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CN-115039248-B - Organic electroluminescent element and electronic device

CN115039248BCN 115039248 BCN115039248 BCN 115039248BCN-115039248-B

Abstract

Provided are an organic electroluminescent element having further improved element performance, and an electronic device comprising such an organic electroluminescent element, wherein an electron transport layer comprises a compound A represented by formula (1), and a light-emitting layer comprises a host material B represented by formula (10). Wherein each symbol is as defined in the specification.

Inventors

  • JI TIANGUI
  • SAITOU MASATOSHI
  • NAKAMURA MASATO
  • MASUDA TETSUYA

Assignees

  • 出光兴产株式会社
  • 出光兴产株式会社

Dates

Publication Date
20260421
Application Date
20210204
Priority Date
20200205

Claims (20)

  1. 1. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, The organic layer includes a light emitting layer and an electron transport layer, The electron transport layer comprises a compound A, the light emitting layer comprises a host material B, The compound A is represented by the formula (1), the host material B is represented by the formula (10-3) or the formula (10-4), In the formula, Y 1 is a nitrogen atom, Y 2 is CR; R is a hydrogen atom; ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms; L 1 and L 2 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms; r 1 ～R 6 is a hydrogen atom; adjacent 2 selected from R 1 ～R 6 are not bonded to each other and thus do not form a ring; Cz is represented by the following formula (1-a) or formula (1-b); In the formula, 1 Selected from R 21 ～R 28 is a single bond bonded to L 3 via a; R 21 ～R 28 or R 31 ～R 38 , which are not single bonds bonded to L 3 via a, are each a hydrogen atom; r a is selected from substituted or unsubstituted aryl groups with 6-18 ring-forming carbon atoms and substituted or unsubstituted alkyl groups with 1-6 carbon atoms; * b represents a bonding position with L 3 , N is an integer of 1 to 3, and when n is 2 or 3, 2 or 3 czs are the same or different from each other; L 3 and L 4 are each independently a single bond or a substituted or unsubstituted phenylene group, wherein, in the case where n is 2 or 3, L 4 is a substituted or unsubstituted phenylene group, In the formula (10-3), R 101A ～R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, L 101A is a single bond or a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, 2L 101A are optionally identical or different, Ar 101A is a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, 2 Ar 101A are optionally the same or different, In the formula (10-4), L 101 is independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring-forming carbon atoms; Ar 101 is a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming carbon atoms, R 101A ～R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, X 11 is O, S or N (R 61 ), R 61 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, 1 Of R 62 ～R 69 is a single bond bonded to L 101 via x, Adjacent 2 selected from at least one group of R 62 ～R 69 other than the single bond to L 101 are optionally bonded to each other to form a substituted or unsubstituted benzene ring or naphthalene ring, or are not bonded to each other to form a ring, R 62 ～R 69 which is not a single bond to L 101 and does not form the benzene ring or naphthalene ring is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, The substituents expressed as "substituted or unsubstituted" are each independently selected from the group consisting of unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted alkyl having 1 to 6 carbon atoms, and unsubstituted cycloalkyl having 3 to 6 ring-forming carbon atoms.
  2. 2. The organic electroluminescent element according to claim 1, wherein, L 3 and L 4 are each independently a substituted or unsubstituted phenylene group.
  3. 3. The organic electroluminescent element according to claim 1, wherein, L 3 and L 4 are single bonds.
  4. 4. The organic electroluminescent element according to claim 1, wherein, The compound A is represented by the formula (1-b-1) or (1-b-2), In the formula, Y 1 、Y 2 、Ar 1 、Ar 2 、L 1 、L 2 and R 1 ～R 6 are as defined in formula (1), R 31 ～R 38 is as defined in formula (1-b), R 41 ～R 42 、R 44 ～R 45 、R 51 ～R 52 and R 54 ～R 55 are each independently selected from a hydrogen atom, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group and an unsubstituted alkyl group having 1 to 6 carbon atoms.
  5. 5. The organic electroluminescent element according to claim 1, wherein, The compound A is represented by any one of formulas (1-b-11) to (1-b-14), In the formula, Y 1 、Y 2 、Ar 1 、Ar 2 、L 1 、L 2 and R 1 ～R 6 are as defined in formula (1), R 31 ～R 38 is as defined in formula (1-b), R 41 、R 44 and R 45 are each independently selected from a hydrogen atom, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group and an unsubstituted alkyl group having 1 to 6 carbon atoms, R 43 is selected from a hydrogen atom, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group and an unsubstituted alkyl group having 1 to 6 carbon atoms.
