JP2022514108A - 化合物およびこれを含む有機発光素子 - Google Patents
化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP2022514108A JP2022514108A JP2021540474A JP2021540474A JP2022514108A JP 2022514108 A JP2022514108 A JP 2022514108A JP 2021540474 A JP2021540474 A JP 2021540474A JP 2021540474 A JP2021540474 A JP 2021540474A JP 2022514108 A JP2022514108 A JP 2022514108A
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- light emitting
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 564
- 239000000126 substance Substances 0.000 claims abstract description 248
- 239000010410 layer Substances 0.000 claims description 240
- 125000004432 carbon atom Chemical group C* 0.000 claims description 181
- 125000002950 monocyclic group Chemical group 0.000 claims description 130
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 125000003367 polycyclic group Chemical group 0.000 claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 87
- -1 polycyclic aliphatic hydrocarbon Chemical class 0.000 claims description 82
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 63
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 57
- 239000002019 doping agent Substances 0.000 claims description 56
- 239000012044 organic layer Substances 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052805 deuterium Inorganic materials 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000003277 amino group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 20
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
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- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 5
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- 0 C*N(C)C1=CCC(*)CC(N(*)I=C2)=C1B2I Chemical compound C*N(C)C1=CCC(*)CC(N(*)I=C2)=C1B2I 0.000 description 247
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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- 229910052782 aluminium Inorganic materials 0.000 description 8
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- FYSWUOGCANSBCW-UHFFFAOYSA-N naphtho[1,2-g][1]benzothiole Chemical group C1=CC=C2C3=CC=C4C=CSC4=C3C=CC2=C1 FYSWUOGCANSBCW-UHFFFAOYSA-N 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- SEKSWDGNGZWLDU-UHFFFAOYSA-N 1,1,2,2-tetramethylcyclohexane Chemical compound CC1(C)CCCCC1(C)C SEKSWDGNGZWLDU-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
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- 125000005264 aryl amine group Chemical group 0.000 description 7
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- 239000000284 extract Substances 0.000 description 7
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- 239000002184 metal Substances 0.000 description 7
- YTIFDAAZLZVHIX-UHFFFAOYSA-N naphtho[1,2-g][1]benzofuran Chemical group C1=CC=C2C3=CC=C4C=COC4=C3C=CC2=C1 YTIFDAAZLZVHIX-UHFFFAOYSA-N 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 7
- 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 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 6
- 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 6
- 239000012153 distilled water Substances 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
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- YRIKDGJWRMHTJP-UHFFFAOYSA-N 1-bromo-3-chloro-5-methylbenzene Chemical compound CC1=CC(Cl)=CC(Br)=C1 YRIKDGJWRMHTJP-UHFFFAOYSA-N 0.000 description 5
