A compound containing quinazoline structure and its application

Abstract

The present invention provides a compound containing a quinazoline structure and application thereof, wherein the compound containing a quinazoline structure has a structure shown in Formula I. The compound of the present invention is used in an electron transport layer to improve luminous efficiency and extend the service life of a device.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials and relates to a compound containing a quinazoline structure and application thereof. Background Art

[0002] OLED devices have attracted much attention in the fields of new display technology and new lighting technology due to their advantages of high brightness, fast response, wide viewing angle, simple process and flexibility. At present, this technology has been widely used in display panels of new lighting fixtures, smart phones and tablet computers, and will be further expanded to large-size display products such as TVs. It is a new display technology with fast development and high technical requirements.

[0003] Organic electroluminescent devices include electrode material films, and organic functional materials sandwiched between different electrode films or self-recommended. Various functional materials are superimposed on each other according to their uses to form organic electroluminescent devices. As a current device, when voltage is applied to the electrodes at both ends of the organic electroluminescent device, positive and negative charges are generated in the organic layer functional material film through the action of the electric field. The positive and negative charges are further compounded in the light-emitting layer to generate light. This process is electroluminescence.

[0004] Research on improving the performance of organic electroluminescent devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to continuously improve the performance of organic electroluminescent devices, it is necessary not only to innovate the structure and manufacturing process of organic electroluminescent devices, but also to continuously research and innovate organic electrophotoelectric functional materials to create higher performance organic electroluminescent functional materials. Summary of the invention

[0005] In view of the deficiencies in the prior art, the present invention aims to provide a compound containing a quinazoline structure and application thereof.

[0006] To achieve this object, the present invention adopts the following technical solutions:

[0007] In one aspect, the present invention provides a quinazoline-containing compound, wherein the quinazoline-containing compound has a structure shown in formula (1-1) or formula (1-2):

[0008]

[0009] L is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C5-C30 heteroarylene group,

[0010] 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,

[0011] 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 C6-C30 aryloxy,

[0012] R n1 -R n8 Each is 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.

[0013] In the present invention, the group of the LUMO energy level distribution of the compound containing quinazoline structure is a ring structure. When used as the main material of the light-emitting layer, it is beneficial to the transmission of carriers in the light-emitting layer and promotes the combination of electrons and holes. When used as an electron transport material, it can effectively improve the electron mobility, improve the efficiency of the device, and extend the life of the device.

[0014] Preferably, Ar is selected from the following carbazole groups:

[0015] R 4 -R 11Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are substituted with —O— or —S— in a manner that the O atom or S atom is not adjacent, substituted or unsubstituted C2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are substituted with —O— or —S— in a manner that the O atom or S atom is not adjacent, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C3 0 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, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C5-C60 heteroarylamine, substituted or unsubstituted C5-C60 arylheteroarylamine,

[0016] 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;

[0017] Preferably, R 4 -R 11 Any one of them connect,

[0018] L 1 is selected from the group consisting of a linker, a phenylene group, a naphthylene group, and a biphenylene group,

[0019] 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.

[0020] R 4 -R 11 Each of them exists independently or two of them are connected to form a ring, and 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 benzoindole ring, or a substituted or unsubstituted naphthoindole ring; and / or R 4With R 11 Connected by benzene ring and naphthalene ring;

[0021] Preferably, R 4 -R 11 Any two adjacent ones of the rings are fused with a benzene ring, and / or R 4 With R 11 Connected through a benzene ring or a naphthalene ring;

[0022] Preferably, Ar is selected from W is selected from O, S, NL 2 Ar 3 , CR 16 R 17 , L 2 is selected from the group consisting of a linker, a phenylene group, a naphthylene group, and a biphenylene group,

[0023] Ar 3 is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, dimethylfluorenyl-substituted phenyl, diphenylfluorenyl, diphenylfluorenyl-substituted phenyl, and spirobifluorenyl,

[0024] 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 is independently selected from hydrogen, deuterium, phenyl and / or two adjacent groups connected to form a benzene ring,

[0025] R 16 , R 17 Each independently selected from methyl, phenyl, or R 16 , R 17 Connect to form a fluorene group,

[0026] and / or R 4 With R 11 Connected through a benzene ring or a naphthalene ring.

