JP6716145B1 - 含ホウ素化合物および有機el素子 - Google Patents
含ホウ素化合物および有機el素子 Download PDFInfo
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- JP6716145B1 JP6716145B1 JP2020022398A JP2020022398A JP6716145B1 JP 6716145 B1 JP6716145 B1 JP 6716145B1 JP 2020022398 A JP2020022398 A JP 2020022398A JP 2020022398 A JP2020022398 A JP 2020022398A JP 6716145 B1 JP6716145 B1 JP 6716145B1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000004429 atom Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 11
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000001454 anthracenes Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 27
- 238000010586 diagram Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 133
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- 239000007924 injection Substances 0.000 description 31
- -1 polycyclic aromatic compound Chemical class 0.000 description 17
- 230000004888 barrier function Effects 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 16
- 238000007740 vapor deposition Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 9
- 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 9
- 150000001639 boron compounds Chemical class 0.000 description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
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- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
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- GZOLRAQBGRLGHQ-UHFFFAOYSA-N 1,2-bis(3-bromophenyl)benzene Chemical group BrC1=CC=CC(C=2C(=CC=CC=2)C=2C=C(Br)C=CC=2)=C1 GZOLRAQBGRLGHQ-UHFFFAOYSA-N 0.000 description 2
- IRPWVEBIMPXCAZ-UHFFFAOYSA-N 1,3-dibromo-2-chlorobenzene Chemical compound ClC1=C(Br)C=CC=C1Br IRPWVEBIMPXCAZ-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 2
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- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- 125000005577 anthracene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 230000005587 bubbling Effects 0.000 description 2
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- 239000010406 cathode material Substances 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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 2
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- WGCOQYDRMPFAMN-ZDUSSCGKSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyrimidin-5-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=NC=1 WGCOQYDRMPFAMN-ZDUSSCGKSA-N 0.000 description 1
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011160 research 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
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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Abstract
Description
有機EL素子は、自己発光性素子としての利点を活かし、高発光効率、高画質、低消費電力、長寿命さらには薄型のデザイン性に優れた発光素子として期待されている。
