CN117946044A - Amino compound with benzophenanthrene furan group and organic light-emitting device - Google Patents
Amino compound with benzophenanthrene furan group and organic light-emitting device Download PDFInfo
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- -1 Amino compound Chemical class 0.000 title claims abstract description 49
- HJZRUJHVLFKLBK-UHFFFAOYSA-N furan triphenylene Chemical group C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.O1C=CC=C1 HJZRUJHVLFKLBK-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 15
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 11
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 11
- 125000006831 (C5-C24) aromatic hydrocarbon group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 74
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- VDESPCTYYGQYKU-UHFFFAOYSA-N 18-oxapentacyclo[12.7.0.02,7.08,13.015,19]henicosa-1(14),2,4,6,8,10,12,15(19),16,20-decaene Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=C(C=CC=C3)C3=C21 VDESPCTYYGQYKU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 19
- 125000005259 triarylamine group Chemical group 0.000 abstract description 13
- 230000021615 conjugation Effects 0.000 abstract description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000012065 filter cake Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- XCHARIIIZLLEBL-UHFFFAOYSA-N Medicagenic acid 3-O-beta-D-glucoside Chemical compound C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C(O)=O)C)(C)C1=CCC2C3(C)CC(O)C4OC1OC(CO)C(O)C(O)C1O XCHARIIIZLLEBL-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
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Abstract
The invention discloses an amino compound with benzophenanthrene furan group and an organic light-emitting device, which are selected from compounds of formula 1: one of a 1-A10 is taken from the group of formula 2, wherein x represents a bond to the basic backbone of formula 1, When A 2 is taken from the group of formula 2, L 1 is p-phenylene, R 1、R2 is taken from a single bond, substituted or unsubstituted C5-C24 aromatic hydrocarbon, substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon, ar 1、Ar2 is taken from C5-C30 aromatic hydrocarbon, substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon; according to the invention, the triarylamine and the benzophenanthrene furan are connected to the transition benzene ring in para position, and the benzene ring connection can enhance the overall stability of the target molecule, enhance the conjugation of the molecule and increase the stacking property of the molecule in the organic luminescent material. According to the invention, phenanthryl, naphthyl or dibenzothiophene groups are arranged on the other two substituents of the triarylamine, so that the electron affinity and electron transport property of the triarylamine are affected; and further extend its useful life.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an amino compound organic light-emitting device with benzophenanthrene furan groups.
Background
An Organic Light-EMITTING DEVICES (OLED) is a Light-emitting device using the following principle: when an electric field is applied, the fluorescent substance emits light by recombination of holes injected from the positive electrode and electrons injected from the negative electrode. The self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, quick response, good temperature adaptability and the like, is ultrathin, can be manufactured on a flexible panel and the like, and is widely applied to the fields of mobile phones, tablet computers, televisions, illumination and the like.
The organic electroluminescent device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, wherein various functional materials are mutually overlapped together according to purposes to form the organic electroluminescent device. When voltage is applied to two end electrodes of the organic electroluminescent device as a current device, positive and negative charges are generated in the organic layer functional material film layer through the action of an electric field, the positive and negative charges are further compounded in the luminescent layer to generate light, and the process is electroluminescence.
The triarylamine compound is a common organic electroluminescent material, a benzophenanthrene furan group is selected on a substituent of the triarylamine, the compound is applied to the organic electroluminescent material, the characteristics of the group are utilized to improve some characteristics of the material, the performance parameters of the product are improved, for example, the material for an organic electroluminescent device is disclosed in patent application with publication number of CN 115956073A, the triarylamine compound is disclosed as a group with the benzophenanthrene furan on the patent, the specific structural formula of the triarylamine compound is disclosed as a specific structural formula of the triarylamine compound directly connected to the benzophenanthrene furan, and the other two groups of the triarylamine are selected from benzene, biphenyl, dimethylfluorene and spirobifluorene substituent; also disclosed in this patent application are compounds wherein a triarylamine is attached to a benzophenanthrofuran group through an excess of a benzene ring, and when the excess is attached to the benzophenanthrofuran at position 2, the triarylamine, benzophenanthrofuran ortho or meta is attached to the excess benzene ring, and the application of such compounds to devices shows significant advantages in terms of the lifetime of the OLED, with other performance data of the OLED being approximately comparable. However, the service life is only one parameter of the performance of the OLED device, and the improvement of the performance of the OLED device is less affected, so that an organic electrofunctional material with better performance needs to be developed on the basis of a triarylamine.
