Organic electroluminescent element and electronic device including same

Abstract

The present invention provides an organic electroluminescent element having further improved element performance by comprising a combination of specific compounds, and an electronic device including the same. An organic electroluminescent element according to one embodiment includes a compound represented by formula (A1) and a compound represented by formula (A2). An organic electroluminescent element according to another embodiment includes a compound represented by formula (B1) and a compound represented by formula (B2).

Description

Technical Field

[0001] This invention relates to an organic electroluminescent element and an electronic device including the same. Background Technology

[0002] Typically, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the luminescent region from the cathode side, and holes are injected into the luminescent region from the anode side. The injected electrons and holes recombine in the luminescent region to form an excited state, which emits light when it returns to the ground state. Therefore, finding a combination of materials that can effectively transport electrons or holes to the luminescent region, facilitate electron-hole recombination, and effectively enable exciton luminescence is crucial for obtaining high-performance organic EL devices.

[0003] Patent documents 1 to 10 disclose organic electroluminescent elements and compounds used as materials thereon.

[0004] Existing technical documents

[0005] Patent Document 1: US Patent No. 11230521 (US11230521B2)

[0006] Patent Document 2: PCT Patent Publication No. 2019 / 044542 (WO2019 / 044542A1)

[0007] Patent Document 3: U.S. Patent Publication No. 2020 / 0144552 (US2020 / 0144552A1)

[0008] Patent Document 4: Korean Patent No. 2355848 (KR10-2355848B1)

[0009] Patent Document 5: PCT Patent Publication No. 2012 / 034627 (WO2012 / 034627A1)

[0010] Patent Document 6: PCT Patent Publication No. 2020 / 226298 (WO2020 / 226298A1)

[0011] Patent Document 7: PCT Patent Publication No. WO2016 / 006710 (WO2016 / 006710A1)

[0012] Patent Document 8: U.S. Patent Publication No. 2017 / 0288147 (US2017 / 0288147A1)

[0013] Patent Document 9: PCT Patent Publication No. 2023 / 140529 (WO2023 / 140529A1)

[0014] Patent Document 10: European Patent Publication No. 3540803 (EP3540803A2) Summary of the Invention

[0015] The problem that the invention aims to solve

[0016] Previously, although many compounds for organic EL elements have been reported, further improvements in the performance of organic EL elements are still needed.

[0017] In order to solve the above problems, the object of the present invention is to provide an organic EL element that has further improved element performance by including a combination of specific compounds, and an electronic device including such an organic EL element.

[0018] Methods for solving problems

[0019] According to one embodiment of the present invention, an organic electroluminescent element is provided, the organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer comprising: a light-emitting layer; a hole transport layer formed between the light-emitting layer and the first electrode; and a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer, the light-emitting layer comprising a luminescent compound exhibiting a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm, the hole transport layer comprising a compound represented by formula (A1), and the light-emitting auxiliary layer comprising a compound represented by formula (A2).

[0020] (A1)

[0021] (A2)

[0022] (In formula (A1),

[0023] N is the central nitrogen atom.

[0024] L a1 L a2 and L a3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms in the cyclic ring.

[0025] Ar a2 It is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted, a heterocyclic group with 5 to 30 carbon atoms that is substituted or unsubstituted, or a cycloalkyl group with 5 to 30 carbon atoms that is substituted or unsubstituted.

[0026] In equation (A2),

[0027] N is the central nitrogen atom.

[0028] X b It represents an oxygen atom or a sulfur atom.

[0029] Selected from R 1 ~R 8 One of them is a single bond that bonds with *2.

[0030] Selected from R 1 ~R 8 The single bond in the *2 is not a bond that bonds with *2 and the two adjacent bonds can bond with each other to form a substituted or unsubstituted benzene ring, or they do not bond with each other and do not form a ring.

[0031] It is not a single bond bonded to *2 and the two adjacent R bonds are not bonded to each other. 1 ~R 8 It is a hydrogen atom.

[0032] L b1 L b2 and L b3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms in the cyclic ring.

[0033] Ar in formula (A1) a3 And Ar in formula (A2) b2 and Ar b3 Each is independently a group represented by any one of the following formulas (a) to (e).

[0034]

[0035] (In equation (a),

[0036] R 10 ~R 25 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0037] Among them, selected from R 10 ~R 14 One of them is a single bond that bonds with *f.

[0038] Selected from R 15 ~R 20 One of them is a single bond that bonds with *g, selected from R 15 ~R 20 The other one is a single bond that bonds with *h.

[0039] *** indicates that L a3 L b2 or L b3 The location of the bond,

[0040] m1 is either 0 or 1, n1 is either 0 or 1.

[0041] When m1 is 0 and n1 is 0, *h and L a3 L b2 or L b3 bonding,

[0042] When m1 is 0 and n1 is 1, *f and L a3 L b2 or L b3 bonding,

[0043] When m1 is 1 and n1 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0044] k1 is 1 or 2.

[0045] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0046] In equation (b),

[0047] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0048] R 26 ~R 33 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0049] Among them, selected from R 26 ~R 33 One of them is a single bond that bonds with *i.

[0050] m2 is either 0 or 1, n2 is either 0 or 1.

[0051] When m2 is 0 and n2 is 0, *h and L a3 L b2 or Lb3 bonding,

[0052] When m2 is 0 and n2 is 1, *f and L a3 L b2 or L b3 bonding,

[0053] When m2 is 1 and n2 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0054] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0055] In equation (c),

[0056] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0057] R 34 ~R 43 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0058] Among them, selected from R 34 ~R 43 One of them is a single bond that bonds with *j.

[0059] m3 is either 0 or 1, n3 is either 0 or 1.

[0060] When m3 is 0 and n3 is 0, *h and L a3 L b2 or L b3 bonding,

[0061] When m3 is 0 and n3 is 1, *f and L a3 L b2 or L b3 bonding,

[0062] When m3 is 1 and n3 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0063] Selected from R 10 ~R14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 15 ~R 20 The two adjacent single bonds that are not any of the stated single bonds, and R 34 and R 35 They do not bond with each other and thus do not form a ring structure.

[0064] In equation (d),

[0065] R 10 ~R 14 The same applies to *f and ***.

[0066] R 44 ~R 51 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0067] X represents an oxygen atom, a sulfur atom, or CR. a R b or NR c ,

[0068] R a R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, or R a and R b They can bond with each other to form substituted or unsubstituted ring structures.

[0069] Among them, selected from R 44 ~R 51 One of them is a single bond that bonds with *k.

[0070] m4 is 0 or 1.

[0071] When m4 is 0, *f and L a3 L b2 or L b3 Bonding.

[0072] Selected from R 44 ~R 51 The single bonds are not the single bonds, and two adjacent bonds can independently bond to each other to form substituted or unsubstituted ring structures.

[0073] In equation (e),

[0074] R10 ~R 14 The same applies to *f and ***.

[0075] R 52 ~R 66 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0076] Among them, selected from R 52 ~R 56 One of them is a single bond bonded to *l, selected from R 52 ~R 56 The other one is a single bond that bonds with *m.

[0077] m5 is 0 or 1.

[0078] When m5 is 0, *f and L a3 L b2 or L b3 Bonding.

[0079] Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 52 ~R 56 The two adjacent R bonds that are not any of the stated single bonds 52 and R 61 and R 56 and R 57 They do not bond with each other and therefore do not form a ring structure.

[0080] According to another embodiment of the present invention, an organic electroluminescent element is provided, the organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer comprising: a light-emitting layer; a hole transport layer formed between the light-emitting layer and the first electrode; and a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer, the plurality of light-emitting auxiliary layers including a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer, the hole transport layer comprising a compound or a diamine of formula (B1), and the light-emitting auxiliary layer b comprising a compound of formula (B2).

[0081] (B1)

[0082] (B2)

[0083] (In equation (B1),

[0084] N is the central nitrogen atom.

[0085] L a1 L a2 and L a3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms in the cyclic ring.

[0086] In equation (B2),

[0087] N is the central nitrogen atom.

[0088] Ar b1 It is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted, a heterocyclic group with 5 to 30 carbon atoms that is substituted or unsubstituted, or a cycloalkyl group with 5 to 30 carbon atoms that is substituted or unsubstituted.

[0089] L b1 L b2 and L b3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms in the cyclic ring.

[0090] Ar in equation (B1) a3 And Ar in formula (B2) b2 and Ar b3 Each is independently a group represented by any one of the following formulas (a) to (e).

[0091]

[0092] (In equation (a),

[0093] R 10 ~R 25 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0094] Among them, selected from R 10 ~R 14 One of them is a single bond that bonds with *f.

[0095] Selected from R 15 ~R 20 One of them is a single bond that bonds with *g, selected from R 15 ~R 20 The other one is a single bond that bonds with *h.

[0096] *** indicates that L a3 L b2 or L b3 The location of the bond,

[0097] m1 is either 0 or 1, n1 is either 0 or 1.

[0098] When m1 is 0 and n1 is 0, *h and L a3 L b2 or L b3 bonding,

[0099] When m1 is 0 and n1 is 1, *f and L a3 L b2 or L b3 bonding,

[0100] When m1 is 1 and n1 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0101] k1 is 1 or 2.

[0102] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0103] In equation (b),

[0104] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0105] R 26 ~R 33 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0106] Among them, selected from R 26 ~R 33 One of them is a single bond that bonds with *i.

[0107] m2 is either 0 or 1, n2 is either 0 or 1.

[0108] When m2 is 0 and n2 is 0, *h and L a3 L b2 or Lb3 bonding,

[0109] When m2 is 0 and n2 is 1, *f and L a3 L b2 or L b3 bonding,

[0110] When m2 is 1 and n2 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0111] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0112] In equation (c),

[0113] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0114] R 34 ~R 43 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0115] Among them, selected from R 34 ~R 43 One of them is a single bond that bonds with *j.

[0116] m3 is either 0 or 1, n3 is either 0 or 1.

[0117] When m3 is 0 and n3 is 0, *h and L a3 L b2 or L b3 bonding,

[0118] When m3 is 0 and n3 is 1, *f and L a3 L b2 or L b3 bonding,

[0119] When m3 is 1 and n3 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0120] Selected from R 10 ~R14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 15 ~R 20 The two adjacent single bonds that are not any of the stated single bonds, and R 34 and R 35 They do not bond with each other and thus do not form a ring structure.

[0121] In equation (d),

[0122] R 10 ~R 14 The same applies to *f and ***.

[0123] R 44 ~R 51 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0124] X represents an oxygen atom, a sulfur atom, or CR. a R b or NR c ,

[0125] R a R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, or R a and R b They can bond with each other to form substituted or unsubstituted ring structures.

[0126] Among them, selected from R 44 ~R 51 One of them is a single bond that bonds with *k.

[0127] m4 is 0 or 1.

[0128] When m4 is 0, *f and L a3 L b2 or L b3 Bonding.

[0129] Selected from R 44 ~R 51 The single bonds are not the single bonds, and two adjacent bonds can independently bond to each other to form substituted or unsubstituted ring structures.

[0130] In equation (e),

[0131] R10 ~R 14 The same applies to *f and ***.

[0132] R 52 ~R 66 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0133] Among them, selected from R 52 ~R 56 One of them is a single bond bonded to *l, selected from R 52 ~R 56 The other one is a single bond that bonds with *m.

[0134] m5 is 0 or 1.

[0135] When m5 is 0, *f and L a3 L b2 or L b3 Bonding.

[0136] Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 52 ~R 56 The two adjacent R bonds that are not any of the stated single bonds 52 and R 61 and R 56 and R 57 They do not bond with each other and therefore do not form a ring structure.

[0137] According to another embodiment of the present invention, an organic electroluminescent element is provided. The organic electroluminescent element includes a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are sequentially disposed from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip. The first light-emitting strip includes a first organic layer. The first organic layer includes: a first light-emitting layer; a first hole transport layer formed between the first light-emitting layer and the first electrode; and a first light-emitting auxiliary layer formed between the first hole transport layer and the first light-emitting layer. The two light-emitting units include a second light-emitting band, the second light-emitting band includes a second organic layer, the second organic layer includes: a second hole transport layer; a second light-emitting layer formed between the second hole transport layer and the second electrode; and a second light-emitting auxiliary layer formed between the second hole transport layer and the second light-emitting layer, at least one of the first light-emitting layer and the second light-emitting layer contains a light-emitting compound exhibiting a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm, at least one of the first hole transport layer and the second hole transport layer contains a compound represented by formula (A1) above, and at least one of the first light-emitting auxiliary layer and the second light-emitting auxiliary layer contains a compound represented by formula (A2) above.

[0138] According to another embodiment of the present invention, an organic electroluminescent element is provided. The organic electroluminescent element includes a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are sequentially disposed from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip. The first light-emitting strip includes a first organic layer. The first organic layer includes: a first light-emitting layer; a first hole transport layer formed between the first light-emitting layer and the first electrode; and a plurality of first light-emitting auxiliary layers formed between the first hole transport layer and the first light-emitting layer. The plurality of first light-emitting auxiliary layers includes a first light-emitting layer adjacent to the first hole transport layer. The first light-emitting unit includes a 1a light-emitting auxiliary layer and a 1b light-emitting auxiliary layer adjacent to the first light-emitting layer. The second light-emitting unit includes a second light-emitting strip, which includes a second organic layer. The second organic layer includes a second hole transport layer, a second light-emitting layer formed between the second hole transport layer and the second electrode, and a plurality of second light-emitting auxiliary layers formed between the second hole transport layer and the second light-emitting layer. The plurality of second light-emitting auxiliary layers includes a 2a light-emitting auxiliary layer adjacent to the second hole transport layer and a 2b light-emitting auxiliary layer adjacent to the second light-emitting layer. At least one of the first hole transport layer and the second hole transport layer contains a compound or diamine as shown in formula (B1) above, and at least one of the 1b light-emitting auxiliary layer and the 2b light-emitting auxiliary layer contains a compound as shown in formula (B2) above.

[0139] According to another embodiment of the present invention, an electronic device is provided, the electronic device including the organic electroluminescent element.

[0140] Invention Effects

[0141] According to the present invention, an organic EL element having further improved element performance by comprising a combination of specific compounds, and an electronic device comprising the same, can be provided. Attached Figure Description

[0142] Figure 1 A simplified diagram illustrating an example of the layer structure of an organic EL element according to one embodiment of the present invention.

[0143] Figure 2 A simplified diagram illustrating another example of the layer structure of an organic EL element according to another embodiment of the present invention. Detailed Implementation

[0144] [definition]

[0145] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0146] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.

[0147] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as such unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluorene and 25 for 9,9'-spirobifluorene.

[0148] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.

[0149] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.

[0150] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.

[0151] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.

[0152] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0153] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0154] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0155] Substituents described in this specification

[0156] The substituents described in this specification are explained below.

[0157] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0158] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0159] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0160] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0161] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0162] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0163] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0164] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0165] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0166] • "Substituted or unsubstituted aryl groups"

[0167] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0168] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.

[0169] • Unsubstituted aryl groups (specific example group G1A):

[0170] phenyl,

[0171] p-phenyl,

[0172] metaphenyl,

[0173] o-phenyl,

[0174] p-terphenyl-4-yl,

[0175] p-terphenyl-3-yl,

[0176] p-terphenyl-2-yl,

[0177] m-terphenyl-4-yl,

[0178] m-terphenyl-3-yl,

[0179] m-terphenyl-2-yl,

[0180] o-terphenyl-4-yl

[0181] o-terphenyl-3-yl

[0182] o-terphenyl-2-yl,

[0183] 1-Naphthyl,

[0184] 2-Naphthyl,

[0185] anthracene,

[0186] Benzanthracene,

[0187] Fiki,

[0188] Benzphenanthrene,

[0189] Finadenyl,

[0190] Pyrene

[0191] Chrysenyl,

[0192] Benzochrysenyl,

[0193] Triphenylenyl,

[0194] Benzo[ghi]triphenylenyl,

[0195] Tetracenyl,

[0196] Pentacenyl,

[0197] Fluorenyl,

[0198] 9,9'-Spirobi[fluorenyl],

[0199] Benzo[h]fluorenyl,

[0200] Dibenzo[def,p]fluorenyl,

[0201] Fluorenyl,

[0202] Benzo[def]chrysenyl,

[0203] Perylenyl and

[0204] A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0205]

[0206]

[0207] · Substituted aryl group (specific example group G1B):

[0208] o-Tolyl,

[0209] m-Tolyl,

[0210] p-Tolyl,

[0211] p-Xylyl,

[0212] m-Xylyl,

[0213] o-Xylyl,

[0214] p-Isopropylphenyl,

[0215] m-Isopropylphenyl,

[0216] o-Isopropylphenyl,

[0217] p-tert-Butylphenyl,

[0218] m-tert-Butylphenyl,

[0219] o-tert-Butylphenyl,

[0220] 3,4,5-Trimethylphenyl

[0221] 9,9-Dimethylfluorenyl,

[0222] 9,9-Diphenylfluorenyl

[0223] 9,9-Bis(4-methylphenyl)fluorenyl,

[0224] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0225] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0226] cyanophenyl,

[0227] Triphenylsilylphenyl

[0228] Trimethylsilylphenyl

[0229] Phenynaphthyl,

[0230] Naphthylphenyl and

[0231] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.

[0232] • "Substituted or unsubstituted heterocyclic groups"

[0233] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0234] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0235] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0236] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0237] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0238] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0239] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).

