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CN-122010983-A - Compound, material for organic electroluminescent element, and electronic device

CN122010983ACN 122010983 ACN122010983 ACN 122010983ACN-122010983-A

Abstract

The present invention provides a compound represented by the following general formula (1), D is a group represented by the following general formula (11), general formula (12) or general formula (13), wherein at least 1D is a group represented by the following general formula (12) or general formula (13), wherein at least 1R is a substituent, and the sum of the number of R as a substituent and the number of groups represented by the following general formula (12) or general formula (13) is 3 or 4.

Inventors

  • Banno Shota
  • YASUKAWA KEIICHI
  • SHIOMI TAKUSHI
  • Titian Yihui

Assignees

  • 出光兴产株式会社

Dates

Publication Date
20260512
Application Date
20200930
Priority Date
20191001

Claims (20)

  1. 1. A compound, characterized in that, Represented by the following general formula (1), [ Chemical 1] In the general formula (1) described above, D is a group represented by the following general formula (11), general formula (12) or general formula (13), Wherein at least 1D is a group represented by the following general formula (12) or general formula (13), M is 1,2 or 3, M is 2 or 3, a plurality of D are the same or different from each other, R is each independently a hydrogen atom, a halogen atom or a substituent, R as substituents are each independently, Substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, Substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, Substituted or unsubstituted cycloalkyl having 3 to 6 ring-forming carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, Substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, Substituted or unsubstituted alkylamino having 2 to 12 carbon atoms, Substituted or unsubstituted alkylthio having 1 to 6 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, Wherein at least 1R is a substituent, At least 1R as a substituent is bonded to the benzene ring in the general formula (1) through a carbon-carbon bond, N is 1, 2 or 3, N is 2 or 3, R are the same or different from each other, The sum of the number of R as a substituent and the number of groups represented by the following general formula (12) or general formula (13) is 3 or 4, [ Chemical 2] [ Chemical 3] [ Chemical 4] R 1 ～R 8 in the general formula (11) is independently a hydrogen atom, a halogen atom or a substituent, R 11 ～R 18 in the general formula (12) is independently a hydrogen atom, a halogen atom or a substituent, or any 1 or more of the group consisting of R 11 and R 12 , the group consisting of R 12 and R 13 , the group consisting of R 13 and R 14 , the group consisting of R 15 and R 16 , the group consisting of R 16 and R 17 , and the group consisting of R 17 and R 18 are bonded to each other to form a ring, R 111 ～R 118 in the general formula (13) is independently a hydrogen atom, a halogen atom or a substituent, or any 1 or more of the group consisting of R 111 and R 112 , the group consisting of R 112 and R 113 , the group consisting of R 113 and R 114 , the group consisting of R 115 and R 116 , the group consisting of R 116 and R 117 , and the group consisting of R 117 and R 118 are bonded to each other to form a ring, R 1 ～R 8 as a substituent, R 11 ～R 18 as a substituent and R 111 ～R 118 as a substituent are each independently, Substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring members, Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, Substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, Substituted or unsubstituted alkylamino having 2 to 30 carbon atoms, Substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, Substituted or unsubstituted alkylthio having 1 to 30 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, In the general formula (12) and the general formula (13), A. b and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulae (14), (15) and (16), The ring structure A, the ring structure B and the ring structure C are condensed with the adjacent ring structure at any position, P, px, and py are each independently 1, 2, 3, or 4, In the case where p is 2, 3 or 4, the plurality of ring structures A are the same or different from each other, In the case where px is 2, 3 or 4, the plurality of ring structures B are the same or different from each other, Where py is 2, 3 or 4, the plurality of ring structures C are the same or different from each other, Wherein at least 1D is p is 2, 3 or 4 and contains, as a group represented by the general formula (12) of the ring structure A, any one ring structure selected from the group represented by the general formula (15) and the general formula (16) below, or at least one of px and py is 2, 3 or 4 and contains, as a group represented by the general formula (13) of the ring structure B or the ring structure C, any one ring structure selected from the group represented by the general formula (15) and the general formula (16) below, The x in the general formulae (11) - (13) represents a position bonded to the benzene ring in the general formula (1), [ Chemical 5] In the general formula (14) described above, R 19 and R 20 are each independently a hydrogen atom, a halogen atom or a substituent, or R 19 and R 20 are bonded to each other to form a ring, In the general formula (15) and the general formula (16), X 1 and X 2 are each independently NR 120 , a sulfur atom or an oxygen atom, R 120 is a hydrogen atom, a halogen atom or a substituent, R 19 、R 20 as substituents and R 120 are each independently synonymous with R 1 ～R 8 as substituents.
