Search

CN-122010962-A - Carbazole compound and organic electroluminescent device thereof

CN122010962ACN 122010962 ACN122010962 ACN 122010962ACN-122010962-A

Abstract

The invention provides a carbazole compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. The carbazole compound has good carrier transmission performance and stability when used in a luminescent layer in a device, which effectively improves the luminous efficiency of the device and prolongs the service life of the device. When the compound is used as a covering layer in a device, the compound has good refractive index and good chemical stability, and can effectively improve the luminous efficiency of the device and prolong the service life of the 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

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260512
Application Date
20260129

Claims (10)

  1. 1. A carbazole compound characterized in that the carbazole compound has a structure represented by formula I: Group 1: Wherein, X 1 、X 2 is independently selected from any one of single bond and O, S, C (R x R y ), and one of X 1 、X 2 is selected from single bond; The ring A, the ring B and the ring C are independently selected from any one of substituted or unsubstituted group 1 structures; Said z is selected from C (R t ); The R t 、R x 、R y is selected from any one of hydrogen, deuterium, tritium, 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 heterocyclic alkane and C6-C30 aromatic ring condensed ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring groups, or R x 、R y is connected to form a substituted or unsubstituted ring; ar 1 is selected from the group shown in a formula II; x is selected from any one of CH and N; The X 3 、X 4 is independently selected from any one of O, S, C (R i R j ), and at least one of X 3 、X 4 is selected from any one of O, S; The R a 、R i 、R j is independently selected from any one of hydrogen, deuterium, tritium, 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 C4-C14 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring groups, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups, wherein the substituent in the substituent R a 、R i 、R j is selected from any one of hydrogen, tritium, halogen, cyano, silyl, C1-C30 alicyclic and C6-C30 aromatic ring fused ring, substituted or unsubstituted C1-C25 alicyclic and C2-C30 heteroaromatic ring fused ring groups; The a 0 is selected from 0,1, 2, 3 or 3, the 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 connected with each other to form a substituted or unsubstituted aromatic ring; The L 1 is selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The v and v 'are independently selected from any one of CH and N, and at most one of v' is selected from N; the ring D is selected from substituted or unsubstituted C3-C10 alicyclic rings; The X 5 、X 6 is independently selected from any one of O, S, N (R s ); The X 7 is any one selected from O, S, C (R p R q )、N(R s ); The R b 、R b '、R p 、R q is independently selected from any one of hydrogen, deuterium, tritium, fluoro, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q is connected to form a substituted or unsubstituted ring, wherein the substituent in the R b is selected from any one of hydrogen, deuterium, tritium, fluoro, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl and C2-C10 heteroaryl; R s is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; Said p is selected from 1,2,3 or 4; The b 1 is selected from 0,1, 2, 3 or 4, the b 2 is selected from 0,1, 2, 3, 4, 5 or 6, the b 3 is selected from 0,1, 2, 3, 4, 5,6, 7 or 8, the b 4 is selected from 0,1 or 2, 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 with each other to form a substituted or unsubstituted ring; Wherein b ' 1 is selected from 0,1 or 2, when two or more R b 's are present, two or more R b 's are the same or different from each other; provided that the following compounds are not included: 、 、 。
  2. 2. a carbazole compound according to claim 1, characterized in that it is selected from any one of the following structures: The Ar 1 、L 1 , ring A, ring B, ring C, R x 、R y are as defined in formula I.
  3. 3. A carbazole compound according to claim 1, characterized in that the group of formula II is selected from any one of the following groups: x is selected from any one of CH and N; The R a 、R i 、R j is selected from the group consisting of hydrogen, deuterium, tritium, 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-cyclohexanyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, phenyl, diphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrimidinyl, triazolyl, quinolyl, quinazolinyl, pyrrolyl, quinazolinyl, and the like; wherein the substituents in the "substituted or unsubstituted" in R a 、R i 、R j are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, any one of a naphthocyclopentylalkyl group, a benzocyclohexenyl group, a naphthocyclohexenyl group, a benzocycloheptyl group, a benzocyclobutenyl group, a benzocyclopentenyl group, a benzocyclohexenyl group, a benzocycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, and a fluoranthryl group; The a 0 is selected from 0, 1, 2, 3 or 3, the a 1 is selected from 0, 1, 2, 3 or 4, the a 2 is selected from 0, 1, 2, 3,4, 5 or 6, the a 3 is selected from 0, 1, 2, 3,4 or 5, 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 connected with each other to form a substituted or unsubstituted ring.
  4. 4. A carbazole compound according to claim 1, characterized in that the group of formula II is selected from any one of the following groups: 。
  5. 5. a carbazole compound according to claim 1, characterized in that L 1 is independently selected from a single bond or any one of the following groups or from a combination of two or more of the following groups: The R b 、R b '、R p 、R q is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, a group of formula II, 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-t-butylsilyl, t-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrole, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, any one of benzocyclopentylalkyl, naphthocyclopentylalkyl, benzocyclohexenyl, naphthocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl; The R s is independently selected from the group consisting of hydrogen, deuterium, tritium, 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, tetrahydropyrrole, piperidinyl, benzocyclopropyl, naphthacylalkyl, benzocyclobutanyl, naphthacyloalkyl, benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, pyrimidinyl, pyridazinyl, triazinyl, and any of the like; The b 1 is selected from 0, 1, 2, 3 or 4, the b 2 is selected from 0, 1, 2, 3, 4, 5 or 6, the b 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the b 4 is selected from 0, 1 or 2, the b 5 is selected from 0, 1, 2 or 3, the b 6 is selected from 0 or 1, the b 7 is selected from 0, 1, 2, 3, 4 or 5, the b 8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when two or more R b are present, two or more R b are the same or different from each other or are connected with each other between two adjacent R b to form a substituted or unsubstituted ring; The b ' 1 is selected from 0,1 or 2, the b' 2 is selected from 0,1, 2, 3 or 4, the b ' 3 is selected from 0,1, 2, 3, 4,5 or 6, the b' 4 is selected from 0,1, 2, 3, 4,5, 6, 7 or 8, the b ' 5 is selected from 0,1, 2, 3, 4,5, 6, 7, 8, 9 or 10, the b' 6 is selected from 0,1, 2, 3, 4,5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, and when two or more R b 'are present, two or more R b ' are the same or different from each other.
  6. 6. A carbazole compound according to claim 1, characterized in that L 1 is independently selected from a single bond or any one of the following groups or from a combination of two or more of the following groups: 。
  7. 7. A carbazole compound according to claim 1, characterized in that 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 located 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 carbazole compounds as claimed in 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 carbazole compounds of 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 carbazole compounds as claimed in any one of claims 1 to 7.

