CN115677670A - Compound containing quinazoline structure and application thereof - Google Patents
Compound containing quinazoline structure and application thereof Download PDFInfo
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- CN115677670A CN115677670A CN202110875615.9A CN202110875615A CN115677670A CN 115677670 A CN115677670 A CN 115677670A CN 202110875615 A CN202110875615 A CN 202110875615A CN 115677670 A CN115677670 A CN 115677670A
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Abstract
The invention provides a compound containing a quinazoline structure and application thereof, wherein the compound containing the quinazoline structure has a structure shown in a formula I. The compound provided by the invention is used for an electron transport layer, so that the luminous efficiency can be improved, and the service life of a device can be prolonged.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to a compound containing a quinazoline structure and application thereof.
Background
Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, so that the technology is a novel display technology with fast development and high technical requirements.
The organic electroluminescent device comprises electrode material film layers and organic functional materials clamped between different electrode film layers or recommended by self, and various different functional materials are mutually superposed together according to the application to form the organic electroluminescent device. When the organic electroluminescent device is used as a current device, voltage is applied to two end electrodes of the organic electroluminescent device, positive and negative charges are generated in the organic layer functional material film layer under the action of an electric field, the positive and negative charges are further compounded in the light emitting layer to generate light, and the process is electroluminescence.
The research on the improvement of the performance of the organic electroluminescent device includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the organic electroluminescent device, not only the innovation of the structure and the manufacturing process of the organic electroluminescent device is required, but also the continuous research and innovation of the organic electro-luminescent functional material are required, so that the organic electroluminescent functional material with higher performance is created.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a compound containing a quinazoline structure and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the invention provides a compound containing a quinazoline structure, wherein the compound containing the quinazoline structure has a structure shown as a formula (1-1) or a formula (1-2):
l is selected from a linkage, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C5-C30 heteroarylene,
ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C5-C60 heteroarylamine, substituted or unsubstituted C5-C60 arylheteroarylamine,
R 1 -R 3 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C1-C30 alkoxyOr unsubstituted C6-C30 aryloxy groups,
R n1 -R n8 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy.
In the invention, the group of the quinazoline structure-containing compound with LUMO energy level distribution is of a ring structure, and when the quinazoline structure-containing compound is used as a main material of a light-emitting layer, the quinazoline structure-containing compound is beneficial to the transmission of current carriers in the light-emitting layer and promotes the combination of electrons and holes, and when the quinazoline structure-containing compound is used as an electron transmission material, the quinazoline structure-containing compound can effectively improve the electron mobility, improve the efficiency of a device and prolong the service life of the device.
Preferably, ar is selected from the following carbazole groups:
R 4 -R 11 <xnotran> , , , , C1-C30 , O S -O- -S- C1-C30 , C2-C30 , O S -O- -S- C2-C30 , C2-C30 , C7-C30 , C6-C30 , C2-C30 , C3-C30 , C3-C30 , C3-C30 , C3-C30 , C1-C30 , C6-C30 , C6-C60 , C5-C60 , C5-C60 , </xnotran>
Preferably, R 4 -R 11 Each independently selected from the group consisting of substituted or unsubstituted: phenyl, carbazolyl, phenyl-substituted carbazolyl, biphenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzofuran-substituted carbazolyl, terphenyl-substituted carbazolyl;
preferably, R 4 -R 11 Either one of them is combined with
The connection is carried out by connecting the two parts,
L 1 selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 1 、Ar 2 each is independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, biphenyl-substituted carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl.
R 4 -R 11 Each independently exists or two adjacent rings are connected to form a ring, wherein the ring is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted benzindole ring, or a substituted or unsubstituted naphthoindole ring; and/or R 4 And R 11 Connected through benzene ring and naphthalene ring;
preferably, R 4 -R 11 Any two adjacent of them are fused with benzene ring, and/or R 4 And R 11 Through benzene ring or naphthalene ring;
preferably, ar is selected from
W is O, S, NL 2 Ar 3 、CR 16 R 17 ，L 2 Selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 3 selected from phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl substituted naphthyl, naphthyl substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuran substituted phenyl, dibenzothiophenyl substituted phenyl, dimethylfluorenyl substituted phenyl, diphenylfluorenyl substituted phenyl, spirobifluorenyl,
R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 each independently selected from hydrogen, deuterium, phenyl and/or adjacent two are connected to form a benzene ring,
R 16 、R 17 each independently selected from methyl, phenyl, or R 16 、R 17 The bonding is carried out to form a fluorenyl group,
and/or R 4 And R 11 Through a benzene ring or a naphthalene ring.
