CN115433168B - Heterocyclic compound, organic electroluminescent material and organic electroluminescent device using same - Google Patents

Heterocyclic compound, organic electroluminescent material and organic electroluminescent device using same Download PDF

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CN115433168B
CN115433168B CN202110621139.8A CN202110621139A CN115433168B CN 115433168 B CN115433168 B CN 115433168B CN 202110621139 A CN202110621139 A CN 202110621139A CN 115433168 B CN115433168 B CN 115433168B
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heterocyclic compound
deuterium
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CN115433168A (en
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李祥智
蔡烨
魏定纬
陈志宽
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Ningbo Dingsheng New Material Co ltd
Ningbo Lumilan Advanced Materials Co Ltd
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Ningbo Dingsheng New Material Co ltd
Ningbo Lumilan Advanced Materials Co Ltd
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Abstract

The invention provides a heterocyclic compound, an organic electroluminescent material and an organic electroluminescent device using the same, wherein the heterocyclic compound has a structure shown in a formula I, and the heterocyclic compound can accelerate electron transmission and avoid overflow of electrons in the transmission process, so that matching of electron and hole transmission capacity is promoted, and the efficiency and the service life of the organic electroluminescent device are improved.

Description

Heterocyclic compound, organic electroluminescent material and organic electroluminescent device using same
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to a heterocyclic compound, an organic electroluminescent material and an organic electroluminescent device using the same.
Background
Compared with the traditional light-emitting technology, the OLED device has the advantages of low driving voltage, high light-emitting efficiency, high contrast ratio, high color saturation, wide viewing angle, quick response time and the like, has great potential to replace a mainstream liquid crystal display, and becomes a star technology in the display field. The growing demand in the display field has also driven the rapid development of OLED device structures and organic photovoltaic materials.
The device prepared by the existing material has short service life and low efficiency, and cannot meet the market development requirement, so how to provide a main material with high efficiency and long service life for an organic electroluminescent device becomes a technical problem to be solved urgently.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a heterocyclic compound, an organic electroluminescent material and an organic electroluminescent device using the same. The heterocyclic compound of the invention can accelerate electron transmission, and avoid electron overflow in the transmission process, thereby promoting the matching of electron and hole transmission capability, improving the efficiency and the service life of the organic electroluminescent device.
To achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a heterocyclic compound having a structure represented by formula I:
y is selected from the group consisting of O, S,
R 1 -R 16 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are not adjacent to an O-or-S-substituted, substituted or unsubstituted C2-C30 alkenyl in which one or more methylene groups are not adjacent to an O-or-S-substitutedSubstituted C2-C30 alkynyl, 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, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino,
R 1 -R 16 each independently or adjacent two are linked to form a ring, the ring being a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring,
l is selected from the group consisting of a bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene,
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
Preferably, R 1 -R 8 Any adjacent two andcondensed, wherein the bond of two asterisks is a shared bond with the benzene ring of the group when condensed;
R n1 -R n4 each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are not adjacent to each other by an O-or-S-substituted C1-C30 alkyl group, substituted or unsubstituted C7-C60 aralkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted C3-C60 heteroaralkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C1-C30 alkoxy group or substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C6-C60 arylamine group, substituted or unsubstituted C6-C60 heteroarylamine group, substituted or unsubstituted C6-C60 aryl groupA heteroaromatic amine group,
R n1 -R n4 each independently or adjacent two are connected into a benzene ring or a naphthalene ring.
Preferably, the heterocyclic compound is a compound having any one of the following structures:
preferably, R n1 And R is R 8 Connected by benzene ring;
preferably, the heterocyclic compound has the following structure:
preferably, R 1 、R 8 The two are connected through naphthalene ring;
preferably, the heterocyclic compound has the following structure:
preferably, R 1 -R 8 Any adjacent two andcondensed, wherein the bond of two asterisks is a shared bond with benzene ring of the group when condensed,
x is selected from O, S, CR X1 R X2 、NR X3 ，
R X1 、R X2 Each independently selected from the group consisting of substituted or unsubstituted C1-C4 straight or branched alkyl, substituted or unsubstituted C6-C18 aryl, R X1 、R X2 Independently or adjacent to each other, are substituted or unsubstituted fluorene rings,
R X3 a heteroaryl group selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30;
R m1 -R m4 each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are not adjacent to each other by an O-or-S-substituted C1-C30 alkyl group, substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 heteroaralkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C1-C30 alkoxy group or substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C6-C30 heteroarylamine group, substituted or unsubstituted C6-C30 arylheteroarylamine group,
R m1 -R m4 each independently or adjacent two are connected into a benzene ring or a naphthalene ring.
