Organic film forming material, organic film forming composition, method for manufacturing organic film, organic electroluminescent element, display, and lighting device

Abstract

To provide an organic film forming material capable of producing organic electroluminescent elements with excellent light-emitting characteristics and long driving life.SOLUTION: An organic film forming material contains the arylcarbazole compound represented by formula (2) and the boron-condensed ring compound represented by a specific formula.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a material for forming an organic film, a composition for forming an organic film, a method for producing an organic film, and organic electroluminescence. The present invention relates to an element, a display device, and a lighting device. [Background technology]

[0002] As a thin-film electroluminescent device, organic electroluminescent devices using organic thin films are being developed. An organic electroluminescent device (OLED) usually has a hole injection layer, a hole transport layer, and a The layer is an organic light-emitting layer, an organic light-emitting layer, an electron transport layer, etc., and materials suitable for each layer are being developed. Development is also underway for red, green, and blue light colors.

[0003] In addition, the organic layer of the organic electroluminescent device can be formed by vacuum deposition or wet film formation (coating). The vacuum deposition method is easy to form layers, so it is possible to use the electrons from the anode and / or cathode. It has the advantages of improving charge injection and facilitating exciton confinement in the light-emitting layer. The film formation method does not require a vacuum process, is easy to scale up, and can mix multiple materials with various functions. By using a mixed coating solution, it is possible to easily form layers containing multiple materials with various functions. Therefore, in recent years, organic electroluminescence devices using wet film formation methods have become popular. Research and development of optical elements is being carried out vigorously.

[0004] In displays using these organic electroluminescent devices, high definition and wide color gamut, i.e. In addition to high color gamut, a long lifespan that maintains brightness and chromaticity is required. There is also a demand for high luminous efficiency, emission with high color purity, and long operating life. The structure for extracting light emitted from the elements inside the display is a top emitter that does not pass through the TFT substrate. In this case, high luminous efficiency and color purity can be achieved by making strong use of optical interference. However, the wavelength range of the emission spectrum that can be extracted is narrower, so The development of devices and light-emitting materials that can emit light with a full half-width is becoming increasingly important.

[0005] As a method to achieve both long life and high efficiency, we have developed an organic electrochemical device using a material that exhibits thermally activated delayed fluorescence. The development of light-emitting devices has been widely carried out. For example, Patent Document 1 discloses a light-emitting device that exhibits thermally activated delayed fluorescence. The structure of the guest is widely disclosed. Patent Document 2 discloses a host material that exhibits thermally activated delayed fluorescence. Patent Document 3 discloses a method of using another fluorescent material as a guest in a thermally activated slow-release material. Organic electroluminescence using a host material that exhibits extended fluorescence and sensitizing emission from a highly efficient phosphorescent dye In both of these documents, an indium fluoride is used as an electron donating group for charge transfer transition. Isocarbazole is featured.

[0006] In addition, Patent Documents 4 and 5 disclose compounds having a polycyclic heterocyclic compound skeleton containing boron and nitrogen. and an organic electroluminescent device having a light-emitting layer containing a light-emitting material. The light-emitting element emits light with a narrow half-width, and is suitable for the top-emission display. is. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Special Publication No. 2020-525437 [Patent Document 2] International Publication No. 2012 / 133188 [Patent Document 3] Special Publication No. 2018-501668 [Patent Document 4] International Publication No. 2016 / 152418 [Patent Document 5] Japanese Patent Publication No. 2021-163964 Summary of the Invention [Problem to be solved by the invention]

[0008] However, the inventors have found that the techniques disclosed in the above Patent Documents 1 to 5 are It was found that each of these has the following problems. The organic electroluminescent devices described in Patent Documents 1 to 3 have the performance required for modern displays. In addition, the half-width of the emission spectrum was wide, and the top emission The material also has a structure suitable for vapor deposition type organic electroluminescent devices. However, the structure does not have a suitable dissolution stability for a coating composition. The organic electroluminescent devices described in Patent Documents 4 and 5 exhibit narrow half-width emission, but The dynamic life was short and the luminescence characteristics were insufficient.

[0009] The present invention has been made in view of the above-mentioned conventional circumstances, and provides a light emitting diode (LED) having high luminous efficiency and long operating life. The present invention aims to provide an organic film-forming material that can provide an organic electroluminescent device with a long life. This is a major issue. [Means for solving the problem]

[0010] As a result of extensive research, the present inventors have found that a polycyclic heterocyclic compound containing boron and a thermally activated slow-acting compound are By using a material for forming an organic film containing a host material with a specific structure that exhibits weak fluorescence, the above problem can be solved. The present invention has been completed based on the discovery that the above problems can be solved.

[0011] That is, the gist of the present invention is as follows. Aspect 1 of the present invention is a compound represented by the following formula (2) and a compound represented by the following formula (71): The organic film forming material contains

[0012] [ka]

[0013] [In formula (2), Ar 1 is a structure represented by formula (2a). Ar 2 each independently represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent; Ar 2 If there are multiple, they may be the same or different. Good too. Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a cyclic group having 1 to 20 carbon atoms. b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, except for hydrogen atoms, may have a substituent. The other pair has a structure represented by formula (2b). m and n each independently represents an integer of 1 to 3.

[0014] [ka]

[0015] [In formula (2a), R 1 are each independently a hydrogen atom, a (hetero)alkyl group having 3 to 20 carbon atoms which may have a substituent, ) aryl group, Ar 2 It is a combination with .]

[0016] [ka]

[0017] [In formula (2b), Ar 3 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hexyl) group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms alkylsilyl groups having 1 to 20 carbon atoms, and arylsilyl groups having 6 to 20 carbon atoms. an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. These groups, except for the hydrogen atom, may have a substituent. "★" indicates the bonding position with formula (2).

[0018] [ka]

[0019] (In equation (71), At least one selected from A1 to A7 is an electron accepting substituent, A1 to A7 other than the electron-accepting substituent each independently represent a hydrogen atom, a fluorine atom, or atom or an alkyl group which may have a substituent, R 71 ~R 78 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an electron-donating substituent, or a combination thereof; At least one hydrogen atom in the compound represented by formula (71) is replaced by a halogen atom or may be substituted with a deuterium atom, A dotted line represents a single bond or no bond.)

[0020] A second aspect of the present invention is the organic film-forming material of the first aspect, further comprising: The organic film-forming material contains a compound having the above structure.

[0021] [ka]

[0022] [In the formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or a substituent represents an aromatic heterocyclic structure which may have the following structure: Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When there are multiple rings A701 and multiple rings A702, they may be the same or different. That's fine. R 701 , R 702 are each independently a structure represented by formula (b), and "*" indicates ring A701 or represents the bonding position with ring A702. 701 , R 702 are the same but different Also, R 701 , R 702 If there are multiple of each, they may be the same but different. It may be possible. Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent. Ar 702 is an aromatic hydrocarbon ring structure which may have a substituent, It represents an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. Ar 701 , Ar 702, and Ar 703 If there are multiple of each, they are the same But it may be different. The substituents bonded to ring A701, the substituents bonded to ring A702, or the substituents bonded to ring A701 The substituents bonded to ring A702 may be bonded to each other to form a ring. good. B 701 -L 700 -B 702 represents an anionic bidentate ligand. 701 and B 7 02 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms form a ring. It may be an atom that 700 is a single bond or B 701 and B 702 With 2 Represents the atomic group that constitutes the dentate ligand. B 701 -L 700 -B 702 If there are multiple They may be the same or different. In addition, in equations (7) and (b), i1 and i2 each independently represent an integer of 0 to 12, i3 is Ar 702 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by j is Ar 701 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by k1 and k2 each independently represent an integer of 0 or greater, with the upper limit being the number of substitutions that can be made on ring A701 and ring A702. Represents the integer above. m is an integer between 1 and 3.

[0023] A third aspect of the present invention is a material for forming an organic film according to the first or second aspect, further comprising a compound represented by the following formula: 1) and a compound represented by the following formula (260): It is a material for forming organic films, including one type.

[0024] [ka]

[0025] [In formula (1), each W independently represents CH or N, and at least one W is N; Xa 1 , Ya 1 , and Za 1 each independently represents a group having 6 to 3 carbon atoms which may have a substituent a divalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents an aromatic heterocyclic group, Xa 2 , Ya 2 and Za 2 each independently represents a hydrogen atom, a carbon atom which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monovalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents a monovalent aromatic heterocyclic group, g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11, h11, and j11 is an integer of 1 or greater, If g11 is 2 or more, multiple Xa 1 may be the same or different, If h11 is 2 or more, multiple Ya 1 may be the same or different, If j11 is 2 or more, multiple Za 1 may be the same or different, R 31 represents a hydrogen atom or a substituent, and 12 R 31 Whether they are the same or different often, However, if g11, h11, or j11 is 0, the corresponding Xa 2 , Ya 2 , Z a 2 is not a hydrogen atom.]

[0026] [ka]

[0027] (In formula (260), Ar 61 ~Ar 65 each independently represents a hydrogen atom or a monovalent group which may have a substituent; an aromatic hydrocarbon group having 6 to 60 carbon atoms, L 1 ~L 5 each independently represents a divalent group having 6 to 60 carbon atoms which may have a substituent; is an aromatic hydrocarbon group of the formula R 60 each independently represents a substituent, m1 to m5 each independently represent an integer of 0 to 5; n represents an integer of 0 to 10, a1 to a3 each independently represent an integer of 0 to 3; However, Ar 61 , Ar 62 , Ar 63 , Ar 64 , and at least when n is 1 or more Another Ar 65 At least one of them is not a hydrogen atom.)

[0028] A fourth aspect of the present invention is a material for forming an organic film according to the third aspect, wherein the material is at least represented by the formula (1). The organic film-forming material contains a compound that is

[0029] A fifth aspect of the present invention is the organic film-forming material according to any one of the first to fourth aspects, R in the formula (2), formula (2a), and formula (2b) 1 , R 2 , Ar 2 and Ar 3 has The optional substituents are each independently an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryl group, an aryloxy ... oxy group, aryloxy group, heteroaryloxy group, alkylsilyl group, arylsilyl group alkyl group, alkylcarbonyl group, arylcarbonyl group, alkylamino group, aryl The organic film-forming material is an amino group, an aryl group, or a heteroaryl group.

[0030] A sixth aspect of the present invention is the organic film-forming material according to any one of the first to fifth aspects, wherein the organic film-forming material is a compound represented by the formula (2) is a material for forming an organic film represented by the following formula (2-1).

[0031] [ka]

[0032] [In formula (2-1), Ar 4 is a structure represented by the formula (2a), Ar 5 is Ar in the formula (2). 2 is a group selected from groups similar to those Ar 6 is Ar in the formula (2b). 3 is a group selected from groups similar to those R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, except for the hydrogen atom, may have a substituent. Ar 5 and Ar 6 When there are a plurality of each of the groups, they may be the same or different. j and k are values ​​selected from the same ranges as m and n in formula (2).

[0033] A seventh aspect of the present invention is the organic film-forming material of the sixth aspect, wherein A in the formula (2-1) r 5 are each independently a 1,3-phenylene group or a 1,4-phenylene group. It is a material used.

[0034] Aspect 8 of the present invention is the organic film-forming material of aspect 6 or aspect 7, wherein R in the formula (2-1) 3 , Ar 5 and Ar 6 The substituents which may be contained in alkyl groups, aralkyl groups, heteroaralkyl groups, alkoxy groups, aryloxy groups , heteroaryloxy group, alkylsilyl group, arylsilyl group, alkylcarbonyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or The organic film-forming material is a heteroaryl group.

[0035] A ninth aspect of the present invention is the organic film-forming material of the third aspect, wherein the formula (1) is represented by the following formula (1- 1) is a material for forming an organic film.

[0036] [ka]

[0037] [In formula (1-1), W1, W2 and W3 each independently represent -CH or a nitrogen atom; at least one of which is a nitrogen atom, Xa 1 , Ya 1 , and Za 1 each independently represents an optionally substituted 1,3-phenylene represents an phenylene group or an optionally substituted 1,4-phenylene group, Za 1at least one of is a 1,3-phenylene group, Xa 2 and Ya 2 each independently represents an optionally substituted phenyl group, Za 2 represents an N-carbazolyl group which may have a substituent, f11 is 1 or 2, g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer from 1 to 6, f11+g11+h11+j11 is greater than or equal to 5, R 11 each independently represents a hydrogen atom or a substituent.

[0038] A tenth aspect of the present invention is the organic film-forming material of the third aspect, wherein the formula (1) is the following formula (1 -2) is a material for forming an organic film.

[0039] [ka]

[0040] [In formula (1-2), W 1 , W 2 and W 3 each independently represents —CH or a nitrogen atom; W 1 , W 2 and W 3 at least one of which is a nitrogen atom, Xa 1 , Ya 1 , and Za 1 each independently represents an optionally substituted 1,3-phenylene represents an phenylene group or an optionally substituted 1,4-phenylene group, Ya 1 and Za 1 At least one of the groups is optionally substituted 1,3-phenylene. It is the basis, Xa2 represents an optionally substituted phenyl group, Ya 2 and Za 2 each independently represents an N-carbazolyl group which may have a substituent; death, f11 is 1 or 2, g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer between 2 and 5, f11+g11+h11+j11 is greater than or equal to 6, R 11 each independently represents a hydrogen atom or a substituent.

[0041] An eleventh aspect of the present invention is the organic film-forming material of the tenth aspect, Ya in the formula (1-2) 1 at least one of Z is a 1,3-phenylene group; a 1 At least one of the above is a 1,3-phenylene group.

[0042] A twelfth aspect of the present invention relates to the organic film-forming material of the tenth or eleventh aspect, Xa in the formula (1-2) 1 At least one of the organic groups is a 1,3-phenylene group. It is a film-forming material.

[0043] A thirteenth aspect of the present invention relates to the organic film-forming material according to any one of the first to twelfth aspects, The singlet energy level S1 (eV) and triplet energy level S2 (eV) of the compound represented by the formula (2) -Difference in level T1 (eV) (ΔE ST 1 ) is 0.2 (eV) or more for forming organic films be.

[0044] A fourteenth aspect of the present invention is a method for producing an organic film comprising the organic film-forming material according to any one of the first to thirteenth aspects and a solvent. The organic film-forming composition is

[0045] A fifteenth aspect of the present invention is a method for forming an organic film by a wet film formation method using the organic film-forming composition of the fourteenth aspect. This is a method for manufacturing a membrane.

[0046] A sixteenth aspect of the present invention is an organic layer comprising the organic film-forming material according to any one of the first to thirteenth aspects. The organic electroluminescent device has the following structure.

[0047] A seventeenth aspect of the present invention is a display device comprising the organic electroluminescent device of the sixteenth aspect.

[0048] An eighteenth embodiment of the present invention is a lighting device comprising the organic electroluminescent device of the sixteenth embodiment. [Effects of the Invention]

[0049] According to the present invention, an organic electroluminescent device having superior light-emitting properties and a longer operating life than conventional devices can be obtained. It is possible to provide a material for forming an organic film. [Brief explanation of the drawings]

[0050] [Figure 1] FIG. 1 is a cross-sectional view showing a structural example of an organic electroluminescent device of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0051] The following describes an organic film-forming material according to one embodiment of the present invention, an organic film-forming material containing the material, and A composition, an organic electroluminescent device having an organic layer containing the material, and a display device having the organic electroluminescent device. The following description will be given in detail of embodiments of a display device and a lighting device including the organic electroluminescent device. The above is a first embodiment, which is one example (typical example) of the present invention. The contents of this document are not limited to those specified above, unless they go beyond the gist of the document.

[0052] [Materials for organic film formation] The organic film-forming material of the present invention comprises a compound represented by the following formula (2) and a compound represented by the following formula (71): This includes compounds that are

[0053] <Compound represented by formula (2)>

[0054] [ka]

[0055] [In formula (2), Ar 1 is a structure represented by formula (2a). Ar 2 each independently represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent; Ar 2 If there are multiple, they may be the same or different. Good too. Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a substituted or unsubstituted alkyl group. b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, excluding hydrogen atoms, may have a substituent. The other pair has a structure represented by formula (2b). m and n each independently represent an integer of 1 to 3.

[0056] [ka]

[0057] [In formula (2a), R 1are each independently a hydrogen atom, a (hetero)alkyl group having 3 to 20 carbon atoms which may have a substituent, ) aryl group, Ar 2 It is a combination with .]

[0058] [ka]

[0059] [In formula (2b), Ar 3 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hexyl) group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms alkylsilyl groups having 1 to 20 carbon atoms, and arylsilyl groups having 6 to 20 carbon atoms. an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. These groups, except for the hydrogen atom, may have a substituent. "★" indicates the bonding position with formula (2).

[0060] Ar 2 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. It is more preferable that the aryl group is an aryl group having 6 to 60 carbon atoms. Ar 2 Specific examples of the ring include a benzene ring, a naphthalene ring, a dibenzofuran ring, and a thiophene ring. It is a divalent group derived from a ring, a dibenzothiophene ring, or a carbazole ring, and these are bonded A divalent group formed by bonding a benzene ring and a thiophene ring, for example, a phenylthio group formed by bonding a benzene ring and a thiophene ring From the viewpoint of device stability, a divalent group derived from phen is preferably used. benzene ring, naphthalene ring, and dibenzofuran ring, and more preferably benzene ring and naphthalene ring. It is a divalent group derived from an olefin ring, particularly preferably a benzene ring. Ar 2 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. It is preferable that:

[0061] Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a substituted or unsubstituted alkyl group. b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms or a (hetero)aryl group having 3 to 30 carbon atoms; From the viewpoint of device life, hydrogen atoms, alkyl groups having 1 to 20 carbon atoms, and heterocyclic groups having 7 to 40 carbon atoms are preferred. b) aralkyl groups, (hetero)aryloxy groups having 3 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms An arylamino group or a (hetero)aryl group having 3 to 30 carbon atoms is preferred, and a more preferred It is preferably a hydrogen atom or an aryl group having 3 to 30 carbon atoms. At least one pair of adjacent Rs has a structure represented by formula (2b). The substituent that R may have is a substituent selected from the substituent group Z described below. preferable.

[0062] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, and hexyl. From the viewpoint of device stability, a methyl group is preferred. , an ethyl group, or a hexyl group, and more preferably a methyl group. Specific examples of the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylmethyl group, and a phenylmethyl group. phenylethyl group, phenylpropyl group, phenylhexyl group, phenyloctyl group, phenyl From the viewpoint of device stability, phenylpropyl is preferred. A propyl group and a phenylhexyl group are preferred. Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a butyloxy group. From the viewpoint of device stability, methoxy and ethoxy groups are preferred. I wish.

[0063] Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group and a naphthyl group. The examples include an oxy group and a carbazolyloxy group, and from the viewpoint of device stability, a phenoxy group is preferred. I wish.

[0064] Examples of alkylsilyl groups having 1 to 20 carbon atoms include trimethylsilyl and triethylsilyl. From the viewpoint of device stability, trimethylsilyl is preferred. It is a methylsilyl group. Examples of the arylsilyl group having 6 to 20 carbon atoms include a dimethylphenylsilyl group, a triphenylsilyl group, and a phenylsilyl group. It is a phenylsilyl group.

[0065] Specific examples of the arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylamino group, and a From the viewpoint of device stability, diphenylamino groups and naphthylphenyl groups are preferred. The amino group is preferred. Specific examples of the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, Anthranyl group, biphenyl group, terphenyl group, carbazolyl group, thienyl group, benzo furyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, phenylthienyl group From the viewpoint of extending the life of the element, phenyl, naphthyl, biphenyl, thiazolinone ... -phenyl group, carbazolyl group, dibenzofuryl group, more preferably phenyl group , a biphenyl group, and a terphenyl group.

[0066] R 1 are each independently a hydrogen atom, a (hetero)alkyl group having 3 to 20 carbon atoms which may have a substituent, ) aryl group, Ar 2 At least one bond is to Ar 2 It is a combination of. Ar 2 R other than the bond with 1 is a hydrogen atom, a group having 3 to 20 carbon atoms which may have a substituent It is preferable that the aryl group is an aryl group represented by the formula: Specific examples of the (hetero)aryl group having 3 to 20 carbon atoms which may have a substituent include: Phenyl group, naphthyl group, anthranyl group, biphenyl group, terphenyl group, carbazole group benzothienyl group, dibenzofuryl group, dibenzothienyl group, From the viewpoint of extending the life of the element, phenyl groups, naphthienyl groups, etc. are preferred. The examples of the alkyl group include phenyl, biphenyl, terphenyl, carbazolyl, and dibenzofuryl groups. More preferred are a phenyl group, a biphenyl group and a terphenyl group. R 1 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. is preferred.

[0067] Ar 3 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. Specific examples of the (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent include: Phenyl group, naphthyl group, anthranyl group, biphenyl group, terphenyl group, carbazole group benzothienyl group, dibenzofuryl group, dibenzothienyl group, From the viewpoint of extending the life of the element, phenyl groups, naphthienyl groups, etc. are preferred. The examples of the alkyl group include phenyl, biphenyl, terphenyl, carbazolyl, and dibenzofuryl groups. More preferred are a phenyl group, a biphenyl group and a terphenyl group. Ar 3 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. It is preferable that:

[0068] R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms or a (hetero)aryl group having 3 to 30 carbon atoms; It is preferably a hydrogen atom or an aryl group having 3 to 30 carbon atoms which may have a substituent. These groups, except for the hydrogen atom, may have a substituent. R 2 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. is preferred.

[0069] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, and hexyl. From the viewpoint of device stability, a methyl group is preferred. , an ethyl group, or a hexyl group, and more preferably a methyl group. Specific examples of the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylmethyl group, and a phenylmethyl group. phenylethyl group, phenylpropyl group, phenylhexyl group, phenyloctyl group, phenyl From the viewpoint of device stability, phenylpropyl is preferred. A propyl group and a phenylhexyl group are preferred.

[0070] Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a butyloxy group. From the viewpoint of device stability, methoxy and ethoxy groups are preferred. I wish. Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group and a naphthyl group. The examples include an oxy group and a carbazolyloxy group, and from the viewpoint of device stability, a phenoxy group is preferred. I wish.