More preferably, ar is selected from the group consisting of substituted or unsubstituted:
wherein the wavy line represents the attachment site of the group;
preferably, ar is selected from the group consisting of substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, quinazolinyl, 2-phenylphenanthrene [3,4-d ] oxazolyl, 2-phenylphenanthrene [3,4-d ] thiazolyl;
preferably, R n1 -R n8 Each independently selected from the group consisting of substituted or unsubstituted hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, 2-phenylphenanthrene [3,4-d ] group]Oxazolyl, 2-phenylphenanthrene [3,4-d]A thiazolyl group;
preferably, L is selected from a linker, phenylene, biphenylene, naphthylene, dibenzofuranylene;
when the group as described above in the present invention contains a substituent, each of the substituents is independently selected from deuterium, halogen, cyano, unsubstituted or R ' substituted C1-C6 alkyl, unsubstituted or R ' substituted C6-C12 aryl, unsubstituted or R ' substituted C2-C20 heteroaryl;
r' is selected from deuterium, halogen, cyano, deuterium-substituted methyl and halogen-substituted methyl;
preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthyl substituted phenyl, dimethylfluorenyl, diphenyl substituted fluorenyl, spirobifluorenyl,
preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzocarbazolyl, dibenzocarbazolyl,
preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, adamantyl;
preferably, the compound containing a quinazoline structure is any one of the following compounds:
as used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine, preferably fluorine.
As used herein, the term "alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.
As used herein, unless otherwise specified, the term "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 30 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane and the like.
Aryl, arylene groups in the present invention include monocyclic, polycyclic or fused ring aryl groups, which rings may be interrupted by short nonaromatic units including, but not limited to, phenyl, biphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthrenyl, benzophenanthrenyl.
Heteroaryl, heteroarylene groups of the invention include monocyclic, polycyclic or fused ring aryl groups, which rings may be interrupted by short non-aromatic units, including, but not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenazinyl, phenothiazinyl, phenanthrolinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof, and the like.
Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, 9,9 '-dimethylfluorenyl, 9,9' -diphenylfluorenyl, or spirobifluorenyl.
Preferably, the heteroaryl group is selected from dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthoimidazolyl, naphthooxazolyl, naphthothiazolyl, phenanthroimidazolyl, phenanthrooxazolyl, phenanthroiothiazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidinyl, benzofuropyrazinyl, benzofuropyrimidinyl, indolopyrazinyl, indolopyridyl, indenopyrazinyl, indenopyrimidinyl, spiro (fluorene-9,1 '-indene) and pyrazinyl, spiro (fluorene-9,1' -indene) and pyrimidinyl, benzofurocarbazolyl, or benzothiophenocarbazolyl.
As used herein, the term "aryloxy" refers to a monovalent substituent represented by RO-, wherein R represents an aryl group having 6 to 30 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
As used herein, the term "substituted" means that the hydrogen atom in the compound is replaced with another substituent. The position is not limited to a specific position as long as hydrogen at the position can be substituted by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.
The phrase "two adjacent groups are linked to form a ring" as used herein means that 2 substituents at adjacent positions on the same or adjacent rings may be linked to each other by chemical bondsThe ring is not limited in the specific manner of connecting the rings (e.g., by a single bond, by
Thickening and passing
Thickening and passing
Thickening and passing
Thickening and passing
Thickening; wherein
Indicating a thick and dense position) has the same meaning as when the same description is referred to below.
