Polymer, and electroluminescence element material and electroluminescence element using the polymer

Abstract

To provide a technique that can improve the performance of an electroluminescence element (particularly durability).SOLUTION: A polymer contains a constitutional unit represented by the formula (1). In the formula (1), each substituent has the same meaning as in the specifications.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a polymer, and an electroluminescence element material and an electroluminescence element using the polymer.

Background Art

[0002] Research and development of electroluminescence elements (EL elements) are actively underway. In particular, EL elements are expected to be used as solid-state light-emitting, inexpensive, large-area full-color display elements and writing light source arrays. An EL element is a light-emitting element having a thin film of several nanometers to several hundred nanometers between an anode and a cathode. Further, an EL element usually further has a hole transport layer, a light-emitting layer, an electron transport layer, and the like.

[0003] Among these, as materials for the light-emitting layer, there are fluorescent light-emitting materials and phosphorescent light-emitting materials. Phosphorescent light-emitting materials are materials that are expected to have higher luminous efficiency compared to fluorescent light-emitting materials. In addition, in order to cover a wide color gamut, an RGB light source is required to have a narrow half-value width emission spectrum. In particular, deep blue is required for blue, but at present, no element that can satisfy the viewpoints of long life and color purity has been found.

[0004] As a method for solving these problems, there is a light-emitting device that uses "quantum dots", which are inorganic light-emitting substances, as a light-emitting material (Patent Document 1). A quantum dot (QD) is a semiconductor material having a crystal structure with a size of several nanometers and is composed of about several hundred to several thousand atoms. Since the size of the quantum dot is very small, the surface area per unit volume is large. For this reason, most of the atoms are present on the surface of the nanocrystal, and it exhibits effects such as quantum confinement. Due to such a quantum confinement effect, the quantum dot can adjust the emission wavelength only by adjusting its size, and has characteristics such as excellent color purity and high photoluminescence (PL) emission efficiency, so it has attracted much attention. A quantum dot light emitting diode (QD LED) is known as a basic element having a three-layer structure including a hole transport layer (HTL) and an electron transport layer (ETL) at both ends with a quantum dot light emitting layer in between.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, in the electroluminescence device (especially the quantum dot electroluminescence device) using the hole transport material described in Patent Document 1, sufficient performance (especially durability) could not be achieved.

[0007] Therefore, the present invention has been made in view of the above circumstances, and an object thereof is to provide a technology capable of improving the performance (especially durability) of an electroluminescence device (especially a quantum dot electroluminescence device).

Means for Solving the Problem

[0008] The inventors of the present invention conducted intensive studies to solve the above problems. As a result, they found that the above problems can be solved by using a polymer having a specific structure, and completed the present invention.

[0009] That is, the above object can be achieved by a polymer having a structural unit (A) represented by the following formula (1).

[0010]

Chemical formula

[0011] In the above formula (1), Ar 1 ~Ar 3 are each independently a divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, which may be substituted or unsubstituted, Ar 4 is a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed, Ar 5 is a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring-forming atoms, Ar 6 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 60 ring-forming atoms, p is 0 or 1.

Advantages of the Invention

[0012] According to the present invention, an electroluminescence element (particularly a quantum dot electroluminescence element) excellent in performance (particularly durability) can be provided.

Brief Description of the Drawings

[0013]

Figure 1

Embodiments for Carrying Out the Invention

[0014] On a first aspect, the present invention provides a polymer having a structural unit (A) represented by the following formula (1):

[0015]

Chemical formula

[0016] In the above formula (1), Ar 1 ~Ar 3 are each independently a divalent aromatic hydrocarbon group having 6 or more and 60 or less ring-forming atoms, which may be substituted or unsubstituted, Ar 4 is a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which 3 or more benzene rings are condensed, Ar 5 is a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 or more and 60 or less ring-forming atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 or more and 60 or less ring-forming atoms, Ar 6 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 or more and 60 or less ring-forming atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 or more and 60 or less ring-forming atoms, p is 0 or 1.

[0017] In this specification, the structural unit (A) represented by the above formula (1) is also referred to as "structural unit (A) represented by formula (1)", "structural unit (A)" or "structural unit (A) according to the present invention". Further, the following structure in the "structural unit (A) represented by formula (1)":

[0018]

Chemical formula

[0019] A structural unit having [specific content] is also referred to as "structural unit X" or "structural unit X according to the present invention". Similarly, the structural unit "-Ar 6 -" in the "structural unit (A) represented by formula (1)" is also referred to as "structural unit Y" or "structural unit Y according to the present invention". Further, a polymer having the structural unit represented by formula (1) is also referred to as "polymer", "polymer according to the present invention", or "polymer according to an embodiment of the present invention".

[0020] In a second aspect, the present invention provides an electroluminescence element material containing a polymer according to the present invention.

[0021] In a third aspect, the present invention provides an electroluminescence element including a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, wherein at least one of the organic films contains a polymer according to the present invention. In this specification, the electroluminescence element is also simply referred to as "LED". The quantum dot electroluminescence element is also simply referred to as "QLED" . The organic electroluminescence element is also simply referred to as "OLED".

[0022] As materials constituting the light-emitting layer and carrier transport layer of the electroluminescence element, various low-molecular materials and high-molecular materials are used. Among these, low-molecular materials are excellent in terms of the efficiency and lifetime of the element. However, when using low-molecular materials, there is a problem that the manufacturing cost is high because it is necessary to fabricate the element by a vacuum process. On the other hand, as high-molecular materials, TFB etc. are known as hole transport materials (for example, paragraphs "0036", "0037" of Patent Document 1). However, such high-molecular materials do not have a sufficiently long durability (light-emitting lifetime) (see Comparative Example 2-1 below). Therefore, the development of high-molecular materials capable of improving durability (light-emitting lifetime) is required.

[0023] The inventors of the present invention have intensively studied means for solving the above problems (particularly, improving durability (light emission lifetime)). As a result, it has been found that by applying a polymer having a structural unit (A) represented by formula (1) to an electroluminescence element, the light emission lifetime can be improved as compared with the case of using a known material. The mechanism by which the above-described effects are exhibited according to the configuration of the present invention is presumed as follows.

[0024] Conventionally, as a polymer material known as a hole transport material, there is a triarylamine-based polymer material such as TFB. Here, TFB has the following structure in which an aryl group or an arylene group is bonded to a nitrogen atom.

[0025]

Chemical formula

[0026] The inventors of the present invention speculated that the reason why the durability (light emission lifetime) of such a triarylamine-based polymer material is not sufficient is mainly due to the weak bond between the nitrogen atom and the aryl group or the arylene group. More specifically, when a triarylamine-based polymer material such as TFB is used as a hole transport material, when electrons leaked from the electron injection layer or excitons generated in the hole transport layer (HTL) come into contact with the polymer material, the bond between the nitrogen atom and the aryl group or the arylene group (particularly, the bond between the nitrogen atom and the aryl group contained as a side chain) is likely to cleave, so that sufficient durability (light emission lifetime) is not obtained.

[0027] On the other hand, the polymer according to an embodiment of the present invention can improve durability (light emission lifetime) by having a structural unit (A) represented by formula (1). Here, the structural unit (A) has three aromatic hydrocarbon groups bonded thereto as “Ar 1 ~Ar 3 ” to the nitrogen atom, and further, “Ar 4It has a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed. That is, the structural unit (A) has, in the side chain, "Ar 3 " via "Ar 4 " and includes the above-mentioned condensed polycyclic aromatic hydrocarbon group as "Ar 4 ". And the condensed polycyclic aromatic hydrocarbon group included as this "Ar " is presumed to bring about a high resonance stabilization effect because of its large resonance energy. Therefore, in the triarylamine-based polymer material, the bond between the nitrogen atom and the aryl group or arylene group becomes stronger (the bond energy becomes larger), and as a result, even when in contact with electrons or excitons, the above bond is less likely to cleave, so it is considered that the durability (luminescence lifetime) is improved.

[0028] In addition, the present inventors have also found that sufficient luminous efficiency can be achieved by applying a polymer having the structural unit (A) represented by the formula (1) to an electroluminescence device (particularly, a quantum dot electroluminescence device (QLED)). The mechanism of the above-described effects exerted by the configuration of the present invention is presumed as follows.

[0029] The valence band level of the quantum dots used in the quantum dot electroluminescence device is, for example, about -5.7 eV for blue QLEDs and about -5.55 eV for red QLEDs. For this reason, there is a large band offset with the HOMO level of the hole transport layer material used in existing organic electroluminescence devices (OLEDs), resulting in problems such as a decrease in carrier injection efficiency and luminous efficiency. In order to solve such problems, a technique is required that can reduce the band offset with the light emitting layer (QD (Quantum Dot) layer) by using a hole transport layer material having a deeper HOMO level in the hole transport layer (HTL).

[0030] On the other hand, according to the polymer according to an embodiment of the present invention, the structure of the above formula (1), particularly the structural unit X in the above formula (1) has the following structure:

[0031]

Chem.

[0032] By doing so, it is presumed that a substance with a deep HOMO level can be obtained. Specifically, the above structural unit X has a structure in which a monoamine (-(Ar 1 )-N(Ar 3 )-(Ar 2 )) is arranged in the main chain. And Ar 3 is a divalent aromatic hydrocarbon group having 6 or more and 60 or less ring-forming atoms, which may be substituted or unsubstituted, and Ar 4 is a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which 3 or more benzene rings are condensed, so there is a large steric hindrance. Therefore, as a stable structure, Ar 3 and Ar 4 will take a twisted structure. As a result, since the conjugation length becomes shorter, it is considered that the HOMO level of the polymer according to one embodiment of the present invention becomes deeper.

[0033] Therefore, in a quantum dot electroluminescence device having a hole injection layer or a hole transport layer (particularly a hole transport layer) containing the polymer according to one embodiment of the present invention and a light-emitting layer containing quantum dots, the HOMO level difference (barrier) between the hole injection layer or the hole transport layer (particularly the hole transport layer) and the light-emitting layer is small, and the injection ability of holes (holes) from these layers into the light-emitting layer can be improved. In addition, since the injection ability of holes (holes) into the light-emitting layer can be improved, it is also possible to widen the light-emitting region. Therefore, by using the polymer according to one embodiment of the present invention, an electroluminescence device that exhibits good luminous efficiency can be manufactured.

[0034] Note that the above mechanism is based on speculation, and the present invention is not restricted by the above mechanism at all.

[0035] Hereinafter, embodiments of the present invention will be described. Note that the present invention is not limited only to the following embodiments. Also, each drawing is exaggerated for convenience of explanation, and the dimensional ratios of the respective components in each drawing may be different from the actual ones. Further, when the embodiments of the present invention are described with reference to the drawings, the same reference numerals are given to the same elements in the description of the drawings, and duplicate descriptions are omitted.

[0036] In this specification, unless otherwise specified, measurements of operations and physical properties are performed under the conditions of room temperature (20°C or higher and 25°C or lower) / relative humidity of 40% RH or higher and 50% RH or lower.

[0037] In this specification, “x and y are each independently” means that x and y may be the same or different.

[0038] In this specification, the group “derived from “compound z” or the group “derived from “compound z” means a group in which, when “compound z” is a cyclic compound, hydrogen atoms directly bonded to the ring-forming atoms are removed by the number of valences from its ring structure and the free valences are formed.

[0039] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, monocyclic, condensed ring, and ring assembly) (for example, monocyclic compound, condensed ring compound, crosslinked compound, carbocyclic compound, and heterocyclic compound). Atoms that do not constitute the ring (for example, hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The number of ring-forming atoms described below is the same unless otherwise specified.

[0040] For example, a benzene ring has 6 ring-forming atoms, a naphthalene ring has 10 ring-forming atoms, a pyridine ring has 6 ring-forming atoms, and a furan ring has 5 ring-forming atoms.

[0041] When, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming atoms of the benzene ring. Therefore, the number of ring-forming atoms of the benzene ring substituted with an alkyl group is 6. Also, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of atoms of the alkyl group is not included in the number of ring-forming atoms of the naphthalene ring. Therefore, the number of ring-forming atoms of the naphthalene ring substituted with an alkyl group is 10.

[0042] For example, the number of hydrogen atoms bonded to a pyridine ring or the atoms constituting a substituent is not included in the number of ring-forming atoms of the pyridine ring. Therefore, the number of ring-forming atoms of the pyridine ring to which a hydrogen atom or a substituent is bonded is 6.

[0043] As used herein, "substituted" means, unless otherwise defined, substituted with an alkyl group, a cycloalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxy group, a cycloalkoxy group, an alkenyl group, an alkynyl group, an amino group, an aryl group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a hydroxy group (-OH), a carboxy group (-COOH), a thiol group (-SH), or a cyano group (-CN). Note that when a group is substituted, substitution forms in which the substituted structure is included in the definition before being further substituted are excluded. For example, when the substituent is an alkyl group, this alkyl group as a substituent is not further substituted with an alkyl group. Also, these substituents may be bonded to each other to form a ring.

[0044] Here, the alkyl group as a substituent may be either linear or branched. is preferably a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms. Specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl-1-isopropylbutyl group, 2-methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, isodecyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, nonadecyl group, icosyl group, etc. are mentioned.

[0045] Examples of the cycloalkyl group as a substituent include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.

[0046] Examples of the hydroxyalkyl group include those in which the above alkyl group is substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) hydroxy groups (e.g., hydroxymethyl group, hydroxyethyl group).

[0047] Examples of the alkoxyalkyl group as a substituent include those in which the above alkyl group is substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) of the above alkoxy groups.

[0048] As the alkoxy group as a substituent, it may be either linear or branched, but preferably a linear alkoxy group having 1 to 20 carbon atoms or a branched alkoxy group having 3 to 20 carbon atoms. For example, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, hexadecyloxy group, heptadecyloxy group, octadecyloxy group, 2-ethylhexyloxy group, 3-ethylpentyloxy group and the like can be mentioned.

[0049] As the cycloalkoxy group as a substituent, for example, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group and the like can be mentioned.

[0050] As the alkenyl group as a substituent, for example, vinyl group, allyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 1-heptenyl group, 2-heptenyl group, 5-heptenyl group, 1-octenyl group, 3-octenyl group, 5-octenyl group and the like can be mentioned.

[0051] As the alkynyl group as a substituent, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 1-heptynyl group, 2-heptynyl group, 5-heptynyl group, 1-octynyl group, 3-octynyl group, 5-octynyl group and the like can be mentioned.

[0052] As the aryl group as a substituent, preferably, an aryl group having 6 to 30 carbon atoms can be mentioned. For example, a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, an anthryl group, a pyrenyl group, an azulenyl group, an acenaphthylenyl group, a terphenyl group, a phenanthryl group and the like can be mentioned.

[0053] As the aryloxy group as a substituent, for example, a phenoxy group, a naphthyloxy group and the like can be mentioned.

[0054] As the alkylthio group as a substituent, for example, a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group and the like can be mentioned.

[0055] As the cycloalkylthio group as a substituent, for example, a cyclopentylthio group, a cyclohexylthio group and the like can be mentioned.

[0056] As the arylthio group as a substituent, for example, a phenylthio group, a naphthylthio group and the like can be mentioned.

[0057] As the alkoxycarbonyl group as a substituent, for example, a methyloxycarbonyl group, an ethyloxycarbonyl group, a butyloxycarbonyl group, an octyloxycarbonyl group, a dodecyloxycarbonyl group and the like can be mentioned.

[0058] As the aryloxycarbonyl group as a substituent, for example, a phenyloxycarbonyl group, a naphthyloxycarbonyl group and the like can be mentioned.