[0240] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0241] pyrrole,

[0242] Imidazole group,

[0243] Pyrazolyl,

[0244] Triazole group,

[0245] Tetrazolyl,

[0246] Oxazolyl,

[0247] Isoxazolyl,

[0248] Oxadiazole group,

[0249] Thiazole group,

[0250] Isothiazolyl,

[0251] Thiadiazole group,

[0252] pyridyl,

[0253] pyridazinyl,

[0254] Pyrimidine group,

[0255] Pyrazinyl,

[0256] Triazine group

[0257] Indole,

[0258] Isoindolyl,

[0259] Indazine-based

[0260] Quinazine-based

[0261] Quinoline,

[0262] Isoquinoline,

[0263] Crenoline group

[0264] Phthaloazine

[0265] Quinazolinyl,

[0266] Quinoxaloyl,

[0267] Benzimidazole group,

[0268] Indazole group,

[0269] phenanthroline,

[0270] phenanthridine,

[0271] acridine group,

[0272] Phenazine group,

[0273] Carbazole group,

[0274] Benzocarbazolyl,

[0275] Morpholinyl,

[0276] phenoxazine group,

[0277] phenothiazine group,

[0278] Azacarbazolyl, and

[0279] Diazacarbazolyl.

[0280] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0281] furanyl,

[0282] Oxazolyl,

[0283] Isoxazolyl,

[0284] Oxadiazole group,

[0285] Xuton base,

[0286] Benzofuranyl,

[0287] Isobenzofuranyl,

[0288] Dibenzofuranyl,

[0289] Naphthobenzofuranyl,

[0290] Benzoxazolyl,

[0291] Benzisoxazole group,

[0292] phenoxazine group,

[0293] Morpholinyl,

[0294] Dinaphthylfuranyl,

[0295] Azadibenzofuranyl,

[0296] diazadibenzofuranyl,

[0297] Azanaphthalenebenzofuranyl and

[0298] Diazanaphthenebenzofuranyl.

[0299] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0300] Thiophene group

[0301] Thiazole group,

[0302] Isothiazolyl,

[0303] Thiadiazole group,

[0304] benzothienyl

[0305] isobenzothienyl

[0306] dibenzothienyl

[0307] Naphthobenzothienyl

[0308] Benzothiazolyl,

[0309] Benzisothiazolyl,

[0310] phenothiazine group,

[0311] dinaphthothienyl

[0312] azadibenzothienyl

[0313] diazadibenzothienyl

[0314] azanaphthobenzothienyl and

[0315] diazanaphthobenzothienyl.

[0316] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0317]

[0318]

[0319] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0320] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0321] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0322] (9-phenyl)carbazole group,

[0323] (9-Biphenyl)carbazolyl,

[0324] (9-Phenyl)phenylcarbazolyl,

[0325] (9-Naphthyl)carbazole,

[0326] Diphenylcarbazole-9-yl,

[0327] Phenylexacarbazole-9-yl,

[0328] Methylbenzimidazole,

[0329] Ethylbenzimidazole,

[0330] Phenylacetyl,

[0331] Biphenyltriazine

[0332] diphenyltriazine group,

[0333] phenylquinazolinyl, and

[0334] Biphenylquinazolinyl.

[0335] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0336] Phenyl dibenzofuranyl,

[0337] Methyldibenzofuranyl,

[0338] tert-butyldibenzofuranyl and

[0339] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0340] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0341] Phenyl dibenzothiophene,

[0342] Methyldibenzothiophene,

[0343] tert-butyldibenzothiophene and

[0344] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0345] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):

[0346] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0347] • "Substituted or unsubstituted alkyl groups"

[0348] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0349] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.

[0350] • Unsubstituted alkyl groups (specific example group G3A):

[0351] methyl,

[0352] Ethyl,

[0353] n-propyl,

[0354] Isopropyl,

[0355] n-Butyl,

[0356] Isobutyl,

[0357] sec-butyl and

[0358] tert-butyl.

[0359] • Substituted alkyl groups (specific example group G3B):

[0360] Heptafluoropropyl (including isomers),

[0361] Pentafluoroethyl,

[0362] 2,2,2-Trifluoroethyl and

[0363] Trifluoromethyl

[0364] • "Substituted or unsubstituted alkenyl groups"

[0365] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0366] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0367] • Unsubstituted alkenyl groups (specific example group G4A):

[0368] vinyl,

[0369] Allyl

[0370] 1-Butenyl,

[0371] 2-Butenyl and

[0372] 3-Butenyl.

[0373] • Substituted alkenyl groups (specific example group G4B):

[0374] 1,3-Butadienyl,

[0375] 1-Methylvinyl

[0376] 1-Methylallyl,

[0377] 1,1-Dimethylallyl,

[0378] 2-Methylallyl and

[0379] 1,2-Dimethylallyl.

[0380] • "Substituted or unsubstituted alkynyl groups"

[0381] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0382] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.

[0383] • Unsubstituted alkynyl group (specific example group G5A):

[0384] Acetylene group.

[0385] • "Substituted or unsubstituted cycloalkyl groups"

[0386] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0387] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0388] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0389] Cyclopropyl

[0390] Cyclobutyl,

[0391] Cyclopentyl,

[0392] Cyclohexyl,

[0393] 1-Adamantyl,

[0394] 2-Adamantyl,

[0395] 1-norborneol and

[0396] 2-norborneol.

[0397] • Substituted cycloalkyl groups (specific example group G6B):

[0398] 4-Methylcyclohexyl.

[0399] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0400] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

[0401] -Si(G1)(G1)(G1),

[0402] -Si(G1)(G2)(G2),

[0403] -Si(G1)(G1)(G2),

[0404] -Si(G2)(G2)(G2),

[0405] -Si(G3)(G3)(G3) and

[0406] -Si(G6)(G6)(G6). Here.

[0407] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0408] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0409] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0410] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0411] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0412] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0413] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0414] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0415] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0416] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0417] ·“-O-(R 904 The group shown in the figure”

[0418] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0419] -O(G1)

[0420] -O(G2),

[0421] -O(G3) and

[0422] -O(G6).

[0423] Here,

[0424] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0425] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0426] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0427] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0428] ·“-S-(R 905 The group shown in the figure”

[0429] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0430] -S(G1),

[0431] -S(G2),

[0432] -S(G3) and

[0433] -S(G6).

[0434] Here,

[0435] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0436] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0437] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0438] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0439] ·"-N(R 906 (R) 907 The group shown in the figure”

[0440] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:

[0441] -N(G1)(G1),

[0442] -N(G2)(G2),

[0443] -N(G1)(G2),

[0444] -N(G3)(G3) and

[0445] -N(G6)(G6).

[0446] Here,

[0447] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0448] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0449] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0450] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0451] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0452] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0453] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0454] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0455] • "Halogen atom"

[0456] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0457] • "Substituted or unsubstituted fluoroalkyl groups"

[0458] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.

[0459] • "Substituted or unsubstituted haloalkyl groups"

[0460] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.

[0461] • "Substituted or unsubstituted alkoxy groups"

[0462] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0463] • "Substituted or unsubstituted alkylthio groups"

[0464] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0465] • "Substituted or unsubstituted aryloxy groups"

[0466] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0467] • "Substituted or unsubstituted arylthio groups"

[0468] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0469] • "Substituted or unsubstituted trialkylsilyl groups"

[0470] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0471] • "Substituted or unsubstituted aralkyl groups"

[0472] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0473] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0474] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirobisfluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc.

[0475] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

[0476] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0477]

[0478] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0479]

[0480] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0481] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0482]

[0483] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0484] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0485] • "Substituted or unsubstituted aryl groups"

[0486] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.

[0487] • "Substituted or unsubstituted divalent heterocyclic groups"

[0488] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0489] • "Substituted or unsubstituted alkylene compounds"

[0490] Unless otherwise stated, "substituted or unsubstituted alkylene groups" as described in this specification are divalent groups derived from "substituted or unsubstituted alkylene groups" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene groups" (specific example group G14) include divalent groups derived from "substituted or unsubstituted alkylene groups" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.

[0491] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).

[0492]

[0493]

[0494] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10Each can be a hydrogen atom or a substituent independently.

[0495] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0496]

[0497] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0498] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0499] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0500]

[0501] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0502] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0503] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0504]

[0505]

[0506]

[0507] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0508]

[0509]

[0510]

[0511]

[0512] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0513] The above is an explanation of "substituents described in this specification".

[0514] • "Cases where bonds form rings"

[0515] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".

[0516] The following description addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0517]

[0518] For example, in the case of R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", a group consisting of two adjacent elements is referred to as R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0519] The phrase "one or more groups" refers to the fact that two or more of the aforementioned groups consisting of two or more adjacent elements can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0520]

[0521] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923 When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .

[0522]

[0523] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one group of two adjacent rings," the "single ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring QC Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0524] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0525] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.

[0526] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.

[0527] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.

[0528] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0529] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.

[0530] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0531] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0532] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0533] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0534] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0535] In the case of “one or more groups consisting of two or more adjacent elements”, “forming a substituted or unsubstituted monocyclic ring by mutual bonding”, or “forming a substituted or unsubstituted fused ring by mutual bonding”, unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent elements are mutually bonded to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0536] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.

[0537] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.

[0538] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together" ("the case of forming a ring by bonding").

[0539] Substituents when described as "substituted or unsubstituted"

[0540] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...

[0541] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0542] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0543] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0544] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0545] -Si(R 901 (R) 902 (R) 903 ),

[0546] -O-(R 904 ),

[0547] -S-(R 905 ),

[0548] -N(R 906 (R) 907 ),

[0549] Halogen atom, cyano group, nitro group,

[0550] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0551] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0552] Groups, etc., in the composition group

[0553] Here, R 901 ~R 907 Each independently

[0554] hydrogen atom,

[0555] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0556] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0557] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0558] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0559] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0560] In R902 When there are more than two, more than two R 902 They are the same or different.

[0561] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0562] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0563] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0564] In R 906 When there are more than two, more than two R 906 They are the same or different.

[0565] In R 907 When there are more than two, more than two R 907 They are the same or different.

[0566] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0567] Alkyl groups with 1 to 50 carbon atoms

[0568] Aryl groups with 6 to 50 carbon atoms and

[0569] Groups in the group consisting of heterocyclic groups with 5 to 50 cyclic atoms.

[0570] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0571] Alkyl groups having 1 to 18 carbon atoms

[0572] aryl groups with 6 to 18 carbon atoms and

[0573] Groups in the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.

[0574] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0575] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0576] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.

[0577] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.

[0578] [Organic EL Components]

[0579] The organic EL element of the present invention will be described below.

[0580] An organic EL element according to one embodiment of the present invention is an organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer comprises: a light-emitting layer; a hole transport layer formed between the light-emitting layer and the first electrode; and a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer. The light-emitting layer contains a luminescent compound exhibiting a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm. The hole transport layer contains a compound represented by formula (A1), and the light-emitting auxiliary layer contains a compound represented by formula (A2).

[0581] Another embodiment of the present invention provides an organic EL element comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer comprises: a light-emitting layer; a hole transport layer formed between the light-emitting layer and the first electrode; and a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer. The plurality of light-emitting auxiliary layers include a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer. The hole transport layer comprises a compound or a diamine represented by formula (B1), and the light-emitting auxiliary layer b comprises a compound represented by formula (B2).

[0582] Another embodiment of the present invention provides an organic electroluminescent element comprising a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are sequentially disposed from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip, which includes a first organic layer. The first organic layer includes: a first light-emitting layer; a first hole transport layer formed between the first light-emitting layer and the first electrode; and a first light-emitting auxiliary layer formed between the first hole transport layer and the first light-emitting layer. The second light-emitting unit... The element includes a second light-emitting band, the second light-emitting band includes a second organic layer, the second organic layer includes: a second hole transport layer; a second light-emitting layer formed between the second hole transport layer and the second electrode; and a second light-emitting auxiliary layer formed between the second hole transport layer and the second light-emitting layer, at least one of the first light-emitting layer and the second light-emitting layer contains a luminescent compound exhibiting a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm, at least one of the first hole transport layer and the second hole transport layer contains a compound represented by formula (A1), and at least one of the first light-emitting auxiliary layer and the second light-emitting auxiliary layer contains a compound represented by formula (A2).

[0583] Another embodiment of the present invention provides an organic electroluminescent element comprising a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit, which are sequentially disposed from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip, which includes a first organic layer. The first organic layer includes: a first light-emitting layer; a first hole transport layer formed between the first light-emitting layer and the first electrode; and a plurality of first light-emitting auxiliary layers formed between the first hole transport layer and the first light-emitting layer. The plurality of first light-emitting auxiliary layers includes a first a light-emitting layer adjacent to the first hole transport layer. The second light-emitting unit includes a second light-emitting strip, which includes a second organic layer, comprising: a second hole transport layer; a second light-emitting layer formed between the second hole transport layer and the second electrode; and a plurality of second light-emitting auxiliary layers formed between the second hole transport layer and the second light-emitting layer. The plurality of second light-emitting auxiliary layers include a second light-emitting auxiliary layer 2a adjacent to the second hole transport layer and a second light-emitting auxiliary layer 2b adjacent to the second light-emitting layer. At least one of the first hole transport layer and the second hole transport layer contains a compound or diamine as shown in formula (B1), and at least one of the first b light-emitting auxiliary layer and the second b light-emitting auxiliary layer contains a compound as shown in formula (B2).

[0584] In this specification, the compound represented by formula (A1) may be referred to as "compound (A1)", the compound represented by formula (A2) may be referred to as "compound (A2)", the compound represented by formula (B1) may be referred to as "compound (B1)", and the compound represented by formula (B2) may be referred to as "compound (B2)".

[0585] In one embodiment of the present invention, the hole transport layer comprises compound (A1). The content of compound (A1) in the hole transport layer is not particularly limited as long as it achieves the effects of the present invention. However, in one embodiment of the present invention, the content of compound (A1) in the total amount of 100% by mass of the compound constituting the hole transport layer is preferably 50-100% by mass, more preferably 75-100% by mass, further preferably 90-100% by mass, even more preferably 95-100% by mass, even more preferably 98-100% by mass, and can be 100% by mass. Additionally, the hole transport layer may also contain compounds other than compound (A1).

[0586] In another embodiment of the present invention, the hole transport layer comprises compound (B1) or a diamine. The content of compound (A1) or diamine in the hole transport layer is not particularly limited as long as it achieves the effects of the present invention. However, in one embodiment of the present invention, the content of the compound constituting the hole transport layer is preferably 50-100% by mass, more preferably 75-100% by mass, further preferably 90-100% by mass, even more preferably 95-100% by mass, even more preferably 98-100% by mass, and can be 100% by mass. Additionally, the hole transport layer may also comprise compounds other than compound (B1) and diamine.

[0587] The hole transport band may include a single hole transport layer or multiple hole transport layers. When the hole transport band includes two or more hole transport layers, they may be the same or different. That is, the specific compounds and their compositions contained in the two or more hole transport layers may be the same or different in each layer. When the hole transport band includes two or more hole transport layers, at least one of the hole transport layers has the composition described above.

[0588] In one embodiment of the present invention, the light-emitting auxiliary layer comprises compound (A2) or compound (B2). Alternatively, the light-emitting auxiliary layer may also comprise compounds other than compound (A2) or compound (B2). The content of compound (A2) or compound (B2) in the light-emitting auxiliary layer is not particularly limited as long as it achieves the effects of the present invention; however, in one embodiment of the present invention, the content of compound (A2) in the total amount of 100% by mass of the compounds constituting the light-emitting auxiliary layer b is preferably 5 to 100% by mass.

[0589] In another embodiment of the present invention, the light-emitting auxiliary layer comprises a plurality of light-emitting auxiliary layers, including a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer, wherein the light-emitting auxiliary layer b comprises the compound (A2) or compound (B2). Additionally, the light-emitting auxiliary layer b may also comprise compounds other than compound (A2) or compound (B2).

[0590] The content of compound (A2) or compound (B2) in the light-emitting auxiliary layer b is not particularly limited as long as it can exert the effect of the present invention. However, in one embodiment of the present invention, the content of the compound constituting the light-emitting auxiliary layer b is preferably 50 to 100% by mass, more preferably 75 to 100% by mass, even more preferably 90 to 100% by mass, even more preferably 95 to 100% by mass, even more preferably 98 to 100% by mass, and can be 100% by mass.

[0591] Furthermore, the content of compound (A2) or compound (B2) in the plurality of light-emitting auxiliary layers is not particularly limited as long as it can exert the effect of the present invention. However, in one embodiment of the present invention, the content of the compound constituting the plurality of light-emitting auxiliary layers is preferably 5 to 100% by mass, more preferably 5 to 70% by mass, even more preferably 5 to 50% by mass, even more preferably 5 to 20% by mass, and even more preferably 5 to 10% by mass.

[0592] <Compounds (A1) and (A2)>

[0593] In one embodiment of the present invention, compound (A1) is shown in formula (A1), and the compound shown in formula (A1) is contained in the hole transport layer of an organic EL element.

[0594] (A1)

[0595] In formula (A1), N is the central nitrogen atom.

[0596] In equation (A1), L a1 L a2 and L a3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 cyclic atoms in the cyclic ring, either substituted or unsubstituted. As an example, in formula (A1), L... a1 L a2 and L a3 Each is an arylene group, either individually single-bonded or substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure. As another example, in formula (A1), L... a1 L a2 and L a3 Each is an arylene group, either independently a single bond, or substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure. a1 L a2 and L a3 At least one of them is a single bond.

[0597] In one implementation, in formula (A1), L a1 L a2 and L a3 Each is independently a single bond, or a substituted or unsubstituted phenylene. In another embodiment, in formula (A1), L a1 L a2 and L a3 Each is independently a single bond or an unsubstituted phenylene. In another embodiment, in formula (A1), L a1 L a2 and L a3Each is independently a single bond or an unsubstituted phenylene group, L a1 L a2 and L a3 At least one of them is a single bond.

[0598] In a specific example, in equation (A1), L a1 It can be bonded to any carbon atom position on the benzene ring that forms the 9,9-dimethyl-9H-fluorenyl group to which it is attached. For example, L a1 It can be bonded to any one of the carbon atoms at positions 1 to 4 of the 9,9-dimethyl-9H-fluorenyl group to which it is attached.