In the present invention, the definition of a group defines a range of carbon numbers, the number of carbon atoms of which is any integer within the defined range, such as a C6-C60 aryl group, and the number of carbon atoms representing an aryl group can be any integer within the range encompassed by 6-60, such as 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55, 60, or the like.
In the invention, the preparation route of the compound containing the quinazoline structure is as follows:
when L is selected from the group consisting of a bond, the third step takes the route of (2);
in another aspect, the present invention provides an organic electroluminescent material comprising any one of or a combination of at least two of the compounds having a quinazoline structure as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising any one of or a combination of at least two of the compounds containing a quinazoline structure as described above;
preferably, the organic layer includes at least a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer;
preferably, the material of the light-emitting layer comprises a host material and a guest material, wherein the host material comprises any one of the compounds containing the quinazoline structure or a combination of at least two of the compounds;
preferably, the electron transport layer comprises any one of or a combination of at least two of the compounds containing a quinazoline structure as described above;
preferably, the guest material is a phosphorescent dopant, which is a transition metal-containing complex, preferably an Ir-or Pt-containing complex.
In another aspect, the present invention provides an optoelectronic product comprising an organic electroluminescent device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the compound is used as a main body material and an electron transport material of an organic electroluminescent device, can limit the flow of current carriers in a luminescent layer, and provides better device performance, including lower driving voltage, higher current efficiency and prolonged service life, so that the driving voltage of the device is below 3.70V, the current efficiency is above 22Cd/A, and the service life is above 367 h.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthetic examples
1-B synthesis, taking a 50 ml two-neck round-bottom flask, putting a stirrer and an upper reflux pipe, drying, introducing nitrogen, respectively adding 1-A (1 mmol), bis (pinacolato) diboron (1.2 mmol), potassium acetate (2 mmol), 1,4-dioxane (20 ml), protecting with nitrogen, adding [1,1-bis (diphenylphosphino) ferrocene ] palladium (II) dichloride (0.05 mmol), refluxing for 12 hours, after the reaction is finished, purifying a crude product by column chromatography (ethyl acetate/n-hexane: volume ratio is 1/10), and obtaining 1-B (0.11 g, yield 47%).
Synthesis of 1-D: taking a 50 ml double-neck round-bottom flask, putting a stirrer and an upper reflux pipe, introducing nitrogen after drying, and respectively adding a compound 1-C (1 mmol), a compound 1-B (1 mmol) and potassium carbonate (K) 2 CO 3 1.5mmol, ethanol (3 ml), water (3 ml), toluene (15 ml) and tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.05 mmol), heated to 60 ℃ and reacted for 12 hours, cooled to room temperature after completion of the reaction, quenched by addition of 20 ml of water, extracted with dichloromethane (3 × 20 ml), the resulting extracts dried over magnesium sulfate, filtered and spun dry in that order, and the crude product purified by chromatography (ethyl acetate/n-hexane: volume ratio 1/10) to obtain 1-D (0.15 g, 43% yield).
Synthesis of 1-F: a100-milliliter two-neck round-bottom flask is taken and placed with a stirrer and an upper reflux pipe, nitrogen is filled after drying, 1-D (1 mmol), carbazole (1 mmol), cesium carbonate (0.012 mol), tris (dibenzylideneacetone) dipalladium (Pd 2 (dba) 3, 0.05mmol) and 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (xphos, 0.055 mmol) are respectively added, then toluene is added, the mixture is refluxed for 24 hours, the reaction system is cooled to room temperature after reaction, the reaction system is filtered and concentrated, and the crude product is purified by chromatography (dichloromethane/n-hexane, 1/10 (volume ratio)) to obtain 1-F (0.38 g, 79% of yield).
Synthesis of Compound 1: taking a 50 ml double-neck round-bottom flask, putting a stirrer and an upper reflux pipe, introducing nitrogen after drying, and respectively adding 1-F (1 mmol) and dichlorobis (tricyclohexylphosphine) palladium (PdCl) 2 (PCy 3 ) 2 0.05 mmol), pivalic acid (t-BuCO) 2 H,2 mmol), carbonCesium acid (Cs) 2 CO 3 2 mmol) and dimethylacetamide (20 ml), stirred at 120 ℃ for 10 hours, cooled to room temperature after the reaction is complete, the reaction is concentrated and the crude product is purified by chromatography (ethyl acetate/n-hexane: volume ratio 1/10), yield 1 (0.27 g, 61% yield).