  2. 2. A compound according to claim 1 wherein, The sum of the number of R as a substituent and the number of groups represented by the general formula (12) or the general formula (13) is 4.
  3. 3. A compound according to claim 1 or 2, The compound represented by the general formula (1) is represented by the following general formula (110), general formula (120) or general formula (130), [ Chemical 6] In the general formulae (110), (120) and (130), D, m, R and n are synonymous with D, m, R and n in the general formula (1), respectively.
  4. 4. A compound according to any one of claim 1 to 3, The compound represented by the general formula (1) is any one compound selected from the group consisting of compounds represented by the following general formulae (111) to (118), [ Chemical 7] In the general formulae (111) and (112), D 11 is a group represented by the general formula (12) or the general formula (13), R 121 ～R 123 is synonymous with R in the general formula (1) independently, wherein at least 1 of R 121 ～R 123 is a substituent, R 121 ～R 123 as a substituent is synonymous with R as a substituent in the general formula (1), [ Chemical 8] In the general formulas (113) - (116), D 11 and D 12 are each independently synonymous with D in the general formula (1), wherein at least 1 of D 11 and D 12 is a group represented by the general formula (12) or the general formula (13), R 121 and R 122 are each independently synonymous with R in the general formula (1), wherein at least 1 of R 121 and R 122 is a substituent, R 121 and R 122 as substituents are synonymous with R as substituents in the general formula (1), [ Chemical 9] In the general formulae (117) and (118), D 11 ～D 13 is synonymous with D in the general formula (1) independently of each other, wherein at least 1 of D 11 ～D 13 is a group represented by the general formula (12) or the general formula (13), R 121 is a substituent, and R 121 as a substituent is synonymous with R as a substituent in the general formula (1).
  5. 5. A compound according to any one of claim 1 to 3, The compound represented by the general formula (1) is any one compound selected from the group consisting of compounds represented by the following general formulae (121) to (129), [ Chemical 10] In the general formulas (121) to (123), D 11 is a group represented by the general formula (12) or the general formula (13), R 121 ～R 123 is synonymous with R in the general formula (1) independently, wherein at least 1 of R 121 ～R 123 is a substituent, R 121 ～R 123 as a substituent is synonymous with R as a substituent in the general formula (1), [ Chemical 11] In the general formulas (124) to (126), D 11 and D 12 are each independently synonymous with D in the general formula (1), wherein at least 1 of D 11 and D 12 is a group represented by the general formula (12) or the general formula (13), R 121 and R 122 are each independently synonymous with R in the general formula (1), wherein at least 1 of R 121 and R 122 is a substituent, R 121 and R 122 as substituents are synonymous with R as substituents in the general formula (1), [ Chemical 12] In the general formulas (127) to (129), D 11 ～D 13 is synonymous with D in the general formula (1) independently of each other, wherein at least 1 of D 11 ～D 13 is a group represented by the general formula (12) or the general formula (13), R 121 is a substituent, and R 121 as a substituent is synonymous with R as a substituent in the general formula (1).
  6. 6. A compound according to any one of claim 1 to 3, The compound represented by the general formula (1) is any one compound selected from the group consisting of compounds represented by the following general formulae (131) to (135), [ Chemical 13] In the general formula (131) described above, D 11 is a group represented by the general formula (12) or the general formula (13), R 121 ～R 123 is synonymous with R in the general formula (1) independently, wherein at least 1 of R 121 ～R 123 is a substituent, R 121 ～R 123 as a substituent is synonymous with R as a substituent in the general formula (1), [ Chemical 14] In the general formulas (132) to (134), D 11 and D 12 are each independently synonymous with D in the general formula (1), wherein at least 1 of D 11 and D 12 is a group represented by the general formula (12) or the general formula (13), R 121 and R 122 are each independently synonymous with R in the general formula (1), wherein at least 1 of R 121 and R 122 is a substituent, R 121 and R 122 as substituents are synonymous with R as substituents in the general formula (1), [ 15] In the general formula (135) described above, D 11 ～D 13 is synonymous with D in the general formula (1) independently of each other, wherein at least 1 of D 11 ～D 13 is a group represented by the general formula (12) or the general formula (13), R 121 is a substituent, and R 121 as a substituent is synonymous with R as a substituent in the general formula (1).
