JP2019108321A - 有機電界発光素子及び有機電界発光素子用アミン化合物 - Google Patents
有機電界発光素子及び有機電界発光素子用アミン化合物 Download PDFInfo
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- JP2019108321A JP2019108321A JP2018222248A JP2018222248A JP2019108321A JP 2019108321 A JP2019108321 A JP 2019108321A JP 2018222248 A JP2018222248 A JP 2018222248A JP 2018222248 A JP2018222248 A JP 2018222248A JP 2019108321 A JP2019108321 A JP 2019108321A
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- -1 amine compound Chemical class 0.000 title claims abstract description 179
- 239000000126 substance Substances 0.000 claims abstract description 158
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 89
- 125000003118 aryl group Chemical group 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000005843 halogen group Chemical group 0.000 claims abstract description 30
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 29
- 125000004431 deuterium atom Chemical group 0.000 claims abstract description 29
- 125000000732 arylene group Chemical group 0.000 claims abstract description 5
- 230000005525 hole transport Effects 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 238000002347 injection Methods 0.000 claims description 31
- 239000007924 injection Substances 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 21
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 138
- 230000000052 comparative effect Effects 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001412 amines Chemical group 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- 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 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000002356 single layer Substances 0.000 description 10
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- 239000007983 Tris buffer Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
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- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 8
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- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 7
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- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 6
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- 229910052749 magnesium Inorganic materials 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
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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 4
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- 125000003277 amino group Chemical group 0.000 description 4
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
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- 150000004706 metal oxides Chemical class 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical compound CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
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- 229910052791 calcium Inorganic materials 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940127573 compound 38 Drugs 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- IPUQGEALWGOFQS-UHFFFAOYSA-N spiro[10h-acridine-9,10'-anthracene]-9'-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC=C2C11C2=CC=CC=C2NC2=CC=CC=C21 IPUQGEALWGOFQS-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical group S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 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
- 238000001931 thermography Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
前記化学式1において、Arは置換若しくは無置換の環形成炭素数10以上60以下のアリール基であり、Lは置換若しくは無置換の環形成炭素数6以上30以下のアリーレン基であり、R1〜R2はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、a及びbはそれぞれ独立して0以上7以下の整数であり、cは1以上4以下の整数である。