Elemental analysis: c 32 H 19 N 3 Theoretical value: c,86.27; h,4.30; n,9.43; measured value: c,86.32; h,4.28; n,9.40; HRMS (ESI) M/z (M +): theoretical value: 445.1579; measured value: 445.1584.
2-F Synthesis: the synthesis of 1-F was identical except that 2-C was used instead of carbazole to give 2-F (0.47 g, 77% yield).
Synthesis of Compound 2: synthesis of Compound 1, except that 1-F was replaced with 2-F, gave Compound 2 (0.38 g, 67% yield).
Elemental analysis: c 42 H 23 N 3 Theoretical value: c,88.55; h,4.07; n,7.38; measured value: c,88.59; h,4.05; n,7.36; HRMS (ESI) M/z (M +): theoretical value: 569.1892; measured value: 569.1898.
synthesis of 3-F: the same synthesis as 1-F, except that carbazole was replaced with 3-C gave 3-F (0.48 g, 75% yield).
Synthesis of Compound 3: synthesis of Compound 1, except that 1-F was replaced with 3-F, gave Compound 3 (0.41 g, 69% yield).
Elemental analysis: c 42 H 23 N 3 Theoretical value of S: c,83.84; h,3.85; n,6.98; s,5.33; measured value: c,83.79; h,3.86; n,7.00; s,5.35; HRMS (ESI) M/z (M +): theoretical value: 601.1613; measured value: 601.1621.
4-F Synthesis: the same synthesis as 1-D except that 1-D was used instead of 1-C,4-C instead of 1-B gave 4-F (0.42 g, 64% yield).
Synthesis of Compound 4: the same synthesis as for compound 1, except that 1-F was replaced with 4-F, gave compound 4 (0.44 g, 71% yield).
Elemental analysis: c 46 H 27 N 3 Theoretical value: c,88.86; h,4.38; n,6.76; measured value: c,88.90; h,4.36; n,6.74; HRMS (ESI) M/z (M +): theoretical value: 621.2205; measured value: 621.2212.
synthesis of 5-F: the same synthesis as 1-F, except that 5-C was used instead of carbazole, gave 5-F (0.49 g, 71% yield).
Synthesis of Compound 5: synthesis of Compound 1, except that 1-F was replaced with 5-F, gave Compound 5 (0.46 g, 70% yield).
Elemental analysis: c 48 H 28 N 4 Theoretical value: c,87.25; h,4.27; n,8.48; measured value: c,87.30; h,4.25; n,8.45; HRMS (ESI) M/z (M +): theoretical value: 660.2314; measured value: 660.2319.
synthesis of 6-F: the same synthesis as 1-D except that 1-D was used instead of 1-C,6-C instead of 1-B gave 6-F (0.43 g, 61% yield).
Synthesis of Compound 6: the same synthesis as that of Compound 1 except that 6-F was used instead of 1-F gave Compound 6 (70% yield).
Elemental analysis: c 51 H 30 N 2 Theoretical values are as follows: c,91.32; h,4.51; n,4.18; measured value: c,9134; h,4.50; n,4.16; HRMS (ESI) M/z (M +): theoretical value: 670.2409; measured value: 670.2415.
synthesis of 7-F: the same synthesis as 1-D except that 1-D was used instead of 1-C, and 7-C was used instead of 1-B gave 7-F (0.42 g, 67% yield).
Synthesis of compound 7: synthesis of Compound 1, except that 1-F was replaced with 7-F, gave Compound 7 (0.45 g, 76% yield).
Elemental analysis: c 44 H 27 N 3 Theoretical value: c,88.42; h,4.55; n,7.03; measured value: c,88.38; h,4.57; n,7.05; HRMS (ESI) M/z (M +): theoretical value: 597.2205; measured value: 597.2213.
synthesis of 8-C: the same synthesis as 1-D, except that 1-C was replaced with 8-A, and 1-B was replaced with 8-B gave 8-C (0.12 g, 35% yield).
