Phenoxasiline based compounds for electronic application

15:

• An organic electronic device comprising at least one compound of the formula (I)
• in which
• R1, R2, R3, R4, R5, R6 and R7
• are each independently hydrogen, C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of C1-C20-alkoxy, C6-C30-aryloxy, C1-C20-alkylthio, C6-C30-arylthio, SiR10R11R12, halogen radicals, halogenated C1-C20-alkyl radicals, carbonyl (—CO(R1′)), carbonylthio (—C═O(SR10)), carbonyloxy (—C═O(OR10)), oxycarbonyl (—OC═O(R10)), thiocarbonyl (—SC═O(R10)), amino (—NR10R11), OH, pseudohalogen radicals, amido (—C═O(NR10)), —NR10C═O(R11), phosphonate (—P(O)(OR10)2), phosphate (—OP(O)(OR10)2), phosphine (—PR10R11), phosphine oxide (—P(O)(R10)2), sulfate (—OS(O)2OR10), sulfoxide (—S(O)R10), sulfonate (—S(O)2OR10), sulfonyl (—S(O)2R10), sulfonamide (—S(O)2NR10R11), NO2, boronic esters (—OB(OR10)2), imino (—C═NR10R11), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroximes and borazines;
• or two adjacent R1, R2, R3, R4, R5, R6 or R7 radicals, in each case together with the carbon atoms to which they are bonded, form a ring having a total of 3 to 12 atoms, where the ring may be saturated or mono- or polyunsaturated and, as well as carbon atoms, may have one or more heteroatoms selected from N, O and P, where the ring may be unsubstituted or mono- or polysubstituted and/or may be fused to further 3- to 12-membered rings;
• R8 and R9
• are each independently C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl or heteroaryl having 5 to 30 ring atoms;
• R10, R11, R12
• are each independently C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms, —O—Si(C1-C20-alkyl)3, —O—Si(C6-C30-aryl)3, C1-C20-alkoxy or C6-C30-aryloxy;
• or two adjacent R10 and R11, R10 and R12 or R11 and R12 radicals, together with the atom to which they are bonded, form a ring having a total of 3 to 12 atoms, where the ring may be saturated or mono- or polyunsaturated and, as well as the atom to which the R10, R11 or R12 radicals are bonded, may have exclusively carbon atoms or one or more further heteroatoms selected from N, O and P, where the ring may be unsubstituted or mono- or polysubstituted and/or may be fused to further 3- to 12-membered rings;
• Y is C2-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of C1-C20-alkoxy, C6-C30-araloxy, C1-C20-alkylthio, C6-C30-arylthio, SiR10R11R12, halogen radicals, halogenated C1-C20-alkyl radicals, carbonyl (—CO(R10)), carbonylthio (—C═O(SR10)), carbonyloxy (—C═O(OR10)), oxycarbonyl (—OC═O(R10)), thiocarbonyl (—SC═O(R10)), amino (—NR10R11), OH, pseudohalogen radicals, amido (—C═O(NR10)), —NR10C═O(R11), phosphonate (—P(O)(OR10)2), phosphate (—OP(O)(OR10)2), phosphine (—PR10R11), phosphine oxide (—P(O)(R11)2), sulfate (—OS(O2)OR10), sulfoxide (—S(O)R10), sulfonate (—S(O)2OR10), sulfonyl (—S(O)2R10), sulfonamide (—S(O)2NR10R11), NO2, boronic esters (—OB(OR10)2), imino (—C═NR10R11), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroximes and electronic device according to claim 15, wherein borazines.

16:

• The organic electronic device according to claim 15, wherein
• Y is heteroaryl having 5 to 30 ring atoms selected from the group consisting of pyrrolyl, furanyl, thienyl, and benzoanellated ring systems thereof and
• R10, R11 and R12
• are each independently C6-C30-aryl.

17:

• The organic electronic device according to claim 15, wherein
• Y is selected from the group consisting of
• and SiPh3,
• wherein
• X is NR10, O or S,
• R10 is C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms, —O—Si(C1-C20-alkyl)3, —O—Si(C6-C30-aryl)3, C1-C20-alkoxy or C6-C30-aryloxy;
• and
• R13 is H or phenoxasilinyl of formula (I′),
• wherein the substituents Y′, R2′, R3′, R4′, R5′, R7′, R8′ and R9′ have independently the same meanings as the substituents Y, R1, R2, R3, R4, R5, R7, R8 and R9 in the phenoxasiline derivatives of formula (I),
• and the symbol ˜ means that there is a binding site at the position marked with ˜.

21:

• The organic electronic device according to claim 15, wherein
• R1, R2, R3, R4, R5, and R7 are hydrogen, and
• R6 is heteroaryl having 5 to 30 ring atoms selected from the group consisting of pyrrolyl, furanyl, thienyl, and benzoanellated ring systems thereof or SiR10R11R12;
• and
• R10, R11 and R12
• are each independently C6-C30-aryl.

