JP2015224250A - 有機電子素子用化合物、これを用いた有機電子素子及びその電子装置 - Google Patents
有機電子素子用化合物、これを用いた有機電子素子及びその電子装置 Download PDFInfo
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- JP2015224250A JP2015224250A JP2015097995A JP2015097995A JP2015224250A JP 2015224250 A JP2015224250 A JP 2015224250A JP 2015097995 A JP2015097995 A JP 2015097995A JP 2015097995 A JP2015097995 A JP 2015097995A JP 2015224250 A JP2015224250 A JP 2015224250A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 227
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- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052710 silicon Inorganic materials 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 28
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 229910052698 phosphorus Inorganic materials 0.000 claims description 27
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
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- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 11
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 11
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 10
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 3
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- 238000000576 coating method Methods 0.000 claims description 2
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- 125000004122 cyclic group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 239
- 230000015572 biosynthetic process Effects 0.000 description 239
- 238000003786 synthesis reaction Methods 0.000 description 238
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 81
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 81
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 48
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- 125000003118 aryl group Chemical group 0.000 description 21
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- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 230000005525 hole transport Effects 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
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- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 10
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- 239000002019 doping agent Substances 0.000 description 8
- -1 oxygen radical Chemical class 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- PHHATHMJJOZFEK-UHFFFAOYSA-N 2,4-dichloro-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C2C3=NC(Cl)=NC(Cl)=C3OC2=C1 PHHATHMJJOZFEK-UHFFFAOYSA-N 0.000 description 5
- RKVFFIZXAPIGNC-UHFFFAOYSA-N 2,4-dichloro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound ClC=1N=C(C2=C(N1)SC1=C2C=CC=C1)Cl RKVFFIZXAPIGNC-UHFFFAOYSA-N 0.000 description 5