[0027] More preferably, Ar is selected from the following substituted or unsubstituted groups:

[0028]

[0029]

[0030]

[0031]

[0032] The wavy lines represent the attachment sites of the groups;

[0033] Preferably, Ar is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenyl substituted naphthyl, naphthyl substituted phenyl, anthracenyl, phenanthryl, triphenylene radical, 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-phenylphenanthren[3,4-d]oxazolyl, 2-phenylphenanthren[3,4-d]thiazolyl;

[0034] 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, phenanthryl, triphenylenyl, 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-phenylphenanthren[3,4-d]oxazolyl, 2-phenylphenanthren[3,4-d]thiazolyl;

[0035] Preferably, L is selected from a linker, a phenylene group, a biphenylene group, a naphthylene group, and a dibenzofuranyl group;

[0036] In the present invention, when the above-mentioned groups contain substituents, 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;

[0037] R' is selected from deuterium, halogen, cyano, deuterium-substituted methyl, halogen-substituted methyl;

[0038] Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, naphthyl-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl,

[0039] 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,

[0040] Preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, and adamantyl;

[0041] Preferably, the compound containing a quinazoline structure is any one of the following compounds:

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine, preferably fluorine.

[0053] 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.

[0054] 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 cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane, and the like.

[0055] In the present invention, the aryl and arylene groups include monocyclic, polycyclic or condensed ring aromatic groups, and the rings may be interrupted by short non-aromatic units, including but not limited to phenyl, biphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthrenyl, and triphenylenyl.

[0056] The heteroaryl and heteroarylene groups in the present invention include monocyclic, polycyclic or condensed ring aromatic groups, and the rings may be interrupted by short non-aromatic units, including but not limited to furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzo Thienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof.

[0057] Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl or spirobifluorenyl.

[0058] Preferably, the heteroaryl group is selected from dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthoimidazolyl, naphthoxazolyl, naphthothiazolyl, phenanthroimidazolyl, phenanthroxazolyl, phenanthrothiazolyl, quinoxalinyl, quinazolinyl, indolecarbazolyl, oxazolyl, indolefluorenyl, benzothienopyrazinyl, benzothienopyrimidinyl, benzofuranopyrazinyl, benzofuranopyrimidinyl, indolepyrazinyl, indolepyrimidinyl, indenopyrazinyl, indenopyrimidinyl, spiro(fluorene-9,1'-indenyl)pyrazinyl, spiro(fluorene-9,1'-indenyl)pyrimidinyl, benzofuranocarbazolyl or benzothienocarbazolyl.

[0059] As used in the present invention, 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 include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.

[0060] As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0061] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium and tritium.

[0062] In the present invention, "two adjacent groups are connected to form a ring" means that two substituents in adjacent positions in the same ring or adjacent rings can be connected to each other through chemical bonds to form a ring. The present invention does not limit the specific way of connecting to form a ring (for example, connecting through a single bond, connecting through Thick, through Thick, through Thick, through Thick, through Thick and; Indicates the position of the thick and thin), and when referring to the same description below, it has the same meaning.

[0063] In the present invention, the range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aromatic group, the number of carbon atoms representing the aromatic group can be any integer within the range of 6-60, for example 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55 or 60, etc.

[0064] In the present invention, the preparation route of the compound containing quinazoline structure is as follows:

[0065]

[0066] When L is selected from the connecting bond, the third step adopts the path of (2);

[0067] In another aspect, the present invention provides an organic electroluminescent material, which comprises any one or a combination of at least two of the compounds containing a quinazoline structure as described above.

