Cyano-substituted polycyclic aromatic compound

Abstract

To provide a novel cyano-substituted polycyclic aromatic compound and an organic EL element including the same.SOLUTION: By introducing a cyano group into a novel polycyclic aromatic compound in which a plurality of aromatic rings are coupled with a boron atom, an oxygen atom, and the like, the range of choices of materials for organic devices, such as materials for organic EL elements, is widened. In addition, by using a novel cyano-substituted polycyclic aromatic compound as a material for organic EL elements, an organic EL element excellent in, for example, luminous efficiency and service life, can be obtained. The compound of the present invention is, for example, a polycyclic aromatic compound as shown below.SELECTED DRAWING: Figure 2

Description

[Technical Field]

[0001] The present invention relates to cyano-substituted polycyclic aromatic compounds and multimers thereof (hereinafter collectively referred to as "polycyclic aromatic compounds"). Aromatic compounds) and organic electroluminescent devices and organic field-effect transistors using them The present invention relates to an organic thin-film solar cell, a display device, and a lighting device. In this case, "organic electroluminescent element" is sometimes written as "organic EL element" or simply "element." be. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been developed to be energy-efficient and thin. Various researches have been conducted, and organic electroluminescent devices made of organic materials are easy to make lighter and larger. In particular, the luminescence properties of blue, one of the three primary colors of light, have been actively investigated. Development of organic materials with charge transport capabilities (holes, electrons, etc.) (potential to become semiconductors or superconductors) Regarding the development of organic materials with the potential for It has been actively researched to date.

[0003] The organic EL element comprises a pair of electrodes consisting of an anode and a cathode, and a light-emitting element disposed between the pair of electrodes. The layer containing the organic compound has a structure consisting of one or more layers. The layers include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons. However, a variety of organic materials suitable for these layers have been developed.

[0004] As a material for the light-emitting layer, for example, benzofluorene-based compounds have been developed (International (Publication No. 2004 / 061047) Examples of hole transport materials include triphenylamine. Compounds based on ZnO have been developed (Japanese Patent Application Laid-Open No. 2001-172232). For example, anthracene-based compounds have been developed (Japanese Patent Laid-Open Publication No. 2005-170911).

[0005] In recent years, triphenylamine has been used as a material for organic EL elements and organic thin-film solar cells. Materials that have been improved from amine derivatives have also been reported (WO 2012 / 118164). The starting material was N,N'-diphenyl-N,N'-bis(3-methylphenyl) )-1,1'-biphenyl-4,4'-diamine (TPD) as a reference A material characterized by enhanced planarity due to the linking of aromatic rings that make up the amine In this paper, for example, the charge transport properties of NO-linked compounds (compound 1 on page 63) are evaluated. However, there is no description of a method for producing materials other than NO-linked compounds. In addition, since the electronic state of the entire compound differs depending on the linked elements, there are many compounds other than NO-linked compounds. The properties that can be obtained from other materials are also unknown. For example, the triplet exciton energy (T1) is large. Compounds with a wider conjugated structure can emit phosphorescence at shorter wavelengths, resulting in blue light. It is useful as a material for the light-emitting layer. It is also useful as an electron transport material or hole transport material sandwiching the light-emitting layer. Therefore, compounds with novel conjugated structures having large T1 are desired.

[0006] The host material for organic EL devices generally contains existing aromatic rings such as benzene and carbazole. It is a molecule that is connected by multiple single bonds or phosphorus or silicon atoms. This is a relatively small conjugated system. By connecting many aromatic rings, the large HOMO-LUMO gap required for the host material can be obtained. This is because the band gap (Eg in the thin film) is guaranteed. The host materials for organic EL devices using thermally activated delayed fluorescent materials have high triplet excitation energy. Ghee (E T ) is also required, but the molecule must have a donor or acceptor aromatic ring or substituent. By linking, SOMO1 and SOMO2 in the triplet excited state (T1) are localized, By reducing the exchange interaction between the two orbitals, the triplet excitation energy (E T ) to improve However, the small aromatic rings in the conjugated system do not have sufficient redox stability. However, existing devices using molecules formed by linking aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability. However, the HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation Electromotive force (E T ) has been considered unsuitable as a host material. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] Japanese Patent Application Laid-Open No. 2001-172232 [Patent Document 3] Japanese Patent Application Laid-Open No. 2005-170911 [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0008] As mentioned above, various materials have been developed for use in organic EL devices. However, in order to increase the options for materials for organic EL devices, In particular, development of new materials other than the NO-linked compounds reported in Patent Documents 1 to 4 is desired. The organic EL characteristics obtained from these devices and their manufacturing methods are not yet known.

[0009] In addition, Patent Document 6 discloses a polycyclic aromatic compound containing boron and an organic EL device using the same. It has been reported that the luminous efficiency and the life span of the device can be improved further to further improve the device characteristics. There is a demand for light-emitting layer materials, particularly dopant materials, that can achieve this. [Means for solving the problem]

[0010] As a result of extensive research to solve the above problems, the present inventors have discovered a polycyclic aromatic compound having a cyano group introduced therein. For example, an organic EL element can be constructed by disposing a layer containing an aromatic compound between a pair of electrodes. The inventors have found that an excellent organic EL device can be obtained by the above method, and have completed the present invention. The present invention relates to the following cyano-substituted polycyclic aromatic compounds or their multimers, and further to the following compounds: Organic devices such as materials for organic EL devices containing cyano-substituted polycyclic aromatic compounds or their multimers Provide materials for chairs.

[0011] In this specification, chemical structures and substituents may be expressed by the number of carbon atoms. When a substituent is substituted, or when a substituent is further substituted, the number of carbon atoms is It means the total number of carbon atoms in the chemical structure and the substituents, or the number of carbon atoms in the substituents. It does not mean the total number of carbon atoms of the substituents. For example, "substituted with substituent A having carbon number X" "Substituent B with carbon number Y" refers to "substituent B with carbon number Y" with "substituent A with carbon number X". The carbon number Y is not the total number of carbon atoms of the substituent A and the substituent B. For example, "substituent B having Y carbon atoms substituted with substituent A" means "substituent B having Y carbon atoms" The number of carbon atoms Y is the number of substituents A and It is not the total number of carbon atoms of the substituents B and C.

[0012] Section 1. A polycyclic aromatic compound represented by the following general formula (1), or a compound having a structure represented by the following general formula (1): A polymer of polycyclic aromatic compounds with multiple structures. [ka] (In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. 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 in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; , X 1 and X 2 are each independently >O, >NR, >S or >Se, R in the above NR is an optionally substituted aryl, an optionally substituted heteroaryl, or aryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the above >NR is a linking group or a single bond, and at least one of the rings A, B and C is may also be combined with one Ring B and ring C may be bonded via a linking group or a single bond; At least one hydrogen atom in the compound or structure represented by formula (1) is replaced by a fluorine atom, a chlorine atom, or a fluorine atom. , optionally substituted with bromine, iodine or deuterium; In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused with at least one cycloalkane. Preferably, at least one hydrogen atom in the cycloalkane may be substituted, and the At least one -CH2- in the cycloalkane may be replaced with -O-; and, At least one hydrogen atom in the compound or structure represented by formula (1) is replaced with cyano. It is being done.)

[0013] Section 2. In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings is replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or is an unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, Substituted or unsubstituted diarylboryl (two aryls are connected via a single bond or a linking group) may be bonded to each other), substituted or unsubstituted alkyl, substituted or unsubstituted cyclohexane substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy or or substituted silyl, and these rings may be substituted with Y 1 , X 1 and X 2 from The above formula (1) has a 5-membered ring or a 6-membered ring that shares a bond with the central fused two-ring structure. , Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R wherein R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; , X 1 and X 2 are each independently >O, >NR, >S or >Se, R in the above NR is aryl optionally substituted with alkyl or cycloalkyl; Heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or is cycloalkyl, and R in the >NR is -O-, -S-, or -C(-R)2-. or may be bonded to at least one of the ring A, ring B and ring C via a single bond; R in the -C(-R)2- is hydrogen, alkyl, or cycloalkyl; The B and C rings are >O, >NR, >Si(-R)2, >C(-R)2, >S, >S and R in the above >NR and >Si(-R)2 may be bonded via a bond or a single bond. each independently represents an optionally substituted aryl, an optionally substituted heteroaryl, alkyl, optionally substituted alkyl, or optionally substituted cycloalkyl. R in the >C(-R)2 is hydrogen, an optionally substituted aryl, a substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl is alkyl, At least one hydrogen atom in the compound or structure represented by formula (1) is replaced by a fluorine atom, a chlorine atom, or a fluorine atom. , optionally substituted with bromine, iodine or deuterium; In the case of a polymer, a dimer or trimer having two or three structures represented by general formula (1) and In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused with at least one cycloalkane. Preferably, at least one hydrogen atom in the cycloalkane may be substituted, and the At least one -CH2- in the cycloalkane may be replaced with -O-; and, At least one hydrogen atom in the compound or structure represented by formula (1) is replaced with cyano. It is being Item 1. The polycyclic aromatic compound or a multimer thereof according to Item 1.

[0014] Section 3. Item 1. A polycyclic aromatic compound or a multimer thereof according to item 1, which is represented by the following general formula (2): [ka] (In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is the formula (2) R 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R) =C(-R)- (where R is R in formula (2) 1 ~R 11 ) is "-N(-R)- ", "-O-", or "-S-", and the "-N(-R)-" R is aryl, alkyl or cycloalkyl; R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diaryla amino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkenyl, alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tri Cycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkyl and aryl, aryl, aryl, heteroaryl, or aryl. may be substituted with alkyl or cycloalkyl, and R 1 ~R 11 Next to my house The adjacent groups are bonded to form an aryl or heteroaryl ring together with the a, b or c ring. At least one hydrogen atom in the formed ring may be selected from the group consisting of aryl, heterocyclic, Diaryl, diarylamino, diheteroarylamino, arylheteroarylamino Diarylboryl (two aryls may be bonded via a single bond or a linking group) (ii), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, Trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or may be substituted with alkyldicycloalkylsilyl, and at least One hydrogen is replaced by aryl, heteroaryl, alkyl, or cycloalkyl. It's okay to be there, Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R in the Si—R and Ge—R is an aryl having 6 to 12 carbon atoms, an aryl having 1 to 6 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms; X 1 and X 2 are each independently >O, >NR, >S or >Se, R in the above NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a carbon atom. alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and R is -O-, -S-, -C(-R)2- or a single bond between the ring a, ring b and ring c R in the -C(-R)2- may be bonded to at least one of the following alkyl groups having 1 to 6 carbon atoms: alkyl or cycloalkyl having 3 to 14 carbon atoms, R in b-ring 8 and R in the c-ring 7 are >O, >NR, >Si(-R)2, >C(-R)2 , >S, >Se or may be bonded via a single bond, and the >NR and >Si( Each R in —R)2 is independently aryl, heteroaryl, alkyl, or cycloalkyl. alkyl, which may be substituted with alkyl, and R in the >C(—R) , hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, may be substituted with alkyl; At least one hydrogen atom in the compound represented by formula (2) is replaced by a fluorine, chlorine, bromine, or iodine atom. may be substituted with iodine or deuterium, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed ring, aryl and heteroaryl has 3 to 24 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, or , and may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. Preferably, at least one -CH2- in the cycloalkane is replaced with -O-. It is also possible to At least one hydrogen atom in the compound represented by formula (2) is substituted with cyano. )

[0015] Section 4. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is the formula (2) R 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R) =C(-R)- (where R is R in formula (2) 1 ~R 11 ) is "-N(-R)- ", "-O-", or "-S-", and the "-N(-R)-" R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a silyl having 5 to 10 carbon atoms. is a chloroalkyl; R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 30 carbon atoms, an aryl having 2 to 3 carbon atoms, 0 heteroaryl, diarylamino (where aryl has 6 to 12 carbon atoms) , diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and two aryls The alkyl group may be bonded via a single bond or a linking group, and the alkyl group may be bonded via a single bond or a linking group, and is a cycloalkyl having 3 to 24 carbon atoms, and R 1 ~R 11 Adjacent groups among are bonded to form an aryl ring having 9 to 16 carbon atoms or an aryl ring having 6 to 1 5 heteroaryl ring, and at least one water atom in the ring formed The element is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a silyl having 3 to 16 carbon atoms. optionally substituted with chloroalkyl; Y 1 is B, P, P=O, P=S or Si-R, and R of the Si-R is the number of carbon atoms 6-10 aryl, 1-5 carbon alkyl, or 5-10 carbon cycloalkyl can be, X 1and X 2 are each independently >O, >NR or >S, and the >N- R in R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or an alkyl having 5 to 10 carbon atoms. is cycloalkyl, R in b-ring 8 and R in the c-ring 7 through >O, ​​>NR, >C(-R)2 or >S R in the >NR may be bonded to each other, and each R is independently an aryl group having 6 to 30 carbon atoms. C2-30 heteroaryl, C1-24 alkyl or C3-24 alkyl These are cycloalkyl groups, which may be substituted with alkyl groups having 1 to 24 carbon atoms. R in the above >C(-R)2 is hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms. aryl, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms; These may be substituted with alkyl having 1 to 24 carbon atoms, At least one hydrogen atom in the compound represented by formula (2) is replaced by a fluorine, chlorine, bromine, or iodine atom. may be substituted with iodine or deuterium, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed ring, aryl and heteroaryl has 3 to 16 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2) is substituted with cyano. Item 3. The polycyclic aromatic compound or a multimer thereof according to Item 3.

[0016] Section 5. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is the formula (2) R 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R) =C(-R)- (where R is R in formula (2) 1 ~R 11 ) is "-N(-R)- ", "-O-", or "-S-", and the "-N(-R)-" R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a silyl having 5 to 10 carbon atoms. is a chloroalkyl; R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 16 carbon atoms, an aryl having 2 to 2 carbon atoms, 0 heteroaryl, diarylamino (where aryl is aryl having 6 to 10 carbon atoms) , diarylboryl (where aryl is an aryl having 6 to 10 carbon atoms, and two aryls The alkyl group may be bonded via a single bond or a linking group, and the alkyl group may be bonded via a single bond or a linking group, and is a cycloalkyl having 3 to 16 carbon atoms, Y 1 is B, P, P=O or P=S, X 1 and X 2 are each independently >O or >NR, and R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. is alkyl, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed ring, aryl and heteroaryl has 3 to 16 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2) is substituted with cyano. Item 3. The polycyclic aromatic compound or a multimer thereof according to Item 3.

[0017] Section 6. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is the formula (2) R 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R) =C(-R)- (where R is R in formula (2) 1 ~R 11 ) is "-N(-R)- ", "-O-", or "-S-", and the "-N(-R)-" R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a silyl having 5 to 10 carbon atoms. is a chloroalkyl; R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 16 carbon atoms, a diaryla amino (where aryl is aryl with 6 to 10 carbon atoms), diarylboryl (where aryl is The aryl is an aryl having 6 to 10 carbon atoms, and two aryls are bonded via a single bond or a linking group. alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, and Y 1 is B, X 1 and X 2 are both >NR, or X 1 is >NR and X 2 HA>O and R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed ring, aryl and heteroaryl has 3 to 16 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2) is substituted with cyano. Item 3. The polycyclic aromatic compound or a multimer thereof according to Item 3.

[0018] Section 7. wherein R of the >NR is a cyano-substituted aryl or heteroaryl; 7. The polycyclic aromatic compound or a multimer thereof according to any one of 6.

[0019] Section 8. Item 7. The polycyclic aromatic compound according to Item 7, wherein R of the >NR is a cyano-substituted phenyl. A compound or a multimer thereof.

[0020] Section 9. Cyano-substituted alkyl or cycloalkyl groups, cyano-substituted alkoxy groups group, cyano-substituted diarylamino group, cyano-substituted diarylboryl group (two wherein the aryl may be bonded via a single bond or a linking group), a cyano-substituted aryl 1 to 8, which are substituted with a benzocarbazolyl group or a cyano-substituted benzocarbazolyl group. 1. A polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 9.

[0021] Section 10. Item 9. Polycyclic aromatic rings substituted with cyano-substituted diarylamino groups. A compound or a multimer thereof.

[0022] Section 11. Item 10. Polycyclic aromatic rings substituted with cyano-substituted diphenylamino groups. A compound or a multimer thereof.

[0023] Section 12. Item 1. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka] (In the above structural formulas, "Me" stands for methyl group, "tBu" stands for t-butyl group, and "CN" stands for cyano) )

[0024] Section 13. The polycyclic aromatic compound or its multimer according to any one of Items 1 to 12 has a reactive substituent. Substituted, reactive compounds.

[0025] Section 14. Item 13. A polymer compound obtained by polymerizing the reactive compound described in Item 13 as a monomer, or and a crosslinked polymer obtained by further crosslinking the polymer compound.

[0026] Section 15. A pendant polymer compound in which the reactive compound described in item 13 is substituted on a main chain polymer. or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. .

[0027] Section 16. Item 13. An organic compound containing a polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 12. Materials for devices.

[0028] Section 17. Item 14. A material for an organic device, comprising the reactive compound according to item 13.

[0029] Section 18. Item 15. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 14.

[0030] Section 19. Item 15. A method for manufacturing a pharmaceutical composition comprising the pendant polymer compound or the pendant polymer crosslinked body according to Item 15. Materials for organic devices.

[0031] Section 20. The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or the like. 20. The organic device according to any one of items 16 to 19, which is a material for a solar cell or a thin film solar cell. Materials for use.

[0032] Section 21. Item 21. The organic electroluminescent element material according to Item 20, wherein the organic electroluminescent element material is a light-emitting layer material. material.

[0033] Section 22. A polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 12 and an organic solvent. An ink composition comprising:

[0034] Section 23. Item 14. An ink composition comprising the reactive compound according to item 13 and an organic solvent.

[0035] Section 24. Item 14. An ink composition comprising a main chain polymer, the reactive compound according to item 13, and an organic solvent. .

[0036] Section 25. Item 15. An ink composition comprising the polymer compound or crosslinked polymer according to item 14 and an organic solvent. thing.

[0037] Section 26. Item 15. A pendant polymer compound or a pendant polymer crosslinked body according to item 15, and an organic and a solvent.

[0038] Section 27. A pair of electrodes consisting of an anode and a cathode, and a device according to any one of items 1 to 12, which is disposed between the pair of electrodes. Item 13. A polycyclic aromatic compound or a polymer thereof according to Item 12. Item 14. A polymer compound or a crosslinked polymer according to Item 15. and an organic layer containing a pendant polymer compound or a pendant polymer crosslinked body. Electroluminescent device.

[0039] Section 28. Item 28. The organic electroluminescent device according to item 27, wherein the organic layer is a light-emitting layer.

[0040] Section 29. The light-emitting layer contains a host and the polycyclic aromatic compound or a large amount thereof as a dopant. compounds, reactive compounds, polymer compounds, crosslinked polymers, pendant polymer compounds or pendant polymer compounds Item 29. The organic electroluminescent device according to item 28, comprising a dant-type crosslinked polymer.

[0041] Section 30. The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound. Item 30. The organic electroluminescent device according to item 29, wherein the compound is a compound.

[0042] Section 31. At least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridinium derivative, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorane derivatives thylene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, Triazine derivatives, benzimidazole derivatives, phenanthroline derivatives and quinolinol Any of items 27 to 30, containing at least one selected from the group consisting of fluorine-based metal complexes. The organic electroluminescent device according to any one of the preceding claims.

[0043] Section 32. At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, Alkali earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkali metals Alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth Halides of alkali metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and dilute Item 31, containing at least one selected from the group consisting of organic complexes of earth metals. Organic electroluminescent device.

[0044] Section 33. At least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer The two layers are polymer compounds made by polymerizing low molecular weight compounds that can form each layer as monomers. Or, a polymer crosslinked body obtained by further crosslinking the polymer compound, or a polymer crosslinked body formed by forming each layer A pendant polymer compound obtained by reacting a low molecular weight compound with a main chain polymer, or Item 2 includes a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. 33. The organic electroluminescent device according to any one of 7 to 32.

[0045] Section 34. A display device or a lighting device comprising the organic electroluminescent device according to any one of items 27 to 33. . [Effects of the Invention]

[0046] According to a preferred embodiment of the present invention, the present invention is directed to a material for an organic device, such as a material for an organic EL element. It is possible to provide novel cyano-substituted polycyclic aromatic compounds that can be used as the By using these cyano-substituted polycyclic aromatic compounds, we have been able to provide excellent organic devices such as organic electroluminescence (EL) elements. It can be provided.

[0047] Specifically, the present inventors have proposed a method for converting an aromatic ring into a heteroatom such as boron, phosphorus, oxygen, nitrogen, or sulfur. Polycyclic aromatic compounds (basic skeleton parts) linked by atoms have a large HOMO-LUMO gap (Band gap in thin films Eg) and high triplet excitation energy (E T ) This is because the six-membered ring containing a heteroatom has low aromaticity, and as the conjugated system expands, The decrease in the HOMO-LUMO gap due to the electronic perturbation of the heteroatom is suppressed. This is due to the localization of SOMO1 and SOMO2 in the triplet excited state (T1). In addition, the polycyclic aromatic compound containing a hetero element according to the present invention (basic The backbone part) is responsible for the localization of SOMO1 and SOMO2 in the triplet excited state (T1). As a result, the exchange interaction between the two orbitals becomes smaller, and the triplet excited state (T1) and the singlet excited state The energy difference between the two states (S1) is small, and the compound exhibits thermally activated delayed fluorescence, making it suitable for use in the fluorescence of organic electroluminescence (EL) devices. It is also useful as an optical material. T ) is a material having Electron transport layer and hole transport layer for phosphorescent organic EL devices and organic EL devices using thermally activated delayed fluorescence Furthermore, these polycyclic aromatic compounds (basic skeleton portion) are also useful as By introducing electrons, the HOMO and LUMO energies can be moved arbitrarily, so that ionization It is possible to optimize the potential and electron affinity depending on the surrounding materials.

[0048] In addition, the polycyclic aromatic compound (basic skeleton portion) containing a hetero element according to the present invention has a rigid structure. Because of this structure, the emission spectrum is sharper, with a half-width of Many compounds emit light with narrow wavelengths and high color purity.

[0049] In addition to these characteristics of the basic skeleton, the compound of the present invention is For example, the emission wavelength can be adjusted by adjusting the position of the cyano group. The wavelength can be made shorter or longer. It is suitable for display applications that require a narrow half-width emission spectrum and high color purity. It is important in blue and green light emitting devices. [Brief explanation of the drawings]

[0050] [Figure 1] 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. [Figure 2] 1 is an absorption spectrum of compound (1-1). [Figure 3] 1 is a fluorescence spectrum of compound (1-1). [Figure 4] 1 is an absorption spectrum of compound (1-4). [Figure 5] Fluorescence spectrum of compound (1-4). DETAILED DESCRIPTION OF THE INVENTION

[0051] 1. Cyano-substituted polycyclic aromatic compounds and their polymers The present invention relates to a polycyclic aromatic compound represented by the following general formula (1), or and preferably a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula: (2) or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2): and at least one of these compounds or structures is a polymer of polycyclic aromatic compounds. The hydrogen atoms in the nucleoside group are replaced by cyano atoms. The "B" in each group is a symbol indicating the ring structure, and the other symbols are as described above. This is the same as the definition given above. [ka]

[0052] In the general formula (1), the rings A, B and C are each independently an aryl ring or Heteroaryl rings, in which at least one hydrogen atom is replaced with a substituent. The substituent may be a substituted or unsubstituted aryl, a substituted or unsubstituted heptane, or a substituted or unsubstituted aryl. Heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted dihetero Arylamino, substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl) substituted or unsubstituted diarylboryl (an amino group having two aryl groups) The alkyl group may be bonded via a single bond or a linking group, and a substituted or unsubstituted alkyl group may be bonded via a single bond or a linking group. , substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkoxy. Preferably, the aryloxy group is unsubstituted or substituted. In this case, the substituents include aryl, heteroaryl, alkyl, or cycloalkyl. The aryl ring or heteroaryl ring may be Y 1 , X 1 and X 2 Composed of The general formula (1) is a 5- or 6-membered ring that shares a bond with the central fused two-ring structure. It is preferable.

[0053] Here, the "fused bicyclic structure" refers to the Y 1 , X 1 and X 2 It means a structure in which two saturated hydrocarbon rings containing The "six-membered ring sharing a bond with the structure" refers to, for example, the fused two rings shown in the general formula (2) above. It means an a-ring (a benzene ring (6-membered ring)) fused to the structure. The phrase "a cycloalkyl ring or heteroaryl ring has this six-membered ring" means that ring A is formed by only this six-membered ring. Or, other rings are condensed to this six-membered ring so as to include this six-membered ring. In other words, the term "having a six-membered ring (with an A ring)" used here means that an A ring is formed. The term "aryl or heteroaryl ring" refers to a 6-membered ring that constitutes all or part of ring A. The term "B ring (b ring)" and "C ring (c ring)" refer to a ring fused to the fused two-ring structure. The same explanation applies to "five-membered ring" and "five-membered ring."

[0054] The ring A (or ring B or ring C) in the general formula (1) is the ring a in the general formula (2) and Substituent R 1 ~R 3 (or ring b and its substituent R 8 ~R 11 , c ring and its substituent R 4 ~R 7 That is, general formula (2) corresponds to the general formula (1) having a six-membered ring as rings A to C. In this sense, each ring in general formula (2) is written in lower case. These are represented by a to c.

[0055] In the general formula (2), the substituents R 1 ~R 11 Adjacent groups among and 1 bonded to form an aryl or heteroaryl ring together with ring a, ring b, or ring c. At least one hydrogen atom in the formed ring may be substituted by an aryl, heteroaryl, or , diarylamino, diheteroarylamino, arylheteroarylamino, diaryl boryl (two aryls may be bonded via a single bond or a linking group), aryl alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl (triarylsilyl) silyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl aryl or alkyldicycloalkylsilyl), and Aryl, diarylamino, diheteroarylamino, arylheteroarylamino , diarylboryl (two aryls may be bonded via a single bond or a linking group) ), alkyl, alkoxy or aryloxy substituted forms are preferred, and diaryl Particularly preferred are substituted amino groups. It may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. The polycyclic aromatic compound represented by the general formula (2) has substituents in the a ring, the b ring, and the c ring. Depending on the mutual bonding form, the compound can be formed as shown in the following formula (2-1) and formula (2-2). The ring structures constituting the ring A', ring B' and ring C' in each formula are the same as those in general formula (1). In each formula, R corresponds to ring A, ring B, and ring C, respectively. 1 ~R 11 , a, b ,c,Y 1 , X 1 and X 2 is the same as that in general formula (2).

