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CN-115160342-B - Compound and application thereof, and organic electroluminescent device comprising compound

CN115160342BCN 115160342 BCN115160342 BCN 115160342BCN-115160342-B

Abstract

The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I, and the compound is a main material of a macroplane polycyclic ring, so that the planar type of a molecular structure is further enlarged on the premise of ensuring that the triplet state energy level of an original macroplane system is unchanged, the transmission performance and stability of the compound are improved, and the compound is applied to an organic electroluminescent device, so that the device has more excellent performance, such as lower voltage, higher efficiency and longer service life.

Inventors

  • LI ZHIYANG
  • GAO WENZHENG
  • LIU SONG

Assignees

  • 北京鼎材科技股份有限公司
  • 北京鼎材科技有限公司

Dates

Publication Date
20260421
Application Date
20210406
Priority Date
20210406

Claims (20)

  1. 1. A compound, characterized in that the compound has a structure according to formula I; In the formula I, X 1 -X 16 is independently selected from CR 1 or N, R 1 is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silane group, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and R 1 is independently connected with a connected aromatic ring or heteroaromatic ring to form a ring or is not connected with the ring; in the formula I, Y is selected from one of CR 2 R 3 、NR 4 , O or S, and is connected with X 11 or X 16 through C, N, O or S in CR 2 R 3 、NR 4 , O or S to form a six-membered ring, when C, N, O or S is connected with X 11 , X 11 is CR 1 , when C, N, O or S is connected with X 16 , X 16 is CR 1 ; The R 2 、R 3 、R 4 is independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R 2 and R 3 are connected into a ring or not; In R 1 、R 2 、R 3 、R 4 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  2. 2. The compound according to claim 1, wherein the compound has a structure represented by formula (I-1) or formula (I-2); The X 1 -X 16 is independently selected from CR 1 or N, the R 1 is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silane group, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and the R 1 is independently connected with or not connected with an aromatic ring or heteroaromatic ring; Y 1 and Y 2 are independently selected from one of CR 2 R 3 、NR 4 , O or S; The R 2 、R 3 、R 4 is independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R 2 and R 3 are connected into a ring or not; In R 1 、R 2 、R 3 、R 4 , the substituted groups are each independently selected from any one or a combination of at least two of cyano, halogen, nitro, hydroxy, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 heteroarylamino, preferably any one or a combination of at least two of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C3-C30 heteroaryl, the substituents being linked to form a ring or not to the attached aromatic or heteroaromatic ring.
  3. 3. The compound according to claim 1, wherein the compound has a structure represented by formula (I-3) or formula (I-4); The X 1 -X 11 and X 16 are independently selected from CR 1 or N, preferably CR 1 , the R 1 is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, the R 1 is independently linked to an attached aromatic or heteroaromatic ring to form a ring or not; Y 1 and Y 2 are independently selected from one of CR 2 R 3 、NR 4 , O or S; The R 2 、R 3 、R 4 is independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R 2 and R 3 are connected into a ring or not; ar 1 is selected from one of hydrogen, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably one of substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; In Ar 1 、R 1 、R 2 、R 3 、R 4 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  4. 4. The compound of claim 1, wherein X 1 -X 11 and X 16 are both CH.
  5. 5. The compound of claim 1, wherein Y is selected from O or S.
  6. 6. The compound of claim 2, wherein Y 1 and Y 2 are independently selected from O or S.
  7. 7. A compound according to claim 3, wherein Ar 1 is selected from any one of structures represented by the following formulae (3-1) to (3-4): In formula (3-1), each of Z 1 、Z 2 、Z 3 、Z 4 and Z 5 is independently selected from CR 7 or an N atom, and at least one of Z 1 、Z 2 、Z 3 、Z 4 and Z 5 is an N atom, In formula (3-2), each of Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 and Z 13 is independently selected from CR 7 or an N atom, and at least one of Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 and Z 13 is an N atom, In the formula (3-3), Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 and Z 23 are each independently selected from CR 7 or an N atom, and at least one of Z 14 、Z 15 、Z 16 、Z 17 、Z 18 、Z 19 、Z 20 、Z 21 、Z 22 and Z 23 is an N atom, In the formula (3-4), Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 and Z 33 are each independently selected from CR 7 or an N atom, and at least one of Z 24 、Z 25 、Z 26 、Z 27 、Z 28 、Z 29 、Z 30 、Z 31 、Z 32 and Z 33 is an N atom, The R 7 is selected from one or a combination of at least two of hydrogen, halogen, cyano, nitro, hydroxyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silane, amino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl and C3-C60 heteroaryl; Wherein, represents the access bond of the group.
  8. 8. The compound of claim 7, wherein Ar 1 has a structure as shown in (3-1) or (3-2).
  9. 9. The compound of claim 8, wherein in formula (3-1), at least two of Z 1 、Z 2 、Z 3 、Z 4 and Z 5 are N atoms.
  10. 10. The compound of claim 8, wherein in formula (3-2), at least two of Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 、Z 12 and Z 13 are N atoms.
  11. 11. A compound according to claim 3 wherein Ar 1 is selected from one of a substituted or unsubstituted pyridyl, quinolinyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl; in Ar 1 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  12. 12. A compound according to claim 3, wherein Ar 1 is selected from one of the substituted or unsubstituted A1 to a26 groups: Wherein, represents an access bond of a group; in Ar 1 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  13. 13. A compound according to claim 3, wherein Ar 1 is selected from one of the groups B1 to B19: Wherein, represents an access bond of a group; in Ar 1 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  14. 14. A compound according to claim 3, wherein Ar 1 is selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted S/O containing C3-C30 heteroaryl, substituted or unsubstituted carbazole, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino; in Ar 1 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  15. 15. The compound of claim 14, wherein Ar 1 is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted diphenylamino; in Ar 1 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  16. 16. The compound of claim 1, wherein X 1 -X 16 is CH.
  17. 17. The compound of claim 1, wherein R 2 、R 3 、R 4 is independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; In R 2 、R 3 、R 4 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  18. 18. The compound of claim 17, wherein R 2 、R 3 、R 4 is selected from one of substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrimidinyl; In R 2 、R 3 、R 4 , each substituent is independently selected from any one or at least two of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silane, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl and C3-C60 heteroarylamino, and the substituent is connected with or not connected with an attached aromatic ring or heteroaromatic ring to form a ring.
  19. 19. The compound of claim 1, wherein the compound has one of the structures shown as P1 to P167:
  20. 20. Use of a compound according to any one of claims 1-19, wherein the compound is applied to an organic electronic device.

