Compound, material for organic elements, ink composition, organic electroluminescent element, display device, and lighting device

Abstract

The invention provides a compound, a material for organic elements, an ink composition, an organic electroluminescent element, a display device, and a lighting device. The present invention increases options for organic element materials such as organic EL element materials by condensing a cycloalkane in a polycyclic aromatic compound in which a plurality of aromatic rings are linked by a boron atom and an oxygen atom or the like. Also provided is an organic EL element having excellent luminous efficiency and element life, for example, by using the novel cycloalkane-condensed polycyclic aromatic compound as a material for an organic EL element.

Description

[0001] This application is a divisional application with application number 202080015059.1 filed on April 14, 2020, and the invention name is compounds, materials for organic elements, ink compositions, organic electroluminescent elements, display devices, and lighting devices. Technical Field

[0002] The present invention relates to a cycloalkane condensation polycyclic aromatic compound and a polymer thereof (hereinafter collectively referred to as a "polycyclic aromatic compound"), an organic element material, an ink composition, and an organic electroluminescent element, an organic field effect transistor, and an organic thin film solar cell using the same, as well as a display device and a lighting device. In this specification, an "organic electroluminescent element" may be referred to as an "organic EL (electroluminescence) element" or simply as an "element". Background Art

[0003] In the past, display devices using light-emitting elements that perform electroluminescence have been studied in various ways because they can achieve power saving or thinning, and organic electroluminescent elements containing organic materials have been actively studied because they can be easily lightweight or large-scaled. In particular, the development of organic materials having luminous properties such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities such as holes and electrons (having the possibility of becoming semiconductors or superconductors) have been actively studied to date, regardless of whether they are polymer compounds or low molecular weight compounds.

[0004] An organic EL element has a structure including a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and including an organic compound. The layers including the organic compound include a light-emitting layer, a charge transport / injection layer for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0005] As materials for light-emitting layers, for example, benzofluorene compounds have been developed (International Publication No. 2004 / 061047). In addition, as hole transport materials, for example, triphenylamine compounds have been developed (Japanese Patent Laid-Open No. 2001-172232). In addition, as electron transport materials, for example, anthracene compounds have been developed (Japanese Patent Laid-Open No. 2005-170911).

[0006] In addition, in recent years, materials obtained by improving triphenylamine derivatives have also been reported as materials for organic EL elements or organic thin-film solar cells (International Publication No. 2012 / 118164). The material is a material in which the aromatic rings constituting triphenylamine are linked to each other with reference to the practical N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), thereby improving its planarity. In the literature, for example, the charge transport properties of NO-linked compounds (Compound 1 on page 63) are evaluated, but the method for producing materials other than NO-linked compounds is not described. In addition, if the linked elements are different, the overall electronic state of the compound is different, so the properties obtained from materials other than NO-linked compounds are still unknown. Examples of such compounds can also be found elsewhere (International Publication No. 2011 / 107186). For example, a compound with a conjugated structure having a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and is therefore useful as a blue light-emitting layer material. In addition, a compound with a novel conjugated structure having a large T1 is also required as an electron transport material or hole transport material sandwiching the light-emitting layer.

[0007] The host material of an organic EL element is usually a molecule formed by linking multiple existing aromatic rings such as benzene or carbazole using single bonds or phosphorus atoms or silicon atoms. The reason is that by linking multiple relatively small conjugated aromatic rings, the large highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gap (band gap Eg of the film) required by the host material is guaranteed. Furthermore, in the host material of an organic EL element using a phosphorescent material or a thermally activated delayed fluorescent material, a high triplet excitation energy (Eg) is also required. T ), but by linking the donor or acceptor aromatic ring or substituent to the molecule, the single occupied molecular orbital (SOMO) 1 and SOMO2 of the triplet excited state (T1) are localized and the exchange interaction between the two orbitals is reduced, thereby increasing the triplet excitation energy (E T ). However, the redox stability of aromatic rings with small conjugated systems is not sufficient, and the life of devices using molecules with existing aromatic rings as main materials is not sufficient. On the other hand, polycyclic aromatic compounds with extended π conjugated systems generally have excellent redox stability, but the HOMO-LUMO gap (band gap Eg of the film) or triplet excitation energy (E T) is low and therefore considered unsuitable as a host material.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: International Publication No. 2004 / 061047

[0011] Patent Document 2: Japanese Patent Application Publication No. 2001-172232

[0012] Patent Document 3: Japanese Patent Application Publication No. 2005-170911

[0013] Patent Document 4: International Publication No. 2012 / 118164

[0014] Patent Document 5: International Publication No. 2011 / 107186

[0015] Patent Document 6: International Publication No. 2015 / 102118 Summary of the invention

[0016] Problems to be solved by the invention

[0017] As described above, various materials have been developed as materials for organic EL elements. In order to increase the selection of materials for organic EL elements, it is desired to develop materials containing compounds different from the existing ones. In particular, organic EL properties obtained from materials other than the NO-linked compounds reported in Patent Documents 1 to 4 or their production methods are still unknown.

[0018] Patent Document 6 reports a polycyclic aromatic compound containing boron and an organic EL element using the same. However, in order to further improve the device characteristics, a light-emitting layer material, particularly a dopant material, that can improve the light-emitting efficiency or the device life is desired.

[0019] Technical means of solving problems

[0020] The inventors have conducted intensive research to solve the above-mentioned problems, and as a result, have found that an excellent organic EL element can be obtained by arranging a layer containing a polycyclic aromatic compound condensed with a cycloalkane between a pair of electrodes to form, for example, an organic EL element, thereby completing the present invention. That is, the present invention provides the following cycloalkane condensed polycyclic aromatic compound or its multimer, and an organic element material including the following cycloalkane condensed polycyclic aromatic compound or its multimer, and the like.

[0021] Furthermore, in this specification, the carbon number is sometimes used to represent the chemical structure or substituent, but when the chemical structure is substituted with a substituent, or when the substituent is further substituted with a substituent, the carbon number refers to the carbon number of the chemical structure or the substituent, and does not refer to the total carbon number of the chemical structure and the substituent, or the total carbon number of the substituent and the substituent. For example, the so-called "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B. In addition, for example, the so-called "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without limiting the carbon number)" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B.

[0022] Item 1.

[0023] A polycyclic aromatic compound or a multimer of a polycyclic aromatic compound, wherein the polycyclic aromatic compound is represented by the following general formula (1), and the multimer of a polycyclic aromatic compound has a plurality of structures represented by the following general formula (1).

[0024] [Chemistry 7]

[0025]

[0026] (In the formula (1),

[0027] Ring A, Ring B and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted.

[0028] Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl,

[0029] X 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S or >Se, the R of the >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted, the >C(-R) 2 R is hydrogen, aryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, and R of the >NR and the >C(-R) 2 At least one of the R's may be bonded to at least one of the A ring, the B ring, and the C ring via a linking group or a single bond,

[0030] At least one hydrogen in the compound or structure represented by formula (1) may be substituted by deuterium, cyano or halogen, and,

[0031] At least one of the A ring, B ring, C ring, aryl group and heteroaryl group in the compound or structure represented by formula (1) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - can be replaced by -O-)

[0032] Item 2.

[0033] The polycyclic aromatic compound or multimer thereof according to item 1, wherein

[0034] In the formula (1),

[0035] The A ring, the B ring and the C ring are each independently an aryl ring or a heteroaryl ring, at least one hydrogen in these rings may be substituted by a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group, and these rings have a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group. 1 , X 1 and X 2 The condensed bicyclic structure in the center of the formula has a total of 5-membered rings or 6-membered rings,

[0036] Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl,

[0037] X 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S or >Se, wherein R of the >NR is an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, and the >C(-R) 2 R is hydrogen, aryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl, and R of the >NR and the >C(-R) 2 At least one of the R can be -O-, -S-, -C(-R) 2 - or a single bond to at least one of the A ring, B ring and C ring, wherein -C(-R) 2 -R is hydrogen, alkyl or cycloalkyl,

[0038] At least one hydrogen in the compound or structure represented by formula (1) may be replaced by deuterium, cyano or halogen.

[0039] In the case of a multimer, it is a dimer or trimer having two or three structures represented by the general formula (1), and,

[0040] At least one of the A ring, B ring, C ring, aryl group and heteroaryl group in the compound or structure represented by formula (1) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-.

[0041] Item 3.

[0042] The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2).

[0043] [Chemistry 8]

[0044]

[0045] (In the formula (2),

[0046] Any "-C(-R)=" (where R is R in formula (2)) in the a ring, b ring and c ring 1 ~R 11 ) may be substituted by "-N=", any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 ) may be substituted with "-N(-R)-", "-O-" or "-S-", wherein R of "-N(-R)-" is aryl, alkyl or cycloalkyl,

[0047] R 1 ~R 11 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, at least one hydrogen in these groups may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group, and R 1 ~R 11The adjacent groups in the group may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group or an alkyldicycloalkylsilyl group, and at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group,

[0048] Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

[0049] X 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S or >Se, wherein R of the >NR is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and the >C(-R) 2 R is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. In addition, R of the >NR and the >C(-R) 2 At least one of the R can be -O-, -S-, -C(-R) 2 - or a single bond to at least one of the a ring, b ring and c ring, the -C(-R) 2 -R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

[0050] At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and

[0051] At least one of the a ring, the b ring, the c ring, the formed ring, the aryl group and the heteroaryl group in the compound represented by formula (2) is condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, at least one -CH 2 - can be replaced by -O-)

[0052] Item 4.

[0053] The polycyclic aromatic compound according to item 3, wherein

[0054] In the formula (2),

[0055] Any "-C(-R)=" (where R is R in formula (2)) in the a ring, b ring and c ring 1 ~R 11 ) may be substituted by "-N=", any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 ) may be substituted with "-N(-R)-", "-O-" or "-S-", wherein R of "-N(-R)-" is an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

[0056] R 1 ~R 11 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and two aryl groups may be bonded via a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a triarylsilyl group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), or a trialkylsilyl group (wherein the alkyl group is an alkyl group having 1 to 6 carbon atoms), and R 1 ~R 11 The adjacent groups in the ring may be bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a triarylsilyl group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms) or a trialkylsilyl group (wherein the alkyl group is an alkyl group having 1 to 5 carbon atoms),

[0057] Y 1 is B, P, P=O, P=S or Si-R, wherein R of Si-R is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

[0058] X 1 and X 2 are independently >O, >NR, >C(-R) 2 or>S, wherein R of the>NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, and the>C(-R) 2 R is hydrogen, an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms,

[0059] At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and

[0060] At least one of the a ring, the b ring, the c ring, the formed ring, the aryl group and the heteroaryl group in the compound represented by formula (2) is condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms.

[0061] Item 5.

[0062] The polycyclic aromatic compound according to item 3, wherein

[0063] In the formula (2),

[0064] Any "-C(-R)=" (where R is R in formula (2)) in the a ring, b ring and c ring 1 ~R 11 ) may be substituted by "-N=", any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 ) may be substituted with "-N(-R)-", "-O-" or "-S-", wherein R of "-N(-R)-" is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

[0065] R 1 ~R 11 are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

[0066] Y 1 is B, P, P=O or P=S,

[0067] X 1 and X 2 are independently >O, >NR or >C(-R) 2 , R of the >NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, and the >C(-R) 2 R is hydrogen, an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms,

[0068] At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and

[0069] In the compound represented by formula (2), at least one of the aromatic groups having 6 to 10 carbon atoms, the aromatic groups having 6 to 10 carbon atoms, the aromatic groups having 6 to 10 carbon atoms and the aromatic groups having 3 to 16 carbon atoms as R of the >NR are condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen atom in the cycloalkane may be replaced by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

[0070] Item 6.

[0071] The polycyclic aromatic compound according to item 3, wherein

[0072] R 1 ~R 11 are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

[0073] Y 1 For B,

[0074] X 1 and X 2 All are >NR, or X 1 is >NR and X 2 is>O, and R of the>NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms,

[0075] At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium or halogen, and

[0076] In the compound represented by formula (2), at least one of the a ring, the b ring, the c ring and the aromatic group having 6 to 10 carbon atoms as R of the >NR is condensed with a cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl group having 1 to 5 carbon atoms.

[0077] Item 7.

[0078] The polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 6, which is substituted with a diarylamino group condensed with a cycloalkane, a carbazole group condensed with a cycloalkane, or a benzocarbazole group condensed with a cycloalkane.

[0079] Item 8.

[0080] The polycyclic aromatic compound according to any one of items 3 to 6, wherein R 2 It is a diarylamino group condensed with a cycloalkane or a carbazole group condensed with a cycloalkane.

[0081] Item 9.

[0082] The polycyclic aromatic compound according to item 7 or 8, wherein the cycloalkane is a cycloalkane having 3 to 20 carbon atoms.

[0083] Item 10.

[0084] The polycyclic aromatic compound or multimer thereof according to any one of items 1 to 8, wherein the halogen is fluorine.

[0085] Item 11.

[0086] The polycyclic aromatic compound according to Item 1, which is represented by any one of the following structural formulas.

[0087] [Chemistry 9]

[0088]

[0089] [Chemistry 10]

[0090]

[0091] [Chemistry 11]

[0092]

[0093] [Chemistry 12]

[0094]

[0095] (“Me” in each of the structural formulas represents a methyl group, and “tBu” represents a tert-butyl group)

[0096] Item 12.

[0097] A reactive compound, wherein a reactive substituent is substituted on the polycyclic aromatic compound or multimer thereof according to any one of items 1 to 11.

[0098] Item 13.

[0099] A polymer compound or a polymer cross-linked product, wherein the polymer compound is obtained by polymerizing the reactive compound according to item 12 as a monomer, and the polymer cross-linked product is obtained by further cross-linking the polymer compound.

[0100] Item 14.

[0101] A pendant polymer compound or a pendant polymer crosslinked product, wherein the pendant polymer compound is formed by substituting the reactive compound according to item 12 in a main chain polymer, and the pendant polymer crosslinked product is formed by further crosslinking the pendant polymer compound.

[0102] Item 15.

[0103] A material for an organic device, comprising the polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 11.

[0104] Item 16.

[0105] A material for an organic element, comprising the reactive compound according to item 12.

[0106] Item 17.

[0107] A material for an organic device, comprising the polymer compound or the polymer crosslinked product according to item 13.

[0108] Item 18.

[0109] A material for an organic element, comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 14.

[0110] Item 19.

[0111] The material for an organic device according to any one of Items 15 to 18, wherein the material for an organic device is a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

[0112] Item 20.

[0113] The material for an organic device according to item 19, wherein the material for an organic electroluminescent device is a material for a light-emitting layer.

[0114] Item 21.

[0115] An ink composition comprising: the polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 11; and an organic solvent.

[0116] Item 22.

[0117] An ink composition comprising: the reactive compound according to item 12; and an organic solvent.

[0118] Item 23.

[0119] An ink composition comprising: a main-chain polymer; the reactive compound according to item 12; and an organic solvent.

[0120] Item 24.

[0121] An ink composition comprising: the polymer compound or polymer crosslinked product according to item 13; and an organic solvent.

[0122] Item 25.

[0123] An ink composition comprising: the pendant polymer compound or the pendant polymer crosslinked body according to item 14; and an organic solvent.

[0124] Item 26.

[0125] An organic electroluminescent element comprises: a pair of electrodes including an anode and a cathode; and an organic layer arranged between the pair of electrodes and containing a polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 11, a reactive compound according to item 12, a polymer compound or a polymer crosslinked product according to item 13, or a pendant polymer compound or a pendant polymer crosslinked product according to item 14.

[0126] Item 27.

[0127] The organic electroluminescent element according to item 26, wherein the organic layer is a light-emitting layer.

[0128] Item 28.

[0129] An organic electroluminescent element according to item 27, wherein the light-emitting layer comprises: a main body; and the polycyclic aromatic compound, its polymer, reactive compound, polymer compound, polymer crosslinked body, pendant polymer compound or pendant polymer crosslinked body as a dopant.

[0130] Item 29.

[0131] The organic electroluminescent device according to item 28, wherein the host is an anthracene compound, a fluorene compound or a dibenzo Series of compounds.

[0132] Item 30.

[0133] An organic electroluminescent element according to any one of items 26 to 29, which has at least one layer of an electron transport layer and an electron injection layer arranged between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives and quinolinol metal complexes.

[0134] Item 31.

[0135] An organic electroluminescent element according to item 30, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes.

[0136] Item 32.

[0137] An organic electroluminescent element according to any one of items 26 to 31, wherein at least one of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the electron injection layer comprises: a polymer compound or a polymer cross-linked body, or a pendant polymer compound or a pendant polymer cross-linked body, the polymer compound is formed by polymerizing a low molecular compound that can form each layer as a monomer, the polymer cross-linked body is formed by further cross-linking the polymer compound, the pendant polymer compound is formed by reacting a low molecular compound that can form each layer with a main chain polymer, and the pendant polymer cross-linked body is formed by further cross-linking the pendant polymer compound.

[0138] Item 33.

[0139] A display device or a lighting device, comprising the organic electroluminescent element according to any one of items 26 to 32.

[0140] Effects of the Invention

[0141] According to a preferred embodiment of the present invention, a novel cycloalkane condensed polycyclic aromatic compound that can be used as a material for an organic element such as an organic EL element can be provided. By using the cycloalkane condensed polycyclic aromatic compound, an excellent organic element such as an organic EL element can be provided.

[0142] Specifically, the inventors have found that polycyclic aromatic compounds (basic skeleton parts) formed by linking aromatic rings with heterogeneous elements such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap (band gap Eg of the film) and a high triplet excitation energy (E T). The reason is believed to be that the aromaticity of the 6-membered ring containing the heteroelement is low, so the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugated system is suppressed, and the electronic disturbance of the heteroelement causes the SOMO1 and SOMO2 of the triplet excited state (T1) to be localized. In addition, the polycyclic aromatic compound (basic skeleton part) containing the heteroelement of the present invention localizes SOMO1 and SOMO2 in the triplet excited state (T1), and the exchange interaction between the two orbitals becomes small, so the energy difference between the triplet excited state (T1) and the singlet excited state (S1) is small, and thermally activated delayed fluorescence is exhibited, so it is also useful as a fluorescent material for organic EL elements (including elements utilizing thermally activated delayed fluorescence). In addition, it has a high triplet excitation energy (E T ) are also useful as electron transport layers or hole transport layers of phosphorescent organic EL elements or organic EL elements utilizing thermally activated delayed fluorescence. Furthermore, these polycyclic aromatic compounds (basic skeleton parts) can arbitrarily change the energies of HOMO and LUMO by introducing substituents, so that the ionization potential or electron affinity can be optimized according to the surrounding materials.

[0143] In addition to the characteristics of this basic skeleton part, the compound of the present invention can also suppress concentration quenching by condensing cycloalkanes, and can also expect improvements in device life or luminous efficiency. Device life or luminous efficiency is an important characteristic value of an organic element. By using the compound of the present application, it can be expected to improve the characteristics of the element. In addition, a reduction in melting point or sublimation temperature can be expected. The situation refers to the fact that in the sublimation refining that is almost indispensable as a refining method for materials for organic elements such as organic EL elements requiring high purity, the refining can be performed at a relatively low temperature, so that the thermal decomposition of the material can be avoided. In addition, the situation is also the same for the vacuum evaporation process, and the process can be implemented at a relatively low temperature, so the thermal decomposition of the material can be avoided, and a high-performance organic element can be obtained as a result. The vacuum evaporation process is a powerful means for making organic elements such as organic EL elements. In addition, with respect to the polymers of polycyclic aromatic compounds, there are many compounds with high sublimation temperatures due to high molecular weight or planarity, so the reduction of the sublimation temperature caused by condensing cycloalkanes becomes more effective. In addition, since the solubility in an organic solvent is improved by the condensation of cycloalkanes, it can also be applied to the production of a device using a coating process. However, the present invention is not particularly limited to these principles. BRIEF DESCRIPTION OF THE DRAWINGS

[0144] Figure 1 It is a schematic cross-sectional view showing the organic EL element according to this embodiment.

[0145] [Explanation of Symbols]

[0146] 100: Organic electroluminescent element

[0147] 101: Substrate

[0148] 102: Anode

[0149] 103: Hole injection layer

[0150] 104: Hole transport layer

[0151] 105: Luminous layer

[0152] 106: Electron transport layer

[0153] 107: Electron injection layer

[0154] 108: cathode. DETAILED DESCRIPTION

[0155] 1. Polycyclic aromatic compounds and their polymers through cycloalkane condensation

[0156] The invention of the present application is a polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1), preferably a polycyclic aromatic compound represented by the following general formula (2), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2), wherein at least one of the A ring, B ring, C ring, aromatic group and heteroaromatic group in these compounds or structures is condensed by at least one cycloalkane.

[0157] [Chemistry 13]

[0158]

[0159] The A ring, the B ring and the C ring in the general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted by a substituent. The substituent is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl group and a heteroaryl group), a substituted or unsubstituted diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silane group. When these groups have a substituent, the substituent includes an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group. In addition, the aryl ring or the heteroaryl ring preferably has a substituted alkyl group containing Y. 1 , X 1 and X 2The central condensed bicyclic structure of the general formula (1) has a bonded 5-membered ring or a 6-membered ring.

[0160] Here, the "condensed bicyclic structure" refers to the structure containing Y 1 , X 1 and X 2 The structure formed by condensation of two saturated hydrocarbon rings. In addition, the so-called "six-membered ring that shares a bond with the condensed bicyclic structure" refers to the a ring (benzene ring (six-membered ring)) condensed in the condensed bicyclic structure, as shown in the general formula (2). In addition, the so-called "(A ring) aryl ring or heteroaryl ring having the six-membered ring" means that the A ring is formed only by the six-membered ring, or that other rings are further condensed in the six-membered ring in a manner that includes the six-membered ring to form the A ring. In other words, the so-called "(A ring) aryl ring or heteroaryl ring having a six-membered ring" mentioned here means that all or part of the six-membered rings constituting the A ring are condensed in the condensed bicyclic structure. The same description also applies to the "B ring (b ring)", "C ring (c ring)" and "5-membered ring".

[0161] The A ring (or B ring, C ring) in the general formula (1) corresponds to the a ring in the general formula (2) and its substituent R 1 ~R 3 (or b ring and its substituent R 8 ~R 11 , c ring and its substituent R 4 ~R 7 ). That is, the general formula (2) corresponds to a structure in which "Ring A to Ring C having a 6-membered ring" are selected as Ring A to Ring C of the general formula (1). In the above meaning, each ring of the general formula (2) is represented by lower case letters a to c.

[0162] In the general formula (2), the substituents R of the a ring, b ring and c ring are 1 ~R 11 The adjacent groups in the formula (2) may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring. At least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group or an alkyldicycloalkylsilyl group. At least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group. Therefore, the polycyclic aromatic compound represented by the general formula (2) changes the ring structure of the compound according to the mutual bonding form of the substituents in the a ring, the b ring and the c ring, as shown in the following formula (2-1) and formula (2-2). The A' ring, the B' ring and the C' ring in each formula correspond to the A ring, the B ring and the C ring in the general formula (1), respectively.

[0163] [Chemistry 14]

[0164]

[0165] When the general formula (2) is used for explanation, the A' ring, B' ring and C' ring in the formula (2-1) and the formula (2-2) represent the substituent R 1 ~R 11 The adjacent groups in the a ring are bonded to each other and form an aryl ring or a heteroaryl ring (which can also be called a condensed ring formed by condensing other ring structures in the a ring, b ring or c ring). Furthermore, although not shown in the formula, there are compounds in which the a ring, b ring and c ring are all changed to the A' ring, B' ring and C' ring. In addition, as can be seen from the above formula (2-1) and formula (2-2), for example, R of the b ring 8 R with c ring 7 , R of b ring 11 R with a ring 1 , c-ring R 4 R with a ring 3 The term "adjacent groups" does not apply to "adjacent groups", and these groups are not bonded. That is, the term "adjacent groups" refers to groups that are adjacent to each other on the same ring.

[0166] The compound represented by the formula (2-1) or (2-2) is, for example, a compound having a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzothiophene ring, which is condensed with a benzene ring as the a ring (or the b ring or the c ring) to form an A' ring (or the B' ring or the C' ring), and the formed condensed ring A' (or the condensed ring B' or the condensed ring C') is respectively a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

[0167] Y in the general formula (1) 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is an aryl group, an alkyl group or a cycloalkyl group. In the case of P=O, P=S, Si-R or Ge-R, the atom bonded to the A ring, the B ring or the C ring is P, Si or Ge. 1 It is preferably B, P, P=O, P=S or Si-R, and particularly preferably B. The above description also applies to Y in the general formula (2). 1 .

