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CN-121974902-A - Heterocyclic compound and organic electroluminescent device thereof

CN121974902ACN 121974902 ACN121974902 ACN 121974902ACN-121974902-A

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. When the compound is used as a main material of a luminescent layer in an organic luminescent device, the mobility of electrons and holes can be improved, the recombination efficiency of the electrons and the holes can be improved, and the energy loss can be limited, so that the photoelectric performance of the organic luminescent device can be improved. The compound has good thermal stability and refractive index when being used as a coating material, can reduce light loss reflected by nearby electrodes when emitting light, effectively improves the stability of a film layer and improves the performance of a device. The compound disclosed by the invention is simple in preparation method, easy in raw material acquisition, capable of being widely applied to the fields of organic thin film transistors, panel display and the like, and good in application effect and industrialization prospect.

Inventors

  • GUO JIANHUA
  • DONG XIUQIN
  • SUN YUE

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260505
Application Date
20260122

Claims (10)

  1. 1. A heterocyclic compound, wherein the heterocyclic compound has a structure represented by formula I: Wherein Ar 1 、Ar 2 、Ar 3 is independently selected from any one of formula a, formula b, hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring, ar 1 、Ar 2 、Ar 3 is selected from at least one of formula a and formula b; The i is independently selected from any one of CH and N, and when the i is bonded with other groups, the i is selected from C atoms; V is independently selected from any one of CH and N, and when v is bonded with other groups, v is selected from a C atom; the X is any one selected from O, S, C (R p R q )、N(R s ); y is selected from any one of O, S; The E is any one selected from O, S, N (R v ); Group 1: the rings A and B are independently selected from any one of substituted or unsubstituted group 1 structures, and at least one of the rings A and B is not selected from ; The z is selected from any one of C (R t ) and N; The R a 、R b 、R p 、R q 、R t is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups; The R s 、R v is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups; Wherein a 1 is selected from 0,1, 2, 3 or 4, when two or more R a are present, two or more R a are the same or different from each other, or two adjacent R a are linked to each other to form a substituted or unsubstituted ring; wherein b 1 is selected from 0, 1, 2, 3,4 or 5, when two or more R b are present, two or more R b are the same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; The L 1 、L 2 、L 3 、L 4 、L 5 is independently selected from any one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C6-C30, substituted or unsubstituted alicyclic of C3-C30 and fused ring group of aromatic ring of C6-C30, substituted or unsubstituted alicyclic of C3-C25 and fused ring group of heteroaromatic ring of C2-C30.
  2. 2. A heterocyclic compound according to claim 1, wherein the heterocyclic compound is selected from any one of the following structures: The Ar 3 , ring A, ring B、Y、L 1 、L 2 、L 3 、L 4 、L 5 、X、i、R a 、R b 、a 1 、b 1 、E are as defined in formula I.
  3. 3. A heterocyclic compound according to claim 1, wherein said Selected from any one of the following groups: The Y 1 is any one selected from O, S, C (R x R y )、N(R z ); R a 、R x 、R y is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R x 、R y ; The R z is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups; The a 1 is selected from 0, 1,2,3 or 4, the a 2 is selected from 0, 1,2 or 3, the a 3 is selected from 0, 1 or 2, the a 4 is selected from 0, 1,2,3,4,5 or 6, the a 5 is selected from 0, 1,2,3,4,5,6, 7 or 8, and when two or more R a are present, the two or more R a are the same or different from each other.
  4. 4. A heterocyclic compound according to claim 1, wherein said formula a is selected from any one of the following groups: x is independently selected from any one of CH and N; Y is independently selected from any one of O, S; The R d is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups such as: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclobutenyl, benzo benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, fluoranthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzofuranyl, benzothienyl, dibenzothiophenyl, and benzodibenzothienyl, indolyl, carbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, benzoimidazolyl, benzoquinolinyl, and benzoquinolinyl, any one of phenanthroline group, naphthyridinyl group, indolyl group, acridinyl group, phenoxazinyl group and phenothiazinyl group; The d 1 is selected from 0,1, 2,3, 4,5 or 6, the d 2 is selected from 0,1, 2 or 3, the d 3 is selected from 0,1, 2,3, 4,5, 6, 7 or 8, the d 4 is selected from 0,1, 2,3 or 4, the d 5 is selected from 0,1, 2,3, 4 or 5, the d 6 is selected from 0,1, 2,3, 4,5, 6 or 7, and when two or more R d are present, the two or more R d are the same or different from each other.
  5. 5. A heterocyclic compound according to claim 1, wherein said formula b is selected from any one of the following groups: The R b is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups such as: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclobutenyl, benzo benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, fluoranthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzofuranyl, benzothienyl, dibenzothiophenyl, and benzodibenzothienyl, indolyl, carbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, benzoimidazolyl, benzoquinolinyl, and benzoquinolinyl, any one of phenanthroline group, naphthyridinyl group, indolyl group, acridinyl group, phenoxazinyl group and phenothiazinyl group; The R v is independently selected from any of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthacylalkyl, benzocyclobutanyl, naphthacene-cyclobutyl, benzocyclopentenyl, naphthacene-cyclohexenyl, naphthacene-cyclohexen, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, terphenyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, phenyl, pyrenyl, pyrimidinyl, triazinyl, and fluoroyl; The b 1 is selected from 0, 1,2, 3,4 or 5, the b 2 is selected from 0, 1,2, 3,4, 5, 6 or 7, the b 3 is selected from 0, 1 or 2, the b 4 is selected from 0, 1,2, 3,4, 5, 6, 7 or 8, the b 5 is selected from 0 or 1, the b 6 is selected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9, and when two or more R b are present, the two or more R b are the same or different from each other.
  6. 6. The heterocyclic compound according to claim 1, wherein when Ar 1 、Ar 2 、Ar 3 is not selected from formula a or formula b, ar 1 、Ar 2 、Ar 3 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, or any of the following groups: the u is independently selected from any one of CH and N atoms, and when the u is bonded with other groups, the u is selected from C atoms; The ring D is selected from substituted or unsubstituted C3-C10 alicyclic rings; The X 4 is any one selected from O, S, N (R w ); the X 5 is selected from any one of C (R u R r )、N(R w ); The X 6 、X 7 is independently selected from any one of O, S, C (R u R r )、N(R w ); The R e 、R e ' is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups; R u 、R r is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R u 、R r is connected to form a substituted or unsubstituted ring; R w is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; the e 1 is selected from 0, 1,2, 3,4 or 5, the e 2 is selected from 0, 1,2, 3 or 4, the e 3 is selected from 0, 1,2, 3,4, 5, 6 or 7, the e 4 is selected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9, the e 5 is selected from 0, 1 or 2, the e 6 is selected from 0, 1,2, 3,4, 5, 6, 7, 8, 9, 10 or 11, the e 7 is selected from 0, 1,2 or 3, the e 8 is selected from 0, 1,2, 3,4, 5 or 6, when two or more R e are present, two or more R e are the same or different from each other, or two adjacent R e are connected with each other to form a substituted or unsubstituted ring; The e ' 1 is selected from 0, 1 or 2, and when two or more R e 's are present, the two or more R e 's are the same or different from each other.
  7. 7. A heterocyclic compound according to claim 1, wherein the compound of formula I is selected from any one of the following structures: 。
  8. 8. an organic electroluminescent device comprising an anode, a cathode and an organic layer between the anode and the cathode or on a side of the cathode facing away from the anode, characterized in that the organic layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 7.
  9. 9. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer comprising at least one of the heterocyclic compounds according to any one of claims 1 to 7.
  10. 10. An organic electroluminescent device as claimed in claim 8, wherein the organic layer is located on the side of the cathode facing away from the anode, wherein the organic layer comprises a capping layer comprising at least one of the heterocyclic compounds according to any one of claims 1 to 7.