[0059] [Polymer] The polymer of the present invention has a structural unit (structural unit (A)) represented by the following formula (1). A polymer having the following structure has a strong bond (large bond energy) between the nitrogen atom contained in the main chain and the aryl group or arylene group, and these bonds are difficult to cleave even when in contact with electrons or excitons. Therefore, an electroluminescence device (particularly a quantum dot electroluminescence device) containing the polymer of the present invention (particularly in a hole transport layer or a hole injection layer) is excellent in durability (luminescence lifetime).

[0060] In addition, a polymer having the following structure has a deep HOMO level (HOMO level). Therefore, an electroluminescence device (particularly a quantum dot electroluminescence device) containing the polymer of the present invention (particularly in a hole transport layer or a hole injection layer) can obtain good luminous efficiency. The polymer of the present invention may contain one kind of the structural unit (structural unit (A)) of formula (1) or may contain two or more kinds of structural units (A). Note that the plurality of structural units (A) may be present in a block form, a random form, an alternating form, or a periodic form.

[0061] [Chemical formula]

[0062] In the above formula (1), the structural unit X (the structural unit on the left side of the above formula (1); that is, Ar 1 and Ar 2 and in which a nitrogen atom (furthermore, Ar 3 etc. as a side chain) is sandwiched) constitutes the polymer according to one embodiment of the present invention. When two or more kinds of structural units (A) are present, the "structural unit X" in each structural unit (A) may be the same or different. Similarly, in the above formula (1), the structural unit Y (the structural unit on the right side of the above formula (1); that is, the structural unit represented by "Ar 6 ") constitutes the polymer according to one embodiment of the present invention, and when two or more kinds of structural units (A) are present, the "structural unit Y" in each structural unit (A) may be the same or different.

[0063] That is, it can be said that the polymer according to the present invention is a copolymer containing the above-mentioned structural unit X and structural unit Y. The polymer according to the present invention contains at least one structural unit (A) represented by the above formula (1), and has a form in which the structural unit X and the structural unit Y are alternately copolymerized (that is, an alternating copolymer).

[0064] In the above formula (1), Ar 1 ~Ar 3 (Ar 1 , Ar 2 and Ar 3 ) each independently represents a divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, which may be substituted or unsubstituted. At this time, Ar 1 ~Ar 3 may be the same or different, but it is preferable that Ar 1 and Ar 2 are the same.

[0065] Ar 1 ~Ar 3 The aromatic hydrocarbon group as may be a monocyclic or a condensed ring. Here, the divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms is not particularly limited, and examples thereof include a phenylene group, an indenylene group, a naphthalenylene group, an anthracenylene, an azulenylene group, an acenaphthenylen group, a phenalenylene group, a fluorenylene group, a phenanthrenylene group, a biphenylene group, a terphenylene group, a quaterphenylene group, a kinkiphenylene group, a pyrenylene group, a spirobifluorenylene group, and a group composed of a combination thereof.

[0066] Ar 1 ~Ar 3 are each independently preferably a divalent aromatic hydrocarbon group having 6 to 30 ring-forming atoms, which may be substituted or unsubstituted, and more preferably a divalent aromatic hydrocarbon group having 6 to 20 ring-forming atoms, which may be substituted or unsubstituted.

[0067] Furthermore, Ar1 ~Ar 3 is preferably a group independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, and a substituted or unsubstituted fluorenylene group, respectively.

[0068] Among these, from the viewpoint of further improving durability, Ar 1 and Ar 2 are more preferably groups independently selected from a substituted or unsubstituted phenylene group (o, m, p-phenylene group) and a substituted or unsubstituted fluorenylene group, respectively. Particularly preferably, Ar 1 and Ar 2 are groups selected from an unsubstituted phenylene group and a substituted fluorenylene group. Most preferably, Ar 1 and Ar 2 are groups selected from an unsubstituted p-phenylene group and a substituted fluorenylene group. Further, in the above aspect, the group substituting the fluorenylene group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. Here, examples of the alkyl group having 1 to 20 carbon atoms are the same alkyl groups as those listed in the above "substituent". Further, the alkyl group may be linear or branched, but is preferably linear.

[0069] Also, from the same viewpoint as above, Ar 3 is more preferably a group selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, and a substituted or unsubstituted fluorenylene group. Particularly preferably, Ar is any of the groups represented by the following formulas (2) to (4): 3 :

[0070]

Chemical formula

[0071] In the above formula (3), R 1 and R 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R 1 and R 2 may be bonded to each other to form a ring.

[0072] Also, at this time, R 1 and R 2 may be the same or different, but it is preferable that R 1 and R 2 are the same.

[0073] The above R 1 and R 2 The number of ring-forming atoms of the aromatic hydrocarbon group as is preferably 6 to 20, more preferably 6 to 15, and particularly preferably 6 to 10.

[0074] Also, the number of carbon atoms of the alkyl group as the above R 1 and R 2 is preferably 1 to 30, more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 3 to 8.

[0075] The above R 1 and R 2 The aromatic hydrocarbon group as may be a monocyclic or condensed ring. Here, R 1 and R 2 Specific examples of the aromatic hydrocarbon group as are not particularly limited, but include, for example, a phenyl group, a naphthyl group, a phenanthryl group, a biphenylenyl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a fluorenyl group, an azulhenyl group, an acenaphthenyl group, a fluoranthenyl group, a naphthacenyl group, a perylenyl group, a pentacenyl group, a terphenylenyl group, a quarterphenylenyl group, a chrysenyl group, and a group composed of a combination thereof.

[0076] The above R 1 , R 2 Specific examples of the alkyl group as, although not particularly limited, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, tert-butyl group, i-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, n-pentyl group, i-pentyl group, neopentyl group, tert-pentyl group (t-pentyl group), cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group, n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group (4-t-butylcyclohexyl group), n-heptyl group, 1-methylpeptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group (t-octyl group), 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyld ecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, n-triacontyl group and the like can be mentioned.

[0077] Also, the above aromatic hydrocarbon group or the above alkyl group as R 1 is R2 The above aromatic hydrocarbon group or the above alkyl group may be bonded to each other via a single bond.

[0078] Among them, from the viewpoint of further improving durability, Ar 3 is preferably any of the groups represented by the above formulas (2) and (3). More preferably, it is preferably a group selected from an unsubstituted phenylene group (o, m, p-phenylene group), a 9,9-diphenylfluorenylene group, and a 9,9-dialkylfluorenylene group. Particularly preferably, Ar 3 is a group selected from a substituted or unsubstituted phenylene group (o, m, p-phenylene group) and a 9,9-dialkylfluorenylene group. Considering the viewpoints of improving the hole injection ability and transportability in addition to durability and obtaining good luminous efficiency, Ar 3 is most preferably a 9,9-dialkylfluorenylene group (particularly, the form in which the 2nd and 7th positions are bonded to N (nitrogen atom) and Ar 4 respectively). Incidentally, regarding the 9,9-dialkylfluorenylene group as a preferred form of Ar 3 , the preferred number of carbon atoms of the alkyl group bonded to the 9th position is the same as the preferred number of carbon atoms of the alkyl group as R 1 and R 2 in the above formula (3). Furthermore, the alkyl group may be linear or branched, but is preferably linear.

[0079] Ar 1 ~Ar 3 By making each of them a combination of the above preferred forms, the resonance stabilization effect by Ar 4 is more likely to spread within the molecule, the bonds between the nitrogen atom and Ar 1 ~Ar 3 become stronger respectively (the binding energy becomes larger), and higher durability can be obtained.

[0080] In the above formula (1), Ar 4represents a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed. That is, Ar 4 is a condensed polycyclic aromatic hydrocarbon group formed by condensing three or more benzene rings, and the condensed polycyclic aromatic hydrocarbon group may be substituted or unsubstituted. The polymer of the present invention has Ar 4 as a condensed polycyclic aromatic hydrocarbon group in the side chain of the polymer, and thus has high durability due to its resonance stabilization effect. Therefore, in order to obtain a high resonance stabilization effect, Ar 4 preferably has a resonance energy of 2.5 eV or more, more preferably 2.8 eV or more, and particularly preferably 3.0 eV or more.

[0081] On the other hand, the upper limit is not particularly limited, but as the resonance energy increases, the polymer may absorb light in the visible light region. Therefore, when the polymer of the present invention is used in a hole injection layer or a hole transport layer (particularly a hole transport layer), from the viewpoint of suppressing the absorption of visible light by these layers, the resonance energy of Ar 4 is preferably 6.0 eV or less, and more preferably 5.5 eV or less.

[0082] Here, the method for determining the resonance energy is as follows. Specifically, it can be determined by the method reported by Dewar and Gleicher et al. in the literature (J. Am. Chem. Soc. 87 685 (1965)). Dewar and Gleich er et al. calculated the heat of atomization of a series of chain-conjugated hydrocarbons using a semi-empirical molecular orbital method, and found that the heat of atomization of these compounds is additive with respect to individual bonds. Specifically, it is calculated by assigning standard bond energies specific to each of the C=C, C-C, and C-H bonds. The resonance energy values in this specification shall adopt the values calculated according to this method.

[0083] Ar 4 To make the resonance energy of Ar 4The number of rings of the condensed polycyclic aromatic hydrocarbon group contained as such is preferably 3 or more and 8 or less, more preferably 3 or more and 5 or less, particularly preferably 3 or 4, and most preferably 3.

[0084] Here, specific examples of the condensed polycyclic aromatic hydrocarbon group include monovalent or divalent groups derived from condensed polycyclic aromatic hydrocarbon compounds such as anthracene (resonance energy: 3.08 eV), phenanthrene (resonance energy: 3.43 eV); tetracene (resonance energy: 3.81 eV), chrysene (resonance energy: 4.51 eV), pyrene (resonance energy: 3.97 eV), triphenylene (resonance energy: 5.20 eV), benzo[a]anthracene; pentacene, perylene (resonance energy: 5.06 eV), and the like.

[0085] Among them, Ar 4 is preferably a monovalent or divalent group derived from a compound selected from substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetracene, substituted or unsubstituted chrysene, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, and substituted or unsubstituted benzo[a]anthracene. More preferably, Ar 4 is a monovalent or divalent group derived from a compound selected from substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetracene, and substituted or unsubstituted chrysene. That is, in formula (1), Ar 4 is preferably a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted tetracenylene group, or a substituted or unsubstituted chrysenylene group. Even more preferably, Ar 4is a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenylene group, or a substituted or unsubstituted phenanthrenylene group. Particularly preferably, it is a substituted or unsubstituted anthracenyl group or a substituted or unsubstituted anthracenylene group, and most preferably, it is a substituted or unsubstituted anthracenylene group (particularly, the 9th and 10th positions are Ar 3 and Ar 5 each bonded thereto, that is, a substituted or unsubstituted 9,10-anthracenylene group).

[0086] In the above formula (1), p represents the number of Ar 5 and is 0 or 1.

[0087] In the above formula (1), when p is 0, Ar 4 is a substituted or unsubstituted divalent condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed. Also, when p is 0, it means that Ar 5 does not exist. That is, when p is 0, the ring-forming atoms of Ar 5 described as being able to be bonded are unsubstituted, indicating that a hydrogen atom is bonded to the ring-forming atoms. Further, in other words, when p is 0, Ar 4 is a substituted or unsubstituted monovalent condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed. 4 is a substituted or unsubstituted monovalent condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed.

[0088] From the viewpoint of improving durability, obtaining a polymer with a deep HOMO level, and applying the polymer to an electroluminescence element (particularly, a quantum dot electroluminescence element (QLED)) to obtain sufficient luminous efficiency, p is preferably 1. From the viewpoint of improving durability, obtaining a polymer with a deep HOMO level, and applying the polymer to an electroluminescence element (particularly, a quantum dot electroluminescence element (QLED)) to obtain sufficient luminous efficiency, p is preferably 1.

[0089] In the above formula (1), when p is 1, Ar 5represents a monovalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, which may be substituted or unsubstituted, or a monovalent aromatic heterocyclic group having 5 to 60 ring-forming atoms, which may be substituted or unsubstituted.

[0090] Ar 5 The aromatic hydrocarbon group and the aromatic heterocyclic group as [Ar] may be a monocyclic ring or a condensed ring. Here, specific examples of the monovalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms include the divalent groups derived from the aromatic hydrocarbon compounds exemplified for the above Ar 1 ~Ar 3 which can be exemplified by converting the divalent groups into monovalent groups.

[0091] In the present specification, the "aromatic heterocyclic group" is a substituent derived from an aromatic compound having one or more heteroatoms (for example, nitrogen atom (N), oxygen atom (O), phosphorus atom (P), sulfur atom (S), silicon atom (Si), selenium atom (Se), etc.) as ring-forming atoms, and the remaining ring-forming atoms are carbon atoms (C). Specific examples of the aromatic heterocyclic group having 5 to 60 ring-forming atoms are not particularly limited, and include, for example, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, benzoquinone, coumarin, fluorenone, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, pyrrole, indole, carbazole, imidazole, benzimidazole, pyrazole, indazole, oxazole, isoxazole, benzoxazole, benzisoxazole, thiazole, isothiazole, benzothiazole, benzisothiazole, imidazolinone, benzimidazolinone, imidazopyridine, imidazopyrimidine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, and monovalent groups derived from aromatic heterocyclic compounds such as combinations thereof.

[0092] Ar 5 is preferably a monovalent aromatic hydrocarbon group having 6 to 30 ring-forming atoms, which may be substituted or unsubstituted, or a monovalent aromatic heterocyclic group having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted. More preferably, it is a monovalent aromatic hydrocarbon group having 6 to 15 ring-forming atoms, which may be substituted or unsubstituted, or a monovalent aromatic heterocyclic group having 5 to 15 ring-forming atoms, which may be substituted or unsubstituted.

[0093] Furthermore, Ar 5 is preferably a monovalent group selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group.

[0094] Furthermore, Ar 5 is preferably a monovalent group selected from a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group.

[0095] Among these, from the viewpoint of further improving durability, in the above formula (1), p is 1, and Ar 5 is preferably a group represented by the following formula (5) or (6):

[0096]

Chemical formula

[0097] In the above formula (5), R 3 and R 4 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R 3 and R 4 may be bonded to each other to form a ring.

[0098] R 3 、R 4 The number of ring-forming atoms of the aromatic hydrocarbon group as R is preferably 6 or more and 20 or less, more preferably 6 or more and 15 or less, and particularly preferably 6 or more and 10 or less.

[0099] Also, R 3 、R 4 The number of carbon atoms of the alkyl group as R is preferably 1 or more and 30 or less, more preferably 1 or more and 15 or less, and particularly preferably 1 or more and 10 or less.

[0100] R 3 、R 4 Specific examples of the aromatic hydrocarbon group and the alkyl group as R are the same as the specific examples of the aromatic hydrocarbon group and the alkyl group exemplified for the above R 1 、R 2 Therefore, the description is omitted. Note that the aromatic hydrocarbon group or the alkyl group as R 3 may be bonded to the aromatic hydrocarbon group or the alkyl group as R 4 via a single bond.

[0101] In the above formula (5), a is 0, 1, 2, or 3, b is 0, 1, 2, 3, or 4, and when either a or b is 2 or more, each R 3 or each R 4 may be the same or different from each other.

[0102] a and b each represent the number of R 3 and R 4 substituted on the ring-forming atoms included in the structure of formula (5). That a or b is 0 means that the corresponding R 3 or R 4 does not exist. That is, in the above formula (5), the ring-forming atoms described as being able to be bonded with the substituent R 3 or R 4 are unsubstituted, indicating that a hydrogen atom is bonded to the ring-forming atoms.