[0071] Examples of alkylsilyl groups having 1 to 20 carbon atoms include trimethylsilyl and triethylsilyl. From the viewpoint of device stability, trimethylsilyl is preferred. It is a methylsilyl group. Examples of the arylsilyl group having 6 to 20 carbon atoms include a dimethylphenylsilyl group, a triphenylsilyl group, and a phenylsilyl group. It is a phenylsilyl group.

[0072] Specific examples of the arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylamino group, and a From the viewpoint of device stability, diphenylamino groups and naphthylphenyl groups are preferred. The amino group is preferred. Specific examples of the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, Anthranyl group, biphenyl group, terphenyl group, carbazolyl group, thienyl group, benzo furyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, phenylthienyl group From the viewpoint of extending the life of the element, phenyl, naphthyl, biphenyl, thiazolinone ... -phenyl group, carbazolyl group, dibenzofuryl group, more preferably phenyl group , a biphenyl group, and a terphenyl group.

[0073] R 1 , R 2 , Ar2 and Ar 3 The substituents which may be possessed by each of the groups may be independently selected from the substituents described below. It is preferably a substituent selected from group Z.

[0074] m and n each independently represent an integer of 1 to 3. m is preferably 1 to 2, and more preferably 2. The charge transport property is appropriately adjusted. From the viewpoint of coordination, n is preferably 1, and from the viewpoint of improving charge transport properties, n is preferably 0. is preferably 2 to 3.

[0075] The compound represented by formula (2) is preferably a charge transport compound, i.e., a charge transport host. Preferably, it is a material. The organic film-forming material of the present invention contains only one compound represented by the formula (2). It may contain two or more kinds of them.

[0076] The singlet energy level S1 (eV) and triplet energy level S2 (eV) of the compound represented by the formula (2) -Difference in level T1 (eV) (ΔE ST 1 ) is preferably 0.15 (eV) or more, It is more preferably 0.2 (eV) or more, and particularly preferably 0.25 (eV) or more. Preferred. ΔE ST 1 When the value of is in the above range, the T1 level of the compound represented by formula (2) is stable. The compound represented by formula (2) is stabilized and transports holes more easily than electrons. As a result, the carrier balance of the organic electroluminescent device of the present invention is stabilized, and the driving life is improved. They tend to live longer.

[0077] The formula (2) is preferably represented by the following formula (2-1).

[0078] [ka]

[0079] [In formula (2-1), Ar 4 is the structure represented by the above formula (2a). 5 is the Ar in the above formula (2). 2 is a group selected from the same groups as Ar 6 is the Ar in the above formula (2b). 3 Similar groups and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. , (hetero)aralkyl groups having 7 to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, and (Hetero)aryloxy groups having up to 20 carbon atoms, alkylsilyl groups having 1 to 20 carbon atoms, and alkylsilyl groups having 6 to 10 carbon atoms. an arylsilyl group having 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or an arylsilyl group having 3 to 30 carbon atoms; These groups, excluding hydrogen atoms, may have a substituent. Ar 5 and Ar 6 When there are a plurality of each of the groups, they may be the same or different. j and k are values ​​selected from the same ranges as m and n in the above formula (2).

[0080] Ar 5 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. It is more preferable that the aryl group is an aryl group having 6 to 60 carbon atoms.

[0081] Ar 5 Specific examples of the ring include a benzene ring, a naphthalene ring, a dibenzofuran ring, and a thiophene ring. It is a divalent group derived from a ring, a dibenzothiophene ring, or a carbazole ring, and these are bonded A divalent group formed by bonding a benzene ring and a thiophene ring, for example, a phenylthio group formed by bonding a benzene ring and a thiophene ring From the viewpoint of device stability, a divalent group derived from phen is preferably used. benzene ring, naphthalene ring, and dibenzofuran ring, and more preferably benzene ring and naphthalene ring. It is a divalent group derived from an olefin ring, particularly preferably a benzene ring. Ar 5 are each independently a 1,3-phenylene group or a 1,4-phenylene group. It is more preferable that:

[0082] Ar 6 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. Specific examples of the (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent include: Phenyl group, naphthyl group, anthranyl group, biphenyl group, terphenyl group, carbazole group benzothienyl group, dibenzofuryl group, dibenzothienyl group, From the viewpoint of extending the life of the element, phenyl groups, naphthienyl groups, etc. are preferred. The examples of the alkyl group include phenyl, biphenyl, terphenyl, carbazolyl, and dibenzofuryl groups. More preferred are a phenyl group, a biphenyl group and a terphenyl group.

[0083] R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hexyl) group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms alkylsilyl groups having 1 to 20 carbon atoms, and arylsilyl groups having 6 to 20 carbon atoms. an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. From the viewpoint of device life, hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, and alkyl groups with 7 to 40 carbon atoms are preferred. (hetero)aralkyl groups, (hetero)aryloxy groups having 3 to 20 carbon atoms, An arylamino group or a (hetero)aryl group having 3 to 30 carbon atoms is preferred, and a more preferred or a hydrogen atom, or an aryl group having 3 to 30 carbon atoms.

[0084] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, and hexyl. From the viewpoint of device stability, a methyl group is preferred. , an ethyl group, or a hexyl group, and more preferably a methyl group. Specific examples of the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylmethyl group, and a phenylmethyl group. phenylethyl group, phenylpropyl group, phenylhexyl group, phenyloctyl group, phenyl From the viewpoint of device stability, phenylpropyl is preferred. A propyl group and a phenylhexyl group are preferred.

[0085] Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a butyloxy group. From the viewpoint of device stability, methoxy and ethoxy groups are preferred. I wish. Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group and a naphthyl group. The examples include an oxy group and a carbazolyloxy group, and from the viewpoint of device stability, a phenoxy group is preferred. I wish.

[0086] Examples of alkylsilyl groups having 1 to 20 carbon atoms include trimethylsilyl and triethylsilyl. From the viewpoint of device stability, trimethylsilyl is preferred. It is a methylsilyl group. Examples of the arylsilyl group having 6 to 20 carbon atoms include a dimethylphenylsilyl group, a triphenylsilyl group, and a phenylsilyl group. It is a phenylsilyl group.

[0087] Specific examples of the arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylamino group, and a From the viewpoint of device stability, diphenylamino groups and naphthylphenyl groups are preferred. The amino group is preferred. Specific examples of the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, Anthranyl group, biphenyl group, terphenyl group, carbazolyl group, thienyl group, benzo furyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, phenylthienyl group From the viewpoint of extending the life of the element, phenyl, naphthyl, biphenyl, thiazolinone ... -phenyl group, carbazolyl group, dibenzofuryl group, more preferably phenyl group , a biphenyl group, and a terphenyl group.

[0088] R 3 , Ar 5 , and Ar 6 The substituents which may be possessed by each of the following groups of substituents may be independently selected from the group of substituents described below. Preferably, the substituent is selected from Z.

[0089] The compound represented by the above formula (2-1) (hereinafter also referred to as compound (2-1)) is preferably Preferably, the compound is a charge transport compound, i.e., a charge transport host material. The organic film-forming material of the present invention contains only one compound represented by the formula (2-1). It may contain two or more kinds.

[0090] The substituents that the compounds represented by formula (2) and formula (2-1) may have are the following substituent groups: Substituents selected from Z are preferred.

[0091] <Substituent group Z> The substituent group Z is an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryl ... aryloxy group, heteroaryloxy group, alkylsilyl group, arylsilyl group, alkyl alkylcarbonyl group, arylcarbonyl group, alkylamino group, arylamino group, aryl It is a aryl group or a heteroaryl group.

[0092] Preferably, the alkyl group has 1 to 20 carbon atoms, the aralkyl group has 7 to 40 carbon atoms, and the alkyl group has 7 to 40 carbon atoms. heteroaralkyl groups having up to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms alkyloxy group, heteroaryloxy group having 3 to 20 carbon atoms, alkylsilyl group having 1 to 20 carbon atoms arylsilyl groups having 6 to 20 carbon atoms, alkylcarbonyl groups having 2 to 20 carbon atoms, Arylcarbonyl groups with 7 to 20 carbon atoms, alkylamino groups with 1 to 20 carbon atoms, and alkylamino groups with 6 to 10 carbon atoms. an arylamino group having 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a hetero group having 3 to 30 carbon atoms; It is an aryl group, and more specifically, it is a substituent described in [Specific examples of substituents] below. More preferably, the alkyl group has 1 to 20 carbon atoms, the aralkyl group has 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms is an aryl group of the formula:

[0093] [Specific examples of substituents] The alkyl group having 1 to 20 carbon atoms may be any of a linear, branched, or cyclic alkyl group. More specifically, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n- Pentyl group, n-hexyl group, n-octyl group, isopropyl group, isobutyl group, isopentyl group Examples include butyl, methyl, and cyclohexyl groups. straight-chain alkyl groups having 1 to 8 carbon atoms, such as n-butyl groups, n-hexyl groups, and n-octyl groups; The aryl group is preferred.

[0094] The (hetero)aralkyl group having 7 to 40 carbon atoms may be a straight-chain alkyl group, a branched alkyl group, or a A part of the hydrogen atoms constituting the alkyl group or cyclic group is an aryl group or a heteroaryl group More specifically, it refers to a group substituted with a 2-phenyl-1-ethyl group, a cumyl group, , 5-phenyl-1-pentyl group, 6-phenyl-1-hexyl group, 7-phenyl-1- Examples include 5-phenyl-1-heptyl and tetrahydronaphthyl groups. Preferred are a phenyl-1-hexyl group, a 6-phenyl-1-pentyl group, and a 7-phenyl-1-heptyl group.

[0095] Specific examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a propoxy group. Pyroxy group, isopropyloxy group, hexyloxy group, cyclohexyloxy group, octyloxy group Among them, a hexyloxy group is preferred. Specific examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group, 4-methylphenyloxy group, etc. Among these, a phenoxy group is preferred.

[0096] The alkylsilyl group having 1 to 20 carbon atoms has a structure in which a part of the alkyl group is substituted with an aryl group. Specific examples thereof include a trimethylsilyl group, a triethylsilyl group, and a methylsilyl group. silyl group, triisopropylsilyl group, dimethylphenylsilyl group, t-butyldimethylsilyl group Among them, triisopropylsilyl and t-butyldiphenylsilyl groups are preferred. A t-butyldimethylsilyl group, a t-butyldiphenylsilyl group are preferred. Specific examples of the arylsilyl group having 6 to 20 carbon atoms include diphenylpyridylsilyl. Among them, the triphenylsilyl group is preferred. stomach.

[0097] Specific examples of the alkylcarbonyl group having 2 to 20 carbon atoms include an acetyl group, a propionyl group, and a methyl group. cyclohexyl group, pivaloyl group, caproyl group, decanoyl group, cyclohexylcarbonyl group, etc. Among these, an acetyl group and a pivaloyl group are preferred. Specific examples of the arylcarbonyl group having 7 to 20 carbon atoms include a benzoyl group, a naphthyl group, and a benzoyl group. Among them, a benzoyl group is preferred. Specific examples of the alkylamino group having 1 to 20 carbon atoms include a methylamino group, a dimethylamino group, and a methylamino group. Amino group, diethylamino group, ethylmethylamino group, dihexylamino group, dioctyl Among these, dimethylamino group, dicyclohexylamino group, etc. are particularly preferred. The cyclohexylamino group is preferred.

[0098] Specific examples of the arylamino group having 6 to 20 carbon atoms include a phenylamino group, a diphenylamino group, and a phenylamino group. di(4-tolyl)amino group, di(2,6-dimethylphenyl)amino group, etc. Among these, a diphenylamino group and a di(4-tolyl)amino group are preferred. The (hetero)aryl group having 3 to 30 carbon atoms is an aromatic group having one free valence. Hydrocarbon groups, aromatic heterocyclic groups, linked aromatic hydrocarbon groups in which multiple aromatic hydrocarbons are linked together, A linked aromatic heterocyclic group in which multiple aromatic heterocyclic groups are linked together, or a combination of an aromatic hydrocarbon and an aromatic It means a group in which at least one heterocycle is arbitrarily linked.

[0099] Specific examples include benzene rings, naphthalene rings, anthracene rings, and the like, which have one free valence. ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, phenylene ring, triphenylene ring, fluoranthene ring, furan ring, benzofuran ring, dibenzofuran Ran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, pyrrole ring, pyrrole ring azole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrrole ring Roimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thieno Thiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazo ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridine ring, a quinolone ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, Examples include a quinoxaline ring, a perimidine ring, a quinazoline ring, a quinazolinone ring, and an azulene ring. Examples of linked aromatic hydrocarbon groups in which multiple aromatic hydrocarbons are linked include biphenyl. groups, terphenyl groups, etc.

[0100] Among (hetero)aryl groups, from the viewpoint of durability, benzophenone having one free valence is preferred. Zene ring, naphthalene ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, A lysine ring, a pyrimidine ring, or a triazine ring is preferred, and among these, a ring having one free valence and A benzene ring, a naphthalene ring or a phenyl ring which may be substituted with an alkyl group having 1 to 8 carbon atoms. An aryl group having 6 to 18 carbon atoms, such as a nanthrene ring, or a A pyridine ring optionally substituted with 1 to 4 alkyl groups is more preferred, and one free a benzene ring, a naphtha ring, or a benzene ring having a valence and optionally substituted with an alkyl group having 1 to 8 carbon atoms; It is more preferably an aryl group having 6 to 18 carbon atoms, such as an aryl ring or a phenanthrene ring. It's nice.

[0101] When a group in a compound has multiple substituents, the combination of these substituents is is, for example, a combination of an aryl group and an alkyl group, a combination of an aryl group and an aralkyl group, A combination of an aryl group, an alkyl group, and an aralkyl group can be used. Examples of the combination of an aryl group and an aralkyl group include, but are not limited to, For example, a phenyl group, a biphenyl group, or a terphenyl group and a 5-phenyl-1-pentyl group Or a combination with a 6-phenyl-1-hexyl group can be used.

[0102] The molecular weight of the compound (2-1) is usually 5,000 or less, preferably 3,000 or less, and more preferably Preferably, it is 2500 or less, particularly preferably 2000 or less, and most preferably 1 The lower limit of the molecular weight of the compound (2-1) is preferably 350 or more. It is more preferably 400 or more, and particularly preferably 500 or more.

[0103] The specific structure of the compound (2-1) is not particularly limited, but examples thereof include the following compounds: It can be obtained.

[0104] [ka]

[0105] [ka]

[0106] <Compound represented by formula (71)>

[0107] [ka]

[0108] (In equation (71), At least one selected from A1 to A7 is an electron accepting substituent, A1 to A7 other than the electron-accepting substituent each independently represent a hydrogen atom, a fluorine atom, or atom or an alkyl group which may have a substituent, R 71 ~R 78 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an electron-donating substituent, or a combination thereof; At least one hydrogen atom in the compound represented by formula (71) is replaced by a halogen atom or may be substituted with a deuterium atom, A dotted line represents a single bond or no bond.)

[0109] In the compound represented by formula (71), A1 to A7 are bonded to the phenyl group at the positions: The electron cloud of the LUMO is localized and gathered. Therefore, at least one of the groups A1 to A7 is selected. By making one of the substituents an electron acceptor, as described later, the electron cloud expands and the LUMO The energy level becomes stable and the energy difference between the HOMO and LUMO becomes smaller. As a result, by using the compound represented by formula (71), it is possible to obtain an emission spectrum with a longer wavelength. This can be done.

[0110] In addition, in the compound represented by formula (71), R 71 ~R 78 , the HOMO electron cloud are localized and gather together. Therefore, R 71 ~R78 At least one selected from the following By using electron-donating substituents, the HOMO electron cloud tends to spread outward, The energy level of the OMO becomes unstable, and the energy difference between the HOMO and LUMO becomes smaller. As a result, the compound represented by formula (71) can obtain an emission spectrum with a longer wavelength. can be done.

[0111] The compound represented by the formula (71) will be described in detail below. When the substituent is selected from the substituent group ZF described below, the substituent is included in the substituent group ZF. Any of the substituents may be used. Among the substituents ZF, alkyl groups, alkoxy groups, and the like are preferred. The alkyl group is an oxy group, an aryloxy group, an aromatic hydrocarbon group, or an aralkyl group.

[0112] (A1~A7) At least one selected from A1 to A7 is an electron accepting substituent, A1 to A7 other than the electron acceptor substituent each independently represent a hydrogen atom, a fluorine atom, or is an alkyl group which may have a substituent.

[0113] At least one selected from A1 to A7 is an electron accepting substituent, There is a tendency that the emission wavelength can be adjusted by changing the number and types of A1 to A7.

[0114] In the present invention, the electron-accepting substituent is a substituent that is chemically bonded to an adjacent chemical structure. It is a substituent in a chemical structure that tends to extract electrons from an atom and become electron-excessive.

[0115] Examples of electron-accepting substituents include electron-accepting heteroaryls. a substituent such as a group, a nitro group, a cyano group, or an aromatic group having any of these substituents Among these, aromatic hydrocarbon groups and aromatic heterocyclic groups are preferred from the viewpoint of increasing wavelength. From this viewpoint, electron-accepting heteroaryl groups are preferred.

[0116] The heteroaryl group contains at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom. An aryl group has one atom. A heteroaryl group has, for example, one carbon atom, one nitrogen atom, and one aryl group. Polycyclic aromatic heteroaryls containing hydrogen atoms, oxygen atoms, sulfur atoms, etc., with 1 to 4 rings Examples of the group include a group having the formula: An electron-accepting heteroaryl group is a group that chemically bonds to and accepts electrons from adjacent chemical structures. is a heteroaryl group that easily becomes electron-excessive by abstracting It is a heteroaryl group having an absolute value α of 3 eV or more.

[0117] Electron-accepting substituents have the following properties: HOMO energy level and LUMO energy level The absolute value of the sum of the levels divided by 2 (hereinafter referred to as "absolute value α") is 3e It is preferable that the absolute value α is 3 eV or more. The electron acceptor property of the compound is improved.

[0118] The absolute value α of the electron-accepting substituent is preferably 3.1 eV or more, and more preferably 3.5 eV or more. More preferably, the electron acceptor property is 4.0 eV or more, and even more preferably, 4.0 eV or more. The upper limit of the absolute value α of the substituent is not particularly set, but is generally 7.0 eV or less. do.

[0119] HOMO energy levels and LUMO energies of electron-accepting substituents The energy levels of the HOMO molecular orbital and the LUM are obtained as follows: This refers to the energy level of the molecular orbital of O. That is, the electron acceptor in formula (1) The single bond between the phenyl group and the adjacent phenyl group is deleted and a hydrogen atom is added. The molecular structure of the obtained electron-accepting substituent was calculated using the molecular orbital calculation software Gaussian In an16, the density functional is calculated using the functional: B3LYP and the basis set: 6-31G(d). A structural optimization calculation can be performed using the following formula.

[0120] The electron-accepting substituent is a group represented by the following formula (71-5), a group represented by the following formula (7 1-6), a group represented by the following formula (71-7), or a group represented by the following formula (71-8): It is preferable that the group is a group such that

[0121] [ka]

[0122] In equations (71-5) to (71-8), R 732 ~R 745 each independently represents a hydrogen atom or an alkyl group which may have a substituent or an aromatic hydrocarbon group which may have a substituent.

[0123] Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an isopropyl group. butyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n- hexyl group, n-octyl group, cyclohexyl group, dodecyl group, etc. Examples of alkyl groups include linear, branched, and cyclic alkyl groups having a molecular weight of 24 or less.

[0124] Examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 60 carbon atoms. Specifically, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, Perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring , acenaphthene ring, fluoranthene ring, fluorene ring, etc., a 6-membered single ring or 2-5 condensed rings Examples include monovalent ring groups.

[0125] R 732 ~R 745 The substituents which may be substituted by the aryl group may be selected from the group ZF of substituents described below. This can be done.

[0126] Specific examples of the above formulae (71-5) to (71-8) include the following formulae (71-2-1 )~(71-2-7) are listed.

[0127] [ka]

[0128] In the above formulas (71-2-1) to (71-2-7), the absolute value α obtained from the calculation is as follows: As shown below.

[0129] Group represented by formula (71-2-4): 4.35 eV Group represented by formula (71-2-6): 4.18 eV Group represented by formula (71-2-3): 4.17 eV Group represented by formula (71-2-7): 4.12 eV Group represented by formula (71-2-5): 4.10 eV Group represented by formula (71-2-2): 3.73 eV Group represented by formula (71-2-1): 3.13 eV

[0130] That is, among A1 to A7 in the above formula (1), the same number of the above formulas are used in the same positions. a group represented by the formula (71-2-4), a group represented by the formula (71-2-6), a group represented by the formula (71- 2-3), a group represented by the above formula (71-2-7), a group represented by the above formula (71-2-5) a group represented by the above formula (71-2-2), or a group represented by the above formula (71-2-1) When a group having the formula (71-2-4) is introduced, the formula (71-2-6) is replaced by the formula (71-2-7). 71-2-3)> Above formula (71-2-7)> Above formula (71-2-5)> Above formula (71-2 The effect of increasing the emission wavelength is obtained in the order of (71-2)>(71-2-1).

[0131] Among these, electron-accepting substituents are advantageous in that they are suitable for longer wavelengths and for production by organic synthesis. From the viewpoint of ease of use, the group represented by the above formula (71-5) is preferred.

[0132] The group represented by the above formula (71-5) has a relatively large absolute value α, and Since there is little steric hindrance between the adjacent phenyl groups in the above formula (7 The π-plane of the group represented by 1-5) has little twist, and the effect of extending the emission wavelength to a longer wavelength is obtained. In addition, the group represented by the above formula (71-5) can be produced relatively easily in organic synthesis. Even if you want to improve the solubility in solvents, 732 , R 733 to a long chain (e.g., carbon Alkyl groups (number of carbon atoms: 4 or more) can be introduced relatively easily.

[0133] By increasing the absolute value α, it becomes easier to obtain a long wavelength emission wavelength, and the solubility in the solvent From the viewpoint of resolvability, R 732 , R 733 At least one selected from the group consisting of The alkyl group may be optionally substituted, and a phenyl group having a tert-butyl group is preferred.

