Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-2016181548-A1
Application number	US-201414908375-A
Country	US
Kind code	A1
Filing date	Jul 7, 2014
Priority date	Jul 30, 2013
Publication date	Jun 23, 2016
Grant date	—

Abstract

The invention relates to compounds comprising functional substituents in a specific spatial arrangement, devices containing same, and the preparation and use thereof.

First claim

1 .- 21 . (canceled)

22 . A compound of the general formula (1)

where the symbols and indices used are as follows:
A and A′ are the same or different and are an aromatic or heteroaromatic ring which has 5 or 6 ring atoms and is optionally substituted by one or more R 1 radicals which is optionally independent of one another;
G 1 and G 2 are the same or different at each instance and are an organic electron-transporting group (ETG) from the group of the electron-deficient heteroaromatic groups;
or an electron-rich organic group which conducts holes (LTG), the LTGs being selected from the group of the arylamines, triarylamines, bridged amines,
where at least one of the two G 1 and G 2 groups must be an electron-transporting group (ETG) and where the G 1 and G 2 groups is optionally substituted by one or more independent R 1 radicals;

Ar 1 is, when G 1 is an electron-transporting group, a bivalent aromatic or heteroaromatic, ring or ring system having 5 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the ETG,
or, when G 1 is a hole-transporting group, an aromatic ring or ring system having 5 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the LTG;

Ar 2 is, when G 2 is an electron-transporting group, a bivalent aromatic or heteroaromatic ring or ring system having 5 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the ETG,
or, when G 2 is a hole-transporting group, an aromatic ring or ring system having 5 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the LTG;

V is a single bond, C═O, C(R 1 ) 2 , NAr 3 , O, S, Si(R 1 ) 2 , BR 1 , PR 1 , P(═O)R 1 , SO or SO 2 , where, in the case of a single bond, the carbon atoms of the A and A′ rings are joined directly to one another by a single bond;
W is a single bond, C═O, C(R 1 ) 2 , NR 1 , O, S, Si(R 1 ) 2 , BR 1 , PR 1 , P(═O)R 1 , SO or SO 2 , where, in the case of a single bond, the carbon atoms of the A and A′ rings are joined directly to one another by a single bond, C(R 1 ) 2 , NR 1 , O and S;
m is either 0 or 1;
n is either 0 or 1,
where m=n;

p is either 0 or 1;
q is either 0 or 1, where p+q is either 1 or 2;
Ar 3 is an aromatic or heteroaromatic ring or ring system having 5 to 30 ring atoms, where the ring id optionally each be substituted by one or more R 2 radicals which is optionally substituted by one or more R 3 radicals, where two or more R 2 radicals together may form a ring;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R 2 radicals, where one or more nonadjacent 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 or CONR 2 and where one or more hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in each case by one or more R 2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or a combination of two or more of these groups or a crosslinkable Q group;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R 3 radicals, where one or more nonadjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in each case by one or more R 3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 3 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R 2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; at the same time, two or more R 3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system;

with the proviso that not more than one R 1 substituent in the A ring and not more than one R 1 substituent in the A′ ring contains an aromatic or heteroaromatic group having 5 to 30 ring atoms.

23 . The compound as claimed in claim 22 , wherein the compound is of the general formula (2)

where the symbols additionally used are as follows:
X is the same or different at each instance and is N or CR 1 ;
Q is the same or different at each instance and is X═X, S, O or NR 1 .

24 . The compound as claimed in claim 22 , wherein the compound is of one of the following general formulae (3) to (11):

25 . The compound as claimed in claim 24 , wherein the compound is of the general formula (4).

26 . The compound as claimed in claim 24 , wherein the compound is of the general formula (4) where X is CR 1 and m is 1.

27 . The compound as claimed in claim 24 , wherein the compound is of the general formula (4) where X is CR 1 , m is 1, p is 0 and q is 1.

28 . The compound as claimed in claim 22 , wherein the compound is of the general formula (13)

where V is O or S and where the aromatic rings each have not more than one R 1 substituent, s is 0 or 1 and t is 0 or 1, where s+t is optionally 0, 1 or 2.

29 . The compound as c

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Martynova Irina
• Jatsch Anja
• Eberle Thomas
• Kroeber Jonas Valentin
• Pflumm Christof

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• C09K2211/1011

  Condensed systems · CPC title