- DRKSMCFPUOMHMK-UHFFFAOYSA-N 2,3,4,5,6,9-hexahydro-1h-carbazole Chemical group C1=CCCC2=C1NC1=C2CCCC1 DRKSMCFPUOMHMK-UHFFFAOYSA-N 0.000 description 5
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- 125000003282 alkyl amino group Chemical group 0.000 description 5
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- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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Abstract
Description
X1は、OまたはSであり、
A1は、置換もしくは非置換のヘテロ環;置換もしくは非置換の芳香族炭化水素環;または置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環であり、
A2は、置換もしくは非置換の芳香族炭化水素環;置換もしくは非置換の脂肪族炭化水素環;または置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、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リール基;置換もしくは非置換のヘテロ環基;または置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環基であり、
R1は、水素;重水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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;置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環基;または置換もしくは非置換のヘテロ環基であり、
r1は、1~3の整数であり、
前記r1が2以上の場合、前記2以上のR1は、互いに同一または異なり、
前記化学式1は、置換もしくは非置換のアルキル基で置換された脂肪族炭化水素縮合環を少なくとも1つ含む。
A1、A2、X1、Ar1、Ar2、R1、およびr1の定義は、前記化学式1で定義したものと同じである。
A1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じである。
A1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じである。
X1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じであり、
A"1は、置換もしくは非置換の脂肪族炭化水素環であり、
R11およびR12は、互いに同一または異なり、それぞれ独立して、水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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るか、隣接した基は、互いに結合して置換もしくは非置換の環を形成し、
r11は、1~4の整数であり、前記r11が2以上の場合、前記2以上のR11は、互いに同一または異なり、
r12は、1または2であり、前記r12が2の場合、前記2個のR12は、互いに同一または異なる。
X1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じであり、
A"1は、置換もしくは非置換の脂肪族炭化水素環であり、
R11およびR12は、互いに同一または異なり、それぞれ独立して、水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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るか、隣接した基は、互いに結合して環を形成し、
r11は、1~4の整数であり、前記r11が2以上の場合、前記2以上のR11は、互いに同一または異なり、
r12は、1または2であり、前記r12が2の場合、前記2個のR12は、互いに同一または異なる。
X1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じであり、
A"1は、置換もしくは非置換の脂肪族炭化水素環であり、
R12は、水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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、
r12は、1または2であり、前記r12が2の場合、前記2個のR12は、互いに同一または異なる。
X1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じであり、
A"1は、置換もしくは非置換の脂肪族炭化水素環であり、
R12は、水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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、
r12は、1または2であり、前記r12が2の場合、前記2個のR12は、互いに同一または異なる。
前記化学式1のAr1がフェニル基であり、前記Ar1に前記アルキル基で置換された脂肪族炭化水素縮合環として前記
L20およびL21は、互いに同一または異なり、それぞれ独立して、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ヘテロ環基であり、
Ar20およびAr21は、互いに同一または異なり、それぞれ独立して、水素;重水素;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、
R20およびR21は、互いに同一または異なり、それぞれ独立して、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、
r21は、1~7の整数であり、前記r21が2以上の場合、2以上のR21は、互いに同一または異なる。
Ar1は、前記化学式Hの-L20-Ar20の定義と同じであり、
2:第1電極
3:発光層
4:第2電極
5:正孔注入層
6:正孔輸送層
7:電子ブロック層
8:第1電子輸送層
9:第2電子輸送層
10:電子注入層
Claims (17)
- 下記化学式1で表される
化合物:
[化学式1]
X1は、OまたはSであり、
A1は、置換もしくは非置換のヘテロ環;置換もしくは非置換の芳香族炭化水素環;または置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環であり、
A2は、置換もしくは非置換の芳香族炭化水素環;置換もしくは非置換の脂肪族炭化水素環;または置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、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リール基;置換もしくは非置換のヘテロ環基;または置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環基であり、
