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CN-113178538-B - Organic electroluminescent element, display device, lighting device, and anthracene compound

CN113178538BCN 113178538 BCN113178538 BCN 113178538BCN-113178538-B

Abstract

The present invention relates to an organic electroluminescent element, a display device, a lighting device, and an anthracene compound, including a pair of electrodes including an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer includes an anthracene compound represented by the following formula (1) as a host material, and a polycyclic aromatic compound represented by the following formula (2) or a multimer thereof (in formula (1), ar c is an aryl group or the like, R c is hydrogen or the like, any two of Ar 11 ～Ar 18 is an aryl group or the like, and the other is hydrogen or the like, at least one hydrogen in formula (1) may be substituted with deuterium or the like, in formula (2), an A ring, a B ring, a C ring are aryl rings or the like that may be substituted, X 1 and X 2 are > O, > -N-R (R is an aryl group or the like), or the like).

Inventors

  • HATAKEYAMA TAKUJI
  • FUJITA YUKIHIRO
  • WANG GUOFANG
  • Tata Akio
  • Sen Xuanzi
  • Shui Gu Ying Ying
  • Liangjie Kawakami
  • HISADA RIKA

Assignees

  • 学校法人关西学院
  • 爱思开新材料捷恩智株式会社

Dates

Publication Date
20260505
Application Date
20210125
Priority Date
20200127

Claims (20)