Synthesis of 8-D: the same synthesis as 1-D was performed except that 1-C was replaced with 8-C and 1-B was replaced with o-chlorobenzoic acid to give 8-D (0.18 g, 48% yield).
Synthesis of 8-E: the same synthesis as 1-D except that 1-C was replaced with 8-D and 1-B was replaced with phenylboronic acid gave 8-E (0.24 g, 58% yield).
Synthesis of 8-F: synthesis of Compound 1, except that 1-F was replaced with 8-E, yielded 8-F (0.30 g, 77% yield).
Synthesis of 8-G: in a 50 ml three-necked flask, 8-F (1 mmol), dichloromethane (20 ml), a solution of boron tribromide (2 mmol) in dichloromethane was added dropwise at 0 ℃ and, after the reaction was completed, the solvent was removed and the crude product was purified by column chromatography (ethyl acetate/n-hexane, 1/10) to obtain 8-G (0.33G, 88% yield).
Synthesis of 8-H: taking a 50 ml two-neck round-bottom flask and putting a stirrer, adding 8-G (1 mm)ol, dichloromethane (20 ml) and pyridine (6 mmol), cooling the reaction system to 0 ℃, and adding Tf 2 O (1.5 mmol), stirring at room temperature for 30 minutes, cooling to 0 ℃, adding 30 ml dichloromethane, 40 ml water, drying the organic phase over anhydrous magnesium sulfate, distilling under reduced pressure to remove the solvent, and isolating the crude product by column chromatography (ethyl acetate/n-hexane, 1/10) to obtain 8-H (0.45 g, 90% yield).
Synthesis of 8-J: taking a 50 ml round-bottom double-neck bottle, putting a stirrer and an upper reflux pipe, adding the double pinacolyl diboron (1.5 mmol), the potassium acetate (2 mmol), protecting with nitrogen, and adding Pd (dppf) Cl 2 (0.05 mmol) and 8-H (1 mmol) are heated to 80 ℃ to react for 2 hours, water is added after the reaction is finished to quench, the system is extracted by ethyl acetate, an organic phase is dried by anhydrous magnesium sulfate to remove an organic solvent, and a crude product is separated by column chromatography (ethyl acetate/n-hexane, 1/10) to obtain 8-J (0.43 g, 89 percent of yield).
Synthesis of compound 8: taking a 50 ml two-neck round-bottom flask, putting a stirrer and an upper reflux pipe, drying, introducing nitrogen, and respectively adding a compound 8-J (1 mmol), a compound 8-K (1 mmol) and a compound potassium carbonate (K) 2 CO 3 1.5mmol, ethanol (3 ml), water (3 ml), toluene (15 ml) and tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.05 mmol), heated to 60 ℃ and reacted for 12 hours, cooled to room temperature after completion of the reaction, quenched by addition of 20 ml of water, extracted with dichloromethane (3 × 20 ml), the resulting extracts dried over magnesium sulfate, filtered and spun dry in that order, and the crude product purified by chromatography (ethyl acetate/n-hexane: volume ratio 1/10), yield 8 (0.48 g, 86% yield).
Elemental analysis: c 40 H 24 N 4 Theoretical value: c,85.69; h,4.31; n,9.99; measured value: c,85.73; h,4.30; n,9.97; HRMS (ESI) M/z (M +): theoretical value: 560.2001; measured value: 560.2009.
synthesis of compound 9: the same synthesis as 8, except that 8-K was replaced with 9-K gave 9 (0.60 g, 85% yield). Elemental analysis: c 50 H 33 N 5 Theoretical value: c,85.32; h,4.73; n,9.95; measured value: c,85.27; h,4.75; n,9.98; HRMS (ESI) M/z (M +): theoretical value: 703.2736; measured value: 703.2742.
synthesis of 10-B: the same synthesis as 1-D, except that 8-A was used instead of 1-C and o-bromobenzoic acid was used instead of 1-B gave 10-B (0.13 g, 42% yield).
