Polycyclic compounds

Patent metadata

Field	Value
Publication number	US-10205106-B2
Application number	US-201414902093-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Jul 2, 2013
Publication date	Feb 12, 2019
Grant date	Feb 12, 2019

Abstract

The present invention relates to compounds having polycyclic structural units and to electronic devices, in particular organic electroluminescent devices, containing said compounds.

First claim

The invention claimed is:

1. A compound of formulae (Ia) or (IIa):

wherein
X is the same or different in each instance and is CR or N;
Y is or phenyl;
R is the same or different in each instance and is H, D, F, Cl, 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 is optionally substituted by one or more R 1 radicals, wherein one or more hydrogen atoms are optionally replaced by D or F, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in by one or more R 1 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and is optionally substituted by one or more R 1 radicals, an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and is optionally 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 is optionally substituted by one or more R 1 radicals; and wherein two adjacent R radicals together optionally define a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system;
R 1 is the same or different in 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 is optionally substituted by one or more R 2 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by R 2 C—CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S, or CONR 2 and wherein one or more hydrogen atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, an aralkyl or heteroaralkyl group which has 5 to 40 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; and wherein two or more adjacent R 1 radicals together, or R 1 together with R, optionally define a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system;
R 2 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by F; and wherein two or more R 2 radicals together optionally define a mono- or polycyclic aliphatic ring system.

2. The compound of claim 1 , wherein the compound comprises a structure of formulae (Ia1), (Ia2), (IIa1), or (IIa2):

3. The compound of claim 1 , wherein the compound comprises a structure of formulae (Ia3) or (Ia4):

4. The compound of claim 1 , wherein the compound comprises structures of formula CyE-(CyF) n , wherein:
n is 2 or 3
CyE is a structural element selected from the group consisting of formulae (CyE-1) through (CyE-27):

CyF is at least one structural element selected from the group consisting of formulae (CyF-3) and (CyF-4):

wherein
U is selected from the group consisting of O, S, C(R) 2 , N(R), B(R), Si(R) 2 , C═O, S═O, SO 2 , P(R) and P(═O)R; and

the dotted line in formulae (CyF-3) and (CyF-4) denotes the bond to the CyE group, and CyF group bonds to CyE in each case at the position denoted by #.

5. The compound of claim 1 , wherein the compounds have structures of formula CyG(CyH) n , wherein CyG and CyH together in each case defined a ring and:
n is 2 or 3
CyG is a structural element selected from the group consisting of formulae (CyG-1) through (CyG-17):

and
CyH is at least one structural element selected from the group consisting of formulae (CyH-1) (CyH-2)

wherein
U is selected from the group consisting of O, S, C(R) 2 , N(R), B(R), Si(R) 2 , C═O, S═O, SO 2 , P(R), and P(═O)R; and
the dotted line in formulae CyH-1 and CyH-2 denotes the bond to CyG, and CyH bonds to CyG in each case at the positions denoted by o so as to define a ring.

6. The compound of claim 1 , wherein the compound is in the form of an enantiomer mixture.

7. The compound of claim 1 , wherein the definitions for X are selected such that the ratio of CR to N is greater than or equal to 3.

8. The compound of claim 1 , wherein the compound has a glass transition temperature of at least 110° C.

9. The compound of claim 1 , wherein the compound has a molecular weight of not more than 5000 g/mol.

10. A composition comprising at least one compound of claim 1 and at least one further organic functional material selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials, and hole blocker materials.

11. A formulation comprising at least one compound of claim 1 and at least one solvent.

12. An electronic device comprising at least one compound of claim 1 .

13. The electronic device of claim 12 , wherein the electronic device is selected from the group consisting of organic electroluminescent devices.

14. The compound of claim 6 , wherein the compound is in the form of a diastereomer mixture.

15. The electronic device of claim 13 , wherein the electronic device is an organic electroluminescent device selected from the group consisting of organic laser diodes, organic light-emitting transistors, organic light-emitting diodes, organic light-emitting electrochemical cells, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic solar cells, organic optical detectors, organic photoreceptors, and organic field quench devices.

16. The compound of cl

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Joosten Dominik
• Koenen Nils

Classifications

• C07D495/08

  Bridged systems · CPC title

• C07D491/18

  Bridged systems · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• H01L51/0071

  Electricity · mapped topic