JP6750784B2 - 化合物およびこれを含む有機電子素子 - Google Patents
化合物およびこれを含む有機電子素子 Download PDFInfo
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- JP6750784B2 JP6750784B2 JP2018549326A JP2018549326A JP6750784B2 JP 6750784 B2 JP6750784 B2 JP 6750784B2 JP 2018549326 A JP2018549326 A JP 2018549326A JP 2018549326 A JP2018549326 A JP 2018549326A JP 6750784 B2 JP6750784 B2 JP 6750784B2
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- 150000001875 compounds Chemical class 0.000 title claims description 120
- 239000010410 layer Substances 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 153
- 125000003118 aryl group Chemical group 0.000 claims description 147
- 125000002560 nitrile group Chemical group 0.000 claims description 103
- 239000000126 substance Substances 0.000 claims description 96
- 125000000623 heterocyclic group Chemical group 0.000 claims description 88
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 75
- -1 sulfoxy group Chemical group 0.000 claims description 75
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 238000002347 injection Methods 0.000 claims description 52
- 239000007924 injection Substances 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 239000011368 organic material Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 84
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 82
- 125000001624 naphthyl group Chemical group 0.000 description 61
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 54
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 54
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 54
- 229910052731 fluorine Inorganic materials 0.000 description 50
- 239000011737 fluorine Substances 0.000 description 50
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 50
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 46
- 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 37
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 33
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 33
- 125000006267 biphenyl group Chemical group 0.000 description 32
- 230000032258 transport Effects 0.000 description 30
- 239000000463 material Substances 0.000 description 26
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 125000005561 phenanthryl group Chemical group 0.000 description 23
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 20
- 125000005567 fluorenylene group Chemical group 0.000 description 18
- 125000004957 naphthylene group Chemical group 0.000 description 18
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 18
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 17
- 229940125904 compound 1 Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- 125000006836 terphenylene group Chemical group 0.000 description 16
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 12
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- 125000002950 monocyclic group Chemical group 0.000 description 11
- 125000003367 polycyclic group Chemical group 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000005264 aryl amine group Chemical group 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001616 biphenylenes Chemical group 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 0 Cc(c(*)c(*)c(*)c1*2)c1-c1c2c(*)c(C)c(*)c1* Chemical compound Cc(c(*)c(*)c(*)c1*2)c1-c1c2c(*)c(C)c(*)c1* 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical group 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000004506 ultrasonic cleaning Methods 0.000 description 4
