Emitter having a condensed ring system

Patent metadata

Field	Value
Publication number	US-10115903-B2
Application number	US-201314652982-A
Country	US
Kind code	B2
Filing date	Nov 27, 2013
Priority date	Dec 18, 2012
Publication date	Oct 30, 2018
Grant date	Oct 30, 2018

Abstract

The present invention relates to organic electroluminescent devices which comprise aromatic ring systems with two or three condensed rings as emitter materials, and to their possible uses.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising at least two electrodes and at least one emitting layer between the electrodes which comprises at least one bi- or tricyclic aromatic or heteroaromatic compound of the
general formulae (130) to (137):

where one or more H atoms of these compounds is replaced by one, two, three or four of a radical R 1 ,
R 1 is, identically or differently on each occurrence, D, F, N(R 2 ) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , P(R 2 ) 2 , S(═O)R 2 , a straight-chain 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 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, or CN, or an uncondensed aromatic ring system having 6 to 18 aromatic ring atoms or an uncondensed heteroaromatic ring system having 5 to 18 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 2 , or a condensed aromatic or heteroaromatic ring system having 8 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or a combination of two or more of these groups, two or more substituents R 1 may also form a mono- or polycyclic aliphatic ring system with one another here;
R 2 is, identically or differently on each occurrence, H, D, F, OH, N(R 3 ) 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , P(═O)(R 3 ) 2 , P(R 2 ) 2 , S(═O)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 , 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 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl or CN, or an uncondensed aromatic ring system having 6 to 18 aromatic ring atoms or an uncondensed haeroaromatic ring system having 5 to 18 aromatic ring atoms, each of which be substituted by one or more radicals R 3 , or a condensed aromatic or heteroaromatic ring system having 8 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or a combination of two or more of these groups; two or more adjacent radicals R 2 may form a mono- or polycyclic aliphatic ring system with one another here; and
R 3 is, identically or differently on each occurrence, H, D, F, 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, an uncondensed aromatic ring system having 6 to 18 aromatic ring atoms or a heteroaromatic ring system having 5 to 12 aromatic ring atoms, in which, in addition, one or more H atoms is optionally replaced by F; two or more substituents R 3 may also form a mono- or polycyclic aliphatic ring system with one another here
wherein the compound of the formulae (130) to (137) is employed as UV light-emitting compound, and wherein the device emits radiation having a wavelength in the range from 280 nm to 380 nm.

2. The electroluminescent device according to claim 1 , wherein the device comprises one or more additional layers between the electrodes.

3. The electroluminescent device according to claim 2 , wherein the additional layer is selected from the group consisting of the following:
(a) an exciton-blocking layer which comprises an exciton-blocking material having a band gap of 3.6 eV or higher;
(b) an electron-blocking layer which comprises an electron-blocking material having an LUMO of higher than −2.2 eV; and
(c) a hole-blocking layer which comprises a hole-blocking material having an HOMO of lower than −6.0 eV.

4. The electroluminescent device according to claim 1 , wherein the device is an organic light-emitting diode (OLED), a polymeric light-emitting diode (PLED), an organic light-emitting electrochemical cell (OLEC, LEEC or LEC), an organic light-emitting transistor (O-LET) or an organic light-emitting electrochemical transistor.

5. The electroluminescent device according to claim 4 , wherein the device is an OLED, PLED or OLEC.

6. A device according to claim 1 for use in medicine for phototherapy.

7. A method for the treatment of the skin by phototherapy comprising utilizing the device according to claim 1 .

8. The electroluminescent device according to claim 1 , wherein
R 1 being a straight-chain alkoxy group having 1 to 12 atoms or an aromatic ring system having 6 to 10 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 , and
R 2 is, identically or differently on each occurrence, D, F, N(R 3 ) 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , P(═O)(R 3 ) 2 , P(R 2 ) 2 , S(═O)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 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , 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 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl or CN, or an uncondensed aromatic ring system having 6 to 18 aromatic ring atoms or an uncondensed heteroaromatic ring system having 5 to 18 aromatic ring atoms, each of which be substituted by one or more radicals R 3 , or a condensed aromatic or heteroaromatic ring system having 8 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or a combination of two or more of these groups; two or more adjacent radicals R 2 may form a mono- or polycyclic aliphatic ring system with one another here.

9. The electroluminescent device according to claim 1 , wherein R 2 being F, OH, or a straight-chain alkyl or alkoxy group having 1 to 12 C atoms.

10. The electroluminescent device according to claim 1 , wherein R 1 is, identically or differently on each occurrence, D, F, N(R 2 ) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , P(R 2 ) 2 , S(═O)R 2 , a straight-chain alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is 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, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, or CN, or an uncondensed aromatic ring system having 6 to 18 aromatic ring atoms or an uncondensed heteroaromatic ring system having 5 to 18 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 2 , or a condensed aromatic or heteroaromatic ring system having 8 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 .

Assignees

• Merck Patent Gmbh

Inventors

• Pan Junyou
• Engel Martin
• Buchholz Herwig

Classifications

• C09K2211/1466

  containing nitrogen as the only heteroatom · CPC title

• C09K2211/1458

  containing sulfur as the only heteroatom · CPC title

• C09K2211/145

  containing oxygen as the only heteroatom · CPC title

• C09D139/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers · CPC title

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title