Disclosure of Invention
The object of the present invention is to solve the above technical problems, and to provide an amine compound having a benzophenanthrene furan group, selected from the compounds of formula 1:
one of a 1-A10 is taken from the group of formula 2, wherein x represents a bond to the basic backbone of formula 1,
When one of A 1、A3-A10 is taken from the group of formula 2, L 1、R1、R2 is taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, ar 1、Ar2 is taken from a C5-C30 aromatic hydrocarbon group, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group and at least one of Ar 1、Ar2 is selected from the group consisting of: substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl;
When a 2 is taken from the group of formula 2, L 1、R1、R2 is taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon and L 1 is not p-phenylene, ar 1、Ar2 is taken from a C5-C30 aromatic hydrocarbon, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon and at least one of Ar 1、Ar2 is selected from: substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl;
When A 2 is taken from the group of formula 2, L 1 is p-phenylene, R 1、R2 is taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, ar 1、Ar2 is taken from a C5-C30 aromatic hydrocarbon group, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group.
As a preferred embodiment of the present invention, one of A 1、A3-A10 is taken from the group of formula 2, L 1、R1、R2 is each independently selected from a single bond, substituted or unsubstituted phenyl; ar 1 is selected from substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl; ar 2 is selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dibenzofuranyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, carbazolyl, N-ethylcarbazolyl, 4-hydroxycarbazolyl, benzocarbazolyl, benzothienyl, furanyl, thienyl, phenylpyrimidinyl, pyrimidinyl, pyridinyl, triazinyl.
As a preferred embodiment of the invention, A 2 is taken from a group of formula 2, L 1、R1、R2 is each independently selected from a single bond, substituted or unsubstituted phenyl and L 1 is not p-phenylene, ar 1 is selected from substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl; ar 2 is selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dibenzofuranyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, carbazolyl, N-ethylcarbazolyl, 4-hydroxycarbazolyl, benzocarbazolyl, benzothienyl, furanyl, thienyl, phenylpyrimidinyl, pyrimidinyl, pyridinyl, triazinyl.
As a preferred embodiment of the invention, A 2 is a group of formula 2, L 1 is p-phenylene, R 1、R2 is a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, ar 1、Ar2 is independently selected from the following groups:
As a preferred embodiment of the present invention, the substituent is selected from at least one of the following atoms or groups: deuterium, hydroxy, cyano, mono-deuterium methyl, di-deuterium methyl, tri-deuterium methyl, C1-C4 straight or branched alkyl, C6-C18 aromatic hydrocarbon, C5-C24 heteroaromatic hydrocarbon.
As a preferred embodiment of the invention, A 2 is taken from the group of formula 2, L 1 is p-phenylene, and the amino compound with a benzophenanthrene furan group is one of the following compounds:
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As a preferred embodiment of the invention, A 2 is taken from the group of formula 2, L 1 is selected from single bonds, and the amino compound with a benzophenanthrene furan group is one of the following compounds:
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as a preferred embodiment of the present invention, one of A 1、A3-A10 is a group of formula 2, L 1 is a single bond, and the amino compound having a benzophenanthrene furan group is one of the following compounds:
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An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer containing the amine-based compound having a benzophenanthrene furan group according to any one of claims 1 to 8.
As a preferable mode of the present invention, the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one layer of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer contains the organic electroluminescent compound.
As a preferred embodiment of the present invention, the electron blocking layer contains the above-mentioned organic electroluminescent compound.