[0168] X in the general formula (1) 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S or >Se, the R of the >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted, the >C(-R)2 R is hydrogen, aryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, the R of the >NR and the >C(-R) 2 At least one of the R's may be bonded to at least one of the A ring, the B ring, and the C ring via a linking group or a single bond, and the linking group is preferably -O-, -S-, or -C(-R) 2 -. Furthermore, the "-C(-R) 2 -" is hydrogen, alkyl or cycloalkyl. The above description also applies to X in the general formula (2) 1 and X 2 .

[0169] Here, in the general formula (1), "the R of the >NR and the >C(-R) 2 The provision that "at least one of the R of >NR and the >C(-R)" is bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond corresponds to the provision that "the R of >NR and the >C(-R) 2 At least one of the R's is -O-, -S-, -C(-R) 2 - or a single bond to at least one of the a ring, b ring and c ring".

[0170] The above-mentioned regulation can be expressed by the following compound, which is represented by the following formula (2-3-1) and has X 1 or X 2 The ring structure introduced into the condensed ring B' and the condensed ring C'. That is, for example, it is a ring structure having other rings to introduce X 1 (or X 2 ) is a compound of a B' ring (or a C' ring) formed by condensing a benzene ring as the b ring (or the c ring) in the general formula (2). The formed condensed ring B' (or condensed ring C') is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.

[0171] In addition, the above provisions can also be expressed by the following compound, which is represented by the following formula (2-3-2) or formula (2-3-3) and has X 1 and X 2 At least one of which is introduced into the condensed ring A'. That is, for example, a ring structure having other rings to introduce X 1 (or X 2 or X 1 and X 2 ) is a compound in which the benzene ring as the a ring in the general formula (2) is condensed to form the A' ring. The condensed ring A' formed is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.

[0172] [Chemistry 15]

[0173]

[0174] In formula (2), any "-C(-R)=" (where R is R in formula (2)) in ring a, ring b and ring c 1 ~R 11 ) can be replaced by "-N=".

[0175] [Chemistry 16]

[0176]

[0177] As shown above, for example, the "-C(-R 5 )=” can be substituted with “-N=”, and thus, the C ring represented by a benzene ring in formula (2) can be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. In addition, as described above, when there is an adjacent group on the C ring (R in the formula 6 and R 7 ), which are bonded together with the c ring to form a heteroaryl ring (a quinoline ring in the formula), and the formed ring may also be substituted (represented by n Rs).

[0178] In addition, there are also the following modified examples.

[0179] [Chemistry 17]

[0180]

[0181] The same applies to the case where other sites are substituted with "-N=" or the case where the a-ring or the b-ring is changed.

[0182] In formula (2), any of "-C(-R)=C(-R)-" (where R is R in formula (2)) in ring a, ring b and ring c 1 ~R 11 ) may be substituted with "-N(-R)-", "-O-" or "-S-", wherein R of "-N(-R)-" is an aryl group, an alkyl group or a cycloalkyl group. The details of the substituents listed here will be summarized later.

[0183] [Chemistry 18]

[0184]

[0185] As shown above, for example, the "-C(-R 7 )=C(-R 6)-" can be substituted with "-N(-R)-", "-O-" or "-S-", so that the c ring represented by the benzene ring in formula (2) can be changed to a pyrrole ring, furan ring, thiophene ring, or other nitrogen / oxygen / sulfur-containing heteroaryl ring substituted with R. In addition, as described above, when there is an adjacent group on the c ring (R in the formula 4 and R 5 ), which are bonded together with the c ring to form a heteroaryl ring (an indole ring, a benzofuran ring or a benzothiophene ring substituted with R in the formula), and the formed ring may also be further substituted (represented by n Rs).

[0186] In addition, there are also the following modified examples.

[0187] [Chemistry 19]

[0188]

[0189] The same applies to cases where other sites are substituted with "-N(-R)-", "-O-" or "-S-", or where the a-ring or b-ring is changed.

[0190] Furthermore, in the description of the above formulas (2-1), (2-2), (2-3-1), (2-3-2) and (2-3-3), the a ring, b ring and c ring are described as benzene rings, and the same applies to the case where the a ring to the c ring are changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen / sulfur heteroaryl ring (5-membered ring).

[0191] Examples of the "aryl ring" of the ring A, ring B and ring C in the general formula (1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. The "aryl ring" corresponds to "R" in the general formula (2). 1 ~R 11 Adjacent groups in the a ring are bonded to each other and form an aryl ring together with the a ring, the b ring or the c ring. In addition, the a ring (or the b ring, the c ring) already contains a benzene ring with 6 carbon atoms, so the total carbon number of 9 in the condensed ring formed by condensing the 5-membered ring therein becomes the lower limit of the carbon number.

[0192] Specific examples of the "aryl ring" include: a benzene ring as a monocyclic ring system, a biphenyl ring as a bicyclic ring system, a naphthalene ring as a condensed bicyclic ring system, a terphenyl ring (meta-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic ring system, an acenaphthene ring, a fluorene ring, a phenanthren ring, a phenanthrene ring, an anthracene ring as a condensed tricyclic ring system, a triphenylene ring, a pyrene ring, a naphthacene ring as a condensed tetracyclic ring system, a perylene ring, a pentacene ring, and the like.

[0193] Examples of the "heteroaryl ring" of the A ring, B ring and C ring of the general formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. In addition, examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon. The "heteroaryl ring" corresponds to "R" in the general formula (2). 1 ~R 11 Adjacent groups in the a ring are bonded to each other and form a heteroaryl ring together with the a ring, the b ring or the c ring. In addition, the a ring (or the b ring, the c ring) already contains a benzene ring with 6 carbon atoms, and therefore, the total carbon number of 6 in the condensed ring formed by condensing the 5-membered ring therein becomes the lower limit of the carbon number.

[0194] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiol ring, a phenoxazine ring, a phenothiazine ring, and a phenazine ring. , cyclopentylboronic acid (phenazasiline) ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophosphole oxide ring, dibenzophosphole oxide ring, furazan ring, thianthrene ring, indolecarbazole ring, benzindazolecarbazole ring, benzobenzoindolecarbazole ring, imidazoline ring, oxazoline ring, etc.

[0195] At least one hydrogen in the “aryl ring” or “heteroaryl ring” may be replaced by a substituted or unsubstituted “aryl”, a substituted or unsubstituted “heteroaryl”, a substituted or unsubstituted “diarylamino”, a substituted or unsubstituted “diheteroarylamino”, a substituted or unsubstituted “arylheteroarylamino”, a substituted or unsubstituted “diarylboryl (two aryl groups may be bonded via a single bond or a linking group)”, a substituted or unsubstituted “alkyl” as a first substituent. , substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy" or substituted "silyl", and the "aryl" or "heteroaryl" as the first substituent, the aryl of "diarylamino", the heteroaryl of "diheteroarylamino", the aryl and heteroaryl of "arylheteroarylamino", the aryl of "diarylboryl", and the aryl of "aryloxy" can be listed as the monovalent group of the "aryl ring" or "heteroaryl ring".

[0196] In addition, the "alkyl" as the first substituent may be any of a straight chain and a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. Preferably, it is an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), more preferably, it is an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), further preferably, it is an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), and particularly preferably, it is an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms) and an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms).

[0197] Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-amyl, n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

[0198] For example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like may be mentioned.

[0199] In addition, examples of the "cycloalkyl" as the first substituent include cycloalkyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, cycloalkyl groups having 5 to 8 carbon atoms, cycloalkyl groups having 5 to 6 carbon atoms, and cycloalkyl groups having 5 carbon atoms.

[0200] Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted groups having 1 to 4 carbon atoms or 1 to 5 carbon atoms thereof, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0201] In addition, examples of the "alkoxy group" as the first substituent include a linear alkoxy group having 1 to 24 carbon atoms or a branched alkoxy group having 3 to 24 carbon atoms. Preferably, it is an alkoxy group having 1 to 18 carbon atoms (branched alkoxy group having 3 to 18 carbon atoms), more preferably, it is an alkoxy group having 1 to 12 carbon atoms (branched alkoxy group having 3 to 12 carbon atoms), further preferably, it is an alkoxy group having 1 to 6 carbon atoms (branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably, it is an alkoxy group having 1 to 5 carbon atoms (branched alkoxy group having 3 to 5 carbon atoms) and an alkoxy group having 1 to 4 carbon atoms (branched alkoxy group having 3 to 4 carbon atoms).

[0202] Specific examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy, 1-methylpentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, tert-octyloxy, 1-methylheptyloxy, 2-ethylhexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, and n-eicosyloxy.

[0203] Examples of the “substituted silyl group” as the first substituent include a silyl group substituted with at least one of an aryl group, an alkyl group and a cycloalkyl group, a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group or an alkyldicycloalkylsilyl group.

[0204] Examples of the “triarylsilyl group” include a group in which three hydrogen atoms in a silyl group are independently substituted by aryl groups. The aryl group may be any of the groups described as the “aryl group” in the first substituent.

[0205] Specific examples of the “triarylsilyl group” include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl groups.

[0206] As the "trialkylsilyl group", there can be mentioned a group in which three hydrogen atoms in the silyl group are independently replaced by an alkyl group, and the alkyl group can be cited as the group described as the "alkyl group" in the first substituent group. The preferred alkyl group for substitution is an alkyl group having 1 to 5 carbon atoms or 1 to 4 carbon atoms, and specifically, there can be mentioned a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a cyclobutyl group, and the like.

[0207] Specific examples of the trialkylsilyl group include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and tert-butyldiisopropylsilyl.

[0208] As the "tricycloalkylsilyl group", there can be mentioned a group in which three hydrogen atoms in the silyl group are independently replaced by a cycloalkyl group, and the cycloalkyl group can be cited as the group described as the "cycloalkyl group" in the first substituent group. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specifically, there can be mentioned cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazulyl, and the like.

[0209] Specific examples of the tricycloalkylsilyl group include a tricyclopentylsilyl group and a tricyclohexylsilyl group.

[0210] Specific examples of the dialkylcycloalkylsilyl group in which two alkyl groups are substituted with one cycloalkyl group and the alkyldicycloalkylsilyl group in which one alkyl group is substituted with two cycloalkyl groups include silyl groups substituted with a group selected from the above-mentioned specific alkyl groups and cycloalkyl groups.

[0211] In addition, the "aryl group" in the "diarylboryl group" as the first substituent can be referred to the description of the aryl group. In addition, the two aryl groups can be linked via a single bond or a linking group (e.g., >C(-R) 2 , >O, >S or >NR). Here, >C(-R) 2 and >NR R is hydrogen (only in >C(-R) 2), aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents), the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above are the second substituents), as specific examples of these groups, the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy as the first substituent can be cited.

[0212] As the first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryl groups may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl" may have at least one hydrogen substituted by a second substituent as described as substituted or unsubstituted. As the second substituent, for example, an aryl, a heteroaryl, an alkyl, or a cycloalkyl group may be mentioned, and specific examples of these may refer to the description of the monovalent group of the "aryl ring" or "heteroaryl ring" and the description of the "alkyl" or "cycloalkyl" as the first substituent. In addition, in the aryl or heteroaryl group as the second substituent, a structure in which at least one hydrogen is replaced by an aryl group such as phenyl (specifically, the groups described above), an alkyl group such as methyl (specifically, the groups described above), or a cycloalkyl group such as cyclohexyl (specifically, the groups described above) is also included in the aryl or heteroaryl group as the second substituent. As one example, in the case where the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is replaced by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in the heteroaryl group as the second substituent.

[0213] As R in the general formula (2) 1 ~R 11 The aryl group, heteroaryl group, aryl group of diarylamino, heteroaryl group of diheteroarylamino, aryl group and heteroaryl group of arylheteroarylamino, aryl group of diarylboryl, or aryl group of aryloxy may be a monovalent group of the "aryl ring" or "heteroaryl ring" described in the general formula (1). 1 ~R 11 The alkyl, cycloalkyl or alkoxy group in the formula (1) may refer to the description of the first substituent "alkyl", "cycloalkyl" or "alkoxy" in the formula (1). 1 ~R 11The triarylsilyl group, trialkylsilyl group, tricycloalkylsilyl group, dialkylcycloalkylsilyl group or alkyldicycloalkylsilyl group in the general formula (1) may refer to the description of the "substituted silyl group" as the first substituent. The same applies to the aryl group, heteroaryl group, alkyl group or cycloalkyl group as a substituent for these groups. 1 ~R 11 The same applies to heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl groups as substituents of these rings, and aryl, heteroaryl, alkyl or cycloalkyl groups as further substituents.

[0214] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating and electron withdrawing properties of the structure of the first substituent. The first substituent is preferably a group represented by the following structural formula, and more preferably a methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a phenyl group, an o-tolyl group, a p-tolyl group, a 2,4-xyl group, a 2,5-xyl group, a 2,6-xyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, a 3,6-di-tert-butylcarbazolyl group and a phenoxy group, and further preferably a methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a phenyl group, an o-tolyl group, a 2,6-xyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group and a 3,6-di-tert-butylcarbazolyl group. From the viewpoint of ease of synthesis, those with greater steric hindrance are preferred for selective synthesis, and specifically, tert-butyl, tert-amyl, tert-octyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-tert-butylcarbazolyl are preferred.

[0215] In the following structural formula, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-amyl group, "tOct" represents a tert-octyl group, and * represents a bonding position.

[0216] [Chemistry 20]

[0217]

[0218] [Chemistry 21]

[0219]

[0220] [Chemistry 22]

[0221]

[0222] [Chemistry 23]

[0223]

[0224] [Chemistry 24]

[0225]

[0226] In the general formula (2), any "-C(-R)=C(-R)-" (where R is R in the general formula (2)) can be 1 ~R 11 ) is substituted with aryl, alkyl or cycloalkyl, and examples of the aryl, alkyl or cycloalkyl include those described above. Particularly preferred are aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0227] Y in the general formula (1) 1 R of Si-R and Ge-R in the formula (2) is an aryl group, an alkyl group or a cycloalkyl group, and the aryl group, the alkyl group or the cycloalkyl group may be the groups described above. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably, cyclohexyl or adamantyl). The above description also applies to Y in the formula (2). 1 .

[0228] X in the general formula (1) 1 and X 2R of the >NR in the NR is an aryl, heteroaryl, alkyl or cycloalkyl group which may be substituted by the second substituent, and at least one hydrogen in the aryl, heteroaryl, alkyl or cycloalkyl group may be substituted by an alkyl or cycloalkyl group, for example. As the aryl, heteroaryl, alkyl or cycloalkyl group, the groups described above can be cited. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl groups having 2 to 15 carbon atoms (e.g., carbazolyl, dibenzofuranyl, dibenzothiophenyl, etc.), alkyl groups having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl), more preferably phenyl, naphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl, and further preferably dibenzofuranyl or dibenzothiophenyl. In addition, the dibenzofuranyl group or dibenzothiophenyl group is particularly preferably substituted by a second substituent. Specifically, as the second substituent, tert-butyl group, phenyl group or d5-phenyl group can be mentioned. These substituents are preferably substituted at the para position of the oxygen atom or sulfur atom. The above description also applies to X in the general formula (2). 1 and X 2 .

[0229] X in the general formula (1) 1 and X 2 >C(-R) 2 R is hydrogen, an aryl group, an alkyl group or a cycloalkyl group which may be substituted by the second substituent, and at least one hydrogen in the aryl group may be substituted by an alkyl group. Examples of the aryl group, alkyl group or cycloalkyl group include the groups described above. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). The above description also applies to X in the general formula (2). 1 and X 2 .

[0230] As the linking group in the general formula (1), "-C(-R) 2 -" is hydrogen, alkyl or cycloalkyl, and the alkyl or cycloalkyl group includes the above-mentioned groups. Particularly preferred are alkyl groups having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). The above description also applies to "-C(-R)" as a linking group in the general formula (2). 2 -".

[0231] In addition, the present invention is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer can be any form as long as it has multiple unit structures in one compound. For example, in addition to the form in which multiple unit structures are bonded by a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthyl group, etc. (a bonded type polymer), it can also be a form in which multiple unit structures share any ring (A ring, B ring or C ring, a ring, b ring or c ring) contained in the unit structure (a ring-sharing type polymer). In addition, it can also be a form in which any ring (A ring, B ring or C ring, a ring, b ring or c ring) contained in the unit structure is condensed with each other (a ring-condensed type polymer). Preferably, it is a ring-sharing type polymer and a ring-condensed type polymer, and more preferably a ring-sharing type polymer.

[0232] As such a polymer, for example, the polymer compounds represented by the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4) or formula (2-6) can be cited. If the general formula (2) is used for explanation, the polymer compound represented by the following formula (2-4) is a polymer compound having a plurality of unit structures represented by the general formula (2) in one compound in a manner that the benzene ring is shared as the a ring (ring-sharing type polymer). In addition, if the general formula (2) is used for explanation, the polymer compound represented by the following formula (2-4-1) is a polymer compound having two unit structures represented by the general formula (2) in one compound in a manner that the benzene ring is shared as the a ring (ring-sharing type polymer). In addition, if the general formula (2) is used for explanation, the polymer compound represented by the following formula (2-4-2) is a polymer compound having three unit structures represented by the general formula (2) in one compound in a manner that the benzene ring is shared as the a ring (ring-sharing type polymer). In addition, if the general formula (2) is used for explanation, the polymer compound represented by any one of the following formulas (2-5-1) to (2-5-4) is a polymer compound having a plurality of unit structures represented by the general formula (2) in one compound in a manner that the benzene ring is shared as the b ring (or c ring) (ring-sharing type polymer). In addition, if explained by general formula (2), the multimer compound represented by the following formula (2-6) is a multimer compound (ring condensation type multimer) having multiple unit structures represented by general formula (2) in one compound, in which, for example, a benzene ring as the b ring (or a ring, c ring) of a certain unit structure is condensed with a benzene ring as the b ring (or a ring, c ring) of a certain unit structure.

[0233] [Chemistry 25]

[0234]

[0235] The multimeric compound may be a multimer formed by combining a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) with any one of formulas (2-5-1) to (2-5-4) or a multimerization form represented by formula (2-6); it may also be a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) with a multimerization form represented by formula (2-6); it may also be a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) with a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) and a multimerization form represented by formula (2-6).

[0236] In addition, all or part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound and its polymer represented by the general formula (1) or the general formula (2) may be deuterium, cyano or halogen. For example, in the formula (1), the A ring, the B ring, the C ring (the A ring to the C ring are aryl rings or heteroaryl rings), the substituents for the A ring to the C ring, Y 1 When R is Si-R or Ge-R (= alkyl, cycloalkyl, aryl), and X 1 and X 2 is >NR or >C(-R) 2 The hydrogen in R (=alkyl, cycloalkyl, aryl) may be substituted by deuterium, cyano or halogen, and among these, the form in which all or part of the hydrogen in the aryl or heteroaryl group is substituted by deuterium, cyano or halogen can be mentioned. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

[0237] In addition, the polycyclic aromatic compound and its polymer of the present invention can be used as a material for an organic element. Examples of organic elements include organic electroluminescent elements, organic field effect transistors, and organic thin film solar cells. In particular, in an organic electroluminescent element, Y is preferably used as a dopant material for the light emitting layer. 1 For B, X 1 and X 2 For compounds with a value greater than NR, Y 1 For B, X 1 is>O、X 2 For compounds with a value greater than NR, Y 1 For B, X 1 and X 2 The compound with a value of >O as the main material of the light-emitting layer is preferably Y 1 For B, X 1 is>O、X 2 For compounds with a value greater than NR, Y1 For B, X 1 and X 2 As the electron transport material, Y 1 For B, X 1 and X 2 Compounds with Y>O 1 P = O, X 1 and X 2 The compound is >O.

[0238] In addition, at least one of the aromatic rings and heteroaromatic rings in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and a polymer thereof is condensed with at least one cycloalkane.

[0239] For example, aryl rings and heteroaryl rings as ring A, ring B, ring C, ring a, ring b and ring c, aryl groups (aryl, diarylamino, arylheteroarylamino, diarylboryl or aryloxy) and heteroaryl groups (heteroaryl, diheteroarylamino or arylheteroarylamino) as the first and second substituents for rings A to C, aryl groups (the same as described above) and heteroaryl groups (the same as described above) as the first and second substituents for rings a to c, 1 That is, the aromatic group of R of Si-R and Ge-R (same as described above), and X 1 and X 2 That is, >NR and >C(-R) 2 At least one of the aryl group (the same as described above) and the heteroaryl group (the same as described above) of R is condensed with at least one cycloalkane.

[0240] Preferred are aryl rings and heteroaryl rings as ring A, ring B, ring C, ring a, ring b and ring c, aryl groups (aryl groups, diarylamino groups, diarylboryl groups or aryloxy groups) and heteroaryl groups (heteroaryl groups or heteroaryl groups in diheteroarylamino groups) as first substituents for rings A to C, aryl groups (the same as those described above) and heteroaryl groups (the same as those described above) as first substituents for rings a to c, and X 1 and X 2 That is, >NR and >C(-R) 2 At least one of the aryl group (the same as described above) and the heteroaryl group (the same as described above) of R is condensed with at least one cycloalkane.

[0241] More preferably, an aryl ring as the A ring, the B ring, the C ring, the a ring, the b ring, and the c ring, an aryl group (aryl moiety in an aryl or diarylamino group) and a heteroaryl group (heteroaryl moiety in a heteroaryl group) as the first substituent for the A ring to the C ring, an aryl group (the same as described above) and a heteroaryl group (the same as described above) as the first substituent for the a ring to the c ring, and X as 1 and X 2 That is, >NR and >C(-R) 2 At least one of the aromatic groups (the same as described) of R is condensed with at least one cycloalkane.

[0242] More preferably, an aryl ring as ring A, ring B, ring C, ring a, ring b and ring c, an aryl group as the first substituent for rings A to C (aryl or aryl moiety in diarylamino), an aryl group as the first substituent for rings a to c (the same as described above), and X 1 and X 2 That is, >NR and >C(-R) 2 At least one of the aromatic groups (the same as described) of R is condensed with at least one cycloalkane.

[0243] Examples of the “cycloalkane” include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0244] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene, decahydroazulene, and alkyl (especially methyl)-substituted products having 1 to 5 carbon atoms or 1 to 4 carbon atoms, halogen (especially fluorine)-substituted products, and deuterium-substituted products thereof.

[0245] Among these, for example, a structure in which at least one hydrogen in the carbon at the α position of the cycloalkane (a carbon adjacent to the carbon at the condensation site in the cycloalkane condensed in the aromatic ring or heteroaromatic ring) is substituted is preferred, a structure in which two hydrogens in the carbon at the α position are substituted is more preferred, and a structure in which a total of four hydrogens in the two carbons at the α position are substituted is further preferred. Examples of the substituent include alkyl (especially methyl) substitutions having 1 to 5 carbon atoms or 1 to 4 carbon atoms, halogen (especially fluorine) substitutions, and deuterium substitutions.

[0246] [Chemistry 26]

[0247]

[0248] The number of cycloalkanes condensed in one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed in one benzene ring (phenyl). Regarding the * in each structural formula, in the case of a benzene ring, it refers to the benzene ring contained in the skeletal structure of the compound, and in the case of a phenyl group, it refers to the bond substituted in the skeletal structure of the compound. Cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) may also be condensed with each other. Regardless of whether the condensed ring (base) is an aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0249] [Chemistry 27]

[0250]

[0251] At least one -CH 2 - can be replaced by -O-. 2 -When substituted by -O-, the adjacent -CH 2 - will not be replaced by -O-. For example, the following shows one or more -CH in a cycloalkane condensed to a benzene ring (phenyl): 2 - is substituted by -O-. In each structural formula, * in the case of a benzene ring refers to a benzene ring contained in the skeleton structure of the compound, and in the case of a phenyl group refers to a bond that is substituted in the skeleton structure of the compound. This is the same whether the condensed ring (base) is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl), or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0252] [Chemistry 28]

[0253]

[0254] At least one hydrogen in the cycloalkane may be substituted, and as the substituent, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silane, deuterium, cyano or halogen can be cited, and the details can be referred to the description of the first substituent. Among these substituents, alkyl (for example, alkyl with 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl with 3 to 14 carbon atoms), halogen (for example, fluorine) and deuterium are preferred. In addition, when the cycloalkyl is substituted, it can be a substitution form that forms a spiro ring structure. For example, the following shows an example of a spiro ring structure formed in a cycloalkane condensed in a benzene ring (phenyl). Regarding the * in each structural formula, in the case of a benzene ring, it refers to the benzene ring contained in the skeleton structure of the compound, and in the case of a phenyl group, it refers to the bond bond that is substituted in the skeleton structure of the compound.