[0599] In equation (A1), Ar a2 This refers to an aryl group (6-30 carbon atoms) that is substituted or unsubstituted, a heterocyclic group (5-30 carbon atoms) that is substituted or unsubstituted, or a cycloalkyl group (5-30 carbon atoms) that is substituted or unsubstituted. As an example, in formula (A1), Ar... a2 It is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted, or a heterocyclic group with 5 to 30 cyclic atoms, either substituted or unsubstituted. As another example, in formula (A1), Ar... a2 It is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0600] The Ar a2 In the definition, the substituted or unsubstituted aryl group with 6 to 30 carbon atoms can be phenyl, p-phenyl, meta-phenyl, o-phenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracene, benzo[a]anthracene, phenanthrene, benzo[a]phenanthrene, phenatenyl, pyrene, benzo[a]benzo[a]phenyl, triphenylene, benzo[a]triphenylene, tetraphenyl, pentaphenyl, fluorene, 9,9'-spirobisfluorene, benzo[a]fluorene, diphenylene Fluorenyl, fluoranthyl, benzofluoranthyl, perylene, o-tolyl, m-tolyl, p-tolyl, p-xylyl, m-xylyl, o-xylyl, p-isopropylphenyl, m-isopropylphenyl, o-isopropylphenyl, p-tert-butylphenyl, m-tert-butylphenyl, o-tert-butylphenyl, 3,4,5-trimethylphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-bis(4-methylphenyl)fluorenyl, 9,9-bis(4-isopropylphenyl)fluorenyl, 9,9-bis(4-tert-butylphenyl)fluorenyl, cyanophenyl, triphenylsilylphenyl, trimethylsilylphenyl, phenylnaphthyl, or naphthylphenyl.

[0601] The Ar a2In the definition, the substituted or unsubstituted heterocyclic group with 5 to 30 cyclic atoms can be pyrroloyl, imidazoyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazoyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrazinyl, triazinyl, indoleyl, isoindoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinoxalolinyl, benzimidazolyl, indoleyl, phenanthrolineyl, phenanthridyl, acridineyl, phenazinyl, carbazoleyl, benzocarbazoleyl, morpholinyl, phenoxazolyl, etc. Azinyl, phenothiazinyl, azacarbazolyl, diazacarbazolyl, furanyl, xanthyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzooxazolyl, benzoisooxazolyl, dinaphthofuranyl, azadibenzofuranyl, diazadibenzofuranyl, azanaphthobenzofuranyl, diazanaphthobenzofuranyl, thiophenyl, benzothienyl, isobenzothienyl, dibenzothienyl l), naphthobenzothienyl, benzothiazolyl, benzoisothiazolyl, dinaphthothienyl, azadibenzothienyl, diazadibenzothienyl, diazadibenzothienyl, azanaphthobenzothienyl, azanaphthobenzothienyl, diazanaphthobenzothienyl obenzothienyl), (9-phenyl)carbazolyl, (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, (9-naphthyl)carbazolyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, methylbenzimidazolyl, ethylbenzimidazolyl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenylquinazolinyl, biphenylquinazolinyl, phenyldibenzofuranyl, methyldibenzofuranyl, tert-butyldibenzofuranyl, phenyldibenzothiophenyl, methyldibenzothiophenyl, or tert-butyldibenzothiophenyl.

[0602] The Ar a2 In the definition, the substituted or unsubstituted cycloalkyl group with 5 to 30 carbon atoms can be cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, or bicyclo[2.2.1]heptyl.

[0603] In one implementation, in formula (A1), Ar a2The substituted or unsubstituted fluorenyl group, substituted or unsubstituted spirobisfluorenyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted bicyclo[2.2.1]heptyl group, or substituted or unsubstituted carbazole group. In another embodiment, in formula (A1), Ar a2 The fluorenyl group may be substituted or unsubstituted, substituted or unsubstituted spirobisfluorenyl group may be substituted or unsubstituted, phenyl group may be substituted or unsubstituted, or adamantyl group may be substituted or unsubstituted. In another embodiment, Ar is a fluorene group in formula (A1). a2 The fluorenyl group may be substituted or unsubstituted, spirobisfluorenyl group may be substituted or unsubstituted, or phenyl group may be substituted or unsubstituted. In another embodiment, Ar is a fluorene group in formula (A1). a2 It can be a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted spirobisfluorenyl group. In another embodiment, in formula (A1), Ar a2 The fluorene group may be substituted or unsubstituted. In another embodiment, Ar is a fluorene group in formula (A1). a2 It is a fluorene group that is substituted with one or more methyl or phenyl groups or is unsubstituted.

[0604] In equation (A1), Ar a3 It is any one of the groups shown in formulas (a) to (e) described later.

[0605] In one implementation, in formula (A1), Ar a3 As shown in the following equation (1a).

[0606] (1a)

[0607] (In equation (1a),

[0608] Selected from R a1 ~R a13 One of them is a single bond that bonds with *1.

[0609] R is not a single bond that bonds with *1 a1 ~R a13 Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group with 1 to 50 carbon atoms, or -Si(R 901 (R) 902 (R) 903 The group shown is -O-(R) 904The group shown as ) or -S-(R 905 The group shown in the figure,

[0610] R 901 ~R 905 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0611] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0612] In R 902 When there are more than two, more than two R 902 They are the same or different.

[0613] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0614] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0615] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0616] R a14 It can be a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0617] Among them, R is selected from single bonds that are not bonded to *1. a1 ~R a13 and R a14 (Two adjacent benzene rings can bond to each other to form a substituted or unsubstituted benzene ring, or they may not bond to each other and thus not form a ring.)

[0618] In one implementation, in formula (1a), R is selected from a1 ~R a13 One of them is a single bond bonded to *1, and the other is an R that is not a single bond bonded to *1. a1 ~R a13 It is a hydrogen atom. In another embodiment, R is not a single bond bonded to *1. a1 ~R a13 They do not bond with each other and thus do not form a ring. In another embodiment, in equation (1a), R a14It is a hydrogen atom, or a substituted or unsubstituted phenyl group.

[0619] In a specific example, in equation (1a), the values ​​selected from R a1 ~R a13 One of them is a single bond bonded to *1, and the other is an R that is not a single bond bonded to *1. a1 ~R a13 For hydrogen atoms, R a14 It is a hydrogen atom, or a substituted or unsubstituted phenyl group, wherein R is not a single bond bonded to *1. a1 ~R a13 and R a14 They do not bond with each other and therefore do not form a ring.

[0620] In one embodiment of the present invention, compound (A2) is shown in formula (A2), and the compound shown in formula (A2) is contained in the light-emitting auxiliary layer of the organic EL element.

[0621] (A2)

[0622] In formula (A2), N is the central nitrogen atom.

[0623] In equation (A2), X b It represents an oxygen atom or a sulfur atom.

[0624] In equation (A2), the values ​​selected from R 1 ~R 8 One of them is a single bond that bonds with *2.

[0625] In equation (A2), the values ​​selected from R 1 ~R 8 The single bond in the *2 is not a bond that bonds with *2 and the two adjacent bonds can bond with each other to form a substituted or unsubstituted benzene ring, or they do not bond with each other and do not form a ring.

[0626] It is not a single bond bonded to *2 and the two adjacent R bonds are not bonded to each other. 1 ~R 8 It is a hydrogen atom.

[0627] In one implementation, in equation (A2), R 1 ~R 4 They do not bond with each other and therefore do not form a ring.

[0628] In another embodiment, in formula (A2), R 1 R 4 R5 or R 8 With *2 bond, R 1 ~R 8 They do not bond with each other and therefore do not form a ring.

[0629] In another embodiment, in formula (A2), R 1 With *2 bond, R 1 ~R 8 They do not bond with each other and therefore do not form a ring.

[0630] In another embodiment, in formula (A2), R 8 Bonded with *2, selected from R 1 ~R 4 Two adjacent benzene rings in the benzene ring bond to each other to form substituted or unsubstituted benzene rings.

[0631] In equation (A2), L b1 L b2 and L b3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 cyclic atoms, either substituted or unsubstituted. As an example, in formula (A2), L... b1 L b2 and L b3 Each is an arylene group, independently of a single bond, substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure. As another example, in formula (A2), L... b1 L b2 and L b3 Each is an arylene group, independently single-bonded, substituted, or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure. b1 L b2 and L b3 At least one of them is a single bond.

[0632] In one implementation, in formula (A2), L b2 It is a single key.

[0633] In another embodiment, in formula (A2), L b1 L b2 and L b3 Each is independently a single bond, or a substituted or unsubstituted phenylene. In another embodiment, in formula (A2), L b1 L b2 and L b3 Each is independently a single bond, or a substituted or unsubstituted phenylene, L b1 L b2 and L b3 At least one of them is a single bond.

[0634] In equation (A2), Ar b2 and Ar b3 Each is an independent group represented by any one of the formulas (a) to (e) described later.

[0635] In one implementation, Ar b2 and Ar b3 At least one of them is a group represented by formula (a) or formula (b). In a specific example, Ar b2 and Ar b3 At least one of them is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthylphenyl.

[0636] In one implementation, in formula (A2), Ar b2 and Ar b3 Any one of them is a group represented by formula (d). In a specific example, in formula (A2), Ar b2 and Ar b3 Any one of them is a group shown in formula (d) above, R 1 ~R 4 They do not bond with each other and therefore do not form a ring.

[0637] In another embodiment, in formula (A2), Ar b2 The group is shown in formula (d), where m4 is 0 and X is an oxygen atom. In a specific example, in formula (A2), L b2 For a single bond, Ar b2 The group is shown in formula (d), where m4 is 0 and X is an oxygen atom.

[0638] Ar in formula (A1) a3 And Ar in formula (A2) b2 and Ar b3 Each is independently a group represented by any one of the following formulas (a) to (e).

[0639]

[0640] In equation (a),

[0641] R 10 ~R 25 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0642] Among them, selected from R 10 ~R 14 One of them is a single bond that bonds with *f.

[0643] Selected from R 15 ~R 20 One of them is a single bond that bonds with *g, selected from R15 ~R 20 The other one is a single bond that bonds with *h.

[0644] *** indicates that L a3 L b2 or L b3 The location of the bond,

[0645] m1 is either 0 or 1, n1 is either 0 or 1.

[0646] When m1 is 0 and n1 is 0, *h and L a3 L b2 or L b3 bonding,

[0647] When m1 is 0 and n1 is 1, *f and L a3 L b2 or L b3 bonding,

[0648] When m1 is 1 and n1 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0649] k1 is 1 or 2.

[0650] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0651] In equation (b),

[0652] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0653] R 26 ~R 33 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0654] Among them, selected from R 26 ~R 33 One of them is a single bond that bonds with *i.

[0655] m2 is either 0 or 1, n2 is either 0 or 1.

[0656] When m2 is 0 and n2 is 0, *h and L a3 L b2 or L b3 bonding,

[0657] When m2 is 0 and n2 is 1, *f and L a3 L b2 or L b3 bonding,

[0658] When m2 is 1 and n2 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0659] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0660] In equation (c),

[0661] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0662] R 34 ~R 43 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0663] Among them, selected from R 34 ~R 43 One of them is a single bond that bonds with *j.

[0664] m3 is either 0 or 1, n3 is either 0 or 1.

[0665] When m3 is 0 and n3 is 0, *h and L a3 L b2 or L b3 bonding,

[0666] When m3 is 0 and n3 is 1, *f and L a3 L b2 or L b3 bonding,

[0667] When m3 is 1 and n3 is 0, the selection is from R. 10 ~R 14One of them is a single bond that bonds with *h.

[0668] Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 15 ~R 20 The two adjacent single bonds that are not any of the stated single bonds, and R 34 and R 35 They do not bond with each other and thus do not form a ring structure.

[0669] In equation (d),

[0670] R 10 ~R 14 The same applies to *f and ***.

[0671] R 44 ~R 51 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0672] X represents an oxygen atom, a sulfur atom, or CR. a R b or NR c ,

[0673] R a R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, or R a and R b They can bond with each other to form substituted or unsubstituted ring structures.

[0674] Among them, selected from R 44 ~R 51 One of them is a single bond that bonds with *k.

[0675] m4 is 0 or 1.

[0676] When m4 is 0, *f and L a3 L b2 or L b3 Bonding.

[0677] Selected from R 44 ~R 51 The single bonds are not the single bonds, and two adjacent bonds can independently bond to each other to form substituted or unsubstituted ring structures.

[0678] In equation (e),

[0679] R 10 ~R 14 The same applies to *f and ***.

[0680] R 52 ~R 66 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0681] Among them, selected from R 52 ~R 56 One of them is a single bond bonded to *l, selected from R 52 ~R 56 The other one is a single bond that bonds with *m.

[0682] m5 is 0 or 1.

[0683] When m5 is 0, *f and L a3 L b2 or L b3 Bonding.

[0684] Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 52 ~R 56 The two adjacent R bonds that are not any of the stated single bonds 52 and R 61 and R 56 and R 57 They do not bond with each other and thus do not form a ring structure.

[0685] In one embodiment, the alkyl group with 1 to 50 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, an alkyl group with 1 to 30 carbon atoms, an alkyl group with 1 to 20 carbon atoms, an alkyl group with 1 to 10 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or an alkyl group with 1 to 3 carbon atoms.

[0686] In one embodiment, the cycloalkyl group with 3 to 50 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, a cycloalkyl group with 3 to 30 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, or a cycloalkyl group with 3 to 6 carbon atoms.

[0687] In one embodiment, the aryl group with 6 to 30 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, an aryl group with 6 to 20 carbon atoms or an aryl group with 6 to 12 carbon atoms.

[0688] In one embodiment, the aryl group with 6 to 50 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, an aryl group with 6 to 30 carbon atoms, an aryl group with 6 to 20 carbon atoms, or an aryl group with 6 to 13 carbon atoms.

[0689] In one embodiment, the heterocyclic group with 5 to 50 cyclic atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, a heterocyclic group with 5 to 30 cyclic atoms, a heterocyclic group with 5 to 20 cyclic atoms, or a heterocyclic group with 5 to 13 cyclic atoms.

[0690] In one implementation, in equation (a), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (a), R is a single bond that is neither bonded to *g nor to *h. 15 ~R 20 All are hydrogen atoms. In another embodiment, in formula (a), R 21 ~R 25 All are hydrogen atoms.

[0691] In one implementation, in equation (b), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In yet another embodiment, in formula (b), R is a single bond that is neither bonded to *g nor to *h. 15 ~R 20 All are hydrogen atoms. In another embodiment, in formula (b), R is not a single bond bonded to *i. 26 ~R 33 All are hydrogen atoms.

[0692] In one implementation, in equation (c), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (c), R is a single bond that is neither bonded to *g nor to *h. 15 ~R 20 All are hydrogen atoms. In another embodiment, in formula (c), R is not a single bond bonded to *j. 34 ~R 43 All are hydrogen atoms.

[0693] In one implementation, in equation (d), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (d), R is not a single bond bonded to *k. 44 ~R 51 All are hydrogen atoms.

[0694] In one implementation, in equation (d), R a R b and R c Each is independently a hydrogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, or R. a and R b They can bond with each other to form substituted or unsubstituted fluorene rings.

[0695] In one implementation, in equation (e), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (e), R is a single bond that is neither bonded to *l nor to *m. 52 ~R 56 All are hydrogen atoms. In another embodiment, in formula (e), R 57 ~R 61 All are hydrogen atoms. In another embodiment, in formula (e), R 62 ~R 66 All are hydrogen atoms.

[0696] As stated above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, compound (A1) or compound (A2) may contain naturally occurring deuterium atoms.

[0697] Furthermore, by using a deuterated compound as part or all of the starting compound, a deuterium atom can be intentionally introduced into compound (A1) or compound (A2). Therefore, in one embodiment of the invention, compound (A1) or compound (A2) contains at least one deuterium atom. That is, compound (A1) or compound (A2) are respectively the compounds represented by formula (A1) and formula (A2), and can be compounds in which at least one of the hydrogen atoms is a deuterium atom.

[0698] The deuteration rate of compound (A1) or compound (A2) depends on the deuteration rate of the starting material compound. Even when using a starting material with a certain deuteration rate, it may still contain a certain proportion of naturally occurring protium isotopes. Therefore, the deuteration rate of compound (A1) or compound (A2) includes a proportion that takes into account trace amounts of naturally occurring isotopes, compared to the proportion obtained by simply calculating the number of deuterium atoms shown in the chemical formula.

[0699] The deuteration rate of compound (A1) or compound (A2) is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0700] Compound (A1) or compound (A2) may be a mixture comprising a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate of such mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%.

[0701] Furthermore, the ratio of the number of deuterium atoms in compound (A1) to the total number of hydrogen atoms is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0702] The details of substituents (any substituents) expressed as “substituted or unsubstituted” in the above definitions are as described in “Substituents expressed as “substituted or unsubstituted””, unless otherwise stated.

[0703] Compound (A1) can be readily prepared by those skilled in the art with reference to the following synthetic examples and known synthetic methods.

[0704] Specific examples of compound (A1) are shown below, but are not limited to the following exemplary compounds.

[0705] In the following specific examples, D represents a deuterium atom.

[0706]

[0707]

[0708]

[0709]

[0710]

[0711]

[0712]

[0713]

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729]

[0730]

[0731]

[0732]

[0733]

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

[0753]

[0754]

[0755]

[0756]

[0757]

[0758]

[0759]

[0760]

[0761]

[0762]

[0763]

[0764]

[0765]

[0766]

[0767]

[0768]

[0769]

[0770]

[0771]

[0772]

[0773]

[0774]

[0775]

[0776]

[0777]

[0778]

[0779]

[0780]

[0781]

[0782]

[0783]

[0784]

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792] In one embodiment, the hole transport layer comprises at least one of the following compounds:

[0793] , , , , , , , , and .

[0794] In another embodiment, the hole transport layer comprises at least one of the following compounds:

[0795] , , , and .

[0796] In another embodiment, the hole transport layer comprises at least one of the following compounds:

[0797] and .

[0798] Compound (A2) can be readily prepared by those skilled in the art with reference to the following synthetic examples and known synthetic methods.

[0799] Specific examples of compound (A2) are shown below, but are not limited to the following exemplary compounds.

[0800] In the following specific examples, D represents a deuterium atom.

[0801]

[0802]

[0803]

[0804]

[0805]

[0806]

[0807]

[0808]

[0809]

[0810]

[0811]

[0812]

[0813]

[0814]

[0815]

[0816]

[0817]

[0818]

[0819]

[0820]

[0821]

[0822]

[0823]

[0824]

[0825]

[0826]

[0827]

[0828]

[0829]

[0830]

[0831]

[0832]

[0833]

[0834]

[0835]

[0836]

[0837]

[0838]

[0839]

[0840]

[0841]

[0842]

[0843]

[0844] In one embodiment, the light-emitting auxiliary layer comprises at least one of the following compounds:

[0845] , , , , , , , and .

[0846] In another embodiment, the light-emitting auxiliary layer comprises at least one of the following compounds:

[0847] , , and .

[0848] In another embodiment, the light-emitting auxiliary layer comprises at least one of the following compounds:

[0849] and .

[0850] <Compounds (B1) and (B2)>

[0851] In another embodiment of the invention, compound (B1) is as shown in formula (B1), and the compound or diamine shown in formula (B1) is contained in the hole transport layer of the organic EL element.

[0852] (B1)

[0853] In formula (B1), N is the central nitrogen atom.

[0854] In equation (B1), L a1 L a2 and L a3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 cyclic atoms in the cyclic ring, either substituted or unsubstituted. As an example, in formula (B1), L... a1 L a2 and L a3 Each is an arylene group, either individually single-bonded or substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure. As another example, in formula (B1), L... a1 La2 and L a3 Each is an arylene group, either independently a single bond, or substituted or unsubstituted, with 6 to 18 carbon atoms in a cyclic structure. a1 L a2 and L a3 At least one of them is a single bond.

[0855] In one implementation, in formula (B1), L a1 L a2 and L a3 Each is independently a single bond, or a substituted or unsubstituted phenylene. In another embodiment, in formula (B1), L a1 L a2 and L a3 Each is independently a single bond or an unsubstituted phenylene. In another embodiment, in formula (B1), L a1 L a2 and L a3 Each is independently a single bond or an unsubstituted phenylene group, L a1 L a2 and L a3 At least one of them is a single bond.

[0856] In a specific example, in equation (B1), L a1 and L a2 They can be bonded to any carbon atom position on the benzene ring that forms the respective 9,9-dimethyl-9H-fluorenyl group to which they are attached. For example, L a1 and L a2 They can be bonded to any of the carbon atoms at positions 1 to 4 of the respective 9,9-dimethyl-9H-fluorenyl groups to which they are attached.

[0857] In equation (B1), Ar a3 It is any one of the groups shown in formulas (a) to (e) described later.

[0858] In one implementation, in formula (B1), Ar a3 As shown in the following equation (1a):

[0859] (1a)

[0860] (In equation (1a),

[0861] Selected from R a1 ~R a13 One of them is a single bond that bonds with *1.

[0862] R is not a single bond that bonds with *1 a1 ~R a13Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group with 1 to 50 carbon atoms, or -Si(R 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown as ) or -S-(R 905 The group shown in the figure,

[0863] R 901 ~R 905 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0864] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0865] In R 902 When there are more than two, more than two R 902 They are the same or different.

[0866] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0867] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0868] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0869] R a14 It can be a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0870] Among them, R is selected from single bonds that are not bonded to *1. a1 ~R a13 and R a14(Two adjacent benzene rings can bond to each other to form a substituted or unsubstituted benzene ring, or they may not bond to each other and thus not form a ring.)

[0871] In one implementation, in formula (1a), R is selected from a1 ~R a13 One of them is a single bond bonded to *1, and the other is an R that is not a single bond bonded to *1. a1 ~R a13 It is a hydrogen atom. In another embodiment, R is not a single bond bonded to *1. a1 ~R a13 They do not bond with each other and thus do not form a ring. In another embodiment, in equation (1a), R a14 It is a hydrogen atom, or a substituted or unsubstituted phenyl group.

[0872] In a specific example, in equation (1a), the values ​​selected from R a1 ~R a13 One of them is a single bond bonded to *1, and the other is an R that is not a single bond bonded to *1. a1 ~R a13 For hydrogen atoms, R a14 It is a hydrogen atom, or a substituted or unsubstituted phenyl group, wherein R is not a single bond bonded to *1. a1 ~R a13 and R a14 They do not bond with each other and therefore do not form a ring.

[0873] In another embodiment of the present invention, compound (B2) is as shown in formula (B2), and the compound shown in formula (B2) is contained in the light-emitting auxiliary layer b of the organic EL element.

[0874] (B2)

[0875] In formula (B2), N is the central nitrogen atom.

[0876] In equation (B2), Ar b1 It is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted, a heterocyclic group with 5 to 30 carbon atoms that is substituted or unsubstituted, or a cycloalkyl group with 5 to 30 carbon atoms that is substituted or unsubstituted.

[0877] The Ar b1In the definition, the substituted or unsubstituted aryl group with 6 to 30 carbon atoms can be phenyl, p-phenyl, meta-phenyl, o-phenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracene, benzo[a]anthracene, phenanthrene, benzo[a]phenanthrene, phenatenyl, pyrene, benzo[a]benzo[a]phenyl, triphenylene, benzo[a]triphenylene, tetraphenyl, pentaphenyl, fluorene, 9,9'-spirobisfluorene, benzo[a]fluorene, diphenylene Fluorenyl, fluoranthyl, benzofluoranthyl, perylene, o-tolyl, m-tolyl, p-tolyl, p-xylyl, m-xylyl, o-xylyl, p-isopropylphenyl, m-isopropylphenyl, o-isopropylphenyl, p-tert-butylphenyl, m-tert-butylphenyl, o-tert-butylphenyl, 3,4,5-trimethylphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-bis(4-methylphenyl)fluorenyl, 9,9-bis(4-isopropylphenyl)fluorenyl, 9,9-bis(4-tert-butylphenyl)fluorenyl, cyanophenyl, triphenylsilylphenyl, trimethylsilylphenyl, phenylnaphthyl, or naphthylphenyl.

[0878] The Ar b1In the definition, the substituted or unsubstituted heterocyclic group with 5 to 30 cyclic atoms can be pyrroloyl, imidazoyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazoyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrazinyl, triazinyl, indoleyl, isoindoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinoxalolinyl, benzimidazolyl, indoleyl, phenanthrolineyl, phenanthridyl, acridineyl, phenazinyl, carbazoleyl, benzocarbazoleyl, morpholinyl, phenoxazolyl, etc. Azinyl, phenothiazinyl, azacarbazolyl, diazacarbazolyl, furanyl, xanthyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzooxazolyl, benzoisooxazolyl, dinaphthofuranyl, azadibenzofuranyl, diazadibenzofuranyl, azanaphthobenzofuranyl, diazanaphthobenzofuranyl, thiophenyl, benzothienyl, isobenzothienyl, dibenzothienyl l), naphthobenzothienyl, benzothiazolyl, benzoisothiazolyl, dinaphthothienyl, azadibenzothienyl, diazadibenzothienyl, diazadibenzothienyl, azanaphthobenzothienyl, azanaphthobenzothienyl, diazanaphthobenzothienyl obenzothienyl), (9-phenyl)carbazolyl, (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, (9-naphthyl)carbazolyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, methylbenzimidazolyl, ethylbenzimidazolyl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenylquinazolinyl, biphenylquinazolinyl, phenyldibenzofuranyl, methyldibenzofuranyl, tert-butyldibenzofuranyl, phenyldibenzothiophenyl, methyldibenzothiophenyl, or tert-butyldibenzothiophenyl.

[0879] The Ar b1 In the definition, the substituted or unsubstituted cycloalkyl group with 5 to 30 carbon atoms can be cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, or bicyclo[2.2.1]heptyl.

[0880] In one implementation, in formula (B2), Ar b1 It can be a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted naphthobenzofuranyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted carbazoyl.

[0881] In one implementation, in formula (B2), Ar b1 It is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted naphthobenzofuranyl group.

[0882] In equation (B2), L b1 L b2 and L b3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms in the cyclic ring.

[0883] In one implementation, in equation (B2), L b2 It is a single key.

[0884] In another embodiment, in formula (B2), L b1 L b2 and L b3 Each is an independent single bond, or a substituted or unsubstituted phenylene.

[0885] In equation (B2), Ar b2 and Ar b3 Each is an independent group represented by any one of the formulas (a) to (e) described later.

[0886] In one implementation, Ar b2 and Ar b3 At least one of them is a group represented by formula (a) or formula (b). In a specific example, Ar b2 and Ar b3 At least one of them is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthylphenyl.

[0887] In one implementation, in formula (B2), Ar b2 and Ar b3 Any one of them is a group represented by formula (d).

[0888] In another embodiment, in formula (B2), Ar b2 The group is shown in formula (d), where m4 is 0 and X is an oxygen atom. In a specific example, in formula (B2), L b2 For a single bond, Ar b2 The group is shown in formula (d), where m4 is 0 and X is an oxygen atom.

[0889] Ar in equation (B1) a3 And Ar in formula (B2) b2 and Ar b3 Each is independently a group represented by any one of the following formulas (a) to (e):

[0890]

[0891] In equation (a),

[0892] R 10 ~R 25 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0893] Among them, selected from R 10 ~R 14 One of them is a single bond that bonds with *f.

[0894] Selected from R 15 ~R 20 One of them is a single bond that bonds with *g, selected from R 15 ~R 20 The other one is a single bond that bonds with *h.

[0895] *** indicates that L a3 L b2 or L b3 The location of the bond,

[0896] m1 is either 0 or 1, n1 is either 0 or 1.

[0897] When m1 is 0 and n1 is 0, *h and L a3 L b2 or L b3 bonding,

[0898] When m1 is 0 and n1 is 1, *f and L a3 L b2 or L b3 bonding,

[0899] When m1 is 1 and n1 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0900] k1 is 1 or 2.

[0901] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0902] In equation (b),

[0903] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0904] R 26 ~R 33 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0905] Among them, selected from R 26 ~R 33 One of them is a single bond that bonds with *i.

[0906] m2 is either 0 or 1, n2 is either 0 or 1.

[0907] When m2 is 0 and n2 is 0, *h and L a3 L b2 or L b3 bonding,

[0908] When m2 is 0 and n2 is 1, *f and L a3 L b2 or L b3 bonding,

[0909] When m2 is 1 and n2 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0910] Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure.

[0911] In equation (c),

[0912] R 10 ~R 20 The same applies to *f, *g, *h, and ***.

[0913] R 34 ~R 43 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0914] Among them, selected from R 34 ~R 43 One of them is a single bond that bonds with *j.

[0915] m3 is either 0 or 1, n3 is either 0 or 1.

[0916] When m3 is 0 and n3 is 0, *h and L a3 L b2 or L b3 bonding,

[0917] When m3 is 0 and n3 is 1, *f and L a3 L b2 or L b3 bonding,

[0918] When m3 is 1 and n3 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h.

[0919] Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 15 ~R 20 The two adjacent single bonds that are not any of the stated single bonds, and R 34 and R 35 They do not bond with each other and thus do not form a ring structure.

[0920] In equation (d),

[0921] R 10 ~R 14 The same applies to *f and ***.

[0922] R 44 ~R 51 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0923] X represents an oxygen atom, a sulfur atom, or CR. a R b or NR c ,

[0924] R a R b and R cEach of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, or R a and R b They can bond with each other to form substituted or unsubstituted ring structures.

[0925] Among them, selected from R 44 ~R 51 One of them is a single bond that bonds with *k.

[0926] m4 is 0 or 1.

[0927] When m4 is 0, *f and L a3 L b2 or L b3 Bonding.

[0928] Selected from R 44 ~R 51 The single bonds are not the single bonds, and two adjacent bonds can independently bond to each other to form substituted or unsubstituted ring structures.

[0929] In equation (e),

[0930] R 10 ~R 14 The same applies to *f and ***.

[0931] R 52 ~R 66 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0932] Among them, selected from R 52 ~R 56 One of them is a single bond bonded to *l, selected from R 52 ~R 56 The other one is a single bond that bonds with *m.

[0933] m5 is 0 or 1.

[0934] When m5 is 0, *f and L a3 L b2 or L b3 Bonding.

[0935] Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 52 ~R 56The two adjacent R bonds that are not any of the stated single bonds 52 and R 61 and R 56 and R 57 They do not bond with each other and thus do not form a ring structure.

[0936] In one embodiment, the alkyl group with 1 to 50 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, an alkyl group with 1 to 30 carbon atoms, an alkyl group with 1 to 20 carbon atoms, an alkyl group with 1 to 10 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or an alkyl group with 1 to 3 carbon atoms.

[0937] In one embodiment, the cycloalkyl group with 3 to 50 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, a cycloalkyl group with 3 to 30 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, or a cycloalkyl group with 3 to 6 carbon atoms.

[0938] In one embodiment, the aryl group with 6 to 30 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, an aryl group with 6 to 20 carbon atoms or an aryl group with 6 to 12 carbon atoms.

[0939] In one embodiment, the aryl group with 6 to 50 carbon atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, an aryl group with 6 to 30 carbon atoms, an aryl group with 6 to 20 carbon atoms, or an aryl group with 6 to 13 carbon atoms.

[0940] In one embodiment, the heterocyclic group with 5 to 50 cyclic atoms mentioned in the definition of substituents in formulas (a) to (e) can be, for example, a heterocyclic group with 5 to 30 cyclic atoms, a heterocyclic group with 5 to 20 cyclic atoms, or a heterocyclic group with 5 to 13 cyclic atoms.

[0941] In one implementation, in equation (a), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (a), R is a single bond that is neither bonded to *g nor to *h. 15 ~R 20 All are hydrogen atoms. In another embodiment, in formula (a), R 21 ~R 25 All are hydrogen atoms.

[0942] In one implementation, in equation (b), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (b), R is neither a single bond bonded to *g nor a single bond bonded to *h.15 ~R 20 All are hydrogen atoms. In another embodiment, in formula (b), R is not a single bond bonded to *i. 26 ~R 33 All are hydrogen atoms.

[0943] In one implementation, in equation (c), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (c), R is a single bond that is neither bonded to *g nor to *h. 15 ~R 20 All are hydrogen atoms. In another embodiment, in formula (c), R is not a single bond bonded to *j. 34 ~R 43 All are hydrogen atoms.

[0944] In one implementation, in equation (d), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (d), R is not a single bond bonded to *k. 44 ~R 51 All are hydrogen atoms.

[0945] In one implementation, in equation (d), R a R b and R c Each is independently a hydrogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, or R. a and R b They can bond with each other to form substituted or unsubstituted fluorene rings.

[0946] In one implementation, in equation (e), R is not a single bond bonded to *f. 10 ~R 14 All are hydrogen atoms. In another embodiment, in formula (e), R is a single bond that is neither bonded to *l nor to *m. 52 ~R 56 All are hydrogen atoms. In another embodiment, in formula (e), R 57 ~R 61 All are hydrogen atoms. In another embodiment, in formula (e), R 62 ~R 66 All are hydrogen atoms.

[0947] As stated above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, compound (B1) or compound (B2) may contain naturally occurring deuterium atoms.

[0948] Furthermore, by using a deuterated compound as part or all of the starting compound, a deuterium atom can be intentionally introduced into compound (B1) or compound (B2). Therefore, in one embodiment of the invention, compound (B1) or compound (B2) contains at least one deuterium atom. That is, compound (B1) or compound (B2) are respectively the compounds represented by formula (B1) and formula (B2), and can be compounds in which at least one of the hydrogen atoms is a deuterium atom.

[0949] The deuteration rate of compound (B1) or compound (B2) depends on the deuteration rate of the starting material compound. Even when using a starting material with a certain deuteration rate, it may still contain a certain proportion of naturally occurring protium isotopes. Therefore, the deuteration rate of compound (B1) or compound (B2) includes a proportion that takes into account trace amounts of naturally occurring isotopes, compared to the proportion obtained by simply calculating the number of deuterium atoms shown in the chemical formula.

[0950] The deuteration rate of compound (B1) or compound (B2) is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0951] Compound (B1) or compound (B2) may be a mixture comprising a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate of such mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%.

[0952] Furthermore, the ratio of the number of deuterium atoms in compound (B1) or compound (B2) to the total number of hydrogen atoms is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0953] The details of substituents (any substituents) expressed as “substituted or unsubstituted” in the above definitions are as described in “Substituents expressed as “substituted or unsubstituted””, unless otherwise stated.

[0954] Compound (B1) can be readily prepared by those skilled in the art with reference to the following synthetic examples and known synthetic methods.

[0955] Specific examples of compound (B1) are shown below, but are not limited to the following exemplary compounds.

[0956] In the following specific examples, D represents a deuterium atom.

[0957]

[0958]

[0959]

[0960]

[0961]

[0962]

[0963]

[0964]

[0965]

[0966]

[0967]

[0968]

[0969]

[0970]

[0971]

[0972]

[0973]

[0974]

[0975]

[0976]

[0977]

[0978]

[0979]

[0980]

[0981]

[0982]

[0983]

[0984]

[0985]

[0986]

[0987]

[0988]

[0989]

[0990]

[0991]

[0992]

[0993]

[0994]

[0995]

[0996]

[0997]

[0998]

[0999]

[1000] In one embodiment, the light-emitting auxiliary layer (i.e., light-emitting auxiliary layer b) comprises at least one of the following compounds:

[1001] , , , , , , , , and .