[0056] [ka]

[0057] The ring A', ring B' and ring C' in the above formula (2-1) and formula (2-2) are each a ring represented by the general formula (2 ), the substituent R 1 ~R 11 Adjacent groups of the , b ring and c ring together form an aryl ring or heteroaryl ring (ring a, ring b) Or it can be said to be a fused ring formed by fusing another ring structure to ring c). However, there are also compounds in which all of the a, b, and c rings have been changed to A', B', and C' rings. As can be seen from the above formulas (2-1) and (2-2), for example, R 8 and R in c-ring 7 , b-ring R 11 and a-ring R 1 , R of ring c 4 and a-ring R 3 etc. are "adjacent These do not fall under the category of "groups" and are not bonded to each other unless otherwise specified. "Adjacent groups" means adjacent groups on the same ring.

[0058] The compounds represented by the above formula (2-1) or (2-2) can be prepared by, for example, forming an a ring (or a b ring or c ring) for the benzene ring, benzene ring, indole ring, pyrrole ring, benzofuran ring Ring A' (or ring B' or ring C') formed by condensing a ring or a benzothiophene ring The compound has the fused ring A' (or fused ring B' or fused ring C ') are a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or It is a dibenzothiophene ring.

[0059] Y in general formula (1) 1is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge—R, wherein R of the Si—R and Ge—R is aryl, alkyl, or In the case of P=O, P=S, Si-R or Ge-R, the A ring, B The atom bonding to the ring or C ring is P, Si or Ge. 1 is B, P, P=O, P =S or Si-R is preferred, and B is particularly preferred. This explanation is based on the general formula (2) 1 But it's the same.

[0060] X in general formula (1) 1 and X 2 are independently >O, >NR, >S or or >Se, and R of the >NR is optionally substituted aryl, substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted silyl R of the >NR is a chloroalkyl, and R of the >NR is a linking group or a single bond, and R of the >NR is a chloroalkyl ... and C ring, and the linking group may be -O-, -S- or -C(-R)2- is preferred. In addition, R in the above "-C(-R)2-" is hydrogen, alkyl or cycloalkyl. X 1 and X 2 are each independently >O or >N- Preferably, one of them is >NR and the other is >O or >NR. More preferably, both are >NR, and even more preferably, both are >NR. X in (2) 1 and X 2 But it's the same.

[0061] In the general formula (1), "R of the above >NR is a linking group or a single bond to the above A The definition of "bonded to at least one of ring B, ring C" in general formula (2) is " R in the >NR represents -O-, -S-, -C(-R)2-, or a single bond to the ring a, b This corresponds to the provision that "the ring is bonded to at least one of the rings c and c."

[0062] This rule is expressed by the following formula (2-3-1), X 1 or X 2 is fused ring B' and fused ring It can be expressed as a compound having a ring structure incorporated into C'. That is, for example, general formula (2) X for the b-ring (or c-ring) of the benzene ring in 1 (or X 2 ) will be imported. In this way, the compound has a B' ring (or C' ring) formed by condensing another ring. The resulting fused ring B' (or fused ring C') is, for example, a phenoxazine ring, a phenothia ring, The ring is an acridine ring.

[0063] In addition, the above provisions are based on the following formulas (2-3-2) and (2-3-3): 1 and X 2 It can also be expressed as a compound having a ring structure in which at least one of the following is incorporated into the fused ring A'. That is, for example, X for the benzene ring which is the a ring in general formula (2) 1 (or X 2 , or X 1 and X 2 ) and other rings are fused to form the A' ring. The fused ring A' formed is, for example, a phenoxazine ring, a phenoxazine ring, or a phenoxazine ring. It is a thiazine ring or an acridine ring.

[0064] [ka]

[0065] The rings B and C may be bonded via a linking group or a single bond (however, preferably A preferred embodiment is one in which ring B and ring C are not bonded. Examples of the linking group include: Examples include >O, >NR, >Si(-R)2, >C(-R)2, >S, and >Se. R in the >NR and >Si(—R)2 may each independently be substituted. aryl, optionally substituted heteroaryl, optionally substituted alkyl or is an optionally substituted cycloalkyl, and R in the >C(—R)2 is hydrogen, substituted optionally substituted aryl, optionally substituted heteroaryl, optionally substituted The alkyl and cycloalkyl groups are optionally substituted. The above description of the first substituent can be cited for the above. and R in at least one of >C(-R)2 is linked to said ring B by a linking group or a single bond. and ring C, and the linking group may be -O-, -S - or -C(-R)2- is preferred. In addition, R in the above "-C(-R)2-" is hydrogen, The details of these groups are described above in the first substitution. The explanation of the group can be referred to. This explanation is based on the linkage connecting the b ring and the c ring in general formula (2). The same is true for the base.

[0066] Here, in the general formula (1), "the above-mentioned >NR, >Si(-R)2 and >C(-R) In at least one of the groups 2 and 3, R is a linking group or a single bond, and at least one of the rings B and C is a linking group or a single bond. The definition of "both are bonded to one ring" means that in the general formula (2), "the above-mentioned >NR, >Si( R in at least one of -R)2 and >C(-R)2 is -O-, -S-, -C( -R)2- or a single bond, and bonded to at least one of the rings b and c. This corresponds to the provision that "

[0067] For details of the form in which ring B and ring C are bonded via a linking group, see the above-mentioned X 1 or X 2 The explanation using equations (2-3-1), (2-3-2) and (2-3-3) is as follows: It can be cited.

[0068] The positions at which the ring B and the ring C are bonded are not particularly limited, but as explained in the general formula (2), Ba, R 7 and R 8 are bonded, for example, >O, >NR, >Si(-R)2, >C(-R )2, >S or >Se. This form is preferred. 1 and (part of) the c-ring , R 7 and R 8 This corresponds to a six-membered ring formed by the binding site of and (part of) ring b. Also, Y 1 and one side of the benzene ring, which is the c-ring, and R 7 and R 8 The binding site of and b ring It can be said that a six-membered ring is formed by the benzene ring surrounded by one side of the ring. 7 and R 8 When Y is bonded to a single bond, 1 and (part of) the c-ring and R 7 Oh BiR 8 This corresponds to a five-membered ring formed by the bonding site (single bond) of ring b and (part of) ring b. do.

[0069] X 1 and X 2and specific examples of the linking group connecting the B ring and the C ring include >O, In >NR, >Si(-R)2, >C(-R)2, >S or >Se, >O, >N -R, >C(-R)2 or >S is preferred, and >O, >NR or >C(-R)2 is more preferred. More preferred is >O or >NR, particularly preferred.

[0070] In formula (2), any "-C(-R)=" (where R is R in equation (2). 1 ~R 11 ) may be replaced with "-N=". [ka] As shown above, for example, "-C(-R 5 )=" is replaced with "-N=" Thus, the c ring, which is represented as a benzene ring in formula (2), can be replaced by Lysine ring, pyrimidine ring, pyridazine ring, pyrazine ring, other nitrogen-containing heteroaryl ring In addition, when an adjacent group is present on the ring c (R 6 and R 7 ) are bonded to form a heteroaryl ring together with ring c (in the above formula, a quinoline ring) The ring formed may be further substituted (represented by n Rs) as described above. That is exactly what I did. In addition, there are the following variations: [ka] If other parts are replaced with "-N=" or if the a or b ring changes, It's the same even if there is one.

[0071] In formula (2), any of "-C(-R)=C(-R)-" in ring a, ring b, and ring c ” (where R is R in Eq. (2) 1 ~R 11 ) are "-N(-R)-", "-O-" or "-S-", and R in the "-N(-R)-" may be replaced with an aryl group. The substituents are alkyl, cycloalkyl, or cycloalkyl. These will be summarized later. [ka] As shown above, for example, "-C(-R 7 )=C(-R 6 )-" It may be replaced with "-N(-R)-", "-O-", or "-S-", like this The c ring shown as a benzene ring in formula (2) is an R-substituted pyrrole ring, a furan ring, It may be changed to a thiophene ring or other nitrogen-, oxygen-, or sulfur-containing heteroaryl ring. When there is an adjacent group on the c ring (in the above formula, R 4 and R 5 ) contains these combined and a heteroaryl ring (indole ring or benzofuran ring substituted with R in the above formula) together with ring c. or a benzothiophene ring), and the ring formed may be further substituted ( As described above, the number of R's is n. In addition, there are the following variations: [ka] If other parts are replaced with "-N(-R)-", "-O-", or "-S-", The same applies when the a or b ring is changed.

[0072] In addition, the above formulas (2-1), (2-2), (2-3-1), (2-3-2), and In the explanation of formula (2-3-3), the rings a, b, and c were explained as benzene rings. The rings a to c are nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen- or sulfur-containing heteroaryl rings. The same applies when it is changed to a heteroaryl ring (5-membered ring).

[0073] The "aryl ring" which is the ring A, ring B and ring C in the general formula (1) includes, for example, Examples thereof include aryl rings having 6 to 30 carbon atoms, and aryl rings having 6 to 16 carbon atoms are preferred. An aryl ring having 12 carbon atoms is more preferred, and an aryl ring having 6 to 10 carbon atoms is particularly preferred. This "aryl ring" is defined as "R 1 ~R 11 Adjacent groups among The aryl ring formed by bonding the aryl group to the ring a, ring b, or ring c corresponds to the aryl ring formed by bonding the aryl group to the ring a, ring b, or ring c, and the aryl ring (or ring b, ring c) is already composed of a benzene ring with 6 carbon atoms, so The minimum carbon number is 9 in total in the fused rings.

[0074] Specific examples of the "aryl ring" include a monocyclic benzene ring and a bicyclic biphenyl ring. ring, a fused bicyclic ring, a naphthalene ring, a tricyclic ring, a terphenyl ring (m-terphenyl, o-Terphenyl, p-Terphenyl), fused tricyclic ring system, acenaphthylene ring, fluoro ene ring, phenalene ring, phenanthrene ring, anthracene ring, fused tetracyclic ring system, triphenylene ring, Nylene ring, pyrene ring, naphthacene ring, perylene ring which is a fused five-ring system, and pentacene ring It can be given.

[0075] Examples of the "heteroaryl ring" which is ring A, ring B and ring C in general formula (1) include: Examples include heteroaryl rings having 2 to 30 carbon atoms, and heteroaryl rings having 2 to 25 carbon atoms are preferred. Heteroaryl rings having 2 to 20 carbon atoms are preferred, and heteroaryl rings having 2 to 15 carbon atoms are even more preferred. An aryl ring is more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Examples of "heteroaryl rings" include ring-constituting atoms such as oxygen, sulfur, and nitrogen in addition to carbon. Examples of heterocyclic rings include those containing 1 to 5 heteroatoms selected from the group consisting of aryl, aryl, aryls ... The "heteroaryl ring" is defined as "R 1 ~R 11 adjacent groups among and a, b, or c rings are bonded together to form a heteroaryl ring. In addition, since the a ring (or b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, In addition, the total number of carbon atoms in the fused ring formed by condensing the five-membered ring is 6, which is the lower limit of the number of carbon atoms.

[0076] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoaryl ring, and an aryl ring. Oxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole 1H-indazole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, Azole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring , quinazoline ring, quinoxaline ring, phenanthroline ring, phthalazine ring, naphthyridine ring , purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenanthrin ring, noxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, Furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring Thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring benzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzo Phosphoroxide ring, dibenzophosphoroxide ring, furazan ring, thianthrene ring, Indolocarbazole ring, benzoindolocarbazole ring, benzobenzoindolocarbazole Examples include a zole ring, an imidazoline ring, and an oxazoline ring.

[0077] At least one hydrogen atom in the above "aryl ring" or "heteroaryl ring" is The substituents of 1 are substituted or unsubstituted "aryl" and substituted or unsubstituted "hetero aryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "dihe substituted or unsubstituted "arylheteroarylamino"; substituted or unsubstituted "arylheteroarylamino"; Or unsubstituted "diarylboryl" (two aryls are bonded via a single bond or a linking group). "substituted or unsubstituted "alkyl", "substituted or unsubstituted "silyl", "substituted or unsubstituted "alkyl", "substituted or unsubstituted "alkyl", "substituted or unsubstituted "silyl ... "chloroalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryl" The first substituent may be substituted with "aza-1-yloxy" or a substituted silyl. "Aryl" and "heteroaryl" and "diarylamino" are aryl and "diheteroaryl" The heteroaryl in "arylamino" and the aryl and heteroaryl in "arylheteroarylamino" As the aryl, the aryl in "diarylboryl", and the aryl in "aryloxy" is a monovalent group of the above-mentioned "aryl ring" or "heteroaryl ring".

[0078] The "alkyl" as the first substituent may be either a straight chain or a branched chain. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, Alkyl having 1 to 12 prime numbers (branched alkyl having 3 to 12 carbon atoms) is more preferred, Alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is more preferred, and alkyl having 1 to 5 carbon atoms is more preferred. Alkyl (branched alkyl having 3 to 5 carbon atoms) is particularly preferred, and alkyl (branched alkyl having 1 to 4 carbon atoms) is particularly preferred. Branched alkyl having 3 or 4 prime numbers is most preferred.

[0079] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, and n-butyl. butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl , t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2- Pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl Cyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl 2-Heptyl, 2-Ethylhexyl, 2-Propylpentyl, n-Nonyl, 2,2-Dimethyl 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n- Decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexyl Cylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecy Examples include n-octadecyl, n-eicosyl, and the like. Also, 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-methyl ethylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl propyl, 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 are also included.

[0080] The "cycloalkyl" as the first substituent is a 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 cycloalkyl, cycloalkyl with 3 to 12 carbon atoms, cycloalkyl with 5 to 10 carbon atoms cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms Examples include alkyl groups.

[0081] Specific cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and and alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbon atoms or 1 to 4 carbon atoms, and norbornene nyl, 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 , diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0082] Furthermore, the "alkoxy" as the first substituent includes, for example, straight chain or alkyl groups having 1 to 24 carbon atoms. or branched alkoxy having 3 to 24 carbon atoms. Branched alkoxy having 3 to 18 carbon atoms) is preferred, and alkoxy having 1 to 12 carbon atoms (carbon Alkoxy having 3 to 12 carbon atoms) is more preferred, and alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred. Alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred, and alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred. Alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred. branched alkoxy) is most preferred.

[0083] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, n -butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentoxy t-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy Siloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-di Methylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy , n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylheptyloxy xyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy Hexyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyl Oxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dode Cyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy oxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n -octadecyloxy, n-eicosyloxy, and the like.

[0084] The "substituted silyl" as the first substituent includes, for example, aryl, alkyl, and cyclohexyl. silyl substituted with at least one of triarylsilyl, ... alkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyl Examples thereof include dicycloalkylsilyl.

[0085] "Triarylsilyl" refers to a silyl group in which the three hydrogen atoms are independently aryl. Examples of such groups include groups substituted with aryl, where the aryl is a monovalent group of the "aryl ring" described above. The aryl group preferably has 6 to 10 carbon atoms. Specific examples include phenyl and naphthyl.

[0086] Specific examples of triarylsilyl include triphenylsilyl and diphenylmononaphthyl. silyl, monophenyldinaphthylsilyl, trinaphthylsilyl, and the like.

[0087] "Trialkylsilyl" refers to a silyl group in which the three hydrogen atoms are independently alkyl. The alkyl may be substituted with the alkyl group described above in the first substituent. The alkyl group preferably used for substitution is a carbonyl group. Alkyl having 1 to 5 prime numbers, specifically methyl, ethyl, propyl, i-propyl, Examples include butyl, sec-butyl, t-butyl, and t-amyl.

[0088] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, and triplylsilyl. Iodopropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl , tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl Isopropylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl silyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-Butyldiethylsilyl, t-Butyldiethylsilyl, t-Amyldiethylsilyl , methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec -Butyldipropylsilyl, t-Butyldipropylsilyl, t-Amyldipropylsilyl , methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl Examples include methyldi-i-propylsilyl.

[0089] "Tricycloalkylsilyl" refers to a silyl group in which the three hydrogen atoms are independently Examples of the cycloalkyl substituted group include a group substituted with cycloalkyl, and the cycloalkyl is the same as the first substituent described above. The group described as "cycloalkyl" in the substituent can be cited. The most preferred cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms, specifically cycloalkyl. cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclo Decyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo [1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]hexyl butyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydronaphthalenyl Examples include hydroazulenyl.

[0090] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl, tricyclo hexylsilyl, etc.

[0091] "Dialkylcycloalkylsilyl" is a compound substituted with two alkyls and one cycloalkyl. " and "alkyldicycloalkyl ... Specific examples of "aryl" include alkyls and cycloalkyls selected from the specific alkyls and cycloalkyls described above. Examples of such silyl include silyl substituted with a group.

[0092] The "aryl" in the "diarylboryl" of the first substituent is the aryl group described above. The two aryls can be linked by a single bond or a linking group (e.g., >C( -R), >O, >S or >NR), where R in R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl , cycloalkyl, alkoxy, aryloxy, or substituted silyl (the first substituent) wherein the first substituent may further comprise an aryl, heteroaryl, alkyl, or cycloaryl. Specific examples of these groups include the above-mentioned alkyl groups. Aryl, heteroaryl, diarylamino, alkyl, cyclohexyl ... The description of alkyl, alkoxy, aryloxy or substituted silyl can be cited.

[0093] Specifically, the steric hindrance, electron donating property, and electron withdrawing property of the first substituent structure cause the emission of light. The wavelength can be adjusted, and the group is preferably represented by the following structural formula: More preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, and adatomyl. Mantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, Bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazo aryl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably , methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenantyl nyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di- p-Tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6 -dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of the stability, a larger steric hindrance is preferable for selective synthesis. -butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4 -xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolyl arylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl Preferred are 3,6-di-t-butylcarbazolyl and 3,6-di-t-butylcarbazolyl.

[0094] In the following structural formula, "Me" is methyl, "tBu" is t-butyl, and "tAm" is t- amyl, "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0095] In the general formula (2), any "-C(-R)=C(-R)-" (where R is in formula (2) R 1 ~R 11 R in "-N(-R)-" which may be substituted by is aryl, alkyl, or cycloalkyl, but the aryl, alkyl or cycloalkyl is Examples include the groups described above. In particular, aryl groups 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) is preferred.

[0096] The first substituent is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", "Diaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted " "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", Substituted or unsubstituted "diarylboryl (two aryls are connected via a single bond or a linking group) "substituted or unsubstituted "alkyl", "substituted or unsubstituted "Cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted The "aryloxy" in the substituents may be substituted or unsubstituted as described above. At least one hydrogen atom may be substituted with a second substituent. Examples of the alkyl group include aryl, heteroaryl, alkyl, and cycloalkyl. Specific examples of these include the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring", The explanation of "alkyl" or "cycloalkyl" as the first substituent can be referred to. In addition, the aryl and heteroaryl groups as the second substituents have a small number of substituents. At least one hydrogen atom is an aryl such as phenyl (specific examples are given above), an alkyl such as methyl alkyl (specific examples are the groups listed above) or cycloalkyl such as cyclohexyl (specific examples are the groups listed above) The aryl and heteroaryl groups as the second substituents are also substituted with the groups mentioned above. For example, when the second substituent is a carbazolyl group, at least one of the 9-positions The other hydrogen is an aryl such as phenyl, an alkyl such as methyl, or a cyclohexyl A carbazolyl group substituted with a cycloalkyl such as Included in the rule.

[0097] R in general formula (2) 1 ~R 11 Aryl, heteroaryl, diarylamino in Aryl, heteroaryl of diheteroarylamino, arylheteroarylamino Aryl and heteroaryl, aryl in diarylboryl, or aryl in aryloxy The ring may be one of the "aryl ring" or "heteroaryl ring" described in the general formula (1). Also, R 1 ~R 11 Alkyl, cycloalkyl, alkoxy in Si, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkyl The cycloalkylsilyl or alkyldicycloalkylsilyl is a silyl group represented by the above-mentioned general formula The first substituent in the description of (1) is “alkyl,” “cycloalkyl,” or “alkoxy.” "triarylsilyl", "trialkylsilyl", "tricycloalkylsilyl", "dialkylcycloalkylsilyl" or "alkyldicycloalkylsilyl" Furthermore, aryl, hydroxyl, and the like as substituents on these groups can be used. The same applies to aryl, alkyl, or cycloalkyl. 1 ~R 11 Of Adjacent groups of the formula (I) are bonded to each other to form an aryl or heteroaryl ring together with ring a, ring b or ring c. When a heteroaryl ring is formed, the heteroaryl and diarylamino groups which are substituents on the ring , diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl aryl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkyl Silyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldi Cycloalkylsilyl and further substituents aryl, heteroaryl, aryl The same applies to alkyl or cycloalkyl.

[0098] Y in general formula (1) 1 In the above, R in Si-R and Ge-R is aryl, alkyl or is cycloalkyl, and the aryl, alkyl or cycloalkyl is as defined above. In particular, aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.) , alkyl having 1 to 5 carbon atoms or alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or alkyl having 5 carbon atoms Cycloalkyl having a carbon number of 10 or less (preferably cyclohexyl or adamantyl) is preferred. The explanation is as follows: Y in general formula (2) 1 But it's the same.

[0099] X in general formula (1) 1 and X 2 In the formula, R in >NR is substituted with the second substituent described above. aryl, heteroaryl, alkyl or cycloalkyl, optionally At least one hydrogen in the aryl or heteroaryl may be replaced by, for example, an alkyl or cycloalkyl group. The aryl, heteroaryl, alkyl and cycloalkyl may be substituted. Examples of the arylalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., fluoro) phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.) , alkyl having 1 to 5 carbon atoms or alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or alkyl having 5 carbon atoms Cycloalkyl having a carbon number of 10 or less (preferably cyclohexyl or adamantyl) is preferred. The explanation is as follows: X in general formula (2) 1 and X 2 But it's the same.

[0100] In the general formula (1), R in the linking group "-C(-R)2-" is hydrogen, alkyl, or is cycloalkyl, and the alkyl and cycloalkyl include the groups described above. In particular, alkyl groups with 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). This explanation also applies to the linking group "-C(-R)2-" in general formula (2). be.

[0101] The present invention also provides a method for producing a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1). A polymer, preferably a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2) The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and more preferably a dimer. The polymer is particularly preferably in a form having a plurality of the above unit structures in one compound. For example, the unit structure may be a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthyl group, or the like. In addition to the form in which multiple units are bonded together with linking groups such as ethylene groups (linked polymers), Any ring (A ring, B ring or C ring, a ring, b ring or c ring) contained in the The unit structure may be a ring-covalent polymer in which the unit structure is bonded to the ring-covalent polymer. Any rings (ring A, ring B or ring C, ring a, ring b or ring c) contained in The bonded form may be a ring-fused multimer, but the ring-covalent multimer and ring-fused multimer may also be used. Covalent multimers are preferred, and ring-covalent multimers are more preferred.

[0102] Examples of such multimers include those represented by the following formula (2-4), formula (2-4-1), and formula (2- 4-2), a polymer represented by formula (2-5-1) to formula (2-5-4) or formula (2-6) The multimeric compound represented by the following formula (2-4) is a compound represented by the general formula (2). In this case, a plurality of units represented by general formula (2) are bonded together so as to share the benzene ring, which is the a-ring. It is a polymeric compound (ring-covalent polymer) having the structure in one compound. The polymer compound represented by general formula (2) is a benzene ring. The unit structures represented by the two general formulas (2) are arranged in one compound so as to share a ring. It is a polymeric compound (ring-covalent polymer) having the following formula (2-4-2): The polymeric compound is, as explained in the general formula (2), formed by sharing the benzene ring, which is the a-ring. A polymeric compound (ring) having three unit structures represented by the general formula (2) in one compound is Covalent multimers). Also, the compound is represented by any one of the following formulas (2-5-1) to (2-5-4): The polymeric compound to be produced is, as explained in general formula (2), a benzene ring (b) (or c ring). A compound having a plurality of unit structures represented by general formula (2) in one compound so as to share a ring. The polymer compound (ring-covalent polymer) is a polymer represented by the following formula (2-6): The compound can be described by the general formula (2), for example, by the b ring (or a ring, c ring) of a certain unit structure. and the b-ring (or a-ring, c-ring) of a certain unit structure are condensed. In this way, a large amount of a compound having a plurality of unit structures represented by general formula (2) in one compound is obtained. The definitions of the symbols in the following structural formula are the same as those in general formula (2). This is the same as the definition of the symbol.

[0103] [ka]

[0104] The polymeric compound is represented by formula (2-4), formula (2-4-1), or formula (2-4-2). and a polymerized form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6). The polymer may be a polymer that combines the polymerized form represented by formula (2-5-1) to formula (2-5-2). (2-5-4) and the polymerized form represented by formula (2-6) The compound may be a polymer having a combination of the above-mentioned structures, and may be represented by the formula (2-4), the formula (2-4-1), or The polymerized form represented by formula (2-4-2) and any of formulas (2-5-1) to (2-5-4) The polymerized form represented by either formula (2-1) and the polymerized form represented by formula (2-6) are combined. It may also be a polymer.

[0105] The chemical structure of polycyclic aromatic compounds and their multimers represented by general formula (1) or (2) is also All or some of the hydrogen in the structure is fluorine, chlorine, bromine, iodine or deuterium. For example, in formula (1), ring A, ring B and ring C (rings A to C are aryl rings or is a heteroaryl ring), substituents on rings A to C, Y 1 When is Si-R or Ge-R R (= alkyl, cycloalkyl, aryl), and X 1 and X 2 >NR When R (= alkyl, cycloalkyl, aryl) is fluorine, chlorine , bromine, iodine or deuterium, among which aryl and heteroaryl are preferred. All or some of the hydrogen atoms in the molecule are replaced by fluorine, chlorine, bromine, iodine, or deuterium. Among chlorine, bromine, and iodine, chlorine or bromine is preferred, and More preferably, it is chlorine.

[0106] The chemical structure of polycyclic aromatic compounds and their multimers represented by general formula (1) or (2) is also At least one of the aromatic and heteroaromatic rings in the structure has at least one cycloalkenyl group. It may be condensed with a carboxylic acid.

[0107] For example, aryl and heteroaryl rings that are rings A, B, C, a, b, and c. Aryl groups (aryl, diaryl) as the first and second substituents on the aryl ring, rings A to C arylamino, arylheteroarylamino, diarylboryl, aryloxy or The aryl group in triarylsilyl) and heteroaryl group (heteroaryl , heteroaryl in diheteroarylamino or arylheteroarylamino portion), aryl groups (similar to above) as the first and second substituents on rings a to c, and and heteroaryl groups (as above), Y 1 The R in Si-R and Ge-R is A aryl group (as above), and X 1 and X 2 Ally as R in NR At least one of the aryl group (as above) and the heteroaryl group (as above) is It may be condensed with at least one cycloalkane.