The compound with the structure shown in the formula 1 has a synthetic reaction route as follows:
the invention has the beneficial effects that:
The triarylamine is excessively connected to the No. 2 position of benzophenanthrene furan through the benzene ring, the triarylamine and the benzophenanthrene furan are in para-position connection to the excessive benzene ring, the overall stability of a target molecule can be enhanced through the benzene ring connection, the conjugation of the molecule can be enhanced through the para-position connection of the benzene ring, the conjugation is beneficial to adjusting the electronic structure of the molecule, the photoelectric property of the molecule is influenced, and the conjugated structure is an important factor for realizing specific electronic properties. Para-linked benzene rings can make molecules flatter, which can help to increase the stacking of molecules in organic luminescent materials, thereby affecting the crystal structure and performance of the materials, especially the charge transport properties in organic semiconductors. The para-position connection benzene ring on the compound can generate a certain steric hindrance effect, influence the steric configuration of the product and also can influence the interaction between molecules.
Benzene is provided with phenanthryl, naphthyl or dibenzothiophene groups on the other two substituents of the triarylamine, so that the electron affinity and electron transport property of the triarylamine are affected. Exhibits good electron transport properties and is useful as an electron transport material in organic electronic devices. The substituent groups can influence the absorption spectrum characteristics, and are beneficial to the design and performance optimization of the photoelectric device. These substituents enhance the stability of the triarylamine molecule, reducing its decomposition or degradation during application, and thereby further extending its useful life.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to the present invention;
The reference numerals in the figures represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-electron blocking layer, 5-light emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode.
FIG. 2 is an HPLC plot of compound 104 of the present invention.
FIG. 3 shows a DSC chart of compound 104 of the present invention, and as can be seen from FIG. 3, the Tg value of compound 104 is 147.43 ℃.
FIG. 4 shows the TGA spectrum of the compound 104 of the present invention, and as can be seen from FIG. 4, the thermal weight loss temperature Td value of the compound 100 is 500.90 ℃.
Detailed Description
Embodiments of the various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the particular aspects described. On the contrary, the intent is to cover alternatives, modifications and equivalents as included within the spirit and scope of the disclosure as defined by the appended claims.
As used herein, in "deuterated" or "non-deuterated," the term "deuterated" refers to the fact that at least one hydrogen in the group is re-coordinated with deuterium. The term "non-deuterated" means that all hydrogens in the group are not re-coordinated to deuterium.
As used herein, "aromatic group", "aryl" or "aromatic group" refers to groups containing one or more aromatic rings, where the aromatic rings include, but are not limited to, benzene, naphthalene, phenanthrene, fluorene, acenaphthylene, pyridine, pyrimidine, pyrrole, furan, thiophene, and the like. C6-C30 in an aromatic radical of C6-C30 means that the radical contains from 6 to 30 carbon atoms. In the C1-C10 alkyl-substituted C6-C20 aromatic group, C1-C10 means the number of carbon atoms of the substituent, and C6-C20 means the number of carbon atoms of the aromatic group containing no substituent. Aromatic groups can be divided into monocyclic aryl groups and polycyclic aryl groups. Specific aromatic groups in the present invention include, but are not limited to, phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothienyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, and the like. The aromatic groups may be substituted and unsubstituted.
"Cycloalkyl" herein refers to a monocyclic or fused ring (fused ring means that each ring in the system shares an adjacent pair of carbon atoms with the other rings in the system) group that is entirely carbon, wherein one or more of the rings is a saturated alicyclic ring, typically having 3 to 20 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms. Cycloalkyl groups can be divided into monocyclic alkyl groups having only one ring and fused ring alkyl groups having multiple rings. Examples of monocyclic alkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. Cycloalkyl groups may be substituted and unsubstituted.
"Cycloalkenyl" herein refers to a single ring or fused ring of all carbons ("fused" ring means that each ring in the system shares an adjacent pair of carbon atoms with the other rings in the system), wherein one or more rings do not have a fully attached pi-electron system and contain at least one alkenyl group, typically having 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms, and examples of cycloalkenyl include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, cycloheptatriene. Cycloalkenyl groups can be substituted and unsubstituted.