[1002] In another embodiment, the light-emitting auxiliary layer (i.e., light-emitting auxiliary layer b) comprises at least one of the following compounds:

[1003] , , , , , and .

[1004] In another embodiment, the light-emitting auxiliary layer (i.e., light-emitting auxiliary layer b) comprises at least one of the following compounds:

[1005] and .

[1006] <Diamine>

[1007] In another embodiment of the invention, a diamine or the compound represented by the aforementioned formula (B1) is contained in the hole transport layer of the organic EL element.

[1008] In one embodiment, the diamine contained in the hole transport layer is a compound represented by the following formula (12):

[1009]

[1010] In the above equation (12),

[1011] L A2 L B2 L C2 and L D2 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[1012] k is 1, 2, 3, or 4.

[1013] When k is 1, L E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[1014] When k is 2, 3, or 4, there are 2, 3, or 4 L E2 They are the same or different.

[1015] When k is 2, 3, or 4, multiple L E2 They may bond together to form substituted or unsubstituted monocyclic rings, or they may bond together to form substituted or unsubstituted fused rings, or they may not bond together.

[1016] L does not form the single ring and does not form the fused ring E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[1017] A 2 B 2 C 2 and D 2 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms, or a -Si(R') group. 901 )(R' 902 )(R' 903 ),

[1018] R' 901 、R' 902 and R' 903 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic formation.

[1019] In R' 901 When there are multiple R's, multiple R's 901 They are the same or different.

[1020] In R' 902 When there are multiple R's, multiple R's 902 They are the same or different.

[1021] In R' 903 When there are multiple R's, multiple R's 903 They are the same or different.

[1022] In equation (12), A 2 B 2 C 2 and D 2 Preferably, each is independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoleyl.

[1023] Furthermore, more preferably, in equation (12), A 2 B 2 C 2 and D 2 At least one of them is a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl or a substituted or unsubstituted carbazoyl.

[1024] A 2 B 2 C 2 and D 2 The preferred fluorenyl group may have a substituent at the 9-position, for example, it may be 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl. Additionally, the substituents at the 9-position may form a ring with each other; for example, the substituents at the 9-position may form a fluorenyl skeleton or a zeolite skeleton.

[1025] L A2 L B2 L C2 and L D2 Preferably, each arylene group is a single bond, substituted or unsubstituted cyclic carbon with 6 to 12 carbon atoms.

[1026] The substituted or unsubstituted arylene groups having 6 to 12 carbon atoms are preferably each independently a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[1027] The phenylene oxide is o-phenylene oxide, m-phenylene oxide, or p-phenylene oxide, with p-phenylene oxide being particularly preferred.

[1028] The phenylene oxide is preferably 4,2'-phenylene oxide, 4,3'-phenylene oxide, 4,4'-phenylene oxide or 3,3'-phenylene oxide, more preferably 4,3'-phenylene oxide, 4,4'-phenylene oxide or 3,3'-phenylene oxide, and particularly preferably 4,4'-phenylene oxide.

[1029] The naphthyl group is preferably 1,4-naphthyl, 2,6-naphthyl, 1,5-naphthyl or 1,8-naphthyl.

[1030] Specific examples of compounds represented by formula (12) may include, for example, the following compounds.

[1031]

[1032] <Detailed Explanation of Organic EL Components>

[1033] An organic EL element according to one embodiment of the present invention is an organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer comprises: a light-emitting layer; a hole transport layer formed between the light-emitting layer and the first electrode; and a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer. The light-emitting layer contains a luminescent compound exhibiting a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm. The hole transport layer contains a compound represented by formula (A1) above, and the light-emitting auxiliary layer contains a compound represented by formula (A2) above.

[1034] Another embodiment of the present invention provides an organic EL element comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer comprises: a light-emitting layer; a hole transport layer formed between the light-emitting layer and the first electrode; and a plurality of light-emitting auxiliary layers formed between the hole transport layer and the light-emitting layer. The plurality of light-emitting auxiliary layers include a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer. The hole transport layer comprises a compound or a diamine as shown in formula (B1) above, and the light-emitting auxiliary layer b comprises a compound as shown in formula (B2) above.

[1035] Another embodiment of the present invention provides an organic electroluminescent element comprising a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are sequentially disposed from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip, which includes a first organic layer. The first organic layer includes: a first light-emitting layer; a first hole transport layer formed between the first light-emitting layer and the first electrode; and a first light-emitting auxiliary layer formed between the first hole transport layer and the first light-emitting layer. The second light-emitting unit... The element includes a second light-emitting band, the second light-emitting band includes a second organic layer, the second organic layer includes: a second hole transport layer; a second light-emitting layer formed between the second hole transport layer and the second electrode; and a second light-emitting auxiliary layer formed between the second hole transport layer and the second light-emitting layer, at least one of the first light-emitting layer and the second light-emitting layer contains a luminescent compound exhibiting a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm, at least one of the first hole transport layer and the second hole transport layer contains a compound represented by formula (A1) above, and at least one of the first light-emitting auxiliary layer and the second light-emitting auxiliary layer contains a compound represented by formula (A2) above.

[1036] Another embodiment of the present invention provides an organic electroluminescent element comprising a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode. The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit, which are sequentially disposed from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip, which includes a first organic layer. The first organic layer includes: a first light-emitting layer; a first hole transport layer formed between the first light-emitting layer and the first electrode; and a plurality of first light-emitting auxiliary layers formed between the first hole transport layer and the first light-emitting layer. The plurality of first light-emitting auxiliary layers includes a first a light-emitting layer adjacent to the first hole transport layer. The second light-emitting unit includes a second light-emitting strip, which includes a second organic layer, comprising: a second hole transport layer; a second light-emitting layer formed between the second hole transport layer and the second electrode; and a plurality of second light-emitting auxiliary layers formed between the second hole transport layer and the second light-emitting layer. The plurality of second light-emitting auxiliary layers include a second light-emitting auxiliary layer 2a adjacent to the second hole transport layer and a second light-emitting auxiliary layer 2b adjacent to the second light-emitting layer. At least one of the first hole transport layer and the second hole transport layer contains a compound or diamine as shown in formula (B1) above, and at least one of the first b light-emitting auxiliary layer and the second b light-emitting auxiliary layer contains a compound as shown in formula (B2) above.

[1037] The first electrode can be an anode, and the second electrode can be a cathode.

[1038] The hole transport band includes one or more hole transport layers, and may further include a hole injection layer, an electron blocking layer, an exciton blocking layer, etc., between the first electrode and the hole transport layer.

[1039] In one embodiment of the present invention, the light-emitting auxiliary layer may include a single light-emitting auxiliary layer or multiple light-emitting auxiliary layers. The single light-emitting auxiliary layer includes a light-emitting auxiliary layer a adjacent to the light-emitting layer. The multiple light-emitting auxiliary layers include a light-emitting auxiliary layer a adjacent to the light-emitting layer and a light-emitting auxiliary layer b adjacent to the light-emitting auxiliary layer a.

[1040] In addition, other examples of organic layers in organic EL devices may include, but are not limited to, spacer layers, electron transport bands (electron injection layers, electron transport layers, hole blocking layers, etc.) disposed between the cathode and the light-emitting layer.

[1041] As one embodiment of the present invention, the organic EL element can be a fluorescent or phosphorescent monochromatic light-emitting element, a fluorescent / phosphorescent hybrid white light-emitting element, a simple type with a single light-emitting unit, or a series type with multiple light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer (at least one of which is a light-emitting layer) and emits light through recombination of injected holes and electrons.

[1042] For example, the following are representative element structures for simple organic EL elements.

[1043] (1) Anode / Light-emitting unit / Cathode

[1044] Furthermore, the light-emitting unit can be a multilayer type with multiple phosphorescent or fluorescent light-emitting layers. In this case, spacer layers can be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer. The following lists representative layer structures of simple light-emitting units. The layers in parentheses are arbitrary.

[1045] (a) (hole injection layer / ) hole transport layer / fluorescent layer / electron transport layer ( / electron injection layer)

[1046] (b) (hole injection layer / ) hole transport layer / fluorescent auxiliary layer / fluorescent layer / electron transport layer ( / electron injection layer)

[1047] (c) (hole injection layer / ) hole transport layer / fluorescent auxiliary layer / fluorescent layer / electron transport layer a / electron transport layer b ( / electron injection layer)

[1048] (d) (hole injection layer / ) hole transport layer / fluorescent auxiliary layer a / fluorescent auxiliary layer b / fluorescent layer / electron transport layer ( / electron injection layer)

[1049] (e) (hole injection layer / ) hole transport layer / fluorescent auxiliary layer a / fluorescent auxiliary layer b / fluorescent layer / electron transport layer a / electron transport layer b ( / electron injection layer)

[1050] (f) (hole injection layer / ) hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer ( / electron injection layer)

[1051] (g) (hole injection layer / ) hole transport layer / phosphorescent layer / spacer layer / fluorescent auxiliary layer / fluorescent layer / electron transport layer ( / electron injection layer)

[1052] (h) (hole injection layer / ) hole transport layer / phosphorescent layer / spacer layer / fluorescent auxiliary layer / fluorescent layer / electron transport layer a / electron transport layer b ( / electron injection layer)

[1053] (i) (hole injection layer / ) hole transport layer / phosphorescent layer / spacer layer / fluorescent auxiliary layer a / fluorescent auxiliary layer b / fluorescent layer / electron transport layer ( / electron injection layer)

[1054] (j) (hole injection layer / ) hole transport layer / phosphorescent layer / spacer layer / fluorescent auxiliary layer a / fluorescent auxiliary layer b / fluorescent layer / electron transport layer a / electron transport layer b ( / electron injection layer)

[1055] Each of the phosphorescent or fluorescent light-emitting layers can exhibit a different light-emitting color.

[1056] It should be noted that electron blocking layers can be appropriately placed between each luminescent layer and the hole transport layer or spacer layer. Additionally, hole blocking layers can also be appropriately placed between each luminescent layer and the electron transport layer. By placing electron or hole blocking layers, electrons or holes can be confined within the luminescent layer, thereby increasing the probability of charge recombination within the luminescent layer and improving luminous efficiency.

[1057] Furthermore, in a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer can function as an electron blocking layer. That is, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can be used as an electron blocking layer.

[1058] Figure 1 This is a simplified diagram illustrating an example of the structure of an organic EL element according to one embodiment of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and an organic layer, the organic layer including a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. Furthermore, the light-emitting unit 10 has a light-emitting auxiliary layer a 5a and a light-emitting auxiliary layer b 5b on the anode 3 side of the light-emitting layer 5. Preferably, the light-emitting auxiliary layer a 5a and the light-emitting auxiliary layer b 5b are in direct contact. And preferably, the light-emitting layer 5 is in contact with the light-emitting auxiliary layer b 5b. A hole transport band disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a and a hole transport layer 6b. Additionally, an electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed by an electron transport layer a 7a and an electron transport layer b 7b.

[1059] This invention is not limited to Figure 1 The structure of the organic EL element is shown.

[1060] The following are representative element structures that serve as examples of tandem organic EL elements.

[1061] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[1062] Here, the first light-emitting unit and the second light-emitting unit can each be independently selected from the aforementioned light-emitting units.

[1063] The intermediate layer, also commonly referred to as the intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, can be composed of known materials that provide electrons to the first light-emitting unit and holes to the second light-emitting unit.

[1064] Figure 2 A simplified diagram illustrating an example of the structure of an organic EL element according to another embodiment of the present invention.

[1065] The organic EL element 100 includes a substrate 20, an anode 30, a cathode 40, and an organic layer 10A disposed between the anode 30 and the cathode 40. The organic layer 10A may sequentially include a first light-emitting unit 110, a first charge-generating band 810, and a second light-emitting unit 120 from the anode 30 side. The first light-emitting unit 110, the first charge-generating band 810, and the second light-emitting unit 120 are sequentially disposed from the anode 30 side. The organic EL element 100 may include a high-refractive-index band and a low-refractive-index band in the organic layer 10A. The organic EL element 100 includes a capping layer 90 on the side of the cathode 40 opposite to the side facing the second light-emitting unit 120.

[1066] The first light-emitting unit 110 may sequentially include a first hole transport band 610, a first light-emitting band 510, and a first electrode transport band 710 from the anode 30 side. The first hole transport band 610, from the anode 30 side, sequentially includes a first hole injection layer 613, a first hole transport layer 612, and a first electron blocking layer 611. The first light-emitting band 510 may include a first light-emitting layer 511. The first electrode transport band 710 includes a first electron transport layer 712. The first charge generation band 810 may sequentially include a first charge generation layer 811 and a second charge generation layer 812 from the first light-emitting unit 110 side.

[1067] The second light-emitting part 120 may sequentially include a second hole transport band 620, a second light-emitting band 520, and a second electrode transport band 720 from the side of the first charge generation band 810. The second hole transport band 620 may sequentially include a second hole transport layer 622 and a second electron blocking layer 621 from the side of the first charge generation band 810. The second light-emitting band 520 may include the second light-emitting layer 521.

[1068] The second electrode transport band 720 can be sequentially derived from the second light-emitting band 520, including a second hole-blocking layer 721, a second electron transport layer 722, and a second electron injection layer 723. Figure 2In this case, the high refractive index band (HN1) includes a first charge-generating layer 811 and a first electron transport layer 712, which serve as high refractive index layers. The low refractive index band (LN1) includes a second charge-generating layer 812 and a second hole transport layer 622, which serve as low refractive index layers. The first charge-generating layer 811 in the two high refractive index layers corresponds to the first high refractive index layer. The second charge-generating layer 812 in the two low refractive index layers corresponds to the first low refractive index layer. The first charge-generating layer 811 (first high refractive index layer) and the second charge-generating layer 812 (first low refractive index layer) are in direct contact.

[1069] Additionally, the first light-emitting strip 510 has a first luminous auxiliary layer 511a and a first luminous auxiliary layer 511b on the anode 30 side of the first light-emitting layer 511. Preferably, the first light-emitting layer 511 is in direct contact with the first luminous auxiliary layer 511a. And preferably, the first luminous auxiliary layer 511a and the first luminous auxiliary layer 511b are in direct contact. Furthermore, the second light-emitting strip 520 has a second luminous auxiliary layer 521a and a second luminous auxiliary layer 521b on the anode 30 side of the second light-emitting layer 521. Preferably, the second light-emitting layer 521 is in direct contact with the second luminous auxiliary layer 521a. And preferably, the second luminous auxiliary layer 521a and the second luminous auxiliary layer 521b are in direct contact.

[1070] This invention is not limited to Figure 2 The structure of the organic EL element is shown.

[1071] It should be noted that in this invention, the substrate combined with a fluorescent dopant material (fluorescent emitting material) is called a fluorescent substrate, and the substrate combined with a phosphorescent dopant material is called a phosphorescent substrate. The difference between a fluorescent substrate and a phosphorescent substrate lies not only in their molecular structure. That is, a phosphorescent substrate refers to the material that forms a phosphorescent emitting layer containing phosphorescent dopant, but this does not mean that the material cannot be used to form a fluorescent emitting layer. The same applies to fluorescent substrates.

[1072] (Substrate)

[1073] The substrate serves as a support for organic EL elements. Examples of substrates include plates made of glass, quartz, or plastic. Flexible substrates can also be used. Examples of flexible substrates include plastic substrates formed from polyimide, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Furthermore, inorganic vapor-deposited films can also be used.

[1074] (anode)

[1075] For the anode formed on the substrate, metals, alloys, conductive compounds, and mixtures thereof with a high work function (specifically 4.0 eV or higher) are preferred. Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Furthermore, examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

[1076] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1–10 wt% zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5–5 wt% tungsten oxide and 0.1–1 wt% zinc oxide relative to indium oxide. Alternatively, they can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, etc.

[1077] (Hollow Conveyor Belt)

[1078] As described above, the hole transport band is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. Furthermore, the hole transport band includes a hole transport layer containing a compound represented by formula (A1) or formula (B1) above.

[1079] The hole injection layer formed in contact with the anode is formed using materials that are easy to inject holes, independent of the work function of the anode. Therefore, materials commonly used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1080] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and their alloys (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb) and their alloys. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[1081] (hole injection layer)

[1082] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material) and is formed between the anode and the light-emitting layer, or, if a hole transport layer is present, it is formed between the hole transport layer and the anode.

[1083] As hole-injection materials, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[1084] Examples of hole injection layer materials include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DN). Aromatic amine compounds such as TPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as: PCzPCN1) are also mentioned.

[1085] Polymers (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymers containing acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[1086] In addition, receptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are preferred.

[1087]

[1088] (In the above formula (K), R) 221 ~R 226 Each can independently represent a cyano group, -CONH2, a carboxyl group, or -COOR. 227 (R) 227 (Refers to alkyl groups having 1 to 20 carbon atoms or cycloalkyl groups having 3 to 20 carbon atoms). Additionally, it is selected from R... 221 and R 222 R 223 and R 224 and R 225 and R 226 Two adjacent groups can bond with each other to form a group represented by -CO-O-CO-.

[1089] As R 227 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[1090] (Hole transport layer, electron blocking layer)

[1091] A hole transport layer is a layer containing a material with high hole transport properties (hole transport material) and is formed between the anode and the light-emitting layer. Alternatively, if a hole injection layer is present, it is formed between the hole injection layer and the light-emitting layer. In a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer can also be used as an electron blocking layer.

[1092] In one embodiment of the invention, the hole transport layer comprises a compound (A1).

[1093] In another embodiment of the invention, the hole transport layer comprises a compound (B1) or a diamine.

[1094] The hole transport band may include one or more hole transport layers. When the hole transport band includes two or more hole transport layers, they may be the same or different. That is, the specific compounds and their compositions contained in the two or more hole transport layers may be the same or different in each layer. When the hole transport band includes two or more hole transport layers, at least one of the hole transport layers has the composition described above.

