
- RIMCUZFCHBCDID-UHFFFAOYSA-N 2-iodo-1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(I)C=CC2=C1 RIMCUZFCHBCDID-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- KNJJGSGPSKPDBR-UHFFFAOYSA-N 5-bromo-7h-benzo[c]carbazole Chemical compound C12=CC=CC=C2C(Br)=CC2=C1C1=CC=CC=C1N2 KNJJGSGPSKPDBR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MAWIMXZUWQPCJQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC(=CC2=CC=CC=C12)[Ir+]C=1N=C(C2=CC=CC=C2C=1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C1=NC(=CC2=CC=CC=C12)[Ir+]C=1N=C(C2=CC=CC=C2C=1)C1=CC=CC=C1 MAWIMXZUWQPCJQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000006930 Pseudomyxoma Peritonei Diseases 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-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
- 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
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 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
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- CSLSCVHILGCSTE-UHFFFAOYSA-N dibenzothiophen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3SC2=C1 CSLSCVHILGCSTE-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 125000002950 monocyclic group Chemical group 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 three or more hetero 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
- C07D403/14—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 three or more hetero rings
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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Description
本発明に使われた用語"アルコキシ基"は他の説明がない限り、1乃至60の炭素数を有し、ここに制限されるものではない。
本発明に使われた用語"アリール基"及び"アリーレン基"は他の説明がない限り、各々6乃至60の炭素数を有し、これに制限されるものではない。
本明細書で使われた用語"ヘテロ原子"は他の説明がない限り、N、O、S、P、及びSiを示す。
前述したヘテロ化合物の以外の異なるヘテロ化合物またはヘテロラジカルは1つ以上のヘテロ原子を含み、ここに制限されるものではない。
図1は、本発明の一実施例に従う有機電気素子に対する例示図である。
本発明に係る有機電気素子は、使われる材料によって、前面発光型、後面発光型、または両面発光型でありうる。
以下、本発明の一態様に係る化合物について説明する。
本発明の一態様に係る化合物は、以下の<化学式1>で表示される。
<化学式1>
上記<化学式1>で、
そして、X1〜X4は互いに独立的で、CR'またはNであり、
上記R'は、水素、C6〜C60のアリール基、フルオレンイル基、O、N、S、Si、及びPのうちの少なくとも1つのヘテロ原子を含むC2〜C60のヘテロ環基、C1〜C50のアルキル基、C6〜C60の芳香族環とC3〜C60の脂肪族環の融合環基、及びC2〜C20のアルケニル基からなる群から選択できる。
一方、上記A環、B環、Ar1、Ar2、及びR'などは他の置換基にさらに置換できる。
一方、上記<化学式1>は以下の化合物のうちの1つで表示できる。
この際、上記化学式2乃至9で、Ar1〜Ar2、X1〜X4、及びLは<化学式1>で定義されたものと同一に定義される。
一方、上記化学式1〜9は以下の化合物で表示できる。
合成例
<反応式1>
1.Sub 1の合成