[0103] a is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. b is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0.

[0104] In the above formula (5), X is a group selected from -C(R 5 )(R 6 ), -O- and -S-. Among them, from the viewpoint of further improving durability, X is preferably a group selected from -C(R 5 )(R 6 )- and -S-.

[0105] In the above formula (5), when X is -C(R 5 )(R 6 ), R 5 and R 6 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 or more and 30 or less ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 or more and 50 or less carbon atoms. At this time, R 5 and R 6 may be bonded to each other to form a ring.

[0106] R 5 and R 6 may be the same or different, but it is preferable that R 5 and R 6 are the same.

[0107] The number of ring-forming atoms of the aromatic hydrocarbon group as the above R 5 , R 6 is preferably 6 or more and 20 or less, more preferably 6 or more and 15 or less, and particularly preferably 6 or more and 10 or less.

[0108] Also, the number of carbon atoms of the alkyl group as the above R 5 , R 6 is preferably 1 or more and 30 or less, more preferably 1 or more and 15 or less, and particularly preferably 1 or more and 10 or less.

[0109] R 5 、R 6 Specific examples of the aromatic hydrocarbon group and the alkyl group as R 1 、R 2 are the same as the specific examples of the aromatic hydrocarbon group and the alkyl group exemplified for the above R 5 respectively, and thus the description thereof is omitted. Note that the aromatic hydrocarbon group or the alkyl group as R 6 may be bonded to the aromatic hydrocarbon group or the alkyl group as R

[0110] In particular, from the viewpoint of further improving durability, R 5 and R 6 are each preferably an unsubstituted or substituted linear or branched alkyl group having 1 to 10 carbon atoms, and more preferably an unsubstituted or substituted linear alkyl group having 1 to 10 carbon atoms.

[0111] In the above formula (6), R 7 and R 8 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R 7 and R 8 may be bonded to each other to form a ring.

[0112] R 7 、R 8 The number of ring-forming atoms of the aromatic hydrocarbon group as is preferably 6 to 20, more preferably 6 to 15, and particularly preferably 6 to 10.

[0113] Also, the number of carbon atoms of the alkyl group as R 7 、R 8 is preferably 1 to 30, more preferably 1 to 15, and particularly preferably 1 to 10.

[0114] Also, R7 , R 8 Specific examples of the aromatic hydrocarbon group and the alkyl group as R 1 , R 2 are the same as the specific examples of the aromatic hydrocarbon group and the alkyl group exemplified for R 7 above, and thus the description is omitted. In addition, the aromatic hydrocarbon group or the alkyl group as R 8 may be bonded to the aromatic hydrocarbon group or the alkyl group as R 8 via a single bond.

[0115] In the above formula (6), c is 0, 1, 2, or 3, d is 0, 1, 2, 3, or 4, and when either c or d is 2 or more, each R 7 or each R 8 may be the same or different from each other.

[0116] c and d each represent the number of R 7 and R 8 substituted on the ring-forming atoms included in the structure of formula (6). That c or d is 0 means that the corresponding R 7 or R 8 does not exist. That is, in the above formula (6), the ring-forming atoms described as being able to be bonded with the substituent R 7 or R 8 are unsubstituted, indicating that a hydrogen atom is bonded to the ring-forming atom.

[0117] c is preferably 0, 1, or 2, more preferably 0 or 1, and particularly preferably 0. d is preferably 0, 1, or 2, more preferably 0 or 1, and particularly preferably 0.

[0118] Furthermore, from the viewpoint of improving durability and obtaining sufficient luminous efficiency, in the above formula (1), p is 1, and Ar 5 is preferably a group represented by the above formula (5).

[0119] Furthermore, at this time, the group represented by the above formula (5) is preferably any one of the groups represented by the following formulas (501) to (515):

[0120]

Chem.

[0121]

Chem.

[0122] In the above formulas (501) to (515), R 301 ~R 315 and R 401 ~R 415 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R 301 and R 401 , R 302 and R 402 , R 303 and R 403 , R 304 and R 404 , R 305 and R 405 , R 306 and R 406 , R 307 and R 407 , R 308 and R 408 , R 309 and R 409 , R 310 and R 410 , R 311 and R 411 , R 312 and R 412 , R 313 and R 413 , R 314 and R 414 , as well as R 315 and R 415 may each be bonded to each other to form a ring.

[0123] In the above formulas (501) to (515), R 301 ~R 315 are R in the above formula (5), 3 and R 401 ~R 415 are R in the above formula (5), 4 is synonymous with.

[0124] R 301 ~R 315 , R 401 ~R 415 The aromatic hydrocarbon group as represented by the formula (I) preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

[0125] Also, R 301 ~R 315 , R 401 ~R 415 The number of carbon atoms in the alkyl group is 1 or more. It is preferably at least 30, more preferably at least 1 and at most 15, and particularly preferably at least 1 and at most 10.

[0126] Also, R 301 ~R 315 , R 401 ~R 415 Specific examples of the aromatic hydrocarbon group and the alkyl group as R 1 , R 2 Since these are the same as the specific examples of the aromatic hydrocarbon group and the alkyl group given for R, their explanation will be omitted. 301 ~R 315 The aromatic hydrocarbon group or alkyl group as R 401 ~R 415 and the aromatic hydrocarbon group or alkyl group as the substituent may be bonded to each other via a single bond.

[0127] In the above formulas (501) to (515), a1 to a15 are each independently 0, 1, 2, or 3, b1 to b15 are each independently 0, 1, 2, 3, or 4, and when any of a1 to a15 and b1 to b15 is 2 or more, each R 301, each R 302 , each R 303 , each R 304 , each R 305 , each R 306 , each R 307 , each R 308 , each R 309 , each R 310 , each R 311 , each R 312 , each R 313 , each R 314 , each R 315 , each R 401 , each R 402 , each R 403 , each R 404 , each R 405 , each R 406 , each R 407 , each R 408 , each R 409 , each R 410 , each R 411 , each R 412 , each R 413 , each R 414 , or each R 415 may be the same or different from each other.

[0128] In the above formulas (501) to (515), a1 to a15 and b1 to b15 respectively represent the numbers of R 301 ~R 315 and R 401 ~R 415 substituted for the ring-forming atoms contained in the structures of formulas (501) to (515), a1 to a15 are 0, 1, 2, or 3, and b1 to b15 are 0, 1, 2, 3, or 4.

[0129] When a1, a2, a3, a4, a5, a6, a7, a8, a9, a10, a11, a12, a13, a14, or a15 is 0, the corresponding R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 , R 308 , R 309 , R 310 , R 311 , R 312 , R313 、R 314 or R 315 does not exist. That is, in the above formulas (501) to (515), the substituent R 301 、R 302 、R 303 、R 304 、R 305 、R 306 、R 307 、R 308 、R 309 、R 310 、R 311 、R 312 、R 313 、R 314 or R 315 The ring-forming atoms described as being optionally bonded are unsubstituted, indicating that a hydrogen atom is bonded to the ring-forming atom.

[0130] Similarly, b1, b2, b3, b4, b5, b6, b7, b8, b9, b10, b11, b12, b13, b14 or b15 being 0 means that the corresponding R 401 、R 402 、R 403 、R 404 、R 405 、R 406 、R 407 、R 408 、R 409 、R 410 、R 411 、R 412 、R 413 、R 414 or R 415 does not exist. That is, in the above formulas (501) to (515), the substituent R 401 、R 402 、R 403 、R 404 、R 405 、R 406 、R 407 、R 408 、R 409 、R 410 、R 411 、R 412 、R 413 、R 414 or R 415The ring-forming atoms described as being able to be bonded may be unsubstituted, indicating that a hydrogen atom is bonded to the ring-forming atom.

[0131] Also, when any of a1 to a15 and b1 to b15 is 2 or more, each R 301 each R 302 each R 303 each R 304 each R 305 each R 306 each R 307 each R 308 each R 309 each R 310 each R 311 each R 312 each R 313 each R 314 each R 315 each R 401 each R 402 each R 403 each R 404 each R 405 each R 406 each R 407 each R 408 each R 409 each R 410 each R 411 each R 412 each R 413 each R 414 or each R 415 may be the same or different.

[0132] a1 to a15 are each preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. b1 to b15 are each preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0.

[0133] In the above formulas (504) to (507), R 504 to R 507 and R 604 to R 607 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R504 and R 604 , R 505 and R 605 , R 506 and R 606 , and R 507 and R 607 may each be bonded to each other to form a ring.

[0134] In the above formulas (504) to (507), R 504 ~R 507 are each synonymous with R 5 in the above formula (5), and R 604 ~R 607 are each synonymous with R 6 in the above formula (5).

[0135] R 504 and R 604 , R 505 and R 605 , R 506 and R 606 , and R 507 and R 607 may each be the same or different, but it is preferable that R 504 and R 604 , R 505 and R 605 , R 506 and R 606 , and R 507 and R 607 are each preferably the same.

[0136] R 504 ~R 507 , R 604 ~R 607 The number of ring-forming atoms of the aromatic hydrocarbon group as R

[0137] Also, the above R 504 ~R 507 , R 604 ~R 607The number of carbon atoms of the alkyl group as [the alkyl group] is preferably 1 or more and 30 or less, more preferably 1 or more and 15 or less, particularly preferably 1 or more and 10 or less, and most preferably 1 or more and 3 or less.

[0138] R 504 ~R 507 、R 604 ~R 607 Specific examples of the aromatic hydrocarbon group and the alkyl group as [the aromatic hydrocarbon group and the alkyl group] are the same as the specific examples of the aromatic hydrocarbon group and the alkyl group exemplified for the above R 1 、R 2 respectively, and thus the description thereof is omitted. Note that the aromatic hydrocarbon group or the alkyl group as [the aromatic hydrocarbon group or the alkyl group] of R 504 ~R 507 may be bonded to the aromatic hydrocarbon group or the alkyl group as [the aromatic hydrocarbon group or the alkyl group] of R 604 ~R 607 via a single bond to each other.

[0139] Among them, from the viewpoint of further improving the durability and obtaining sufficient luminous efficiency, R 504 ~R 507 and R 604 ~R 607 are each independently preferably a substituted or unsubstituted linear or branched alkyl group having 1 or more and 10 or less carbon atoms, more preferably a substituted or unsubstituted linear alkyl group having 1 or more and 10 or less carbon atoms, and particularly preferably a substituted or unsubstituted linear alkyl group having 1 or more and 3 or less carbon atoms.

[0140] Among the above, the group represented by the above formula (5) is preferably any of the groups represented by the above formulas (504) to (507) and the above formulas (512) to (515). That is, in the above formula (1), p is 1, and Ar 5 is preferably any of the groups represented by the above formulas (504) to (507) and the above formulas (512) to (515).

[0141] 《Preferred Forms of Structural Unit X》 In the above formula (1), as a preferred form of structural unit X, Ar1 ~Ar 3 is one of the groups represented by the above formula (2) or (3), p is 0 or 1, and when p is 1, Ar 4 is a substituted or unsubstituted anthracenylene group, or a substituted or unsubstituted phenanthrenylene group, and when p is 0, Ar 4 is substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted phenanthrenyl group, and when p is 1, Ar 5 is one of the groups represented by the above formula (504) to (507) and the above formula (512) to (515). In a more preferred form, Ar 1 and Ar 2 are groups represented by the above formula (2), Ar 3 is one of the groups represented by the above formula (2) or (3), p is 0 or 1, and when p is 1, Ar 4 is a substituted or unsubstituted anthracenylene group, or a substituted or unsubstituted phenanthrenylene group, and when p is 0, Ar 4 is a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted phenanthrenyl group, and when p is 1, Ar 5 is one of the groups represented by the above formula (504) to (507) and the above formula (512) to (515). In a particularly preferred form, Ar 1 and Ar 2 are groups represented by the above formula (2), Ar 3 is one of the groups represented by the above formula (2) or (3), p is 0 or 1, and when p is 1, Ar 4 is an unsubstituted anthracenylene group, or an unsubstituted phenanthrenylene group, and when p is 0, Ar 4 is an unsubstituted anthracenyl group, or an unsubstituted phenanthrenyl group, and when p is 1, Ar 5is any of the groups represented by the above formulas (504) to (507) and the above formulas (512) to (515), and in the above formulas (504) to (507) and the above formulas (512) to (515), a4 to a7, a12 to a15, b4 to b7, and b12 to b15 are 0.

[0142] The polymer having the structural unit X as described above is Ar 4 has excellent durability due to the resonance stabilization effect of. Further, the polymer having the above structure has a deep HOMO level (therefore, the light emission efficiency of an LED (especially a QLED) using the polymer according to an embodiment of the present invention can be made good).

[0143] Preferable examples of the structural unit X according to the present invention include, for example, the following structures.

[0144]

Chemical formula

[0145]

Chemical formula

[0146]

Chemical formula

[0147]

Chemical formula

[0148]

Chemical formula

[0149]

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[0150]

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[0151]

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[0280] In the above structural formula, the group represented by "-C n H 2n+1 (where n is a natural number)" represents a linear alkyl group. Also, * is the bonding site forming the main chain. The same applies to the structural formulas described in this specification unless otherwise specified.

[0281] Among them, as the constitutional unit X, it is preferable to be selected from the above structures (X-a1-1) to (X-a1-12), (X-a2-1) to (X-a2-12), (X-a3-1) to (X-a3-12), (X-a5-1) to (X-a5-12), (X-o4-1) to (X-o4-9).

[0282] Furthermore, particularly preferred examples of the constitutional unit X according to the present invention include the following structures (X-1) to (X-8). The following structures (X-1) to (X-8) correspond to the above structures (X-a1-5) , (X-a1-1), (X-a2-1), (X-a1-2), (X-a3-5), (X-a3-2), (X-a5-5), (X-o4-1), respectively.

[0283] [Chemical]

[0284] In the above formula (1), Ar 6(That is, the structural unit Y) constitutes a polymer according to an embodiment of the present invention in addition to the above structural unit X, and represents a divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, which may be substituted or unsubstituted, or a divalent aromatic heterocyclic group having 5 to 60 ring-forming atoms, which may be substituted or unsubstituted.

[0285] Ar 6 The aromatic hydrocarbon group and the aromatic heterocyclic group as [Ar] may be monocyclic or condensed rings. Here, specific examples of the divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms include the divalent groups derived from the aromatic hydrocarbon compounds exemplified for the above Ar 1 ~Ar 3 Since they are the same as those exemplified above, the description thereof is omitted. Further, specific examples of the divalent aromatic heterocyclic group having 5 to 60 ring-forming atoms can be exemplified by converting the monovalent groups derived from the aromatic heterocyclic compounds exemplified for the above Ar 5 into divalent groups.

[0286] Ar 6 is preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 ring-forming atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 30 ring-forming atoms, and more preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 20 ring-forming atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 20 ring-forming atoms.

[0287] Among these, Ar 6 is preferably selected from the groups represented by the following formulas (7) to (22). That is, in a preferred embodiment of the present invention, in the above formula (1), Ar 6 is any of the groups represented by the following formulas (7) to (22):

[0288]

Chemical formula

[0289] In the above formulas (7) to (22), R 9~R 35 each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring-forming atoms, an alkyl group having 1 to 60 carbon atoms, or a hydrogen atom. Here, R 9 ~R 35 may be the same or different from each other.

