Phenoxasiline based compounds for electronic application

Patent metadata

Field	Value
Publication number	US-10319917-B2
Application number	US-201314440637-A
Country	US
Kind code	B2
Filing date	Nov 6, 2013
Priority date	Nov 6, 2012
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

Organic electronics applications, especially an organic light-emitting diode (OLED), an organic solar cell (organic photovoltaics) or a switching element such as an organic transistor, for example an organic FET (Field Effect Transistor) and an organic TFT (Thin Film Transistor), comprising at least one substituted phenoxasiline derivative, a organic semiconductor layer, a host material, electron/hole/exciton blocking material or electron/hole injection material comprising at least one substituted phenoxasiline derivative, the use of a substituted phenoxasiline derivative in organic electronics applications, an organic light-emitting diode, wherein at least one substituted phenoxasiline derivative is present in the electron/hole/exciton blocking layer, the electron/hole injection layer and/or the light-emitting layer, a light-emitting layer, an electron/hole/exciton blocking layer and an electron/hole injection layer comprising at least one substituted phenoxasiline derivative and 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 organic light-emitting diode, at least one light-emitting layer, at least one electron/hole/exciton blocking layer and/or at least one electron/hole injection layer according to the present invention.

First claim

The invention claimed is:

1. An organic electronic device comprising at least one compound of the formula (I):

in which
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7
are each independently hydrogen, C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl, heteroaryl having 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of C 1 -C 20 -alkoxy, C 6 -C 30 -aryloxy, C 1 -C 20 -alkylthio, C 6 -C 30 -arylthio, SiR 10 R 11 R 12 , halogen radicals, halogenated C 1 -C 20 -alkyl radicals, carbonyl (—CO(R 1′ )), carbonylthio (—C═O(SR 10 )), carbonyloxy (—C═O(OR 10 )), oxycarbonyl (—OC═O(R 10 )), thiocarbonyl (—SC═O(R 10 )), amino (—NR 10 R 11 ), OH, pseudohalogen radicals, amido (—C═O(NR 10 R 11 )), —NR 10 C═O(R 11 ), phosphonate (—P(O)(OR 10 ) 2 ), phosphate (—OP(O)(OR 10 ) 2 ), phosphine (—PR 10 R 11 ), phosphine oxide (—P(O)R 10 2 ), sulfate (—OS(O) 2 OR 10 ), sulfoxide (—S(O)R 10 ), sulfonate (—S(O) 2 OR 10 ), sulfonyl (—S(O) 2 R 10 ), sulfonamide (—S(O) 2 NR 10 R 11 ), NO 2 , boronic esters (—OB(OR 10 ) 2 ), imino (—C═NR 10 ), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroxines and borazines;
or two adjacent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 or R 7 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;
R 8 and R 9
are each independently C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl or heteroaryl having 5 to 30 ring atoms;
R 10 , R 11 , R 12
are each independently C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl, heteroaryl having 5 to 30 ring atoms, —O—Si(C 1 -C 20 -alkyl) 3 , —O—Si(C 6 -C 30 -aryl) 3 , C 1 -C 20 -alkoxy or C 6 -C 30 -aryloxy;
or two adjacent R 10 and R 11 , R 10 and R 12 or R 11 and R 12 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 R 10 , R 11 or R 12 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 C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl, heteroaryl having 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of C 1 -C 20 -alkoxy, C 6 -C 30 -aryloxy, C 1 -C 20 -alkylthio, C 6 -C 30 -arylthio, SiR 10 R 11 R 12 , halogen radicals, halogenated C 1 -C 20 -alkyl radicals, carbonyl (—CO(R 10 )), carbonylthio (—C═O(SR 10 )), carbonyloxy (—C═O(OR 10 )), oxycarbonyl (—OC═O(R 10 )), thiocarbonyl (—SC═O(R 10 )), amino (—NR 10 R 11 ), OH, pseudohalogen radicals, amido (—C═O(NR 10 R 11 )), —NR 10 C═O(R 11 ), phosphonate (—P(O)(OR 10 ) 2 ), phosphate (—OP(O)(OR 10 ) 2 ), phosphine (—PR 10 R 11 ), phosphine oxide (—P(O)R 11 2 ), sulfate (—OS(O 2 )OR 10 ), sulfoxide (—S(O)R 10 ), sulfonate (—S(O) 2 OR 10 ), sulfonyl (—S(O) 2 R 10 ), sulfonamide (—S(O) 2 NR 10 R 11 ), NO 2 , boronic esters (—OB(OR 10 ) 2 ), imino (—C═NR 10 ), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroxines and borazines.