上記<反応式1>のSub 1は以下の<反応式2>の反応経路により合成できるが、これに限定されるものではない。
<反応式2>
Sub 1に属する具体的化合物の合成例は、次の通りである。
(1)Sub 1−1合成例(L=単一結合)
<反応式3>
中間体M 1−I−1合成
中間体M 1−II−1合成
中間体Sub 1−I−1合成
中間体Sub 1−II−1合成
中間体Sub 1−III−1合成
Sub 1−1合成例
(2)Sub 1−18合成例
<反応式4>
中間体Sub 1−IV−18合成
中間体Sub 1−V−18合成
Sub 1−18合成例
(3)Sub 1−22合成例(L=単一結合)
<反応式5>
中間体Sub 1−I−22合成
中間体Sub 1−II−22合成
中間体Sub 1−III−22合成
Sub 1−22合成例
(4)Sub 1−32合成例(L=単一結合)
<反応式6>
中間体M 2−I−32合成
中間体Sub 1−I−32合成
中間体Sub 1−II−32合成
中間体Sub 1−III−32合成
Sub 1−32合成例
(5)Sub 1−47合成例(L=単一結合)
<反応式7>
中間体M 2−I−47合成
中間体Sub 1−I−47合成
中間体Sub 1−II−47合成
中間体Sub 1−III−47合成
Sub 1−47合成例
(6)Sub 1−52合成例(L=単一結合)
<反応式8>
(7)Sub 1−76合成例
<反応式9>
中間体Sub 1−IV−76合成
中間体Sub 1−V−76合成
Sub 1−76合成例
一方、Sub 1の例示は以下の通りであるが、これに限定されるものではなく、これらのFD−MSは以下の<表1>の通りである。
2.Sub 2の合成
上記<反応式1>のSub 2は以下の<反応式10>の反応経路により合成できるが、これに限定されるものではない。
<反応式10>
Sub 2に属する具体的化合物の合成例は、次の通りである。
(1)Sub 2−2合成例
<反応式11>
(2)Sub 2−8合成例
<反応式12>
(3)Sub 2−14合成例
<反応式13>
(4)Sub 2−27合成例
<反応式14>
(5)Sub 2−29合成例
<反応式15>
(6)Sub 2−34合成例
<反応式16>
一方、Sub 2の例示は以下の通りであるが、これに限定されるものではなく、これらのFD−MSは以下の<表2>の通りである。
(1)Product 1−1合成例
<反応式17>
(2)Product 1−10合成例
<反応式18>
(3)Product 1−53合成例
<反応式19>
(4)Product 1−58合成例
<反応式20>
(5)Product 1−89合成例
<反応式21>
(6)Product 1−130合成例
<反応式22>
(7)Product 1−133合成例
<反応式23>
(8)Product 1−136合成例
<反応式24>
(9)Product 2−14合成例
<反応式25>
(10)Product 2−60合成例
<反応式26>
有機電気素子の製造評価
[実施例1]発光層(燐光レッドホスト)
合成を通じて得た本発明の化合物を発光層の発光ホスト物質に使用して通常的な方法により有機電気発光素子を製作した。
[実施例2]乃至[実施例268]発光層(燐光レッドホスト)
[比較例1]
<比較化合物1>
bis(10-hydroxybenzo[h]qinolinato)beryllium(以下、Bebq2と略記する)
[比較例2]
<比較化合物2>
[比較例3]
<比較化合物3>
[比較例4]
<比較化合物4>
[比較例5]
<比較化合物5>
[比較例6]
<比較化合物6>
[比較例7]
<比較化合物7>
120:第1電極 130:正孔注入層
140:正孔輸送層 141:バッファ層
150:発光層 151:発光補助層
160:電子輸送層 170:電子注入層
180:第2電極
CROSS-REFERENCE TO RELATED APPLICATION
Claims (9)
- 以下の<化学式1>で表示される化合物。
<化学式1>
[前記<化学式1>で、
A環及びB環は互いに独立してフェニルとナフタレンからなる群から選択され(但し、A環とB環が同時にフェニルであることは除外する)、
Lは単結合、C6〜C60のアリーレン基、フルオレンイレン基、O、N、S、Si、及びPのうち、少なくとも1つのヘテロ原子を含むC2〜C60のヘテロ環基、及び2価の脂肪族炭化水素基からなる群から選択され、
Ar1及びAr2は互いに独立してフルオレンイル基、シラン基、C6〜C60のアリール基、C2〜C20のアルケニル基、O、N、S、Si、及びPのうち、少なくとも1つのヘテロ原子を含むC2〜C60のヘテロ環基、C1〜C50のアルキル基、及びC6〜C60の芳香族環とC3〜C60の脂肪族環の縮合環基からなる群から選択され、
X1〜X4は互いに独立して、CR'またはNであり、
前記R'は、水素、C6〜C60のアリール基、フルオレンイル基、O、N、S、Si、及びPのうち、少なくとも1つのヘテロ原子を含むC2〜C60のヘテロ環基、C1〜C50のアルキル基、C6〜C60の芳香族環とC3〜C60の脂肪族環の縮合環基、及びC2〜C20のアルケニル基からなる群から選択される。