[1095] In one embodiment of the present invention, from the viewpoint of manufacturing cost, the compound (A1), compound (B1) and diamine contained in the hole transport layer are each independently protium.

[1096] The protium is a compound (A1), a compound (B1), and a diamine in which all hydrogen atoms are protium atoms.

[1097] Therefore, in one embodiment of the present invention, for example, an organic EL element preferably includes a hole transport layer comprising at least one selected from a compound (A1) substantially composed only of protium, a compound (B1), and a diamine. "A1 substantially composed only of protium" means that, relative to the total amount of compound (A1), the content of protium is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (all including 100%). "B1 substantially composed only of protium" means that, relative to the total amount of compound (B1), the content of protium is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (all including 100%). "Diamine substantially composed only of protium" means that, relative to the total amount of diamine, the content of protium is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (all including 100%).

[1098] As a hole transport layer material other than compound (A1), compound (B1) and diamine, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., other than compound (A1), compound (B1) and diamine can be used.

[1099] Examples of the aromatic amine compounds mentioned above include 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA). The hole mobility of these compounds is 10. -6 cm 2 / Vs and above.

[1100] Examples of carbazole derivatives include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PczPA).

[1101] Examples of anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (t-BuDNA), 9,10-bis(2-naphthyl)anthracene (DNA), and 9,10-diphenylanthracene (DPAnth).

[1102] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) or poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1103] Other compounds besides those mentioned above can also be used, as long as the hole transport property of the compound is higher than that of the electron transport property.

[1104] In one embodiment of the organic EL element of the present invention, the thickness of the hole transport layer is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less.

[1105] In one embodiment of the organic EL element of the present invention, in the case of an organic EL element having a double-layer or triple-layer hole transport layer, the total thickness of these hole transport layers is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less.

[1106] (Light-emitting band)

[1107] According to one embodiment of the present invention, the light-emitting strip includes a light-emitting auxiliary layer located between the light-emitting layer and the anode side of the light-emitting layer (i.e., between the hole transport layer and the light-emitting layer). The light-emitting auxiliary layer may be a single layer or multiple layers, and the plurality of light-emitting auxiliary layers may include a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer.

[1108] In addition, the light-emitting strip may include a single light-emitting layer, multiple light-emitting layers, multiple light-emitting layers and spacer layers located between each light-emitting layer.

[1109] (Dopant material of the light-emitting layer)

[1110] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent or phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, while phosphorescent materials are compounds that emit light from a triplet excited state.

[1111] In one embodiment of the organic EL element of the present invention, the light-emitting layer is preferably a single layer.

[1112] In another embodiment of the organic EL element of the present invention, the light-emitting layer preferably comprises two or more layers. That is, the light-emitting layer preferably comprises a first light-emitting layer and a second light-emitting layer.

[1113] In another embodiment of the organic EL element of the present invention, the light-emitting layer is preferably a bilayer structure composed of a first light-emitting layer and a second light-emitting layer.

[1114] As blue fluorescent materials that can be used in the luminescent layer, pyrene derivatives, styrylamine derivatives, phenanthrene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCPAPA).

[1115] As green fluorescent materials that can be used in the luminescent layer, aromatic amine derivatives can be used. Specifically, examples include N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), and N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPA). PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as: DPhAPhA), etc.

[1116] As red-based fluorescent materials that can be used in the luminescent layer, tetraphenyl derivatives, diamine derivatives, etc., can be used. Specifically, examples include N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[1117] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are employed. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (FIracac).

[1118] As a green phosphorescent material that can be used in the luminescent layer, iridium complexes are used. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[1119] As red phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are employed. Specifically, examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP).

[1120] In addition, rare earth metal complexes such as tri(acetylacetonyl)(monophenanthrene)terbium(III) (abbreviated as Tb(acac)3(Phen)), tri(1,3-diphenyl-1,3-propanedione)(monophenanthrene)eupium(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupium(III) (abbreviated as Eu(TTA)3(Phen)) can be used as phosphorescent materials because their luminescence originates from the luminescence of rare earth metal ions (electronic transitions between different multiplicity levels).

[1121] In one embodiment of the invention, the light-emitting layer comprises a luminescent compound exhibiting emission with a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm. When the luminescent compound with the maximum peak wavelength is included, an organic EL element and an electronic device including the same can be provided, exhibiting further improved element performance through the inclusion of a combination of specific compounds of the present invention.

[1122] For example, the luminescent compound exhibiting a maximum peak wavelength of 600 nm to 640 nm can be a red fluorescent luminescent material or a red phosphorescent luminescent material as exemplified above, and the luminescent compound exhibiting a maximum peak wavelength of 500 nm to 550 nm can be a green fluorescent luminescent material or a red phosphorescent luminescent material as exemplified above.

[1123] (Main material of the light-emitting layer)

[1124] The light-emitting layer can be constructed by dispersing the aforementioned dopant material in other materials (the host material). Preferably, a material with a lower least occupied molecular orbital (LUMO) energy level higher than that of the dopant material and a higher highest occupied molecular orbital (HOMO) energy level lower than that of the dopant material is used.

[1125] As the main material, for example, the following compounds can be used:

[1126] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1127] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1128] (3) Fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or thionyl derivatives,

[1129] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1130] In one embodiment of the organic EL element of the present invention, preferably, the light-emitting layer comprises the fused aromatic compounds such as the carbazole derivative, anthracene derivative, phenanthrene derivative, pyrene derivative or β derivative as the main material, and more preferably, it comprises anthracene derivative (also known as "anthracene compound").

[1131] In one embodiment of the organic EL element of the present invention, the anthracene compound that can be contained as a suitable host material as the light-emitting layer is preferably an anthracene compound having an anthracene ring and a dibenzofuran ring.

[1132] For example, the following compounds can be used:

[1133] Tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ) and other metal complexes;

[1134] Heterocyclic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 2,2',2''-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), phenanthrene-rhein (abbreviated as BPhen), and copper bath (abbreviated as BCP);

[1135] 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDN) A) fused aromatic compounds such as 9,9'-bianthracite (BANT), 9,9'-(stilbene-3,3'-diyl)phenanthrene (DPNS), 9,9'-(stilbene-4,4'-diyl)phenanthrene (DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), and 6,12-dimethoxy-5,11-diphenylanthracene; and others; and

[1136] N,N-Diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviation: DPhPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-Diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. A variety of host materials can be employed.

[1137] In particular, in the case of blue fluorescent elements, the following anthracene compounds are preferred as the host material.

[1138]

[1139]

[1140]

[1141] In one embodiment of the organic EL element of the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the component constituting the second light-emitting layer. For example, cases can be given where the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, or cases can be given where the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[1142] In one embodiment of the organic EL element of the present invention, the light-emitting layer may also contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of less than 500 nm (hereinafter sometimes simply referred to as "fluorescent compound").

[1143] The method for measuring the main peak wavelength of a compound is as follows: Prepare a 5 μmol / L toluene solution of the compound to be tested, place it in a quartz dish, and measure the emission spectrum of the sample at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a fluorescence spectrophotometer (equipment name: F-7000) manufactured by Hitachi Advanced Technology Co., Ltd. It should be noted that the emission spectrum measurement device is not limited to the device used in this article.

[1144] In a emission spectrum, the peak wavelength of the emission spectrum with the highest emission intensity is called the main peak wavelength. It should be noted that in this specification, the main peak wavelength is sometimes also referred to as the fluorescence emission main peak wavelength (FL-peak).

[1145] The fluorescent compound can be either the dopant material or the host material.

[1146] When the light-emitting layer is a single layer, only one of the dopant material and the host material can be the fluorescent luminescent compound, or both can be the fluorescent luminescent compound.

[1147] Furthermore, when the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first and second light-emitting layers may contain the fluorescent luminescent compound, or both light-emitting layers may contain the fluorescent luminescent compound. When the first light-emitting layer contains the fluorescent luminescent compound, only one of the dopant material and the host material contained in the first light-emitting layer may be the fluorescent luminescent compound, or both may be the fluorescent luminescent compound. Similarly, when the second light-emitting layer contains the fluorescent luminescent compound, only one of the dopant material and the host material contained in the second light-emitting layer may be the fluorescent luminescent compound, or both may be the fluorescent luminescent compound.

[1148] The thickness of the light-emitting band in an organic EL element is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting band is 5 nm or more, it is easy to form the light-emitting band and easy to adjust the color. When the thickness of the light-emitting band is 50 nm or less, it is easy to suppress the rise of the driving voltage.

[1149] (Light-emitting auxiliary layer)

[1150] The light-emitting auxiliary layer can be a single layer or multiple layers.

[1151] In one embodiment, the light-emitting auxiliary layer comprises a compound represented by formula (A2) or formula (B2) above.

[1152] In another embodiment, the light-emitting auxiliary layer is multilayered, and the plurality of light-emitting auxiliary layers include a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer, wherein the light-emitting auxiliary layer b contains a compound represented by formula (A2) or formula (B2) above.

[1153] The specific descriptions of the compounds shown in formula (A2) and formula (B2) above are as described above.

[1154] The thickness of the light-emitting auxiliary layer in an organic EL element is preferably 3 nm or more and 100 nm or less, more preferably 4 nm or more and 90 nm or less, and even more preferably 5 nm or more and 80 nm or less. When the film thickness is within the above-mentioned preferred range, it is easy to form a light-emitting band, easy to adjust the color, and easy to suppress the rise of the driving voltage.

[1155] In another embodiment of the organic EL element of the present invention, when the organic EL element includes multiple light-emitting auxiliary layers (e.g., light-emitting auxiliary layer a and light-emitting auxiliary layer b), the total thickness of these light-emitting auxiliary layers is preferably 3 nm or more and 100 nm or less, more preferably 4 nm or more and 90 nm or less, and even more preferably 5 nm or more and 80 nm or less. When the film thickness is within the above-mentioned preferred range, it is easy to form a light-emitting band, easy to adjust the color, and easy to suppress the rise of the driving voltage.

[1156] Furthermore, in one embodiment of the organic EL element of the present invention, the thickness of the light-emitting auxiliary layer a is preferably 50 nm or more and 100 nm or less, more preferably 60 nm or more and 90 nm or less, and even more preferably 70 nm or more and 80 nm or less. Additionally, the thickness of the light-emitting auxiliary layer b is preferably 3 nm or more and 10 nm or less, more preferably 4 nm or more and 8 nm or less, and even more preferably 5 nm or more and 7 nm or less. When the film thickness is within the above-mentioned preferred ranges, it is easy to form a light-emitting band, easy to adjust the color temperature, and easy to suppress the rise of the driving voltage.

[1157] Furthermore, in one embodiment of the organic EL element of the present invention, the thickness ratio of the light-emitting auxiliary layer a to the light-emitting auxiliary layer b is preferably 1:1 or more and 100:1 or less, more preferably 5:1 or more and 50:1 or less, and even more preferably 10:1 or more and 25:1 or less. When the film thickness is within the above-mentioned preferred range, it is easy to form a light-emitting band, easy to adjust the color, and easy to suppress the rise of the driving voltage.

[1158] (Electronic transmission belt)

[1159] The electron transport band is composed of an electron injection layer, an electron transport layer, and a hole blocking layer. Any layer of the electron transport band, especially the electron transport layer, preferably contains one or more elements selected from the group consisting of: alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals.

[1160] (Electron transport layer)

[1161] The electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light-emitting layer and the cathode, or, if an electron injection layer is present, it is formed between the electron injection layer and the light-emitting layer.

[1162] The electron transport layer can be a single-layer structure or a multi-layer structure comprising two or more layers. For example, the electron transport layer can be a bilayer structure comprising a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the invention, the electron transport layer of the single-layer structure is preferably adjacent to (in direct contact with) the light-emitting layer. Furthermore, in the multi-layer structure, the electron transport layer closest to the anode, such as the first electron transport layer in the bilayer structure, is preferably adjacent to (in direct contact with) the light-emitting layer. In another embodiment of the invention, a hole-blocking layer, etc., as described later, can be placed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer and the light-emitting layer in the multi-layer structure.

[1163] In the electron transport layer, for example, the following compounds can be used:

[1164] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes.

[1165] (2) Imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[1166] (3) Polymer compounds.

[1167] Examples of metal complexes include tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ).

[1168] Examples of heteroaromatic compounds include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs).

[1169] Examples of high molecular weight compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[1170] The material has a content of 10 -6 cm 2 Materials with electron mobility greater than / Vs. It should be noted that materials other than those mentioned above can also be used in the electron transport layer, as long as the electron transport property is higher than the hole transport property.

[1171] The electron transport layer can be a single layer or a multilayer comprising two or more layers. For example, the electron transport layer can be a layer comprising a first electron transport layer (anode side) and a second electron transport layer (cathode side). Both or more electron transport layers are formed of the electron transport material.

[1172] (Electron injection layer)

[1173] The electron injection layer is a layer containing a material with high electron injection capability. Alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used in the electron injection layer. Examples of such compounds include alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides, and organic complexes containing rare earth metals (e.g., lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiO)). x (etc.). Additionally, multiple compounds can be mixed for use.

[1174] Furthermore, alkali metals, alkaline earth metals, or compounds containing them can also be used as electron transport materials. Specifically, materials containing magnesium (Mg) in Alq can also be used. It should be noted that in this case, electron injection from the cathode can be performed more efficiently.

[1175] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. This composite material exhibits excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material that exhibits excellent electron transport properties; specifically, materials constituting the electron transport layer as described above (e.g., metal complexes or heteroaromatic compounds) can be used. The electron donor can be any material that has electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides or alkaline earth metal oxides are also preferred, such as lithium oxides, calcium oxides, and barium oxides. Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[1176] (cathode)

[1177] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and their alloys (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb) and their alloys.

[1178] It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[1179] It should be noted that by setting an electron injection layer, various conductive materials such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide can be used to form the cathode, regardless of their work function. These conductive materials can be deposited using sputtering, inkjet printing, spin coating, or other methods.

[1180] (Insulation layer)

[1181] Organic EL elements are prone to pixel defects caused by leakage or short circuits due to the application of an electric field to the ultrathin film. To prevent this, an insulating layer consisting of an insulating thin film layer can be inserted between a pair of electrodes.

[1182] Materials used in the insulating layer include, for example, aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures or laminates of these materials may also be used.

[1183] (Spare layer)

[1184] The spacer layer, for example, is disposed between a fluorescent emitting layer and a phosphorescent emitting layer. Its purpose is to prevent excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer during the stacking of the fluorescent and phosphorescent emitting layers, or to regulate the carrier balance. Alternatively, the spacer layer can also be disposed between multiple phosphorescent emitting layers. It should be noted that the term "charge carrier" as used here refers to the charge carrier in the material.

[1185] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that simultaneously possesses electron transport and hole transport properties. Furthermore, to prevent the diffusion of triplet energy within adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or higher. The same materials used in the spacer layer as those used in the aforementioned hole transport layer can be cited as examples.

[1186] (Barrier layer)

[1187] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can be placed adjacent to (in direct contact with) the light-emitting layer. An electron blocking layer prevents electrons from leaking from the light-emitting layer to the hole transport layer, while a hole blocking layer prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer prevents excitons generated in the light-emitting layer from diffusing into surrounding layers, thus confining the excitons within the light-emitting layer.

[1188] (Layer formation method)

[1189] The layers of the organic EL element can be formed using existing known methods such as vapor deposition and coating. For example, layers can be formed using known methods, such as vapor deposition, vacuum vapor deposition, molecular beam epitaxy (MBE), etc.; dry film formation methods, such as sputtering, plasma deposition, ion plating, etc.; and wet film formation methods using solutions of compounds for forming layers, such as dip coating, spin coating, casting, flow coating, bar coating, roll coating, inkjet coating, etc.

[1190] The film thickness of the aforementioned layers is not particularly limited, but from the viewpoint of preventing defects such as pinholes, it is preferably 5 nm or more, and from the viewpoint of easily suppressing the rise of the driving voltage, it is preferably 10 nm or less. From this viewpoint, it is preferably 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm. It should be noted that the thickness of the light-emitting band is as described above.

[1191] [Electronic Devices]

[1192] An organic EL element according to one embodiment of the present invention can be used in electronic devices such as display devices or light-emitting devices. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablet computers, or personal computers. Examples of light-emitting devices include lighting or vehicle lamps.

[1193] The organic EL element can be used in electronic devices, such as display components like organic EL panel modules, display devices like televisions, mobile phones, and personal computers, as well as light-emitting devices like lighting and vehicle lamps.

[1194] Example

[1195] The present invention will be described in more detail below through embodiments, but the present invention is not limited to the following embodiments.

[1196] The compounds of formula (A1) or formula (B1) used in the manufacture of the organic EL elements of Examples 1 to 11 are shown below:

[1197]

[1198]

[1199] The compounds of formula (A2) or formula (B2) used in the manufacture of the organic EL elements of Examples 1 to 11 are shown below:

[1200]

[1201]

[1202]

[1203] The comparative compounds used in the manufacture of the organic EL element in Comparative Example 1 are shown below:

[1204]

[1205] Other compounds used in the manufacture of the organic EL elements of Examples 1 to 11 and Comparative Example 1 are as follows:

[1206]

[1207] <Manufacturing of Organic EL Components>

[1208] The fabrication and evaluation of organic EL components are as follows.

[1209] Example 1

[1210] A glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) attached, measuring 25mm × 75mm × 1.1mm, was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130nm.

[1211] The cleaned glass substrate with the ITO transparent electrode attached was mounted on the substrate holder of the vacuum evaporation apparatus. First, compounds cHT-1 and HA-1 were co-deposited on the side where the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound cHT-1 to compound HA-1 was 97:3.

[1212] Next, compound cHT-1 is deposited on the hole injection layer to form a hole transport layer with a thickness of 125 nm.

[1213] Next, compound RHT-1 is deposited on the hole transport layer to form a light-emitting auxiliary layer a with a thickness of 75 nm.