[0068] 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, wherein the organic layer comprises any one or a combination of at least two of the above-mentioned compounds containing a quinazoline structure;

[0069] Preferably, the organic layer comprises at least a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer;

[0070] Preferably, the material of the light-emitting layer comprises a host material and a guest material, and the host material comprises any one or a combination of at least two of the compounds containing a quinazoline structure as described above;

[0071] Preferably, the electron transport layer comprises any one or a combination of at least two of the compounds containing a quinazoline structure as described above;

[0072] Preferably, the guest material is a phosphorescent dopant, and the phosphorescent dopant is a complex containing a transition metal, preferably a complex containing Ir or Pt.

[0073] In another aspect, the present invention provides an optoelectronic product, which comprises the organic electroluminescent device as described above.

[0074] Compared with the prior art, the present invention has the following beneficial effects:

[0075] The compound of the present invention is used as the main material and electron transport material of the organic electroluminescent device, which can limit the flow of carriers in the light-emitting layer and provide better device performance, including lower driving voltage, higher current efficiency and extended 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 367h. DETAILED DESCRIPTION

[0076] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0077] Synthesis Example

[0078]

[0079] Synthesis of 1-B: Take a 50 ml double-necked round-bottom flask and put it in a stirring bar and a reflux tube. After drying, fill it with nitrogen, add 1-A (1 mmol), bis(pinacol)diboron (1.2 mmol), potassium acetate (2 mmol), 1,4-dioxane (20 ml), respectively, protect it with nitrogen, add [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.05 mmol), reflux for 12 hours, and after the reaction is completed, the crude product is purified by column chromatography (ethyl acetate / n-hexane: volume ratio 1 / 10) to obtain 1-B (0.11 g, yield 47%).

[0080] Synthesis of 1-D: Take a 50 ml double-necked round-bottom flask and put it in a stirring rod and a reflux tube. After drying, fill it with nitrogen and add compounds 1-C (1 mmol), 1-B (1 mmol), potassium carbonate (K 2 CO 3 , 1.5 mmol), ethanol (3 ml), water (3 ml), toluene (15 ml) and tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4, 0.05 mmol), heated to 60 degrees Celsius and reacted for 12 hours. After the reaction was completed, it was cooled to room temperature and quenched by adding 20 ml of water. It was extracted with dichloromethane (3×20 ml). The extract was dried by adding magnesium sulfate, filtered and spin-dried. The crude product was purified by chromatography (ethyl acetate / n-hexane: volume ratio 1 / 10) to obtain 1-D (0.15 g, yield 43%).

[0081] Synthesis of 1-F: Take a 100 ml double-necked round-bottom flask and put it in a stirring bar and a reflux tube. After drying, fill it with nitrogen, add 1-D (1 mmol), carbazole (1 mmol), cesium carbonate (0.012 mol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.05 mmol) and 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (xphos, 0.055 mmol) respectively, then add toluene, reflux the mixture for 24 hours, cool to room temperature after the reaction, filter and concentrate the reaction system, and purify the crude product by chromatography (dichloromethane / n-hexane, 1 / 10 (volume ratio)) to obtain 1-F (0.38 g, yield 79%).

[0082] Synthesis of compound 1: Take a 50 ml double-necked round-bottom flask and put it in a stirring rod and a reflux tube. After drying, fill it with nitrogen and add 1-F (1 mmol), dichlorobis (tricyclohexylphosphine) palladium (PdCl 2 (PCy 3 ) 2 , 0.05mmol), pivalic acid (t-BuCO 2 H, 2 mmol), cesium carbonate (Cs 2 CO 3 , 2 mmol) and dimethylacetamide (20 ml), stirred at 120 °C for 10 hours. After the reaction was completed, it was cooled to room temperature. The reaction system was concentrated and the crude product was purified by chromatography (ethyl acetate / n-hexane: volume ratio 1 / 10) to obtain 1 (0.27 g, yield 61%).

