Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9425409-B2
Application number	US-201113878332-A
Country	US
Kind code	B2
Filing date	Sep 8, 2011
Priority date	Oct 9, 2010
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The present invention relates to compounds of the

to the use of the compounds in electronic devices, to processes for the preparation of the compounds, and to electronic devices comprising the compounds, preferably as electron-transport materials, as hole-blocking materials, as matrix materials and/or as emitter materials.

First claim

The invention claimed is:

1. A compound of the formula (I-1a), (I-1b), (I-1c), (I-1d), (I-2a), (I-2b), (I-2c), (I-2d), (I-3b) or (I-3d)

R 1 is H, D, F, Cl, Br, I, CHO, N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OS(═O) 2 R 3 , SO 3 H, C(═O)OR 3 , OR 3 , 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 3 , where one or more non-adjacent 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 ), S═O, S(═O) 2 , NR 3 , —O—, —S— or C(═O)NR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , and where, furthermore, R 1 is optionally linked to a group R 2 bonded in the 1,3-position adjacent to R 1 and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OS(═O) 2 R 3 , SO 3 H, C(═O)OR 3 , OR 3 , 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 3 , where one or more non-adjacent 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 ), S═O, S(═O) 2 , NR 3 , —O—, —S— or C(═O)NR 3 and where one or more H atoms is optionally 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 , and which is optionally condensed with the ring to which it is bonded, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of these systems, where two or more radicals R 2 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system,
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , CR 4 ═C(R 4 ) 2 , CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OS(═O) 2 R 4 , SO 3 H, C(═O)OR 4 , OR 4 , 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, each of which is optionally substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), S═O, S(═O) 2 , NR 4 , —O—, —S— or C(═O)NR 4 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , or a combination of these systems, where two or more radicals R 3 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system,
R 4 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 is optionally replaced by D or F; two or more identical or different substituents R 4 here may also be linked to one another and form a mono- or polycyclic, aliphatic or aromatic ring system;
X is on each occurrence, identically or differently, CR 3 or N, with the proviso that not more than two adjacent X are simultaneously equal to N;
and where at least one radical R 2 must be selected from the group comprising
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 3 and which is optionally condensed with the ring to which they are bonded, and
fully conjugated alkenyl or alkynyl groups having 2 to 40 C atoms, which is optionally substituted by one or more radicals R 3 .

2. The compound according to claim 1 , wherein the compound corresponds to one of the formulae (I-1e) to (I-1k), (I-2e) to (I-2k) and (I-3e), (I-3g) to (I-3k)

where R 1 , R 2 and X are as defined in claim 1 .

3. The compound according to claim 2 , wherein X is equal to CR 3 .

4. The compound according to claim 1 , wherein the following applies to R 1 :
R 1 is H, D, F, N(R 3 ) 2 , C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, Si(R 3 ) 3 , OR 3 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms or an alkenyl or alkynyl group having 2 to 10 C atoms, where the said groups may each be substituted by one or more radicals R 3 and where one or more adjacent or non-adjacent CH 2 groups is optionally replaced by —C≡C—, R 3 C═CR 3 , Si(R 3 ) 2 , C═O, C═NR 3 , NR 3 , —O—, —S— or C(═O)NR 3 .

5. A process for the preparation of the compound according to claim 1 , wherein the process includes one or more condensation reactions between one or more amino groups and one or more carbonyl or carboxyl functions with formation of a heterocyclic ring.

6. A formulation comprising at least one compound according to claim 1 and at least one solvent.

7. A mixture comprising at least one compound according to claim 1 and at least one phosphorescent emitter compound.

8. An electronic device which comprises the compound according to claim 1 .

9. An organic electroluminescent device which comprises the compound according to claim 1 .

10. The electronic device according to claim 8 , wherein the device is an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, an organic laser diode or an organic electroluminescent device.

11. An organic electroluminescent device which comprises the compound according to claim 1 is employed as electron-transport material in an electron-transport layer and/or is employed as hole-blocking material in a hole-blocking layer and/or is employed as emitter material in an emitting layer and/or is employed as matrix material in an emitting layer.

Assignees

• Schwaiger Jochen
• Becker Heinrich
• Merck Patent Gmbh

Inventors

• Schwaiger Jochen
• Becker Heinrich

Classifications

• H01L51/0052

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic

• C07D487/04 Primary

  Ortho-condensed systems · CPC title