Synthesis of 10-D: the same synthesis as 1-D except that 10-B was used instead of 1-C, and 10-C was used instead of 1-B gave 10-D (0.22 g, 58% yield).
Synthesis of 10-E: the same synthesis as 1-D except that 10-D was used instead of 1-C and phenylboronic acid was used instead of 1-B gave 10-E (0.33 g, 78% yield).
Synthesis of 10-F: synthesis of Compound 1 except that 1-F was replaced with 10-E gave 10-F (0.30 g, 78% yield).
Synthesis of 10-G: the same synthesis as for 8-G, except that 8-F was replaced with 10-F, gave 10-G (0.32G, 86% yield).
Synthesis of 10-H: the same synthesis as for 8-H except that 8-G was replaced with 10-G gave 10-H (0.45G, 91% yield).
Synthesis of 10-J: the synthesis of 8-J was identical except that 10-H was used instead of 8-H to give 10-J (0.42 g, 88% yield).
Synthesis of compound 10: the synthesis was identical to that of 8, except that 8-J, 2-bromobenzo [9,10] phenanthrene was replaced with 8-K by 10-J, to give 9 (0.49 g, 85% yield).
Elemental analysis: c 44 H 26 N 2 Theoretical value: c,90.69; h,4.50; n,4.81; measured value: c,90.73; h,4.48; n,4.79; HRMS (ESI) M/z (M +): theoretical value:582.2096; measured value: 582.2106.
synthesis of 11-F: the same synthesis as 1-F was performed except that 11-C was used instead of carbazole, to give 11-F (0.54 g, 73% yield).
Synthesis of compound 11: synthesis of Compound 1, except that 1-F was replaced with 11-F, gave Compound 11 (74% yield).
Elemental analysis: c 50 H 30 N 4 Theoretical value of O: c,85.45; h,4.30; n,7.97; o,2.28; measured value: c,85.40; h,4.32; n,8.00; o,2.28; HRMS (ESI) M/z (M +): theoretical value: 702.2420; measured value: 702.2414.
synthesis of 12-F: the same synthesis as 1-D except that 1-D was used instead of 1-C,12-C was used instead of 1-B gave 12-F (0.56 g, 72% yield).
Synthesis of compound 12: synthesis of Compound 1 except substituting 12-F for 1-F gave Compound 12 (0.58 g, 79% yield).
Elemental analysis: c 53 H 33 N 5 Theoretical value: c,86.04; h,4.50; n,9.47; measured value: c,85.98; h,4.52; n,9.50; HRMS (ESI) M/z (M +): theoretical value: 739.2736; measured value: 739.2744.
synthesis of 13-F: the same synthesis as 1-D except that 1-D was used instead of 1-C,13-C was used instead of 1-B gave 13-F (0.43 g, 70% yield).
Synthesis of compound 13: synthesis of Compound 1, except that 1-F was replaced with 13-F, gave Compound 13 (0.45 g, 79% yield).
Elemental analysis: c 41 H 23 N 3 Theoretical value of O: c,85.84; h,4.04; n,7.33; measured value: c,85.88; h,4.02; n,7.31; HRMS (ESI) M/z (M +): theoretical value: 573.1841; measured value: 573.1850.
synthesis of 14-F: the same synthesis as 1-D except that 1-D was used instead of 1-C, and 14-C was used instead of 1-B gave 14-F (0.48 g, 74% yield).
Synthesis of compound 14: synthesis of Compound 1, except that 1-F was replaced with 14-F, gave Compound 14 (0.50 g, 82% yield).
Elemental analysis: c 44 H 26 N 4 Theoretical value: c,86.53; h,4.29; n,9.17; measured value: c,86.52; h,4.28; n,9.20; HRMS (ESI) M/z (M +): theoretical value: 610.2157; measured value: 610.2164.
device embodiments
The OLED has the following layer structure: a base ((ITO) coated glass substrate)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/emissive layer (EML)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL), and finally a cathode.
The materials used are specifically shown in table 1, and the materials required to make an OLED are as follows.
