Triphenylene-based materials for organic electroluminescent devices

• US 10,971,689 B2
• Filed: 05/21/2018
• Issued: 04/06/2021
• Est. Priority Date: 10/15/2010
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Stoessel, Philipp, Joosten, Dominik, Buesing, Arne
• Primary Examiner(s): Clark, Gregory D
• Application Number:
  US15/985,120
• Publication Number:
  US 20180269411A1
• Time in Patent Office: 1,051 Days
• Field of Search: None
• CPC Class Codes: C07C 13/62 with more than three condensed rings
• CPC Class Codes: C07C 211/58 Naphthylamines; N-substituted derivatives thereof
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07D 209/56 Ring systems containing three or more rings
• CPC Class Codes: C07D 209/80 [b, c]- or [b, d]-condensed
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 209/90 Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07D 251/24 to three ring carbon atoms
• CPC Class Codes: C07D 307/77 ortho- or peri-condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 313/06 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 333/50 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 401/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/10 : linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/14 : containing three or more hetero rings
• CPC Class Codes: C07F 15/0033 : Iridium compounds
• CPC Class Codes: C07F 15/0086 : Platinum compounds
• CPC Class Codes: C07F 5/027 : Organoboranes and organoborohydrides
• CPC Class Codes: C07F 7/025 : without C-silicon linkages
• CPC Class Codes: C07F 7/0807 : comprising Si as a ring atom
• CPC Class Codes: C07F 7/0812 : comprising a heterocyclic ring
• CPC Class Codes: C07F 9/5022 : Aromatic phosphines (P-C aromatic linkage)
• CPC Class Codes: C07F 9/5325 : Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
• CPC Class Codes: C07F 9/58 : Pyridine rings
• CPC Class Codes: C09B 1/00 : Dyes with anthracene nucleus not condensed with any other ring
• CPC Class Codes: C09B 57/00 : Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/001 : Pyrene dyes
• CPC Class Codes: C09B 57/007 : Squaraine dyes
• CPC Class Codes: C09B 57/008 : Triarylamine dyes containing no other chromophores
• CPC Class Codes: C09B 57/10 : Metal complexes of organic compounds not being dyes in uncomplexed form
• CPC Class Codes: C09K 11/06 : containing organic luminescent materials
• CPC Class Codes: C09K 2211/1416 : Condensed systems
• CPC Class Codes: C09K 2211/1433 : bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/145 : containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1458 : containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1491 : containing other combinations of heteroatoms
• CPC Class Codes: H05B 33/14 : characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 85/40 : Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/624 : containing six or more rings
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

The present invention relates to compounds of the formula (1) and (2) which are suitable for use in electro¬nic devices, in particular organic electroluminescent devices.

Claims

1. A neutral compound of the formula (2),

2. The compound according to claim 1, wherein the compound is selected from the compounds of the formula (7),

3. The compound according to claim 1, wherein the compound is selected from the compounds of the formula (7a),

4. The compound according claim 1, wherein, and in that in compounds of the formula (2) the two radicals R are identical.

5. The compound according claim 2, wherein, and in that in compounds of the formula (7) the two radicals R are identical.

6. The compound according claim 3, wherein, and in that in compounds of the formula (7a), the two radicals R are identical.

7. A process for the preparation of the compound according to claim 1 which comprises reacting 1,12-dilithiotriphenylene derivatives with electrophiles or by reaction of halogen- or amino-substituted triphenylene derivatives in a metal-catalyzed coupling reaction.

8. An oligomer, polymer or dendrimer containing one or more of the compounds according to claim 1, where one or more bonds are present from the compound to the polymer, oligomer or dendrimer.

9. An electronic device which comprises the compound according to claim 1.

10. An electronic device which comprises the oligomer, polymer or dendrimer according to claim 8.

11. The electronic device as claimed in claim 9, wherein the device is selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic plasmon emitting devices.

12. An organic electroluminescent device which comprises the compound according to claim 1 is employed as matrix material for fluorescent or phosphorescent emitters and/or as fluorescent emitter and/or in a hole-blocking layer and/or in an electron-transport layer and/or in an electron-blocking or exciton-blocking layer and/or in a hole-transport or hole-injection layer and/or in an optical coupling-out layer.

13. An organic electroluminescent device which comprises the compound according to claim 1 is used as matrix material for phosphorescent emitters and where the group Ar¹ or the radicals on Ar¹ or the aromatic or heteroaromatic ring system or the radicals R³ on the aromatic or heteroaromatic ring system contains no condensed aryl groups having more than 10 C atoms and no condensed heteroaryl groups in which more than two aryl or 6-membered heteroaryl groups are condensed directly onto one another;

and/or in that, in the compound of the formula (2) or formula (7) or formula (7a), R stands, identically or differently on each occurrence, for N(Ar¹)₂, C(═

O)Ar¹, P(═

O)(Ar¹)₂ or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, where the group Ar¹ or the radicals on Ar¹ or the aromatic or heteroaromatic ring system contains no condensed aryl groups having more than 10 C atoms and no condensed heteroaryl groups in which more than two aryl or 6-membered heteroaryl groups are condensed directly onto one another.

14. The organic electroluminescent device according to claim 13, wherein at least one radical R is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, ortho-, meta- or para-terphenyl, ortho-, meta-, para- or branched quaterphenyl, fluorene or spirobifluorene, each of which is optionally substituted by one or more radicals R³, and at least one radical R is selected from the structures of the formulae (8) to (38),

15. An organic electroluminescent device which comprises the compound according to claim 1 is used as electron-transport material and at least one radical R stands for C(═

O)Ar¹, P(═

O)(Ar¹)₂ or for an electron-deficient heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R³.

16. The organic electroluminescent device according to claim 15, wherein the electron-deficient heteroaromatic ring system R contains, as heteroaryl group, triazine, pyrimidine, pyrazine, pyridazine, pyridine, imidazole, pyrazole, oxazole, oxadiazole, triazole, thiazole, thiadiazole, benzimidazole, quinoline, isoquinoline or quinoxaline and in particular is selected from the structures of the formulae (8) to (11) or from the formulae (42) to (45),

17. An organic electroluminescent device which comprises the compound according to claim 1 is used as hole-transport material or as emitting compound and at least one radical R stands for N(Ar¹)₂, for a triarylamino group or for an electron-rich heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R³.

18. A formulation comprising at least one compound according to claim 1 and at least one solvent.

19. A formulation comprising at least one or more polymers, oligomers or dendrimers according to claim 8 and at least one solvent.

20. An organic electroluminescent device which comprises the compound according to claim 1 is used as an electron transport material.