  7. 7. A compound according to any one of claim 1 to 6, The group of R 11 and R 12 , the group of R 12 and R 13 , the group of R 13 and R 14 , the group of R 15 and R 16 , the group of R 16 and R 17 , and also the group of R 17 and R 18 in the general formula (12) are not bonded to each other, The group of R 111 and R 112 , the group of R 112 and R 113 , the group of R 113 and R 114 , the group of R 115 and R 116 , the group of R 116 and R 117 , and the group of R 117 and R 118 in the general formula (13) are not bonded to each other.
  8. 8. A compound according to any one of claim 1 to 7, Has at least 1 group represented by the general formula (12).
  9. 9. A compound according to any one of claim 1 to 8, The group represented by the general formula (12) is any one selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E) and (12F), [ 16] [ Chemical 17] [ Chemical 18] [ Chemical 19] [ Chemical 20] [ Chemical 21] In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), R 11 ～R 18 is each independently synonymous with R 11 ～R 18 in the general formula (12), R 19 and R 20 are each independently synonymous with R 19 and R 20 in the general formula (14), X 1 is synonymous with X 1 in the general formula (15), The x in the general formulae (12A), (12B), (12C), (12D), (12E), and (12F) represent a position bonded to the benzene ring in the general formula (1).
  10. 10. A compound according to claim 9 wherein, The group represented by the general formula (12) is any one selected from the group consisting of the groups represented by the general formulae (12A), (12D) and (12F).
  11. 11. A compound according to any one of claim 1 to 10, X 1 is an oxygen atom or a sulfur atom.
  12. 12. A compound according to any one of claim 1 to 11, R 1 ～R 8 as a substituent, R 11 ～R 18 as a substituent and R 111 ～R 118 as a substituent are each independently, Substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or Substituted or unsubstituted cycloalkyl having 3 to 30 ring-forming carbon atoms.
  13. 13. A compound according to any one of claim 1 to 12, R 1 ～R 8 as a substituent, R 11 ～R 18 as a substituent and R 111 ～R 118 as a substituent are each independently, Substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, Substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or Substituted or unsubstituted cycloalkyl having 3 to 6 ring-forming carbon atoms.
  14. 14. A compound according to any one of claim 1 to 11, R 1 ～R 8 as a substituent, R 11 ～R 18 as a substituent and R 111 ～R 118 as a substituent are each independently, Unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, Unsubstituted alkyl group having 1 to 30 carbon atoms, Unsubstituted cycloalkyl having 3 to 30 ring-forming carbon atoms, Unsubstituted alkylsilyl group having 3 to 30 carbon atoms, Unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, Unsubstituted alkoxy group having 1 to 30 carbon atoms, Unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, Unsubstituted alkylamino having 2 to 30 carbon atoms, Unsubstituted arylamino groups having 6 to 60 ring-forming carbon atoms, Unsubstituted alkylthio having 1 to 30 carbon atoms, or Unsubstituted arylthio groups having 6 to 30 ring-forming carbon atoms.
  15. 15. A compound according to any one of claim 1 to 11, R 1 ～R 8 as a substituent, R 11 ～R 18 as a substituent and R 111 ～R 118 as a substituent are each independently, Unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Unsubstituted alkyl group having 1 to 30 carbon atoms, or Unsubstituted cycloalkyl having 3 to 30 ring-forming carbon atoms.
  16. 16. A compound according to any one of claim 1 to 15, R is each independently a hydrogen atom, a halogen atom or a substituent, R as substituents are each independently, Substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, Substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or Substituted or unsubstituted cycloalkyl having 3 to 6 ring-forming carbon atoms.
  17. 17. A compound according to any one of claim 1 to 15, R is each independently a hydrogen atom, a halogen atom or a substituent, R as substituents are each independently, Unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, Unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, Unsubstituted alkyl group having 1 to 6 carbon atoms, Unsubstituted cycloalkyl having 3 to 6 ring-forming carbon atoms, Unsubstituted alkylsilyl group having 3 to 6 carbon atoms, Unsubstituted arylsilyl group having 3 to 6 carbon atoms, Unsubstituted alkoxy group having 1 to 6 carbon atoms, Unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, Unsubstituted alkylamino having 2 to 12 carbon atoms, Unsubstituted alkylthio having 1 to 6 carbon atoms, or Unsubstituted arylthio groups having 6 to 14 ring-forming carbon atoms.
  18. 18. A compound according to any one of claim 1 to 15, R is each independently a hydrogen atom, a halogen atom or a substituent, R as substituents are each independently, Unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, Unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, Unsubstituted alkyl group having 1 to 6 carbon atoms, or Unsubstituted cycloalkyl having 3 to 6 ring-forming carbon atoms.
  19. 19. A material for an organic electroluminescent element, characterized in that, A compound according to any one of claims 1 to 18.
  20. 20. An organic electroluminescent element, characterized in that, Has an anode, a cathode and an organic layer, The organic layer contains the compound according to any one of claims 1 to 18 as a first compound.