[0255] [Chemistry 29]

[0256]

[0257] As other forms of cycloalkane condensation, examples include: polycyclic aromatic compounds represented by general formula (1) or general formula (2) and polymers thereof, for example, substituted with diarylamino groups condensed from cycloalkane (condensed to the aryl portion thereof), carbazolyl groups condensed from cycloalkane (condensed to the benzene ring portion thereof), or benzocarbazolyl groups condensed from cycloalkane (condensed to the benzene ring portion thereof). The “diarylamino group” may be the group described as the “first substituent”.

[0258] As more specific examples, R in the polycyclic aromatic compound represented by the general formula (2) and its polymers can be cited. 2 Examples are diarylamino groups condensed with cycloalkane (condensed to the aryl portion thereof) or carbazolyl groups condensed with cycloalkane (condensed to the benzene ring portion thereof).

[0259] As an example, a polycyclic aromatic compound represented by the following general formula (2-A) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2-A) can be cited. Cy in the following structural formula is a cycloalkane, n is independently an integer of 1 to 3 (preferably 1), and "=(Cy)n" means that n cycloalkanes are condensed at any position of the structure to be condensed (in the following structural formula, n cycloalkanes are condensed in a benzene ring (phenyl)), and the definition of each symbol in the structural formula is the same as the definition of each symbol in the general formula (2).

[0260] [Chemistry 30]

[0261]

[0262] Specifically, the compounds represented by the following formulas "1-Cy-(1)" to "1-Cy-(4401)" can be cited. In the following formulas, "Cy" represents a cycloalkane, and n is independently 0 to the maximum number that can be condensed (wherein not all n become 0), preferably 0 to 2 (wherein not all n become 0), and more preferably 1, and "=(Cy)n" means that n cycloalkanes are condensed at any position of the structure that is the condensation object (for example, in the following formula "1-Cy-(1)", n cycloalkanes are condensed at any position of each benzene ring). Furthermore, in the following structural formula, "OPh" represents a phenoxy group, and "Me" represents a methyl group, and each compound may be substituted by the first substituent and the second substituent.

[0263] [Chemistry 31]

[0264]

[0265] [Chemistry 32]

[0266]

[0267] [Chemistry 33]

[0268]

[0269] [Chemistry 34]

[0270]

[0271] [Chemistry 35]

[0272]

[0273] [Chemistry 36]

[0274]

[0275] [Chemistry 37]

[0276]

[0277] [Chemistry 38]

[0278]

[0279] [Chemistry 39]

[0280]

[0281] [Chemistry 40]

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[0283] [Chemistry 41]

[0284]

[0285] [Chemistry 42]

[0286]

[0287] [Chemistry 43]

[0288]

[0289] [Chemistry 44]

[0290]

[0291] As more specific examples of the polycyclic aromatic compounds condensed by cycloalkane of the present invention, the compounds represented by the following structural formulas can be cited. Furthermore, in the following structural formulas, "D" represents deuterium, "Me" represents methyl, "Et" represents ethyl, "iPr" represents isopropyl, "tBu" represents tert-butyl, "tAm" represents tert-amyl, "Ph" represents phenyl, "F" represents fluorine, "CN" represents cyano, "TMS" represents trimethylsilyl, and "TPhS" represents triphenylsilyl. Furthermore, in formula (1-1001) to formula (1-1265), the representation of methyl (Me) in the structural formula is omitted.

[0292] [Chemistry 45]

[0293]

[0294] [Chemistry 46]

[0295]

[0296] [Chemistry 47]

[0297]

[0298] [Chemistry 48]

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[0300] [Chemistry 49]

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[0480] [Chemistry 139]

[0481]

[0482] [Chemistry 140]

[0483]

[0484] [Chemistry 141]

[0485]

[0486] [Chemistry 142]

[0487]

[0488] [Chemistry 143]

[0489]

[0490] [Chemistry 144]

[0491]

[0492] [Chemistry 145]

[0493]

[0494] [Chemistry 146]

[0495]

[0496] [Chemistry 147]

[0497]

[0498] [Chemistry 148]

[0499]

[0500] [Chemistry 149]

[0501]

[0502] [Chemistry 150]

[0503]

[0504] [Chemistry 151]

[0505]

[0506] [Chemistry 152]

[0507]

[0508] [Chemistry 153]

[0509]

[0510] [Chemistry 154]

[0511]

[0512] [Chemistry 155]

[0513]

[0514] [Chemistry 156]

[0515]

[0516] [Chemistry 157]

[0517]

[0518] [Chemistry 158]

[0519]

[0520] [Chemistry 159]

[0521]

[0522] [Chemistry 160]

[0523]

[0524] [Chemistry 161]

[0525]

[0526] [Chemistry 162]

[0527]

[0528] [Chemistry 163]

[0529]

[0530] [Chemistry 164]

[0531]

[0532] [Chemistry 165]

[0533]

[0534] [Chemistry 166]

[0535]

[0536] [Chemistry 167]

[0537]

[0538] [Chemistry 168]

[0539]

[0540] [Chemistry 169]

[0541]

[0542] [Chemistry 170]

[0543]

[0544] [Chemistry 171]

[0545]

[0546] [Chemistry 172]

[0547]

[0548] [Chemistry 173]

[0549]

[0550] [Chemistry 174]

[0551]

[0552] [Chemistry 175]

[0553]

[0554] [Chemistry 176]

[0555]

[0556] [Chemistry 177]

[0557]

[0558] [Chemistry 178]

[0559]

[0560] [Chemistry 179]

[0561]

[0562] [Chemistry 180]

[0563]

[0564] [Chemistry 181]

[0565]

[0566] [Chemistry 182]

[0567]

[0568] [Chemistry 183]

[0569]

[0570] [Chemistry 184]

[0571]

[0572] [Chemistry 185]

[0573]

[0574] [Chemistry 186]

[0575]

[0576] [Chemistry 187]

[0577]

[0578] [Chemistry 188]

[0579]

[0580] [Chemistry 189]

[0581]

[0582] [Chemistry 190]

[0583]

[0584] [Chemistry 191]

[0585]

[0586] [Chemistry 192]

[0587]

[0588] [Chemistry 193]

[0589]

[0590] [Chemistry 194]

[0591]

[0592] [Chemistry 195]

[0593]

[0594] [Chemistry 196]

[0595]

[0596] [Chemistry 197]

[0597]

[0598] [Chemistry 198]

[0599]

[0600] [Chemistry 199]

[0601]

[0602] [Chemistry 200]

[0603]

[0604] [Chemistry 201]

[0605]

[0606] [Chemistry 202]

[0607]

[0608] [Chemistry 203]

[0609]

[0610] [Chemistry 204]

[0611]

[0612] [Chemistry 205]

[0613]

[0614] [Chemistry 206]

[0615]

[0616] [Chemistry 207]

[0617]

[0618] [Chemistry 208]

[0619]

[0620] [Chemistry 209]

[0621]

[0622] [Chemistry 210]

[0623]

[0624] [Chemistry 211]

[0625]

[0626] [Chemistry 212]

[0627]

[0628] [Chemistry 213]

[0629]

[0630] [Chemistry 214]

[0631]

[0632] [Chemistry 215]

[0633]

[0634] [Chemistry 216]

[0635]

[0636] [Chemistry 217]

[0637]

[0638] [Chemistry 218]

[0639]

[0640] [Chemistry 219]

[0641]

[0642] [Chemistry 220]

[0643]

[0644] [Chemistry 221]

[0645]

[0646] [Chemistry 222]

[0647]

[0648] [Chemistry 223]

[0649]

[0650] [Chemistry 224]

[0651]

[0652] [Chemistry 225]

[0653]

[0654] [Chemistry 226]

[0655]

[0656] [Chemistry 227]

[0657]

[0658] [Chemistry 228]

[0659]

[0660] [Chemistry 229]

[0661]

[0662] [Chemistry 230]

[0663]

[0664] [Chemistry 231]

[0665]

[0666] [Chemistry 232]

[0667]

[0668] [Chemistry 233]

[0669]

[0670] [Chemistry 234]

[0671]

[0672] [Chemistry 235]

[0673]

[0674] [Chemistry 236]

[0675]

[0676] [Chemistry 237]

[0677]

[0678] Furthermore,

[0679] (A) is preferably that at least one of the A ring, B ring, C ring and R>NR in the formula (1) is a heteroaryl ring or a heteroaryl group, and preferably the a ring, b ring, c ring, R in the formula (2) 1 ~R 11 Adjacent groups in the ring are bonded to each other and form a ring together with the a ring, the b ring or the c ring, and at least one of the Rs in >NR is a heteroaryl ring or a heteroaryl group.

[0680] in addition,

[0681] (B) is preferably at least one of "-C(-R)=" (where R is R in formula (2)) among the a ring, b ring and c ring in formula (2) 1 ~R 11 ) is substituted by "-N=", or at least one "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 ) is replaced by “-N(-R)-”, “-O-” or “-S-”.

[0682] and then,

[0683] (C) is preferably at least one of the a ring, b ring and c ring in the formula (2) "-C(-R)=C(-R)-" (here, R is R in the formula (2) 1 ~R 11 ) is replaced by “-S-”.

[0684] The above (A) to (C) are more preferably Y 1 is B and X 1 and X 2 For the case of >NR.

[0685] The polycyclic aromatic compound represented by the general formula (1) of the present invention and its multimer can also be used as the following polymer compound (the monomer used to obtain the polymer compound has a polymerizable substituent) or polymer crosslinked body (the polymer compound used to obtain the polymer crosslinked body has a crosslinkable substituent), or the following pendant polymer compound (the reactive compound used to obtain the pendant polymer compound has a reactive substituent) or pendant polymer crosslinked body (the pendant polymer compound used to obtain the pendant polymer crosslinked body has a crosslinkable substituent) Materials for organic elements, such as materials for organic electroluminescent elements, materials for organic field effect transistors or materials for organic thin film solar cells, wherein the polymer compound is obtained by polymerizing a reactive compound having a reactive substituent substituted in the polycyclic aromatic compound represented by the general formula (1) and its polymer as a monomer, the polymer crosslinked body is obtained by further crosslinking the polymer compound, the pendant polymer compound is obtained by reacting a main chain polymer with the reactive compound, and the pendant polymer crosslinked body is obtained by further crosslinking the pendant polymer compound.

[0686] The reactive substituent (including the polymerizable substituent, the cross-linkable substituent, and the reactive substituent for obtaining the pendant type polymer, hereinafter also referred to as "reactive substituent") is not particularly limited as long as it is a substituent that can make the polycyclic aromatic compound or its polymer high molecular weight, a substituent that can further cross-link the polymer compound obtained in this way, and a substituent that can undergo a pendant reaction in the main chain type polymer, but preferably a substituent of the following structure. * in each structural formula represents a bonding position.

[0687] [Chemistry 238]

[0688]

[0689] L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene group having 1 to 12 carbon atoms, an oxyalkylene group having 1 to 12 carbon atoms, and a polyoxyalkylene group having 1 to 12 carbon atoms. Among the substituents, a group represented by Formula (XLS-1), Formula (XLS-2), Formula (XLS-3), Formula (XLS-9), Formula (XLS-10), or Formula (XLS-17) is preferred, and a group represented by Formula (XLS-1), Formula (XLS-3), or Formula (XLS-17) is more preferred.

[0690] The use of such polymer compounds, polymer crosslinked products, pendant polymer compounds and pendant polymer crosslinked products (hereinafter also simply referred to as "polymer compounds and polymer crosslinked products") will be described in detail later.

[0691] 2. Method for producing polycyclic aromatic compounds and polymers thereof by condensation of cycloalkanes

[0692] The polycyclic aromatic compounds and polymers thereof represented by the general formula (1) or (2) are basically firstly prepared by using a bonding group (including X 1 or X 2 The intermediate is prepared by bonding the ring A (ring a) with the ring B (ring b) and the ring C (ring c) by using the bonding group (including Y 1 The first reaction is carried out by bonding ring A (ring a), ring B (ring b) and ring C (ring c) to produce the final product (second reaction). In the first reaction, for example, if it is an etherification reaction, common reactions such as nucleophilic substitution reaction and Ullmann reaction can be used, and if it is an amination reaction, common reactions such as Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same below) can be used. In addition, at some point in these reaction steps, a raw material condensed with cycloalkane or a step of adding condensed cycloalkane is used, thereby, the compound of the present invention condensed with cycloalkane at the desired position can be produced.

[0693] As shown in the following process (1) or process (2), the second reaction is to bond Y to ring A (ring a), ring B (ring b) and ring C (ring c). 1 The reaction introduced, as an example, is as follows: 1 is a boron atom, X 1 and X 2 First, use n-butyllithium, sec-butyllithium or tert-butyllithium to remove X 1 With X 2 The hydrogen atoms between are ortho-metallated. Subsequently, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange, and then a Bronsted base such as N,N-diisopropylethylamine is added to carry out a tandem Bora-Friedel-Crafts reaction, thereby obtaining the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. Furthermore, the definitions of the symbols of the structural formulas in the following processes (1) and (2), and in the subsequent processes (3) to (28) are the same as those described above.

[0694] [Chemistry 239]

[0695]

[0696] [Chemistry 240]

[0697]

[0698] Furthermore, the above process (1) or process (2) mainly represents a method for producing a polycyclic aromatic compound represented by general formula (1) or general formula (2), but its multimer can be produced by using an intermediate having a plurality of A rings (a rings), B rings (b rings) and C rings (c rings). In detail, the following processes (3) to (5) are used for explanation. In the above case, the target product can be obtained by setting the amount of the reagent such as butyl lithium used to 2 times or 3 times.

[0699] [Chemistry 241]

[0700]

[0701] [Chemistry 242]

[0702]

[0703] [Chemistry 243]

[0704]

[0705] In the above process, lithium is introduced to the desired position by ortho-metallation. However, bromine atoms or the like may be introduced at the position where lithium is to be introduced as in the following processes (6) and (7), and lithium may also be introduced to the desired position by halogen-metal exchange.

[0706] [Chemistry 244]

[0707]

[0708] [Chemistry 245]

[0709]

[0710] In addition, regarding the method for producing the polymer described in process (3), a halogen such as a bromine atom or a chlorine atom may be introduced at the position where lithium is to be introduced as in the above-mentioned processes (6) and (7), and lithium may be introduced to the desired position by halogen-metal exchange (the following processes (8), (9) and (10)).

[0711] [Chemistry 246]

[0712]

[0713] [Chemistry 247]

[0714]

[0715] [Chemistry 248]

[0716]

[0717] The above method is useful because it allows the synthesis of a target compound even when ortho-metallation cannot be performed due to the influence of a substituent.

[0718] By appropriately selecting the above-mentioned synthesis method and the raw materials used, a compound having a substituent at a desired position and Y 1 is a boron atom, X 1 and X 2 Polycyclic aromatic compounds containing oxygen atoms and their polymers.

[0719] Then, Y 1 is a boron atom, X 1 and X 2 The case where X is a nitrogen atom is shown as an example in the following schemes (11) and (12). 1 and X 2 In the case of an oxygen atom, first, X is reacted with n-butyl lithium or the like. 1 With X 2 The hydrogen atoms between the two are ortho-metallated. Subsequently, boron tribromide or the like is added to carry out lithium-boron metal exchange, and then a Brünster base such as N,N-diisopropylethylamine is added to carry out a tandem boro-friedel-quafft reaction, thereby obtaining the target product. Here, in order to promote the reaction, a Lewis acid such as aluminum trichloride may also be added. In addition, at some point in these reaction steps, a raw material condensed with cycloalkane is used, or a step of condensing cycloalkane is added, thereby, the compound of the present invention in which the desired position is condensed with cycloalkane can be manufactured.

[0720] [Chemistry 249]

[0721]

[0722] [Chemistry 250]

[0723]

[0724] In addition, about Y 1 is a boron atom, X 1 and X 2In the case of a polymer in which a nitrogen atom is present, a halogen such as a bromine atom or a chlorine atom may be introduced at the position where lithium is to be introduced as in the above-mentioned processes (6) and (7), and lithium may be introduced at the desired position by halogen-metal exchange (the following processes (13), (14) and (15)).

[0725] [Chemistry 251]

[0726]

[0727] [Chemistry 252]

[0728]

[0729] [Chemistry 253]

[0730]

[0731] Then, Y 1 is phosphorus sulfide, phosphorus oxide or phosphorus atom, X 1 and X 2 The case where X is an oxygen atom is shown as an example in the following schemes (16) to (19). 1 With X 2 Then, phosphorus trichloride and sulfur are added in sequence, and finally a Lewis acid such as aluminum trichloride and a Brünster base such as N,N-diisopropylethylamine are added to perform a tandem Phospha-Friedel-Crafts Reaction, thereby obtaining Y 1 Y can be obtained by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA). 1 Y is a phosphorus oxide compound, which can be obtained by treating it with triethylphosphine. 1 In addition, by using a cycloalkane-condensed raw material at any point in these reaction steps, or by adding a cycloalkane-condensed step, the compound of the present invention in which a desired position is condensed with a cycloalkane can be produced.

[0732] [Chemistry 254]

[0733]

[0734] [Chemistry 255]

[0735]

[0736] [Chemistry 256]

[0737]

[0738] [Chemistry 257]

[0739]

[0740] In addition, about Y 1 For phosphorus sulfide, X 1 and X 2 In the case of a polymer in which Y is an oxygen atom, a halogen such as a bromine atom or a chlorine atom may be introduced at the position where lithium is to be introduced as in the above-mentioned process (6) and process (7), and lithium may be introduced at the desired position by halogen-metal exchange (the following process (20), process (21) and process (22)). 1 For phosphorus sulfide, X 1 and X 2 The polymers when the oxygen atom is present can also be treated with m-chloroperbenzoic acid (m-CPBA) as in the above-mentioned process (18) and process (19) to obtain Y 1 Y is a phosphorus oxide compound, which can be obtained by treating it with triethylphosphine. 1 A compound containing phosphorus atoms.

[0741] [Chemistry 258]

[0742]

[0743] [Chemistry 259]

[0744]

[0745] [Chemistry 260]

[0746]

[0747] Here, Y is recorded 1 is B, P, P=O or P=S, X 1 and X 2 is an example of O or NR, but Y can also be synthesized by appropriately changing the raw materials. 1 Al, Ga, As, Si-R or Ge-R, or X 1 and X 2 A compound of S.

[0748] Specific examples of the solvent used in the above reaction include tert-butylbenzene and xylene.

[0749] In the general formula (2), the substituents R on the a ring, b ring and c ring are 1 ~R 11The adjacent groups in the formula (2) can be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring can be substituted by an aryl group or a heteroaryl group. Therefore, the polycyclic aromatic compound represented by the general formula (2) changes the ring structure of the compound according to the mutual bonding form of the substituents in the a ring, the b ring and the c ring, as shown in the formula (2-1) and the formula (2-2) of the following flow (23) and flow (24). These compounds can be synthesized by applying the synthesis method shown in the above flow (1) to the intermediate shown in the following flow (23) and flow (24). In addition, at some point in these reaction steps, a raw material condensed with a cycloalkane is used, or a step of adding a condensation step of a cycloalkane is added, thereby, the compound of the present invention in which the desired position is condensed with a cycloalkane can be produced.

[0750] [Chemistry 261]

[0751]

[0752] [Chemistry 262]

[0753]

[0754] In the formula (2-1) and (2-2), the A' ring, the B' ring and the C' ring represent a substituent R 1 ~R 11 The adjacent groups in the formula are bonded to each other and form an aryl ring or a heteroaryl ring (which may also be referred to as a condensed ring formed by condensing other ring structures in the a ring, b ring or c ring) together with the a ring, b ring and c ring. Furthermore, although not shown in the formula, there are compounds in which the a ring, b ring and c ring are all changed to the A' ring, B' ring and C' ring.

[0755] In addition, in the general formula (2), "the R of the >NR and the >-C(-R) 2 -At least one of the R's is -O-, -S-, -C(-R) 2 - or a single bond to at least one of the a ring, b ring and c ring" can be represented by the following compound, which is represented by formula (2-3-1) in the following scheme (25) and has X 1 or X 2 The ring structure introduced into the condensed ring B' and the condensed ring C', or the ring structure represented by the formula (2-3-2) or the formula (2-3-3) and having X 1 or X 2The ring structure introduced into the condensed ring A'. These compounds can be synthesized by applying the synthesis methods shown in the above-mentioned schemes (1) to (19) to the intermediates shown in the following scheme (25). In addition, at any point in these reaction steps, a raw material condensed with a cycloalkane is used, or a step of condensing a cycloalkane is added, thereby producing the compound of the present invention in which the desired position is condensed with a cycloalkane.

[0756] [Chemistry 263]

[0757]

[0758] In the synthesis methods of the above-mentioned processes (1) to (17) and (20) to (25), it is indicated that before adding boron trichloride or boron tribromide, butyl lithium or the like is used to react X 1 With X 2 This is an example of a tandem heterofriedel-quafft reaction whereby ortho-metallation of hydrogen atoms (or halogen atoms) between the two atoms is performed. However, the reaction may be performed by adding boron trichloride or boron tribromide instead of ortho-metallation using butyl lithium or the like.

[0759] In addition, in Y 1 In the case of a phosphorus system, as shown in the following process (26) or process (27), n-butyl lithium, sec-butyl lithium or tert-butyl lithium is used to treat X 1 With X 2 (O in the following formula) is ortho-metallated, then bis(diethylamino)chlorophosphine is added, after the metal exchange of lithium-phosphorus, Lewis acids such as aluminum chloride are added, thus tandem phosphafrid-Quaft reaction is carried out, thus target can be obtained. The reaction method is also recorded in International Publication No. 2010 / 104047 (for example, 27 pages). In addition, somewhere in these reactions steps, the raw material of cycloalkane condensation or the step of appending condensed cycloalkane is used, thus, the compound of the present invention of the desired position through cycloalkane condensation can be manufactured.

[0760] [Chemistry 264]

[0761]

[0762] [Chemistry 265]

[0763]

[0764] Furthermore, in the above process (26) or process (27), a multimeric compound can be synthesized by using an ortho-metallating agent such as butyl lithium in an amount of 2 or 3 times the molar amount of the intermediate 1. In addition, a halogen such as a bromine atom or a chlorine atom is introduced in advance at the position where a metal such as lithium is to be introduced, and a halogen-metal exchange is performed, thereby introducing a metal to the desired position.

[0765] In addition, regarding the polycyclic aromatic compound represented by the general formula (2-A), a polycyclic aromatic compound condensed with cycloalkane at a desired position can be synthesized by synthesizing an intermediate condensed with cycloalkane as shown in the following process (28). In the process (28), X represents a halogen or hydrogen, and the definitions of other symbols are the same as those of the symbols in the general formula (20).

[0766] [Chemistry 266]

[0767]

[0768] The intermediate before cyclization in the process (28) can also be synthesized by the method shown in the process (1) or the like. That is, the intermediate having the desired substituent can be synthesized by appropriately combining the Buchwald-Hartwig reaction or the Suzuki coupling reaction, or the etherification reaction using the nucleophilic substitution reaction or the Ullmann reaction or the like. In these reactions, the raw materials that become the precursors of the cycloalkane condensation can also be commercially available products.

[0769] The compound of the general formula (2-A) having a cycloalkane-condensed diphenylamino group can also be synthesized, for example, by the following method. That is, cycloalkane-condensed bromobenzene and trihalogenated aniline are subjected to an amination reaction such as the Buchwald-Hartwig reaction to introduce a cycloalkane-condensed diphenylamino group, and then 1 , X 2 In the case of NR, an amination reaction such as the Buchwald-Hartwig reaction is used to derive the intermediate (M-3), and in the case of X 1 , X 2 When it is O, it can be derived into an intermediate (M-3) by etherification using phenol, and then, for example, a metalation reagent such as butyl lithium is allowed to act to perform transmetalation, then a boron halide such as boron tribromide is allowed to act, and then a Brünster base such as diethylisopropylamine is allowed to act to synthesize a compound of the general formula (2-A). These reactions can also be applied to other compounds that have undergone cycloalkane condensation.