ここで、前記アリール基、フルオレンイル基、ヘテロ環基、縮合環基、アルキル基、アルケニル基、芳香族環、脂肪族炭化水素基、アリーレン基、フルオレンイレン基が1つ以上の置換基にさらに置換される場合には、各々重水素、ハロゲン、シラン基、シロキサン基、ホウ素基、ゲルマニウム基、シアノ基、ニトロ基、アミン基、C1〜C20のアルキルチオ基、C1〜C20のアルコキシル基、C1〜C20のアルキル基、C2〜C20のアルケニル基、C2〜C20のアルキニル基、C6〜C20のアリール基、重水素に置換されたC6〜C20のアリール基、フルオレンイル基、C2〜C20のヘテロ環基、C3〜C20のシクロアルキル基、C7〜C20のアリルアルキル基、及びC8〜C20のアリルアルケニル基からなる群から選択された1つ以上の置換基にさらに置換される。
- 以下の化合物のうちの1つであることを特徴とする、請求項1に記載の化合物。
(前記化学式2乃至9で、Ar1〜Ar2、X1〜X4、及びLは前記<化学式1>で定義されたものと同一である) - 以下の化合物のうちの1つであることを特徴とする、請求項1に記載の化合物。
- 第1電極、第2電極、及び前記第1電極と第2電極との間に位置する有機物層を含む有機電気素子において、
前記有機物層は、請求項1の化合物を含有することを特徴とする、有機電気素子。 - 前記化合物を溶液プロセス(soluble process)により前記有機物層に形成することを特徴とする、請求項4に記載の有機電気素子。
- 前記有機物層は、発光層、正孔注入層、正孔輸送層、電子注入層、電子輸送層、及び発光補助層のうち、少なくとも1つを含むことを特徴とする、請求項4に記載の有機電気素子。
- 前記化合物は発光層のホスト物質で使われることを特徴とする、請求項4に記載の有機電気素子。
- 請求項4の有機電気素子を含むディスプレイ装置と、
前記ディスプレイ装置を駆動する制御部と、を含むことを特徴とする電子装置。 - 前記有機電気素子は、有機電気発光素子、有機太陽電池、有機太陽電池、有機感光体、有機トランジスタ及び単色または白色照明用素子のうち、少なくとも1つであることを特徴とする、請求項8に記載の電子装置。
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KR101431644B1 (ko) * | 2009-08-10 | 2014-08-21 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101153910B1 (ko) | 2010-02-19 | 2012-06-07 | 덕산하이메탈(주) | 인돌 유도체를 핵심으로 하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
KR101172053B1 (ko) | 2010-03-12 | 2012-08-07 | 덕산하이메탈(주) | 두개의 3차 아민이 치환된 인돌 유도체를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
KR101441177B1 (ko) * | 2010-04-20 | 2014-09-17 | 이데미쓰 고산 가부시키가이샤 | 비스카르바졸 유도체를 사용한 유기 일렉트로루미네선스 소자 |
KR101477614B1 (ko) * | 2010-09-17 | 2014-12-31 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR20120052879A (ko) | 2010-11-16 | 2012-05-24 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR101463298B1 (ko) | 2011-04-01 | 2014-11-20 | 주식회사 엘지화학 | 새로운 유기 발광 소자 재료 및 이를 이용한 유기 발광 소자 |
KR102008134B1 (ko) | 2011-05-30 | 2019-08-09 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101513006B1 (ko) * | 2012-06-13 | 2015-04-17 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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KR102061571B1 (ko) | 2020-01-02 |
US20180083204A1 (en) | 2018-03-22 |
US10446762B2 (en) | 2019-10-15 |
US20160005981A1 (en) | 2016-01-07 |
KR20140082273A (ko) | 2014-07-02 |
US20190173023A1 (en) | 2019-06-06 |
US10672992B2 (en) | 2020-06-02 |
WO2014104585A1 (ko) | 2014-07-03 |
US10763443B2 (en) | 2020-09-01 |
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