Description

Compound, material for organic electroluminescent element, and electronic device The present invention is a divisional application filed in China, which is based on International application No. PCT/JP2020/037282, subject matter "Compound, material for organic electroluminescent element, organic electroluminescent element and electronic device" of Ministry of China, wherein the application No. 202080068066.8 of China is the application No. 2020, and the application date is 09/30 of the year 2020. Technical Field The present invention relates to a compound, a material for an organic electroluminescent element, and an electronic device. Background When a voltage is applied to an organic electroluminescent element (hereinafter, sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light emitting layer, the injected holes recombine with electrons to form excitons. At this time, according to the statistical theorem of electron spin, singlet excitons are generated at a proportion of 25%, and triplet excitons are generated at a proportion of 75%. A fluorescent organic EL element using light emission from singlet excitons is being applied to full-color displays such as mobile phones and televisions, but the internal quantum efficiency of 25% is called a limit. Accordingly, studies for improving the performance of the organic EL element are being conducted. For example, it is expected that the organic EL element emits light more efficiently by utilizing triplet excitons in addition to singlet excitons. Under such a background, a highly efficient fluorescent organic EL element using thermally activated delayed fluorescence (hereinafter, sometimes simply referred to as "delayed fluorescence") has been proposed and studied. The TADF (THERMALLY ACTIVATED DELAYED Fluorescence) mechanism (mechanism) is a mechanism that uses a material having a small energy difference (Δst) between a singlet energy level and a triplet energy level, and uses a phenomenon in which a reverse-system transition from a triplet exciton to a singlet exciton occurs under the action of heat. The thermally activated delayed fluorescence is described in, for example, "Anda Kibo, physical Properties of organic semiconductor device", published by Anda, 2012, 4/1/261 to 268 pages). As a compound showing heat-activated delayed fluorescence (TADF characteristic) (hereinafter, also referred to as TADF-type compound), for example, a compound having a donor site and an acceptor site bonded in a molecule is known. As the documents related to the organic EL element and the compound for the organic EL element, patent document 1, patent document 2, patent document 3, patent document 4, and patent document 5 can be exemplified. Prior art literature Patent literature Patent document 1 International publication No. 2019/107932 Patent document 2 International publication No. 2019/107933 Patent document 3 International publication No. 2019/107934 Patent document 4 International publication No. 2014/208698 Patent document 5 International publication No. 2018/237389 Disclosure of Invention Technical problem to be solved by the invention In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is desired. The performance of the organic EL element may be, for example, luminous efficiency. Examples of the element for improving the light-emitting efficiency include a compound having a high photo-luminescence quantum yield (PLQY: photoluminescence quantum yield). Further, the performance of the organic EL element may be low in driving voltage. The present invention aims to provide a compound having a high PLQY. The present invention also provides a material for an organic electroluminescent element, which contains a compound having a high PLQY, an organic electroluminescent element, and an electronic device equipped with the organic electroluminescent element. The present invention also provides a high-performance organic EL element and an electronic device having the organic EL element mounted thereon. Solution to the above technical problems According to an embodiment of the present invention, there is provided a compound represented by the following general formula (1). [ Chemical 1] (In the general formula (1), D is a group represented by the following general formula (11), general formula (12) or general formula (13), Wherein at least 1D is a group represented by the following general formula (12) or general formula (13), M is 1,2 or 3, M is 2 or 3, a plurality of D are the same or different from each other, R is each independently a hydrogen atom, a halogen atom or a substituent, R as substituents are each independently, Substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, A substituted or unsubstituted heteroaryl