2. The organic electronic device according to claim 1 , 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
R 10 , R 11 and R 12
are each independently C 6 -C 30 -aryl.

3. The organic electronic device according to claim 1 , wherein
Y is selected from the group consisting of

and SiPh 3 ,
wherein
X is NR 10 , O or S,
R 10 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl, heteroaryl having 5 to 30 ring atoms, —O—Si(C 1 -C 20 -alkyl) 3 , —O—Si(C 6 -C 30 -aryl) 3 , C 1 -C 20 -alkoxy or C 6 -C 30 -aryloxy; and
R 13 is H or phenoxasilinyl of formula (I′),

wherein the substituents Y′, R 2′ , R 3′ , R 4′ , R 5′ , R 7′ , R 8′ and R 9′ have independently the same meanings as the substituents Y, R 2 , R 3 , R 4 , R 5 , R 7 , R 8 and R 9 in the phenoxasiline derivatives of formula (I),
and the symbol ˜ means that there is a binding site at the position marked with ˜.

4. The organic electronic device according to claim 1 , wherein
R 8 and R 9
are each independently C 6 -C 30 -aryl or heteroaryl having 5 to 30 ring atoms.

5. The organic electronic device according to claim 1 , wherein
R 8 and R 9 are identical.

6. The organic electronic device according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are each hydrogen and R 6 is hydrogen or heteroaryl having 5 to 30 ring atoms selected from the group consisting of pyrrolyl, furanyl, thienyl, and benzoanellated ring systems thereof or SiR 10 R 11 R 12 ; or
R 1 , R 2 ; R 5 , and R 7 are each hydrogen and R 3 and R 4 are each independently C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl, heteroaryl having 5 to 30 ring atoms, methoxy, phenyloxy, halogenated C 1 -C 4 -alkyl, halogen, CN, SiR 10 R 11 R 12 , P(O)Ph 2 or diphenylamino and R 6 is hydrogen or heteroaryl having 5 to 30 ring atoms selected from the group consisting of pyrrolyl, furanyl, thienyl, and benzoanellated ring systems thereof or SiR 10 R 11 R 12 .

7. The organic electronic device according to claim 6 , wherein the compound of formula (I) is selected from the compounds of formulae (Ia), (Ib), (Ic) and (Id)

wherein
Y and R 6
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 SiR 10 R 11 R 12 ;
R 3 and R 4
are each independently C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, heterocycloalkyl having 3 to 20 ring atoms, C 6 -C 30 -aryl, heteroaryl having 5 to 30 ring atoms, methoxy, phenyloxy, halogenated C 1 -C 4 -alkyl, or halogen;
R 10 , R 11 and R 12
are each independently C 6 -C 30 -aryl;
and
R 8 and R 9
are each independently C 6 -C 30 -aryl or heteroaryl having 5 to 30 ring atoms.

8. The organic electronic device according to claim 1 , wherein
R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are hydrogen, and
R 6 is heteroaryl having 5 to 30 ring atoms selected from the group consisting of pyrrolyl, furanyl, thienyl, and benzoanellated ring systems thereof or SiR 10 R 11 R 12 , and
R 10 , R 11 and R 12
are each

Assignees

• Udc Ireland Ltd

Inventors

• Watanabe Soichi
• Lennartz Christian
• Wagenblast Gerhard
• Langer Nicolle
• Kido Junji
• Sasabe Hisahiro
• Kimura Masato

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07F9/6596

  having atoms other than oxygen, sulfur, selenium, tellurium, nitrogen or phosphorus as ring hetero atoms · CPC title

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• H01L2251/5384

  Electricity · mapped topic