[0290] R 9 ~R 35 The aromatic hydrocarbon group and the aromatic heterocyclic group as R 1 ~Ar 3 ~Ar 5 may each be a monocyclic or condensed ring. Here, specific examples of the monovalent aromatic hydrocarbon group having 6 to 60 ring-forming carbon atoms can be exemplified by converting the divalent group derived from the aromatic hydrocarbon compound exemplified for the above Ar 1 R 2 to a monovalent group. Further, specific examples of the monovalent aromatic heterocyclic group having 5 to 60 ring-forming atoms are the same as the specific examples of the aromatic heterocyclic group exemplified for the above Ar

[0291] R 9 ~R 35 The number of ring-forming atoms of the aromatic hydrocarbon group as R

[0292] ~R 9 ~R 35 is preferably 6 to 20, more preferably 6 to 15, and particularly preferably 6 to 10.

[0293] R 9 ~R 35The number of carbon atoms of the alkyl group as [specified] is preferably 1 or more and 30 or less, more preferably 3 or more and 20 or less, and particularly preferably 5 or more and 15 or less.

[0294] Among these, R 9 ~R 35 are each independently preferably a group selected from the group consisting of a monovalent aromatic heterocyclic group having 10 to 15 ring-forming atoms, which may be substituted or unsubstituted, a linear alkyl group having 3 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, and a hydrogen atom, and more preferably a group selected from the group consisting of a monovalent aromatic heterocyclic group having 10 to 15 ring-forming atoms, which may be substituted or unsubstituted, a linear alkyl group having 5 to 15 carbon atoms, and a hydrogen atom.

[0295] Furthermore, the aromatic heterocyclic group, which is a preferred form as R 9 ~R 35 is preferably substituted, and among them, it is preferably substituted by an alkyl group, a cycloalkyl group, an aryl group, and a combination thereof.

[0296] In the above formulas (7) to (22), Q 1 ~Q 9 each independently represents -O-, -S-, -Se-, -CR 36 R 37 -, or -SiR 38 R 39 -, and in this case, R 36 ~R 39 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 36 and R 37 may be the same or different, but it is preferable that R 36 and R 37 are the same. Similarly, R 38 and R 39 may be the same or different, but it is preferable that R 38 and R 39It is preferably the same.

[0297] Here, as the alkyl group and the aryl group, the specific examples of the alkyl group and the aromatic hydrocarbon group exemplified for the above R 1 、R 2 are the same as the specific examples respectively, and thus the description thereof is omitted. Further, as the heteroaryl group, for example, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group and the like can be mentioned.

[0298] The above R 36 、R 37 The number of carbon atoms of the alkyl group as is preferably 1 or more and 30 or less, more preferably 3 or more and 20 or less, particularly preferably 5 or more and 15 or less, and most preferably 10 or more and 13 or less.

[0299] The above R 36 、R 37 The number of ring-forming atoms of the aryl group as is preferably 6 or more and 20 or less, more preferably 6 or more and 15 or less, and particularly preferably 6 or more and 10 or less.

[0300] The above R 36 、R 37The number of ring-forming atoms of the heteroaryl group as such is preferably 6 or more and 20 or less, more preferably 6 or more and 15 or less, and particularly preferably 6 or more and 10 or less.

[0301] In the above formulas (7) to (22), Z 1 ~Z 7 each independently represents -CR 40 =, -N=, or -SiR 41 =, and at this time, R 40 and R 41 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 40 and R 41 may be the same or different.

[0302] Here, as the alkyl group and the aryl group, they are the same as the specific examples of the alkyl group and the aromatic hydrocarbon group exemplified for the above R 1 , R 2 , respectively, so the description is omitted. Further, as the heteroaryl group, the same heteroaryl groups as those listed in the description of the above R 36 and R 37 are exemplified.

[0303] In the above formulas (7) to (22), * is a bonding site forming the main chain.

[0304] 《Preferred Forms of Structural Unit Y》 In the above formula (1), the preferred form of the structural unit Y (that is, Ar 6 ) is a group represented by formulas (7) to (9), and at this time, R 9 ~R 11 each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 or more and 30 or less ring-forming carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 or more and 30 or less ring-forming atoms, a linear or branched alkyl group having 1 or more and 30 or less carbon atoms, or a hydrogen atom, and Q 1 is -CR 36 R37 represents -, where R 36 and R 37 are each independently a substituted or unsubstituted linear or branched alkyl group having 3 to 20 carbon atoms. More preferably, Ar 6 is a group represented by formulas (7) to (9), where R 9 ~R 11 are each independently a substituted or unsubstituted monovalent aromatic heterocyclic group having 10 to 15 ring-forming atoms, a linear or branched alkyl group having 5 to 15 carbon atoms, or a hydrogen atom, and Q 1 represents -CR 36 R 37 -, where R 36 and R 37 are each independently a substituted or unsubstituted linear or branched alkyl group having 5 to 15 carbon atoms. Particularly preferably, Ar 6 is a group represented by formulas (7) to (9), where R 9 ~R 11 are each independently a substituted or unsubstituted monovalent aromatic heterocyclic group having 10 to 15 ring-forming atoms, a linear or branched alkyl group having 5 to 15 carbon atoms, or a hydrogen atom, and Q 1 represents -CR 36 R 37 -, where R 36 and R 37 are each independently a substituted or unsubstituted linear or branched alkyl group having 10 to 13 carbon atoms.

[0305] In the polymer having the structural unit Y as described above, the resonance stabilization effect of Ar 4 is more likely to spread throughout the whole molecule, and the durability is further improved. In addition, the polymer having the above structure has a deep HOMO level (therefore, the luminous efficiency of an LED (particularly a QLED) using the polymer according to an embodiment of the present invention can be made good).

[0306] Particularly preferred examples of the structural unit Y according to the present invention include the following structures (Y-1) to (Y-4).

[0307] [Chemical formula]

[0308] "Preferred Forms of Structural Unit (A)" From the above, the particularly preferred forms of the structural unit (A) constituting the polymer of the present invention include the following. That is, the structural unit (A) represented by the above formula (1) is preferably any one represented by the following formulas (A-1) to (A-11):

[0309] [Chemical formula]

[0310] [Chemical formula]

[0311] The polymer according to one embodiment of the present invention essentially includes a structural unit X and a structural unit Y. However, in addition to these structural units X and Y, it may have other structural units. Here, examples of the other structural units include structural units derived from compounds such as azulene, naphthalene, and anthracene. Here, when the polymer according to one embodiment of the present invention has other structural units, the composition of the other structural units is not particularly limited. Considering the durability of the polymer and the HOMO level (therefore, the hole transport ability of the layer formed using the polymer (for example, the hole injection layer, the hole transport layer), the effect of improving the light emission efficiency), etc., the other structural units are preferably more than 0 mol% and less than 15 mol%, more preferably 0.5 mol% or more and 10 mol% or less, based on all the structural units constituting the polymer. Note that when the polymer contains two or more other structural units, the content of the above other structural units means the total amount of the other structural units.

[0312] The weight average molecular weight (Mw) of the polymer according to an embodiment of the present invention is not particularly limited as long as the object and effect of the present invention can be obtained. The weight average molecular weight (Mw) is preferably, for example, 5,000 or more and 1,000,000 or less, more preferably 8,000 or more and 500,000 or less, and particularly preferably 10,000 or more and 250,000 or less. With such a weight average molecular weight, the viscosity of the coating solution for forming a layer (for example, a hole injection layer, a hole transport layer) using the polymer can be appropriately adjusted to form a layer with a uniform film thickness.

[0313] Also, the number average molecular weight (Mn) of the polymer is not particularly limited as long as the object and effect of the present invention can be obtained. The number average molecular weight (Mn) is preferably, for example, 3,000 or more and 500 ,000 or less, more preferably 5,000 or more and 300,000 or less, and particularly preferably 8,000 or more and 100,000 or less. With such a number average molecular weight, the viscosity of the coating solution for forming a layer (for example, a hole injection layer, a hole transport layer) using the polymer can be appropriately adjusted to form a layer with a uniform film thickness. Further, the polydispersity (weight average molecular weight / number average molecular weight) of the polymer of the present embodiment is, for example, 1.10 or more and 15.0 or less, preferably 1.30 or more and 13.0 or less, and more preferably 1.50 or more and 5.00 or less.

[0314] Here, the measurement of the number average molecular weight (Mn) and the weight average molecular weight (Mw) is not particularly limited, and known methods can be used or known methods can be appropriately modified and applied. In this specification, the number average molecular weight (Mn) and the weight average molecular weight (Mw) adopt the values measured by the following method. Incidentally, the polydispersity (Mw / Mn) of the polymer is calculated by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn) measured by the following method.

[0315] (Measurement of number average molecular weight (Mn) and weight average molecular weight (Mw)) The number average molecular weight (Mn) and weight average molecular weight (Mw) of the polymer are measured under the following conditions by SEC (Size Exclusion Chromatography) using polystyrene as a standard substance.

[0316] [Chemical formula]

[0317] The terminal of the main chain of the polymer according to one embodiment of the present invention is not particularly limited and is appropriately defined depending on the type of raw material used, but is usually a hydrogen atom.

[0318] The polymer according to one embodiment of the present invention can be synthesized by using a known organic synthesis method. Those skilled in the art who refer to the examples described later can easily understand the specific synthesis method of the polymer according to one embodiment of the present invention. Specifically, it can be produced by a copolymerization reaction using one or more monomers (X) represented by the following formula (X') and one or more monomers (Y) represented by the following formula (Y'). At this time, if necessary, other monomers corresponding to the above other structural units may be further added.

[0319] [Chemical formula]

[0320] [Chemical formula]

[0321] Alternatively, the polymer according to one embodiment of the present invention can be produced by a polymerization reaction using one or more monomers (A) represented by the following formula (A'). At this time, if necessary, other monomers corresponding to the above other structural units may be further added.

[0322] [Chemical formula]

[0323] The above monomers used in the polymerization of the polymer according to an embodiment of the present invention can be synthesized by appropriately combining known synthetic reactions, and their structures can also be confirmed by known methods (for example, NMR, LC-MS, etc.).

[0324] In the above formulas (X'), (Y'), and (A'), Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and p, and Ar 6 are respectively synonymous with those in the above formula (1). Further, in the above formulas (X'), (Y'), and (A'), Z 1 and Z 2 , Z 1’ and Z 2’ , and Z 1” and Z 2” are each independently a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, particularly bromine atom) or a group having the following structure. In the following structure, R A ~R D are each independently an alkyl group having 1 to 3 carbon atoms. Preferably, R A ~R D is a methyl group. In the above formula (X'), Z 1 and Z 2 , Z 1’ and Z 2’ in the above formula (Y'), and Z 1” and Z 2” in the above formula (A') may be the same or different from each other. However, in order to suppress the polymerization of monomers (X) with each other, Z 1 and Z 2 in the above formula (X') are preferably atoms or groups that do not react with each other. Similarly, in order to suppress the polymerization of monomers (B) with each other, Z 1’ and Z 2 in the above formula (Y') are preferably atoms or groups that do not react with each other. Preferably, Z 1and Z 2 and Z in the above formula (Y') 1’ and Z 2’ are the same. Also, preferably, Z in the above formula (A') 1” and Z 2” are different.

[0325] [Chemical formula]

[0326] The polymer according to one embodiment of the present invention has a structural unit X and a structural unit Y. Therefore, the polymer has a deep HOMO level. Thus, when the polymer according to one embodiment of the present invention is used as a hole injection material or a hole transport material (especially a hole transport material), good luminous efficiency can be achieved.

[0327] Specifically, the HOMO level of the polymer according to one embodiment of the present invention is not particularly limited but is, for example, -5.8 eV or more and -5.5 eV or less. Because of having such a polymer with a deep HOMO level, in a quantum dot electroluminescence device having a hole transport layer containing the polymer according to one embodiment of the present invention and a light emitting layer containing quantum dots, the band offset (barrier) between the hole transport layer and the light emitting layer is small, and the transport ability of holes (holes) from the hole transport layer to the light emitting layer can be improved. Thus, by using the polymer according to one embodiment of the present invention, an electroluminescence device (especially a QLED) that exhibits good luminous efficiency can be provided.

[0328] The glass transition temperature (Tg) of the polymer according to one embodiment of the present invention is not particularly limited, but 60°C or higher is preferable, 80°C or higher is more preferable, 90°C or higher is particularly preferable, and 100°C or higher is most preferable. On the other hand, the upper limit is also not particularly limited, but 250°C or lower is preferable, 240°C or lower is more preferable, and 230°C or lower is particularly preferable.

[0329] When the glass transition temperature (Tg) of the polymer is within the above range, it is suitable for device fabrication, and a device with more improved characteristics can be obtained. The glass transition temperature (Tg) of the polymer can be measured using a differential scanning calorimeter (DSC) (manufactured by Seiko Instruments Inc., trade name: DSC6000). The details of the measurement method are described in the examples.

[0330] [Electroluminescence device material] The polymer according to one embodiment of the present invention is suitably used as an electroluminescence device material. According to this embodiment, an electroluminescence device material having excellent durability (luminescence lifetime) is provided. Also, according to the polymer according to one embodiment of the present invention, an electroluminescence device material having good luminous efficiency is also provided. Therefore, according to the second aspect of the present invention, an electroluminescence device material containing the polymer of the present invention is provided. Alternatively, the use of the polymer according to one embodiment of the present invention as an electroluminescence device material is provided.

[0331] Further, the polymer according to one embodiment of the present invention has a deep HOMO level of -5.5 eV or less. Therefore, the polymer according to one embodiment of the present invention can be suitably used for a quantum dot electroluminescence device (especially the hole transport layer).

[0332] [Electroluminescence device] As described above, the polymer according to an embodiment of the present invention is suitably used in an electroluminescence device. That is, there is provided an electroluminescence device including a pair of electrodes and one or more organic films disposed between the electrodes and containing the polymer or an electroluminescence device material of an embodiment of the present invention. Such an electroluminescence device can exhibit excellent durability (luminescence lifetime). Further, the above electroluminescence device can exhibit good luminous efficiency (particularly good luminous efficiency at a low driving voltage). Therefore, according to a third aspect of the present invention, there is provided an electroluminescence device including a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, wherein at least one of the organic films contains the polymer of the present invention. The object (or effect) of the present invention can also be achieved by the electroluminescence device according to such an embodiment. As a preferred form of the above aspect, the electroluminescence device further includes a light-emitting layer disposed between the above electrodes and containing a light-emitting material capable of emitting light from triplet excitons. Note that the electroluminescence device of the present embodiment is an example of the electroluminescence device according to the present invention.

[0333] Furthermore, an embodiment of the present invention also provides a method for manufacturing an electroluminescence device including a pair of electrodes and one or more organic films disposed between the electrodes and containing the polymer of the present invention, the method including forming at least one of the organic films by a coating method. Also, according to such a method, an embodiment of the present invention provides an electroluminescence device in which at least one of the organic films is formed by a coating method.

[0334] The polymer of one embodiment of the present invention and the electroluminescent element material (EL element material) according to one embodiment of the present invention (hereinafter, also collectively referred to as "polymer / EL element material") also have good solubility in organic solvents. Therefore, the polymer / EL element material according to one embodiment of the present invention is particularly preferably used for manufacturing elements (especially thin films) by a coating method (wet process). For this reason, one embodiment of the present invention provides a liquid composition containing the polymer of the present invention and a solvent or a dispersion medium. Note that the liquid composition of the present embodiment is an example of the liquid composition according to the present invention.