"Deuterated aromatic group" herein refers to a group in which one or more hydrogen atoms in the aromatic group are replaced with deuterium.
"Deuterated phenyl" herein refers to a group in which 1 or more hydrogens in the phenyl group are replaced with deuterium.
"Heteroaryl" as used herein refers to heteroaryl groups in which one or more C' S in the structure of the "aryl" are substituted with one or more heteroatoms (e.g., N, O or S).
The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Example 1:
Compound 104:
compound 104 was prepared as follows:
Scheme 104-ZJ1 The process comprises the following steps: 104-SM1 (250 g,0.89mol,1 eq), binaphthol bisborate (293.2 g,1.154mol,1.3 eq), potassium acetate (261 g, 2.284 mol,3 eq), pdCl2 (dppf) (13 g,17.76mmol,0.02 eq) and 1, 4-dioxane (1500 ml) were added to a 2L three-necked flask, and the mixture was heated to 90-100 ℃ under N2 protection, stirred and reacted, and HPLC was monitored to 104-SM1 not more than 0.5%.
Post-treatment: stopping the reaction, filtering with silica gel while the reaction is hot, leaching the filter cake with 600ml of DCM, concentrating the filtrate under reduced pressure until the filtrate is dry, adding 250ml of ethanol, cooling, stirring for crystallization, filtering, and drying the filter cake by air blast at 85 ℃ to obtain 197.2g of gray solid with the yield of 67.6%.
Scheme 104-ZJ2
The process comprises the following steps: into a 3L three-necked flask were charged 104-ZJ1 (197.2 g,0.6mol,1 eq), 104-SM2 (103.3 g,0.6mol,1 eq), potassium carbonate (166 g,1.2mol,2 eq), pd (PPd 3) 4 (13.9 g,12mmol,0.02 eq) and toluene/ethanol/water (160 ml+800ml+480 ml), and the reaction was performed under reflux at a temperature rise under N2 protection, with HPLC monitoring to 104-ZJ 1.ltoreq.0.5%.
Post-treatment: the reaction was stopped, the liquid was stirred, the aqueous phase was extracted with DCM, the organic phases were combined, filtered through silica gel powder, and the filtrate was concentrated to dryness under reduced pressure and used directly in the next reaction without purification.
Scheme 104-ZJ3
The process comprises the following steps: 104-ZJ2 (theoretical 176.3g,0.6mol,1 eq) and acetic acid (1500 ml) are added into a 3L three-necked flask, cooled to below 10 ℃, concentrated sulfuric acid (212 ml) is added dropwise, the mixture is stirred for 30min under heat preservation, cooled to 0-10 ℃, aqueous solution (150 ml) of sodium nitrite (82.5 g,1.2mol,2 eq) is added dropwise, the mixture is heated to 115 ℃ and stirred for reaction overnight.
Post-treatment: stopping heating, cooling to room temperature, suction filtering, leaching the filter cake with water, dissolving the filter cake with DCM, suction filtering, filtering to remove insoluble substances, adding PE into the filtrate, concentrating under reduced pressure to remove most of the solvent, suction filtering, and drying the filter cake at 85 ℃ by air blast to obtain 35.7g of brown yellow solid, wherein the yield of the two steps is 21.5%.
Scheme 104-ZJ4
The process comprises the following steps: 104-ZJ3 (25 g,90.3mmol,1 eq), binaphthol ester of biboronic acid (29.8 g,0.117mol,1.3 eq), potassium acetate (26.6 g,0.271mol,3 eq), XPhos (2.58 g,5.42mmol,0.06 eq), pd2 (dba) 3 (2.48 g,2.71mmol,0.03 eq) and 1, 4-dioxane (300 ml) were placed in a 500ml three-necked flask, and the mixture was stirred under N2 protection by heating to 90 to 100℃and monitored by HPLC to give 104-ZJ3 as 0.5% or less.
Post-treatment: stopping the reaction, filtering with silica gel while the reaction is hot, leaching the filter cake with 300ml of DCM, concentrating the filter cake under reduced pressure until the filter cake is dry, adding 100ml of ethanol for crystallization, filtering, and drying the filter cake by blowing at 85 ℃ to obtain 33.2g of gray solid with the yield of 99.7%.