Description

Compound and application thereof, and organic electroluminescent device comprising compound Technical Field The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof, and an organic electroluminescent device comprising the compound. Background In recent years, optoelectronic devices based on organic materials have been rapidly developed, and have become a hot spot for research in the field. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like. The OLED device core is a multi-layer thin film structure containing a plurality of organic functional materials. Common functional organic materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, light-emitting host materials, light-emitting guests (dyes), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light. Common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition from triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property, and sensitizes the luminophor in an energy transfer mode, so that higher luminous efficiency can be realized. Although products using OLED display technology are commercialized at present, performance such as lifetime and efficiency of devices is still required to be continuously improved, so as to meet pursuit of higher quality. Therefore, there is a need in the art to develop a larger variety of organic materials for use in organic electroluminescent devices, which results in higher luminous efficiency, lower driving voltage and longer lifetime of the device. Disclosure of Invention The invention provides a compound, in particular to an organic electroluminescent material, and especially provides a luminescent layer main body material for an organic electroluminescent device, which can effectively improve luminous efficiency, reduce driving voltage and prolong service life. To achieve the purpose, the invention adopts the following technical scheme: the invention provides a compound, which has a structure shown in a formula I; In the formula I, the R 1 is independently selected from CR 1 or N, the R 1 is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silane group, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, the R 1 is independently connected with a connected aromatic ring or heteroaromatic ring to form a ring, and when at least two of the X 1-X16 are selected from CR 1, at least two R 1 can be selected from the same group or different groups (namely 'at least two combination'); In the formula I, Y is selected from one of CR 2R3、NR4, O, S or SiR 5R6, and is connected with X 11 or X 16 through C, N, O, S or Si in CR 2R3、NR4, O, S or SiR 5R6 to form a six-membered ring, wherein when C, N, O, S or Si is connected with X 11, X 11 is CR 1, and when C, N, O, S or Si is connected with X 16, X 16 is CR 1; The R 2、R3、R4、R5 and the R 6 are independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R 2 and R 3 are connected into a ring or not, R 5 and R 6 are connected into a ring or not, R 2 and R 3 can be independently substituted on C or can be connected into a ring