  6. 6. The organic electroluminescent element according to claim 1, wherein, The compound A is represented by any one of formulas (1-a-1) to (1-a-4), In the formula, Y 1 、Y 2 、Ar 1 、Ar 2 、L 1 、L 2 and R 1 ～R 6 are as defined in formula (1), R a and R 21 ～R 28 are as defined for formula (1-a), R 41 ～R 42 and R 44 ～R 45 are each independently selected from a hydrogen atom, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group and an unsubstituted alkyl group having 1 to 6 carbon atoms.
  7. 7. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, 1 Of L 1 and L 2 is a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, and the remaining 1 is a single bond.
  8. 8. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms.
  9. 9. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The unsubstituted arylene groups of the substituted or unsubstituted arylene groups having 6 to 18 ring-forming carbon atoms represented by L 1 and L 2 are each independently selected from phenylene, biphenylene, naphthylene and phenanthrylene.
  10. 10. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The unsubstituted aryl groups of the substituted or unsubstituted aryl groups having 6 to 18 ring-forming carbon atoms represented by Ar 1 and Ar 2 are each independently selected from phenyl, biphenyl, naphthyl, phenanthryl, anthracyl and fluoranthenyl.
  11. 11. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The molecular weight of the compound A is more than 650.
  12. 12. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The molecular weight of the compound A is 650-3000.
  13. 13. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The molecular weight of the compound A is 650-2000.
  14. 14. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, Compound a contains at least one deuterium atom.
  15. 15. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The host material B is represented by the formula (10-6), In the formula, L 101 and Ar 101 are as defined in formula (10-4), R 101A ～R 108A is as defined in formula (10-4), R 66 ～R 69 is as defined in formula (10-4), X 12 is O or S.
  16. 16. The organic electroluminescent element according to claim 15, wherein, The host material B represented by the formula (10-6) is represented by the following formula (10-6H), In the formula, L 101 and Ar 101 are as defined in formula (10-4); r 66 ～R 69 is as defined in formula (10-4); X 12 is O or S.
  17. 17. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein, The host material B is represented by the following formula (10-7), In the formula, L 101 and Ar 101 are as defined in formula (10-4), R 101A ～R 108A is as defined in formula (10-4), X 11 is as defined in formula (10-4), R 62 ～R 69 is as defined in formula (10-4), wherein 2 adjacent groups selected from the group consisting of R 66 and R 67 、R 67 and R 68 and R 68 and R 69 are bonded to each other to form a substituted or unsubstituted benzene ring or naphthalene ring.
  18. 18. The organic electroluminescent element according to claim 17, wherein, The host material B represented by the formula (10-7) is represented by the following formula (10-7H), In the formula, L 101 and Ar 101 are as defined in formula (10-4); X 11 is as defined in formula (10-4); R 62 ～R 69 is as defined in formula (10-4), wherein 2 adjacent groups selected from the group consisting of R 66 and R 67 、R 67 and R 68 and R 68 and R 69 are bonded to each other to form a substituted or unsubstituted benzene ring or naphthalene ring.
  19. 19. The organic electroluminescent element according to claim 1, wherein, The host material B is represented by the formula (10-8), In the formula, L 101 and Ar 101 are as defined in formula (10-4), R 101A ～R 108A is as defined in formula (10-4), X 12 is O or S, and the total number of the components is equal to or less than zero, R 66 ～R 69 is as defined in formula (10-4), wherein 2 adjacent groups selected from the group consisting of R 66 and R 67 、R 67 and R 68 and R 68 and R 69 are bonded to each other to form a substituted or unsubstituted benzene ring or naphthalene ring.
  20. 20. The organic electroluminescent element as claimed in claim 18 or 19, wherein, Adjacent 2 selected from the group consisting of R 66 and R 67 、R 67 and R 68 and R 68 and R 69 form a ring represented by formula (10-8-1), In the formula, 2 X 2 ring-forming carbon atoms bonded to 2 adjacent groups selected from the group 1 of R 66 and R 67 、R 67 and R 68 and R 68 and R 69 respectively, R 80 ～R 83 is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms.

