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CN-122010954-A - Carbazole fused ring compound and organic light-emitting device

CN122010954ACN 122010954 ACN122010954 ACN 122010954ACN-122010954-A

Abstract

The application belongs to the technical field of materials, and particularly relates to a carbazole condensed ring compound and an organic light-emitting device. According to the application, based on an indolocarbazole structure, alicyclic units with branched structures are introduced, a mother nucleus structure with a more stable three-dimensional framework is constructed, and a new electroluminescent material is formed. The organic compound has good stability and fluorescence efficiency, and can effectively reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency of the device and prolong the service life of the device when being used as the luminous layer of the organic electroluminescent device.

Inventors

  • MU GUANGYUAN
  • ZHUANG SHAOQING
  • WANG DONGQI
  • WANG LIN

Assignees

  • 湖北尚赛光电材料有限公司

Dates

Publication Date
20260512
Application Date
20251216

Claims (10)

  1. 1. A carbazole condensed-ring compound is characterized in that the compound has a structural formula shown in a formula I: Any two adjacent bonds in X 1 、X 2 、X 3 、X 4 are formed The rest is CH, L is selected from direct connection bond, phenylene or condensed arylene with 10-15 carbon atoms, A is selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted arylamine with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 6-30 carbon atoms.
  2. 2. The carbazole condensed-ring compound according to claim 1, wherein the compound has a structural formula represented by formulae 1-1 to 1-3: 。
  3. 3. The carbazole condensed ring compound according to claim 1, wherein the condensed arylene group having 10 to 15 carbon atoms is an arylene group having 2 to 3 phenyl groups; Aryl with the carbon number of 6-30 is aromatic hydrocarbon radical containing 2-4 phenyl groups, and each phenyl group is connected by single bond connection, condensed connection or the combination of the two; An arylamine group having 6 to 30 carbon atoms is-NR 1 R 2 ,R 1 、R 2 an aromatic hydrocarbon group or a heteroaromatic hydrocarbon group containing 2 to 4 phenyl groups, and the connection mode between the phenyl groups is selected from any one or a combination of a plurality of single bond connection, condensed connection or heteroatom connection; heteroaryl having 6 to 30 carbon atoms is a heteroaryl hydrocarbon group having 1 to 2 heteroatoms and 2 to 4 phenyl groups; The substituent in the substituted aryl group with 6-30 carbon atoms, the substituted arylamine group with 6-30 carbon atoms and the substituted heteroaryl group with 6-30 carbon atoms is alkyl, cyano and phenyl with 1-4 carbon atoms; The heteroatom is O, S, N.
  4. 4. The carbazole condensed-cyclic compound according to claim 1, wherein a is selected from the group consisting of 、 、 、 ; In the formula A-1, R 3 -R 7 is independently H, cyano, hydroxyl, mercapto or C 1-4 alkyl, or is C 6-12 aryl substituted by cyano, C 1-4 alkyl, phenyl or unsubstituted, and any two adjacent groups in R 3-7 are not related or bonded to form a condensed aromatic ring or a heteroaromatic ring; In the formula A-2, n is selected from 0, 1 or 2, each R 8 is independently cyano, alkyl of C 1-4 , or aryl of C 6-12 substituted or unsubstituted by cyano, alkyl of C 1-4 , phenyl, or heteroaryl of C 6-18 substituted or unsubstituted by cyano, alkyl of C 1-4 , phenyl, R 9 is alkyl of H, C 1-4 , aryl of C 6-12 , or R 9 is a connection site with L; R 10 -R 13 is independently represented by the structure shown as A-1 or A-2; Z 1 -Z 3 is independently represented as N or CH, and at least one is N.
  5. 5. The carbazole condensed-cyclic compound according to claim 4, wherein: The aryl of C 6-12 is selected from phenyl, biphenyl, naphthyl; the heteroaryl group of C 6-12 is selected from carbazolyl, dibenzofuranyl, dibenzothiophenyl.
  6. 6. The carbazole condensed-cyclic compound according to claim 4, wherein, Substituted or unsubstituted alkyl having cyano, C 1-4 , phenyl having the formula: 、 、 ; Substituted or unsubstituted alkyl having cyano, C 1-4 , phenyl having the formula: 、 、 、 ; The Z 4 is selected from C (CH 3 ) 2 、O、S;Z 5 is selected from C (CH 3 ) 2 , O, S, N-Ph).
  7. 7. The carbazole condensed-ring compound according to claim 1, wherein the condensed arylene group having 10 to 15 carbon atoms is selected from any one of the following structural formulas: 、 。
  8. 8. the carbazole condensed-ring compound according to claim 7, wherein the compound is any one of the following formulas 1 to 170: 。
  9. 9. An organic light-emitting device comprising a cathode, an anode, and an organic material layer disposed between the cathode and the anode, wherein the organic material layer comprises the carbazole condensed ring compound according to any one of claims 1 to 8.
  10. 10. The organic light-emitting device according to claim 9, wherein the organic layer includes any one, two or more of a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light-emitting layer, and a light-emitting auxiliary layer, and the organic layer including the organic condensed ring compound is a light-emitting layer.