[0134] From the viewpoint of solubility in solvents and narrowing the half-width of the emission wavelength, R 732 and R 73 At least one selected from the group consisting of 3 is an aromatic hydrocarbon group which may have a substituent. The substituent that the aromatic hydrocarbon group may have is selected from the group ZF of substituents described below. It is possible.

[0135] In addition, A1 to A7 other than the electron-accepting substituent each independently represent a hydrogen atom, a fluorine atom, or It is a hydrogen atom or an alkyl group which may have a substituent.

[0136] Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an isopropyl group. butyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n- hexyl group, n-octyl group, cyclohexyl group, dodecyl group, etc. Examples of alkyl groups include linear, branched, and cyclic alkyl groups having a molecular weight of 24 or less.

[0137] The substituents that A1 to A7 may have can be selected from the substituent group ZF described below. do.

[0138] Each of A1 to A7 independently represents a fluorine atom or an alkyl group which may have a substituent. When A1 to A7 are each a hydrogen atom, their electron-accepting properties make it more preferable than when A1 to A7 are each a hydrogen atom. The emission wavelength will be slightly shorter or longer, so select the substituent according to the desired wavelength. is preferred.

[0139] In addition, when a wet film-forming method is used, A1 to A7 each independently improve the solubility in a solvent. For the purpose of improving the solubility, a long-chain alkyl group is preferred.

[0140] Among A1 to A7, the degree of localization of the LUMO electron cloud is not uniform, but varies depending on the position. Therefore, among A1 to A7, the longer wavelength is due to the electron-accepting substituent. The positions where the effect is strongest are A4>A1=A7>A3=A5>A2=A6. That is, the effect of electron-accepting substituents on wavelength increase is strongest in A4. It appears quickly.

[0141] Therefore, at least one selected from A1, A4, and A7 has electron acceptor properties. It is preferable that the substituent is a group represented by the formula (71-5), and more preferable that the substituent is a group represented by the formula (71-5) .

[0142] When both A1 and A7 are electron-accepting substituents, only A4 is an electron-accepting substituent. Compared to the case where the substituent has acceptor properties, the effect of increasing the wavelength is almost the same. In addition, two or more selected from A1 to A7 are electron-accepting substituents. It is preferable for the wavelength to be longer, and two or more selected from A1 to A7 are electron acceptors. and at least one of A4 is an electron-accepting substituent. is preferable because it further increases the wavelength.

[0143] In the formula (71), the single bonds connecting A1 to A7 and the adjacent phenyl groups are twisted. The π plane of the main aromatic hydrocarbon group of the adjacent phenyl group and the electron-accepting substituent is It is preferable to avoid twisting. This twisting allows electrons to pass between adjacent phenyl groups. The charge transfer between the acceptor substituents is difficult to carry out smoothly, and the luminescence of the above formula (71) This is because the wavelength is less likely to be lengthened.

[0144] R 71 ~R 78 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an electron-donating substituent, or a combination thereof.

[0145] Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an isopropyl group. butyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n- hexyl group, n-octyl group, cyclohexyl group, dodecyl group, etc. Examples of alkyl groups include linear, branched, and cyclic alkyl groups having a molecular weight of 24 or less.

[0146] Examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 60 carbon atoms. Specifically, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, Perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring , acenaphthene ring, fluoranthene ring, fluorene ring, etc., a 6-membered single ring or 2-5 condensed rings Examples include monovalent ring groups.

[0147] The aromatic heterocyclic group is preferably an aromatic heterocyclic group having 3 to 60 carbon atoms. Specifically, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, Pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienopyrrole ring, Enothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxa azole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, Pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinone ring a 5- or 6-membered monocyclic ring or one of 2 to 4 condensed rings such as azoline ring, quinazolinone ring, azulene ring, etc. Examples of such groups include:

[0148] R 71 ~R 78 The substituents which may be substituted by the group ZF may be selected from the group of substituents ZF described below. can.

[0149] Also, R 71 ~R 78 At least one selected from the group consisting of: This is preferable from the viewpoint of increasing the wavelength.

[0150] In the present invention, the electron-donating substituent is a group that is chemically bonded to and receives electrons from the adjacent chemical structure. It is a substituent with a chemical structure that is prone to donating electrons and becoming electron deficient.

[0151] In the compound represented by formula (71), R 71 ~R 78 The HOMO electron cloud is localized at Therefore, R 71 ~R 78 At least one selected from the group consisting of By using the substituent, the electron cloud of the HOMO tends to spread outward, and the energy of the HOMO The energy levels become unstable, and the energy difference between the HOMO and LUMO becomes smaller. As a result, the compound represented by formula (71) can obtain an emission spectrum with a longer wavelength. can.

[0152] The electron donating substituent is preferably a group having an absolute value α of less than 3 eV. When the value α is less than 3 eV, the electron donating ability of the substituent is empirically improved.

[0153] The absolute value α of the electron-donating substituent is preferably less than 2.97 eV from the viewpoint of increasing the wavelength. More preferably, it is less than 2.8 eV, and particularly preferably less than 2.6 eV. The lower limit of the absolute value α of the electron donating substituent is not particularly set, but is generally 1 eV That's all.

[0154] HOMO and LUMO energy levels of electron-donating substituents. The positions are the energy levels of the HOMO molecular orbital and the LUMO distribution obtained as follows: The energy level of the electron donating substituent in formula (71) is the electron donating orbital of the The single bond between the two phenyl groups is removed and a hydrogen atom is added. The molecular structure of the electron-donating substituent was calculated using the molecular orbital calculation software Gaussian 16. Geometry optimization using density functional theory with B3LYP and 6-31G(d) basis set Just do the calculations.

[0155] The electron donating substituent is a group represented by the following formula (71-2), a group represented by the following formula (71-3) ) or a group represented by the following formula (71-4):

[0156] [ka]

[0157] In equations (71-2) to (71-4), R 709 ~R 724 , R 727 ~R 731 each independently may have a substituent It is an alkyl group, an aromatic hydrocarbon group which may have a substituent, or a hydrogen atom.

[0158] Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an isopropyl group. butyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n- hexyl group, n-octyl group, cyclohexyl group, dodecyl group, etc. Examples of alkyl groups include linear, branched, and cyclic alkyl groups having a molecular weight of 24 or less.

[0159] Examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 60 carbon atoms. Specifically, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, Perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring , acenaphthene ring, fluoranthene ring, fluorene ring, etc., a 6-membered single ring or 2-5 condensed rings Examples include monovalent ring groups.

[0160] R 709 ~R 724 , R 727 ~R 731 The substituents which may be contained in It can be selected from the group ZF.

[0161] Specific examples of the above formulae (71-2) to (71-4) include the following formulae (71-4-1 )~(71-4-3) are listed.

[0162] [ka]

[0163] In the above formulas (71-4-1) to (71-4-3), the absolute value α obtained from the calculation is as follows: As shown below.

[0164] Group represented by formula (71-4-3): 2.96 eV Group represented by formula (71-4-2): 2.91 eV Group represented by formula (71-4-1): 2.46 eV

[0165] That is, R in the above formula (71) 71 ~R 78 Of these, the same number in the same location A group represented by the above formula (71-4-3), a group represented by the above formula (71-4-2), or When a group represented by formula (71-4-1) is introduced, the above formula (71-4-1)>the above formula (7 The effect of increasing the emission wavelength is obtained in the order of (1-4-2)>(71-4-3). Also, R 71 ~R 78 Preferably, two or more selected from the above are electron-donating substituents. This is preferable because it results in a longer wavelength.

[0166] Among these, electron-donating substituents are preferred because they are suitable for longer wavelengths and easier to produce by organic synthesis. From the viewpoint of the balance of structural stability, the group represented by the above formula (71-2) is preferred. I wish.

[0167] The group represented by the above formula (71-2) has a relatively small absolute value of α and is suitable for shifting the emission wavelength to a longer wavelength. In addition, the group represented by the above formula (71-2) can be obtained relatively easily in organic synthesis. Even if you want to improve the solubility in solvents, 709 ~R 716 Long chain a The alkyl group can be introduced relatively easily.

[0168] R 709 ~R 716 At least one selected from the above is soluble in a solvent and easy to synthesize. From the viewpoint of size, a tert-butyl group is preferred.

[0169] In addition, R 71 ~R 78 each independently represents an optionally substituted alkyl group, an aromatic hydrocarbon group which may have one or more substituents, an aromatic heterocyclic group which may have one or more substituents, When the substituents are donor groups, or a combination thereof, their electron-accepting properties make R 71 ~R 78 The emission wavelength is slightly shorter or longer than when the atom is a hydrogen atom. Therefore, it is preferable to select a substituent according to the target wavelength.

[0170] In addition, when a wet film formation method is used, R 71 ~R 78 are each independently the solubility in a solvent For the purpose of improving the above, a long-chain alkyl group is preferred.

[0171] R 71 ~R 78 The degree of localization of the HOMO electron cloud is not uniform and varies depending on the position. There are strengths and weaknesses. 71 ~R 78 Among these, the longer wavelength due to electron donor substituents The position where the effect of is most pronounced is R 74 =R 75 >R 71 =R 78 >R 73 =R 76 >R7 2=R 77 That is, R 74 and R 75 In this case, the electron donor substituent The effect of increasing wavelength is most pronounced.

[0172] At least one hydrogen atom in the compound represented by formula (71) is replaced by a halogen atom or It may be substituted with a deuterium atom.

[0173] In formula (71), the dotted line may represent a single bond or no bond. The dotted line is preferably a single bond. When the dotted line is a single bond, the electron cloud expands and light is emitted. The wavelength becomes slightly longer. Also, if the dotted line is a single bond, the electron access in A1 to A7 Substituent groups and R 71 ~R 78 By introducing electron-donating substituents in It becomes easier.

[0174] The compound represented by the formula (71) is asymmetric, which narrows the half width of the emission wavelength. This is preferable because it has the effect of reducing the symmetry in the asymmetric type. The compounds represented by formula (71) are less likely to associate with each other, and the interaction between the compounds represented by formula (71) is reduced. Therefore, it is considered that the half width of the emission spectrum becomes narrow.

[0175] The compound represented by formula (71) is asymmetric when B and A When the line connecting the bond axis of 4 is used as the rotation axis, the same or the polycyclic heterocyclic structure of the compound represented by the formula (71) including the bond axis. The problem is that it is not a mirror image of the plane perpendicular to the plane formed by the ring.

[0176] Specifically, a structure that satisfies at least one of the following (i) and (ii) is preferred. (i) A1 to A7, R 71 ~R 78 When rotated 180° about the bond axis, A structure that does not have the same structure. (ii) A1 and A7 are different, A2 and A6 are different, A3 and A5 are different, R 71 and R 78 are different or R 72 and R 77are different or R 73 and R 76 are different, or R 74 and R 75 But the structure is different.

[0177] The structure of the compound represented by formula (71) is not particularly limited, but for example, the following structure is Examples include:

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181] [ka]

[0182] [ka]

[0183] [ka]

[0184] [ka]

[0185] [ka]

[0186] [ka]

[0187] [ka]

[0188] [ka]

[0189] <Substituent group ZF> Examples of the substituent group ZF include the following structures. The substituent group ZF is an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, Oxy group, heteroaryloxy group, alkoxycarbonyl group, dialkylamino group, di Arylamino group, arylalkylamino group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, siloxy group, cyano group, aromatic hydrocarbon The group consisting of alkyl groups, aromatic heterocyclic groups, aralkyl groups, and heteroaralkyl groups. Preferred structures and specific examples of these substituents are as follows:

[0190] The alkyl group usually has 1 or more carbon atoms, preferably 4 or more carbon atoms, and usually has 24 or more carbon atoms. linear, branched, or cyclic alkyl groups, preferably 12 or less; for example, Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, Dodecyl group, cyclohexyl group, etc. The alkenyl group usually has 2 or more carbon atoms and usually 24 or less carbon atoms, and preferably Alkenyl groups having 12 or less carbon atoms; for example, vinyl groups, etc. The alkynyl group usually has 2 or more carbon atoms and usually has 24 or less carbon atoms, and preferably Alkynyl groups having 12 or less carbon atoms; for example, ethynyl groups, etc. The alkoxy group usually has 1 or more carbon atoms and usually has 24 or less carbon atoms, and preferably Alkoxy groups having an alkyl group of 12 or less; for example, methoxy groups, ethoxy groups, etc. The (hetero)aryloxy group usually has 4 or more carbon atoms, preferably 5 or more carbon atoms. and the number of aryloxy groups or heteroaryl groups is usually 36 or less, preferably 24 or less. Aryloxy groups; for example, phenoxy groups, naphthoxy groups, pyridyloxy groups, etc. The alkoxycarbonyl group usually has 2 or more carbon atoms and usually has 24 or less carbon atoms. Alkoxycarbonyl groups, preferably 12 or less; for example, methoxycarbonyl groups, ethoxycarbonyl groups, hydroxycarbonyl group, etc. The dialkylamino group usually has 2 or more carbon atoms and usually has 24 or less carbon atoms, and is preferably or a dialkylamino group having 12 or less carbon atoms; for example, a dimethylamino group, a diethylamino group, Moto etc. The diarylamino group usually has 10 or more carbon atoms, preferably 12 or more carbon atoms. and usually not more than 36, preferably not more than 24 diarylamino groups; for example, diphenyl Amino group, ditolylamino group The arylalkylamino group usually has 7 or more carbon atoms and usually has 36 or less carbon atoms. , preferably 24 or less arylalkylamino groups; for example, phenylmethylamino Moto etc. The acyl group usually has 2 or more carbon atoms and usually has 24 or less carbon atoms, preferably 12 or less carbon atoms. Acyl groups such as acetyl, benzoyl, etc. Examples of halogen atoms include halogen atoms such as fluorine atoms and chlorine atoms. The haloalkyl group usually has 1 or more carbon atoms and usually has 12 or less carbon atoms, and preferably haloalkyl groups having 6 or less; for example, trifluoromethyl groups, etc. The alkylthio group usually has 1 or more carbon atoms and usually has 24 or less carbon atoms, and preferably is an alkylthio group having 12 or less; for example, a methylthio group, an ethylthio group, etc. The arylthio group usually has 4 or more carbon atoms, preferably 5 or more carbon atoms, and usually has 36 or more carbon atoms. an arylthio group having a ring structure of 24 or less, preferably 24 or less; for example, a phenylthio group, a naphthylthio group, thio group, pyridylthio group, etc. The silyl group usually has 2 or more carbon atoms, preferably 3 or more carbon atoms, and usually has 36 or less carbon atoms. silyl groups, preferably 24 or less; for example, trimethylsilyl groups, triphenylsilyl groups, Lyle group etc. The siloxy group usually has 2 or more carbon atoms, preferably 3 or more carbon atoms, and usually has 36 or more carbon atoms. siloxy groups having a carbon number of 24 or less, preferably 24 or less; for example, trimethylsiloxy groups, trimethylsiloxy groups, Triphenylsiloxy group, etc. Cyano group As an aromatic hydrocarbon group, the number of carbon atoms is usually 6 or more and usually 36 or less. aromatic hydrocarbon groups, preferably 24 or less; for example, phenyl groups, biphenyl groups, Phenyl group, terphenyl group, quaterphenyl group, naphthyl group, phenanthrenyl group, Triphenylene group, naphthylphenyl group, etc. The aromatic heterocyclic group usually has 3 or more carbon atoms, preferably 4 or more carbon atoms. Aromatic heterocyclic groups having a ring structure of 36 or less, preferably 24 or less; for example, thienyl groups, pyridyl groups, Dimethyl group, etc. The aralkyl group has 7 or more carbon atoms, preferably 8 or more carbon atoms, and 40 or less carbon atoms, preferably Aralkyl groups having 30 or less, more preferably 20 or less; for example, 1,1-dimethyl- 1-phenylmethyl group, 1,1-di(n-butyl)-1-phenylmethyl group, 1,1-di (n-hexyl)-1-phenylmethyl group, 1,1-di(n-octyl)-1-phenyl Methyl group, phenylmethyl group, phenylethyl group, 3-phenyl-1-propyl group, 4- Phenyl-1-n-butyl group, 1-methyl-1-phenylethyl group, 5-phenyl-1- n-Propyl group, 6-phenyl-1-n-hexyl group, 6-naphthyl-1-n-hexyl group group, 7-phenyl-1-n-heptyl group, 8-phenyl-1-n-octyl group, 4-phenyl cyclohexyl group, etc. The heteroaralkyl group has 2 or more, preferably 4 or more, and 40 or less carbon atoms. Heteroaralkyl groups, preferably 30 or less, more preferably 20 or less; 1,1-dimethyl 1,1-di(n-hexyl)-1-(2-pyridyl)methyl group, 1,1-di(n-hexyl)-1-(2-pyridyl)methyl group )methyl group, (2-pyridyl)methyl group, (2-pyridyl)ethyl group, 3-(2-pyridyl 4-(2-pyridyl)-1-n-butyl group, 1-methyl-1-( 2-pyridyl)ethyl group, 5-(2-pyridyl)-1-n-propyl group, 6-(2-pyridyl)- 6-(2-pyrimidyl)-1-n-hexyl group, 6-(2-pyrimidyl)-1-n-hexyl group, 6-(2 ,6-diphenyl-1,3,5-triazin-4-yl)-1-n-hexyl group, 7-( 2-pyridyl)-1-n-heptyl group, 8-(2-pyridyl)-1-n-octyl group, 4 -(2-pyridyl)cyclohexyl group, etc.

[0191] <Effects of the organic film-forming material of the present invention> The organic film forming material according to the embodiment of the present invention is suitably used as a material for forming a light emitting layer. The reason why this material is effective in organic electroluminescent devices using this material in the light-emitting layer is unclear. However, it is speculated as follows. When using a compound with a carbazole skeleton, the benzene ring contained in the skeleton is electron-dense. The reactivity of the 3rd and 6th positions is particularly high, and it is thought that they react easily with electron-donating compounds. Therefore, it is believed that the degradation of this compound causes a decrease in the operating life. In contrast, the compound represented by formula (2) has an indolocarbazole skeleton. It is believed that the deterioration of the compound due to the above mechanism can be suppressed. In addition, the compound represented by formula (71) has an empty p orbital on the boron atom, so various It tends to react with various reactive species and deteriorate easily. The degradation products produced by the reaction with electron-donating compounds at the ion-exchange position cause further degradation reactions, and the catalyst This is thought to cause a decrease in dynamic life. Since the compound represented by formula (2) has an indolocarbazole skeleton, No reaction occurs between the degradation products derived from the hydroxyl skeleton and the compound represented by formula (71). The organic film-forming material of the present invention contains a compound represented by formula (2) and a compound represented by formula (71). The organic electroluminescent device using the material in the light-emitting layer is resistant to deterioration of the compound that constitutes the device, and the driving It is believed that the dynamic life will be longer. The compound represented by formula (2) is a wide-gap material, and the compound represented by formula (71) It is thought that the excited state on the compound is difficult to quench. It is believed that the MO is deep and can transfer charge effectively to the compound represented by formula (71). Furthermore, both the compound represented by formula (2) and the compound represented by formula (71) are planar. By improving the molecular orientation within the film, charge and energy transfer between molecules can be improved. As a result, an organic electroluminescent device using the organic film-forming material of the present invention in the light-emitting layer can be is considered to show high efficiency.

[0192] <Phosphorescent compounds> The organic film-forming material of the present invention preferably contains a phosphorescent compound. When the material for use contains a phosphorescent compound, the phosphorescent compound can be emitted by using the material for the light-emitting layer. The excitons generated on the luminescent compound are effectively transferred to the compound represented by formula (71) to emit light. This allows direct bonding of the compound represented by formula (71) The suppression of exciton generation of the compound suppresses deterioration of the compound, and the compound contained in the light-emitting layer In particular, the phosphorescent compound is In the case of a compound represented by formula (7), hole trapping by a compound represented by formula (71) The compound represented by formula (7) has high luminous efficiency and is therefore preferably Therefore, the material is suitable for energy transfer to the compound represented by formula (71). Organic electroluminescent devices containing it in the light-emitting layer are believed to be highly efficient.

[0193] A phosphorescent compound is a compound that emits light from an excited triplet state. For example, Ir Typical examples are metal complex compounds containing Pt, Eu, etc. Those containing complexes are preferred. Among metal complexes, phosphorescent organometallic complexes that emit light via triplet states have been popular for a long time. Periodic Table (Hereinafter, unless otherwise specified, when we say "periodic table", we mean the long-period periodic table) (This refers to the table below.) Werner compounds containing a metal selected from Groups 7 to 11 as the central metal As such phosphorescent compounds, there may be mentioned: For example, International Publication No. 2014 / 024889, International Publication No. 2015 / 087961, Described in International Publication No. 2016 / 194784 and Japanese Patent Application Laid-Open No. 2014-074000 Examples of phosphorescent compounds include: The phosphorescent compound is preferably a compound represented by the following formula (7).

[0194] [ka]

[0195] In formula (7), ring A701 is an aromatic hydrocarbon ring structure which may have a substituent or a substituent represents an aromatic heterocyclic structure which may have the following structure: Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When there are multiple rings A701 and multiple rings A702, they may be the same or different. That's fine.

[0196] R 701 , R 702 are each independently a structure represented by formula (b), and "*" indicates ring A701 or represents the bonding position with ring A702. 701 , R 702 are the same but different Also, R 701 , R 702 If there are multiple of each, they may be the same but different. It may be possible. Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent. Ar 702 is an aromatic hydrocarbon ring structure which may have a substituent, It represents an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. Ar 701 , Ar 702 , and Ar 703 If there are multiple of each, they are the same But it may be different.

[0197] The substituents bonded to ring A701, the substituents bonded to ring A702, or the substituents bonded to ring A701 The substituents bonded to ring A702 may be bonded to each other to form a ring. good.

[0198] B 701 -L 700 -B 702 represents an anionic bidentate ligand. 701 and B 7 02 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms form a ring. It may be an atom that constitutes L 700 is a single bond or B 701 and B 702 Together represents the atomic group that constitutes the bidentate ligand. 701 -L 700 -B 702 If there are multiple If so, they may be the same or different.

[0199] In addition, in equations (7) and (b), i1 and i2 each independently represent an integer of 0 to 12, i3 is Ar 702 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by i4 is Ar 701 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by k1 and k2 each independently represent the upper limit of the number of substitutions that can be made on ring A701 and ring A702. represents an integer greater than or equal to 0, m represents an integer of 1 to 3.