[0108] Preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, and hetero rings. Aryl group (aryl, diaryla) as the first substituent on the aryl ring, ring A to ring C the aryl group in amino, diarylboryl, or aryloxy) and heteroaryl Aryl group (heteroaryl moiety in heteroaryl or diheteroarylamino) , an aryl group (similar to above) and a heteroaryl as the first substituent on rings a to c groups (as above), and X 1 and X 2 An aryl group as R in NR ( at least one of a aryl group (as above) and a heteroaryl group (as above) Each of the cycloalkanes may be condensed with one cycloalkane.

[0109] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, and ring A to ring C are An aryl group as the first substituent on the C ring (aryl in aryl or diarylamino) aryl group portion) and heteroaryl group (heteroaryl portion of heteroaryl) , an aryl group (similar to above) and a heteroaryl as the first substituent on rings a to c groups (as above), and X 1 and X 2 An aryl group as R in NR ( at least one of the above-mentioned cycloalkanes is condensed with at least one cycloalkane. It's fine.

[0110] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c. An aryl group as the first substituent on the C ring (in aryl or diarylamino aryl group portion), aryl group as the first substituent on rings a to c (same as above), etc. Rabii, X 1 and X 2 Of the aryl groups (similar to above) as R in NR, At least one may be fused with at least one cycloalkane.

[0111] "Cycloalkane" includes cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, Cycloalkanes, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, Cycloalkanes with prime numbers 5-10, cycloalkanes with carbon numbers 5-8, cycloalkanes with carbon numbers 5-6 Examples include alkanes and cycloalkanes with five carbon atoms.

[0112] Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, Cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, nor Bornene, 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 Hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adaman naphthalene, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbon atoms or 1 to 4 carbon atoms, halogen (especially fluorine) substituted derivatives Examples include hydrogen-substituted and deuterium-substituted compounds.

[0113] Among these, for example, the carbon atom at the α-position of cycloalkane (aromatic In cycloalkanes fused to aromatic or heteroaromatic rings, the carbon atom adjacent to the fused site is A structure in which at least one hydrogen atom at the α-position carbon is substituted is preferred, and A structure in which two hydrogen atoms are replaced at the α-position carbon atom is more preferable, and a total of four hydrogen atoms at the two α-position carbon atoms are The substituent is preferably a group having 1 to 5 carbon atoms or a group having 1 to 5 carbon atoms. 1 to 4 alkyl (especially methyl) substituted, halogen (especially fluorine) substituted and deuterium substituted Examples include transformations. [ka]

[0114] The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3. Preferably, one or two rings are preferable, and one ring is even more preferable. For example, one benzene ring Examples of phenyl groups fused with one or more cycloalkanes are shown below. In the above, * indicates a benzene ring included in the skeletal structure of the compound if it is a benzene ring. In the case of a phenyl group, it means a bond that is substituted on the skeleton structure of the compound. The condensed cycloalkanes shown in formula (Cy-1-4) and formula (Cy-2-4) are The fused ring (group) may be an aromatic ring other than a benzene ring (phenyl group) or Even if the condensed cycloalkane is a cyclopentane or heteroaromatic ring, The same applies to cycloalkanes other than cyclohexane. [ka]

[0115] At least one -CH2- in the cycloalkane may be replaced with -O- However, when multiple -CH2- are replaced with -O-, adjacent -CH2- are replaced with -O-. It is not substituted. For example, a cycloalkane fused to one benzene ring (phenyl group) Examples of the structure in which one or more -CH2- groups are replaced with -O- are shown below. In the above, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond that is substituted on the skeleton structure of the compound. The condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group). Even in the case of a ring, the condensed cycloalkane is cyclopentane or cyclohexane or The same applies to other cycloalkanes. [ka]

[0116] At least one hydrogen atom in the cycloalkane may be substituted, and this substituent and Examples of such groups include aryl, heteroaryl, diarylamino, and diheteroarylamino. Aryl, heteroaryl, amino, diarylboryl (two aryls are single bond or (which may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryl Examples of the silyl group include aryloxy, substituted silyl, deuterium, cyano, and halogen. The explanation of the first substituent mentioned above can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), Preferred are cycloalkyl, halogen (e.g., fluorine), and deuterium. When the ring is substituted, it may be substituted to form a spiro structure, for example, one benzene ring ( Examples of spiro structures formed in cycloalkanes fused to a phenyl group are shown below. In the formula, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond that substitutes for the skeletal structure of the compound. do. [ka]

[0117] Another form of cycloalkane condensation is a polycyclic aromatic ring represented by general formula (1) or (2): Aromatic compounds and their multimers are, for example, diarylamino compounds condensed with cycloalkanes. a carbazolyl group (fused to the aryl moiety), a cycloalkane-fused carbazolyl group (fused to the aryl moiety), benzocarbazolyl group (fused to the benzene ring moiety) or fused to a cycloalkane (this Examples of "diarylamino groups" include those substituted with a benzene ring moiety (condensed with the benzene ring moiety). Examples thereof include the groups explained above as the "first substituent".

[0118] Further specific examples include polycyclic aromatic compounds represented by general formula (2) and R in multimers of 2 is a diarylamino group fused with a cycloalkane (this aryl a carbazolyl group (fused to the benzene ring portion) or a carbazolyl group (fused to the benzene ring portion) Examples include condensation into olefins.

[0119] As an example, a polycyclic aromatic compound represented by the following general formula (2-Cy) or Examples include a multimer of a polycyclic aromatic compound having a plurality of structures represented by the general formula (2-Cy). In the following structural formula, Cy represents a cycloalkane, and n represents an integer of 1 to 3 (preferably 1). and "=(Cy)n" is an integer, and n cycloalkanes are condensed at any position in the structure. (In the structural formula below, n cycloalkanes are attached to the benzene ring (phenyl group). The definitions of the symbols in the structural formula are the same as those in general formula (2). That is correct. [ka]

[0120] Specifically, compounds represented by the following formulas can be mentioned: "Cy" in the following formulas represents cycloaliphatic alkyl groups. Each n is independently 0 to the maximum condensable number (however, all n's are 0). n is preferably 0 to 2 (but all n's are not 0), more preferably Preferably, it is 1, and "=(Cy)n" is any structure in which n cycloalkanes are condensed. For example, in the following formula "2-Cy-(1)", the benzene ring may be fused at any position. (n cycloalkanes are condensed at the OP position) "h" represents a phenoxy group, "Me" represents a methyl group, and each compound has the first substituent and and a second substituent, and at least one hydrogen in each compound is substituted with a thiol. It has been replaced by .

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

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[0127] [ka]

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[0130] [ka]

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[0135] Furthermore, the polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of organic devices that can be used include organic electroluminescent devices, organic field effect devices, and the like. Examples include transistors and organic thin-film solar cells. In particular, organic electroluminescent devices In the case of the dopant material of the light-emitting layer, Y 1 is B, X 1 and X 2 Compounds where is >NR Things, Y 1 is B, X1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 but As a host material of the light-emitting layer, a compound in which Y 1 is B, X 1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 Compounds in which is >O are preferred, As a child transport material, Y 1 is B, X 1 and X 2 Compounds where Y is >O 1 P=O,X 1 and X 2 Compounds in which is >O are preferably used.

[0136] The chemical structure of polycyclic aromatic compounds and their multimers represented by general formula (1) or (2) is also At least one hydrogen atom in the structure is replaced by a cyano group, and all or some of the hydrogen atoms are The substituent may be a cyano group.

[0137] The form of cyano substitution includes a form in which a cyano group is directly substituted on rings A to C of formula (1), or a form in which a cyano group is directly substituted on rings A to C of formula (1), 2) R 1 ~R 11 In addition to the form in which the hydrogen selected as the hydroxyl group is replaced with a cyano group, The first substituent is an aryl, heteroaryl (especially a carbazolyl group or a benzocaine group). rubazolyl group), diarylamino, diheteroarylamino, arylheteroaryl Amino, diarylboryl (two aryls are bonded via a single bond or a linking group) may be), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl At least one of hydrogen, the second substituent, aryl, heteroaryl, aryl, At least one hydrogen atom of alkyl or cycloalkyl is substituted with a cyano group. In addition, R in >NR may be an aryl, heteroaryl, alkyl, or silyl. In the chloroalkyl (first substituent) or the substituent (second substituent) At least one of the hydrogen atoms may be substituted with a cyano group. Among these, there are those in which a cyano group is directly substituted on rings A to C of formula (1), and those in which R 1 ~R 1 1 A form in which the hydrogen selected as the formula (I) is substituted with a cyano group is preferred.

[0138] Another form of cyano substitution is a polycyclic aromatic compound represented by general formula (1) or (2). The compounds and polymers thereof may be, for example, cyano-substituted aryl groups, cyano-substituted alkyl groups, cycloalkyl groups, cyano-substituted alkoxy groups, cyano-substituted dialkyl groups, arylamino group, cyano-substituted diarylboryl group (two aryls are single bond or a cyano-substituted carbazolyl group or a cyano-substituted carbazolyl group, which may be bonded via a linking group; Examples of the substituted benzocarbazolyl group include "aryl groups," "alkyl groups," and "alkyl groups." "cycloalkyl groups," "alkoxy groups," "diarylamino groups," and "diaryl The "arylboryl group" includes the groups explained above as the "first substituent." To arylamino, diarylboryl, carbazolyl and benzocarbazolyl groups The substitution of the cyano group in these groups may be a part of the aryl ring or benzene ring. Alternatively, all hydrogen atoms may be substituted with cyano groups. Y in general formula (1) or (2) 1 is B and X 1 and X 2 is >NR, and At least one hydrogen atom in the A ring of formula (1) is replaced with a cyano group, or R 1 ~R 3 is preferably a cyano group. ) or Y in (2) 1 is B and X 1 and X 2 is >NR and the formula (1) At least one hydrogen atom in the B ring and the C ring of formula (2) is substituted with a cyano group, R 4 ~R 11 , especially R 5 and R 10 is preferably a cyano group.

[0139] The "aryl" substituted with a cyano group is an "aryl" in which at least one of the hydrogen atoms of the aryl is cyano. Examples include groups substituted with an aryl group, specifically those represented by the following structural formulae (S-100) to (S- Among these, preferred are groups represented by the formula (S -100) to (S-107), and more preferably a group represented by the formula (S- 100), equation (S-103), equation (S-104) or equation (S-105). "Diarylamino", "arylheteroarylamino", "diaryl This also applies when a cyano group is substituted on the aryl moiety of "arylboryl" or "aryloxy." The description applies. [ka]

[0140] The "alkyl" substituted with a cyano group is one in which at least one hydrogen atom of the alkyl is substituted with a cyano group. The alkyl part of "alkoxy (alkyloxy)" is This explanation also applies when a cyano group is substituted at the position. The "cycloalkyl" refers to a group in which at least one hydrogen atom of the cycloalkyl is substituted with a cyano group. Examples of groups that have been mentioned include:

[0141] Further specific examples include polycyclic aromatic compounds represented by general formula (2) and R in multimers of 2 cyano-substituted diarylamino groups, cyano-substituted diarylamino groups, an arylboryl group (two aryls may be bonded via a single bond or a linking group); or a cyano-substituted carbazolyl group.

[0142] As an example, a polycyclic aromatic compound represented by the following general formula (2-A) or Examples include a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-A). The definitions of the symbols in the formula are the same as those in general formula (2). [ka]

[0143] Specific examples of the cyano-substituted polycyclic aromatic compounds and multimers thereof of the present invention include In this case, at least one hydrogen atom in one or more aromatic rings in the compound is replaced by one or more hydrogen atoms. Examples include compounds substituted with multiple cyano groups, such as compounds substituted with 1 to 2 cyano groups. The number of substituted cyano groups is preferably 1 to 4, more preferably 2 to 4. Preferably, 2 to 3 is more preferable, and 3 is particularly preferable.

[0144] Specifically, compounds represented by the following structural formulas are included: Each independently represents 0 to 2, preferably 1. In the following structural formula, "CN" represents a cyano group, "OPh" represents a phenoxy group, "Me" represents a methyl group, and "Et" represents an ethyl group.

[0145] [ka]

[0146] [ka]

[0147] [ka]

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[0159] [ka]

[0160] Further specific examples of the cyano-substituted polycyclic aromatic compounds of the present invention include those having the following structures: In the structural formula below, "CN" represents a cyano group, and "D" represents Deuterium, "Me" is a methyl group, "Et" is an ethyl group, "tBu" is a t-butyl group, and "tA "m" indicates t-amyl.

[0161] [ka]

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[0183]

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[0184] A polycyclic aromatic compound represented by the above general formula (1), or a compound having a structure represented by the above general formula (1) As a polymer of polycyclic aromatic compounds having multiple structures, Y 1 is preferably boron, Furthermore, a monomer compound is preferred. The A ring (a ring) and the C ring (c ring) are connected to each other by a linking group or a single bond. Preferably, X is not bonded to the ring. 1 or X 2 R when is >NR In the above, the A ring, the B ring and the C ring (the a ring, the b ring and the c ring) are connected by a linking group or a single bond. In particular, the ring A, the ring B and the ring C (the ring a, the ring b and the ring A form in which the ring is not bonded to any of the rings (ring c) is preferred.

[0185] The polycyclic aromatic compound represented by the general formula (1) and its multimer according to the present invention are A polymer compound (this) is a polymer made by polymerizing a reactive compound substituted with a reactive substituent as a monomer. The monomer for obtaining the polymer compound has a polymerizable substituent), or A polymer crosslinked body obtained by further crosslinking the polymer compound (the polymer The compound has a crosslinkable substituent), or a main chain polymer is reacted with the reactive compound. The pendant polymer compound (the reactive compound for obtaining the pendant polymer compound) The polymer compound has a reactive substituent), or the pendant polymer compound is further crosslinked. The pendant-type crosslinked polymer (the pendant-type crosslinked polymer obtained by the above-mentioned pendant-type crosslinked polymer) Even if the polymer compound has a crosslinkable substituent, it can be used as a material for organic devices, for example, Materials for organic electroluminescent devices, organic field-effect transistors, or organic thin-film solar cells It can be used for food.

[0186] The reactive substituents described above (the polymerizable substituent, the crosslinkable substituent, and the pendant type (including reactive substituents for obtaining polymers, hereinafter also referred to simply as "reactive substituents") is a substituent capable of increasing the molecular weight of the polycyclic aromatic compound, Substituents that can further crosslink the polymer, and those that can react pendantly with the main chain polymer. Although there are no particular limitations, substituents having the following structures are preferred: * in each structural formula indicates the bonding position Shows. [ka]

[0187] L's each independently represent a single bond, -O-, -S-, >C=O, -OC(=O)-, Alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and Among the above substituents, the polyoxyalkylenes represented by the formula (XLS-1), the formula (XLS- 2), Formula (XLS-3), Formula (XLS-9), Formula (XLS-10) or Formula (XLS-1 A group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-7) is preferred, The group represented by 17) is more preferred.

[0188] Such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant polymer compounds The crosslinked polymer is a compound having a repeating unit of a polycyclic aromatic compound represented by formula (1) or (2). In addition to the positions, substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraazine phenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylsilane, Phenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted The compound is a compound having at least one repeating unit selected from the group consisting of substituted dibenzofurans. It may also include. Substituents in these repeating units include, for example, aryl, heteroaryl, Diarylamino, diheteroarylamino, arylheteroarylamino, diaryl aryl (two aryls may be bonded via a single bond or a linking group); aryl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkyl Silyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyl Examples include dicycloalkylsilyl. The "aryl" in triarylamine and For details of these substituents, see the polycyclic aromatic compounds represented by formula (1) or (2). You can quote explanations that are relevant to the topic.

[0189] Such polymer compounds, crosslinked polymers, pendant polymer compounds and pendant polymer compounds Details of the use of the polymer crosslinked body (hereinafter also referred to simply as "polymer compound and polymer crosslinked body") The details will be described later.

[0190] 2. Method for producing cyano-substituted polycyclic aromatic compounds and their multimers The polycyclic aromatic compounds and their multimers represented by the general formula (1) and (2) are basically First, the A ring (a ring) is bonded to the B ring (b ring) and the C ring (c ring) by bonding groups (X 1 or X 2 a group containing The intermediate is produced by bonding the rings A (a ring) and B (b ring) together (first reaction). ) and C ring (c ring) by bonding group (Y 1 The final product is produced by bonding the In the first reaction, for example, in the case of an etherification reaction, nucleophilic substitution occurs. General reactions such as the Buchwald reaction and the Ullmann reaction can be used for amination reactions. In the second reaction, a tandem reaction can be used. Hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, same below) can be used. In addition, in some of these reaction steps, a cyanated raw material is used, or cyanation or cyano By adding a step of introducing an ano-containing substituent, the desired position can be cyanated. The compound of formula (I) can be prepared.

[0191] The second reaction is as shown in the following schemes (1) and (2), which converts the A ring (a ring) and the B ring (b ring) and Y bonding the C ring (c ring) 1 is a reaction that introduces Y 1 is a boron atom, X 1 and X 2 The case where X is an oxygen atom is shown below. First, 1 and X 2 The hydrogen atoms between n- Orthometalation with butyllithium, sec-butyllithium, or t-butyllithium Next, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange. Then, by adding a Bronsted base such as N,N-diisopropylethylamine, The target product can be obtained by a tandem boron-Friedel-Crafts reaction. In some cases, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The structures in the above schemes (1) and (2), and the subsequent schemes (3) to (28) The symbols in the formulas are defined as above.

[0192] [ka] [ka]

[0193] The above schemes (1) and (2) are based on the polycyclic aromatic compounds represented by the general formulas (1) and (2). The method for producing the compound is mainly shown, but the multimer is also shown in the following. It can be produced by using an intermediate having (b ring) and C ring (c ring). The reaction is explained in the following schemes (3) to (5). The desired product can be obtained by doubling or tripling the amount of medicine.

[0194] [ka] [ka] [ka]

[0195] In the above scheme, lithium was introduced to the desired position by orthometalation. As shown in the following schemes (6) and (7), a bromine atom or the like is introduced at the desired position for lithium introduction. However, lithium can also be introduced into the desired position by halogen-metal exchange.

[0196] [ka] [ka]

[0197] The method for producing the multimer described in Scheme (3) can also be carried out in the same manner as in Scheme (6) and Scheme (7). and (7) introducing halogen atoms such as bromine atoms or chlorine atoms into the desired position of lithium. Lithium can also be introduced into the desired position by halogen-metal exchange (see below). Schemes (8), (9) and (10) are given below.

[0198] [ka] [ka] [ka]

[0199] This method allows the target compound to be obtained even in cases where ortho-metallation is not possible due to the influence of substituents. It is useful to be able to synthesize

[0200] By appropriately selecting the above synthesis method and the raw materials to be used, the desired position can be cyano. and Y 1 is a boron atom, X 1 and X 2 is an oxygen atom It is possible to synthesize polycyclic aromatic compounds and their multimers.

[0201] Next, as an example, Y 1 is a boron atom, X 1 and X 2 When is a nitrogen atom, the following scheme ( 11) and (12). X 1 and X 2 As in the case where X is an oxygen atom, first 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. After adding borane, etc., and carrying out lithium-boron metal exchange, N,N-diisopropylethyl Addition of a Bronsted base such as an amine can induce a tandem boron-Friedel-Crafts reaction. In this case, aluminum trichloride or the like is used to promote the reaction, and the target product can be obtained. Furthermore, as shown in the following scheme (12'), If the reaction is carried out at high temperature, the target product can be obtained using only boron tribromide. At some stage in the process, a cyanated raw material is used, or a process for cyanation or introduction of a cyano-containing substituent is performed. By adding a step, the compound of the present invention having a cyanated position at the desired position can be produced. can be done.

[0202] [ka] [ka] [ka]

[0203] Also, Y 1 is a boron atom, X 1 and X 2 For the multimer in which is a nitrogen atom, As shown in schemes (6) and (7), bromine atoms, chlorine atoms, etc. are introduced at the desired position for lithium introduction. The halogen is introduced, and lithium is introduced into the desired position by halogen-metal exchange. (Schemes (13), (14), and (15) below) As shown in (13'), halogen-metal hydrides can be prepared using boron triiodide and triphenylborane. Even without using the exchange, Y 1 is a boron atom, X 1 and X 2 When nitrogen atoms are It can also be synthesized.

[0204] [ka] [ka] [ka] [ka]

[0205] Next, as an example, Y 1 is a phosphorus sulfide, a phosphorus oxide, or a phosphorus atom, and X 1 oh Call X 2 The cases where is an oxygen atom are shown in the following schemes (16) to (19). First of all, X 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Then, add phosphorus trichloride and sulfur in that order, and finally add a Lewis acid such as aluminum trichloride and N By adding a Bronsted base such as N-diisopropylethylamine, tandem holosilane can be obtained. Sphagnum Friedel-Crafts reaction, Y 1 It is possible to obtain a compound in which the The obtained phosphorus sulfide compound can be treated with m-chloroperbenzoic acid (m-CPBA). By processing Y 1 is a phosphorus oxide, and By processing with Y 1 In addition, compounds in which the atom is a phosphorus atom can be obtained. Somewhere in the reaction process, a cyanated raw material is used, or cyanation or introduction of a cyano-containing substituent is performed. or by adding the step (a) above, the compound of the present invention having a cyanated group at the desired position can be produced. It is possible.

[0206] [ka] [ka] [ka] [ka]

[0207] Also, Y 1 is phosphorus sulfide, X 1 and X 2 For the polymers where is an oxygen atom, As shown in the above schemes (6) and (7), a bromine atom or a chlorine atom is introduced at the desired position for lithium introduction. Lithium can also be introduced into the desired position by halogen-metal exchange. This can be achieved by the following schemes (20), (21) and (22). Y 1 is phosphorus sulfide, X 1 and X 2 The polymer when is an oxygen atom is also m-Chloroperbenzoic acid (m-CPBA) can be prepared as shown in schemes (18) and (19). By processing with Y 1 is a phosphorus oxide, and By processing with fins, Y 1 is a phosphorus atom.

[0208] [ka] [ka] [ka]

[0209] Here, Y 1 is B, P, P=O or P=S, and X 1 and X 2 is > O or >Although an example of NR is given, by changing the raw materials appropriately, Y 1 However, Al, Ga, As , Si-R or Ge-R, or X 1 and X 2 Compounds with >S can also be synthesized. This can be done.

[0210] In addition to cyano-substituted alkyl groups, cyano-substituted aryl groups, and cyano-substituted alkyl groups The raw materials used are substituted with cyano-substituted heteroaryl groups, cyano-substituted aryloxy groups, etc. By adding a step of introducing these functional groups, the desired position can be Anodized compounds of the invention can be prepared.

[0211] Specific examples of solvents used in the above reactions include t-butylbenzene and xylene.

[0212] In addition, in the general formula (2), the substituents R 1 ~R 11 Adjacent of The groups bond together to form an aryl ring or a heteroaryl ring together with the ring a, ring b, or ring c. At least one hydrogen atom in the formed ring may be substituted with an aryl or heterocyclic group. Therefore, the polycyclic aromatic compound represented by the general formula (2) The compound can be represented by the following scheme ( As shown in formulas (2-1) and (2-2) of (23) and (24), the compounds constituting the These compounds are shown in the following schemes (23) and (24). It can be synthesized by applying the synthetic methods shown in the above schemes (1) to (19) to the compound. In addition, in some of these reaction steps, a cyanated raw material is used, or cyanation or cyano By adding a step of introducing an ano-containing substituent, the desired position can be cyanated. The compound of formula (I) can be prepared.

[0213] [ka] [ka]

[0214] The rings A', B' and C' in the formula (2-1) and (2-2) are each independently a substituent R 1 ~R 11 Adjacent groups of the formula (I) are bonded to each other to form rings a, b, and c, respectively. (Other ring structures are fused to ring a, ring b, or ring c) Although not shown in the formula, the a ring, b ring and c ring In some compounds, all of the rings are changed to A', B', and C' rings.

[0215] In addition, in the general formula (2), R in NR is -O-, -S-, -C(-R)2- or is bonded to at least one of the ring a, ring b and ring c by a single bond." , represented by formula (2-3-1) in the following scheme (25), X 1 or X 2 is a fused ring B' and Compounds having a ring structure incorporated into the fused ring C', and compounds of formula (2-3-2) and formula (2-3-3 ) is represented by X 1 or X 2 is expressed as a compound having a ring structure incorporated into fused ring A' These compounds can be synthesized by converting the intermediate shown in the following scheme (25) into the above scheme (1). )~(19) can be applied to the synthesis of these compounds. At some stage in the reaction process, a cyanated raw material is used, or the cyanation or introduction of a cyano-containing substituent is performed. By adding a step, the compound of the present invention in which the desired position is cyanated can be produced. This can be done.

[0216] [ka]

[0217] In addition, in the synthesis methods of the above schemes (1) to (17) and (20) to (25), trichloride Before adding boron or boron tribromide, etc., 1 and X 2 The hydrogen atom (or halogen atom) between ) by orthometalation with butyllithium, etc., to obtain tandem hetero-Friedel-Crafts The example of the reaction is shown, but without orthometalation using butyllithium etc., The reaction can also be promoted by adding boron, boron tribromide, or the like.

[0218] Also, Y 1 When the compound is phosphorus-based, X 1 and X 2 (In the formula below, the hydrogen atom between the O and n-butyllithium and sec-butyllithium are used. orthometalation with t-butyllithium or t-butyllithium, and then bis(diethylamino)chloro Phosphine is added to carry out lithium-phosphorus metal exchange, and then aluminum trichloride or other lithium-phosphorus compounds are added. By adding an acid, a tandem phosphatase Friedel-Crafts reaction is carried out to obtain the desired product. This reaction method is described in WO 2010 / 104047 (e.g., page 27). In addition, in some of these reaction steps, a cyanated raw material is used. By adding a step of cyanation or introduction of a cyano-containing substituent, the desired position can be cyanoated. The compounds of the present invention can be prepared by silylating them.

[0219] [ka] [ka]

[0220] In the above schemes (26) and (27), orthometalates such as butyllithium are also used. By using 2 or 3 times the molar amount of the methylation reagent relative to the molar amount of intermediate 1, a polymeric compound can be obtained. In addition, a bromine atom can be added in advance to the position where a metal such as lithium is to be introduced. By introducing halogen atoms such as atoms or chlorine atoms, the desired position can be achieved by halogen-metal exchange. Metal can be introduced to

[0221] In addition, the polycyclic aromatic compound represented by the general formula (2-A) can be synthesized by the following scheme (2 As shown in 8), the cyanated intermediate is synthesized and then cyclized to obtain the desired cyanide. Polycyclic aromatic compounds substituted with an aryl group can be synthesized. In Scheme (28), X is a halogen atom. or hydrogen, and the definitions of the other symbols are the same as those of the symbols in general formula (2).

