JP7504535B2 - 新規な化合物、それを含むコーティング組成物、それを用いた有機発光素子およびその製造方法 - Google Patents
新規な化合物、それを含むコーティング組成物、それを用いた有機発光素子およびその製造方法 Download PDFInfo
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- JP7504535B2 JP7504535B2 JP2023506319A JP2023506319A JP7504535B2 JP 7504535 B2 JP7504535 B2 JP 7504535B2 JP 2023506319 A JP2023506319 A JP 2023506319A JP 2023506319 A JP2023506319 A JP 2023506319A JP 7504535 B2 JP7504535 B2 JP 7504535B2
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- 125000001424 substituent group Chemical group 0.000 claims description 37
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- 238000000034 method Methods 0.000 claims description 19
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- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 11
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
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- -1 9,9-dimethylfluorenyl Chemical group 0.000 description 11
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
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- WQYVKKIHXMVIAN-UHFFFAOYSA-N 4-[4-(4-fluoroanilino)phenyl]-n-(4-fluorophenyl)aniline Chemical compound C1=CC(F)=CC=C1NC1=CC=C(C=2C=CC(NC=3C=CC(F)=CC=3)=CC=2)C=C1 WQYVKKIHXMVIAN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
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- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 1
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
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- HRZTZLCMURHWFY-UHFFFAOYSA-N 2-bromo-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Br HRZTZLCMURHWFY-UHFFFAOYSA-N 0.000 description 1
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- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-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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Description
本発明は、新規な化合物、前記化合物を含むコーティング組成物、前記コーティング組成物を用いて形成された有機発光素子およびその製造方法に関する。
Lは置換または非置換の二価の炭化水素環基;または置換または非置換の二価のヘテロ環基であり、
L1およびL2は互いに同一または異なり、それぞれ独立して、直接結合;置換または非置換のアリーレン基;または置換または非置換のヘテロアリーレン基であり、
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、置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
L10およびL11は互いに同一または異なり、それぞれ独立して、置換または非置換のアリーレン基であり、
X1およびX2は互いに同一または異なり、それぞれ独立して、硬化性基であり、
R1~R4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;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
n1およびn2はそれぞれ0~7の整数であり、n1およびn2がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m1は、1~Ar1に置換基が結合できる結合位置の数であり、
m2は、1~Ar2に置換基が結合できる結合位置の数であり、
n3およびn4は、それぞれ0~4の整数であり、n3およびn4がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m3およびm4はそれぞれ1~5の整数であり、n3+m3は5以下であり、n4+m4は5以下である。
L、L1、L2、Ar1、Ar2、L10、L11、X1、X2、R1~R4、n1~n4、およびm1~m4の定義は化学式1と同様である。
L、L1、L2、Ar1、Ar2、X1、X2、R1~R4、n1~n4およびm1~m4の定義は化学式1と同様であり、
R5およびR6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;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
n5およびn6は、それぞれ0~4の整数であり、n5およびn6がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なる。
前記構造において、・・・は結合位置を意味する。
製造例1.化合物1の製造
1)中間体1-1の合成
化合物1のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.83(m,4H)、7.45-7.36(m,12H)、7.27(t,2H)、7.17-6.86(m,36H)、6.65-6.57(m,2H)、5.65(dd,2H)、5.11(dd,2H)
化合物2のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.87(t,4H)、7.50(d,4H)、7.44-7.27(m,12H)、7.11-7.00(m,22H)6.94-6.83(m,10H)、6.66-6.59(m,2H)、5.66(dd,2H)、5.12(dd,2H)
化合物3のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.86-7.83(m,4H)、7.46-7.37(m,14H)、7.30-7.22(m,6H)、7.10-6.87(m,28H)、6.65-6.56(m,2H)、5.66(dd,2H)、5.11(dd,2H)
化合物4のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.80-7.74(m,6H)、7.69(d,2H)、7.44-7.33(m,8H)、7.30-7.24(m,4H))、7.06-6.80(m,36H)、6.71-6.63(m,2H)、6.56(m,2H)、6.30-6.28(m,2H)、5.70(dd,2H)、5.17(dd,2H)
1)中間体5-1の合成
化合物5のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.84-7.81(m,4H)、7.46(d,2H)、7.43-7.34(m,12H)、7.27(t,2H)、7.18-7.12(m,6H)、7.09-6.95(m,14H)、6.95-6.87(m,8H)、6.83(t,4H)、6.64-6.55(m,2H)、5.64(dd,2H)、5.10(dd,2H)
化合物6のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.79-7.73(m,6H)、7.69-7.66(m,2H)、7.44-7.40(m,6H)、7.36-7.22(m,8H)、7.08-6.85(m,22H)、6.85-6.67(m,10H)、6.71-6.63(m,2H)、6.58-6.55(m,2H)、6.26(m,2H)、2H)、5.70(dd,2H)、5.17(dd,2H)
化合物7のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.84-7.81(m,4H)、7.46(d,2H)、7.43-7.34(m,10H)、7.27(t,2H)、7.18-7.12(m,6H)、7.09-6.95(m,14H)、6.95-6.87(m,8H)、6.83(t,4H)、6.64-6.55(m,2H)、5.64(dd,2H)、5.10(dd,2H)、2.33(s,6H)
1)中間体8-1の合成
化合物8のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.84-7.81(m,4H)、7.46(d,2H)、7.43-7.33(m,12H)、7.26(t,2H)、7.19-7.13(m,6H)、7.09-6.96(m,14H)、6.94-6.87(m,8H)、6.83(t,4H)、6.64-6.55(m,2H)、5.64(dd,2H)、5.16(s,4H)5.10(dd,2H)
1)中間体9-1の合成
化合物9のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.83(m,4H)、7.45-7.36(m,12H)、7.27(t,2H)、7.17-6.86(m,28H)、6.65-6.57(m,2H)、5.65(dd,2H)、5.11(dd,2H)
実験例1.