[0083] Elemental analysis: C 32 H 19 N 3 Calculated value: C, 86.27; H, 4.30; N, 9.43; Found value: C, 86.32; H, 4.28; N, 9.40; HRMS (ESI) m / z (M+): Calculated value: 445.1579; Found value: 445.1584.

[0084]

[0085] Synthesis of 2-F: The same as the synthesis of 1-F, except that 2-C was used instead of carbazole to obtain 2-F (0.47 g, yield 77%).

[0086] Synthesis of compound 2: The synthesis was the same as that of compound 1, except that 2-F was used instead of 1-F to obtain compound 2 (0.38 g, yield 67%).

[0087] Elemental analysis: C 42 H 23 N 3 Calculated value: C, 88.55; H, 4.07; N, 7.38; Found value: C, 88.59; H, 4.05; N, 7.36; HRMS (ESI) m / z (M+): Calculated value: 569.1892; Found value: 569.1898.

[0088]

[0089] Synthesis of 3-F: The same as the synthesis of 1-F, except that 3-C was used instead of carbazole to obtain 3-F (0.48 g, yield 75%).

[0090] Synthesis of compound 3: The synthesis was the same as that of compound 1, except that 3-F was used instead of 1-F to obtain compound 3 (0.41 g, yield 69%).

[0091] Elemental analysis: C 42 H 23 N 3 S theoretical value: C, 83.84; H, 3.85; N, 6.98; S, 5.33; found value: C, 83.79; H, 3.86; N, 7.00; S, 5.35; HRMS (ESI) m / z (M+): theoretical value: 601.1613; found value: 601.1621.

[0092]

[0093] Synthesis of 4-F: The same as the synthesis of 1-D, except that 1-D is used to replace 1-C, and 4-C is used to replace 1-B, to obtain 4-F (0.42 g, yield 64%).

[0094] Synthesis of compound 4: The synthesis was the same as that of compound 1, except that 4-F was used instead of 1-F to obtain compound 4 (0.44 g, yield 71%).

[0095] Elemental analysis: C 46 H 27 N 3 Calculated value: C, 88.86; H, 4.38; N, 6.76; Found value: C, 88.90; H, 4.36; N, 6.74; HRMS (ESI) m / z (M+): Calculated value: 621.2205; Found value: 621.2212.

[0096]

[0097] Synthesis of 5-F: The same as the synthesis of 1-F, except that 5-C was used instead of carbazole to obtain 5-F (0.49 g, yield 71%).

[0098] Synthesis of compound 5: The synthesis was the same as that of compound 1, except that 5-F was used instead of 1-F to obtain compound 5 (0.46 g, yield 70%).

[0099] Elemental analysis: C 48 H 28 N 4 Calculated value: C, 87.25; H, 4.27; N, 8.48; Found value: C, 87.30; H, 4.25; N, 8.45; HRMS (ESI) m / z (M+): Calculated value: 660.2314; Found value: 660.2319.

[0100]

[0101] Synthesis of 6-F: The same as the synthesis of 1-D, except that 1-D is used to replace 1-C, and 6-C is used to replace 1-B, to obtain 6-F (0.43 g, yield 61%).

[0102] Synthesis of compound 6: The synthesis was the same as that of compound 1, except that 6-F was used instead of 1-F to obtain compound 6 (yield 70%).

[0103] Elemental analysis: C 51 H 30 N 2 Calculated value: C, 91.32; H, 4.51; N, 4.18; Found value: C, 91.34; H, 4.50; N, 4.16; HRMS (ESI) m / z (M+): Calculated value: 670.2409; Found value: 670.2415.

[0104]

[0105] Synthesis of 7-F: The same as the synthesis of 1-D, except that 1-D is used to replace 1-C, and 7-C is used to replace 1-B, to obtain 7-F (0.42 g, yield 67%).

[0106] Synthesis of compound 7: The synthesis was the same as that of compound 1, except that 7-F was used instead of 1-F to obtain compound 7 (0.45 g, yield 76%).