22:

• The organic electronic device according to claim 20, wherein the compound of formula (I) is selected from the compounds of formulae (Ia), (Ib), (Ic) and (Id)
• wherein
• Y and R6
• are each independently heteroaryl having 5 to 30 ring atoms selected from the group consisting of pyrrolyl, furanyl, thienyl, and benzoanellated ring systems thereof or SiR10R11R12;
• R3 and R4
• are each independently C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms, methoxy, phenyloxy, halogenated C1-C4-alkyl, or halogen;
• R10, R11 and R12
• are each independently C6-C30-aryl;
• and
• R8 and R9
• are each independently C6-C30-aryl or heteroaryl having 5 to 30 ring atoms.

26:

• A light-emitting layer, electron/exciton transport layer, hole/exciton transport layer, hole/exciton blocking layer, electron/exciton blocking layer, hole/exciton injection layer and/or electron/exciton injection layer comprising at least one compound of formula (I)
• in which
• R1, R2, R3, R4, R5, R6 and R7
• are each independently hydrogen, C1-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of C1-C20-alkoxy, C6-C30-aryloxy, C1-C20-alkylthio, C6-C30-arylthio, SiR10R11R12, halogen radicals, halogenated C1-C20-alkyl radicals, carbonyl (—CO(R10)), carbonylthio (—C═O(SR10)), carbonyloxy (—C═O(OR10)), oxycarbonyl (—OC═O(R10)), thiocarbonyl (—SC═O(R10)), amino (—NR10R11), OH, pseudohalogen radicals, amido (—C═O(NR10)), —NR10C═O(R11), phosphonate (—P(O)(OR10), phosphate (—OP(O)(OR10)2), phosphine (—PR10R11), phosphine oxide (—P(O)(R10)2), sulfate (—OS(O)2OR10), sulfoxide (—S(O)R10), sulfonate (—S(O)2OR10), sulfonyl (—S(O)2R10), sulfonamide (—S(O)2NR10R11), NO2, boronic esters (—OB(OR10)2), imino (—C═NR10R11), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroximes and borazines;
• or two adjacent R1, R2, R3, R4, R5, R6 or R7 radicals, in each case together with the carbon atoms to which they are bonded, form a ring having a total of 3 to 12 atoms, where the ring may be saturated or mono- or polyunsaturated and, as well as carbon atoms, may have one or more heteroatoms selected from N, O and P, where the ring may be unsubstituted or mono- or polysubstituted and/or may be fused to further 3- to 12-membered rings;
• R8 and R9
• are each independently C1-C20-alkyl, C1-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl or heteroaryl having 5 to 30 ring atoms;
• R10, R11, R12
• are each independently C1-C20-alkyl, C1-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms, —O—Si(C1-C20-alkyl)3, —O—Si(C6-C30-aryl)3, C1-C20-alkoxy or C6-C30-aryloxy;
• or two adjacent R10 and R11, R10 and R12 or R11 and R12 radicals, together with the atom to which they are bonded, form a ring having a total of 3 to 12 atoms, where the ring may be saturated or mono- or polyunsaturated and, as well as the atom to which the R10, R11 or R12 radicals are bonded, may have exclusively carbon atoms or one or more further heteroatoms selected from N, O and P, where the ring may be unsubstituted or mono- or polysubstituted and/or may be fused to further 3- to 12-membered rings;
• Y is C2-C20-alkyl, C3-C20-cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C6-C30-aryl, heteroaryl having 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of C1-C20-alkoxy, C6-C30-araloxy, C1-C20-alkylthio, C6-C30-arylthio, SiR10R11R12 halogen radicals, halogenated C1-C20-alkyl radicals, carbonyl (—CO(R10)), carbonylthio (—C═O(SR10)), carbonyloxy (—C═O(OR10)), oxycarbonyl (—OC═O(R10)), thiocarbonyl (—SC═O(R10)), amino (—NR10R11), OH, pseudohalogen radicals, amido (—C═O(NR10)), —NR10C═O(R11), phosphonate (—P(O)(OR10)2), phosphate (—OP(O)(OR10)2), phosphine (—PR10R11), phosphine oxide (—P(O)(R10)2), sulfate (—OS(O2)OR10), sulfoxide (—S(O)R10), sulfonate (—S(O)2OR10), sulfonyl (—S(O)2R10), sulfonamide (—S(O),NR10R11), NO2, boronic esters (—OB(OR10)2), imino (—C═NR10R11), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroximes and borazines.

27:

• A device selected from the group consisting of stationary visual display units;
• mobile visual display units;
• illumination units;
• keyboards;
• garments;
• furniture and wallpaper comprising at least one OLED as claimed in claim 23.