前記化学式2−1〜化学式2−3において、dは0または1であり、R9は重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、nは0以上6以下の整数である。Ar、R1、R2、a及びbは、化学式1の説明において定義したとおりである。
前記化学式2−1−1〜化学式2−3−2において、n1、n3及びn5は、それぞれ独立して0以上4以下の整数であり、n2、n4及びn6はそれぞれ独立して0以上6以下の整数である。Ar、R1、R2、R9、a及びbは、化学式1及び化学式2−1〜化学式2−3の説明において定義したとおりである。
前記化学式3−1〜化学式3−3において、R3〜R5はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、eは0以上7以下の整数であり、f及びgはそれぞれ独立して0以上9以下の整数である。前記化学式3−1〜化学式3−3において、R1、R2、a、b、及びLは、化学式1の説明において定義したとおりである。
前記化学式4において、h及びiは0以上2以下の整数で、h及びiのうち少なくとも一つは1または2であり、R1〜R2はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基である。前記化学式4において、Ar、L及びcは、化学式1の説明において定義したとおりである。
前記化学式5において、R11〜R14、及びR21〜R24は、それぞれ独立して水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、R11〜R14、及びR21〜R24のうち少なくとも一つは重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であってもよい。R11及びR21、R12及びR22、R13及びR23、R14及びR24のうち少なくとも一対は互いに異なってもよい。前記化学式5において、Ar、L及びcは、化学式1の説明において定義したとおりである。
前記化学式6において、R6、R7及びR10はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、R8はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であるか、複数のR8が互いに結合されて環を形成し、j及びkはそれぞれ独立して0以上7以下の整数であり、lは0以上7以下の整数であり、mは0または1であり、uは0以上6以下の整数である。
化合物A(14.0g、63.9mmol)、化合物B(33.6g、127.7mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(Pd2(dba)3)(5.8g、6.4mmol)、トリ(tert−ブチルホスフィン)(P(tBu)3)(2.1g、10.2mmol)、ナトリウムtert−ブトキシド(NaO(tBu))(24.5g、6.4mmol)のトルエン懸濁液(1150mL)を脱気し、アルゴン(Ar)雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、化合物1(26.5g、45.3mmol、71%)を得た。FAB−MS測定で測定された化合物1の分子量は583であった。
(中間体Eの合成)
化合物C(37.6g、146.1mmol)、化合物D(20.0g、146.1mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(Pd(PPh3)4)(8.4g、7.3mmol)、炭酸カリウム(K2CO3)(24.2g、175.3mmol)のトルエン/EtOH/H2O懸濁液(1200/120/240mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、中間体E(25.5g、94.9mmol、65%)を得た。FAB−MS測定で測定された中間体Eの分子量は269であった。
中間体E(14.0g、52.0mmol)、化合物B(27.4g、104.0mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(Pd2(dba)3)(4.8g、5.2mmol)、トリ(tert−ブチルホスフィン)(1.7g、8.3mmol)(P(tBu)3)、ナトリウムtert−ブトキシド(NaO(tBu))(20.0g、5.2mmol)のトルエン懸濁液(940mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、化合物4(22.4g、35.4mmol、68%)を得た。FAB−MS測定で測定された化合物4の分子量は633であった。
(中間体Hの合成)
化合物F(22.1g、107.0mmol)、化合物G(20.0g、187.0mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(Pd(PPh3)4)(6.2g、5.35mmol)、炭酸カリウム(K2CO3)(17.7g、128.3mmol)のトルエン/EtOH/H2O懸濁液(880/90/180mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、中間体H(15.8g、58.8mmol、55%)を得た。FAB−MS測定で測定された中間体Hの分子量は269であった。
中間体H(14.0g、52.0mmol)、化合物B(27.4g、104.0mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(Pd2(dba)3)(4.8g、5.2mmol)、トリ(tert−ブチルホスフィン))(P(tBu)3)(1.7g、8.3mmol)、ナトリウムtert−ブトキシド(NaO(tBu))(20.0g、5.2mmol)のトルエン懸濁液(940mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、化合物12(24.7g、39.0mmol、75%)を得た。FAB−MS測定で測定された化合物12の分子量は633であった。
(中間体Iの合成)
中間体A(20.0g、91.2mmol)、化合物B(24.0g、91.2mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(Pd2(dba)3)(8.4g、9.1mmol)、トリ(tert−ブチルホスフィン)(P(tBu)3)(3.0g、14.6mmol)、ナトリウムtert−ブトキシド(NaO(tBu))(17.5g、182.4mmol)のトルエン懸濁液(1600mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、中間体I(28.9g、72.1mmol、79%)を得た。
中間体I(25.0g、62.3mmol)、化合物J(21.1g、62.3mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(Pd2(dba)3)(5.7g、6.2mmol)、トリ(tert−ブチルホスフィン)(P(tBu)3)(2.0g、10.0mmol)、ナトリウムtert−ブトキシド(NaO(tBu))(12.0g、124.5mmol)のトルエン懸濁液(1100mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、化合物27(29.6g、44.8mmol、72%)を得た。FAB−MS測定で測定された化合物の分子量は659であった。前記結果を介して、合成した化合物が化合物27であることが分かった。
中間体I(20.0g、49.8mmol)、化合物K(22.2g、49.8mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(Pd2(dba)3)(4.6g、5.0mmol)、トリ(tert−ブチルホスフィン)(P(tBu)3)(1.6g、8.0mmol)、ナトリウムtert−ブトキシド(NaO(tBu))(9.6g、99.6mmol)のトルエン懸濁液(900mL)を脱気し、アルゴン雰囲気下で4時間80℃に加熱した。空冷後、反応液をフロリジルろ過・濃縮して得られた残渣をカラムクロマトグラフィで精製して、化合物38(25.9g、33.9mmol、68%)を得た。FAB−MS測定で測定された化合物の分子量は765であった。前記結果を介して、合成した化合物が化合物38であることが分かった。