[0107] Elemental analysis: C 44 H 27 N 3Calculated value: C, 88.42; H, 4.55; N, 7.03; Found value: C, 88.38; H, 4.57; N, 7.05; HRMS (ESI) m / z (M+): Calculated value: 597.2205; Found value: 597.2213.

[0108]

[0109] Synthesis of 8-C: The same as the synthesis of 1-D, except that 8-A is used to replace 1-C, and 8-B is used to replace 1-B, to obtain 8-C (0.12 g, yield 35%).

[0110] Synthesis of 8-D: The same as the synthesis of 1-D, except that 8-C was used instead of 1-C, and o-chlorophenylboronic acid was used instead of 1-B, to give 8-D (0.18 g, yield 48%).

[0111] Synthesis of 8-E: The same as the synthesis of 1-D, except that 8-D was used to replace 1-C, and phenylboronic acid was used to replace 1-B, to obtain 8-E (0.24 g, yield 58%).

[0112] Synthesis of 8-F: The synthesis was the same as compound 1, except that 8-E was used instead of 1-F to obtain 8-F (0.30 g, yield 77%).

[0113] Synthesis of 8-G: In a 50 ml three-necked flask, add 8-F (1 mmol) and dichloromethane (20 ml), and then add dropwise a dichloromethane solution of boron tribromide (2 mmol) at 0 degrees Celsius. After the reaction, remove the solvent and purify the crude product by column chromatography (ethyl acetate / n-hexane, 1 / 10) to obtain 8-G (0.33 g, yield 88%).

[0114] Synthesis of 8-H: Take a 50 ml double-necked round-bottom flask and put it in a stirrer, add 8-G (1 mmol), dichloromethane (20 ml), pyridine (6 mmol), cool the reaction system to 0 degrees Celsius, add Tf 2 O (1.5 mmol), the system was stirred at room temperature for 30 minutes, then cooled to 0 degrees Celsius, 30 ml of dichloromethane and 40 ml of water were added, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The crude product was separated by column chromatography (ethyl acetate / n-hexane, 1 / 10) to obtain 8-H (0.45 g, yield 90%).

[0115] Synthesis of 8-J: Take a 50 ml round-bottom double-necked flask and put it in a stirring rod and a reflux tube, add double pinacol diboron (1.5 mmol), potassium acetate (2 mmol), and add Pd(dppf)Cl under nitrogen protection. 2(0.05mmol), 8-H (1mmol), heated to 80 degrees Celsius, reacted for 2 hours, after the reaction was completed, water was added to quench, the system was extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate and the organic solvent was removed, the crude product was separated by column chromatography (ethyl acetate / n-hexane, 1 / 10) to obtain 8-J (0.43 g, yield 89%).

[0116]

[0117] Synthesis of compound 8: Take a 50 ml double-necked round-bottom flask and put it into a stirring rod and a reflux tube. After drying, fill it with nitrogen and add compounds 8-J (1 mmol), 8-K (1 mmol), potassium carbonate (K 2 CO 3 , 1.5 mmol), ethanol (3 ml), water (3 ml), toluene (15 ml) and tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 , 0.05 mmol), heated to 60 degrees Celsius and reacted for 12 hours. After the reaction was completed, it was cooled to room temperature and quenched with 20 ml of water. It was extracted with dichloromethane (3×20 ml). The extract was dried over magnesium sulfate, filtered and spin-dried. The crude product was purified by chromatography (ethyl acetate / n-hexane: volume ratio 1 / 10) to obtain 8 (0.48 g, yield 86%).

[0118] Elemental analysis: C 40 H 24 N 4 Calculated value: C, 85.69; H, 4.31; N, 9.99; Found value: C, 85.73; H, 4.30; N, 9.97; HRMS (ESI) m / z (M+): Calculated value: 560.2001; Found value: 560.2009.