  1. 1. An organic electroluminescent element comprising a pair of electrodes comprising an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer comprises a host material, and a polycyclic aromatic compound represented by the following formula (2) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2) as a dopant material, the host material is an anthracene compound represented by the following formula (1) or a combination of two or more anthracene compounds represented by the following formula (1), In the formula (1), the components are as follows, Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, R c is hydrogen, alkyl or cycloalkyl, Any two of Ar 11 、Ar 12 、Ar 13 、Ar 14 、Ar 15 、Ar 16 、Ar 17 and Ar 18 are an optionally substituted aryl or an optionally substituted heteroaryl, and the other six are hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl or an optionally substituted alkoxy, At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano or deuterium, In the formula (2), the amino acid sequence of the compound, The A, B and C rings are each independently an aryl or heteroaryl ring, at least one hydrogen of which may be substituted, X 1 and X 2 are each independently > O, > N-R, > C (-R) 2 , > S or > Se, R of the > N-R being an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the > C (-R) 2 being hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, additionally R of the > N-R and/or R of the > C (-R) 2 being bonded to the A ring, the B ring and/or the C ring by a linking group or a single bond, At least one of the aryl ring and the heteroaryl ring in the compound represented by formula (2) or a multimer thereof may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH 2 -in the cycloalkane may be substituted with-O-, At least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano or halogen.
  2. 2. The organic electroluminescent element according to claim 1, wherein the polycyclic aromatic compound represented by formula (2) or the polymer of the polycyclic aromatic compound having a plurality of structures represented by formula (2) is a polymer of the polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or the polycyclic aromatic compound having a plurality of structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f), In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f), R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 And R 11 is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboronyl, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl groups, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl groups ,R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 and the adjacent groups in R 11 may be bonded to each other and form together with the a-, b-or c-ring an aryl or heteroaryl ring, at least one of which may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboronyl, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl groups, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl groups, X X is each independently > O, > S, > N-R, or > C (-R) 2 , R of the > N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the > C (-R) 2 is each independently hydrogen, an optionally alkyl-or cycloalkyl-substituted aryl, an optionally alkyl-or cycloalkyl-substituted heteroaryl, an alkyl, or cycloalkyl, X 1 and X 2 are each independently > O, > N-R, > C (-R) 2 , > S or > Se, wherein R of > N-R is an aryl group of 6 to 12 carbon atoms which may be substituted with an alkyl group of 1 to 6 carbon atoms or a cycloalkyl group of 3 to 14 carbon atoms, a heteroaryl group of 2 to 15 carbon atoms which may be substituted with an alkyl group of 1 to 6 carbon atoms or a cycloalkyl group of 3 to 14 carbon atoms, R of > C (-R) 2 is hydrogen, an aryl group of 6 to 12 carbon atoms which may be substituted with an alkyl group of 1 to 6 carbon atoms or a cycloalkyl group of 3 to 14 carbon atoms, R of > N-R and/or R of > C (-R) 2 may be bonded to the a ring, the b ring and/or the C (-R) 2 -or the C (-R) ring is independently R of 4 to the C (-R) 2 -or the C (-R) 4 carbon atoms, At least one of the aryl ring and the heteroaryl ring in the compound represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) or the formula (2-f) or a multimer thereof may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH 2 -in the cycloalkane may be substituted with-O-group, At least one hydrogen in the compound or structure represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) may be substituted with deuterium, cyano or halogen, In the case of a multimer, it is a dimer or trimer having a structure represented by two or three of the formulae (2-a), (2-b), (2-c), (2-d), (2-e) or (2-f).
  3. 3. The organic electroluminescent element according to claim 2, wherein the compound represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a) or formula (2-b) or a multimer of a plurality of polycyclic aromatic compounds represented by formula (2-a) or formula (2-b).
  4. 4. The organic electroluminescent element according to claim 3, wherein the compound represented by formula (2) is any one of compounds represented by the following formulas, In the formula, me is methyl, tBu is tertiary butyl, tAm is tertiary amyl, and D is deuterium.
  5. 5. The organic electroluminescent element according to any one of claims 1 to 4, wherein the anthracene compound represented by formula (1) is an anthracene compound represented by the following formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E), In the formula (1A), the formula (1B), the formula (1C), the formula (1D) or the formula (1E), Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 ' are each independently a phenyl group, a biphenyl group, a terphenyl group, a tetrabiphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a fu group, a triphenylene group, a pyrenyl group, or a group represented by the formula (A), at least one hydrogen of these groups may be substituted by a phenyl group, a biphenyl group, a terphenyl group, a tetrabiphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a fu group, a triphenylene group, a pyrenyl group, or a group represented by the formula (A), where when both hydrogens of methylene groups in the fluorenyl group and the benzofluorenyl group are substituted by phenyl groups, these phenyl groups may be bonded to each other by a single bond, Instead of hydrogen, methyl or tert-butyl groups may be bonded to carbon atoms on the anthracycline to which Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'or Ar 18 ' are not bonded, At least one hydrogen in the compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) may be substituted with halogen, cyano or deuterium, The group represented by the formula (A) is a group obtained by removing one hydrogen at an arbitrary position of the formula (A), The position is indicated by the fact that, In the formula (A), Y is-O-, -S-or > N-R 39 ,R 21 ～R 28 is independently hydrogen, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, a substitutable amino group, a halogen, a hydroxyl group or a cyano group, adjacent groups in R 21 ～R 28 may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable arylthio group, a trialkylsilyl group, a tricycloalkylsycloalkylsycloalkylsilyl group, a bicycloalkylsilyl group, a substitutable amino group, a halogen, a hydroxyl group or a cyano group, or a substitutable aryl group may be substituted 39 .
  6. 6. The organic electroluminescent element according to claim 5, wherein The group represented by the formula (A) is a group represented by any one of the formulas (A-1) to (A-14), The groups represented by the formulae (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of each of the formulae (A-1) to (A-14), The position is indicated by the fact that, In the formulae (A-1) to (A-14), Y is-O-, -S-or > N-R 39 ,R 39 is hydrogen or aryl, at least one hydrogen in the group represented by the formulae (A-1) to (A-14) may be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl or cyano, 。
  7. 7. The organic electroluminescent element according to claim 5, wherein Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 ' are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4), at least one hydrogen of these groups may be substituted by a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4), At least one hydrogen in the compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) may be substituted with halogen, cyano or deuterium.
  8. 8. The organic electroluminescent element according to any one of claims 1 to 4, wherein Ar 14 and Ar 15 are aryl groups which may be substituted or heteroaryl groups which may be substituted, and Ar 11 、Ar 12 、Ar 13 、Ar 16 、Ar 17 and Ar 18 are each hydrogen.
  9. 9. The organic electroluminescent element according to claim 8, wherein at least one selected from the group consisting of Ar c 、Ar 14 and Ar 15 is an anthracycline-containing group.
  10. 10. The organic electroluminescent device according to claim 8, wherein at least one selected from the group consisting of Ar c 、Ar 14 and Ar 15 comprises a group represented by formula (A'), In formula (a'), R 21 ～R 28 is each independently hydrogen, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, a substitutable amino group, a halogen, a hydroxyl group, or a cyano group, and adjacent groups in R 21 ～R 28 may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, at least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted by a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloakyl group, an alkylbicycloalkyl group, a substitutable amino group, a halogen, a hydroxyl group, or a cyano group.
  11. 11. The organic electroluminescent element according to claim 8, wherein at least one hydrogen in the compound represented by formula (1) is substituted with deuterium.
  12. 12. The organic electroluminescent element according to any one of claims 1 to 4, comprising an electron-transporting layer and/or an electron-injecting layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron-transporting layer and the electron-injecting layer contains at least one selected from the group consisting of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, an aryl nitrile derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, a hydroxyquinoline metal complex, a thiazole derivative, a benzothiazole derivative, a silole derivative, and an oxazoline derivative.
  13. 13. The organic electroluminescent element according to claim 12, wherein the electron transporting layer and/or the electron injecting layer further contains at least one selected from the group consisting of alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth metal halide, rare earth metal oxide, rare earth metal halide, organic complex of alkali metal, organic complex of alkaline earth metal, and organic complex of rare earth metal.
  14. 14. A display device comprising the organic electroluminescent element as claimed in any one of claims 1 to 13.
  15. 15. A lighting device comprising the organic electroluminescent element as claimed in any one of claims 1 to 13.
  16. 16. An anthracene compound represented by the following formula (1): in the formula (1), the components are as follows, Ar c 、Ar 14 and Ar 15 are optionally substituted aryl or optionally substituted heteroaryl, R c is hydrogen, alkyl or cycloalkyl, Ar 11 、Ar 12 、Ar 13 、Ar 16 、Ar 17 and Ar 18 are hydrogen, At least one of Ar 14 and Ar 15 is an anthracycline-containing group, At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano or deuterium.
  17. 17. The anthracene compound according to claim 16, represented by the following formula (1 Aa): In the formula (1 Aa), ar c '、Ar 14 'and Ar 15 ' are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a fu group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulas (A-1) to (A-14), at least one hydrogen of these groups may be substituted by a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a fu group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulas (A-1) to (A-14), where when hydrogen of a methylene group in the fluorenyl group and the benzofluorenyl group is substituted by a phenyl group, these phenyl groups may be bonded to each other by a single bond, a methyl group or a tert-butyl group may be bonded to a carbon atom on an anthracene ring which is not bonded to Ar c '、Ar 14 'or Ar 15 ', At least one of Ar 14 'and Ar 15 ' is an anthracycline-containing group, At least one hydrogen in the compound represented by the formula (1 Aa) may be substituted with halogen, cyano or deuterium, The groups represented by the formulae (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of each of the formulae (A-1) to (A-14), The position is indicated by the fact that, In the formulae (A-1) to (A-14), Y is-O-, -S-or > N-R 39 ,R 39 is hydrogen or aryl, at least one hydrogen in the group represented by the formulae (A-1) to (A-14) may be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl or cyano, Wherein at least one hydrogen in the compound represented by formula (1 Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (1 Aa) is substituted with deuterium.
  18. 18. The anthracene compound according to claim 17, wherein 、 And Each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4), And At least one of these groups is an anthracycline-containing group, and at least one hydrogen of these groups may be substituted with a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulas (A-1) to (A-4).
  19. 19. The anthracene compound according to claim 17 or 18, wherein in the formula (1 Aa), at least hydrogen bonded to the 10-position of the anthracycline is substituted with deuterium.
  20. 20. An anthracene compound represented by any one of the following formulas: in the formula, D represents deuterium.