Preferably, R X1 、R X2 Each independently selected from methyl, ethyl, phenyl or R X1 、R X2 The two are connected into fluorenyl;
preferably, R X3 Selected from the group consisting of substituted or unsubstituted: phenyl, pyridyl, biphenyl, terphenyl, naphthyl, benzosubstituted naphthyl, naphthalene substituted phenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dinaphthofuranyl, dinaphthothiophenyl, dimethylfluorenyl, benzocarbazolyl, benzofluorenyl, benzosubstituted dimethylfluorenyl, benzosubstituted dibenzofuranyl, benzosubstituted dibenzothiophenyl, dimethylfluorene substituted phenyl, dibenzofuran substituted phenyl, dibenzothiophene substituted phenyl.
Preferably, the heterocyclic compound is a compound having any one of the following structures:
preferably, R X3 And R is R 8 Connected by benzene ring;
preferably, the heterocyclic compound has the following structure:
preferably, the method comprises the steps of,selected from the group consisting of substituted or unsubstituted:
the wavy line represents the attachment position of the group.
Preferably, said L is selected from the group consisting of a bond, a substituted or unsubstituted group consisting of: phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl or carbazolyl;
preferably, when the 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; r' is selected from deuterium, halogen, cyano, deuterium substituted methyl, halogen substituted methyl.
Preferably, the heterocyclic compound is any one of the following compounds:
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wherein D is deuterium.
As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine, preferably fluorine.
As used herein, the term "alkyl" refers to monovalent substituents derived from straight or branched chain saturated hydrocarbons having from 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 indicated, 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.
As used herein, the term "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 30 carbon atoms and having at least one carbon-carbon double bond. Examples include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
As used herein, the term "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond and having 2 to 30 carbon atoms. Examples include, but are not limited to, ethynyl, 2-propynyl, and the like.
In the present invention, aryl, arylene includes monocyclic, polycyclic or fused ring aryl groups, which may be interrupted between rings by short non-aromatic units, including, but not limited to, phenyl, biphenyl, naphthyl, binaphthyl, phenyl naphthyl, naphthyl phenyl, fluorenyl, phenyl fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenyl phenanthryl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthacene, perylenyl, droxy, fused tetraphenyl, fluoranthracenyl or spirobifluorenyl, derivatives thereof, and the like.
Heteroaryl, heteroarylene, includes monocyclic, polycyclic or fused ring aryl groups, which may be interrupted by a short non-aromatic unit between the rings, including, but not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazayl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof, and the like.
Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl or spirobifluorenyl.
Preferably, the heteroaryl is selected from dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, pyridinyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthazazolyl, phenanthroimidazolyl, phenanthroxazinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothiophenopyrimidinyl, benzofuranopyrazinyl, benzofuranopyrimidinyl, indolopyrazinyl, indenopyrazinyl, indenopyrimidinyl, spiro (fluorene-9, 1' -indene) opyrazinyl, benzofuranocarzolyl or benzothiophenocarzolyl.
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" refers to a compound in which a hydrogen atom is replaced with another substituent. The position is not limited to a specific position as long as hydrogen at the position can be substituted with 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 indicated, hydrogen atoms include protium, deuterium, and tritium.
In the present invention, "adjacent two groups are connected to form a ring" means that 2 substituents at adjacent positions in the same ring or adjacent rings can be connected to each other by chemical bonds to form a ring, and the present invention is not limited to a specific connection form, and has the same meaning when the following description refers to the same.
In the present invention, the definition of a group defines a range of carbon atoms, the number of carbon atoms being any integer within the defined range, for example, a C6-C60 aryl group, and the number of carbon atoms representing the aryl group may be any integer within the range of 6-60 inclusive, for example, 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55, 60, or the like.
In the invention, the preparation route of the heterocyclic compound is as follows:
wherein Bpin is a pinacol borate group.
In another aspect, the present invention provides an organic electroluminescent material comprising any one or a combination of at least two of the heterocyclic compounds described above.
In another aspect, the present invention provides an organic electroluminescent composition comprising any one or a combination of at least two of the heterocyclic compounds 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 or a combination of at least two of the organic electroluminescent compounds as described above.