Description

Carbazole compound and organic electroluminescent device thereof Technical Field The invention relates to the technical field of organic photoelectric materials, in particular to a carbazole compound and an organic electroluminescent device thereof. Background In the 21 st century, display devices have become an important component of the electronic information industry as a carrier for human-computer interaction, which indicates that display technology has become an important part of information technology. With the development of society and the advancement of technology, demands of consumers for color performance and practical performance of display devices are continuously increased, and in particular, higher demands are being made on high definition, high quality imaging, wide color gamut, full color display, flexible foldability, long life and the like. Conventional cathode ray tube displays (CRTs) and liquid crystal technology (LCDs) relying on backlight modules have failed to meet these demands, and Organic Light Emitting Diode (OLED) display technology based on organic semiconductor materials has been developed. Compared with CRT and LCD, OLED display screen has the advantages of high luminous efficiency, high contrast ratio, low power consumption, wide viewing angle, short response time, light weight, etc. OLEDs have become one of the most competitive candidate devices in future display and lighting technology. OLED devices have undergone a number of significant developments and improvements such as single layer devices, dual layer devices, three layer devices, multi-layer devices, stacked layer devices, top emission devices, and the like. The device basic structure comprises an anode, a cathode and an organic layer. Wherein the organic layer further comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Different functional layers can better play respective roles, can be independently optimized and can be combined with each other, so that higher-efficiency luminous performance is realized. The light emitting direction of the device may be classified into a top emission device and a bottom emission device. The top emission device is characterized in that a covering layer is evaporated outside a metal electrode in a vertical direction, the structure optimizes the electrode design and a light extraction path, enables the theoretical value of luminous efficiency to be 100%, solves various limitations of the bottom emission device, and has irreplaceable advantages in large-size display, flexible display, high-brightness application and other scenes. The luminous principle of the OLED is that under certain voltage, hole carriers start from an anode to overcome potential barriers between layers to reach a luminous layer, and electron carriers start from a cathode to overcome potential barriers between layers to reach the luminous layer. The hole carriers and the electron carriers are combined in the light-emitting layer to form excitons, and the excitons pass through transition, so that the light emission of the OLED device is realized. The light emitting layer is a core part of the device, and in order to improve efficiency, a host-guest doped form is generally used, electrons and holes are injected into the doped light emitting layer by applying an external voltage, the electrons and holes are recombined on a host material to form excitons, and then energy is transferred from the host material to a guest material by way of energy transfer. So that the host material with excellent performance plays an important role in determining the performance of the device. This requires a host material having good thermal stability, as well as good hole transport and charge transport capabilities. The existing main material has the problems that the luminous efficiency and the stability are difficult to be compatible, the carrier transmission performance is relatively poor, and therefore, effective balance transmission of electrons and holes is difficult to realize, and the luminous efficiency, the performance stability and the service life of the material of the device are influenced. The cover layer is used for coupling out light of the top-emission device, so that the light-emitting efficiency of the top-emission OLED device can be effectively improved. The optical fiber is positioned outside the device, does not influence the electrical property of the device, only needs to consider the optical property of the device, and generally needs to have the characteristics of high transparency, high refractive index, good chemical stability, no chemical reaction with an adjacent layer and the like. In order to improve the light-emitting performance of the device, development of a light-emitting layer material and a cover layer material with excellent performance, so that the devi