Scheme 104-ZJ5
The process comprises the following steps: 104-ZJ4 (33.2 g,90.2mmol,1 eq), 104-SM3 (26.8 g,94.7mmol,1.05 eq), potassium carbonate (24.9 g,0.18mol,2 eq), pd (PPd 3) 4 (2.08 g, 1.514 mmol,0.02 eq) and toluene/ethanol/water (600 ml+300ml+180 ml) were added to a 2L three-necked flask, and the mixture was refluxed under N2 protection at an elevated temperature until the HPLC level was monitored to be 104-ZJ 4. Ltoreq.0.5%.
Post-treatment: stopping the reaction, adding 1L of ethanol, cooling, stirring, crystallizing, carrying out suction filtration, leaching a filter cake with water and ethanol, and carrying out forced air drying on the filter cake at 85 ℃ to obtain 24.3g of gray solid, wherein the yield is 67.8%.
Scheme 104
The process comprises the following steps: into a 500mL three-necked flask were charged 104-ZJ5 (24.3 g,61.2mmol,1 eq), 104-SM4 (21.14 g,61.2mmol,1 eq), sodium t-butoxide (7.06 g,73.44mol,1.2 eq), tri-t-butylphosphine (5 mL, 2.447 mmol,0.04 eq) and toluene (250 mL), pd2 (dba) 3 (1.12 g,1.224mmol,0.02 eq) was added under nitrogen protection, and the mixture was stirred and heated to 110℃to effect a reaction, and the CP8470-ZJ5 was monitored by HPLC to be not more than 0.5%.
Post-treatment: stopping the reaction, adding water, stirring and separating, extracting with water-phase DCM, merging organic phases, adding 20g of 100-200 mesh silica gel for sand production, loading 300g of 100-200 mesh silica gel into a column, carrying out column chromatography, collecting product points, concentrating under reduced pressure to dryness, adding 50ml of ethanol into a sample for hot pulping overnight, carrying out suction filtration, recrystallizing a filter cake with toluene/ethanol for 8 times, and carrying out forced air drying at 85 ℃ on the filter cake to obtain 5.6g of off-white solid with the purity of 99.8670% and the yield of 13.8%.
Compounds ：2、4、5、6、7、8、9、11、13、15、17、18、19、21、25、27、34、35、40、41、51、53、54、55、89、90、99、100、106、110、111、107、126、127、129、131、171、172、174、175、179、182、190、191、215、216、222、223、225、226、249、250 obtained in a similar manner are detailed in Table 1 below
TABLE 1
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Example 54:
compound 271:
Compound 271 was prepared as follows:
Scheme 271-ZJ1
Post-process treatment is described in 104-ZJ1.
Scheme 271-ZJ2Post-process treatment 104-ZJ2.
Scheme 271-ZJ3Post-process treatment is described in 104-ZJ3.
Scheme 271
Post-process treatment see 104, 63.7% yield.
The compounds were obtained in a similar manner: 272. 273, 274, 285, 286 are detailed in Table 2 below
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Example 60: compound 300:
Compound 300 was prepared as follows:
Scheme 300-ZJ1 Post-process treatment is described in 104-ZJ1.
Scheme 300-ZJ2Post-process treatment 104-ZJ2.
Scheme 300-ZJ3Post-process treatment is described in 104-ZJ3.
Scheme 300Post-process treatment see 104, 57.9% yield.
The compounds were obtained in a similar manner: 301. 302, 303, 315, 311 are detailed in Table 3 below
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The synthetic identification results of the compounds prepared in tables 1-3 above are shown in table 4 below:
TABLE 4 Table 4
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Material property testing:
The compounds 104、2、4、5、6、7、8、9、11、13、15、17、18、19、21、25、27、34、35、40、41、51、53、54、55、89、90、99、100、106、110、111、107、126、127、129、131、171、172、174、175、179、182、190、191、215、216、222、223、225、226、249、250、271、272、273、274、285、286、300、301、302、303、315、311 of the present invention were tested for thermal weight loss temperature Td and glass transition temperature Tg and the test results are shown in table 5 below.