Description

Organic electroluminescent element, display device, lighting device, and anthracene compound Technical Field The present invention relates to an organic electroluminescent element, and a display device and a lighting device using the same. In addition, the present invention relates to an anthracene compound useful as a light-emitting material. Background Various studies have been made in the past on display devices using light emitting elements that perform Electroluminescence, because of the reduction in power consumption and thickness, and further, organic Electroluminescence (hereinafter, sometimes referred to as "organic EL element") elements including organic materials have been actively studied because of the easiness in weight reduction and size increase. In particular, development of organic materials having light emission characteristics such as blue, which is one of three primary colors of light, and combination of various materials exhibiting optimal light emission characteristics, whether high molecular compounds or low molecular compounds, have been actively studied so far. The organic EL element has a structure including a pair of electrodes including an anode and a cathode, and one or more layers including an organic compound and disposed between the pair of electrodes. The organic compound-containing layer includes a light-emitting layer, a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed. Patent document 1 describes the use of an anthracene compound as a light-emitting material for an organic electroluminescent element. In recent years, a polycyclic aromatic compound in which a plurality of aromatic rings are condensed with boron or the like as a central atom has been reported as a material for an organic electroluminescent element (patent document 2). [ Prior Art literature ] [ Patent literature ] [ Patent document 1] International publication No. 2006/003842 [ Patent document 2] International publication No. 2015/102118 Disclosure of Invention [ Problem to be solved by the invention ] As described above, various materials have been developed as materials for organic EL elements, but in order to increase options for materials for organic EL elements, it is desired to develop a material containing a compound different from the existing materials. The invention provides an organic EL element using a combination of new materials. The present invention addresses the problem of providing an organic EL element having a high external quantum efficiency. [ Means of solving the problems ] The present inventors have made an intensive study to solve the above-mentioned problems, and as a result, have found that an excellent organic EL element can be obtained by using a light-emitting layer containing a specific anthracene compound as a host material and a polycyclic aromatic compound having a plurality of aromatic rings condensed as a dopant material, and have completed the present invention. Namely, the present invention provides an organic electroluminescent device and an anthracene compound as described below. <1> An organic electroluminescent element comprising a pair of electrodes comprising an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer comprises an anthracene compound represented by the following formula (1) as a host material, and a polycyclic aromatic compound represented by the following formula (2) or a polymer of a plurality of polycyclic aromatic compounds having a structure represented by the following formula (2) as a dopant material, [ Chemical 1] In the formula (1), the components are as follows, Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, R c is hydrogen, alkyl or cycloalkyl, Ar 11、Ar12、Ar13、Ar14、Ar15、Ar16、Ar17 and Ar 18 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano or deuterium. In the formula (2), the amino acid sequence of the compound, The A, B and C rings are each independently an aryl or heteroaryl ring, at least one hydrogen of which may be substituted, X 1 and X 2 are each independently > O, > N-R, > C (-R) 2, > S or > Se, R of the > N-R being an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the > C (-R) 2 being hydrogen, an optionally substituted ary