Preferably, the organic layer at least comprises 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 or a combination of at least two of the organic electroluminescent compounds 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.
In the present invention, the organic electroluminescent device or the electro-optical product as described above may be applied to optoelectronics, medicine, biotechnology, optical fiber, lighting device, electrophotographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light emitting field effect transistor, image sensor, and dye laser.
Compared with the prior art, the invention has the following beneficial effects:
the heterocyclic compound of the invention can accelerate electron transmission, and avoid electron overflow in the transmission process, thereby promoting the matching of electron and hole transmission capability, improving the efficiency and the service life of the organic electroluminescent device.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Synthetic examples
1-B synthesis: 1-A (0.34 g,1 mmol), phenylselenious anhydride (1.2 mmol), chlorobenzene (15 mL) and the system were added to a 50 mL two-necked round bottom flask, the reaction was refluxed for 10 hours, cooled to room temperature after the completion of the reaction, the solvent was removed by distillation under reduced pressure, and the crude product was washed with n-hexane to give 1-B (0.35 g).
1-C synthesis: 1-B (0.35 g), hydroxylamine hydrochloride (5 mmol), methanol (15 ml), pyridine (1.5 ml) were added into a 25 ml two-necked flask, the system was heated to 90 ℃ for reaction for 3 hours, after the reaction was completed, the solvent of the system was removed by distillation under reduced pressure, the product was added into an aqueous solution of methanol (volume ratio 1:10), and a precipitate was obtained after filtration;
1-D synthesis: in a 25 ml two neck round bottom flask, 10 ml ethanol was added under nitrogen protection, nitrogen was purged for 15 minutes, the air in the solvent was removed, the sediment obtained in the previous step was added, the system was heated to 60 degrees celsius, pd/C (0.1 g) was added, hydrazine hydrate (2 ml) was slowly added after 10 minutes, ethanol 2 ml, after overnight reaction, the system was cooled to room temperature, impurities were removed by filtration, water was added, dichloromethane extraction was performed, and the solvent was removed by distillation under reduced pressure to obtain 1-D (0.35 g).
1-E synthesis: in a 25 ml two-necked round bottom flask, 1-D (0.35 g), 4mol/L aqueous hydrochloric acid (10 ml) and oxalic acid (1.5 mmol) aqueous hydrochloric acid (4 mol/L,2 ml) were added, and the system was refluxed for 2 hours, cooled to room temperature after the reaction was completed, filtered to obtain a solid, washed with water and dried to obtain 1-E (0.41 g).
1-F synthesis: in a 25 mL two-necked round bottom flask, a solution of 1-E (0.41 g), thionyl chloride (3 mmol) in dichloroethane (10 mL) was added, DMF (0.1 mmol) was slowly added, the system was heated at reflux for 2 hours, dichloroethane was removed, and the system was separated by column chromatography (dichloromethane/n-hexane, 1/10 (volume ratio)) to give 1-F (0.42 g, yield 90%).
1-G synthesis: in a 50 mL three-necked flask, 1-F (0.46G, 1 mmol), phenylboronic acid pinacol ester (1 mmol), tetrakis (triphenylphosphine) palladium (0.05 mmol), toluene (20 mL), sodium bicarbonate (1.2 mol) in water (4 mL) was added, heated to 100℃and reacted for 8 hours, after the reaction was completed, water was added to quench the reaction, methylene chloride was extracted three times, the organic layer was dried over anhydrous magnesium sulfate, the organic solvent was removed, and the crude product was separated by column chromatography (methylene chloride/n-hexane, 1/10 (volume ratio)) to give 1-G (0.26G, yield 51%).
Synthesis of Compound 1: a50 mL two-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, after drying, nitrogen was charged, 1-G (0.50G, 1 mmol), 7H-dibenzocarbazole (0.27G, 1 mmol), cesium carbonate (1.5 mol), tris (dibenzylideneacetone) dipalladium (0.05 mmol) and 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.055 mmol) were added respectively, toluene was then added, the mixture was refluxed for 12 hours, cooled to room temperature after the reaction, the reaction system was filtered and concentrated, and the crude product was purified by column chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to give compound 1 (0.45G, yield 61%).
HRMS-ESI m/z[M+H] + :736.31。
Synthesis of 3-B: the synthesis of 1-B was repeated except that 3-A was used instead of 1-A to give 3-B (0.24 g).