[0200] In formula (7) and (b), unless otherwise specified, examples of the substituents that may be present include: A group selected from the following substituent group S is preferred.

[0201] <Substituent group S> An alkyl group, preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms. alkyl groups having 1 to 8 carbon atoms, more preferably alkyl groups having 1 to 8 carbon atoms, and particularly preferably alkyl groups having 1 to 8 carbon atoms. 6 alkyl groups. An alkoxy group, preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 20 carbon atoms 12 alkoxy groups, more preferably alkoxy groups having 1 to 6 carbon atoms. An aryloxy group, preferably an aryloxy group having 6 to 20 carbon atoms, more preferably an aryloxy group having 6 to 20 carbon atoms An aryloxy group having 6 to 14 carbon atoms, more preferably an aryloxy group having 6 to 12 carbon atoms. An aryloxy group having 6 carbon atoms is particularly preferred. Heteroaryloxy groups, preferably heteroaryloxy groups having 3 to 20 carbon atoms, more preferably Preferably, it is a heteroaryloxy group having 3 to 12 carbon atoms. An alkylamino group, preferably an alkylamino group having 1 to 20 carbon atoms, more preferably an alkylamino group having 1 to 20 carbon atoms Alkylamino groups with prime numbers 1 to 12.

[0202] An arylamino group, preferably an arylamino group having 6 to 36 carbon atoms, more preferably an arylamino group having 6 to 36 carbon atoms Arylamino groups with prime numbers 6 to 24. An aralkyl group, preferably an aralkyl group having 7 to 40 carbon atoms, more preferably an aralkyl group having 7 to 40 carbon atoms 18 aralkyl groups, more preferably aralkyl groups having 7 to 12 carbon atoms. Heteroaralkyl groups, preferably heteroaralkyl groups having 7 to 40 carbon atoms, more preferably is a heteroaralkyl group having 7 to 18 carbon atoms. An alkenyl group, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 20 carbon atoms Alkenyl groups having 12 carbon atoms, more preferably alkenyl groups having 2 to 8 carbon atoms, particularly preferably alkenyl groups having 1 to 8 carbon atoms. Alkenyl groups with prime numbers 2 to 6. An alkynyl group, preferably an alkynyl group having 2 to 20 carbon atoms, more preferably an alkynyl group having 2 to 20 carbon atoms 12 alkynyl groups.

[0203] An aryl group, preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, and particularly preferably an aryl group having 6 ~14 aryl groups. Heteroaryl groups, preferably heteroaryl groups having 3 to 30 carbon atoms, more preferably Heteroaryl groups having 3 to 24 carbon atoms, more preferably heteroaryl groups having 3 to 18 carbon atoms Particularly preferred is a heteroaryl group having 3 to 14 carbon atoms. Alkylsilyl groups, preferably alkylsilyl groups in which the alkyl group has 1 to 20 carbon atoms More preferably, it is an alkylsilyl group in which the alkyl group has 1 to 12 carbon atoms. Arylsilyl groups, preferably arylsilyl groups having 6 to 20 carbon atoms in the aryl group More preferably, it is an arylsilyl group having 6 to 14 carbon atoms in the aryl group. An alkylcarbonyl group, preferably an alkylcarbonyl group having 2 to 20 carbon atoms. An arylcarbonyl group, preferably an arylcarbonyl group having 7 to 20 carbon atoms. The above groups have one or more hydrogen atoms replaced by fluorine atoms or one or more The hydrogen atoms above may be replaced with deuterium atoms. Unless otherwise specified, aryl is an aromatic hydrocarbon ring and heteroaryl is an aromatic heterocyclic ring. It is an elementary ring.

[0204] Hydrogen atom, deuterium atom, fluorine atom, cyano group, or -SF 5。

[0205] Among the above-mentioned substituent group S, alkyl groups, alkoxy groups, aryloxy groups, Arylamino group, aralkyl group, alkenyl group, aryl group, heteroaryl group, alkoxy group, alkylsilyl groups, arylsilyl groups, and groups in which one or more hydrogen atoms are replaced by fluorine atoms. a substituted group, a fluorine atom, a cyano group, or -SF5; More preferably, it is an alkyl group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, or an arylamino group. and heteroaryl groups, and one or more hydrogen atoms of these groups are replaced with fluorine atoms. a substituted group, a fluorine atom, a cyano group, or -SF5; More preferably, an alkyl group, an alkoxy group, an aryloxy group, or an arylamino group. , aralkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, is a arylsilyl group, Particularly preferred are alkyl groups, arylamino groups, aralkyl groups, alkenyl groups, and aryl groups. a aryl group, a heteroaryl group, Most preferably, it is an alkyl group, an arylamino group, an aralkyl group, an aryl group, a heteroaromatic group, or a It is a aryl group.

[0206] These substituent groups S further have a substituent selected from the substituent group S as a substituent. The preferred groups, more preferred groups, further more preferred groups, and particularly preferred groups of the substituents that may be present are The preferred groups and most preferred groups for the substituent group S are the same as the preferred groups for the substituent group S.

[0207] Ring A701 has an aromatic hydrocarbon ring structure or a substituent which may be substituted. It also represents an aromatic heterocyclic structure. The aromatic hydrocarbon ring is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms. Specifically, benzene ring, naphthalene ring, anthracene ring, triphenylyl ring, acenaphthene ring, A fluoranthene ring, a fluorenone ring, and a fluorene ring are preferred. The aromatic heterocycle may contain any one of a nitrogen atom, an oxygen atom, and a sulfur atom as a heteroatom. Aromatic heterocycles having 3 to 30 carbon atoms, including benzophenone, ... These are benzofuran ring, thiophene ring, and benzothiophene ring.

[0208] Ring A701 is more preferably a benzene ring, a naphthalene ring, or a fluorene ring. Particularly preferred is a benzene ring or a fluorene ring, and most preferred is a benzene ring.

[0209] Ring A702 represents an aromatic heterocyclic structure which may have a substituent. The aromatic heterocycle preferably contains a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom. Specifically, it is an aromatic heterocycle having 3 to 30 carbon atoms, which contains one of the following rings: a pyridine ring, Pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, oxazole ring, thiazo ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring , isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridine ring, phenanthridine rings, preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, an imidazole ring, Benzothiazole ring, benzoxazole ring, quinoline ring, isoquinoline ring, quinoxazole ring A pyridine ring, an imidazole ring, a benzothiazoline ring, and the like are more preferred. The most preferred rings are azole ring, quinoline ring, isoquinoline ring, quinoxaline ring and quinazoline ring. Preferably, the ring is a pyridine ring, an imidazole ring, a benzothiazole ring, a quinoline ring, or a quinoxalyl ring. The rings are quinazoline and quinazoline rings.

[0210] Preferred combinations of ring A701 and ring A702 include (ring A701-ring A702) and The notation is (benzene ring-pyridine ring), (benzene ring-quinoline ring), (benzene ring -quinoxaline ring), (benzene ring-quinazoline ring), (benzene ring-benzothiazole ring), (benzene ring-imidazole ring), (benzene ring-pyrrole ring), (benzene ring- diazole ring), and (benzene ring-thiophene ring). The substituents that the ring A701 and the ring A702 may have can be selected arbitrarily, but are preferably The substituent is one or more kinds of substituents selected from the above-mentioned group S of substituents.

[0211] Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent. Ar 702 is an aromatic hydrocarbon ring structure which may have a substituent, It represents an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent.

[0212] Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent In the case of an aromatic hydrocarbon ring structure, the aromatic hydrocarbon ring structure preferably has 6 to 30 carbon atoms. Specifically, the aromatic hydrocarbon ring is a benzene ring, a naphthalene ring, an anthracene ring, A triphenylyl ring, an acenaphthene ring, a fluoranthene ring, or a fluorene ring is preferred, and more preferred is a A benzene ring, a naphthalene ring, or a fluorene ring is preferred, and a benzene ring is most preferred. It is a ring.

[0213] Ar 701 , Ar 702 When either of the following is an optionally substituted benzene ring: At least one benzene ring is bonded to an adjacent structure at the ortho or meta position. Preferably, at least one benzene ring is bonded to an adjacent structure at a meta position. More preferable.

[0214] Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent When the fluorene ring is a fluorene ring, the 9- and 9'-positions of the fluorene ring may have a substituent or an adjacent structure. It is preferred that the compound is bonded to

[0215] Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent In the case of an aromatic heterocyclic structure, the heteroatom is preferably a nitrogen atom. an aromatic heterocycle having 3 to 30 carbon atoms containing either an oxygen atom or a sulfur atom, Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, o-ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring dazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridin phenanthridine ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring and preferably a pyridine ring, a pyrimidine ring, a triazine ring, a carbazole ring, Dibenzofuran ring and dibenzothiophene ring. Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent When the carbazole ring is a carbazole ring, the N-position of the carbazole ring has a substituent or is bonded to an adjacent structure. It is preferable that

[0216] Ar 702 When the aliphatic hydrocarbon structure may have a substituent, or an aliphatic hydrocarbon structure having a cyclic structure, preferably having 1 to 24 carbon atoms. and more preferably, the number of carbon atoms is 1 or more and 12 or less, and still more preferably, the number of carbon atoms is 1 or more. Top 8 or below.

[0217] i1 and i2 each independently represent an integer of 0 to 12, preferably 1 to 12, more preferably The number is preferably 1 to 8, and more preferably 1 to 6. By keeping the number in this range, the solubility is improved. and improved charge transport properties are expected. i3 preferably represents an integer of 0 to 5, more preferably 0 to 2, and even more preferably 0 or is 1. i4 preferably represents an integer of 0 to 2, and more preferably 0 or 1. k1 and k2 each independently represent an integer of preferably 0 to 3, more preferably 1 to 3. It is 3, more preferably 1 or 2, and particularly preferably 1.

[0218] Ar 701 , Ar 702 , Ar 703 The substituents that may be possessed by may be selected arbitrarily. Preferably, it is one or more substituents selected from the above-mentioned substituent group S. Preferred groups are also As in the above-mentioned substituent group S, more preferably, it is unsubstituted (hydrogen atom), alkyl group, aryl group, or the like. A alkyl group is particularly preferred, and an unsubstituted (hydrogen atom) alkyl group is particularly preferred, and the most preferred Unsubstituted (hydrogen atom) or tertiary butyl group, and the tertiary butyl group is Ar 7 03 If Ar exists, 703 To, Ar 703 If Ar does not exist, 702 To, Ar 702 and Ar 703 If Ar does not exist, 701 It is preferred that the substituent is

[0219] The compound represented by the formula (7) satisfies any one or more of the following (I) to (IV): It is preferable that the compound is a compound having the above structure.

[0220] (I) Phenylene-linked The structure represented by formula (b) is a structure having a group connected to a benzene ring, i.e., a benzene ring structure, i1 is 1 to 6, and at least one of the benzene rings is adjacent at the ortho or meta position It is preferred that the hydroxyl group is bonded to a structure that binds the hydroxyl group. Such a structure improves solubility and charge transport properties. is expected.

[0221] (II) (phenylene)-aralkyl(alkyl) Aromatic carbon atoms having an alkyl or aralkyl group bonded to ring A701 or ring A702 A structure having a hydrogen group or an aromatic heterocyclic group, i.e., Ar 701 is an aromatic hydrocarbon structure or aromatic heterocyclic structure, i1 is 1 to 6, Ar 702 is an aliphatic hydrocarbon structure, and i2 is 1 to 12, preferably 3 to 8, Ar 703 is a benzene ring structure, i3 is 0 or 1, Preferably, Ar 701is the aromatic hydrocarbon structure, and more preferably, a benzene ring is It is a structure in which 1 to 5 rings are linked together, and more preferably one benzene ring. Such a structure improves solubility and charge transport properties. is expected.

[0222] (III) Dendron A structure in which a dendron is bonded to the ring A701 or the ring A702, for example, Ar 701 , Ar 702 is a benzene ring structure, Ar 703 is a biphenyl or terphenyl structure, i1 and i2 are 1~6, i3 is 2, j is 2. Such a structure improves solubility and charge transport properties. is expected.

[0223] (IV)B 701 -L 700 -B 702 B 701 -L 700 -B 702 The structure represented by the following formula (203) or the following formula (204) ) is preferable.

[0224] [ka]

[0225] In formula (203), R 211 , R 212 , R 213 each independently represents a substituent. In formula (204), ring B3 is an aromatic heterocycle containing a nitrogen atom which may have a substituent. The ring B3 is preferably a pyridine ring.

[0226] The compound represented by the formula (7) is not particularly limited, but the following are preferred: The following are some examples:

[0227] [ka]

[0228] [ka]

[0229] [ka]

[0230] The molecular weight of the phosphorescent compound is preferably 5,000 or less, more preferably 4,000 or less. 0 or less, particularly preferably 3,000 or less. Preferably 1,200 or more, more preferably 1,400 or more, and even more preferably 1,600 That's all. By keeping the molecular weight within this range, the phosphorescent compounds do not aggregate together, and the charge transport material It is believed that this allows the compound to be uniformly mixed with the compound to obtain a light-emitting layer with high light-emitting efficiency.

[0231] The molecular weight of phosphorescent compounds is high, and the Tg, melting point, decomposition temperature, etc. and the light-emitting layer formed has excellent heat resistance, and gas generation, recrystallization, and molecular migration are prevented. The film quality is less likely to deteriorate due to oxidation, and the impurity concentration is less likely to increase due to thermal decomposition of the material. On the other hand, the molecular weight of the phosphorescent compound is determined by the purity of the organic compound. A small size is preferable in terms of ease of manufacturing.

[0232] [Other charge transport materials] The organic film-forming material of the present invention further contains a compound represented by the following formula (1) and a compound represented by the following formula ( 260), and at least one compound selected from the group consisting of It is more preferable that both of them contain a compound represented by the following formula (1):

[0233] A compound having a structure in which a nitrogen-containing six-membered heteroaromatic ring and a benzene ring are linked, represented by the following formula: When the compound represented by (1) is contained as a host material, the organic film-forming material of the present invention is used. The charge transport properties in the light-emitting layer formed by this process are appropriately adjusted, reducing the voltage required and improving the light-emitting efficiency. The compound represented by the formula (71) and the compound represented by the formula (7) are light-emitting materials. It is believed that this will suppress deterioration and extend the driving life. When the compound has a triazine structure in which all atoms are nitrogen atoms, the LUMO is relatively deep and electron transport properties are good. In addition, the compound represented by the formula (71) and the compound represented by the formula (7 By not supplying excess electrons to the compound represented by the formula (71), which is a light-emitting material, The durability of the compound represented by formula (7) is improved, and as a result, the organic electrochemical It is believed that the operating life of the light-emitting device will be longer. An electron enters the empty p orbital of the boron atom of the compound represented by the formula It is believed that this may have the potential to inhibit the deterioration of the compound represented by (71).

[0234] The compound represented by the formula (2) is a wide-gap material, and the compound contained in the material The compound represented by the formula (2) and the compound represented by the formula (1) below are in the category of compounds with shallow LUMO levels. When the compound represented by formula (2) contains both a compound represented by formula (1) This inhibits electron transport in the compound and adjusts the carrier balance. It is believed that an organic electroluminescent device having an organic layer will have a longer operating life. A compound represented by the following formula (260), which is a compound having a structure in which many benzene rings are linked together. When the material is contained as a host material, the light-emitting layer formed using the organic thin film-forming material of the present invention The charge transport property of the compound represented by the formula (71) is appropriately adjusted, and the compound is a light-emitting material. It is believed that this can suppress the deterioration of the compound represented by the formula (7), thereby extending the operating life. In particular, the compound represented by the following formula (260) has the effect of suppressing the charge transport property. In particular, when a compound represented by the following formula (1) having excellent electron transport properties is used as a host, By further adding the compound represented by the formula (260) as a host material, a light-emitting material The compound represented by the formula (71) or the compound represented by the formula (7) is excessively reduced. This is thought to suppress the electron transport in the light-emitting layer so that the device does not deteriorate due to the electron transport, thereby extending the device's operating life. In addition, in a light-emitting device in which electron injection is dominant, a compound represented by the following formula (260) is used. By suppressing electron transport with a material, the charge transport property in the light-emitting layer is appropriately adjusted, and light is emitted. It is believed that efficiency will improve.

[0235] <Substituent group Z2> In the following formula (1), the substituent that may be possessed is selected from the substituent group Z2.

[0236] The substituent group Z2 is an alkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an alkoxycarbonyl group, a dialkylamino group, a diarylamino group, an arylamino group, alkylamino group, acyl group, halogen atom, haloalkyl group, alkylthio group, aryl Thio group, silyl group, siloxy group, cyano group, aromatic hydrocarbon group, and aromatic heterocyclic group These substituents may include any of straight-chain, branched, and cyclic structures. .

[0237] More specifically, the substituent group Z2 includes the following structures. For example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group The carbon number of the hydroxyl group, dodecyl group, etc. is usually 1 or more, preferably 4 or more, and usually 24 or less, preferably 12 or less, more preferably 8 or less, and even more preferably or a linear, branched, or cyclic alkyl group having 6 or less carbon atoms; For example, the number of carbon atoms of a methoxy group, an ethoxy group, etc. is usually 1 or more and usually 24 or less. alkoxy groups, preferably 12 or less; For example, phenoxy group, naphthoxy group, pyridyloxy group, etc., which usually have 4 or more carbon atoms, Preferably, the number is 5 or more, usually 36 or less, preferably 24 or less. an aryloxy group or a heteroaryloxy group; For example, a methoxycarbonyl group, an ethoxycarbonyl group, or the like, usually has two or more carbon atoms. alkoxycarbonyl groups, typically 24 or less, preferably 12 or less; For example, a dimethylamino group, a diethylamino group, etc., usually has two or more carbon atoms, dialkylamino groups having 24 or less, preferably 12 or less; For example, the number of carbon atoms is usually 10 or more, such as a diphenylamino group or a ditolylamino group, Preferably, it is 12 or more, usually 36 or less, preferably 24 or less diaryl amines. Noki; For example, the number of carbon atoms is usually 7 or more and usually 36 or less, such as a phenylmethylamino group. an arylalkylamino group, preferably having a molecular weight of 24 or less; For example, acetyl groups, benzoyl groups, etc., usually have 2 or more carbon atoms and usually have 24 or less carbon atoms. acyl groups, preferably 12 or less; For example, halogen atoms such as fluorine atoms and chlorine atoms; For example, the number of carbon atoms is usually 1 or more and usually 12 or less, such as a trifluoromethyl group. haloalkyl groups, preferably 6 or less; For example, a methylthio group, an ethylthio group, etc., usually has 1 or more carbon atoms and usually has 24 or less carbon atoms. an alkylthio group, preferably having 12 or less carbon atoms; For example, a phenylthio group, a naphthylthio group, a pyridylthio group, etc., which usually have 4 or more carbon atoms and preferably 5 or more, usually 36 or less, preferably 24 or less. thio group; For example, a trimethylsilyl group, a triphenylsilyl group, etc., which usually have two or more carbon atoms silyl groups, preferably 3 or more and usually 36 or less, preferably 24 or less; For example, trimethylsiloxy groups, triphenylsiloxy groups, and other groups with carbon atoms of usually 2 or more Preferably, the number of silyl groups is 3 or more, and usually 36 or less, preferably 24 or less. Si group; cyano group; For example, the number of carbon atoms is usually 6 or more and usually 36 or less, such as a phenyl group and a naphthyl group. an aromatic hydrocarbon group, preferably having 24 or less aromatic hydrocarbon groups; For example, a thienyl group, a pyridyl group, etc., usually have 3 or more carbon atoms, preferably 4 or more carbon atoms. and the aromatic heterocyclic group has a ring structure of usually 36 or less, preferably 24 or less.

[0238] Among the above-mentioned substituent group Z2, alkyl groups, alkoxy groups, diaryla groups, From the viewpoint of charge transport properties, the substituted group is an amino group, an aromatic hydrocarbon group, or an aromatic heterocyclic group. The group is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, more preferably an aromatic hydrocarbon group. It is more preferable that the group is a hydrogen group and has no substituents. The group is preferably an alkyl group or an alkoxy group.

[0239] Each of the substituents in the above-mentioned substituent group Z2 may further have a substituent. Examples of the substituents include the same as those in the above-mentioned substituent group Z2. Each of the optional substituents is preferably an alkyl group having 8 or less carbon atoms, an alkoxy group having 8 or less carbon atoms, or an oxy group or a phenyl group, more preferably an alkyl group having 6 or less carbon atoms, an alkyl group having 6 or less carbon atoms, Each of the substituents in the above-mentioned substituent group Z2 is an alkoxy group or a phenyl group, and each of the substituents in the above-mentioned substituent group Z2 is It is more preferred that the group has no further substituents.

[0240] <Compound represented by formula (1)> When the organic film-forming material of the present invention contains a compound represented by the following formula (1), The compound represented by 1) may be contained in one kind or in two or more kinds. .

[0241] [ka]

[0242] [In formula (1), each W independently represents CH or N, and at least one W is N; Xa 1 , Ya 1 , and Za 1 each independently represents a group having 6 to 3 carbon atoms which may have a substituent a divalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents an aromatic heterocyclic group, Xa 2 , Ya 2 and Za 2 each independently represents a hydrogen atom, a carbon atom which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monovalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents a monovalent aromatic heterocyclic group, g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11, h11, and j11 is an integer of 1 or greater, If g11 is 2 or more, multiple Xa 1 may be the same or different, If h11 is 2 or more, multiple Ya 1 may be the same or different, If j11 is 2 or more, multiple Za 1 may be the same or different, R 31 represents a hydrogen atom or a substituent, and 12 R 31 Whether they are the same or different often, However, if g11, h11, or j11 is 0, the corresponding Xa 2 , Ya 2 , Z a 2 is not a hydrogen atom.]

[0243] The compound represented by the above formula (1) is a charge transport compound, i.e., a charge transport host material. It is preferable.

[0244] In the formula (1), W represents CH or N, and at least one of them is N. However, from the viewpoint of electron transport property and electron durability, it is preferable that at least two of them are N, It is more preferable that they are all N.