- BSWVSKQCYPFXJF-UHFFFAOYSA-N 2,4-dichloro-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C1=CC=C2C3=NC(Cl)=NC(Cl)=C3SC2=C1 BSWVSKQCYPFXJF-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
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- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 4
- 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 4
- 101150003085 Pdcl gene Proteins 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 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 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
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- 239000000470 constituent Substances 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
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- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
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- 125000006267 biphenyl group Chemical group 0.000 description 2
- 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 2
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- HXITXNWTGFUOAU-RALIUCGRSA-N (2,3,4,5,6-pentadeuteriophenyl)boronic acid Chemical compound [2H]C1=C([2H])C([2H])=C(B(O)O)C([2H])=C1[2H] HXITXNWTGFUOAU-RALIUCGRSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- XDKCHGWZDWHBQO-UHFFFAOYSA-N (6-phenylnaphthalen-2-yl)boronic acid Chemical compound C1=CC2=CC(B(O)O)=CC=C2C=C1C1=CC=CC=C1 XDKCHGWZDWHBQO-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
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- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-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
- 239000005416 organic matter Substances 0.000 description 1
- MWIZGXJYCNZVDW-UHFFFAOYSA-N phenanthren-2-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3C=CC2=C1 MWIZGXJYCNZVDW-UHFFFAOYSA-N 0.000 description 1
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- FZEWPLIHPXGNTB-UHFFFAOYSA-N thianthren-1-ylboronic acid Chemical compound S1C2=CC=CC=C2SC2=C1C=CC=C2B(O)O FZEWPLIHPXGNTB-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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Abstract
Description
各図面の構成要素に参照符号を付すにおいて、同一の構成要素に対しては、たとえ他の図面上に表示されていても可能な限り同一の符号を有するようにしていることに留意すべきである。また、本発明を説明するにおいて、関連する公知の構成又は機能に関する具体的な説明が本発明の要旨を曖昧にするおそれがあると判断される場合には、その詳細な説明は省略する。
前記R1〜R3は互いに独立して、ハロゲン;重水素;シアノ基;C6-C60のアリル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含むC2-C60のヘテロ環基;C1-C30のアルコキシ基;C1-C60のアルキル基;C2-C60のアルケニル基;フルオレニル基;及び-L1-N(R’)(R”);からなる群より選択されることができ、好ましくは、C6-C20のアリル基、C3-C20のヘテロ環基などであり得、より好ましくは、C6のアリル基、C5のヘテロ環基などであり得る。例えば、R1〜R3は互いに独立して、フェニル、ピリジン、メチルフェニルなどであり得る。
また、前記式1のZは、具体的に下記式のうちの1つで表されることができる。
より具体的に、前記式1は、下記式のうちの1つで表されることができる。