[0335] Also, as described above, the electroluminescent element material according to the embodiment is preferably used for manufacturing elements (especially thin films) by a coating method (wet process). From the above viewpoints, one embodiment of the present invention provides a thin film containing the polymer of the present invention. Note that the thin film of the present embodiment is an example of the thin film according to the present invention.

[0336] In addition, the EL element material according to one embodiment of the present invention is excellent in hole injection property and hole mobility. Therefore, it can be preferably used for forming any organic film such as a hole injection material, a hole transport material, or a light-emitting material (host). Among these, from the viewpoint of hole transport property, it is preferably used as a hole injection material or a hole transport material, and particularly preferably used as a hole transport material.

[0337] That is, one embodiment of the present invention provides a composition containing a polymer and at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light-emitting material. Here, the light-emitting material contained in the composition is not particularly limited, but may contain an organometallic complex (luminescent organometallic complex compound) or semiconductor nanoparticles (semiconductor inorganic nanoparticles).

[0338] Hereinafter, with reference to FIG. 1, an electroluminescence element according to an embodiment of the present invention will be described in detail. FIG. 1 is a schematic diagram showing an electroluminescence element according to an embodiment of the present invention. In the present specification, the "electroluminescence element" may be abbreviated as "EL element".

[0339] As shown in FIG. 1, an EL element 100 according to an embodiment of the present invention includes a substrate 110, a first electrode 120 disposed on the substrate 110, a hole injection layer 130 disposed on the first electrode 120, a hole transport layer 140 disposed on the hole injection layer 130, a light-emitting layer 150 disposed on the hole transport layer 140, an electron transport layer 160 disposed on the light-emitting layer 150, an electron injection layer 170 disposed on the electron transport layer 160, and a second electrode 180 disposed on the electron injection layer 170.

[0340] Here, the polymer / EL element material of the present embodiment is included, for example, in any organic film (organic layer) disposed between the first electrode 120 and the second electrode 180. Specifically, the polymer / EL element material is preferably included in the hole injection layer 130 as a hole injection material, or in the hole transport layer 140 as a hole transport material, or in the light-emitting layer 150 as a light-emitting material (host). The polymer / EL element material is more preferably included in the hole injection layer 130 as a hole injection material or in the hole transport layer 140 as a hole transport material. The polymer / EL element material is particularly preferably included in the hole transport layer 140 as a hole transport material. That is, in a preferred form of the present invention, the organic film containing the polymer / EL element material is a hole transport layer, a hole injection layer, or a light-emitting layer. In a more preferred form of the present invention, the organic film containing the polymer is a hole transport layer or a hole injection layer. In a particularly preferred form of the present invention, the organic film containing the polymer is a hole transport layer.

[0341] In addition, the organic film containing the polymer / EL element material of the present embodiment is formed by a coating method (solution coating method). Specifically, the organic film is formed by a spin coat method, a casting method, a micro gravure coat method, a gravure coat method, a bar coat method, a roll coat method, a wire bar coat method, a dip coat method, a spry coat method, a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, or other solution coating methods.

[0342] Note that any solvent can be used for the solution coating method as long as it can dissolve the polymer / EL element material, and it can be appropriately selected according to the type of polymer used. For example, toluene, xylene, ethylbenzene, diethylbenzene, methylxylene, propylbenzene, cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl, dimethylanisole, phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, cyclohexane, etc. can be exemplified. Also, the amount of the solvent used is not particularly limited, but considering the ease of coating, etc., the concentration of the polymer is preferably 0.1% by mass or more and 10% by mass or less, more preferably about 0.5% by mass or more and 5% by mass or less.

[0343] Note that the film formation method for the layer other than the organic film containing the polymer / EL element material is not particularly limited. The layer other than the organic film containing the polymer / EL element material of the present embodiment may be formed by, for example, a vacuum evaporation method or a solution coating method.

[0344] The substrate 110 can use a substrate used in a general EL element. For example, the substrate 110 may be a glass substrate, a semiconductor substrate such as a silicon substrate, or a transparent plastic substrate or the like.

[0345] A first electrode 120 is formed on the substrate 110. Specifically, the first electrode 120 is an anode and is formed of a material with a large work function among metals, alloys, or conductive compounds, etc. For example, the first electrode 120 may be formed as a transmissive electrode by indium tin oxide (In2O3 - SnO2: ITO), indium zinc oxide (In2O3 - ZnO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are excellent in transparency and conductivity. Also, the first electrode 120 may be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), etc. on the above transparent conductive film. Further, after forming the first electrode 120 on the substrate 110, if necessary, cleaning, UV - ozone treatment may be performed.

[0346] A hole injection layer 130 is formed on the first electrode 120. The hole injection layer 130 is a layer that facilitates the injection of holes from the first electrode 120, and specifically, it may be formed with a thickness of about 10 nm or more and about 1000 nm or less, more specifically, about 20 nm or more and about 50 nm or less (dry film thickness; the same applies hereinafter).

[0347] The hole injection layer 130 can be formed of a known hole injection material. Examples of known hole injection materials for forming the hole injection layer 130 include poly(ether ketone)-containg triphenylamine (TPAPEK), 4-isopropyl-4’-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N’-diphenyl-N,N’-bis-[4-(phenyl - m - tolyl -amino)-phenyl]-biphenyl-4,4'-diamine (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine: DNTPD), copper phthalocyanine (copper phthalocyanine), 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (4,4',4”-tris(3-methylphenylphenylamino)triphenylamine: m-MTDATA), N,N'-di(1-naphthyl)-N,N'-di phenylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine: NPB), 4,4',4”-tris(diphenylamino)triphenylamine (4,4',4”-tris(diphenylamino)triphenylamine: TDATA), 4,4',4”-tris(N,N-2-naphth ylphenylamino)triphenylamine (4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine: 2-TNATA), polyaniline / dodecylbenzenesulphonic acid, poly(3,4-ethylenedioxythiophene ) / poly(4-styrenesulfonate) (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate): PEDOT / PSS), and polyaniline / 10-camphorsulf onic acid (polyaniline / 10-camphorsulfonic acid), etc. can be mentioned.

[0348] ​On the positive hole injection layer 130, a positive hole transport layer 140 is formed. The positive hole transport layer 140 is a layer having a function of transporting positive holes, and may be formed, for example, with a thickness of about 10 nm or more and about 150 nm or less, more specifically, about 20 nm or more and about 50 nm or less. The positive hole transport layer 140 is preferably formed by a solution coating method using a polymer of an embodiment of the present invention. According to this method, it is possible to extend the durability (light emission life) of the EL element 100. In addition, the performance (light emission efficiency) of the EL element 100 can be made good. Furthermore, since the positive hole transport layer can be formed by the solution coating method, it is possible to efficiently form a film over a large area.

[0349] However, when any other organic film of the EL element 100 contains a polymer of an embodiment of the present invention, the positive hole transport layer 140 may be formed of a known positive hole transport material. Examples of the known positive hole transport material include 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole, and polyvinylcarbazole carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole such as N,N’-bis(3-methylphenyl)-N,N’-diphenyl-[1,1-biphenyl]-4,4’-diamine (TPD), 4,4 ’,4”-tris(N-carbazolyl)triphenylamine (TCTA), and N,N’-di(1-naphthyl)-N,N’-diphenylbenzidine (NPB).

[0350] On the positive hole transport layer 140, a light emitting layer 150 is formed. The light emitting layer 150 is a layer that emits light by fluorescence, phosphorescence, etc., and is formed using a vacuum evaporation method, a spin coating method, an inkjet printing method, or the like. The light emitting layer 150 may be formed, for example, with a thickness of about 10 nm or more and about 60 nm or less, more specifically, about 20 nm or more and about 50 nm or less. As the light emitting material of 150, known light emitting materials can be used. However, the light emitting material contained in the light emitting layer 150 is preferably a light emitting material capable of emitting light from triplet excitons (that is, phosphorescent emission). In such a case, the driving life of the EL element 100 can be further improved.

[0351] The light emitting layer 150 is not particularly limited and can have a known configuration. Preferably, the light emitting layer contains semiconductor nanoparticles or organometallic complexes. That is, in a preferred form of the present invention, the organic film has a light emitting layer containing semiconductor nanoparticles or organometallic complexes. When the light emitting layer contains semiconductor nanoparticles, the EL element is a quantum dot electroluminescence element (QLED), a quantum dot light emitting element, or a quantum dot light emitting element. When the light emitting layer contains an organometallic complex, the EL element is an organic electroluminescence element (OLED).

[0352] In the form (QLED) in which the light emitting layer contains semiconductor nanoparticles, the light emitting layer is one in which a large number of semiconductor nanoparticles (quantum dots) are arranged in a single layer or multiple layers. Here, the semiconductor nanoparticles (quantum dots) are particles of a predetermined size having a quantum confinement effect. The diameter of the semiconductor nanoparticles (quantum dots) is not particularly limited, but is about 1 nm or more and about 20 nm or less.

[0353] The semiconductor nanoparticles (quantum dots) arranged in the light emitting layer can be synthesized by a wet chemical process, an organometallic chemical vapor deposition process, a molecular beam epitaxy process, or other similar processes. Among them, the wet chemical process is a method of growing particles by putting a precursor substance in an organic solvent.

[0354] In the wet chemical process, when crystals grow, an organic solvent is naturally coordinated on the surface of the quantum dot crystals to play the role of a dispersant, thereby regulating the crystal growth. Therefore, in the wet chemical process, it is possible to control the growth of semiconductor nanoparticles easily and at low cost compared to vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE). Compared with the methods, the growth of semiconductor nanoparticles can be controlled easily and at low cost.

[0355] By adjusting the size of semiconductor nanoparticles (quantum dots), the energy band gap can be adjusted, and light in various wavelength bands can be obtained in the light-emitting layer (quantum dot light-emitting layer). Therefore, by using quantum dots of a plurality of different sizes, it is possible to enable a display that emits (or emits) light of a plurality of wavelengths. The size of the quantum dots can be selected so that red, green, and blue light are emitted so as to be able to form a color display. In addition, the sizes of the quantum dots can be combined so that various color lights emit white light.

[0356] As the semiconductor nanoparticles (quantum dots), semiconductor materials selected from the group consisting of II-VI group semiconductor compounds; III-V group semiconductor compounds; IV-VI group semiconductor compounds; group IV elements or compounds; and combinations thereof can be used.

[0357] The II-VI semiconductor compounds are selected from the group consisting of binary compounds selected from the group consisting of, but not particularly limited to, for example, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnTeSe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, and mixtures thereof; and quaternary compounds selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0358] The III-V semiconductor compounds are selected from the group consisting of binary compounds selected from the group consisting of, but not particularly limited to, for example, GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAl NAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof.

[0359] The group III-V semiconductor compounds can be selected from the group consisting of binary compounds selected from the group consisting of, but not particularly limited to, for example, SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

[0360] The group IV element or compound can be selected from the group consisting of, but not particularly limited to, for example, monoelement compounds selected from the group consisting of Si, Ge, and mixtures thereof; and binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0361] The semiconductor nanoparticles (quantum dots) can have a homogeneous single structure or a core-shell double structure. The core-shell can contain different substances. The substances constituting each core and shell can be composed of different semiconductor compounds. However, the energy band gap of the shell material is larger than that of the core material. Specifically, structures such as ZnTeSe / ZnSe / ZnS, InP / ZnSe / ZnS, CdSe / ZnS, InP / ZnS are preferred.

[0362] For example, the case of producing quantum dots having a core (CdSe)-shell (ZnS) structure will be described. First, TOPO (trioctylphosphine oxide) was used as a surfactant Precursor substances of the core (CdSe) such as (CH3)2Cd (dimethylcadmium) and TOPSe (trioctylphosphine selenide) were injected into an organic solvent to form crystals. At this time , maintain at a high temperature for a certain period of time so that the crystal grows to a certain size, and then inject the precursor material of the shell (ZnS) to form a shell on the surface of the already formed core. In this way, CdSe / ZnS quantum dots capped with TOPO can be fabricated.

[0363] Also, in the form where the light-emitting layer contains an organometallic complex (OLED), the light-emitting layer 150 uses, as a host material, for example, 6,9-diphenyl-9'-(5'-phenyl-[1,1':3',1''-terphenyl]-3-yl) 3,3'-bi[9H-carbazole], 3,9-diphenyl-5-(3-(4-phenyl-6-(5'-phenyl-[1,1':3',1''-terphenyl]-3-yl)-1,3,5,-triazin-2-yl)phenyl)-9H-carbazole, 9,9'-diphenyl-3,3'-bi[9H-carbazole], tris(8-quinolinato)aluminium (Alq3), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), poly(n-vinyl carbazole) (PVK ), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphth-2-yl) anthracene (TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazole)- rilarylene (DSA), 4,4'-bis(9-carbazole)- It may contain 2,2’-dimethyl-biphenyl (4,4’-bis(9-carbazole)2,2’-dimethyl-bipheny: dmCBP), etc.

[0364] Also, as a dopant material, the light-emitting layer 150 may contain, for example, perylene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (4-dicyanomethylene-2-(pdimethylaminostyryl)-6-methyl-4H-pyran: DC M) and its derivatives, bis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium(III) (bis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium(III): FIrpic), bis(1-phenylisoquinoline)(acetylacetonate)iridium(III) (bis(1-phenylisoquinoline)(acetylacetonate)iridium(III): Ir(piq)2(acac)), tris(2-phenylpyridine)iridium(III) (tris(2-phenylpyridine)iridium(III): Ir(ppy)3), tris(2-(3-p-tolyl)phenyl)pyridine iridium(III), etc., iridium (Ir) complexes, osmium (Os) complexes, platinum complexes, etc. Among these, it is preferable that the light-emitting material is a luminescent organometallic complex compound.

[0365] The method for forming the light-emitting layer is not particularly limited. It can be formed by applying a coating solution containing semiconductor nanoparticles or an organometallic complex (solution coating method). At this time, as the solvent constituting the coating solution, it is preferable to select a solvent that does not dissolve the material (hole transport material, particularly polymer) in the hole transport layer.

[0366] On the light-emitting layer 150, an electron transport layer 160 is formed. The electron transport layer 160 is a layer having a function of transporting electrons and is formed using a vacuum evaporation method, a spin coating method, an inkjet method, or the like. The electron transport layer 160 may be formed, for example, with a thickness of about 15 nm or more and about 50 nm or less.

[0367] The electron transport layer 160 may be formed of a known electron transport material. Examples of the known electron transport material include (8-quinolinolato)lithium (lithium quinolate) (Liq), tris(8-quinolinato)aluminum (Alq3), and compounds having a nitrogen-containing aromatic ring. Specific examples of the compound having a nitrogen-containing aromatic ring include compounds containing a pyridine ring such as 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, compounds containing a triazine ring such as 2,4,6-tris(3’-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, and 2-(4-(N-phenylbenzoimidazolyl-1-yl-phenyl)-9,10-dinaphthylanthracene , and compounds containing an imidazole ring such as 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI). The above electron transport materials may be used alone or as a mixture of two or more.

[0368] An electron injection layer 170 is formed on the electron transport layer 160. The electron injection layer 170 is a layer having a function of facilitating the injection of electrons from the second electrode 180. The electron injection layer 170 is formed using a vacuum evaporation method or the like. The electron injection layer 170 may be formed with a thickness of about 0.1 nm or more and about 5 nm or less, more specifically, about 0.3 nm or more and about 2 nm or less. Any known material can be used as the material for forming the electron injection layer 170. For example, the electron injection layer 170 is a lithium compound such as (8-quinolinato)lithium (lithium quinolate: Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li2O), or may be formed of barium oxide (BaO) or the like.

