Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12108665-B2
Application number	US-202017639348-A
Country	US
Kind code	B2
Filing date	Aug 31, 2020
Priority date	Sep 2, 2019
Publication date	Oct 1, 2024
Grant date	Oct 1, 2024

Abstract

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

First claim

The invention claimed is:

1. An electronic device comprising at least one compound of formula (1)

wherein
Z is the same or different at each instance and is O or S;
A is R or Z;
R b is Ar or a free electron pair;

where, when A=Z, the oxygen or sulfur atom represented by Z is bonded to the carbon atom via a double bond, and R b is Ar;
in addition, R b is a free electron pair when A=R, and there is a double bond between the carbon atom to which A is bonded and the nitrogen atom to which R b is bonded;
R a is the same or different and is R, or the two R a groups together with the nitrogen atom and the carbon atom to which they bind form a group of one of the formulae (2), (3) and (4); R radical is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and which may be substituted by one or more R 1 radicals;

where the dotted bond in each case indicates the linkage within formula (1);
X is the same or different at each instance and is CR or N; or two adjacent X groups are a group of the formula (5) or (6)

where the dotted bonds indicate the linkage of this group in the formula (2), formula (3) or formula (4);
Y is the same or different at each instance and is CR or N;
W is the same or different at each instance and is NAr, O, S or C(R) 2 ;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals;
R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′) 2 , N(R 1 ) 2 , OAr′, Sar′, CN, NO 2 , OR 1 , SR 1 , COOR 1 , 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 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R 1 radicals, where one or more nonadjacent CH 2 , groups may be replaced by Si(R 1 ) 2 , C═O, NR 1 , O, S or CONR 1 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R 1 radicals; at the same time, two R radicals together may also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 2 ) 2 , CN NO 2 , OR 2 , SR 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 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 group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 and where one or more hydrogen atoms in the alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN, or 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 2 radicals; at the same time, two or more R 1 radicals together may form an aliphatic ring system;
R 2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F.

2. The electronic device as claimed in claim 1 , wherein the compound of the formula (1) contains at least one substituent Ar and at least one substituent R which is an aromatic or heteroaromatic ring system.

3. The electronic device as claimed in claim 1 , wherein the compound of the formula (1) is selected from the compounds of the formulae (7a) and (8a)

where the symbols used have the definitions given in claim 1 .

4. The electronic device as claimed in claim 1 , selected from the compounds of the formulae (7-1) to (7-9) and (8-1) to (8-11)

where the symbols have the definitions given in claim 1 .

5. The electronic device as claimed in claim 4 , wherein, when A=R, the R radical shown explicitly in formulae (8) and (8-1) to (8-11) which is bonded to the triazinone skeleton is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals.

6. The electronic device as claimed in claim 1 , wherein the compound of the formula (1) is selected from the compounds of the formulae (7-1a) to (7-9a) and (8-1a) to (8-11a)

where the symbols have the definitions given in claim 1 .

7. The electronic device as claimed in claim 1 , wherein Ar is the same or different at each instance and represents an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more R radicals.

8. The electronic device as claimed in claim 1 , wherein R is the same or different at each instance and is selected from the group consisting of H, D, F, N(Ar′) 2 , CN, OR 1 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl or alkenyl group may each be substituted by one or more R 1 radicals, but is preferably unsubstituted, and where one or more nonadjacent CH 2 groups may be replaced by O, or an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals; at the same time, two R radicals together may also form an aliphatic, aromatic or heteroaromatic ring system.

9. The electronic device as claimed in claim 1 , wherein Ar and R, if R is an aromatic or heteroaromatic ring system, are the same or different at each instance and are selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of th

Assignees

• Merck Patent Gmbh
• Merck Kgaa

Inventors

• Parham Amir
• Stoessel Philipp
• Ehrenreich Christian

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

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

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title