一方、前記式1のArは、具体的に下記式のうちの1つで表されることができる。
更に他の実施形態において、本発明は、前記式1で表される化合物を含有する有機電子素子を提供する。
例示的に本発明に係る化合物(Final Product)は、下記反応式1のようにSub 1とSub 2を反応させて製造されるが、これに限定されるものではない。
前記反応式1のSub 1は、下記反応式2の反応経路により合成され得るが、これに限定されるものではない。
1.Sub 1-1の合成例
5-bromobenzo[b]naphtha[1,2-d]thiophene(50g、0.16mol)、bis(pinacolato)diboron(48.65g、0.19mol)、KOAc(47g、0.48mol)、PdCl2(dppf)(5.21g、4mol%)をDMF溶媒に溶かした後、120℃で12時間還流させた。反応が終了すれば、反応物の温度を常温に冷却し、CH2Cl2で抽出し、水で拭き取った。有機層をMgSO4で乾燥させ、濃縮した後、生成された有機物をCH2Cl2とmethanol溶媒を用いて再結晶化して1-1-C1(46g、80%)を得た。
1-1-C1(40g、0.11mol)、bromo-2-nitrobenzene(26.91g、0.13mol)、K2CO3(46.03g、0.33mol)、Pd(PPh3)4(5.13g、4mol%)を無水THFと少量の水に溶かした後、80℃で12時間還流させた。反応が終了すれば、反応物の温度を常温に冷却し、CH2Cl2で抽出し、水で拭き取った。有機層をMgSO4で乾燥させ、濃縮した後、生成された有機物をsilicagel columnで分離して1-1-C2(27.62g、70%)を得た。
1-1-C2(20g、0.05mol)とtriphenylphosphine(44.28g、0.17mol)をo-dichlorobenzeneに溶かし、24時間還流させた。反応が終了すれば、減圧蒸留を用いて溶媒を除去した後、濃縮された生成物をsilicagel column及び再結晶してSub 1-1(13.65g、75%)を得た。
6-bromobenzo[b]naphtha[1,2-d]thiophene(50g、0.16mol)、bis(pinacolato)diboron(48.65g、0.19mol)、KOAc(47g、0.48mol)、PdCl2(dppf)(5.21g、4mol%)及びDMFを前記1-1-C1の合成例と同様の方法で行って1-2-C1(42g、73%)を得た。
1-2-C1(40g、0.11mol)、bromo-2-nitrobenzene(26.91g、0.13mol)、K2CO3(46.03g、0.33mol)、Pd(PPh3)4(5.13g、4mol%)、無水THF及び水を前記1-1-C2の合成例と同様の方法で行って1-2-C2(25.52g、65%)を得た。
1-2-C2(20g、0.05mol)とtriphenylphosphine(44.28g、0.17mol)及びo-dichlorobenzeneを前記Sub 1-1の合成例と同様の方法で行ってSub 1-2(12.4g、68%)を得た。
5-bromobenzo[b]naphtha[2,1-d]thiophene(50g、0.16mol)、bis(pinacolato)diboron(48.65g、0.19mol)、KOAc(47g、0.48mol)、PdCl2(dppf)(5.21g、4mol%)及びDMFを前記1-1-C1の合成例と同様の方法で行って1-3-C1(49.5g、86%)を得た。
得られた1-3-C1(40g、0.11mol)、bromo-2-nitrobenzene(26.91g、0.13mol)、K2CO3(46.03g、0.33mol)、Pd(PPh3)4(5.13g、4mol%)、無水THF及び水を前記1-1-C2の合成例と同様の方法で行って1-3-C2(30g、76%)を得た。
1-3-C2(20g、0.05mol)とtriphenylphosphine(44.28g、0.17mol)及びo-dichlorobenzeneを前記Sub 1-1の合成例と同様の方法で行ってSub 1-3(12.43g、68%)を得た。
6-bromobenzo[b]naphtha[2,1-d]thiophene(50g、0.16mol)、bis(pinacolato)diboron(48.65g、0.19mol)、KOAc(47g、0.48mol)、PdCl2(dppf)(5.21g、4mol%)及びDMFを前記1-1-C1の合成例と同様の方法で行って1-4-C1(43.5g、75%)を得た。
1-4-C1(40g、0.11mol)、bromo-2-nitrobenzene(26.91g、0.13mol)、K2CO3(46.03g、0.33mol)、Pd(PPh3)4(5.13g、4mol%)、無水THF及び水を前記1-1-C2の合成例と同様の方法で行って1-4-C2(22g、56%)を得た。
1-3-C2(20g、0.05mol)とtriphenylphosphine(44.28g、0.17mol)及びo-dichlorobenzeneを前記Sub 1-1の合成例と同様の方法で行ってSub 1-4(10.5g、58%)を得た。
前記反応式1のSub 2は、下記反応式3の反応経路により合成され得るが、これに限定されるものではない。
(1)Sub 2-1-0-(1)の合成例
(1)Sub 2-1-S-(6)の合成例
(1)Sub 2-2-0-(11)の合成例
(1)Sub 2-2-S-(16)の合成例
Sub 1(1当量)、Sub 2(1.2当量)、Pd2(dba)3(4mol%)、t-Bu3P(8mol%)、KOtBu(3当量)をtoluene溶媒に溶かした後、100℃で12時間還流させた。反応が終了すれば、反応物の温度を常温に冷却し、CH2Cl2で抽出し、水で拭き取った。有機層をMgSO4で乾燥させ、濃縮した後、生成された化合物をsilicagel column及び再結晶して最終生成物(Final Product)を得た。
