Heterocyclic spiro compounds

Patent metadata

Field	Value
Publication number	US-2016308147-A1
Application number	US-201415105759-A
Country	US
Kind code	A1
Filing date	Nov 21, 2014
Priority date	Dec 19, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

The present invention relates to spiro compounds containing electron-conducting groups and to electronic devices, in particular organic electroluminescent devices, comprising these compounds.

First claim

1 - 31 . (canceled)

32 . A compound of formula (I)

wherein
X is O, S, or C(R 1 ) 2 ;
Ar is on each occurrence, identically or differently, an aryl group having 6 to 40 C atoms or a heteroaryl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl alkoxy, or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , and wherein one or more non-adjacent CH 2 groups are 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, P(═O)(R 2 ), SO, SO 2 , O, S, or CONR 2 , and wherein one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems; and wherein two or more adjacent substituents R 1 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , wherein one or more non-adjacent CH 2 groups are optionally replaced by C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S, or CONR 3 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or a combination of these systems; and wherein two or more adjacent substituents R 2 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; wherein two radicals Ar 1 bonded to the same phosphorus atom are also optionally linked to one another by a single bond or a bridge selected from the group consisting of B(R 3 ), C(R 3 ) 2 , Si(R 3 ) 2 , C═O, C═NR 3 , C═C(R 3 ) 2 , O, S, S═O, SO 2 , N(R 3 ), P(R 3 ), and P(═O)R 3 ;
R 3 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, wherein one or more H atoms of the hydrocarbon radical are optionally replaced by F; and wherein two or more adjacent substituents R 3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
n is on each occurrence, identically or differently, 0, 1, 2, 3, or 4;
m is on each occurrence, identically or differently, 0, 1, 2, or 3;
o is on each occurrence, identically or differently, 0, 1, or 2;
p, q, r, s, t, and u are on each occurrence, identically or differently, 0 or 1;
E is an electron-transporting group, which in each case is optionally substituted by one or more radicals R 1 ;
R a is R 1 or a group —[Ar] p -E, wherein Ar, p, and E are as defined above;
R b is R 1 or a group —[Ar] p -E, where Ar, p, and E are as defined above;
with the proviso that
the compound of formula (I) contains at least one electron-transporting group E;
the sum of all indices m, s and, t is less than 7;
the sum of all indices n, q and, u is less than 9;
the sum of the indices r and o is less than 3;
R b is H, D or F, if R a is a group —[Ar] p -E and the compound of formula (I) contains at most two electron-transporting groups E; and
if R b is a group —[Ar] p -E and the compound of formula (I) contains at most two electron-transporting groups E, R a is H, D, or F.

33 . The compound of claim 32 , wherein the sum of s, t, and the electron-transporting groups E present in the groups R a and R b is less than or equal to 1.

34 . The compound of claim 32 , wherein p is 0, so that E is bonded directly to the benzofuran or spiro group.

35 . The compound of claim 32 , wherein one of the radicals R a or R b i a group —[Ar] p -E.

36 . The compound of claim 32 , wherein at least one radical containing an electron-transporting group E is bonded in position 1, 1′, 3, 3′, 4, 4′, 5, 5′, 6, 6′, 8, 8′ of the spirobifluorene skeleton.

37 . The compound of claim 32 , wherein the compound of formula (I) comprises one or two electron-transporting groups E.

38 . The compound of claim 32 , wherein the electron-transporting group E is a heteroaryl group having 5 to 60 aromatic ring atoms.

39 . The compound of claim 38 , wherein the electron-transporting group E comprises at least one structure selected from the group consisting of triazines, pyrimidines, pyrazines, imidazoles, benzimidazoles, and pyridines.

40 . The compound of claim 38 , wherein the electron-transporting group E comprises at least one structure selected from the group consisting of formulae (E-1) through (E10):

wherein
the dashed bond marks the bonding position,
Q′ is on each occurrence, identically or differently, CR 1 or N, and
Q″ is NR 1 , O, or S, and
wherein at least one Q′ is N and/or at least one Q″ is NR 1 .

41 . The compound of claim 38 , wherein the electron-transporting group E comprises at least one structure selected from the group consisting of formulae (E-11) through (E19):

wherein the dashed bond marks the bonding position.

42 . The compound of claim 40 , wherein at least one of the radicals R 1 in the structures of formulae (E-1) through (E-10) is Ar.

43 . The compound of claim 41 , wherein at least one of the radicals R 1 in the structures of formulae (E-11) through (E-19) is Ar.

44 . The compound of claim 32 , wherein the compound comprises a compound of formulae (II), (III), (IV), (V), (VI), and/or (VII):

45 . An oligomer, polymer, or dendrimer comprising one or more compounds of claim 32 , wherein one or more bonds are present from the compound to the oligomer, polymer, or dendrimer.

46 . A composition comprising at least one compound of claim 32 and at least one organofunctional material.

47 . A composition comprising at least one oligomer, polymer, or dendrimer of claim 45 and at least one organofunctional material.

48 . A formulation comprising at

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Montenegro Elvira
• Jatsch Anja
• Pflumm Christof
• Kroeber Jonas Valentin
• Grossmann Tobias
• Eberle Thomas
• Dobelmann Lars

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D409/04

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

• C07F9/65517

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title