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WO2014075382A1 - Dérivé de benzothiophène et son utilisation dans le domaine des dispositifs électroluminescents organiques - Google Patents

Dérivé de benzothiophène et son utilisation dans le domaine des dispositifs électroluminescents organiques Download PDF

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Publication number
WO2014075382A1
WO2014075382A1 PCT/CN2013/001190 CN2013001190W WO2014075382A1 WO 2014075382 A1 WO2014075382 A1 WO 2014075382A1 CN 2013001190 W CN2013001190 W CN 2013001190W WO 2014075382 A1 WO2014075382 A1 WO 2014075382A1
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Prior art keywords
substituted
group
compound
benzothiophene
unsubstituted
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Chinese (zh)
Inventor
邱勇
范洪涛
王星
段炼
任雪艳
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
Beijing Eternal Material Technology Co Ltd
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
Beijing Eternal Material Technology Co Ltd
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Priority to KR1020157011386A priority Critical patent/KR101778416B1/ko
Priority to JP2015533410A priority patent/JP6120972B2/ja
Publication of WO2014075382A1 publication Critical patent/WO2014075382A1/fr
Anticipated expiration legal-status Critical
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/58—Radicals substituted by nitrogen atoms
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/74—Naphthothiophenes
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to an organic compound, and more particularly to a benzothiophene derivative for use in an organic electroluminescent device and its use in the field of organic electroluminescent display technology.
  • Scenery technology a benzothiophene derivative for use in an organic electroluminescent device and its use in the field of organic electroluminescent display technology.
  • the hole injecting and transporting materials used in organic electroluminescent devices are generally triarylamine derivatives (for example, the light-emitting patent: Publication No. CN 1152607C, published on 2004, 6, 2)
  • the general structural feature is that As the injection material, the triarylamine structural unit is at least three or more in one molecule, and the two N are separated by a benzene ring, as in the structural formula 1; as a transport material, the triarylamine structural unit is generally used in one molecule. It is two, and the two N are separated by biphenyl. In this type of material, a typical example is NPB.
  • the problem to be solved by the present invention is to provide a novel type of double hole transport group-substituted benzothiophene derivative, and apply the derivative to the organic light-emitting functional layer as a hole transporting material and/or hole injection, respectively.
  • the host material of the material and/or the organic light-emitting layer further provides an organic electroluminescent device having a low driving voltage and high luminous efficiency.
  • the materials disclosed herein regardless of the structure of the substituent, contain at least two S atoms in the molecule, ensuring that the material readily gives electrons and transports holes.
  • the benzothiophene-substituted material substituted by the two-hole transport group has a high triplet energy level, a glass transition temperature, a strong hole transporting ability, and can effectively avoid fluorescence quenching caused by molecular aggregation in a thin film state.
  • the advantages enable the series of derivatives to be applied to the organic light-emitting functional layer as a hole transporting material and/or a hole injecting material, and to have potential applications as a host material, particularly a fluorescent blue host material.
  • the present invention provides a benzothiophene derivative having a structure represented by the formula (I):
  • Ri R 2 is independently selected from a C4 to C40 substituted or unsubstituted arylamine group, a C4 to C40 substituted or unsubstituted carbazole group, a C4 to C40 substituted or unsubstituted benzothiophene group, One of a substituted or unsubstituted benzofuran group of C4 to C40;
  • L is a bridging group selected from the group consisting of a single bond, a substituted aromatic amine of C4 to C40, a substituted carbazole of C4 to C40, a substituted benzothiophene of C4 to C40, one of an oxygen atom, a nitrogen atom or a sulfur atom;
  • R 3 -R 1() are independently selected from the group consisting of H atoms, dC ⁇ aliphatic straight or branched chain hydrocarbon groups or C 6 -C 3 .
  • An aromatic group, or, two adjacent groups are joined to form a ring, forming
  • n are selected from integers of 0-3, but m plus n is greater than 0 and less than or equal to 3.
  • the two adjacent groups are joined to form a ring to form one or more ring-closing structures.
  • the structural formula of the compound is as follows:
  • the benzothiophene derivative is used as a hole injecting material and/or a hole transporting material in an organic electroluminescent device.
  • the benzothiophene derivative can also be used as an organic light-emitting material of an organic light-emitting layer in an organic electroluminescent device, and the organic light-emitting material includes a host material and a dye.
  • the benzothiophene derivative can be used. It is used as a host material in the light-emitting layer in the organic electroluminescence device.