Description

Carbazole fused ring compound and organic light-emitting device Technical Field The invention belongs to the technical field of materials, and particularly relates to a carbazole condensed ring compound and an organic light-emitting device. Background Compared with the traditional display technology, such as a liquid crystal display LCD, the OLED device has self-luminous property, does not need to depend on a backlight source, can realize extremely thin and light device design, can reduce the thickness to a level of several micrometers, has the outstanding advantages of high response speed, high contrast, flexibility, low power consumption and the like, and is widely applied to the fields of smart phones, smart wearable devices, televisions, vehicle-mounted displays and the like. With the continuous expansion of OLED application scenes, the market puts forward more severe standards and requirements on device performance. The performance of the light-emitting layer, which is a core functional layer of an OLED device, directly determines the brightness, efficiency, lifetime, and color purity of the device, and the light-emitting layer is typically composed of a host material and a doped light-emitting material (guest material). The main function of the host material is to dissolve and disperse the guest material, avoid luminescence quenching caused by aggregation of the guest material, realize effective transmission, capture and recombination of holes and electrons, and provide energy for the guest material to excite the guest material to emit light. However, the OLED host luminescent materials in the prior art still have many defects, which are difficult to meet the requirements of high performance devices, namely, firstly, the charge transmission balance is poor, most host materials tend to transmit holes or electrons, so that the recombination region of charges in the luminescent layer deviates from an interlayer interface, exciton quenching is easy to be caused, the luminescent efficiency of the device is reduced, secondly, the thermal stability and the morphological stability are insufficient, the glass transition temperature (Tg) of part of the host materials is lower (usually lower than 120 ℃), crystallization or phase separation is easy to occur in the preparation process (such as evaporation and encapsulation) and long-term use of the device, the structural integrity of the luminescent layer is damaged, the brightness attenuation of the device is accelerated, the service life is shortened, thirdly, the energy gap matching degree is low, the Highest Occupied Molecular Orbital (HOMO) energy level and the Lowest Unoccupied Molecular Orbital (LUMO) energy level of the existing host materials cannot realize effective energy transfer, the energy reverse transfer or exciton leakage easily occurs, and the color purity of the device is reduced, and the efficiency is reduced. Aiming at the problems of unbalanced charge transmission, poor thermal stability, low energy matching degree and the like of the OLED main body luminescent material in the prior art, a new material for an organic luminescent device is required to be continuously developed. Disclosure of Invention In order to solve the defects in the prior art, the invention provides a carbazole condensed ring compound and an organic light-emitting device. The technical scheme provided by the invention is as follows: A carbazole fused ring compound having a structural formula represented by formula one: Any two adjacent bonds in X 1、X2、X3、X4 are formed The rest is CH, L is selected from direct bond, phenylene or condensed arylene with 10-15 carbon atoms, A is selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted arylamine with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 6-30 carbon atoms. The "substitution" means that a hydrogen atom on a compound group is replaced by other atoms or groups, and the substitution position is any position, and the "unsubstituted" means that the hydrogen atom on the compound group is not replaced by other atoms or groups. The formula one further has the structural formula shown in the formulas 1-1 to 1-3: 。 specifically, the condensed arylene group having 10 to 15 carbon atoms is an arylene group having 2 to 3 phenyl groups. Specifically, the aryl group with the carbon number of 6-30 is an aromatic hydrocarbon group containing 2-4 phenyl groups, and the phenyl groups are connected by single bond connection, condensed connection or a combination of the two. Specifically, the arylamine group with 6-30 carbon atoms is-NR 1R2,R1、R2 or an aryl or heteroaryl group with 2-4 phenyl groups, and the connection mode between the phenyl groups is selected from any one or a combination of a plurality of single bond connection, condensed connection or heteroatom connection. Specifically, the heteroaryl group having 6 to 30 carbon atoms is a heteroaryl hydrocarbon group h