Note that: the thermal weight loss temperature Td is a temperature at which the weight loss is 5% in a nitrogen atmosphere, and is measured on a TGAN-1000 thermogravimetric analyzer with a nitrogen flow rate of 10mL/min, and Tg (glass transition temperature) is measured by differential scanning calorimetry (DSC, new DSC N-650) at a heating rate of 10 ℃/min.
Table 5:
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From the data, the compound synthesized by the invention has excellent thermal stability, and the compounds have higher Td values, so that the compound conforming to the structural general formula of the invention has excellent thermal stability, and can well meet the use requirement of the organic electroluminescent material.
Device performance test:
Application example 1:
ITO is adopted as a reflecting layer anode substrate material, and is subjected to surface treatment by water, acetone and N 2 plasma in sequence;
Depositing 10nm of HT-1 containing 3wt% of NDP-9 in HT-1 on the ITO anode substrate to form a Hole Injection Layer (HIL);
evaporating HT-1 of 100nm above a Hole Injection Layer (HIL) to form a Hole Transport Layer (HTL);
Vacuum evaporating the organic electroluminescent compound 104 prepared in example 1 of the present invention over a Hole Transport Layer (HTL) to form an electron blocking layer (BP) having a thickness of 10 nm;
BH-1 is used as a blue light host material, BD-1 is used as a blue light doping material (BD-1 is used as 3% of ADN weight) and is evaporated at different rates to form a light-emitting layer with the thickness of 20nm on a Hole Transport Layer (HTL);
Evaporating HB-1 on the light-emitting layer to obtain a Hole Blocking Layer (HBL) with the thickness of 20 nm;
Evaporating ET-1 as an electron transport layer material (ET) on a Hole Blocking Layer (HBL) to obtain an Electron Transport Layer (ETL) with the thickness of 30nm, and evaporating LiQ with the thickness of 2nm above the Electron Transport Layer (ETL) to form an Electron Injection Layer (EIL);
Thereafter, magnesium (Mg) and silver (Ag) were mixed and evaporated at a ratio of 9:1 to obtain a cathode having a thickness of 15nm, DNTPD having a thickness of 50nm was deposited on the above cathode sealing layer, and in addition, the surface of the cathode was sealed with a UV hardening adhesive and a sealing film (seal cap) containing a moisture scavenger to protect the organic electroluminescent device from oxygen or moisture in the atmosphere, so that the organic electroluminescent device was manufactured.
Application examples 2 to 53
The compound 2、4、5、6、7、8、9、11、13、15、17、18、19、21、25、27、34、35、40、41、51、53、54、55、89、90、99、100、106、110、111、107、126、127、129、131、171、172、174、175、179、182、190、191、215、216、222、223、225、226、249、250 of the present invention was used as BP, and the other parts were the same as in application example 1, whereby organic electroluminescent devices of application examples 2 to 53 were produced.
Comparative examples 1 to 8:
The difference from application example 1 is that the compounds P4c, P3b, P2a, P1c, 123-12, 123-13, 123-14, 123-15 in "CN 115956073A" were used as BP instead of the compound 104 in the present application, respectively, and the rest was the same as application example 1.
The characteristics of the organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example were measured under the condition that the current density was 10mA/cm 2, and the results are shown in Table 6.
Table 6:
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As shown in the above Table 6, the compound of the invention is applied to the blue-light organic electroluminescent device as BP, the luminous efficiency is greatly improved under the same current density, the starting voltage of the device is reduced, and the power consumption of the device is relatively reduced.
The organic electroluminescent devices prepared in comparative examples 1 to 8, application examples 1 to 5, 12, 13, 18, 19, 30, 33, 34, 35, 40, 41, 44, 45, 50, 51 were subjected to luminescence lifetime test, respectively, to obtain luminescence lifetime T97% data (time for which luminescence luminance was reduced to 97% of initial luminance), and the test equipment was a TEO luminescent device lifetime test system. The results are shown in Table 7:
Table 7:
As can be seen from the above Table 7, the application of the compound of the present invention as BP in organic electroluminescent devices can further improve the service life of the organic electroluminescent devices, and thus has a wide application prospect.