(1)1-1-1-0-(1)の合成例
(1)1-2-1-0-(6)の合成例
(1)1-3-1-0-(11)の合成例
(1)1-4-1-0-(16)の合成例
[実施形態I-1]レッド有機電子発光素子(燐光ホスト)
本発明の一実施形態に係る化合物を発光層の燐光ホスト物質として用いて通常の方法によって有機電子発光素子を製作した。まず、ガラス基板に形成されたITO層(正極)上に4,4’,4”-Tris[2-naphthyl(phenyl)amino]triphenylamine(以下、「2-TNATA」と略す)膜を真空蒸着して60nmの厚さの正孔注入層を形成した。次いで、前記正孔注入層上に4,4-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(以下、「NPD」と略す)を60nmの厚さで真空蒸着して正孔輸送層を形成した。そして、前記正孔輸送層上に本発明の化合物1-1-1-0-(1)をホスト物質として、下記化合物Aをドーパント物質として95:5の重量比でドーピングして30nmの厚さで真空蒸着して発光層を形成した。次に、前記発光層上に(1,1’-ビスフェニル)-4-オレート)ビス(2-メチル-8-キノリナト)アルミニウム(以下「BAlq」と略す)を10nmの厚さで真空蒸着して正孔阻止層を形成し、前記正孔阻止層上にトリス(8-キノリノール)アルミニウム(以下「Alq3」と略す)を40nmの厚さで真空蒸着して電子輸送層を形成した。その後、前記電子輸送層上にハロゲン化アルカリ金属であるLiFを0.2nmの厚さで蒸着して電子注入層を形成し、次いでAlを150nmの厚さで蒸着して負極を形成することで、有機電子発光素子を製造した。
発光層のホスト物質として本発明の化合物1-1-1-0-(1)の代わりに、下記表4に記載された本発明の化合物1-1-1-0-(2)〜1-4-2-S-(23)を用いた点を除いては、前記実施形態I-1と同様の方法で有機電子発光素子を製造した。
発光層のホスト物質として本発明の化合物1-1-1-0-(1)の代わりに、下記比較化合物1〜17を用いた点を除いては、前記実施形態I-1と同様の方法で有機電子発光素子を製造した。
本発明の一実施形態に係る化合物を発光層の燐光ホスト物質として用いて通常の方法によって有機電子発光素子を製作した。まず、ガラス基板に形成されたITO層(正極)上に2-TNATA膜を真空蒸着して60nmの厚さの正孔注入層を形成した。次いで、前記正孔注入層上にNPDを60nmの厚さで真空蒸着して正孔輸送層を形成した。そして、前記正孔輸送層上に本発明の化合物1-1-1-0-(1)をホスト物質として、下記化合物Bをドーパント物質として95:5の重量比でドーピングして30nmの厚さで真空蒸着して発光層を形成した。次に、前記発光層上にBAlqを10nmの厚さで真空蒸着して正孔阻止層を形成し、前記正孔阻止層上にAlq3を40nmの厚さで真空蒸着して電子輸送層を形成した。その後、前記電子輸送層上にハロゲン化アルカリ金属であるLiFを0.2nmの厚さで蒸着して電子注入層を形成し、次いでAlを150nmの厚さで蒸着して負極を形成することで、有機電子発光素子を製造した。
発光層のホスト物質として本発明の化合物1-1-1-0-(1)の代わりに、下記表5に記載された本発明の化合物1-1-1-0-(2)〜1-4-2-S-(23)を用いた点を除いては、前記実施形態II-1と同様の方法で有機電子発光素子を製造した。
発光層のホスト物質として本発明の化合物1-1-1-0-(1)の代わりに、前記比較化合物1〜16を用いた点を除いては、前記実施形態II-1と同様の方法で有機電子発光素子を製造した。
本発明の実施形態II-1〜実施形態II-243及び比較例II-1〜比較例II-16により製造された有機電子発光素子に順バイアス直流電圧を加えてフォトリサーチ(photoresearch)社のPR-650で電気発光(EL)特性を測定し、5000cd/m2の基準輝度でマックサイエンス社で製造された寿命測定装置によってT95寿命を測定した。その測定結果は、下記表5の通りである。
110 基板
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
本特許出願は、2014年5月28日に韓国に出願した特許出願番号第10-2014-0064229号に対して米国特許法119(a)条(35 U.S.C§119(a))によって優先権を主張し、そのあらゆる内容は参考文献として本特許出願に併合される。なお、本特許出願は米国以外に国に対しても上記のような理由で優先権を主張すれば、その全内容は参考文献として本特許出願に組み込まれる。
前記R1〜R3は互いに独立して、ハロゲン;重水素;シアノ基;C6-C60のアリール基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含むC2-C60のヘテロ環基;C1-C30のアルコキシ基;C1-C60のアルキル基;C2-C60のアルケニル基;フルオレニル基;及び-L1-N(R’)(R”);からなる群より選択されることができ、好ましくは、C6-C20のアリール基、C3-C20のヘテロ環基などであり得、より好ましくは、C6のアリール基、C5のヘテロ環基などであり得る。例えば、R1〜R3は互いに独立して、フェニル、ピリジン、メチルフェニルなどであり得る。
Claims (13)
- 下記式1で表される化合物:
S環(ring)は、硫黄(Sulfur)を含むC4-C8のヘテロ環であり、
N環(ring)は、窒素(Nitrogen)を含むC4-C8のヘテロ環であり、
l、m及びnは互いに独立して0〜4の整数であり、
R1〜R3は互いに独立して、i)ハロゲン;重水素;シアノ基;C6-C60のアリル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含むC2-C60のヘテロ環基;C1-C30のアルコキシ基;C1-C60のアルキル基;C2-C60のアルケニル基;フルオレニル基;-L1-N(R’)(R”);からなる群より選択されるか、又はii)隣り合う基同士で互いに結合して少なくとも1つの環を形成でき、このとき、環を形成しないR1〜R3は前記i)で定義されたものと同一に定義され、
