Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11245079-B2
Application number	US-201916390675-A
Country	US
Kind code	B2
Filing date	Apr 22, 2019
Priority date	Feb 21, 2014
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

The invention relates to compounds which are suitable for use in electronic devices, and electronic devices, in particular organic electroluminescent devices, containing said compounds.

First claim

The invention claimed is:

1. A compound of formula (3)

where the symbols and indices used are as follows:
X is the same or different at each instance and is CR 1 or N; or two adjacent Xs are a group of the following formula (4), (5) or (6):

where {circumflex over ( )} indicates the corresponding adjacent X groups in the formula (2) or (3);

V is the same or different at each instance and is C(R 1 ) 2 , NR 1 , O, S, BR 1 , Si(R 1 ) 2 or C═O;
Z is the same or different at each instance and is CR 1 or N;
Ar is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms, does not contain any electron-deficient heteroaryl groups and may be substituted by one or more R 2 radicals;
R, R 1 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 3 ) 2 , C(═O)Ar 1 , C(═O)R 3 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 3 ) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 3 C═CR 3 , Si(R 3 ) 2 , C═O, C═S, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 3 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals; at the same time, it is optionally possible for two R 1 substituents bonded to the same carbon atom to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 3 radicals;
R 2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 3 ) 2 , C(═O)Ar 1 , C(═O)R 3 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 3 ) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 3 C═CR 3 , Si(R 3 ) 2 , C═O, C═S, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, does not contain any electron-deficient heteroaryl groups and may be substituted in each case by one or more R 3 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms, does not contain any electron-deficient heteroaryl groups and may be substituted by one or more R 3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms, does not contain any electron-deficient heteroaryl groups and may be substituted by one or more R 3 radicals; at the same time, it is possible for two or more adjacent R 3 substituents together to form a mono- or polycyclic aliphatic ring system;
Ar 1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5-30 aromatic ring atoms and may be substituted by one or more nonaromatic R 3 radicals; at the same time, two Ar 1 radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R 3 ), C(R 3 ) 2 , O and S;
R 3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent R 3 substituents together may form a mono- or polycyclic, aliphatic ring system;
p is the same or different at each instance and is 0, 1, 2, 3 or 4;
q is 0, 1 or 2.

2. The compound as claimed in claim 1 , wherein X is the same or different at each instance and is CR 1 or N, where not more than one X group per cycle is N, or in that two adjacent X groups are a group of the formula (4), where Z is the same or different at each instance and is CR 1 and V is the same or different at each instance and is NR 1 , C(R 1 ) 2 , O or S, and the rest of the X groups in the cycle are CR 1 .

3. The compound as claimed in claim 1 , wherein the compound is selected from the compounds of the formula (15)

4. The compound as claimed in claim 1 , wherein the compound is selected from the compounds of the formula (15a)

5. The compound as claimed in claim 1 , wherein R is the same or different at each instance and is selected from the group consisting of H, F, CN, N(Ar 1 ) 2 , a straight-chain alkyl group having 1 to 10 carbon atoms and a branched or cyclic alkyl group having 3 to 10 carbon atoms and an aromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R 3 radicals.

6. The compound as claimed in claim 1 , wherein the compound is selected from the compounds of the formula (15b)

7. The compound as claimed in claim 1 , wherein the compounds of formula (3) contains a total of at least 12 aromatic ring atoms in the Ar, R 1 and R 2 substituents.

8. The compound as claimed in claim 1 , wherein Ar is selected from the groups of the formulae Ar-1 to Ar-58

where R* has the definitions given in claim 1 , the dotted bond represents the bond to t

Assignees

• Merck Patent Gmbh

Inventors

• Jatsch Anja
• Grossmann Tobias
• Parham Amir Hossain
• Eberle Thomas
• Pflumm Christof
• Kroeber Jonas
• Stoessel Philipp
• Montenegro Elvira
• Linge Rouven

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D491/20

  Spiro-condensed systems · CPC title

• C09B11/00

  Diaryl- or thriarylmethane dyes · CPC title

• C07D405/04

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

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title