[0770] Furthermore, examples of ortho-metallating agents used in the processes (1) to (28) include alkyl lithiums such as methyl lithium, n-butyl lithium, sec-butyl lithium, and tert-butyl lithium, organic basic compounds such as lithium diisopropylamide, lithium tetramethylpiperidinide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide, and dispersed alkali metals such as organic solvent-dispersed Na.

[0771] Furthermore, as the metal-Y used in the above-mentioned processes (1) to (28), 1 The metal exchange reagents include: Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Triiodide, etc. 1 Halides, CIPN(NEt 2 ) 2 Wait for Y 1 Amine halide, Y 1 Alkoxylate, Y 1 Aryloxy compounds, etc.

[0772] Furthermore, examples of the Brünster base used in the above-mentioned processes (1) to (28) include: N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-dimethylpyridine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar 4 BNa、Ar 4 BK、Ar 3 B. Ar 4 Si (herein, Ar is an aryl group such as phenyl) and the like.

[0773] Examples of the Lewis acid used in the above-mentioned processes (1) to (28) include: AlCl 3 , AlBr 3 , AlF 3 , BF 3 ·OEt 2 , BCl 3 , BBr 3 、GaCl 3 , GaBr 3 、InCl 3 、InBr 3 、In(OTf) 3 SnCl 4 SnBr 4 、AgOTf、ScCl 3 Sc(OTf) 3 、ZnCl2 、ZnBr 2 、Zn(OTf) 2 MgCl 2 MgBr 2 、Mg(OTf) 2 、LiOTf、NaOTf、KOTf、Me 3 SiOTf, Cu(OTf) 2 , CuCl 2 , YCl 3 、Y(OTf) 3 、TiCl 4 、TiBr 4 、ZrCl 4 , ZrBr 4 、FeCl 3 , FeBr 3 、CoCl 3 ,CoBr 3 wait.

[0774] In the above-mentioned processes (1) to (28), in order to promote the tandem heterofriedel-quafft reaction, a Brünster base or a Lewis acid may be used. 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Triiodide, etc. 1 In the case of halides, as the aromatic electrophilic substitution reaction proceeds, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated, so it is effective to use a Brünster base to capture the acid. 1 Amine halide, Y 1 In the case of alkoxylates, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds. Therefore, in many cases, it is not necessary to use a Brünster base. However, since the amino group or alkoxy group has low ability to leave, it is effective to use a Lewis acid that promotes its leaving.

[0775] In addition, the polycyclic aromatic compounds or polymers thereof of the present invention also include compounds in which at least a portion of the hydrogen atoms are substituted by deuterium or cyano, or compounds in which at least a portion of the hydrogen atoms are substituted by halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials that are deuterated, cyanated, fluorinated or chlorinated at the desired positions.

[0776] 3. Organic components

[0777] The cycloalkane-condensed polycyclic aromatic compound of the present invention can be used as a material for an organic device, such as an organic electroluminescent device, an organic field effect transistor, or an organic thin film solar cell.

[0778] 3-1. Organic electroluminescent element

[0779] Hereinafter, the organic EL element of this embodiment will be described in detail with reference to the drawings. Figure 1 It is a schematic cross-sectional view showing the organic EL element according to this embodiment.

[0780] <Structure of organic electroluminescent element>

[0781] Figure 1 The organic EL element 100 shown includes: a substrate 101, an anode 102 arranged on the substrate 101, a hole injection layer 103 arranged on the anode 102, a hole transport layer 104 arranged on the hole injection layer 103, a light-emitting layer 105 arranged on the hole transport layer 104, an electron transport layer 106 arranged on the light-emitting layer 105, an electron injection layer 107 arranged on the electron transport layer 106, and a cathode 108 arranged on the electron injection layer 107.

[0782] Furthermore, the organic EL element 100 can also reverse the production order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0783] Not all of the above layers are required, and the minimum structural unit is set to a structure including an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers provided arbitrarily. In addition, each of the above layers may include a single layer or a plurality of layers.

[0784] The morphology of the layers constituting the organic EL element may be, in addition to the structural morphology of “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / luminescent layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / luminescent layer / electron injection layer / cathode”, The structural morphology of the substrate is as follows: substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", and "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0785] <Substrates in organic electroluminescent devices>

[0786] The substrate 101 is a support of the organic EL element 100, and quartz, glass, metal, plastic, etc. are generally used. The substrate 101 is formed into a plate, film, or sheet according to the purpose, for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. can be used. Among them, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. If it is a glass substrate, soda-lime glass or alkali-free glass can be used. In addition, the thickness only needs to be thick enough to maintain mechanical strength, so for example, it only needs to be 0.2 mm or more. The upper limit of the thickness is, for example, less than 2 mm, preferably less than 1 mm. Regarding the material of the glass, since the less ions dissolved from the glass, the better, alkali-free glass is preferably used. Since SiO 2 Soda lime glass with an isolation coating such as is also commercially available, so the soda lime glass can be used. In addition, in order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film can also be provided on at least one side of the substrate 101. In particular, when a plate, film or sheet made of a synthetic resin with low gas barrier property is used as the substrate 101, it is preferred to provide a gas barrier film.

[0787] <Anode in organic electroluminescent device>

[0788] The anode 102 plays a role of injecting holes into the light-emitting layer 105. When at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers.

[0789] As materials for forming the anode 102, inorganic compounds and organic compounds can be cited. As inorganic compounds, for example, metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (Indium Tin Oxide, ITO), indium-zinc oxide (Indium Zinc Oxide, IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass or Nesser (NESA) glass, etc. As organic compounds, for example, polythiophenes such as poly (3-methylthiophene), polypyrrole, conductive polymers such as polyaniline, etc. can be cited. In addition, it can be appropriately selected from the substances used as the anode of the organic EL element for use.

[0790] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light emission of the light emitting element, but from the perspective of the power consumption of the light emitting element, low resistance is ideal. For example, if it is an ITO substrate below 300Ω / Y, it functions as an element electrode, but now it is also possible to supply a substrate of about 10Ω / Y, so it is particularly ideal to use, for example, 100Ω / Y~5Ω / Y, preferably a low resistance product of 50Ω / Y~5Ω / Y. The thickness of ITO can be arbitrarily selected in accordance with the resistance value, but it is usually used between 50nm and 300nm.

[0791] <Hole injection layer and hole transport layer in organic electroluminescent element>

[0792] The hole injection layer 103 plays a role in efficiently injecting holes migrated from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role in efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are formed by stacking or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. In addition, an inorganic salt such as iron (III) chloride can be added to the hole injection / transport material to form a layer.

[0793] As a hole injection and transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, and it is ideal to have high hole injection efficiency and efficiently transport the injected holes. Therefore, it is preferred to have a small ionization potential, a large hole mobility, and excellent stability, and it is not easy to generate impurities that become traps during manufacturing and use.

[0794] As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials and known compounds used for hole injection layers and hole transport layers of p-type semiconductors and organic EL elements. Specific examples of these materials include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having aromatic tertiary amino groups in the main chain or side chain), 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 '-Diphenyl-N 4 ,N 4 '-Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4 ',N 4 '-tetrakis[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. Among polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole and polysilane having the above-mentioned monomers on the side chain are preferred, but there is no particular limitation as long as it is a compound that can form a thin film required for the production of a light-emitting element, can inject holes from the anode, and can further transport holes.

[0795] In addition, it is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials contain compounds with good electron donating properties or compounds with good electron accepting properties. In order to dope electron donating materials, strong electron acceptors such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4TCNQ) are known (for example, see the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo (M. Pfeiffer , A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes through the electron transfer process of the electron-donating base material (hole transport material). The conductivity of the base material varies greatly depending on the number and mobility of the holes. As host materials having hole transport properties, known materials include, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (4,4',4"-tris(N,N-diphenylamino)triphenylamine (4,4',4"-tris(N,N-diphenylamino)triphenylamine, TDATA), etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Gazette No. 2005-167175).

[0796] The hole injection layer material and the hole transport layer material can also be used as the following polymer compound or its polymer crosslinked body, or the following pendant polymer compound or its pendant polymer crosslinked body for the hole layer material, wherein the polymer compound is obtained by polymerizing the reactive compound substituted with a reactive substituent in the hole injection layer material and the hole transport layer material as a monomer, and the pendant polymer compound is obtained by reacting a main chain polymer with the reactive compound. As the reactive substituent in the above case, the description in the polycyclic aromatic compound represented by formula (1) can be cited.

[0797] The details of the uses of such polymer compounds and polymer crosslinked products will be described later.

[0798] <Light-emitting layer in organic electroluminescent element>

[0799] The light-emitting layer 105 is a layer that emits light by allowing holes injected from the anode 102 to recombine with electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material forming the light-emitting layer 105 can be any compound (luminescent compound) that is excited to emit light by the recombination of holes and electrons, and is preferably a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in a solid state. In the present invention, as the material for the light-emitting layer, a host material and, for example, a polycyclic aromatic compound represented by the general formula (1) as a dopant material can be used.

[0800] The light-emitting layer may be a single layer or may include multiple layers, either of which is acceptable, and is formed of materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may be one type or a combination of multiple types, either of which is acceptable. The dopant material may be contained in the entire host material or in part of the host material, either of which is acceptable. As a doping method, it can be formed by co-evaporation with the host material, or it can be mixed with the host material in advance and then evaporated simultaneously.

[0801] The amount of the host material used varies depending on the type of the host material and can be determined based on the characteristics of the host material. The base amount of the host material used is preferably 50% to 99.999% by weight of the total material for the light-emitting layer, more preferably 80% to 99.95% by weight, and even more preferably 90% to 99.9% by weight.

[0802] The amount of the dopant material used varies depending on the type of the dopant material and can be determined by matching the characteristics of the dopant material. The base amount of the dopant used is preferably 0.001 wt% to 50 wt% of the total luminescent layer material, more preferably 0.05 wt% to 20 wt%, and further preferably 0.1 wt% to 10 wt%. If it is within the above range, it is preferred, for example, in terms of preventing concentration quenching.

[0803] The host material can be exemplified by anthracene, pyrene, dibenzo[deg.] or condensed ring derivatives such as fluorene, bis-styryl anthracene derivatives or distyryl benzene derivatives, tetraphenyl butadiene derivatives, cyclopentadiene derivatives, etc. Anthracene compounds, fluorene compounds or dibenzophenone compounds are particularly preferred. Series of compounds.

[0804] <Anthracene compounds>

[0805] The main anthracene compound is, for example, a compound represented by the following general formula (3).

[0806] [Chemistry 267]

[0807]

[0808] In formula (3),

[0809] X and Ar 4 are each independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, diarylamino which may be substituted, diheteroarylamino which may be substituted, arylheteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted or silyl which may be substituted, and all X and Ar 4 will not become hydrogen at the same time,

[0810] At least one hydrogen in the compound represented by formula (3) may be substituted by a halogen, a cyano group, a deuterium group or a substituted heteroaryl group.

[0811] In addition, the structure represented by formula (3) can also be used as a unit structure to form a polymer (preferably a dimer). In the above case, for example, the unit structures represented by formula (3) are bonded to each other via X, and as the above X, there can be listed: a single bond, an arylene group (phenylene, biphenylene and naphthylene, etc.) and a heteroarylene group (a group having a divalent bonding valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring and a phenyl-substituted carbazole ring), etc.

[0812] The details of the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl are described in the following preferred form column. In addition, as substituents for these groups, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl can be listed, and the details of these groups are also described in the following preferred form column.

[0813] Preferred embodiments of the anthracene-based compound are described below. The definitions of the symbols in the following structures are the same as those described above.

[0814] [Chemistry 268]

[0815]

[0816] In the general formula (3), X is independently a group represented by the formula (3-X1), the formula (3-X2) or the formula (3-X3), and the group represented by the formula (3-X1), the formula (3-X2) or the formula (3-X3) is bonded to the anthracene ring of the formula (3) at *. Preferably, two Xs are not simultaneously a group represented by the formula (3-X3). More preferably, two Xs are not simultaneously a group represented by the formula (3-X2).

[0817] In addition, the structure represented by formula (3) can also be used as a unit structure to form a polymer (preferably a dimer). In the above case, for example, the unit structures represented by formula (3) are bonded to each other via X, and as the above X, there can be listed: a single bond, an arylene group (phenylene, biphenylene and naphthylene, etc.) and a heteroarylene group (a group having a divalent bonding valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring and a phenyl-substituted carbazole ring), etc.

[0818] The naphthylene moiety in formula (3-X1) and formula (3-X2) can be condensed with one benzene ring. The structure formed by condensation in this manner is shown below.

[0819] [Chemistry 269]

[0820]

[0821] Ar 1 and Ar 2 are independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, phenyl, triphenylene, pyrene, or a group represented by the formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 In the case of a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at its *.

[0822] Ar 3 is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, phenyl, triphenylene, pyrene, or a group represented by the formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 3 In the case of a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by the straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3) is directly bonded to the group represented by formula (A).

[0823] In addition, Ar 3 It may also have a substituent, Ar 3The at least one hydrogen in the alkyl radical may be replaced by an alkyl radical having 1 to 4 carbon atoms, a cycloalkyl radical having 5 to 10 carbon atoms, a phenyl radical, a biphenyl radical, a terphenyl radical, a naphthyl radical, a phenanthrenyl radical, a fluorenyl radical, substituted with a phenylene group, a triphenylene group, a pyrene group, or a group represented by the formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). 3 When the substituent is a group represented by formula (A), the group represented by formula (A) is in the position * with Ar in formula (3-X3). 3 Bond.

[0824] Ar 4 Each independently represents hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms (such as methyl, ethyl, and tert-butyl) and / or a cycloalkyl group having 5 to 10 carbon atoms.

[0825] Examples of the alkyl group having 1 to 4 carbon atoms substituting in the silyl group include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, and cyclobutyl. Three hydrogen atoms in the silyl group are independently substituted with these alkyl groups.

[0826] Specific examples of the “silyl group substituted with an alkyl group having 1 to 4 carbon atoms” include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and tert-butyldiisopropylsilyl.

[0827] Examples of the cycloalkyl group having 5 to 10 carbon atoms which substitutes in the silyl group include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazulenyl and the like, and three hydrogen atoms in the silyl group are independently substituted by these cycloalkyl groups.

[0828] Specific examples of the "silyl group substituted with a cycloalkyl group having 5 to 10 carbon atoms" include a tricyclopentylsilyl group and a tricyclohexylsilyl group.

[0829] The substituted silyl group includes a dialkylcycloalkylsilyl group in which two alkyl groups are substituted with one cycloalkyl group, and an alkyldicycloalkylsilyl group in which one alkyl group is substituted with two cycloalkyl groups. Specific examples of the substituted alkyl group and cycloalkyl group include the above groups.

[0830] In addition, the hydrogen in the chemical structure of the anthracene compound represented by the general formula (3) may also be replaced by the group represented by the formula (A). In the case of substitution by the group represented by the formula (A), the group represented by the formula (A) replaces at least one hydrogen in the compound represented by the formula (3) at its *.

[0831] The group represented by formula (A) is one of substituents that the anthracene compound represented by formula (3) may have.

[0832] [Chemistry 270]

[0833]

[0834] In the formula (A), Y is -O-, -S- or >NR 29 , R 21 ~R 28 are each independently hydrogen, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, an amino group which may be substituted, a halogen group, a hydroxyl group or a cyano group, and R 21 ~R 28 The adjacent groups in the group may be bonded to each other to form a hydrocarbon ring, an aromatic ring or a heteroaromatic ring, R 29 is hydrogen or an aryl group which may be substituted.

[0835] As R 21 ~R 28 The "alkyl" in the "alkyl which may be substituted" may be any of a straight chain and a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms. Preferably, it is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), more preferably, it is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), further preferably, it is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and particularly preferably, it is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

[0836] Specific examples of the "alkyl group" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-amyl, n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

[0837] As R 21 ~R 28 The “cycloalkyl” of the “cycloalkyl which may be substituted” includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0838] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituents having 1 to 4 carbon atoms in these groups, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, and decahydroazulyl.

[0839] As R 21 ~R 28 The "aryl group" of the "aryl group which may be substituted" in the above-mentioned formula includes, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms.

[0840] Specific examples of "aryl" include: phenyl as a monocyclic ring system; biphenyl as a bicyclic ring system; naphthyl as a condensed bicyclic ring system; terphenyl as a tricyclic ring system (inter-terphenyl, o-terphenyl, p-terphenyl); acenaphthenyl, fluorenyl, phenanthrenyl, phenanthrenyl as a condensed tricyclic ring system; triphenylene, pyrenyl, naphthylene as a condensed tetracyclic ring system; perylenyl, condensed pentaphenyl, etc. as a condensed pentacyclic ring system.

[0841] As R 21 ~R 28The "heteroaryl" in the "heteroaryl which may be substituted" includes, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, further preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. In addition, examples of the heteroaryl include a heterocycle containing 1 to 5 hetero atoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon.

[0842] Specific examples of the "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl , phenothiazinyl, phenazinyl, cyclopentylboronic acid group (phenazasilinyl), indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of benzophosphoryl oxide ring, a monovalent group of dibenzophosphoryl oxide ring, furazanyl, thianthrenyl, indolecarbazolyl, benzindazolecarbazolyl and benzobenzoindolecarbazolyl, etc.

[0843] As R 21 ~R 28 The "alkoxy group" of the "alkoxy group which may be substituted" in the above-mentioned alkoxy group may be, for example, a linear alkoxy group having 1 to 24 carbon atoms or a branched alkoxy group having 3 to 24 carbon atoms. Preferably, it is an alkoxy group having 1 to 18 carbon atoms (branched alkoxy group having 3 to 18 carbon atoms), more preferably, it is an alkoxy group having 1 to 12 carbon atoms (branched alkoxy group having 3 to 12 carbon atoms), further preferably, it is an alkoxy group having 1 to 6 carbon atoms (branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably, it is an alkoxy group having 1 to 4 carbon atoms (branched alkoxy group having 3 to 4 carbon atoms).

[0844] Specific examples of the "alkoxy group" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy groups.

[0845] As R 21 ~R 28 The "aryloxy group" in the "aryloxy group which may be substituted" is a group in which the hydrogen of the -OH group is substituted by an aryl group, and the aryl group can be cited as the R 21 ~R 28The group described with reference to the “aryl group”.

[0846] As R 21 ~R 28 The "arylthio group" in the "arylthio group which may be substituted" is a group in which the hydrogen of the -SH group is substituted by an aryl group, and the aryl group can be cited as the R 21 ~R 28 The group described with reference to the “aryl group”.

[0847] As R 21 ~R 28 The "trialkylsilyl group" in the above description includes groups in which three hydrogen atoms in the silyl group are independently replaced by alkyl groups, and the alkyl groups can be cited as the R 21 ~R 28 The group described with reference to the "alkyl" in the above. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, and cyclobutyl.

[0848] Specific examples of the “trialkylsilyl group” include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and tert-butyldiisopropylsilyl.

[0849] As R 21 ~R 28 The "tricycloalkylsilyl group" in the above description may be a group in which three hydrogen atoms in the silyl group are independently replaced by cycloalkyl groups, and the cycloalkyl group may be cited as the R 21 ~R 28 The group described with reference to the "cycloalkyl" in . Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples thereof include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, and decahydroazulyl.

[0850] Specific examples of the "tricycloalkylsilyl group" include a tricyclopentylsilyl group and a tricyclohexylsilyl group.

[0851] Specific examples of the dialkylcycloalkylsilyl group in which two alkyl groups are substituted with one cycloalkyl group and the alkyldicycloalkylsilyl group in which one alkyl group is substituted with two cycloalkyl groups include silyl groups substituted with a group selected from the above-mentioned specific alkyl groups and cycloalkyl groups.

[0852] As R 21 ~R 28 The "substituted amino group" of the "amino group which may be substituted" in the above-mentioned "substitutable amino group" includes, for example, an amino group in which two hydrogen atoms are replaced by aryl or heteroaryl groups. An amino group in which two hydrogen atoms are replaced by aryl groups is a diaryl-substituted amino group, an amino group in which two hydrogen atoms are replaced by heteroaryl groups is a diheteroaryl-substituted amino group, and an amino group in which two hydrogen atoms are replaced by aryl and heteroaryl groups is an arylheteroaryl-substituted amino group. The aryl or heteroaryl group may be cited as the R 21 ~R 28 The group described with reference to the “aryl” or “heteroaryl” in the formula (a) is a group described with reference to the “aryl” or “heteroaryl” in the formula (b).

[0853] Specific examples of the "substituted amino group" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, and naphthylpyridylamino.

[0854] As R 21 ~R 28 The "halogen" in the formula includes fluorine, chlorine, bromine and iodine.

[0855] As R 21 ~R 28 Among the groups described, some groups may be substituted as described above. In such cases, the substituents include alkyl, cycloalkyl, aryl or heteroaryl. The alkyl, cycloalkyl, aryl or heteroaryl groups may be cited as the R 21 ~R 28 The group described with reference to “alkyl”, “cycloalkyl”, “aryl” or “heteroaryl” in the formula (a) is a group described with reference to “alkyl”, “cycloalkyl”, “aryl” or “heteroaryl”.

[0856] As Y's ">NR 29 "R" 29 is hydrogen or an aryl group which may be substituted. As the aryl group, the following may be cited as R 21 ~R 28 In addition, as the substituent, the following can be cited as the group explained for R 21 ~R 28 The group described above is a substituent.

[0857] R 21 ~R 28The adjacent groups in the formula (A-1) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where a ring is not formed is a group represented by the following formula (A-1). As the case where a ring is formed, for example, a group represented by any one of the following formulas (A-2) to (A-14) may be listed. Y and * in the formula have the same definition as described above. Furthermore, at least one hydrogen in the group represented by any one of the formulas (A-1) to (A-14) may be substituted by an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a diaryl substituted amino group, a diheteroaryl substituted amino group, an arylheteroaryl substituted amino group, a halogen, a hydroxyl group or a cyano group. The * in each structural formula represents a bonding position.

[0858] [Chemistry 271]

[0859]

[0860] Examples of the ring formed by bonding adjacent groups include a hydrocarbon ring such as a cyclohexane ring, and examples of the aryl ring or heteroaryl ring include the R 21 ~R 28 The ring structures described in the "aryl" or "heteroaryl" in the formula (A-1) are formed by condensing with one or two benzene rings.

[0861] As the group represented by formula (A), for example, a group represented by any one of the formulas (A-1) to (A-14) can be listed, preferably a group represented by any one of the formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably a group represented by any one of the formulas (A-1) to (A-4), further preferably a group represented by any one of the formulas (A-1), (A-3) and (A-4), and particularly preferably a group represented by the formula (A-1).

[0862] The group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or (3-X2), the single bond in formula (3-X3), Ar in formula (3-X3) at the * in formula (A). 3 In addition, the case of replacing at least one hydrogen in the compound represented by formula (3) is as described above, but among these bonding forms, it is preferably with the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3) and Ar in formula (3-X3). 3 The morphology of at least one bond.

[0863] In the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), Ar in formula (3-X3) 3The bonding position, and the position in the structure of the group represented by formula (A) that replaces at least one hydrogen in the compound represented by formula (3), may be any position in the structure of formula (A), for example, any one of the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 Any ring formed by bonding adjacent groups in the formula (A) to each other, or ">NR 29 "R 29 Bond at any position in .

[0864] Examples of the group represented by formula (A) include the following groups: Y and * in the formula have the same definitions as described above.

[0865] [Chemistry 272]

[0866]

[0867] [Chemistry 273]

[0868]

[0869] In addition, all or part of the hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) may be deuterium.

[0870] Specific examples of anthracene compounds include compounds represented by any of the following formulae (3-1) to (3-142): In the following structural formulae, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a tert-butyl group.

[0871] [Chemistry 274]

[0872]

[0873] [Chemistry 275]

[0874]

[0875] [Chemistry 276]

[0876]

[0877] [Chemistry 277]

[0878]

[0879] [Chemistry 278]

[0880]

[0881] [Chemistry 279]

[0882]

[0883] [Chemistry 280]

[0884]

[0885] The anthracene compound represented by formula (3) may be a compound having a reactive group at a desired position of the anthracene skeleton, and a compound having a reactive group at a desired position of X, Ar 4 The invention relates to a method for preparing a catalytically active ...

[0886] <Fluorene compounds>

[0887] The compound represented by the general formula (4) basically functions as a main body.