  • the present invention also provides an organic electroluminescent device comprising a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;
  • the material for the organic light-emitting functional layer includes a hole injecting material, a hole transporting material, an organic light-emitting material, and an electron transporting material, and the material for the organic light-emitting functional layer is a compound having the formula (I):
  • Ri is independently selected from a substituted or unsubstituted arylamine group of C4 to C40, a substituted or unsubstituted carbazole group of C4 to C40, a substituted or unsubstituted benzothiophene group of C4 to C40, C4 ⁇ One of a substituted or unsubstituted benzofuran group of C40;
  • L is a bridging group selected from the group consisting of a single bond, a substituted aromatic amine of C4 to C40, a substituted carbazole of C4 to C40, a substituted benzothiophene of C4 to C40, one of an oxygen atom, a nitrogen atom or a sulfur atom;
  • n are selected from integers of 0-3, but m plus n is greater than 0 and less than or equal to 3.
  • the present invention also provides an organic electroluminescent device comprising a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;
  • the material for the organic light-emitting functional layer includes a hole injecting material, a hole transporting material, an organic light-emitting material, and an electron transporting material, the hole injecting material being a compound having the formula (I):
  • Ri is independently selected from a substituted or unsubstituted arylamine group of C4 to C40, a substituted or unsubstituted carbazole group of C4 to C40, a substituted or unsubstituted benzothiophene group of C4 to C40, C4 ⁇ One of a substituted or unsubstituted benzofuran group of C40;
  • L is a bridging group selected from the group consisting of a single bond, a substituted aromatic amine of C4 to C40, a substituted carbazole of C4 to C40, a substituted benzothiophene of C4 to C40, one of an oxygen atom, a nitrogen atom or a sulfur atom;
  • n are selected from integers of 0-3, but m plus n is greater than 0 and less than or equal to 3.
  • the present invention also provides an organic electroluminescent device comprising a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;
  • Materials for the organic light-emitting functional layer include a hole injecting material, a hole transporting material, an organic light-emitting material, and an electron transporting material, the holes
  • Ri is independently selected from a substituted or unsubstituted arylamine group of C4 to C40, a substituted or unsubstituted carbazole group of C4 to C40, a substituted or unsubstituted benzothiophene group of C4 to C40, C4 ⁇ One of a substituted or unsubstituted benzofuran group of C40;
  • L is a bridging group selected from the group consisting of a single bond, a substituted aromatic amine of C4 to C40, a substituted carbazole of C4 to C40, a substituted benzothiophene of C4 to C40, one of an oxygen atom, a nitrogen atom or a sulfur atom;
  • R 3 -R 1() are independently selected from the group consisting of H atoms, dC ⁇ aliphatic straight or branched chain hydrocarbon groups or C 6 -C 3 . Or aromatic groups, or two adjacent groups are linked to form a naphthothiophene derivative;
  • n are selected from integers of 0-3, but m plus n is greater than 0 and less than or equal to 3.
  • the present invention also provides an organic electroluminescent device comprising a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;
  • Materials for the organic light-emitting functional layer include a hole injecting material, a hole transporting material, an organic light-emitting material, and an electron transporting material, the organic
  • Ri is independently selected from a substituted or unsubstituted arylamine group of C4 to C40, a substituted or unsubstituted carbazole group of C4 to C40, a substituted or unsubstituted benzothiophene group of C4 to C40, C4 ⁇ One of a substituted or unsubstituted benzofuran group of C40;
  • L is a bridging group selected from the group consisting of a single bond, a substituted aromatic amine of C4 to C40, a substituted carbazole of C4 to C40, a substituted benzothiophene of C4 to C40, one of an oxygen atom, a nitrogen atom or a sulfur atom;
  • R 3 -R 1() are independently selected from the group consisting of H atoms, dC ⁇ aliphatic straight or branched chain hydrocarbon groups or C 6 -C 3 . Or aromatic groups, or two adjacent groups are linked to form a naphthothiophene derivative;
  • n are selected from integers of 0-3, but m plus n is greater than 0 and less than or equal to 3.
  • the benzothiophene derivative disclosed in the present invention has at least one thiophene group, and a lone pair of electrons on the S atom easily loses electrons to form a hole, thereby making the compound have a hole injecting and/or transporting material. High carrier injection and transfer capability.
  • the benzothiophene derivatives disclosed in the present invention have a high molecular weight and a large number of twig structures, and have a high glass transition temperature, so that the stability of the compound is high, and the life of the device is further improved. Big benefits.
  • the benzothiophene derivatives disclosed in the present invention can be used as a hole injecting and/or transporting material, and the luminous efficiency of the device is greatly improved due to the high carrier injection and transport ability.
  • Device Examples OLED1 to OLED80 show that by using the organic compound of the present invention as an organic light-emitting functional layer material, a device can be effectively reduced in driving voltage and improved in current efficiency.