Description

Organic electroluminescent element and electronic device Technical Field The present invention relates to an organic electroluminescent element and an electronic device including the same. Background In general, an organic electroluminescent element (hereinafter, also referred to as an "organic EL element") is composed of an anode, a cathode, and an organic layer interposed between the anode and the cathode. When a voltage is applied between the electrodes, electrons are injected from the cathode side into the light-emitting region, holes are injected from the anode side into the light-emitting region, and the injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, it has been found that a combination of materials that efficiently transport electrons or holes to a light-emitting region, allow the electrons and holes to be easily recombined, and allow excitons to efficiently emit light is important in obtaining a high-performance organic EL element. Patent documents 1 to 9 disclose a compound used as a material for an organic EL element and an organic EL element including the compound. Prior art literature Patent literature Patent document 1 WO2005/112519A1 Patent document 2 wo2017/200210A1 Patent document 3 KR2014-0006708 Patent document 4 wo2019/139419A1 Patent document 5 WO2018/105888A1 Patent document 6 wo2018/056645A1 Patent document 7, NC 107880031 Patent document 8 wo2012/108881A1 Patent document 9 U.S. Pat. No. 5,103, 0361268 Disclosure of Invention Problems to be solved by the invention A large number of compounds for organic EL elements have been reported in the past, but there is still a need for further improvement in the performance of organic EL elements. The present invention has been made to solve the above-described problems, and an object thereof is to provide an organic EL element having further improved element performance by including a combination of specific compounds, and an electronic device including such an organic EL element. Means for solving the problems The present inventors have conducted intensive studies on the performance of an organic EL element comprising the compound described in patent documents 1 to 9, and as a result, have found that an organic EL element having a hole blocking layer comprising the compound a described below and a light emitting layer comprising the host material B described below exhibits higher performance. In one aspect, the present invention provides the following organic EL element. The organic EL element has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including a light-emitting layer and an electron-transporting layer, the electron-transporting layer including a compound A, the light-emitting layer including a host material B, the compound A being represented by formula (1), the host material B being represented by formula (10). [ Chemical formula 1] (In the formula (I), 1 Of Y 1 and Y 2 is a nitrogen atom, and the remaining 1 is CR; R is selected from a hydrogen atom, a substituted or unsubstituted aryl group with 6-50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group with 5-50 ring-forming carbon atoms, a substituted or unsubstituted alkyl group with 1-50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3-50 ring-forming carbon atoms, a fluorine atom and a cyano group; Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming carbon atoms; l 1 and L 2 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms; R 1～R6 is independently selected from a hydrogen atom, a 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 carbon atoms, a 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, a fluorine atom and a cyano group; Adjacent 2 selected from R 1～R6 may be bonded to each other to form a substituted or unsubstituted ring, or may not be bonded to each other to form a ring; Cz is represented by the following formula (1-a) or formula (1-b); [ chemical formula 2] (In the formula (I), R 21～R28 and R 31～R38 are each independently a hydrogen atom or a substituent selected from the group consisting of a 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 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 t