The preparation of the organic electroluminescent device comprises the following steps:
(1) Substrate cleaning: carrying out ultrasonic treatment on the ITO-coated glass substrate in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are that ethylene glycol solvent is less than or equal to 10wt percent and triethanolamine is less than or equal to 1wt percent), washing in deionized water, and carrying out ultrasonic treatment in a water-based solvent system under the conditions of acetone: ultrasonic degreasing in an ethanol mixed solvent (1:1 in volume ratio), baking in a clean environment until water is completely removed, and then cleaning by ultraviolet light and ozone.
(2) Evaporating an organic light-emitting functional layer:
placing the glass substrate with the anode layer in a vacuum chamber, and vacuumizing to 1 × 10 -6 To 2X 10 -4 Pa, performing vacuum evaporation on the anode layer film to form a PD as a hole injection layer, wherein the evaporation thickness is 5nm;
a hole transport layer is evaporated on the hole injection layer, and the thickness of the evaporated film is 80nm;
the luminescent layer is vapor-plated on the hole transport layer, and the specific preparation method comprises the following steps: carrying out vacuum evaporation on a luminescent host material and an object material in a co-evaporation mode, wherein the total film thickness of evaporation is 30nm;
a layer of electron transport layer is vacuum evaporated on the luminescent layer, and the preparation method comprises the following steps: carrying out vacuum evaporation on Bphen and LiQ in a co-evaporation mode, wherein the total film thickness of evaporation is 30nm;
vacuum evaporating an electron injection layer on the electron transport layer, wherein the total film thickness of the evaporation is 1nm;
and evaporating Mg and Ag on the electron injection layer, wherein the total thickness of the evaporated film is 80nm.
The parameters of the layers in the device, their materials and thicknesses, etc., are shown in table 1.
TABLE 1
Testing the performance of the device:
the instrument comprises: the characteristics of the device such as current, voltage, brightness, luminescence spectrum and the like are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
and (3) testing conditions are as follows: the current density is 10mA/cm 2 Room temperature.
And (3) testing the service life: the time (in hours) was recorded when the device brightness dropped to 95% of the original brightness.
The device performance test results are shown in table 2:
TABLE 2
As shown in Table 2, when the compound of the present invention is used as a host material of an organic electroluminescent device, or as a luminescent layer material and an electron transport layer material, the compound of the present invention can reduce a driving voltage, improve a luminescent efficiency, and prolong a lifetime of the device, such that the driving voltage of the device is less than 3.70V, the current efficiency is more than 22Cd/A, and the lifetime is more than 367 h.
The applicant states that the invention is illustrated by the above examples to the compounds containing quinazoline structure and their use, but the invention is not limited to the above examples, i.e. it is not meant that the invention must be practiced by relying on the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A compound containing a quinazoline structure, wherein the compound containing the quinazoline structure has a structure shown in formula I:
l is selected from a linkage, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C5-C30 heteroarylene,
ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C5-C60 heteroarylamine, substituted or unsubstituted C5-C60 arylheteroarylamine,
R 1 -R 3 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkaneA substituted or unsubstituted C7-C30 aralkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 heteroaralkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, or a substituted or unsubstituted C6-C30 aryloxy group,
R n1 -R n8 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, or substituted or unsubstituted C6-C30 aryloxy.
2. The quinazoline structure-containing compound according to claim 1, wherein Ar is selected from the following carbazole groups:
R 4 -R 11 <xnotran> , , , , C1-C30 , O S -O- -S- C1-C30 , C2-C30 , O S -O- -S- C2-C30 , C2-C30 , C7-C30 , C6-C30 , C2-C30 , C3-C30 , C3-C30 , C3-C30 , C3-C30 , C1-C30 , C6-C30 , C6-C60 , C5 </xnotran>-a C60 heteroarylamino group, a substituted or unsubstituted aryl-heteroaryl amino group of C5-C60;
preferably, R 4 -R 11 Each is independently selected from the following substituted or unsubstituted groups: phenyl, carbazolyl, phenyl-substituted carbazolyl, biphenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzofuran-substituted carbazolyl, terphenyl-substituted carbazolyl;
preferably, R 4 -R 11 Either one of them is combined with
The connection is carried out by connecting the two parts,
L 1 selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, biphenyl-substituted carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl.