[0245] In the formula (1), Xa 1 , Ya 1 , Za 1 may have a substituent and have 6 carbon atoms and Xa is a divalent aromatic hydrocarbon group having a molecular weight of 1 to 30; 2 , Ya 2 , Za 2 is a substituent In the case of an aromatic hydrocarbon group having 6 to 30 carbon atoms which may be present, The aromatic hydrocarbon ring of the aromatic hydrocarbon group is preferably a 6-membered monocyclic ring or 2 to 5 condensed rings. Specifically, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluoro ring, Olene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triflate ring phenylene ring, fluoranthene ring, indenofluorene ring, etc. is a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a fluorene ring and more preferably a benzene ring, a naphthalene ring, a phenanthrene ring or a fluorene ring. g1 is preferably a benzene ring, a naphthalene ring, or a fluorene ring, and more preferably a benzene ring, a naphthalene ring, or a fluorene ring. -Xa, which is a terminal partial structure when 1 is 2 or more 1 -Xa 2 , h11 is 2 or more The terminal partial structure, -Ya 1 -Ya 2 , and the end when j11 is 2 or more The edge substructure, -Za 1 -Za 2 may be a spirofluorene structure.

[0246] The compound represented by formula (1) is a terminal partial structure when g11 is 2 or more, - Xa 1 -Xa 2 , -Ya is a terminal partial structure when h11 is 2 or more. 1 -Ya2 and a terminal partial structure when j11 is 2 or more, -Za 1 -Za 2 At least The other one is preferably a spirofluorene structure.

[0247] In the formula (1), Xa 1 , Ya 1 , Za 1 may have a substituent and have 3 carbon atoms and Xa is a divalent aromatic heterocyclic group having a ring structure of 1 to 30; 2 , Ya 2 , Za 2 has a substituent In the case where the aromatic heterocyclic group has 3 to 30 carbon atoms, the aromatic heterocyclic group having 3 to 30 carbon atoms may be The aromatic heterocyclic ring of the heterocyclic group is preferably a 5- or 6-membered monocyclic ring or 2 to 5 condensed rings. Specifically, furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiazol-1-yl ring, thiophene ring, dibenzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxazole ring Sadiazole ring, indole ring, carbazole ring, indolocarbazole ring, indenocarbazole ring, Rubazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thieno Pyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzyl Benzoisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring , pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, perimidine ring, quinazoline ring, quinazolinone ring, etc. Among these, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, Pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzofuran oran ring, dibenzothiophene ring, indolocarbazole ring, phenanthroline ring, or iridium ring a pyridine ring, a pyrimidine ring, or a triazine ring. , quinoline ring, quinazoline ring, carbazole ring, indolocarbazole ring, indenocarbazole ring a dibenzofuran ring, a dibenzothiophene ring, or a benzobenzol ring, and more preferably a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring. a dibenzothiophene ring, an indolocarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring. do. Xa in the formula (1) 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , and Za 2 In Particularly preferred aromatic hydrocarbon rings are benzene ring, naphthalene ring and phenanthrene ring. Particularly preferred aromatic heterocycles are carbazole ring, indolocarbazole ring, dibenzoyl It is a zofran ring or a dibenzothiophene ring.

[0248] g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11 is an integer of 1 or more. From the viewpoint of charge transport property and durability, It is preferable that at least one of h11 and j11 is 2 or greater, or that at least one of h11 and j11 is 3 or greater. In addition, the compound represented by the formula (1) includes a ring having three central Ws. The presence of a total of 8 to 18 rings is advantageous in terms of charge transport properties, durability, and solubility in organic solvents. Therefore, it is preferable.

[0249] (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11 At least one selected from From the viewpoint of the solubility and durability of the compound, the other group is independently represented by the following formula (11): a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13): It is preferable that the partial structure is selected from the following structures: a 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11、 and j11 is 1 or more In this case (Za 1 ) j11 each independently represents a partial structure represented by the following formula (11), 12) and a portion selected from the partial structure represented by the following formula (13): It is more preferable that the structure is:

[0250] [ka]

[0251] In each of the above formulas (11) to (13), * represents a bond to an adjacent structure, or X a 2 , Ya 2 , or Za 2 represents the hydrogen atom when there are two At least one of the * marks represents the bonding position with the adjacent structure. Unless otherwise stated, * is defined similarly.

[0252] More preferably, when g11 is 1 or more, (Xa 1 ) g11 , h11 is 1 or more In this case (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 Each is unique Specifically, it has a partial structure represented by formula (11) or a partial structure represented by formula (12). More preferably, when g11 is 1 or more, (Xa 1 ) g11 , h11 is 1 or more In some cases (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 are each It independently has a partial structure represented by formula (11) and a partial structure represented by formula (12).

[0253] The partial structure represented by formula (12) is preferably a portion represented by the following formula (12-2): It is a structure.

[0254] [ka]

[0255] The partial structure represented by formula (12) is more preferably a partial structure represented by the following formula (12-3): It is a partial structure that is

[0256] [ka]

[0257] A partial structure having a partial structure represented by formula (11) and a partial structure represented by formula (12) The partial structure is selected from the partial structure represented by formula (11) and the partial structure represented by formula (12). a partial structure selected from the following formulas (14) to (17), which is a structure including a plurality of structures represented by the formulas (14) to (17): That is, when g11 is 1 or more, (Xa 1 ) g11 , h11 is 1 or more When (Ya 1 ) h11、 and j11 is 1 or more (Za 1 ) j11 Each are independently selected from the formulas (11) to (13) and the following formulas (14) to (17): It is preferable that the compound has a partial structure selected from the group consisting of methyl, ...

[0258] [ka]

[0259] A structure selected from the partial structure represented by formula (11) and the partial structure represented by formula (12) The structure containing a plurality of the following is, for example, a partial structure represented by formula (14) as shown in the following formula (14a): , having one partial structure represented by formula (11) and two partial structures represented by formula (12) It is a partial structure that can be considered as follows.

[0260] [ka]

[0261] More preferably, (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11 few At least one of the partial structures is represented by formula (14) or formula (15). More preferably, when g11 is 1 or more, (Xa 1 ) g11 , h1 (Ya when 1 is 1 or more 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 has a partial structure represented by formula (14) or a partial structure represented by formula (15) .

[0262] The partial structure represented by formula (14) is preferably a part represented by the following formula (14-2): It is a structure.

[0263] [ka]

[0264] The partial structure represented by formula (14) is more preferably represented by the following formula (14-3): It is a partial structure.

[0265] [ka]

[0266] The partial structure represented by formula (15) is preferably a portion represented by the following formula (15-2): It is a structure.

[0267] [ka]

[0268] The partial structure represented by formula (15) is more preferably represented by the following formula (15-3): It is a partial structure.

[0269] [ka]

[0270] The partial structure represented by formula (17) is preferably a part represented by the following formula (17-2): It is a structure.

[0271] [ka]

[0272] (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11At least one of the formula As a partial structure containing the partial structure represented by formula (13), a partial structure represented by the following formula (19) Alternatively, it is more preferable that the compound has a partial structure represented by the following formula (20):

[0273] [ka]

[0274] In each of the above formulas (14) to (20), * represents a bond to an adjacent structure, or X a 2 , Ya 2 , or Za 2 represents the hydrogen atom when there are two At least one of the * marks represents the bonding position to the adjacent structure.

[0275] Among the partial structures represented by formulas (14) to (20), the partial structure represented by formula (14-3) The partial structure represented by formula (15-3) is preferred, and formula (14-3) is more preferred. .

[0276] -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) each independently represent a partial structure represented by formula (11), a partial structure represented by formula (12-3) a partial structure represented by formula (14-3) or a partial structure represented by formula (15-3) It is preferable that the compound has a partial structure.

[0277] Also, -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya2 ), and -( Za 1 ) j11 -(Za 2 ) is at least one of the following formula (250-1) to the following formula (25 0-10) or a terminal structure.

[0278] [ka]

[0279] [In the above structure, * indicates the bonding position. 250 represents an aromatic hydrocarbon group having 6 to 20 carbon atoms. Represents. R 32 represents a substituent. These structures may further have a substituent.]

[0280] The substituents that these structures may have are R 32 is the same as:

[0281] Ar 250 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably Preferably, the alkyl group is a phenyl group or a biphenyl group, and more preferably a phenyl group.

[0282] R 32 In a structure having two R 32 may be the same or different. It's okay to have it. R 32 is preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylsilyl group, an arylsilyl group having 6 to 20 carbon atoms, or an alkyl group having 1 to 8 carbon atoms; substituted with an optionally substituted aryl group having 6 to 30 carbon atoms or an alkyl group having 1 to 8 carbon atoms; and more preferably, a heteroaryl group having 1 to 30 carbon atoms. an alkyl group having 7 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, It may be substituted with an aryloxy group having 6 to 20 carbon atoms or an alkyl group having 1 to 8 carbon atoms. An aryl group having 6 to 30 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms is more preferable. Aralkyl groups with 7 to 20 prime numbers, alkoxy groups with 1 to 8 carbon atoms, aryl groups with 6 to 14 carbon atoms Aryl having 6 to 14 carbon atoms which may be substituted with an oxy group or an alkyl group having 1 to 8 carbon atoms It is the base.

[0283] R when it is a substituent 31 is preferably a group having 6 to 10 carbon atoms which may have a substituent. an aromatic hydrocarbon group having 3 to 30 carbon atoms or an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent; From the viewpoint of improving durability and charge transportability, an aromatic carbon which may have a substituent is preferred. It is more preferably a hydrogen group. 31 If there are multiple They may be different.

[0284] The substituents which the aromatic hydrocarbon group having 6 to 30 carbon atoms may have are The substituents that the aromatic heterocyclic group of R 31 may have The substituent can be selected from the above-mentioned substituent group Z2.

[0285] The molecular weight of the compound represented by formula (1) is usually 5,000 or less, preferably 3,000 or less. Preferably, it is 2,500 or less, more preferably 2,000 or less, The most preferred molecular weight is 1,800 or less. The lower limit of the molecular weight is usually 350 or more. , more preferably 400 or more, and particularly preferably 500 or more.

[0286] The compound represented by formula (1) is not particularly limited, but examples thereof include the following compounds: can be.

[0287] [ka]

[0288] [ka]

[0289] [ka]

[0290] [ka]

[0291] [ka]

[0292] The compound represented by formula (1) is a compound represented by the following formula (1-1) or (1-2): Preferably, it is a material.

[0293] <Compound represented by formula (1-1)>

[0294] [ka]

[0295] [In formula (1-1), W1, W2 and W3 each independently represent -CH or a nitrogen atom; at least one of which is a nitrogen atom, Xa1 , Ya 1 , and Za 1 each independently represents an optionally substituted 1,3-phenylene represents an phenylene group or an optionally substituted 1,4-phenylene group, Za 1 at least one of is a 1,3-phenylene group, Xa 2 and Ya 2 each independently represents an optionally substituted phenyl group, Za 2 represents an N-carbazolyl group which may have a substituent, f11 is 1 or 2, g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer between 1 and 6, f11+g11+h11+j11 is greater than or equal to 5, R 11 each independently represents a hydrogen atom or a substituent.

[0296] In formula (1-1), a 1,3-phenylene group, a 1,4-phenylene group, a phenyl group, The substituent that the N-carbazolyl group may have is selected from the aforementioned substituent group Z2.

[0297] R in formula (1-1) 11 each independently represents a hydrogen atom or a substituent. R is a substituent other than a hydrogen atom 11 Examples of the substituent Z include groups selected from the above-mentioned substituent group Z2. Among the substituent group Z2, preferred are those having 6 to 30 carbon atoms which may have a substituent. or an aromatic hydrocarbon group or an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent. do. From the viewpoint of improving durability and charge transportability, an aromatic hydrocarbon group which may have a substituent It is more preferable that R in the case of being a substituent in formula (1-1) is 11There are multiple If multiple R 11 may be the same or different from each other. The substituents which the aromatic hydrocarbon group having 6 to 30 carbon atoms may have are The substituents that the aromatic heterocyclic group of R 11 may have The substituent can be selected from the above-mentioned substituent group Z2.

[0298] In formula (1-1), W1, W2, and W3 each independently represent -CH or a nitrogen atom. At least one of W1, W2 and W3 is a nitrogen atom. From the viewpoint of durability, it is preferable that at least W1 is a nitrogen atom, and at least W1 and W2 is preferably a nitrogen atom, and W1, W2 and W3 are all preferably nitrogen atoms. is more preferable. That is, from the viewpoint of improving the electron transport property, the group bonded to the para position is preferably one having two or more benzene rings. Three of the atoms are linked at the para position to extend the conjugation. W1 is preferably a nitrogen atom. A pyrimidine structure in which one of W2 and W3 is a nitrogen atom is more preferred, A triazine structure in which all of W and W3 are nitrogen atoms is most preferred.

[0299] In formula (1-1), Xa 1 At least one of the groups is a 1,3-phenylene group. Among them, -(Xa 1 ) g11 -Xa 2 is selected from the structure group of the following formula (Xa-1): It is more preferable that

[0300] [ka]

[0301] In these structures, hydrogen atoms are substituted with substituents selected from the above-mentioned substituent group Z2. Preferably, the hydrogen atom is not substituted.

[0302] In formula (1-1), Ya 1 At least one of the groups is a 1,3-phenylene group. Among them, -(Ya 1 ) h11 -Ya 2 is selected from the structure group of the following formula (Ya-1): It is more preferable that

[0303] [ka]

[0304] In these structures, hydrogen atoms are substituted with substituents selected from the above-mentioned substituent group Z2. Preferably, the hydrogen atom is not substituted.

[0305] In formula (1-1), Za 1 At least one of the groups is a 1,3-phenylene group. Among them, -(Za 1 ) j11 -Za 2 is selected from the structure group of the following formula (Za-1) It is more preferable that

[0306] [ka]

[0307] In these structures, hydrogen atoms are substituted with substituents selected from the above-mentioned substituent group Z2. Preferably, the hydrogen atom is not substituted.

[0308] The molecular weight of the compound represented by formula (1-1) is usually 5,000 or less, and is 3,000 or less. is preferred, more preferably 2,500 or less, and particularly preferably 2,000 or less. The lower limit of the molecular weight is preferably 350 or more, and most preferably 1,800 or less. , more preferably 400 or more, and particularly preferably 500 or more.

[0309] The specific structure of the compound represented by formula (1-1) is not particularly limited, but may be, for example, the following: Examples of such compounds include:

[0310] [ka]

[0311] [ka]

[0312] [ka]

[0313] [ka]

[0314] [ka]

[0315] [ka]

[0316] [ka]

[0317] The compound represented by formula (1-1) is a compound in which the group bonded to the para position of W1 has two or more benzene rings. Three molecules are linked at the para position, spreading the conjugation, and the LUMO is distributed here, resulting in excellent electron transport properties. In addition, the number of benzene rings conjugated to the para position of W1 is three or less. Therefore, the conjugation is not too long, it has a wide energy gap, and it is suitable as a matrix material for the light-emitting layer. When used as a light-emitting material, it is thought to be preferable because it is less likely to quench the light-emitting material.

[0318] In the compound represented by formula (1-1), in the nitrogen-containing 6-membered ring containing W1, W2, and W3, The group bonded to the para position of W3 is a 1,3-phenylene group, so it is not conjugated. The compound represented by formula (1-1) has a wide energy gap and is a matrix of the light-emitting layer. When used as a material, it is considered preferable because it is less likely to quench the light-emitting material. Za of the compound represented by formula (1-1) 1 At least one of them is a 1,3-phenylene group. Therefore, the carbazolyl group Za 2 Therefore, the equation (1-1) The compound has a wide energy gap, and when used as a matrix material for the light-emitting layer, This is considered to be preferable because it is difficult to quench the light-emitting material.

[0319] Furthermore, -(Xa 1 ) g11 -Xa 2 , -(Ya 1 ) h11 -Ya 2 , -(Za 1 ) j 11 -Za 2 When the preferable structure is as described above, it has a wide energy gap, and the When used as a trix material, it is difficult to quench the light-emitting material.

[0320] <Compound represented by formula (1-2)>

[0321] [ka]

[0322] [In formula (1-2), W1, W2 and W3 each independently represent -CH or a nitrogen atom; at least one of which is a nitrogen atom, Xa 1 , Ya 1 , and Za 1 each independently represents an optionally substituted 1,3-phenylene represents an phenylene group or an optionally substituted 1,4-phenylene group, Ya 1 and Za 1 At least one of the groups is optionally substituted 1,3-phenylene. It is the basis, Xa 2 represents an optionally substituted phenyl group, Ya 2 and Za 2 each independently represents an N-carbazolyl group which may have a substituent; death, f11 is 1 or 2, g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer between 2 and 5, f11+g11+h11+j11 is greater than or equal to 6, R 11 each independently represents a hydrogen atom or a substituent.

[0323] In formula (1-2), W1, W2, and W3 each independently represent -CH or a nitrogen atom. At least one of W1, W2 and W3 is a nitrogen atom. From the viewpoint of durability, it is preferable that at least W1 is a nitrogen atom, and at least W1 and W2 is preferably a nitrogen atom, and W1, W2 and W3 are all preferably nitrogen atoms. is more preferable.

[0324] That is, from the viewpoint of improving the electron transport property, the group bonded to the para position is preferably one having two or more benzene rings. Three of the atoms are linked at the para position to extend the conjugation. W1 is preferably a nitrogen atom. A pyrimidine structure in which one of W2 and W3 is a nitrogen atom is more preferred, A triazine structure in which all of W and W3 are nitrogen atoms is most preferred.

[0325] In formula (1-2), a 1,3-phenylene group, a 1,4-phenylene group, a phenyl group, The substituent that the N-carbazolyl group may have is selected from the aforementioned substituent group Z2.

[0326] R in formula (1-2) 11 each independently represents a hydrogen atom or a substituent. R is a substituent other than a hydrogen atom 11 Examples of the substituent Z include groups selected from the above-mentioned substituent group Z2. Among the substituent group Z2, preferred are those having 6 to 30 carbon atoms which may have a substituent. or an aromatic hydrocarbon group or an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent. do. From the viewpoint of improving durability and charge transportability, an aromatic hydrocarbon group which may have a substituent It is more preferable that R in the case of being a substituent in formula (1-2) is 11 There are multiple If multiple R 11 may be the same or different from each other. The substituents which the aromatic hydrocarbon group having 6 to 30 carbon atoms may have are The substituents that the aromatic heterocyclic group of R 11 may have The substituent can be selected from the above-mentioned substituent group Z2.

[0327] In formula (1-2), Xa 1 At least one of the groups is a 1,3-phenylene group. Among them, -(Xa 1 ) g11 -Xa 2 is selected from the structure group of the following formula (Xa-2) It is more preferable that

[0328] [ka]

[0329] In these structures, hydrogen atoms are substituted with substituents selected from the above-mentioned substituent group Z2. Preferably, the hydrogen atom is not substituted.

[0330] In formula (1-2), Ya 1 At least one of the groups is a 1,3-phenylene group. Among them, -(Ya 1 ) h11 -Ya 2 is selected from the structure group of the following formula (Ya-2) It is more preferable that

[0331] [ka]

[0332] In these structures, Ya 2 Including the hydrogen atoms on the benzene ring of the N-carbazolyl group and all hydrogen atoms on the benzene ring are substituted with a substituent selected from the above-mentioned substituent group Z2. Preferably, the hydrogen atoms are not substituted.

[0333] In formula (1-2), Za 1 At least one of the groups is a 1,3-phenylene group. Among them, -(Za 1 ) j11 -Za 2 is selected from the structure group of the following formula (Za-2) It is more preferable that

[0334] [ka]

[0335] In these structures, Za 2 Including the hydrogen atoms on the benzene ring of the N-carbazolyl group and all hydrogen atoms on the benzene ring are substituted with a substituent selected from the above-mentioned substituent group Z2. Preferably, the hydrogen atoms are not substituted.

[0336] In formula (1-2), h11 is preferably 2 or more, and is preferably 2 or 4. preferable. Furthermore, j11 is preferably 2 or more, and more preferably 2 or 4. When h11 and j11 are equal to or greater than the lower limit, the solubility and stability are good. .

[0337] In formula (1-2), Xa 1 At least one of the groups is a 1,3-phenylene group. Preferably, Xa 1 It is more preferable that all of Xa are 1,3-phenylene groups. 1 but The 1,3-phenylene group breaks the conjugation and increases solubility. In addition, in formula (1-2), Ya 1At least one of the groups is a 1,3-phenylene group. It is preferable that 1 It is more preferable that all of Y are 1,3-phenylene groups. a 1 The 1,3-phenylene group breaks the conjugation and increases the solubility. In addition, in formula (1-2), Za 1 At least one of the groups is a 1,3-phenylene group. It is preferable that Za 1 It is more preferable that all of Z are 1,3-phenylene groups. a 1 The 1,3-phenylene group breaks the conjugation and increases the solubility. In addition, in formula (1-2), Ya 1 At least one of the groups is a 1,3-phenylene group. , Za 1 At least one of these is preferably a 1,3-phenylene group.

[0338] The molecular weight of the compound represented by formula (1-2) is usually 5,000 or less, and is 3,000 or less. is preferred, more preferably 2,500 or less, and particularly preferably 2,000 or less. The molecular weight of the compound represented by formula (1-2) is preferably 1,800 or less, and most preferably 1,800 or less. The limit is preferably 350 or more, more preferably 400 or more, and particularly preferably 500 or more. Above.

[0339] The specific structure of the compound represented by formula (1-2) is not particularly limited, but may be, for example, the following: Examples of such compounds include:

[0340] [ka]

[0341] [ka]

[0342] [ka]

[0343] [ka]

[0344] [ka]

[0345] [ka]

[0346] [ka]

[0347] [ka]

[0348] The compound represented by formula (1-2) is a compound in which the group bonded to the para position of W1 has two or more benzene rings. Since the group is linked at the three para positions, the conjugation is widespread, and the LUMO is distributed there, In addition, the benzene ring conjugated to the para position of W1 Since the number of groups is three or less, the conjugation is not too long and the energy gap is wide. When used as a matrix material, it is considered preferable because it is less likely to quench the light-emitting material.