[0222] [ka]

[0223] The intermediate before cyclization in scheme (28) can also be synthesized by the method shown in scheme (1) etc. This can be achieved by the Buchwald-Hartwig reaction and Suzuki coupling. Reactions such as nucleophilic substitution reactions and etherification reactions by Ullmann reaction are also included. By combining these reactions, intermediates with desired substituents can be synthesized. In the above, commercially available products can also be used as raw materials for the cyanated precursors.

[0224] In addition, precursors containing halogens or leaving groups such as trifluoromethanesulfonyl groups can be used. The cyano group can also be synthesized by subsequent substitution of the leaving group with a cyano group using cyanide. Polycyclic aromatic compounds substituted with hydroxyl groups can be synthesized. Cyanide salts such as potassium cyanide and potassium hexacyanoferrate(II) are also available. This reaction can be accelerated by using a catalyst such as palladium. It is possible.

[0225] The compound of general formula (2-A) having a cyanated diphenylamino group can be prepared, for example, by the following method: It can also be synthesized by the following method: Rehalogenated anilines and amination reactions such as the Buchwald-Hartwig reaction After introducing the cyanated diphenylamino group by 1 , X 2 is >NR In the case of amination reactions such as the Buchwald-Hartwig reaction, X 1 , X 2 When is >O, etherification with phenol leads to intermediate (M-3). Then, a metallation reagent such as butyllithium is used to transmetallate the compound. After that, it is reacted with a boron halide such as boron tribromide, and then diethyl isopropyl alcohol is added. Tandem boron-Friedel-Kraft reaction by the action of Bronsted bases such as amines The compound of general formula (2-A) can be synthesized by the Tsu reaction. It can also be applied to other cyanated compounds.

[0226] The orthometalation reagents used in the above schemes (1) to (28) include methyl Al such as lithium, n-butyllithium, sec-butyllithium, and t-butyllithium Lithium, Lithium diisopropylamide, Lithium tetramethylpiperidide, Lithium Organic alkaline compounds such as ammonium hexamethyldisilazide and potassium hexamethyldisilazide Things can be given.

[0227] The metal-Y used in the above schemes (1) to (28) 1 As a metal exchange reagent for , Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Y triiodide etc. 1 of Halides, such as CIPN(NEt2)2 1 Aminated halides of Y 1 Al Koxylate, Y 1 Examples include aryloxy compounds of the above.

[0228] The Bronsted bases used in the above schemes (1) to (28) include N,N -Diisopropylethylamine, Triethylamine, 2,2,6,6-Tetramethylpiperidine Lysine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N ,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, tetraphenylborate Potassium triphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa , Ar4BK, Ar3B, Ar4Si (where Ar is an aryl such as phenyl). It can be obtained.

[0229] The Lewis acids used in the above schemes (1) to (28) include AlCl3, AlBr3 , AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InC l3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl 3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, Mg Br2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, C u(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, Z Examples include rCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3. can be.

[0230] In the above schemes (1) to (28), the promotion of the tandem hetero-Friedel-Crafts reaction For this purpose, a Bronsted base or Lewis acid may be used, provided that Y 1 trifluoride , Y 1 trichloride, Y 1 tribromide, Y 1 Y triiodide etc. 1 Using halides of In this case, hydrogen fluoride, hydrogen chloride, hydrogen bromide, and iodide are produced as the aromatic electrophilic substitution reaction proceeds. Since acids such as hydrogen fluoride are generated, it is effective to use a Bronsted base to capture the acid. On the other hand, Y 1 Aminated halides of Y 1When an alkoxylated product of As the aromatic electrophilic substitution reaction progresses, amines and alcohols are produced, so in many cases, It is not necessary to use a Bronsted base, but the amino and alkoxy groups have low leaving ability. Therefore, the use of a Lewis acid that promotes the elimination is effective.

[0231] In addition, in the polycyclic aromatic compound and its multimer of the present invention, at least some of the hydrogen atoms are replaced with fluorine atoms. The structures are substituted with halogens such as hydrogen, chlorine, bromine, and iodine, and with deuterium. These compounds may also be used in the case where the desired position is fluorinated, chlorinated, or brominated. By using iodinated or deuterated raw materials, it can be synthesized in the same manner as above. do.

[0232] 3. Organic Devices The cyano-substituted polycyclic aromatic compound according to the present invention can be used as a material for an organic device. Examples of organic devices include organic electroluminescent devices, organic field effect transistors, and the like. Examples include organic thin-film solar cells and organic thin-film solar cells.

[0233] 3-1. Organic electroluminescent device The organic EL element according to this embodiment will be described in detail below with reference to the drawings. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention.

[0234] <Structure of organic electroluminescent device> The organic EL device 100 shown in FIG. 1 comprises a substrate 101 and an anode provided on the substrate 101. 102, a hole injection layer 103 provided on the anode 102, and a a hole transport layer 104 formed on the hole transport layer 104; a light emitting layer 105 formed on the hole transport layer 104; An electron transport layer 106 is provided on the layer 105, and an electron transport layer 108 is provided on the electron transport layer 106. The device has an injection layer 107 and a cathode 108 provided on the electron injection layer 107 .

[0235] The organic EL element 100 can be fabricated in the reverse order, for example, by fabricating the substrate 101 and the substrate 102. a cathode 108 provided on the cathode 108; an electron injection layer 107 provided on the cathode 108; An electron transport layer 106 provided on the injection layer 107, and a a light-emitting layer 105, a hole transport layer 104 provided on the light-emitting layer 105, and a hole transport layer 104 a hole injection layer 103 provided thereon, and an anode 102 provided on the hole injection layer 103; The configuration may also include the following.

[0236] Not all of the above layers are necessary, but the minimum structural unit is the anode 102 and the light-emitting layer. The cathode 108 is made up of a hole injection layer 103, a hole transport layer 104, an electron The transport layer 106 and the electron injection layer 107 are layers that are optionally provided. Each of them may consist of a single layer or multiple layers.

[0237] The organic EL element may be configured as a layer structure of the above-mentioned "substrate / anode / hole injection layer / hole In addition to the "transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, there is also the "substrate / anode / cathode" configuration. Hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode," "Substrate / anode / hole injection layer / light-emitting layer" layer / electron transport layer / electron injection layer / cathode," "substrate / anode / hole injection layer / hole transport layer / light-emitting layer" / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport 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 transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / positive electrode hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", The structure may be "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0238] <Substrate in organic electroluminescent device> The substrate 101 is a support for the organic EL element 100 and is usually made of quartz, glass, metal, or plastic. The substrate 101 may be in the form of a plate, a film, or a sheet depending on the purpose. For example, glass plates, metal plates, metal foils, plastic films, plastics, etc. Among them, glass plates, polyester, polymethacrylate, etc. are used. A plate made of a transparent synthetic resin such as polyethylene, polycarbonate, or polysulfone is preferred. For glass substrates, soda lime glass or alkali-free glass is used. It is sufficient that the thickness is sufficient to maintain mechanical strength, so for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material, it is better to have less ions dissolved from the glass, so alkali-free glass is preferred. is preferred, but soda lime glass coated with a barrier coating such as SiO2 is also commercially available. In addition, the substrate 101 is provided with a material for enhancing the gas barrier property. A gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate. When a synthetic resin plate, film, or sheet with low barrier properties is used as the substrate 101 It is preferable to provide a gas barrier film on the surface of the substrate.

[0239] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. At least one layer of a hole injection layer 103 and a hole transport layer 104 is provided between the layer 105 and the hole injection layer 103. When the organic layer 104 is provided with the organic EL element, holes are injected into the light-emitting layer 105 via the organic EL element.

[0240] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (I TO), indium zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), Examples include copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of such polythiophenes include poly(3-methylthiophene), polypyrrole, Examples include conductive polymers such as polyaniline. The material can be appropriately selected from those currently used.

[0241] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emitting element to emit light. However, from the viewpoint of power consumption of the light emitting element, low resistance is desirable. For example, 300Ω / ITO substrates with a resistance of 10Ω / □ or less can function as device electrodes, but currently, substrates with a resistance of about 10Ω / □ are required. Therefore, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □ It is especially desirable to use a low resistance product. The thickness of the ITO can be selected arbitrarily according to the resistance value. Although it is possible to increase the thickness, it is usually used in the range of 50 to 300 nm.

[0242] <Hole injection layer and hole transport layer in organic electroluminescent device> The hole injection layer 103 efficiently injects holes moving from the anode 102 into the light emitting layer 105. The hole transport layer 104 serves to inject electrons from the anode 102 into the hole transport layer 104. The injected holes or holes injected from the anode 102 through the hole injection layer 103 are efficiently The hole injection layer 103 and the hole transport layer 104 serve to transport electrons to the light-emitting layer 105. , respectively, one or more kinds of hole injection and transport materials are laminated or mixed, or hole injection and It is formed by a mixture of a transport material and a polymer binder. Also, iron chloride is used as the hole injection / transport material. An inorganic salt such as (III) may be added to form a layer.

[0243] As a hole injection / transport material, it efficiently transports holes from the positive electrode between electrodes with an applied electric field. It is necessary to have good hole injection and transport efficiency, and to have high hole injection efficiency and efficient transport of injected holes. To achieve this, it is necessary to have a small ionization potential and a high hole mobility. It is large and has excellent stability, making it difficult for impurities to be trapped during manufacturing and use. In the present invention, the materials for the hole injection layer and the hole transport layer are preferably Polycyclic aromatic compounds represented by general formula (1) or formula (2) can be used.

[0244] The hole injection layer 103 and the hole transport layer 104 are made of a photoconductive material. Compounds that have been conventionally used as charge transport materials for holes, p-type semiconductors, organic EL devices, Any compound can be selected from known compounds used in the hole injection layer and hole transport layer of the polymer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, carbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or Biscarbazole derivatives such as bis(N-alkylcarbazole), triarylamine Derivatives (polymers with 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'-dinaphtho N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 ’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl) -[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’ -Tet La[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-dia amine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenyl amines, triphenylamine derivatives, starburst amine derivatives, etc.), stilbe Phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives , hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene benzophenone-2,3,6,7,10,11-hexacarbonitrile, porphyrin derivatives, etc. In the polymer system, the polymer having the above-mentioned monomer in the side chain is Preferred are polycarbonates, styrene derivatives, polyvinylcarbazole and polysilane. However, it is necessary to form a thin film necessary for manufacturing a light-emitting element, and it is also necessary to inject holes from the anode. There is no particular limitation as long as the compound can transport the

[0245] It is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials are compounds with good electron donating properties, or , and is composed of compounds with good electron-accepting properties. For doping with electron-donating substances, Tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetrafluoroethane Strong electron acceptors such as cyano-1,4-benzoquinone dimethane (F4TCNQ) are known. (For example, see the reference "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 32 02-3204(1998)" and the document "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731(1998)). These are electron-donating base materials (hole-transporting materials) ) generates so-called holes by an electron transfer process. The conductivity of the base material changes considerably depending on the Examples of the oxidizing agent include benzidine derivatives (such as TPD) or starburst amine. derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanines) ZnPc and the like) are known (Japanese Patent Laid-Open Publication No. 2005-167175).

[0246] The above-mentioned hole injection layer material and hole transport layer material are substituted with reactive substituents. Polymer compounds obtained by polymerizing reactive compounds as monomers, or polymer crosslinked compounds thereof or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound. or its pendant polymer crosslinked product can also be used as a hole layer material. In this case, the reactive substituent is the same as that of the polycyclic aromatic compound represented by formula (1). Can be used. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0247] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 reacts with holes injected from the anode 102 between the electrodes to which an electric field is applied. The layer emits light by recombining with the electrons injected from the cathode 108. The material for forming 105 is a compound that emits light when excited by the recombination of holes and electrons. Any substance (luminescent compound) can be used, and it can be formed into a stable thin film shape and can be used in a solid state. In the present invention, the material for the light-emitting layer is preferably a compound that exhibits strong luminescence (fluorescence) efficiency in the light-emitting state. As the material, a host material and, for example, a poly(azoline) compound represented by the above general formula (1) as a dopant material are used. Aromatic ring compounds can be used.

[0248] The light-emitting layer may be a single layer or a multi-layer. The host material and the dopant material are The dopant material may be one kind or a combination of two or more kinds. It may be contained entirely or partially in the stock material. The doping method can be a co-evaporation method with the host material. Alternatively, the material may be mixed with the catalyst material in advance and then vapor-deposited simultaneously.

[0249] The amount of the host material used varies depending on the type of host material, and should be adjusted to suit the properties of the host material. The amount of the host material to be used is preferably 50 to 100% of the total amount of the materials for the light-emitting layer. 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably The content is preferably 90 to 99.9% by weight.

[0250] The amount of dopant material used varies depending on the type of dopant material. The amount of dopant material to be used should preferably be determined according to the characteristics of the light-emitting layer. It is 0.001 to 50% by weight of the total material, and more preferably 0.05 to 20% by weight. The concentration is preferably 0.1 to 10% by weight. In addition, from the viewpoint of durability, it is preferable to use hydrogen as a dopant material. It is also preferred that the atoms are partially or fully deuterated.

[0251] The host materials used were anthracene, pyrene, and dibenzyl benzoate, which have long been known as light emitters. fused ring derivatives such as benzochrysene or fluorene, bisstyryl anthracene derivatives, Bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives , cyclopentadiene derivatives, etc. In particular, anthracene compounds, fluorene compounds, etc. From the viewpoint of durability, phosphazene-based compounds and dibenzochrysene-based compounds are preferred. It is also preferable that some or all of the hydrogen atoms in the material are deuterated. Alternatively, a host compound in which all hydrogen atoms are deuterated and a compound in which some or all hydrogen atoms are deuterated are used. It is also preferable to form the light-emitting layer by combining a hydrogenated dopant compound.

[0252] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following general formula (3): be. [ka]

[0253] In formula (3), X and Ar 4 are each independently hydrogen, an optionally substituted aryl, a substituted optionally substituted heteroaryl, optionally substituted diarylamino, substituted optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino , optionally substituted alkyl, optionally substituted cycloalkyl, substituted optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryl oxy, optionally substituted arylthio, or optionally substituted silyl; All X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen atom in the compound represented by formula (3) is replaced by a halogen atom, a cyano atom, or a deuterium atom. Or it may be substituted by an optionally substituted heteroaryl.

[0254] Furthermore, a polymer (preferably a dimer) is formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X. X may be a single bond, arylene (phenylene, biphenylene, and naphthylene), ethylene, etc.) and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, etc.) phenyl ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring. (a group having a divalent bond) and the like.

[0255] The above aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryl Details of aryloxy, arylthio, and silyl will be explained in the preferred embodiments section below. In addition, the substituents on these include aryl, heteroaryl, diarylamino, diheteroaryl, and the like. arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy aryl, alkoxy, aryloxy, arylthio, or silyl, and the like. The details of the above will also be explained in the preferred embodiments section below.

[0256] Preferred embodiments of the above anthracene-based compounds are described below. The definition is the same as above. [ka]

[0257] In the general formula (3), each X independently represents the above formula (3-X1), formula (3-X2), or A group represented by formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X The group represented by (3) is bonded to the anthracene ring of formula (3) at *. Preferably, two The Xs are not simultaneously a group represented by the formula (3-X3). At the same time, it does not become a group represented by formula (3-X2).

[0258] Furthermore, a polymer (preferably a dimer) is formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X. X may be a single bond, arylene (phenylene, biphenylene, and naphthylene), ethylene, etc.) and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, etc.) phenyl ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring. (a group having a divalent bond) and the like.

[0259] The naphthylene moieties in formula (3-X1) and formula (3-X2) are fused with one benzene ring. The resulting condensed structure is as follows: [ka]

[0260] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenyl phenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorene phenylenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) groups (including carbazolyl groups, benzocarbazolyl groups, and phenyl-substituted carbazolyl groups) In addition, Ar 1 or Ar 2 is a group represented by formula (A), The group bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at * do.

[0261] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl , phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl , pyrenylyl, or a group represented by the above formula (A) (carbazolyl group, benzocarbazolyl group) (This also includes phenyl-substituted carbazolyl groups and phenyl-substituted carbazolyl groups.) 3 is expressed by formula (A) In the case where the group represented by formula (A) is a group represented by formula (3-X3), the group represented by formula (A) is a group represented by formula (3-X3) at the *. That is, the anthracene ring of formula (3) is bonded to a single bond represented by formula (A). The group is directly bonded.

[0262] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in In addition, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenyl fluorenyl, chrysenyl, triphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenyl pyrenyl, pyrenyl, or a group represented by the above formula (A) (carbazolyl group and phenyl group) The Ar may be substituted with a phenyl-substituted carbazolyl group. 3 The substituents of is a group represented by formula (A), the group represented by formula (A) is represented by the formula (3- X3) in Ar 3 and combine.

[0263] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, alkyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and / or The silyl group is preferably silyl substituted with cycloalkyl having 5 to 10 carbon atoms.

[0264] The alkyl having 1 to 4 carbon atoms to be substituted on the silyl is methyl, ethyl, propyl, i-propyl Examples of silyl include butyl, sec-butyl, t-butyl, and cyclobutyl. Three hydrogen atoms are independently substituted with these alkyl groups.

[0265] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl. silyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl silyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, proton propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyl t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl Isopropylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropyl methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl Examples include:

[0266] The cycloalkyl having 5 to 10 carbon atoms that substitutes for the silyl is 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, decahydronaphthalenyl, decahydro azulenyl, and the three hydrogens in the silyl are independently It is substituted with cycloalkyl.

[0267] Specific examples of "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include trimethylsilyl, trimethylsilyl, and cycloalkyl. Examples include cyclopentylsilyl and tricyclohexylsilyl.

[0268] Substituted silyls include di-substituted silyls with two alkyls and one cycloalkyl. Alkylcycloalkylsilyl and alkyl substituted with one alkyl and two cycloalkyl There is also alkyldicycloalkylsilyl, and specific examples of substituted alkyl and cycloalkyl are Examples of the group include the groups mentioned above.

[0269] In addition, hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) are represented by the formula (A When it is substituted with a group represented by formula (A), it may be substituted with a group represented by formula The group represented by (A) is at least one of the groups represented by * in the compound represented by formula (3). Replaces hydrogen with

[0270] The group represented by formula (A) is a substituent that the anthracene compound represented by formula (3) may have. It is one of the following. [ka]

[0271] In the above formula (A), Y is —O—, —S—, or >NR 29 and R 21 ~R 28 Haso each independently represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, alkyl, optionally substituted aryl, optionally substituted heteroaryl, substituted optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted Arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkyi alkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen , hydroxy or cyano, and R 21 ~R 28 Adjacent groups are bonded to each other and form carbon atoms. may form a hydrogen ring, an aryl ring, or a heteroaryl ring, and R 29 is hydrogen or is an optionally substituted aryl.

[0272] R 21 ~R 28 The "alkyl" in the "optionally substituted alkyl" is It may be either a straight chain or a branched chain, and may be, for example, a straight chain alkyl or a carbon Examples include branched alkyls having 3 to 24 carbon atoms. alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is preferred, alkyl) is more preferred, and alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is More preferred is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). It's nice.

[0273] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl- 2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methyl Hexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1- Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-di Methylheptyl, 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-heptyl Examples include tadecyl, n-octadecyl, and n-eicosyl.

[0274] R 21 ~R 28 "Cycloalkyl" of "optionally substituted cycloalkyl" in " 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, cycloalkyl having 5 carbon atoms Examples include cycloalkyl of the following.

[0275] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl. cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, norbornenyl, bis(methyl) chloro[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 Bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl Examples include decahydronaphthalenyl, decahydroazulenyl, and the like.

[0276] R 21 ~R 28The "aryl" in the "optionally substituted aryl" is For example, aryl having 6 to 30 carbon atoms is mentioned, and aryl having 6 to 16 carbon atoms is preferred. An aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred.

[0277] Specific examples of "aryl" include phenyl, which is a monocyclic ring, biphenylyl, which is a bicyclic ring, The fused bicyclic ring system naphthyl, the tricyclic ring system terphenylyl (m-terphenylyl, o-terphenylyl), p-Terphenylyl), fused tricyclic ring systems, acenaphthylenyl, fluorenyl, phenylenyl, phenalenyl, phenanthrenyl, fused tetracyclic ring systems triphenylenyl, pyrenyl , naphthacenyl, and fused five-ring systems such as perylenyl and pentacenyl.

[0278] R 21 ~R 28 "Heteroaryl" of "optionally substituted heteroaryl" in Examples of the heteroaryl include heteroaryls having 2 to 30 carbon atoms, and heteroaryls having 2 to 25 carbon atoms. Heteroaryl having 2 to 20 carbon atoms is preferred, and heteroaryl having 2 to 20 carbon atoms is more preferred. Heteroaryl having 15 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. In addition, heteroaryl includes, for example, ring-constituting atoms other than carbon, such as oxygen, sulfur, and and heterocycles containing 1 to 5 heteroatoms selected from nitrogen and the like.

[0279] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, and isoxa. Zolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl , quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalic acid dinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phen Noxathiinil, phenoxazinil, phenothiazinil, phenazinil, phenazinil Indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl benzothiophenyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl , naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophospho Monovalent radicals of dibenzophosphole oxide rings, monovalent radicals of dibenzophosphole oxide rings, furazanyl, thiazol-1, Indolocarbazolyl, benzindolocarbazolyl and benzobenzoyl Examples include benzoxazole and benzoxazole.

[0280] R 21 ~R 28 As the "alkoxy" in "optionally substituted alkoxy" in Examples of the alkoxy include linear alkoxy having 1 to 24 carbon atoms and branched alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred. Alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred. alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred, Alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0281] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, and isopropoxy. , n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n- Pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n- Hexyloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3 -dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy oxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethyloxy n-Hexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethyl Heptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy Cyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n- Dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy , n-octadecyloxy, n-eicosyloxy, and the like.

[0282] R 21 ~R 28 "Aryloxy" in "optionally substituted aryloxy" " is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is as defined above. R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0283] R 21 ~R 28 and the "arylthio" in the "optionally substituted arylthio" The hydrogen atom of the -SH group is replaced with an aryl group, and the aryl group is the same as the above-mentioned R 2 1 ~R 28The group described as "aryl" in the above formula can be used.

[0284] R 21 ~R 28 The "trialkylsilyl" in the silyl group is a group consisting of three water atoms. and the alkyl is a group in which each atom is independently substituted with an alkyl group. 2 1 ~R 28 The groups described as "alkyl" in the above can be cited. The most preferred alkyl is alkyl having 1 to 4 carbon atoms, specifically methyl, ethyl, Examples include propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl. can be done.

[0285] Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, trimethylsilyl, and trimethylsilyl. Tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl silyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyl propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl methyldiethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldi Ethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propyl Pyridilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyl Examples include butyldi-i-propylsilyl and t-butyldi-i-propylsilyl.

[0286] R 21 ~R28 The "tricycloalkylsilyl" in the above context refers to a silyl group with 3 and a group in which two hydrogen atoms are independently substituted with cycloalkyl. Kill is the R mentioned above. 21 ~R 28 The group described as "cycloalkyl" in The cycloalkyl to be substituted is preferably a cycloalkyl having 5 to 10 carbon atoms. Specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl Cyclonyl, 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, de Examples include decahydronaphthalenyl and decahydroazulenyl.

[0287] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclopentylsilyl, and tricyclopentylsilyl. Examples include cyclohexylsilyl.

[0288] Dialkylcycloalkylsilyl, which is substituted with two alkyls and one cycloalkyl, , alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyl groups Specific examples include groups selected from the specific alkyl and cycloalkyl groups listed above. An example is Cyril, which has been replaced by

[0289] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" Examples of such groups include amino groups in which two hydrogen atoms are replaced by aryl or heteroaryl groups. An amino in which two hydrogen atoms are replaced by aryl atoms is called a diaryl-substituted amino. is a heteroaryl-substituted amino, and two hydrogen atoms are is aryl and heteroaryl substituted amino; is arylheteroaryl substituted amino; The aryl and heteroaryl are the same as those described above. 21 ~R 28 "Aryl" in Reference may be made to groups described as "heteroaryl".

[0290] Specific examples of "substituted amino" include diphenylamino, dinaphthylamino, phenylamino, and the like. Nylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridyl Examples include mino.

[0291] R 21 ~R 28 The "halogens" in this document include fluorine, chlorine, bromine, and iodine. can be.

[0292] R 21 ~R 28 Some of the groups described as may be substituted as described above. In this case, the substituents are alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl or heteroaryl may be any of the above. TA R 21 ~R 28 "Alkyl," "cycloalkyl," "aryl," or "hexaalkyl" in Reference can be made to the group described as "heteroaryl."

[0293] Y as 'NR' 29 "R" 29 is hydrogen or an optionally substituted aryl The aryl is the same as R 21~R 28 The term "aryl" is used in The groups described above can be cited, and the substituents thereof include R 21 ~R 28 Substituents for The groups described above can be cited.

[0294] R 21 ~R 28 Adjacent groups among them are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heterocyclic ring. The case where no ring is formed is represented by the following formula (A-1): When a ring is formed, it is, for example, a group represented by any one of the following formulae (A-2) to (A-14): The group represented by any one of formulas (A-1) to (A-14) is exemplified. At least one hydrogen atom in the group is alkyl, cycloalkyl, aryl, or heteroaryl. alkyl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkenyl alkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, di Aryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino , halogen, hydroxy or cyano. Y and * in the formula are as defined above. is the same definition as [ka]

[0295] Examples of rings formed by bonding adjacent groups to each other include hydrocarbon rings such as cyclohexane. The aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 To These rings are the ring structures described in "aryl" and "heteroaryl" above. It is formed so as to be fused with one or two benzene rings in formula (A-1).

[0296] The group represented by formula (A) is, for example, any one of the above formulae (A-1) to (A-14). and the groups represented by the above formulae (A-1) to (A-5) and (A-12) to (A-6) are exemplified. A-14) is preferred, and a group represented by any one of the above formulas (A-1) to (A-4) is preferred. The groups represented by the above formula (A-1), formula (A-3) and formula (A-4) are more preferred. A group represented by any one of the following formulas is more preferred, and a group represented by the above formula (A-1) is particularly preferred. stomach.

[0297] The group represented by formula (A) is a group represented by formula (3-X1) or formula (3-X 2), the naphthalene ring in formula (3-X3), the single bond in formula (3-X3), Ar in formula (3-X3) 3 Combined with In addition, the substitution of at least one hydrogen atom in the compound represented by formula (3) is as described above. Among these bonding forms, the naphthyl group in formula (3-X1) or formula (3-X2) is The talene ring, the single bond in formula (3-X3), and Ar in formula (3-X3) 3 At least one of The form in which it is bonded to the hydroxyl group is preferred.