  • the benzothiophene derivatives disclosed in the present invention can also be used as a host material of an organic light-emitting layer, particularly as a fluorescent blue host material, and the materials in the present invention can also be combined with other commonly used fluorescent blue light bodies.
  • the double body because its molecular orbital level falls within the energy level of the host material, facilitates the transmission of electrons and holes, so that the luminous efficiency of the device is greatly improved.
  • the device examples OLED 81 to OLED 134 show that the organic compound of the present invention can be used as an organic light-emitting functional layer material, and the device can effectively reduce the driving voltage and improve the current efficiency.
  • Figure 1 is a nuclear magnetic resonance spectrum (1H) of an intermediate ⁇ 4-1 of the benzothiophene derivative of the present invention
  • Figure 2 is a mass spectrum of the benzothiophene derivative 3 ⁇ 4 ⁇ of the present invention.
  • Figure 3 is a graph showing the thermogravimetric spectrum of the benzothiophene derivative M ⁇ 1 according to the present invention.
  • Figure 4 is an absorption spectrum of the benzothiophene derivative 3 ⁇ 4 ⁇ of the present invention.
  • Figure is an emission spectrum of the benzothiophene derivative 3 ⁇ 4 ⁇ of the present invention.
  • Figure ⁇ is a nuclear magnetic spectrum (13C) of the benzothiophene derivative 3 ⁇ 4 ⁇ of the present invention. detailed description
  • Benzothiophene 3-bromo-9-phenyl-oxazole, 9-(4-bromophenyl)-oxazole, 4-bromo-triphenylamine, 2-bromo-9-phenyl- used in the present invention Carbazole, 3-bromo-9-methyl-carbazole, 9-(4-bromophenyl)-3,6-dimethyl-oxazole, diphenylamine, 2-bromodibenzo(b,d) Thiophene, 2-bromodibenzo(b,d)furan, aniline, bis(4-bromophenyl)ether, bis(4-bromophenyl) sulfide, 2, 8-dibromo-dibenzo(b) , d) thiophene, 3, 7-dibromo-dibenzo (b,d) thiophene, 2, 8-dibromo-dibenzo(b,d)furan, 3,7-d
  • the compound M1 prepared in this example has the structural formula and synthetic route as follows: N COg, - ⁇ ,, "to
  • compound M5 was prepared, and its structural formula and synthetic route are as follows:
  • compound M6 was prepared, and its structural formula and synthetic route are as follows:
  • the preparation method is:
  • M7 was prepared in exactly the same manner as in Example 1, except that 2,3'-di was replaced by 2,2'-dibromo-3,3'-biphenyl(b)thiophene and 4-oxazolylbenzoic acid, respectively. Bromo-2,2'-biphenyl(b)thiophene and 9-phenyl-9/-carbazole-3-boronic acid gave M7 (yield: 6.1 g, yield 81%).
  • compound M8 was prepared, and its structural formula and synthetic route were prepared.
  • compound M9 was prepared, and its structural formula and synthetic route are as follows:
  • compound M10 was prepared, and its structural formula and synthetic route are as follows:
  • intermediate M10-1-1 was brominated by NBS to give intermediate M10-1-2, which was coupled with diphenylamine by Buchwald to give intermediate M10-1-3. Hydrogen is obtained by reacting a lithium salt with diisopropyl borate and then acidifying to obtain boric acid M10-1.
  • Intermediate M10-2 is obtained by hydrogen extraction of n-decyllithium to obtain lithium salt diisopropyl borate and acid hydrolysis to obtain boronic acid Ml 0-2-2, ⁇ j 3-bromo-N -ethylcarbazole is coupled to the intermediate M10-2-3 via Suzuki coupling, and the intermediate M10-2 is obtained by bromination with NBS.
  • compound Ml 1 was prepared, and its structural formula and synthetic route are as follows:
  • Example 12 A similar method to Example 4 was used, except that 4-carbazolylbenzoic acid and dimethyl-4-oxazole boronic acid of M were substituted for 9-tolyl-9H-indazole-3-boronic acid and 4-di. Aniline phenylboronic acid, other conditions are unchanged, the compound M l 1 is obtained (white body, yield 45%).
  • Example 12
  • compound M 12 was prepared, and its structural formula and synthetic route are as follows:
  • intermediate M12-1 2, 3-dioxabenzothiophene and 4-boronic acid triphenylamine were coupled by Suzuki to obtain intermediate M12-1-1.
  • Intermediate M12-1 was obtained by the general preparation method of boric acid.