[0349] In the compound represented by formula (1-2), in the nitrogen-containing 6-membered ring containing W1, W2, and W3, The group bonded to the para position of W3 is a 1,3-phenylene group, so it is not conjugated. The compound represented by formula (1-2) has a wide energy gap and is a matrix of the light-emitting layer. When used as a material, it is considered preferable because it is less likely to quench the light-emitting material. Ya of the compound represented by formula (1-2) 1 and Za 1 At least one of each is 1,3 -phenylene group, so it is an N-carbazolyl group, Ya 2 or Za 2 is not conjugated with Therefore, the compound represented by formula (1-2) has a wide energy gap, and the light-emitting layer When used as a matrix material, it is considered preferable because it is less likely to quench the light-emitting material.

[0350] Furthermore, -(Xa 1 ) g11 -Xa 2 , -(Ya 1 ) h11 -Ya 2 , -(Za 1 ) j 11 -Za 2 When the preferable structure is as described above, it has a wide energy gap, and the When used as a trix material, it is difficult to quench the light-emitting material.

[0351] The compound represented by formula (1-2) is a compound having a nitrogen-containing six-membered ring containing W1, W2, and W3 and a compound having a carbonyl group. There are three or more phenylene groups between the rubazolyl groups, and there are a moderate number of 1,3-phenylene groups. It does not contain a 1,4-phenylene linkage structure longer than the terphenylene group, so it is easy to dissolve. It has excellent resolvability.

[0352] <Compound represented by formula (260)> When the organic film-forming material of the present invention contains a compound represented by formula (260), 0) may contain only one kind of compound, or may contain two or more kinds of compounds.

[0353] [ka]

[0354] (In formula (260), Ar 61 ~Ar 65 each independently represents a hydrogen atom or a monovalent group which may have a substituent; an aromatic hydrocarbon group having 6 to 60 carbon atoms, L 1 ~L 5 each independently represents a divalent group having 6 to 60 carbon atoms which may have a substituent; is an aromatic hydrocarbon group of the formula R 60 each independently represents a substituent, m1 to m5 each independently represent an integer of 0 to 5; n represents an integer of 0 to 10, a1 to a3 each independently represent an integer of 0 to 3; However, Ar 61 , Ar 62 , Ar 63 , Ar 64 , and at least when n is 1 or more Another Ar 65 At least one of them is not a hydrogen atom.)

[0355] (Ar 61 , Ar 62 , Ar 65 ) Ar in formula (260) 61 , Ar 62 and Ar 65 are each independently a hydrogen atom or is an optionally substituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0356] Ar in formula (260) 61 , Ar 62 and Ar65 is the solubility and durability of the compound. From this viewpoint, a hydrogen atom, a monovalent group of a benzene ring, a monovalent group of a naphthalene ring, a monovalent group of the following formula (261 ) or a structure represented by the following formula (262), which is preferably a hydrogen atom, a monovalent group of a benzene ring, The structure represented by the following formula (261) or (262) is more preferred, and The monovalent group of the Zene ring is more preferably a structure represented by the following formula (262), and the following formula (262) ) is particularly preferred.

[0357] From the viewpoint of durability and charge transport property, Ar 61 , Ar 62 and at least one Ar 6 5 Among them, one or more and three or less are the following formula (261) or the following formula (262). Preferably, Ar 61 , Ar 62 and at least one of and Ar 65 One or more of the following: It is more preferable that three or less of them are represented by the following formula (262). From the viewpoint of charge transport property and solubility, Ar 61 , Ar 62 and at least one Ar 65 Among these, it is preferable that one of them is represented by the following formula (262). From the viewpoint of durability, Ar 61 , Ar 62 and at least one Ar 65 2 of them It is preferable that at least one of them is represented by the following formula (262), and three of them are represented by the following formula (262). It is even more preferable that

[0358] [ka]

[0359] (In formula (261) or formula (262), The asterisk (*) indicates the bond position with the adjacent structure. R 101 ~R 126 each independently represents a hydrogen atom or a substituent.

[0360] Ar 61 is formula (261) or formula (262), m1 is preferably 0 or 1, and 0 More preferred is Ar 62 is formula (261) or formula (262), m2 is 0 or 1 is preferred, and 0 is more preferred. 65 is the formula (261) or the formula (262), m5 is preferably 0 or 1, and more preferably 0.

[0361] (Ar 63 , Ar 64 ) Ar in formula (260) 63 and Ar 64 each independently represents a hydrogen atom or a substituent represents an optionally present monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms. Examples of monovalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include benzene rings, naphthyl groups, and the like. phenylene ring, anthracene ring, phenanthrene ring, tetraphenylene ring, chrysene ring, pyrene a monovalent group of a ring, a benzanthracene ring, a perylene ring, a biphenyl ring, or a terphenyl ring Examples include:

[0362] Ar in formula (260) 63 , Ar 64 From the viewpoint of compound solubility and durability, Independently, a hydrogen atom, a monovalent group of a benzene ring, or a monovalent group of a naphthalene ring is preferred, and hydrogen A monovalent group of an atom or a benzene ring is more preferred.

[0363] In formula (260), Ar 61 , Ar62 , Ar 63 , Ar 64 , and n is 1 or more At least one Ar in the case 65 At least one of them is not a hydrogen atom.

[0364] (L 1 ~L 5 ) L in equation (260) 1 ~L 5 each independently represents a divalent carbon atom which may have a substituent; It represents an aromatic hydrocarbon group having a prime number of 6 or more and 60 or less. Examples of divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include benzene rings, naphthyl groups, and the like. phenylene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene Examples of the divalent ring include a divalent group of a benzanthracene ring, a divalent group of a perylene ring, and a divalent group of a benzoanthracene ring. L 1 ~L 5 each independently represents an optionally substituted phenylene group or a phenylene A divalent group having two or more groups, for example, 2 to 5 groups, connected by direct bonds is preferred, and the group may have a substituent. In terms of solubility, it is more preferable that the alkyl group is a 1,3-phenylene group.

[0365] (R 60 ) R in equation (260) 60 Each independently represents a substituent. Examples of the substituent include the above-mentioned Substituents selected from the group Z2 can be used. Among them, alkyl groups, Alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkoxycarbonyl group groups, acyl groups, halogen atoms, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups A siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred. From the viewpoint of the above, alkyl groups, alkenyl groups, alkoxy groups, aryloxy groups, alkoxy groups, carbonyl group, acyl group, halogen atom, haloalkyl group, silyl group, siloxy group, aryl group, Ralalkyl groups and aromatic hydrocarbon groups are preferred, and alkyl groups, alkoxy groups, aralkyl groups, Aromatic hydrocarbon groups are more preferred, and alkyl groups having 10 or less carbon atoms and alkyl groups having 30 or less carbon atoms are preferred. A raryl group and an aromatic hydrocarbon group having 30 or less carbon atoms are more preferred, and a benzene ring or benzene ring is more preferred. A group in which 2 to 5 Zene rings are linked together is particularly preferred.

[0366] (m1~m5) In formula (260), m1, m2, and m5 each independently represent an integer of 0 to 5, m3 and m4 each independently represent an integer of 0 to 5. In formula (260), m1, m2, and m5 are determined from the viewpoint of the solubility and durability of the compound. Preferably, it is 4 or less, more preferably 3 or less, even more preferably 2 or less, and particularly preferably 1 or less. Preferably, 0 is the most preferable.

[0367] Also, Ar 61 is the formula (261) or the formula (262), m1, Ar 62 is the formula (2 61) or formula (262), m2, and Ar 65 is the formula (261) or the formula (26 In the case of 2), m5 is preferably 0.

[0368] In the formula (260), m3 and m4 are each 1 or more from the viewpoint of the solubility and durability of the compound. is preferred, 4 or less is preferred, 3 or less is more preferred, and 2 or less is particularly preferred. When m1 in formula (260) is 2 or more, multiple L 1 may be the same or different If m2 in formula (260) is 2 or more, multiple L 2are the same or different If m3 in equation (260) is 2 or more, multiple L 3 are the same but different If m4 in formula (260) is 2 or more, multiple L 4 are the same but different If m5 in formula (260) is 2 or more, multiple L 5 are the same but different It is also possible.

[0369] ((L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , (L 5 ) m5 ) (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and and at least one (L 5 ) m5 At least one of the groups is responsible for the solubility and resistance of the compound. From the viewpoint of durability, the partial structure represented by the following formula (11) and the partial structure represented by the following formula (12) and a partial structure selected from the partial structures represented by the following formula (13): When m1 is 1 or more, 1 ) m1 , when m2 is 1 or more (L 2 ) m2 and n is 1 or more and m5 is 1 or more (L 5 ) m5 , and when m3 is 1 or more, (L 3 ) m 3 and m4 are 1 or more (L 4 ) m4is a partial structure represented by the following formula (11), A partial structure selected from a partial structure represented by formula (12) and a partial structure represented by formula (13) below: It is more preferable that the compound has a partial structure.

[0370] [ka]

[0371] In each of the above formulas (11) to (13), * indicates the bonding position with the adjacent structure or A r 61 , Ar 62 , Ar 63 , Ar 64 or Ar 65 is a hydrogen atom At least one of the two * marks represents the bonding position with the adjacent structure. Unless otherwise specified, the definition of * is the same in the rest of this document.

[0372] More preferably, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 At least one of the following must be satisfied: ) or a partial structure represented by formula (12). More preferably, in formula (260), when m1 is 1 or more, (L 1 ) m1 , m2 When is 1 or more, (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , if m4 is 1 or more Combined (L 4 ) m4, and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 are respectively, It has a partial structure represented by formula (11) or a partial structure represented by formula (12). Particularly preferably, in formula (260), when m1 is 1 or more, (L 1 ) m1 , m2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , if m4 is 1 or more (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 are the formulas It has a partial structure represented by formula (11) and a partial structure represented by formula (12).

[0373] In formula (260), formula (12) is preferably the following formula (12-2).

[0374] [ka]

[0375] In formula (260), formula (12) is more preferably the following formula (12-3): is.

[0376] [ka]

[0377] In addition, from the viewpoint of the solubility and durability of the compound, (L 1 ) m1 , ( L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , at least one of and (L5 ) m5 Of these, The partial structure that is preferably contained in at least one of the compounds is a partial structure represented by formula (11) and It is a partial structure having a partial structure represented by formula (12).

[0378] In formula (260), the partial structure represented by formula (11) and the partial structure represented by formula (12) The partial structure having the structure includes a partial structure represented by formula (11) and a partial structure represented by formula (12). The following formula (14) to the following formula (17) are structures including a plurality of structures selected from the partial structures In other words, when m1 is 1 or more, (L 1 ) m1 , m When 2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , m4 is 1 or more In the case of (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 are independent and a compound selected from the formulas (11) to (13) and the following formulas (14) to (17): It is preferable that the compound has a partial structure.

[0379] [ka]

[0380] In formula (260), the partial structure represented by formula (11) and the partial structure represented by formula (12) The structure including a plurality of structures selected from the structures of, for example, formula (14) is represented by the following formula (14a): Similarly, there is one partial structure represented by formula (11) and two partial structures represented by formula (12). This is a partial structure that can be considered as such.

[0381] [ka]

[0382] More preferably, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 At least one of the It has a partial structure represented by formula (14) or a partial structure represented by formula (15). For example, when m1 is 1 or more, 1 ) m1 , when m2 is 1 or more (L 2 ) m2 , m3 1 or more (L 3 ) m3 , when m4 is 1 or more (L 4 ) m4 , and n is 1 or more and When m5 is 1 or more, (L 5 ) m5 is a partial structure represented by formula (14) or formula (15) It has a partial structure represented by the following formula:

[0383] In formula (260), formula (14) is preferably the following formula (14-2).

[0384] [ka]

[0385] In formula (260), formula (14) is more preferably the following formula (14-3): do.

[0386] [ka]

[0387] In formula (260), formula (15) is preferably the following formula (15-2).

[0388] [ka]

[0389] In formula (260), formula (15) is more preferably the following formula (15-3): do.

[0390] [ka]

[0391] In formula (260), formula (17) is preferably the following formula (17-2).

[0392] [ka]

[0393] Also, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m 4, and at least one (L 5 ) m5 At least one of the parts is represented by formula (13). As a partial structure containing the structure, a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) It is more preferable that the compound has a partial structure such that

[0394] [ka]

[0395] In each of the above formulas (14) to (20), * indicates a bonding position with an adjacent structure or a water bond. It represents an elementary atom, and at least one of the two * marks represents the bonding position with the adjacent structure. In the formula (260), among the formulas (14) to (20), the formulas (14-3) and (15) -3) is preferred, and formula (14-3) is more preferred.

[0396] (L 1 ~L 5 (preferred substructure of In formula (260), L 1 ~L 5 is a partial structure represented by formula (11), a partial structure represented by formula (14-3) or a part represented by formula (15-3) It is preferable to have a structure.

[0397] (n) In the formula (260), n represents an integer of 0 to 10. In the formula (260), n is preferably 1 or more from the viewpoint of the solubility and durability of the compound. Preferably, the number is 2 or more, more preferably 6 or less, even more preferably 5 or less, and especially 4 or less. Preferred.

[0398] (a1~a3) a1 to a3 each independently represent an integer of 0 to 3. a1 to a3 are selected from the viewpoints of the solubility and durability of the compound. It is preferable that a1 to a3 each independently represent 0 or 1. It is most preferable that a1=a2=a3=0.

[0399] (R 101 ~R 126 ) In equation (260), R 101 ~R 126 each independently represents a hydrogen atom or a substituent. As the substituent, those selected from the above-mentioned substituent group Z2 can be used. Among these, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups, A silyl group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, a thio group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group From the viewpoint of durability, alkyl groups, alkenyl groups, alkoxy groups, aryl groups, etc. are preferred. oxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, silyl group , a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred, and a hydrogen atom, an aromatic hydrocarbon group is preferred. A group is more preferred, and a hydrogen atom is particularly preferred.

[0400] In formula (260), Ar 61 ~Ar 65 Monovalent carbon atoms of 6 or more and 60 or less Aromatic hydrocarbon groups and L 1 ~L 5 Aromatic carbon with a divalent carbon number of 6 or more and 60 or less The substituents that the hydrogen hydride group may have are each independently selected from the above-mentioned substituent group Z2. Among them, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, group, aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkoxy group a silyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic group; Aromatic hydrocarbon groups are preferred, and alkyl groups, alkenyl groups, alkoxy groups, aryloxy groups, etc. groups, alkoxycarbonyl groups, acyl groups, halogen atoms, haloalkyl groups, silyl groups, An alkoxy group, an aralkyl group, or an aromatic hydrocarbon group is more preferred.

[0401] The molecular weight of the compound represented by formula (260) is preferably 3,000 or less, more preferably is 2,500 or less, more preferably 2,000 or less, and particularly preferably 1, 500 or less, and usually 400 or more, preferably 500 or more, more preferably 60 Greater than or equal to 0.

[0402] Specific examples of the compound represented by formula (260) are shown below, but the compound is not limited to these. There is no.

[0403] [ka]

[0404] [ka]

[0405] [ka]

[0406] <Content of each compound> The preferred contents of various compounds contained in the organic film-forming material of the present invention are shown below. vinegar.

[0407] The content of the compound represented by formula (2) is, with the total organic film-forming material being 100 parts by mass, Usually, it is 90 parts by mass or less, preferably 70 parts by mass or less, and more preferably 50 parts by mass or less. and usually 1 part by mass or more, preferably 5 parts by mass or more, and more preferably 10 parts by mass or more. Above.

[0408] The compound represented by formula (2) acts as a host, mainly transporting holes. It is preferable that the compound contains a host that carries out the transport. The content of the compound represented by formula (2) falls within this range. This suppresses electron transport and widens the recombination and light-emitting regions near the hole transport interface. , the operating life tends to be extended.

[0409] The content of the compound represented by formula (71) is 100 parts by mass of the entire organic film-forming material. The amount is usually 20 parts by mass or less, preferably 10 parts by mass or less, and more preferably 5 parts by mass or less. and usually 0.01 parts by mass or more, preferably 0.1 parts by mass or more, and more preferably 1 part by mass or more. parts by mass or more.

[0410] The compound represented by formula (71) is a compound in which excitons in the material ultimately lead to light emission. In most cases, the energy gap is smallest and the LUMO level is deepest. If the content is higher than the upper limit, the driving voltage of the organic electroluminescent device increases. In addition, as the content increases, concentration quenching due to aggregation occurs. On the other hand, if the content is lower than the lower limit, the luminous efficiency expressed by the formula (71) The emission of compounds other than those used will not produce a narrow half-width emission, and the operating life will be shortened. There is a tendency.

[0411] The organic film-forming material of the present invention contains, in addition to the compound represented by formula (71), a phosphorescent compound The phosphorescent compound is preferably a compound represented by formula (7): It's nice. When the organic film-forming material of the present invention contains a compound represented by formula (7), The content of the compound is usually 50 parts by mass or less, preferably 100 parts by mass of the entire material. It is preferably 30 parts by mass or less, more preferably 15 parts by mass or less, and is usually 1 part by mass or more, preferably The content is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more. By this, the excitons recombined in the compound represented by formula (7) and the excitons recombined in the host material are The combined excitons tend to be transferred to the compound represented by formula (71). Depending on the combination of HOMO levels in the materials used, the compound represented by formula (7) may have hole transport properties. This tends to increase the recombination probability and exciton utilization rate. The driving voltage of the element can be reduced by adjusting the content of the compound represented by formula (7). In addition, when the organic film-forming material of the present invention contains a compound represented by formula (7), The compound represented by formula (71) and the compound represented by formula (7) are organic film-forming materials. The material may contain only one type, or two or more types in combination.

[0412] The organic film-forming material of the present invention includes a host material that transports electrons and a compound that controls the transport of holes and electrons. It is preferable that the compound further contains a host material that is regulated by the above-mentioned formula (1). As described above, the compound represented by formula (260) is suitable. The total content of the host materials other than the compound represented by formula (2) is 100 parts by mass of the entire material. As a result, the amount is usually 90 parts by mass or less, preferably 70 parts by mass or less, and more preferably 50 parts by mass or less. and is usually 1 part by mass or more, preferably 5 parts by mass or more, and more preferably 10 parts by mass or more. The content of the host material other than the compound represented by formula (2) is in this range. By this, holes injected from the hole transport layer and electrons injected from the electron transport layer are transported to the light emitting layer. This allows for well-balanced transport to the recombination region within the electrons, resulting in low drive voltage and high luminous efficiency. There is a tendency.

[0413] [Composition for organic film formation] The organic film-forming composition of the present invention contains the organic film-forming material and a solvent. The forming composition is preferably a composition for forming a light-emitting layer.

[0414] The method for forming an organic film containing the organic film-forming material of the present invention is a vacuum deposition method or a wet film formation method. In the case of the wet film formation method, the organic film formation method of the present invention is The organic film can be formed by applying the composition and drying it.

[0415] The solvent contained in the organic film-forming composition is a material for forming an organic film by wet film formation. It is a volatile liquid component used to form an organic film.

[0416] The solvent is a solvent in which each compound contained in the organic film-forming material, which is a solute, is well dissolved. There are no particular limitations on the solvent as long as it is capable of carrying out the reaction, but organic solvents are preferred.

[0417] Preferred organic solvents include, for example, n-decane, cyclohexane, and ethylcyclohexane. Alkanes such as toluene, xylene, mesitylene, Aromatic hydrocarbons such as phenylcyclohexane, tetralin, and methylnaphthalene; chloro Halogenated aromatic hydrocarbons such as benzene, dichlorobenzene, and trichlorobenzene; 1 ,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-Methoxytoluene, 3-Methoxytoluene, 4-Methoxytoluene, 2,3-Dimethyl Aromatic ethers such as diphenyl ether, 2,4-dimethylanisole, and diphenyl ether Phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propionate aromatic esters such as propyl, n-butyl benzoate, etc.; cyclohexanone, cyclooctanoic acid, etc. alicyclic ketones such as cyclohexanol and cyclooctanol; Aliphatic alcohols; aliphatic ketones such as methyl ethyl ketone and dibutyl ketone; butanol aliphatic alcohols such as hexanol; ethylene glycol dimethyl ether, ethylene glycol dimethyl ether, Propylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate aliphatic ethers such as methyl ether (PGMEA); and the like.

[0418] Among these, from the viewpoint of viscosity and boiling point, alkanes, aromatic hydrocarbons, and aromatic ethers are the most popular. Preferred are aromatic hydrocarbons, aromatic ethers and aromatic esters, and Esters are more preferred, and aromatic hydrocarbons and aromatic esters are particularly preferred.

[0419] These organic solvents may be used alone or in any combination of two or more. , and may be used in ratios.

[0420] The boiling point of the organic solvent used is usually 80°C or higher, preferably 100°C or higher, more preferably 1 20°C or higher, and usually 350°C or lower, preferably 330°C or lower, more preferably 300°C or lower. If the boiling point of the organic solvent is below this range, the composition may be dissolved in water during wet film formation. The evaporation of the solvent may cause a decrease in film formation stability. If the temperature is too high, the stability of the film may be reduced due to residual solvent after film formation. be.

[0421] In particular, two or more of the above organic solvents having a boiling point of 150°C or higher are combined. This is considered to facilitate the formation of a more uniform coating film, which is preferable.

[0422] The content of the organic film-forming material in the organic film-forming composition of the present invention is usually 0.00 1% by mass or more, preferably 0.01% by mass or more, and usually 30.0% by mass or less, preferably The content is 20.0 mass % or less.

[0423] The content of the organic solvent in the organic film-forming composition of the present invention is usually 10% by mass or more, and preferably Preferably, it is 50% by mass or more, particularly preferably 80% by mass or more, and usually 99.95% by mass or more. % or less, preferably 99.9% by mass or less, and particularly preferably 99.8% by mass or less. If the content of the organic solvent is equal to or greater than the above lower limit, the composition will have a suitable viscosity and the coating properties will be improved. If the temperature is lower than this, a uniform film is easily obtained and film formation properties are good.

[0424] (Other ingredients) The organic film-forming composition of the present invention may contain, in addition to the above-mentioned compounds, other compounds, if necessary. As other compounds, preferably, diamines known as antioxidants may be contained. Examples include phenols such as butylhydroxytoluene and dibutylphenol.