[0298] In addition, in the structure of the group represented by formula (A), Phthalene ring, single bond in formula (3-X3), Ar in formula (3-X3) 3 The position where In addition, in the structure of the group represented by formula (A), at least one The position at which the two hydrogen atoms are substituted may be any position in the structure of formula (A), for example, Either of the two benzene rings in the structure of formula (A) or R 21 ~R28 of Any of the rings formed by bonding adjacent groups to each other, or Y in the structure of formula (A) Te no ">NR 29 "R" 29 The bond can be at any position within the

[0299] Examples of the group represented by formula (A) include the following groups: This is the same definition as above. [ka] [ka]

[0300] In addition, all of the hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) are Alternatively, a portion of the hydrogen may be deuterium.

[0301] In addition, the anthracene-based compound may be an anthracene-based compound represented by the following formula (3-2-H): Compounds can be mentioned. [ka]

[0302] In formula (3-2-H), Ar c ', Ar 14 ', and Ar 15 ' each independently represents phenyl, biphenyl, aryl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl , chrysenyl, triphenylenyl, pyrenyl, or the above formula (A-1) to formula (A-14) and at least one hydrogen atom in these groups is a phenyl group. , biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzof fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or the above formula (A-1) to formula (A-2) A-14). Here, the hydrogen atoms of the methylene groups in fluorenyl and benzofluorenyl are all fluorinated. When substituted with phenyl, these phenyls may be bonded to each other via a single bond. Also, Ar c ', Ar 14 ', and Ar 15 on the anthracene ring to which ' is not attached The carbon atoms may be substituted with methyl or t-butyl in place of hydrogen. In addition, at least one hydrogen atom in the compound represented by formula (3-2-H) is a halogen atom or or cyano, and in the compound represented by formula (3-2-H), At least one hydrogen may be replaced with deuterium.

[0303] In formula (3-2-H), Ar c ', Ar 14 ', and Ar 15 ' are each independently , phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl or a group represented by any one of the above formulae (A-1) to (A-4). At least one hydrogen atom in these groups is phenyl, naphthyl, phenanthryl, substituted with fluorenyl or a group represented by any one of formulas (A-1) to (A-4) It's fine.

[0304] In the compound represented by formula (3-2-H), at least the 10-position of the anthracene ring of carbon (Ar c The hydrogen bonded to the carbon atom to which ' is bonded is the 9th position) is replaced with deuterium. That is, the compound represented by formula (3-2-H) is preferably a compound represented by the following formula (3-2- In the formula (3-2-Hb), D is preferably Deuterium, Ar c ', Ar 14 ', and Ar 15 ' is defined as in formula (3-2-H). In formula (3-2-Hb), D is at least one deuterium atom at this position. and any one or more other hydrogens in the formula (3-2-Hb) are simultaneously deuterium. It is also preferred that all hydrogen atoms in formula (3-2-Hb) are deuterium atoms. It's nice. [ka]

[0305] Specific examples of the anthracene-based compound include compounds of the following formulae (3-1) to (3-7) 2), Equations (3-79) to (3-142), and Equations (3-600) to (3-620) In the structural formula below, "Me" represents a methyl group, "D" represents deuterium, "tBu" refers to a t-butyl group.

[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] [ka]

[0310] [ka]

[0311] [ka]

[0312] [ka]

[0313] [ka]

[0314] [ka]

[0315] The anthracene compound represented by formula (3) has a reactive group at a desired position on the anthracene skeleton. a compound having X, Ar groups; 4 and a structure having a reactive group in a partial structure such as the structure of formula (A) Starting from the compound, Suzuki coupling, Negishi coupling, and other known coupling These reactive compounds can be produced by applying a ring-pulling reaction. Examples of the suitable organic compounds include halogens and boronic acids. The synthesis methods in paragraphs

[0089] to

[0175] of Publication No. 2014 / 141725 can be referred to.

[0316] <Fluorene-based compounds> The compound represented by the general formula (4) basically functions as a host. [ka]

[0317] In the above formula (4), R 1 From R 10 are each independently hydrogen, aryl, heteroaryl (the heteroaryl The alkyl may be bonded to the fluorene skeleton in the above formula (4) via a linking group), Diarylamino, diheteroarylamino, arylheteroarylamino, alkyl , cycloalkyl, alkenyl, alkoxy or aryloxy, At least one hydrogen atom is an aryl, heteroaryl, alkyl, or cycloalkyl. may be substituted, Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 Ma or R 9 and R 10 may each independently bond to form a fused ring or a spiro ring. At least one hydrogen atom in the formed ring is substituted with an aryl, heteroaryl (the heteroaryl the diarylamino group may be bonded to the formed ring via a linking group; No, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl may be substituted with aryl, alkenyl, alkoxy or aryloxy; At least one hydrogen atom in the formula (I) is aryl, heteroaryl, alkyl, or cycloalkyl. and At least one hydrogen atom in the compound represented by formula (4) is halogen, cyano or heavy It may be substituted with hydrogen.

[0318] The details of each group in the definition of the above formula (4) are as follows: The explanation in aromatic compounds can be cited.

[0319] R 1 From R 10 The alkenyl in the formula (I) is, for example, an alkenyl having 2 to 30 carbon atoms. Alkenyl having 2 to 20 carbon atoms is preferable, and alkenyl having 2 to 10 carbon atoms is more preferable. Alkenyl having 2 to 6 carbon atoms is preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butene, nyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl , 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl , or 5-hexenyl.

[0320] Specific examples of heteroaryl include the following formulae (4-Ar1), (4-Ar2), and (4-Ar3), (4-Ar4) or (4-Ar5) Monovalent groups represented by excluding atom(s) are also included. [ka] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen. the law of nature, At least one hydrogen atom in the structures of the above formulas (4-Ar1) to (4-Ar5) is a hydrogen atom. Phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl , propyl, or butyl.

[0321] These heteroaryls are linked to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton in formula (4) and the heteroaryl and may be bonded directly or via a linking group. Examples include phenylene, biphenylene, naphthylene, anthracenylene, methylene, and ethylene. -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc. It can be given.

[0322] Furthermore, R in equation (4) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 Ma or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10 are bonded to form a spiro ring R 1 From R 8 The fused ring formed by The ring fused to the Zene ring is an aliphatic ring or an aromatic ring. Preferably, it is an aromatic ring. The structure containing the benzene ring in formula (4) includes a naphthalene ring and a phenanthrene ring. Examples include: R 9 and R 10 The spiro ring formed by The spiro-bonded ring is an aliphatic ring or an aromatic ring, preferably an aromatic ring; An example is a fluorene ring.

[0323] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or are compounds represented by formula (4-3), and in general formula (4), R 1 and R 2 but A compound in which a benzene ring formed by bonding is condensed, in general formula (4), R 3 and R 4 Conclusion a compound in which a benzene ring formed by bonding is condensed, and in general formula (4), R 1 From R 8 Noi All of them are unbound compounds. [ka]

[0324] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of is given by the formula ( 4) The corresponding R 1 From R 10 is the same as Equation (4-1) and Equation (4-2). R in 11 From R 14 The definition of R in Eq. (4) 1 From R 10 is the same as

[0325] The compound represented by the general formula (4) is more preferably a compound represented by the following formula (4-1A), 2A) or (4-3A), and the compounds are represented by formula (4-1), formula (4 -2) or in formula (4-3), R 9 and R 10 are bonded to form a spiro-fluorene ring It is a compound that has been [ka]

[0326] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of In formula (4-1), formula (4-2) and formula (4-3), the corresponding R 2 From R 7 Same as In formula (4-1A) and formula (4-2A), R 11 From R 14 The definition of formula (4- 1) and R in formula (4-2) 11 From R 14 is the same as

[0327] In addition, all or part of the hydrogen atoms in the compound represented by formula (4) may be replaced by halogen, chlorine, or the like. It may be substituted with anhydrous or deuterium.

[0328] Specific examples of the fluorene-based compound include compounds represented by the following formulae (4-4) to (4-22): ) In the structural formula below, "Me" represents a methyl group. Shows. [ka]

[0329] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following general formula (5): It is a thing. [ka]

[0330] In the above formula (5), R 1 From R 16 are each independently hydrogen, aryl, heteroaryl (the heteroaryl The alkyl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group. (ii), diarylamino, diheteroarylamino, arylheteroarylamino, a alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy; At least one hydrogen atom in may be replaced by kill, Also, R 1 From R 16 adjacent groups may be bonded to each other to form a fused ring, At least one hydrogen atom in the formed ring is substituted with an aryl, heteroaryl (the heteroaryl the aryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, It may be substituted with alkenyl, alkoxy or aryloxy, At least one hydrogen is replaced by an aryl, heteroaryl, alkyl, or cycloalkyl. may be replaced, and At least one hydrogen atom in the compound represented by formula (5) is halogen, cyano or heavy It may be substituted with hydrogen.

[0331] The details of each group in the definition of the above formula (5) are as follows: The explanation in aromatic compounds can be cited.

[0332] The alkenyl in the definition of the above formula (5) is, for example, an alkenyl having 2 to 30 carbon atoms. Alkenyl having 2 to 20 carbon atoms is preferred, and alkenyl having 2 to 10 carbon atoms is also preferred. More preferably, alkenyl having 2 to 6 carbon atoms is further preferred, and alkenyl having 2 to 4 carbon atoms is further preferred. is particularly preferred. Preferred alkenyls include vinyl, 1-propenyl, 2-propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl thenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl hexenyl, or 5-hexenyl.

[0333] Specific examples of heteroaryl include those represented by the following formulae (5-Ar1), (5-Ar2), and (5-Ar3). (5-Ar3), (5-Ar4) or (5-Ar5) Monovalent groups represented by excluding atom(s) are also included. [ka] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen. the law of nature, At least one hydrogen atom in the structures of the above formulas (5-Ar1) to (5-Ar5) is a hydrogen atom. Phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl , propyl, or butyl.

[0334] These heteroaryls can be linked to the dibenzochrysene in the above formula (5) via a linking group. That is, the dibenzochrysene skeleton in formula (5) may be bonded to the above-mentioned skeleton. The heteroaryl may be directly bonded to the heteroaryl, or may be bonded to the heteroaryl via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methyl Stylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH Examples include 2O-.

[0335] The compound represented by general formula (5) is preferably R1 , R 4 , R 5 , R 8 , R 9 , R 1 2 , R 13 and R 16 is hydrogen. In this case, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are each independently hydrogen, phenyl, biphenyl, phenylyl, naphthyl, anthracenyl, phenanthrenyl, the above formula (5-Ar1), formula (5 -Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (The monovalent group having the structure is phenylene, biphenylene, naphthylene, Anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or Or, it is bonded to the dibenzochrysene skeleton in the above formula (5) via -OCH2CH2O-. Preferably, the alkyl group is methyl, ethyl, propyl, or butyl. .

[0336] The compound represented by general formula (5) is more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, the formula (5)R 3 , R 6 , R 11 and R 14At least one (preferably one or two) of and more preferably one) is a single bond, phenylene, biphenylene, naphthylene, anthylene, Racenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or The above formula (5-Ar1), formula (5-Ar2), formula (5-A r3), a monovalent group having a structure of formula (5-Ar4) or formula (5-Ar5), Other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl At least one hydrogen atom in these groups is phenyl, biphenyl, or butyl, substituted with phenyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl; It may be replaced.

[0337] Furthermore, R in equation (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 and A monovalent group having a structure represented by formula (5-Ar5) is selected from the above formula (5-Ar1). When selected, at least one hydrogen atom in the structure is R 1 From R 1 6 may be bonded to any one of the following to form a single bond.

[0338] Specific examples of the dibenzochrysene-based compound include compounds represented by the following formulas (5-1) to (5 -39) In addition, "tBu" in the following structural formula is This represents a t-butyl group. [ka]

[0339] [ka]

[0340] The above-mentioned materials for the light-emitting layer (host material and dopant material) may have reactive substituents. A polymer compound obtained by polymerizing a reactive compound substituted with , as a monomer, or a polymer compound obtained by polymerizing the polymer A molecular crosslinked body or a pendant polymer obtained by reacting a main chain polymer with the reactive compound. The compound or its pendant polymer crosslinked product can also be used as a material for the light-emitting layer. In this case, the reactive substituent is a polycyclic aromatic compound represented by formula (1). You can quote the explanation. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0341] <Example of polymer host material> [ka]

[0342] In formula (SPH-1), Each MU is independently a bivalent group represented by removing any two hydrogen atoms from an aromatic compound. The groups EC are each independently represented by removing any one hydrogen atom from an aromatic compound. It is a monovalent group, and two hydrogen atoms in MU are replaced with EC or MU, and k is 2 to 50,000. is an integer.

[0343] More specifically, Each MU independently represents an arylene, heteroarylene, or diarylylenearyl group. amino, diarylylenearylboryl, oxaborine-diyl, azaborine-diyl , EC independently represents hydrogen, aryl, heteroaryl, diarylamino, diaryl, heteroarylamino, arylheteroarylamino or aryloxy; At least one hydrogen in MU and EC may further be aryl, heteroaryl, optionally substituted with diarylamino, alkyl and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer of 20 to 50,000, and is preferably an integer of 100 to 50,000. It is more preferable that

[0344] At least one hydrogen atom in MU and EC in formula (SPH-1) is a hydrogen atom having 1 to 2 carbon atoms. 4 alkyl, cycloalkyl having 3 to 24 carbon atoms, substituted with halogen or deuterium Any -CH2- in the alkyl may be -O- or -Si(CH 3) may be substituted with 2-, and the alkyl may be directly substituted with EC in formula (SPH-1). Any -CH2- except the bonding -CH2- is replaced with an arylene having 6 to 24 carbon atoms. Any hydrogen in the alkyl may be substituted with fluorine.

[0345] For example, MU can be obtained by removing any two hydrogen atoms from any of the following compounds: Examples of such divalent groups include: [ka]

[0346] More specifically, divalent groups represented by any of the following structures are included: In this case, MU binds to another MU or EC at *.

[0347] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0348] Examples of EC include monovalent groups represented by any of the following structures: In these, EC binds to MU at *.

[0349] [ka] [ka]

[0350] The compound represented by formula (SPH-1) has the following structure in the molecule from the viewpoint of solubility and coating film-forming property. It is preferred that 10 to 100% of the total number of MUs (k) have alkyl groups having 1 to 24 carbon atoms. Of the total number of MUs in the molecule (k), 30-100% are alkyl (carbon number 1-18). It is more preferable that the total number of MU in the molecule (k) is 3 to 18. 50-100% of MU is alkyl with 1-12 carbon atoms (branched alkyl with 3-12 carbon atoms) On the other hand, from the viewpoint of in-plane orientation and charge transport, it is more preferable that the molecular 10-100% of the total number of MUs (k) in the Preferably, 30 to 100% of the total number of MUs (k) in the molecule are alkyl groups having 7 to 24 carbon atoms. It is more preferable that the alkyl group has a branched chain having 7 to 24 carbon atoms.

[0351] The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0352] <Electron injection layer and electron transport layer in organic electroluminescent device> The electron injection layer 107 efficiently injects electrons moving from the cathode 108 into the light-emitting layer 105. The electron transport layer 106 serves to inject electrons from the cathode 108 into the electron transport layer 106. The injected electrons or the electrons injected from the cathode 108 through the electron injection layer 107 are efficiently The electron transport layer 106 and the electron injection layer 107 serve to transport electrons to the light-emitting layer 105. , respectively, one or more kinds of electron transporting and injecting materials are laminated or mixed, or electron transporting and It is formed by a mixture of an injectable material and a polymeric binder.

[0353] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them further. It is desirable that the layer has high electron injection efficiency and efficiently transports the injected electrons. To achieve this, the electron affinity must be large, the electron mobility must be large, and the stability must be excellent. It is preferable that the material be one that is unlikely to generate impurities that act as traps during production and use. However, when considering the balance of hole and electron transport, the holes from the anode do not recombine and When the electron transport ability is the main function of the cathode, the electron transport ability is the main function of the cathode. Even if the electron transport capacity is not so high, the effect of improving the luminous efficiency is equivalent to that of a material with a high electron transport capacity. Therefore, the electron injection / transport layer in this embodiment can efficiently block the movement of holes. The functions of the layer may also be included.

[0354] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 is: Compounds that have been conventionally used as electron transport compounds in photoconductive materials, organic EL devices The compound is arbitrarily selected from known compounds used in the electron injection layer and electron transport layer. In the present invention, the electron transport material may be a compound represented by general formula (1) or formula (2): Polycyclic aromatic compounds represented by the following formula can be used.

[0355] Materials used in the electron transport layer or the electron injection layer include carbon, hydrogen, oxygen, sulfur, ketone, and the like. Aromatic or heteroaromatic rings composed of one or more atoms selected from among silicon and phosphorus Compounds consisting of a ring, pyrrole derivatives and their fused ring derivatives, and compounds having an electron-accepting nitrogen It is preferable that the compound contains at least one metal complex selected from the group consisting of naphthalene, ... Condensed ring aromatic derivatives such as phthalene and anthracene, 4,4'-bis(diphenylene) Styryl aromatic ring derivatives, represented by (thenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, Examples include phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having an electron-accepting nitrogen include hydroxyphenyloxazole complexes. Hydroxyazole complexes, azomethine complexes, tropolone metal complexes, flavonols, etc. These materials can be used alone. However, it is acceptable to use a mixture of different materials.

[0356] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, and ammonium salts. Thracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalene Imide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives , perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl )1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazoles Derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiazides Azole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives Conductors, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazoles perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzophenone derivatives, benzoquinoline derivative (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-s pyrobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole Derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzo Oxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridines, etc. Polypyridine derivatives, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-( 2,2':6',2"-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis (1-Naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxa ides, aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxides Examples of the styryl derivatives include styryl derivatives and bisstyryl derivatives.

[0357] Metal complexes having an electron-accepting nitrogen atom can also be used, for example, quinolinol-based Metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomes tin complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Examples include:

[0358] The above-mentioned materials may be used alone or in combination with other materials.

[0359] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives , pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives The compounds, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0360] <Borane derivatives> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and in detail This is disclosed in Japanese Patent Application Laid-Open No. 2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, X is optionally substituted arylene or optionally substituted aryl; and Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl or optionally substituted carbazolyl, and n is independently 0 to The integer is 3. Also, the substitution in the case of "optionally substituted" or "substituted" The group may be an aryl, heteroaryl, alkyl, or cycloalkyl. do.

[0361] Among the compounds represented by the above general formula (ETM-1), the compound represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, R is an alkyl or optionally substituted aryl; 21 and R 22 are independent of each other. and hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted at least one of silyl, an optionally substituted nitrogen-containing heterocycle, or cyano; X 1 represents an optionally substituted arylene having 20 or less carbon atoms, and each n is independently Each m is an integer of 0 to 3, and each m is independently an integer of 0 to 4. In the case of "optionally substituted" or "substituted", the substituents include aryl, heteroaryl, Examples of the alkyl include aryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, X is an alkyl group or an optionally substituted aryl group; 1 is an optionally substituted carbon atom number of 2 0 or less, and n is independently an integer of 0 to 3. Substituents in the "optionally substituted" or "substituted" cases include aryl, Examples include heteroaryl, alkyl, and cycloalkyl.

[0362] X 1 Specific examples of the compound include those represented by any one of the following formulas (X-1) to (X-9). In each structural formula, * indicates the bonding position. [ka] (In each formula, R aare each independently an alkyl group, a cycloalkyl group, or a substituted It is a phenyl group that may be

[0363] Specific examples of the borane derivative include the following compounds: [ka]

[0364] This borane derivative can be produced using known raw materials and known synthesis methods.

[0365] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably The compound is represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0366] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring phenylene ring), and n is an integer of 1 to 4.

[0367] In the above formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably alkyl having 3 to 4 carbon atoms), cycloalkyl having 6 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). do.

[0368] In the above formula (ETM-2-2), R 11 and R 12 are each independently hydrogen , alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms) and R 11 and R 12 may be bonded to form a ring.

[0369] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15): The pyridine-based substituents are each independently an alkyl group having 1 to 4 carbon atoms or a carbon atom. The pyridine-based substituent may be substituted with a cycloalkyl having 5 to 10 carbon atoms. In each formula, the φ is bonded to an anthracene ring or a fluorene ring via an ethylene group or a naphthylene group. In each structural formula, * indicates the bonding position.

[0370] [ka]

[0371] The pyridine-based substituent is any one of the above formulas (Py-1) to (Py-15). Among these, any one of the following formulas (Py-21) to (Py-44) is preferred. * in each structural formula indicates the bond position. [ka]

[0372] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium. In addition, the two "pyridine-based compounds" in the above formula (ETM-2-1) and formula (ETM-2-2) One of the "substituents" may be replaced by an aryl.

[0373] R 11 ~R 18The "alkyl" in the formula (I) may be either a straight chain or a branched chain. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (alkyl having 3 to 12 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms. Particularly preferred "alkyl" is a branched alkyl having 1 to 6 carbon atoms. 4 alkyl (branched alkyl having 3 to 4 carbon atoms).

[0374] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl- 2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methyl Hexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1- Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-di Methylheptyl, 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-heptyl Examples include tadecyl, n-octadecyl, and n-eicosyl. Also, 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-methyl ethylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl propyl, 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 are also included.

[0375] The alkyl having 1 to 4 carbon atoms that is substituted on the pyridine-based substituent is the same as the alkyl described above. It can be cited.

[0376] R 11 ~R 18 The "cycloalkyl" in the above formula includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl. cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, Examples include cyclooctyl and dimethylcyclohexyl.

[0377] The cycloalkyl having 5 to 10 carbon atoms that is substituted on the pyridine-based substituent includes the above-mentioned cycloalkyl. We can quote Lukil's explanation:

[0378] R 11 ~R 18 As for the "aryl" in the above, preferred aryl is an aryl having 6 to 30 carbon atoms. Aryl is more preferably an aryl having 6 to 18 carbon atoms, and even more preferably Preferably, it is an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms. do.

[0379] Specific examples of "aryl having 6 to 30 carbon atoms" include monocyclic aryl such as phenyl, condensed aryl, and the like. (1-,2-)naphthyl is a fused bicyclic aryl; acenaphthyl is a fused tricyclic aryl; ethylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9 -)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenalen triphenylene-(1-,2-)yl, pyrene-( 1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl Perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-) Examples include Iru.

[0380] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, and chlorine. phenyl, 1-naphthyl, and the like are preferred. Particularly preferred are phenyl, 1-naphthyl and phenanthryl. Examples include 2-naphthyl and 2-naphthyl.

[0381] R in the above formula (ETM-2-2) 11 and R 12 Even if they bond to form a ring, As a result, the five-membered ring of the fluorene skeleton is often cyclobutane, cyclopentane, cyclopentane, Pentene, cyclopentadiene, cyclohexane, fluorene or indene, etc. may be spi ro-bonded.

[0382] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0383] This pyridine derivative can be produced using known raw materials and known synthesis methods. [[ID=***]]

[0384] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), Specifically, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0385] In the above 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, when substituted, the substituents include aryl, heteroaryl, alkyl or cycloalkyl, etc. .

[0386] [[ID=5***]]This fluoranthene derivative's specific examples include, for example, the following compounds. <000441**]][[ID=***]]

Chemical formula

[0387] <BO-based derivative> The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4): It is a polymer of polycyclic aromatic compounds having multiple structures represented by the formula (ETM-4). [ka]

[0388] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diaryla amino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 The two aryls may be bonded via a single bond or a linking group) alkyl, alkoxy, aryloxy or substituted silyl, One hydrogen is replaced by aryl, heteroaryl, alkyl, or cycloalkyl. That's fine.

[0389] Also, R 1 ~R 11 Adjacent groups among these are bonded to form a ring together with the a, b or c ring. It may form an aryl ring or a heteroaryl ring, and at least one of the rings formed may be The other hydrogen is aryl, heteroaryl, diarylamino, diheteroarylamino , arylheteroarylamino, diarylboryl (two aryls are single bond or linked) (which may be bonded via a bonding group), alkyl, cycloalkyl, alkoxy, aryl may be substituted with oxy or substituted silyl, and at least one hydrogen atom in these may be may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0390] In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) It may be substituted with halogen or deuterium.

[0391] The substituents and ring formation forms in formula (ETM-4), and the structure of formula (ETM-4) The explanation of the multimers that can be formed by combining them is as follows: Descriptions of aromatic compounds and their polymers can be cited.

[0392] Specific examples of the BO derivative include the following compounds: [ka]

[0393] This BO derivative can be produced using known raw materials and known synthesis methods.

[0394] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1): do. [ka]

[0395] Ar are each independently a divalent benzene or naphthalene; R 1 ~R 4 teeth, Each independently represents hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or is an aryl having 6 to 20 carbon atoms.

[0396] Ar may be independently selected from divalent benzene or naphthalene. The two Ar groups may be different or the same, but the synthesis of anthracene derivatives From the viewpoint of easiness, it is preferable that they are the same. Ar is bonded to pyridine, and and a pyridine moiety" is formed, and this moiety is, for example, represented by the following formula (Py-1) to formula ( Py-12) is bonded to anthracene. * indicates the bond position.

[0397] [ka]

[0398] Among these groups, the group represented by any one of the above formulas (Py-1) to (Py-9) A group represented by any one of the above formulae (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" that bind to anthracene have the same structure. However, from the viewpoint of ease of synthesis of the anthracene derivative, it is preferable to use the same However, from the viewpoint of device characteristics, it is preferable that the two "Ar and pyrimidine" structures are the same. The structures of the "sin-containing moieties" may be the same or different.

[0399] R 1 ~R 4 The alkyl group having 1 to 6 carbon atoms can be either a straight chain or a branched chain. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl. butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl t-amyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, and methyl, ethyl, n -propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl Preferred are methyl, ethyl, or t-butyl.

[0400] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl Examples include cyclohexyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl. can be done.

[0401] R 1 ~R 4 For aryls having 6 to 20 carbon atoms, aryls having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Preferred.

[0402] Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryl such as phenyl, ( o-,m-,p-)tolyl, (2,3-,2,4-,2,5-,2,6-,3,4-,3 ,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p- ) cumenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, fused bicyclic aryl (1-,2-)naphthyl, a tricyclic aryl; terphenylyl (m-terphenyl); m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-Terphenyl-3'-yl, o-Terphenyl-4'-yl, p-Terphenyl-2 '-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terpheny o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terfenyl p-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, ... phenyl-4-yl), fused tricyclic aryl anthracene-(1-, 2-, 9-phenyl-4-yl), -)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2 -,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2- )yl, pyrene-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, Examples include perylene-(1-, 2-, 3-)yl, which is a fused pentacyclic aryl.

[0403] Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, and terphenylyl. or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2- naphthyl or m-terphenyl-5'-yl, more preferably phenyl, biphenyl It is preferably phenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0404] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2): do. [ka]

[0405] Ar 1 are each independently a single bond, a divalent benzene, a divalent naphthalene, an anthracene, fluorene or phenalene.