Synthesis of 3-C: the synthesis of 1-C is different in that 3-B is used for replacing 1-B, and 3-C is obtained.
Synthesis of 3-D: the synthesis of 1-D was followed except that 3-C was used instead of 1-C to give 3-D (0.24 g).
Synthesis of 3-E: the synthesis of 1-E was followed except that 3-D was used instead of 1-D to give 3-E (0.29 g).
Synthesis of 3-F: the synthesis of 1-F was repeated except that 3-E was used instead of 1-E to give 3-F (0.30 g, 88% yield).
Synthesis of 3-H: the synthesis of 1-G was repeated except that 3-F was used instead of 1-F and 3-G was used instead of pinacol phenylboronate to give 3-H (0.19G, 41%).
3, synthesis: the synthesis was identical to that of compound 1 except that 3-H was used in place of 1-G to give compound 3 (0.4G, 57%).
HRMS-ESI m/z[M+H] + :704.32。
7-B synthesis: the synthesis of 1-B was repeated except that 7-A was used instead of 1-A to give 7-B (0.29 g).
7-C synthesis: the synthesis of 1-C is different in that 7-B is used for replacing 1-B, and 7-C is obtained.
7-D synthesis: the synthesis of 1-D was repeated except that 7-C was used instead of 1-C to give 7-D (0.28 g).
7-E synthesis: the synthesis of 1-E was followed except that 7-D was used in place of 1-D to give 7-E (0.32 g).
7-F synthesis: the synthesis of 1-F was repeated except that 7-E was used instead of 1-E to give 7-F (0.35 g, 89% yield).
7-H synthesis: the synthesis of 1-G was repeated except that 7-F was used instead of 1-F and 7-G was used instead of pinacol ester of phenylboronic acid to give 7-H (0.20G, 47%).
7, synthesis: the synthesis was identical to that of compound 1, except that 7-H was used in place of 1-G and 7-J was used in place of 1-H to give compound 7 (0.38G, 51%).
HRMS-ESI m/z[M+H] + :742.34。
11-B synthesis: the synthesis of 1-B was repeated except that 11-A was used instead of 1-A to give 11-B (0.29 g).
11-C synthesis: the synthesis of 1-C is different in that 11-B is used instead of 1-B to obtain 11-C.
11-D synthesis: the synthesis of 1-D was repeated except that 11-C was used instead of 1-C to give 11-D (0.28 g).
Synthesis of 11-E: the synthesis of 1-E was repeated except that 11-D was used instead of 1-D to give 11-E (0.33 g).
11-F synthesis: the synthesis of 1-F was repeated except that 11-E was used instead of 1-E to give 11-F (0.35 g, yield 90%).
Synthesis of 11-H: the synthesis of 1-G was repeated except that 11-F was used instead of 1-F and 11-G was used instead of pinacol ester of phenylboronic acid to give 11-H (0.23G, 53%).
11 synthesis: the synthesis was identical to that of compound 1 except that 11-H was used in place of 1-G to give compound 11 (0.35G, 48%).
HRMS-ESI m/z[M+H] + :740.24。
12-B synthesis: the synthesis of 1-B was repeated except that 12-A was used instead of 1-A to obtain 12-B (0.21 g).
12-C synthesis: the synthesis of 1-C is different in that 12-B is used for replacing 1-B, and 12-C is obtained.
12-D synthesis: the synthesis of 1-D was repeated except that 12-C was used instead of 1-C to obtain 12-D (0.22 g).
12-E synthesis: the synthesis of 1-E was repeated except that 12-D was used instead of 1-D to give 12-E (0.25 g).
12-F synthesis: the synthesis of 1-F was repeated except that 12-E was used instead of 1-E to give 12-F (0.29 g, 91% yield).
12-G synthesis: the synthesis of 1-G was repeated except that 12-F was used instead of 1-F to give 12-G (0.19G, 54%).
12 synthesis: the synthesis was identical to that of compound 1, except that 12-G was used in place of 1-G and 12-H was used in place of 1-H to give compound 12 (0.24G, 39%).
HRMS-ESI m/z[M+H] + :614.17。
15-B synthesis: the synthesis of 1-B was repeated except that 1-A was replaced with 15-A to give 15-B (0.22 g).
15-C synthesis: the synthesis of 1-C is similar to that of 1-C except that 15-B is used instead of 1-B to obtain 15-C.
