Heterocyclic compounds

Patent metadata

Field	Value
Publication number	US-9893299-B2
Application number	US-201415021027-A
Country	US
Kind code	B2
Filing date	Aug 13, 2014
Priority date	Sep 11, 2013
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

The invention concerns heterocyclic compounds and electronic devices, in particular organic electroluminescent devices, containing these compounds.

First claim

The invention claimed is:

1. A compound of the general formula (1)

where the symbols used are as follows:
Q is the same or different at each instance and is X═X, O, NR, S, SO, SO 2 , PR, POR or BR, where at least one Q is X═X;
X 1 is CR or N;
X is the same or different at each instance and is N or CR;
Y is the same or different at each instance and is CR;
R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, NO 2 , OH, COOH, C(═O)N(R 1 ) 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, each of which may be substituted by one or more R 1 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, NR 1 , O, S or CONR 1 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two adjacent R radicals together may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
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 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 and where one or more hydrogen atoms may be 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 may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be 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 may be substituted by one or more R 2 radicals; at the same time, two or more adjacent R 1 radicals together, or R 1 together with R, may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
R 2 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 2 substituents together may also form a mono- or polycyclic aliphatic ring system;

which is characterized in that
the respective R radicals of the two Y groups together with the carbon atoms of the heteroaromatic ring form a ring of the following formulae:

where
A 1 , A 3 is the same or different at each instance and is C(R 3 ) 2 , O, S, NR 3 or C(═O);
A 2 is C(R 1 ) 2 , O, S, NR 3 or C(═O);
G is a bivalent group selected from O, S, N(R 2 ), B(R 2 ), Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , S═O, SO 2 , P(R 2 ) and P(═O)R 2 , an alkylene group which has 1, 2 or 3 carbon atoms and may be substituted by one or more R 2 radicals, —CR 2 ═CR 2 - or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R 2 radicals;

and where the carbon-carbon double bond shown in the formulae (5) to (11) corresponds to an aromatic double bond from the heteroaromatic ring to which the groups of the formulae (5) to (11) bind;
R 3 is the same or different at each instance and is F, a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 , and where one or more hydrogen atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 24 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 24 aromatic ring atoms and may be substituted by one or more R 2 radicals; at the same time, two R 3 radicals bonded to the same carbon atom together may form an aliphatic or aromatic ring system and thus form a Spiro system; in addition, R 3 with an adjacent R or R 1 radical may form an aliphatic ring system;

with the proviso that no two identical heteroatoms in the aforementioned groups are bonded directly to one another and no two C═O groups are bonded directly to one another, and, in addition,
if the two Y groups together are a ring structure of the formulae (12) or (13)

the X 1 radical is not a group of the formula (14)

in which X is as defined above and the dotted lines represent the bonds of the carbon atom of the X 1 radical to two further carbon atoms of the ring including the X 1 radical of formula (1);
wherein, in the ring structures of one of the formulae (5), (6), (7), (8), (9), (10), and/or (11), not more than one of the A 1 , A 2 , and A 3 groups is O, S or NR 3 .

2. The compound of claim 1 , wherein the heteroaromatic ring system having the X 1 radical is a system having 10 to 30 aromatic ring atoms.

3. The compound of claim 1 , wherein the compound has a general structure having the formula (15):

where X″ is the same or different at each instance and is CR 1 or N, where the symbols used are each as defined above.

4. The compound of claim 1 , wherein Q is the same or different at each instance and is X═X.

5. The compound of claim 1 , wherein, in the ring structures of one of the formulae (5), (6), (7), (8), (9), (10) and/or (11), the A 1 and A 3 groups are the same or different at each instance and are C(R 3 ) 2 and A 2 is C(R 1 ) 2 .

6. The compound of claim 1 , wherein, in the ring structures of formulae (8), (9), (10) and/or (11), the R 1 radicals bonded to the bridgehead are H, D, F or CH 3 .

7. The compound of claim 1 , wherein, in the structure of formula (1), the two Y groups form a ring structure of one of the foll

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Koenen Nils

Classifications

• C07D221/16 Primary

  containing carbocyclic rings other than six-membered · CPC title

• C07D237/26

  condensed with carbocyclic rings or ring systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09B57/001

  Pyrene dyes · CPC title

• C07D221/20

  Spiro-condensed ring systems · CPC title