  • intermediate M12-2 Intermediate M12-2-1 was obtained by bromination with NBS with intermediate M12-2-2, and coupled with the substrate M12-2-3 by Suzuki to give intermediate M12-2-4. , intermediate M12-2 was obtained by bromination with NBS.
  • the synthesis step is completely referred to the preparation of the compound M7 in Example 7, except that W 3-boronic acid-N-phenylcarbazole is substituted for 4-oxazolylbenzeneboronic acid, thereby obtaining a compound M13 (A color, yield 57 %)
  • compound M]5 was prepared, and its structural formula and synthetic route are as follows:
  • the compound ⁇ 16 prepared in this example has the structural formula and synthetic route as follows:
  • compound M17 was prepared, and its structural formula and synthetic route are as follows:
  • compound M18 was prepared, and its structural formula and synthetic route are as follows:
  • compound M19 was prepared, and its structural formula and synthetic route are as follows:
  • Example 20 Using a method similar to that in Example 1, a compound such as dibenzo(b,d)furan-2-boronic acid was replaced by 9-phenyl-9-indazole-3-boronic acid, and the other conditions were unchanged to obtain a compound. M19 (white body, yield 56%) Example 20
  • compound M20 was prepared, and its structural formula and synthetic route are as follows:
  • M21-1 is hydrogenated to a lithium salt by n-butyllithium. Under the action of copper chloride, hydrazine is coupled to form intermediate M21-2, which is brominated by NBS to obtain intermediate M21-3, with 4-boronic acid diphenylamine via Suzuki. Coupling gave compound M21 (white body, yield 65%).
  • compound M22 was prepared, and its structural formula and synthetic route are as follows:
  • compound M23 was prepared, and its structural formula and synthetic route are as follows:
  • Example 25 A similar method as in Example 22 was carried out, in which the diphenylamine-4-boronic acid was replaced by 9-phenyl-9 /-carbazole-3-boronic acid to obtain the compound M24 (white, yield 69%).
  • Example 25 A similar method as in Example 22 was carried out, in which the diphenylamine-4-boronic acid was replaced by 9-phenyl-9 /-carbazole-3-boronic acid to obtain the compound M24 (white, yield 69%).
  • Example 25 A similar method as in Example 22 was carried out, in which the diphenylamine-4-boronic acid was replaced by 9-phenyl-9 /-carbazole-3-boronic acid to obtain the compound M24 (white, yield 69%).
  • compound M26 was prepared, and its structural formula and synthetic route are as follows.
  • compound M28 was prepared, and its structural formula and synthetic route are as follows:
  • the first two steps of the synthesis step are the same as the compound M30 in the embodiment 30, and the third step refers to the synthesis method of the compound M30 except that one of the starting materials, 9-phenyl-9H-carbazole-3-boronic acid, is changed to 4-diphenyl. Aminophenylboronic acid, other reagents, solvents and reaction conditions were unchanged, and a white product was obtained.
  • Example 29
  • the first two steps of the synthesis step are the same as the compound M30 in the embodiment 30, and the second step is based on the synthesis method of the compound M30' except that one of the starting materials, 9-phenyl-9H-carbazole-3-boronic acid, is changed to 9-(9H- Carbazole) Phenyl-4-boronic acid, other reagents, solvents and reaction conditions are unchanged, and a white optic product is obtained.
  • the first two steps of the synthesis step are the same as the compound M30 in the embodiment 30, and the second step refers to the synthesis method of the compound M30 except that one of the starting materials, 9-phenyl-9H-carbazole-3-boronic acid, is changed to 9-phenyl- 9H-carbazole-2-boronic acid, other reagents, solvents and reaction conditions are unchanged, and an A color l*l product is obtained.
  • compound M32 was prepared, and its structural formula and synthetic route are as follows:
  • Example 30 In the first two steps of the synthesis step, the compound M30 in Example 30 is the same, and the synthesis method of the compound M30 is carried out in two steps, except that one of the starting materials, 9-phenyl-9H-carbazole-3-boronic acid, is changed to dibenzothiophene-2. - Boric acid, other reagents, solvents and reaction conditions are unchanged to give a white homologous product.
  • Example 33
  • the compound M30 in Example 30 is the same, and the second step refers to the synthesis method of the compound M30 except that one of the starting materials, 9-phenyl-9H-carbazole-3-boronic acid, is changed to dibenzofuran-2. - Boric acid, other reagents, solvents and reaction conditions are unchanged to obtain A color product.
  • the first two steps of the synthesis step are the same as the compound M30 in the embodiment 30, and the third step refers to the synthesis method of the compound M30 except that one of the starting materials, 9-phenyl-9H-carbazole-3-boronic acid, is changed to 3-phenylbenzene.