Application example 54:
ITO is adopted as a reflecting layer anode substrate material, and is subjected to surface treatment by water, acetone and N 2 plasma in sequence;
depositing HT-1 doped with 2% NDP-9 by mass ratio at 10nm on the ITO anode substrate to form a Hole Injection Layer (HIL);
Evaporating HT-1 of 100nm above a Hole Injection Layer (HIL) to form a first Hole Transport Layer (HTL);
Vacuum evaporating a compound 271 designed according to the present invention over the first Hole Transport Layer (HTL) to form a second hole transport layer (GPL) having a thickness of 30 nm;
Performing co-evaporation on the compound G1 and the compound G2 serving as green light main materials according to the mass ratio of 5:5, and performing evaporation on the compound G1 and the compound G2 serving as doping materials (the GD-1 is 8% of the total mass of the G1 and the G2) to form a light-emitting layer with the thickness of 30nm on a second hole transport layer (GPL);
Evaporating HB-1 on the light-emitting layer to obtain a Hole Blocking Layer (HBL) with the thickness of 20 nm;
co-evaporating ET-1 and LiQ on a Hole Blocking Layer (HBL) according to the mass ratio of 5:5 to obtain an Electron Transport Layer (ETL) with the thickness of 30 nm;
mixing and evaporating magnesium (Mg) and silver (Ag) in a mass ratio of 9:1 to form an Electron Injection Layer (EIL) with a thickness of 50nm above an Electron Transport Layer (ETL);
thereafter, silver (Ag) was evaporated over the electron injection layer to form a cathode having a thickness of 100nm, DNTPD having a thickness of 50nm was deposited on the above cathode sealing layer, and in addition, the surface of the cathode was sealed with UV hardening adhesive and a sealing film (seal cap) containing a moisture scavenger to protect the organic electroluminescent device from oxygen or moisture in the atmosphere, so that the organic electroluminescent device was fabricated.
Application examples 55 to 65
The organic electroluminescent devices of application examples 55 to 65 were fabricated by using the compounds 272, 273, 274, 285, 286, 300, 301, 302, 303, 315, and 316 of the present invention as GPLs, respectively, and the other parts were identical to application example 54. Comparative examples 1 to 4:
The difference from application example 54 is that the compounds P2a, P7a, P4c, and P10c in "CN 115956073 a" were used as GPL instead of the compound 271 in the present application, and the other is the same as application example 1.
The characteristics of the organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example were measured under the condition that the current density was 10mA/cm 2, and the results are shown in Table 8.
Table 8:
As can be seen from the above Table 8, when the compound of the invention is applied to the green organic electroluminescent device as GPL, the luminous efficiency is greatly improved under the same current density, the starting voltage of the device is reduced, and the power consumption of the device is relatively reduced.
The organic electroluminescent devices prepared in comparative examples 1 to 4 and application examples 55 to 65 were subjected to luminescence lifetime test, respectively, to obtain luminescence lifetime T97% data (time for which luminescence luminance was reduced to 97% of initial luminance), and the test equipment was a TEO luminescence device lifetime test system. The results are shown in Table 9:
Table 9:
as shown in table 9 above, the compound of the present invention is applied to the green organic electroluminescent device as GPL, and the service life of the compound is further improved compared with the compound in the comparative document under the same current density, thus having a wide application prospect.