[0888] [Chemistry 281]

[0889]

[0890] In the formula (4),

[0891] R 1 To R 10 are independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the formula (4) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in these groups may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group,

[0892] In addition, R 1 With R 2 , R 2 With R 3 , R 3 With R 4 , R 5 With R 6 , R 6 With R 7 , R 7 With R 8 or R 9 With R 10may be independently bonded to form a condensed ring or a spiro ring, at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the formed ring via a linking group), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group or an aryloxy group, at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and,

[0893] At least one hydrogen in the compound represented by formula (4) may be substituted by a halogen, a cyano group or a deuterium group.

[0894] The details of the groups defined in the formula (4) can be referred to the description of the polycyclic aromatic compound of the formula (1) described above.

[0895] As R 1 To R 10 The alkenyl in the group includes, for example, alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0896] Furthermore, specific examples of heteroaryl groups include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4) or (4-Ar5).

[0897] [Chemistry 282]

[0898]

[0899] In Formula (4-Ar1) to Formula (4-Ar5), Y 1 are independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen,

[0900] At least one hydrogen in the structures of Formula (4-Ar1) to Formula (4-Ar5) may be substituted by a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a methyl group, an ethyl group, a propyl group, or a butyl group.

[0901] These heteroaryl groups may be bonded to the fluorene skeleton in the formula (4) via a linking group. That is, the fluorene skeleton in the formula (4) may be bonded to the heteroaryl group not only directly, but also between them via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthrylene, methylene, ethylene, -OCH 2 CH2 -、-CH 2 CH 2 O- or -OCH 2 CH 2 O-etc.

[0902] In addition, R in formula (4) 1 With R 2 , R 2 With R 3 , R 3 With R 4 , R 5 With R 6 , R 6 With R 7 or R 7 With R 8 can be independently bonded to form a condensed ring, R 9 With R 10 Can bond to form a spiro ring. 1 To R 8 The formed condensed ring is a ring condensed with the benzene ring in formula (4) and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples of the structure including the benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. 9 With R 10 The spiro ring formed is a ring spiro-bonded to the 5-membered ring in formula (4) and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and a fluorene ring and the like are examples.

[0903] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), and R in the general formula (4) is 1 With R 2 The compound formed by condensation of the benzene ring formed by bonding, in the general formula (4) R 3 With R 4 The compound formed by condensation of the benzene ring formed by bonding, in the general formula (4) R 1 To R 8 A compound in which neither of the is bonded.

[0904] [Chemistry 283]

[0905]

[0906] R in formula (4-1), formula (4-2) and formula (4-3) 1 To R 10 The definition of R in formula (4) corresponds to 1 To R 10 The same, and R in formula (4-1) and formula (4-2) 11 To R 14The definition of is also the same as R in formula (4) 1 To R 10 same.

[0907] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), and R in formula (4-1), formula (4-2) or formula (4-3) is 9 With R 10 A compound that is bonded to form a spiro-fluorene ring.

[0908] [Chemistry 284]

[0909]

[0910] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 To R 7 The definition of is the same as the corresponding R in formula (4-1), formula (4-2) and formula (4-3) 2 To R 7 The same, and R in formula (4-1A) and formula (4-2A) 11 To R 14 The definition of is also the same as R in formula (4-1) and formula (4-2) 11 To R 14 same.

[0911] In addition, all or part of the hydrogen atoms in the compound represented by formula (4) may be substituted by halogen, cyano or deuterium.

[0912] Specific examples of the fluorene-based compound include compounds represented by any one of the following formulae (4-4) to (4-22). In addition, "Me" in the following structural formulae represents a methyl group.

[0913] [Chemistry 285]

[0914]

[0915] <Dibenzo Series compounds>

[0916] As the main The compound is, for example, a compound represented by the following general formula (5).

[0917] [Chemistry 286]

[0918]

[0919] In the formula (5),

[0920] R 1 To R 16are independently hydrogen, aryl, heteroaryl (the heteroaryl may be connected to the dibenzoylmethane in the formula (5) via a linking group) backbone bond), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen of which may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group,

[0921] In addition, R 1 To R 16 The adjacent groups in the group may be bonded to each other to form a condensed ring, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the formed ring via a linking group), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, or an aryloxy group, and at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group, and,

[0922] At least one hydrogen in the compound represented by formula (5) may be substituted by halogen, cyano or deuterium.

[0923] The details of the groups defined in the formula (5) can be referred to the description of the polycyclic aromatic compound of the formula (1) described above.

[0924] Examples of the alkenyl group defined in the formula (5) include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, further preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0925] Furthermore, specific examples of heteroaryl groups include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5).

[0926] [Chemistry 287]

[0927]

[0928] In formula (5-Ar1) to formula (5-Ar5), Y 1 are independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen,

[0929] At least one hydrogen in the structures of Formula (5-Ar1) to Formula (5-Ar5) may be substituted by a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a methyl group, an ethyl group, a propyl group, or a butyl group.

[0930] These heteroaryl groups may be connected to the dibenzoylmethane in the formula (5) via a linking group. That is, the dibenzo The skeleton and the heteroaryl group may be bonded not only directly but also via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH 2 CH 2 -、-CH 2 CH 2 O- or -OCH 2 CH 2 O-etc.

[0931] The compound represented by the general formula (5) is preferably 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 In this case, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 Preferably, each of them is independently hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, a monovalent group having a structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having the above structure may be substituted by phenylene, biphenylene, naphthylene, anthracenyl, methylene, ethylene, -OCH 2 CH 2 -、-CH 2 CH 2 O- or -OCH 2 CH 2 O- and the dibenzo backbone bond), methyl, ethyl, propyl or butyl.

[0932] The compound represented by the general formula (5) is more preferably 1 , R 2 , R 4 , R 5 , R7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 In this case, R in formula (5) 3 , R 6 , R 11 and R 14 At least one (preferably one or two, more preferably one) of the following is a phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH 2 CH 2 -、-CH 2 CH 2 O- or -OCH 2 CH 2 O- is a monovalent group of the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5),

[0933] Other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl, and at least one of the hydrogens may be substituted by phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl.

[0934] In addition, when a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5) is selected as R in formula (5), 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 In the case of 1 To R 16 to form a single bond.

[0935] As dibenzo Specific examples of the compounds include compounds represented by any one of the following formulae (5-1) to (5-39). In addition, "tBu" in the following structural formula represents a tert-butyl group.

[0936] [Chemistry 288]

[0937]

[0938] [Chemistry 289]

[0939]

[0940] The light-emitting layer material (host material and dopant material) can also be used as the following polymer compound or its polymer crosslinked product, or the following pendant polymer compound or its pendant polymer crosslinked product, wherein the polymer compound is obtained by polymerizing a reactive compound substituted with a reactive substituent in the light-emitting layer material (host material and dopant material) as a monomer, and the pendant polymer compound is obtained by reacting a main chain polymer with the reactive compound. As the reactive substituent in the above case, the description of the polycyclic aromatic compound represented by formula (1) can be cited.

[0941] The details of the uses of such polymer compounds and polymer crosslinked products will be described later.

[0942] <An example of a polymer host material>

[0943] [Chemistry 290]

[0944]

[0945] In formula (SPH-1),

[0946] MU is independently a divalent group obtained by removing any two hydrogen atoms from an aromatic compound, EC is independently a monovalent group obtained by removing any one hydrogen atom from an aromatic compound, two hydrogen atoms in MU are substituted with EC or MU, and k is an integer of 2 to 50,000.

[0947] More specifically,

[0948] MU is independently arylene, heteroarylene, diarylene arylamino, diarylene arylboryl, oxaborane-diyl, azaborane-diyl,

[0949] EC are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy,

[0950] At least one hydrogen in MU and EC may be further substituted by an aryl group, a heteroaryl group, a diarylamino group, an alkyl group or a cycloalkyl group, and k is an integer of 2 to 50,000.

[0951] k is preferably an integer of 20 to 50,000, more preferably an integer of 100 to 50,000.

[0952] At least one hydrogen atom in MU and EC in formula (SPH-1) may be replaced by an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom or a deuterium atom.2 - can be composed of -O- or -Si(CH 3 ) 2 -substituted, except for the -CH 2 Any -CH other than - 2 - may be substituted by an arylene group having 6 to 24 carbon atoms, and any hydrogen in the alkyl group may be substituted by fluorine.

[0953] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds.

[0954] [Chemistry 291]

[0955]

[0956] More specifically, the divalent group may be represented by any of the following structures: Among these, MU is bonded to other MU or EC at *.

[0957] [Chemistry 292]

[0958]

[0959] [Chemistry 293]

[0960]

[0961] [Chemistry 294]

[0962]

[0963] [Chemistry 295]

[0964]

[0965] [Chemistry 296]

[0966]

[0967] [Chemistry 297]

[0968]

[0969] [Chemistry 298]

[0970]

[0971] [Chemistry 299]

[0972]

[0973] [Chemistry 300]

[0974]

[0975] In addition, examples of EC include monovalent groups represented by any of the following structures. Among these, EC is bonded to MU at *.

[0976] [Chemistry 301]

[0977]

[0978] [Chemistry 302]

[0979]

[0980] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (SPH-1) preferably has an alkyl group having 1 to 24 carbon atoms in 10% to 100% of the total number of MUs (k) in the molecule, more preferably has an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), and further preferably has an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms) in 50% to 100% of the total number of MUs (k) in the molecule. On the other hand, from the viewpoint of in-plane orientation and charge transport, preferably has an alkyl group having 7 to 24 carbon atoms in 10% to 100% of the total number of MUs (k) in the molecule, and more preferably has an alkyl group having 7 to 24 carbon atoms (branched alkyl group having 7 to 24 carbon atoms) in 30% to 100% of the total number of MUs (k) in the molecule.

[0981] The details of the uses of such polymer compounds and polymer crosslinked products will be described later.

[0982] <Electron injection layer and electron transport layer in organic electroluminescent elements>

[0983] The electron injection layer 107 plays a role in efficiently injecting electrons migrated from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role in efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are respectively formed by stacking or mixing one or more electron transport / injection materials, or are formed by a mixture of an electron transport / injection material and a polymer binder.

[0984] The so-called electron injection and transport layer is a layer responsible for injecting electrons from the cathode and then transporting electrons. It is ideal that the electron injection efficiency is high and the injected electrons are efficiently transported. Therefore, it is preferably a material with large electron affinity, large electron mobility, excellent stability, and impurities that are not easy to produce as traps during manufacture and use. However, considering the transmission balance of holes and electrons, in the case of mainly playing the role of efficiently preventing holes from the anode from recombining and flowing to the cathode side, even if the electron transport ability is not so high, it has the effect of improving luminous efficiency equally with the material with high electron transport ability. Therefore, the electron injection and transport layer in the present embodiment may also include the function of a layer that can efficiently prevent hole migration.

[0985] The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials and known compounds used for electron injection layers and electron transport layers of organic EL devices.

[0986] As the material used in the electron transport layer or the electron injection layer, it is preferably containing at least one selected from the following compounds: compounds containing aromatic rings or heteroaromatic rings containing one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes with electron-accepting nitrogen. Specifically, examples include: condensed ring aromatic ring derivatives such as naphthalene and anthracene, styrene aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl, purple ring ketone derivatives, coumarin derivatives, naphthalene dicarboxylic acid imide derivatives, quinone derivatives such as anthraquinone or diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives. As a metal complex with electron-accepting nitrogen, for example, hydroxylazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes can be listed. These materials can be used alone or in combination with different materials.

[0987] In addition, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline (oxine) derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, indole (benzazole) compounds, gallium complexes, pyrazole derivatives , perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6',2"-terpyridyl))benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, bisphenylvinyl derivatives, etc.

[0988] In addition, metal complexes having electron-accepting nitrogen can also be used, examples of which include hydroxyquinoline metal complexes, hydroxyoxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0989] The materials can be used alone or in combination with different materials.

[0990] Among the above materials, preferred are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline metal complexes.

[0991] <Borane derivatives>

[0992] The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and its details are disclosed in Japanese Patent Application Laid-Open No. 2007-27587.

[0993] [Chemistry 303]

[0994]

[0995] In the formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, substituted silyl, nitrogen-containing heterocyclic which may be substituted, or cyano, and R 13 ~R 16 Each of them is independently an alkyl group which may be substituted, a cycloalkyl group which may be substituted or an aryl group which may be substituted, X is an arylene group which may be substituted, Y is an aryl group having 16 or less carbon atoms which may be substituted, a substituted boron group or a substituted carbazolyl group which may be substituted, and n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group.

[0996] Among the compounds represented by the general formula (ETM-1), preferred are compounds represented by the following general formula (ETM-1-1) or compounds represented by the following general formula (ETM-1-2).

[0997] [Chemistry 304]

[0998]

[0999] In the formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, substituted silyl, nitrogen-containing heterocyclic which may be substituted, or cyano, and R 13 ~R 16 are each independently an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, and R 21 and R 22 are each independently at least one of hydrogen, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, a substituted silyl group, a nitrogen-containing heterocycle which may be substituted, or a cyano group, and X 1 is an arylene group having 20 or less carbon atoms which may be substituted, n is each independently an integer of 0 to 3, and m is each independently an integer of 0 to 4. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl groups.

[1000] [Chemistry 305]

[1001]

[1002] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, substituted silyl, nitrogen-containing heterocyclic which may be substituted, or cyano, and R13 ~R 16 are independently substituted alkyl, substituted cycloalkyl or substituted aryl, X 1 is an arylene group having 20 or less carbon atoms which may be substituted, and n is each independently an integer of 0 to 3. In the case of "may be substituted" or "substituted", examples of the substituent include aryl, heteroaryl, alkyl, and cycloalkyl.

[1003] As X 1 Specific examples include divalent groups represented by any of the following formulae (X-1) to (X-9). * in each structural formula represents a bonding position.

[1004] [Chemistry 306]

[1005]

[1006] (In each formula, R a are independently alkyl, cycloalkyl or phenyl which may be substituted)

[1007] Specific examples of the borane derivatives include the following compounds.

[1008] [Chemistry 307]

[1009]

[1010] The borane derivatives can be prepared using known starting materials and known synthesis methods.

[1011] <Pyridine derivatives>

[1012] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

[1013] [Chemistry 308]

[1014]

[1015] φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1-4.

[1016] In the formula (ETM-2-1), R 11 ~R 18 Each independently represents hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms).

[1017] In the formula (ETM-2-2), R11 and R 12 are each independently hydrogen, alkyl (preferably an alkyl group having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl group having 3 to 12 carbon atoms), or aryl (preferably an aryl group having 6 to 30 carbon atoms), R 11 and R 12 Can bond to form a ring.

[1018] In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15), and the pyridine substituent may be substituted independently by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. In addition, the pyridine substituent may be bonded to φ, an anthracene ring or a fluorene ring in each formula via a phenylene group or a naphthylene group. * in each structural formula indicates a bonding position.

[1019] [Chemistry 309]

[1020]

[1021] The pyridine substituent is any one of the above formulae (Py-1) to (Py-15), and among these, any one of the following formulae (Py-21) to (Py-44) is preferred. * in each structural formula represents a bonding position.

[1022] [Chemistry 310]

[1023]

[1024] At least one hydrogen in each pyridine derivative may be substituted by deuterium, and one of the two "pyridine substituents" in the formula (ETM-2-1) and the formula (ETM-2-2) may be substituted by an aryl group.

[1025] As R 11 ~R 18 The "alkyl" in the formula may be any of a straight chain and a branched chain, for example, a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. A preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl group" is an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms). A further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms).

[1026] Specific examples of the "alkyl group" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-amyl, n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

[1027] For example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like may be mentioned.

[1028] As the alkyl group having 1 to 4 carbon atoms substituting in the pyridine-based substituent, the description of the above-mentioned alkyl group can be cited.

[1029] As R 11 ~R 18 The "cycloalkyl" in the formula (a) includes, for example, a cycloalkyl group having 3 to 12 carbon atoms. A preferred "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. A more preferred "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. A further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms.

[1030] Specific examples of the "cycloalkyl group" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl.

[1031] As R 11 ~R 18 The "aryl group" in the formula (a) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, further preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

[1032] Specific examples of the "aryl group having 6 to 30 carbon atoms" include: phenyl as a monocyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl as a condensed tricyclic aromatic group, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, condensed tetraphenyl-(1-, 2-, 5-)yl as a condensed tetracyclic aromatic group, perylene-(1-, 2-, 3-)yl, condensed pentaphenyl-(1-, 2-, 5-, 6-)yl as a condensed pentacyclic aromatic group, and the like.

[1033] Preferred "aryl group having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, Preferably, there are phenyl, 1-naphthyl, 2-naphthyl and phenanthryl, and particularly preferably, there are phenyl, 1-naphthyl and 2-naphthyl.

[1034] R in the formula (ETM-2-2) 11 and R 12 They can be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like can be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[1035] Specific examples of the pyridine derivatives include the following compounds.

[1036] [Chemistry 311]

[1037]

[1038] The pyridine derivatives can be produced using known starting materials and known synthesis methods.

[1039] <Fluoranthene derivatives>

[1040] The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and its details are disclosed in International Publication No. 2010 / 134352.

[1041] [Chemistry 312]

[1042]

[1043] In the formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent in the case of substitution include aryl, heteroaryl, alkyl or cycloalkyl.

[1044] Specific examples of the fluoranthene derivatives include the following compounds.

[1045] [Chemistry 313]

[1046]

[1047] <BO derivatives>

[1048] The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by the following formula (ETM-4).

[1049] [Chemistry 314]

[1050]

[1051] R 1 ~R 11 Each independently represents hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group.

[1052] In addition, R 1 ~R 11 The adjacent groups in the group may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkoxy group or an aryloxy group, and at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group.

[1053] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted by halogen or deuterium.

[1054] The description of the substituents or the ring formation in the formula (ETM-4) can be based on the description of the polycyclic aromatic compound represented by the general formula (1) or (2).

[1055] Specific examples of the BO derivatives include the following compounds.

[1056] [Chemistry 315]

[1057]

[1058] The BO derivatives can be produced using known raw materials and known synthesis methods.

[1059] <Anthracene derivatives>

[1060] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

[1061] [Chemistry 316]

[1062]

[1063] Ar is independently divalent benzene or naphthalene, R 1 ~R 4 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[1064] Ar can be appropriately selected from divalent benzene or naphthalene, and the two Ars can be different or the same. From the perspective of the ease of synthesis of anthracene derivatives, they are preferably the same. Ar is bonded to pyridine to form a "site containing Ar and pyridine", and the site is bonded to anthracene as a group represented by any one of the following formulas (Py-1) to (Py-12). The * in each structural formula represents a bonding position.

[1065] [Chemistry 317]

[1066]

[1067] Among these groups, a group represented by any one of the formulas (Py-1) to (Py-9) is preferred, and a group represented by any one of the formulas (Py-1) to (Py-6) is more preferred. The structures of the two "parts containing Ar and pyridine" bonded to anthracene may be the same or different, and are preferably the same structure from the perspective of ease of synthesis of anthracene derivatives. Among them, from the perspective of device characteristics, it is preferred that the structures of the two "parts containing Ar and pyridine" are the same or different.

[1068] About R 1 ~R 4 The alkyl group having 1 to 6 carbon atoms may be any of a straight chain and a branched chain. That is, it is a straight chain alkyl group having 1 to 6 carbon atoms or a branched chain alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms). As specific examples, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-amyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl or 2-ethylbutyl, etc. are listed, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, and more preferably methyl, ethyl or tert-butyl.

[1069] As R 1 ~R 4Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in the group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl.

[1070] About R 1 ~R 4 The aryl group having 6 to 20 carbon atoms in is preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms.

[1071] Specific examples of the "aryl group having 6 to 20 carbon atoms" include phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-)cumenyl, (2-, 3-, 4-)biphenyl, (1-, 2-)naphthyl, and triphenyl groups (terphenyl-2'-yl, terphenyl-4'-yl, terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, terphenyl-2'-yl, terphenyl-3'-yl, terphenyl-4'-yl, as condensed tricyclic aromatic groups, such as anthracene-(1-, 2-, 9-)yl, acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl; as condensed tetracyclic aromatic groups, such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, fused tetraphenyl-(1-, 2-, 5-)yl; as condensed pentacyclic aromatic groups, such as perylene-(1-, 2-, 3-)yl.

[1072] Preferred "aryl group having 6 to 20 carbon atoms" is phenyl, biphenyl, terphenyl or naphthyl, more preferably phenyl, biphenyl, 1-naphthyl, 2-naphthyl or terphenyl-5'-yl, further preferably phenyl, biphenyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[1073] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).

[1074] [Chemistry 318]

[1075]

[1076] Ar 1 Each is independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[1077] Ar 2 Each independently represents an aryl group having 6 to 20 carbon atoms, and the same description as for the "aryl group having 6 to 20 carbon atoms" in the formula (ETM-5-1) can be cited. Preferably, it is an aryl group having 6 to 16 carbon atoms, more preferably, it is an aryl group having 6 to 12 carbon atoms, and particularly preferably, it is an aryl group having 6 to 10 carbon atoms. Specific examples include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenanthrenyl, phenanthrenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, etc.

[1078] R 1 ~R 4 Each of them is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and the descriptions in the above formula (ETM-5-1) can be referred to.

[1079] Specific examples of these anthracene derivatives include the following compounds.

[1080] [Chemistry 319]

[1081]

[1082] These anthracene derivatives can be produced using known starting materials and known synthesis methods.

[1083] <Benzofluorene derivatives>

[1084] The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

[1085] [Chemistry 320]

[1086]

[1087] Ar 1 Each independently represents an aryl group having 6 to 20 carbon atoms, and the same description as for the "aryl group having 6 to 20 carbon atoms" in the formula (ETM-5-1) can be cited. Preferably, it is an aryl group having 6 to 16 carbon atoms, more preferably, it is an aryl group having 6 to 12 carbon atoms, and particularly preferably, it is an aryl group having 6 to 10 carbon atoms. Specific examples include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenanthrenyl, phenanthrenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, etc.

[1088] Ar 2 are each independently hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms), and the two Ar 2 Can bond to form a ring.

[1089] As Ar2 The "alkyl" in the formula (a) may be any of a straight chain and a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. A preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl group" is an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms). A further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms). Specific examples of "alkyl groups" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-amyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[1090] As Ar 2 The "cycloalkyl" in the above-mentioned group includes, for example, a cycloalkyl group having 3 to 12 carbon atoms. A preferred "cycloalkyl" group is a cycloalkyl group having 3 to 10 carbon atoms. A more preferred "cycloalkyl" group is a cycloalkyl group having 3 to 8 carbon atoms. A further preferred "cycloalkyl" group is a cycloalkyl group having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[1091] As Ar 2 The "aryl group" in the formula (a) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, further preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

[1092] Specific examples of the "aryl group having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalenyl, phenanthrenyl, triphenylene, pyrenyl, naphthacene, perylenyl, and pentadienyl.

[1093] Two Ar 2 They can be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like can be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[1094] Specific examples of the benzofluorene derivatives include the following compounds.

[1095] [Chemistry 321]

[1096]

[1097] The benzofluorene derivatives can be prepared using known raw materials and known synthesis methods.

[1098] <Phosphine oxide derivatives>

[1099] The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). The details are also described in International Publication No. 2013 / 079217.

[1100] [Chemistry 322]

[1101]

[1102] R 5 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 carbon atoms,

[1103] R 6 is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms,

[1104] R 7 and R 8 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms, R 9 is oxygen or sulfur,

[1105] j is 0 or 1, k is 0 or 1, r is an integer of 0-4, and q is an integer of 1-3.

[1106] Here, examples of the substituent in the case of being substituted include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

[1107] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

[1108] [Chemistry 323]

[1109]

[1110] R 1 ~R 3 The substituents may be the same or different and are selected from the group consisting of hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, arylthioether, aryl, heterocyclic, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silanyl and the condensed ring formed therewith.

[1111] Ar 1 Ar may be the same or different and may be an arylene group or a heteroarylene group. 2 can be the same or different and can be aryl or heteroaryl. 1and Ar 2 At least one of the substituents has a substituent, or forms a condensed ring with an adjacent substituent. n is an integer from 0 to 3. When n is 0, there is no unsaturated structure. When n is 3, there is no R 1 .

[1112] Among these substituents, the so-called alkyl group refers to, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group, etc., which may be unsubstituted or substituted. The substituent group in the case of substitution is not particularly limited, and examples thereof include an alkyl group, an aryl group, a heterocyclic group, etc., which are also common in the following descriptions. In addition, the carbon number of the alkyl group is not particularly limited, and is generally in the range of 1 to 20 in terms of ease of acquisition or cost.

