Compounds for electronic devices
The present invention relates to compounds of the formula (1) or (2) and to the use thereof in electronic devices, and to electronic devices which comprise these compounds. The invention furthermore relates to the preparation of the compounds of the formula (1) or (2) and to formulations comprising one or more compounds of the formula (1) or (2).
1. A compound of the formula (2′)
where the following applies to the symbols and indices occurring:
W is on each occurrence equal to Z,
where a unit comprising two adjacent groups W may optionally be replaced by a group of the formula (3)
where the group of the formula (3) is arranged in such a way that the bond between the C atoms labelled with * is condensed onto the six-membered ring of the carbazole derivative;
X is a divalent group selected from the group consisting of C(R) 2 , Si(R) 2 , NR, PR, P(═O)R, BR, O, S, C═O, C═S, C═NR, S═O and S(═O) 2 ;
Z is identically or differently on each occurrence, and is equal to CR or is equal to C if a substituent is bonded to the group Z;
L is on each occurrence, identically or differently C(R 3 ) 2 ;
R is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , CR 1 ═C(R 1 ) 2 , CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , OSO 2 R 1 , OH, COOR 1 , CON(R 1 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by —R 1 C═CR 1 —, —C═C—, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , —O—, —S—, —COO— or CONR 1 — and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms, which is optionally in each case substituted by one or more radicals R 1 , or an aryloxy group having 6 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or a combination of these systems, where two or more radicals R do not link to one another to form a ring;
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , CR 2 ═C(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , OH, COOR 2 , CON(R 2 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 —, —C═C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , —O—, —S—, —COO— or —CONR 2 — and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R 2 , or an aryloxy group having 6 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems, where two or more radicals R 1 is optionally linked to one another and may form a ring;
R 2 is, identically or differently on each occurrence, H, D, F or an aliphatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more identical or different substituents R 2 here optionally also be linked to one another and may form a ring;
R 3 is, identically or differently on each occurrence, selected from a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , where two or more radicals R 2 is optionally linked to one another and optionally form a ring;
j is equal to 0, 1 or 2, where, for j=0, the two groups which are bonded to the group with the index j are connected directly to one another.
2. The compound according to claim 1 , wherein X is C(R) 2 , NR, O, S, C═O, C═NR, S═O or S(═O) 2 .
3. The compound according to claim 1 , wherein R on each occurrence, identically or differently, is H, D, F, CN, Si(R 1 ) 3 , or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 1 , or aryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 .
4. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any desired positions substituted by a radical R in formula (2′).
5. A formulation comprising at least one compound according to claim 1 and at least one solvent.
6. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 4 and at least one solvent.
7. A process for the preparation of the compound of the formula (2′) according to claim 1 , comprising at least one coupling reaction for the linking of the moiety containing the carbazole group to the moiety containing the arylamino group.
8. An organic electroluminescent device (OLED) comprising at least one compound according to claim 1 .
9. An electronic device comprising at least one compound according to claim 1 .
10. An electronic device comprising at least one polymer, oligomer or dendrimer according to claim 4 .
11. The electronic device according to claim 9 , wherein the device is an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench devices (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser) or an organic electroluminescent device (OLED).
12. An organic electroluminescent device which comprises the compound according to claim 1 , wherein the compound according to claim 1 is employed as hole-transport material in a hole-transport layer or hole-injection layer and/or as matrix material in an emitting layer.
13. The compound according to claim 1 , wherein the compound is of the formula
14. The compound according to claim 1 , wherein R 1 is selected on each occurrence, identically or differently, from H, D, F, CN, Si(R 2 ) 3 , or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 2 , or an aryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 .
15. The compound according to claim 1 , wherein R 2 is, identically or differently on each occurrence, H, D, F or an aliphatic, and/or aromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F.
16. The compound according to claim 1 , wherein W is at each occurrence CR.
17. The compound according to claim 1 , wherein j=0.
18. A compound of the formula (2′)
where the following applies to the symbols and indices occurring:
W is on each occurrence equal to Z,
where a unit comprising two adjacent groups W may optionally be replaced by a group of the formula (3)
where the group of the formula (3) is arranged in such a way that the bond between the C atoms labelled with * is condensed onto the six-membered ring of the carbazole derivative;
X is a divalent group selected from the group consisting of C(R) 2 , Si(R) 2 , NR, PR, P(═O)R, BR, O, S, C═O, C═S, C═NR, S═O and S(═O) 2 ;
Z is identically or differently on each occurrence, and is equal to CR or is equal to C if a substituent is bonded to the group Z;
L is on each occurrence, identically or differently C(R 3 ) 2 ;
R is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , CR 1 ═C(R 1 ) 2 , CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , OSO 2 R 1 , OH, COOR 1 , CON(R 1 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by —R 1 C═CR 1 —, —C═C—, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , —O—, —S—, —COO— or —CONR 1 — and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms, which is optionally in each case substituted by one or more radicals R 1 , or an aryloxy group having 6 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or a combination of these systems, where two or more radicals R do not link to one another to form a ring;
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , CR 2 ═C(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , OH, COOR 2 , CON(R 2 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by —R 2 C═CR 2 —, —C═C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , —O—, —S—, —COO— or —CONR 2 — and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms, which optionally in each case is substituted by one or more radicals R 2 , or an aryloxy group having 6 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems, where two or more radicals R 1 do not link to one another to form a ring;
R 2 is, identically or differently on each occurrence, H, D, F or an aliphatic organic radical having 1 to 20 C atoms or an aromatic and/or heteroaromatic organic radical having up to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more identical or different substituents R 2 here optionally also be linked to one another and may form a ring;
R 3 is, identically or differently on each occurrence, selected from a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , where two or more radicals R 3 is optionally linked to one another and optionally form a ring;
j is equal to 0, 1 or 2, where, for j=0, the two groups which are bonded to the group with the index j are connected directly to one another.