3. The quinazoline structure-containing compound of claim 2, wherein R is 4 -R 11 Each independently exists or two adjacent rings are connected to form a ring, wherein the ring is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted benzindole ring, or a substituted or unsubstituted naphthoindole ring;
and/or R 4 And R 11 Connected through benzene ring and naphthalene ring;
preferably, R 4 -R 11 Any two adjacent of them are fused with benzene ring, and/or R 4 And R 11 Through a benzene ring or a naphthalene ring;
preferably, ar is selected from
W is O, S, NL 2 Ar 3 、CR 16 R 17 ，
L 2 Selected from the group consisting of a linking bond, phenylene, naphthylene, biphenylene,
Ar 3 selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothienyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, diphenylfluorenyl-substituted phenyl, spirobifluorenyl,
R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 each independently selected from hydrogen, deuterium, phenyl and/or adjacent two are connected to form a benzene ring,
R 16 、R 17 each independently selected from methyl, phenyl, or R 16 、R 17 The bonding is carried out to form a fluorenyl group,
and/or R 4 And R 11 Through a benzene ring or a naphthalene ring.
4. A quinazoline structure-containing compound according to any one of claims 1 to 3, characterised in that Ar is selected from the following substituted or unsubstituted groups:
wherein the wavy line represents the attachment site of the group.
5. A quinazoline structure-containing compound according to any one of claims 1 to 4, characterised in that Ar is selected from the group consisting of substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, quinazolyl, 2-phenylphenanthrene [3,4-d ] oxazolyl, 2-phenylphenanthrene [3,4-d ] thiazolyl.
6. A compound containing a quinazoline structure according to any one of claims 1 to 5, characterised in that R is n1 -R n8 Each independently selected from the group consisting of substituted or unsubstituted hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl, triazinyl, quinoxalinyl, 2-phenylphenanthrene [3,4-d]Oxazolyl, 2-phenylphenanthrene [3,4-d]A thiazolyl group;
preferably, L is selected from a linker, phenylene, biphenylene, naphthylene, dibenzofuranylene;
preferably, the substituents are each independently selected from deuterium, halogen, cyano, unsubstituted or R ' substituted C1-C6 alkyl, unsubstituted or R ' substituted C6-C12 aryl, unsubstituted or R ' substituted C2-C20 heteroaryl;
r' is selected from deuterium, halogen, cyano, deuterium-substituted methyl and halogen-substituted methyl;
preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, naphthyl-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl,
preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, dibenzocarbazolyl,
preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, adamantyl.
7. The quinazoline structure-containing compound according to any one of claims 1 to 6, wherein the quinazoline structure-containing compound is any one of the following compounds:
8. an organic electroluminescent material comprising any one of the quinazoline structure-containing compounds according to any one of claims 1 to 7 or a combination of at least two thereof.
9. An organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising any one of the quinazoline structure-containing compounds according to any one of claims 1 to 7 or a combination of at least two thereof;
preferably, the organic layer includes at least a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer;
preferably, the material of the light-emitting layer comprises a host material and a guest material, the host material comprising any one of the quinazoline structure-containing compounds according to any one of claims 1 to 7 or a combination of at least two thereof;
preferably, the electron transport layer comprises any one of the quinazoline structure-containing compounds according to any one of claims 1 to 7 or a combination of at least two thereof;
preferably, the guest material is a phosphorescent dopant, which is a transition metal-containing complex, preferably an Ir-or Pt-containing complex.
10. An optoelectronic product comprising the organic electroluminescent device according to claim 9.
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| CN112939946A (en) * | 2019-12-10 | 2021-06-11 | 北京鼎材科技有限公司 | Compound and application thereof |
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| CN112159412A (en) * | 2020-10-19 | 2021-01-01 | 宁波卢米蓝新材料有限公司 | Organic nitrogen-containing heterocyclic compound and application thereof |
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