[1214] Next, compound EB-1 is deposited on the aforementioned light-emitting auxiliary layer a to form a light-emitting auxiliary layer b with a film thickness of 5 nm.

[1215] Next, compounds PRH-1 and PRD-1 were co-deposited on the aforementioned light-emitting auxiliary layer b to form a light-emitting layer with a thickness of 40 nm. The mass ratio of compound PRH-1 to compound PRD-1 (PRH-1:PRD-1) was 96:4.

[1216] Next, compound ET-1 is deposited on the above-mentioned light-emitting layer to form an electron transport layer a with a film thickness of 5 nm.

[1217] Next, compounds ET-2 and Liq were co-deposited on electron transport layer a to form electron transport layer b with a thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Liq is an abbreviation for (8-hydroxyquinoline) lithium.

[1218] Next, Liq is deposited on the electron transport layer b to form an electron injection electrode with a film thickness of 1 nm.

[1219] Then, Al metal is deposited on the aforementioned electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1220] The following is a brief description of the structure of the organic EL element in Example 1.

[1221] ITO(130) / cHT-1:HA-1(10,97:3) / cHT-1(125) / RHT-1(75) / EB-1(5) / PRH-1:PRD-1(40,96:4) / ET-1(5) / ET-2:Liq(31,50:50) / Liq(1) / Al(80)

[1222] In the above component structure, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratio of the compounds used.

[1223] Examples 2 to 11

[1224] The organic EL elements of Examples 2 to 11 were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of the compounds cHT-1 or EB-1 in Example 1.

[1225] Comparative Example 1

[1226] The organic EL element of Comparative Example 1 was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of compound cHT-1 in Example 1.

[1227] Evaluation of Organic EL Components

[1228] The manufactured organic EL devices were evaluated as follows. The evaluation results are shown in Table 1.

[1229] Measurement of driving voltage

[1230] A voltage is applied to the organic EL element such that the current density is 10 mA / cm². 2 Measure the voltage at this time (unit: V).

[1231] Measurement of external quantum efficiency (EQE)

[1232] The organic EL device obtained as described above is subjected to a voltage at room temperature such that the current density is 10 mA / cm². 2 The spectroradiometer (CS-1000, manufactured by Konica Minolta) was used to measure the spectroradiometer spectrum at this time. Based on the obtained spectroradiometer spectrum, assuming that Lambertian radiation occurred, the external quantum efficiency EQE (%) was calculated.

[1233] Measurement of 95% lifespan (LT95)

[1234] A voltage is applied to the organic EL element such that the current density is 50 mA / cm². 2 And a 95% lifetime (LT95) assessment is performed. Here, LT95 refers to the time (in hours) required for the brightness to drop to 95% of the initial brightness under constant current drive.

[1235] Table 1

[1236]

[1237] As can be seen from the results in Table 1, compared with organic EL elements containing the comparative compound cHT-A, organic EL elements containing the compounds cHT-1 / cHT-2 / cHT-3 / cHT-4 / cHT-5 and compounds EB-1 / EB-2 / EB-3 / EB-4 / EB-5 / EB-6 / EB-7 of the present invention have lower driving voltage, higher external quantum efficiency, and longer 95% lifetime.

[1238] Synthesis of Hole Transport Layer Compounds

[1239] Example 1-1 of intermediate synthesis: Synthesis of intermediate 1A

[1240]

[1241] Under an argon atmosphere, a mixture of 1-bromo-2-iodobenzene (11.37 g, 40.2 mmol), 2-biphenylboronic acid (6.58 g, 33.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.16 g, 1.66 mmol), sodium carbonate (19.02 g, 179 mmol), DME (200 mL), ethanol (8 mL), and water (90 mL) was stirred at 80 °C for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give intermediate 1A as a colorless liquid (8.05 g). The yield was 78%.

[1242] Example 1-2 of intermediate synthesis: Synthesis of intermediate 1B

[1243]

[1244] Under an argon atmosphere, a mixture of the obtained intermediate 1A (8.05 g, 26 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)aniline (5.99 g, 27.3 mmol), tris(dibenzylacetone)dipalladium(0) (0.238 g, 0.26 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (Xphos) (0.496 g, 1.04 mmol), tripotassium phosphate (16.58 g, 78 mmol), 1,4-dioxane (174 mL), and water (39 mL) was stirred at 100 °C for 5 hours. The reaction mixture was cooled to room temperature, water was added, and then the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give intermediate 1B as a pale yellow solid (8.28 g). The yield was 99%.

[1245] Synthesis Examples of Intermediates 1-3: Synthesis of Intermediate 1C

[1246]

[1247] Under an argon atmosphere, a mixture of 2-bromobiphenyl (4.66 g, 20 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)aniline (4.82 g, 22.0 mmol), tris(dibenzylacetone)dipalladium(O) (0.183 g, 0.20 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (Xphos) (0.381 g, 0.8 mmol), tripotassium phosphate aqueous solution (30 mL, 60 mmol), and 1,4-dioxane (133 mL) was stirred at 100 °C for 5 hours. The reaction mixture was cooled to room temperature, water was added, and then the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give intermediate 1C as a pale yellow solid (4.9 g). The yield was 99%.

[1248] Synthesis Example 1-1: Synthesis of compound cHT-1

[1249]

[1250] A mixture of intermediate 1C (4.5 g, 18.34 mmol), 2-bromo-9,9-dimethylfluorene (11.02 g, 40.4 mmol), tris(dibenzylacetone)dipalladium(0) (0.672 g, 0.734 mmol), tri-tert-butylphosphine tetrafluoroborate (0.851 g, 0.293 mmol), sodium tert-butoxide (4.940 g, 51.4 mmol), and xylene (122 mL) was stirred at 120 °C for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to give 4.29 g of a white solid. The yield was 37%.

[1251] Mass spectrometry analysis revealed the substance to be compound cHT-1, with a molecular weight of 629.85 and an m / e ratio of 630.

[1252] Synthesis Example 1-2: Synthesis of compound cHT-2

[1253]

[1254] A mixture of intermediate 1B (2.7 g, 8.4 mmol), 2-bromo-9,9-dimethylfluorene (5.736 g, 21 mmol), tris(dibenzylacetone)dipalladium(0) (0.154 g, 0.168 mmol), tri-tert-butylphosphine tetrafluoroborate (0.195 g, 0.672 mmol), sodium tert-butoxide (2.260 g, 23.52 mmol), and xylene (56 mL) was stirred at 120 °C for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to give 4.03 g of a white solid. The yield was 68%.

[1255] Mass spectrometry analysis revealed that the white solid obtained was compound cHT-2, with a molecular weight of 705.95 and m / e = 706.

[1256] Synthesis Examples 1-3: Synthesis of compound cHT-3

[1257] Refer to KR 10-2355848 B1 to synthesize compound cHT-3.

[1258] Synthetic Examples 1-4: Synthesis of compound cHT-4

[1259] Refer to WO 2012 / 034627 A1 for the synthesis of compound cHT-4.

[1260] Synthesis Examples 1-5: Synthesis of compound cHT-5

[1261] Refer to WO 2020 / 226298 A1 for the synthesis of compound cHT-5.

[1262] Synthesis of Luminescent Assist Layer Compounds

[1263] Example 2-1 of intermediate synthesis: Synthesis of intermediate 2A

[1264]

[1265] (1-1) Synthesis of intermediate 2A-1

[1266] Under an argon atmosphere, a mixture of 1200 g (4.86 mol) of 4-bromodibenzofuran, 573 g (9.71 mol) of acetamide, 184.98 g (971 mmol) of cuprous iodide, 85.62 g (971 mmol) of N,N'-dimethylethylenediamine, 1342 g (97.1 mol) of potassium carbonate, and 6 L of xylene was reacted at 135 °C for 5 hours. The reaction mixture was cooled to room temperature, and then 4 L of water was added. The mixture was stirred for 1 hour, and crystals precipitated. The precipitated crystals were collected by filtration and washed with water and n-heptane to give 950 g of intermediate 2A-1. The yield was 75%.

[1267] (1-2) Synthesis of intermediate 2A-2

[1268] Under an argon atmosphere, 809 g (5.06 mol) of bromine was added to 7.1 L of a solution of 950 g (4.22 mol) of intermediate 2A-1 synthesized in (1-1) and stirred at room temperature for 6 hours. 7 L of water was added dropwise to the resulting solution, followed by 63 g of sodium thiosulfate, and the mixture was stirred overnight at room temperature, resulting in crystal precipitation. The precipitated crystals were collected by filtration and washed successively with water, methanol, toluene, and n-heptane to obtain 1044 g of intermediate 2A-2. The yield was 78%.

[1269] (1-3) Synthesis of intermediate 2A-3

[1270] 1925 g (34.3 mmol) of potassium hydroxide was added to a solution of 1044 g (3.43 mmol) of intermediate 2A-2 synthesized in (1-2) in 5 L of xylene and 700 mL of ethylene glycol, and the mixture was stirred at 130 °C for 24 hours. 500 mL of ethylene glycol was added to the resulting solution, and the reaction was continued at 130 °C for 3 days with stirring. The reaction mixture was cooled, 3 L of water was added, and the mixture was separated and the organic layer concentrated. The residue was purified by silica gel column chromatography to give 721 g of intermediate 2A-3. The yield was 80%.

[1271] (1-4) Synthesis of intermediate 2A

[1272] Under an argon atmosphere, 2698 g (27.5 mmol) of concentrated sulfuric acid was added dropwise to a solution of 721 g (2.75 mol) of intermediate 2A-3 synthesized in (1-3) in 3.6 L of acetonitrile and 3.6 L of water at -5–15 °C, and the mixture was stirred at -5 °C for 30 min. Next, 483 g (4.13 mol) of isoamyl nitrite was added dropwise to the resulting solution while maintaining a temperature below -3 °C, and the mixture was stirred at -5 °C for 1 h. Then, 908 g (13.8 mol) of hypophosphite was added to the solution while maintaining a temperature below -2 °C. Next, 3 L of methanol was added to the solution, and the reaction was stirred overnight at room temperature. Toluene was added to the reaction mixture, and the mixture was separated. The toluene layer was washed with saturated brine. The residue was purified by silica gel column chromatography to give 418 g of intermediate 2A. The yield was 61.4%.

[1273] Example 2-2 of intermediate synthesis: Synthesis of intermediate 2B

[1274] (2-1) Synthesis of intermediate 2B-1

[1275]

[1276] Under an argon atmosphere, a mixture of 3.72 g (15 mmol) of 4-(1-naphthyl)phenylboronic acid, 2.87 g (15 mmol) of 4-bromochlorobenzene, 347 mmol (0.30 mmol) of tetrakis(triphenylphosphine)palladium(O), 22.5 mL of 2M sodium carbonate aqueous solution, and 45 mL of toluene, synthesized according to the method described in International Publication No. 2019 / 146781, was stirred at 100 °C for 7 hours. After returning to room temperature, water was added, and the mixture was extracted with toluene. The resulting toluene layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3.07 g of intermediate 2B-1 as a white solid. The yield was 65%.

[1277] (2-2) Synthesis of intermediate 2B

[1278]

[1279] Under an argon atmosphere, a 1.2 L solution of 67 g (258 mmol) of 4-(dibenzo[b,d]furan-4-yl)aniline synthesized according to the method described in International Publication No. 2016 / 006711 and 54 g (172 mmol) of intermediate 2B-1 synthesized in (2-1) in xylene was heated to 100 °C. 3.14 g (3.43 mmol) of tris(dibenzylacetone)dipalladium(0), 3.27 g (6.86 mmol) of XPhos, and 19.78 g (206 mmol) of sodium tert-butoxide were added, and the mixture was stirred at 130 °C for 3 hours. The reaction solution was cooled to room temperature, and methanol was added for filtration. The resulting residue was dissolved in toluene, silica gel was added, and the mixture was stirred for 30 minutes, then filtered. Methanol was added to the filtrate, and the mixture was filtered to give 70 g of a white solid. The yield was 76%.

[1280] Synthesis Example 2-1: Synthesis of Compound EB-1

[1281]

[1282] Under an argon atmosphere, a xylene solution containing 47.87 g (89 mmol) of intermediate 2A, 22 g (89 mmol) of intermediate 2B, 0.4 g (1.781 mmol) of palladium(II) acetate, and 0.72 g (3.56 mmol) of tri-tert-butylphosphine was heated to 90 °C, and 10.27 g (107 mmol) of sodium tert-butoxide was added. The mixture was stirred at 110 °C for 22 hours. The reaction solution was cooled to room temperature, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to give 46 g of a white solid.

[1283] Mass spectrometry analysis revealed that the obtained substance was compound 3, as shown in the above chemical structure, with a molecular weight of 703.84 and an m / e ratio of 704. The yield was 73%.

[1284] Example 2-3 of intermediate synthesis: Synthesis of intermediate 3A

[1285]

[1286] (1) Synthesis of intermediate 3A-1

[1287] Under an argon atmosphere, 7.2 g of 2,2,6,6-tetramethylpiperidine and 60 mL of dehydrated tetrahydrofuran were added to a flask and cooled to -43 °C. 33 mL of n-BuLi (1.55 M in hexane) was added, and the mixture was stirred at -40 °C for 30 min. The mixture was then cooled to -69 °C, and 16.0 mL of (iPrO)₃B was added. After stirring at -78 °C for 5 min, 20 mL of THF solution containing 5.00 g of 1-fluoronaphthalene was added dropwise, and the mixture was stirred in an ice bath for 10 h. After the reaction was complete, 100 mL of 1 N HCl aqueous solution was added, and the mixture was stirred at room temperature for 1 h. The solution was then transferred to a separatory funnel and extracted with ethyl acetate. The solution was dried over anhydrous magnesium sulfate, concentrated, and washed with hexane to give 6.13 g of a white solid of (1-fluoronaphthyl-2-yl)boronic acid (intermediate 3A-1) (yield 71%).

[1288] (2) Synthesis of intermediate 3A-2

[1289] Under an argon atmosphere, 4.52 g of (1-fluoronaphthyl-2-yl)boronic acid (intermediate 3A-1), 4.30 g of 2-bromo-1,3-dimethoxybenzene, 0.91 g of tris(dibenzylacetone)dipalladium(0), 0.81 g of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (SPhos), 12.6 g of tripotassium phosphate, and 10 mL of dehydrated toluene were added to a flask and heated under reflux for 7 hours. The mixture was cooled to room temperature, and the reaction solution was extracted with toluene to remove the aqueous layer. The organic layer was then washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the residue was purified by silica gel column chromatography to give 4.70 g of 2-(2,6-dimethoxyphenyl)-1-fluoronaphthyl (intermediate 3A-2) (yield 84%).

[1290] (3) Synthesis of intermediate 3A-3

[1291] Under an argon atmosphere, 4.70 g of 2-(2,6-dimethoxyphenyl)-1-fluoronaphthalene (intermediate 3A-2) and 210 mL of dehydrated dichloromethane were added to a flask and cooled to 0 °C. 41 mL of a 1.0 mol / L boron tribromide dichloromethane solution was added, and the mixture was stirred at room temperature for 4 hours. After the reaction was complete, the solution was cooled to -78 °C, carefully quenched with methanol, and then quenched again with sufficient water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with anhydrous sodium sulfate, and then impurities were removed by passing through a short silica gel column. The solution was concentrated, and the resulting sample was vacuum dried at room temperature for 3 hours to obtain 4.00 g of a transparent oily substance of 2-(3-fluoronaphthyl-2-yl)phenyl-1,3-diol (intermediate 3A-3) (yield 94%).

[1292] (4) Synthesis of intermediate 3A-4

[1293] Under an argon atmosphere, 4.00 g of 2-(3-fluoronaphthyl-2-yl)phenyl-1,3-diol (intermediate 3A-3), 15 mL of N-methyl-2-pyrrolidone (dehydrated), and 3.26 g of K₂CO₃ were added to a flask, and the mixture was stirred at 150 °C for 2 hours. After the reaction was complete, the solution was cooled to room temperature, 200 mL of ethyl acetate was added, and the mixture was transferred to a separatory funnel and washed with water. The solution was dried over anhydrous sodium sulfate and then purified by silica gel column chromatography to give 1.25 g of naphtho[1,2-b]benzofuran-7-ol (intermediate 3A-4) as a white solid (yield 34%).

[1294] (5) Synthesis of intermediate 3A

[1295] Under an argon atmosphere, 1.25 g of naphtho[1,2-b]benzofuran-7-ol (intermediate 3A-4), 65 mg of N,N-dimethyl-4-aminopyridine, 1.08 mL of trifluoromethanesulfonic anhydride, and 27 mL of dichloromethane (dehydrated) were added to a flask and cooled to 0 °C. 10.6 mL of pyridine (dehydrated) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the mixture was quenched with sufficient water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried over anhydrous sodium sulfate, and then impurities were removed using a short silica gel column. The solution was concentrated, and the resulting sample was vacuum dried at room temperature for 3 hours to obtain 1.50 g of a white solid of naphtho[1,2-b]benzofuran-7-yl trifluoromethanesulfonate (intermediate 3A) (yield 77%).

[1296] Intermediate Synthesis Example 2-4: Synthesis of 3D Intermediates

[1297]

[1298] Under an argon atmosphere, a mixture of 7.33 g (20.0 mmol) of intermediate 3A, 3.75 g (24.0 mmol) of 2-chlorophenylboronic acid, 0.327 g (0.400 mmol) of [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloromethane adduct, 20 mL (40.0 mmol) of 2M sodium carbonate aqueous solution, and 66.7 mL of DME was stirred at 80 °C for 2 hours. The reaction mixture was cooled to room temperature, water was added, and then filtered. The residue was purified by silica gel column chromatography and recrystallization to give 5.94 g of intermediate compound 3D as a white solid. The yield was 90%.