上述した化合物1、4、12、27及び38を正孔輸送材料として使用し、実施例1〜5の有機電界発光素子を製作した。
[実施例化合物]
[比較例化合物]
上述した実験例化合物1、4、12、27、及び38、及び比較例化合物c1〜c6で製作した有機電界発光素子の発光効率及び発光寿命を評価した。評価結果を下記表1に示す。発光効率及び発光寿命は、比較例1の有機電界発光素子の発光効率及び発光寿命を100%とした際の各実施例及び比較例の相対的な発光効率比及び発光寿命比を測定した。
Claims (14)
- 下記化学式1で表されるアミン化合物。
(前記化学式1において、
Arは置換若しくは無置換の環形成炭素数10以上60以下のアリール基であり、
Lは置換若しくは無置換の環形成炭素数6以上30以下のアリーレン基であり、
R1及びR2はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
a及びbはそれぞれ独立して0以上7以下の整数であり、
cは1以上4以下の整数である。) - 前記Lは、置換若しくは無置換のフェニレン基、または置換若しくは無置換のナフチレン基である請求項1に記載のアミン化合物。
- 前記化学式1で表されるアミン化合物は、下記化学式2−1〜化学式2−3のうちいずれか一つで表される請求項1に記載のアミン化合物。
(前記化学式2−1〜化学式2−3において、
dは0または1であり、
R9は重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
nは0以上6以下の整数である。) - 前記化学式2−1〜化学式2−3のうちいずれか一つで表されるアミン化合物は、下記化学式2−1−1〜化学式2−3−2のうちいずれか一つで表される請求項3に記載のアミン化合物。
(前記化学式2−1−1〜化学式2−3−2において、
n1、n3及びn5は、それぞれ独立して0以上4以下の整数であり、
n2、n4及びn6はそれぞれ独立して0以上6以下の整数である。) - 前記Arは置換若しくは無置換のナフチル基、または置換若しくは無置換のフェナントリル基である請求項1に記載のアミン化合物。
- 前記化学式1で表されるアミン化合物は、下記化学式3−1〜化学式3−3のうちいずれか一つで表される請求項1に記載のアミン化合物。
(前記化学式3−1〜化学式3−3において、
R3〜R5はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
eは0以上7以下の整数であり、
fはそれぞれ独立して0以上9以下の整数である。) - 前記a及びbのうち少なくとも一つが1または2であり、
前記R1及びR2はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換のフェナントリル基、置換若しくは無置換のカルバゾリル基、置換若しくは無置換のジベンゾフラニル基、または置換若しくは無置換のジベンゾチオフェニル基である請求項1に記載のアミン化合物。 - 前記化学式1で表されるアミン化合物は、下記化学式4で表される請求項1に記載のアミン化合物。
前記化学式4において、
h及びiは0以上2以下の整数で、h及びiのうち少なくとも一つは1または2である。 - 前記化学式1で表されるアミン化合物は、下記化学式5で表される請求項1に記載のアミン化合物。
(前記化学式5において、
R11〜R14、及びR21〜R24は、はそれぞれ独立して水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、R11〜R14、及びR21〜R24のうち少なくとも一つは重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
R11及びR21、R12及びR22、R13及びR23、R14及びR24のうち少なくとも一対は互いに異なる。) - 前記化学式1で表されるアミン化合物は、下記化学式6で表される請求項1に記載のアミン化合物。
(前記化学式6において、
R6、R7、及びR10は、それぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
R8はそれぞれ独立して重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、R8が複数の場合、2つ以上のR8が互いに結合されて環を形成し、
j及びkはそれぞれ独立して0以上7以下の整数であり、
lは0以上7以下の整数であり、
uは0以上6以下の整数であり、
mは0または1である。) - 前記化学式1で表されるアミン化合物は、下記第1化合物群に示した化合物のうちから選択されるいずれか一つである請求項1に記載のアミン化合物。
[第1化合物群]
- 第1電極と、
前記第1電極の上に配置され、請求項1乃至請求項11のうちいずれか一つのアミン化合物を含む正孔輸送領域と、
前記正孔輸送領域の上に配置される発光層と、
前記発光層の上に配置される電子輸送領域と、
前記電子輸送領域の上に配置される第2電極と、を含む有機電界発光素子。 - 前記正孔輸送領域は、
前記第1電極の上に配置される正孔注入層と、
前記正孔注入層の上に配置される正孔輸送層と、を含うが、
前記正孔輸送層は、請求項1乃至請求項11のうちいずれか一つのアミン化合物を含む請求項12に記載の有機電界発光素子。 - 前記正孔輸送領域は複数の層を含み、
前記複数の層のうち、前記発光層に接触する層は前記請求項1乃至請求項11のうちいずれか一つのアミン化合物を含む請求項12に記載の有機電界発光素子。
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KR20160143627A (ko) * | 2014-02-28 | 2016-12-14 | 머티어리얼사이언스 주식회사 | 유기전계발광소자용 유기화합물 및 상기 유기화합물을 포함하는 유기전계발광소자 |
US20170125689A1 (en) * | 2014-06-18 | 2017-05-04 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
KR20160059609A (ko) * | 2014-11-19 | 2016-05-27 | 덕산네오룩스 주식회사 | 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자 |
KR20160113783A (ko) * | 2015-03-23 | 2016-10-04 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US20160301004A1 (en) * | 2015-04-07 | 2016-10-13 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
JP7123466B2 (ja) * | 2017-05-10 | 2022-08-23 | 三星ディスプレイ株式會社 | アミン化合物及びこれを含む有機el素子 |
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EP3521280B1 (en) | 2023-05-10 |
US11101442B2 (en) | 2021-08-24 |
CN109928950A (zh) | 2019-06-25 |
EP3521280A1 (en) | 2019-08-07 |
US20190189950A1 (en) | 2019-06-20 |
JP7264626B2 (ja) | 2023-04-25 |
KR20190074329A (ko) | 2019-06-28 |
KR102468708B1 (ko) | 2022-11-22 |
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