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 3
- ZOBYHXVPNDMBNM-UHFFFAOYSA-N Cc(cc1)cc(C)c1N(c1cccc(c2ccc3)c1[o]c2c3C#N)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 Chemical compound Cc(cc1)cc(C)c1N(c1cccc(c2ccc3)c1[o]c2c3C#N)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 ZOBYHXVPNDMBNM-UHFFFAOYSA-N 0.000 description 3
- YZZKEPMDGOIKPV-UHFFFAOYSA-N Cc(cc1)cc(C)c1N(c1cccc2c1[o]c1c(C(F)(F)F)cccc21)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 Chemical compound Cc(cc1)cc(C)c1N(c1cccc2c1[o]c1c(C(F)(F)F)cccc21)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 YZZKEPMDGOIKPV-UHFFFAOYSA-N 0.000 description 3
- ZLOUMYBLKSLFRU-UHFFFAOYSA-N Cc(cccc1)c1N(c1cccc2c1[o]c1c(C(F)(F)F)cccc21)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 Chemical compound Cc(cccc1)c1N(c1cccc2c1[o]c1c(C(F)(F)F)cccc21)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 ZLOUMYBLKSLFRU-UHFFFAOYSA-N 0.000 description 3
- GHHJEFWEZYJMOI-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c1cccc2c1[o]c1c2cccc1C(F)(F)F)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 Chemical compound N#Cc(cc1)ccc1N(c1cccc2c1[o]c1c2cccc1C(F)(F)F)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 GHHJEFWEZYJMOI-UHFFFAOYSA-N 0.000 description 3
- ZFXSIDQQJSUOOE-UHFFFAOYSA-N N#Cc1cccc(c2ccc3)c1[o]c2c3N(c1ccccc1)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 Chemical compound N#Cc1cccc(c2ccc3)c1[o]c2c3N(c1ccccc1)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 ZFXSIDQQJSUOOE-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005377 alkyl thioxy group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001975 deuterium Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- RLTYMXMRZGMDAQ-UHFFFAOYSA-N 6-tert-butyl-N-(2-methylphenyl)dibenzofuran-4-amine Chemical compound C(C)(C)(C)C1=CC=CC=2C3=C(OC=21)C(=CC=C3)NC1=C(C=CC=C1)C RLTYMXMRZGMDAQ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- SMQDGQARDRFFHX-UHFFFAOYSA-N CCc(cc1)ccc1N(c1cccc2c1[o]c1c2cccc1C(F)(F)F)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 Chemical compound CCc(cc1)ccc1N(c1cccc2c1[o]c1c2cccc1C(F)(F)F)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4c2cccc4)c-3c2c1cccc2 SMQDGQARDRFFHX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LQWDTSPVHCDMTR-UHFFFAOYSA-N Cc(cc1)ccc1N(c1c2[o]c(c(C#N)ccc3)c3c2ccc1)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 Chemical compound Cc(cc1)ccc1N(c1c2[o]c(c(C#N)ccc3)c3c2ccc1)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 LQWDTSPVHCDMTR-UHFFFAOYSA-N 0.000 description 2
- ONFMHAWLHPRUNF-UHFFFAOYSA-N Cc(cccc1)c1N(c1cccc2c1[o]c1c2cccc1C#N)c1cc(C2(c3ccc(cccc4)c4c3-3)c(cccc4)c4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 Chemical compound Cc(cccc1)c1N(c1cccc2c1[o]c1c2cccc1C#N)c1cc(C2(c3ccc(cccc4)c4c3-3)c(cccc4)c4-[n]4c5c2cccc5c2c4cccc2)c-3c2ccccc12 ONFMHAWLHPRUNF-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NXNTWSNOXJVGPK-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c(cc1c2c3cccc2)ccc1[n]3-c1ccccc1)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4ccccc24)c-3c2c1cccc2 Chemical compound N#Cc(cc1)ccc1N(c(cc1c2c3cccc2)ccc1[n]3-c1ccccc1)c1cc(C2(c3ccc(cccc4)c4c3-3)c4ccccc4N(c4ccccc4)c4ccccc24)c-3c2c1cccc2 NXNTWSNOXJVGPK-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Description
[化学式1]
R1〜R25のうちの少なくとも1つは、
前記L101、L1、およびL2は、互いに同一または異なり、それぞれ独立に、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
前記Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R1〜R25のうち
前記
本明細書の一実施態様において、前記L101は、置換もしくは非置換のアリーレン基である。