  • the thiophene-2-boronic acid, other reagents, solvent and reaction conditions are unchanged, and the A color 1 ancient 1 product is obtained.
  • the compound M35 in Example 35 is the same, and the second step refers to the synthesis method of the compound M35 except that one of the starting materials, 4-carbazolylbenzoic acid, is changed to 9-phenyl-9-carbazole-3- Boric acid, other reagents, solvents and reaction conditions are unchanged, and an A color product is obtained.
  • compound M38 was prepared, and its structural formula and synthetic route are as follows:
  • Example 39 For the synthesis procedure, refer to the compound M37 in Example 37 except that one of the starting materials, 4-diphenylaminophenylboronic acid, was changed to 9-(9H-carbazole)phenyl-4-boronic acid, and other reagents, solvents and reaction conditions were determined. No change, the A color product is obtained.
  • Example 39
  • the compound M64 is the same in the first step, and the second step is based on the synthesis method of the compound M64, except that one of the raw materials 3,3'-dibromo-2,2'-biphenyl(b)thiophene is changed. It is 2,8-dibromo-dibenzothiophene, and other reagents, solvents and reaction conditions are unchanged, and an A color ⁇ steroid product is obtained.
  • Example 41 For the synthesis step, referring to the compound ⁇ 64 in Example 64, one of the starting materials, 3-boronic acid-indole-phenylcarbazole, was changed to 4-diphenylaminophenylboronic acid, and in the second step, one of the raw materials 3, 3' -Dibromo-2,2'-biphenyl(b)thiophene is changed to 2,8-dibromo-dibenzothiophene, and other reagents, solvents and reaction conditions are unchanged, and an A color I ancient product is obtained.
  • Example 41 Example 41
  • the synthesis step refers to the compound ⁇ 35 in Example 35, and one of the raw materials 4,4'-diphenyl ether diboric acid is changed to 3,7-diboronic acid-dibenzothiophene.
  • one of the raw materials 9- (9 ⁇ -carbazole) The phenyl-4-boronic acid was changed to 4-diphenylaminophenylboronic acid, and the other reagents, solvent and reaction conditions were unchanged to obtain a white homologous product.
  • the synthesis step refers to the compound ⁇ 35 in Example 35, and one of the raw materials 4,4'-diphenyl ether diboric acid is changed to 2,8-diboronic acid-dibenzothiophene, and the second step is to use one of the raw materials 9-( 9 ⁇ -carbazole) phenyl-4-boronic acid was changed to 4-diphenylaminophenylboronic acid, and other reagents, solvents and reaction conditions were unchanged, and a white product was obtained.
  • the compound M64 is the same in the first step, and the second step is based on the synthesis method of the compound M64, except that one of the raw materials 3,3'-dibromo-2,2'-biphenyl(b)thiophene is changed. It is 3,7-dibromo-dibenzothiophene, and other reagents, solvents and reaction conditions are unchanged, and an A color W product is obtained.
  • the first step of the synthesis step is the same as the compound M64 of Example 64.
  • the second step is to refer to the synthesis method of the compound M64, except that one of the raw materials 3,3'-dibromo-2,2'-biphenyl(b)thiophene is changed to 2, 8-dibromo-benzofuran, other reagents, solvents and reaction conditions are unchanged, and a product of A color is obtained.
  • the synthesis step refers to the compound M35 in the embodiment 35, and one of the raw materials 4,4'-diphenyl ether diboric acid is changed to 2,8 diboric acid-dibenzofuran, and in the second step, one of the raw materials 9-( 9H-carbazole) phenyl-4-boronic acid was changed to 4-diphenylaminophenylboronic acid, and other reagents, solvents and reaction conditions were unchanged, and a product of A color was obtained.
  • the compound M64 is the same in the first step, and the second step refers to the synthesis method of the compound M64, except that one of the raw materials 3,3'-bromo-2,2'-biphenyl(b)thiophene is changed. It is 3,7-bromo-benzofuran, and other reagents, solvents and reaction conditions are unchanged, and an internal color M product is obtained.
  • the second step refers to the synthesis method of the compound M64, except that one of the raw materials 3,3'-bromo-2,2'-biphenyl(b)thiophene is changed. It is 3,7-bromo-benzofuran, and other reagents, solvents and reaction conditions are unchanged, and an internal color M product is obtained.
  • Example 64 In a similar manner to the method of Example 64, the same was used to replace the 3-boronic acid-N-p-tolylcarbazole and 3,6-dibromo-9-phenyl-9//-carbazole as M. -boronic acid-N-phenyloxazole and 3,3'-dibromo-2,2'-biphenyl(b)thiophene to give compound M47 (white compound, yield 56%).