[0425] [Method for forming organic film] The method for forming an organic film using the composition for forming an organic film of the present invention is preferably a wet film formation method. The wet film-forming method involves applying a composition to form a liquid film, drying it to remove the organic solvent, and This is a method for forming a film. Examples of coating methods include spin coating and dip coating. method, die coating method, bar coating method, blade coating method, roll coating method, spray coating method method, capillary coating method, inkjet method, nozzle printing method, screen printing We use wet methods such as printing, gravure printing, and flexographic printing to form the film, and then dry the coating film. Among these coating methods, spin coating and spray coating are the most popular. The inkjet method, the nozzle printing method, etc. are preferred. When manufacturing an organic EL display device, the inkjet method or nozzle printing method is preferred. The ink jet method is particularly preferred.

[0426] The drying method is not particularly limited, but may be natural drying, drying under reduced pressure, drying with heat, or drying with heat. Heat drying can be carried out after natural drying or reduced pressure drying. This may be carried out to remove residual organic solvents.

[0427] The drying under reduced pressure is preferably carried out at a pressure equal to or lower than the vapor pressure of the organic solvent contained in the composition.

[0428] When heating, the heating method is not particularly limited, but heating on a hot plate, heating in an oven, etc. Heating in a furnace or infrared heating can be used. The heating time is usually 80°C or higher, 100 ° C. or higher, more preferably 110 ° C. or higher, and more preferably 200 ° C. or lower. A temperature of 50°C or less is more preferable.

[0429] The heating time is usually 1 minute or more, preferably 2 minutes or more, and usually 60 minutes or less, preferably 30 minutes or less. It is preferable that the time is 20 minutes or less.

[0430] [Organic electroluminescent device] The organic electroluminescent device of the present invention has an organic layer containing an organic film-forming material. An example of the structure of the organic electroluminescent device of the present invention is an organic electroluminescent device 8 shown in FIG. In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, and 5 is a light emitting layer. , 6 represents an electron transport layer, and 7 represents a cathode.

[0431] The organic layer containing the organic film-forming material of the present invention is preferably the light-emitting layer 5. The compound represented by (2) is more preferably used as the charge transport compound in the light-emitting layer 5. It's nice.

[0432] As an example of the structure of the organic electroluminescent device of the present invention, an example of the structure of the organic electroluminescent device 8 is shown in FIG. In Fig. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, and 4 is a hole 5 represents a light-emitting layer, 6 represents an electron-transporting layer, and 7 represents a cathode.

[0433] The substrate 1 serves as a support for the organic electroluminescent device, and is usually made of a quartz or glass plate, a gold plate, or a metal plate. Metal plates, metal foils, plastic films and sheets, etc. are used. Among these, glass plates and transparent composites such as polyester, polymethacrylate, polycarbonate, and polysulfone. A resin plate is preferable. The substrate is less likely to cause deterioration of the organic electroluminescent element due to the outside air. Therefore, it is preferable to use a material with high gas barrier properties. When using a material with low gas barrier properties, such as It is preferable to provide a protective film or the like to improve the gas barrier properties.

[0434] The anode 2 has the function of injecting holes into the layer on the light-emitting layer 5 side.

[0435] The anode 2 is usually made of a metal such as aluminum, gold, silver, nickel, palladium, or platinum; Metal oxides such as zinc and / or tin oxide; metal halides such as copper iodide; carbon Black and highly conductive materials such as poly(3-methylthiophene), polypyrrole, and polyaniline It is composed of molecules, etc.

[0436] The anode 2 is usually formed by a dry method such as sputtering or vacuum deposition. In addition, there are many metal particles such as silver, copper iodide particles, carbon black, conductive gold When forming the anode using metal oxide fine particles, conductive polymer fine powder, etc., a suitable binder is required. Alternatively, the layer may be dispersed in a dye resin solution and applied to a substrate. In the case of conductive polymers, a thin film can be formed directly on the substrate by electrolytic polymerization, or a conductive film can be formed on the substrate. The anode can also be formed by coating a polymer (Appl. Phys. Lett. ,Vol. 60, p. 2711, 1992).

[0437] The anode 2 usually has a single-layer structure, but may have a laminated structure as appropriate. In this case, a different conductive material may be laminated on the first anode layer.

[0438] The thickness of the anode 2 may be determined depending on the required transparency and material. When this is required, the thickness is preferably such that the transmittance of visible light is 60% or more. The thickness of the anode 2 is preferably 5 nm or more, more preferably 80% or more. It is usually 10 nm or more, and is usually 1000 nm or less, preferably 500 nm or less. On the other hand, when transparency is not required, the thickness of the anode 2 can be arbitrarily determined depending on the required strength, etc. In this case, the anode 2 may have the same thickness as the substrate.

[0439] When forming another layer on the surface of the anode 2, ultraviolet light / ozone, oxygen plasma, By applying argon plasma treatment or the like, impurities on the anode 2 are removed and the It is preferable to adjust the ionization potential to improve the hole injection property.

[0440] The layer that transports holes from the anode 2 side to the light-emitting layer 5 side is usually a hole injection transport layer or This layer is called a hole transport layer. It transports holes from the anode 2 side to the light-emitting layer 5 side. When there are two or more layers, the layer closer to the anode side is sometimes called the hole injection layer 3. The injection layer 3 is formed to enhance the function of transporting holes from the anode 2 to the light-emitting layer 5. When the hole injection layer 3 is formed, the hole injection layer 3 is usually formed on the anode 2. can be.

[0441] The thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, and is usually 1000 nm or less, preferably 500 nm or less.

[0442] The hole injection layer may be formed by a vacuum deposition method or a wet film formation method. is preferably formed by a wet film forming method.

[0443] A general method for forming a hole injection layer will be described below. In the device, the hole injection layer is formed by a wet film formation method using a composition for forming a hole injection layer. It is preferable that

[0444] The composition for forming a hole injection layer usually contains a hole transporting compound that will become the hole injection layer 3 . In addition, in the case of a wet film-forming method, the composition for forming a hole injection layer usually further contains a solvent. The composition for forming a hole injection layer has a high hole transporting property and can efficiently transport injected holes. Therefore, it is preferable that the hole mobility is large and impurities that become traps are removed during manufacturing, use, etc. Furthermore, it is preferable that the ionization potential is small and the ionization rate is high. It is preferable that the transparency to visible light is high. In particular, when the hole injection layer is in contact with the light emitting layer, Those that do not quench the light emitted from the light-emitting layer or form exciplexes with the light-emitting layer to increase the light-emitting efficiency It is preferable that the above-mentioned properties are not reduced.

[0445] As the hole transporting compound, from the viewpoint of the charge injection barrier from the anode to the hole injection layer, 4.5 A compound having an ionization potential of 6.0 eV to 6.0 eV is preferred. Examples of the compounds include aromatic amine compounds, phthalocyanine compounds, and porphyrin compounds. , oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, Compounds in which tertiary amines are linked via fluorene groups, hydrazone compounds, silazane compounds, Examples thereof include nacridone compounds.

[0446] Among the above-mentioned exemplary compounds, aromatic amine compounds are preferred in terms of amorphousness and visible light transmittance. An aromatic tertiary amine compound is particularly preferred. is a compound having an aromatic tertiary amine structure, and having a group derived from an aromatic tertiary amine Also includes compounds.

[0447] The type of aromatic tertiary amine compound is not particularly limited, but it is preferable to use a compound having a uniform surface smoothing effect. Polymerization with a weight average molecular weight of 1,000 or more and 1,000,000 or less is preferred because it is easy to obtain light emission. It is preferable to use a polymer compound (a polymer compound having a series of repeating units).

[0448] When the hole injection layer 3 is formed by a wet film formation method, the material for the hole injection layer is usually a soluble material. Mix with a solvent (solvent for hole injection layer) to prepare a film-forming composition (composition for forming hole injection layer) Then, this hole injection layer-forming composition is applied to a layer corresponding to the layer below the hole injection layer (usually, The hole injection layer 3 is formed by applying the solution onto the anode (electrode) to form a film and drying it.

[0449] The concentration of the hole transporting compound in the composition for forming the hole injection layer significantly improves the effect of the present invention. However, in terms of uniformity of the film thickness, a lower value is preferable. A higher content is preferable in that defects are less likely to occur in the hole injection layer. It is preferably 0.1% by mass or more, more preferably 0.5% by mass or more. It is particularly preferable that the content is 70% by mass or less, and more preferably 60% by mass or less. It is more preferable that the content is less than 50% by mass, and particularly preferable that the content is 50% by mass or less.

[0450] Examples of the solvent include ether solvents, ester solvents, aromatic hydrocarbon solvents, and Examples include mide-based solvents.

[0451] Examples of ether solvents include ethylene glycol dimethyl ether, ethylene glycol Licorice diethyl ether, propylene glycol-1-monomethyl ether acetate Aliphatic ethers such as (PGMEA) and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene Dibenzoylbenzene, Anisole, Phenetole, 2-Methoxytoluene, 3-Methoxytoluene , 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, etc. Examples of aromatic ethers include the following.

[0452] Examples of ester solvents include phenyl acetate, phenyl propionate, and methyl benzoate. aromatic esters such as benzoic acid ethyl, benzoic acid ethyl, benzoic acid propyl, benzoic acid n-butyl, etc. Examples include:

[0453] Examples of aromatic hydrocarbon solvents include toluene, xylene, and cyclohexylbenzene. benzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diphenyl Examples include isopropylbenzene, cyclohexylbenzene, and methylnaphthalene.

[0454] Examples of amide solvents include N,N-dimethylformamide and N,N-dimethylazoline. cetoamide and the like.

[0455] In addition to these, dimethyl sulfoxide and the like can also be used.

[0456] The formation of the hole injection layer 3 by a wet film formation method is usually carried out by preparing a composition for forming the hole injection layer, followed by: This is applied to the layer below the hole injection layer 3 (usually the anode 2) to form a film, and then dried. This is done by:

[0457] After the hole injection layer 3 is formed, the coated film is usually dried by heating, drying under reduced pressure, or the like.

[0458] When the hole injection layer 3 is formed by vacuum deposition, the material of the hole injection layer 3 is usually One or more types of materials are placed in a crucible installed in a vacuum chamber (using two or more types of materials) In this case, each is usually placed in a separate crucible), and the vacuum chamber is evacuated by a vacuum pump for 10 -4 Pa level Then, the crucible is heated (when two or more materials are used, usually each crucible is The material in the crucible is evaporated while controlling the amount of evaporation (when two or more materials are used, When using a crucible, the evaporation rate is usually controlled independently. A hole injection layer is formed on the anode on the substrate. When two or more materials are used, Alternatively, the mixture can be placed in a crucible, heated, and evaporated to form a hole injection layer. .

[0459] The degree of vacuum during deposition is not limited as long as it does not significantly impair the effects of the present invention. x10 -6 Torr (0.13 × 10 -4 Pa) or more, 9.0×10 -6 Torr(12 .0×10 -4 The deposition rate is not more than 100 Pa. The deposition rate is not limited as long as it does not significantly impair the effects of the present invention. The deposition rate is not fixed, but is usually between 0.1 Å / sec and 5.0 Å / sec. There are no particular limitations as long as the effect of the present invention is not significantly impaired, but the temperature is preferably 10°C or higher, 50°C or higher. It is done below.

[0460] The hole injection layer 3 may be crosslinked.

[0461] The hole transport layer 4 is a layer that transports holes from the anode 2 side to the light-emitting layer 5 side. In the organic electroluminescent device of the present invention, the transport layer 4 has a function of transporting holes from the anode 2 to the light-emitting layer 5. In order to enhance the hole transporting property, it is preferable to form this layer. The hole transport layer 4 is usually formed between the anode 2 and the light emitting layer 5. In some cases, it is formed between the hole injection layer 3 and the light emitting layer 5 .

[0462] The thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more. , usually 300 nm or less, preferably 100 nm or less.

[0463] The hole transport layer 4 may be formed by vacuum deposition or wet film formation. In this case, it is preferable to form the film by a wet film forming method.

[0464] The hole transport layer 4 usually contains a hole transporting compound, and examples of the hole transporting compound include For example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl is a typical example. Aromatic compounds containing two or more tertiary amines and two or more condensed aromatic rings substituted on the nitrogen atom. Diamine (Japanese Patent Publication No. 5-234681), 4,4',4''-tris(1-naphthalene) Aromatic amines with starburst structures such as (butylphenylamino)triphenylamine compounds (J. Lumin., vol. 72-74, p. 985, 1997), triphenylazoline Aromatic amine compounds consisting of tetramers of amine (Chem. Commun., p. 2175, 1 996), 2,2',7,7'-tetrakis-(diphenylamino)-9,9'-spiro[a]pyridin-2-one Spiro compounds such as bromofluorene (Synth. Metals, Vol. 91, p. 209, 19 1997), carbazole derivatives such as 4,4'-N,N'-dicarbazole biphenyl, etc. Also, for example, polyvinyl carbazole, polyvinyl triazole, etc. are preferred. phenylamine (Japanese Patent Publication No. 7-53953), tetraphenylbenzidine Polyarylene ether sulfone (Polym. Adv. Tech., Vol. 7, 33 p. 1996).

[0465] When forming a hole transport layer by a wet film formation method, the hole injection layer is usually formed by a wet film formation method. In the same manner as in the case of forming a hole transport layer, the hole transport layer forming composition is used instead of the hole injection layer forming composition. It is formed using.

[0466] When the hole transport layer is formed by a wet film formation method, the composition for forming the hole transport layer is usually further dissolved. The solvent used in the composition for forming a hole transport layer is the same as that used in the composition for forming a hole injection layer. The same solvent as used in the step 1 can be used.

[0467] The concentration of the hole transport compound in the composition for forming the hole transport layer is The concentration of the hole transporting compound in the material can be in the same range as that of the hole transporting compound in the material.

[0468] The hole transport layer can be formed by a wet film formation method in the same manner as the hole injection layer formation method described above. Cut.

[0469] When forming a hole transport layer by vacuum deposition, the hole injection layer is usually formed by vacuum deposition. In the same manner as in the case of forming the hole injection layer by the deposition method, a hole transport layer forming composition is used instead of the hole injection layer forming composition. The film can be formed using a composition. The film formation conditions, such as the degree of vacuum during deposition, deposition rate, and temperature, can be adjusted. The film can be formed under the same conditions as those for the vacuum deposition of the hole injection layer.

[0470] When an electric field is applied between the pair of electrodes, the light-emitting layer 5 converts holes injected from the anode 2 and electrons injected from the cathode This layer is excited by the recombination of electrons injected from 7 and emits light. The light-emitting layer 5 is a layer formed between the anode 2 and the cathode 7. The light-emitting layer is formed on the anode by hole injection. If there is a hole injection layer, it is formed between the hole injection layer and the cathode, and if there is a hole transport layer on the anode, is formed between the hole transport layer and the cathode.

[0471] A general method for forming a light-emitting layer will be described below. The light-emitting layer is formed by a wet film-forming method using the organic film-forming composition of the present invention. is preferred. The compound represented by formula (2) contained in the composition for forming an organic film of the present invention can be used as a hole transport layer. In contrast to the common hole transport materials based on aromatic amines and carbazoles, Therefore, a moderate positive charge is generated at the interface between the hole transport layer and the light emitting layer. A hole injection barrier is provided. This barrier provides a region within the light-emitting layer where electrons and holes can recombine. This narrows the film thickness range, allowing more light to be emitted within the film thickness range where light is reinforced by optical interference. Therefore, a highly efficient organic electroluminescent device can be obtained. By combining with the compound represented by formula (71), which shows a high full-width at half maximum, a strong optical interference can be observed. It is believed that by using the top emission method in a coordinated manner, synergistic effects will be achieved. can be.

[0472] The thickness of the light-emitting layer 5 is arbitrary as long as it does not significantly impair the effects of the present invention. On the other hand, a thinner film is preferable because it is easier to achieve a low driving voltage. Therefore, it is preferable that the thickness is 3 nm or more, and more preferably 5 nm or more. On the other hand, it is usually preferably 200 nm or less, more preferably 100 nm or less. It's nice.

[0473] The light-emitting layer 5 contains at least a material having a light-emitting property as a light-emitting material, and Preferably, the host material contains one or more charge transporting compounds.

[0474] The charge transport material is a material that has the ability to transport positive charges (holes) or negative charges (electrons). There are no particular limitations, and known materials can be used as long as they do not impair the effects of the invention.

[0475] The charge transport material may be a compound that has been used in the light emitting layer 5 of an organic electroluminescent device. In particular, the compounds used as the host material of the light-emitting layer 5 are preferred.

[0476] Specific examples of the charge transport material include aromatic amine compounds and phthalocyanine compounds. compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzophenone compounds, Dylphenyl compounds, compounds with tertiary amines linked via fluorene groups, hydrazone compounds Silazane compounds, silanamine compounds, phosphamine compounds, quinacridone compounds In addition to the compounds exemplified as the hole transporting compound of the hole injection layer 3, Thracene compounds, pyrene compounds, carbazole compounds, pyridine compounds, phenanthracene compounds, Electron transporting compounds such as thoroline compounds, oxadiazole compounds, and silole compounds Examples include:

[0477] Also, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenanthrin Contains two or more tertiary amines, typically phenyl, and two or more fused aromatic rings substituted on the nitrogen atom Aromatic diamines (JP Patent Publication No. 5-234681), 4,4',4''-triamine Starburst structure such as bis(1-naphthylphenylamino)triphenylamine Aromatic amine compounds (J. Lumin., vol. 72-74, p. 985, 1997), Aromatic amine compounds consisting of tetramers of phenylamine (Chem. Commun., 2175, 1996), 2,2',7,7'-tetrakis-(diphenylamino)- Fluorene-based compounds such as 9,9'-spirobifluorene (Synth.Metals,9 1, p. 209, 1997), 4,4'-N,N'-dicarbazole biphenyl, etc. Compounds exemplified as the hole transporting compound for the hole transport layer 4, such as rubazoline compounds, are also preferred. In addition, 2-(4-biphenylyl)-5-(p-tert-butyl) (tBu-PBD), 2,5-bis(2,5-dimethylphenyl)-1,3,4-oxadiazole (tBu-PBD), Oxadiazoles such as bis(1-naphthyl)-1,3,4-oxadiazole (BND) The compound, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3, Silole compounds such as 4-diphenylsilole (PyPySPyPy), bathophenanthrene Lorin (BPhen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthate Phenanthroline compounds such as bathocuproine (BCP) are also included.

[0478] The light-emitting layer may be formed by vacuum deposition or wet film formation. From these viewpoints, wet film-forming methods are preferred, and spin coating and ink-jet methods are more preferred. The above composition for organic electroluminescent devices is used to form a hole injection layer or a hole transport layer which is a layer below the light emitting layer. When a transfer layer is formed, lamination by a wet film forming method is easy, so the wet film forming method is adopted. When the light-emitting layer is formed by a wet film-forming method, the hole-injecting layer is usually formed by a wet film-forming method. In the same manner as in the case of forming the layer by the film-forming method, a layer to be used as the light-emitting layer is used instead of the hole-injection layer-forming composition. The light-emitting layer is formed using a composition for forming a light-emitting layer prepared by mixing the material to be formed with a soluble solvent (solvent for the light-emitting layer). Complete.

[0479] Examples of the solvent include the ether-based solvents and ester-based solvents mentioned for forming the hole injection layer. Solvents, aromatic hydrocarbon solvents, amide solvents, alkane solvents, halogenated aromatic carbon Hydrogen hydride solvents, aliphatic alcohol solvents, alicyclic alcohol solvents, aliphatic ketone solvents Specific examples of solvents are listed below, but the effects of the present invention can be achieved by The present invention is not limited to these examples, provided that they do not impair the rights of the applicant.

[0480] For example, ethylene glycol dimethyl ether, ethylene glycol diethyl ether , aliphatic alcohols such as propylene glycol-1-monomethyl ether acetate (PGMEA) Ether solvents; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene 2,3-dimethylanisole, 2,4-dimethylanisole, diphenyl ether, etc. Aromatic ether solvents; phenyl acetate, phenyl propionate, methyl benzoate, benzoic acid Aromatic ester solvents such as ethyl benzoate, propyl benzoate, and n-butyl benzoate; toluene benzene, xylene, mesitylene, cyclohexylbenzene, tetralin, 3-isopropylbenzene Phenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, Aromatic hydrocarbon solvents such as cyclohexylbenzene and methylnaphthalene; N,N-dimethyl Amide solvents such as methylformamide and N,N-dimethylacetamide; n-decane, cyclohexane Alkane solvents such as hexane, ethylcyclohexane, decalin, and bicyclohexane; Halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene Solvents: Aliphatic alcohol solvents such as butanol, hexanol, etc.; cyclohexanol, cyclohexanol, etc. Alicyclic alcohol solvents such as cyclooctanol; methyl ethyl ketone, dibutyl ketone, etc. Aliphatic ketone solvents such as cyclohexanone, cyclooctanone, and fenchone; Among these, alkane solvents and aromatic hydrocarbon solvents are Particularly preferred.

[0481] A hole-blocking layer may be provided between the light-emitting layer 5 and the electron-injecting layer described below. This layer is laminated on the optical layer 5 so as to be in contact with the interface of the light-emitting layer 5 on the cathode 7 side.

[0482] This hole blocking layer has the role of preventing holes migrating from the anode 2 from reaching the cathode 7. and efficiently transports electrons injected from the cathode 7 toward the light-emitting layer 5. The properties required for the material that constitutes the hole blocking layer are high electron mobility and low hole mobility. The energy gap (difference between HOMO and LUMO) is large, and the excited triplet level ( T1) is high.

[0483] Examples of materials for the hole blocking layer that satisfy these conditions include bis(2-methyl-8- Quinolinolato) (phenolato) aluminum, bis(2-methyl-8-quinolinolato) ( Mixed ligand complexes such as triphenylsilanolate)aluminum, bis(2-methyl-8-oxo) (2-methyl-8-quinolinolato)aluminum-μ-oxo-bis-(2-methyl-8-quinolinolato)aluminum metal complexes such as dinuclear metal complexes, styryl compounds such as distyrylbiphenyl derivatives (Japan) JP-A-11-242996), 3-(4-biphenylyl)-4-phenyl-5- Triazole derivatives such as (4-tert-butylphenyl)-1,2,4-triazole (Japanese Patent Application Laid-Open No. 7-41759), phenanthroline derivatives such as bathocuproine ( Japanese Patent Application Laid-Open No. 10-79297 and the like. Compounds having at least one pyridine ring substituted at the 2, 4, and 6 positions described in No. 22962 The material is also preferred as the hole blocking layer material.

