IP Library › Granted Patent US 11,588,117
Granted Patent B2
US 11,588,117 · App. 14/908,375 · Granted Feb 21, 2023

Materials for electronic devices

Inventors: Amir Hossain Parham (Frankfurt am Main, DE); Irina Martynova (Griesheim, DE); Anja Jatsch (Frankfurt am Main, DE); Thomas Eberle (Landau, DE); Jonas Valentin Kroeber (Frankfurt am Main, DE); Christof Pflumm (Darmstadt, DE)
Assignee: MERCK PATENT GMBH
H01L51/0073C07D209/86C07D209/88C07D239/26C07D251/24C07D307/91C07D403/10C07D403/14C07D405/04C07D405/10C07D405/14C07D409/14C07D417/10C07D487/04C07D495/14C07D498/04C07F5/025C07F7/0812C09K11/025C09K11/06H01L51/008H01L51/0052H01L51/0061H01L51/0067H01L51/0071H01L51/0072H01L51/0085H01L51/0087H01L51/0094H05B33/10C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1096C09K2211/185H01L51/0002H01L51/5012H01L51/5056Y02E10/549
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,588,117
App. No.
14/908,375
Granted
Feb 21, 2023
Kind
B2
Abstract

The invention relates to compounds comprising functional substituents in a specific spatial arrangement, devices containing same, and the preparation and use thereof.

Claims (23)

1. A compound of the general formula (16a)

where the symbols and indices used are as follows:

G 1 is an organic electron-transporting group (ETG) of the formula E-11

Formula (E-11), where the dotted bond indicates the binding positions to the structure of formula (16a);

G 2 is an electron-rich organic group selected from the a group of the formula (L-18)-(L-30) and L(34)-L(36):

Formula (L-36)

where dotted bonds indicate the binding positions to the structure of formula (16a), which may be substituted by one or more independent R 2 radicals;

R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, 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 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, which is optionally substituted by one or more R 2 radicals; where one or more nonadjacent 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 hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms which is optionally substituted by one or more R 2 radicals; or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms which 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 which is optionally substituted by one or more R 2 radicals, or a combination of two or more of these groups or a crosslinkable Q group;

R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, which is optionally substituted by one or more R 3 radicals, where one or more nonadjacent 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 hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 ; or an aromatic ring system which has 6 to 60 aromatic ring atoms which is optionally substituted by one or more R 3 radicals; or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms which is optionally substituted by one or more R 3 radicals; or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms which is optionally substituted by one or more R 3 radicals; or a combination of two or more of these groups; at the same time, two or more adjacent R 2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system;

R 3 is the same or different at each instance and is H, D, F or an aliphatic, or aromatic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; at the same time, two or more R 3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system.

2. A formulation comprising at least one compound as claimed in claim 1 and at least one solvent.

3. The compound as claimed in claim 1 , wherein G 1 is selected from the formula E-17, E-22, E-24, E-25, E-26, E-27, E-28, or E-29:

which may be substituted by one or more independent R 2 radicals.

4. The compound as claimed in claim 1 , wherein each R 1 is independently selected from the group consisting of H and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more R 2 radicals.

5. An electronic device comprising at least one compound as claimed in claim 1 in an emission layer (EML), electron transport layer (ETL) or in a hole blocker layer (HBL).

6. The electronic device as claimed in claim 5 , wherein the device is an organic electroluminescent device which is selected from the group consisting of organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

7. An electronic device comprising at least one compound as claimed in claim 1 .

8. The electronic device as claimed in claim 7 , wherein the device is an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic electroluminescent device (OLED), an organic light-emitting electrochemical cell (OLEC, LEEC, LEC), an organic solar cell (OSC), an organic optical detector, or an organic photoreceptor.

9. A process for producing an electronic device as claimed in claim 7 , which comprises applying at least one organic layer by gas phase deposition or from solution.

10. The electronic device as claimed in claim 9 , for use in medicine for phototherapy.

11. A composition comprising at least one additional compound as claimed in claim 1 and at least one further compound 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.

12. The composition as claimed in claim 11 , wherein the additional compound is a host or matrix material.

13. The composition as claimed in claim 11 , wherein the additional compound has a band gap of 2.5 eV or more.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2016
From: PARHAM, AMIR HOSSAIN; MARTYNOVA, IRINA; JATSCH, ANJA; EBERLE, THOMAS; KROEBER, JONAS VALENTIN; PFLUMM, CHRISTOF
To: MERCK PATENT GMBH
Reel/Frame 037616/0253 →
Priority Claims (1)
EP 13003800 · Jul 30, 2013 · regional
Continuity (1)
Related Publication 20160181548A1 · Jun 23, 2016
Cited By (3)
US 12,232,416 US 12,336,426 US 12,359,118