このような発光層では、ホストに注入された電荷から効率よく励起子を生成することができる。そして、生成された励起子のエネルギーをドーパントに移動させ、ドーパントから高効率の発光を得ることができる。
Cy1は核原子数5〜30のアリール基を表す。
一般式(1)で表される骨格の水素の一部または全部は、重水素、ハロゲン、炭素数1〜6のアルキル基、核原子数5〜30のアリール基、置換もしくは無置換のシリル基、置換もしくは無置換のアミノ基、または、シアノ基で置換されていてもよい。
前記Cy1は、具体的には下記構造式で表されるベンゼン環、ナフタレン環またはキノキサリン環である。式中、波線は結合位置を表す。
一般式(2)で表される骨格の水素の一部または全部は、重水素、ハロゲン、炭素数1〜6のアルキル基、核原子数5〜30のアリール基、置換もしくは無置換のシリル基、置換もしくは無置換のアミノ基、または、シアノ基で置換されていてもよい。
本発明の有機EL素子は、前記含ホウ素化合物を発光帯域に含有する。
本発明の有機EL素子は、前記含ホウ素化合物を発光層に含有する。
本発明の有機EL素子は、前記含ホウ素化合物を発光層に0.1〜20wt%含有する。
前記有機EL素子では、発光層のホストとしてアントラセン誘導体を用いることが好ましい。
前記有機EL素子では、発光層のホストとして、下記一般式(3)で表される骨格を有するアントラセン誘導体を用いることが好ましい。
本発明の含ホウ素化合物は、一般式(1)で表される骨格を有する。
一般式(1)で表される骨格の水素の一部または全部は、重水素、ハロゲン、炭素数1〜6のアルキル基、核原子数5〜30のアリール基、置換もしくは無置換のシリル基、置換もしくは無置換のアミノ基、または、シアノ基で置換されていてもよい。
炭素数1〜6のアルキル基および核原子数5〜30のアリール基は、一般式(1)の炭素数1〜6のアルキル基および核原子数5〜30のアリール基について説明したものと同じである。ただし、核原子数5〜30のアリール基において、R4またはR5がフェニル基である場合、該フェニル基のオルト位にある炭素とC1またはC2とは連結してもよい。なお、C1およびC2は炭素原子を表す。
一般式(2)で表される骨格の水素の一部または全部は、重水素、ハロゲン、炭素数1〜6のアルキル基、核原子数5〜30のアリール基、置換もしくは無置換のシリル基、置換もしくは無置換のアミノ基、または、シアノ基で置換されていてもよい。
正孔注入層2を形成する正孔注入材料には、例えば、(ポリ(アリーレンエーテルケトン)含有トリフェニルアミン(KLHIP:PPBI)、1,4,5,8,9,11−ヘキサアザトリフェニレンヘキサカルボニトリル(HATCN)およびPEDOT−PSS等が挙げられる。これらの材料からなる正孔注入層2はポリマーバッファー層とも呼ばれ、有機EL素子の駆動電圧を下げる効果を発揮する。
Yは芳香族環式置換基または非芳香族環式置換基を表す。芳香族環式置換基または非芳香族環式置換基は、フェニル基、ビフェニル基、ナフチル基、およびジベンゾフラニル基等が好ましく、フェニル基、1−ビフェニル基、および1−ナフチル基、および2−ジベンゾフラニル基等がより好ましい。
ホストの添加量は、発光層5用材料全体の50〜99.9wt%が好ましく、80〜95wt%がより好ましい。
得られた化合物AはFD−MS(電界脱離質量分析)の測定により、m/Z=494.4の質量スペクトルが観測されたので化合物Aを記載の構造の化合物と同定した。
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。
この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HIM(正孔注入材料)を入れたモリブデン製蒸着用ボート、HTM(正孔輸送材料)を入れたモリブデン製蒸着用ボート、EBL(電子障壁材料)を入れたモリブデン製蒸着用ボート、BH1(ホスト)を入れたモリブデン製蒸着用ボート、本発明の化合物Aを入れたモリブデン製蒸着用ボート、HBL(正孔障壁材料)を入れたモリブデン製蒸着用ボート、ETM(電子輸送材料)を入れたモリブデン製蒸着用ボート、LiFを入れたモリブデン製蒸着用ボート、およびアルミニウムを入れたタングステン製蒸着用ボートを装着した。それぞれの材料の構造式を以下に示す。
次にHBLが入った蒸着用ボートを加熱して膜厚20nmになるように蒸着して正孔障壁層6を形成した。次いでETMが入った蒸着用ボートを加熱して膜厚10nmになるように蒸着して電子輸送層7を形成した。
その後、電子注入層8の材料であるLiFが入った蒸着用ボートを加熱して膜厚1nmになるように0.01〜0.1nm/秒の蒸着速度で蒸着した。次いで、アルミニウムが入った蒸着用ボートを加熱して100nmになるように0.01〜2nm/秒の蒸着速度で蒸着することにより陰極9を形成し、有機EL素子を得た。
ITO電極を陽極1、LiF/アルミニウム電極を陰極9として直流電圧を印加すると青色発光が得られた。
これを初期輝度1000nitで定電流駆動した時に、輝度が95%になるまでの時間を測定した。
化合物Aの代わりに、下記構造式で表される化合物を用いた以外は実施例1と全く同様に素子を作製した。
これを初期輝度1000nitで定電流駆動した時に、輝度が95%になるまでの時間を測定した。
2 正孔注入層
3 正孔輸送層
4 電子障壁層
5 発光層
6 正孔障壁層
7 電子輸送層
8 電子注入層
9 陰極
Claims (8)
- 下記一般式(1)で表される骨格を有する含ホウ素化合物。
- 請求項1または2に記載の含ホウ素化合物を含有する有機EL素子。
- 請求項1または2に記載の含ホウ素化合物を発光帯域に含有する有機EL素子。
- 請求項1または2の含ホウ素化合物を発光層に含有する有機EL素子。
- 請求項1または2の含ホウ素化合物を発光層に0.1〜20wt%含有する有機EL素子。
- 発光層のホストとしてアントラセン誘導体を用いることを特徴とする、請求項6記載の有機EL素子。
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WO2022176543A1 (ja) * | 2021-02-18 | 2022-08-25 | コニカミノルタ株式会社 | トリアリールホウ素化合物、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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