[1113] The cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, but is usually in the range of 3 to 20.

[1114] The term "aralkyl" refers to an aromatic hydrocarbon group such as benzyl or phenylethyl, which is substituted by an aliphatic hydrocarbon. The aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually in the range of 1 to 20.

[1115] In addition, the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, and a butadienyl group, and may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[1116] The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexenyl group, and may be unsubstituted or substituted.

[1117] The term "alkynyl group" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as ethynyl, and may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is generally in the range of 2 to 20.

[1118] The term "alkoxy group" refers to an aliphatic hydrocarbon group such as a methoxy group through an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

[1119] The alkylthio group is a group in which the oxygen atom in the ether bond of an alkoxy group is substituted with a sulfur atom.

[1120] The cycloalkylthio group is a group in which the oxygen atom in the ether bond of a cycloalkyloxy group is substituted with a sulfur atom.

[1121] The term "aryl ether group" refers to an aromatic hydrocarbon group such as a phenoxy group through an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[1122] The arylthioether group is a group in which the oxygen atom in the ether bond of an arylether group is substituted with a sulfur atom.

[1123] In addition, the so-called aryl group refers to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, and pyrenyl. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[1124] In addition, the heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[1125] The halogen refers to fluorine, chlorine, bromine and iodine.

[1126] The aldehyde group, carbonyl group, and amino group may include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

[1127] In addition, the aliphatic hydrocarbon, the alicyclic hydrocarbon, the aromatic hydrocarbon, and the heterocycle may be unsubstituted or substituted.

[1128] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The carbon number of the silyl group is not particularly limited, but is usually in the range of 3 to 20. The silicon number is usually 1 to 6.

[1129] The condensed ring formed between the adjacent substituents is, for example, 1 With R 2 ,Ar 1 With R 3 ,Ar 2 With R 2 ,Ar 2 With R 3 , R 2 With R 3 ,Ar 1 with Ar 2 Here, when n is 1, the two R 1 They may form conjugated or non-conjugated condensed rings with each other. These condensed rings may contain nitrogen atoms, oxygen atoms, and sulfur atoms in the ring structure, and may further condense with other rings.

[1130] Specific examples of the phosphine oxide derivatives include the following compounds.

[1131] [Chemical Formula 324]

[1132]

[1133] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[1134] <Pyrimidine Derivative>

[1135] The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011 / 021689.

[1136] [Chemical Formula 325]

[1137]

[1138] Ar is independently a substituted aryl group or a substituted heteroaryl group. n is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 2 or 3.

[1139] Examples of the "aryl group" of the "substituted aryl group" include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and still more preferably aryl groups having 6 to 12 carbon atoms.

[1140] Specific examples of the "aryl group" include: phenyl as a monocyclic aryl group, (2-, 3-, 4-) biphenyl as a bicyclic aryl group, (1-, 2-) naphthyl as a condensed bicyclic aryl group, terphenyl (meta-terphenyl-2'-yl, meta-terphenyl-4'-yl, meta-terphenyl-5'-yl, ortho-terphenyl-3'-yl, ortho-terphenyl-4'-yl, para-terphenyl-2'-yl, meta-terphenyl-2-yl, meta-terphenyl-3-yl, meta-terphenyl-4-yl, ortho-terphenyl-2-yl, ortho-terphenyl-3-yl, ortho-terphenyl-4-yl, para-terphenyl-2-yl, para-terphenyl-3-yl, para-terphenyl-4-yl) as a tricyclic aryl group, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl as a condensed tricyclic aryl group, quaterphenyl (5'-phenyl-meta-terphenyl-2-yl, 5'-phenyl-meta-terphenyl-3-yl, 5'-phenyl-meta-terphenyl-4-yl, meta-quaterphenyl) as a tetracyclic aryl group, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, benzo[c]phenanthrene-(1-, 2-, 5-)yl as a condensed tetracyclic aryl group, perylene-(1-, 2-, 3-)yl, benzo[ghi]perylene-(1-, 2-, 5-, 6-)yl as a condensed pentacyclic aryl group, etc.

[1141] The "heteroaryl" as the "replaceable heteroaryl" may include, for example, heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, still more preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. In addition, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms in addition to carbon.

[1142] Specific examples of the heteroaryl include: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, cyclopentylboronic acid group (phenazasilinyl), indazinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, naphthobenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphonyl, dibenzophosphonyl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindazolocarbazolyl, and benzobenzindazolocarbazolyl, etc.

[1143] In addition, the aryl and heteroaryl may be substituted, and may be substituted by the aryl or heteroaryl, respectively, for example.

[1144] Specific examples of the pyrimidine derivative include the following compounds, for example.

[1145] [Chemical formula 326]

[1146]

[1147] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[1148] <Carbazole derivative>

[1149] The carbazole derivative is, for example, a compound represented by the following formula (ETM-9) or a polymer formed by bonding multiple thereof through a single bond or the like. Details are described in U.S. Patent Publication No. 2014 / 0197386.

[1150] [Chemical formula 327]

[1151]

[1152] Ar is independently an aryl group which may be substituted or a heteroaryl group which may be substituted. n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

[1153] Examples of the "aryl group" of the "aryl group which may be substituted" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and still more preferably an aryl group having 6 to 12 carbon atoms.

[1154] Specific examples of the "aryl group" include: phenyl as a monocyclic aromatic group, (2-, 3-, 4-)biphenyl as a bicyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, terphenyl as a tricyclic aromatic group (terphenyl-2'-yl, terphenyl-4'-yl, terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, terphenyl-2-yl, terphenyl-3-yl, terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aromatic group. Acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl, tetraphenyl (5'-phenyl-terphenyl-2-yl, 5'-phenyl-terphenyl-3-yl, 5'-phenyl-terphenyl-4-yl, tetraphenyl) as a tetracyclic aromatic group, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, condensed tetraphenyl-(1-, 2-, 5-)yl as a condensed pentacyclic aromatic group, perylene-(1-, 2-, 3-)yl, condensed pentaphenyl-(1-, 2-, 5-, 6-)yl as a tetracyclic aromatic group, and the like.

[1155] Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon.

[1156] As specific heteroaryl groups, for example, the following can be mentioned: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, cyclopentylboranyl (phenazasilinyl), indazinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, naphthobenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphonyl, dibenzophosphonyl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, and benzobenzindolocarbazolyl, etc.

[1157] In addition, the aryl and heteroaryl groups may be substituted, and may be substituted by the aryl or heteroaryl group, respectively, for example.

[1158] The carbazole derivative may be a polymer formed by bonding a plurality of the compounds represented by the formula (ETM-9) through a single bond or the like. In this case, in addition to the single bond, it may also be bonded through an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring).

[1159] As specific examples of the carbazole derivative, for example, the following compounds can be mentioned.

[1160] [Chemical formula 328]

[1161]

[1162] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[1163] <Triazine derivative>

[1164] The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Details are described in U.S. Patent Publication No. 2011 / 0156013.

[1165] [Chemical formula 329]

[1166]

[1167] Ar is independently an aryl group which may be substituted or a heteroaryl group which may be substituted. n is an integer of 1 to 3, and is preferably 2 or 3.

[1168] Examples of the "aryl group" of the "aryl group which may be substituted" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and still more preferably an aryl group having 6 to 12 carbon atoms.

[1169] Specific examples of the "aryl group" include: phenyl as a monocyclic aromatic group, (2-, 3-, 4-)biphenyl as a bicyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, terphenyl as a tricyclic aromatic group (terphenyl-2'-yl, terphenyl-4'-yl, terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, terphenyl-2-yl, terphenyl-3-yl, terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aromatic group. Acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl, tetraphenyl (5'-phenyl-terphenyl-2-yl, 5'-phenyl-terphenyl-3-yl, 5'-phenyl-terphenyl-4-yl, tetraphenyl) as a tetracyclic aromatic group, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, condensed tetraphenyl-(1-, 2-, 5-)yl as a condensed pentacyclic aromatic group, perylene-(1-, 2-, 3-)yl, condensed pentaphenyl-(1-, 2-, 5-, 6-)yl as a tetracyclic aromatic group, and the like.

[1170] Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon.

[1171] Specific examples of the heteroaryl group include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiol, phenoxazinyl, Phenothiazinyl, phenazinyl, cyclopentylboronic acid group (phenazasilinyl), indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of benzophospholine oxide ring, a monovalent group of dibenzophospholine oxide ring, furazanyl, thianthrenyl, indolecarbazolyl, benzindazolecarbazolyl and benzobenzoindolecarbazolyl, etc.

[1172] In addition, the aryl group and the heteroaryl group may be substituted, for example, they may be substituted by the aryl group or the heteroaryl group, respectively.

[1173] Specific examples of the triazine derivatives include the following compounds.

[1174] [Chemistry 330]

[1175]

[1176] The triazine derivatives can be produced using known raw materials and known synthesis methods.

[1177] <Benzimidazole derivatives>

[1178] The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

[1179] [Chemistry 331]

[1180] φ-(Benzimidazole-based substituent)n (ETM-11)

[1181] φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenanthren ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, and the "benzimidazole substituent" is a substituent in which the pyridine substituent in the "pyridine substituent" of the formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced by a benzimidazole substituent, and at least one hydrogen in the benzimidazole derivative may be replaced by deuterium. The * in the following structural formula indicates a bonding position.

[1182] [Chemistry 332]

[1183]

[1184] The R 11 is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R in the above formula (ETM-2-1) and formula (ETM-2-2) can be cited. 11 Description.

[1185] φ is further preferably an anthracene ring or a fluorene ring. In this case, the structure can be referred to the description in the formula (ETM-2-1) or the formula (ETM-2-2). In each formula, R 11 ~R 18 The description in the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, the above formula (ETM-2-1) or formula (ETM-2-2) is described in the form of two pyridine substituents bonded together, but when these are replaced by benzimidazole substituents, the two pyridine substituents can be replaced by benzimidazole substituents (i.e., n=2), or any one pyridine substituent can be replaced by a benzimidazole substituent and R 11 ~R 18 Substitute another pyridine substituent (ie, n = 1). Furthermore, for example, R in the formula (ETM-2-1) may be substituted by a benzimidazole substituent. 11 ~R 18 At least one of R 11 ~R 18 Substituted "pyridine substituent".

[1186] Specific examples of the benzimidazole derivatives include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalene-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole, ]imidazole, 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

[1187] [Chemistry 333]

[1188]

[1189] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[1190] <Phenanthroline derivative>

[1191] The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006 / 021982.

[1192] [Chemical formula 334]

[1193]

[1194] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[b]fluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4.

[1195] In each formula, R 11 ~R 18 are each independently hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms). In addition, in the formula (ETM-12-1), any one of R 11 ~R 18 is bonded to φ as an aryl ring.

[1196] At least one hydrogen in each phenanthroline derivative can be replaced by deuterium.

[1197] As the alkyl group, cycloalkyl group, and aryl group in R 11 ~R 18 , the description of R 11 ~R 18 in the formula (ETM-2) can be cited. In addition, regarding φ, in addition to the above examples, the following structural formulas can be cited, for example. Furthermore, in the following structural formulas, R are each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or terphenyl. In addition, * in each structural formula indicates the bonding position.

[1198] [Chemical formula 335]

[1199]

[1200] Specific examples of the phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), 2,9-dimethyl-4,7-biphenyl-1,10-phenanthroline (bathocuproine), 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, or compounds represented by the following structural formulas.

[1201] [Chemistry 336]

[1202]

[1203] The phenanthroline derivatives can be prepared using known raw materials and known synthesis methods.

[1204] <Hydroxyquinoline metal complex>

[1205] The hydroxyquinoline metal complex is, for example, a compound represented by the following general formula (ETM-13).

[1206] [Chemistry 337]

[1207]

[1208] In the formula, R 1 ~R 6 Each is independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

[1209] Specific examples of the hydroxyquinoline metal complex include 8-hydroxyquinoline lithium, tris(8-hydroxyquinoline)aluminum, tris(4-methyl-8-hydroxyquinoline)aluminum, tris(5-methyl-8-hydroxyquinoline)aluminum, tris(3,4-dimethyl-8-hydroxyquinoline)aluminum, tris(4,5-dimethyl-8-hydroxyquinoline)aluminum, tris(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(4-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(5-methylphenol)aluminum, bis(3-methylphenol)aluminum, bis(4,5-dimethyl-8-hydroxyquinoline)aluminum, bis(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(5-methylphenol)aluminum, bis(3-methylphenol)aluminum, bis(4,5-dimethyl-8-hydroxyquinoline)aluminum, bis(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(3-methylphenol)aluminum, bis(4,5-dimethyl-8- 2-Methyl-8-hydroxyquinoline)(4-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,3-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,4-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-dimethylphenol) Aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-diphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-triphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-trimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,5,6-tetramethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(1-naphthol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-naphthol)aluminum, bis(2,4-dimethyl bis(2,4-dimethyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-8-hydroxyquinoline)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2,Aluminum bis(4-dimethyl-8-hydroxyquinoline), aluminum bis(2-methyl-4-ethyl-8-hydroxyquinoline)-μ-oxo-bis(2-methyl-4-ethyl-8-hydroxyquinoline), aluminum bis(2-methyl-4-methoxy-8-hydroxyquinoline)-μ-oxo-bis(2-methyl-4-methoxy-8-hydroxyquinoline), aluminum bis(2-methyl-5-cyano-8-hydroxyquinoline)-μ-oxo-bis(2-methyl-5-cyano-8-hydroxyquinoline), aluminum bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline), beryllium bis(10-hydroxybenzo[h]quinoline), etc.,

[1210] The hydroxyquinoline-based metal complex can be produced using known raw materials and known synthesis methods.

[1211] <Thiazole derivatives and benzothiazole derivatives>

[1212] Thiazole derivatives are, for example, compounds represented by the following formula (ETM-14-1).

[1213] [Chemical formula 338]

[1214] φ-(thiazole-based substituent)n (ETM-14-1)

[1215] Benzothiazole derivatives are, for example, compounds represented by the following formula (ETM-14-2).

[1216] [Chemical formula 339]

[1217] φ-(benzothiazole-based substituent)n (ETM-14-2)

[1218] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, and the "thiazole-based substituent" or "benzothiazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" of the formula (ETM-2), formula (ETM-2-1), and formula (ETM-2-2) is replaced by the following thiazolyl group or benzothiazolyl group. At least one hydrogen in the thiazole derivative and benzothiazole derivative can be replaced by deuterium. * in the following structural formula indicates the bonding position.

[1219] [Chemical formula 340]

[1220]

[1221] φ is further preferably an anthracene ring or a fluorene ring. In this case, the structure can refer to the description in the formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18The description in the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, the above formula (ETM-2-1) or formula (ETM-2-2) is described in the form of two pyridine substituents bonded together, but when these are replaced by thiazole substituents (or benzothiazole substituents), the two pyridine substituents can be replaced by thiazole substituents (or benzothiazole substituents) (i.e., n=2), and any one of the pyridine substituents can be replaced by a thiazole substituent (or benzothiazole substituent) and R 11 ~R 18 Substitute another pyridine substituent (ie, n = 1). Furthermore, for example, R in the formula (ETM-2-1) may be substituted by a thiazole substituent (or a benzothiazole substituent). 11 ~R 18 At least one of R 11 ~R 18 Substituted "pyridine substituent".

[1222] These thiazole derivatives or benzothiazole derivatives can be produced using known starting materials and known synthesis methods.

[1223] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. The reducing substance may be a variety of substances as long as it has a certain reducing property, for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes may be appropriately used.

[1224] As preferred reducing substances, alkali metals such as Na (work function is 2.36eV), K (work function is 2.28eV), Rb (work function is 2.16eV) or Cs (work function is 1.95eV), or alkaline earth metals such as Ca (work function is 2.9eV), Sr (work function is 2.0eV~2.5eV), or Ba (work function is 2.52eV), and substances with a work function of 2.9eV or less are particularly preferred. Among these reducing substances, more preferred reducing substances are alkali metals of K, Rb or Cs, and more preferably Rb or Cs, and most preferably Cs. The reducing ability of these alkali metals is particularly high. By adding a relatively small amount of these alkali metals to the material forming the electron transport layer or the electron injection layer, the luminous brightness in the organic EL element can be improved or the life can be prolonged. In addition, as the reducing substance having a work function of 2.9 eV or less, a combination of two or more of the alkali metals is also preferred, and a combination containing Cs is particularly preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of the light emission in the organic EL element can be improved or the life can be prolonged.

[1225] The electron injection layer material and the electron transport layer material can also be used as the following polymer compound or its polymer crosslinked body, or the following pendant polymer compound or its pendant polymer crosslinked body for the electron layer material, wherein the polymer compound is obtained by polymerizing the reactive compound substituted with a reactive substituent in the electron injection layer material and the electron transport layer material as a monomer, and the pendant polymer compound is obtained by reacting a main chain polymer with the reactive compound. As the reactive substituent in the above case, the description in the polycyclic aromatic compound represented by formula (1) can be cited.

[1226] The details of the uses of such polymer compounds and polymer crosslinked products will be described later.

[1227] <Cathode in organic electroluminescent device>

[1228] The cathode 108 plays a role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

[1229] As the material forming the cathode 108, if it is a substance that can efficiently inject electrons into the organic layer, it is not particularly limited, and the same material as the material forming the anode 102 can be used. Among them, preferably metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy of lithium fluoride / aluminum, etc.) and the like. In order to improve the efficiency of electron injection to improve the characteristics of the element, lithium, sodium, potassium, cesium, calcium, magnesium or alloys containing these low work function metals are effective. However, these low work function metals are usually unstable in the atmosphere. In order to improve this point, it is known that there is a method of doping a trace amount of lithium, cesium or magnesium into the organic layer and using an electrode with high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. Among them, it is not limited to these.

[1230] Furthermore, the following preferred examples can be cited: for the purpose of protecting the electrode, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys of these metals, inorganic substances such as silicon dioxide, titanium dioxide and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, etc. are laminated. The method for producing these electrodes is not particularly limited as long as it is a method that can achieve conductivity such as resistance heating, electron beam evaporation, sputtering, ion plating and coating.

[1231] <Adhesives that can be used for each layer>

[1232] The materials used for the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer may form each layer independently, or may be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, acrylonitrile-butadiene-styrene (ABS) resin, polyurethane resin, or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc., as polymer binders.

[1233] <Method for producing organic electroluminescent element>

[1234] Each layer constituting the organic EL element can be formed by making the material to constitute each layer into a thin film using a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular stacking, printing, spin coating, casting, coating, etc. The film thickness of each layer formed in the above manner is not particularly limited and can be appropriately set according to the properties of the material, but is generally in the range of 2nm to 5000nm. The film thickness can generally be measured using a crystal oscillation film thickness measuring device or the like. When using the vapor deposition method for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, etc. The vapor deposition conditions are generally preferably a boat heating temperature of +50°C to +400°C, a vacuum degree of 10 -6 Pa~10 -3 Pa, vapor deposition rate 0.01 nm / sec to 50 nm / sec, substrate temperature -150°C to +300°C, and film thickness 2 nm to 5 μm are appropriately set.

[1235] When a direct current voltage is applied to the organic EL element obtained in the above manner, it can be applied with the anode as + polarity and the cathode as - polarity. If a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or translucent electrode side (anode or cathode, or both). In addition, the organic EL element also emits light when a pulse current or an alternating current is applied. Furthermore, the waveform of the applied alternating current can be arbitrary.

[1236] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element including anode / hole injection layer / hole transport layer / light-emitting layer including a host material and a dopant material / electron transport layer / electron injection layer / cathode is described.

[1237] <Evaporation method>

[1238] On a suitable substrate, a thin film of an anode material is formed by a vapor deposition method to make an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A main material and a dopant material are co-evaporated thereon to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and then a thin film containing a cathode material is formed by a vapor deposition method as a cathode, thereby obtaining a target organic EL element. Furthermore, in the production of the organic EL element, the production order can also be reversed, and the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, anode are produced in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, anode.

[1239] <Wet film forming method>

[1240] A low molecular weight compound that can form each organic layer of an organic EL element is prepared as a liquid organic layer-forming composition, and the composition is used to perform a wet film-forming method. In the absence of an appropriate organic solvent that dissolves the low molecular weight compound, the organic layer-forming composition can also be prepared from a high molecular weight compound that is polymerized together with other monomers or main chain polymers that have a solubility function as a reactive compound that replaces a reactive substituent in the low molecular weight compound.

[1241] The wet film forming method is usually formed by the following steps, the steps are the coating step of coating the organic layer forming composition on the substrate and the drying step of removing the solvent from the coated organic layer forming composition. In the case where the polymer compound has a cross-linking substituent (also referred to as a cross-linking polymer compound), the drying step is further cross-linked to form a polymer cross-linked body. According to the difference in the coating step, the method using a spin coater is called a spin coating method, the method using a slit coater is called a slit coating method, the method using a plate is called a gravure, a lithography, a reverse lithography, a flexographic printing method, the method using an inkjet printer is called an inkjet method, and the method of blowing attached to a mist is called a spray method. There are methods such as air drying, heating, and reduced pressure drying in the drying step. The drying step can be performed only once, or it can be performed multiple times using different methods or conditions. In addition, for example, different methods can be used as calcination under reduced pressure.

[1242] The so-called wet film forming method is a film forming method using a solution, such as a partial printing method (inkjet method), spin coating method or casting method, coating method, etc. The wet film forming method is different from the vacuum evaporation method, and does not require the use of expensive vacuum evaporation equipment, and can be formed under atmospheric pressure. In addition, the wet film forming method can be large-scale or continuously produced, thereby reducing manufacturing costs.

[1243] On the other hand, when compared with the vacuum evaporation method, there are cases where the wet film forming method is difficult to laminate. When using the wet film forming method to make a laminated film, it is necessary to prevent the dissolution of the bottom layer caused by the composition of the upper layer, and use a composition that controls the solubility, cross-linking of the bottom layer, and an orthogonal solvent (solvents that do not dissolve each other). However, even if these technologies are used, there are cases where it is difficult to use the wet film forming method for coating all films.

[1244] Therefore, a method is generally adopted in which only some layers are formed by a wet film-forming method and the remaining layers are formed by a vacuum evaporation method to produce an organic EL element.

[1245] For example, the following shows a part of the procedure for manufacturing an organic EL element by applying the wet film formation method.

[1246] (Procedure 1) Anode film formation by vacuum deposition method

[1247] (Procedure 2) Film formation of a hole injection layer-forming composition containing a hole injection layer material by a wet film formation method

[1248] (Procedure 3) Film formation of a hole transport layer-forming composition containing a hole transport layer material by a wet film formation method

[1249] (Procedure 4) Film formation of a composition for forming a light-emitting layer containing a host material and a dopant material by a wet film formation method

[1250] (Procedure 5) Film formation of electron transport layer by vacuum deposition method

[1251] (Procedure 6) Film formation of electron injection layer by vacuum deposition method

[1252] (Procedure 7) Cathode film formation by vacuum deposition method

[1253] By going through the above process, an organic EL element including anode / hole injection layer / hole transport layer / light-emitting layer including a host material and a dopant material / electron transport layer / electron injection layer / cathode can be obtained.

[1254] Of course, by providing a means for preventing the dissolution of the underlying light-emitting layer and using a means for film formation from the cathode side in the reverse order to the above-described procedure, a layer-forming composition containing an electron transport layer material or an electron injection layer material can be prepared and these can be formed into films by a wet film-forming method.

[1255] <Other film forming methods>

[1256] Laser heating drawing method (Laser Induced Thermal Imaging (LITI)) can be used for film formation of the composition for forming an organic layer. LITI is a method of heating and evaporating a compound attached to a substrate using a laser, and the composition for forming an organic layer can be used in the material coated on the substrate.

[1257] <Optional Step>

[1258] Before and after each film forming step, appropriate treatment steps, cleaning steps and drying steps may be added as appropriate. Examples of the treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heating treatment. Furthermore, a series of steps for making a bank may be mentioned.

[1259] Photolithography can be used in the production of the bank. As the bank material that can be photolithographically processed, positive resist materials and negative resist materials can be used. In addition, printing methods that can be patterned, such as inkjet printing, gravure lithography, reverse lithography, and screen printing, can also be used. At this time, a permanent resist material can also be used.

[1260] Examples of materials for the bank include polysaccharides and their derivatives, homopolymers and copolymers of vinyl monomers having hydroxyl groups, biopolymers, polyacryl compounds, polyesters, polystyrene, polyimides, polyamide-imides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, (meth)acrylate epoxy esters, (meth)acrylate melamine esters, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetates, polynorbornene, synthetic rubbers, fluorinated polymers such as polyvinylidene fluoride, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, and fluorocarbon polymers, but the present invention is not limited thereto.