[0406] Ar 2 are each independently an aryl having 6 to 20 carbon atoms, and The same explanation as for "aryl having 6 to 20 carbon atoms" in -1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 16 carbon atoms is more preferred. Particularly preferred is an aryl having a carbon number of 10 or less. Specific examples include phenyl, biphenylyl, and naphthyl. , terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl. can be.

[0407] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, is a chloroalkyl or an aryl having 6 to 20 carbon atoms, and The following explanation can be cited:

[0408] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0409] These anthracene derivatives can be produced using known raw materials and known synthesis methods. Cut.

[0410] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0411] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and The same explanation as for "aryl having 6 to 20 carbon atoms" in -1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 16 carbon atoms is more preferred. Particularly preferred is an aryl having a carbon number of 10 or less. Specific examples include phenyl, biphenylyl, and naphthyl. , terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl. can be.

[0412] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), ), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably Preferably, it is an aryl having 6 to 30 carbon atoms, and two Ar 2 are bonded to form a ring Good too.

[0413] Ar 2 The "alkyl" in the above may be either a straight chain or a branched chain, for example, Examples include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. The preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (e.g., alkyl having 3 to 12 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (a branched alkyl). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms. alkyl (branched alkyl with 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl t-pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, Examples include 2-ethylbutyl, n-heptyl, and 1-methylhexyl.

[0414] Ar 2 The "cycloalkyl" in the above formula includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or or dimethylcyclohexyl.

[0415] Ar 2 As for the "aryl" in the above, preferred aryl is an aryl having 6 to 30 carbon atoms. The aryl is more preferably an aryl having 6 to 18 carbon atoms, and further preferably an aryl having 6 to 18 carbon atoms. It is an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms.

[0416] Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, and acenaphthyl. nyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, na Examples include phthalocenyl, perylenyl, and pentacenyl.

[0417] Two Ar 2 may be bonded to form a ring, resulting in a five-membered ring of the fluorene skeleton. These include cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, and cyclohexene. The oxane, fluorene, or indene may be spiro-linked.

[0418] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0419] This benzofluorene derivative can be produced using known raw materials and known synthesis methods. Cut.

[0420] <Phosphine oxide derivatives> 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. [ka] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, alkyl, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms; R 6 is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, silyl having 3 to 20 carbon atoms chloroalkyl, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, aryl having 5 carbon atoms Heteroaryl with up to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, or aryl with 6 to 20 carbon atoms It is oxy, R 7 and R 8 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. aryl or heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. is an integer. In the case where the group is substituted, the substituent may be an aryl, a heteroaryl, an alkyl, or the like. Or cycloalkyl, etc.

[0421] The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-2): Good too. [ka]

[0422] R 1 ~R 3 may be the same or different and are hydrogen, an alkyl group, a cycloalkyl group, Aralkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, alkoxy groups, alkoxy groups, alkylthio group, cycloalkylthio group, aryl ether group, aryl thioether group, aryl Aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl Among the fused rings formed between the substituted groups, amino groups, nitro groups, silyl groups, and adjacent substituents, are selected.

[0423] Ar 1 may be the same or different and are arylene or heteroarylene groups. Ar 2 may be the same or different and are aryl or heteroaryl groups However, Ar 1 and Ar 2 At least one of the groups has a substituent, or the adjacent groups A condensed ring is formed between the substituted and unsaturated groups. n is an integer of 0 to 3. When n is 0, the unsaturated group is When n is 3, R 1 does not exist.

[0424] Among these substituents, the alkyl group includes, for example, a methyl group, an ethyl group, a propyl group, a bromine group, and the like. refers to a saturated aliphatic hydrocarbon group, such as a methyl group, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and examples thereof include alkyl groups and aryl groups. , heterocyclic groups, etc., which are also included in the following description. The number of carbon atoms in the group is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost. It is an enclosure.

[0425] The cycloalkyl group includes, for example, cyclopropyl, cyclohexyl, norbornyl, It refers to saturated alicyclic hydrocarbon groups such as benzoyl, benzoyl, and adamantyl, which can be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20. be.

[0426] The aralkyl group is an aliphatic hydrocarbon group such as a benzyl group or a phenylethyl group. It indicates an aromatic hydrocarbon group mediated by a substituent, and both aliphatic and aromatic hydrocarbons are unsubstituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but it is usually 1. The range is ~20.

[0427] The alkenyl group is a double bonded group such as a vinyl group, an allyl group, or a butadienyl group. represents an unsaturated aliphatic hydrocarbon group containing a bond, which 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.

[0428] The cycloalkenyl group includes, for example, a cyclopentenyl group, a cyclopentadienyl group, and the like. It refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclohexene group or a cyclohexene group. It doesn't matter if it's a substitution or a replacement.

[0429] The alkynyl group is an unsaturated aliphatic group containing a triple bond, such as an acetylenyl group. represents a hydrocarbon group, which may be unsubstituted or substituted. The number is not particularly limited, but is usually in the range of 2 to 20.

[0430] The alkoxy group is an aliphatic carbonized group via an ether bond, such as a methoxy group. represents a hydrogen group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the group is not particularly limited, but is usually in the range of 1-20.

[0431] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced with a sulfur atom. It is a group that has been

[0432] A cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is sulfur. It is a group substituted with a yellow atom.

[0433] The aryl ether group is an aromatic group formed via an ether bond, such as a phenoxy group. 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.

[0434] In addition, an aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is It is a group substituted with a sulfur atom.

[0435] The aryl group includes, for example, a phenyl group, a naphthyl group, a biphenyl group, a phenanthrene group, and the like. The aryl group refers to an aromatic hydrocarbon group such as an alkyl group, a terphenyl group, or a pyrenyl group. The number of carbon atoms in the aryl group is not particularly limited, but is usually , ranging from 6 to 40.

[0436] The heterocyclic group includes, for example, a furanyl group, a thiophenyl group, an oxazolyl group, a pyridinyl group, and the like. a cyclic structural group having atoms other than carbon, such as a quinolinyl group, a carbazolyl group, The heterocyclic group may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited. , usually in the range of 2 to 30.

[0437] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0438] Aldehyde groups, carbonyl groups, and amino groups are used in aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic hydrocarbons. It may also include groups substituted with aromatic hydrocarbons, heterocycles, etc.

[0439] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic rings may be unsubstituted or substituted. It doesn't matter if it's broken.

[0440] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which is an unsubstituted silyl group. The number of carbon atoms in the silyl group is not particularly limited, but is usually 3. The silicon number is usually in the range of 1 to 20.

[0441] The fused ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , A r 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar2 Conjugates formed between etc. or It is a non-conjugated fused ring. Here, when n is 1, two R 1 Conjugate or non-conjugate condensation These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure. Alternatively, it may be condensed with another ring.

[0442] Specific examples of the phosphine oxide derivative include the following compounds: . [ka]

[0443] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods. can be done.

[0444] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and is preferably is a compound represented by the following formula (ETM-8-1). This is also described in Publication No. 1689. [ka]

[0445] Ar each independently represents an optionally substituted aryl or an optionally substituted n is an integer of 1 to 4, preferably an integer of 1 to 3, More preferably, it is 2 or 3.

[0446] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0447] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terf phenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be done.

[0448] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0449] Specific examples of heteroaryl include pyrrolyl, oxazolyl, and isoxazolyl. thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, Quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxy Sathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, Indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, Benzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphoro Monovalent radicals of oxide rings, monovalent radicals of dibenzophosphole oxide rings, furazanyl, thianthus Renyl, indolocarbazolyl, benzoindolocarbazolyl and benzobenzoindolocarbazolyl Examples include locarbazolyl.

[0450] In addition, at least one hydrogen atom in the above aryl and heteroaryl is substituted. Each of these may be substituted with, for example, the above-mentioned aryl or heteroaryl.

[0451] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0452] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0453] <Carbazole derivatives> The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or It is a polymer formed by multiple bonds such as single bonds. For details, see U.S. Patent Publication 2014 / 0197386 This is described in publication no. [ka]

[0454] Ar each independently represents an optionally substituted aryl or an optionally substituted Each n is independently an integer of 0 to 4, preferably It is an integer of 0 to 3, and more preferably 0 or 1.

[0455] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0456] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terf phenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be done.

[0457] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0458] Specific examples of heteroaryl include pyrrolyl, oxazolyl, and isoxazolyl. thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, Quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxy Sathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, Indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, Benzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphoro Monovalent radicals of oxide rings, monovalent radicals of dibenzophosphole oxide rings, furazanyl, thianthus Renyl, indolocarbazolyl, benzoindolocarbazolyl and benzobenzoindolocarbazolyl Examples include locarbazolyl.

[0459] In addition, at least one hydrogen atom in the above aryl and heteroaryl is substituted. Each of these may be substituted with, for example, the above-mentioned aryl or heteroaryl.

[0460] The carbazole derivative is a compound represented by the above formula (ETM-9) that is bonded by multiple bonds such as single bonds. In this case, in addition to the single bond, an aryl ring (preferably a polyvalent Benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phen The rings may be bonded together via a naphthylene ring, a naphthylene ring, a phenanthrene ring, or a triphenylene ring).

[0461] Specific examples of the carbazole derivative include the following compounds: [ka]

[0462] This carbazole derivative can be produced using known raw materials and known synthesis methods. .

[0463] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and is preferably The compound is represented by the following formula (ETM-10-1). This is described in Publication No. / 0156013. [ka]

[0464] Ar each independently represents an optionally substituted aryl or an optionally substituted n is an integer of 1 to 3, preferably 2 or 3.

[0465] The "aryl" in "optionally substituted aryl" is, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0466] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terf phenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be done.

[0467] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0468] Specific examples of heteroaryl include pyrrolyl, oxazolyl, and isoxazolyl. thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, Quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxy Sathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, Indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, Benzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphoro Monovalent radicals of oxide rings, monovalent radicals of dibenzophosphole oxide rings, furazanyl, thianthus Renyl, indolocarbazolyl, benzoindolocarbazolyl and benzobenzoindolocarbazolyl Examples include locarbazolyl.

[0469] In addition, at least one hydrogen atom in the above aryl and heteroaryl is substituted. Each of these may be substituted with, for example, the above-mentioned aryl or heteroaryl.

[0470] Specific examples of the triazine derivative include the following compounds: [ka]

[0471] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0472] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11): . [ka]

[0473] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring a phenylene ring), n is an integer of 1 to 4, and the "benzimidazole-based substituent" is The "pyriferous" in formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) It is a substituent in which the pyridyl group in the "pyridyl-based substituent" is replaced with a benzimidazole group, At least one hydrogen atom in the benzimidazole derivative may be replaced by deuterium. In the structural formula below, * indicates the bond position. [ka]

[0474] R in the benzimidazole group 11 is hydrogen, alkyl with 1 to 24 carbon atoms, carbon cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms, 2-1) and R in Equation (ETM-2-2) 11 The explanation can be cited.

[0475] φ is preferably an anthracene ring or a fluorene ring, and in this case, The structure can be explained by referring to the explanation of the above formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18 is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation in the above formula (ETM-2-1) or formula (ETM- 2-2) is explained as a form in which two pyridine-based substituents are bonded, but these are When replacing both pyridine-based substituents with benzimidazole-based substituents, It may be replaced by an azole-based substituent (i.e., n=2), or any one of the pyridine-based substituents. The substituent is replaced with a benzimidazole-based substituent and the other pyridine-based substituent is replaced with R 11 ~R 1 8 (i.e., n=1). Furthermore, for example, in the above formula (ETM-2-1), R in 11 ~R 18 At least one of the groups is replaced with a benzimidazole-based substituent to form a "pi Lysine-based substituents" R 11 ~R 18 may be replaced with .

[0476] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-( 10-Phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole , 2-(4-(10-(naphthalen-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]imide dazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2- Diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2- (yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imida 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)azole phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10- Di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H -benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracene) (2-phenyl-1H-benzo[d]imidazole) do. [ka]

[0477] This benzimidazole derivative can be produced using known raw materials and known synthesis methods. can.

[0478] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or the formula (ETM-12- 1). Details are described in International Publication No. 2006 / 021982. are. [ka]

[0479] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring phenylene ring), and n is an integer of 1 to 4.

[0480] R in each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably having 1 to 10 carbon atoms), 24 alkyl), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or is an aryl (preferably an aryl having 6 to 30 carbon atoms). 2-1) R 11 ~R 18 Either of these bonds to φ, an aryl ring.

[0481] At least one hydrogen atom in each phenanthroline derivative is replaced with a deuterium atom. good.

[0482] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the formula ( R in ETM-2 11 ~R 18 The explanation of the above can be cited. In addition to the above examples, the following structural formulas are also available. In the structural formulas below, R represents Independently, hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, The aryl group is 2-naphthyl, biphenylyl, or terphenylyl. * indicates the bond position. [ka]

[0483] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10 -phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Phosphorus, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6- Di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10- phenanthrolin-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl)benzene 1,3-bis(2-phenyl-1,10-furan-5-yl) phenanthroline-9-yl)benzene and compounds represented by the following structural formula: [ka]

[0484] This phenanthroline derivative can be produced using known raw materials and known synthesis methods. Cut.

[0485] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13): do. [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, It is Ga, Be or Zn, and n is an integer of 1 to 3.

[0486] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium and tris(8- Tris(4-methyl-8-quinolinolato)aluminum, Tris(4-methyl-8-quinolinolato)aluminum aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl Tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum tris(4,6-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, Bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl Bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum -8-quinolinolato)(3-methylphenolato)aluminum, bis(2-methyl- 8-quinolinolato)(4-methylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(2-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(3-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(4-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(2,3-dimethylphenolato)aluminum, bis(2-methyl -8-quinolinolato)(2,6-dimethylphenolato)aluminum, bis(2-methyl- bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolato)aluminum -methyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis (2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminium ammonium, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolato)a Aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenyl) Aluminum bis(2-methyl-8-quinolinolate)(2,4,6-trimethyl-8-quinolinolate) Methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4 ,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinol) bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate) (2-naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)( 2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinol) bis(2,4-dimethyl-8-quinolinyl)aluminum(triphenylphenolate) bis(2,4-dimethyl-8-)(4-phenylphenolate)aluminum Quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2,4-dimethylphenolato)aluminum (3,5-di-t-butylphenolate)aluminum, bis(methyl-8-quinolinolato) Bis(2-methyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl- 8-quinolinolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)aluminum Aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolato)aluminum , bis(2-methyl-4-ethyl-8-quinolinolato)aluminum-μ-oxo-bi Bis(2-methyl-4-ethyl-8-quinolinolato)aluminum, Bis(2-methyl- 4-Methoxy-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4 -Methoxy-8-quinolinolato)aluminum, bis(2-methyl-5-cyano-8- Quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quino Aluminum linoleate, bis(2-methyl-5-trifluoromethyl-8-quinolinol) bis(2-methyl-5-trifluoromethyl-8-methyl-2-oxo-2-methyl-5-trifluoromethyl-4-methyl-2-methyl-2-oxo ... Quinolinolate)aluminum, Bis(10-hydroxybenzo[h]quinoline)beryl Examples include Umu.

[0487] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods. Cut.

[0488] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2): do. [ka]

[0489] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, a helical ring, a fluorene ring, a benzofluorene ring, a phenalene ring, a phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4. The "zothiazole-based substituent" is a group represented by the above formula (ETM-2), formula (ETM-2-1) and formula (E The pyridyl group in the "pyridine-based substituent" in TM-2-2) is the following thiazole group or It is a substituent substituted for the benzothiazole group, and is used in thiazole derivatives and benzothiazo At least one hydrogen atom in the aryl derivative may be substituted with a deuterium atom. The * in the figure indicates the bond position. [ka]

[0490] φ is preferably an anthracene ring or a fluorene ring, and in this case, The structure can be explained by referring to the explanation of the above formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18 is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation in the above formula (ETM-2-1) or formula (ETM- 2-2) is explained as a form in which two pyridine-based substituents are bonded, but these are When replacing with an azole-based substituent (or a benzothiazole-based substituent), both pyridines Even if the thiazole-based substituent is replaced with a thiazole-based substituent (or a benzothiazole-based substituent), (i.e., n=2), any one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or or benzothiazole-based substituent) and the other pyridine-based substituent is replaced by R 11 ~R 18 (i.e., n=1). Furthermore, for example, in the above formula (ETM-2-1), KerR 11 ~R 18 At least one of the following is a thiazole-based substituent (or a benzothiazole-based substituent) Substituent) and replace "pyridine-based substituent" with R 11 ~R 18 may be replaced with .

[0491] These thiazole derivatives or benzothiazole derivatives are synthesized using known raw materials and known synthesis methods. It can be produced using the method.

[0492] The electron transport layer or the electron injection layer may further include a material for forming the electron transport layer or the electron injection layer. The reducing agent may contain a substance capable of reducing the feedstock. If so, various substances can be used, such as alkali metals, alkaline earth metals, and 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, Organic complexes of alkaline metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals. At least one selected from the following group can be suitably used.

[0493] Preferred reducing substances include Na (work function 2.36 eV) and K (work function 2.28 eV). , alkali metals such as Rb (2.16 eV) or Cs (1.95 eV), and Ca ( 2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV) Alkali earth metals are preferred, and substances with a work function of 2.9 eV or less are particularly preferred. Among them, the more preferred reducing substance is an alkali metal such as K, Rb or Cs, and even more preferred Preferably, Rb or Cs, and most preferably Cs. These alkali metals are In particular, it has a high reducing ability and is added in a relatively small amount to the material forming the electron transport layer or the electron injection layer. By adding the above, the luminance of the organic EL element can be improved and the life span can be extended. As a reducing substance having a valence of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred. Preferably, combinations containing Cs, such as Cs and Na, Cs and K, Cs and Rb, Alternatively, a combination of Cs, Na and K is preferred. By including Cs, the reduction ability is effectively improved. By adding it to the material that forms the electron transport layer or the electron injection layer, This will improve the luminance and extend the life of organic EL elements.

[0494] The above-mentioned electron injection layer material and electron transport layer material are substituted with reactive substituents. Polymer compounds obtained by polymerizing reactive compounds as monomers, or polymer crosslinked compounds thereof or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound. or its pendant polymer crosslinked product can also be used as an electronic layer material. In this case, the reactive substituent is the same as that of the polycyclic aromatic compound represented by formula (1). Can be used. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0495] <Cathode in organic electroluminescent device> The cathode 108 supplies electricity to the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 . It plays a role in injecting the offspring.

[0496] The material for forming the cathode 108 can be any material that can efficiently inject electrons into the organic layer. Although not particularly limited, the same material as that used to form the anode 102 can be used. However, tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold , platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium, etc. metals or their alloys (magnesium-silver alloy, magnesium-indium alloy, Aluminum-lithium alloys such as lithium fluoride / aluminum are preferred. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, and potassium Cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, trace amounts of lithium, cesium, or magnesium are added to the organic layer. A method is known in which highly stable electrodes are obtained by doping with other dopants. Examples include lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, other inorganic salts can also be used, including, but not limited to, the following:

[0497] In addition, platinum, gold, silver, copper, iron, tin, aluminum and indium are used to protect the electrodes. Metals such as titanium, or alloys using these metals, as well as silica, titania and silicon nitride Inorganic materials such as silicon dioxide, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is also based on resistance heating, electron Beam evaporation, sputtering, ion plating and coating, etc. There are no particular limitations as long as it can be done.

[0498] <Binders that may be used in each layer> The materials used in the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer are Each layer can be formed using a single material, but polyvinyl chloride, polycarbonate, etc. can be used as a polymer binder. Carbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate Polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide Polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl Solvent-soluble resins such as cellulose, vinyl acetate resin, ABS resin, and polyurethane resin, Phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester Dispersed in curable resins such as terephthalate resin, alkyd resin, epoxy resin, and silicone resin. It is also possible to use them together.

[0499] <Method for producing organic electroluminescent device> Each layer that makes up an organic EL element is made by depositing the material that makes up each layer using evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating or casting, It can be formed by forming a thin film using a coating method or the like. There are no particular limitations on the thickness of each layer formed, and it is set appropriately depending on the properties of the material. The film thickness is usually in the range of 2 nm to 5000 nm. When thinning is performed using a vapor deposition method, the vapor deposition conditions depend on the type of material. The deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Heating temperature +50 to +400℃, vacuum degree 10 -6 ~10 -3 Pa, deposition rate 0.01~ 50 nm / sec, substrate temperature -150 to +300°C, film thickness 2 nm to 5 μm. It is preferable that

[0500] When applying a DC voltage to the organic EL element obtained in this way, the anode is connected to + and the cathode is connected to When a voltage of 2 to 40 V is applied, the material becomes transparent or translucent. Light emission can be observed from the electrode side (anode or cathode, or both). The element also emits light when a pulse current or an AC current is applied. It can be optional.

[0501] Next, as an example of a method for fabricating an organic EL element, anode / hole injection layer / hole transport layer / hole The organic layer consists of an emitting layer made of a resist material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. The method for producing the EL element will be explained.

[0502] <Vapor deposition method> A thin film of anode material is formed on a suitable substrate by vapor deposition or the like to create an anode. A thin film of a hole injection layer and a hole transport layer is formed on the anode. The light-emitting layer is formed by co-evaporating a phototransport material and a thin film. An injection layer is formed, and then a thin film made of a cathode material is formed by vapor deposition or the like to form a cathode. By doing so, the desired organic EL element can be obtained. In this case, the fabrication order is reversed to form a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, and a cathode. It is also possible to form the hole injection layer and the anode in this order.

[0503] <Wet film formation method> The wet film formation method involves forming organic layers from liquid low molecular weight compounds that can form each organic layer of an organic EL element. The method is carried out by preparing a composition for use in the preparation of a solution containing the low molecular weight compound and using the solution. If there is no suitable organic solvent for this reaction, a reaction in which a reactive substituent is substituted on the low molecular weight compound is carried out. As a soluble compound, it is polymerized with other monomers or main chain polymers that have solubility functions. The organic layer-forming composition may be prepared from a molecular compound or the like.

[0504] The wet film formation method generally includes a coating step of coating a substrate with a composition for forming an organic layer and a coating step of applying a coating composition to the substrate. A coating film is formed by a drying process in which the solvent is removed from the organic layer-forming composition. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), The drying process further crosslinks the polymer to form a crosslinked polymer. The method using a spin coater is called the spin coating method, and the method using a slit coater is called the slit coating method. The method using the plate is gravure, offset, reverse offset, flexography Printing method, inkjet method using an inkjet printer, mist spray method This is called the spray method. There are several drying methods, such as air drying, heating, and vacuum drying. This may be carried out only once, or may be carried out multiple times using different methods or conditions. For example, different methods may be used in combination, such as calcination under reduced pressure.

[0505] The wet film formation method is a film formation method using a solution, for example, some printing methods (inkjet method ), spin coating or casting, coating, etc. Wet film formation methods include vacuum evaporation. Unlike conventional deposition methods, there is no need to use expensive vacuum deposition equipment, and films can be formed under atmospheric pressure. In addition, the wet film formation method allows for large-area and continuous production, which leads to reduced manufacturing costs. .

[0506] On the other hand, compared to the vacuum deposition method, the wet film formation method can be difficult to form layers. When a laminated film is produced using the film-forming method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer. This allows for controlled solubility compositions, underlying crosslinking and orthogonal solvents. However, even with these techniques, It can be difficult to apply the film using a wet deposition method.

[0507] Therefore, in general, only some layers are formed by wet deposition, and the rest are formed by vacuum deposition. A method of fabricating an L element is adopted.

[0508] For example, the procedure for producing an organic EL element by partially applying a wet film formation method is shown below. (Step 1) Forming the anode film by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a composition for forming an emitting layer containing a host material and a dopant material by a wet film formation method film (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum evaporation By going through this procedure, the anode / hole injection layer / hole transport layer / host material and dopant material An organic EL element comprising a light-emitting layer / electron transport layer / electron injection layer / cathode is obtained. Of course, there are ways to prevent the lower emitting layer from dissolving, and there are also ways to reverse the above procedure and start from the cathode side. By using a method for forming a film from a material for an electron transport layer or a material for an electron injection layer, a layer including the material for an electron transport layer and the material for an electron injection layer can be formed. The composition can be prepared as a coating composition and then formed into a film by a wet film-forming method.

[0509] <Other film formation methods> The composition for forming the organic layer can be formed into a film by laser thermal imaging (LITI). LITI is a method of heating and vapor-depositing a compound attached to a substrate with a laser. The organic layer-forming composition can be used for the material to be applied.

[0510] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be inserted as appropriate. Examples of the treatment process include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, Examples of such treatments include washing with an appropriate solvent and heating. A series of steps can also be mentioned.

[0511] The bank can be fabricated using photolithography. Positive resist materials and negative resist materials can be used as bank materials. In addition, inkjet printing, gravure offset printing, reverse offset printing, Printing methods that allow for patterns, such as printing and screen printing, can also be used. A permanent resist material may also be used.

[0512] Materials used for the bank include polysaccharides and their derivatives, hydroxyl-containing enzymes, and Homopolymers and copolymers of ethylenic monomers, biopolymers, polyacryloylation Compounds, polyester, polystyrene, polyimide, polyamideimide, polyetherimide Polysulfide, polysulfone, polyphenylene, polyphenyl ether, polyurethane Tan, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefin , cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (AB S), silicone resin, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, Polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetrafluoroethylene Fluorinated polymers such as fluoroethylene and polyhexafluoropropylene, fluoroolefins Examples of the copolymer include olefin-hydrocarbon olefin copolymers and fluorocarbon polymers. However, it is not limited to this.

[0513] <Composition for forming organic layer used in wet film formation method> The organic layer-forming composition is a low molecular weight compound capable of forming each organic layer of an organic EL element, or The low molecular weight compound is polymerized to form a polymer compound, which is then dissolved in an organic solvent. The composition for forming the light-emitting layer contains at least one polycyclic aromatic compound as a dopant material as a first component. An aromatic compound (or a polymeric compound thereof) and at least one host material as a second component. and a third component, at least one organic solvent. The first component functions as a dopant component in the resulting light-emitting layer, and the second component functions as a host component in the light-emitting layer. The third component functions as a solvent to dissolve the first and second components in the composition, and Sometimes the controlled evaporation rate of the third component itself provides a smooth, uniform surface profile.

[0514] <Organic solvents> The composition for forming the organic layer contains at least one organic solvent. By controlling the above, film forming properties, the presence or absence of coating defects, surface roughness, and smoothness can be controlled and improved. In addition, when forming a film using the inkjet method, the inkjet head It is possible to control the meniscus stability at the pinhole and control and improve the ejection performance. By controlling the drying speed of the film and the orientation of the derivative molecules, The electrical characteristics, light-emitting characteristics, efficiency, and life of an organic EL device having the obtained organic layer are improved. It is possible.

