# US 2014/0197401 A1 · Organic electroluminescence device

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- Number: US 2014/0197401 A1
- Document ID: US20140197401A1
- Status: Published application
- Kind: A1
- Application number: 14/240,203
- Filed: 2012-07-25
- Published: 2014-07-17
- Earliest claimed: 2011-08-22
- Assignees: Merck Patent GmbH
- Inventors: Jonas Valentin Kroeber; Frank Voges; Susanne Heun; Joachim Kaiser
- Web page: https://patentgrep.com/patent/US20140197401A1

## CPC

- C09B 57/00: Other synthetic dyes of known constitution
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/165: comprising dopants
- H10K 71/00: Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 71/164: {using vacuum deposition}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present invention relates to organic electroluminescent devices which comprise a mixture of at least two materials in the electron-transport layer.

## Claims

### Claim at position 1

1-16. (canceled)

### Claim 17

An organic electroluminescent device comprising anode, cathode, at least one emitting layer and at least one electron-transport layer which is directly adjacent to the emitting layer on the cathode side, wherein the electron-transport layer comprises a mixture of at least two materials ETM1 and ETM2, where the following conditions apply to ETM1 and ETM2:
a) T1(ETM1)>2.2 eV; and
b) T1(ETM2)>2.2 eV; and
c) −3.2 eV<LUMO(ETM1)<−2.0 eV; and
d) LUMO(ETM2)>LUMO(ETM1);
where T1 stands for the lowest triplet energy of the respective material and LUMO stands for the energy of the lowest unoccupied molecular orbital of the respective material.

### Claim 18 (depends on 17)

The organic electroluminescent device according to claim 17, wherein ETM1 and ETM2 are purely organic materials.

### Claim 19 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the triplet energy T1 of ETM1 and ETM2 and of any further materials present in the electron-transport layer is >2.4 eV.

### Claim 20 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the LUMO of ETM1 is in the range from −3.1 eV to −2.2 eV.

### Claim 21 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the triplet energy T1 of ETM1 and ETM2 and of any further materials present in the electron-transport layer is >2.6 eV and wherein the LUMO of ETM1 is in the range from −3.0 eV to −2.4 eV.

### Claim 22 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the LUMO of ETM2 is at least 0.1 eV greater than the LUMO of ETM1.

### Claim 23 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the HOMO of ETM1 is <−5.3 eV.

### Claim 24 (depends on 17)

The organic electroluminescent device according to claim 17, wherein HOMO (ETM1)<HOMO (EML) and HOMO (ETM2)<HOMO (EML), where HOMO (EML) represents the HOMO of the emitting layer or of the material of the emitting layer which has the highest HOMO.

### Claim 25 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the proportion of ETM2 is ≧10% by vol. and furthermore the proportion of ETM2 is ≦90% by vol.

### Claim 26 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the proportion of ETM2 is ≧30% by vol. and furthermore the proportion of ETM2 is ≦80% by vol.

### Claim 27 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the electron-transport layer comprises no further materials apart from ETM1 and ETM2.

### Claim 28 (depends on 17)

The organic electroluminescent device according to claim 17, wherein ETM1 is selected from the group consisting of compounds containing six-membered heteroaryl ring groups, and compounds containing five-membered heteroaromatic rings having at least two heteroatoms.

### Claim 29 (depends on 17)

The organic electroluminescent device according to claim 17, wherein ETM1 is triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives or quinoline derivatives, oxadiazole derivatives or benzimidazole derivatives, or of aromatic ketones, boranes, lactams, diazaphosphole derivatives or phosphine oxide derivatives.

### Claim 30 (depends on 17)

The organic electroluminescent device according to claim 17, wherein a compound of one of the formulae (1) to (8) is used as ETM1,
where the following applies to the symbols used:
Ar is, identically or differently on each occurrence, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1;
Ar1 is a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R1;
R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)Ar2, P(═O)(Ar2)2, S(═O)Ar2, S(═O)2Ar2, CR2═CR2Ar2, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems; two or more adjacent substituents R1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2;
R2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by F; two or more adjacent substituents R2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another.
or wherein a ketone of the formula (23) or a phosphine oxide of the formula (24) is used as ETM1,
where Ar has the meaning given above.

### Claim 31 (depends on 17)

The organic electroluminescent device according to claim 17, wherein ETM2 is a pure hydrocarbon, or in that ETM2 is a carbazole derivative, a diazasilole derivative or a tetraazasilole derivative.

### Claim 32 (depends on 17)

The organic electroluminescent device according to claim 17, wherein ETM2 is an aromatic hydrocarbon, or in that ETM2 is a carbazole derivative, a diazasilole derivative or a tetraazasilole derivative.

### Claim 33 (depends on 17, 27)

The organic electroluminescent device according to claim 17, wherein ETM2 is selected from compounds of the formulae (36), (37) and (38),
where
R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)Ar2, P(═O)(Ar2)2, S(═O)Ar2, S(═O)2Ar2, CR2═CR2Ar2, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C=5, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or a combination of these systems; two or more adjacent substituents R1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R2;
R2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by F; two or more adjacent substituents R2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another.
Ar3 is on each occurrence, identically or differently, an aromatic ring system having 6 to 60 aromatic C atoms which contains no non-aromatic groups other than carbon or hydrogen; Ar3 here is optionally substituted by one or more radicals R4;
R3 is on each occurrence, identically or differently, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, or an aromatic ring system having 6 to 60 aromatic C atoms which contains no non-aromatic groups other than carbon or hydrogen and which is optionally substituted by one or more radicals R4; two or more radicals R3 here may also form a ring system with one another;
R4 is on each occurrence, identically or differently, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms; two or more radicals R4 here may also form a ring system with one another;
n is, identically or differently on each occurrence, 0 or 1;
or characterised in that a compound of the formula (39) or (40) is used as ETM2,
where the symbols used have the meanings given in claim 27.

### Claim 34 (depends on 17)

The organic electroluminescent device according to claim 17, wherein an electron-injection layer which comprises an alkali-metal or alkaline-earth metal fluoride, an alkali-metal or alkaline-earth metal oxide, an alkali-metal or alkaline-earth metal carbonate or an alkali-metal or alkaline-earth metal complex is used between the electron-transport layer and the metallic cathode.

### Claim 35 (depends on 17)

The organic electroluminescent device according to claim 17, wherein the emitting layer is phosphorescent and comprises a mixture of two or more matrix materials.

### Claim 36 (depends on 17)

A process for the production of the organic electroluminescent device according to claim 17, which comprises coating one or more layers by means of a sublimation process and/or in that one or more layers are coated by means of the OVPD process or with the aid of carrier-gas sublimation and/or in that one or more layers are coated from solution.