[1261] <Organic layer forming composition used in wet film forming method>

[1262] The composition for forming an organic layer is obtained by dissolving a low molecular compound that can form each organic layer of an organic EL element, or a high molecular compound obtained by polymerizing the low molecular compound, in an organic solvent. For example, the composition for forming a luminescent layer contains at least one polycyclic aromatic compound (or its high molecular compound) as a dopant material as a first component, at least one main material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the luminescent layer obtained from the composition, and the second component functions as a main component of the luminescent layer. The third component functions as a solvent that dissolves the first component and the second component in the composition, and obtains a smooth and uniform surface shape by the controlled evaporation rate of the third component itself during coating.

[1263] <Organic solvent>

[1264] The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, the film-forming property and the presence or absence of defects, surface roughness, and smoothness of the coating film can be controlled and improved. In addition, when the film is formed by an inkjet method, the stability of the meniscus at the pinhole of the inkjet head can be controlled, and the ejection property can be controlled and improved. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical properties, luminescent properties, efficiency, and life of the organic EL element having the organic layer obtained from the composition for forming an organic layer can be improved.

[1265] (1) Physical properties of organic solvents

[1266] The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and further preferably 150°C to 250°C. From the perspective of inkjet ejection, the boiling point is preferably higher than 130°C. In addition, from the perspective of defects, surface roughness, residual solvent and smoothness of the coating film, the boiling point is preferably lower than 300°C. From the perspective of good inkjet ejection, film forming properties, smoothness and low residual solvent, the organic solvent is more preferably a structure containing two or more organic solvents. On the other hand, depending on the situation, taking into account transportability, etc., it can also be a composition made into a solid state by removing the solvent from the organic layer forming composition.

[1267] Furthermore, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is particularly preferably GS ) is lower than the boiling point (BP) of the bad solvent (PS) PS ) structure.

[1268] By adding a high-boiling-point poor solvent, the low-boiling-point good solvent evaporates first during film formation, increasing the concentration of the components and the poor solvent in the composition and promoting rapid film formation. As a result, a coating film with fewer defects, less surface roughness, and high smoothness can be obtained.

[1269] The difference in solubility (S GS -S PS ) is preferably 1% or more, more preferably 3% or more, and still more preferably 5% or more. The difference in boiling point (BP PS -BP GS ) is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[1270] The organic solvent is removed from the coating by drying steps such as vacuum, decompression, heating, etc. after film formation. When heating, from the perspective of improving the coating film-forming property, it is preferably carried out at a glass transition temperature (Tg) of at least one of the solutes + 30°C or less. In addition, from the perspective of reducing the residual solvent, it is preferably heated at a glass transition temperature (Tg) of at least one of the solutes -30°C or more. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is fully removed because the film is thin. In addition, multiple dryings can be performed at different temperatures, and multiple drying methods can also be used in combination.

[1271] (2) Specific examples of organic solvents

[1272] Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene-based solvents, phenyl ether-based solvents, alkyl ether-based solvents, cyclic ketone-based solvents, aliphatic ketone-based solvents, monocyclic ketone-based solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptane-2-ol, octane-2-ol, decane-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and diethylene glycol. Dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-dimethylpyridine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4 -Fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, tert-butylbenzene, 2-methylanisole, phenethyl ether, benzodioxole, 4-methylanisole, sec-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoro-o-dimethoxybenzene (4-fluoroveratrole), 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decahydronaphthalene, neopentylbenzene, 2, 5-Dimethylanisole, 2,4-Dimethylanisole, benzonitrile, 3,5-Dimethylanisole, diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-Dimethylanisole, o-tolunitrile, n-pentylbenzene, o-dimethoxybenzene (veratrole), 1,2,3,4-Tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-Methylnaphthalene, butyl benzoate, 2-Methylbiphenyl, 3-phenoxytoluene, 2,2'-Dimethylbiphenyl (2,2'-bitolyl), dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butoxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, benzyl octyl ether, etc., but are not limited thereto. In addition, the solvent may be used alone or in combination.

[1273] <Optional ingredients>

[1274] The composition for forming an organic layer may contain an optional component within a range that does not impair its properties. Examples of the optional component include a binder and a surfactant.

[1275] (1) Adhesive

[1276] The composition for forming an organic layer may also contain a binder. The binder is used to bond the obtained film to the substrate while forming the film. In addition, it plays a role in dissolving, dispersing and bonding other components in the composition for forming an organic layer.

[1277] Examples of the binder used in the composition for forming the organic layer include acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene (ABS) resins, acrylonitrile-styrene (AS) resins, phenol resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers, but the present invention is not limited thereto.

[1278] The binder used in the composition for forming an organic layer may be used alone or in combination of two or more.

[1279] (2) Surfactants

[1280] For example, in order to control the uniformity of the film surface, the affinity of the solvent and the liquid repellency of the film surface of the organic layer forming composition, the organic layer forming composition may also contain a surfactant. Surfactants are classified into ionic and nonionic according to the structure of the hydrophilic group, and are further classified into alkyl, silicon and fluorine according to the structure of the hydrophobic group. In addition, according to the structure of the molecule, it is classified into a monomolecular system with a simple structure having a relatively small molecular weight and a polymer system with a side chain or branch having a large molecular weight. In addition, according to the composition, it is classified into a single system, a mixed system mixed with two or more surfactants and a substrate. As a surfactant that can be used for the organic layer forming composition, all types of surfactants can be used.

[1281] Examples of the surfactant include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, and Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, and Disperbyk 164. 4. Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK 300, BYK 306, BYK 310, BYK 320, BYK 330, BYK 342, BYK 344, BYK 346 (trade name, BYK-Chemie Japan), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade names, Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade names, Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade names, NEOS Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade names, Mitsubishi Materials Co., Ltd. Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (trade names, manufactured by DIC Corporation),Fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethyleneethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglyceroltetra(fluoroalkylpolyoxyethyleneethers), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylenenonylphenylether, polyoxyethyleneoctylphenylether, polyoxyethylenealkylethers, polyoxyethylenelaurate, polyoxyethyleneoleate, polyoxyethylenestearate, polyoxyethylenelaurylamine, sorbitanlaurate, sorbitanpalmitate, sorbitanstearate, sorbitanoleate, sorbitanfatty acid esters, polyoxyethylenesorbitanlaurate, polyoxyethylenesorbitanpalmitate, polyoxyethylenesorbitanstearate, polyoxyethylenesorbitanoleate, polyoxyethylenenaphthylether, alkylbenzenesulfonates and alkyldiphenyletherdisulfonates.

[1282] Furthermore, the surfactant may be used alone or in combination of two or more.

[1283] <Composition and physical properties of the organic layer-forming composition>

[1284] The content of each component in the organic layer-forming composition is determined from the viewpoints of good solubility, storage stability and film-forming property of each component in the organic layer-forming composition, high-quality film quality of the coating obtained from the organic layer-forming composition, good ejection property when using the inkjet method, and good electrical properties, luminescent properties, efficiency and life of an organic EL element having an organic layer made using the composition. For example, in the case of a light-emitting layer-forming composition, it is preferred that the first component is 0.0001% by weight to 2.0% by weight relative to the total weight of the light-emitting layer-forming composition, the second component is 0.0999% by weight to 8.0% by weight relative to the total weight of the light-emitting layer-forming composition, and the third component is 90.0% by weight to 99.9% by weight relative to the total weight of the light-emitting layer-forming composition.

[1285] More preferably, the first component accounts for 0.005 to 1.0% by weight of the total weight of the composition for forming a light-emitting layer, the second component accounts for 0.095 to 4.0% by weight of the total weight of the composition for forming a light-emitting layer, and the third component accounts for 95.0 to 99.9% by weight of the total weight of the composition for forming a light-emitting layer. Even more preferably, the first component accounts for 0.05 to 0.5% by weight of the total weight of the composition for forming a light-emitting layer, the second component accounts for 0.25 to 2.5% by weight of the total weight of the composition for forming a light-emitting layer, and the third component accounts for 97.0 to 99.7% by weight of the total weight of the composition for forming a light-emitting layer.

[1286] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components by stirring, mixing, heating, cooling, dissolving, dispersing, etc. using a known method. In addition, filtering, degassing (also called degassing), ion exchange treatment, and inert gas replacement and sealing treatment can also be appropriately selected after preparation.

[1287] Regarding the viscosity of the composition for forming an organic layer, a high viscosity can obtain good film-forming properties and good ejection properties when using an inkjet method. On the other hand, a low viscosity is easy to make a thin film. Therefore, the viscosity of the composition for forming an organic layer is preferably 0.3mPa·s to 3mPa·s at 25°C, and more preferably 1mPa·s to 3mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer.

[1288] Regarding the surface tension of the composition for forming an organic layer, a low surface tension can obtain good film forming properties and a defect-free coating film. On the other hand, a high surface tension can obtain good inkjet ejection properties. Therefore, the viscosity of the composition for forming an organic layer is preferably such that the surface tension at 25° C. is 20 mN / m to 40 mN / m, more preferably 20 mN / m to 30 mN / m. In the present invention, the surface tension is a value measured using a hanging drop method.

[1289] <Crosslinkable polymer compound: compound represented by general formula (XLP-1)>

[1290] Next, the case where the polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).

[1291] [Chemistry 341]

[1292]

[1293] In formula (XLP-1),

[1294] MUx, ECx and k have the same definitions as MU, EC and k in the formula (SPH-1), wherein the compound represented by the formula (XLP-1) has at least one cross-linking substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a cross-linking substituent in the molecule is 0.1 wt% to 80 wt%.

[1295] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5% by weight to 50% by weight, more preferably 1% by weight to 20% by weight.

[1296] As the crosslinkable substituent (XLS), if it is a group capable of further crosslinking the polymer compound, there is no particular limitation, and a substituent having the following structure is preferred. In each structural formula, * indicates the bonding position.

[1297] [Chemical formula 342]

[1298]

[1299] L is each independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, an alkylene group having 1 to 12 carbon atoms, an oxyalkylene group having 1 to 12 carbon atoms, and a polyoxyalkylene group having 1 to 12 carbon atoms. Among the substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10), or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3), or formula (XLS-17) is more preferred.

[1300] As the divalent aromatic compound having a crosslinkable substituent, for example, a compound having the following partial structure can be cited. In the following structural formula, * indicates the bonding position.

[1301] [Chemical formula 343]

[1302]

[1303] [Chemical formula 344]

[1304]

[1305] [Chemical formula 345]

[1306]

[1307] [Chemical formula 346]

[1308]

[1309] <Manufacturing methods of polymer compounds and crosslinkable polymer compounds>

[1310] Regarding the manufacturing methods of polymer compounds and crosslinkable polymer compounds, the compounds represented by the formula (SPH-1) and the compound represented by the formula (XLP-1) will be described as examples. These compounds can be synthesized by appropriately combining known manufacturing methods.

[1311] As the solvent used in the reaction, aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc. can be cited. For example, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, etc. can be cited.

[1312] Alternatively, the reaction may be carried out in a two-phase system. In the case of carrying out the reaction in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[1313] When the compound of formula (SPH-1) and the compound of formula (XLP-1) are manufactured, they can be manufactured in one stage or in multiple stages. In addition, it can be carried out by a general polymerization method in which all the raw materials are placed in a reaction vessel and then the reaction is started, it can also be carried out by a drop polymerization method in which the raw materials are added dropwise to the reaction vessel, it can also be carried out by a precipitation polymerization method in which the product is precipitated as the reaction proceeds, and these can be appropriately combined to synthesize. For example, when the compound represented by formula (SPH-1) is synthesized in one stage, the target is obtained by reacting the monomer unit (MU) and the end-capping unit (EC) in a state where the monomer unit (MU) and the end-capping unit (EC) are added to the reaction vessel. In addition, when the compound represented by general formula (SPH-1) is synthesized in multiple stages, the target is obtained by adding the end-capping unit (EC) and reacting after the monomer unit (MU) is polymerized to the target molecular weight. If different types of monomer units (MU) are added in multiple stages to react, a polymer having a concentration gradient for the structure of the monomer unit can be produced. In addition, after the precursor polymer is prepared, a polymer as the target can be obtained by subsequent reactions.

[1314] In addition, if the polymerizable group of the monomer unit (MU) is selected, the primary structure of the polymer can be controlled. For example, as shown in synthesis schemes 1 to 3, a polymer having a random primary structure (synthesis scheme 1), a polymer having a regular primary structure (synthesis schemes 2 and 3), etc. can be synthesized, and can be used in appropriate combinations according to the target. Furthermore, if a monomer unit having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[1315] [Chemistry 347]

[1316]

[1317] The monomer units that can be used in the present invention are those described in Japanese Patent Application Laid-Open No. 2010-189630, International Publication No. 2012 / 086671, International Publication No. 2013 / 191088, International Publication No. 2002 / 045184, International Publication No. 2011 / 049241, International Publication No. 2013 / 146806, International Publication No. 2005 / 049546, and International Publication No. 2015 / 145871. , Japanese Patent Laid-Open No. 2010-215886, Japanese Patent Laid-Open No. 2008-106241, Japanese Patent Laid-Open No. 2010-215886, International Publication No. 2016 / 031639, Japanese Patent Laid-Open No. 2011-174062, International Publication No. 2016 / 031639, International Publication No. 2016 / 031639, and International Publication No. 2002 / 045184.

[1318] In addition, regarding the specific polymer synthesis procedure, it can be based on Japanese Patent Laid-Open No. 2012-036388, International Publication No. 2015 / 008851, Japanese Patent Laid-Open No. 2012-36381, Japanese Patent Laid-Open No. 2012-144722, International Publication No. 2015 / 194448, International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, International Publication No. The present invention can be synthesized by the method described in International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2016 / 031639, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2015 / 145871, International Publication No. 2011 / 049241, and Japanese Patent Application Laid-Open No. 2012-144722.

[1319] <Application examples of organic electroluminescent elements>

[1320] Furthermore, the present invention can also be applied to a display device including an organic EL element, a lighting device including an organic EL element, or the like.

[1321] A display device or lighting device having an organic EL element can be manufactured by a known method such as connecting the organic EL element of this embodiment to a known driving device, and can be driven using a known driving method such as DC driving, pulse driving, AC driving, etc. as appropriate.

[1322] As display devices, for example, panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (for example, refer to Japanese Patent Laid-Open No. 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281086, etc.). In addition, as display modes of displays, for example, matrix and segment modes can be listed. Furthermore, matrix display and segment display can coexist in the same panel.

[1323] The matrix is ​​a two-dimensional arrangement of pixels for display in a grid or mosaic shape, etc., which displays text or images through a collection of pixels. The shape or size of the pixel is determined according to the purpose. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with a side of less than 300μm are usually used. In addition, in the case of large displays such as display panels, pixels with a side of mm are used. In the case of monochrome display, it is sufficient to arrange pixels of the same color. In the case of color display, red, green, and blue pixels are displayed in parallel. In this case, typical ones are triangular and stripe types. Moreover, as a driving method of the matrix, it can be either a line-sequential driving method or an active matrix. Line-sequential driving has the advantage of a simple structure, but in the case of considering the operating characteristics, an active matrix is ​​sometimes more excellent, so the driving method also needs to be used according to the purpose.

[1324] In the segmented method (type), a pattern is formed in a manner to display predetermined information, and the determined area is illuminated. Examples include: time or temperature display in a digital clock or thermometer, operating status display of an audio device or induction cooker, and panel display of a car.

[1325] As lighting devices, for example, lighting devices for indoor lighting, backlight sources for liquid crystal display devices, etc. (for example, refer to Japanese Patent Laid-Open No. 2003-257621, Japanese Patent Laid-Open No. 2003-277741, Japanese Patent Laid-Open No. 2004-119211, etc.). Backlight sources are mainly used to improve the visibility of display devices that do not emit light by themselves, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display boards, and logos. In particular, as a backlight source for personal computers where thinning is becoming a problem in liquid crystal display devices, if it is considered that the existing methods are difficult to be thinned due to the inclusion of fluorescent lamps or light guide plates, the backlight source using the light-emitting element of this embodiment has the characteristics of being thin and lightweight.

[1326] 3-2. Other organic components

[1327] In addition to the organic electroluminescent element, the polycyclic aromatic compound of the present invention can be used to prepare organic field effect transistors or organic thin film solar cells.

[1328] An organic field effect transistor is a transistor that controls current by using an electric field generated by voltage input. In addition to the source electrode and the drain electrode, a gate electrode is provided. If a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. Compared with a single transistor (bipolar transistor), a field effect transistor is easy to miniaturize and is often used as a component constituting an integrated circuit.

[1329] The structure of an organic field effect transistor is usually provided by making the source electrode and the drain electrode contact the organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and further providing the gate electrode via an insulating layer (dielectric layer) contacting the organic semiconductor active layer. As its element structure, for example, the following structure can be cited.

[1330] (1) Substrate / gate electrode / insulator layer / source electrode / drain electrode / organic semiconductor active layer

[1331] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode / drain electrode

[1332] (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode

[1333] (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode

[1334] The organic field effect transistor having such a structure can be used as a pixel driving switch element of an active matrix driven liquid crystal display or an organic electroluminescent display.

[1335] Organic thin film solar cells have a structure in which an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode of ITO or the like are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention can be used as materials for hole transport layers, p-type semiconductor layers, n-type semiconductor layers, and electron transport layers according to their physical properties. In organic thin film solar cells, the polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials. In addition to the above, organic thin film solar cells may also be appropriately equipped with hole blocking layers, electron blocking layers, electron injection layers, hole injection layers, smoothing layers, etc. In organic thin film solar cells, known materials used for organic thin film solar cells can be appropriately selected for use in combination.

[1336] Example

[1337] The present invention will be described in more detail below by way of examples, but the present invention is not limited to these examples. First, a synthesis example of a polycyclic aromatic compound will be described below.

[1338] Synthesis Example (1): Synthesis of Compound (1-411)

[1339] [Chemistry 348]

[1340]

[1341] Under a nitrogen atmosphere, 2,3-dichloroaniline (6.0 g), 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene (25 g), dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 0.44 g), sodium tert-butoxide (NaOtBu, 14.8 g) and xylene (120 ml) were placed in a flask and heated at 120° C. for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. After the crude product was purified using a silica gel short column (eluent: toluene), the solvent was concentrated, methanol was added to the obtained crude product and ice-cooled, the precipitated crystals were filtered and washed with methanol, thereby obtaining compound (IA) (17.0 g).

[1342] [Chemistry 349]

[1343]

[1344] Under nitrogen environment, compound (IA) (8.0 g), bis (4-tert-butylphenyl) amine (25 g), Pd-132 (0.10 g), NaOtBu (2.1 g) and xylene (40 ml) were placed in a flask and heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. After the crude product was purified using a short silica gel column (eluent: toluene), the solvent was concentrated, methanol was added to the obtained crude product and ice-cooled, the precipitated crystals were filtered and washed with methanol, thereby obtaining compound (IB) (9.7 g).

[1345] [Chemistry 350]

[1346]

[1347] Under nitrogen atmosphere, 1.53M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing compound (IB) (8.6 g) and tert-butylbenzene (80 ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and added with boron tribromide (5.8 g), and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and the temperature was raised to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled by an ice bath were added in sequence and stirred for 1 hour. The yellow suspension was filtered and its precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating, and then purified by a short silica gel column (eluent: toluene). The obtained crude product was added to toluene and concentrated, and then Solmix (A-11) was added. The precipitated crystals were filtered and washed with methanol to obtain Compound (1-411) (3.0 g).

[1348] [Chemistry 351]

[1349]

[1350] The structure of the obtained compound was confirmed by nuclear magnetic resonance (NMR) measurement.

[1351] 1 H-NMR (CDCl 3 ): δ=1.09(s,6H),1.27(s,6H),1.42(s,6H),1.46(s,9H),1.48(s,9H),1.49(s,6H),1.71-1.80(m,8H),6.11(d,1H),6.23(d,1H) ,6.59(s,1H),6.73(d,1H),7.09(dd,1H),7.25-7.30(m,5H),7.51(dd,1H),7.59(d,1H),7.67(d,2H),8.92(s,1H),8.99(d,1H).

[1352] Synthesis Example (2): Synthesis of Compound (1-590)

[1353] [Chemistry 352]

[1354]

[1355] Under nitrogen atmosphere, 2,3-dichloro-5-methylaniline (6.6 g), 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene (25 g), Pd-132 (0.54 g), NaOtBu (9.0 g) and xylene (90 ml) were placed in a flask and heated at 120°C for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. After the crude product was purified using a short silica gel column (eluent: toluene), the solvent was concentrated, methanol was added to the obtained crude product and ice-cooled, the precipitated crystals were filtered and washed with methanol, thereby obtaining compound (IC) (13.0 g).

[1356] [Chemistry 353]

[1357]

[1358] Under nitrogen environment, compound (IC) (8.0 g), bis (4-tert-butylphenyl) amine (4 g), Pd-132 (0.10 g), NaOtBu (2.1 g) and xylene (40 ml) were placed in a flask and heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. After the crude product was purified using a short silica gel column (eluent: toluene), the solvent was concentrated, ethyl acetate and methanol were added to the obtained crude product in sequence, the precipitated crystals were filtered and washed with methanol, thereby obtaining compound (ID) (11.0 g).

[1359] [Chemistry 354]

[1360]

[1361] Under nitrogen atmosphere, 1.53M tert-butyllithium pentane solution (18.9 ml) was added to a flask containing compound (ID) (11.0 g) and tert-butylbenzene (110 ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (7.3 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled by ice bath were added in sequence and stirred for 1 hour. After the organic layer was separated, it was washed with water (twice) and the solvent was distilled off under reduced pressure. Methanol was added to the obtained residue and cooled in an ice bath, and the precipitate was filtered and washed with methanol. The yellow crystals were dissolved in toluene by heating, and then purified by a short silica gel column (eluent: toluene). The obtained crude product was added to toluene and concentrated, and then ethyl acetate and Solmix (A-11) were added in sequence, and then ethyl acetate was distilled off, the precipitated crystals were filtered, and then the crystals were washed with methanol to obtain compound (1-590) (4.0 g).

[1362] [Chemistry 355]

[1363]

[1364] The structure of the obtained compound was confirmed by NMR measurement.

[1365] 1 H-NMR (CDCl 3 ): δ=1.08(s,6H),1.27(s,6H),1.42(s,6H),1.46(s,9H),1.47(s,9H),1.48(s,6H),1.69-1.81(m,8H),2.18(s,3H),5.97(s,1H),6.06 (s,1H),6.52(s,1H),6.67(d,1H),7.08(dd,1H),7.25-7.29(m,3H),7.48(dd,1H),7.59(d,1H),7.67(d,2H),8.89(s,1H),8.97(d,1H).

[1366] Synthesis Example (3): Synthesis of Compound (1-1301)

[1367] [Chemistry 356]

[1368]

[1369] Under nitrogen atmosphere, compound (IA) (8.0 g), compound (IE) (5.6 g), tris(dibenzylideneacetone)dipalladium(0) [Pd 2 (dba) 3 , 0.16g], dicyclohexyl (2', 6'-dimethoxy-[1,1'-biphenyl]-2-yl) phosphine (SPhos, 0.24g), NaOtBu (2.1g) and xylene (40ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. After the crude product was purified using a short silica gel column (eluent: toluene), the solvent was concentrated, heptane was added to the obtained crude product and ice-cooled, the precipitated crystals were filtered and washed with heptane, thereby obtaining compound (IF) (10.5g).

[1370] [Chemistry 357]

[1371]

[1372] Under nitrogen atmosphere, 1.53M tert-butyllithium pentane solution (14.4 ml) was added to a flask containing compound (IF) (10.5 g) and tert-butylbenzene (200 ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (5.9 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (3.1 g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled by an ice bath were added in sequence and stirred for 1 hour. The organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated, and the obtained crude product was purified using a silica gel (NH silica) short column (eluent: toluene / heptane = 1 / 9 (volume ratio)). After the obtained crude product was concentrated, heptane was added and the precipitated crystals were filtered and further washed with heptane to obtain compound (1-1301) (1.9 g).

[1373] [Chemistry 358]

[1374]

[1375] The structure of the obtained compound was confirmed by NMR measurement.