[0369] A second electrode 180 is formed on the electron injection layer 170. The second electrode 180 is formed using a vacuum evaporation method or the like. Specifically, the second electrode 180 is a cathode and is formed of a material having a small work function among metals, alloys, or conductive compounds. For example, the second electrode 180 may be formed as a reflective electrode of a metal such as lithium (Li), magnesium (Mg), aluminum (Al), calcium (Ca), or an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag). The second electrode 180 may be formed with a thickness of about 10 nm or more and about 200 nm or less, more specifically, about 50 nm or more and about 150 nm or less. Alternatively, the second electrode 180 may be formed as a transmissive electrode by a thin film of 20 nm or less of the above metal material, a transparent conductive film such as indium tin oxide (In2O3-SnO2) and indium zinc oxide (In2O3-ZnO).

[0370] As an example of the electroluminescence element according to an embodiment of the present invention, the EL element 100 according to this embodiment has been described above. The EL element 100 according to this embodiment can further improve durability (light emission lifetime) by providing an organic film (particularly a hole transport layer or a hole injection layer) containing the polymer according to an embodiment of the present invention. Also, with the above configuration, good luminous efficiency can be obtained.

[0371] Note that the stacked structure of the EL element 100 according to this embodiment is not limited to the above example. The EL element 100 according to this embodiment may be formed with other known stacked structures. For example, in the EL element 100, one or more of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, and the electron injection layer 170 may be omitted, or additional other layers may be provided. Also, each layer of the EL element 100 may be formed of a single layer or a plurality of layers.

[0372] For example, the EL element 100 may further include a hole blocking layer between the hole transport layer 140 and the light emitting layer 150 in order to prevent excitons or holes from diffusing into the electron transport layer 160. Note that the hole blocking layer can be formed of, for example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the like.

[0373] Furthermore, the polymer according to this embodiment can be applied to electroluminescence elements other than the above QLED or OLED. Other electroluminescence elements to which the polymer according to this embodiment can be applied are not particularly limited, but examples include organic-inorganic perovskite light emitting elements.

Examples

[0374] The effects of the present invention will be described using the following examples and comparative examples. However, the technical scope of the present invention is not limited only to the following examples. In the following examples, unless otherwise specified, the operations were carried out at room temperature (25 °C). Also, unless otherwise specified, “%” and “parts” mean “mass %” and “parts by mass”, respectively.

[0375] Synthesis Example 1 (Synthesis of Intermediate 1-1) Intermediate 1-1 was synthesized according to the following reaction.

[0376]

Chemical formula

[0377] Under an argon atmosphere, N,N-bis(4-chlorophenyl)-2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine (6.3 g, 14.3 mmol), 9-bromo-10-(2-naphthyl)anthracene (5.0 g, 13.0 mmol), sodium carbonate (1.38 g, 13.0 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.058 g, 0.26 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos, 0.21 g, 0.52 mmol) were added and the mixture was heated under reflux with stirring for 9 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 6.25 g of a white solid (Intermediate 1-1) (yield 77%).

[0378] (Synthesis of Compound 1) Compound 1 was synthesized according to the following reaction.

[0379]

Chemical formula

[0380] Under an argon atmosphere, the above intermediate 1-1 (5.0 g, 8.1 mmol), bis(pinacolato)diboron (8.2 g, 32.4 mmol), potassium acetate (4.8 g, 32.4 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.22 g, 0.24 mmol) and XPhos (0.46 g, 0.97 mmol) were added, and the mixture was stirred under heating to reflux for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, using Celite (registered trademark), the reaction mixture was filtered to remove impurities. Next, after distilling off the solvent from the filtrate, purification was performed by column chromatography to obtain compound 1 (5.35 g) (yield: 83%).

[0381] Synthesis Example 2 (Synthesis of Intermediate 2-1) Intermediate 2-1 was synthesized according to the following reaction.

[0382]

Chemical formula

[0383] Under an argon atmosphere, N,N-bis(4-chlorophenyl)-2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine (11.3 g, 25.7 mmol), 9-bromoanthracene (6.0 g, 23.3 mmol), sodium carbonate (2.47 g, 23.3 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.104 g, 0.46 mmol) and XPhos (0.38 g, 0.93 mmol) were added, and the mixture was stirred under heating to reflux for 12 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 6.60 g of a white solid (Intermediate 2-1) (yield 58%).

[0384] (Synthesis of Intermediate 2-2) Intermediate 2-2 was synthesized according to the following reaction.

[0385] [Chemical formula]

[0386] Under an argon atmosphere, the above Intermediate 2-1 (6.6 g, 13.4 mmol) and dimethylformamide (DMF) (100 mL) were placed in a reaction vessel and stirred at 50 °C. N-Bromosuccinimide (2.3 g, 12.8 mmol) dissolved in DMF (200 mL) was added dropwise, and the mixture was stirred for 5 hours. Water (50 mL) was added to precipitate a solid. The obtained solid was washed with methanol to obtain 7.35 g of a solid (Intermediate 2-2) (yield 96%).

[0387] (Synthesis of Intermediate 2-3) Intermediate 2-3 was synthesized according to the following reaction.

[0388] [Chemical formula]

[0389] Under an argon atmosphere, the above Intermediate 2-2 (7.35 g, 12.9 mmol), 9,9-dimethylfluorene-2-boronic acid (3.4 g, 14.2 mmol), sodium carbonate (1.64 g, 15.4 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.057 g, 0.25 mmol) and XPhos (0.21 g, 0.51 mmol) were added, and the mixture was heated under reflux and stirred for 5 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 6.45 g of a white solid (Intermediate 2-3) (yield 73%).

[0390] (Synthesis of Compound 2) Compound 2 was synthesized according to the following reaction.

[0391]

Chem.

[0392] Under an argon atmosphere, the above intermediate 2-3 (6.4 g, 9.3 mmol), bis(pinacolato)diboron (9.5 g, 37.4 mmol), potassium acetate (5.5 g, 56.2 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.25 g, 0.28 mmol) and XPhos (0.53 g, 1.12 mmol) were added, and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain Compound 2 (7.64 g) (yield: 94%).

[0393] Synthesis Example 3 (Synthesis of Intermediate 3-1) Intermediate 3-1 was synthesized according to the following reaction.

[0394]

Chem.

[0395] Under an argon atmosphere, the above intermediate 2-2 (10.0 g, 17.5 mmol), dibenzothiophene-2-boronic acid (4.4 g, 19.3 mmol), sodium carbonate ( 2.23 g (21.0 mmol), 100 mL of toluene, and 50 mL of water were added and stirred for 30 minutes. Then, palladium acetate (0.057 g, 0.25 mmol) and XPhos (0.21 g, 0.51 mmol) were added and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 5.18 g of a white solid (Intermediate 3-1) (yield 44%).

[0396] (Synthesis of Compound 3) Compound 3 was synthesized according to the following reaction.

[0397] [Chemical formula]

[0398] Under an argon atmosphere, the above Intermediate 3-1 (5.2 g, 7.3 mmol), bis(pinacolato)diboron (7.8 g, 30.9 mmol), potassium acetate (4.5 g, 46.3 mmol), and dioxane (80 ml) were added to the reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.21 g, 0.23 mmol) and XPhos (0.44 g, 0.92 mmol) were added and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate and the residue was purified by column chromatography to obtain Compound 3 (5.17 g) (yield: 78%).

[0399] Synthesis Example 4 (Synthesis of Intermediate 4-1) Intermediate 4-1 was synthesized according to the following reaction.

[0400] [Chemical formula]

[0401] Under an argon atmosphere, 2-bromo-9,9-dibutylfluorene (10.0 g, 27.9 mmol), 9-anthraceneboronic acid (6.8 g, 30.7 mmol), sodium carbonate (3.55 g, 33.5 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.12 g, 0.56 mmol) and XPhos (0.46 g, 1.12 mmol) were added, and the mixture was heated under reflux with stirring for 12 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO 4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 13.66 g of a solid (Intermediate 4-1) (yield 100%).

[0402] (Synthesis of Intermediate 4-2) Intermediate 4-2 was synthesized according to the following reaction.

[0403]

Chemical formula

[0404] Under an argon atmosphere, the above Intermediate 4-1 (13.7 g, 30.0 mmol) and dimethylformamide (DMF) (100 mL) were placed in a reaction vessel and stirred at 50 °C. N-Bromosuccinimide (5.0 g, 28.5 mmol) dissolved in DMF (200 mL) was added dropwise, and the mixture was stirred for 5 hours. Water (50 mL) was added to precipitate a solid. The obtained solid was washed with methanol to obtain 13.2 g of a solid (Intermediate 4-2) (yield 82%).

[0405] (Synthesis of Intermediate 4-3) Intermediate 4-3 was synthesized according to the following reaction.

[0406]

Chemical formula

[0407] Under an argon atmosphere, N,N-bis(4-chlorophenyl)-2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine (4.5 g, 10.3 mmol), the above intermediate 4-2 (5.0 g, 9.3 mmol), sodium carbonate (0.99 g, 9.3 mmol), 80 mL of toluene, and 40 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.042 g, 0.18 mmol) and XPhos (0.15 g, 0.37 mmol) were added, and the mixture was heated under reflux with stirring for 18 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 4.36 g of a solid (intermediate 4-3) (yield 60%).

[0408] (Synthesis of Compound 4) Compound 4 was synthesized according to the following reaction.

[0409] [Chemical formula]

[0410] Under an argon atmosphere, the above intermediate 4-3 (4.3 g, 5.6 mmol), bis(pinacolato)diboron (5.7 g, 22.7 mmol), potassium acetate (3.3 g, 34.1 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.15 g, 0.17 mmol) and XPhos (0.32 g, 0.68 mmol) were added, and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Next, the solvent was distilled off from the filtrate and purified by column chromatography to obtain Compound 4 (5.0 g) (yield: 92%).

[0411] Synthesis Example 5 (Synthesis of Intermediate 5-1) The intermediate 5-1 was synthesized according to the following reaction.

[0412]

Chemical formula

[0413] Under an argon atmosphere, 2-bromo-7-iodo-9,9-dimethylfluorene (9.0 g, 22.6 mmol), 4,4,5,5-tetramethyl-2-[10-(2-naphthyl)anthracen-9-yl]-1,3,2-dioxaborolane (10.7 g, 24.8 mmol), sodium carbonate (2.86 g, 27.0 mmol), 120 mL of toluene, and 60 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.10 g, 0.45 mmol) and XPhos (0.37 g, 0.90 mmol) were added, and the mixture was heated under reflux with stirring for 17 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.98 g of a white solid (intermediate 5-1) (yield 84%).

[0414] (Synthesis of intermediate 5-2) The intermediate 5-2 was synthesized according to the following reaction.

[0415]

Chemical formula

[0416] Under an argon atmosphere, the above intermediate 5-1 (11.0 g, 19.1 mmol), bis(4-chlorophenyl)amine (5.0 g, 21.0 mmol), sodium t-butoxide (2.2 g, 22.9 mmol), and 160 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.17 g, 0.19 mmol) and 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.42 g, 0.76 mmol) were added, and the mixture was heated under reflux with stirring for 4 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities by filtration. Next, after distilling off the solvent from the filtrate, the residue was purified by column chromatography to obtain a solid of intermediate 5-2 (3.75 g) (yield 26%).

[0417] (Synthesis of Compound 5) Compound 5 was synthesized according to the following reaction.

[0418] [Chemical formula]

[0419] Under an argon atmosphere, the above intermediate 5-2 (3.75 g, 5.1 mmol), bis(pinacolato)diboron (5.2 g, 20.4 mmol), potassium acetate (3.0 g, 30.7 mmol), and 80 mL of dioxane were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.14 g, 0.15 mmol) and XPhos (0.29 g, 0.61 mmol) were added, and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities by filtration. Next, after distilling off the solvent from the filtrate, the residue was purified by column chromatography to obtain Compound 5 (3.8 g) (yield: 81%).

[0420] Synthesis Example 6 (Synthesis of Intermediate 6-1) Intermediate 6-1 was synthesized according to the following reaction.

[0421]

Chemical formula

[0422] Under an argon atmosphere, the above intermediate 4-2 (8.2 g, 15.3 mmol), bis(pinacolato)diboron (11.7 g, 46.1 mmol), potassium acetate (9.1 g, 92.2 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf), 0.67 g, 0.922 mmol) was added, and the mixture was heated to reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain intermediate 6-1 (7.05 g) (yield: 79%).

[0423] (Synthesis of Intermediate 6-2) Intermediate 6-2 was synthesized according to the following reaction.

[0424]

Chemical formula

[0425] Under an argon atmosphere, 2-bromo-7-iodo-9,9-dimethylfluorene (4.4 g, 11.0 mmol), the above intermediate 6-1 (7.0 g, 12.1 mmol), sodium carbonate (1.4 g, 13.2 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.098 g, 0.44 mmol) and XPhos (0.36 g, 0.88 mmol) were added, and the mixture was stirred under heating under reflux for 12 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain intermediate 6-2 (6.96 g) (yield 87%).

[0426] (Synthesis of Intermediate 6-3) Intermediate 6-3 was synthesized according to the following reaction.

[0427] [Chemical formula]

[0428] Under an argon atmosphere, the above intermediate 6-2 (7.0 g, 9.6 mmol), bis(4-chlorophenyl)amine (2.3 g, 9.6 mmol), sodium t-butoxide (1.1 g, 11.5 mmol), and 200 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.044 g, 0.048 mmol) and (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 0.090 g, 0.144 mmol) were added, and the mixture was stirred under heating under reflux for 4 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter off impurities. Next, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain a solid of intermediate 6-3 (2.07 g) (yield 24%).

[0429] (Synthesis of Compound 6) Compound 6 was synthesized according to the following reaction.

[0430]

Chem.

[0431] Under an argon atmosphere, the above intermediate 6-3 (2.10 g, 2.4 mmol), bis(pinacolato)diboron (2.4 g, 9.5 mmol), potassium acetate (1.4 g, 14.3 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.065 g, 0.07 mmol) and XPhos (0.13 g, 0.28 mmol) were added, and the mixture was heated under reflux with stirring for 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain Compound 6 (2.2 g) (yield: 88%).

[0432] Synthesis Example 7 (Synthesis of Intermediate 7-1) Intermediate 7-1 was synthesized according to the following reaction.

[0433]

Chem.

[0434] Under an argon atmosphere, 2-bromo-7-iodo-9,9-dihexylfluorene (6.0 g, 11.1 mmol), 4,4,5,5-tetramethyl-2-[10-(2-naphthyl)anthracen-9-yl]-1,3,2-dioxaborolane (4.5 g, 10.6 mmol), sodium carbonate (1.4 g, 13.3 mmol), 100 mL of toluene, 10 mL of EtOH, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd[PPh3]4) (0.77 g, 0.067 mmol) was added, and the mixture was heated under reflux with stirring for 8 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain intermediate 7-1 (4.87 g) (yield 61%).

[0435] (Synthesis of Intermediate 7-2) Intermediate 7-2 was synthesized according to the following reaction.

[0436] [Chemical formula]

[0437] Under an argon atmosphere, the above intermediate 7-1 (4.9 g, 6.8 mmol), bis(4-chlorophenyl)amine (1.6 g, 6.8 mmol), sodium t-butoxide (0.78 g, 8.1 mmol), and 100 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.016 g, 0.017 mmol) and (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 0.032 g, 0.051 mmol) were added, and the mixture was heated under reflux with stirring for 25 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Next, the solvent was distilled off from the filtrate and purified by column chromatography to obtain a solid of intermediate 7-2 (3.91 g) (yield 65%).