[0484] There is no limitation on the method for forming the hole blocking layer. Therefore, the hole blocking layer may be formed by a wet film forming method, a vapor deposition method, or other methods. It can be formed.

[0485] The thickness of the hole blocking layer is arbitrary as long as it does not significantly impair the effect of the present invention. nm or more, preferably 0.5 nm or more, and is usually 100 nm or less, preferably 5 0nm or less.

[0486] The electron transport layer 6 is formed between the light-emitting layer 5 and the cathode in order to further improve the current efficiency of the device. It is located between 7.

[0487] The electron transport layer 6 efficiently transports electrons injected from the cathode 7 between the electrodes to which an electric field is applied. The electron transport layer 6 is made of a compound that can transport electrons in the direction of the light-emitting layer 5. The electron transporting compound to be used is one that has a high electron injection efficiency from the cathode 7 and a high electron mobility. It is necessary that the compound has a high conductivity and can efficiently transport injected electrons. do.

[0488] Specific examples of the electron transporting compound used in the electron transport layer include 8-hydroxybenzophenone-1, ...2, 8-hydroxybenzophenone-3, 8-hydroxybenzophenone-4, 8-hydroxybenzophenone-5, 8-hydroxybenzophenone-6, 8-hydroxybenzophenone-7, 8-hydroxybenzophenone-8, 8-hydroxybenzophenone-9, 8-hydroxybenzophenone-1, Metal complexes such as aluminum complexes of quinoline (Japanese Patent Publication No. 59-194393), Metal complexes of 10-hydroxybenzo[h]quinoline, oxadiazole derivatives, distyriazoles Iridium biphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone Ciflavonoid metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, tris Benzimidazolylbenzene (U.S. Pat. No. 5,645,948), quinoxaline compounds (Japanese Unexamined Patent Publication No. 6-207169), phenanthroline derivatives (Japanese Unexamined Patent Publication No. 5-207169), -331459), 2-tert-butyl-9,10-N,N'-dicyanoanthracene Laquinone diimine, n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, n-type zinc selenide, etc. Examples include:

[0489] The thickness of the electron transport layer 6 is usually 1 nm or more, preferably 5 nm or more. 00 nm or less, preferably 100 nm or less.

[0490] The electron transport layer 6 is formed by the wet film formation method or the vacuum deposition method in the same manner as described above. It is formed by laminating it on the hole blocking layer, usually by vacuum deposition.

[0491] In order to efficiently inject electrons injected from the cathode 7 into the electron transport layer 6 or the light emitting layer 5, An electron injection layer may be provided between the electron transport layer 6 and the cathode 7 .

[0492] To efficiently inject electrons, the material forming the electron injection layer is preferably a metal with a low work function. Examples include alkali metals such as sodium and cesium, and barium and calcium. The thickness of the film is preferably 0.1 nm or more and 5 nm or less. It's nice.

[0493] Furthermore, nitrogen-containing heterocyclic compounds such as bathophenanthroline and alkane derivatives of 8-hydroxyquinoline Organic electron transport materials, such as metal complexes, are often used in combination with sodium, potassium, and cerium. Doping with alkali metals such as sodium, lithium, rubidium, etc. (Japanese Patent Application Laid-Open No. 2008-27 Publication No. 0171, Japanese Patent Application Publication No. 2002-100478, Japanese Patent Application Publication No. 2002-10 0482, etc.), it is possible to improve electron injection and transport properties and achieve excellent film quality. This is preferable because it is possible to

[0494] The thickness of the electron injection layer is usually 5 nm or more, preferably 10 nm or more, and is usually 20 The thickness is in the range of 0 nm or less, preferably 100 nm or less.

[0495] The electron injection layer is formed by a wet film formation method or a vacuum deposition method on the light-emitting layer 5 or the hole-blocking layer thereon. The insulating layer 10 is formed by laminating it on the electron transport layer 6 . The details of the wet film formation method are the same as those of the light-emitting layer described above.

[0496] The hole blocking layer, electron transport layer, and electron injection layer are formed by co-doping the electron transport material with a lithium complex. It may also be made into one layer.

[0497] The cathode 7 serves to inject electrons into the layer (electron injection layer or light-emitting layer, etc.) on the light-emitting layer 5 side. vinegar.

[0498] The cathode 7 may be made of the same material as the anode 2. For efficient electron injection, it is preferable to use a metal with a low work function, for example, , tin, magnesium, indium, calcium, aluminum, silver, or other metals or Specific examples include magnesium-silver alloys, magnesium -Indium alloy, aluminum-lithium alloy, and other low work function alloy electrodes. do.

[0499] In terms of the stability of the organic electroluminescent device, a material with a high work function and stability against the atmosphere is placed on the cathode. It is preferable to laminate a metal layer having a low work function to protect the cathode. Examples of metals that can be used include aluminum, silver, copper, nickel, chromium, gold, and platinum. Examples include:

[0500] The thickness of the cathode is usually the same as that of the anode.

[0501] The organic electroluminescent device of the present invention may further comprise other layers as long as the effects of the present invention are not significantly impaired. That is, any of the other layers described above may be present between the anode and the cathode. stomach.

[0502] The organic electroluminescent device of the present invention has a structure opposite to that described above, i.e., a cathode on a substrate. , electron injection layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode in this order. Stacking is also possible.

[0503] When the organic electroluminescent element of the present invention is applied to an organic electroluminescent device, a single organic electroluminescent element When used as an element, a plurality of organic electroluminescent elements are arranged in an array. Alternatively, the anodes and cathodes may be arranged in an XY matrix.

[0504] The organic EL display device (organic electroluminescent device display device, also simply referred to as "display device") of the present invention ) is a display device equipped with the organic electroluminescent device of the present invention. There is no particular limitation on the type or structure of the organic electroluminescent device of the present invention. It can be assembled.

[0505] For example, "Organic EL Display" (Ohmsha, August 20, 2004, Shizuo Tokito) The organic EL display device of the present invention can be manufactured by a method such as that described in the publications by Adachi Chihaya and Murata Hideyuki. can be formed.

[0506] The organic EL lighting (organic electroluminescent element lighting, also simply referred to as "lighting device") of the present invention is The organic electroluminescent device of the present invention is a lighting device. There are no particular restrictions on the method, and the organic electroluminescent device of the present invention can be assembled in accordance with a conventional method. It is possible. [Example]

[0507] The present invention will be described in more detail below with reference to the following examples. The present invention is not limited to the above, and can be implemented by any modification without departing from the spirit of the invention. do.

[0508] [Example 1] An organic electroluminescent device was fabricated in the following manner. A transparent conductive film of indium tin oxide (ITO) was deposited on a glass substrate to a thickness of 50 nm. The product (manufactured by Geomatec, sputtered film) was then processed using ordinary photolithography technology. The anode was formed by patterning into stripes of 2 mm width using hydrochloric acid etching. The substrate on which the ITO pattern was formed was then subjected to ultrasonic cleaning with a surfactant solution and ultrapure water. After washing with water, ultrasonic cleaning with ultrapure water, and then washing with ultrapure water, the product was dried with compressed air. Finally, UV ozone cleaning was performed.

[0509] The composition for forming a hole injection layer is a compound having a repeating structure represented by the following formula (P-1): 3.0% by mass of a hole transporting polymer compound and an electron accepting compound represented by the following formula (HI-1): 0.6% by mass of the compound was dissolved in ethyl benzoate to prepare a composition.

[0510] This solution was spin-coated onto the substrate in the atmosphere, and then heated on a hot plate in the atmosphere for 24 The coating was dried at 0° C. for 30 minutes to form a uniform thin film with a thickness of 40 nm, which served as a hole injection layer.

[0511] [ka]

[0512] Next, 100 mass % of a charge transport polymer compound having a structure represented by the following formula (HT-1) was added. The resulting part was dissolved in mesitylene to prepare a 2.0 mass % solution. This solution was spin-coated on the substrate on which the hole injection layer had been formed in a nitrogen glove box. The coated film was dried at 230°C for 30 minutes on a hot plate in a nitrogen glove box. A uniform thin film with a thickness of 40 nm was formed as a hole transport layer.

[0513] [ka]

[0514] Subsequently, as a material for the light-emitting layer, 50 parts by mass of a compound represented by the following formula (H-1) 50 parts by mass of the compound represented by the formula (H-2) and 2 parts by mass of the compound represented by the formula (D-1) 0 parts by mass, and 2 parts by mass of the compound represented by the following formula (D-2) were weighed, and the compounds represented by each formula were The mass ratio is (H-1):(H-2):(D-1):(D-2) = 50:50:20:2 The resulting solution was dissolved in cyclohexylbenzene to give a 3.2% by mass solution, which was used as a composition for forming a light-emitting layer. It was prepared as follows.

[0515] [ka]

[0516] This composition for forming a light-emitting layer was applied to the substrate on which the hole transport layer had been formed by coating in a nitrogen globe box. After vacuum drying, the substrate was spin-coated on a hot plate in a nitrogen glove box. The coating was dried at 120° C. for 20 minutes to form a uniform thin film with a thickness of 62 nm, which served as the light-emitting layer.

[0517] The substrate on which the light-emitting layer had been formed was placed in a vacuum deposition device, and the inside of the device was heated to 2 × 10 -4 Pa or less It was vented until

[0518] Next, a compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatolithium were co-deposited on the light-emitting layer at a rate of 1 Å / sec by vacuum deposition so that the film thickness ratio was 2:3. A hole blocking layer having a thickness of 30 nm was formed.

[0519] [ka]

[0520] Next, a 2mm wide striped shadow mask was used as a mask for cathode evaporation, and the anode The ITO stripes were then placed in a vacuum deposition chamber. Then, aluminum was heated in a molybdenum boat and evaporated at a rate of 1 to 8.6 Å / s. An aluminum layer having a thickness of 58 nm was formed as a cathode.

[0521] In this way, an organic electroluminescent device having a light-emitting area of ​​2 mm x 2 mm was obtained. Obtained.

[0522] [Example 2] The compound represented by the following formula (H-4) is used, and the composition for forming the light-emitting layer is The mass ratio of the compounds is (H-1):(H-2):(H-4):(D-1):(D-2) The organic electrochemical reaction was carried out in the same manner as in Example 1, except that the ratio was 50:16.7:33.3:20:2. A field light emitting device was fabricated.

[0523] [ka]

[0524] [Comparative Example 1] Instead of the compound represented by formula (H-2), a compound represented by the following formula (H-3) was used to produce The composition for forming the optical layer was set to a mass ratio of the compounds represented by the formulas (H-1):(H-3). The same as in Example 1 except that the ratio of (D-1):(D-2) was 50:50:20:2. Thus, an organic electroluminescent device was fabricated.

[0525] [ka]

[0526] [Evaluation of organic electroluminescent devices] When a current was applied to the organic electroluminescent devices obtained in Examples 1 and 2 and Comparative Example 1, the In the organic electroluminescent device, green light emission originating from the compound represented by formula (D-2) was also observed. These organic electroluminescent devices were fabricated with a brightness of 1000 cd / m 2 Voltage (V) when emitting light The current efficiency (cd / A) was measured. 2 After aging for 10 minutes, the brightness of the element was reduced to 80% of the initial brightness. The time it took for the concentration to drop to 0 (LT80) was measured.

[0527] The voltage difference (referred to as relative voltage) between Examples 1 and 2 and Comparative Example 1 relative to the voltage of Comparative Example 1, The current efficiency of Comparative Example 1 and the relative values ​​of Examples 1 to 2 and Comparative Example 1 when LT80 is set to 1 The values ​​(referred to as relative current efficiency and relative life, respectively) are shown in Table 1.

[0528] [Table 1]

[0529] As shown in the results in Table 1, the compound (H-2) according to this embodiment can be used as a charge transport host. The organic electroluminescent device (Example 1) used in the composition for forming the light-emitting layer emits the compound (H-3). Compared with the organic electroluminescent device using the composition for forming an optical layer (Comparative Example 1), the driving voltage is low. It was found that the device had a long operating life.

[0530] In addition, the compound (H-2) and the compound (H-4) according to this embodiment are used as charge transport hosts. The organic electroluminescent device (Example 2) used in the composition for forming the light-emitting layer emits the compound (H-3). Compared with the organic electroluminescent device using the composition for forming an optical layer (Comparative Example 1), the efficiency is higher and the life is longer. It was found to be a long-lasting element. [Industrial Applicability]

[0531] The organic electroluminescent device of the present invention is suitably used for, for example, organic EL display devices and organic EL lighting. You can be there. [Explanation of symbols]

[0532] 1 board 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Cathode 8. Organic electroluminescent device

Claims

1. Formation of an organic film containing a compound represented by the following formula (2) and a compound represented by the following formula (71): Materials for use. 【Chemical 1】 [In formula (2), Ar １ is a structure represented by formula (2a). Ar ２ each independently represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent; Ar is a aryl group. ２ If there are multiple, they may be the same or different. Good too. Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a hetero group having 7 to 40 carbon atoms, or b) an aralkyl group, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryl group having 3 to 20 carbon atoms; an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 20 carbon atoms; an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, except for hydrogen atoms, may have a substituent. The other group has a structure represented by formula (2b). m and n each independently represent an integer of 1 to 3. 【Chemistry 2】 [In formula (2a), R １ each independently represents a hydrogen atom, a heterocyclic group having 3 to 20 carbon atoms which may have a substituent, ) an aryl group, Ar ２ It is a combination with 【Chemistry 3】 [In formula (2b), Ar ３ represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a hydroxy group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. These groups, except for the hydrogen atom, may have a substituent. "★" indicates the bonding position with formula (2). 【Chemistry 4】 (In formula (71), A １ ~A ７ At least one selected from the following is an electron accepting substituent; A other than the electron accepting substituent １ ~A ７ are each independently a hydrogen atom, a fluorine atom, atom or an alkyl group which may have a substituent, R ７１ ~R ７８ each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an electron-donating substituent, or a combination thereof; At least one hydrogen atom in the compound represented by formula (71) is replaced by a halogen atom or may be substituted with a deuterium atom, A dotted line represents a single bond or no bond.)

2. The organic film-forming material according to claim 1 , further comprising a compound represented by the following formula (7): 【Chemistry 5】 [In formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or a substituent represents an aromatic heterocyclic structure which may have the following structure: Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When there are a plurality of rings A701 and A702, they may be the same or different. That's fine. R ７０１ , R ７０２ are each independently a structure represented by formula (b), and "*" represents ring A701. or represents the bonding position with ring A702. ７０１ , R ７０２ are the same but different Also, R ７０１ , R ７０２ If there are multiple of each, they may be the same but different. It may be possible. Ar ７０１ , Ar ７０３ each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent. Ar ７０２ is an aromatic hydrocarbon ring structure which may have a substituent, It represents an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. Ar ７０１ , Ar ７０２ , and Ar ７０３ If there are multiple of each, they are the same But it may be different. The substituents bonded to ring A701, the substituents bonded to ring A702, or the substituents bonded to ring A701 and the substituents bonded to ring A702 may be bonded to each other to form a ring. good. B ７０１ -L ７００ -B ７０２ represents an anionic bidentate ligand. ７０１ and B ７ ０２ each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms form a ring. It may be an atom that ７００ is a single bond, or B ７０１ and B ７０２ Together 2 represents the atomic group constituting the dentate ligand. ７０１ -L ７００ -B ７０２ If there are multiple They may be the same or different. In addition, in the formulas (7) and (b), i1 and i2 each independently represent an integer of 0 to 12, i3 is Ar ７０２ represents an integer of 0 or more, with the upper limit being the number that can be replaced by j is Ar ７０１ represents an integer of 0 or more, with the upper limit being the number that can be replaced by k1 and k2 each independently represent an integer of 0 or greater, with the upper limit being the number of groups that can be substituted on ring A701 and ring A702. Represents the integer above. m is an integer from 1 to 3.

3. Furthermore, a compound selected from the compounds represented by the following formula (1) and the compounds represented by the following formula (260) is The organic film-forming material according to claim 1 , comprising at least one selected from the group consisting of: 【Chemistry 6】 [In formula (1), Each W independently represents CH or N, and at least one W is N; Xa １ , Ya １ , and Za １ each independently represents a group having 6 to 3 carbon atoms which may have a substituent a divalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents an aromatic heterocyclic group, Xa ２ , Ya ２ and Za ２ each independently represents a hydrogen atom, a carbon atom which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monovalent aromatic hydrocarbon group having 3 to 30 carbon atoms, which may have a substituent; represents a monovalent aromatic heterocyclic group, g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11, h11, and j11 is an integer of 1 or more, When g11 is 2 or more, a plurality of Xa １ may be the same or different, When h11 is 2 or more, multiple Ya １ may be the same or different, If j11 is 2 or more, multiple Za １ may be the same or different, R ３１ represents a hydrogen atom or a substituent, and 12 R ３１ Whether they are the same or different often, However, when g11, h11, or j11 is 0, the corresponding Xa ２ , Ya ２ , Z a ２ is not a hydrogen atom. 【Chemistry 7】 (In formula (260), Ar ６１ ~Ar ６５ each independently represents a hydrogen atom or a monovalent group which may have a substituent; an aromatic hydrocarbon group having 6 to 60 carbon atoms, L １ ~L ５ each independently represents a divalent group having 6 to 60 carbon atoms which may have a substituent; is an aromatic hydrocarbon group of the formula R ６０ each independently represents a substituent, m1 to m5 each independently represent an integer of 0 to 5; n represents an integer of 0 to 10; a1 to a3 each independently represent an integer of 0 to 3; However, Ar ６１ , Ar ６２ , Ar ６３ , Ar ６４ , and at least when n is 1 or more Another Ar ６５ At least one of them is not a hydrogen atom.)

4. The material for forming an organic film according to claim 3, which contains at least a compound represented by formula (1): 。

5. R in the formula (2), formula (2a), and formula (2b) １ , R ２ , Ar ２ and Ar ３ has The optional substituents are each independently an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryl group, an aryloxy ... oxy group, aryloxy group, heteroaryloxy group, alkylsilyl group, arylsilyl group alkyl group, alkylcarbonyl group, arylcarbonyl group, alkylamino group, aryl 2. The organic film-forming material according to claim 1, wherein the aryl group is an amino group, an aryl group, or a heteroaryl group. Fee.

6. The organic film-forming material according to claim 1, wherein the formula (2) is represented by the following formula (2-1): 【Chemistry 8】 [In formula (2-1), Ar ４ is a structure represented by the formula (2a), Ar ５ is Ar in the formula (2). ２ is a group selected from groups similar to those Ar ６ is Ar in the formula (2b). ３ is a group selected from groups similar to those R ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a hydroxy group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, except for the hydrogen atom, may have a substituent. Ar ５ and Ar ６ When there are multiple of each, they may be the same or different. 。 j and k are values ​​selected from the same ranges as m and n in formula (2).

7. Ar in the formula (2-1) ５ each independently represents a 1,3-phenylene group or a 1,4- The organic film-forming material according to claim 6 , which is a phenylene group.

8. R in the formula (2-1) ３ , Ar ５ and Ar ６ The substituents which may be contained in alkyl groups, aralkyl groups, heteroaralkyl groups, alkoxy groups, aryloxy groups , heteroaryloxy group, alkylsilyl group, arylsilyl group, alkylcarbonyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or The organic film-forming material according to claim 6 , which is a heteroaryl group.

9. The organic film-forming material according to claim 3, wherein the formula (1) is represented by the following formula (1-1): 【Chemistry 9】 [In formula (1-1), W １ , W ２ and W ３ each independently represents —CH or a nitrogen atom; W １ , W ２ and W ３ at least one of which is a nitrogen atom, Xa １ , Ya １ , and Za １ each independently represents a 1,3-phenylene group which may have a substituent; represents an phenylene group or an optionally substituted 1,4-phenylene group, Za １ at least one of is a 1,3-phenylene group, Xa ２ and Ya ２ each independently represents an optionally substituted phenyl group, Za ２ represents an N-carbazolyl group which may have a substituent, f11 is 1 or 2, g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer from 1 to 6, f11+g11+h11+j11 is 5 or more, R １１ each independently represents a hydrogen atom or a substituent.

10. The organic film-forming material according to claim 3, wherein the formula (1) is represented by the following formula (1-2): 【Chemistry 10】 [In formula (1-2), W １ , W ２ and W ３ each independently represents —CH or a nitrogen atom; W １ , W ２ and W ３ at least one of which is a nitrogen atom, Xa １ , Ya １ , and Za １ each independently represents a 1,3-phenylene group which may have a substituent; represents an phenylene group or an optionally substituted 1,4-phenylene group, Ya １ and Za １ At least one of the groups is 1,3-phenylene which may have a substituent. It is the basis, Xa ２ represents an optionally substituted phenyl group, Ya ２ and Za ２ each independently represents an N-carbazolyl group which may have a substituent; death, f11 is 1 or 2, g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer from 2 to 5, f11+g11+h11+j11 is 6 or more, R １１ each independently represents a hydrogen atom or a substituent.

11. Ya in the formula (1-2) １ at least one of Z is a 1,3-phenylene group; a １ 11. The organic film forming method according to claim 10, wherein at least one of the groups is a 1,3-phenylene group. material.

12. Xa in the formula (1-2) １ at least one of which is a 1,3-phenylene group; 11. The organic film-forming material according to claim 10.

13. The singlet energy level S of the compound represented by the formula (2) １ (eV) and triplet energy -Level T １ (eV) difference (ΔE ＳＴ １ ) is 0.2 (eV) or more according to claim 1 Material for organic film formation.

14. An organic film forming method comprising the organic film forming material according to any one of claims 1 to 13 and a solvent. Composition for use.

15. A method for producing an organic film by forming the organic film-forming composition according to claim 14 by a wet film-forming method. Law.

16. An organic film having an organic layer containing the organic film-forming material according to any one of claims 1 to 13. Electroluminescent device.

17. A display device comprising the organic electroluminescent device according to claim 16.

18. A lighting device comprising the organic electroluminescent device according to claim 16.

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