  • compound M48 was prepared, and its structural formula and synthetic route are as follows:
  • the synthesis step refers to the synthesis of the compound M45 in the embodiment 45, and one of the raw materials 4,4'-diphenyl ether diboric acid is changed to the illustrated diboric acid M48-1, and the other reagents, solvent and reaction conditions are unchanged.
  • the product was obtained as a white solid with a yield of 76%.
  • compound M50 was prepared, and its structural formula and synthetic route are as follows:
  • compound M51 was prepared, and its structural formula and synthetic route are as follows:
  • reaction steps of the II body are all referred to the preparation method of the compound 51 in the example 51 except that 2-brom-N-phenylcarbazole is used instead of 3-lj acid-N-phenylcarbazole, and the other conditions are unchanged to obtain a compound.
  • M53 color 1 ancient 1 body, yield 55%).
  • compound M54 was prepared, and its structural formula and synthetic route are as follows:
  • Example 56 A similar method to Example 56 was used, except that 4-oxazolidine-boronic acid was used instead of p-diphenylaminophenylboronic acid to give Compound M57 (A color, yield 52%).
  • Example 26 A similar method as in Example 56 was used, using equimolar; lit 9-phenyl-9H-carbazole-3-boronic acid in place of p-diphenylaminophenylboronic acid to give compound M58 (white, yield 43%).
  • Example 59
  • compound M61 was prepared, and its structural formula and synthetic route are as follows:
  • Example 62 The synthesis was similar to that of Example 60 except that in the second step, the intermediate M61-1 (refer to journal of the Chemical Society, 1942, p. 404, 412) was substituted for 3,3'-dibromo-2,2'-biphenyl. And (b) thiophene, to compound M61 (white body, yield 18%).
  • Example 62 the intermediate M61-1 (refer to journal of the Chemical Society, 1942, p. 404, 412) was substituted for 3,3'-dibromo-2,2'-biphenyl. And (b) thiophene, to compound M61 (white body, yield 18%).
  • Example 62 The synthesis was similar to that of Example 60 except that in the second step, the intermediate M61-1 (refer to journal of the Chemical Society, 1942, p. 404, 412) was substituted for 3,3'-dibromo-2,2'-biphenyl. And (b) thiophene, to compound M61 (white
  • compound M62 was prepared, and its structural formula and synthetic route are as follows:
  • Example 63 In a similar manner to that of Example 64, a 3-bromo 3-boronic acid-N-methylcarbazole was substituted for 3-boronic acid-N-phenylindole-azole to obtain a compound M62 (white
  • Example 63
  • compound M63 was prepared, and its structural formula and synthetic route are as follows:
  • N 3.00%, S: 10.29%; measured values C: 82.19%, H: 4.53%, N: 3.00%, S: 10.29%.
  • a general organic electroluminescent device is composed of a substrate, an anode, an organic light-emitting functional layer and a cathode, wherein the organic light-emitting functional layer may include a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, and an electron injection layer.
  • a hole injecting material is used for the hole injecting layer
  • a hole transporting material is used for the hole transporting layer
  • an organic light emitting material is used for the organic light emitting layer.
  • the organic light emitting material includes a host material and a doping dye, and the electron transporting layer is used.
  • electron transport materials the same is used for the electron injecting layer as an electron injecting material.
  • the host material of the organic light-emitting layer may be one type or a double-host material composed of two materials.
  • the comparative material of the hole injecting material uses the hole injecting layer material 2-TNATA commonly used in the prior art.
  • the comparative material of the hole transporting material uses the hole transporting material NPB commonly used in the prior art, and the TDNe is doped with ADN as the organic light emitting layer (ADN is a host material, and TBPe is a light emitting material).
  • the substrate may use a substrate in a conventional organic light-emitting device, for example : Glass or plastic.
  • a glass substrate is used, and ITO is used as an anode material.
  • the material of the present invention was used in the examples, and 2-TNATA was used in the comparative example.
  • the hole transport layer, the material of the present invention was used in the examples, and NPB was used in the comparative example.
  • the luminescent layer is blue
  • the cathode may be made of a metal or a mixture thereof, such as Mg: Ag, Ca: Ag, or the like, or may be an electron injecting layer/metal layer structure, such as a common cathode structure such as LiF/Al or Li20/Al.
  • the cathode material selected for use in the fabrication of the organic electroluminescent device of the present invention is LiF/Al.