[0119]

[0120] Synthesis of compound 9: Same as the synthesis of 8, except that 9-K was used instead of 8-K, to obtain 9 (0.60 g, yield 85%). Elemental analysis: C 50 H 33 N 5 Calculated value: C, 85.32; H, 4.73; N, 9.95; Found value: C, 85.27; H, 4.75; N, 9.98; HRMS (ESI) m / z (M+): Calculated value: 703.2736; Found value: 703.2742.

[0121]

[0122] Synthesis of 10-B: The same as the synthesis of 1-D, except that 8-A was used instead of 1-C, and o-bromophenylboronic acid was used instead of 1-B, to obtain 10-B (0.13 g, yield 42%).

[0123] Synthesis of 10-D: The synthesis was the same as that of 1-D, except that 10-B was used to replace 1-C, and 10-C was used to replace 1-B, to obtain 10-D (0.22 g, yield 58%).

[0124] Synthesis of 10-E: The same as the synthesis of 1-D, except that 10-D was used to replace 1-C, and phenylboronic acid was used to replace 1-B, to obtain 10-E (0.33 g, yield 78%).

[0125] Synthesis of 10-F: The synthesis was the same as compound 1, except that 10-E was used instead of 1-F to obtain 10-F (0.30 g, yield 78%).

[0126] Synthesis of 10-G: The synthesis was the same as that of 8-G, except that 10-F was used instead of 8-F to obtain 10-G (0.32 g, yield 86%).

[0127] Synthesis of 10-H: The synthesis was the same as that of 8-H, except that 10-G was used instead of 8-G to obtain 10-H (0.45 g, yield 91%).

[0128] Synthesis of 10-J: The synthesis was the same as that of 8-J, except that 10-H was used instead of 8-H to obtain 10-J (0.42 g, yield 88%).

[0129] Synthesis of compound 10: The synthesis was the same as that of 8, except that 10-J was used instead of 8-J, and 2-bromobenzo[9,10]phenanthrene was used instead of 8-K to obtain 9 (0.49 g, yield 85%).

[0130] Elemental analysis: C 44 H 26 N 2 Calculated value: C, 90.69; H, 4.50; N, 4.81; Found value: C, 90.73; H, 4.48; N, 4.79; HRMS (ESI) m / z (M+): Calculated value: 582.2096; Found value: 582.2106.

[0131]

[0132] Synthesis of 11-F: The same as the synthesis of 1-F, except that 11-C was used instead of carbazole to obtain 11-F (0.54 g, yield 73%).

[0133] Synthesis of compound 11: The synthesis was the same as compound 1, except that 11-F was used instead of 1-F to obtain compound 11 (yield 74%).

[0134] Elemental analysis: C 50 H 30 N 4 O theoretical value: C, 85.45; H, 4.30; N, 7.97; O, 2.28; found value: C, 85.40; H, 4.32; N, 8.00; O, 2.28; HRMS (ESI) m / z (M+): theoretical value: 702.2420; found value: 702.2414.

[0135]

[0136] Synthesis of 12-F: The same as the synthesis of 1-D, except that 1-D was used to replace 1-C, and 12-C was used to replace 1-B, to obtain 12-F (0.56 g, yield 72%).

[0137] Synthesis of compound 12: The synthesis was the same as that of compound 1, except that 12-F was used instead of 1-F to obtain compound 12 (0.58 g, yield 79%).

[0138] Elemental analysis: C 53 H 33 N 5 Calculated value: C, 86.04; H, 4.50; N, 9.47; Found value: C, 85.98; H, 4.52; N, 9.50; HRMS (ESI) m / z (M+): Calculated value: 739.2736; Found value: 739.2744.

[0139]

[0140] Synthesis of 13-F: The same as the synthesis of 1-D, except that 1-D was used to replace 1-C, and 13-C was used to replace 1-B, to obtain 13-F (0.43 g, yield 70%).

[0141] Synthesis of compound 13: The synthesis was the same as that of compound 1, except that 13-F was used instead of 1-F to obtain compound 13 (0.45 g, yield 79%).