[1299] Synthesis Example 2-2: Synthesis of Compound EB-2

[1300]

[1301] Under an argon atmosphere, a mixture of N-[4-(1-naphthyl)phenyl][1,1'-biphenyl]-4-amine (11.1 g (33.0 mmol)), intermediate 3D (10.9 g (33.0 mmol)), tris(dibenzylacetone)dipalladium(0) (0.549 g (0.60 mmol)), SPhos (0.985 g (2.40 mmol)), sodium tert-butoxide (4.04 g (42.0 mmol)), and xylene (300 mL) was stirred at 120 °C for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to give 17.7 g of a white solid. The yield was 89%.

[1302] Mass spectrometry analysis revealed that the product was compound EB-2, with a molecular weight of 663.82 and m / e = 664.

[1303] Synthesis Example 2-3: Synthesis of Compound EB-3

[1304] The compound EB-3 was synthesized with reference to PCT International Publication WO 2016 / 006710 A1.

[1305] Synthesis Example 2-4: Synthesis of Compound EB-4

[1306] The compound EB-4 was synthesized with reference to US Patent Publication 2017 / 0288147 A1.

[1307] Synthesis Example 2-5: Synthesis of Compound EB-5

[1308]

[1309] Under an argon atmosphere, a mixture of 1-bromo-9,9-dimethyl-9H-fluorene (9.01 g, 33.0 mmol), N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine (13.6 g, 33.0 mmol), tris(dibenzylacetone)dipalladium(O) (0.549 g, 0.60 mmol), SPhos (0.985 g, 2.40 mmol), sodium tert-butoxide (4.04 g, 42.0 mmol), and 300 mL of xylene was stirred at 120 °C for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to give 12.1 g of a white solid. The yield was 61%.

[1310] Mass spectrometry analysis revealed that the product was compound EB-5, with a molecular weight of 603.76 and an m / e ratio of 604.

[1311] Synthesis Example 2-6: Synthesis of Compound EB-6

[1312] Refer to WO 2023 / 140529 A1 for the synthesis of compound EB-6.

[1313] Synthesis Example 2-7: Synthesis of Compound EB-7

[1314] Synthesize compound EB-7 according to EP 3540803 A2.

[1315] Explanation of reference numerals in the attached figures

[1316] 1, 100: Organic EL element; 2, 20: Substrate; 3, 30: Anode (first electrode); 4, 40: Cathode (second electrode); 5: Light-emitting layer; 5a: Light-emitting auxiliary layer a; 5b: Light-emitting auxiliary layer b; 6a: Hole injection layer; 6b: Hole transport layer; 7a: Electron transport layer a; 7b: Electron transport layer b; 10: Light-emitting unit; 10A: Organic layer; 110: First light-emitting unit; 120: Second light-emitting unit; 510: First light-emitting strip; 511: First light-emitting layer; 511a: First a light-emitting auxiliary layer; 511b: First b light-emitting auxiliary layer; 52 0: Second luminescent band; 521: Second luminescent layer; 521a: 2a luminescent auxiliary layer; 521b: 2b luminescent auxiliary layer; 610: First hole transport band; 611: First electron blocking layer; 612: First hole transport layer; 613: First hole injection layer; 621: Second electron blocking layer; 622: Second hole transport layer; 712: First electron transport layer; 721: Second hole blocking layer; 722: Second electron transport layer; 723: Second electron injection layer; 810: First charge generation band; 811: First charge generation layer; 812: Second charge generation layer.

Claims

1. An organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein, The organic layer includes: Emissive layer; A hole transport layer is formed between the light-emitting layer and the first electrode; and A light-emitting auxiliary layer is formed between the hole transport layer and the light-emitting layer. The light-emitting layer contains a luminescent compound that exhibits luminescence with a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm. The hole transport layer comprises a compound represented by the following formula (A1). The light-emitting auxiliary layer comprises a compound represented by the following formula (A2), (A1) (A2) In equation (A1), N is the central nitrogen atom. L a1 L a2 and L a3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms. Ar a2 It can be a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 5 to 30 carbon atoms. In equation (A2), N is the central nitrogen atom. X b Represents oxygen or sulfur atoms. Selected from R 1 ~R 8 One of them is a single bond that bonds with *2. Selected from R 1 ~R 8 The single bond in the *2 group is not bonded to *2 and the two adjacent bonds can be optionally bonded to each other to form a substituted or unsubstituted benzene ring, or they can not be bonded to each other and thus not form a ring. It is not a single bond bonded to *2 and the two adjacent R bonds are not bonded to each other. 1 ~R 8 It is a hydrogen atom. L b1 L b2 and L b3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms. Ar in formula (A1) a3 And Ar in formula (A2) b2 and Ar b3 Each is independently a group represented by any one of the following formulas (a) to (e): In equation (a), R 10 ~R 25 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 10 ~R 14 One of them is a single bond that bonds with *f. Selected from R 15 ~R 20 One of them is a single bond that bonds with *g, selected from R 15 ~R 20 The other one is a single bond that bonds with *h. *** indicates that L a3 L b2 or L b3 The location of the bond, m1 is either 0 or 1, n1 is either 0 or 1. When m1 is 0 and n1 is 0, *h and L a3 L b2 or L b3 bonding, When m1 is 0 and n1 is 1, *f and L a3 L b2 or L b3 bonding, When m1 is 1 and n1 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h. k1 is 1 or 2. Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure. In equation (b), R 10 ~R 20 The same applies to *f, *g, *h, and ***. R 26 ~R 33 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 26 ~R 33 One of them is a single bond that bonds with *i. m2 is either 0 or 1, n2 is either 0 or 1. When m2 is 0 and n2 is 0, *h and L a3 L b2 or L b3 bonding, When m2 is 0 and n2 is 1, *f and L a3 L b2 or L b3 bonding, When m2 is 1 and n2 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h. Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure. In equation (c), R 10 ~R 20 The same applies to *f, *g, *h, and ***. R 34 ~R 43 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 34 ~R 43 One of them is a single bond that bonds with *j. m3 is either 0 or 1, n3 is either 0 or 1. When m3 is 0 and n3 is 0, *h and L a3 L b2 or L b3 bonding, When m3 is 0 and n3 is 1, *f and L a3 L b2 or L b3 bonding, When m3 is 1 and n3 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h. Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 15 ~R 20 The two adjacent single bonds that are not any of the stated single bonds, and R 34 and R 35 They do not bond with each other and therefore do not form a ring structure. In equation (d), R 10 ~R 14 The same applies to *f and ***. R 44 ~R 51 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. X represents an oxygen atom, a sulfur atom, or CR. a R b or NR c , R a R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, or R a and R b The rings can be substituted or unsubstituted by selective bonding. Among them, selected from R 44 ~R 51 One of them is a single bond that bonds with *k. m4 is 0 or 1. When m4 is 0, *f and L a3 L b2 or L b3 bonding, Selected from R 44 ~R 51 The single bonds in the ring are not the single bonds described above, and two adjacent bonds are optionally bonded to each other independently to form substituted or unsubstituted ring structures. In equation (e), R 10 ~R 14 The same applies to *f and ***. R 52 ~R 66 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 52 ~R 56 One of them is a single bond bonded to *l, selected from R 52 ~R 56 The other one is a single bond that bonds with *m. m5 is 0 or 1. When m5 is 0, *f and L a3 L b2 or L b3 bonding, Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 52 ~R 56 The two adjacent R bonds that are not any of the stated single bonds 52 and R 61 and R 56 and R 57 They do not bond with each other and thus do not form a ring structure.

2. An organic electroluminescent element, comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein, The organic layer includes: Emissive layer; A hole transport layer is formed between the light-emitting layer and the first electrode; and Multiple light-emitting auxiliary layers are formed between the hole transport layer and the light-emitting layer. The plurality of light-emitting auxiliary layers include a light-emitting auxiliary layer a adjacent to the hole transport layer and a light-emitting auxiliary layer b adjacent to the light-emitting layer. The hole transport layer comprises a compound or diamine represented by the following formula (B1), The light-emitting auxiliary layer b comprises a compound represented by the following formula (B2). (B1) (B2) In equation (B1), N is the central nitrogen atom. L a1 L a2 and L a3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms. In equation (B2), N is the central nitrogen atom. Ar b1 It can be a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 5 to 30 carbon atoms. L b1 L b2 and L b3 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms. Ar in equation (B1) a3 Ar in formula (B2) b2 and Ar b3 Each is independently a group represented by any one of the following formulas (a) to (e): In equation (a), R 10 ~R 25 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 10 ~R 14 One of them is a single bond that bonds with *f. Selected from R 15 ~R 20 One of them is a single bond that bonds with *g, selected from R 15 ~R 20 The other one is a single bond that bonds with *h. *** indicates that L a3 L b2 or L b3 The location of the bond, m1 is either 0 or 1, n1 is either 0 or 1. When m1 is 0 and n1 is 0, *h and L a3 L b2 or L b3 bonding, When m1 is 0 and n1 is 1, *f and L a3 L b2 or L b3 bonding, When m1 is 1 and n1 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h. k1 is 1 or 2. Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure. In equation (b), R 10 ~R 20 The same applies to *f, *g, *h, and ***. R 26 ~R 33 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 26 ~R 33 One of them is a single bond that bonds with *i. m2 is either 0 or 1, n2 is either 0 or 1. When m2 is 0 and n2 is 0, *h and L a3 L b2 or L b3 bonding, When m2 is 0 and n2 is 1, *f and L a3 L b2 or L b3 bonding, When m2 is 1 and n2 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h. Selected from R 10 ~R 14 The two bonds that are not the single bonds and are adjacent to each other, and the two bonds selected from R 15 ~R 20 The bonds in the structure are not arbitrary single bonds, and adjacent bonds do not bond to each other to form a ring structure. In equation (c), R 10 ~R 20 The same applies to *f, *g, *h, and ***. R 34 ~R 43 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 34 ~R 43 One of them is a single bond that bonds with *j. m3 is either 0 or 1, n3 is either 0 or 1. When m3 is 0 and n3 is 0, *h and L a3 L b2 or L b3 bonding, When m3 is 0 and n3 is 1, *f and L a3 L b2 or L b3 bonding, When m3 is 1 and n3 is 0, the selection is from R. 10 ~R 14 One of them is a single bond that bonds with *h. Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 15 ~R 20 The two adjacent single bonds that are not any of the stated single bonds, and R 34 and R 35 They do not bond with each other and therefore do not form a ring structure. In equation (d), R 10 ~R 14 The same applies to *f and ***. R 44 ~R 51 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. X represents an oxygen atom, a sulfur atom, or CR. a R b or NR c , R a R b and R c Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, or R a and R b The rings can be substituted or unsubstituted by selective bonding. Among them, selected from R 44 ~R 51 One of them is a single bond that bonds with *k. m4 is 0 or 1. When m4 is 0, *f and L a3 L b2 or L b3 bonding, Selected from R 44 ~R 51 The single bonds in the ring are not the single bonds described above, and two adjacent bonds are optionally bonded to each other independently to form substituted or unsubstituted ring structures. In equation (e), R 10 ~R 14 The same applies to *f and ***. R 52 ~R 66 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. Among them, selected from R 52 ~R 56 One of them is a single bond bonded to *l, selected from R 52 ~R 56 The other one is a single bond that bonds with *m. m5 is 0 or 1. When m5 is 0, *f and L a3 L b2 or L b3 bonding, Selected from R 10 ~R 14 The two adjacent bonds that are not the single bonds mentioned above, selected from R 52 ~R 56 The two adjacent R bonds that are not any of the stated single bonds 52 and R 61 and R 56 and R 57 They do not bond with each other and thus do not form a ring structure.

3. The organic electroluminescent element according to claim 2, wherein, The luminescent layer contains a luminescent compound that exhibits luminescence with a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm.

4. The organic electroluminescent element according to claim 1, wherein, Ar a2 It can be a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobisfluorenyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted adamantyl group.

5. The organic electroluminescent element according to claim 1 or 2, wherein, Ar a3 It is represented by the following formula (1a): (1a) In equation (1a), Selected from R a1 ~R a13 One of them is a single bond that bonds with *1. R is not a single bond that bonds with *1 a1 ~R a13 Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group with 1 to 50 carbon atoms, or -Si(R 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown as ) or -S-(R 905 The group shown in the figure, R 901 ~R 905 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms. In R 901 When there are more than two, more than two R 901 They are the same or different. In R 902 When there are more than two, more than two R 902 They are the same or different. In R 903 When there are more than two, more than two R 903 They are the same or different. In R 904 When there are more than two, more than two R 904 They are the same or different. In R 905 When there are more than two, more than two R 905 They are the same or different. R a14 It can be a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group. Among them, R is selected from single bonds that are not bonded to *1. a1 ~R a13 and R a14 Two adjacent benzene rings may be optionally bonded to each other to form substituted or unsubstituted benzene rings, or they may not be bonded to each other to form a ring.

6. The organic electroluminescent element according to claim 5, wherein, In equation (1a), the values ​​selected from R a1 ~R a13 One of them is a single bond that bonds with *1. R is not a single bond that bonds with *1 a1 ~R a13 It is a hydrogen atom. R a14 It is a hydrogen atom, or a substituted or unsubstituted phenyl group. Among them, R is not a single bond bonded to *1. a1 ~R a13 and R a14 They do not bond with each other and therefore do not form a ring.

7. The organic electroluminescent element according to claim 2, wherein, In equation (B2), Ar b1 It is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted naphthobenzofuranyl group.

8. The organic electroluminescent element according to claim 1, wherein, Ar b2 and Ar b3 Any one of them is a group represented by formula (d). R 1 ~R 4 They do not bond with each other and therefore do not form a ring.

9. The organic electroluminescent element according to claim 1 or 2, wherein, L b2 It is a single key. Ar b2 The group represented by formula (d) In equation (d), m4 is 0 and X is an oxygen atom.

10. The organic electroluminescent element according to claim 1, wherein, In equation (A2), R 1 Bonded with *2, R 1 ~R 8 They do not bond with each other and therefore do not form a ring.

11. The organic electroluminescent element according to claim 1, wherein, In equation (A2), R 8 Bonded with *2, Selected from R 1 ~R 4 Two adjacent benzene rings in the benzene ring bond to each other to form substituted or unsubstituted benzene rings.

12. The organic electroluminescent element according to claim 1 or 2, wherein, L a1 L a2 L a3 L b1 L b2 and L b3 Each is an independent single bond, or a substituted or unsubstituted phenylene.

13. The organic electroluminescent element according to claim 1, wherein, The hole transport layer comprises at least one of the following compounds:

14. The organic electroluminescent element according to claim 2, wherein, The hole transport layer comprises at least one of the following compounds:

15. The organic electroluminescent element according to claim 1 or 2, wherein, The hole transport layer comprises at least one of the following compounds:

16. The organic electroluminescent element according to claim 1, wherein, The light-emitting auxiliary layer comprises at least one of the following compounds:

17. The organic electroluminescent element according to claim 2, wherein, The light-emitting auxiliary layer comprises at least one of the following compounds:

18. The organic electroluminescent element according to claim 1 or 2, wherein, The light-emitting auxiliary layer comprises at least one of the following compounds:

19. An organic electroluminescent element, comprising a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode, wherein, The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are arranged sequentially from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip, and the first light-emitting strip includes a first organic layer. The first organic layer includes: First luminescent layer; A first hole transport layer is formed between the first light-emitting layer and the first electrode; and A first light-emitting auxiliary layer is formed between the first hole transport layer and the first light-emitting layer. The second light-emitting unit includes a second light-emitting strip, and the second light-emitting strip includes a second organic layer. The second organic layer includes: Second hole transport layer; A second light-emitting layer is formed between the second hole transport layer and the second electrode; and A second light-emitting auxiliary layer is formed between the second hole transport layer and the second light-emitting layer. At least one of the first and second light-emitting layers contains a luminescent compound exhibiting luminescence with a maximum peak wavelength of 600 nm to 640 nm or 500 nm to 550 nm. At least one of the first hole transport layer and the second hole transport layer comprises a compound represented by the following formula (A1). At least one of the first light-emitting auxiliary layer and the second light-emitting auxiliary layer comprises a compound represented by the following formula (A2). The definitions of each substituent in formulas (A1) and (A2) are the same as those in claim 1.

20. An organic electroluminescent element, comprising a first electrode, a second electrode, and two or more light-emitting units disposed between the first electrode and the second electrode, wherein, The two or more light-emitting units include at least a first light-emitting unit and a second light-emitting unit. The first light-emitting unit and the second light-emitting unit are arranged sequentially from the first electrode side to the second electrode side. The first light-emitting unit includes a first light-emitting strip, and the first light-emitting strip includes a first organic layer. The first organic layer includes: First luminescent layer; A first hole transport layer is formed between the first light-emitting layer and the first electrode; and Multiple first light-emitting auxiliary layers are formed between the first hole transport layer and the first light-emitting layer. The plurality of first light-emitting auxiliary layers include a first a light-emitting auxiliary layer adjacent to the first hole transport layer and a first b light-emitting auxiliary layer adjacent to the first light-emitting layer. The second light-emitting unit includes a second light-emitting strip, and the second light-emitting strip includes a second organic layer. The second organic layer includes: Second hole transport layer; A second light-emitting layer is formed between the second hole transport layer and the second electrode; and Multiple second light-emitting auxiliary layers are formed between the second hole transport layer and the second light-emitting layer. The plurality of second light-emitting auxiliary layers include a 2a light-emitting auxiliary layer adjacent to the second hole transport layer and a 2b light-emitting auxiliary layer adjacent to the second light-emitting layer. At least one of the first hole transport layer and the second hole transport layer contains a compound or diamine as shown in formula (B1). At least one of the first b light-emitting auxiliary layer and the second b light-emitting auxiliary layer comprises a compound represented by the following formula (B2). The definitions of each substituent in formulas (B1) and (B2) are the same as those in claim 2.

21. An electronic device comprising the organic electroluminescent element according to any one of claims 1, 2, 19 and 20.

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