Claims (10)
1. An amine compound having a benzophenanthrene furan group, characterized in that it is selected from the compounds of formula 1:
one of a 1-A10 is taken from the group of formula 2, wherein x represents a bond to the basic backbone of formula 1,
When one of A 1、A3-A10 is taken from the group of formula 2, L 1、R1、R2 is taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, ar 1、Ar2 is taken from a C5-C30 aromatic hydrocarbon group, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group and at least one of Ar 1、Ar2 is selected from the group consisting of: substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl;
When a 2 is taken from the group of formula 2, L 1、R1、R2 is taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon and L 1 is not p-phenylene, ar 1、Ar2 is taken from a C5-C30 aromatic hydrocarbon, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon and at least one of Ar 1、Ar2 is selected from: substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl;
When A 2 is taken from the group of formula 2, L 1 is p-phenylene, R 1、R2 is taken from a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, ar 1、Ar2 is taken from a C5-C30 aromatic hydrocarbon group, a substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group.
2. An amine compound having a benzophenanthrene furan group as claimed in claim 1, wherein one of a 1、A3-A10 is taken from the group of formula 2, L 1、R1、R2 is each independently selected from a single bond, substituted or unsubstituted phenyl; ar 1 is selected from substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl; ar 2 is selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dibenzofuranyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, carbazolyl, N-ethylcarbazolyl, 4-hydroxycarbazolyl, benzocarbazolyl, benzothienyl, furanyl, thienyl, phenylpyrimidinyl, pyrimidinyl, pyridinyl, triazinyl.
3. An amine compound having a benzophenanthrofuran group according to claim 1, wherein A2 is taken from the group of formula 2, L 1、R1、R2 is each independently selected from the group consisting of a single bond, substituted or unsubstituted phenyl and L 1 is not p-phenylene, ar 1 is selected from the group consisting of substituted or unsubstituted phenanthryl, naphthyl, dibenzothienyl; ar 2 is selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dibenzofuranyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, carbazolyl, N-ethylcarbazolyl, 4-hydroxycarbazolyl, benzocarbazolyl, benzothienyl, furanyl, thienyl, phenylpyrimidinyl, pyrimidinyl, pyridinyl, triazinyl.
4. An amine compound having a benzophenanthrene furan group according to claim 1, wherein a 2 is taken from the group of formula 2, L 1 is p-phenylene, R 1、R2 is taken from the group consisting of a single bond, a substituted or unsubstituted C5-C24 aromatic hydrocarbon group, a substituted or unsubstituted C5-C24 heteroaromatic hydrocarbon group, ar 1、Ar2 is each independently selected from the group consisting of:
5. An amine compound having a benzophenanthrene furan group as set forth in claim 1, wherein the substituent is selected from at least one of the following atoms or groups: deuterium, hydroxy, cyano, mono-deuterium methyl, di-deuterium methyl, tri-deuterium methyl, C1-C4 straight or branched alkyl, C6-C18 aromatic hydrocarbon, C5-C24 heteroaromatic hydrocarbon.
6. An amine compound having a benzophenanthrene furan group as claimed in claim 1, wherein a 2 is taken from the group of formula 2, L 1 is p-phenylene, and the amine compound having a benzophenanthrene furan group is one of the following structural compounds:
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7. An amine compound having a benzophenanthrene furan group as claimed in claim 1, wherein a 2 is taken from the group of formula 2, L 1 is selected from single bonds, and the amine compound having a benzophenanthrene furan group is one of the following compounds of formula:
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8. An amine compound having a benzophenanthrene furan group as claimed in claim 1, wherein one of a 1、A3-A10 is taken from the group of formula 2, L 1 is selected from single bonds, and the amine compound having a benzophenanthrene furan group is one of the following structural compounds:
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9. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the amine-based compound having a benzophenanthrene furan group according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer; at least one layer of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer contains the organic electroluminescent compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311830250.3A CN117946044A (en) | 2023-12-28 | 2023-12-28 | Amino compound with benzophenanthrene furan group and organic light-emitting device |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311830250.3A CN117946044A (en) | 2023-12-28 | 2023-12-28 | Amino compound with benzophenanthrene furan group and organic light-emitting device |
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| CN117946044A true CN117946044A (en) | 2024-04-30 |
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| CN202311830250.3A Pending CN117946044A (en) | 2023-12-28 | 2023-12-28 | Amino compound with benzophenanthrene furan group and organic light-emitting device |
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| Country | Link |
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| CN (1) | CN117946044A (en) |
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