ITO(indium tin oxide)が1,500Åの厚さで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、超音波で洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)の製品を使用し、蒸留水としてはミリポア社(Millipore Co.)の製品のフィルター(Filter)で2次にかけてろ過されたた蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間進行した。蒸留水洗浄が終わった後、イソプロピル、アセトンの溶剤で超音波洗浄をして乾燥させた後、前記基板を5分間洗浄した後、グローブボックスで基板を輸送させた。
正孔注入層(HIL)の製造時、前記化合物1の代わりに下記の表1に記載の化合物を用いたことを除いては、前記実験例1と同様の方法で有機発光素子を製造した。
正孔注入層の製造時に、前記化合物1の代わりに下記の表1に記載のように、下記の化合物CE1~CE3のうちいずれか1つの化合物を用いたことを除いては、前記実験例1と同様の方法で有機発光素子を製造した。
201 ・・・第1の電極
301 ・・・正孔注入層
401 ・・・正孔輸送層
501 ・・・発光層
601 ・・・電子輸送および注入層
701 ・・・第2の電極
Claims (14)
- 下記化学式1で表される化合物:
Lは置換または非置換の二価の炭化水素環基であり、
L1およびL2は互いに同一または異なり、それぞれ独立して、単結合;または置換または非置換のアリーレン基であり、
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、置換または非置換のアリール基であり、
L10およびL11は互いに同一または異なり、それぞれ独立して、置換または非置換のアリーレン基であり、
X1およびX2は互いに同一または異なり、それぞれ独立して、硬化性基であり、
R1~R4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;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
n1およびn2はそれぞれ0~7の整数であり、n1およびn2がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m1は、1~Ar1に置換基が結合できる結合位置の数であり、
m2は、1~Ar2に置換基が結合できる結合位置の数であり、
n3およびn4は、それぞれ0~4の整数であり、n3およびn4がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m3およびm4は、それぞれ1~5の整数であり、n3+m3は5以下であり、n4+m4は5以下である。 - 前記硬化性基は、下記構造から選択されるいずれか一つであり、
下記の構造において、--は結合位置を意味する、請求項1に記載の化合物:
- 前記化学式1は、下記の化学式2で表される、請求項1または2に記載の化合物:
L、L1、L2、Ar1、Ar2、L10、L11、X1、X2、R1~R4、n1~n4、およびm1~m4の定義は、化学式1と同様である。 - 前記化学式1は、下記の化学式3で表される、請求項1~3のいずれか一項に記載の化合物:
L、L1、L2、Ar1、Ar2、X1、X2、R1~R4、n1~n4およびm1~m4の定義は、化学式1と同様であり、
R5およびR6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;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
n5およびn6はそれぞれ0~4の整数であり、n5およびn6がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なる。 - 前記Lは、C1-20のアルキル基で置換または非置換のC6-30の二価の炭化水素環基である、請求項1~4のいずれか一項に記載の化合物。
- 前記Lは、下記の構造から選択されるいずれか一つである、請求項1~5のいずれか一項に記載の化合物:
前記構造において、・・・は結合位置を意味する。 - 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、置換または非置換のフェニル基;置換または非置換のビフェニル基;または置換または非置換のターフェニル基である、請求項1~6のいずれか一項に記載の化合物。
- 前記m1およびm2は、それぞれ1~5の整数である、請求項1~7のいずれか一項に記載の化合物。
- 前記化学式1は、下記の化合物のいずれか一つで表される、請求項1~8のいずれか一項に記載の化合物。
- 請求項1ないし9のいずれか一項に記載の化合物を含むコーティング組成物。
- 第1の電極;
第2の電極;および
前記第1の電極と前記第2の電極との間に設けられる1層以上の有機物層を含み、
前記1層以上の有機物層のうち1層以上は、請求項10のコーティング組成物またはその硬化物を含む、有機発光素子。 - 前記コーティング組成物またはその硬化物を含む有機物層は、正孔輸送層または正孔注入層である、請求項11に記載の有機発光素子。
- 第1の電極を準備する段階;
前記第1の電極上に1層以上の有機物層を形成する段階;および
前記1層以上の有機物層上に第2の電極を形成する段階を含み、
前記1層以上の有機物層を形成する段階は、請求項10のコーティング組成物を用いて有機物層を形成する段階を含む、有機発光素子の製造方法。 - 前記コーティング組成物を用いて有機物層を形成する段階は、
前記コーティング組成物をコーティングする段階;および
前記コーティングされたコーティング組成物を熱処理または光処理することを含む、請求項13に記載の有機発光素子の製造方法。
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