15-D synthesis: the synthesis of 1-D was repeated except that 15-C was used instead of 1-C to give 15-D (0.22 g).
15-E synthesis: the synthesis of 1-E was repeated except that 1-D was replaced with 15-D to give 15-E (0.26 g).
15-F synthesis: the synthesis of 1-F was repeated except that 15-E was used instead of 1-E to give 15-F (0.29 g, 89% yield).
15-G synthesis: the synthesis of 1-G was identical except that 15-F was used instead of 1-F, giving 15-G (0.20G, 53%).
15 synthesis: the synthesis was identical to that of compound 1, except that 15-G was used instead of 1-G and 15-H was used instead of 1-H to give compound 15 (0.36G, 48%).
HRMS-ESI m/z[M+H] + :745.28。
The raw materials in Table 1 are synthesized into intermediates by adopting a 1-G synthesis method, and the specific structural formula of the product in Table 1 is shown.
TABLE 1
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The raw materials in table 2 were synthesized into compounds 2, 4, 5, 6, 8, 9, 10, 13, 14, 16 and the compound of comparative example 1 by the synthesis method of compound 1.
TABLE 2
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Device embodiment
The OLED has the following layer structure: a base (indium tin oxide (ITO) coated glass substrate)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/light emitting layer (EML)/Electron Transport Layer (ETL)/optional Electron Injection Layer (EIL), and finally a cathode.
The materials used are specifically shown in table 3, and the structures of the materials required for manufacturing the OLED are as follows.
The preparation of the organic electroluminescent device comprises the following steps:
the patterned Indium Tin Oxide (ITO) coated glass substrate (NHT, 2 mm. Times.2 mm, 20. OMEGA.cm) -2 ) And oxygen plasma (150W, 5min, 4X 10) -2 torr) process. The organic material was purified by thermal sublimation prior to the device experiments. In a multi-source thermal evaporation system, at 3×10 -6 the organic light emitting diode is fabricated at a base pressure of torr or below. The deposition rate of the organic material controlled by the dopant (Infinione IC/5) isBut to exclude dopants to suitWhen co-evaporated at a rate to obtain the desired doping level.
TABLE 3 Table 3
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Device performance test:
instrument: the characteristics of current, voltage, brightness, luminescence spectrum and the like of the device are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
test conditions: the current density was 20mA/cm 2 Room temperature.
Life test: the time (in hours) for the device brightness to drop to 95% of the original brightness was recorded.
The device performance test results are shown in table 4:
TABLE 4 Table 4
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As can be seen from table 4, the compounds of the present invention allow the organic electroluminescent device to have a lower driving voltage (below 4.7V), a higher current efficiency (above 16 Cd/a) and a longer lifetime (above 91 h).
The applicant states that the present invention is illustrated by the above examples for the heterocyclic compound, the organic electroluminescent material and the organic electroluminescent device using the same, but the present invention is not limited to the above examples, i.e., it does not mean that the present invention must be practiced depending on the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.

Claims (24)

1. A heterocyclic compound, wherein the heterocyclic compound has a structure according to formula I:
y is selected from the group consisting of O, S,
R 1 -R 16 each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are not adjacent to each other by an O-or-S-substituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl in which one or more methylene groups are not adjacent to each other by an O-or-S-substituted C2-C30 alkenyl group, substituted or unsubstituted C2-C30 alkynyl group, substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 heteroaralkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C1-C30 alkoxy group or substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C60 heteroaryl group,
R 1 -R 16 each independently or adjacent two are linked to form a ring, the ring being a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 heteroaromatic ring,
l is selected from the group consisting of a bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene,
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
when the groups contain substituents, 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, halogen substituted methyl.
2. The heterocyclic compound according to claim 1, wherein R 1 -R 8 Any adjacent two andcondensed, wherein the bond of two asterisks is a shared bond with the benzene ring of the group when condensed;
R n1 -R n4 each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are not adjacent to each other by an O-or-S-substituted C1-C30 alkyl group, substituted or unsubstituted C7-C60 aralkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted C3-C60 heteroaralkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C1-C30 alkoxy group or substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C6-C60 arylamine group, substituted or unsubstituted C6-C60 heteroarylamine group, substituted or unsubstituted C6-C60 arylheteroarylamine group,
R n1 -R n4 each independently exists or adjacent two are connected into a benzene ring or a naphthalene ring;
when the groups contain substituents, 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, halogen substituted methyl.
3. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is a compound having any one of the following structures:
4. a heterocyclic compound according to any one of claims 1-3, characterized in that R n1 And R is R 8 Connected by a benzene ring.
5. The heterocyclic compound of claim 1, wherein the heterocyclic compound has the structure:
6. the heterocyclic compound according to claim 1, wherein R 1 、R 8 The two are connected through naphthalene ring.
7. The heterocyclic compound of claim 1, wherein the heterocyclic compound has the structure:
8. the heterocyclic compound according to claim 1, wherein R 1 -R 8 Any adjacent two andcondensed, wherein the bond of two asterisks is a shared bond with benzene ring of the group when condensed,
x is selected from O, S, CR X1 R X2 、NR X3 ，
R X1 、R X2 Each independently selected from substituted or unsubstituted C1-C4 straight or branched chainsAlkyl, substituted or unsubstituted C6-C18 aryl, R X1 、R X2 Independently or adjacent to each other, are substituted or unsubstituted fluorene rings,
R X3 a heteroaryl group selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30; r is R m1 -R m4 Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are not adjacent to each other by an O-or-S-substituted C1-C30 alkyl group, substituted or unsubstituted C7-C30 aralkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 heteroaralkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C1-C30 alkoxy group or substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C6-C30 heteroarylamine group, substituted or unsubstituted C6-C30 arylheteroarylamine group,
R m1 -R m4 each independently exists or adjacent two are connected into a benzene ring or a naphthalene ring;
when the groups contain substituents, 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, halogen substituted methyl.
9. The heterocyclic compound according to claim 8, wherein R X1 、R X2 Each independently selected from methyl, ethyl, phenyl or R X1 、R X2 The two are connected into fluorenyl.
10. The heterocyclic compound according to claim 8, wherein R X3 Selected from the group consisting of substituted or unsubstituted: phenyl, pyridyl, biphenyl, terphenyl, naphthyl, benzene-substituted naphthyl, naphthalene-substituted phenyl, carbazolyl, and diBenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dinaphthofuranyl, dinaphthothiophenyl, dimethylfluorenyl, benzocarbazolyl, benzofluorenyl, benzosubstituted dimethylfluorenyl, benzosubstituted dibenzofuranyl, benzosubstituted dibenzothiophenyl, dimethylfluorenyl substituted phenyl, dibenzofuran substituted phenyl, dibenzothiophene substituted phenyl;
when the groups contain substituents, 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, halogen substituted methyl.
11. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is a compound having any one of the following structures:
12. the heterocyclic compound according to claim 8, wherein R X3 And R is R 8 Connected by a benzene ring.
13. The heterocyclic compound of claim 1, wherein the heterocyclic compound has the structure:
14. the heterocyclic compound according to claim 1, wherein,selected from the group consisting of substituted or unsubstituted:
wavy lines represent the attachment position of the group;
when the groups contain substituents, 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, halogen substituted methyl.
15. The heterocyclic compound according to claim 1, wherein L is selected from the group consisting of a bond, a substituted or unsubstituted group consisting of: phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl or carbazolyl;
when the groups contain substituents, 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, halogen substituted methyl.
16. A heterocyclic compound, characterized in that the heterocyclic compound is any one of the following compounds:
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wherein D is deuterium.
17. An organic electroluminescent material comprising any one or a combination of at least two of the heterocyclic compounds according to any one of claims 1 to 16.
18. An organic electroluminescent composition comprising any one or a combination of at least two of the heterocyclic compounds according to any one of claims 1 to 16.
19. 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, the organic layer comprising any one or a combination of at least two of the organic electroluminescent compounds according to any one of claims 1 to 16.
20. The organic electroluminescent device of claim 19, wherein the organic layer comprises at least a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
21. The organic electroluminescent device according to claim 20, wherein the material of the light-emitting layer comprises a host material and a guest material, the host material comprising any one or a combination of at least two of the organic electroluminescent compounds according to any one of claims 1 to 16.
22. The organic electroluminescent device of claim 21, wherein the guest material is a phosphorescent dopant that is a complex comprising a transition metal.
23. The organic electroluminescent device of claim 22, wherein the transition metal-containing complex is an Ir-or Pt-containing complex.
24. An optoelectronic product comprising an organic electroluminescent device as claimed in any one of claims 19 to 23.
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