R1は、水素;重水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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;置換もしくは非置換の芳香族炭化水素環および脂肪族炭化水素環の縮合環基;または置換もしくは非置換のヘテロ環基であり、
r1は、1~3の整数であり、
前記r1が2以上の場合、前記2以上のR1は、互いに同一または異なり、
前記化学式1は、置換もしくは非置換のアルキル基で置換された脂肪族炭化水素縮合環を少なくとも1つ含む。 - 前記化学式1は、下記化学式1-3または1-4で表される、
請求項1に記載の化合物:
[化学式1-3]
X1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じであり、
A"1は、置換もしくは非置換の脂肪族炭化水素環であり、
R11およびR12は、互いに同一または異なり、それぞれ独立して、水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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るか、隣接した基は、互いに結合して置換もしくは非置換の環を形成し、
r11は、1~4の整数であり、前記r11が2以上の場合、前記2以上のR11は、互いに同一または異なり、
r12は、1または2であり、前記r12が2の場合、2個の前記R12は、互いに同一または異なる。 - 前記化学式1-4は、下記化学式1-4-1または1-4-2で表される、
請求項3に記載の化合物:
[化学式1-4-1]
X1、A2、Ar1、Ar2、R1およびr1の定義は、前記化学式1で定義したものと同じであり、
A"1は、置換もしくは非置換の脂肪族炭化水素環であり、
R12は、水素;ハロゲン基;シアノ基;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アルキル基;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シリル基;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、
r12は、1または2であり、前記r12が2の場合、前記2個のR12は、互いに同一または異なる。 - 前記化学式1は、重水素で置換もしくは非置換の炭素数1~30の直鎖もしくは分枝鎖のアルキル基で置換された炭素数3~10の単環もしくは多環の脂肪族炭化水素縮合環を少なくとも1つ含む、
請求項1から4のいずれか1項に記載の化合物。 - 前記A1は、置換もしくは非置換の炭素数2~30の単環もしくは多環のヘテロ環;置換もしくは非置換の6~30の単環もしくは多環の芳香族炭化水素環;置換もしくは非置換の3~30の単環もしくは多環の脂肪族炭化水素環;または置換もしくは非置換の炭素数6~30の単環もしくは多環の芳香族炭化水素環および炭素数3~30の単環もしくは多環の脂肪族炭化水素環の縮合環であり、
前記A2は、置換もしくは非置換の炭素数6~30の単環もしくは多環の芳香族炭化水素環;置換もしくは非置換の炭素数3~30の単環もしくは多環の脂肪族炭化水素環;または置換もしくは非置換の炭素数6~30の単環もしくは多環の芳香族炭化水素環および炭素数3~30の単環もしくは多環の脂肪族炭化水素環の縮合環であり、
前記Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数6~30の単環もしくは多環のアリール基;置換もしくは非置換の炭素数2~30の単環もしくは多環のヘテロ環基;または置換もしくは非置換の炭素数6~30の単環もしくは多環の芳香族炭化水素環および炭素数3~30の単環もしくは多環の脂肪族炭化水素環の縮合環基であり、
前記R1は、水素;置換もしくは非置換の直鎖もしくは分枝鎖の炭素数1~30のアルキル基;置換もしくは非置換の炭素数3~30の単環もしくは多環のシクロアルキル基;置換もしくは非置換のアミン基;置換もしくは非置換の炭素数6~30の単環もしくは多環のアリール基;置換もしくは非置換の炭素数6~30の単環もしくは多環の芳香族炭化水素環および炭素数3~30の単環もしくは多環の脂肪族炭化水素環の縮合環基;または炭素数2~30の単環もしくは多環のヘテロ環基である、
請求項1から5のいずれか1項に記載の化合物。 - 第1電極と、
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1~7のいずれか1項に記載の化合物を含む
有機発光素子。 - 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、
請求項8に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、ドーパント物質を含み、
前記ドーパント物質は、前記化合物を含む、
請求項8に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、下記化学式Hで表される化合物をさらに含む、
請求項8から10のいずれか1項に記載の有機発光素子:
[化学式H]
L20およびL21は、互いに同一または異なり、それぞれ独立して、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ヘテロ環基であり、
Ar20およびAr21は、互いに同一または異なり、それぞれ独立して、水素;重水素;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、
R20およびR21は、互いに同一または異なり、それぞれ独立して、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、
r21は、1~7の整数であり、前記r21が2以上の場合、2以上のR21は、互いに同一または異なる。 - 前記Ar20は、置換もしくは非置換のヘテロ環基であり、
前記Ar21は、置換もしくは非置換のアリール基である、
請求項11に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、ホスト化合物をさらに含み、
前記ホスト化合物は、置換可能な位置の少なくとも1つの水素が重水素で置換されたものである、
請求項8に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、1種以上のドーパントおよびホストを含む、
請求項8に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、2種以上の混合ドーパントおよびホストを含む、
請求項8に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、1種以上のホストと、ドーパントとを含む、
請求項8に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、2種以上の混合ホストと、ドーパントとを含む、
請求項8に記載の有機発光素子。
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