Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9876171-B2
Application number	US-201214110946-A
Country	US
Kind code	B2
Filing date	Mar 15, 2012
Priority date	Apr 13, 2011
Publication date	Jan 23, 2018
Grant date	Jan 23, 2018

Abstract

The present invention relates to an electronic device comprising one or more compounds of a formula (I) or (II). Furthermore, the invention encompasses the use of a compound of the formula (I) or (II) in an electronic device, and the provision of certain compounds of the formula (I) or (II).

First claim

The invention claimed is:

1. An electronic device, comprising an anode, a cathode and at least one organic layer, wherein the organic layer comprises at least one compound of the formula (I) or (II)

wherein:
Y is C(R 1 ) 2 ;
Z are on each occurrence, identically or differently, CR 1 or N;
Q is CR 1 ;
L is selected from C═O, C═NR 1 , Si(R 1 ) 2 , NR 1 , P(═O)(R 1 ), O, S, SO, SO 2 , alkylene groups having 1 to 20 C atoms or alkenylene or alkynylene groups having 2 to 20 C atoms, where one or more CH 2 groups in the said groups may be replaced by Si(R 1 ) 2 , O, S, C═O, C═NR 1 , C(═O)O, (C═O)NR 1 , NR 1 , P(═O)(R 1 ), SO or SO 2 and where one or more H atoms in the said groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , and aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , and any desired combinations of 1, 2, 3, 4 or 5 identical or different groups selected from the above-mentioned groups; or L is a single bond, where p in this case is equal to 2;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , N(R 2 ) 2 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned groups may be 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 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy, heteroaryloxy, aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 ;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more CH 2 groups in the above-mentioned groups may be 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 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy, heteroaryloxy, aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 3 , where two or more radicals R 2 may be linked to one another and may form a ring or a ring system;
R 3 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F; two or more substituents R 3 here may also be linked to one another and form a ring or a ring system;
n is on each occurrence, identically or differently, 0 or 1, where, in the case n=0, the group in brackets is not present and optionally groups R 1 are instead bonded to the central benzene ring;
p is equal to 2, 3, 4, 5 or 6; and
where the group Y and the nitrogen atom at any desired adjacent positions may be bonded to the aromatic six-membered ring;
where, in the formulae (I) and (II), in each case no or 1, 2 or 3 carbon atoms which are constituents of the central aromatic six-membered ring may be replaced by N if the sum of the indices n is equal to 0, and where, in the formulae (I) and (II), in each case no or 1 or 2 carbon atoms which are constituents of the central aromatic six-membered ring may be replaced by N if the sum of the indices n is equal to 1, and
where, in formula (II), the moieties in square brackets with index p which are bonded to L may be identical or different; and
where, in formula (II), the group L may be bonded at any desired position of the moiety in square brackets with index p.

2. The electronic device according to claim 1 , wherein p is equal to 2.

3. The electronic device according to claim 1 , wherein the sum of the values for n in formula (I) and the sum of the values for n per unit in square brackets with index p in formula (II) is equal to 0.

4. The electronic device according to claim 1 , wherein 0 or 1 group Z per aromatic ring is equal to N.

5. The electronic device according to claim 1 , wherein L is selected from a single bond, where in this case p=2, or from C═O, NR 1 , O or S, where in these cases p=2, or from alkylene groups having 1 to 10 C atoms, alkenylene groups having 2 to 10 C atoms, where one or more CH 2 groups in the said groups may be replaced by C═O, NR 1 , P(═O)(R 1 ), O or S, and arylene or heteroarylene groups having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or from divalent aromatic or heteroaromatic ring systems of the formula (L-1)
* E i Ar 1 k E i Ar 1 l E i *  formula (L-1),

where p in this case is equal to 2 and wherein:
Ar 1 is on each occurrence, identically or differently, an aryl or heteroaryl group having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 ;
E is on each occurrence, identically or differently, a single bond, C═O, NAr 1 , P(═O)(R 1 ), O, S, SO or SO 2 ;
i is on each occurrence, identically or differently, 0 or 1;
k,l are on each occurrence, identically or differently, 0, 1, 2 or 3, where the sum of the values of k and 1 is greater than 0; and
where the groups Ar 1 may be connected to one another via one or more divalent groups T, where
T is selected on each occurrence, identically or differently, from a single bond, BR 1 , C(R 1 ) 2 , C═O, C═S, C═NR 1 , C═C(R 1 ) 2 , CR 1 ═CR 1 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, S═O and S(═O) 2 ; and
the symbols * mark bonds from the group L to the remainder of the compound.

6. The electronic device according to claim 1 , wherein the compound of the formula (I) is selected from the formulae

where the compounds may be substituted by radicals R 1 at all unsubstituted positions.

7. The electronic device according to claim 1 , wherein the compound of the formula (II) is selected from the formulae

Assignees

• Mujica-Fernaud Teresa
• Pflumm Christof
• Martynova Irina
• Merck Patent Gmbh

Inventors

• Mujica-Fernaud Teresa
• Pflumm Christof
• Martynova Irina

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title