Description

Heterocyclic compound and organic electroluminescent device thereof Technical Field The invention relates to the technical field of organic photoelectric materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof. Background Compared with the traditional LED, the Organic LIGHT EMITTING Diode (OLED) is a light-emitting device which directly converts electric energy into light energy based on an Organic photoelectric material, can directly emit light by using the Organic material, has higher luminous efficiency, faster response speed, large flexibility and simple preparation process, is expected to replace the traditional liquid crystal display and fluorescent lamp illumination, fully utilizes the Organic light-emitting device in the electronic display field and illumination products, and has wider application and development prospects. The organic electroluminescent device is mainly composed of three parts, namely an anode electrode material film layer, a cathode electrode material film layer and different organic material functional layers. The light-emitting principle is that electrons and holes are respectively injected into a light-emitting layer from a cathode and an anode by applying voltage to two electrodes, and the electrons and the holes are combined to generate excitons, so that the excitons are subjected to radiation transition to realize light emission. The electrode material film layer and the different functional layers of the organic electroluminescent device are composed of various organic semiconductor materials. The excellent organic electroluminescent device needs to have the characteristics of low driving voltage, high luminous efficiency, long service life and the like of the functional material. Wherein the main material of the light-emitting layer of the OLED device needs to have good bipolar property, proper HOMO/LUMO energy level and the like, and the material of the covering layer needs to have proper refractive index and thickness and the like. However, due to the physical and chemical properties of the organic semiconductor material, the OLED device has the problems of low luminous efficiency, reduced resolution, improved driving voltage and the like, and the optimization and development of the organic light-emitting device are hindered. Therefore, aiming at the problems of the main material and the cover layer material of the light-emitting layer in the current organic light-emitting device, the design and development of the organic functional material with high performance are urgently needed for breaking through the break-over, improving the light-emitting efficiency, resolution frequency and other photoelectric properties of the device, and promoting the more advanced application and development of the OLED device. Disclosure of Invention In order to solve the problems, the invention aims to provide a heterocyclic compound and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the device. The invention provides a heterocyclic compound, which has a structure represented by a formula I: Wherein Ar 1、Ar2、Ar3 is independently selected from any one of formula a, formula b, hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring, ar 1、Ar2、Ar3 is selected from at least one of formula a and formula b; The i is independently selected from any one of CH and N, and when the i is bonded with other groups, the i is selected from C atoms; V is independently selected from any one of CH and N, and when v is bonded with other groups, v is selected from a C atom; the X is any one selected from O, S, C (R pRq)、N(Rs); y is selected from any one of O, S; The E is any one selected from O, S, N (R v); Group 1: the rings A and B are independently selected from any one of substituted or unsubstituted group 1 structures, and at least one of the rings A and B is not selected from ; The z is selected from any one of C (R t) and N; The R a、Rb、Rp、Rq、Rt is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicycli