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CN-122003425-A - Compound, light-emitting element material, organic electroluminescent element, and electronic device

CN122003425ACN 122003425 ACN122003425 ACN 122003425ACN-122003425-A

Abstract

A compound having a structure represented by the general formula (1). In the general formula (1), R 101 ～R 121 is each independently a hydrogen atom or a substituent, wherein R 101 ～R 121 is not a substituted or unsubstituted N-carbazolyl group. The structure represented by the general formula (1) has at least 1 group represented by the general formula (2). In the general formula (2), at least one of X 1 ～X 5 is represented by a nitrogen atom.

Inventors

  • YASUKAWA KEIICHI
  • Fukaito takuto
  • MATSUMOTO NAOTO
  • Noda Oki
  • NAGAO KAZUMASA

Assignees

  • 东丽株式会社

Dates

Publication Date
20260508
Application Date
20241018
Priority Date
20231026

Claims (19)

  1. 1. A compound having a structure represented by the general formula (1), [ Chemical 1] In the general formula (1), R 101 ～R 121 is independently selected from From hydrogen atoms, Halogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkenyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms, A group represented by-O- (R 190 ), A group represented by-S- (R 191 ), Substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, A group represented by-C (=O) -O- (R 192 ), A group represented by-C (=O) -N (R 193 ）（R 194 ), A group represented by-N (R 195 ）（R 196 ), Nitro group Selected from the group consisting of groups represented by-Si (R 197 ）（R 198 ）（R 199 ), In the compound having the structure represented by the general formula (1), R 190 ～R 199 are each independently, A hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted, Wherein R 101 ～R 121 is not substituted or unsubstituted N-carbazolyl, The structure represented by the general formula (1) has at least 1 group represented by the following general formula (2), [ Chemical 2] Among the groups represented by the general formula (2), X 1 represents a nitrogen atom or C-R 201 , X 2 represents a nitrogen atom or C-R 202 , X 3 represents a nitrogen atom or C-R 203 , X 4 represents a nitrogen atom or C-R 204 , X 5 represents a nitrogen atom or C-R 205 , R 201 ～R 205 is each independently a group consisting of, A hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted, Wherein at least one of X 1 ～X 5 is represented by a nitrogen atom, * Represents a position bonded to other atoms in the structure represented by the general formula (1).
  2. 2. The compound of claim 1, wherein any one of X 1 ～X 5 is a nitrogen atom and the remaining 4 of X 1 ～X 5 are not nitrogen atoms.
  3. 3. A compound according to claim 1 or claim 2 wherein at least one of R 201 ～R 205 is independently selected from substituents other than a hydrogen atom.
  4. 4. A compound according to any one of claims 1 to 3, wherein any one of X 1 ～X 5 is a nitrogen atom and at least one of R 201 ～R 205 bonded to a carbon atom ortho to the nitrogen atom is independently selected from substituents other than hydrogen atoms.
  5. 5. The compound of any one of claims 1-4, wherein X 3 is a nitrogen atom.
  6. 6. The compound of any one of claims 1-5, wherein at least one of R 202 and R 204 is selected from substituents other than hydrogen atoms.
  7. 7. The compound of any one of claims 1-6, wherein R 202 and R 204 are each independently selected from Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and process for producing the same The substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  8. 8. The compound according to any one of claim 1 to 7, wherein R 101 ～R 121 which is not a group represented by the general formula (2) is each independently, A hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted.
  9. 9. The compound of any one of claims 1-8, wherein at least 1 of R 108 、R 109 、R 110 and R 111 are each independently selected from substituents other than hydrogen atoms.
  10. 10. The compound of any one of claims 1 to 9, wherein R 110 is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring-forming atoms.
  11. 11. The compound according to any one of claims 1 to 10, wherein at least one of R 115 ～R 121 is a group represented by the general formula (2).
  12. 12. The compound according to any one of claims 1 to 11, wherein at least one of R 115 ～R 118 is a group represented by the general formula (2).
  13. 13. A light-emitting element material comprising the compound according to any one of claims 1 to 12.
  14. 14. An organic electroluminescent element characterized by comprising a cathode, an anode, and an organic layer interposed between the cathode and the anode, The organic layer comprises a light-emitting layer, At least 1 layer of the organic layer contains the compound according to any one of claims 1 to 12 as a first compound.
  15. 15. The organic electroluminescent element according to claim 14, wherein the light-emitting layer contains the first compound.
  16. 16. The organic electroluminescent element according to claim 15, wherein the light-emitting layer further contains a delayed fluorescence light-emitting material.
  17. 17. The organic electroluminescent element according to claim 16, wherein the lowest excited singlet energy S1 (M2) of the delayed fluorescence light-emitting material and the lowest excited singlet energy S1 (M1) of the first compound satisfy the following formula (number 1), S1 (M2) > S1 (M1), (number 1).
  18. 18. The organic electroluminescent element as claimed in claim 17, wherein the light-emitting layer further comprises a third compound, The minimum excited singlet energy S1 (M2) of the delayed fluorescent light-emitting material and the minimum excited singlet energy S1 (M3) of the third compound satisfy the following formula (number 2), S1 (M3) > S1 (M2), (number 2).
  19. 19. An electronic device mounted with the organic electroluminescent element according to any one of claims 14 to 18.

Description

Compound, light-emitting element material, organic electroluminescent element, and electronic device Technical Field The present invention relates to a compound, a light-emitting element material, 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 ratio of 25% and triplet excitons are generated at a ratio 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, and the internal quantum efficiency of 25% is called a limit. Accordingly, studies for improving the performance of the organic EL element are being conducted. Examples of the performance of the organic EL element include luminance, emission wavelength, half-width value, chromaticity, emission efficiency, driving voltage, and lifetime. 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), for example, a compound having a donor site and an acceptor site bonded in a molecule is known. Patent document 1, for example, discloses an organic EL element and a compound used for the organic EL element. Prior art literature Patent literature Patent document 1 International publication No. 2021/215446 Disclosure of Invention Technical problem to be solved by the invention Further performance improvement is demanded in an organic EL element using a TADF mechanism. The purpose of the present invention is to provide a compound that can cause an organic electroluminescent element to emit light with high efficiency and long life, a light-emitting element material containing the compound, an organic electroluminescent element that emits light with high efficiency and long life, and an electronic device that incorporates the organic electroluminescent element. Solution to the above technical problems According to an embodiment of the present invention, there can be provided a compound having a structure represented by the following general formula (1). [ Chemical 1] (In the general formula (1), R 101～R121 is independently selected from From hydrogen atoms, Halogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkenyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms, A group represented by-O- (R 190), A group represented by-S- (R 191), Substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, A group represented by-C (=O) -O- (R 192), A group represented by-C (=O) -N (R 193）（R194), A group represented by-N (R 195）（R196), Nitro group The group represented by-Si (R 197）（R198）（R199) is selected from the group consisting of. (In the compound having the structure represented by the general formula (1), R 190～R199 are each independently, A hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted. Wherein R 101～R121 is not a substituted or unsubstituted N-carbazolyl group. The structure represented by the general formula (1) has at least 1 group represented by the following general formula (2). ) [ Chemica