JP2019512499A - 化合物およびこれを用いる有機発光素子 - Google Patents
化合物およびこれを用いる有機発光素子 Download PDFInfo
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- JP2019512499A JP2019512499A JP2018548405A JP2018548405A JP2019512499A JP 2019512499 A JP2019512499 A JP 2019512499A JP 2018548405 A JP2018548405 A JP 2018548405A JP 2018548405 A JP2018548405 A JP 2018548405A JP 2019512499 A JP2019512499 A JP 2019512499A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 195
- 239000010410 layer Substances 0.000 claims description 172
- 238000002347 injection Methods 0.000 claims description 74
- 239000007924 injection Substances 0.000 claims description 74
- 239000012044 organic layer Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 26
- 125000003367 polycyclic group Chemical group 0.000 claims description 22
- 125000002950 monocyclic group Chemical group 0.000 claims description 17
- 125000006267 biphenyl group Chemical group 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 10
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 9
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 9
- 125000005581 pyrene group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
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- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
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- 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 7
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- 229910052782 aluminium Inorganic materials 0.000 description 7
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 5
- ICQAKBYFBIWELX-UHFFFAOYSA-N (4-naphthalen-2-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=C(C=CC=C2)C2=C1 ICQAKBYFBIWELX-UHFFFAOYSA-N 0.000 description 5
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 3
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- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 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 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-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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- 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
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
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Abstract
Description
[化学式1]
R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;シアノ基;置換もしくは非置換の炭素数1〜20のアルキル基;置換もしくは非置換の炭素数3〜20のシクロアルキル基;置換もしくは非置換の炭素数6〜20の単環もしくは多環のアリール基;または置換もしくは非置換の炭素数3〜20の単環もしくは多環のヘテロ環基であり、
Ar1、Ar2および−L−(Y)nは、互いに異なり、
Ar1およびAr2は、互いに異なり、それぞれ独立に、水素;重水素;置換もしくは非置換の炭素数1〜20のアルキル基;置換もしくは非置換の炭素数6〜20の単環もしくは多環のアリール基;または置換もしくは非置換の炭素数3〜20の単環もしくは多環のヘテロ環基であり、
Lは、直接結合;置換もしくは非置換の炭素数6〜20の単環もしくは多環の2価〜6価のアリール基;または置換もしくは非置換の炭素数3〜20の単環もしくは多環の2価〜6価のヘテロアリール基であり、
Yは、ナフチル基;フェナントレン基;ジメチルフルオレン基;アントラセン基;トリフェニレン基;ピレン基;テトラセン基;クリセン基;ペリレン基;またはフルオランテン基であり、
nは、2〜5の整数であり、複数のYは、同一または異なる。
[反応式1]
化合物3−Bの代わりに化合物5−Bを用い、(4−(1−ナフタレニル)フェニル)ボロン酸の代わりに(4−(2−ナフタレニル)フェニル)ボロン酸を用いたことを除き、化合物3と同様の方法で化合物5を製造した。
<製造例14>化合物14の合成
1)化合物16−Aの合成
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。
前記実施例1における化合物1の代わりに化合物2を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物3を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物4を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物5を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物6を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物7を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物8を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物9を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物10を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物11を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物12を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物13を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物14を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物16を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物17を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物18を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物19を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物20を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物21を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物22を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物23を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物24を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物25を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
前記実施例1における化合物1の代わりに化合物26を用いたことを除けば、実施例1と同様の方法で有機発光素子を作製した。
2:陽極
3:発光層
4:陰極
5:正孔注入層
6:正孔輸送層
7:電子輸送層
Claims (10)
- 下記化学式1で表される化合物:
[化学式1]
R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;シアノ基;置換もしくは非置換の炭素数1〜20のアルキル基;置換もしくは非置換の炭素数3〜20のシクロアルキル基;置換もしくは非置換の炭素数6〜20の単環もしくは多環のアリール基;または置換もしくは非置換の炭素数3〜20の単環もしくは多環のヘテロ環基であり、
Ar1、Ar2および−L−(Y)nは、互いに異なり、
Ar1およびAr2は、互いに異なり、それぞれ独立に、水素;重水素;置換もしくは非置換の炭素数1〜20のアルキル基;置換もしくは非置換の炭素数6〜20の単環もしくは多環のアリール基;または置換もしくは非置換の炭素数3〜20の単環もしくは多環のヘテロ環基であり、
Lは、直接結合;置換もしくは非置換の炭素数6〜20の単環もしくは多環の2価〜6価のアリール基;または置換もしくは非置換の炭素数3〜20の単環もしくは多環の2価〜6価のヘテロアリール基であり、
Yは、ナフチル基;フェナントレン基;ジメチルフルオレン基;アントラセン基;トリフェニレン基;ピレン基;テトラセン基;クリセン基;ペリレン基;またはフルオランテン基であり、
nは、2〜5の整数であり、複数のYは、同一または異なる。 - 前記Lは、2価〜4価のフェニル基;2価〜4価のビフェニル基;2価〜4価のナフチル基;2価〜4価のフェナントレン基;2価〜4価のカルバゾール基;2価〜4価のピリジン基;2価〜4価のピリミジン基;2価〜4価のトリアジン基;2価〜4価のキノリン基;2価〜4価のジベンゾフラン基;または2価〜4価のジベンゾチオフェン基である、請求項1に記載の化合物。
- 前記Lは、3価のフェニル基;または3価のビフェニル基である、請求項1に記載の化合物。
- 前記複数のYは、同一である、請求項1から3のいずれか一項に記載の化合物。
- 前記複数のYは、異なる、請求項1から3のいずれか一項に記載の化合物。
- 前記Ar1およびAr2は、互いに異なり、それぞれ独立に、置換もしくは非置換のフェニル基;置換もしくは非置換のビフェニル基;置換もしくは非置換のフェナントレン基;置換もしくは非置換のジメチルフルオレン基;置換もしくは非置換のジベンゾフラン基;置換もしくは非置換のジベンゾチオフェン基;置換もしくは非置換のナフチル基;または置換もしくは非置換のピレン基である、請求項1から5のいずれか一項に記載の化合物。
- 前記Yは、ナフチル基またはフェナントレン基である、請求項1から6のいずれか一項に記載の化合物。
- 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発光素子であって、前記有機物層のうちの1層以上は、請求項1から8のいずれか一項に記載の化合物を含むものである有機発光素子。
- 前記有機物層は、電子輸送層、電子注入層、または電子注入または輸送を同時に行う層を含み、前記電子注入層、電子輸送層、または電子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9に記載の有機発光素子。
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CN108884059A (zh) | 2018-11-23 |
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KR20170113397A (ko) | 2017-10-12 |
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