[0142] Elemental analysis: C 41 H 23 N 3 O Calculated value: C, 85.84; H, 4.04; N, 7.33; Found: C, 85.88; H, 4.02; N, 7.31; HRMS (ESI) m / z (M+): Calculated value: 573.1841; Found: 573.1850.

[0143]

[0144] Synthesis of 14-F: The synthesis is the same as that of 1-D, except that 1-D is used to replace 1-C, and 14-C is used to replace 1-B, to obtain 14-F (0.48 g, yield 74%).

[0145] Synthesis of compound 14: The synthesis was the same as compound 1, except that 14-F was used instead of 1-F to obtain compound 14 (0.50 g, yield 82%).

[0146] Elemental analysis: C 44 H 26 N 4 Calculated value: C, 86.53; H, 4.29; N, 9.17; Found value: C, 86.52; H, 4.28; N, 9.20; HRMS (ESI) m / z (M+): Calculated value: 610.2157; Found value: 610.2164.

[0147] Device Embodiment

[0148] OLEDs have the following layer structure: substrate ((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 the cathode.

[0149] The materials used are specifically shown in Table 1. The materials required to manufacture OLED are as follows.

[0150]

[0151] The preparation of the organic electroluminescent device comprises the following steps:

[0152] (1) Substrate cleaning: The ITO-coated glass substrate is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0153] (2) Evaporation of organic light-emitting functional layer:

[0154] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, PD is vacuum evaporated on the above anode layer as a hole injection layer with a thickness of 5 nm;

[0155] A hole transport layer is evaporated on the hole injection layer, and the evaporated film thickness is 80nm;

[0156] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is: vacuum depositing the light-emitting host material and the guest material in a co-evaporation manner, and the total film thickness of the deposition is 30 nm;

[0157] An electron transport layer is vacuum-deposited on the light-emitting layer. The specific preparation method is as follows: Bphen and LiQ are vacuum-deposited in a co-evaporation manner, and the total film thickness of the evaporation is 30 nm;

[0158] An electron injection layer is vacuum-deposited on the electron transport layer, and the total thickness of the evaporated layer is 1 nm;

[0159] Mg:Ag was evaporated on the electron injection layer, and the total film thickness was 80 nm.

[0160] The parameters of each layer in the device, its material, thickness and so on are shown in Table 1.

[0161] Table 1

[0162]

[0163]

[0164] Device performance test:

[0165] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0166] Test conditions: current density is 10mA / cm 2 , room temperature.

[0167] Life test: Record the time (in hours) when the device brightness drops to 95% of the original brightness.

[0168] The device performance test results are shown in Table 2:

[0169] Table 2

[0170]

[0171] As can be seen from Table 2, when the compounds of the present invention are used as the main material of an organic electroluminescent device, or are used as both a light-emitting layer material and an electron transport layer material, the driving voltage can be reduced, the luminous efficiency can be improved, and the service life of the device can be extended, so that the driving voltage of the device is below 3.70 V, the current efficiency is above 22 Cd / A, and the service life is above 367 h.

[0172] The applicant declares that the present invention illustrates the compound containing quinazoline structure and its application by the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, the equivalent replacement of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode and a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer; The material of the light-emitting layer comprises a host material and a guest material, and the host material comprises any one or a combination of at least two of the compounds containing a quinazoline structure; The electron transport layer comprises any one or a combination of at least two of the compounds containing a quinazoline structure; The compound containing quinazoline structure has the structure shown below:

2. The organic electroluminescent device according to claim 1, characterized in that: The guest material is a phosphorescent dopant, and the phosphorescent dopant is a complex containing a transition metal.

3. The organic electroluminescent device according to claim 2, characterized in that: The phosphorescent dopant is a complex containing Ir or Pt.

4. A photoelectric product, characterized in that: It comprises the organic electroluminescent device as claimed in any one of claims 1 to 3.

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