Polycyclic aromatic compounds

Abstract

A polycyclic aromatic compound composed of a partial structure represented by formula (1A) and at least two partial structures each represented by formula (1B) (wherein the rings A to C independently represent an aryl ring which may be substituted; RXD represents an aryl group which may be substituted, in which the broken line is -X- and thereby RXD is bonded to the ring A; the partial structure represented by formula (1B) is bonded, at a position indicated by *, to a ring-constituting atom in one ring selected from the group consisting of the rings A and B, RXD, and the ring C and RXE in another partial structure represented by formula (1B); the broken line in the ring C is -X- and thereby the ring C is bonded to the above-selected ring; RXE represents an aryl group which may be substituted, in which the broken line is -X- or a single bond and thereby RXE is bonded to the above-selected ring or X; Y represents B; and X represents >N-R (wherein R represents an aryl group which may be substituted) ) is useful as a material for an organic device, particularly a light-emitting layer material for forming a light-emitting layer for an organic electroluminescent element.

Claims

1. Polycyclic aromatic compounds represented by formula (III-10); 【Chemistry 1】 During the ceremony, Y is independently B, P, P=O or P=S, X is independently >C(-R)2, >N-R, >O, >S, or >Se, where R in >N-R is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl. Z is independent of each other, -C(-R Ｚ ) = or -N = and two adjacent Zs are -C(-R Ｚ ) ２ -, -Si(-R Ｚ ) ２ -, -N(-R Ｚ ) -, -O-, -S- or -Se- may be substituted, R Ｚ Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted silyl, or -L-Ak. L is >N-R, >O or >S, where R in >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and R in >N-R is >O, >S, >Si(-R) ２ and may be bonded to Ak by a single bond, and R in >Si(-R) ２ is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms Ak is hydrogen, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group, and the alkyl and cycloalkyl groups contain at least one -CH group. ２ The - may be substituted with -O- and -S-. At least one selected from the group consisting of aryl rings and heteroaryl rings in the polycyclic aromatic compound may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted with an alkyl group having 1 to 5 carbon atoms, and at least one -CH in the cycloalkane ２ The - can also be substituted with -O-. In formula (III-10), the substituents that may be substituted, or are substituted or unsubstituted, are aryl, heteroaryl, alkyl, or cycloalkyl. At least one hydrogen atom in the polycyclic aromatic compound may be substituted with deuterium, cyano, or halogen.

2. The polycyclic aromatic compound according to claim 1, wherein Y is all B.

3. R Ｚ The polycyclic aromatic compound according to claim 1 or 2, wherein each is independently hydrogen, a phenyl molecule which may be substituted with an alkyl group having 1 to 5 carbon atoms, a diphenylamino molecule which may be substituted with an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms.

4. A polycyclic aromatic compound according to claim 1, represented by one of the following formulas. 【Chemistry 2】 In the formula, Me represents methyl and tBu represents t-butyl.

5. A polycyclic aromatic compound represented by formula (III-12); 【Transformation 3】 During the ceremony, Y is independently B, P, P=O or P=S, Each X is independently >C(-R)2, >N-R, >O, >S, or >Se, wherein at least one X is >O or >S, and R in >N-R is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl. Z is independent of each other, -C(-R Ｚ ) = or -N = and two adjacent Zs are -C(-R Ｚ ) ２ -, -Si(-R Ｚ ) ２ -, -N(-R Ｚ ) -, -O-, -S- or -Se- may be substituted, R Ｚ Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted silyl, or -L-Ak. L is >N-R, >O, or >S, where R in >N-R is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >N-R is >O, >S, or >Si(-R). ２ Alternatively, it may be bonded to Ak by a single bond, and the above >Si(-R) ２ R is hydrogen, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. Ak is hydrogen, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group, and the alkyl and cycloalkyl groups contain at least one -CH group. ２ The - may be substituted with -O- and -S-. At least one selected from the group consisting of aryl rings and heteroaryl rings in the polycyclic aromatic compound may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted with an alkyl group having 1 to 5 carbon atoms, and at least one -CH in the cycloalkane ２ The - can also be substituted with -O-. In formula (III-12), the substituents that may be substituted, or are substituted or unsubstituted, are aryl, heteroaryl, alkyl, or cycloalkyl. At least one hydrogen atom in the polycyclic aromatic compound may be substituted with deuterium, cyano, or halogen.

6. The polycyclic aromatic compound according to claim 5, wherein Y is B in all cases.

7. R Ｚ The polycyclic aromatic compound according to claim 5 or 6, wherein each is independently hydrogen, a phenyl molecule which may be substituted with an alkyl group having 1 to 5 carbon atoms, a diphenylamino molecule which may be substituted with an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms.

8. A polycyclic aromatic compound according to claim 5, represented by any of the following formulas; 【Chemistry 4】 In the formula, Me represents methyl.

9. A material for an organic device containing a polycyclic aromatic compound according to any one of claims 1 to 8.

10. The organic device material according to claim 9, wherein the organic device material is a material for an organic electroluminescent device, a material for an organic field-effect transistor, or a material for an organic thin-film solar cell.

11. The material for an organic device according to claim 10, wherein the material for the organic electroluminescent element is a material for the light-emitting layer.

12. A composition for an organic electroluminescent element, comprising a polycyclic aromatic compound according to any one of claims 1 to 8 and an organic solvent.

13. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing a polycyclic aromatic compound according to any one of claims 1 to 8.

14. The organic electroluminescent element according to claim 13, wherein the organic layer is a light-emitting layer.

15. The organic electroluminescent element according to claim 14, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

16. The organic electroluminescent element according to claim 15, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

17. The organic electroluminescent element according to any one of claims 14 to 16, further comprising at least one electron transport layer and electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes.

18. The organic electroluminescent device according to claim 17, wherein at least one layer of the electron transport layer and electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes.

19. An organic field light-emitting element according to any one of claims 14 to 18, wherein at least one of the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a polymer crosslinked material obtained by further crosslinking the polymer compound, or a pendant-type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant-type polymer crosslinked material obtained by further crosslinking the pendant-type polymer compound.

20. A display device or lighting device comprising an organic electroluminescent element according to any one of claims 13 to 19.

21. A wavelength conversion material containing a polycyclic aromatic compound according to any one of claims 1 to 8.

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