前記L及びL1は互いに独立して単一結合;C6-C60のアリレン基;フルオレニレン基;及びO、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含むC2-C60のヘテロアリレン基;からなる群より選択され、これら(単一結合を除く)のそれぞれは、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;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のアリル基;重水素で置換されたC6-C20のアリル基;フルオレニル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含む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;からなる群より選択された1つ以上の置換基で置換され得、
Ar、R’及びR”は互いに独立してC6-C60のアリル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含むC2-C60のヘテロ環基;及びフルオレニル基;からなる群より選択され、
X及びYは互いに独立して単一結合、C(R4)(R5)、N(R4)、O、S、Se及びSi(R4)(R5)からなる群より選択され、
前記R4及びR5は互いに独立して、水素;重水素;C6-C60のアリル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含むC2-C60のヘテロ環基;C1-C30のアルコキシ基;C1-C50のアルキル基;C2-C20のアルケニル基;及びフルオレニル基;からなる群より選択され、
ここで、前記Ar、R1〜R5、R’及びR”のアリル基、フルオレニル基及びヘテロ環基のそれぞれは、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;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のアリル基;重水素で置換されたC6-C20のアリル基;フルオレニル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含む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;からなる群より選択された1つ以上の置換基で置換され得、
前記R1〜R5のアルキル基、アルケニル基及びアルコキシル基のそれぞれは、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;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のアリル基;重水素で置換されたC6-C20のアリル基;フルオレニル基;O、N、S、Si及びPからなる群より選択された少なくとも1つのヘテロ原子を含む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;からなる群より選択された1つ以上の置換基で置換され得る。 - 以下の式のうちの1つで表されることを特徴とする請求項1に記載の化合物:
- 前記Zは、以下の式のうちの1つで表されることを特徴とする請求項1に記載の化合物:
- 以下の式のうちの1つで表されることを特徴とする請求項1に記載の化合物:
- 前記Arは、以下の式のうちの1つで表されることを特徴とする請求項1に記載の化合物。
- 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子素子において、
前記有機物層は、請求項1〜6の何れか1項に記載の化合物を含有することを特徴とする有機電子素子。 - 前記化合物は、前記有機物層の発光層に含有されており、
前記化合物は、同種の化合物又は2以上の異種の化合物であることを特徴とする請求項7に記載の有機電子素子。 - 前記化合物は、前記発光層の燐光ホスト物質として用いられることを特徴とする請求項8に記載の有機電子素子。
- 前記第1電極と第2電極の一面のうちの前記有機物層と反対となる少なくとも一面に形成される光効率改善層を更に含むことを特徴とする請求項7に記載の有機電子素子。
- 前記有機物層は、スピンコーティング工程、ノズルプリンティング工程、インクジェットプリンティング工程、スロットコーティング工程、ディップコーティング工程又はロールツーロール工程により形成されることを特徴とする請求項7に記載の有機電子素子。
- 請求項7に記載の有機電子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、を含む電子装置。 - 前記有機電子素子は、有機電子発光素子、有機太陽電池、有機感光体、有機トランジスタ、及び単色又は白色照明用素子のうちの少なくとも1つであることを特徴とする請求項12に記載の電子装置。
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US9331288B2 (en) | 2016-05-03 |
US9570689B2 (en) | 2017-02-14 |
US20150349272A1 (en) | 2015-12-03 |
JP5990622B2 (ja) | 2016-09-14 |
CN105131020B (zh) | 2018-03-09 |
EP2949725A1 (en) | 2015-12-02 |
KR101561566B1 (ko) | 2015-10-27 |
CN105131020A (zh) | 2015-12-09 |
EP2949725B1 (en) | 2016-12-14 |
US20160233433A1 (en) | 2016-08-11 |
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