[0438] (Synthesis of Compound 7) Compound 7 was synthesized according to the following reaction.

[0439] [Chemical Structure Diagram]

[0440] Under an argon atmosphere, the above intermediate 7-2 (6.35 g, 7.3 mmol), bis(pinacolato)diboron (9.2 g, 36.4 mmol), potassium acetate (4.3 g, 43.6 mmol), and dioxane (150 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.19 g, 0.22 mmol) and XPhos (0.42 g, 0.87 mmol) were added, and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain Compound 7 (6.7 g) (yield: 87%).

[0441] Synthesis Example 8 (Synthesis of Intermediate 8-1) Intermediate 8-1 was synthesized according to the following reaction.

[0442] [Chemical Structure Diagram]

[0443] Under an argon atmosphere, 2-bromo-7-iodo-9,9-dioctylfluorene (6.0 g, 10.1 mmol), 9-phenanthreneboronic acid (2.1 g, 9.6 mmol), sodium carbonate (1.4 g, 13.3 mmol), 100 mL of toluene, 10 mL of EtOH, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd[PPh3]4) (0.70 g, 0.061 mmol) was added, and the mixture was stirred under heating reflux for 5 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain intermediate 8-1 (6.21 g) (yield 95%).

[0444] (Synthesis of Intermediate 8-2) Intermediate 8-2 was synthesized according to the following reaction.

[0445] [Chemical formula]

[0446] Under an argon atmosphere, the above intermediate 8-1 (6.2 g, 9.6 mmol), bis(4-chlorophenyl)amine (2.3 g, 9.6 mmol), sodium t-butoxide (1.11 g, 11.5 mmol), and 150 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.11 g, 0.12 mmol) and 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.27 g, 0.48 mmol) were added, and the mixture was stirred under heating reflux for 7 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Next, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain a solid of intermediate 8-2 (3.71 g) (yield 48%).

[0447] (Synthesis of Compound 8) Compound 8 was synthesized according to the following reaction.

[0448] [Chemistry]

[0449] Under an argon atmosphere, the above intermediate 8-2 (3.71 g, 4.6 mmol), bis(pinacolato)diboron (4.7 g, 18.4 mmol), potassium acetate (2.7 g, 27.7 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.13 g, 0.14 mmol) and XPhos (0.26 g, 0.55 mmol) were added, and the mixture was heated under reflux with stirring for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain compound 8 (4.2 g) (yield: 91%).

[0450] Synthesis Example 9 (Synthesis of Intermediate 9-1) Intermediate 9-1 was synthesized according to the following reaction.

[0451] [Chemistry]

[0452] Into a 1L four-necked flask, 3-chloro-carbazole (42.2 g, 0.209 mol), 4-bromohexylbenzene (50.2 g, 0.208 mol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (9.57 g), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3·BF4) (4.55 g), sodium tert-butoxide (40.2 g), and toluene (500 mL) were added. Under a nitrogen atmosphere, the mixture was heated and stirred at 100 °C for 8 hours. After cooling to room temperature (25 °C), the insoluble matter was filtered off through Celite (registered trademark). The solvent was distilled off under reduced pressure from the filtrate, and the residue was purified by column chromatography to obtain Intermediate 9-1 (56.5 g, 0.157 mol).

[0453] (Synthesis of Intermediate 9-2) Intermediate 9-2 was synthesized according to the following reaction.

[0454] [Chemical formula]

[0455] Under an argon atmosphere, Intermediate 9-1 (6.3 g, 17.3 mmol) obtained above, bis(pinacolato)diboron (8.8 g, 34.6 mmol), potassium acetate (5.1 g, 51.9 mmol), and dioxane (80 ml) were added to the reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (0.47 g, 0.52 mmol) and Xphos (0.99 g, 2.08 mmol) were added, and the mixture was heated under reflux with stirring for 8 hours.

[0456] After the reaction was completed, the reaction mixture was cooled to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to remove impurities. Then, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain Intermediate 9-2 (4.7 g) (yield: 60%).

[0457] (Synthesis of Compound 9) Compound 9 was synthesized according to the following reaction.

[0458]

Chem.

[0459] Under an argon atmosphere, the intermediate 9-2 (9.0 g, 19.8 mmol) obtained above, 1,4-dibromo-2-iodobenzene (10.8 g, 29.8 mmol), sodium carbonate (3.2 g, 29.8 mmol), 120 mL of dioxane, and 60 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd[PPh3]4) (1.15 g, 0.99 mmol) was added, and the mixture was heated under reflux with stirring for 12 hours.

[0460] After completion of the reaction, the reaction mixture was cooled to room temperature, transferred to a separatory funnel, and extracted with toluene. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 4.5 g of a white solid (Compound 9) (yield: 73%).

[0461] Example 1-1 (Synthesis of Polymer Compound A-1) Under an argon atmosphere, compound 1 (1.575 g) synthesized in Synthesis Example 1 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.080 g), palladium acetate (8.8 mg), tris(2-methoxyphenyl)phosphine (83.3 mg), toluene (53 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (10.15 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (238.4 mg), bis(triphenylphosphine)palladium(II) dichloride (83.0 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (10.15 g) were added, and the mixture was heated to reflux for 6 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 6 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate a polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain a polymer compound A-1 (0.90 g).

[0462] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained polymer compound A-1 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer compound A-1 were 138,900 and 3.34, respectively.

[0463] The polymer compound A-1 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

[0464]

Chemical formula

[0465] Example 1-2 (Synthesis of polymer compound A-2) Under an argon atmosphere, the compound 2 (1.727 g) synthesized in Synthesis Example 2 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.094 g), palladium acetate (9.0 mg), tris(2-methoxyphenyl)phosphine (84.4 mg), toluene (56 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (10.28 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (241.1 mg), bis(triphenylphosphine)palladium(II) dichloride (84.0 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (10.28 g) were added, and the mixture was heated under reflux for 7 hours. Then, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate a polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain a polymer compound A-2 (1.06 g).

[0466] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained polymer compound A-2 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer compound A-2 were 40,900 and 2.49, respectively.

[0467] The polymer compound A-2 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the constitutional unit (X) and the constitutional unit (Y) according to the present invention are polymerized alternately.

[0468]

Chemical formula

[0469] Example 1-3 (Synthesis of Polymer Compound A-3) Under an argon atmosphere, Compound 3 (1.724 g) synthesized in Synthesis Example 3 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.105 g), palladium acetate (9.0 mg), tris(2-methoxyphenyl)phosphine (85.2 mg), toluene (57 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (10.39 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (243.8 mg), bis(triphenylphosphine)palladium(II) dichloride (84.9 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (10.39 g) were added, and the mixture was heated to reflux for 7 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.59 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-3 (1.40 g).

[0470] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-3 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-3 were 132,900 and 3.20, respectively.

[0471] The Polymer Compound A-3 thus obtained is presumed to be a polymer compound in which the constituent unit (X) and the constituent unit (Y) according to the present invention are polymerized alternately, and has the following repeating units from the monomer charge ratio.

[0472] [Chemical formula]

[0473] Examples 1-4 (Synthesis of Polymer Compound A-4) Under an argon atmosphere, Compound 4 (1.748 g) synthesized in Synthesis Example 4 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.009 g), palladium acetate (8.3 mg), tris(2-methoxyphenyl)phosphine (77.8 mg), toluene (55 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.49 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (222.7 mg), bis(triphenylphosphine)palladium(II) dichloride (77.5 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.49 g) were added, and the mixture was heated to reflux for 6 hours. Then, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 6 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-4 (1.22 g).

[0474] The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-4 were measured by SEC. As a result, the weight-average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-4 were 76,900 and 2.38, respectively.

[0475] The Polymer Compound A-4 thus obtained is presumed to be a polymer compound in which the repeating units below are present from the monomer charge ratio and the constitutional unit (X) and the constitutional unit (Y) according to the present invention are polymerized alternately.

[0476] [Chemical formula]

[0477] Examples 1-5 (Synthesis of Polymer Compound A-5) Under an argon atmosphere, Compound 5 (1.740 g) synthesized in Synthesis Example 5 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.042 g), palladium acetate (8.5 mg), tris(2-methoxyphenyl)phosphine (80.3 mg), toluene (56 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.79 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (229.9 mg), bis(triphenylphosphine)palladium(II) dichloride (80 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.79 g) were added, and the mixture was heated to reflux for 7 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.55 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-5 (1.21 g).

[0478] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-5 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-5 were 90,000 and 2.50, respectively.

[0479] The Polymer Compound A-5 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the constitutional unit (X) and the constitutional unit (Y) according to the present invention are polymerized alternately.

[0480] [Chemical formula]

[0481] Examples 1-6 (Synthesis of Polymer Compound A-6) Under an argon atmosphere, Compound 6 (1.621 g) synthesized in Synthesis Example 6 above, 2,7-dibromo-9,9-di-n-dodecylfluorene (1.005 g), palladium acetate (6.8 mg), tris(2-methoxyphenyl)phosphine (64.3 mg), toluene (53 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (7.84 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (184 mg), bis(triphenylphosphine)palladium(II) dichloride (64.1 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (7.84 g) were added, and the mixture was heated under reflux for 7 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-6 (1.01 g).

[0482] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-6 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-6 were 53,500 and 2.81, respectively.

[0483] The Polymer Compound A-6 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the constitutional unit (X) and the constitutional unit (Y) according to the present invention are polymerized alternately.

[0484] [Chemical formula]

[0485] Example 1-7 (Synthesis of Polymer Compound A-7) Under an argon atmosphere, Compound 7 (1.771 g) synthesized in Synthesis Example 7 above, 2,7-dibromo-9,9-di-n-octylfluorene (0.920 g), palladium acetate (7.5 mg), tris(2-methoxyphenyl)phosphine (70.9 mg), toluene (54 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.64 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (202.9 mg), bis(triphenylphosphine)palladium(II) dichloride (70.6 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.64 g) were added, and the mixture was heated to reflux for 7 hours. Then, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-7 (1.02 g).

[0486] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-7 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-7 were 51,800 and 2.04, respectively.

[0487] The Polymer Compound A-7 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

[0488] [Chemical formula]

[0489] Example 1-8 (Synthesis of Polymer Compound A-8) Under an argon atmosphere, Compound 7 (2.014 g) synthesized in Synthesis Example 7 above, 1,3-dibromo-5-dodecylbenzene (0.771 g), palladium acetate (8.6 mg), tris(2-methoxyphenyl)phosphine (80.7 mg), toluene (56 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.83 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (230.8 mg), bis(triphenylphosphine)palladium(II) dichloride (80.3 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.83 g) were added, and the mixture was heated to reflux for 7 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (9.67 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85°C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-8 (1.19 g).

[0490] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-8 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-8 were 14,300 and 1.73, respectively.

[0491] The Polymer Compound A-8 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

[0492]

Chemical Formula

[0493] Example 1-9 (Synthesis of Polymer Compound A-9) Under an argon atmosphere, Compound 7 (1.752 g) synthesized in Synthesis Example 7 above, Compound 9 (0.931 g), palladium acetate (7.4 mg), tris(2-methoxyphenyl)phosphine (35.1 mg), toluene (54 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.55 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (200.7 mg), bis(triphenylphosphine)palladium(II) dichloride (69.9 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.55 g) were added, and the mixture was heated to reflux for 7 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (8.41 g) and ion-exchanged water (53 mL) were added, and the mixture was stirred at 85°C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-9 (1.37 g).

[0494] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-9 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-9 were 38,000 and 1.97, respectively.

[0495] [Chemical formula]

[0496] Example 1-10 (Synthesis of Polymer Compound A-10) Under an argon atmosphere, the compound 8 (1.581 g) synthesized in Synthesis Example 8 above, 2,7-dibromo-9,9-di-n-octylfluorene (0.879 g), palladium acetate (7.2 mg), tris(2-methoxyphenyl)phosphine (67.8 mg), toluene (49 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.26 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (194 mg), bis(triphenylphosphine)palladium(II) dichloride (67.5 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.26 g) were added, and the mixture was heated to reflux for 7 hours. Thereafter, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (5.46 g) and ion-exchanged water (54 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate a polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain a polymer compound A-10 (1.02 g).

[0497] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained polymer compound A-10 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer compound A-10 were 226,900 and 10.68, respectively.

[0498] The polymer compound A-10 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

[0499]

Chemical formula

[0500] Example 1-11 (Synthesis of polymer compound A-11) Under an argon atmosphere, Compound 1 (1.525 g) synthesized in Synthesis Example 1 above, 2,7-dibromo-9,9-di-n-dodecylfluorene (1.260 g), palladium acetate (8.6 mg), tris(2-methoxyphenyl)phosphine (80.7 mg), toluene (56 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.83 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (230.8 mg), bis(triphenylphosphine)palladium(II) dichloride (80.3 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.83 g) were added, and the mixture was heated to reflux for 7 hours. Then, the aqueous layer was removed, sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, and the mixture was stirred at 85 °C for 2 hours. After separating the organic layer from the water layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered off and dried to obtain Polymer Compound A-11 (1.23 g).

[0501] The weight average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained Polymer Compound A-11 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of Polymer Compound A-7 were 59,900 and 2.26, respectively.

[0502] The Polymer Compound A-11 thus obtained has the following repeating units from the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

[0503]

Chemical formula

[0504] [Characteristic evaluation of each polymer compound] For the polymer compounds A-1 to A-11 of the above Examples 1-1 to 1-11, the HOMO level (eV) and the glass transition temperature (Tg) (°C) were measured by the following method. The results are shown in Table 1 below.

[0505] (Measurement of HOMO level) Each polymer compound is dissolved in xylene so that the concentration becomes 1% by mass to prepare a coating solution. Using the coating solution prepared above on a glass substrate with ITO that has been UV-cleaned, a film is formed by spin coating under the condition of a rotation speed of 2000 rpm. After that, it is dried on a hot plate at 150 °C for 30 minutes to prepare a sample for measurement. Using an atmospheric photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd., AC-3), the HOMO level of the sample is measured. At this time, from the measurement results, the intersection point of the rising tangent line is calculated and taken as the HOMO level (eV). Note that the HOMO level is usually a negative value.

[0506] (Glass transition temperature (Tg)) Using a differential scanning calorimeter (DSC) (manufactured by Seiko Instruments Inc., product name: DSC6000), a sample obtained by heating each polymer compound to 300 °C at a heating rate of 10 °C / min and holding for 10 minutes, cooling to 25 °C at a cooling rate of 10 °C / min and holding for 10 minutes, and then heating to 300 °C at a heating rate of 10 °C / min for measurement. After the measurement is completed, it is cooled to room temperature (25 °C) at a rate of 10 °C / min.

[0507] [Table 1-1]

[0508] [Table 1-2]

[0509] [Table 1-3]

[0510] Reference Example (Fabrication of Hall-only device) As the first electrode (anode), a glass substrate with a strip-shaped indium tin oxide (ITO) film formed thereon with a film thickness of 150 nm was prepared. On the glass substrate, PEDOT-PSS (manufactured by Sigma-Aldrich) was spin-coated so that the dry film thickness would be 30 nm and dried to form a hole injection layer with a dry film thickness of 30 nm. After that, the polymer compound A-7 (hole transport material) obtained in Examples 1-7 was dissolved in xylene, which is a solvent, at a concentration of 1 mass% to prepare a polymer coating solution. The polymer coating solution prepared above was spin-coated onto the hole injection layer formed above so that the dry film thickness would be 30 nm and heated and dried at 150 °C for 30 minutes. As a result, a hole transport layer with a dry film thickness of 30 nm was formed.