[1376] 1 H-NMR (CDCl 3): δ=1.09(s,12H),1.27(s,12H),1.42(s,12H),1.49(s,12H),1.70-1.80(m,16H),6 .20(d,2H),6.56(s,2H),7.09(dd,2H),7.25-7.30(m,3H),7.58(d,2H),8.91(s,2H).

[1377] Synthesis Example (4): Synthesis of Compound (1-1302)

[1378] [Chemistry 359]

[1379]

[1380] Under nitrogen atmosphere, compound (IG) (8.0 g), compound (IE) (19.7 g), Pd 2 (dba) 3 (0.52g), SPhos (0.94g), NaOtBu (5.5g) and xylene (80ml) were placed in a flask, heated and stirred at 120°C for 3 hours, and then stirred at 130°C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified by a silica gel column (eluent: toluene / heptane = 10 / 90 (volume ratio) → 15 / 85 (volume ratio)), and the solvent was concentrated to obtain compound (IH) (15.3g).

[1381] [Chemistry 360]

[1382]

[1383] Under nitrogen atmosphere, 1.53M tert-butyllithium pentane solution (13.2 ml) was added to a flask containing compound (IH) (15.3 g) and tert-butylbenzene (100 ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (5.3 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (2.7 g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled by an ice bath were added in sequence and stirred for 1 hour. After the organic layer was separated, it was washed with water (twice), and the precipitate precipitated by the addition of heptane was filtered. The precipitate was washed with methanol and water, and the obtained yellow crystals were dissolved in toluene by heating, and then purified by a silica gel short column (eluent: toluene). The solvent was distilled off, heptane was added to the obtained crude product, the obtained crystals were filtered, and then washed with heptane to obtain compound (1-1302) (7.23 g).

[1384] [Chemistry 361]

[1385]

[1386] The structure of the obtained compound was confirmed by NMR measurement.

[1387] 1 H-NMR (CDCl 3 ): δ=1.07(s,12H),1.11(s,6H),1.19(s,6H),1.24(s,6H),1.35(s,6H),1.48(s,12H),1.68-1.75(m,16H),5.63(s,2H) ,6.55(s,2H),6.89(t,2H),6.91-6.92(m,2H),6.93-6.95(m,4H),7.04(t,4H),7.13(dd,2H),7.37(d,2H),8.85(s,2H).

[1388] Synthesis Example (5): Synthesis of Compound (1-1823)

[1389] [Chemistry 362]

[1390]

[1391] Under nitrogen atmosphere, compound (II) (35.0 g), 3-bromo-5-tert-butyl-benzo[b]thiophene (compound IJ: 17.4 g), Pd(dba)2 (1.86 g), NaOtBu (10.4 g), tri-tert-butylphosphonium tetrafluoroborate ([(tBu) 3 PH]BF 4 ): 1.87 g and xylene (300 ml) were placed in a flask and heated at 120° C. for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene / heptane=1 / 4 (volume ratio)), and the solvent was concentrated. The glassy solid was dried using a vacuum pump to obtain compound (IK) (35 g).

[1392] [Chemistry 363]

[1393]

[1394] Under nitrogen atmosphere, 1.60 M tert-butyllithium pentane solution (25.0 ml) was added to a flask containing compound (IK) (16.7 g) and tert-butylbenzene (400 ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and added with boron tribromide (10.0 g), and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (5.2 g) was added, and stirred at room temperature until the heat generation was stopped, and the temperature was raised to 90°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added in sequence and stirred for 1 hour. After the toluene solution was concentrated, heptane was added and purified using a silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)). The obtained crude product was repeatedly recrystallized from toluene to obtain compound (1-1823) (2.8 g).

[1395] [Chemistry 364]

[1396]

[1397] The structure of the obtained compound was confirmed by NMR measurement.

[1398] 1 H-NMR (CDCl 3): δ=0.99(s,9H),1.11(s,9H),1.30(s,6H),1.43(s,3H),1.46(m,12H),1.51(s,9H),1.78-1.86(m,4H),6.15(s,1H),6.65( s,1H),6.74(s,1H),7.23-7.29(d,4H),7.41(d,1H),7.46(d,1H),7.53(s,1H),7.66-7.68(m,3H),7.90(d,1H),8.78(s,1H).

[1399] Synthesis Example (6): Synthesis of Compound (1-1821)

[1400] [Chemistry 365]

[1401]

[1402] Under nitrogen atmosphere, compound (IL) (71.0 g), compound (IJ) (37.8 g), Pd (dba) 2 (2.14g), NaOtBu(16.9g), [(tBu) 3 PH]BF 4 (1.36 g) and xylene (710 ml) were placed in a flask and heated to reflux at 130° C. for 1 hour. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified using a silica gel column (eluent: toluene), and then washed with heptane to obtain compound (IM) (71.3 g).

[1403] [Chemistry 366]

[1404]

[1405] Under nitrogen atmosphere, 1.60M tert-butyllithium pentane solution (50.0ml) was added to a flask containing compound (IM) (32.0g) and tert-butylbenzene (400ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and added with boron tribromide (20.0g), and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (10.4g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and the temperature was raised to 70°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled in an ice bath were added in sequence and stirred for 1 hour, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was washed with ethyl acetate and then purified using a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The obtained crude product was washed with heptane to obtain compound (1-1821) (7.1 g).

[1406] [Chemistry 367]

[1407]

[1408] Synthesis Example (7): Synthesis of Compound (1-3623)

[1409] [Chemistry 368]

[1410]

[1411] Under nitrogen atmosphere, compound (IN) (60.0 g), compound (IJ) (28.6 g), Pd(dba) 2 (2.93g), NaOtBu(12.3g), [(tBu) 3 PH]BF 4 (2.96 g) and xylene (660 ml) were placed in a flask and heated at 120° C. for 2 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified using a silica gel column (eluent: toluene / heptane = 1 / 3 (volume ratio)), and then washed with methanol to obtain compound (IO) (68.0 g).

[1412] [Chemistry 369]

[1413]

[1414] Under a nitrogen atmosphere and at 0 °C, 1.61 M tert-butyllithium pentane solution (50.0 ml) was added to a flask containing compound (I-O) (35.8 g) and tert-butylbenzene (800 ml). After the addition was completed, the temperature was raised to 60 °C and stirred for 0.5 hour, and then the components with boiling points lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50 °C and boron tribromide (20.0 g) was added, and then the temperature was raised to room temperature and stirred for 0.5 hour. Thereafter, the temperature was raised to 50 °C and heated with stirring for 0.5 hour. The reaction solution was cooled to room temperature, an aqueous solution of sodium acetate cooled with an ice bath and ethyl acetate were added in sequence and stirred for 1 hour, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, the residue was washed with ethyl acetate, and then purified by silica gel column (eluent: toluene). Further purification was carried out by recrystallization from toluene, whereby compound (1-3623) (9.3 g) was obtained.

[1415] [Chemical formula 370]

[1416]

[1417] Synthesis Example (8): Synthesis of Compound (1-3621)

[1418] [Chemical formula 371]

[1419]

[1420] Under a nitrogen atmosphere, compound (I-P) (65.0 g), compound (I-J) (31.7 g), Pd(dba) 2 (1.79 g), NaOtBu (14.1 g), [(tBu) 3 PH]BF 4 (1.14 g) and xylene (520 ml) were placed in a flask and heated at 130 °C for 2 hours. After the reaction solution was cooled to room temperature, water and toluene were added, the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)). The glassy solid was dried with a vacuum pump, whereby compound (I-Q) (52 g) was obtained.

[1421] [Chemical formula 372]

[1422]

[1423] Under a nitrogen atmosphere and at 0 °C, 1.60 M tert-butyllithium pentane solution (50.0 ml) was added to a flask containing compound (I-Q) (35.0 g) and tert-butylbenzene (280 ml). The temperature was raised to 60 °C and stirred for 0.5 hour. Subsequently, it was cooled to -50 °C and boron tribromide (20.6 g) was added. The temperature was raised to room temperature and stirred for 0.5 hour. Thereafter, it was cooled again to 0 °C and N,N-diisopropylethylamine (10.6 g) was added. After stirring at room temperature until the heat generation ended, the temperature was raised to 90 °C and heated with stirring for 1 hour. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were successively added and stirred for 1 hour. The organic layer was separated and washed with water. The solution was concentrated under reduced pressure, the residue was washed with ethyl acetate, and then purified by silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). Further purification was carried out by recrystallization from toluene, whereby compound (1-3621) (7.2 g) was obtained.

[1424] [Chemical formula 373]

[1425]

[1426] The structure of the obtained compound was confirmed by NMR measurement.

[1427] 1 H-NMR(CDCl 3 ): δ = 1.11 (s, 9H), 1.19 (s, 9H), 1.26 (s, 3H), 1.28 (s, 3H), 1.37 (s, 18H), 1.44 - 1.47 (m, 6H), 1.77 - 1.86 (m, 4H), 2.21 (s, 3H), 6.08 (s, 1H), 6.10 (s, 1H), 6.53 (d, 1H), 6.61 (d, 1H), 7.20 (d, 2H), 7.26 (dd, 1H), 7.31 (dd, 1H), 7.40 (dd, 1H), 7.48 (d, 1H), 7.61 (t, 1H), 7.66 (d, 1H), 7.88 (d, 1H), 8.69 (d, 1H).

[1428] Synthesis Example (9): Synthesis of Compound (1-1828)

[1429] [Chemical formula 374]

[1430]

[1431] Under a nitrogen atmosphere, compound (I-R) (63.8 g), compound (I-J) (24.2 g), Pd(dba) 2(0.939 g), NaOtBu (11.8 g), tris-tert-butylphosphine ((tBu) 3 P: 3.27 ml) and toluene (630 ml) were placed in a flask and heated at 110 °C for 4 hours. After cooling the reaction solution to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified using a silica gel column (eluent: toluene / heptane = 1 / 6 (volume ratio)). The glassy solid was dried using a vacuum pump to obtain compound (I-S) (44 g).

[1432] [Chemical formula 375]

[1433]

[1434] Under a nitrogen atmosphere and at 0 °C, a 1.61 M solution of tert-butyllithium in pentane (56.7 ml) was added to a flask containing compound (I-S) (44.3 g) and tert-butylbenzene (400 ml). After the addition was complete, the temperature was raised to 60 °C and stirred for 0.5 hours, and then the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. It was cooled to -50 °C and boron tribromide (22.9 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, it was cooled again to 0 °C and N,N-diisopropylethylamine (16.0 g) was added, and it was stirred at room temperature until the heat generation ended, then the temperature was raised to 120 °C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled with an ice bath and toluene were added and stirred, and then the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated, and the obtained crude product was purified using a silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)), and further purified by recrystallization from a mixed solvent of toluene and heptane (toluene / heptane = 1 / 1 (volume ratio)) to obtain compound (1-1828) (5.0 g).

[1435] [Chemical formula 376]

[1436]

[1437] The structure of the obtained compound was confirmed by NMR measurement.

[1438] 1 H-NMR(CDCl 3):δ=0.96 - 0.99(m, 9H), 1.10(s, 9H), 1.12(s, 9H), 1.25 - 1.32(m, 6H), 1.39 - 1.51(m, 24H), 1.76 - 1.86(m, 4H), 6.05 - 6.28(m, 2H), 6.66 - 6.80(m, 2H), 7.01 - 7.08(m, 2H), 7.12 - 7.24(m, 4H), 7.37 - 7.47(m, 2H), 7.48 - 7.69(m, 3H), 7.70(s, 1H), 7.88(d, 1H), 8.70(s, 1H).

[1439] Synthesis Example (10): Synthesis of Compound (1 - 3604)

[1440] [Chemical Formula 377]

[1441]

[1442] Under a nitrogen atmosphere, Compound (I - T) (49.7 g), Compound (I - J) (22.8 g), Pd(dba) 2 (2.44 g), NaOtBu (13.6 g), [(tBu) 3 PH]BF 4 (2.46 g) and xylene (600 ml) were placed in a flask and heated at 120 °C for 3 hours. After cooling the reaction solution to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified using a silica gel column (eluent: heptane). Furthermore, it was purified by recrystallization from heptane to obtain Compound (I - U) (45 g).

[1443] [Chemical Formula 378]

[1444]

[1445] Under a nitrogen atmosphere and at 0 °C, 1.60 M tert-butyllithium pentane solution (50.0 ml) was added to a flask containing compound (I-U) (40.4 g) and tert-butylbenzene (270 ml). After completion of the dropwise addition, the temperature was raised to 60 °C and stirred for 0.5 hour, and then the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. It was cooled to -50 °C and boron tribromide (20.0 g) was added, and the temperature was raised to 50 °C and stirred for 0.5 hour. Thereafter, it was cooled again to 0 °C and N,N-diisopropylethylamine (10.4 g) was added, and it was stirred at room temperature until the heat generation ended, then the temperature was raised to 80 °C and heated with stirring for 0.5 hour. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were added in sequence and stirred for 1 hour, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, the residue was washed with ethyl acetate, and then purified by a silica gel column (eluent: toluene). Furthermore, it was purified by recrystallization from toluene, whereby compound (1-3604) (3.8 g) was obtained.

[1446] [Chemical formula 379]

[1447]

[1448] Synthesis Example (11): Synthesis of Compound (1-1851)

[1449] [Chemical formula 380]

[1450]

[1451] Under a nitrogen atmosphere, compound (I-L) (29.0 g), compound (I-V) (18.9 g), Pd(dba) 2 (0.55 g), NaOtBu (6.9 g), [(tBu) 3 PH]BF 4 (0.55 g) and xylene (100 ml) were placed in a flask and heated under reflux at 120 °C for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, the residue was purified by a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)), ethyl acetate was added after concentration, the obtained crystals were filtered, and then washed with methanol, whereby compound (I-W) (25.0 g) was obtained.

[1452] [Chemical formula 381]

[1453]

[1454] Under nitrogen atmosphere, 1.60M tert-butyllithium pentane solution (39.3ml) was added to a flask containing compound (IW) (25.0g) and tert-butylbenzene (160ml) at 0°C. After the addition was completed, the temperature was raised to 60°C and stirred for 0.5 hours, and the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (15.7g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (8.1g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and the temperature was raised to 80°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled in an ice bath were added in sequence and stirred for 1 hour, and the organic layer was separated and washed with water. T...

Claims

1. A polycyclic aromatic compound, which is a monomer or a polymer, wherein the monomer is represented by the following general formula (1), and the polymer has a plurality of structures represented by the following general formula (1); In the formula (1), Ring A, Ring B and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted. Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl, X 1 and X 2 are independently >O, >NR, >C(-R)2, >S or >Se, wherein the R of the >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted, and the R of the >C(-R)2 is hydrogen, an aryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted. In addition, at least one of the R of the >NR and the R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring via a linking group or a single bond, At least one hydrogen in the compound represented by formula (1) may be substituted by deuterium, cyano or halogen, and At least one of the A ring, B ring, C ring, aryl group and heteroaryl group in the compound represented by formula (1) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane can be replaced, and at least one -CH2- in the cycloalkane can be replaced by -O-.

2. The polycyclic aromatic compound according to claim 1, wherein In the formula (1), The A ring, the B ring and the C ring are each independently an aryl ring or a heteroaryl ring, at least one hydrogen in these rings may be substituted by a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group, the two aryl groups of the diarylboryl group may be bonded via a single bond or a linking group, and these rings have a substituted or unsubstituted alkyl group with a Y-containing radical. 1 , X 1 and X 2 The condensed bicyclic structure in the center of the formula (1) has a total of 5-membered rings or 6-membered rings, Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl, X 1 and X 2 are independently >O, >NR, >C(-R)2, >S or >Se, wherein the R of the >NR is an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, and the R of the >C(-R)2 is hydrogen, an aryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, and in addition, at least one of the R of the >NR and the R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring through -O-, -S-, -C(-R)2- or a single bond, and the R of the -C(-R)2- is hydrogen, an alkyl group or a cycloalkyl group, At least one hydrogen in the compound represented by formula (1) may be substituted by deuterium, cyano or halogen. In the case of a multimer, it is a dimer or trimer having two or three structures represented by the general formula (1), and, At least one of the A ring, B ring, C ring, aryl group and heteroaryl group in the compound represented by formula (1) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane can be replaced, and at least one -CH2- in the cycloalkane can be replaced by -O-.

3. The polycyclic aromatic compound according to claim 1, which is represented by the following general formula (2); In the formula (2), Any -C(-R)= in the a ring, b ring and c ring may be substituted with -N=, any -C(-R)=C(-R)- may be substituted with -N(-R)-, -O- or -S-, wherein R of the -N(-R)- is an aryl group, an alkyl group or a cycloalkyl group, and R of the -C(-R)= is R in formula (2) 1 ~R 11 , the R of -C(-R)=C(-R)- is R in formula (2) 1 ~R 11 , R 1 ~R 11 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, at least one hydrogen in these may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group, the two aryl groups of the diarylboryl may be bonded via a single bond or a linking group, and R 1 ~R 11 The adjacent groups in the group may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group or an alkyldicycloalkylsilyl group, at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and the two aryl groups in the diarylboryl group may be bonded via a single bond or a linking group, Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, X 1 and X 2 are independently >O, >NR, >C(-R)2, >S or >Se, wherein the R of the >NR is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the R of the >C(-R)2 is hydrogen, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. In addition, at least one of the R of the >NR and the R of the >C(-R)2 may be bonded to at least one of the a ring, the b ring and the c ring through -O-, -S-, -C(-R)2- or a single bond, and the R of the -C(-R)2- is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and At least one of the a ring, the b ring, the c ring, the formed ring, the aryl group and the heteroaryl group in the compound represented by formula (2) is condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted by -O-.

4. The polycyclic aromatic compound according to claim 3, wherein In the formula (2), Any -C(-R)= in the a ring, b ring and c ring may be substituted with -N=, any -C(-R)=C(-R)- may be substituted with -N(-R)-, -O- or -S-, wherein R of the -N(-R)- is an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and R of the -C(-R)= is R in formula (2) 1 ~R 11 , the R of -C(-R)=C(-R)- is R in formula (2) 1 ~R 11 , R 1 ~R 11 are independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a triarylsilyl group or a trialkylsilyl group, wherein the aryl group in the diarylamino group is an aryl group having 6 to 12 carbon atoms, the aryl group in the diarylboryl group is an aryl group having 6 to 12 carbon atoms, and the two aryl groups may be bonded via a single bond or a linking group, the aryl group in the triarylsilyl group is an aryl group having 6 to 12 carbon atoms, and the alkyl group in the trialkylsilyl group is an alkyl group having 1 to 6 carbon atoms, and R 1 ~R 11 The adjacent groups in the group may be bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a triarylsilyl group or a trialkylsilyl group, wherein the aryl group in the triarylsilyl group is an aryl group having 6 to 12 carbon atoms, and the alkyl group in the trialkylsilyl group is an alkyl group having 1 to 5 carbon atoms, Y 1 is B, P, P=O, P=S or Si-R, wherein R of Si-R is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, X 1 and X 2 are independently >O, >NR, >C(-R)2 or >S, wherein R of >NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R of >C(-R)2 is hydrogen, an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and At least one of the a ring, the b ring, the c ring, the formed ring, the aryl group and the heteroaryl group in the compound represented by formula (2) is condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms.

5. The polycyclic aromatic compound according to claim 3, wherein In the formula (2), Any -C(-R)= in the a ring, b ring and c ring may be substituted with -N=, any -C(-R)=C(-R)- may be substituted with -N(-R)-, -O- or -S-, wherein R of the -N(-R)- is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R of the -C(-R)= is R in formula (2) 1 ~R 11 , the R of -C(-R)=C(-R)- is R in formula (2) 1 ~R 11 , R 1 ~R 11 are independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein the aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, Y 1 is B, P, P=O or P=S, X 1 and X 2 are independently >O, >NR or >C(-R)2, wherein R of >NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R of >C(-R)2 is hydrogen, an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and In the compound represented by formula (2), at least one of the aromatic groups having 6 to 10 carbon atoms, the aromatic groups having 6 to 10 carbon atoms, the aromatic groups having 6 to 10 carbon atoms and the aromatic groups having 3 to 16 carbon atoms as R of the >NR are condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen atom in the cycloalkane may be replaced by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

6. The polycyclic aromatic compound according to claim 3, wherein R 1 ~R 11 are independently hydrogen, an aryl group having 6 to 16 carbon atoms, a diarylamino group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein the aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, Y 1 For B, X 1 and X 2 All are >NR, or X 1 is >NR and X 2 is>O, and R of the>NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium or halogen, and In the compound represented by formula (2), at least one of the a ring, the b ring, the c ring and the aromatic group having 6 to 10 carbon atoms as R of the >NR is condensed with a cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl group having 1 to 5 carbon atoms. 7 . The polycyclic aromatic compound according to claim 1 , which is substituted with a diarylamino group condensed with a cycloalkane, a carbazole group condensed with a cycloalkane, or a benzocarbazole group condensed with a cycloalkane.

8. The polycyclic aromatic compound according to any one of claims 3 to 6, wherein R 2 It is a diarylamino group condensed with a cycloalkane or a carbazole group condensed with a cycloalkane.

9. The polycyclic aromatic compound according to claim 7 or 8, wherein The cycloalkane is a cycloalkane having 3 to 20 carbon atoms.

10. The polycyclic aromatic compound according to any one of claims 1 to 8, wherein The halogen is fluorine.

11. The polycyclic aromatic compound according to claim 1, which is represented by any one of the following structural formulas; In each structural formula, Me represents a methyl group, and tBu represents a tert-butyl group. 12 . A reactive compound, wherein a reactive substituent is substituted on the polycyclic aromatic compound according to claim 1 .

13. A polymer compound obtained by polymerizing the reactive compound according to claim 12 as a monomer, or a polymer crosslinked product obtained by further crosslinking the polymer compound.

14. A pendant type polymer compound, which is a pendant type polymer compound obtained by substituting the reactive compound according to claim 12 into a main chain polymer, or a pendant type polymer crosslinked product obtained by further crosslinking the pendant type polymer compound.

15. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 11.

16. A material for an organic element, comprising the reactive compound according to claim 12.

17. A material for an organic device, comprising the polymer compound according to claim 13.

18. A material for an organic element, comprising the pendant-type polymer compound according to claim 14.

19. The organic element material according to any one of claims 15 to 18, wherein The organic element material is an organic electroluminescent element material, an organic field effect transistor material or an organic thin film solar cell material.

20. The material for an organic element according to claim 19, wherein The material for the organic electroluminescent element is a material for a light-emitting layer.

21. An ink composition comprising: the polycyclic aromatic compound according to any one of claims 1 to 11; and an organic solvent.

22. An ink composition comprising: the reactive compound according to claim 12; and an organic solvent.

23. An ink composition comprising: a main-chain polymer; the reactive compound according to claim 12; and an organic solvent.

24. An ink composition comprising: the polymer compound according to claim 13; and an organic solvent.

25. An ink composition comprising: the pendant polymer compound according to claim 14; and an organic solvent.

26. An organic electroluminescent element comprising: a pair of electrodes, including an anode and a cathode; and an organic layer, arranged between the pair of electrodes and containing the polycyclic aromatic compound as described in any one of claims 1 to 11, the reactive compound as described in claim 12, the polymer compound as described in claim 13, or the pendant polymer compound as described in claim 14.

27. The organic electroluminescent element according to claim 26, wherein: The organic layer is a light-emitting layer.

28. The organic electroluminescent element according to claim 27, wherein The light-emitting layer includes: a host; and the polycyclic aromatic compound, reactive compound, polymer compound or pendant polymer compound as a dopant.

29. The organic electroluminescent element according to claim 28, wherein The main body is an anthracene compound, a fluorene compound or a dibenzo Series of compounds.

30. An organic electroluminescent element according to any one of claims 27 to 29, comprising at least one layer of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives and hydroxyquinoline metal complexes.

31. The organic electroluminescent element according to claim 30, wherein: At least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes.

32. The organic electroluminescent element according to any one of claims 26 to 31, wherein At least one of the hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer comprises: a polymer compound or a polymer cross-linked body, or a suspended polymer compound or a suspended polymer cross-linked body, wherein the polymer compound is formed by polymerizing a low molecular compound that can form each layer as a monomer, and the polymer cross-linked body is formed by further cross-linking the polymer compound, the suspended polymer compound is formed by reacting a low molecular compound that can form each layer with a main chain polymer, and the suspended polymer cross-linked body is formed by further cross-linking the suspended polymer compound.

33. A display device comprising the organic electroluminescent element according to any one of claims 26 to 32.

34. A lighting device comprising the organic electroluminescent element according to any one of claims 26 to 32.

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