[0515] (1) Physical properties of organic solvents The boiling point of the at least one organic solvent is 130°C to 300°C, and preferably 140°C to 270°C. More preferably, the boiling point is 150°C to 250°C, and even more preferably 150°C to 250°C. In addition, when the boiling point is lower than 300°C, the coating film In view of defects, surface roughness, residual solvent and smoothness, organic solvents are preferred. From the viewpoint of jet ejection, film formation, smoothness and low residual solvent, two or more organic solvents are used. On the other hand, in some cases, taking into consideration transportability, etc., an organic layer structure is preferred. The composition may be a composition that has been solidified by removing the solvent from the composition.

[0516] Furthermore, the organic solvent is a good solvent (GS) and a poor solvent (PS) for at least one of the solutes. The boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP) of the poor solvent (PS) PS ) than A low, configuration is particularly preferred. By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, and the content of the composition The concentration of the solvent and the concentration of the poor solvent increase, promoting rapid film formation. A coating film with low surface roughness and high smoothness can be obtained.

[0517] Difference in solubility (S GS -S PS ) is preferably 1% or more, and more preferably 3% or more. The difference in boiling point (BP) is more preferably 5% or more, and even more preferably 5% or more. PS -BP G S ) is preferably 10°C or higher, more preferably 30°C or higher, and ° C. or higher is more preferable.

[0518] After film formation, the organic solvent is removed from the coating by a drying process using vacuum, reduced pressure, or heat. When heating is performed, from the viewpoint of improving the coating film forming property, it is necessary to heat the solution to a temperature above the glass transition temperature of at least one of the solutes. It is preferable to carry out the reaction at a temperature of Tg + 30°C or lower. It is preferable to heat the material at a temperature equal to or higher than the glass transition point (Tg) of at least one of the materials minus 30°C. Even if the heat temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Drying may be carried out multiple times at different temperatures, or multiple drying methods may be used in combination.

[0519] (2) Specific examples of organic solvents The organic solvent used in the composition for forming the organic layer includes alkylbenzene solvents, phenyl alkyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, Examples include monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, and nonanol. decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecane- 2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol Pineol, δ-terpineol, terpineol (mixture), ethylene glycol mono Methyl ether acetate, propylene glycol monomethyl ether acetate, diene ethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene 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 ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene , o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o- Xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluoro Toluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzyl Benzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole Nisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methyl Chilanisole, Phenetole, Benzodioxole, 4-Methylanisole, s-Butylanisole Benzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1 ,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile 4-Fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3 -Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene , 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5 -Dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene Benzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-toluni Tolyl, n-amylbenzene, veratrole, 1,2,3,4-tetrahydronaphthalene , ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene , 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxyethanol ene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene benzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-Methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)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. There is no limitation. The solvent may be used alone or in combination.

[0520] <Optional ingredients> The composition for forming an organic layer may contain optional components to the extent that the properties of the composition are not impaired. Optional components include a binder and a surfactant.

[0521] (1) Binder The composition for forming an organic layer may contain a binder. A film is formed, and the obtained film is bonded to a substrate. It serves to dissolve, disperse and bind the other ingredients.

[0522] Examples of binders used in the organic layer-forming composition include acrylic resins, polyesters, and the like. Ethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer Polymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, ionomer , chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene Polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate Nyl, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, Acrylonitrile-styrene copolymer (AS) resin, phenolic resin, epoxy resin, amine resins, urea resins, alkyd resins, polyurethanes, and the like, as well as the above resins and polymers. Copolymers, but are not limited to these.

[0523] The binder used in the organic layer-forming composition may be a single type or a mixture of multiple types. It may also be used as such.

[0524] (2) Surfactants The organic layer-forming composition is, for example, a composition for forming an organic layer that has a uniform film surface, a solvent affinity on the film surface, and the like. A surfactant may be contained to control the liquid repellency. They are classified into ionic and nonionic types based on their structure, and further into alkyl and nonionic types based on the structure of their hydrophobic groups. They are classified into silicon-based and fluorine-based. Also, due to the molecular structure, the molecular weight is relatively small. Simple monomolecular systems and large polymer systems with side chains and branches In addition, based on the composition, they are classified into a single system, a mixture of two or more surfactants and base materials, and The surfactants that can be used in the organic layer-forming composition are all Any type of surfactant can be used.

[0525] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Poly Flow No. 75, Polyflow No. 90, Polyflow No. 95 (product names, Kyoeisha Chemical Co., Ltd.) Disperbyk 161, Disperbyk 1 62, Disperbake 163, Disperbake 164, Disperbake 166, De Disperbake 170, Disperbake 180, Disperbake 181, Disper Bake 182, BYK300, BYK306, BYK310, BYK320, BYK33 0, BYK342, BYK344, BYK346 (trade name, BYK Japan Co., Ltd.) ), KP-341, KP-358, KP-368, KF-96-50CS, KF-5 0-100CS (product name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflo KH-40 (product name, manufactured by Seimi Chemical Co., Ltd.), Futergent 222F, Futerji Fent 251, FTX-218 (product name, manufactured by Neos Co., Ltd.), EFTOP EF-351 , EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-47 0, Megafuck F-471, Megafuck F-475, Megafuck R-08, Megaf F-477, Megafuck F-479, Megafuck F-553, Megafuck F -554 (trade name, manufactured by DIC Corporation), fluoroalkylbenzene sulfonate, fluoro Fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalcohol Ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate , diglycerin tetrakis (fluoroalkyl polyoxyethylene ether), fluoro Alkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxy Ethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, poly Oxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene Oleate, Polyoxyethylene Stearate, Polyoxyethylene Laurylamine, Sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, poly Oxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, Polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, arsenic alkylbenzene sulfonates and alkyldiphenyl ether disulfonates. This can be done.

[0526] The surfactant may be used alone or in combination of two or more.

[0527] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the organic layer-forming composition is determined based on the desired properties of each component in the organic layer-forming composition. The organic layer-forming composition has excellent solubility, storage stability and film-forming property, and a coating film obtained from the composition. The composition has good film quality, good ejection properties when using an ink jet method, and The organic EL device having the prepared organic layer has good electrical characteristics, light-emitting characteristics, efficiency, and lifespan. For example, in the case of a composition for forming a light-emitting layer, the first component is 0.0001% by weight to 2.0% by weight of the total weight of the composition, the second component is in the form of a light-emitting layer 0.0999% by weight to 8.0% by weight of the total weight of the composition, the third component is a light-emitting layer type The content is preferably 90.0% by weight to 99.9% by weight based on the total weight of the composition.

[0528] More preferably, the first component is 0.005% by weight based on the total weight of the composition for forming a light-emitting layer. and the second component is 0.095% by weight or more relative to the total weight of the composition for forming the light-emitting layer. 4.0% by weight, and the third component is 95.0% by weight to 99.0% by weight based on the total weight of the composition for forming the light-emitting layer. More preferably, the first component is 0.9% by weight based on the total weight of the composition for forming the light-emitting layer. , 0.05% by weight to 0.5% by weight, and the second component is 0. 0.25% by weight to 2.5% by weight, and the third component is 97. It is 0% by weight to 99.7% by weight.

[0529] The composition for forming the organic layer can be prepared by stirring, mixing, heating, cooling, dissolving, etc. the above-mentioned components in a known manner. After preparation, the mixture can be produced by appropriately selecting and performing the steps of filtration, degassing ( (also called degassing), ion exchange treatment, and inert gas replacement / filling treatment are selected appropriately. It is also possible.

[0530] The higher the viscosity of the composition for forming the organic layer, the better the film-forming properties and ink-jet printing properties. On the other hand, low viscosity makes it easier to form a thin film. From this, it is considered that the viscosity of the composition for forming an organic layer is 0.3 to 3 mJ at 25°C. The viscosity is preferably 1 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In this case, the viscosity is a value measured using a cone-plate type rotational viscometer. do.

[0531] The lower the surface tension of the composition for forming the organic layer, the better the film-forming properties and the more defect-free the coating film. On the other hand, the higher the value, the better the inkjet ejection properties. The viscosity of the composition for forming the organic layer is such that the surface tension at 25°C is 20 to 40 mN / m. In the present invention, the surface tension is preferably 20 to 30 mN / m. is a value measured using the hanging drop method.

[0532] <Crosslinkable polymer compound: Compound represented by general formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. An example of such a crosslinkable polymer compound is a compound represented by the following general formula (XLP-1). [ka] In formula (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in the above formula (SPH-1). and the compound represented by formula (XLP-1) has at least one crosslinkable substituent ( XLS), preferably containing a monovalent or divalent aromatic compound having a crosslinkable substituent. The amount is 0.1 to 80% by weight in the molecule.

[0533] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.5 to 50% by weight. is preferable, and 1 to 20% by weight is more preferable.

[0534] The crosslinkable substituent (XLS) is a group that can further crosslink the above-mentioned polymer compound. Although there is no particular limitation, substituents having the following structures are preferred: * in each structural formula indicates a bonding position. show. [ka]

[0535] L's each independently represent a single bond, -O-, -S-, >C=O, -OC(=O)-, Alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and Among the above substituents, the polyoxyalkylenes represented by the formula (XLS-1), the formula (XLS- 2), Formula (XLS-3), Formula (XLS-9), Formula (XLS-10) or Formula (XLS-1 A group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-7) is preferred, The group represented by 17) is more preferred.

[0536] Examples of divalent aromatic compounds having a crosslinkable substituent include compounds having the following partial structure: In the structural formula below, * indicates the bond position. [ka] [ka] [ka] [ka]

[0537] <Methods of producing polymer compounds and crosslinkable polymer compounds> Regarding the method for producing the polymer compound and the crosslinkable polymer compound, The compounds represented by (XLP-1) and (XLP-2) are used as examples. The compound of formula (I) can be synthesized by appropriately combining known production methods.

[0538] The solvents used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, and alcohols. Examples of solvents include dimethoxyethane, 2-(2-methoxy-2-methyl-2-methylpropane, 2-(2-methoxy-2-methylpropane), and ether-based solvents. 2-(ethoxy)ethane, 2-(2-ethoxyethoxy)ethane, etc.

[0539] The reaction may also be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a fourth phase may be added as necessary. A phase transfer catalyst such as a primary ammonium salt may be added.

[0540] When preparing the compound of formula (SPH-1) and the compound of formula (XLP-1), the compound is prepared in one step. Alternatively, the raw materials may be all placed in a reaction vessel and then reacted. The polymerization may be carried out by a batch polymerization method in which the reaction is started at the beginning, or by a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel. The polymerization may be carried out by a precipitation polymerization method in which the product precipitates as the reaction proceeds. For example, the compound represented by formula (SPH-1) The compound to be synthesized in one step is composed of a monomer unit (MU) and an end-capping unit. The target product is obtained by carrying out the reaction with ethylenediamine (EC) added to the reaction vessel. When synthesizing the compound represented by (SPH-1) in multiple steps, the monomer unit (MU) is targeted. After polymerization reaches the target molecular weight, an end cap unit (EC) is added and reacted. By adding different types of monomer units (MU) in multiple stages and carrying out the reaction, It is possible to create polymers with a concentration gradient of the monomer unit structure. After the precursor polymer is prepared, the target polymer can be obtained by post-reaction.

[0541] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). For example, as shown in synthetic schemes 1 to 3, Polymers with regular primary structures (synthetic scheme 1), polymers with regular primary structures (synthetic scheme 2) and 3) can be synthesized and can be used in appropriate combination depending on the target product. Furthermore, if a monomer unit having three or more polymerizable groups is used, it is possible to obtain a hyperpolymerizable polymer. It is possible to synthesize branched polymers and dendrimers.

[0542] [ka]

[0543] The monomer units that can be used in the present invention include those described in JP-A-2010-189630, International Publication No. 2012 / 086671, International Publication No. 2013 / 191088, International Publication No. 2002 / 045184, International Publication International Publication No. 2011 / 049241, International Publication No. 2013 / 146806, International Publication No. 2005 / 049546, International Publication No. 015 / 145871, JP 2010-215886, JP 2008-106241, JP 2010-215886, International Publication No. 2016 / 031639, JP 2011-174062 A, International Publication No. 2016 / 031639, International Publication It can be synthesized according to the methods described in WO 2016 / 031639 and WO 2002 / 045184. do.

[0544] For specific polymer synthesis procedures, see JP 2012-036388 A and WO 201 5 / 008851, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A , International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2016 / 031639, International Publication No. 2016 / 031639, International Publication Patent Publication No. 2016 / 125560, International Publication No. 2015 / 145871, International Publication No. 2011 / 049241, JP 2012-14 It can be synthesized according to the method described in JP-A-4722.

[0545] <Application examples of organic electroluminescent devices> The present invention also relates to a display device including an organic EL element or a lighting device including an organic EL element. It can also be applied to the following: A display device or a lighting device including an organic EL element is provided with the organic EL element according to this embodiment. It can be manufactured by a known method, for example by connecting it to a known driving device, and can be driven by DC, power The driving method can be appropriately selected from known driving methods such as pulse driving and AC driving.

[0546] The display device may be, for example, a panel display such as a color flat panel display. flexible displays such as flexible color organic electroluminescent (EL) displays Examples of such games include the game of the same name (for example, Japanese Patent Application Laid-Open No. 10-335066, Japanese Patent Application Laid-Open No. 2003-321546, (See, for example, Japanese Patent Application Laid-Open Publication No. 2004-281086.) In addition, the display method may be, for example, The matrix display and segment table are examples of this method. The indications may coexist in the same panel.

[0547] In a matrix, the pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern. A set of pixels is used to display characters and images. The shape and size of the pixels are determined by the application. For example, images and text displayed on computers, monitors, and televisions usually have a side length of 300 μm or more. The square pixels below are used, and in the case of large displays such as display panels, In the case of monochrome display, pixels of the same color are arranged. In the case of a color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta type and stripe type. The method may be either a line sequential driving method or an active matrix method. has the advantage of being simpler in structure, but when considering the operating characteristics, the active matrix There are cases where Ricks is superior, so it is necessary to use it depending on the purpose. .

[0548] In the segment type, patterns are formed to display predetermined information. For example, the time on a digital clock or thermometer is Time and temperature displays, operating status displays for audio equipment and induction cookers, and automobile panel displays Examples include:

[0549] Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (For example, Japanese Patent Application Laid-Open No. 2003-257621, Japanese Patent Application Laid-Open No. 2003-277741, Japanese Patent Application Laid-Open No. 2004-1 (See, for example, Patent Publication No. 19211.) Backlights are primarily used to improve the visibility of non-self-luminous display devices. It is used for the purpose of displaying images, and is used in LCD displays, clocks, audio equipment, automobile panels, display boards, and They are used in LCD displays, especially in personal computers, where thinning is an issue. Backlights for LCD screens have traditionally been made using fluorescent lamps and light guide plates, making them thinner. Considering the difficulty of this, the backlight using the light-emitting element according to this embodiment is thin and lightweight. Quantity is a feature.

[0550] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used in organic electroluminescent devices as well as in organic field effect transistors. It can be used to manufacture transistors or organic thin-film solar cells.

[0551] Organic field-effect transistors control current flow by generating an electric field through voltage input. A transistor that has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and a current flows between the source electrode and the drain electrode. A transistor that can control the current by arbitrarily blocking the flow of electrons (or holes). A field effect transistor is a simple transistor (bipolar transistor). It is easier to miniaturize than silicon dioxide, and is often used as an element that makes up integrated circuits.

[0552] The structure of an organic field effect transistor is usually formed using the polycyclic aromatic compound according to the present invention. A source electrode and a drain electrode are provided in contact with the organic semiconductor active layer formed thereon. Furthermore, a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. The element structure may be, for example, as follows: (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode / drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field-effect transistor configured in this way is an active matrix driving system. Pixel driving switching for liquid crystal displays and organic electroluminescence displays It can be used as a sensing element.

[0553] Organic thin-film solar cells are made up of an anode such as ITO, a hole transport layer, and a photovoltaic cell on a transparent substrate such as glass. It has a laminated structure of a photoelectric conversion layer, an electron transport layer, and a cathode. The photoelectric conversion layer has a p-type semiconductor on the anode side. The polycyclic aromatic compound according to the present invention has an n-type semiconductor layer on the cathode side. Depending on the physical properties of the material, it can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer. The polycyclic aromatic compound according to the present invention can be used in an organic thin-film solar cell. They can function as hole transport materials or electron transport materials. The layer may be provided with a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. For the organic thin-film solar cell, known materials used for organic thin-film solar cells may be appropriately selected. can be selected and used in combination. [Example]

[0554] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples. First, an example of the synthesis of a polycyclic aromatic compound will be described below.

[0555] Synthesis example (1) Compound (1-1): 5,9-bis(3,5-dimethylphenyl)-3,11-dimethyl -5,9-Dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]antho Synthesis of helicene-7-carbonitrile [ka]

[0556] Under a nitrogen atmosphere, 7-chloro-5,9-bis(3,5-dimethylphenyl)-3,11- Dimethyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de ]Anthracene (108 mg, 0.20 mmol), potassium hexacyanoferrate(II) (36.8 mg, 0.10 mmol), bis(di-t-butyl(4-dimethylaminophenyl) (AMPHOS)2PdCl2, 4. 25mg, 0.0060mmol), sodium carbonate (4.24mg, 0.040mmol) l) and a flask containing N,N-dimethylacetamide (DMAc, 2.0 ml) The mixture was heated to 140°C and stirred for 16 hours. After cooling to room temperature, the reaction solution was poured into water. The aqueous layer was extracted with toluene, and the resulting organic layer was washed with water and brine, and then with sulfuric acid anhydride. The solution was dried over magnesium, concentrated under reduced pressure, and the residue was purified by silica gel column (eluent Compound (1) was purified with hexane / dichloromethane (3 / 1 by volume). -1) was obtained as a yellow solid (64.7 mg, 61%). [ka]

[0557] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl3): δ=2.36(s,6H), 2.46(s ,12H), 6.36(s,2H), 6.62(s,2H), 6.92(s,4H), 7 .14(dd,J=1.2,8.0Hz,2H), 7.25(s,2H), 8.81(d ,J=8.0Hz,2H).

[0558] Synthesis example (2) Compound (1-4): 7-(t-butyl)-5,9-bis(3,5-dimethylphenyl) -5,9-Dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]antho Synthesis of helical-3,11-dicarbonitrile [ka]

[0559] Under a nitrogen atmosphere, 7-(t-butyl)-3,11-dichloro-5,9-bis(3,5-di Methylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2, 1-de]anthracene (90.2 mg, 0.15 mmol), hexacyanoferrate(II) Potassium phosphate (55.3 mg, 0.15 mmol), (AMPHOS)2PdCl2 (7. 28 mg, 0.0090 mmol), sodium carbonate (12.7 mg, 0.12 mmol ), and DMAc (1.5 ml) were added to the flask and heated to 130°C. The mixture was stirred for 20 hours. After the reaction solution was cooled to room temperature, it was poured into water, and the aqueous layer was extracted with toluene. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and the residue was purified using a silica gel short pass (eluent: toluene). Furthermore, the product was purified using a silica gel column (eluent: hexane / toluene = 1 / 2 (volume ratio)). Compound (1-4) was obtained as a yellow solid (48.7 mg, 54%). . [ka]

[0560] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl3): δ=1.04(s,9H), 2.46(s ,12H), 6.33(s,2H), 6.94(s,4H), 7.14(d,J=1.5 Hz,2H), 7.28(s,2H), 7.44(dd,J=1.4,7.8Hz,2H ), 8.85(d,J=7.8Hz,2H).

[0561] Synthesis example (3) Compound (1-357): 7-(t-butyl)-5,9-bis(3,5-dimethylphenyl) (Iron)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]a Synthesis of benzothracene-2,12-dicarbonitrile Compound (1-358): 7-(t-butyl)-5,9-bis(3,5-dimethylphenyl) (Iron)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]a Synthesis of benzothracene-2-carbonitrile [ka]

[0562] Under a nitrogen atmosphere, 7-(t-butyl)-2,12-dichloro-5,9-bis(3,5-di Methylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2, 1-de]anthracene and 7-(t-butyl)-12-chloro-5,9-bis(3, 5-dimethylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3 ,2,1-de]anthracene mixture (0.171 g, molar ratio = 1:2), hexathiocyanate Potassium ferrate(II) (77.6 mg, 0.21 mmol), bis(di-t-butyl( 4-Dimethylaminophenyl)phosphine)dichloropalladium(II)((AMPHO S)2PdCl2) (10.6 mg, 0.013 mmol), sodium carbonate (17.7 mg, 0.16 mmol), and N,N-dimethylacetamide (DMAc) (3.0 The flask containing 100 ml of HCl was heated to 130°C and stirred for 24 hours. The reaction solution was cooled to room temperature. After cooling, the mixture was poured into water, and the aqueous layer was extracted with toluene. The solution was washed with ethyl acetate, and then dried over anhydrous magnesium sulfate. After filtering, the solution was concentrated under reduced pressure. The residue was purified by silica gel column (eluent: hexane / toluene = 3 / 1 → 1 / 2, then hexane Compound (1-357) (26.9 ml) was obtained by purifying with ethanol / ethyl acetate (5 / 1). g, 47% yield) as an orange solid, to give compound (1-358) (19.6 mg, 18% yield) ) as an orange solid. [ka]

[0563] The structure of compound (1-357) was confirmed by NMR measurement. 1 H-NMR (400MHz, CDCl3): δ=1.03(s,9H), 2.45(s ,12H), 6.37(s,2H), 6.89(d,J=9.2Hz,2H), 6.95 (s,4H), 7.26(s,2H), 7.63(dd,J=1.8,9.2Hz,2H ), 9.02(d,J=1.8Hz,2H).

[0564] The structure of compound (1-358) was confirmed by NMR measurement. 1 H-NMR (400MHz, CDCl3): δ=1.03(s,9H), 2.43(s ,6H), 2.44(s,6H), 6.25(d,J=1.4Hz,1H), 6.34( d,J=1.4Hz,1H), 6.82(d,J=9.2Hz,1H), 6.89(d, J=8.2Hz,1H), 6.96(s,2H), 6.97(s,2H), 7.22(s ,1H), 7.24(s,1H), 7.30(t,J=7.8Hz,1H), 7.45- 7.49(m,1H), 7.57(dd,J=1.8,9.2Hz,1H), 8.80( d,J=7.8Hz,1H), 9.17(d,J=1.8Hz,1H).

[0565] Comparative synthesis example (1) Compound (C-1): N,N,5,9-tetraphenyl-5,9-dihydro-5,9-di Synthesis of aza-13b-boranaphtho[3,2,1-de]anthracen-7-amine [ka]

[0566] N 1 ,N 1 ,N 3 ,N 3 ,N 5 ,N 5 -Hexaphenyl-1,3,5-benzenethiazolinone amine (11.6 g, 20 mmol) and orthodichlorobenzene (ODCB, 120 m l) was added with boron tribromide (3.78 ml, 40 mmol) at room temperature under a nitrogen atmosphere. The mixture was heated and stirred at 170°C for 48 hours. Thereafter, the reaction solution was distilled off under reduced pressure at 60°C. The mixture was filtered through a Rolisil short-path column, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was washed to obtain the compound of formula (C-1) as a yellow solid (11.0 g, Yield 94%). [ka]

[0567] The structure of the compound obtained was confirmed by NMR measurement. 1 H-NMR (400MHz, CDCl3): δ=5.62 (brs, 2H), 6.71 (d,2H), 6.90-6.93(m,6H), 7.05-7.09(m,4H), 7 .20-7.27(m,6H), 7.33-7.38(m,4H), 7.44-7.48 (m,4H), 8.90(dd,2H). 13 C-NMR (101MHz, CDCl3): δ=98.4(2C), 116.8(2 C), 119.7(2C), 123.5(2C), 125.6(4C), 128.1(2 C), 128.8(4C), 130.2(4C), 130.4(2C), 130.7(4 C), 134.8(2C), 142.1(2C), 146.6(2C), 147.7(2 C), 147.8(2C), 151.1(4H).

[0568] Comparative synthesis example (2) Compound (C-2):N 7 ,N 7 ,N 13 ,N 13 ,5,9,11,15-octapheny 5,9,11,15-tetrahydro-5,9,11,15-tetraaza-19b,2 0b-diborazinenaphtho[3,2,1-de:1',2',3'-jk]pentacene-7, Synthesis of 13-diamines [ka]

[0569] Under a nitrogen atmosphere, 1,3-dibromobenzene (25.0 g, 106 mmol), aniline (20.3ml, 223mmol), Pd2(dba)3(971mg, 1.06mmol) l), BINAP (1.98g, 3.18mmol), NaOtBu (25.5g, 26 A flask containing 18 methylpropional (5 mmol) and toluene (400 ml) was heated to 110°C. The reaction mixture was cooled to room temperature and filtered through silica gel (eluent: toluene). The solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was dissolved in toluene, and then An appropriate amount was distilled off under reduced pressure, and hexane was added to reprecipitate the product. 1 ,N 3 -Diphenylben Zene-1,3-diamine was obtained as a white solid (16.5 g, 60% yield). [ka]

[0570] The structure of the compound obtained was confirmed by NMR spectroscopy. 1 H-NMR (400MHz, CDCl3): δ=5.63(s,2H), 6.60(d d,2H), 6.74(t,1H), 6.90(t,2H), 7.06(d,4H), 7 .12(t,1H), 7.24(dt,4H).

[0571] Under a nitrogen atmosphere, 1,3-dibromo-5-chlorobenzene (8.11 g, 30 mmol) , diphenylamine (10.1 g, 60 mmol), Pd2(dba)3 (550 mg, 0.6 mmol), SPhos (0.493 g, 1.2 mmol), NaOtBu (8. A flask containing 60 g (90 mmol) and toluene (300 ml) was heated to 80°C. The reaction mixture was cooled to room temperature and filtered through silica gel (eluent: toluene). The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was dissolved in toluene and The saturated solution was prepared by distilling off the chloroform under reduced pressure, and hexane was added to reprecipitate the chloroform. Lo-N 1 ,N 1 ,N 3 ,N 3-Tetraphenylbenzene-1,3-diamine was obtained as a white solid. The compound was obtained as follows (5.66 g, yield 43%). [ka]

[0572] The structure of the compound obtained was confirmed by NMR spectroscopy. 1 H-NMR (400MHz, CDCl3): δ=6.56(d,2H), 6.64(t ,1H), 7.00(t,4H), 7.05(d,8H), 7.21(dd,8H).