[0511]

[0512] Next, in octane, a blue quantum dot of ZnTeSe / ZnSe / ZnS (core / shell / shell; average diameter = about 10 nm) having the following structure:

[0513]

Chemical formula

[0514]

[0515] was dispersed to a concentration of 2.0 mass% to prepare a quantum dot dispersion solution. Note that the hole transport layer (especially the polymer compound P-1) is not soluble in octane. This quantum dot dispersion solution was spin-coated onto the hole transport layer formed above so that the dry film thickness would be 20 nm and heated and dried at 80 °C for 30 minutes. As a result, a quantum dot light-emitting layer (QD layer) with a dry film thickness of 20 nm was formed.​Next, ZnCl was dissolved in ethanol as a solvent at a concentration of 0.7 mol / L to prepare a ZnCl coating solution. The prepared ZnCl coating solution was slowly dropped so as to cover the light-emitting surface formed above, left standing for 60 seconds, and then rotated at 1000 rpm for 40 seconds by the spin coating method, and dried by heating at 80 °C for 20 minutes. Subsequently, ethanol was slowly dropped so as to cover the light-emitting surface formed above, and the operation of rotating at 1000 rpm by the spin coating method was repeated twice, and dried by heating at 80 °C for 20 minutes.

[0516] α-NPD (N,N'-di-1-naphthyl-N,N'-diphenylbenzidine) and HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) were sequentially vapor-deposited on the hole transport layer formed above by the vacuum vapor deposition method to form an electron blocking layer to have thicknesses of 36 nm and 10 nm, respectively, and a hole-only device 1 was fabricated.

[0517] Comparative Example 1-1 (Fabrication of hole-only device) In the reference example, except that poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB) (manufactured by Luminescence Technology Corp.) having the following structural unit was used instead of the polymer compound A-7, the same operations as in the reference example were performed to fabricate a hole-only device. The weight average molecular weight (Mw) and dispersity (Mw / Mn) of TFB were measured by SEC . As a result, the weight average molecular weight (Mw) and dispersity (Mw / Mn) of TFB were 359,000 and 3.4, respectively.

[0518] [Chemical formula]

[0519] [Evaluation of hole-only device] Regarding the hole-only devices fabricated in the above Reference Example and Comparative Example 1-1, respectively, using a DC constant voltage power supply (manufactured by KEYENCE, source meter), the voltage was gradually increased, and the current value (current density (A / m 2 )) at 8V was measured, and this was designated as "current value @ 8V". The results are shown in Table 2 below.

[0520]

Table 2

[0521] From the results in Table 2 above, it can be said that the hole-only device of the Reference Example has a higher current value at 8V compared to that of Comparative Example 1-1. Therefore, A-7 having fluorene substituted with Ar 3 , which is an example of the polymer (high molecular compound) according to the present invention, was shown to be excellent in hole (positive hole) mobility to the QD layer, which is the light-emitting layer.

[0522] Example 2-1 (Fabrication of Quantum Dot Electroluminescence Device 1) As the first electrode (anode), an ITO-coated glass substrate with indium tin oxide (ITO) patterned to a film thickness of 150 nm was used. This ITO-coated glass substrate was sequentially washed using a neutral detergent, deionized water, water, and isopropyl alcohol, and then UV-ozone treatment was carried out. Next, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS) (manufactured by Sigma-Aldrich) was spin-coated on this ITO-coated glass substrate so that the dry film thickness became 30 nm, and then dried. As a result, a hole injection layer with a thickness (dry film thickness) of 30 nm was formed on the ITO-coated glass substrate.

[0523] Next, the polymer compound A-1 (hole transport material) synthesized in Example 1-1 was dissolved in toluene (solvent) at a concentration of 1% by mass to prepare a coating solution (1) for forming a hole transport layer. On the hole injection layer formed above, this coating solution (1) for forming a hole transport layer was applied by spin coating so that the thickness (dry film thickness) became 30 nm, and then heated at 230 °C for 1 hour. The thickness (dry film thickness) A hole transport layer with a thickness (dry film thickness) of 30 nm was formed on the hole injection layer.

[0524] In cyclohexane, the following structure:

[0525]

Chemical formula

[0526] Green quantum dots of InP / ZnSe / ZnS (core / shell / shell; average diameter = about 15 nm) having the above structure were dispersed to a concentration of 1.0% by mass to prepare a quantum dot dispersion. Note that the hole transport layer (especially the polymer compound A-1) is insoluble in cyclohexane. This quantum dot dispersion was applied onto the above hole transport layer by spin coating so that the dry film thickness became 30 nm, and then dried. As a result, a quantum dot light-emitting layer with a thickness (dry film thickness) of 30 nm was formed on the hole transport layer. The light emitted by irradiating the quantum dot dispersion with ultraviolet light had a central wavelength of 550 nm and a full width at half maximum of 45 nm.

[0527] This quantum dot light-emitting layer was completely dried. On this quantum dot light-emitting layer, lithium quinolate (Liq) and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (manufactured by Sigma-Aldrich) as an electron transport material were co-evaporated using a vacuum evaporation apparatus. As a result, an electron transport layer with a thickness of 36 nm was formed on the quantum dot light-emitting layer.

[0528] Using a vacuum evaporation apparatus, (8-quinolinolato)lithium (lithium quinolate) (Liq) was evaporated onto this electron transport layer. As a result, an electron injection layer with a thickness of 0.5 nm was formed on the electron transport layer.

[0529] On the electron injection layer formed above, aluminum (hereinafter referred to as Al) was deposited using a vacuum deposition apparatus to form a second electrode (cathode) with a thickness of 100 nm on the electron injection layer. Thereby, the quantum dot electroluminescence element 1 was obtained.

[0530] Example 2-2 (Fabrication of Quantum Dot Electroluminescence Element 2) In Example 2-1, except that the polymer compound A-2 of Example 2 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence element 2.

[0531] Example 2-3 (Fabrication of Quantum Dot Electroluminescence Element 3) In Example 2-1, except that the polymer compound A-3 of Example 3 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence element 3.

[0532] Example 2-4 (Fabrication of Quantum Dot Electroluminescence Element 4) In Example 2-1, except that the polymer compound A-4 of Example 4 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence element 4.

[0533] Example 2-5 (Fabrication of Quantum Dot Electroluminescence Element 5) In Example 2-1, except that the polymer compound A-5 of Example 5 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence element 5.

[0534] Example 2-6 (Fabrication of Quantum Dot Electroluminescence Element 6) In Example 2-1, except that the polymer compound A-6 of Example 6 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence device 6.

[0535] Example 2-7 (Fabrication of Quantum Dot Electroluminescence Device 7) In Example 2-1, except that the polymer compound A-7 of Example 7 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence device 7.

[0536] Example 2-8 (Fabrication of Quantum Dot Electroluminescence Device 8) In Example 2-1, except that the polymer compound A-8 of Example 8 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence device 8.

[0537] Example 2-9 (Fabrication of Quantum Dot Electroluminescence Device 9) In Example 2-1, except that the polymer compound A-9 of Example 9 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence device 9.

[0538] Example 2-10 (Fabrication of Quantum Dot Electroluminescence Device 10) In Example 2-1, except that the polymer compound A-9 of Example 10 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were performed to fabricate the quantum dot electroluminescence device 10.

[0539] Example 2-11 (Fabrication of Quantum Dot Electroluminescence Device 11) In Example 2-1, except that the polymer compound A-9 of Example 11 was used instead of the polymer compound A-1, the same operations as in Example 2-1 were carried out to fabricate the quantum dot electroluminescence device 11.

[0540] Comparative Example 2-1 (Fabrication of Comparative Quantum Dot Electroluminescence Device 1) In Example 2-1, except that TFB used in Comparative Example 1-1 described above was used instead of the polymer compound A-1, the same operations as in Example 2-1 were carried out to fabricate the comparative quantum dot electroluminescence device 1.

[0541] [Evaluation of Quantum Dot Electroluminescence Devices] For the quantum dot electroluminescence devices 1 to 11 fabricated in Examples 2-1 to 2-11 and the comparative quantum dot electroluminescence device 1 fabricated in Comparative Example 2-1, the luminous efficiency and the luminous lifetime were evaluated by the following method. The results are shown in Table 3 below.

[0542] (Luminous Efficiency) When a voltage is applied to each quantum dot electroluminescence device, a current starts to flow at a certain voltage and the quantum dot electroluminescence device emits light. Using a DC constant voltage power supply (manufactured by Keyence Corporation, source meter), the voltage of each device was gradually increased, the current value at that time was measured, and the luminance at the time of light emission was measured using a luminance measuring device (manufactured by Topcon Corporation, SR-3). Here, the measurement is terminated when the luminance starts to decay. The current value per unit area (current density) was calculated from the area of each device, and the luminance (cd / m 2 ) was divided by the current density (A / m 2 ) to calculate the current efficiency (cd / A).

[0543] Also, assuming that Lambertian emission was performed from the spectral radiant luminance spectrum measured by the luminance measuring device, the external quantum efficiency (EQE) (%) at Cd / A max was calculated to evaluate the luminous efficiency.

[0544] (Emission lifetime) Using a DC constant voltage power supply (manufactured by Keyence Corporation, source meter), a predetermined voltage is applied to each quantum dot electroluminescence element to cause the quantum dot electroluminescence element to emit light. While measuring the light emission of the quantum dot electroluminescence element with a luminance measuring device (manufactured by Topcon Corporation, SR-3), the current is gradually increased until the luminance reaches 5400 nit (cd / m 2 ), and then the current is fixed and left standing. The time until the luminance value measured by the luminance measuring device gradually decreases to 50% of the initial luminance is defined as "LT50 (hr)".

[0545]

Table 3

[0546] From the results in Table 3 above, it can be seen that the quantum dot electroluminescence elements 1 to 11 of the examples exhibit significantly higher durability (significantly longer emission lifetime) compared to the comparative quantum dot electroluminescence element 1. Also, it was shown that the quantum dot electroluminescence elements 1 to 11 of the examples can achieve good luminous efficiency (EQE).

[0547] In this example, the green quantum dot electroluminescence element was evaluated, but it is considered that the same results as above can be obtained for red quantum dot electroluminescence elements and the like.

[0548] As described above, the present invention has been described with reference to embodiments and examples. However, the present invention is not limited to specific embodiments and examples, and various modifications and changes are possible within the scope of the invention described in the claims.

Explanation of reference numerals

[0549] 100... Electroluminescence element (EL element), 110... Substrate, 120... The first electrode, 130... The hole injection layer, 140... The hole transport layer, 150... The light-emitting layer, 160... The electron transport layer, 170... The electron injection layer, 180... The second electrode.

Claims

1. A polymer comprising a structural unit (A) represented by the following formula (1): 【Chemical Formula 1】 In the above formula (1), Ar １ ~Ar ３ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, which may be substituted or unsubstituted; Ar ４ is a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed, Ar ５ is a group represented by the following formula (5) or (6), Ar ６ is a divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms which may be substituted or unsubstituted, or a divalent aromatic heterocyclic group having 5 to 60 ring-forming atoms which may be substituted or unsubstituted, p is 1: 【Chemical 2】 In the above formula (5), X is a group selected from -C(R5)(R6)-, -O-, and -S-; R3 and R4 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R3 and R4 may be bonded to each other to form a ring; R5 and R6 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R5 and R6 may be bonded to each other to form a ring; a is 0, 1, 2, or 3, and b is 0, 1, 2, 3, or 4; When either a or b is 2 or more, each R3 or each R4 may be the same or different; In the above formula (6), R7 and R8 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R7 and R8 may be bonded to each other to form a ring; c is 0, 1, 2, or 3, and d is 0, 1, 2, 3, or 4; When either c or d is 2 or more, each R7 or each R8 may be the same or different.

2. In the formula (1), Ar ４ is a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted tetracenylene group, or a substituted or unsubstituted chrysenylene group, the polymer according to claim 1.

3. In the formula (1), Ar ３ is any one of the groups represented by the following formulas (2) to (4), the polymer according to claim 1 or 2: 【Chemical Formula 3】 In the above formula (3), R １ and R ２ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, where R １ and R ２ may be bonded to each other to form a ring.

4. The polymer according to any one of Claims 1 to 3, wherein the group represented by the above formula (5) is any one of the groups represented by the following formulas (501) to (515): 【Chemical Formula 4】 [Chemical Formula 5] In the above formulas (501) to (515), R ３０１ to R ３１５ and R ４０１ to R ４１５ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R ３０１ and R ４０１ , R ３０２ and R ４０２ , R ３０３ and R ４０３ , R ３０４ and R ４０４ , R ３０５ and R ４０５ , R ３０６ and R ４０６ , R ３０７ and R ４０７ , R ３０８ and R ４０８ , R ３０９ and R ４０９ , R ３１０ and R ４１０ , R ３１１ and R ４１１ , R ３１２ and R ４１２ , R ３１３ and R ４１３ , R ３１４ and R ４１４ , as well as R ３１５ and R ４１５ may each be bonded to each other to form a ring. R ５０４ to R ５０７ and R ６０４ to R ６０７ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring-forming atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. At this time, R ５０４ and R ６０４ , R ５０５ and R ６０５ , R ５０６ and R ６０６ , and R ５０７ and R ６０７ may each be bonded to each other to form a ring. a1 to a15 are each independently 0, 1, 2, or 3, and b1 to b15 are each independently 0, 1, 2, 3, or 4; When any of a1 to a15 and b1 to b15 is 2 or more, each R ３０１ each R ３０２ each R ３０３ each R ３０４ each R ３０５ each R ３０６ each R ３０７ each R ３０８ each R ３０９ each R ３１０ each R ３１１ each R ３１２ each R ３１３ each R ３１４ each R ３１５ each R ４０１ each R ４０２ each R ４０３ each R ４０４ each R ４０５ each R ４０６ each R ４０７ each R ４０８ each R ４０９ each R ４１０ each R ４１１ each R ４１２ each R ４１３ each R ４１４ or each R ４１５ may be the same or different from each other.

5. In the formula (1), Ar ６ is any of the groups represented by the following formulas (7) to (22), the polymer according to any one of claims 1 to 4: 【Chemical Formula 6】 In the above formulas (7) to (22), R ９ to R ３５ each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring-forming atoms, an alkyl group having 1 to 60 carbon atoms, or a hydrogen atom, Q １ to Q ９ each independently represents -O-, -S-, -Se-, -CR ３６ R ３７ -, or -SiR ３８ R ３９ -, and in this case, R ３６ to R ３９ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Z １ to Z ７ each independently represents -CR ４０ =, -N=, or -SiR ４１ =, and in this case, R ４０ and R ４１ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. * is a bonding site forming the main chain.

6. A polymer comprising any one of the structural units represented by the following formulas (A-1) to (A-11). 【Chemical Formula 7】 【Chemical 8】

7. An electroluminescence element material comprising the polymer according to any one of Claims 1 to 6.

8. An electroluminescence device including a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, wherein: at least one of the organic films contains the polymer according to any one of claims 1 to 6, the electroluminescence device.

9. The electroluminescence device according to claim 8, wherein the organic film containing the polymer is a hole transport layer or a hole injection layer.

10. The electroluminescence device according to claim 8 or 9, wherein the organic film has a light emitting layer containing semiconductor nanoparticles or an organometallic complex.

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