  • the compound in the present embodiment is used as an electron transporting material in an organic electroluminescent device, and an ADN-doped blue dye TBPe is used as a light-emitting layer material, and a plurality of organic electroluminescent devices are prepared, and the device structure thereof: ITO/hole injection material (60 nm) / hole transport material (20 nm) / ADN: 5% wtTBPe (30 nm) / BPhen (20 nm) / LiF (0.5 nm) / Al (150 nm)
  • Compounds M1 to M65 were used as hole injection layers, respectively, using M1, M5, M10, M17, M20, M24, M25, M27, M29, M33, M35, M41, M48, M49, M51, M56, M60 and M65 as empty The hole transport material is proved.
  • the glass plate coated with the ITO transparent conductive layer is sonicated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, and used ultraviolet Light and ozone cleaning, and bombard the surface with a low energy cation beam;
  • the above-mentioned glass substrate with an anode is placed in a vacuum chamber, and evacuated to lx lO_ 5 to 9 x lO_ 3 Pa ;
  • the hole injection layer is vacuum-deposited on the anode layer film, the evaporation rate is Ol nm/s, and the vapor deposition film thickness is 60 nm, and the material used for the layer is different according to the embodiment, as shown in the embodiment part;
  • the hole transport layer is vacuum-deposited on the hole injection layer film, the evaporation rate is O. l nm / s, the vapor deposition film thickness is 20 nm;
  • a double source co-evaporation method is used on the above hole transport layer, and the host material ADN and the doped luminescent material TBPe are vacuum-evaporated.
  • the evaporation rate of ADN is 0.1 nm/s, and the evaporation rate of TBPe is 0.005 nm/ s. , the total thickness of the vapor deposition is 30 nm;
  • BPhen is vacuum-deposited as an electron transport layer of an organic electro-device, and the evaporation rate is 0.1 nm/s, and the total vapor deposition thickness is 20 nm;
  • ETL electron transport layer
  • the preparation method of the comparative example was the same as the example, and only the compound as a hole injecting material or a hole transporting material was changed.
  • OLED 1 to OLED 17 respectively use the novel organic material of the present invention as the hole injecting layer material and the hole transporting layer material of the organic electroluminescent device, and can significantly reduce the turning-on voltage and improve the comparison with the comparative example 1.
  • Current efficiency; OLED18-OLED65 uses the novel organic material of the present invention as a hole injection layer material of an organic electroluminescence device, using NPB as a hole transport material, and OLED66 ⁇ OLED80 adopts the novel organic material of the present invention as organic electroluminescence
  • the hole transport layer material of the device uses 2-TNATA as a hole injecting material. Compared with Comparative Example 1, the voltage drop of these devices is lv, and the current efficiency of the device is remarkably improved.
  • the novel organic material provided by the present invention has a thiophene group, and a lone pair of electrons on the S atom easily loses electrons to form a hole, so that the compound has high carrier injection and transport capability as a hole injection and/or transport material. Therefore, the luminous efficiency of the device is greatly improved.
  • Example 68
  • HIL Hole Injection Layer
  • HTL Hole Transport Layer
  • EL Blue Luminescent Dye
  • ETL Electron Transport Layer
  • the substrate may use a substrate in a conventional organic light-emitting device such as glass or plastic.
  • a substrate is used, and ITO is used as an anode material.
  • the hole injecting material uses a hole injecting layer material 2-TNATA which is conventionally used in the prior art.
  • the hole transporting material uses the hole transporting material NPB which is conventionally used in the prior art.
  • the electron transporting material uses the electron transporting material Alq3 which is commonly used in the prior art.
  • the cathode may be made of a metal or a mixture thereof, such as Mg: Ag, Ca: Ag, or the like, or may be an electron injecting layer/metal layer structure, such as a common cathode structure such as LiF/Al, Li 2 O/Al.
  • the electron injecting material selected for use in the fabrication of the device of the present invention is LiF and the cathode material is Al.
  • the compound in this embodiment is used as a host material in an organic electroluminescent device, or one of two bodies, and a plurality of organic electroluminescent devices are prepared, the structure of which is:
  • ITO/2-TNATA 60nm) / NPB ( 20nm ) / host: blue luminescent dye ( 30nm ) I Alq3 (20nm) / LiF (0.5nm) / AL (150nm), or,
  • ITO/2-TNATA 60 nm) / NPB (20 nm) / first host: second host: blue luminescent dye (30 nm) I Alq3 (20 nm) / LiF (0.5 nm) / AL (150 nm).