本明細書の一実施態様において、前記L101は、置換もしくは非置換のフェニレン基、置換もしくは非置換のビフェニレン基、置換もしくは非置換のナフチレン基、または置換もしくは非置換のフルオレニレン基である。
本明細書の一実施態様において、前記L101は、置換もしくは非置換の2価のヘテロ環基である。
本明細書の一実施態様において、前記L4は、アルキル基、シクロアルキル基、ハロゲン基、ハロゲン化アルキル基、ニトリル基、シリル基、アリール基、またはヘテロ環基で置換もしくは非置換の2価のカルバゾール基である。
本明細書の一実施態様において、前記L4は、アルキル基、シクロアルキル基、ハロゲン基、ハロゲン化アルキル基、ニトリル基、シリル基、−OCF3、アリール基、またはヘテロ環基で置換もしくは非置換の2価のジベンゾチオフェン基である。
[反応式1]
[反応式6]
[化合物1]
MS[M+H]+=1,162
[化合物2]
MS[M+H]+=1,162
[化合物3]
MS[M+H]+=970
[化合物4]
MS[M+H]+=1,160
[化合物5]
MS[M+H]+=1,168
[化合物6]
MS[M+H]+=827
[化合物7]
MS[M+H]+=865
[化合物8]
MS[M+H]+=903
<実験例1−1>
ITO(indium tin oxide)が1,000Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
[HAT]
前記実験例1−1における化合物1の代わりに前記化合物2を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における化合物1の代わりに前記化合物3を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における化合物1の代わりに前記化合物4を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における化合物1の代わりに前記化合物5を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
ITO(indium tin oxide)が1,000Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
[HAT]
前記実験例2−1における化合物1の代わりに前記化合物2を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例2−1における化合物1の代わりに前記化合物3を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例2−1における化合物1の代わりに前記化合物4を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例2−1における化合物1の代わりに前記化合物5を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
20:基板
30:第1電極
40:発光層
50:第2電極
60:正孔注入層
70:正孔輸送層
80:電子ブロック層
90:電子輸送層
100:電子注入層
Claims (13)
- 下記化学式1で表される化合物:
[化学式1]
R1〜R25のうち1つまたは2つは、
前記L1、およびL2は、互いに同一または異なり、それぞれ独立に、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
前記L101は、直接結合であり、
前記Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R1〜R25のうち
前記
R4およびR5が結合せず、かつR9およびR10が結合しない場合、
前記化学式1において、L1またはL2が置換もしくは非置換のアリーレン基であること、および、
Ar1またはAr2が置換もしくは非置換のアリール基であることの少なくともいずれかを満たす。 - 前記Ar1およびAr2のうちのいずれか1つ以上は、下記化学式1Aである、請求項1に記載の化合物:
[化学式1A]
Xは、S、O、CRR'、またはNRであり、
R、R'、およびR26〜R29は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であるか、隣接した基と互いに結合して置換もしくは非置換の環を形成してもよいし、
R30〜R33のうちのいずれか1つは、前記化学式1のL1またはL2と結合し、前記R30〜R33のうち前記化学式1のL1またはL2と結合しない基は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であるか、隣接した基と互いに結合して置換もしくは非置換の環を形成してもよい。 - 前記化学式1は、下記化学式2〜8のうちのいずれか1つで表される、請求項1に記載の化合物:
[化学式2]
R1〜R25、L101、L1、L2、Ar1、およびAr2に関する定義は、前記化学式1で定義したものと同じであり、
L3およびL4は、互いに同一または異なり、それぞれ独立に、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
L102は、直接結合;または置換もしくは非置換の窒素原子を含む2価のヘテロ環基であり、
Ar3およびAr4は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。 - 第1電極と、前記第1電極に対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含む有機電子素子であって、前記有機物層のうちの1層以上は、請求項1〜4のいずれか1項に記載の化合物を含むものである有機電子素子。
- 前記有機物層は、発光層を含み、前記発光層は、前記化合物を含むものである、請求項5に記載の有機電子素子。
- 前記有機物層は、電子注入層を含み、前記電子注入層は、前記化合物を含むものである、請求項5または6に記載の有機電子素子。
- 前記有機物層は、電子ブロック層を含み、前記電子ブロック層は、前記化合物を含むものである、請求項5〜7のいずれか1項に記載の有機電子素子。
- 前記有機物層は、正孔注入層、正孔輸送層、または正孔注入および輸送を同時に行う層を含み、前記正孔注入層、正孔輸送層、または正孔注入および輸送を同時に行う層は、前記化合物を含むものである、請求項5〜8のいずれか一項に記載の有機電子素子。
- 前記有機電子素子は、発光層、正孔注入層、正孔輸送層、電子注入層、および電子ブロック層からなる群より選択される1層または2層以上をさらに含むものである、請求項5〜9のいずれか一項に記載の有機電子素子。
- 前記有機電子素子は、有機発光素子、有機燐光素子、有機太陽電池、有機感光体(OPC)、および有機トランジスタからなる群より選択される、請求項5〜10のいずれか一項に記載の有機電子素子。
- 前記有機物層は、発光層を含み、前記発光層は、前記化合物をドーパント物質として含み、下記化学式9で表される化合物をホスト物質として含むものである、請求項5に記載の有機電子素子:
[化学式9]
Yは、OまたはSであり、
G11は、置換もしくは非置換のアリール基であり、
G12〜G15は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;イミド基;アミド基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
g12、g13およびg15は、それぞれ1〜4の整数であり、
g14は、1〜3の整数であり、
前記g12〜g15がそれぞれ2以上の時、2以上のG12〜G15は、それぞれ互いに同一または異なる。
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