[0573] Under nitrogen atmosphere, N 1 ,N 3 -Diphenylbenzene-1,3-diamine (1.34g, 5 .1mmol), 5-chloro-N 1 ,N 1 ,N 3 ,N 3 -tetraphenylbenzene-1, 3-diamine (4.80 g, 11 mmol), Pd2(dba)3 (0.140 g, 0. 15mmol), tri-tert-butylphosphine (60.7mg, 0.30mmol ), NaOtBu (1.47 g, 15 mmol) and toluene (200 ml) The flask was heated to 110°C and stirred for 8 hours. The reaction mixture was cooled to room temperature and silica gel was added. The mixture was filtered using a filtration filter (eluent: toluene), and the solvent was evaporated under reduced pressure to obtain a crude product. The product was washed with hexane and then methanol to remove N 1 ,N 1 '-(1,3-phenylene N)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 -Pentaphenylbenzene-1,3,5-tri amine) was obtained as a white solid (4.80 g, 87% yield). [ka]

[0574] The structure of the compound obtained was confirmed by NMR spectroscopy. 1 H-NMR (400MHz, CDCl3): δ=6.38(d,4H), 6.41(t ,2H), 6.58(dd,2H), 6.70(t,1H), 6.88-6.90(m, 14H), 6.85(t,1H), 6.99(d,16H), 7.08-7.15(m, 20H).

[0575] N 1 ,N 1 '-(1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 -Penta phenylbenzene-1,3,5-triamine) (3.24 g, 3.0 mmol) and A flask containing 400 ml of dichlorobenzene was heated at room temperature under a nitrogen atmosphere. After the dropwise addition, the temperature was raised to 180°C. The mixture was stirred for 20 hours. After that, it was cooled to room temperature again and N-diisopropylethylamine ( The mixture was stirred until the heat generation subsided. The reaction solution was distilled off under reduced pressure to obtain a crude product. The crude product was washed with methanol and toluene in that order, and purified using a silica gel column (eluent: toluene). Recrystallized twice from o-dichlorobenzene, and then 1 × 10 -4 mmHg vacuum, 44 Purification by sublimation at 0°C gave the compound of formula (C-2) (1.17 g). [ka]

[0576] The structure of the compound obtained was confirmed by NMR spectroscopy. 1 H-NMR (400MHz, CDCl3): δ=5.72(s,2H), 5.74(s ,2H), 5.86(s,1H), 6.83(d,2H), 6.88-6.93(m,1 2H), 7.05(t,8H), 7.12-7.19(m,6H), 7.24-7.26 (m,4H), 7.05(d,4H), 7.12(dd,8H), 7.12-7.19( m,6H), 7.32(d,4H), 7.38(dd,2H), 7.42(t,2H), 7.46(dd,2H), 7.47(dd,4H), 9.30(d,2H), 10.5( s,1H). 13 C-NMR (101MHz, CDCl3):99.5(2C+2C), 103.4(1 C), 116.8(2C), 120.0(2C), 123.1(4C), 125.3(8C) ), 127.1(2C), 127.6(2C), 128.5(8C), 129.6(4C), 129.8(4C), 130.2(4C+2C), 130.3(4C), 135.0(2C) , 142.1(2C), 142.5(2C), 143.3(1C), 146.8(4C) , 147.9(2C+2C), 148.0(2C), 150.1(2C), 151.1(2 C).

[0577] By appropriately changing the raw material compounds, other compounds of the present invention can be obtained by the method similar to the synthesis example described above. The polycyclic aromatic compound can be synthesized.

[0578] Next, in order to explain the present invention in more detail, the organic EL device using the compound of the present invention will be described. Examples are given below, but the present invention is not limited to these.

[0579] <Evaluation of basic physical properties> Sample preparation When evaluating the absorption and emission properties (fluorescence and phosphorescence) of a compound, the compound is placed in a solvent. In some cases, the material is dissolved in a solvent and evaluated, and in other cases, it is evaluated in a thin film state. When evaluating, the compound alone is coated as a thin film depending on the mode of use of the compound in the organic EL device. The compound is dispersed in an appropriate matrix material to form a thin film for evaluation. There is a match.

[0580] As the matrix material, commercially available PMMA (polymethyl methacrylate) etc. is used. In this example, PMMA and the compound to be evaluated were dissolved in toluene, and then A thin film was formed on a transparent quartz substrate (10 mm × 10 mm) by spin coating. The samples were formed.

[0581] In addition, thin film samples in which the matrix material is the host compound are prepared as follows: A transparent support substrate (10 mm × 10 mm × 1.0 mm) made of quartz was prepared using a commercially available evaporation system. The substrate was fixed to a substrate holder (manufactured by Choshu Sangyo Co., Ltd.) and a molybdenum deposition Then, a molybdenum evaporation boat containing the dopant material was installed. 5×10 -4 The pressure was reduced to 100 Pa, and the evaporation boat containing the host compound and the dopant material were The deposition boat containing the host compound and dopant material is heated simultaneously to deposit the appropriate film thickness. A mixed thin film (sample) of the host compound and the dopant material was formed by co-evaporation in such a manner that the dopant material was mixed with the host compound. Here, the deposition rate was controlled according to the set weight ratio of the host compound and the dopant material.

[0582] Absorption and emission properties The absorption spectrum was measured using a UV-visible near-infrared spectrophotometer (Shimadzu Corporation, UV-26 00). The measurement of the fluorescence spectrum or phosphorescence spectrum was carried out using a spectrofluorometer. Measurement was carried out using a photometer (Hitachi High-Tech Corporation, F-7000).

[0583] For measuring the fluorescence spectrum, photoluminescence was measured at room temperature using an appropriate excitation wavelength. For the measurement of phosphorescence spectrum, the attached cooling unit was used. The sample was immersed in liquid nitrogen (temperature 77K) and the measurement was performed. Therefore, an optical chopper was used to adjust the delay time from irradiation of the excitation light to the start of measurement. The pull was excited with an appropriate excitation wavelength and photoluminescence was measured.

[0584] In addition, an absolute PL quantum yield measurement device (Hamamatsu Photonics, C9920-02G) was used. The fluorescence quantum yield (PLQY) was measured using the

[0585] Evaluation of fluorescence lifetime (delayed fluorescence) A fluorescence lifetime measurement device (Hamamatsu Photonics, C11367-01) was used at 300K. The fluorescence lifetime was measured at the maximum emission wavelength measured at an appropriate excitation wavelength. The emission components with a short and long fluorescent lifetime were observed. In the measurement of the fluorescence lifetime of the material at room temperature, the triplet component was thermally deactivated, resulting in the emission of phosphorescence. The slow emission component involving the triplet component is rarely observed. When a slow emission component is observed in This indicates that the energy is transferred to singlet state by the fluorescein fluorine-containing fluorescein and observed as delayed fluorescence.

[0586] Calculation of energy gap (Eg) From the long wavelength end A (nm) of the absorption spectrum obtained by the above method, Eg = 1240 / A was calculated as follows.

[0587] E(S,Sh), E(T,Sh), E(S,PT), E(T,PT) and ΔE(ST) Calculation of The singlet excited energy level E(S,Sh) is the shoulder shift on the short wavelength side of the peak of the fluorescence spectrum. From the wavelength BSh (nm) at the intersection of the tangent line passing through the inflection point and the baseline, E(S,Sh ) = 1240 / BSh. The triplet excitation energy level E(T,Sh) is At the intersection of the tangent line passing through the inflection point on the short wavelength side of the peak of the phosphorescence spectrum and the baseline Calculation was made from the wavelength CSh (nm) using the formula E(T,Sh) = 1240 / CSh. The singlet excited energy level E(S,PT) is the maximum emission wavelength BPT( The triplet excitation energy was calculated from the energy of the triplet excitation energy (S, PT) = 1240 / BPT. The level E(T,PT) is the maximum emission wavelength CPT (nm) of the phosphorescence spectrum to E(T,PT ) = 1240 / CPT.

[0588] ΔE(ST) is the energy difference between E(S,PT) and E(T,PT) ΔE(ST) = It is defined as E(S,PT)-E(T,PT). Also, ΔE(ST) is, for example, y organic electroluminescent material realizing 100% conversion from electricity to light", H. Kaji, H. Suzuki, T. Fukushima, K. Shizu, K. Katsuaki, S. Kubo,T. Komino, H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, C. Adachi, Nat. Commun. 2015 , 6, 8476.

[0589] Evaluation of the basic physical properties of compound (1-1) [ka]

[0590] [Absorption characteristics] The absorption spectrum of compound (1-1) was measured using a 2.0 × 10 -5 mol / L toluene solution As a result, the maximum absorption wavelength in the visible light region was 450 nm (Fig. 2).

[0591] [Light Emitting Properties] The fluorescence spectrum was measured using 2.0 × 10 -5 mol / L toluene solution The solution was prepared and excited at room temperature with an excitation wavelength of 405 nm. The peak length was 458 nm and the half-width was 17 nm (Figure 3). is particularly suitable for blue dopant materials with narrow half-bandwidth.

[0592] Evaluation of the basic physical properties of compounds (1-4) [ka]

[0593] [Absorption characteristics] The absorption spectrum of compound (1-4) was measured at 2.0 × 10 -5 mol / L toluene solution As a result, the maximum absorption wavelength in the visible light region was 492 nm (Fig. 4).

[0594] [Light Emitting Properties] The fluorescence spectrum was measured using 2.0 × 10 -5 mol / L toluene solution The solution was prepared and excited at room temperature with an excitation wavelength of 405 nm. The length was 511 nm and the half-width was 31 nm (Fig. 5).

[0595] <Evaluation of vapor-deposited organic EL elements> Organic EL devices according to Examples 1-1 to 1-4 and Comparative Example 1-1 were fabricated. 0 cd / m 2 The voltage (V) and external quantum efficiency (%), which are light-emitting characteristics, were measured.

[0596] The quantum efficiency of a light-emitting element is divided into internal quantum efficiency and external quantum efficiency. The internal quantum efficiency is External energy injected into the light-emitting layer of a light-emitting device as electrons (or holes) is converted purely into photons. On the other hand, the external quantum efficiency indicates the rate at which these photons are converted outside the light-emitting element. The amount of photons emitted from the light-emitting layer is calculated based on the amount of photons emitted from the light-emitting element. Because the light is absorbed or reflected inside the , the external quantum efficiency is lower than the internal quantum efficiency.

[0597] The external quantum efficiency was measured using the Advantest R6 voltage / current generator. 144, the brightness of the element is 1000 cd / m 2 The device emits light by applying a voltage that Using a TOPCON SR-3AR spectroradiometer, the The spectral radiance in the visible light region was measured from the light source. The spectral radiance value of each wavelength component is divided by the wavelength energy and multiplied by π. Next, the number of photons is integrated over the entire wavelength range observed, and the number of photons emitted from the element is calculated. The applied current value divided by the elementary charge is the total number of photons injected into the element. The photon number is calculated by dividing the total number of photons emitted from the element by the number of carriers injected into the element. is the external quantum efficiency.

[0598] Materials of each layer in the organic EL devices according to Examples 1-1 to 1-4 and Comparative Example 1-1 The fee structure is shown in Table 1A below. [Table 1A]

[0599] In Table 1A, "HI" stands for N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -bis(9-fu (phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diazo amine, and "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, and "HT-1" is N-([1,1'-biphenyl]-4-isopropyl) 9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl) phenyl)-9H-fluoren-2-amine, and "HT-2" is N,N-bis(4- (Dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terf phenyl]-4-amine, and "BH-1" is 2-(10-phenylanthracene-9- ET-1 is 4,6,8,10-tetramethylbenzofuran. tetraphenyl[1,4]benzoxaborinino[2,3,4-kl]phenoxaborinine "ET-2" is 3,3'-((2-phenylanthracene-9,10-diyl)biphenyl) It is bis(4,1-phenylene)bis(4-methylpyridine). The chemical structure is shown in.

[0600] [ka]

[0601] <Example 1-1> ITO was deposited to a thickness of 180 nm by sputtering and polished to a thickness of 150 nm. Transparent support for a 26mm x 28mm x 0.7mm glass substrate (manufactured by Optoscience Co., Ltd.) This transparent support substrate was placed on a substrate holder of a commercially available deposition device (manufactured by Showa Vacuum Co., Ltd.). Fixed, HI, HAT-CN, HT-1, HT-2, BH-1, compound (1-1), ET Molybdenum evaporation boats containing ET-1 and ET-2, respectively, Liq, LiF, and An aluminum nitride evaporation boat containing aluminum was attached.

[0602] The following layers were formed in order on the ITO film of the transparent support substrate. -4 Pa The pressure was reduced to 100 psi, and HI was first heated and evaporated to a thickness of 40 nm. N was heated and evaporated to a thickness of 5 nm, and then HT-1 was heated to a thickness of 45 nm. Next, HT-2 was hea...

Claims

1. A polycyclic aromatic compound represented by the following general formula (1), or a compound having a structure represented by the following general formula (1): A polymer of polycyclic aromatic compounds with multiple structures. 【Chemical 1】 (In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. 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 R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl. 、 X １ and X ２ are each independently >O, >N—R, >S or >Se, R in the above N-R is an optionally substituted aryl, an optionally substituted heteroaryl, aryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the above >N-R is a linking group or a single bond, and at least one of the rings A, B and C is may also be combined with one another, Ring B and ring C may be bonded via a linking group or a single bond; At least one hydrogen atom in the compound or structure represented by formula (1) is replaced by a fluorine atom, a chlorine atom, or a fluorine atom. , optionally substituted with bromine, iodine or deuterium; In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused with at least one cycloalkane. Preferably, at least one hydrogen atom in the cycloalkane may be substituted, and the At least one —CH in the cycloalkane ２ - may be replaced by -O-, and, At least one hydrogen atom in the compound or structure represented by formula (1) is replaced with a cyano atom. It is being done.)

2. In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings is replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or is an unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, Substituted or unsubstituted diarylboryl (two aryls are connected via a single bond or a linking group) may be bonded to each other), substituted or unsubstituted alkyl, substituted or unsubstituted cyclohexane substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy or or substituted silyl, and these rings may be substituted with Y １ , X １ and X ２ from The above formula (1) has a 5-membered ring or a 6-membered ring that shares a bond with the central fused bicyclic structure. 、 Y １ is B, P, P═O, P═S, Al, Ga, As, Si—R or Ge—R R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl. 、 X １ and X ２ are each independently >O, >N—R, >S or >Se, R in N—R is an aryl optionally substituted with alkyl or cycloalkyl, Heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or is cycloalkyl, and R in the above >N—R is —O—, —S—, —C(—R) ２ - or may be bonded to at least one of the ring A, ring B and ring C via a single bond; -C (-R) ２ R in - is hydrogen, alkyl or cycloalkyl; The B and C rings are >O, >N—R, >Si(—R) ２ , >C(-R) ２ , > S, > S and the >N—R and >Si(—R) groups may be bonded via a single bond or a single bond. ２ R each independently represents an optionally substituted aryl, an optionally substituted heteroaryl, alkyl, optionally substituted alkyl, or optionally substituted cycloalkyl. and the above >C(-R) ２ R is hydrogen, optionally substituted aryl, substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl is alkyl, At least one hydrogen atom in the compound or structure represented by formula (1) is replaced by a fluorine atom, a chlorine atom, or a fluorine atom. , optionally substituted with bromine, iodine or deuterium; In the case of a polymer, a dimer or trimer having two or three structures represented by general formula (1) and In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused with at least one cycloalkane. Preferably, at least one hydrogen atom in the cycloalkane may be substituted, and the At least one —CH in the cycloalkane ２ - may be replaced by -O-, and, At least one hydrogen atom in the compound or structure represented by formula (1) is replaced with a cyano atom. It is being The polycyclic aromatic compound or a multimer thereof according to claim 1.

3. The polycyclic aromatic compound or a multimer thereof according to claim 1, which is represented by the following general formula (2): 。 【Chemistry 2】 (In the above formula (2), In the ring a, ring b, and ring c, any "-C(-R)=" (where R is the group represented by the formula (2) R １ ~R １１ ) may be replaced with "-N=", and any "-C(-R) =C(-R)-" (where R is R in formula (2) １ ~R １１ ) is "-N(-R)- "," "-O-," or "-S-," and the "-N(-R)-" R is aryl, alkyl or cycloalkyl; R １ ~R １１ are each independently hydrogen, aryl, heteroaryl, diaryla amino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkenyl alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tri Cycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkyl and aryl, aryl, aryl, heteroaryl, or aryl. It may be substituted with alkyl or cycloalkyl, and R １ ~R １１ Next to my house Adjacent groups are bonded to form an aryl or heteroaryl ring together with ring a, ring b or ring c. At least one hydrogen atom in the formed ring may be selected from the group consisting of aryl, heterocyclic, Diaryl, diarylamino, diheteroarylamino, arylheteroarylamino and diarylboryl (two aryls may be bonded via a single bond or a linking group). alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, Trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or may be substituted with alkyldicycloalkylsilyl, and at least One hydrogen is replaced by an aryl, heteroaryl, alkyl, or cycloalkyl. It's okay to be there, Y １ is B, P, P═O, P═S, Al, Ga, As, Si—R or Ge—R R in the Si—R and Ge—R is an aryl having 6 to 12 carbon atoms, an aryl having 1 to 6 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms; X １ and X ２ are each independently >O, >N—R, >S or >Se, R in N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and R is -O-, -S-, -C(-R) ２ or the ring a, ring b and ring c are bonded together by a single bond. and may be bonded to at least one of the -C(-R) ２ -R is an alkyl group having 1 to 6 carbon atoms alkyl or cycloalkyl having 3 to 14 carbon atoms, R on ring b ８ and R on ring c ７ are >O, >N-R, >Si(-R) ２ , >C(-R) ２ , >S, >Se or may be bonded via a single bond, and the >N—R and >Si ( -R) ２ R is independently aryl, heteroaryl, alkyl, or cycloalkyl. alkyl, which may be substituted with alkyl, and the above >C(—R) ２ The R in , hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, may be substituted with alkyl; At least one hydrogen atom in the compound represented by formula (2) is replaced by a fluorine, chlorine, bromine, or iodine atom. may be substituted with iodine or deuterium, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed ring, aryl and heteroaryl has 3 to 24 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, or , and may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. Preferably, at least one —CH in the cycloalkane ２ - is replaced by -O- It is also possible to At least one hydrogen atom in the compound represented by formula (2) is substituted with cyano. ）

4. In the above formula (2), In the ring a, ring b, and ring c, any "-C(-R)=" (where R is the group represented by the formula (2) R １ ~R １１ ) may be replaced with "-N=", and any "-C(-R) =C(-R)-" (where R is R in formula (2) １ ~R １１ ) is "-N(-R)- "," "-O-," or "-S-," and the "-N(-R)-" R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a silyl having 5 to 10 carbon atoms. is a chloroalkyl; R １ ~R １１ are each independently hydrogen, an aryl having 6 to 30 carbon atoms, an aryl having 2 to 3 carbon atoms, heteroaryl, diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms) , diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and two aryls alkyl having 1 to 24 carbon atoms; is a cycloalkyl having 3 to 24 carbon atoms, and R １ ~R １１ Adjacent groups among are bonded to form an aryl ring having 9 to 16 carbon atoms or an aryl ring having 6 to 1 5 heteroaryl rings, and at least one water atom in the ring formed The element is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a silyl having 3 to 16 carbon atoms. optionally substituted with chloroalkyl; Y １ is B, P, P=O, P=S or Si-R, and R in the Si-R is the number of carbon atoms aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; can be, X １ and X ２ are each independently >O, >N-R or >S, and the >N- R in R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a is cycloalkyl, R on ring b ８ and R on ring c ７ are >O, >N-R, >C(-R) ２ or via >S R in the >N-R may be bonded to each other, and each R is independently an aryl group having 6 to 30 carbon atoms. C2-C30 heteroaryl, C1-C24 alkyl or C3-C24 alkyl These are cycloalkyl groups, which may be substituted with alkyl groups having 1 to 24 carbon atoms. Above>C(-R) ２ R is hydrogen, aryl having 6 to 30 carbon atoms, heterocyclic group having 2 to 30 carbon atoms. aryl, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms; These may be substituted with alkyl having 1 to 24 carbon atoms, At least one hydrogen atom in the compound represented by formula (2) is replaced by a fluorine, chlorine, bromine, or iodine atom. may be substituted with iodine or deuterium, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed rings, aryl and heteroaryl has 3 to 16 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2) is substituted with a cyano atom. The polycyclic aromatic compound or a multimer thereof according to claim 3.

5. In the above formula (2), In the ring a, ring b, and ring c, any "-C(-R)=" (where R is the group represented by the formula (2) R １ ~R １１ ) may be replaced with "-N=", and any "-C(-R) =C(-R)-" (where R is R in formula (2) １ ~R １１ ) is "-N(-R)- "," "-O-," or "-S-," and the "-N(-R)-" R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a silyl having 5 to 10 carbon atoms. is a chloroalkyl; R １ ~R １１ are each independently hydrogen, an aryl having 6 to 16 carbon atoms, an aryl having 2 to 2 carbon atoms, heteroaryl, diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms) , diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls alkyl having 1 to 12 carbon atoms; is a cycloalkyl having 3 to 16 carbon atoms, Y １ is B, P, P=O or P=S, X １ and X ２ are each independently >O or >N—R, and R in the >N—R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. is alkyl, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed rings, aryl and heteroaryl has 3 to 16 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2) is substituted with a cyano atom. The polycyclic aromatic compound or a multimer thereof according to claim 3.

6. In the above formula (2), In the ring a, ring b, and ring c, any "-C(-R)=" (where R is the group represented by the formula (2) R １ ~R １１ ) may be replaced with "-N=", and any "-C(-R) =C(-R)-" (where R is R in formula (2) １ ~R １１ ) is "-N(-R)- "," "-O-," or "-S-," and the "-N(-R)-" R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a silyl having 5 to 10 carbon atoms. is a chloroalkyl; R １ ~R １１ are each independently hydrogen, an aryl having 6 to 16 carbon atoms, a diaryla boryl (where aryl is aryl with 6 to 10 carbon atoms), diarylboryl (where aryl is The aryl is an aryl having 6 to 10 carbon atoms, and two aryls are bonded via a single bond or a linking group. alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms; and Y １ is B, X １ and X ２ are both >N-R, or X １ is > N-R and X ２ Ha>O and R in the >N—R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, In the compound or structure represented by formula (2), the ring a, the ring b, the ring c, At least one of the formed rings, aryl and heteroaryl has 3 to 16 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2) is substituted with a cyano atom. The polycyclic aromatic compound or a multimer thereof according to claim 3.

7. R of the >N-R is a cyano-substituted aryl or heteroaryl.

7. The polycyclic aromatic compound or a multimer thereof according to any one of 1 to 6.

8. The polycyclic aromatic ring according to claim 7, wherein R in the >N-R is a cyano-substituted phenyl. Aromatic compounds or polymers thereof.

9. Cyano-substituted alkyl or cycloalkyl groups, cyano-substituted alkoxy groups group, a cyano-substituted diarylamino group, a cyano-substituted diarylboryl group (two wherein the aryl may be bonded via a single bond or a linking group), a cyano-substituted aryl substituted with a benzocarbazolyl group or a cyano-substituted benzocarbazolyl group.

9. The polycyclic aromatic compound or a multimer thereof according to any one of 8.

10. The polycyclic aromatic ring of claim 9, which is substituted with a cyano-substituted diarylamino group. Aromatic compounds or polymers thereof.

11. The polycyclic aromatic ring according to claim 10, which is substituted with a cyano-substituted diphenylamino group. Aromatic compounds or polymers thereof.

12. The polycyclic aromatic compound according to claim 1, which is represented by any one of the following structural formulas: 【Chemistry 3】 (In the above structural formulas, "Me" stands for methyl group, "tBu" stands for t-butyl group, and "CN" stands for cyano. (represents a group)

13. The polycyclic aromatic compound or its multimer according to any one of claims 1 to 12, Group-substituted, reactive compounds.

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

15. A pendant-type polymer obtained by substituting the reactive compound according to claim 13 into a main chain polymer. or a pendant polymer crosslinked by further crosslinking the pendant polymer compound. Bridge body.

16. A composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 12. Materials for organic devices.

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

18. A material for organic devices, comprising the polymer compound or crosslinked polymer according to claim 14. Fee.

19. A polymer comprising the pendant polymer compound or the pendant polymer crosslinked product according to claim 15. A material for organic devices.

20. The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or the like. The organic device according to any one of claims 16 to 19, which is a material for an organic thin-film solar cell. Material for vices.

21. The organic device according to claim 20, wherein the material for an organic electroluminescent device is a material for a light-emitting layer. Materials for use.

22. A polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 12 and an organic solvent. An ink composition comprising:

23. An ink composition comprising the reactive compound according to claim 13 and an organic solvent.

24. An ink composition comprising a main chain polymer, the reactive compound according to claim 13, and an organic solvent. Finished product.

25. An ink comprising the polymer compound or crosslinked polymer according to claim 14 and an organic solvent. composition.

26. The pendant polymer compound or pendant polymer crosslinked product according to claim 15; and an organic solvent.

27. A pair of electrodes consisting of an anode and a cathode, and a gas supply device according to any one of claims 1 to 12, which is disposed between the pair of electrodes. The polycyclic aromatic compound or a multimer thereof according to any one of claims 13 to 15, a compound, a polymer compound or a crosslinked polymer according to claim 14, or claim 15 2. An organic compound containing a pendant polymer compound or a pendant polymer crosslinked body according to claim 1. and a layer.

28. 28. The organic electroluminescent device according to claim 27, wherein the organic layer is a light-emitting layer.

29. The light-emitting layer contains a host and the polycyclic aromatic compound or a large amount thereof as a dopant. compounds, reactive compounds, polymer compounds, crosslinked polymers, pendant polymer compounds or pendant polymer compounds 29. The organic electroluminescent device according to claim 28, comprising a dant-type crosslinked polymer.

30. The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

30. The organic electroluminescent device according to claim 29, which is a compound.

31. At least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridinium derivative, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorane derivatives, thylene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, Triazine derivatives, benzimidazole derivatives, phenanthroline derivatives and quinolinol The present invention relates to a compound according to any one of claims 27 to 30, which contains at least one selected from the group consisting of fluorine-based metal complexes. The organic electroluminescent device according to any one of the preceding claims.

32. At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, Alkali earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkali metals Alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth Halides of alkali metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and dilute 32. The method according to claim 31, further comprising the step of: The organic electroluminescent device according to claim 1.

33. At least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer The two layers are polymer compounds made by polymerizing low molecular weight compounds that can form each layer as monomers. Or, a polymer crosslinked body obtained by further crosslinking the polymer compound, or a polymer crosslinked body formed by forming each layer A pendant polymer compound obtained by reacting a low molecular weight compound with a main chain polymer, or The present invention also provides a crosslinked pendant polymer obtained by further crosslinking the pendant polymer compound. Item 33. An organic electroluminescent device according to any one of Items 27 to 32.

34. A display device or lighting device comprising the organic electroluminescent device according to any one of claims 27 to 33. Device.

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