  • the glass plate coated with the ITO transparent conductive layer is sonicated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, and used ultraviolet Light and ozone cleaning, and bombard the surface with a low energy cation beam;
  • the above-mentioned glass substrate with an anode is placed in a vacuum chamber, and evacuated to lx lO_ 5 to 9 x lO_ 3 Pa ;
  • the hole transport layer is vacuum-deposited on the hole injection layer film, the evaporation rate is O. l nm / s, the vapor deposition film thickness is 20 nm;
  • the evaporation rate of the main body is 0.1%/s, and the evaporation rate of the dye is 0.005 nm/s.
  • the evaporation rate of the main body is 0.1%/s, and the evaporation rate of the dye is 0.005 nm/ s.
  • the first body, the second body and the luminescent dye are vapor-deposited at a rate of 0.1 nm/s, the second body of the second body.
  • the evaporation rate varies according to various embodiments.
  • the evaporation rate of the dye is 0.005 nm/ s , and the total thickness of the vapor deposition is 30 nm; in particular, the luminescence of OLED104-OLED 134 in the following table
  • the ratio in parentheses in the layer structure is the evaporation rate ratio of the first body and the second body;
  • Alq3 was vacuum-deposited on the above-mentioned light-emitting layer as an electron transport layer of the device, and the evaporation rate was 0.1 nm/ s , and the total vapor deposition thickness was 20
  • the LiF and A1 layers were vacuum evaporated on the electron transport layer (ETL) as the cathode of the device, with thicknesses of 0.5 nm and 150 nm, respectively.
  • ETL electron transport layer
  • the organic electroluminescent device is shown in the following table:
  • OLED81 Ml TBPe 1000 5.7 6.5
  • OLED82 M5 TBPe 1000 5.5 6.4
  • OLED83 M10 TBPe 1000 5.4 6.7
  • OLED84 M13 TBPe 1000 5.0 7.3
  • OLED85 M17 TBPe 1000 5.1 7.0
  • OLED86 M20 TBPe 1000 4.9 7.2
  • OLED88 M25 TBPe 1000 5.0 7.2
  • OLED90 M29 TBPe 1000 5.0 7.3
  • OLED122 ADN M35: TBPe (l: 0.2) 1000 4.7 7.0
  • OLED123 ADN M41: TBPe (10.2) 1000 5.1 7.4
  • OLED124 ADN M48: TBPe (10.2) 1000 5.0 7.2
  • OLED125 ADN M49: TBPe (l: 0.2) 1000 4.9 6.9
  • OLED126 ADN M51: TBPe (10.2) 1000 4.8 6.8
  • OLED127 ADN M53: TBPe (10.2) 1000 5.2 7.7
  • OLED128 ADN M56: TBPe (l: 0.2) 1000 5.3 7.9
  • OLED129 ADN M59: TBPe (l: 0.2) 1000 5.1 7.8
  • OLED134 M51 M20: TBPe (l: 0.2) 1000 5.1 6.8
  • the data in the above table shows that the material in the present invention can also be used as a fluorescent blue host material, and the material in the present invention can also be combined with other commonly used fluorescent blue body. As a dual body, compared with Comparative Example 2, the voltage of the device is reduced and the efficiency is improved.

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Abstract

La présente invention porte sur un composé tel que représenté par la formule (I), dans laquelle R1 et R2 sont indépendamment choisis parmi l'un d'un groupe arylamine en C4-C30 substitué ou non substitué, d'un groupe carbazole en C4-C40 substitué ou non substitué, d'un groupe benzothiophène en C4-C40 substitué ou non substitué ou d'un groupe benzofurane en C4-C40 substitué ou non substitué; L représente un groupe de pontage choisi parmi l'un d'une simple liaison, d'un groupe arylamine en C4-C40 substitué, d'un groupe carbazole en C4-C40 substitué, d'un groupe benzothiophène en C4-C40 substitué, d'un atome d'oxygène, d'un atome d'azote ou d'un atome de soufre; R3-R10 sont chacun indépendamment choisis parmi l'atome H, un groupe hydrocarbyle aliphatique en C1-C20 à chaîne droite ou à chaîne ramifiée ou un groupe aromatique en C6-C30; ou les deux groupes voisins sont reliés en un cycle pour former un dérivé de benzothiophène; m et n sont choisis parmi les nombres entiers allant de 0 à 3 et 0 < m + n ≤ 3. La présente invention porte également sur des utilisations du composé dans un dispositif électroluminescent organique, en particulier comme substance de transport de trous et substance d'injection de trous dans un dispositif OLED ou comme substance principale d'une substance luminescente organique.
PCT/CN2013/001190 2012-09-29 2013-09-30 Dérivé de benzothiophène et son utilisation dans le domaine des dispositifs électroluminescents organiques Ceased WO2014075382A1 (fr)

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